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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o882.
Published online 2010 March 20. doi:  10.1107/S1600536810009803
PMCID: PMC2983948

2-[2-(2,6-Dichloro­anilino)phen­yl]-N-[(2S)-2-methyl-3-oxo-8-phenyl-1-thia-4-aza­spiro­[4.5]dec-4-yl]acetamide

Abstract

In the title compound, C29H29Cl2N3O2S, the phenyl ring is disordered over two orientations with occupancies of 0.55 (3) and 0.45 (3). The mol­ecular packing in the crystal is stabilized by inter­molecular N—H(...)O inter­actions, linking the mol­ecules into infinite chains along the c axis. In addition, there are weak C—H(...)S and C—H(...)π inter­actions.

Related literature

For general background to chemical modifications of the non-steroidal anti-inflammatory drug diclofenac {[2-(2,6-dichloro­anilino)phen­yl]acetic acid}, see: Amir & Shikha (2004 [triangle]); Bandarage et al. (2000 [triangle]); Bhandari et al. (2008 [triangle]); Galanakis et al. (2004 [triangle]); Sriram et al. (2006 [triangle]); Wittine et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o882-scheme1.jpg

Experimental

Crystal data

  • C29H29Cl2N3O2S
  • M r = 554.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o882-efi1.jpg
  • a = 11.6105 (6) Å
  • b = 24.3130 (12) Å
  • c = 9.8137 (5) Å
  • β = 95.335 (2)°
  • V = 2758.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 296 K
  • 0.34 × 0.17 × 0.12 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • 30871 measured reflections
  • 6792 independent reflections
  • 3599 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.216
  • S = 1.03
  • 6792 reflections
  • 380 parameters
  • 29 restraints
  • H-atom parameters constrained
  • Δρmax = 0.71 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009803/bt5217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009803/bt5217Isup2.hkl

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

supplementary crystallographic information

Comment

Diclofenac, [2-(2,6-dichloroanilino)phenyl]acetic acid, is being used for its antiinflammatory activity for over 30 years and is a tolerable drug when compared with other NSAIDs. Still, its chronic use may elicit appreciable GI irritation, bleeding and ulceration due to its free –COOH group. Chemical modifications on the molecule have been made both to improve the safety profile and also to obtain derivatives with antimicrobial, antioxidant and anticancer properties by derivatization of the carboxylate function (Bandarage et al., 2000; Amir & Shikha, 2004; Galanakis et al., 2004; Sriram et al., 2006; Bhandari et al., 2008; Wittine et al., 2009). Following the same strategy, we prepared the title molecule bearing a spirothiazolidinone moiety to investigate its antimicrobial potential.

The phenyl ring of the title molecule (Fig. 1) is disordered over two orientations with occupancies of 0.55 (3) and 0.45 (3). The dihedral angle between the planes of the disorder phenyl rings (C24/C25A–C29A and C24/C25B–C29B) is 15.8 (9)°. The two benzene rings (C1–C6 and C7–C12) form dihedral angles of 25.2 (5), 26.6 (8)° and 67.7 (5), 83.4 (8)°, respectively, with these disorder phenyl rings.

Intermolecular N—H···O interactions link the molecules into infinite chains stretching along the c axis of the crystal (Fig. 2 and Table 1). In the crystal structure, weak C—H···π interactions occur between the (C17A)H17A atom of the methyl group and the C7–C12 benzene ring (Table 1).

Experimental

A mixture of 2-[2-(2,6-dichloroanilino)phenyl]-N'-(4-phenylcyclohexylidene)acetohydrazide(0.0025 mol) and 2-mercaptopropionic acid (2.5 ml) was refluxed in dry benzene (20 ml) using a Dean-Stark water separator for 6 h. The reaction mixture thus obtained was concentrated under vacuum and neutralized by addition of saturated NaHCO3 solution until CO2 evolution ceased. After refrigeration overnight, the precipitate was filtered, dried and purified by recrystallization from EtOH. Yield, 56.1 %, m.p. 492.7-494.3 K. UV (EtOH) λmax.= 279.6, 205.4 nm. IR (KBr) ν = 3219 (N—H), 1721, 1682 (C=O) cm-1. 1H-NMR (DMSO-d6, 500 MHz) δ= 1.42 (3H, d, J= 6.83 Hz, CH3), 1.50-1.72 (8H, m, CH2-sp.*), 2.33 (1H, t, J= 12.20 Hz, CH-sp.), 3.74 (2H, s, CH2CO), 3.93 (1H, q, J= 6.83 Hz, SCH), 6.29 (1H, d, J= 7.81 Hz, Ar—H*), 6.90 (1H, t, J= 6.83 Hz, Ar—H), 7.07 (1H, t, J= 7.80 Hz, Ar—H), 7.14-7.20 (4H, m, Ar—H and C6H5-sp.), 7.27 (2H, t, J= 7.32 Hz, C6H5-sp), 7.31 (1H, d, J= 7.80 Hz, Ar—H), 7.51 (2H, d, J= 7.81 Hz, Ar—H), 7.41 (1H, s, NH), 10.51 (1H, s, CONH).(sp= spirodecane, Ar= aromatic). Analysis calculated for C29H29Cl2N3O2S: C 62.81, H 5.27, N 7.58 %. Found: C 62.79, H 5.34, N 7.50 %.

