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N'-(2-Chloro-benzyl-idene)-2-(3,4-dimethyl-5,5-dioxo-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zin-2-yl)acetohydrazide.
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MedLine Citation:
PMID:  21522717     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The asymmetric unit of the title compound, C(20)H(18)ClN(5)O(3)S, contains two independent mol-ecules with significantly different conformations of the heterocyclic thia-zine rings. In both mol-ecules, the thia-zine rings adopt half-chair conformations, with the S atoms displaced by 0.382 (3) and 0.533 (3) Å and N atoms -0.351 and -0.275 Å, respectively, from the planes formed by the remaining ring atoms. The crystal structure is stabilized by weak inter-molecular N-H⋯O and C-H⋯O inter-actions.
Authors:
Matloob Ahmad; Hamid Latif Siddiqui; Manzoor Iqbal Khattak; Saeed Ahmad; Masood Parvez
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Publication Detail:
Type:  Journal Article     Date:  2010-12-24
Journal Detail:
Title:  Acta crystallographica. Section E, Structure reports online     Volume:  67     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr Sect E Struct Rep Online     Publication Date:  2010  
Date Detail:
Created Date:  2011-04-27     Completed Date:  2011-07-14     Revised Date:  2013-03-28    
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Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr Sect E Struct Rep Online     Country:  England    
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Languages:  eng     Pagination:  o218-9     Citation Subset:  -    
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Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
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A full version of this article is available from Crystallography Journals Online.© Ahmad et al. 2011
open-access:
Received Day: 07 Month: 12 Year: 2010
Accepted Day: 13 Month: 12 Year: 2010
collection publication date: Day: 01 Month: 1 Year: 2011
Electronic publication date: Day: 24 Month: 12 Year: 2010
pmc-release publication date: Day: 24 Month: 12 Year: 2010
Volume: 67 Issue: Pt 1
First Page: o218 Last Page: o219
ID: 3050389
PubMed Id: 21522717
Publisher Id: jh2243
DOI: 10.1107/S160053681005227X
Coden: ACSEBH
Publisher Item Identifier: S160053681005227X

N′-(2-Chloro­benzyl­idene)-2-(3,4-dimethyl-5,5-dioxo-2H,4H-pyrazolo­[4,3-c][1,2]benzothia­zin-2-yl)acetohydrazide Alternate Title:C20H18ClN5O3S
Matloob Ahmadab
Hamid Latif Siddiquia*
Manzoor Iqbal Khattakc
Saeed Ahmadd
Masood Parveze
aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan
cDepartment of Chemistry, University of Baluchistan, Quetta 6700, Pakistan
bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan
dDepartment of Chemistry, Gomal University, Dera Ismail Khan, Pakistan
eDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
Correspondence: Correspondence e-mail: drhamidlatif@yahoo.com

Related literature

For related structures, see: Ahmad et al. (2008, 2009, 2011); Siddiqui et al. (2008). For puckering parameters, see: Cremer & Pople (1975).[Chemical Structure ID: scheme1]


Experimental
Crystal data

  • C20H18ClN5O3S
  • Mr = 443.90
  • Triclinic,
  • a = 11.4881 (2) Å
  • b = 12.7518 (3) Å
  • c = 15.5690 (4) Å
  • α = 71.2778 (11)°
  • β = 78.6837 (13)°
  • γ = 70.4911 (12)°
  • V = 2025.92 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.33 mm−1
  • T = 173 K
  • 0.20 × 0.18 × 0.16 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SORTAV; Blessing, 1997) Tmin = 0.938, Tmax = 0.950
  • 13799 measured reflections
  • 7106 independent reflections
  • 5649 reflections with I > 2σ(I)
  • Rint = 0.024

Refinement

  • R[F2 > 2σ(F2)] = 0.036
  • wR(F2) = 0.106
  • S = 1.00
  • 7106 reflections
  • 545 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.


Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005227X/jh2243sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005227X/jh2243Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


Notes

fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2243).

The authors are grateful to the Higher Education Commission, Pakistan and the Institute of Chemistry, University of the Punjab, Lahore, Pakistan for financial assistance.

supplementary crystallographic information
Comment

In continuation to our research exploring potential biologically active derivatives of benzothiazines (Ahmad et al., 2008; 2009), we have devised the fusion of the pyrazole moiety with 1,2-benzothiazine nucleus in an attempt to synthesize novel bioactive molecules. In this paper, we report the synthesis and crystal structure of the title compound, (I).

In the structure of the title compound, there are two independent molecules (molecule a and molecule b) in an asymmetric unit with significantly different conformations of the heterocyclic thiazine rings (Figs. 1 and 2). In both molecules, the thiazine rings adopt half-chair conformations. In molecule a, S1 and N1 atoms are displaced by 0.382 (3) and -0.351 (3) Å, respectively, from the plane formed by the remaining ring atoms(C5–C8). In molecule b, S2 and N6 atoms are displaced by 0.533 (3) and -0.275 (3) Å, respectively, from the plane formed by the remaining ring atoms(C25–C28). The methyl groups attached to N1 and N6 are displaced by significantly different distances from the basal planes of the thiazine rings in the two molecules; 1.802 (4) and 1.694 (4) Å, respectively. The pertinent puckering parameters (Cremer & Pople, 1975) in molecules a and b are: Q = 0.475 (2) and 0.532 (4) Å, θ = 60.0 (4) and 63.4 (2)° and φ = 27.8 (3) and 20.0 (2)°, respectively. Similar conformations of the corresponding rings have been reported in some closely related molecules (Siddiqui et al., 2008; Ahmad et al., 2011).

