N-(2-Chloro-benzo-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C(13)H(10)ClNO(3)S, contains two independent mol-ecules, the chloro-phenyl ring of one of them being disordered over two orientations with occupancies of 0.836 (2) and 0.164 (2). In one of the independent mol-ecules, the sulfonyl-bound phenyl ring and the chloro-phenyl ring form dihedral angles of 87.3 (1) and 46.8 (1)°, respectively, with the -S-NH-C=O segment, while in the other mol-ecule the corresponding angles are 76.0 (1) and 39.6 (1)°. In the crystal, mol-ecules are linked into tetra-meric units by N-H⋯O hydrogen bonds.

Related literature

For background literature and similar structures, see: Gowda et al. (2009 ▶); Suchetan et al. (2009 ▶).

Experimental

Crystal data

C13H10ClNO3S

M = 295.73

Triclinic,

a = 7.3390 (5) Å

b = 10.828 (1) Å

c = 17.685 (1) Å

α = 93.088 (6)°

β = 96.863 (7)°

γ = 103.057 (8)°

V = 1354.46 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 299 K

0.50 × 0.44 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.811, T max = 0.902

9641 measured reflections

5521 independent reflections

4327 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.03

5521 reflections

359 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data 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/S1600536809055482/ci5004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055482/ci5004Isup2.hkl

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

C13H10ClNO3S	Z = 4
Mr = 295.73	F(000) = 608
Triclinic, P1	Dx = 1.450 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3390 (5) Å	Cell parameters from 4232 reflections
b = 10.828 (1) Å	θ = 2.9–27.8°
c = 17.685 (1) Å	µ = 0.44 mm−1
α = 93.088 (6)°	T = 299 K
β = 96.863 (7)°	Rod, colourless
γ = 103.057 (8)°	0.50 × 0.44 × 0.24 mm
V = 1354.46 (17) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5521 independent reflections
Radiation source: fine-focus sealed tube	4327 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→9
Tmin = 0.811, Tmax = 0.902	k = −13→13
9641 measured reflections	l = −22→21

