N'-(4-Bromo-phenyl-sulfon-yl)isonicotino-hydrazide.

The title compound, C(12)H(10)BrN(3)O(3)S, crystallizes with two crystallographically independent mol-ecules in the asymmetric unit. The dihedral angles between the two six-membered rings in the mol-ecules are 34.1 (3) and 45.1 (2)°. In the crystal structure, mol-ecules are connected via N-H⋯O and N-H⋯N hydrogen bonding.

Related literature

For general background to isonicotinic acid hydrazides, see: Carlton (1967 ▶). For a related structure, see: Wang et al. (2008 ▶). For the synthesis and biological activity of isoniazid and hydrazide derivatives, see: Lourenco et al. (2008 ▶); Kucukguzel et al. (2003 ▶); Carvalho et al. (2008 ▶), For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H10BrN3O3S

M = 356.20

Monoclinic,

a = 10.1229 (6) Å

b = 19.0440 (12) Å

c = 15.0640 (7) Å

β = 96.862 (2)°

V = 2883.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 3.01 mm−1

T = 296 K

0.36 × 0.30 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.349, T max = 0.641

29398 measured reflections

6601 independent reflections

3473 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.146

S = 1.01

6601 reflections

373 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.06 e Å−3

Δρmin = −0.88 e Å−3

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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028475/nc2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028475/nc2151Isup2.hkl

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

C12H10BrN3O3S	F(000) = 1424
Mr = 356.20	Dx = 1.641 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5184 reflections
a = 10.1229 (6) Å	θ = 2.1–22.9°
b = 19.0440 (12) Å	µ = 3.01 mm−1
c = 15.0640 (7) Å	T = 296 K
β = 96.862 (2)°	Needle, white yellow
V = 2883.2 (3) Å3	0.36 × 0.30 × 0.15 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	6601 independent reflections
Radiation source: fine-focus sealed tube	3473 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→11
Tmin = 0.349, Tmax = 0.641	k = −24→23
29398 measured reflections	l = −17→19

