2-Chloro-N-(3-chloro-benzo-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C(13)H(9)Cl(2)NO(3)S, contains two independent mol-ecules. The conformation of the C=O bond is anti to the meta-Cl group in the chloro-benzoyl group of one of the mol-ecules and syn in the other. The dihedral angles between the sulfonyl and benzoyl benzene rings are 77.8 (1) and 83.5 (1)°. In the crystal structure, two pairs of independent mol-ecules are linked into a tetra-mer by N-H⋯O hydrogen bonds.

Related literature

For background literature and related structures, see: Gowda et al. (2009 ▶, 2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C13H9Cl2NO3S

M = 330.17

Triclinic,

a = 7.4399 (6) Å

b = 11.679 (1) Å

c = 17.138 (2) Å

α = 75.346 (7)°

β = 83.188 (8)°

γ = 77.732 (7)°

V = 1404.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.62 mm−1

T = 299 K

0.20 × 0.14 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.887, T max = 0.952

9768 measured reflections

5694 independent reflections

4267 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.154

S = 1.04

5694 reflections

367 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.10 e Å−3

Δρmin = −0.50 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/S1600536810016909/ci5091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016909/ci5091Isup2.hkl

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

C13H9Cl2NO3S	Z = 4
Mr = 330.17	F(000) = 672
Triclinic, P1	Dx = 1.561 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4399 (6) Å	Cell parameters from 3572 reflections
b = 11.679 (1) Å	θ = 2.5–27.8°
c = 17.138 (2) Å	µ = 0.62 mm−1
α = 75.346 (7)°	T = 299 K
β = 83.188 (8)°	Rod, colourless
γ = 77.732 (7)°	0.20 × 0.14 × 0.08 mm
V = 1404.5 (2) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5694 independent reflections
Radiation source: fine-focus sealed tube	4267 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→5
Tmin = 0.887, Tmax = 0.952	k = −14→14
9768 measured reflections	l = −19→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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0682P)2 + 1.64P] where P = (Fo2 + 2Fc2)/3
5694 reflections	(Δ/σ)max = 0.014
367 parameters	Δρmax = 1.10 e Å−3
2 restraints	Δρmin = −0.50 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.2455 (4)	1.0034 (3)	0.13610 (19)	0.0380 (7)
C2	0.4149 (4)	1.0391 (3)	0.1159 (2)	0.0432 (8)
C3	0.4422 (5)	1.1225 (3)	0.0442 (2)	0.0543 (9)
H3	0.5556	1.1464	0.0304	0.065*
C4	0.3009 (6)	1.1700 (4)	−0.0067 (2)	0.0594 (10)
H4	0.3199	1.2258	−0.0548	0.071*
C5	0.1320 (5)	1.1358 (3)	0.0128 (2)	0.0564 (10)
H5	0.0372	1.1690	−0.0217	0.068*