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0558P)2 + 0.4941P] where P = (Fo2 + 2Fc2)/3
5521 reflections	(Δ/σ)max = 0.001
359 parameters	Δρmax = 0.38 e Å−3
4 restraints	Δρmin = −0.34 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	Occ. (<1)
Cl1A	0.80617 (12)	0.24676 (7)	0.30758 (5)	0.0701 (3)	0.836 (2)
Cl1B	0.8403 (6)	−0.1454 (3)	0.1258 (2)	0.0654 (14)	0.164 (2)
S1	0.74595 (8)	0.18519 (6)	0.00953 (3)	0.05430 (17)
O1	0.5985 (3)	0.11237 (18)	−0.04655 (8)	0.0717 (5)
O2	0.9314 (3)	0.22227 (19)	−0.00917 (10)	0.0716 (5)
O3	0.9713 (2)	0.22974 (14)	0.16030 (8)	0.0560 (4)
N1	0.7439 (3)	0.09130 (18)	0.08133 (10)	0.0518 (5)
H1N	0.649 (3)	0.029 (2)	0.0776 (14)	0.062*
C1	0.6742 (3)	0.3164 (2)	0.04645 (11)	0.0523 (5)
C2	0.4851 (4)	0.3057 (3)	0.05382 (14)	0.0684 (7)
H2	0.3965	0.2303	0.0373	0.082*
C3	0.4304 (5)	0.4070 (4)	0.08556 (17)	0.0816 (9)
H3	0.3041	0.4001	0.0910	0.098*
C4	0.5603 (6)	0.5189 (3)	0.10952 (17)	0.0851 (9)
H4	0.5218	0.5875	0.1309	0.102*
C5	0.7469 (5)	0.5298 (3)	0.10189 (17)	0.0813 (8)
H5	0.8339	0.6061	0.1181	0.098*
C6	0.8074 (4)	0.4290 (2)	0.07053 (14)	0.0628 (6)
H6	0.9341	0.4364	0.0656	0.075*
C7	0.8515 (3)	0.13091 (19)	0.15128 (11)	0.0434 (5)
C8	0.8065 (3)	0.04413 (19)	0.21252 (11)	0.0430 (5)
C9	0.7874 (3)	0.0905 (2)	0.28521 (12)	0.0519 (5)
H13B	0.8026	0.1775	0.2962	0.062*	0.164 (2)
C10	0.7457 (4)	0.0082 (3)	0.34149 (15)	0.0696 (7)
H10	0.7321	0.0399	0.3899	0.083*
C11	0.7248 (4)	−0.1190 (3)	0.32582 (18)	0.0775 (8)
H11	0.6967	−0.1738	0.3637	0.093*
C12	0.7444 (4)	−0.1672 (3)	0.25526 (18)	0.0727 (7)
H12	0.7317	−0.2542	0.2451	0.087*
C13	0.7833 (3)	−0.0856 (2)	0.19942 (14)	0.0568 (6)
H13A	0.7944	−0.1190	0.1511	0.068*	0.836 (2)
Cl2	0.23536 (16)	0.10580 (9)	0.45805 (4)	0.1023 (3)
S2	0.29519 (8)	0.52286 (5)	0.28419 (3)	0.04751 (15)
O4	0.1951 (3)	0.54542 (16)	0.21405 (9)	0.0656 (5)
O5	0.4931 (2)	0.57334 (16)	0.30069 (11)	0.0668 (5)
O6	0.4183 (3)	0.35322 (17)	0.39635 (9)	0.0690 (5)
N2	0.2562 (2)	0.36633 (16)	0.28095 (10)	0.0435 (4)
