N-(3-Chloro-1-methyl-1H-indazol-5-yl)-4-methylbenzene-sulfonamide.

The asymmetric unit of the title compound, C15H14ClN3O2S, contains two independent mol-ecules showing different conformations: in one mol-ecule, the indazole ring system makes a dihedral angle of 51.5 (1)° with the benzene ring whereas in the other, the indazole unit is almost perpendicular to the benzene ring [dihedral angle 77.7 (1)°]. In the crystal, the mol-ecules are linked by N-H⋯N and N-H⋯O hydrogen bonds, forming a set of four mol-ecules linked in pairs about an inversion centre.

Related literature

For the biological activity of sulfonamides, see: El-Sayed et al. (2011 ▶); Mustafa et al. (2012 ▶); Scozzafava et al. (2003 ▶); Abbassi et al. (2012 ▶); Bouissane et al. (2006 ▶). For similar compounds see: Abbassi et al. (2013 ▶); Chicha et al. (2013 ▶).

Experimental

Crystal data

C15H14ClN3O2S

M = 335.80

Monoclinic,

a = 8.4580 (13) Å

b = 34.920 (6) Å

c = 10.8333 (17) Å

β = 97.226 (7)°

V = 3174.2 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.43 × 0.34 × 0.29 mm

Data collection

Bruker X8 APEX Diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.693, T max = 0.747

24523 measured reflections

7548 independent reflections

5730 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.137

S = 1.04

7548 reflections

398 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001184/rz5102sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001184/rz5102Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001184/rz5102Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H14ClN3O2S	F(000) = 1392
Mr = 335.80	Dx = 1.405 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7548 reflections
a = 8.4580 (13) Å	θ = 1.2–27.9°
b = 34.920 (6) Å	µ = 0.38 mm−1
c = 10.8333 (17) Å	T = 296 K
β = 97.226 (7)°	Block, colourless
V = 3174.2 (9) Å3	0.43 × 0.34 × 0.29 mm
Z = 8

Bruker X8 APEX Diffractometer	7548 independent reflections
Radiation source: fine-focus sealed tube	5730 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.9°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.693, Tmax = 0.747	k = −45→45
24523 measured reflections	l = −14→14