C6	0.1041 (5)	1.0522 (3)	0.0839 (2)	0.0473 (8)
H6	−0.0095	1.0283	0.0970	0.057*
C7	0.3347 (4)	0.7053 (3)	0.1700 (2)	0.0421 (7)
C8	0.4322 (4)	0.5771 (3)	0.1922 (2)	0.0403 (7)
C9	0.5166 (5)	0.5225 (3)	0.1304 (2)	0.0488 (8)
H9	0.5157	0.5659	0.0768	0.059*
C10	0.6012 (5)	0.4034 (4)	0.1500 (3)	0.0539 (9)
C11	0.5995 (5)	0.3361 (4)	0.2282 (3)	0.0596 (10)
H11	0.6549	0.2550	0.2399	0.072*
C12	0.5148 (6)	0.3901 (4)	0.2892 (3)	0.0614 (10)
H12	0.5135	0.3450	0.3424	0.074*
C13	0.4315 (5)	0.5106 (3)	0.2723 (2)	0.0487 (8)
H13	0.3757	0.5468	0.3138	0.058*
N1	0.3355 (4)	0.7713 (2)	0.22646 (18)	0.0434 (7)
H1N	0.423 (4)	0.755 (3)	0.2573 (19)	0.052*
O1	0.0127 (3)	0.8835 (2)	0.22699 (17)	0.0600 (7)
O2	0.2495 (4)	0.9355 (2)	0.29433 (14)	0.0529 (6)
O3	0.2575 (4)	0.7488 (2)	0.10731 (15)	0.0548 (6)
S1	0.19546 (11)	0.90062 (8)	0.22791 (5)	0.0418 (2)
Cl1	0.59757 (13)	0.98058 (10)	0.17710 (6)	0.0621 (3)
Cl2	0.71150 (19)	0.33696 (12)	0.07272 (9)	0.0864 (4)
C14	0.7395 (4)	0.7963 (3)	0.4444 (2)	0.0418 (7)
C15	0.9034 (5)	0.8353 (3)	0.4444 (2)	0.0469 (8)
C16	0.9072 (6)	0.9573 (4)	0.4233 (2)	0.0573 (10)
H16	1.0162	0.9838	0.4240	0.069*
C17	0.7485 (7)	1.0391 (4)	0.4014 (3)	0.0648 (11)
H17	0.7510	1.1211	0.3875	0.078*
C18	0.5875 (6)	1.0018 (4)	0.3996 (3)	0.0633 (11)
H18	0.4816	1.0582	0.3841	0.076*
C19	0.5817 (5)	0.8804 (3)	0.4208 (2)	0.0506 (9)
H19	0.4722	0.8550	0.4193	0.061*
C20	0.7982 (5)	0.6143 (3)	0.3232 (2)	0.0473 (8)
C21	0.9079 (5)	0.5420 (3)	0.2688 (2)	0.0470 (8)
C22	0.9803 (5)	0.4209 (3)	0.2962 (2)	0.0511 (9)
H22	0.9681	0.3831	0.3507	0.061*
C23	1.0719 (5)	0.3567 (4)	0.2401 (3)	0.0597 (10)
C24	1.0906 (6)	0.4131 (5)	0.1593 (3)	0.0659 (11)
H24	1.1511	0.3691	0.1225	0.079*
C25	1.0212 (6)	0.5326 (5)	0.1332 (3)	0.0721 (12)
H25	1.0363	0.5703	0.0788	0.087*
C26	0.9289 (5)	0.5978 (4)	0.1869 (2)	0.0587 (10)
H26	0.8803	0.6793	0.1687	0.070*
N2	0.8416 (4)	0.5803 (3)	0.40323 (18)	0.0477 (7)
H2N	0.946 (3)	0.537 (3)	0.415 (2)	0.057*
O4	0.5315 (3)	0.6379 (3)	0.4726 (2)	0.0700 (8)
O5	0.8139 (3)	0.5845 (2)	0.54567 (15)	0.0547 (6)
O6	0.6750 (4)	0.6993 (2)	0.30102 (18)	0.0620 (8)
S2	0.71956 (11)	0.64315 (8)	0.47362 (6)	0.0466 (2)
Cl3	1.10996 (13)	0.73583 (10)	0.46678 (7)	0.0686 (3)
Cl4	1.1539 (2)	0.20474 (11)	0.27335 (10)	0.0915 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0388 (16)	0.0328 (16)	0.0392 (17)	−0.0003 (13)	−0.0070 (13)	−0.0059 (13)
C2	0.0401 (18)	0.0421 (18)	0.0462 (19)	−0.0046 (14)	−0.0122 (14)	−0.0067 (15)
C3	0.054 (2)	0.054 (2)	0.053 (2)	−0.0187 (18)	−0.0060 (17)	−0.0012 (17)
C4	0.075 (3)	0.048 (2)	0.049 (2)	−0.0125 (19)	−0.0116 (19)	0.0042 (17)
C5	0.058 (2)	0.050 (2)	0.053 (2)	−0.0010 (18)	−0.0241 (18)	0.0023 (17)