The mean-planes defined by the pyrazolo and benzene rings of the benzothiazin fragment are inclined with respt to each other at 12.55 (7) and 18.04 (8)°, in the molecules a and b, respectively. The chlorophenyl-methylidene-acetohydrazide moieties in the two molecules display identical conformation. In the molecules labeled as a, intermolecular hydrogen bonds N4—H04···O3 result in the formation of dimmers and C18—H18···O1 link the molecules into chains. Similarly, the molecules b also exhibit intermolecular hydrogen bonds N9—H09···O6 resulting in the formation of dimmers while C38—H38···O4 link the molecules into chains. The molecules a and b are connected via C29—H29B···O2 hydrogen bonds further stabilizing the crystal structure (Tab. 1).

Experimental

A mixture of 2-(3,4-dimethyl-5,5-dioxidopyrazolo[4,3-c][1,2]benzothiazin- 2(4H)-yl)acetohydrazide (1.0 g, 3.12 mmol) and 2-chlorobenzaldehyde (0.44 g, 3.12 mmol) were dissolved in ethanol (50 ml) followed by the addition of 2 drops of glacial acetic acid. The mixture was subjected to reflux for 4 - 5 h. The completion of reaction was monitored with the help of thin layer chromatography (TLC). The precipitates formed were collected and washed with methanol (yield = 77%). The crystals of (I) suitable for crystallographic analysis were grown from its solution in dimethylamide at room temperature by slow evaporation.

Refinement

All the H atoms were discernible in the difference electron density map. However, they were positioned at the idealized positions and refined by the riding-model approximation using constraints: N—H = 0.88 Å, C—H = 0.98, 0.99 and 0.95 Å for methyl, methylene and aryl H-atoms, respectively, and Uiso(H) = 1.2Ueq(parent atoms). The methyl groups were allowed to rotate about their axes during the refinement.

Figures
Crystal data
Data collection
Refinement
Special details
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, °)
Hydrogen-bond geometry (Å, °)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y−1, −z+1; (iii) x+1, y, z−1; (iv) x+1, y−1, z; (v) x−1, y, z+1.


References
Ahmad, M., Siddiqui, H. L., Aslam, S., Ahmad, S. & Parvez, M. (2011). Acta Cryst. E67, o216–o217.
Ahmad, M., Siddiqui, H. L., Azam, M., Siddiqui, W. A. & Parvez, M. (2009). Acta Cryst. E65, o2185.
Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M., Ashiq, M. I. & Tizzard, G. J. (2008). Acta Cryst. E64, o788.
Blessing, R. H. (1997). J. Appl. Cryst.30, 421–426.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
Hooft, R. (1998). COLLECT Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4–o6.

Figures

[Figure ID: Fap1]
Fig. 1. 

The molecule a plotted with the displacement ellipsoids at 50% probability level (Farrugia, 1997).



[Figure ID: Fap2]
Fig. 2. 

The molecule b plotted with the displacement ellipsoids at 50% probability level (Farrugia, 1997).



Tables
[TableWrap ID: d1e136]
C20H18ClN5O3S Z = 4
Mr = 443.90 F(000) = 920
Triclinic, P1 Dx = 1.455 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 11.4881 (2) Å Cell parameters from 8973 reflections
b = 12.7518 (3) Å θ = 1.0–27.5°
c = 15.5690 (4) Å µ = 0.33 mm1
α = 71.2778 (11)° T = 173 K
β = 78.6837 (13)° Block, colorless
γ = 70.4911 (12)° 0.20 × 0.18 × 0.16 mm
V = 2025.92 (8) Å3

[TableWrap ID: d1e273]
Nonius KappaCCD diffractometer 7106 independent reflections
Radiation source: fine-focus sealed tube 5649 reflections with I > 2σ(I)
graphite Rint = 0.024
ω and φ scans θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SORTAV; Blessing, 1997) h = −13→13
Tmin = 0.938, Tmax = 0.950 k = −15→15
13799 measured reflections l = −18→18

[TableWrap ID: d1e390]
Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036 Hydrogen site location: difference Fourier map
wR(F2) = 0.106 H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.061P)2 + 0.760P] where P = (Fo2 + 2Fc2)/3
7106 reflections (Δ/σ)max = 0.001
545 parameters Δρmax = 0.25 e Å3
0 restraints Δρmin = −0.39 e Å3

[TableWrap ID: d1e547]
Experimental. Colorless crystals; mp 482 - 484 K. IR (KBr) cm-1: 3478, 1699, 1595, 1340, 1155. 1H-NMR (DMSO– d6) (400 MHz) δ 2.32 (3H, s, CCH3), 2.98 (3H, s, NCH3), 5.52 (2H, s, NCH2), 7.63–7.69 (2H, m, ArH), 7.76–7.80 (2H, q, J = 17.9, 7.6 Hz, ArH), 7.86 (1H, d, J = 7.80 Hz, ArH), 7.93 (1H, d, J = 7.7 Hz, ArH), 8.08 (1H, d, J = 8.2 Hz, ArH), 8.16 (1H, d, J = 8.0 Hz, ArH), 8.46 (1H, s, N═CH), 12.09 (1H, br s, NH). 13C NMR: 8.5, 38.9, 51.3, 121.4, 122.4, 123.1, 124.6, 124.7, 124.9, 126.2, 126.4, 127.5, 127.7, 127.8, 128.1, 130.6, 132.9, 134.2, 136.2, 136.8, 166.3. MS m/z: 444.0(M+).
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

