N-(4-Amino-phen-yl)-4-methylbenzene-sulfonamide.

The title compound, C(13)H(14)N(2)O(2)S, crystallized with two independent mol-ecules in the asymmetric unit. They both have V-shaped conformations: the dihedral angles between their benzene rings are identical [45.86 (13)°] and their C-S-N-C torsion angles are similar [67.9 (3) and 70.2 (3)°]. In the crystal, the mol-ecules are linked by N-H⋯O and N-H⋯N hydrogen bonds, generating a three-dimensional network.

Related literature

For related structures and background to sulfonamides, see: Xing & Zeng (2005 ▶); Gelbrich et al. (2007 ▶); Khan et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C13H14N2O2S

M = 262.32

Orthorhombic,

a = 5.0598 (3) Å

b = 14.7702 (11) Å

c = 35.026 (2) Å

V = 2617.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.41 × 0.35 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.907, T max = 0.953

14160 measured reflections

6049 independent reflections

3138 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.122

S = 0.98

6049 reflections

345 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 2266 Friedel pairs

Flack parameter: −0.03 (8)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811036191/su2300sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036191/su2300Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036191/su2300Isup3.cml

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

C13H14N2O2S	F(000) = 1104
Mr = 262.32	Dx = 1.331 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2101 reflections
a = 5.0598 (3) Å	θ = 2.3–21.0°
b = 14.7702 (11) Å	µ = 0.24 mm−1
c = 35.026 (2) Å	T = 296 K
V = 2617.7 (3) Å3	Cut needle, brown
Z = 8	0.41 × 0.35 × 0.20 mm

Bruker APEXII CCD diffractometer	6049 independent reflections
Radiation source: fine-focus sealed tube	3138 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 28.3°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.907, Tmax = 0.953	k = −18→19
14160 measured reflections	l = −42→44

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0447P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.003
6049 reflections	Δρmax = 0.19 e Å−3
345 parameters	Δρmin = −0.23 e Å−3
0 restraints	Absolute structure: Flack (1983), 2266 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (8)