Refinement

All hydrogen atoms except those of the disordered phenyl ring were located in a difference map. They were refined using a riding model with N—H = 0.86 Å and C—H = 0.93 - 0.98 Å, and with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(Cmethyl). The phenyl ring of the molecule shows a positional disorder over two sites with refined occupancies of 0.55 (3) and 0.45 (3).

Figures

Fig. 1.
The molecule of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. The atoms of the minor component of the disorder in the molecule have been omitted.
Fig. 2.
View of the unitcell contents and the hydrogen bonding of the title compound. For the sake of clarity, the atoms of the minor component of the disorder in the molecule and H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C29H29Cl2N3O2SF(000) = 1160
Mr = 554.52Dx = 1.335 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6879 reflections
a = 11.6105 (6) Åθ = 2.3–23.7°
b = 24.3130 (12) ŵ = 0.34 mm1
c = 9.8137 (5) ÅT = 296 K
β = 95.335 (2)°Irregular, off white
V = 2758.3 (2) Å30.34 × 0.17 × 0.12 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer3599 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.036
graphiteθmax = 28.4°, θmin = 1.8°
[var phi] and ω scansh = −15→15
30871 measured reflectionsk = −32→32
6792 independent reflectionsl = −13→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.098P)2 + 1.278P] where P = (Fo2 + 2Fc2)/3
6792 reflections(Δ/σ)max < 0.001
380 parametersΔρmax = 0.71 e Å3
29 restraintsΔρmin = −0.39 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Cl10.98524 (9)0.89260 (5)0.18049 (12)0.0906 (4)
Cl20.59184 (11)0.94402 (5)−0.12658 (18)0.1208 (6)
S10.25302 (7)0.71472 (4)0.01238 (14)0.0855 (4)
O10.62380 (18)0.75690 (11)−0.1282 (2)0.0635 (8)
O20.4694 (2)0.83356 (11)0.0547 (3)0.0853 (10)
N10.7725 (2)0.86657 (10)−0.0040 (3)0.0645 (10)
N20.5873 (2)0.73711 (11)0.0866 (2)0.0555 (9)
N30.4692 (2)0.74017 (11)0.0565 (3)0.0523 (8)
C10.8883 (3)0.94012 (14)0.1066 (4)0.0623 (11)
C20.9084 (3)0.99493 (16)0.1345 (4)0.0749 (14)
C30.8308 (4)1.03345 (16)0.0839 (4)0.0788 (16)
C40.7329 (3)1.01787 (15)0.0046 (4)0.0774 (15)
C50.7154 (3)0.96296 (14)−0.0258 (4)0.0671 (11)
C60.7921 (3)0.92223 (13)0.0223 (4)0.0571 (10)
C70.8511 (2)0.83528 (12)−0.0746 (3)0.0499 (10)
C80.9222 (3)0.85998 (14)−0.1622 (4)0.0649 (11)
C91.0001 (3)0.82913 (17)−0.2277 (4)0.0680 (13)
C101.0088 (3)0.77434 (16)−0.2055 (4)0.0641 (13)
C110.9380 (2)0.74935 (13)−0.1189 (3)0.0556 (10)
C120.8588 (2)0.77898 (12)−0.0517 (3)0.0441 (9)
C130.7841 (2)0.75166 (13)0.0447 (3)0.0510 (9)
