N-(4-Chloro-benzo-yl)-4-methyl-benzene-sulfonamide.

The asymmetric unit of the title compound, C(14)H(12)ClNO(3)S, contains two independent mol-ecules. The dihedral angles between the two aromatic rings in each mol-ecule are 81.0 (1) and 76.3 (1)°. In the crystal, mol-ecules are linked 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

C14H12ClNO3S

M = 309.76

Monoclinic,

a = 25.675 (3) Å

b = 12.0508 (8) Å

c = 22.191 (3) Å

β = 122.16 (1)°

V = 5812.5 (11) Å3

Z = 16

Mo Kα radiation

μ = 0.41 mm−1

T = 299 K

0.50 × 0.48 × 0.44 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.821, T max = 0.840

12864 measured reflections

5931 independent reflections

3733 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.07

5931 reflections

367 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.35 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/S1600536809055585/bt5156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055585/bt5156Isup2.hkl

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

C14H12ClNO3S	F(000) = 2560
Mr = 309.76	Dx = 1.416 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3720 reflections
a = 25.675 (3) Å	θ = 2.4–27.8°
b = 12.0508 (8) Å	µ = 0.41 mm−1
c = 22.191 (3) Å	T = 299 K
β = 122.16 (1)°	Prism, colourless
V = 5812.5 (11) Å3	0.50 × 0.48 × 0.44 mm
Z = 16

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5931 independent reflections
Radiation source: fine-focus sealed tube	3733 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −25→32
Tmin = 0.821, Tmax = 0.840	k = −10→15
12864 measured reflections	l = −27→26

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0686P)2 + 0.2769P] where P = (Fo2 + 2Fc2)/3
5931 reflections	(Δ/σ)max < 0.001
367 parameters	Δρmax = 0.22 e Å−3
2 restraints	Δρmin = −0.35 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.38789 (4)	0.05434 (7)	0.38377 (5)	0.0983 (3)
S1	0.14332 (3)	−0.10122 (5)	0.50954 (3)	0.05366 (19)
O1	0.11216 (9)	−0.19893 (15)	0.47163 (12)	0.0881 (6)
O2	0.18104 (8)	−0.10514 (17)	0.58521 (9)	0.0788 (6)
O3	0.22829 (9)	0.08559 (16)	0.54283 (10)	0.0806 (6)
N1	0.18659 (8)	−0.06886 (16)	0.47816 (9)	0.0452 (5)
H1N	0.1773 (10)	−0.1095 (16)	0.4431 (9)	0.054*
C1	0.09034 (10)	0.00583 (18)	0.48616 (12)	0.0442 (5)
C2	0.09089 (11)	0.0707 (2)	0.53769 (14)	0.0585 (7)
H2	0.1209	0.0605	0.5855	0.070*
C3	0.04631 (14)	0.1506 (2)	0.51720 (18)	0.0740 (8)