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	0.7219 (6)	0.5980 (2)	0.52219 (9)	0.0461 (9)
C2	0.5551 (7)	0.6031 (3)	0.55343 (11)	0.0676 (11)
H2	0.4207	0.5608	0.5565	0.081*
C3	0.5892 (9)	0.6712 (3)	0.57994 (11)	0.0745 (13)
H3	0.4774	0.6735	0.6010	0.089*
C4	0.7816 (9)	0.7354 (3)	0.57630 (11)	0.0650 (11)
C5	0.9476 (8)	0.7288 (3)	0.54593 (11)	0.0672 (11)
H5	1.0827	0.7710	0.5433	0.081*
C6	0.9217 (7)	0.6609 (3)	0.51874 (10)	0.0577 (10)
H6	1.0386	0.6579	0.4983	0.069*
C7	0.8067 (12)	0.8109 (3)	0.60412 (11)	0.1064 (17)
H7A	0.7568	0.8667	0.5921	0.160*
H7B	0.9864	0.8150	0.6127	0.160*
H7C	0.6929	0.7998	0.6256	0.160*
C8	0.7725 (7)	0.3749 (2)	0.53228 (10)	0.0470 (9)
C9	0.8953 (7)	0.3861 (3)	0.56689 (11)	0.0588 (10)
H9	1.0308	0.4282	0.5695	0.071*
C10	0.8171 (9)	0.3350 (3)	0.59756 (11)	0.0667 (11)
H10	0.9024	0.3423	0.6209	0.080*
C11	0.6143 (7)	0.2728 (3)	0.59452 (11)	0.0573 (10)
C12	0.4958 (7)	0.2624 (3)	0.55924 (10)	0.0581 (10)
H12	0.3598	0.2206	0.5564	0.070*
C13	0.5747 (7)	0.3124 (3)	0.52862 (10)	0.0521 (9)
H13	0.4935	0.3040	0.5051	0.062*
S1	0.67974 (18)	0.51473 (7)	0.48702 (3)	0.0565 (3)
N1	0.8513 (6)	0.4261 (2)	0.49950 (10)	0.0574 (9)
H1N	0.988 (7)	0.429 (3)	0.4975 (11)	0.069*
N2	0.5408 (8)	0.2184 (3)	0.62512 (10)	0.0775 (11)
H2N	0.589 (8)	0.235 (3)	0.6483 (10)	0.093*
H3N	0.362 (8)	0.195 (3)	0.6230 (10)	0.093*
O1	0.7922 (5)	0.54737 (18)	0.45226 (7)	0.0748 (8)
O2	0.4094 (4)	0.48778 (19)	0.48757 (8)	0.0759 (8)
C14	0.1982 (6)	0.7212 (2)	0.73078 (9)	0.0433 (8)
C15	0.0384 (8)	0.7105 (3)	0.69949 (11)	0.0661 (11)
H15	−0.0987	0.7509	0.6947	0.079*
C16	0.0848 (9)	0.6391 (3)	0.67542 (12)	0.0760 (13)
H16	−0.0247	0.6315	0.6543	0.091*
C17	0.2854 (9)	0.5789 (3)	0.68115 (11)	0.0652 (11)
C18	0.4447 (8)	0.5923 (3)	0.71206 (11)	0.0625 (11)
H18	0.5846	0.5527	0.7163	0.075*
C19	0.4044 (6)	0.6623 (2)	0.73690 (11)	0.0518 (9)
H19	0.5157	0.6701	0.7578	0.062*
C20	0.3247 (11)	0.4991 (3)	0.65535 (13)	0.1056 (17)
H20A	0.4187	0.4525	0.6688	0.158*
H20B	0.4248	0.5173	0.6334	0.158*
H20C	0.1559	0.4763	0.6473	0.158*
C21	0.2515 (6)	0.9433 (2)	0.71400 (10)	0.0434 (9)
C22	0.0559 (7)	1.0077 (3)	0.71480 (10)	0.0551 (10)
H22	−0.0298	1.0205	0.7377	0.066*
C23	−0.0137 (7)	1.0527 (3)	0.68273 (10)	0.0581 (10)
H23	−0.1487	1.0954	0.6838	0.070*
C24	0.1128 (7)	1.0364 (2)	0.64826 (10)	0.0517 (9)
C25	0.3122 (8)	0.9737 (3)	0.64794 (11)	0.0659 (11)
H25	0.4034	0.9627	0.6254	0.079*
C26	0.3792 (7)	0.9273 (2)	0.68016 (10)	0.0563 (10)
H26	0.5131	0.8842	0.6792	0.068*
S2	0.14355 (16)	0.81143 (6)	0.76258 (3)	0.0478 (3)
N3	0.3200 (5)	0.89631 (19)	0.74834 (8)	0.0448 (7)
H4N	0.474 (6)	0.886 (2)	0.7494 (9)	0.054*
N4	0.0471 (8)	1.0859 (3)	0.61552 (10)	0.0748 (11)