C140.6583 (2)0.74927 (12)−0.0099 (3)0.0450 (9)
C150.4177 (3)0.79046 (15)0.0432 (4)0.0635 (11)
C160.2869 (3)0.78542 (16)0.0060 (5)0.0794 (16)
C170.2194 (4)0.82223 (18)0.0830 (6)0.103 (2)
C180.4014 (2)0.68929 (12)0.0445 (3)0.0477 (9)
C190.4340 (3)0.65415 (13)−0.0732 (3)0.0551 (10)
C200.3638 (3)0.60153 (14)−0.0850 (3)0.0627 (11)
C210.3770 (3)0.56817 (14)0.0470 (4)0.0636 (11)
C220.3460 (3)0.60400 (14)0.1664 (3)0.0624 (11)
C230.4159 (3)0.65690 (14)0.1768 (3)0.0615 (11)
C240.3100 (4)0.51492 (16)0.0429 (5)0.0862 (18)
C25A0.3440 (11)0.4680 (6)0.1147 (16)0.085 (4)0.55 (3)
C26A0.2744 (18)0.4224 (3)0.113 (2)0.101 (7)0.55 (3)
C27A0.167 (2)0.4217 (5)0.0386 (15)0.114 (7)0.55 (3)
C28A0.1244 (19)0.4675 (9)−0.0298 (17)0.151 (8)0.55 (3)
C29A0.1961 (13)0.5155 (6)−0.0263 (17)0.127 (6)0.55 (3)
C27B0.230 (3)0.4101 (6)0.064 (3)0.152 (12)0.45 (3)
C28B0.178 (3)0.4464 (13)−0.030 (3)0.22 (2)0.45 (3)
C29B0.221 (2)0.4988 (9)−0.044 (2)0.175 (12)0.45 (3)
C25B0.3636 (13)0.4808 (7)0.1432 (17)0.115 (7)0.45 (3)
C26B0.322 (2)0.4272 (5)0.155 (2)0.139 (10)0.45 (3)
H30.844301.070500.103200.0940*
H91.046900.84610−0.287300.0810*
H40.678901.04400−0.028400.0930*
H80.917400.89770−0.177100.0780*
H13A0.790900.771500.130800.0610*
H13B0.812100.714500.062700.0610*
H16A0.272700.79640−0.090100.0950*
H17A0.138700.817500.054300.1540*
H17B0.241400.859600.067000.1540*
H101.062300.75360−0.248400.0770*
H110.943600.71150−0.105400.0670*
H19B0.421100.67480−0.157800.0660*
H20A0.388800.57940−0.159100.0750*
H20B0.282900.61050−0.107100.0750*
H210.459100.558700.064600.0760*
H22A0.264300.612900.154200.0750*
H22B0.360200.583500.251100.0750*
H23A0.391200.679300.250600.0740*
H23B0.497100.648100.198500.0740*
H25A0.415900.467300.165200.1020*0.55 (3)
H26A0.299500.391500.163500.1210*0.55 (3)
H27A0.123500.389600.034800.1370*0.55 (3)
H28A0.051100.46750−0.076900.1810*0.55 (3)
H29A0.168100.54750−0.069600.1530*0.55 (3)
H17C0.233300.814100.178900.1540*
H19A0.515700.64510−0.059300.0660*
H10.712000.851000.022800.0780*
HN20.615700.727400.167100.0670*
H20.974901.005600.188000.0900*
H25B0.426100.493300.201200.1380*0.45 (3)
H26B0.354100.403600.223100.1650*0.45 (3)
H27B0.203800.373900.065500.1830*0.45 (3)
H28B0.112100.43550−0.084900.2640*0.45 (3)
H29B0.188400.52230−0.112100.2100*0.45 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0807 (7)0.0962 (8)0.0934 (8)0.0224 (5)0.0001 (6)−0.0116 (6)
Cl20.0885 (8)0.0901 (8)0.1737 (14)0.0009 (6)−0.0423 (8)−0.0296 (8)
S10.0438 (4)0.0637 (6)0.1487 (11)0.0024 (4)0.0068 (5)−0.0140 (6)
O10.0474 (11)0.1089 (18)0.0334 (11)−0.0139 (11)−0.0010 (9)0.0081 (11)
