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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1769.
Published online 2010 June 26. doi:  10.1107/S1600536810023871
PMCID: PMC3006884

N-(2-Meth­oxy­phen­yl)benzene­sulfonamide

Abstract

The asymmetric unit of the title compound, C13H13NO3S, contains two crystallographically independent mol­ecules in which the dihedral angles between the phenyl and benzene rings are 88.16 (12) and 44.50 (12)°. One of the mol­ecules features an intra­molecular N—H(...)O hydrogen bond. In the crystal, the mol­ecules are linked into dimers by pairs of N—H(...)O hydrogen bonds. The dimers are further connected by C—H(...)O and C—H(...)π inter­actions, forming a three-dimensional network.

Related literature

For the biological activity of sulfonamides, see: Arshad et al. (2008 [triangle]); Gennarti et al. (1994 [triangle]); Kayser et al. (2004 [triangle]); Rough et al. (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1769-scheme1.jpg

Experimental

Crystal data

  • C13H13NO3S
  • M r = 263.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1769-efi1.jpg
  • a = 8.7705 (2) Å
  • b = 28.1684 (7) Å
  • c = 10.7256 (3) Å
  • β = 105.968 (1)°
  • V = 2547.53 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 296 K
  • 0.25 × 0.17 × 0.07 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • 24823 measured reflections
  • 6318 independent reflections
  • 4145 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.113
  • S = 1.02
  • 6318 reflections
  • 333 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.29 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 (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/S1600536810023871/hb5501sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023871/hb5501Isup2.hkl

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

supplementary crystallographic information

Comment

Sulfonamides are well known for their enormous potential as biologically active molecules (Rough et al., 1998) in areas such as anti-microbial (Kayser et al., 2004), anti-convulsant (Arshad et al., 2008), anti-cancer agents and for the treatment of inflammatory rheumatic and non-rheumatic processes including onsets and traumatologic lesions (Gennarti et al., 1994). In the present paper, the structure of N-(2-methoxyphenyl)benzene sulfonamide has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing compounds.

In the crystal structure of the title compound (I), (Fig. 1), there exist two independent molecules, A (with S1) and B (with S1'). Both independent molecules are bent at their S atoms with the C—S—N(H)—C torsion angles of 67.25 (15)° in molecule A and -81.17 (16)° in molecule B. The dihedral angles between the phenyl and benzene rings is 88.16 (12)° in molecule A and 44.50 (12)° in molecule B.

Molecular packing of (I) is stabilized by N–H···O, C—H···O interactions and C—H···π interactions, forming a three dimensional network (Table 1). Fig. 2 shows N—H···O hydrogen bonds between the molecules A and B in the asymmetric unit.

Experimental

A mixture benzenesulfonyl chloride (10.0 mmol; 1.45 ml), ortho-methoxy aniline (o-anisidine) (10.0 mmol; 1.12 ml), aqueous sodium carbonate (10%; 15.0 ml) and water (25 ml) was stirred for one hour at room temperature. The crude mixture was washed with water and dried. The product was dissolved in methanol and recrystallized by slow evaporation of the solvent, to generate colourless blocks of (I) in 74% yield.

Refinement

The H atoms of the NH groups were located in a difference Fourier map and refined with the N—H distance restrained to 0.86 (2) %A. The other H atoms were positioned geometrically using a riding model with C–H = 0.93 and 0.96 Å. All H atoms were refined with isotropic displacement parameters with Uiso(H) = 1.2Ueq(aromatic, NH) and Uiso(H) = 1.5Ueq(methyl).

Figures

Fig. 1.
View of the two independent molecules in the asymmetric unit of (I0 with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
View of N—H···O hydrogen bonds shown as dashed lines between the two independent molecules in the asymmetric unit.

Crystal data

C13H13NO3SF(000) = 1104
Mr = 263.31Dx = 1.373 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5117 reflections
a = 8.7705 (2) Åθ = 2.5–23.9°
b = 28.1684 (7) ŵ = 0.25 mm1
c = 10.7256 (3) ÅT = 296 K
β = 105.968 (1)°Block, colourless
V = 2547.53 (11) Å30.25 × 0.17 × 0.07 mm
Z = 8

Data collection

Bruker APEXII CCD diffractometer4145 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.043
graphiteθmax = 28.3°, θmin = 3.3°
[var phi] and ω scansh = −11→11
24823 measured reflectionsk = −37→37
6318 independent reflectionsl = −14→14

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0488P)2 + 0.3381P] where P = (Fo2 + 2Fc2)/3
6318 reflections(Δ/σ)max = 0.001
333 parametersΔρmax = 0.29 e Å3
2 restraintsΔρmin = −0.29 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 e.s.d.'s 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*/Ueq
S10.33115 (5)0.81887 (2)0.56961 (5)0.0412 (2)
O10.29814 (16)0.77142 (5)0.59898 (15)0.0561 (5)
O20.21225 (14)0.84480 (5)0.47617 (14)0.0518 (5)
O30.68975 (15)0.82034 (5)0.38159 (14)0.0507 (5)
N10.48440 (18)0.81979 (6)0.51516 (16)0.0430 (5)
C10.3503 (3)0.83266 (9)0.8243 (2)0.0681 (9)
C20.3878 (4)0.85873 (11)0.9379 (3)0.0865 (11)
C30.4523 (3)0.90282 (11)0.9397 (3)0.0764 (10)
C40.4848 (3)0.92123 (8)0.8326 (3)0.0663 (9)
C50.4496 (2)0.89536 (7)0.7189 (2)0.0511 (7)
C60.3823 (2)0.85108 (7)0.71581 (19)0.0424 (6)
C70.6322 (2)0.79744 (6)0.57144 (18)0.0388 (6)
C80.6717 (3)0.77602 (7)0.6914 (2)0.0536 (7)
C90.8209 (3)0.75621 (9)0.7392 (3)0.0681 (9)
C100.9276 (3)0.75748 (9)0.6684 (3)0.0728 (9)
C110.8897 (2)0.77854 (8)0.5478 (3)0.0596 (8)
C120.7411 (2)0.79839 (6)0.4983 (2)0.0417 (6)
C130.7966 (3)0.82674 (9)0.3050 (2)0.0653 (9)
S1'0.31232 (5)0.92918 (2)0.25688 (5)0.0434 (2)
O1'0.41671 (16)0.89021 (5)0.30204 (16)0.0599 (5)
O2'0.37153 (17)0.97058 (5)0.21000 (15)0.0587 (5)
O3'−0.07087 (16)0.95549 (5)0.29180 (16)0.0619 (5)
N1'0.24881 (18)0.94574 (6)0.37937 (16)0.0432 (6)
C1'0.1023 (3)0.86096 (7)0.1393 (2)0.0540 (7)
C2'−0.0250 (3)0.84437 (9)0.0434 (3)0.0675 (9)
C3'−0.1041 (3)0.87391 (10)−0.0551 (2)0.0720 (10)
C4'−0.0567 (3)0.92019 (9)−0.0586 (2)0.0687 (9)
C5'0.0710 (3)0.93721 (8)0.0355 (2)0.0542 (7)
C6'0.1504 (2)0.90740 (7)0.13445 (18)0.0412 (6)
C7'0.1746 (2)0.99118 (7)0.37841 (18)0.0415 (6)
C8'0.2668 (3)1.02998 (7)0.4245 (2)0.0570 (8)
C9'0.1992 (3)1.07399 (8)0.4279 (3)0.0711 (10)
C10'0.0390 (3)1.07863 (9)0.3853 (3)0.0694 (10)
C11'−0.0561 (3)1.04027 (8)0.3392 (2)0.0593 (8)
C12'0.0103 (2)0.99586 (7)0.33485 (19)0.0453 (7)
C13'−0.2368 (3)0.95970 (11)0.2309 (3)0.0931 (13)
H10.303700.802900.821500.0820*
H1N0.476 (2)0.8381 (6)0.4514 (17)0.0520*
H20.369100.846201.012600.1040*
H30.474600.920601.015600.0910*
H40.530600.951100.836000.0800*
H50.471200.907700.645100.0610*
H80.598700.774900.740000.0640*
H90.848300.741900.820500.0820*
H101.027300.744000.701700.0870*
H110.963600.779400.500100.0710*
H13A0.882700.846700.350500.0980*
H13B0.742100.841400.224200.0980*
H13C0.837300.796500.288400.0980*
H1'0.155500.841100.206500.0650*
H1N'0.210 (2)0.9225 (6)0.4068 (19)0.0520*
H2'−0.057700.813000.045300.0810*
H3'−0.190200.86250−0.119700.0860*
H4'−0.111300.94010−0.125200.0820*
H5'0.103700.968500.032800.0650*
H8'0.376401.026600.453800.0680*
H9'0.262601.100200.459100.0850*
H10'−0.006801.108300.387400.0830*
H11'−0.165601.044100.310800.0710*
H13D−0.289500.970500.293100.1400*
H13E−0.278600.929300.197700.1400*
H13F−0.253900.982100.160900.1400*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0350 (2)0.0431 (3)0.0485 (3)0.0004 (2)0.0165 (2)−0.0006 (2)
O10.0577 (9)0.0437 (8)0.0721 (11)−0.0080 (7)0.0265 (8)−0.0027 (7)
O20.0329 (7)0.0658 (9)0.0574 (9)0.0070 (6)0.0137 (6)0.0053 (7)
O30.0403 (7)0.0654 (9)0.0508 (8)0.0048 (7)0.0200 (6)0.0008 (7)
N10.0351 (8)0.0546 (10)0.0419 (9)0.0105 (7)0.0148 (7)0.0079 (7)
C10.0940 (18)0.0595 (15)0.0663 (16)−0.0063 (13)0.0479 (14)−0.0035 (12)
C20.114 (2)0.098 (2)0.0639 (18)0.0013 (19)0.0522 (17)−0.0102 (16)
C30.0722 (17)0.093 (2)0.0642 (17)0.0062 (15)0.0193 (14)−0.0275 (15)
C40.0516 (13)0.0576 (15)0.0858 (19)−0.0042 (11)0.0126 (13)−0.0189 (13)
C50.0466 (11)0.0494 (12)0.0588 (14)−0.0019 (10)0.0169 (10)0.0001 (10)
C60.0410 (10)0.0436 (11)0.0469 (11)0.0050 (8)0.0195 (9)0.0004 (9)
C70.0333 (9)0.0354 (10)0.0463 (11)0.0035 (8)0.0084 (8)−0.0031 (8)
C80.0521 (12)0.0505 (13)0.0560 (13)0.0049 (10)0.0114 (10)0.0089 (10)
C90.0635 (15)0.0601 (15)0.0686 (16)0.0082 (12)−0.0022 (13)0.0190 (12)
C100.0448 (12)0.0618 (16)0.101 (2)0.0167 (11)0.0017 (13)0.0162 (14)
C110.0365 (11)0.0537 (13)0.0886 (18)0.0076 (10)0.0174 (11)−0.0007 (12)
C120.0328 (9)0.0362 (10)0.0543 (12)0.0000 (8)0.0091 (8)−0.0062 (9)
C130.0596 (13)0.0753 (16)0.0730 (16)−0.0073 (12)0.0383 (13)−0.0062 (13)
S1'0.0351 (2)0.0419 (3)0.0543 (3)0.0050 (2)0.0143 (2)0.0066 (2)
O1'0.0452 (8)0.0579 (9)0.0768 (11)0.0199 (7)0.0172 (7)0.0121 (8)
O2'0.0542 (8)0.0521 (9)0.0770 (11)−0.0079 (7)0.0304 (8)0.0062 (8)
O3'0.0368 (7)0.0664 (10)0.0780 (11)−0.0051 (7)0.0085 (7)−0.0066 (8)
N1'0.0405 (9)0.0425 (10)0.0463 (10)0.0013 (7)0.0113 (7)0.0067 (7)
C1'0.0641 (13)0.0433 (12)0.0555 (13)0.0007 (10)0.0178 (11)0.0076 (10)
C2'0.0769 (16)0.0555 (15)0.0686 (16)−0.0142 (12)0.0174 (14)−0.0068 (12)
C3'0.0709 (16)0.0831 (19)0.0549 (15)−0.0082 (14)0.0053 (12)−0.0136 (13)
C4'0.0729 (16)0.0741 (17)0.0503 (14)0.0100 (13)0.0023 (12)0.0064 (12)
C5'0.0635 (13)0.0466 (12)0.0515 (13)0.0081 (10)0.0141 (11)0.0089 (10)
C6'0.0431 (10)0.0406 (11)0.0429 (11)0.0061 (8)0.0168 (9)0.0027 (8)
C7'0.0403 (10)0.0456 (11)0.0391 (10)0.0035 (8)0.0120 (8)0.0001 (8)
C8'0.0460 (11)0.0542 (13)0.0696 (15)−0.0039 (10)0.0141 (11)−0.0114 (11)
C9'0.0695 (16)0.0507 (14)0.094 (2)−0.0067 (12)0.0242 (14)−0.0202 (13)
C10'0.0766 (17)0.0563 (15)0.0807 (18)0.0155 (13)0.0306 (14)−0.0106 (13)
C11'0.0474 (12)0.0714 (16)0.0611 (15)0.0170 (11)0.0183 (11)−0.0006 (12)
C12'0.0389 (10)0.0543 (13)0.0433 (11)0.0013 (9)0.0122 (9)−0.0005 (9)
C13'0.0414 (13)0.098 (2)0.123 (3)−0.0113 (13)−0.0060 (14)−0.0054 (18)

Geometric parameters (Å, °)

S1—O11.4212 (15)C5—H50.9300
S1—O21.4319 (15)C8—H80.9300
S1—N11.6063 (17)C9—H90.9300
S1—C61.760 (2)C10—H100.9300
S1'—C6'1.7582 (19)C11—H110.9300
S1'—N1'1.6299 (17)C13—H13A0.9600
S1'—O1'1.4260 (15)C13—H13C0.9600
S1'—O2'1.4235 (15)C13—H13B0.9600
O3—C121.357 (2)C1'—C2'1.375 (4)
O3—C131.417 (3)C1'—C6'1.380 (3)
O3'—C12'1.354 (2)C2'—C3'1.374 (4)
O3'—C13'1.427 (3)C3'—C4'1.372 (4)
N1—C71.418 (2)C4'—C5'1.372 (3)
N1—H1N0.843 (17)C5'—C6'1.382 (3)
N1'—C7'1.435 (3)C7'—C12'1.394 (3)
N1'—H1N'0.828 (18)C7'—C8'1.369 (3)
C1—C21.383 (4)C8'—C9'1.379 (3)
C1—C61.372 (3)C9'—C10'1.359 (4)
C2—C31.363 (4)C10'—C11'1.371 (4)
C3—C41.360 (4)C11'—C12'1.386 (3)
C4—C51.381 (4)C1'—H1'0.9300
C5—C61.376 (3)C2'—H2'0.9300
C7—C121.393 (3)C3'—H3'0.9300
C7—C81.376 (3)C4'—H4'0.9300
C8—C91.385 (4)C5'—H5'0.9300
C9—C101.358 (4)C8'—H8'0.9300
C10—C111.378 (4)C9'—H9'0.9300
C11—C121.383 (3)C10'—H10'0.9300
C1—H10.9300C11'—H11'0.9300
C2—H20.9300C13'—H13D0.9600
C3—H30.9300C13'—H13E0.9600
C4—H40.9300C13'—H13F0.9600
O1—S1—O2118.77 (9)C9—C10—H10120.00
O1—S1—N1109.73 (9)C11—C10—H10120.00
O1—S1—C6107.75 (9)C10—C11—H11120.00
O2—S1—N1104.98 (9)C12—C11—H11120.00
O2—S1—C6108.59 (9)O3—C13—H13A109.00
N1—S1—C6106.38 (9)H13A—C13—H13C109.00
O1'—S1'—O2'119.21 (9)H13B—C13—H13C109.00
O1'—S1'—N1'106.05 (9)H13A—C13—H13B109.00
O1'—S1'—C6'107.24 (9)O3—C13—H13B109.00
O2'—S1'—N1'106.80 (9)O3—C13—H13C110.00
O2'—S1'—C6'108.68 (9)C2'—C1'—C6'119.2 (2)
N1'—S1'—C6'108.48 (9)C1'—C2'—C3'120.3 (2)
C12—O3—C13119.21 (16)C2'—C3'—C4'120.3 (2)
C12'—O3'—C13'117.44 (18)C3'—C4'—C5'120.3 (2)
S1—N1—C7126.62 (14)C4'—C5'—C6'119.3 (2)
C7—N1—H1N118.8 (12)S1'—C6'—C5'119.63 (16)
S1—N1—H1N114.2 (12)C1'—C6'—C5'120.68 (19)
S1'—N1'—C7'120.30 (13)S1'—C6'—C1'119.68 (15)
C7'—N1'—H1N'118.5 (13)C8'—C7'—C12'119.96 (19)
S1'—N1'—H1N'109.0 (13)N1'—C7'—C8'119.22 (18)
C2—C1—C6119.5 (2)N1'—C7'—C12'120.80 (17)
C1—C2—C3119.6 (3)C7'—C8'—C9'120.8 (2)
C2—C3—C4121.2 (3)C8'—C9'—C10'119.3 (2)
C3—C4—C5119.8 (2)C9'—C10'—C11'121.0 (2)
C4—C5—C6119.3 (2)C10'—C11'—C12'120.3 (2)
C1—C6—C5120.58 (19)C7'—C12'—C11'118.65 (19)
S1—C6—C1119.96 (16)O3'—C12'—C7'115.67 (17)
S1—C6—C5119.42 (15)O3'—C12'—C11'125.68 (18)
C8—C7—C12119.97 (19)C2'—C1'—H1'120.00
N1—C7—C8123.93 (19)C6'—C1'—H1'120.00
N1—C7—C12116.10 (16)C1'—C2'—H2'120.00
C7—C8—C9119.5 (2)C3'—C2'—H2'120.00
C8—C9—C10120.6 (3)C2'—C3'—H3'120.00
C9—C10—C11120.7 (3)C4'—C3'—H3'120.00
C10—C11—C12119.5 (2)C3'—C4'—H4'120.00
C7—C12—C11119.7 (2)C5'—C4'—H4'120.00
O3—C12—C7115.04 (16)C4'—C5'—H5'120.00