H3	0.0462	0.1941	0.5518	0.089*
C4	0.00175 (14)	0.1678 (3)	0.4465 (2)	0.0793 (9)
C5	0.00290 (14)	0.1015 (3)	0.39662 (17)	0.0886 (10)
H5	−0.0269	0.1118	0.3487	0.106*
C6	0.04580 (12)	0.0223 (2)	0.41515 (14)	0.0691 (7)
H6	0.0455	−0.0211	0.3803	0.083*
C7	0.22739 (10)	0.01850 (19)	0.50176 (12)	0.0477 (6)
C8	0.26807 (10)	0.02355 (18)	0.47333 (11)	0.0417 (5)
C9	0.28899 (10)	0.12670 (19)	0.46694 (13)	0.0532 (6)
H9	0.2778	0.1901	0.4812	0.064*
C10	0.32578 (11)	0.1362 (2)	0.44001 (13)	0.0566 (7)
H10	0.3397	0.2055	0.4361	0.068*
C11	0.34187 (11)	0.0432 (2)	0.41897 (13)	0.0547 (6)
C12	0.32329 (11)	−0.0603 (2)	0.42626 (13)	0.0580 (7)
H12	0.3360	−0.1233	0.4133	0.070*
C13	0.28596 (10)	−0.06994 (19)	0.45281 (12)	0.0494 (6)
H13	0.2726	−0.1396	0.4570	0.059*
C14	−0.04607 (16)	0.2566 (3)	0.4263 (2)	0.1319 (16)
H14A	−0.0263	0.3246	0.4500	0.158*
H14B	−0.0740	0.2341	0.4402	0.158*
H14C	−0.0684	0.2679	0.3757	0.158*
Cl2	0.10332 (4)	0.14098 (7)	0.31950 (5)	0.0936 (3)
S2	0.33983 (3)	0.23886 (6)	0.17178 (3)	0.0584 (2)
O4	0.31253 (8)	0.18435 (17)	0.10439 (8)	0.0764 (6)
O5	0.35779 (10)	0.35126 (16)	0.17631 (11)	0.0853 (6)
O6	0.33220 (8)	0.33394 (15)	0.29154 (9)	0.0688 (5)
N2	0.28714 (9)	0.22737 (16)	0.19241 (10)	0.0510 (5)
H2N	0.2582 (8)	0.1838 (16)	0.1619 (10)	0.061*
C15	0.40193 (10)	0.1613 (2)	0.23652 (12)	0.0501 (6)
C16	0.39912 (11)	0.0479 (2)	0.23028 (13)	0.0613 (7)
H16	0.3644	0.0142	0.1926	0.074*
C17	0.44735 (13)	−0.0156 (3)	0.27945 (16)	0.0755 (8)
H17	0.4450	−0.0924	0.2745	0.091*
C18	0.49838 (13)	0.0307 (4)	0.33503 (16)	0.0806 (9)
C19	0.50120 (13)	0.1440 (4)	0.34170 (15)	0.0901 (11)
H19	0.5361	0.1766	0.3797	0.108*
C20	0.45307 (13)	0.2109 (3)	0.29301 (14)	0.0734 (8)
H20	0.4552	0.2876	0.2984	0.088*
C21	0.29100 (11)	0.27162 (19)	0.25229 (12)	0.0486 (6)
C22	0.24186 (10)	0.23757 (18)	0.26438 (11)	0.0433 (5)
C23	0.22642 (11)	0.3098 (2)	0.30130 (12)	0.0533 (6)
H23	0.2454	0.3788	0.3154	0.064*
C24	0.18339 (12)	0.2803 (2)	0.31707 (13)	0.0585 (7)
H24	0.1725	0.3296	0.3408	0.070*
C25	0.15648 (11)	0.1773 (2)	0.29750 (13)	0.0555 (6)
C26	0.17150 (12)	0.1034 (2)	0.26192 (13)	0.0576 (6)
H26	0.1531	0.0338	0.2490	0.069*
C27	0.21412 (11)	0.13404 (19)	0.24571 (12)	0.0517 (6)
H27	0.2246	0.0844	0.2218	0.062*
C28	0.55230 (14)	−0.0392 (4)	0.38905 (19)	0.1392 (17)
H28A	0.5748	−0.0653	0.3685	0.167*
H28B	0.5374	−0.1014	0.4026	0.167*
H28C	0.5789	0.0050	0.4303	0.167*