H5N	−0.110 (8)	1.104 (3)	0.6191 (12)	0.090*
H6N	0.099 (8)	1.055 (3)	0.5963 (11)	0.090*
O3	−0.1258 (4)	0.83822 (17)	0.75914 (7)	0.0647 (7)
O4	0.2457 (5)	0.78643 (19)	0.79860 (6)	0.0668 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0446 (19)	0.049 (2)	0.045 (2)	0.0025 (18)	0.0005 (17)	0.0031 (17)
C2	0.057 (2)	0.082 (3)	0.064 (3)	−0.005 (2)	0.016 (2)	0.006 (3)
C3	0.081 (3)	0.091 (4)	0.052 (3)	0.012 (3)	0.021 (2)	−0.010 (3)
C4	0.081 (3)	0.062 (3)	0.053 (3)	0.016 (3)	−0.001 (2)	0.004 (2)
C5	0.074 (3)	0.057 (3)	0.070 (3)	−0.009 (2)	−0.012 (2)	−0.002 (2)
C6	0.056 (2)	0.065 (3)	0.052 (2)	−0.007 (2)	0.0099 (19)	0.003 (2)
C7	0.164 (5)	0.076 (3)	0.079 (3)	0.030 (4)	−0.005 (3)	−0.028 (3)
C8	0.042 (2)	0.048 (2)	0.051 (2)	0.0038 (18)	0.0044 (18)	−0.0066 (19)
C9	0.057 (2)	0.053 (3)	0.066 (3)	−0.010 (2)	−0.013 (2)	−0.002 (2)
C10	0.080 (3)	0.060 (3)	0.061 (3)	−0.010 (2)	−0.026 (2)	−0.008 (2)
C11	0.065 (3)	0.046 (2)	0.061 (3)	0.002 (2)	−0.010 (2)	−0.003 (2)
C12	0.062 (2)	0.056 (3)	0.057 (2)	−0.014 (2)	−0.010 (2)	−0.003 (2)
C13	0.055 (2)	0.052 (2)	0.049 (2)	−0.007 (2)	−0.0062 (17)	−0.007 (2)
S1	0.0551 (6)	0.0642 (7)	0.0502 (6)	−0.0055 (5)	−0.0044 (5)	−0.0030 (5)
N1	0.0490 (18)	0.062 (2)	0.061 (2)	−0.001 (2)	0.0063 (19)	−0.0103 (17)
N2	0.092 (3)	0.080 (3)	0.061 (2)	−0.018 (2)	−0.016 (2)	0.015 (2)
O1	0.098 (2)	0.087 (2)	0.0397 (15)	−0.0100 (18)	0.0080 (15)	0.0010 (14)
O2	0.0483 (14)	0.088 (2)	0.092 (2)	−0.0104 (15)	−0.0146 (14)	−0.0059 (18)
C14	0.0405 (18)	0.044 (2)	0.046 (2)	−0.0038 (17)	0.0029 (17)	0.0089 (17)
C15	0.059 (2)	0.071 (3)	0.068 (3)	0.007 (2)	−0.010 (2)	−0.006 (2)
C16	0.084 (3)	0.079 (3)	0.065 (3)	−0.008 (3)	−0.017 (2)	−0.006 (3)
C17	0.089 (3)	0.050 (3)	0.057 (3)	−0.014 (3)	0.016 (3)	−0.003 (2)
C18	0.078 (3)	0.040 (2)	0.070 (3)	0.005 (2)	0.008 (2)	0.011 (2)
C19	0.052 (2)	0.044 (2)	0.059 (2)	−0.0008 (19)	−0.0048 (19)	0.010 (2)
C20	0.163 (5)	0.071 (3)	0.083 (3)	−0.004 (4)	0.010 (3)	−0.021 (3)
C21	0.0367 (19)	0.039 (2)	0.054 (2)	0.0010 (17)	0.0005 (17)	−0.0027 (18)
C22	0.062 (2)	0.058 (3)	0.046 (2)	0.021 (2)	0.0102 (18)	0.003 (2)
C23	0.060 (2)	0.055 (3)	0.059 (3)	0.021 (2)	0.003 (2)	0.002 (2)
C24	0.065 (2)	0.044 (2)	0.046 (2)	0.002 (2)	−0.004 (2)	0.0006 (19)
C25	0.072 (3)	0.067 (3)	0.059 (3)	0.017 (3)	0.017 (2)	0.000 (2)
C26	0.055 (2)	0.053 (2)	0.061 (3)	0.018 (2)	0.007 (2)	0.000 (2)
S2	0.0404 (5)	0.0560 (6)	0.0469 (6)	0.0052 (5)	0.0017 (4)	0.0051 (5)
N3	0.0351 (14)	0.0449 (17)	0.0546 (18)	0.0059 (15)	−0.0076 (14)	0.0033 (15)
N4	0.092 (3)	0.071 (3)	0.061 (2)	0.009 (2)	0.004 (2)	0.004 (2)
O3	0.0423 (14)	0.0779 (19)	0.0739 (17)	0.0104 (13)	0.0112 (13)	0.0022 (15)
O4	0.0828 (19)	0.077 (2)	0.0406 (14)	0.0086 (15)	−0.0042 (13)	0.0097 (13)