[TableWrap ID: d1e755]
x y z Uiso*/Ueq
Cl1 0.25790 (5) 0.47702 (5) −0.33819 (4) 0.03347 (14)
Cl2 −0.26345 (5) −0.48073 (5) 0.84350 (4) 0.03564 (15)
S1 −0.50025 (5) 0.25138 (5) 0.37138 (3) 0.03121 (15)
S2 0.50831 (4) −0.18110 (4) 0.15070 (3) 0.02402 (13)
O1 −0.61045 (14) 0.22302 (16) 0.41864 (11) 0.0472 (4)
O2 −0.48908 (16) 0.36345 (13) 0.35969 (11) 0.0462 (4)
O3 −0.11061 (14) 0.42389 (13) 0.08697 (10) 0.0364 (4)
O4 0.61488 (12) −0.22162 (13) 0.09197 (10) 0.0330 (3)
O5 0.50899 (13) −0.10151 (12) 0.19769 (10) 0.0305 (3)
O6 0.10093 (14) −0.41879 (13) 0.41403 (10) 0.0336 (4)
N1 −0.48174 (14) 0.23141 (14) 0.26951 (11) 0.0256 (4)
N2 −0.14910 (15) 0.17558 (14) 0.21567 (11) 0.0257 (4)
N3 −0.19344 (14) 0.23215 (14) 0.13286 (11) 0.0235 (4)
N4 0.00120 (15) 0.38951 (15) −0.04161 (11) 0.0271 (4)
H04 0.0281 0.4500 −0.0526 0.033*
N5 0.03678 (15) 0.32466 (14) −0.10331 (11) 0.0247 (4)
N6 0.47766 (14) −0.29427 (14) 0.22751 (11) 0.0232 (4)
N7 0.15457 (14) −0.16124 (14) 0.29530 (11) 0.0240 (4)
N8 0.19665 (14) −0.23898 (14) 0.37419 (11) 0.0226 (4)
N9 −0.00865 (15) −0.38815 (15) 0.54391 (11) 0.0264 (4)
H09 −0.0389 −0.4461 0.5523 0.032*
N10 −0.04085 (14) −0.32727 (14) 0.60840 (11) 0.0235 (4)
C1 −0.15139 (19) 0.05007 (17) 0.41734 (14) 0.0271 (4)
H1 −0.0729 0.0304 0.3834 0.033*
C2 −0.1625 (2) 0.00523 (19) 0.51109 (14) 0.0317 (5)
H2 −0.0914 −0.0450 0.5409 0.038*
C3 −0.2761 (2) 0.03255 (19) 0.56234 (15) 0.0339 (5)
H3 −0.2822 0.0019 0.6268 0.041*
C4 −0.3804 (2) 0.10447 (18) 0.51930 (14) 0.0318 (5)
H4 −0.4588 0.1226 0.5537 0.038*
C5 −0.36949 (18) 0.14994 (17) 0.42513 (13) 0.0259 (4)
C6 −0.25467 (17) 0.12395 (16) 0.37233 (13) 0.0234 (4)
C7 −0.25122 (17) 0.17367 (16) 0.27358 (13) 0.0214 (4)
C8 −0.35875 (17) 0.22887 (17) 0.22753 (13) 0.0226 (4)
C9 −0.5213 (2) 0.1342 (2) 0.26466 (16) 0.0358 (5)
H9A −0.5154 0.1350 0.2008 0.043*
H9B −0.6074 0.1426 0.2917 0.043*
H9C −0.4674 0.0607 0.2983 0.043*
C10 −0.31995 (17) 0.26745 (17) 0.13709 (13) 0.0237 (4)
C11 −0.3911 (2) 0.3342 (2) 0.05664 (14) 0.0342 (5)
H11A −0.4802 0.3497 0.0762 0.041*
H11B −0.3686 0.2891 0.0122 0.041*
H11C −0.3713 0.4076 0.0286 0.041*
C12 −0.10719 (18) 0.25138 (18) 0.05219 (13) 0.0264 (4)
H12A −0.1446 0.2551 −0.0012 0.032*
H12B −0.0307 0.1852 0.0593 0.032*
C13 −0.07352 (18) 0.36260 (18) 0.03483 (13) 0.0256 (4)
C14 0.10219 (17) 0.36567 (18) −0.17459 (13) 0.0257 (4)
H14 0.1229 0.4339 −0.1801 0.031*
C15 0.14552 (17) 0.30888 (17) −0.24767 (13) 0.0239 (4)
C16 0.21805 (17) 0.35203 (18) −0.32574 (14) 0.0262 (4)
C17 0.25943 (19) 0.2978 (2) −0.39504 (15) 0.0339 (5)
H17 0.3080 0.3289 −0.4479 0.041*
C18 0.2294 (2) 0.1983 (2) −0.38658 (15) 0.0375 (5)
H18 0.2584 0.1601 −0.4334 0.045*
C19 0.1572 (2) 0.1542 (2) −0.31005 (15) 0.0355 (5)
H19 0.1366 0.0859 −0.3044 0.043*
C20 0.11527 (19) 0.20949 (19) −0.24212 (14) 0.0300 (5)
H20 0.0646 0.1793 −0.1904 0.036*
C21 0.15474 (18) −0.05797 (17) 0.08887 (14) 0.0264 (4)
H21 0.0741 −0.0537 0.1200 0.032*
C22 0.16845 (19) −0.00809 (18) −0.00436 (14) 0.0301 (5)
H22 0.0967 0.0316 −0.0362 0.036*
C23 0.28514 (19) −0.01504 (18) −0.05205 (14) 0.0300 (5)
H23 0.2931 0.0184 −0.1161 0.036*
C24 0.38999 (19) −0.07118 (17) −0.00546 (13) 0.0262 (4)
H24 0.4703 −0.0775 −0.0375 0.031*
C25 0.37652 (17) −0.11814 (16) 0.08832 (13) 0.0223 (4)
C26 0.25873 (17) −0.11432 (16) 0.13714 (13) 0.0227 (4)
C27 0.25414 (17) −0.17512 (16) 0.23418 (13) 0.0215 (4)
C28 0.35753 (17) −0.25970 (17) 0.27479 (13) 0.0223 (4)
C29 0.5033 (2) −0.39860 (18) 0.19582 (15) 0.0322 (5)
H29A 0.4899 −0.4631 0.2476 0.039*
H29B 0.5895 −0.4193 0.1689 0.039*
H29C 0.4473 −0.3823 0.1500 0.039*
C30 0.31849 (17) −0.30032 (16) 0.36504 (13) 0.0225 (4)
C31 0.38679 (19) −0.39090 (18) 0.44001 (14) 0.0311 (5)
H31A 0.4756 −0.4133 0.4194 0.037*
H31B 0.3560 −0.4587 0.4575 0.037*
H31C 0.3739 −0.3605 0.4926 0.037*
C32 0.11075 (18) −0.25551 (17) 0.45531 (13) 0.0252 (4)
H32A 0.0379 −0.1858 0.4501 0.030*
H32B 0.1516 −0.2658 0.5091 0.030*
C33 0.06770 (17) −0.36078 (17) 0.46880 (13) 0.0242 (4)
C34 −0.10689 (17) −0.36873 (17) 0.67866 (13) 0.0245 (4)
H34 −0.1301 −0.4350 0.6822 0.029*
C35 −0.14732 (17) −0.31510 (17) 0.75402 (13) 0.0227 (4)
C36 −0.21890 (17) −0.35873 (18) 0.83283 (14) 0.0262 (4)
C37 −0.25619 (18) −0.3068 (2) 0.90357 (14) 0.0316 (5)
H37 −0.3026 −0.3390 0.9573 0.038*
C38 −0.22519 (19) −0.2081 (2) 0.89518 (15) 0.0339 (5)
H38 −0.2522 −0.1710 0.9426 0.041*
C39 −0.15498 (19) −0.16290 (19) 0.81798 (15) 0.0318 (5)
H39 −0.1339 −0.0949 0.8125 0.038*
C40 −0.11553 (18) −0.21659 (18) 0.74900 (14) 0.0272 (4)
H40 −0.0656 −0.1859 0.6969 0.033*