O3—C12—C11125.23 (19)C6'—C5'—H5'120.00
C6—C1—H1120.00C7'—C8'—H8'120.00
C2—C1—H1120.00C9'—C8'—H8'120.00
C3—C2—H2120.00C8'—C9'—H9'120.00
C1—C2—H2120.00C10'—C9'—H9'120.00
C4—C3—H3119.00C9'—C10'—H10'119.00
C2—C3—H3119.00C11'—C10'—H10'120.00
C5—C4—H4120.00C10'—C11'—H11'120.00
C3—C4—H4120.00C12'—C11'—H11'120.00
C4—C5—H5120.00O3'—C13'—H13D109.00
C6—C5—H5120.00O3'—C13'—H13E109.00
C7—C8—H8120.00O3'—C13'—H13F109.00
C9—C8—H8120.00H13D—C13'—H13E109.00
C10—C9—H9120.00H13D—C13'—H13F109.00
C8—C9—H9120.00H13E—C13'—H13F110.00
O1—S1—N1—C7−49.05 (18)C4—C5—C6—S1177.86 (17)
O2—S1—N1—C7−177.75 (15)C4—C5—C6—C10.0 (3)
C6—S1—N1—C767.25 (18)C12—C7—C8—C91.0 (3)
O1—S1—C6—C1−14.8 (2)N1—C7—C12—O3−0.7 (2)
O1—S1—C6—C5167.32 (15)N1—C7—C8—C9−178.4 (2)
O2—S1—C6—C1115.07 (18)C8—C7—C12—O3179.93 (17)
O2—S1—C6—C5−62.83 (17)C8—C7—C12—C11−1.2 (3)
N1—S1—C6—C1−132.41 (18)N1—C7—C12—C11178.21 (18)
N1—S1—C6—C549.70 (18)C7—C8—C9—C10−0.5 (4)
N1'—S1'—C6'—C5'95.33 (18)C8—C9—C10—C110.1 (4)
O1'—S1'—N1'—C7'163.92 (14)C9—C10—C11—C12−0.3 (4)
O2'—S1'—N1'—C7'35.80 (17)C10—C11—C12—C70.8 (3)
C6'—S1'—N1'—C7'−81.17 (16)C10—C11—C12—O3179.6 (2)
O1'—S1'—C6'—C1'30.5 (2)C6'—C1'—C2'—C3'−0.7 (4)
O1'—S1'—C6'—C5'−150.54 (17)C2'—C1'—C6'—S1'179.66 (19)
O2'—S1'—C6'—C1'160.64 (17)C2'—C1'—C6'—C5'0.7 (3)
O2'—S1'—C6'—C5'−20.4 (2)C1'—C2'—C3'—C4'0.0 (4)
N1'—S1'—C6'—C1'−83.61 (19)C2'—C3'—C4'—C5'0.7 (4)
C13—O3—C12—C7174.60 (17)C3'—C4'—C5'—C6'−0.6 (4)
C13—O3—C12—C11−4.2 (3)C4'—C5'—C6'—S1'−179.01 (18)
C13'—O3'—C12'—C7'−172.1 (2)C4'—C5'—C6'—C1'−0.1 (3)
C13'—O3'—C12'—C11'8.2 (3)N1'—C7'—C8'—C9'−178.5 (2)
S1—N1—C7—C8−8.1 (3)C12'—C7'—C8'—C9'−0.3 (3)
S1—N1—C7—C12172.47 (14)N1'—C7'—C12'—O3'−1.5 (3)
S1'—N1'—C7'—C8'−88.1 (2)N1'—C7'—C12'—C11'178.22 (18)
S1'—N1'—C7'—C12'93.8 (2)C8'—C7'—C12'—O3'−179.62 (18)
C2—C1—C6—C5−0.7 (4)C8'—C7'—C12'—C11'0.1 (3)
C6—C1—C2—C31.6 (4)C7'—C8'—C9'—C10'0.3 (4)
C2—C1—C6—S1−178.6 (2)C8'—C9'—C10'—C11'0.1 (4)
C1—C2—C3—C4−1.9 (5)C9'—C10'—C11'—C12'−0.3 (4)
C2—C3—C4—C51.2 (4)C10'—C11'—C12'—O3'179.9 (2)
C3—C4—C5—C6−0.2 (4)C10'—C11'—C12'—C7'0.2 (3)

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C7'–C12' phenyl ring.
D—H···AD—HH···AD···AD—H···A
N1'—H1N'···O20.828 (18)2.310 (17)3.074 (2)153.6 (17)
N1—H1N···O1'0.843 (17)2.129 (17)2.961 (2)168.7 (17)
N1—H1N···O30.843 (17)2.258 (18)2.592 (2)103.8 (14)
C4—H4···O2'i0.932.473.377 (3)167
C4'—H4'···Cg4ii0.932.853.601 (2)138

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5501).

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