C1—C6	1.378 (4)	C14—C15	1.371 (4)
C1—C2	1.384 (4)	C14—C19	1.375 (4)
C1—S1	1.754 (4)	C14—S2	1.759 (3)
C2—C3	1.380 (5)	C15—C16	1.370 (5)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.364 (5)	C16—C17	1.365 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.359 (5)	C17—C18	1.364 (5)
C4—C7	1.487 (5)	C17—C20	1.498 (6)
C5—C6	1.389 (5)	C18—C19	1.367 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—H7A	0.9600	C20—H20A	0.9600
C7—H7B	0.9600	C20—H20B	0.9600
C7—H7C	0.9600	C20—H20C	0.9600
C8—C13	1.368 (4)	C21—C26	1.371 (4)
C8—C9	1.372 (4)	C21—C22	1.373 (4)
C8—N1	1.431 (5)	C21—N3	1.431 (4)
C9—C10	1.372 (5)	C22—C23	1.352 (4)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.381 (5)	C23—C24	1.388 (4)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.382 (4)	C24—C25	1.369 (5)
C11—N2	1.391 (5)	C24—N4	1.400 (5)
C12—C13	1.362 (4)	C25—C26	1.363 (5)
C12—H12	0.9300	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300
S1—O2	1.425 (2)	S2—O4	1.413 (2)
S1—O1	1.428 (3)	S2—O3	1.424 (2)
S1—N1	1.630 (4)	S2—N3	1.618 (3)
N1—H1N	0.70 (3)	N3—H4N	0.79 (3)
N2—H2N	0.88 (4)	N4—H5N	0.85 (4)
N2—H3N	0.97 (4)	N4—H6N	0.86 (4)
C6—C1—C2	118.7 (3)	C15—C14—C19	120.0 (3)
C6—C1—S1	120.0 (3)	C15—C14—S2	120.0 (3)
C2—C1—S1	121.3 (3)	C19—C14—S2	120.0 (3)
C3—C2—C1	119.7 (4)	C16—C15—C14	118.6 (4)
C3—C2—H2	120.2	C16—C15—H15	120.7
C1—C2—H2	120.2	C14—C15—H15	120.7
C4—C3—C2	122.2 (4)	C17—C16—C15	122.6 (4)
C4—C3—H3	118.9	C17—C16—H16	118.7
C2—C3—H3	118.9	C15—C16—H16	118.7
C5—C4—C3	117.7 (4)	C18—C17—C16	117.5 (4)
C5—C4—C7	120.9 (4)	C18—C17—C20	121.0 (5)
C3—C4—C7	121.4 (4)	C16—C17—C20	121.5 (4)
C4—C5—C6	122.0 (4)	C17—C18—C19	121.8 (4)
C4—C5—H5	119.0	C17—C18—H18	119.1
C6—C5—H5	119.0	C19—C18—H18	119.1
C1—C6—C5	119.7 (3)	C18—C19—C14	119.5 (4)
C1—C6—H6	120.1	C18—C19—H19	120.2
C5—C6—H6	120.1	C14—C19—H19	120.2
C4—C7—H7A	109.5	C17—C20—H20A	109.5
C4—C7—H7B	109.5	C17—C20—H20B	109.5
H7A—C7—H7B	109.5	H20A—C20—H20B	109.5
C4—C7—H7C	109.5	C17—C20—H20C	109.5
H7A—C7—H7C	109.5	H20A—C20—H20C	109.5
H7B—C7—H7C	109.5	H20B—C20—H20C	109.5
C13—C8—C9	119.7 (3)	C26—C21—C22	118.5 (3)
C13—C8—N1	119.0 (3)	C26—C21—N3	121.9 (3)
C9—C8—N1	121.2 (3)	C22—C21—N3	119.6 (3)
C10—C9—C8	119.6 (4)	C23—C22—C21	120.8 (3)
C10—C9—H9	120.2	C23—C22—H22	119.6
C8—C9—H9	120.2	C21—C22—H22	119.6
C9—C10—C11	121.3 (3)	C22—C23—C24	121.1 (3)
C9—C10—H10	119.3	C22—C23—H23	119.4
C11—C10—H10	119.3	C24—C23—H23	119.4
C10—C11—C12	117.7 (4)	C25—C24—C23	117.7 (3)
C10—C11—N2	121.6 (4)	C25—C24—N4	121.4 (4)
C12—C11—N2	120.6 (4)	C23—C24—N4	120.8 (4)
C13—C12—C11	121.1 (4)	C26—C25—C24	121.1 (3)
C13—C12—H12	119.4	C26—C25—H25	119.4
C11—C12—H12	119.4	C24—C25—H25	119.4
C12—C13—C8	120.4 (3)	C25—C26—C21	120.8 (3)
C12—C13—H13	119.8	C25—C26—H26	119.6
