4-Chloro-N-(2,5-dimethyl-phen-yl)benzene-sulfonamide.

The title compound, C(14)H(14)ClNO(2)S, contains two molecules in the asymmetric unit with different conformations. The C-SO(2)-NH-C torsion angles are 65.3 (2) and 54.6 (2)° and the aromatic rings are tilted relative to each other by 59.3 (1) and 45.8 (1)° in the two mol-ecules. In the crystal, inversion symmetry results in dimers linked by pairs of N-H⋯O hydrogen bonds for both molecules.

Related literature

For hydrogen-bonding modes of n class="Chemical">sulfonamides, see: Adsmond & Grant (2001 ▶). For our studies of the effect of substituents upon the structures of N-(ar­yl)-amides, aryl­sulfonamides and methane­sulfonamides, see: Gowda et al. (2000 ▶, 2007 ▶, 2009 ▶); Shakuntala et al. (2011 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Triclinic,

a = 10.624 (1) Å

b = 11.165 (1) Å

c = 13.845 (2) Å

α = 74.643 (8)°

β = 67.654 (7)°

γ = 82.195 (8)°

V = 1463.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 293 K

0.44 × 0.40 × 0.36 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.844, T max = 0.869

10424 measured reflections

5971 independent reflections

4355 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.03

5971 reflections

353 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019660/tk2748sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019660/tk2748Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019660/tk2748Isup3.cml