H2N	0.175 (3)	0.327 (2)	0.2468 (11)	0.052*
C14	0.1875 (3)	0.57205 (18)	0.36012 (12)	0.0446 (5)
C15	−0.0041 (3)	0.5674 (2)	0.34812 (15)	0.0566 (6)
H15	−0.0752	0.5370	0.3010	0.068*
C16	−0.0869 (4)	0.6085 (3)	0.40744 (17)	0.0702 (7)
H16	−0.2158	0.6045	0.4008	0.084*
C17	0.0204 (4)	0.6556 (3)	0.47655 (17)	0.0726 (7)
H17	−0.0365	0.6843	0.5161	0.087*
C18	0.2094 (4)	0.6607 (3)	0.48769 (15)	0.0662 (7)
H18	0.2805	0.6930	0.5346	0.079*
C19	0.2947 (3)	0.6181 (2)	0.42967 (13)	0.0533 (5)
H19	0.4230	0.6204	0.4372	0.064*
C20	0.3323 (3)	0.3006 (2)	0.33667 (11)	0.0437 (5)
C21	0.3018 (3)	0.16165 (19)	0.31408 (12)	0.0429 (4)
C22	0.2646 (3)	0.0685 (2)	0.36477 (14)	0.0568 (6)
C23	0.2407 (4)	−0.0596 (3)	0.3413 (2)	0.0743 (8)
H23	0.2131	−0.1209	0.3757	0.089*
C24	0.2578 (4)	−0.0950 (3)	0.2678 (2)	0.0776 (8)
H24	0.2428	−0.1805	0.2523	0.093*
C25	0.2967 (4)	−0.0054 (3)	0.21684 (17)	0.0689 (7)
H25	0.3091	−0.0300	0.1669	0.083*
C26	0.3177 (3)	0.1217 (2)	0.23930 (13)	0.0515 (5)
H26	0.3429	0.1817	0.2040	0.062*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0738 (5)	0.0520 (4)	0.0757 (5)	−0.0070 (3)	0.0281 (4)	−0.0179 (3)
Cl1B	0.091 (3)	0.050 (2)	0.055 (2)	0.0276 (19)	−0.0028 (18)	−0.0126 (15)
S1	0.0569 (3)	0.0613 (4)	0.0326 (3)	−0.0079 (3)	0.0006 (2)	0.0020 (2)
O1	0.0812 (12)	0.0787 (12)	0.0339 (8)	−0.0156 (9)	−0.0091 (8)	0.0000 (8)
O2	0.0661 (11)	0.0814 (13)	0.0610 (10)	−0.0014 (9)	0.0200 (9)	0.0044 (9)
O3	0.0544 (9)	0.0511 (9)	0.0462 (8)	−0.0111 (7)	−0.0141 (7)	0.0070 (7)
N1	0.0528 (11)	0.0503 (11)	0.0386 (9)	−0.0097 (8)	−0.0066 (8)	0.0021 (8)
C1	0.0548 (13)	0.0623 (14)	0.0334 (10)	0.0021 (10)	−0.0014 (9)	0.0125 (9)
C2	0.0586 (15)	0.091 (2)	0.0481 (13)	0.0007 (14)	0.0062 (11)	0.0157 (13)
C3	0.0758 (19)	0.118 (3)	0.0602 (16)	0.0336 (19)	0.0178 (14)	0.0238 (17)
C4	0.110 (3)	0.093 (2)	0.0608 (17)	0.039 (2)	0.0141 (17)	0.0143 (16)
C5	0.102 (2)	0.0620 (17)	0.0726 (18)	0.0102 (16)	−0.0015 (17)	0.0043 (14)
C6	0.0606 (15)	0.0611 (15)	0.0589 (14)	0.0022 (12)	−0.0020 (11)	0.0095 (12)