[TableWrap ID: d1e2187]
U11 U22 U33 U12 U13 U23
Cl1 0.0357 (3) 0.0364 (3) 0.0268 (3) −0.0187 (2) 0.0064 (2) −0.0037 (2)
Cl2 0.0393 (3) 0.0396 (3) 0.0294 (3) −0.0234 (2) 0.0074 (2) −0.0053 (2)
S1 0.0320 (3) 0.0300 (3) 0.0205 (3) −0.0019 (2) 0.0051 (2) −0.0043 (2)
S2 0.0226 (2) 0.0284 (3) 0.0189 (3) −0.0114 (2) 0.00193 (19) −0.0018 (2)
O1 0.0310 (8) 0.0627 (11) 0.0270 (9) −0.0042 (8) 0.0108 (7) −0.0027 (8)
O2 0.0704 (11) 0.0260 (8) 0.0323 (9) −0.0015 (8) −0.0032 (8) −0.0091 (7)
O3 0.0515 (9) 0.0381 (9) 0.0277 (8) −0.0269 (7) 0.0168 (7) −0.0175 (7)
O4 0.0253 (7) 0.0407 (9) 0.0231 (8) −0.0080 (6) 0.0070 (6) −0.0029 (7)
O5 0.0337 (8) 0.0335 (8) 0.0287 (8) −0.0181 (6) −0.0019 (6) −0.0066 (7)
O6 0.0458 (9) 0.0357 (8) 0.0272 (8) −0.0248 (7) 0.0162 (7) −0.0172 (7)
N1 0.0224 (8) 0.0312 (9) 0.0190 (9) −0.0097 (7) 0.0034 (7) −0.0027 (7)
N2 0.0277 (9) 0.0294 (9) 0.0206 (9) −0.0130 (7) 0.0013 (7) −0.0048 (7)
N3 0.0270 (8) 0.0282 (9) 0.0162 (8) −0.0137 (7) 0.0040 (7) −0.0049 (7)
N4 0.0356 (9) 0.0314 (10) 0.0209 (9) −0.0203 (8) 0.0084 (7) −0.0114 (8)
N5 0.0273 (8) 0.0280 (9) 0.0207 (9) −0.0103 (7) 0.0029 (7) −0.0100 (7)
N6 0.0234 (8) 0.0243 (9) 0.0179 (8) −0.0083 (7) 0.0015 (7) −0.0014 (7)
N7 0.0257 (8) 0.0247 (9) 0.0198 (9) −0.0113 (7) 0.0006 (7) −0.0012 (7)
N8 0.0269 (8) 0.0238 (9) 0.0172 (8) −0.0128 (7) 0.0039 (7) −0.0039 (7)
N9 0.0338 (9) 0.0304 (9) 0.0218 (9) −0.0191 (8) 0.0094 (7) −0.0133 (8)
N10 0.0256 (8) 0.0270 (9) 0.0196 (9) −0.0102 (7) 0.0037 (7) −0.0094 (7)
C1 0.0289 (10) 0.0294 (11) 0.0258 (11) −0.0132 (9) −0.0026 (8) −0.0064 (9)
C2 0.0347 (11) 0.0344 (12) 0.0267 (12) −0.0134 (9) −0.0100 (9) −0.0016 (10)
C3 0.0451 (13) 0.0373 (13) 0.0197 (11) −0.0202 (10) −0.0026 (9) −0.0003 (9)
C4 0.0370 (12) 0.0323 (12) 0.0217 (11) −0.0115 (9) 0.0030 (9) −0.0034 (9)
C5 0.0313 (11) 0.0246 (11) 0.0202 (11) −0.0106 (8) 0.0017 (8) −0.0038 (9)
C6 0.0289 (10) 0.0221 (10) 0.0218 (10) −0.0132 (8) −0.0003 (8) −0.0050 (8)
C7 0.0246 (10) 0.0222 (10) 0.0187 (10) −0.0110 (8) 0.0019 (8) −0.0055 (8)
C8 0.0229 (10) 0.0250 (10) 0.0197 (10) −0.0096 (8) 0.0026 (8) −0.0060 (8)
C9 0.0299 (11) 0.0446 (14) 0.0354 (13) −0.0199 (10) 0.0006 (10) −0.0073 (11)
C10 0.0267 (10) 0.0251 (10) 0.0205 (10) −0.0115 (8) 0.0010 (8) −0.0060 (8)