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

C14H14ClNO2S	Z = 4
Mr = 295.77	F(000) = 616
Triclinic, P1	Dx = 1.342 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.624 (1) Å	Cell parameters from 4045 reflections
b = 11.165 (1) Å	θ = 2.9–27.8°
c = 13.845 (2) Å	µ = 0.40 mm−1
α = 74.643 (8)°	T = 293 K
β = 67.654 (7)°	Prism, light-brown
γ = 82.195 (8)°	0.44 × 0.40 × 0.36 mm
V = 1463.6 (3) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5971 independent reflections
Radiation source: fine-focus sealed tube	4355 reflections with I > 2σ(I)
graphite	Rint = 0.012
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→13
Tmin = 0.844, Tmax = 0.869	k = −13→12
10424 measured reflections	l = −16→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.217P] where P = (Fo2 + 2Fc2)/3
5971 reflections	(Δ/σ)max = 0.022
353 parameters	Δρmax = 0.24 e Å−3
2 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.36006 (9)	0.53177 (6)	0.87418 (6)	0.1008 (3)
S1	0.20650 (4)	−0.02218 (5)	1.01469 (4)	0.04847 (14)
O1	0.31155 (13)	−0.09429 (13)	1.04686 (11)	0.0597 (4)
O2	0.06835 (12)	−0.03204 (15)	1.08715 (11)	0.0634 (4)
N1	0.20717 (15)	−0.05945 (15)	0.90863 (14)	0.0505 (4)
H1N	0.1347 (18)	−0.0308 (19)	0.8978 (17)	0.061*
C1	0.24889 (17)	0.13475 (18)	0.97593 (14)	0.0455 (4)
C2	0.1538 (2)	0.2278 (2)	0.96025 (17)	0.0558 (5)
H2	0.0662	0.2077	0.9720	0.067*
C3	0.1887 (2)	0.3495 (2)	0.92738 (18)	0.0635 (6)
H3	0.1254	0.4126	0.9162	0.076*
C4	0.3191 (2)	0.3775 (2)	0.91104 (17)	0.0617 (5)
C5	0.4142 (2)	0.2861 (2)	0.92548 (19)	0.0697 (6)
H5	0.5017	0.3066	0.9136	0.084*
C6	0.3798 (2)	0.1642 (2)	0.95757 (18)	0.0619 (5)
H6	0.4441	0.1014	0.9670	0.074*
C7	0.32965 (17)	−0.06143 (17)	0.81716 (16)	0.0470 (4)
C8	0.3468 (2)	0.02420 (19)	0.72070 (17)	0.0541 (5)
C9	0.4666 (2)	0.0123 (2)	0.63506 (19)	0.0702 (6)
H9	0.4815	0.0683	0.5691	0.084*
C10	0.5638 (2)	−0.0801 (3)	0.6452 (2)	0.0747 (7)
H10	0.6425	−0.0851	0.5860	0.090*
C11	0.5473 (2)	−0.1649 (2)	0.7408 (2)	0.0668 (6)
C12	0.42823 (19)	−0.15453 (18)	0.82663 (18)	0.0556 (5)
H12	0.4139	−0.2112	0.8922	0.067*
C13	0.2426 (3)	0.1260 (2)	0.7063 (2)	0.0774 (7)
H13A	0.2250	0.1754	0.7576	0.093*
H13B	0.1598	0.0900	0.7172	0.093*
H13C	0.2766	0.1776	0.6350	0.093*
C14	0.6526 (3)	−0.2670 (3)	0.7534 (3)	0.0968 (9)
H14A	0.6897	−0.2547	0.8032	0.116*
H14B	0.7242	−0.2652	0.6850	0.116*
H14C	0.6108	−0.3460	0.7800	0.116*
Cl2	0.09005 (14)	1.02785 (8)	0.31731 (10)	0.1497 (5)
S2	0.29930 (4)	0.49101 (6)	0.46867 (4)	0.05870 (17)
O3	0.20405 (14)	0.40575 (15)	0.48001 (13)	0.0677 (4)
O4	0.43982 (14)	0.47354 (19)	0.40614 (14)	0.0838 (5)
N2	0.29581 (15)	0.49000 (17)	0.58726 (14)	0.0545 (4)
H2N	0.3663 (18)	0.517 (2)	0.5847 (18)	0.065*
C15	0.2409 (2)	0.6403 (2)	0.41858 (16)	0.0589 (5)
C16	0.3320 (3)	0.7294 (3)	0.34757 (19)	0.0790 (7)
H16	0.4247	0.7086	0.3222	0.095*
C17	0.2868 (4)	0.8466 (3)	0.3148 (2)	0.0987 (10)
H17	0.3477	0.9064	0.2662	0.118*
C18	0.1494 (4)	0.8763 (3)	0.3542 (2)	0.0922 (9)
C19	0.0557 (3)	0.7888 (3)	0.4245 (2)	0.0815 (7)
H19	−0.0368	0.8103	0.4499	0.098*
C20	0.1023 (2)	0.6699 (2)	0.45579 (18)	0.0627 (6)
H20	0.0412	0.6091	0.5019	0.075*
C21	0.17227 (17)	0.52401 (17)	0.66661 (15)	0.0450 (4)
C22	0.16013 (19)	0.63472 (18)	0.69746 (16)	0.0516 (5)
C23	0.0385 (2)	0.6576 (2)	0.77699 (18)	0.0636 (6)
H23	0.0280	0.7294	0.8018	0.076*
C24	−0.0666 (2)	0.5780 (2)	0.82014 (18)	0.0641 (6)
H24	−0.1468	0.5972	0.8729	0.077*
C25	−0.05576 (19)	0.4699 (2)	0.78675 (16)	0.0578 (5)
C26	0.06623 (18)	0.44264 (18)	0.71042 (15)	0.0502 (4)
H26	0.0774	0.3690	0.6882	0.060*
C27	0.2709 (2)	0.7278 (2)	0.6475 (2)	0.0720 (6)
H27A	0.3544	0.6876	0.6533	0.086*
H27B	0.2455	0.7941	0.6842	0.086*
H27C	0.2834	0.7608	0.5731	0.086*
C28	−0.1723 (2)	0.3822 (3)	0.8332 (2)	0.0877 (8)
H28A	−0.2081	0.3685	0.9100	0.105*
H28B	−0.1398	0.3044	0.8134	0.105*
H28C	−0.2427	0.4180	0.8055	0.105*