C7	0.0413 (10)	0.0411 (11)	0.0410 (10)	0.0019 (9)	−0.0047 (8)	−0.0005 (8)
C8	0.0359 (10)	0.0459 (11)	0.0406 (10)	0.0008 (8)	−0.0038 (8)	0.0038 (8)
C9	0.0401 (11)	0.0575 (13)	0.0489 (12)	−0.0036 (9)	0.0002 (9)	−0.0010 (10)
C10	0.0580 (15)	0.095 (2)	0.0468 (13)	−0.0030 (14)	0.0085 (11)	0.0107 (13)
C11	0.0737 (18)	0.081 (2)	0.0735 (19)	0.0039 (15)	0.0069 (14)	0.0341 (16)
C12	0.0743 (17)	0.0556 (15)	0.087 (2)	0.0093 (13)	0.0099 (15)	0.0240 (14)
C13	0.0589 (14)	0.0477 (13)	0.0601 (14)	0.0073 (10)	0.0029 (11)	0.0055 (10)
Cl2	0.1560 (9)	0.1102 (7)	0.0606 (4)	0.0553 (6)	0.0380 (5)	0.0304 (4)
S2	0.0530 (3)	0.0358 (3)	0.0472 (3)	0.0006 (2)	0.0003 (2)	0.0021 (2)
O4	0.0932 (13)	0.0518 (10)	0.0497 (9)	0.0166 (9)	−0.0012 (8)	0.0118 (7)
O5	0.0538 (9)	0.0578 (10)	0.0762 (11)	−0.0117 (8)	0.0120 (8)	−0.0072 (8)
O6	0.0854 (12)	0.0619 (10)	0.0536 (10)	0.0279 (9)	−0.0276 (9)	−0.0126 (8)
N2	0.0445 (9)	0.0359 (9)	0.0430 (9)	0.0046 (7)	−0.0099 (7)	−0.0036 (7)
C14	0.0483 (11)	0.0318 (10)	0.0508 (11)	0.0082 (8)	−0.0018 (9)	0.0021 (8)
C15	0.0538 (13)	0.0473 (12)	0.0654 (14)	0.0139 (10)	−0.0096 (11)	0.0058 (11)
C16	0.0562 (15)	0.0707 (17)	0.091 (2)	0.0311 (13)	0.0045 (14)	0.0136 (15)
C17	0.087 (2)	0.0755 (18)	0.0693 (17)	0.0443 (16)	0.0174 (15)	0.0069 (14)
C18	0.0777 (18)	0.0701 (16)	0.0520 (14)	0.0290 (14)	−0.0031 (12)	−0.0059 (12)
C19	0.0502 (12)	0.0504 (12)	0.0556 (13)	0.0129 (10)	−0.0056 (10)	−0.0037 (10)
C20	0.0420 (11)	0.0476 (11)	0.0415 (11)	0.0163 (9)	−0.0031 (8)	−0.0019 (9)
C21	0.0389 (10)	0.0435 (11)	0.0478 (11)	0.0149 (8)	0.0033 (8)	0.0011 (9)
C22	0.0599 (14)	0.0578 (14)	0.0602 (14)	0.0251 (11)	0.0128 (11)	0.0132 (11)
C23	0.0720 (17)	0.0556 (15)	0.102 (2)	0.0234 (13)	0.0166 (16)	0.0241 (15)
C24	0.0751 (18)	0.0477 (15)	0.111 (2)	0.0223 (13)	0.0070 (17)	−0.0074 (15)
C25	0.0631 (15)	0.0697 (17)	0.0738 (17)	0.0223 (13)	0.0086 (13)	−0.0216 (14)
C26	0.0457 (12)	0.0537 (13)	0.0549 (13)	0.0145 (10)	0.0053 (10)	−0.0055 (10)

Cl1A—C9	1.687 (2)	C13—H13A	0.93
Cl1B—C13	1.565 (4)	Cl2—C22	1.727 (3)
S1—O2	1.4137 (18)	S2—O5	1.4201 (17)
S1—O1	1.4320 (16)	S2—O4	1.4261 (16)
S1—N1	1.6683 (19)	S2—N2	1.6506 (17)
S1—C1	1.744 (3)	S2—C14	1.754 (2)
O3—C7	1.211 (2)	O6—C20	1.204 (2)
N1—C7	1.376 (2)	N2—C20	1.383 (3)
N1—H1N	0.845 (17)	N2—H2N	0.822 (16)
C1—C2	1.389 (3)	C14—C19	1.380 (3)
C1—C6	1.389 (3)	C14—C15	1.386 (3)
C2—C3	1.366 (4)	C15—C16	1.376 (4)
C2—H2	0.93	C15—H15	0.93
C3—C4	1.373 (5)	C16—C17	1.377 (4)
C3—H3	0.93	C16—H16	0.93
C4—C5	1.371 (5)	C17—C18	1.366 (4)
C4—H4	0.93	C17—H17	0.93
C5—C6	1.381 (4)	C18—C19	1.375 (3)
C5—H5	0.93	C18—H18	0.93
C6—H6	0.93	C19—H19	0.93
C7—C8	1.490 (3)	C20—C21	1.495 (3)
C8—C13	1.380 (3)	C21—C22	1.388 (3)
C8—C9	1.389 (3)	C21—C26	1.396 (3)
C9—C10	1.387 (3)	C22—C23	1.392 (4)
C9—H13B	0.93	C23—C24	1.363 (4)
C10—C11	1.361 (4)	C23—H23	0.93
C10—H10	0.93	C24—C25	1.366 (4)
C11—C12	1.363 (4)	C24—H24	0.93
C11—H11	0.93	C25—C26	1.380 (3)
C12—C13	1.373 (3)	C25—H25	0.93
C12—H12	0.93	C26—H26	0.93
O2—S1—O1	119.45 (11)	C12—C13—H13A	118.8
O2—S1—N1	109.51 (11)	C8—C13—H13A	118.8
O1—S1—N1	102.84 (10)	O5—S2—O4	119.97 (11)
O2—S1—C1	110.60 (11)	O5—S2—N2	107.85 (10)
O1—S1—C1	109.12 (12)	O4—S2—N2	103.72 (9)
N1—S1—C1	103.99 (10)	O5—S2—C14	108.61 (10)
C7—N1—S1	122.29 (15)	O4—S2—C14	108.75 (11)
C7—N1—H1N	119.6 (17)	N2—S2—C14	107.22 (10)
S1—N1—H1N	115.2 (17)	C20—N2—S2	124.21 (14)
C2—C1—C6	120.7 (3)	C20—N2—H2N	119.4 (17)
C2—C1—S1	119.5 (2)	S2—N2—H2N	115.8 (17)
C6—C1—S1	119.7 (2)	C19—C14—C15	121.1 (2)
C3—C2—C1	119.4 (3)	C19—C14—S2	119.95 (17)
C3—C2—H2	120.3	C15—C14—S2	118.89 (17)
C1—C2—H2	120.3	C16—C15—C14	118.6 (2)
C2—C3—C4	120.5 (3)	C16—C15—H15	120.7
C2—C3—H3	119.7	C14—C15—H15	120.7
C4—C3—H3	119.7	C15—C16—C17	120.2 (2)
C5—C4—C3	120.1 (3)	C15—C16—H16	119.9
C5—C4—H4	120.0	C17—C16—H16	119.9
C3—C4—H4	120.0	C18—C17—C16	120.8 (3)
C4—C5—C6	121.0 (3)	C18—C17—H17	119.6
C4—C5—H5	119.5	C16—C17—H17	119.6
C6—C5—H5	119.5	C17—C18—C19	120.1 (2)
C5—C6—C1	118.3 (3)	C17—C18—H18	120.0
C5—C6—H6	120.8	C19—C18—H18	120.0
C1—C6—H6	120.8	C18—C19—C14	119.2 (2)
O3—C7—N1	120.84 (19)	C18—C19—H19	120.4
O3—C7—C8	124.36 (17)	C14—C19—H19	120.4
N1—C7—C8	114.79 (17)	O6—C20—N2	121.96 (19)
C13—C8—C9	117.3 (2)	O6—C20—C21	124.54 (19)
C13—C8—C7	121.28 (19)	N2—C20—C21	113.47 (16)
C9—C8—C7	121.41 (19)	C22—C21—C26	117.3 (2)
C10—C9—C8	120.6 (2)	C22—C21—C20	123.27 (19)
C10—C9—Cl1A	117.6 (2)	C26—C21—C20	119.43 (19)
C8—C9—Cl1A	121.79 (18)	C21—C22—C23	121.1 (2)
C10—C9—H13B	119.7	C21—C22—Cl2	121.50 (18)