C11 0.0361 (12) 0.0405 (13) 0.0215 (11) −0.0138 (10) −0.0023 (9) −0.0001 (10)
C12 0.0308 (10) 0.0299 (11) 0.0210 (11) −0.0167 (9) 0.0093 (8) −0.0093 (9)
C13 0.0277 (10) 0.0305 (11) 0.0202 (10) −0.0140 (9) 0.0048 (8) −0.0074 (9)
C14 0.0263 (10) 0.0313 (11) 0.0216 (11) −0.0148 (9) 0.0048 (8) −0.0079 (9)
C15 0.0240 (10) 0.0287 (11) 0.0180 (10) −0.0081 (8) −0.0003 (8) −0.0055 (8)
C16 0.0241 (10) 0.0322 (11) 0.0208 (10) −0.0097 (8) 0.0006 (8) −0.0052 (9)
C17 0.0326 (11) 0.0463 (14) 0.0213 (11) −0.0135 (10) 0.0074 (9) −0.0109 (10)
C18 0.0384 (12) 0.0500 (15) 0.0286 (12) −0.0148 (11) 0.0080 (10) −0.0218 (11)
C19 0.0415 (12) 0.0390 (13) 0.0314 (12) −0.0148 (10) 0.0017 (10) −0.0169 (10)
C20 0.0334 (11) 0.0360 (12) 0.0226 (11) −0.0170 (9) 0.0061 (9) −0.0088 (9)
C21 0.0264 (10) 0.0281 (11) 0.0258 (11) −0.0138 (8) −0.0021 (8) −0.0033 (9)
C22 0.0327 (11) 0.0336 (12) 0.0246 (11) −0.0143 (9) −0.0088 (9) −0.0005 (9)
C23 0.0386 (12) 0.0335 (12) 0.0187 (10) −0.0171 (9) −0.0024 (9) −0.0018 (9)
C24 0.0315 (10) 0.0271 (11) 0.0200 (10) −0.0136 (9) 0.0012 (8) −0.0033 (9)
C25 0.0266 (10) 0.0212 (10) 0.0189 (10) −0.0103 (8) −0.0004 (8) −0.0027 (8)
C26 0.0281 (10) 0.0219 (10) 0.0192 (10) −0.0125 (8) 0.0012 (8) −0.0037 (8)
C27 0.0232 (9) 0.0227 (10) 0.0189 (10) −0.0116 (8) 0.0013 (8) −0.0030 (8)
C28 0.0224 (9) 0.0261 (10) 0.0178 (10) −0.0111 (8) 0.0015 (8) −0.0031 (8)
C29 0.0386 (12) 0.0261 (11) 0.0296 (12) −0.0097 (9) 0.0006 (9) −0.0066 (9)
C30 0.0250 (10) 0.0239 (10) 0.0199 (10) −0.0115 (8) 0.0016 (8) −0.0057 (8)
C31 0.0331 (11) 0.0323 (12) 0.0201 (11) −0.0096 (9) 0.0011 (9) 0.0008 (9)
C32 0.0301 (10) 0.0269 (11) 0.0197 (10) −0.0145 (8) 0.0084 (8) −0.0080 (9)
C33 0.0255 (10) 0.0277 (11) 0.0201 (10) −0.0122 (8) 0.0044 (8) −0.0066 (9)
C34 0.0267 (10) 0.0280 (11) 0.0217 (10) −0.0141 (8) 0.0042 (8) −0.0083 (9)
C35 0.0208 (9) 0.0285 (11) 0.0174 (10) −0.0079 (8) 0.0012 (8) −0.0055 (8)
C36 0.0222 (10) 0.0335 (12) 0.0219 (11) −0.0097 (8) 0.0003 (8) −0.0062 (9)
C37 0.0269 (10) 0.0478 (14) 0.0185 (11) −0.0136 (10) 0.0051 (8) −0.0086 (10)
C38 0.0294 (11) 0.0512 (14) 0.0263 (12) −0.0114 (10) 0.0033 (9) −0.0215 (11)
C39 0.0320 (11) 0.0368 (12) 0.0314 (12) −0.0124 (9) 0.0006 (9) −0.0155 (10)
C40 0.0273 (10) 0.0329 (11) 0.0234 (11) −0.0131 (9) 0.0030 (8) −0.0094 (9)