	U11	U22	U33	U12	U13	U23
Cl1	0.1146 (7)	0.0990 (6)	0.1408 (8)	0.0175 (5)	0.1081 (6)	0.0329 (5)
S1	0.0629 (4)	0.0522 (4)	0.0623 (4)	0.0014 (3)	0.0443 (3)	0.0062 (3)
O1	0.1045 (15)	0.0493 (11)	0.1475 (19)	−0.0261 (11)	0.0920 (15)	−0.0236 (12)
O2	0.0802 (12)	0.1132 (16)	0.0579 (12)	0.0377 (12)	0.0467 (10)	0.0363 (11)
O3	0.0916 (14)	0.0817 (14)	0.0988 (15)	−0.0321 (11)	0.0711 (13)	−0.0506 (12)
N1	0.0521 (11)	0.0500 (12)	0.0439 (11)	−0.0115 (9)	0.0326 (10)	−0.0143 (9)
C1	0.0444 (12)	0.0488 (14)	0.0459 (14)	−0.0055 (10)	0.0283 (11)	0.0032 (10)
C2	0.0564 (15)	0.0642 (17)	0.0577 (16)	−0.0022 (13)	0.0323 (13)	−0.0058 (13)
C3	0.080 (2)	0.0623 (19)	0.107 (3)	0.0012 (16)	0.069 (2)	−0.0054 (17)
C4	0.0615 (18)	0.074 (2)	0.124 (3)	0.0162 (16)	0.064 (2)	0.042 (2)
C5	0.0615 (18)	0.129 (3)	0.074 (2)	0.020 (2)	0.0349 (17)	0.041 (2)
C6	0.0667 (17)	0.091 (2)	0.0517 (17)	0.0017 (16)	0.0326 (14)	0.0052 (15)
C7	0.0526 (14)	0.0490 (14)	0.0448 (14)	−0.0029 (12)	0.0281 (11)	−0.0081 (11)
C8	0.0420 (12)	0.0412 (13)	0.0431 (13)	−0.0006 (10)	0.0233 (10)	−0.0018 (10)
C9	0.0556 (14)	0.0412 (14)	0.0663 (16)	0.0040 (11)	0.0348 (13)	−0.0005 (11)
C10	0.0555 (15)	0.0457 (15)	0.0730 (18)	0.0020 (12)	0.0372 (14)	0.0153 (12)
C11	0.0552 (14)	0.0602 (17)	0.0630 (16)	0.0089 (13)	0.0411 (13)	0.0166 (13)
C12	0.0678 (16)	0.0494 (15)	0.0771 (18)	0.0106 (13)	0.0522 (15)	0.0037 (13)
C13	0.0585 (14)	0.0401 (14)	0.0625 (16)	−0.0003 (11)	0.0408 (13)	0.0012 (11)
C14	0.101 (3)	0.113 (3)	0.227 (5)	0.051 (2)	0.118 (3)	0.081 (3)
Cl2	0.0976 (6)	0.1036 (7)	0.1202 (7)	−0.0049 (5)	0.0852 (6)	0.0033 (5)
S2	0.0639 (4)	0.0694 (5)	0.0533 (4)	−0.0019 (3)	0.0388 (3)	0.0103 (3)
O4	0.0730 (12)	0.1215 (16)	0.0424 (10)	0.0038 (12)	0.0358 (9)	−0.0008 (10)
O5	0.1050 (15)	0.0662 (13)	0.1101 (17)	−0.0067 (11)	0.0744 (14)	0.0229 (11)
O6	0.0759 (12)	0.0704 (12)	0.0660 (12)	−0.0237 (10)	0.0417 (10)	−0.0165 (10)
N2	0.0519 (12)	0.0614 (14)	0.0430 (11)	−0.0046 (10)	0.0275 (10)	−0.0021 (9)
C15	0.0492 (14)	0.0624 (17)	0.0465 (14)	−0.0135 (12)	0.0307 (12)	−0.0030 (12)
C16	0.0503 (15)	0.0705 (19)	0.0578 (17)	−0.0067 (14)	0.0252 (13)	−0.0029 (14)
C17	0.0630 (18)	0.082 (2)	0.080 (2)	0.0059 (16)	0.0372 (18)	0.0178 (17)
C18	0.0546 (18)	0.127 (3)	0.064 (2)	0.000 (2)	0.0343 (16)	0.024 (2)
C19	0.0490 (17)	0.157 (4)	0.0515 (19)	−0.036 (2)	0.0178 (15)	−0.010 (2)
C20	0.0704 (18)	0.087 (2)	0.0611 (18)	−0.0333 (17)	0.0337 (16)	−0.0167 (16)
C21	0.0584 (15)	0.0430 (14)	0.0453 (14)	0.0013 (12)	0.0281 (12)	0.0025 (11)
C22	0.0521 (13)	0.0399 (13)	0.0380 (12)	0.0053 (11)	0.0241 (11)	0.0052 (10)
C23	0.0672 (16)	0.0379 (13)	0.0566 (15)	−0.0008 (12)	0.0341 (13)	−0.0041 (11)
C24	0.0702 (17)	0.0538 (16)	0.0626 (17)	0.0121 (14)	0.0428 (14)	−0.0011 (13)
C25	0.0586 (15)	0.0609 (17)	0.0552 (15)	0.0058 (13)	0.0358 (13)	0.0081 (13)
C26	0.0703 (16)	0.0476 (15)	0.0643 (16)	−0.0079 (13)	0.0421 (14)	−0.0018 (13)
C27	0.0667 (16)	0.0457 (14)	0.0510 (15)	0.0020 (12)	0.0369 (13)	−0.0026 (11)
C28	0.069 (2)	0.233 (5)	0.096 (3)	0.032 (3)	0.030 (2)	0.081 (3)