O20.0841 (17)0.0699 (16)0.105 (2)−0.0231 (14)0.0252 (15)−0.0047 (15)
N10.0560 (15)0.0461 (14)0.096 (2)−0.0102 (11)0.0310 (15)−0.0135 (14)
N20.0434 (13)0.0856 (18)0.0367 (13)−0.0132 (12)−0.0007 (10)0.0080 (12)
N30.0427 (12)0.0654 (16)0.0492 (15)−0.0081 (11)0.0069 (11)0.0030 (12)
C10.0593 (19)0.063 (2)0.067 (2)0.0010 (15)0.0184 (17)−0.0100 (16)
C20.069 (2)0.070 (2)0.086 (3)−0.0117 (19)0.009 (2)−0.025 (2)
C30.088 (3)0.056 (2)0.095 (3)−0.0124 (19)0.022 (2)−0.023 (2)
C40.082 (3)0.0510 (19)0.099 (3)0.0018 (17)0.008 (2)−0.0074 (19)
C50.0622 (19)0.0591 (19)0.080 (2)−0.0057 (16)0.0061 (17)−0.0102 (17)
C60.0548 (17)0.0496 (17)0.070 (2)−0.0072 (14)0.0231 (16)−0.0128 (16)
C70.0422 (14)0.0510 (16)0.0583 (19)−0.0077 (12)0.0145 (13)−0.0086 (14)
C80.0619 (19)0.0583 (19)0.077 (2)−0.0173 (15)0.0195 (18)−0.0074 (17)
C90.0492 (17)0.095 (3)0.062 (2)−0.0205 (17)0.0162 (16)−0.0116 (19)
C100.0367 (15)0.087 (3)0.069 (2)0.0002 (15)0.0064 (15)−0.0250 (19)
C110.0400 (15)0.0591 (18)0.066 (2)0.0044 (13)−0.0041 (14)−0.0133 (15)
C120.0335 (12)0.0517 (16)0.0460 (16)−0.0054 (11)−0.0013 (11)−0.0062 (12)
C130.0429 (15)0.0582 (17)0.0501 (17)−0.0044 (13)−0.0059 (13)0.0065 (14)
C140.0424 (14)0.0562 (16)0.0359 (15)−0.0081 (12)0.0006 (12)0.0031 (13)
C150.0611 (19)0.070 (2)0.062 (2)−0.0110 (17)0.0199 (16)−0.0037 (17)
C160.060 (2)0.080 (3)0.101 (3)−0.0003 (18)0.022 (2)0.004 (2)
C170.074 (3)0.080 (3)0.151 (5)0.020 (2)−0.012 (3)−0.021 (3)
C180.0371 (13)0.0624 (17)0.0448 (17)−0.0053 (12)0.0096 (12)−0.0045 (14)
C190.0565 (17)0.070 (2)0.0404 (16)−0.0002 (15)0.0124 (14)−0.0008 (15)
C200.068 (2)0.071 (2)0.0510 (19)−0.0034 (16)0.0161 (16)−0.0150 (16)
C210.0618 (19)0.062 (2)0.069 (2)0.0014 (15)0.0163 (17)−0.0030 (17)
C220.067 (2)0.071 (2)0.0505 (19)−0.0101 (16)0.0120 (16)0.0059 (16)
C230.071 (2)0.075 (2)0.0405 (17)−0.0179 (17)0.0159 (15)−0.0001 (15)
C240.117 (4)0.061 (2)0.087 (3)−0.014 (2)0.043 (3)−0.013 (2)
C25A0.101 (7)0.026 (5)0.138 (10)0.007 (4)0.063 (6)0.005 (6)
C26A0.124 (15)0.043 (6)0.148 (14)−0.014 (6)0.074 (11)−0.010 (8)
C27A0.162 (15)0.082 (9)0.110 (10)−0.028 (9)0.074 (10)−0.029 (7)
C28A0.216 (17)0.145 (15)0.090 (9)−0.094 (14)0.000 (9)0.009 (9)
C29A0.177 (13)0.110 (10)0.086 (8)−0.092 (10)−0.032 (9)0.015 (9)
C27B0.15 (2)0.068 (9)0.25 (3)−0.053 (12)0.09 (2)−0.076 (13)
C28B0.28 (4)0.14 (2)0.23 (4)−0.12 (3)−0.04 (3)−0.04 (2)
C29B0.28 (3)0.102 (12)0.138 (17)−0.092 (15)−0.001 (17)−0.053 (12)
C25B0.137 (11)0.052 (9)0.170 (15)−0.031 (8)0.091 (11)−0.050 (10)
C26B0.126 (17)0.097 (12)0.21 (2)−0.031 (9)0.106 (14)−0.071 (13)