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0597P)2 + 2.5287P] where P = (Fo2 + 2Fc2)/3
6601 reflections	(Δ/σ)max = 0.001
373 parameters	Δρmax = 1.06 e Å−3
0 restraints	Δρmin = −0.88 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 > 2sigma(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
Br1	0.01531 (7)	0.40221 (5)	0.59324 (5)	0.1083 (3)
Br2	1.07622 (6)	0.14607 (4)	0.37352 (6)	0.1046 (3)
S1	0.46424 (10)	0.38694 (6)	0.33172 (7)	0.0392 (3)
S2	0.46755 (9)	0.10499 (5)	0.43498 (6)	0.0328 (2)
O1	0.1616 (3)	0.49151 (15)	0.28196 (19)	0.0467 (7)
O2	0.4756 (3)	0.31692 (15)	0.2999 (2)	0.0510 (8)
O3	0.5802 (3)	0.42527 (17)	0.3664 (2)	0.0566 (9)
O4	0.2996 (2)	0.20910 (13)	0.59686 (17)	0.0376 (7)
O5	0.3909 (3)	0.16199 (14)	0.39574 (18)	0.0420 (7)
O6	0.4282 (3)	0.03415 (14)	0.41370 (17)	0.0413 (7)
N1	−0.2166 (3)	0.3447 (2)	0.1433 (3)	0.0533 (10)
N2	0.2699 (3)	0.41007 (18)	0.2107 (2)	0.0340 (8)
H2	0.270 (4)	0.383 (2)	0.174 (3)	0.041*
N3	0.3969 (3)	0.43457 (18)	0.2456 (2)	0.0353 (8)
H3	0.398 (4)	0.474 (2)	0.259 (3)	0.042*
N4	0.5582 (4)	0.42464 (18)	0.6902 (2)	0.0474 (9)
N5	0.5095 (3)	0.17527 (17)	0.5802 (2)	0.0327 (8)
H5	0.590 (4)	0.176 (2)	0.600 (3)	0.039*
N6	0.4645 (3)	0.11035 (17)	0.5443 (2)	0.0336 (8)
H6	0.493 (4)	0.077 (2)	0.577 (3)	0.040*
C1	0.0288 (4)	0.4054 (2)	0.1991 (3)	0.0352 (9)
C2	0.0182 (4)	0.3454 (3)	0.1500 (4)	0.0685 (16)
H2A	0.0942	0.3235	0.1342	0.082*
C3	−0.1055 (5)	0.3172 (3)	0.1236 (4)	0.0732 (17)
H3A	−0.1102	0.2761	0.0900	0.088*
C4	−0.2061 (5)	0.4033 (3)	0.1895 (4)	0.0774 (18)
H4	−0.2837	0.4244	0.2038	0.093*
C5	−0.0851 (4)	0.4357 (3)	0.2184 (4)	0.0668 (15)
H5A	−0.0828	0.4775	0.2505	0.080*
C6	0.1592 (4)	0.4400 (2)	0.2344 (3)	0.0351 (9)
C7	0.3474 (4)	0.3869 (2)	0.4092 (2)	0.0368 (9)
C8	0.2620 (4)	0.3310 (2)	0.4126 (3)	0.0453 (11)
H8	0.2713	0.2909	0.3786	0.054*
C9	0.1620 (5)	0.3355 (3)	0.4677 (3)	0.0574 (13)
H9	0.1031	0.2984	0.4711	0.069*
C10	0.1508 (5)	0.3954 (3)	0.5172 (3)	0.0559 (13)
C11	0.2374 (5)	0.4504 (3)	0.5151 (3)	0.0557 (13)
H11	0.2291	0.4899	0.5504	0.067*
C12	0.3362 (4)	0.4468 (2)	0.4607 (3)	0.0460 (11)
H12	0.3953	0.4840	0.4581	0.055*
C13	0.4719 (4)	0.29175 (19)	0.6327 (2)	0.0301 (8)
C14	0.5961 (4)	0.3167 (2)	0.6178 (3)	0.0482 (11)
H14	0.6526	0.2894	0.5877	0.058*
C15	0.6342 (5)	0.3825 (2)	0.6483 (3)	0.0556 (12)
H15	0.7183	0.3984	0.6390	0.067*
C16	0.4389 (4)	0.4011 (2)	0.7026 (3)	0.0424 (10)
H16	0.3832	0.4305	0.7306	0.051*
C17	0.3926 (4)	0.3353 (2)	0.6764 (2)	0.0363 (9)
H17	0.3089	0.3205	0.6881	0.044*
C18	0.4181 (4)	0.22155 (19)	0.6023 (2)	0.0288 (8)
C19	0.6340 (4)	0.1167 (2)	0.4150 (2)	0.0346 (9)
C20	0.6736 (4)	0.1792 (3)	0.3808 (3)	0.0514 (11)
H20	0.6125	0.2151	0.3669	0.062*
C21	0.8050 (5)	0.1878 (3)	0.3674 (3)	0.0654 (14)
H21	0.8330	0.2298	0.3443	0.078*
C22	0.8945 (5)	0.1344 (3)	0.3881 (3)	0.0606 (14)
C23	0.8545 (5)	0.0717 (3)	0.4216 (3)	0.0581 (13)
H23	0.9158	0.0357	0.4350	0.070*
C24	0.7237 (4)	0.0623 (2)	0.4352 (3)	0.0477 (11)
H24	0.6957	0.0201	0.4576	0.057*