[TableWrap ID: d1e3399]
Cl1—C16 1.744 (2) C11—H11C 0.9800
Cl2—C36 1.744 (2) C12—C13 1.521 (3)
S1—O2 1.4276 (17) C12—H12A 0.9900
S1—O1 1.4298 (17) C12—H12B 0.9900
S1—N1 1.6481 (17) C14—C15 1.460 (3)
S1—C5 1.769 (2) C14—H14 0.9500
S2—O4 1.4295 (14) C15—C20 1.395 (3)
S2—O5 1.4315 (15) C15—C16 1.398 (3)
S2—N6 1.6440 (16) C16—C17 1.388 (3)
S2—C25 1.7734 (19) C17—C18 1.384 (3)
O3—C13 1.225 (2) C17—H17 0.9500
O6—C33 1.228 (2) C18—C19 1.384 (3)
N1—C8 1.430 (2) C18—H18 0.9500
N1—C9 1.483 (3) C19—C20 1.378 (3)
N2—C7 1.334 (2) C19—H19 0.9500
N2—N3 1.363 (2) C20—H20 0.9500
N3—C10 1.365 (2) C21—C22 1.386 (3)
N3—C12 1.448 (2) C21—C26 1.393 (3)
N4—C13 1.343 (2) C21—H21 0.9500
N4—N5 1.380 (2) C22—C23 1.389 (3)
N4—H04 0.8800 C22—H22 0.9500
N5—C14 1.278 (2) C23—C24 1.387 (3)
N6—C28 1.430 (2) C23—H23 0.9500
N6—C29 1.484 (3) C24—C25 1.388 (3)
N7—C27 1.338 (2) C24—H24 0.9500
N7—N8 1.362 (2) C25—C26 1.410 (3)
N8—C30 1.361 (2) C26—C27 1.460 (3)
N8—C32 1.446 (2) C27—C28 1.405 (3)
N9—C33 1.341 (2) C28—C30 1.373 (3)
N9—N10 1.382 (2) C29—H29A 0.9800
N9—H09 0.8800 C29—H29B 0.9800
N10—C34 1.274 (2) C29—H29C 0.9800
C1—C2 1.383 (3) C30—C31 1.483 (3)
C1—C6 1.394 (3) C31—H31A 0.9800
C1—H1 0.9500 C31—H31B 0.9800
C2—C3 1.388 (3) C31—H31C 0.9800
C2—H2 0.9500 C32—C33 1.521 (3)
C3—C4 1.383 (3) C32—H32A 0.9900
C3—H3 0.9500 C32—H32B 0.9900
C4—C5 1.390 (3) C34—C35 1.466 (3)
C4—H4 0.9500 C34—H34 0.9500
C5—C6 1.408 (3) C35—C40 1.396 (3)
C6—C7 1.461 (3) C35—C36 1.401 (3)
C7—C8 1.407 (3) C36—C37 1.388 (3)
C8—C10 1.371 (3) C37—C38 1.381 (3)
C9—H9A 0.9800 C37—H37 0.9500
C9—H9B 0.9800 C38—C39 1.383 (3)
C9—H9C 0.9800 C38—H38 0.9500
C10—C11 1.488 (3) C39—C40 1.379 (3)
C11—H11A 0.9800 C39—H39 0.9500
C11—H11B 0.9800 C40—H40 0.9500
O2—S1—O1 119.67 (11) C20—C15—C14 120.97 (18)
O2—S1—N1 107.75 (9) C16—C15—C14 121.48 (18)
O1—S1—N1 107.62 (10) C17—C16—C15 121.44 (19)
O2—S1—C5 106.56 (10) C17—C16—Cl1 118.40 (16)
O1—S1—C5 109.55 (10) C15—C16—Cl1 120.16 (15)
N1—S1—C5 104.71 (9) C18—C17—C16 119.5 (2)
O4—S2—O5 119.73 (9) C18—C17—H17 120.3
O4—S2—N6 108.16 (9) C16—C17—H17 120.3
O5—S2—N6 107.65 (8) C17—C18—C19 120.1 (2)
O4—S2—C25 109.04 (9) C17—C18—H18 119.9
O5—S2—C25 107.54 (9) C19—C18—H18 119.9
N6—S2—C25 103.53 (8) C20—C19—C18 120.0 (2)
C8—N1—C9 113.18 (16) C20—C19—H19 120.0
C8—N1—S1 110.51 (12) C18—C19—H19 120.0
C9—N1—S1 115.83 (13) C19—C20—C15 121.4 (2)
C7—N2—N3 103.85 (15) C19—C20—H20 119.3
N2—N3—C10 113.56 (15) C15—C20—H20 119.3
N2—N3—C12 119.49 (15) C22—C21—C26 120.25 (18)
C10—N3—C12 126.94 (17) C22—C21—H21 119.9
C13—N4—N5 121.66 (16) C26—C21—H21 119.9
C13—N4—H04 119.2 C21—C22—C23 121.22 (19)
N5—N4—H04 119.2 C21—C22—H22 119.4
C14—N5—N4 113.66 (16) C23—C22—H22 119.4
C28—N6—C29 115.32 (15) C24—C23—C22 119.52 (19)
C28—N6—S2 109.81 (12) C24—C23—H23 120.2
C29—N6—S2 115.80 (13) C22—C23—H23 120.2
C27—N7—N8 103.62 (15) C23—C24—C25 119.43 (19)
C30—N8—N7 113.79 (15) C23—C24—H24 120.3
C30—N8—C32 126.45 (17) C25—C24—H24 120.3
N7—N8—C32 119.58 (15) C24—C25—C26 121.56 (17)
C33—N9—N10 121.36 (16) C24—C25—S2 120.38 (15)