Geometric parameters (Å, °)

Cl1—C11.725 (4)C25A—C26A1.37 (2)
Cl2—C51.728 (4)C25B—C26B1.40 (2)
S1—C161.766 (4)C26A—C27A1.39 (3)
S1—C181.830 (3)C26B—C27B1.39 (4)
O1—C141.207 (4)C27A—C28A1.37 (3)
O2—C151.208 (4)C27B—C28B1.38 (4)
N1—C61.392 (4)C28A—C29A1.43 (3)
N1—C71.418 (4)C28B—C29B1.38 (4)
N2—N31.378 (3)C2—H20.9300
N2—C141.345 (3)C3—H30.9300
N3—C151.362 (4)C4—H40.9300
N3—C181.465 (4)C8—H80.9300
N1—H10.8600C9—H90.9300
N2—HN20.8600C10—H100.9300
C1—C21.376 (5)C11—H110.9300
C1—C61.396 (5)C13—H13A0.9700
C2—C31.361 (6)C13—H13B0.9700
C3—C41.370 (6)C16—H16A0.9800
C4—C51.379 (5)C17—H17A0.9600
C5—C61.385 (5)C17—H17B0.9600
C7—C81.383 (5)C17—H17C0.9600
C7—C121.389 (4)C19—H19A0.9700
C8—C91.379 (5)C19—H19B0.9700
C9—C101.352 (6)C20—H20A0.9700
C10—C111.377 (5)C20—H20B0.9700
C11—C121.383 (4)C21—H210.9800
C12—C131.497 (4)C22—H22A0.9700
C13—C141.509 (3)C22—H22B0.9700
C15—C161.534 (5)C23—H23A0.9700
C16—C171.448 (6)C23—H23B0.9700
C18—C191.513 (4)C25A—H25A0.9300
C18—C231.515 (4)C25B—H25B0.9300
C19—C201.516 (5)C26A—H26A0.9300
C20—C211.524 (5)C26B—H26B0.9300
C21—C241.509 (5)C27A—H27A0.9300
C21—C221.530 (5)C27B—H27B0.9300
C22—C231.519 (5)C28A—H28A0.9300
C24—C29A1.429 (16)C28B—H28B0.9300
C24—C25A1.379 (15)C29A—H29A0.9300
C24—C25B1.389 (17)C29B—H29B0.9300
C24—C29B1.34 (2)
Cl1···N12.991 (3)C29B···H20B2.8900
Cl1···C73.148 (3)C29B···H20A3.0500
Cl1···C83.467 (4)H1···Cl22.9700
Cl1···C17i3.423 (5)H1···O22.8900
Cl1···C27Aii3.483 (18)H1···C132.5600
Cl2···N12.987 (3)H1···O12.8600
Cl2···C22iii3.544 (4)H1···H13A2.3500
Cl2···C23iii3.631 (4)H1···C142.5600
Cl1···H17Ai2.9100HN2···H23B2.4100
Cl2···H12.9700HN2···H13A2.3600
Cl2···H22Biii2.9200HN2···C232.8900
Cl2···H23Biii2.9700HN2···O1v2.0400
Cl2···H25Biii2.8800H2···H28Axii2.4800
S1···N32.582 (3)H3···H17Bix2.5200
S1···C10iv3.686 (4)H4···H17Bix2.5600
S1···H20B2.8300H8···H28Bx2.5000
S1···H22A2.8400H8···C13.0200
O1···N32.698 (3)H8···C62.6100
O1···C73.258 (3)H11···H13B2.3500
O1···C153.158 (4)H13A···C11v2.9000
O1···C193.407 (4)H13A···N12.6600
O1···N2iii2.795 (3)H13A···H12.3500
O2···N22.719 (4)H13A···C10v3.0800
O2···C143.110 (4)H13A···HN22.3600
O1···HN2iii2.0400H13B···C9v3.0500
O1···H12.8600H13B···C10v3.0800
O2···H12.8900H13B···H27Bxi2.4900
O2···H17B2.7400H13B···H112.3500
N1···Cl12.991 (3)H16A···H23Aiii2.2600
N1···Cl22.987 (3)H17A···C9iv3.0800
N1···C143.143 (4)H17A···Cl1iv2.9100
N2···O22.719 (4)H17A···C10iv3.0300
N2···O1v2.795 (3)H17B···C4ix3.0800
N3···O12.698 (3)H17B···O22.7400