	U11	U22	U33	U12	U13	U23
Br1	0.0866 (5)	0.1511 (8)	0.0966 (5)	0.0053 (5)	0.0490 (4)	−0.0107 (5)
Br2	0.0489 (3)	0.1069 (6)	0.1655 (7)	−0.0228 (3)	0.0441 (4)	−0.0377 (5)
S1	0.0289 (5)	0.0374 (6)	0.0504 (6)	0.0021 (4)	0.0004 (4)	−0.0027 (5)
S2	0.0309 (5)	0.0262 (5)	0.0410 (5)	0.0004 (4)	0.0034 (4)	−0.0016 (4)
O1	0.0373 (16)	0.0419 (19)	0.0602 (18)	0.0023 (13)	0.0028 (14)	−0.0199 (15)
O2	0.0537 (18)	0.0331 (17)	0.0663 (19)	0.0106 (14)	0.0074 (15)	−0.0016 (15)
O3	0.0308 (16)	0.064 (2)	0.072 (2)	−0.0041 (15)	−0.0075 (14)	−0.0053 (17)
O4	0.0277 (14)	0.0306 (16)	0.0552 (17)	−0.0032 (12)	0.0079 (12)	0.0012 (13)
O5	0.0397 (16)	0.0371 (17)	0.0483 (16)	0.0046 (13)	0.0015 (13)	0.0059 (13)
O6	0.0444 (16)	0.0295 (17)	0.0488 (16)	−0.0045 (13)	0.0005 (13)	−0.0060 (13)
N1	0.0282 (19)	0.061 (3)	0.070 (3)	−0.0053 (18)	0.0023 (17)	−0.004 (2)
N2	0.0266 (17)	0.030 (2)	0.045 (2)	−0.0025 (14)	0.0027 (15)	−0.0088 (15)
N3	0.0266 (17)	0.0263 (19)	0.052 (2)	−0.0036 (15)	0.0010 (14)	−0.0082 (17)
N4	0.047 (2)	0.030 (2)	0.062 (2)	−0.0042 (17)	−0.0051 (18)	−0.0024 (18)
N5	0.0257 (16)	0.0244 (19)	0.047 (2)	−0.0017 (14)	0.0003 (14)	−0.0068 (15)
N6	0.0396 (19)	0.0233 (19)	0.0373 (18)	−0.0021 (15)	0.0028 (14)	0.0028 (15)
C1	0.029 (2)	0.038 (2)	0.038 (2)	−0.0023 (17)	0.0013 (16)	−0.0056 (18)
C2	0.019 (2)	0.076 (4)	0.110 (4)	0.002 (2)	0.005 (2)	−0.043 (3)
C3	0.039 (3)	0.070 (4)	0.109 (4)	−0.003 (3)	0.000 (3)	−0.045 (3)
C4	0.030 (3)	0.089 (5)	0.115 (5)	0.005 (3)	0.016 (3)	−0.032 (4)
C5	0.034 (3)	0.067 (4)	0.101 (4)	−0.001 (2)	0.013 (3)	−0.039 (3)
C6	0.033 (2)	0.029 (2)	0.042 (2)	0.0000 (18)	0.0043 (18)	0.0011 (19)
C7	0.036 (2)	0.032 (2)	0.040 (2)	0.0027 (18)	−0.0041 (17)	0.0008 (19)
C8	0.050 (3)	0.035 (3)	0.050 (3)	−0.001 (2)	0.004 (2)	−0.003 (2)
C9	0.054 (3)	0.054 (3)	0.064 (3)	−0.014 (2)	0.007 (2)	0.007 (3)
C10	0.053 (3)	0.068 (4)	0.047 (3)	0.010 (3)	0.009 (2)	0.002 (3)
C11	0.064 (3)	0.056 (3)	0.046 (3)	0.010 (3)	0.002 (2)	−0.009 (2)
C12	0.050 (3)	0.042 (3)	0.044 (2)	0.001 (2)	−0.006 (2)	−0.004 (2)
C13	0.0307 (19)	0.025 (2)	0.034 (2)	−0.0031 (16)	0.0013 (16)	0.0014 (17)
C14	0.036 (2)	0.031 (2)	0.080 (3)	0.0004 (19)	0.017 (2)	−0.007 (2)
C15	0.039 (2)	0.036 (3)	0.091 (4)	−0.010 (2)	0.009 (2)	−0.004 (3)
C16	0.055 (3)	0.032 (3)	0.041 (2)	0.007 (2)	0.005 (2)	−0.0044 (19)
C17	0.038 (2)	0.031 (2)	0.040 (2)	−0.0023 (18)	0.0058 (18)	−0.0013 (18)
C18	0.029 (2)	0.025 (2)	0.031 (2)	−0.0024 (16)	0.0007 (16)	0.0026 (16)
C19	0.034 (2)	0.031 (2)	0.040 (2)	−0.0039 (18)	0.0096 (17)	−0.0066 (18)
C20	0.044 (3)	0.048 (3)	0.063 (3)	−0.003 (2)	0.008 (2)	0.004 (2)
C21	0.059 (3)	0.059 (4)	0.081 (4)	−0.021 (3)	0.019 (3)	−0.004 (3)
C22	0.037 (3)	0.068 (4)	0.079 (3)	−0.008 (3)	0.018 (2)	−0.023 (3)
C23	0.043 (3)	0.052 (3)	0.081 (3)	0.005 (2)	0.011 (2)	−0.017 (3)
C24	0.044 (3)	0.033 (3)	0.068 (3)	−0.001 (2)	0.015 (2)	−0.001 (2)

Br1—C10	1.893 (5)	C4—H4	0.9300
Br2—C22	1.891 (4)	C5—H5A	0.9300
S1—O2	1.426 (3)	C7—C8	1.376 (6)
S1—O3	1.427 (3)	C7—C12	1.392 (6)
S1—N3	1.661 (4)	C8—C9	1.386 (6)
S1—C7	1.758 (4)	C8—H8	0.9300
S2—O5	1.421 (3)	C9—C10	1.375 (7)
S2—O6	1.432 (3)	C9—H9	0.9300
S2—N6	1.654 (3)	C10—C11	1.370 (7)
S2—C19	1.760 (4)	C11—C12	1.369 (6)
O1—C6	1.213 (5)	C11—H11	0.9300
O4—C18	1.216 (4)	C12—H12	0.9300
N1—C3	1.306 (6)	C13—C17	1.375 (5)
N1—C4	1.313 (6)	C13—C14	1.387 (5)
N2—C6	1.343 (5)	C13—C18	1.495 (5)
N2—N3	1.409 (4)	C14—C15	1.375 (6)
N2—H2	0.75 (4)	C14—H14	0.9300
N3—H3	0.77 (4)	C15—H15	0.9300
N4—C15	1.322 (6)	C16—C17	1.379 (5)
N4—C16	1.323 (5)	C16—H16	0.9300
N5—C18	1.348 (5)	C17—H17	0.9300
N5—N6	1.403 (4)	C19—C20	1.375 (6)
N5—H5	0.83 (4)	C19—C24	1.386 (6)
N6—H6	0.83 (4)	C20—C21	1.379 (6)
C1—C5	1.351 (6)	C20—H20	0.9300
C1—C2	1.359 (6)	C21—C22	1.372 (7)
C1—C6	1.513 (5)	C21—H21	0.9300
C2—C3	1.377 (6)	C22—C23	1.376 (7)
C2—H2A	0.9300	C23—C24	1.376 (6)
C3—H3A	0.9300	C23—H23	0.9300
C4—C5	1.393 (7)	C24—H24	0.9300
O2—S1—O3	120.34 (19)	C9—C8—H8	120.6
O2—S1—N3	106.87 (17)	C10—C9—C8	119.3 (4)
O3—S1—N3	104.46 (18)	C10—C9—H9	120.3
O2—S1—C7	108.10 (19)	C8—C9—H9	120.3
O3—S1—C7	110.28 (19)	C11—C10—C9	121.9 (4)
N3—S1—C7	105.78 (17)	C11—C10—Br1	118.2 (4)
O5—S2—O6	120.20 (17)	C9—C10—Br1	119.9 (4)
O5—S2—N6	107.03 (17)	C12—C11—C10	119.4 (4)
O6—S2—N6	104.08 (17)	C12—C11—H11	120.3
O5—S2—C19	108.57 (18)	C10—C11—H11	120.3
O6—S2—C19	109.09 (18)	C11—C12—C7	119.3 (4)
N6—S2—C19	107.09 (17)	C11—C12—H12	120.4
C3—N1—C4	116.3 (4)	C7—C12—H12	120.4
C6—N2—N3	120.9 (3)	C17—C13—C14	117.6 (4)
C6—N2—H2	124 (3)	C17—C13—C18	118.3 (3)
N3—N2—H2	115 (3)	C14—C13—C18	124.1 (3)
N2—N3—S1	112.5 (3)	C15—C14—C13	118.7 (4)
N2—N3—H3	114 (3)	C15—C14—H14	120.6
S1—N3—H3	109 (3)	C13—C14—H14	120.6
C15—N4—C16	117.0 (4)	N4—C15—C14	123.9 (4)
C18—N5—N6	118.1 (3)	N4—C15—H15	118.1
C18—N5—H5	125 (3)	C14—C15—H15	118.1
N6—N5—H5	114 (3)	N4—C16—C17	123.5 (4)
N5—N6—S2	113.2 (2)	N4—C16—H16	118.2
N5—N6—H6	111 (3)	C17—C16—H16	118.2
S2—N6—H6	120 (3)	C13—C17—C16	119.2 (4)
C5—C1—C2	117.5 (4)	C13—C17—H17	120.4
C5—C1—C6	118.0 (4)	C16—C17—H17	120.4
C2—C1—C6	124.5 (4)	O4—C18—N5	123.8 (3)
C1—C2—C3	119.7 (4)	O4—C18—C13	121.0 (3)
C1—C2—H2A	120.2	N5—C18—C13	115.2 (3)
C3—C2—H2A	120.2	C20—C19—C24	121.0 (4)
N1—C3—C2	123.8 (5)	C20—C19—S2	120.1 (3)
N1—C3—H3A	118.1	C24—C19—S2	118.9 (3)
C2—C3—H3A	118.1	C19—C20—C21	119.2 (5)
N1—C4—C5	123.6 (4)	C19—C20—H20	120.4
N1—C4—H4	118.2	C21—C20—H20	120.4
C5—C4—H4	118.2	C22—C21—C20	120.1 (5)
C1—C5—C4	119.0 (5)	C22—C21—H21	120.0
C1—C5—H5A	120.5	C20—C21—H21	120.0
C4—C5—H5A	120.5	C21—C22—C23	120.7 (4)
O1—C6—N2	122.8 (4)	C21—C22—Br2	120.8 (4)
O1—C6—C1	121.0 (3)	C23—C22—Br2	118.5 (4)
N2—C6—C1	116.2 (3)	C24—C23—C22	119.8 (5)
C8—C7—C12	121.3 (4)	C24—C23—H23	120.1
C8—C7—S1	120.1 (3)	C22—C23—H23	120.1
C12—C7—S1	118.4 (3)	C23—C24—C19	119.2 (4)
C7—C8—C9	118.8 (4)	C23—C24—H24	120.4
C7—C8—H8	120.6	C19—C24—H24	120.4
C6—N2—N3—S1	97.7 (4)	Br1—C10—C11—C12	−180.0 (3)
O2—S1—N3—N2	60.2 (3)	C10—C11—C12—C7	−0.6 (6)
O3—S1—N3—N2	−171.2 (3)	C8—C7—C12—C11	−0.7 (6)
C7—S1—N3—N2	−54.8 (3)	S1—C7—C12—C11	173.8 (3)
C18—N5—N6—S2	103.9 (3)	C17—C13—C14—C15	1.0 (6)
O5—S2—N6—N5	−55.9 (3)	C18—C13—C14—C15	179.4 (4)
O6—S2—N6—N5	175.8 (2)	C16—N4—C15—C14	−0.1 (7)
C19—S2—N6—N5	60.3 (3)	C13—C14—C15—N4	−1.2 (7)
C5—C1—C2—C3	−1.4 (8)	C15—N4—C16—C17	1.7 (6)
C6—C1—C2—C3	177.8 (5)	C14—C13—C17—C16	0.4 (6)
C4—N1—C3—C2	1.2 (9)	C18—C13—C17—C16	−178.1 (3)