C6	0.0389 (18)	0.0459 (19)	0.055 (2)	−0.0031 (15)	−0.0151 (15)	−0.0060 (16)
C7	0.0380 (17)	0.0400 (18)	0.0467 (19)	−0.0116 (14)	−0.0031 (14)	−0.0040 (14)
C8	0.0340 (16)	0.0381 (17)	0.0496 (19)	−0.0107 (13)	−0.0064 (14)	−0.0067 (14)
C9	0.050 (2)	0.048 (2)	0.051 (2)	−0.0133 (16)	−0.0048 (16)	−0.0118 (16)
C10	0.047 (2)	0.051 (2)	0.069 (3)	−0.0105 (17)	−0.0015 (18)	−0.0247 (19)
C11	0.054 (2)	0.042 (2)	0.078 (3)	−0.0032 (17)	−0.006 (2)	−0.0086 (19)
C12	0.063 (2)	0.047 (2)	0.062 (3)	−0.0045 (19)	−0.003 (2)	0.0032 (19)
C13	0.0467 (19)	0.0434 (19)	0.052 (2)	−0.0079 (15)	−0.0009 (16)	−0.0050 (16)
N1	0.0409 (15)	0.0375 (15)	0.0500 (17)	−0.0019 (12)	−0.0174 (12)	−0.0052 (13)
O1	0.0351 (13)	0.0638 (17)	0.0706 (18)	−0.0073 (12)	−0.0041 (12)	0.0016 (13)
O2	0.0630 (16)	0.0529 (15)	0.0388 (13)	−0.0027 (12)	−0.0037 (11)	−0.0104 (11)
O3	0.0632 (16)	0.0486 (14)	0.0504 (15)	−0.0082 (12)	−0.0212 (12)	−0.0019 (11)
S1	0.0359 (4)	0.0405 (4)	0.0432 (5)	−0.0018 (3)	−0.0037 (3)	−0.0033 (3)
Cl1	0.0421 (5)	0.0781 (7)	0.0618 (6)	−0.0153 (4)	−0.0194 (4)	0.0017 (5)
Cl2	0.0947 (9)	0.0792 (8)	0.0946 (9)	−0.0088 (7)	0.0062 (7)	−0.0494 (7)
C14	0.0397 (17)	0.0442 (18)	0.0381 (17)	−0.0008 (14)	−0.0055 (13)	−0.0082 (14)
C15	0.0420 (18)	0.058 (2)	0.0384 (18)	−0.0080 (16)	−0.0051 (14)	−0.0075 (16)
C16	0.063 (2)	0.062 (2)	0.051 (2)	−0.022 (2)	−0.0014 (18)	−0.0133 (18)
C17	0.087 (3)	0.046 (2)	0.059 (2)	−0.008 (2)	−0.006 (2)	−0.0116 (18)
C18	0.066 (3)	0.052 (2)	0.067 (3)	0.008 (2)	−0.017 (2)	−0.014 (2)
C19	0.0440 (19)	0.052 (2)	0.056 (2)	0.0047 (16)	−0.0138 (16)	−0.0199 (17)
C20	0.0471 (19)	0.0395 (18)	0.059 (2)	−0.0079 (15)	−0.0202 (16)	−0.0107 (16)
C21	0.0423 (18)	0.0457 (19)	0.056 (2)	−0.0091 (15)	−0.0205 (16)	−0.0082 (16)
C22	0.052 (2)	0.046 (2)	0.058 (2)	−0.0081 (16)	−0.0127 (17)	−0.0133 (17)
C23	0.051 (2)	0.051 (2)	0.083 (3)	−0.0113 (18)	−0.012 (2)	−0.022 (2)
C24	0.057 (2)	0.086 (3)	0.066 (3)	−0.024 (2)	0.001 (2)	−0.032 (2)
C25	0.072 (3)	0.086 (3)	0.060 (3)	−0.027 (3)	−0.006 (2)	−0.010 (2)
C26	0.056 (2)	0.060 (2)	0.060 (2)	−0.0166 (19)	−0.0180 (19)	−0.0027 (19)
N2	0.0421 (16)	0.0456 (17)	0.0520 (18)	0.0066 (13)	−0.0206 (13)	−0.0100 (13)
O4	0.0343 (13)	0.0585 (17)	0.112 (2)	−0.0072 (12)	−0.0075 (14)	−0.0100 (16)
O5	0.0500 (14)	0.0572 (15)	0.0441 (14)	0.0009 (12)	−0.0030 (11)	0.0020 (11)
O6	0.0612 (16)	0.0461 (15)	0.0787 (19)	0.0104 (12)	−0.0416 (14)	−0.0149 (13)
S2	0.0334 (4)	0.0445 (5)	0.0555 (5)	−0.0009 (3)	−0.0062 (4)	−0.0041 (4)
Cl3	0.0357 (5)	0.0757 (7)	0.0822 (7)	−0.0091 (4)	−0.0112 (4)	0.0057 (5)
Cl4	0.1048 (10)	0.0482 (6)	0.1177 (11)	0.0030 (6)	−0.0070 (8)	−0.0277 (7)