	U11	U22	U33	U12	U13	U23
Cl1	0.1377 (7)	0.0670 (4)	0.1017 (5)	−0.0271 (4)	−0.0484 (5)	−0.0069 (4)
S1	0.0310 (2)	0.0595 (3)	0.0527 (3)	−0.00033 (18)	−0.0184 (2)	−0.0050 (2)
O1	0.0427 (7)	0.0663 (9)	0.0697 (9)	0.0027 (6)	−0.0308 (7)	−0.0015 (7)
O2	0.0353 (7)	0.0890 (11)	0.0576 (8)	−0.0060 (6)	−0.0148 (6)	−0.0044 (7)
N1	0.0350 (8)	0.0568 (10)	0.0635 (10)	0.0006 (7)	−0.0234 (7)	−0.0131 (8)
C1	0.0349 (9)	0.0585 (11)	0.0458 (10)	0.0029 (7)	−0.0177 (8)	−0.0144 (8)
C2	0.0466 (11)	0.0637 (13)	0.0664 (13)	0.0083 (9)	−0.0284 (10)	−0.0237 (10)
C3	0.0696 (14)	0.0636 (14)	0.0691 (14)	0.0143 (11)	−0.0379 (12)	−0.0241 (11)
C4	0.0773 (15)	0.0615 (13)	0.0491 (11)	−0.0110 (11)	−0.0230 (11)	−0.0128 (10)
C5	0.0529 (12)	0.0781 (16)	0.0766 (15)	−0.0165 (11)	−0.0232 (11)	−0.0090 (12)
C6	0.0396 (10)	0.0680 (14)	0.0762 (14)	0.0011 (9)	−0.0247 (10)	−0.0096 (11)
C7	0.0394 (9)	0.0480 (10)	0.0613 (12)	−0.0007 (7)	−0.0222 (9)	−0.0199 (9)
C8	0.0525 (11)	0.0582 (12)	0.0592 (12)	−0.0001 (9)	−0.0247 (10)	−0.0204 (10)
C9	0.0687 (15)	0.0865 (17)	0.0580 (13)	−0.0067 (12)	−0.0207 (11)	−0.0226 (12)
C10	0.0515 (13)	0.1006 (19)	0.0762 (16)	0.0014 (12)	−0.0118 (11)	−0.0465 (15)
C11	0.0479 (12)	0.0732 (15)	0.0932 (18)	0.0087 (10)	−0.0277 (12)	−0.0443 (14)
C12	0.0502 (11)	0.0478 (11)	0.0767 (14)	0.0029 (8)	−0.0288 (10)	−0.0208 (10)
C13	0.0839 (17)	0.0796 (17)	0.0654 (14)	0.0161 (13)	−0.0341 (13)	−0.0106 (12)
C14	0.0618 (15)	0.093 (2)	0.144 (3)	0.0291 (14)	−0.0373 (16)	−0.0580 (19)
Cl2	0.2453 (13)	0.0760 (5)	0.1754 (10)	−0.0184 (6)	−0.1439 (10)	0.0009 (6)
S2	0.0326 (2)	0.0867 (4)	0.0650 (3)	−0.0024 (2)	−0.0138 (2)	−0.0367 (3)
O3	0.0480 (8)	0.0808 (10)	0.0881 (11)	−0.0032 (7)	−0.0245 (7)	−0.0420 (9)
O4	0.0359 (8)	0.1438 (16)	0.0843 (11)	0.0026 (8)	−0.0118 (7)	−0.0648 (11)
N2	0.0333 (8)	0.0728 (11)	0.0646 (11)	0.0008 (7)	−0.0191 (8)	−0.0271 (9)
C15	0.0503 (11)	0.0830 (15)	0.0516 (11)	−0.0199 (10)	−0.0201 (9)	−0.0176 (10)
C16	0.0724 (15)	0.108 (2)	0.0584 (14)	−0.0385 (15)	−0.0176 (12)	−0.0143 (14)
C17	0.124 (3)	0.111 (3)	0.0714 (17)	−0.059 (2)	−0.0420 (18)	0.0003 (17)
C18	0.146 (3)	0.0692 (17)	0.0907 (19)	−0.0251 (17)	−0.079 (2)	−0.0017 (14)
C19	0.0865 (18)	0.0819 (18)	0.0928 (19)	−0.0031 (14)	−0.0538 (16)	−0.0153 (15)
C20	0.0518 (12)	0.0731 (15)	0.0692 (14)	−0.0102 (10)	−0.0297 (10)	−0.0105 (11)
C21	0.0376 (9)	0.0522 (11)	0.0472 (10)	0.0033 (7)	−0.0189 (8)	−0.0118 (8)
C22	0.0525 (11)	0.0521 (11)	0.0546 (11)	0.0000 (8)	−0.0248 (9)	−0.0122 (9)
C23	0.0683 (14)	0.0615 (13)	0.0644 (13)	0.0138 (11)	−0.0253 (11)	−0.0264 (11)
C24	0.0456 (11)	0.0851 (16)	0.0550 (12)	0.0095 (11)	−0.0122 (9)	−0.0203 (11)
C25	0.0438 (10)	0.0742 (14)	0.0512 (11)	−0.0052 (9)	−0.0175 (9)	−0.0059 (10)
C26	0.0462 (10)	0.0489 (11)	0.0570 (11)	−0.0004 (8)	−0.0222 (9)	−0.0102 (9)
C27	0.0792 (16)	0.0642 (14)	0.0781 (16)	−0.0187 (11)	−0.0282 (13)	−0.0175 (12)
C28	0.0626 (15)	0.111 (2)	0.0774 (17)	−0.0310 (14)	−0.0087 (13)	−0.0132 (15)