C1—C2—C3—N1	−0.1 (10)	N4—C16—C17—C13	−1.8 (6)
C3—N1—C4—C5	−0.8 (9)	N6—N5—C18—O4	3.7 (5)
C2—C1—C5—C4	1.7 (8)	N6—N5—C18—C13	−175.0 (3)
C6—C1—C5—C4	−177.5 (5)	C17—C13—C18—O4	16.8 (5)
N1—C4—C5—C1	−0.7 (9)	C14—C13—C18—O4	−161.5 (4)
N3—N2—C6—O1	4.6 (6)	C17—C13—C18—N5	−164.5 (3)
N3—N2—C6—C1	−174.9 (3)	C14—C13—C18—N5	17.2 (5)
C5—C1—C6—O1	3.2 (6)	O5—S2—C19—C20	10.3 (4)
C2—C1—C6—O1	−176.0 (5)	O6—S2—C19—C20	143.0 (3)
C5—C1—C6—N2	−177.3 (4)	N6—S2—C19—C20	−105.0 (4)
C2—C1—C6—N2	3.5 (6)	O5—S2—C19—C24	−170.3 (3)
O2—S1—C7—C8	−16.3 (4)	O6—S2—C19—C24	−37.6 (4)
O3—S1—C7—C8	−149.7 (3)	N6—S2—C19—C24	74.4 (4)
N3—S1—C7—C8	97.9 (3)	C24—C19—C20—C21	−0.7 (7)
O2—S1—C7—C12	169.1 (3)	S2—C19—C20—C21	178.7 (4)
O3—S1—C7—C12	35.7 (4)	C19—C20—C21—C22	0.0 (7)
N3—S1—C7—C12	−76.7 (3)	C20—C21—C22—C23	0.6 (8)
C12—C7—C8—C9	1.1 (6)	C20—C21—C22—Br2	−178.2 (4)
S1—C7—C8—C9	−173.4 (3)	C21—C22—C23—C24	−0.5 (8)
C7—C8—C9—C10	−0.1 (7)	Br2—C22—C23—C24	178.3 (4)
C8—C9—C10—C11	−1.2 (7)	C22—C23—C24—C19	−0.2 (7)
C8—C9—C10—Br1	−179.7 (3)	C20—C19—C24—C23	0.8 (6)
C9—C10—C11—C12	1.6 (7)	S2—C19—C24—C23	−178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.76 (4)	2.15 (4)	2.882 (4)	165.09
N3—H3···N4ii	0.78 (4)	2.10 (4)	2.868 (5)	168.21
N6—H6···O6iii	0.83 (4)	2.26 (4)	2.998 (4)	147.35
N5—H5···N1iv	0.83 (4)	2.03 (4)	2.847 (4)	168.32
N3—H3···O1	0.78 (4)	2.49 (4)	2.732 (4)	100 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.76 (4)	2.15 (4)	2.882 (4)	165.09
N3—H3⋯N4ii	0.78 (4)	2.10 (4)	2.868 (5)	168.21
N6—H6⋯O6iii	0.83 (4)	2.26 (4)	2.998 (4)	147.35
N5—H5⋯N1iv	0.83 (4)	2.03 (4)	2.847 (4)	168.32
N3—H3⋯O1	0.78 (4)	2.49 (4)	2.732 (4)	100 (3)

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