C1—C2	1.389 (5)	C14—C19	1.388 (5)
C1—C6	1.394 (4)	C14—C15	1.390 (5)
C1—S1	1.775 (3)	C14—S2	1.765 (4)
C2—C3	1.386 (5)	C15—C16	1.384 (5)
C2—Cl1	1.730 (3)	C15—Cl3	1.736 (4)
C3—C4	1.377 (5)	C16—C17	1.375 (6)
C3—H3	0.93	C16—H16	0.93
C4—C5	1.377 (6)	C17—C18	1.365 (6)
C4—H4	0.93	C17—H17	0.93
C5—C6	1.381 (5)	C18—C19	1.380 (6)
C5—H5	0.93	C18—H18	0.93
C6—H6	0.93	C19—H19	0.93
C7—O3	1.220 (4)	C20—O6	1.214 (4)
C7—N1	1.382 (4)	C20—N2	1.384 (5)
C7—C8	1.493 (5)	C20—C21	1.475 (5)
C8—C9	1.391 (5)	C21—C22	1.382 (5)
C8—C13	1.396 (5)	C21—C26	1.396 (5)
C9—C10	1.374 (5)	C22—C23	1.393 (6)
C9—H9	0.93	C22—H22	0.93
C10—C11	1.372 (6)	C23—C24	1.379 (6)
C10—Cl2	1.738 (4)	C23—Cl4	1.719 (4)
C11—C12	1.377 (6)	C24—C25	1.359 (7)
C11—H11	0.93	C24—H24	0.93
C12—C13	1.383 (5)	C25—C26	1.371 (6)
C12—H12	0.93	C25—H25	0.93
C13—H13	0.93	C26—H26	0.93
N1—S1	1.647 (3)	N2—S2	1.650 (3)
N1—H1N	0.845 (18)	N2—H2N	0.846 (19)
O1—S1	1.418 (3)	O4—S2	1.416 (3)
O2—S1	1.427 (3)	O5—S2	1.435 (3)
C2—C1—C6	119.5 (3)	C19—C14—C15	119.4 (3)
C2—C1—S1	123.1 (2)	C19—C14—S2	117.3 (3)
C6—C1—S1	117.3 (3)	C15—C14—S2	123.2 (3)
C3—C2—C1	119.9 (3)	C16—C15—C14	120.0 (3)
C3—C2—Cl1	118.1 (3)	C16—C15—Cl3	117.6 (3)
C1—C2—Cl1	122.0 (3)	C14—C15—Cl3	122.4 (3)
C4—C3—C2	119.9 (4)	C17—C16—C15	119.5 (4)
C4—C3—H3	120.1	C17—C16—H16	120.2
C2—C3—H3	120.1	C15—C16—H16	120.2
C5—C4—C3	120.8 (4)	C18—C17—C16	121.0 (4)
C5—C4—H4	119.6	C18—C17—H17	119.5
C3—C4—H4	119.6	C16—C17—H17	119.5
C4—C5—C6	119.7 (3)	C17—C18—C19	120.0 (4)
C4—C5—H5	120.1	C17—C18—H18	120.0
C6—C5—H5	120.1	C19—C18—H18	120.0
C5—C6—C1	120.2 (3)	C18—C19—C14	120.0 (4)
C5—C6—H6	119.9	C18—C19—H19	120.0
C1—C6—H6	119.9	C14—C19—H19	120.0
O3—C7—N1	122.1 (3)	O6—C20—N2	120.3 (3)
O3—C7—C8	122.8 (3)	O6—C20—C21	123.3 (3)
N1—C7—C8	115.0 (3)	N2—C20—C21	116.4 (3)
C9—C8—C13	120.1 (3)	C22—C21—C26	120.2 (4)
C9—C8—C7	118.4 (3)	C22—C21—C20	121.8 (3)
C13—C8—C7	121.4 (3)	C26—C21—C20	117.9 (3)
C10—C9—C8	118.8 (4)	C21—C22—C23	118.5 (4)
C10—C9—H9	120.6	C21—C22—H22	120.8
C8—C9—H9	120.6	C23—C22—H22	120.8
C9—C10—C11	121.9 (4)	C24—C23—C22	120.6 (4)
C9—C10—Cl2	118.5 (3)	C24—C23—Cl4	120.8 (4)
C11—C10—Cl2	119.6 (3)	C22—C23—Cl4	118.6 (3)
C12—C11—C10	119.2 (4)	C25—C24—C23	120.5 (4)
C12—C11—H11	120.4	C25—C24—H24	119.7
C10—C11—H11	120.4	C23—C24—H24	119.7
C11—C12—C13	120.8 (4)	C24—C25—C26	120.2 (4)
C11—C12—H12	119.6	C24—C25—H25	119.9
C13—C12—H12	119.6	C26—C25—H25	119.9
C12—C13—C8	119.2 (4)	C25—C26—C21	120.1 (4)