Cl1—C11	1.734 (2)	Cl2—C25	1.732 (2)
S1—O1	1.4205 (19)	S2—O5	1.4170 (19)
S1—O2	1.4242 (18)	S2—O4	1.4294 (18)
S1—N1	1.6417 (18)	S2—N2	1.6487 (19)
S1—C1	1.741 (2)	S2—C15	1.744 (2)
O3—C7	1.209 (2)	O6—C21	1.209 (3)
N1—C7	1.377 (3)	N2—C21	1.385 (3)
N1—H1N	0.838 (9)	N2—H2N	0.867 (9)
C1—C2	1.379 (3)	C15—C16	1.371 (3)
C1—C6	1.383 (3)	C15—C20	1.378 (3)
C2—C3	1.375 (3)	C16—C17	1.368 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.380 (4)	C17—C18	1.352 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.377 (5)	C18—C19	1.371 (4)
C4—C14	1.507 (4)	C18—C28	1.515 (4)
C5—C6	1.345 (4)	C19—C20	1.387 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.481 (3)	C21—C22	1.481 (3)
C8—C13	1.382 (3)	C22—C27	1.386 (3)
C8—C9	1.391 (3)	C22—C23	1.390 (3)
C9—C10	1.365 (3)	C23—C24	1.372 (3)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.361 (3)	C24—C25	1.374 (3)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.375 (3)	C25—C26	1.374 (3)
C12—C13	1.371 (3)	C26—C27	1.372 (3)
C12—H12	0.9300	C26—H26	0.9300
C13—H13	0.9300	C27—H27	0.9300
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	119.07 (13)	O5—S2—O4	118.25 (12)
O1—S1—N1	103.93 (10)	O5—S2—N2	110.16 (11)
O2—S1—N1	108.60 (10)	O4—S2—N2	103.53 (10)
O1—S1—C1	109.47 (12)	O5—S2—C15	109.49 (12)
O2—S1—C1	108.00 (11)	O4—S2—C15	109.86 (12)
N1—S1—C1	107.18 (10)	N2—S2—C15	104.58 (10)
C7—N1—S1	124.74 (15)	C21—N2—S2	125.70 (17)
C7—N1—H1N	125.6 (16)	C21—N2—H2N	125.2 (16)
S1—N1—H1N	109.4 (16)	S2—N2—H2N	108.9 (16)
C2—C1—C6	120.0 (2)	C16—C15—C20	119.8 (3)
C2—C1—S1	120.74 (19)	C16—C15—S2	118.36 (18)
C6—C1—S1	119.16 (19)	C20—C15—S2	121.8 (2)
C3—C2—C1	118.9 (3)	C17—C16—C15	120.0 (3)
C3—C2—H2	120.5	C17—C16—H16	120.0
C1—C2—H2	120.5	C15—C16—H16	120.0
C2—C3—C4	121.4 (3)	C18—C17—C16	121.5 (3)
C2—C3—H3	119.3	C18—C17—H17	119.2
C4—C3—H3	119.3	C16—C17—H17	119.2
C5—C4—C3	117.9 (3)	C17—C18—C19	118.6 (3)
C5—C4—C14	122.4 (4)	C17—C18—C28	121.8 (4)
C3—C4—C14	119.7 (4)	C19—C18—C28	119.6 (3)
C6—C5—C4	122.0 (3)	C18—C19—C20	121.4 (3)
C6—C5—H5	119.0	C18—C19—H19	119.3
C4—C5—H5	119.0	C20—C19—H19	119.3
C5—C6—C1	119.8 (3)	C15—C20—C19	118.6 (3)
C5—C6—H6	120.1	C15—C20—H20	120.7
C1—C6—H6	120.1	C19—C20—H20	120.7
O3—C7—N1	120.2 (2)	O6—C21—N2	121.2 (2)
O3—C7—C8	124.0 (2)	O6—C21—C22	123.0 (2)
N1—C7—C8	115.83 (18)	N2—C21—C22	115.7 (2)
C13—C8—C9	118.7 (2)	C27—C22—C23	118.5 (2)
C13—C8—C7	122.7 (2)	C27—C22—C21	123.2 (2)
C9—C8—C7	118.6 (2)	C23—C22—C21	118.1 (2)
C10—C9—C8	121.0 (2)	C24—C23—C22	120.6 (2)
C10—C9—H9	119.5	C24—C23—H23	119.7
C8—C9—H9	119.5	C22—C23—H23	119.7
C11—C10—C9	119.2 (2)	C23—C24—C25	119.4 (2)
C11—C10—H10	120.4	C23—C24—H24	120.3