C8—C9—H13B	119.7	C23—C22—Cl2	117.3 (2)
C11—C10—C9	119.9 (3)	C24—C23—C22	119.9 (3)
C11—C10—H10	120.0	C24—C23—H23	120.0
C9—C10—H10	120.0	C22—C23—H23	120.0
C10—C11—C12	120.9 (3)	C23—C24—C25	120.3 (3)
C10—C11—H11	119.6	C23—C24—H24	119.9
C12—C11—H11	119.6	C25—C24—H24	119.9
C11—C12—C13	119.0 (3)	C24—C25—C26	120.2 (3)
C11—C12—H12	120.5	C24—C25—H25	119.9
C13—C12—H12	120.5	C26—C25—H25	119.9
C12—C13—C8	122.3 (2)	C25—C26—C21	121.2 (2)
C12—C13—Cl1B	115.1 (3)	C25—C26—H26	119.4
C8—C13—Cl1B	121.4 (2)	C21—C26—H26	119.4
O2—S1—N1—C7	59.3 (2)	C7—C8—C13—Cl1B	11.9 (3)
O1—S1—N1—C7	−172.73 (19)	O5—S2—N2—C20	49.5 (2)
C1—S1—N1—C7	−59.0 (2)	O4—S2—N2—C20	177.73 (18)
O2—S1—C1—C2	166.94 (17)	C14—S2—N2—C20	−67.30 (19)
O1—S1—C1—C2	33.6 (2)	O5—S2—C14—C19	−16.8 (2)
N1—S1—C1—C2	−75.60 (19)	O4—S2—C14—C19	−148.99 (18)
O2—S1—C1—C6	−15.2 (2)	N2—S2—C14—C19	99.45 (18)
O1—S1—C1—C6	−148.54 (18)	O5—S2—C14—C15	161.18 (17)
N1—S1—C1—C6	102.27 (19)	O4—S2—C14—C15	29.0 (2)
C6—C1—C2—C3	−0.4 (3)	N2—S2—C14—C15	−82.52 (18)
S1—C1—C2—C3	177.40 (19)	C19—C14—C15—C16	−0.7 (3)
C1—C2—C3—C4	0.5 (4)	S2—C14—C15—C16	−178.68 (19)
C2—C3—C4—C5	−0.2 (4)	C14—C15—C16—C17	1.3 (4)
C3—C4—C5—C6	−0.3 (5)	C15—C16—C17—C18	−0.9 (4)
C4—C5—C6—C1	0.3 (4)	C16—C17—C18—C19	−0.2 (4)
C2—C1—C6—C5	0.0 (3)	C17—C18—C19—C14	0.8 (4)
S1—C1—C6—C5	−177.8 (2)	C15—C14—C19—C18	−0.4 (3)
S1—N1—C7—O3	−10.0 (3)	S2—C14—C19—C18	177.59 (19)
S1—N1—C7—C8	169.48 (16)	S2—N2—C20—O6	7.9 (3)
O3—C7—C8—C13	−134.5 (2)	S2—N2—C20—C21	−170.30 (15)
N1—C7—C8—C13	46.0 (3)	O6—C20—C21—C22	39.0 (3)
O3—C7—C8—C9	45.0 (3)	N2—C20—C21—C22	−142.8 (2)
N1—C7—C8—C9	−134.4 (2)	O6—C20—C21—C26	−138.5 (2)
C13—C8—C9—C10	−0.3 (3)	N2—C20—C21—C26	39.6 (3)
C7—C8—C9—C10	−179.9 (2)	C26—C21—C22—C23	−1.2 (3)
C13—C8—C9—Cl1A	−178.19 (16)	C20—C21—C22—C23	−178.8 (2)
C7—C8—C9—Cl1A	2.2 (3)	C26—C21—C22—Cl2	−178.16 (17)
C8—C9—C10—C11	0.5 (4)	C20—C21—C22—Cl2	4.3 (3)
Cl1A—C9—C10—C11	178.5 (2)	C21—C22—C23—C24	1.4 (4)
C9—C10—C11—C12	0.1 (4)	Cl2—C22—C23—C24	178.5 (2)
C10—C11—C12—C13	−0.9 (4)	C22—C23—C24—C25	−0.5 (4)
C11—C12—C13—C8	1.1 (4)	C23—C24—C25—C26	−0.5 (4)
C11—C12—C13—Cl1B	169.1 (3)	C24—C25—C26—C21	0.7 (4)
C9—C8—C13—C12	−0.5 (3)	C22—C21—C26—C25	0.2 (3)
C7—C8—C13—C12	179.1 (2)	C20—C21—C26—C25	177.9 (2)
C9—C8—C13—Cl1B	−167.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.09 (2)	2.922 (2)	168 (2)
N2—H2N···O3ii	0.82 (2)	2.06 (2)	2.883 (2)	179 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.09 (2)	2.922 (2)	168 (2)
N2—H2N⋯O3ii	0.82 (2)	2.06 (2)	2.883 (2)	179 (3)

Symmetry codes: (i) ; (ii) .