C12—C13—H13	120.4	C25—C26—H26	119.9
C8—C13—H13	120.4	C21—C26—H26	119.9
C7—N1—S1	123.8 (2)	C20—N2—S2	122.5 (2)
C7—N1—H1N	121 (3)	C20—N2—H2N	119 (3)
S1—N1—H1N	114 (3)	S2—N2—H2N	117 (3)
O1—S1—O2	120.43 (17)	O4—S2—O5	119.14 (18)
O1—S1—N1	107.77 (16)	O4—S2—N2	109.45 (18)
O2—S1—N1	103.83 (15)	O5—S2—N2	104.14 (15)
O1—S1—C1	107.48 (16)	O4—S2—C14	107.70 (16)
O2—S1—C1	109.82 (15)	O5—S2—C14	110.08 (16)
N1—S1—C1	106.73 (15)	N2—S2—C14	105.52 (16)
C6—C1—C2—C3	−0.2 (5)	C19—C14—C15—C16	2.0 (5)
S1—C1—C2—C3	−178.1 (3)	S2—C14—C15—C16	−177.8 (3)
C6—C1—C2—Cl1	−179.0 (3)	C19—C14—C15—Cl3	−175.8 (3)
S1—C1—C2—Cl1	3.1 (4)	S2—C14—C15—Cl3	4.5 (4)
C1—C2—C3—C4	0.2 (6)	C14—C15—C16—C17	−1.0 (6)
Cl1—C2—C3—C4	179.1 (3)	Cl3—C15—C16—C17	176.9 (3)
C2—C3—C4—C5	0.2 (6)	C15—C16—C17—C18	−0.4 (6)
C3—C4—C5—C6	−0.6 (6)	C16—C17—C18—C19	0.6 (7)
C4—C5—C6—C1	0.7 (6)	C17—C18—C19—C14	0.4 (6)
C2—C1—C6—C5	−0.3 (5)	C15—C14—C19—C18	−1.7 (5)
S1—C1—C6—C5	177.7 (3)	S2—C14—C19—C18	178.1 (3)
O3—C7—C8—C9	31.9 (5)	O6—C20—C21—C22	−149.0 (4)
N1—C7—C8—C9	−149.0 (3)	N2—C20—C21—C22	30.7 (5)
O3—C7—C8—C13	−144.7 (4)	O6—C20—C21—C26	27.5 (5)
N1—C7—C8—C13	34.4 (4)	N2—C20—C21—C26	−152.8 (3)
C13—C8—C9—C10	−1.1 (5)	C26—C21—C22—C23	−0.7 (5)
C7—C8—C9—C10	−177.8 (3)	C20—C21—C22—C23	175.8 (3)
C8—C9—C10—C11	2.2 (6)	C21—C22—C23—C24	0.4 (6)
C8—C9—C10—Cl2	−178.3 (3)	C21—C22—C23—Cl4	−177.4 (3)
C9—C10—C11—C12	−1.7 (6)	C22—C23—C24—C25	0.5 (6)
Cl2—C10—C11—C12	178.8 (3)	Cl4—C23—C24—C25	178.3 (3)
C10—C11—C12—C13	0.2 (6)	C23—C24—C25—C26	−1.1 (7)
C11—C12—C13—C8	0.8 (6)	C24—C25—C26—C21	0.8 (6)
C9—C8—C13—C12	−0.3 (5)	C22—C21—C26—C25	0.1 (5)
C7—C8—C13—C12	176.3 (3)	C20—C21—C26—C25	−176.5 (3)
O3—C7—N1—S1	15.6 (5)	O6—C20—N2—S2	5.7 (5)
C8—C7—N1—S1	−163.5 (2)	C21—C20—N2—S2	−173.9 (2)
C7—N1—S1—O1	52.6 (3)	C20—N2—S2—O4	53.1 (3)
C7—N1—S1—O2	−178.6 (3)	C20—N2—S2—O5	−178.5 (3)
C7—N1—S1—C1	−62.6 (3)	C20—N2—S2—C14	−62.6 (3)
C2—C1—S1—O1	−178.8 (3)	C19—C14—S2—O4	−4.5 (3)
C6—C1—S1—O1	3.3 (3)	C15—C14—S2—O4	175.2 (3)
C2—C1—S1—O2	48.6 (3)	C19—C14—S2—O5	−135.9 (3)
C6—C1—S1—O2	−129.4 (3)	C15—C14—S2—O5	43.9 (3)
C2—C1—S1—N1	−63.4 (3)	C19—C14—S2—N2	112.3 (3)
C6—C1—S1—N1	118.7 (3)	C15—C14—S2—N2	−67.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6	0.84 (2)	2.02 (2)	2.836 (4)	162 (4)
N2—H2N···O5i	0.85 (2)	2.10 (2)	2.937 (4)	173 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O6	0.84 (2)	2.02 (2)	2.836 (4)	162 (4)
N2—H2N⋯O5i	0.85 (2)	2.10 (2)	2.937 (4)	173 (4)

Symmetry code: (i) .