C9—C10—H10	120.4	C25—C24—H24	120.3
C10—C11—C12	121.3 (2)	C26—C25—C24	121.3 (2)
C10—C11—Cl1	119.64 (19)	C26—C25—Cl2	120.2 (2)
C12—C11—Cl1	119.06 (19)	C24—C25—Cl2	118.56 (19)
C13—C12—C11	119.5 (2)	C27—C26—C25	118.9 (2)
C13—C12—H12	120.2	C27—C26—H26	120.5
C11—C12—H12	120.2	C25—C26—H26	120.5
C12—C13—C8	120.2 (2)	C26—C27—C22	121.2 (2)
C12—C13—H13	119.9	C26—C27—H27	119.4
C8—C13—H13	119.9	C22—C27—H27	119.4
C4—C14—H14A	109.5	C18—C28—H28A	109.5
C4—C14—H14B	109.5	C18—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C4—C14—H14C	109.5	C18—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	−177.1 (2)	O5—S2—N2—C21	−49.9 (2)
O2—S1—N1—C7	−49.4 (2)	O4—S2—N2—C21	−177.2 (2)
C1—S1—N1—C7	67.1 (2)	C15—S2—N2—C21	67.7 (2)
O1—S1—C1—C2	132.2 (2)	O5—S2—C15—C16	−164.32 (18)
O2—S1—C1—C2	1.2 (2)	O4—S2—C15—C16	−32.9 (2)
N1—S1—C1—C2	−115.67 (19)	N2—S2—C15—C16	77.7 (2)
O1—S1—C1—C6	−45.1 (2)	O5—S2—C15—C20	15.6 (2)
O2—S1—C1—C6	−176.12 (19)	O4—S2—C15—C20	147.08 (19)
N1—S1—C1—C6	67.0 (2)	N2—S2—C15—C20	−102.4 (2)
C6—C1—C2—C3	0.6 (4)	C20—C15—C16—C17	−1.0 (4)
S1—C1—C2—C3	−176.69 (19)	S2—C15—C16—C17	179.0 (2)
C1—C2—C3—C4	−0.7 (4)	C15—C16—C17—C18	0.3 (4)
C2—C3—C4—C5	0.5 (4)	C16—C17—C18—C19	0.1 (4)
C2—C3—C4—C14	−179.7 (2)	C16—C17—C18—C28	−179.1 (3)
C3—C4—C5—C6	−0.2 (4)	C17—C18—C19—C20	0.2 (5)
C14—C4—C5—C6	180.0 (3)	C28—C18—C19—C20	179.4 (3)
C4—C5—C6—C1	0.1 (4)	C16—C15—C20—C19	1.2 (4)
C2—C1—C6—C5	−0.3 (4)	S2—C15—C20—C19	−178.8 (2)
S1—C1—C6—C5	177.0 (2)	C18—C19—C20—C15	−0.8 (4)
S1—N1—C7—O3	−8.7 (3)	S2—N2—C21—O6	8.0 (3)
S1—N1—C7—C8	171.77 (16)	S2—N2—C21—C22	−172.02 (15)
O3—C7—C8—C13	151.8 (3)	O6—C21—C22—C27	−147.2 (2)
N1—C7—C8—C13	−28.6 (3)	N2—C21—C22—C27	32.8 (3)
O3—C7—C8—C9	−28.3 (4)	O6—C21—C22—C23	27.5 (3)
N1—C7—C8—C9	151.2 (2)	N2—C21—C22—C23	−152.5 (2)
C13—C8—C9—C10	0.9 (3)	C27—C22—C23—C24	−1.8 (3)
C7—C8—C9—C10	−179.0 (2)	C21—C22—C23—C24	−176.8 (2)
C8—C9—C10—C11	0.2 (4)	C22—C23—C24—C25	1.5 (4)
C9—C10—C11—C12	−1.9 (4)	C23—C24—C25—C26	−0.5 (4)
C9—C10—C11—Cl1	179.30 (18)	C23—C24—C25—Cl2	178.81 (18)
C10—C11—C12—C13	2.4 (4)	C24—C25—C26—C27	−0.2 (4)
Cl1—C11—C12—C13	−178.81 (18)	Cl2—C25—C26—C27	−179.45 (17)
C11—C12—C13—C8	−1.2 (4)	C25—C26—C27—C22	−0.2 (4)
C9—C8—C13—C12	−0.4 (3)	C23—C22—C27—C26	1.2 (3)
C7—C8—C13—C12	179.4 (2)	C21—C22—C27—C26	175.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5i	0.84 (1)	2.35 (1)	3.133 (3)	156 (2)
N2—H2N···O2ii	0.87 (1)	2.03 (1)	2.890 (3)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O5i	0.84 (1)	2.35 (1)	3.133 (3)	156 (2)
N2—H2N⋯O2ii	0.87 (1)	2.03 (1)	2.890 (3)	170 (2)

Symmetry codes: (i) ; (ii) .