Cl1—C4	1.728 (2)	Cl2—C18	1.737 (3)
S1—O1	1.4270 (13)	S2—O3	1.4200 (15)
S1—O2	1.4277 (13)	S2—O4	1.4296 (14)
S1—N1	1.6261 (17)	S2—N2	1.6252 (18)
S1—C1	1.759 (2)	S2—C15	1.755 (2)
N1—C7	1.432 (2)	N2—C21	1.436 (2)
N1—H1N	0.845 (15)	N2—H2N	0.830 (15)
C1—C2	1.382 (3)	C15—C16	1.383 (3)
C1—C6	1.385 (3)	C15—C20	1.387 (3)
C2—C3	1.368 (3)	C16—C17	1.353 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.382 (3)	C17—C18	1.377 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.367 (3)	C18—C19	1.385 (4)
C5—C6	1.369 (3)	C19—C20	1.370 (3)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.384 (3)	C21—C22	1.386 (3)
C7—C12	1.390 (3)	C21—C26	1.389 (3)
C8—C9	1.390 (3)	C22—C23	1.388 (3)
C8—C13	1.504 (3)	C22—C27	1.509 (3)
C9—C10	1.376 (3)	C23—C24	1.369 (3)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.373 (4)	C24—C25	1.379 (3)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.384 (3)	C25—C26	1.382 (3)
C11—C14	1.509 (3)	C25—C28	1.516 (3)
C12—H12	0.9300	C26—H26	0.9300
C13—H13A	0.9600	C27—H27A	0.9600
C13—H13B	0.9600	C27—H27B	0.9600
C13—H13C	0.9600	C27—H27C	0.9600
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600
O1—S1—O2	119.67 (9)	O3—S2—O4	119.34 (10)
O1—S1—N1	108.40 (9)	O3—S2—N2	108.59 (10)
O2—S1—N1	104.99 (8)	O4—S2—N2	105.32 (9)
O1—S1—C1	107.65 (8)	O3—S2—C15	107.35 (9)
O2—S1—C1	108.48 (9)	O4—S2—C15	109.38 (11)
N1—S1—C1	107.02 (9)	N2—S2—C15	106.13 (9)
C7—N1—S1	121.67 (12)	C21—N2—S2	120.23 (12)
C7—N1—H1N	118.1 (15)	C21—N2—H2N	115.1 (16)
S1—N1—H1N	109.0 (14)	S2—N2—H2N	112.1 (16)
C2—C1—C6	120.22 (19)	C16—C15—C20	120.4 (2)
C2—C1—S1	120.27 (14)	C16—C15—S2	120.56 (19)
C6—C1—S1	119.47 (15)	C20—C15—S2	118.96 (16)
C3—C2—C1	119.89 (19)	C17—C16—C15	120.2 (3)
C3—C2—H2	120.1	C17—C16—H16	119.9
C1—C2—H2	120.1	C15—C16—H16	119.9
C2—C3—C4	119.20 (19)	C16—C17—C18	119.2 (3)
C2—C3—H3	120.4	C16—C17—H17	120.4
C4—C3—H3	120.4	C18—C17—H17	120.4
C5—C4—C3	121.3 (2)	C17—C18—C19	121.9 (3)
C5—C4—Cl1	119.91 (18)	C17—C18—Cl2	119.9 (3)
C3—C4—Cl1	118.74 (18)	C19—C18—Cl2	118.3 (3)
C4—C5—C6	119.5 (2)	C20—C19—C18	118.5 (3)
C4—C5—H5	120.2	C20—C19—H19	120.8
C6—C5—H5	120.2	C18—C19—H19	120.8
C5—C6—C1	119.80 (19)	C19—C20—C15	119.8 (2)
C5—C6—H6	120.1	C19—C20—H20	120.1
C1—C6—H6	120.1	C15—C20—H20	120.1
C8—C7—C12	120.94 (19)	C22—C21—C26	121.60 (18)
C8—C7—N1	120.78 (17)	C22—C21—N2	120.70 (17)
C12—C7—N1	118.22 (18)	C26—C21—N2	117.70 (17)
C7—C8—C9	116.84 (19)	C21—C22—C23	116.47 (18)
C7—C8—C13	122.87 (19)	C21—C22—C27	122.79 (19)
C9—C8—C13	120.3 (2)	C23—C22—C27	120.73 (19)
C10—C9—C8	121.8 (2)	C24—C23—C22	122.1 (2)
C10—C9—H9	119.1	C24—C23—H23	118.9
C8—C9—H9	119.1	C22—C23—H23	118.9
C11—C10—C9	121.5 (2)	C23—C24—C25	121.2 (2)