N3···S12.582 (3)H17B···C3ix3.0700
N1···H13A2.6600H17B···H4ix2.5600
N2···H19A2.7400H17B···H3ix2.5200
N2···H23B2.6800H17C···H19Bv2.6000
C1···C83.332 (5)H19A···H23B2.5600
C1···C26Aii3.51 (2)H19A···C26Axi3.0200
C1···C26Bii3.55 (2)H19A···N22.7400
C2···C2vi3.549 (5)H19A···C143.0400
C6···C26Bii3.55 (2)H19A···H212.5400
C7···Cl13.148 (3)H19A···C26Bxi2.8000
C7···O13.258 (3)H19A···H26Bxi2.5900
C8···C13.332 (5)H19B···C15iii3.0500
C8···Cl13.467 (4)H19B···H17Ciii2.6000
C10···C13iii3.468 (5)H20A···H25Axi2.5400
C10···S1i3.686 (4)H20A···C29B3.0500
C13···C10v3.468 (5)H20B···S12.8300
C14···C193.495 (4)H20B···H29B2.4100
C14···N13.143 (4)H20B···H22A2.5900
C14···O23.110 (4)H20B···H29A2.0900
C15···O13.158 (4)H20B···C29A2.6700
C17···Cl1iv3.423 (5)H20B···C29B2.8900
C19···O13.407 (4)H21···H25A2.5000
C19···C143.495 (4)H21···H25B2.1400
C22···Cl2v3.544 (4)H21···H23B2.5600
C23···Cl2v3.631 (4)H21···H19A2.5400
C26A···C1vii3.51 (2)H21···C25Axi3.0800
C26B···C6vii3.55 (2)H22A···C29A3.0200
C26B···C1vii3.55 (2)H22A···S12.8400
C27A···Cl1vii3.483 (18)H22A···H20B2.5900
C28A···C28Aviii3.39 (3)H22B···Cl2v2.9200
C1···H83.0200H22B···C25B2.7100
C3···H17Bix3.0700H22B···H25B2.3900
C4···H17Bix3.0800H23A···C16v3.0100
C6···H82.6100H23A···H16Av2.2600
C8···H28Bx3.0800H23A···C15v2.9500
C9···H13Biii3.0500H23B···H212.5600
C9···H17Ai3.0800H23B···Cl2v2.9700
C10···H17Ai3.0300H23B···N22.6800
C10···H13Aiii3.0800H23B···HN22.4100
C10···H13Biii3.0800H23B···H19A2.5600
C11···H13Aiii2.9000H25A···H212.5000
C13···H12.5600H25A···H20Axi2.5400
C14···H12.5600H25B···C222.8600
C14···H19A3.0400H25B···Cl2v2.8800
C15···H23Aiii2.9500H25B···H212.1400
C15···H19Bv3.0500H25B···H22B2.3900
C16···H23Aiii3.0100H26B···H19Axi2.5900
C20···H29B2.8000H27B···H13Bxi2.4900
C20···H29A2.6400H28A···H2xiii2.4800
C22···H25B2.8600H28A···H28Aviii2.5500
C23···HN22.8900H28A···C28Aviii2.8500
C25A···H21xi3.0800H28B···C8xiv3.0800
C25B···H22B2.7100H28B···H8xiv2.5000
C26A···H19Axi3.0200H29A···H20B2.0900
C26B···H19Axi2.8000H29A···C202.6400
C28A···H28Aviii2.8500H29B···C202.8000
C29A···H22A3.0200H29B···H20B2.4100
C29A···H20B2.6700
C16—S1—C1897.22 (15)C1—C2—H2120.00
C6—N1—C7120.7 (3)C3—C2—H2120.00
N3—N2—C14120.0 (2)C2—C3—H3120.00
N2—N3—C15119.2 (3)C4—C3—H3120.00
N2—N3—C18119.2 (2)C3—C4—H4120.00
C15—N3—C18121.5 (2)C5—C4—H4120.00
C7—N1—H1120.00C7—C8—H8120.00
C6—N1—H1120.00C9—C8—H8120.00
N3—N2—HN2120.00C8—C9—H9120.00
C14—N2—HN2120.00C10—C9—H9120.00
Cl1—C1—C6119.7 (3)C9—C10—H10120.00
Cl1—C1—C2118.2 (3)C11—C10—H10120.00