C8—C13—H13	119.8	C21—C26—H26	119.6
O2—S1—O1	119.24 (18)	O4—S2—O3	119.89 (16)
O2—S1—N1	106.46 (18)	O4—S2—N3	106.01 (16)
O1—S1—N1	106.72 (17)	O3—S2—N3	106.66 (16)
O2—S1—C1	107.65 (17)	O4—S2—C14	108.04 (16)
O1—S1—C1	108.28 (17)	O3—S2—C14	107.91 (17)
N1—S1—C1	108.05 (16)	N3—S2—C14	107.78 (15)
C8—N1—S1	119.4 (2)	C21—N3—S2	120.1 (2)
C8—N1—H1N	113 (4)	C21—N3—H4N	112 (2)
S1—N1—H1N	117 (4)	S2—N3—H4N	112 (3)
C11—N2—H2N	119 (3)	C24—N4—H5N	106 (3)
C11—N2—H3N	113 (2)	C24—N4—H6N	107 (3)
H2N—N2—H3N	115 (4)	H5N—N4—H6N	125 (4)
C6—C1—C2—C3	1.0 (5)	C19—C14—C15—C16	1.7 (5)
S1—C1—C2—C3	−178.0 (3)	S2—C14—C15—C16	−179.5 (3)
C1—C2—C3—C4	0.8 (6)	C14—C15—C16—C17	−0.7 (6)
C2—C3—C4—C5	−2.1 (6)	C15—C16—C17—C18	−0.7 (6)
C2—C3—C4—C7	176.9 (4)	C15—C16—C17—C20	177.3 (4)
C3—C4—C5—C6	1.5 (6)	C16—C17—C18—C19	1.0 (6)
C7—C4—C5—C6	−177.4 (4)	C20—C17—C18—C19	−177.0 (4)
C2—C1—C6—C5	−1.5 (5)	C17—C18—C19—C14	0.0 (5)
S1—C1—C6—C5	177.5 (3)	C15—C14—C19—C18	−1.4 (5)
C4—C5—C6—C1	0.2 (6)	S2—C14—C19—C18	179.8 (3)
C13—C8—C9—C10	−0.5 (5)	C26—C21—C22—C23	1.6 (5)
N1—C8—C9—C10	−179.1 (3)	N3—C21—C22—C23	−179.6 (3)
C8—C9—C10—C11	−0.8 (6)	C21—C22—C23—C24	−1.0 (6)
C9—C10—C11—C12	1.3 (6)	C22—C23—C24—C25	−0.6 (6)
C9—C10—C11—N2	177.6 (4)	C22—C23—C24—N4	−177.4 (4)
C10—C11—C12—C13	−0.6 (5)	C23—C24—C25—C26	1.7 (6)
N2—C11—C12—C13	−176.9 (4)	N4—C24—C25—C26	178.5 (4)
C11—C12—C13—C8	−0.6 (5)	C24—C25—C26—C21	−1.2 (6)
C9—C8—C13—C12	1.2 (5)	C22—C21—C26—C25	−0.5 (5)
N1—C8—C13—C12	179.8 (3)	N3—C21—C26—C25	−179.2 (3)
C6—C1—S1—O2	−154.1 (3)	C15—C14—S2—O4	154.8 (3)
C2—C1—S1—O2	24.9 (3)	C19—C14—S2—O4	−26.5 (3)
C6—C1—S1—O1	−23.9 (3)	C15—C14—S2—O3	23.8 (3)
C2—C1—S1—O1	155.1 (3)	C19—C14—S2—O3	−157.5 (3)
C6—C1—S1—N1	91.3 (3)	C15—C14—S2—N3	−91.1 (3)
C2—C1—S1—N1	−89.7 (3)	C19—C14—S2—N3	87.7 (3)
C13—C8—N1—S1	81.6 (4)	C26—C21—N3—S2	−100.0 (4)
C9—C8—N1—S1	−99.8 (4)	C22—C21—N3—S2	81.2 (4)
O2—S1—N1—C8	−47.4 (3)	O4—S2—N3—C21	−174.3 (2)
O1—S1—N1—C8	−175.8 (3)	O3—S2—N3—C21	−45.5 (3)
C1—S1—N1—C8	67.9 (3)	C14—S2—N3—C21	70.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.70 (3)	2.33 (4)	2.996 (4)	161 (5)
N2—H2N···O4ii	0.88 (4)	2.18 (4)	3.052 (4)	172 (4)
N2—H3N···N4iii	0.97 (4)	2.28 (4)	3.191 (5)	155 (4)
N3—H4N···O3i	0.79 (3)	2.17 (3)	2.957 (3)	170 (3)
N4—H5N···N2iv	0.85 (4)	2.45 (4)	3.241 (5)	155 (4)
N4—H6N···O1v	0.86 (4)	2.47 (4)	3.323 (5)	171 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.70 (3)	2.33 (4)	2.996 (4)	161 (5)
N2—H2N⋯O4ii	0.88 (4)	2.18 (4)	3.052 (4)	172 (4)
N2—H3N⋯N4iii	0.97 (4)	2.28 (4)	3.191 (5)	155 (4)
N3—H4N⋯O3i	0.79 (3)	2.17 (3)	2.957 (3)	170 (3)
N4—H5N⋯N2iv	0.85 (4)	2.45 (4)	3.241 (5)	155 (4)
N4—H6N⋯O1v	0.86 (4)	2.47 (4)	3.323 (5)	171 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .