N-(2,3-Dichloro-phen-yl)-4-methyl-benzene-sulfonamide.

The title compound, C(13)H(11)Cl(2)NO(2)S, contains two molecules in the asymmetric unit in which the dihedral angles between the benzene rings are 76.0 (1) and 79.9 (1)°. The conformations of the N-H bonds with respect to their adjacent ortho-chlorine atoms are syn. In the crystal, N-H⋯O hydrogen bonds link the molecules into dimers.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009 ▶, 2010a ▶,b ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 14.035 (3) Å

b = 12.386 (2) Å

c = 15.993 (3) Å

β = 98.30 (1)°

V = 2751.1 (9) Å3

Z = 8

Cu Kα radiation

μ = 5.64 mm−1

T = 299 K

0.50 × 0.45 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

9784 measured reflections

4903 independent reflections

4359 reflections with I > 2σ(I)

R int = 0.131

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.176

S = 1.11

4903 reflections

352 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.56 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536810044375/bq2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044375/bq2248Isup2.hkl

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

C13H11Cl2NO2S	F(000) = 1296
Mr = 316.19	Dx = 1.527 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.035 (3) Å	θ = 5.6–19.2°
b = 12.386 (2) Å	µ = 5.64 mm−1
c = 15.993 (3) Å	T = 299 K
β = 98.30 (1)°	Prism, colourless
V = 2751.1 (9) Å3	0.50 × 0.45 × 0.40 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	Rint = 0.131
Radiation source: fine-focus sealed tube	θmax = 67.0°, θmin = 3.9°
graphite	h = −16→16
ω/2θ scans	k = −14→0
9784 measured reflections	l = −19→19
4903 independent reflections	3 standard reflections every 120 min
4359 reflections with I > 2σ(I)	intensity decay: 1.0%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.176	w = 1/[σ2(Fo2) + (0.0914P)2 + 0.5192P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
4903 reflections	Δρmax = 0.81 e Å−3
352 parameters	Δρmin = −0.56 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (4)

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
C1	0.88559 (18)	0.0982 (2)	0.42938 (14)	0.0312 (6)
C2	0.9254 (2)	0.0053 (2)	0.40037 (17)	0.0404 (6)
H2	0.8955	−0.0612	0.4038	0.048*
C3	1.0094 (2)	0.0132 (3)	0.36653 (18)	0.0473 (7)
H3	1.0361	−0.0489	0.3468	0.057*
C4	1.05552 (19)	0.1107 (3)	0.36089 (16)	0.0412 (7)
C5	1.0132 (2)	0.2032 (3)	0.38929 (19)	0.0453 (7)
H5	1.0423	0.2700	0.3849	0.054*
C6	0.9292 (2)	0.1972 (2)	0.42354 (18)	0.0413 (6)
H6	0.9020	0.2592	0.4427	0.050*
C7	0.66060 (17)	0.0946 (2)	0.32818 (17)	0.0353 (6)
C8	0.64433 (18)	0.1597 (2)	0.25643 (17)	0.0375 (6)
C9	0.6067 (2)	0.1151 (3)	0.17875 (18)	0.0428 (7)
C10	0.5881 (2)	0.0062 (3)	0.1720 (2)	0.0578 (9)
H10	0.5641	−0.0237	0.1199	0.069*
C11	0.6048 (3)	−0.0574 (3)	0.2417 (3)	0.0637 (10)
H11	0.5925	−0.1311	0.2365	0.076*
C12	0.6398 (2)	−0.0151 (3)	0.3207 (2)	0.0530 (8)
H12	0.6493	−0.0597	0.3680	0.064*
C13	1.1486 (2)	0.1179 (4)	0.3250 (2)	0.0625 (10)
H13A	1.1354	0.1367	0.2662	0.075*
H13B	1.1809	0.0495	0.3311	0.075*
H13C	1.1888	0.1723	0.3548	0.075*
N1	0.69333 (16)	0.1410 (2)	0.40784 (15)	0.0379 (5)
H1N	0.700 (3)	0.2081 (15)	0.410 (2)	0.045*
O1	0.75897 (16)	−0.02137 (18)	0.48773 (13)	0.0491 (5)
O2	0.78830 (16)	0.16207 (18)	0.54657 (12)	0.0470 (5)
Cl1	0.67147 (7)	0.29473 (6)	0.26491 (5)	0.0542 (3)
Cl2	0.58337 (8)	0.19562 (9)	0.09061 (5)	0.0690 (3)
S1	0.77998 (4)	0.08962 (6)	0.47581 (4)	0.0344 (2)
C14	0.62488 (18)	0.4300 (2)	0.57233 (14)	0.0302 (5)
C15	0.5861 (2)	0.3271 (2)	0.57427 (16)	0.0372 (6)
H15	0.6173	0.2680	0.5548	0.045*
C16	0.5007 (2)	0.3142 (2)	0.60547 (18)	0.0420 (6)
H16	0.4740	0.2455	0.6066	0.050*
C17	0.45287 (19)	0.4019 (3)	0.63566 (16)	0.0397 (6)
C18	0.4933 (2)	0.5035 (3)	0.63213 (18)	0.0437 (7)
H18	0.4619	0.5629	0.6510	0.052*
C19	0.5792 (2)	0.5186 (2)	0.60121 (17)	0.0383 (6)
H19	0.6059	0.5872	0.5998	0.046*
C20	0.83949 (17)	0.4415 (2)	0.68958 (16)	0.0322 (5)
C21	0.87507 (17)	0.3732 (2)	0.75535 (16)	0.0318 (5)
C22	0.89966 (18)	0.4133 (2)	0.83721 (17)	0.0375 (6)
C23	0.8875 (2)	0.5210 (3)	0.8543 (2)	0.0484 (7)
H23	0.9037	0.5475	0.9089	0.058*
C24	0.8515 (2)	0.5880 (3)	0.7900 (2)	0.0509 (7)
H24	0.8421	0.6605	0.8014	0.061*
C25	0.8284 (2)	0.5505 (2)	0.70714 (19)	0.0440 (7)
H25	0.8056	0.5982	0.6639	0.053*
C26	0.3602 (2)	0.3853 (3)	0.6705 (2)	0.0560 (9)
H26A	0.3739	0.3697	0.7298	0.067*
H26B	0.3257	0.3259	0.6418	0.067*
H26C	0.3218	0.4495	0.6620	0.067*
N2	0.81882 (17)	0.39956 (19)	0.60644 (14)	0.0370 (5)
H2N	0.826 (2)	0.3316 (16)	0.603 (2)	0.044*
O3	0.73700 (16)	0.37678 (18)	0.46284 (11)	0.0475 (5)
O4	0.75082 (16)	0.55963 (18)	0.52425 (13)	0.0480 (5)
Cl3	0.88652 (6)	0.23746 (6)	0.73614 (5)	0.0526 (3)
Cl4	0.94255 (7)	0.32756 (8)	0.91866 (5)	0.0600 (3)
S2	0.73465 (5)	0.44706 (5)	0.53342 (4)	0.0342 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0288 (12)	0.0371 (14)	0.0268 (11)	0.0076 (10)	0.0013 (10)	−0.0017 (10)
C2	0.0439 (15)	0.0369 (14)	0.0404 (13)	0.0106 (12)	0.0061 (12)	−0.0029 (11)
C3	0.0477 (16)	0.0519 (17)	0.0430 (14)	0.0209 (15)	0.0094 (13)	−0.0032 (13)
C4	0.0297 (13)	0.0630 (19)	0.0302 (12)	0.0149 (13)	0.0021 (10)	0.0059 (12)
C5	0.0375 (15)	0.0479 (16)	0.0507 (16)	0.0007 (13)	0.0070 (13)	0.0035 (13)
C6	0.0379 (14)	0.0394 (15)	0.0475 (14)	0.0070 (12)	0.0089 (12)	−0.0044 (12)
C7	0.0203 (11)	0.0388 (14)	0.0458 (14)	0.0026 (10)	0.0010 (10)	−0.0021 (11)
C8	0.0250 (11)	0.0403 (14)	0.0472 (14)	0.0050 (11)	0.0055 (11)	−0.0079 (12)
C9	0.0314 (13)	0.0523 (17)	0.0436 (14)	0.0073 (13)	0.0021 (11)	−0.0059 (13)
C10	0.0478 (17)	0.056 (2)	0.0638 (19)	0.0036 (16)	−0.0109 (16)	−0.0218 (17)
C11	0.060 (2)	0.0422 (17)	0.080 (2)	−0.0048 (16)	−0.0183 (19)	−0.0116 (17)
C12	0.0467 (17)	0.0407 (16)	0.067 (2)	−0.0051 (14)	−0.0069 (16)	0.0032 (15)
C13	0.0407 (17)	0.099 (3)	0.0501 (17)	0.0165 (18)	0.0151 (14)	0.0137 (19)
N1	0.0304 (11)	0.0368 (12)	0.0465 (12)	0.0050 (10)	0.0062 (10)	−0.0011 (10)
O1	0.0523 (12)	0.0440 (12)	0.0517 (11)	−0.0005 (10)	0.0096 (10)	0.0120 (9)
O2	0.0531 (12)	0.0547 (12)	0.0342 (9)	0.0095 (10)	0.0102 (9)	−0.0046 (9)
Cl1	0.0739 (6)	0.0381 (4)	0.0496 (4)	0.0011 (3)	0.0049 (4)	0.0001 (3)
Cl2	0.0888 (7)	0.0725 (6)	0.0424 (4)	0.0130 (5)	−0.0019 (4)	0.0002 (4)
S1	0.0341 (4)	0.0386 (4)	0.0314 (3)	0.0055 (3)	0.0076 (3)	0.0024 (2)
C14	0.0315 (12)	0.0331 (12)	0.0247 (10)	0.0062 (10)	−0.0002 (10)	0.0018 (9)
C15	0.0435 (14)	0.0300 (12)	0.0386 (12)	0.0062 (12)	0.0076 (12)	−0.0001 (11)
C16	0.0411 (15)	0.0397 (15)	0.0445 (14)	−0.0033 (13)	0.0034 (12)	0.0034 (12)
C17	0.0295 (13)	0.0564 (17)	0.0308 (12)	0.0052 (12)	−0.0035 (10)	0.0041 (12)
C18	0.0374 (14)	0.0464 (16)	0.0472 (15)	0.0149 (13)	0.0062 (12)	−0.0023 (13)
C19	0.0418 (14)	0.0304 (13)	0.0410 (13)	0.0066 (12)	0.0005 (12)	−0.0027 (11)
C20	0.0214 (11)	0.0346 (13)	0.0403 (13)	−0.0015 (10)	0.0036 (10)	−0.0017 (11)
C21	0.0220 (11)	0.0311 (12)	0.0424 (13)	0.0003 (10)	0.0047 (10)	−0.0023 (11)
C22	0.0259 (11)	0.0449 (15)	0.0406 (13)	−0.0018 (11)	0.0007 (10)	0.0028 (12)
C23	0.0416 (15)	0.0538 (18)	0.0476 (15)	−0.0032 (14)	−0.0011 (13)	−0.0150 (14)
C24	0.0511 (17)	0.0367 (15)	0.0613 (18)	0.0000 (14)	−0.0044 (15)	−0.0127 (14)
C25	0.0441 (15)	0.0334 (14)	0.0509 (15)	0.0025 (12)	−0.0055 (13)	0.0003 (12)
C26	0.0375 (15)	0.083 (3)	0.0479 (16)	0.0029 (16)	0.0082 (13)	0.0082 (17)
N2	0.0370 (12)	0.0364 (12)	0.0379 (11)	0.0087 (10)	0.0061 (10)	−0.0006 (9)
O3	0.0581 (13)	0.0548 (12)	0.0315 (9)	0.0080 (11)	0.0128 (9)	−0.0008 (9)
O4	0.0569 (12)	0.0404 (11)	0.0480 (11)	−0.0015 (10)	0.0121 (10)	0.0119 (9)
Cl3	0.0709 (5)	0.0328 (4)	0.0515 (4)	0.0090 (3)	0.0001 (4)	0.0004 (3)
Cl4	0.0666 (5)	0.0630 (5)	0.0455 (4)	0.0009 (4)	−0.0081 (4)	0.0085 (4)
S2	0.0375 (4)	0.0354 (4)	0.0306 (3)	0.0034 (3)	0.0077 (3)	0.0043 (2)

C1—C6	1.380 (4)	C14—C19	1.384 (4)
C1—C2	1.387 (4)	C14—C15	1.388 (4)
C1—S1	1.754 (2)	C14—S2	1.756 (2)
C2—C3	1.370 (4)	C15—C16	1.373 (4)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.380 (5)	C16—C17	1.399 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.396 (4)	C17—C18	1.385 (4)
C4—C13	1.503 (4)	C17—C26	1.500 (4)
C5—C6	1.371 (4)	C18—C19	1.379 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C12	1.392 (4)	C20—C21	1.386 (4)
C7—C8	1.394 (4)	C20—C25	1.392 (4)
C7—N1	1.413 (4)	C20—N2	1.418 (3)
C8—C9	1.392 (4)	C21—C22	1.396 (4)
C8—Cl1	1.716 (3)	C21—Cl3	1.721 (3)
C9—C10	1.375 (5)	C22—C23	1.378 (4)
C9—Cl2	1.719 (3)	C22—Cl4	1.720 (3)
C10—C11	1.358 (6)	C23—C24	1.361 (5)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.390 (5)	C24—C25	1.397 (4)
C11—H11	0.9300	C24—H24	0.9300
C12—H12	0.9300	C25—H25	0.9300
C13—H13A	0.9600	C26—H26A	0.9600
C13—H13B	0.9600	C26—H26B	0.9600
C13—H13C	0.9600	C26—H26C	0.9600
N1—S1	1.638 (2)	N2—S2	1.645 (2)
N1—H1N	0.837 (18)	N2—H2N	0.851 (18)
O1—S1	1.425 (2)	O3—S2	1.430 (2)
O2—S1	1.436 (2)	O4—S2	1.424 (2)
C6—C1—C2	120.7 (2)	C19—C14—C15	121.2 (2)
C6—C1—S1	119.5 (2)	C19—C14—S2	119.7 (2)
C2—C1—S1	119.8 (2)	C15—C14—S2	119.1 (2)
C3—C2—C1	118.9 (3)	C16—C15—C14	118.8 (2)
C3—C2—H2	120.5	C16—C15—H15	120.6
C1—C2—H2	120.5	C14—C15—H15	120.6
C2—C3—C4	121.8 (3)	C15—C16—C17	121.5 (3)
C2—C3—H3	119.1	C15—C16—H16	119.3
C4—C3—H3	119.1	C17—C16—H16	119.3
C3—C4—C5	118.1 (3)	C18—C17—C16	118.1 (3)
C3—C4—C13	121.2 (3)	C18—C17—C26	121.5 (3)
C5—C4—C13	120.6 (3)	C16—C17—C26	120.4 (3)
C6—C5—C4	121.1 (3)	C19—C18—C17	121.5 (3)
C6—C5—H5	119.5	C19—C18—H18	119.3
C4—C5—H5	119.5	C17—C18—H18	119.3
C5—C6—C1	119.4 (3)	C18—C19—C14	118.9 (3)
C5—C6—H6	120.3	C18—C19—H19	120.6
C1—C6—H6	120.3	C14—C19—H19	120.6
C12—C7—C8	119.1 (3)	C21—C20—C25	118.5 (2)
C12—C7—N1	120.8 (3)	C21—C20—N2	119.3 (2)
C8—C7—N1	120.0 (3)	C25—C20—N2	122.1 (2)
C9—C8—C7	120.0 (3)	C20—C21—C22	120.5 (2)
C9—C8—Cl1	120.6 (2)	C20—C21—Cl3	119.61 (19)
C7—C8—Cl1	119.4 (2)	C22—C21—Cl3	119.9 (2)
C10—C9—C8	120.2 (3)	C23—C22—C21	120.6 (3)
C10—C9—Cl2	119.5 (2)	C23—C22—Cl4	119.1 (2)
C8—C9—Cl2	120.3 (2)	C21—C22—Cl4	120.2 (2)
C11—C10—C9	119.8 (3)	C24—C23—C22	118.9 (3)
C11—C10—H10	120.1	C24—C23—H23	120.5
C9—C10—H10	120.1	C22—C23—H23	120.5
C10—C11—C12	121.6 (3)	C23—C24—C25	121.7 (3)
C10—C11—H11	119.2	C23—C24—H24	119.2
C12—C11—H11	119.2	C25—C24—H24	119.2
C11—C12—C7	119.2 (3)	C20—C25—C24	119.7 (3)
C11—C12—H12	120.4	C20—C25—H25	120.1
C7—C12—H12	120.4	C24—C25—H25	120.1
C4—C13—H13A	109.5	C17—C26—H26A	109.5
C4—C13—H13B	109.5	C17—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C4—C13—H13C	109.5	C17—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5
C7—N1—S1	123.66 (19)	C20—N2—S2	124.27 (18)
C7—N1—H1N	117 (2)	C20—N2—H2N	114 (2)
S1—N1—H1N	107 (2)	S2—N2—H2N	113 (2)
O1—S1—O2	119.51 (13)	O4—S2—O3	119.53 (12)
O1—S1—N1	108.38 (13)	O4—S2—N2	108.34 (13)
O2—S1—N1	104.38 (12)	O3—S2—N2	104.28 (12)
O1—S1—C1	108.59 (13)	O4—S2—C14	108.40 (13)
O2—S1—C1	108.57 (12)	O3—S2—C14	109.14 (13)
N1—S1—C1	106.70 (12)	N2—S2—C14	106.39 (11)
C6—C1—C2—C3	0.7 (4)	C19—C14—C15—C16	0.1 (4)
S1—C1—C2—C3	−178.1 (2)	S2—C14—C15—C16	179.4 (2)
C1—C2—C3—C4	0.3 (4)	C14—C15—C16—C17	−0.5 (4)
C2—C3—C4—C5	−1.3 (4)	C15—C16—C17—C18	1.0 (4)
C2—C3—C4—C13	178.9 (3)	C15—C16—C17—C26	−179.2 (3)
C3—C4—C5—C6	1.4 (4)	C16—C17—C18—C19	−1.1 (4)
C13—C4—C5—C6	−178.8 (3)	C26—C17—C18—C19	179.1 (3)
C4—C5—C6—C1	−0.5 (4)	C17—C18—C19—C14	0.7 (4)
C2—C1—C6—C5	−0.5 (4)	C15—C14—C19—C18	−0.2 (4)
S1—C1—C6—C5	178.3 (2)	S2—C14—C19—C18	−179.5 (2)
C12—C7—C8—C9	0.8 (4)	C25—C20—C21—C22	−0.4 (4)
N1—C7—C8—C9	−176.2 (2)	N2—C20—C21—C22	177.4 (2)
C12—C7—C8—Cl1	−179.0 (2)	C25—C20—C21—Cl3	178.2 (2)
N1—C7—C8—Cl1	4.0 (3)	N2—C20—C21—Cl3	−4.0 (3)
C7—C8—C9—C10	−1.9 (4)	C20—C21—C22—C23	1.1 (4)
Cl1—C8—C9—C10	177.9 (2)	Cl3—C21—C22—C23	−177.6 (2)
C7—C8—C9—Cl2	178.22 (19)	C20—C21—C22—Cl4	179.30 (18)
Cl1—C8—C9—Cl2	−2.0 (3)	Cl3—C21—C22—Cl4	0.7 (3)
C8—C9—C10—C11	1.2 (5)	C21—C22—C23—C24	−0.3 (4)
Cl2—C9—C10—C11	−178.9 (3)	Cl4—C22—C23—C24	−178.5 (2)
C9—C10—C11—C12	0.5 (6)	C22—C23—C24—C25	−1.2 (5)
C10—C11—C12—C7	−1.7 (5)	C21—C20—C25—C24	−1.0 (4)
C8—C7—C12—C11	1.0 (4)	N2—C20—C25—C24	−178.8 (3)
N1—C7—C12—C11	177.9 (3)	C23—C24—C25—C20	1.9 (5)
C12—C7—N1—S1	47.9 (3)	C21—C20—N2—S2	150.1 (2)
C8—C7—N1—S1	−135.2 (2)	C25—C20—N2—S2	−32.2 (3)
C7—N1—S1—O1	−51.4 (2)	C20—N2—S2—O4	54.7 (2)
C7—N1—S1—O2	−179.8 (2)	C20—N2—S2—O3	−177.0 (2)
C7—N1—S1—C1	65.4 (2)	C20—N2—S2—C14	−61.7 (2)
C6—C1—S1—O1	−169.9 (2)	C19—C14—S2—O4	−10.5 (2)
C2—C1—S1—O1	8.9 (3)	C15—C14—S2—O4	170.1 (2)
C6—C1—S1—O2	−38.5 (3)	C19—C14—S2—O3	−142.2 (2)
C2—C1—S1—O2	140.3 (2)	C15—C14—S2—O3	38.4 (2)
C6—C1—S1—N1	73.5 (2)	C19—C14—S2—N2	105.8 (2)
C2—C1—S1—N1	−107.8 (2)	C15—C14—S2—N2	−73.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.84 (2)	2.29 (2)	3.086 (3)	160 (3)
N1—H1N···Cl1	0.84 (2)	2.54 (3)	2.957 (2)	112 (3)
N2—H2N···O2	0.85 (2)	2.32 (2)	3.104 (3)	154 (3)
N2—H2N···Cl3	0.85 (2)	2.46 (3)	2.944 (2)	117 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.84 (2)	2.29 (2)	3.086 (3)	160 (3)
N2—H2N⋯O2	0.85 (2)	2.32 (2)	3.104 (3)	154 (3)