C2—C1—C6122.1 (3)C10—C11—H11119.00
C1—C2—C3120.0 (4)C12—C11—H11119.00
C2—C3—C4120.2 (4)C12—C13—H13A109.00
C3—C4—C5119.2 (3)C12—C13—H13B109.00
Cl2—C5—C4118.7 (3)C14—C13—H13A109.00
Cl2—C5—C6118.6 (3)C14—C13—H13B109.00
C4—C5—C6122.8 (3)H13A—C13—H13B108.00
N1—C6—C1121.4 (3)S1—C16—H16A106.00
N1—C6—C5122.9 (3)C15—C16—H16A106.00
C1—C6—C5115.7 (3)C17—C16—H16A106.00
N1—C7—C12119.0 (2)C16—C17—H17A109.00
C8—C7—C12119.7 (3)C16—C17—H17B110.00
N1—C7—C8121.3 (3)C16—C17—H17C110.00
C7—C8—C9120.6 (3)H17A—C17—H17B109.00
C8—C9—C10120.2 (3)H17A—C17—H17C109.00
C9—C10—C11119.6 (3)H17B—C17—H17C109.00
C10—C11—C12121.7 (3)C18—C19—H19A109.00
C7—C12—C13120.5 (2)C18—C19—H19B109.00
C11—C12—C13121.4 (3)C20—C19—H19A109.00
C7—C12—C11118.2 (3)C20—C19—H19B109.00
C12—C13—C14113.0 (2)H19A—C19—H19B108.00
O1—C14—N2122.7 (2)C19—C20—H20A109.00
O1—C14—C13124.0 (2)C19—C20—H20B109.00
N2—C14—C13113.3 (2)C21—C20—H20A109.00
O2—C15—C16124.4 (3)C21—C20—H20B109.00
N3—C15—C16111.6 (3)H20A—C20—H20B108.00
O2—C15—N3124.1 (3)C20—C21—H21107.00
S1—C16—C15106.8 (3)C22—C21—H21107.00
C15—C16—C17113.5 (4)C24—C21—H21107.00
S1—C16—C17116.8 (3)C21—C22—H22A109.00
N3—C18—C19111.6 (2)C21—C22—H22B109.00
S1—C18—C23110.6 (2)C23—C22—H22A109.00
S1—C18—N3102.64 (19)C23—C22—H22B109.00
N3—C18—C23110.7 (2)H22A—C22—H22B108.00
C19—C18—C23110.2 (2)C18—C23—H23A109.00
S1—C18—C19111.0 (2)C18—C23—H23B109.00
C18—C19—C20111.4 (3)C22—C23—H23A109.00
C19—C20—C21111.9 (3)C22—C23—H23B109.00
C20—C21—C22109.6 (3)H23A—C23—H23B108.00
C20—C21—C24115.0 (3)C24—C25A—H25A119.00
C22—C21—C24110.6 (3)C26A—C25A—H25A119.00
C21—C22—C23111.8 (3)C24—C25B—H25B121.00
C18—C23—C22111.5 (2)C26B—C25B—H25B121.00
C21—C24—C25A125.0 (7)C25A—C26A—H26A119.00
C25B—C24—C29B123.1 (12)C27A—C26A—H26A119.00
C21—C24—C29A117.1 (7)C25B—C26B—H26B121.00
C21—C24—C25B107.3 (7)C27B—C26B—H26B121.00
C21—C24—C29B129.4 (10)C26A—C27A—H27A119.00
C25A—C24—C29A117.3 (9)C28A—C27A—H27A120.00
C24—C25A—C26A121.5 (13)C26B—C27B—H27B120.00
C24—C25B—C26B118.7 (14)C28B—C27B—H27B120.00
C25A—C26A—C27A121.1 (13)C27A—C28A—H28A121.00
C25B—C26B—C27B118.4 (16)C29A—C28A—H28A121.00
C26A—C27A—C28A121.0 (15)C27B—C28B—H28B119.00
C26B—C27B—C28B120.1 (19)C29B—C28B—H28B119.00
C27A—C28A—C29A117.9 (18)C24—C29A—H29A120.00
C27B—C28B—C29B121 (3)C28A—C29A—H29A120.00
C24—C29A—C28A120.9 (13)C24—C29B—H29B121.00
C24—C29B—C28B118 (2)C28B—C29B—H29B121.00
C16—S1—C18—N33.3 (3)C12—C7—C8—C90.4 (5)
C16—S1—C18—C19−116.0 (3)C8—C7—C12—C11−0.3 (4)