C33—N9—H09 119.3 C26—C25—S2 118.03 (14)
N10—N9—H09 119.3 C21—C26—C25 117.97 (17)
C34—N10—N9 113.79 (16) C21—C26—C27 124.23 (17)
C2—C1—C6 120.39 (19) C25—C26—C27 117.72 (17)
C2—C1—H1 119.8 N7—C27—C28 111.17 (16)
C6—C1—H1 119.8 N7—C27—C26 126.21 (17)
C1—C2—C3 121.03 (19) C28—C27—C26 122.61 (17)
C1—C2—H2 119.5 C30—C28—C27 106.59 (16)
C3—C2—H2 119.5 C30—C28—N6 128.76 (17)
C4—C3—C2 119.8 (2) C27—C28—N6 124.65 (17)
C4—C3—H3 120.1 N6—C29—H29A 109.5
C2—C3—H3 120.1 N6—C29—H29B 109.5
C3—C4—C5 119.4 (2) H29A—C29—H29B 109.5
C3—C4—H4 120.3 N6—C29—H29C 109.5
C5—C4—H4 120.3 H29A—C29—H29C 109.5
C4—C5—C6 121.53 (19) H29B—C29—H29C 109.5
C4—C5—S1 119.17 (15) N8—C30—C28 104.83 (16)
C6—C5—S1 119.13 (15) N8—C30—C31 124.68 (17)
C1—C6—C5 117.93 (18) C28—C30—C31 130.49 (17)
C1—C6—C7 123.84 (18) C30—C31—H31A 109.5
C5—C6—C7 118.22 (17) C30—C31—H31B 109.5
N2—C7—C8 111.11 (16) H31A—C31—H31B 109.5
N2—C7—C6 125.81 (17) C30—C31—H31C 109.5
C8—C7—C6 123.06 (16) H31A—C31—H31C 109.5
C10—C8—C7 106.71 (16) H31B—C31—H31C 109.5
C10—C8—N1 128.69 (17) N8—C32—C33 111.10 (15)
C7—C8—N1 124.34 (17) N8—C32—H32A 109.4
N1—C9—H9A 109.5 C33—C32—H32A 109.4
N1—C9—H9B 109.5 N8—C32—H32B 109.4
H9A—C9—H9B 109.5 C33—C32—H32B 109.4
N1—C9—H9C 109.5 H32A—C32—H32B 108.0
H9A—C9—H9C 109.5 O6—C33—N9 121.04 (18)
H9B—C9—H9C 109.5 O6—C33—C32 122.09 (17)
N3—C10—C8 104.75 (17) N9—C33—C32 116.87 (16)
N3—C10—C11 124.02 (17) N10—C34—C35 120.56 (18)
C8—C10—C11 131.22 (18) N10—C34—H34 119.7
C10—C11—H11A 109.5 C35—C34—H34 119.7
C10—C11—H11B 109.5 C40—C35—C36 117.36 (18)
H11A—C11—H11B 109.5 C40—C35—C34 120.32 (18)
C10—C11—H11C 109.5 C36—C35—C34 122.32 (18)
H11A—C11—H11C 109.5 C37—C36—C35 121.51 (19)
H11B—C11—H11C 109.5 C37—C36—Cl2 118.54 (16)
N3—C12—C13 112.17 (16) C35—C36—Cl2 119.96 (15)
N3—C12—H12A 109.2 C38—C37—C36 119.40 (19)
C13—C12—H12A 109.2 C38—C37—H37 120.3
N3—C12—H12B 109.2 C36—C37—H37 120.3
C13—C12—H12B 109.2 C37—C38—C39 120.28 (19)
H12A—C12—H12B 107.9 C37—C38—H38 119.9
O3—C13—N4 121.57 (18) C39—C38—H38 119.9
O3—C13—C12 122.80 (17) C40—C39—C38 120.0 (2)
N4—C13—C12 115.63 (17) C40—C39—H39 120.0
N5—C14—C15 120.76 (18) C38—C39—H39 120.0
N5—C14—H14 119.6 C39—C40—C35 121.42 (19)
C15—C14—H14 119.6 C39—C40—H40 119.3
C20—C15—C16 117.54 (18) C35—C40—H40 119.3
O2—S1—N1—C8 64.64 (15) C20—C15—C16—Cl1 179.16 (15)
O1—S1—N1—C8 −165.04 (13) C14—C15—C16—Cl1 −0.5 (3)
C5—S1—N1—C8 −48.53 (15) C15—C16—C17—C18 −0.6 (3)
O2—S1—N1—C9 −164.98 (14) Cl1—C16—C17—C18 179.75 (17)
O1—S1—N1—C9 −34.66 (17) C16—C17—C18—C19 0.9 (3)
C5—S1—N1—C9 81.85 (15) C17—C18—C19—C20 −0.1 (3)
C7—N2—N3—C10 1.0 (2) C18—C19—C20—C15 −1.1 (3)
C7—N2—N3—C12 179.57 (16) C16—C15—C20—C19 1.3 (3)
C13—N4—N5—C14 176.32 (19) C14—C15—C20—C19 −179.00 (19)
O4—S2—N6—C28 −167.43 (12) C26—C21—C22—C23 1.4 (3)
O5—S2—N6—C28 61.86 (14) C21—C22—C23—C24 −1.1 (3)
C25—S2—N6—C28 −51.83 (14) C22—C23—C24—C25 −0.9 (3)
O4—S2—N6—C29 −34.67 (16) C23—C24—C25—C26 2.6 (3)
O5—S2—N6—C29 −165.37 (13) C23—C24—C25—S2 −175.41 (15)
C25—S2—N6—C29 80.94 (15) O4—S2—C25—C24 −26.45 (19)
C27—N7—N8—C30 0.4 (2) O5—S2—C25—C24 104.80 (16)