C11—C10—H10	119.2	C23—C24—H24	119.4
C9—C10—H10	119.2	C25—C24—H24	119.4
C10—C11—C12	117.3 (2)	C24—C25—C26	117.83 (19)
C10—C11—C14	122.3 (2)	C24—C25—C28	121.5 (2)
C12—C11—C14	120.5 (3)	C26—C25—C28	120.7 (2)
C11—C12—C7	121.6 (2)	C25—C26—C21	120.71 (19)
C11—C12—H12	119.2	C25—C26—H26	119.6
C7—C12—H12	119.2	C21—C26—H26	119.6
C8—C13—H13A	109.5	C22—C27—H27A	109.5
C8—C13—H13B	109.5	C22—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C8—C13—H13C	109.5	C22—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
C11—C14—H14A	109.5	C25—C28—H28A	109.5
C11—C14—H14B	109.5	C25—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C11—C14—H14C	109.5	C25—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5
O1—S1—N1—C7	−50.51 (17)	O3—S2—N2—C21	−60.53 (18)
O2—S1—N1—C7	−179.50 (15)	O4—S2—N2—C21	170.55 (16)
C1—S1—N1—C7	65.34 (16)	C15—S2—N2—C21	54.62 (17)
O1—S1—C1—C2	−167.76 (15)	O3—S2—C15—C16	−144.82 (18)
O2—S1—C1—C2	−36.91 (18)	O4—S2—C15—C16	−14.0 (2)
N1—S1—C1—C2	75.89 (17)	N2—S2—C15—C16	99.20 (19)
O1—S1—C1—C6	14.51 (19)	O3—S2—C15—C20	38.66 (19)
O2—S1—C1—C6	145.36 (16)	O4—S2—C15—C20	169.51 (16)
N1—S1—C1—C6	−101.84 (17)	N2—S2—C15—C20	−77.32 (18)
C6—C1—C2—C3	−0.6 (3)	C20—C15—C16—C17	0.8 (3)
S1—C1—C2—C3	−178.30 (16)	S2—C15—C16—C17	−175.64 (19)
C1—C2—C3—C4	−0.4 (3)	C15—C16—C17—C18	0.9 (4)
C2—C3—C4—C5	1.0 (3)	C16—C17—C18—C19	−1.7 (4)
C2—C3—C4—Cl1	−177.72 (16)	C16—C17—C18—Cl2	177.4 (2)
C3—C4—C5—C6	−0.5 (4)	C17—C18—C19—C20	0.6 (4)
Cl1—C4—C5—C6	178.20 (18)	Cl2—C18—C19—C20	−178.53 (18)
C4—C5—C6—C1	−0.6 (4)	C18—C19—C20—C15	1.2 (4)
C2—C1—C6—C5	1.1 (3)	C16—C15—C20—C19	−1.9 (3)
S1—C1—C6—C5	178.82 (17)	S2—C15—C20—C19	174.61 (18)
S1—N1—C7—C8	−112.12 (18)	S2—N2—C21—C22	−109.42 (18)
S1—N1—C7—C12	70.4 (2)	S2—N2—C21—C26	70.3 (2)
C12—C7—C8—C9	−0.1 (3)	C26—C21—C22—C23	2.2 (3)
N1—C7—C8—C9	−177.55 (17)	N2—C21—C22—C23	−178.08 (17)
C12—C7—C8—C13	179.6 (2)	C26—C21—C22—C27	−176.96 (19)
N1—C7—C8—C13	2.2 (3)	N2—C21—C22—C27	2.7 (3)
C7—C8—C9—C10	0.0 (3)	C21—C22—C23—C24	−2.5 (3)
C13—C8—C9—C10	−179.7 (2)	C27—C22—C23—C24	176.7 (2)
C8—C9—C10—C11	−0.2 (4)	C22—C23—C24—C25	0.5 (3)
C9—C10—C11—C12	0.5 (3)	C23—C24—C25—C26	1.8 (3)
C9—C10—C11—C14	179.9 (2)	C23—C24—C25—C28	−179.2 (2)
C10—C11—C12—C7	−0.6 (3)	C24—C25—C26—C21	−2.1 (3)
C14—C11—C12—C7	−180.0 (2)	C28—C25—C26—C21	179.0 (2)
C8—C7—C12—C11	0.4 (3)	C22—C21—C26—C25	0.1 (3)
N1—C7—C12—C11	177.91 (17)	N2—C21—C26—C25	−179.65 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (2)	2.12 (2)	2.950 (2)	166 (2)
N2—H2N···O4ii	0.83 (2)	2.13 (2)	2.931 (2)	162 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (2)	2.12 (2)	2.950 (2)	166 (2)
N2—H2N⋯O4ii	0.83 (2)	2.13 (2)	2.931 (2)	162 (2)

Symmetry codes: (i) ; (ii) .