C16—S1—C18—C23121.5 (3)C8—C7—C12—C13178.9 (3)
C18—S1—C16—C17−133.4 (4)C7—C8—C9—C10−0.9 (6)
C18—S1—C16—C15−5.3 (3)C8—C9—C10—C111.1 (6)
C7—N1—C6—C1−63.7 (5)C9—C10—C11—C12−1.0 (5)
C6—N1—C7—C12153.6 (3)C10—C11—C12—C13−178.6 (3)
C7—N1—C6—C5120.2 (4)C10—C11—C12—C70.6 (4)
C6—N1—C7—C8−24.5 (5)C7—C12—C13—C1470.6 (3)
C14—N2—N3—C15−73.3 (4)C11—C12—C13—C14−110.2 (3)
C14—N2—N3—C18108.9 (3)C12—C13—C14—O115.6 (4)
N3—N2—C14—O1−8.8 (5)C12—C13—C14—N2−165.1 (3)
N3—N2—C14—C13171.9 (3)N3—C15—C16—S15.9 (4)
C18—N3—C15—O2178.6 (3)N3—C15—C16—C17135.9 (4)
C18—N3—C15—C16−3.8 (5)O2—C15—C16—S1−176.5 (3)
N2—N3—C18—S1177.5 (2)O2—C15—C16—C17−46.5 (6)
C15—N3—C18—C19118.7 (3)S1—C18—C19—C20−66.3 (3)
C15—N3—C18—C23−118.2 (3)N3—C18—C19—C20179.9 (2)
N2—N3—C18—C2359.5 (3)C23—C18—C19—C2056.5 (3)
C15—N3—C18—S1−0.2 (4)S1—C18—C23—C2266.8 (3)
N2—N3—C18—C19−63.6 (3)N3—C18—C23—C22179.9 (3)
N2—N3—C15—C16178.5 (3)C19—C18—C23—C22−56.2 (3)
N2—N3—C15—O20.9 (5)C18—C19—C20—C21−56.9 (4)
C6—C1—C2—C32.7 (6)C19—C20—C21—C2255.0 (4)
Cl1—C1—C2—C3−176.6 (3)C19—C20—C21—C24−179.7 (3)
C2—C1—C6—C5−3.1 (6)C20—C21—C22—C23−54.6 (4)
Cl1—C1—C6—N1−0.1 (5)C24—C21—C22—C23177.6 (3)
Cl1—C1—C6—C5176.3 (3)C20—C21—C24—C25A148.6 (8)
C2—C1—C6—N1−179.5 (3)C20—C21—C24—C29A−40.0 (9)
C1—C2—C3—C4−0.3 (6)C22—C21—C24—C25A−86.6 (9)
C2—C3—C4—C5−1.5 (6)C22—C21—C24—C29A84.8 (8)
C3—C4—C5—C61.0 (6)C21—C22—C23—C1856.1 (4)
C3—C4—C5—Cl2−179.7 (3)C21—C24—C25A—C26A175.4 (12)
Cl2—C5—C6—N1−1.8 (5)C29A—C24—C25A—C26A4.0 (19)
C4—C5—C6—N1177.5 (3)C21—C24—C29A—C28A−177.1 (12)
C4—C5—C6—C11.2 (6)C25A—C24—C29A—C28A−5.0 (19)
Cl2—C5—C6—C1−178.1 (3)C24—C25A—C26A—C27A0(3)
N1—C7—C12—C11−178.4 (3)C25A—C26A—C27A—C28A−4(3)
N1—C7—C12—C130.8 (4)C26A—C27A—C28A—C29A2(3)
N1—C7—C8—C9178.5 (3)C27A—C28A—C29A—C242(2)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x−1, y, z; (v) x, −y+3/2, z+1/2; (vi) −x+2, −y+2, −z; (vii) −x+1, y−1/2, −z+1/2; (viii) −x, −y+1, −z; (ix) −x+1, −y+2, −z; (x) −x+1, y+1/2, −z−1/2; (xi) −x+1, −y+1, −z; (xii) x+1, −y+3/2, z+1/2; (xiii) x−1, −y+3/2, z−1/2; (xiv) −x+1, y−1/2, −z−1/2.

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C7–C12 benzene ring.
D—H···AD—HH···AD···AD—H···A
N2—HN2···O1v0.862.042.795 (3)146
C20—H20B···S10.972.833.220 (4)105
C22—H22A···S10.972.843.224 (3)105
C17—H17A···Cg3iv0.962.963.862 (5)157

Symmetry codes: (v) x, −y+3/2, z+1/2; (iv) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5217).

References

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