C27—N7—N8—C32 −175.10 (15) N6—S2—C25—C24 −141.43 (16)
C33—N9—N10—C34 −175.35 (18) O4—S2—C25—C26 155.45 (15)
C6—C1—C2—C3 0.0 (3) O5—S2—C25—C26 −73.30 (16)
C1—C2—C3—C4 0.8 (3) N6—S2—C25—C26 40.48 (17)
C2—C3—C4—C5 −1.0 (3) C22—C21—C26—C25 0.3 (3)
C3—C4—C5—C6 0.4 (3) C22—C21—C26—C27 −176.28 (18)
C3—C4—C5—S1 −174.74 (16) C24—C25—C26—C21 −2.3 (3)
O2—S1—C5—C4 95.97 (18) S2—C25—C26—C21 175.79 (14)
O1—S1—C5—C4 −34.8 (2) C24—C25—C26—C27 174.49 (17)
N1—S1—C5—C4 −150.01 (16) S2—C25—C26—C27 −7.4 (2)
O2—S1—C5—C6 −79.25 (17) N8—N7—C27—C28 −0.7 (2)
O1—S1—C5—C6 149.94 (16) N8—N7—C27—C26 178.13 (17)
N1—S1—C5—C6 34.76 (18) C21—C26—C27—N7 −19.1 (3)
C2—C1—C6—C5 −0.6 (3) C25—C26—C27—N7 164.35 (18)
C2—C1—C6—C7 −179.12 (18) C21—C26—C27—C28 159.56 (19)
C4—C5—C6—C1 0.4 (3) C25—C26—C27—C28 −17.0 (3)
S1—C5—C6—C1 175.55 (14) N7—C27—C28—C30 0.7 (2)
C4—C5—C6—C7 179.03 (18) C26—C27—C28—C30 −178.12 (17)
S1—C5—C6—C7 −5.9 (2) N7—C27—C28—N6 −179.99 (16)
N3—N2—C7—C8 −0.2 (2) C26—C27—C28—N6 1.2 (3)
N3—N2—C7—C6 −178.90 (17) C29—N6—C28—C30 83.4 (2)
C1—C6—C7—N2 −14.4 (3) S2—N6—C28—C30 −143.56 (18)
C5—C6—C7—N2 167.13 (18) C29—N6—C28—C27 −95.7 (2)
C1—C6—C7—C8 167.05 (18) S2—N6—C28—C27 37.3 (2)
C5—C6—C7—C8 −11.5 (3) N7—N8—C30—C28 0.0 (2)
N2—C7—C8—C10 −0.7 (2) C32—N8—C30—C28 175.16 (17)
C6—C7—C8—C10 178.07 (17) N7—N8—C30—C31 −179.45 (17)
N2—C7—C8—N1 173.85 (17) C32—N8—C30—C31 −4.3 (3)
C6—C7—C8—N1 −7.4 (3) C27—C28—C30—N8 −0.4 (2)
C9—N1—C8—C10 82.0 (2) N6—C28—C30—N8 −179.69 (18)
S1—N1—C8—C10 −146.19 (18) C27—C28—C30—C31 179.02 (19)
C9—N1—C8—C7 −91.3 (2) N6—C28—C30—C31 −0.2 (3)
S1—N1—C8—C7 40.5 (2) C30—N8—C32—C33 −76.9 (2)
N2—N3—C10—C8 −1.5 (2) N7—N8—C32—C33 97.98 (19)
C12—N3—C10—C8 −179.88 (17) N10—N9—C33—O6 176.29 (17)
N2—N3—C10—C11 177.98 (18) N10—N9—C33—C32 −3.5 (3)
C12—N3—C10—C11 −0.4 (3) N8—C32—C33—O6 −2.4 (3)
C7—C8—C10—N3 1.2 (2) N8—C32—C33—N9 177.41 (17)
N1—C8—C10—N3 −172.99 (18) N9—N10—C34—C35 179.12 (16)
C7—C8—C10—C11 −178.1 (2) N10—C34—C35—C40 1.0 (3)
N1—C8—C10—C11 7.6 (4) N10—C34—C35—C36 −179.33 (19)
N2—N3—C12—C13 −87.3 (2) C40—C35—C36—C37 −0.5 (3)
C10—N3—C12—C13 91.0 (2) C34—C35—C36—C37 179.91 (18)
N5—N4—C13—O3 −175.86 (18) C40—C35—C36—Cl2 179.38 (14)
N5—N4—C13—C12 4.7 (3) C34—C35—C36—Cl2 −0.3 (3)
N3—C12—C13—O3 3.9 (3) C35—C36—C37—C38 1.9 (3)
N3—C12—C13—N4 −176.66 (17) Cl2—C36—C37—C38 −177.96 (16)
N4—N5—C14—C15 −178.77 (16) C36—C37—C38—C39 −1.6 (3)
N5—C14—C15—C20 0.9 (3) C37—C38—C39—C40 −0.1 (3)
N5—C14—C15—C16 −179.43 (19) C38—C39—C40—C35 1.5 (3)
C20—C15—C16—C17 −0.5 (3) C36—C35—C40—C39 −1.3 (3)
C14—C15—C16—C17 179.85 (18) C34—C35—C40—C39 178.39 (19)

[TableWrap ID: d1e5434]
D—H···A D—H H···A D···A D—H···A
C14—H14···Cl1 0.95 2.64 3.048 (2) 106.
C34—H34···Cl2 0.95 2.67 3.068 (2) 106.
N4—H04···O3i 0.88 2.01 2.883 (2) 172.
N9—H09···O6ii 0.88 1.96 2.837 (2) 173.
C18—H18···O1iii 0.95 2.55 3.204 (3) 127.
C29—H29A···O2iv 0.98 2.31 3.266 (3) 165.
C38—H38···O4v 0.95 2.54 3.233 (2) 130.
C9—H9B···O1 0.98 2.49 2.843 (3) 101.
C29—H29B···O4 0.98 2.51 2.851 (3) 100.


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