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.066P)2 + 1.0641P] where P = (Fo2 + 2Fc2)/3
7548 reflections	(Δ/σ)max = 0.001
398 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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	1.0746 (3)	0.91347 (6)	0.79881 (19)	0.0504 (5)
C2	1.0407 (2)	0.87989 (6)	0.72723 (17)	0.0419 (4)
C3	0.9081 (2)	0.85660 (6)	0.69368 (18)	0.0434 (4)
H3	0.8109	0.8619	0.7216	0.052*
C4	0.9252 (2)	0.82564 (6)	0.61843 (18)	0.0423 (4)
C5	1.0743 (3)	0.81730 (6)	0.57778 (19)	0.0486 (5)
H5	1.0831	0.7959	0.5278	0.058*
C6	1.2054 (3)	0.83968 (6)	0.60973 (19)	0.0495 (5)
H6	1.3029	0.8339	0.5830	0.059*
C7	1.1868 (2)	0.87174 (6)	0.68471 (17)	0.0420 (4)
C8	1.4506 (3)	0.90628 (9)	0.7010 (3)	0.0770 (8)
H8A	1.4792	0.8864	0.6466	0.115*
H8B	1.5234	0.9061	0.7765	0.115*
H8C	1.4556	0.9307	0.6608	0.115*
C9	0.7224 (2)	0.81651 (6)	0.3369 (2)	0.0480 (5)
C10	0.7436 (3)	0.78368 (7)	0.2700 (2)	0.0555 (5)
H10	0.7121	0.7601	0.2983	0.067*
C11	0.8113 (3)	0.78596 (8)	0.1618 (2)	0.0630 (6)
H11	0.8253	0.7637	0.1170	0.076*
C12	0.8592 (3)	0.82078 (9)	0.1178 (2)	0.0647 (7)
C13	0.8353 (3)	0.85328 (8)	0.1854 (3)	0.0699 (7)
H13	0.8658	0.8769	0.1565	0.084*
C14	0.7677 (3)	0.85179 (7)	0.2943 (2)	0.0631 (6)
H14	0.7526	0.8740	0.3386	0.076*
C15	0.9348 (4)	0.82282 (12)	−0.0009 (3)	0.0958 (11)
H15A	0.9758	0.8481	−0.0105	0.144*
H15B	0.8564	0.8170	−0.0704	0.144*
H15C	1.0203	0.8046	0.0026	0.144*
C16	−0.0868 (3)	0.68888 (6)	0.5237 (2)	0.0461 (5)
C17	−0.1129 (2)	0.65302 (6)	0.57713 (18)	0.0400 (4)
C18	−0.0879 (2)	0.61439 (6)	0.54823 (17)	0.0409 (4)
H18	−0.0357	0.6077	0.4807	0.049*
C19	−0.1426 (2)	0.58688 (6)	0.62205 (18)	0.0424 (4)
C20	−0.2169 (3)	0.59712 (7)	0.7270 (2)	0.0550 (6)
H20	−0.2535	0.5779	0.7755	0.066*
C21	−0.2365 (3)	0.63448 (7)	0.7594 (2)	0.0558 (6)
H21	−0.2825	0.6409	0.8302	0.067*
C22	−0.1853 (2)	0.66258 (6)	0.68257 (19)	0.0439 (4)
C23	−0.2682 (3)	0.72545 (7)	0.7723 (2)	0.0621 (6)
H23A	−0.3477	0.7416	0.7275	0.093*
H23B	−0.1879	0.7411	0.8181	0.093*
H23C	−0.3170	0.7095	0.8289	0.093*
C24	0.1019 (2)	0.52481 (6)	0.76926 (18)	0.0426 (4)
C25	0.2386 (3)	0.52368 (7)	0.7115 (2)	0.0555 (6)
H25	0.2331	0.5167	0.6282	0.067*
C26	0.3831 (3)	0.53297 (7)	0.7785 (2)	0.0590 (6)
H26	0.4748	0.5321	0.7393	0.071*
C27	0.3950 (3)	0.54353 (6)	0.9019 (2)	0.0512 (5)
C28	0.2566 (3)	0.54467 (8)	0.9573 (2)	0.0630 (6)
H28	0.2620	0.5518	1.0405	0.076*
C29	0.1113 (3)	0.53550 (7)	0.8926 (2)	0.0581 (6)
H29	0.0196	0.5365	0.9318	0.070*
C30	0.5535 (3)	0.55361 (9)	0.9739 (2)	0.0703 (7)
H30A	0.5504	0.5487	1.0607	0.105*
H30B	0.5756	0.5802	0.9622	0.105*
H30C	0.6356	0.5383	0.9447	0.105*
N1	1.2903 (2)	0.89975 (5)	0.72974 (16)	0.0508 (4)
N2	1.2212 (2)	0.92559 (5)	0.79962 (17)	0.0536 (5)
N3	0.7936 (2)	0.80055 (5)	0.58368 (17)	0.0510 (4)
H3N	0.8174	0.7786	0.5734	0.061*
N4	−0.1959 (2)	0.70164 (5)	0.68515 (17)	0.0507 (4)
N5	−0.1351 (2)	0.71778 (5)	0.58704 (18)	0.0511 (4)
N6	−0.1321 (2)	0.54756 (5)	0.58771 (16)	0.0481 (4)
H6N	−0.1053	0.5437	0.5194	0.048 (6)*
O1	0.5382 (2)	0.78159 (7)	0.47439 (19)	0.0876 (7)
O2	0.5960 (2)	0.85057 (6)	0.51171 (18)	0.0796 (6)
O3	−0.06493 (19)	0.48003 (4)	0.60889 (14)	0.0518 (4)
O4	−0.19633 (19)	0.51112 (5)	0.77251 (15)	0.0572 (4)
S1	0.64646 (7)	0.81318 (2)	0.47990 (6)	0.05832 (17)
S2	−0.08315 (6)	0.512747 (14)	0.68561 (5)	0.04431 (14)
Cl1	0.94290 (10)	0.93782 (2)	0.87784 (8)	0.0867 (3)
Cl2	−0.00273 (9)	0.697034 (19)	0.39037 (6)	0.06916 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0641 (14)	0.0440 (11)	0.0436 (11)	0.0153 (10)	0.0092 (10)	−0.0055 (9)
C2	0.0534 (11)	0.0389 (10)	0.0338 (9)	0.0118 (9)	0.0069 (8)	0.0006 (8)
C3	0.0489 (11)	0.0449 (11)	0.0380 (10)	0.0096 (9)	0.0113 (8)	0.0027 (8)
C4	0.0500 (11)	0.0416 (10)	0.0357 (9)	0.0032 (9)	0.0071 (8)	0.0031 (8)
C5	0.0575 (12)	0.0465 (12)	0.0435 (11)	0.0050 (10)	0.0131 (9)	−0.0104 (9)
C6	0.0505 (11)	0.0533 (13)	0.0468 (11)	0.0059 (10)	0.0145 (9)	−0.0097 (10)
C7	0.0495 (11)	0.0432 (11)	0.0334 (9)	0.0062 (9)	0.0050 (8)	−0.0019 (8)
C8	0.0678 (16)	0.0822 (19)	0.0854 (19)	−0.0212 (14)	0.0272 (14)	−0.0310 (16)
C9	0.0411 (10)	0.0535 (13)	0.0486 (12)	−0.0007 (9)	0.0028 (9)	0.0009 (10)
C10	0.0622 (13)	0.0516 (13)	0.0525 (13)	−0.0028 (11)	0.0058 (10)	0.0013 (10)
C11	0.0679 (15)	0.0713 (17)	0.0494 (13)	0.0015 (13)	0.0058 (11)	−0.0075 (12)
C12	0.0559 (13)	0.092 (2)	0.0455 (12)	−0.0060 (13)	0.0021 (10)	0.0076 (13)
C13	0.0734 (17)	0.0663 (17)	0.0688 (16)	−0.0111 (14)	0.0046 (13)	0.0183 (14)
C14	0.0682 (15)	0.0523 (14)	0.0684 (16)	−0.0010 (12)	0.0066 (12)	−0.0025 (12)
C15	0.084 (2)	0.152 (3)	0.0528 (15)	−0.015 (2)	0.0146 (14)	0.0132 (19)
C16	0.0468 (11)	0.0431 (11)	0.0490 (11)	−0.0042 (9)	0.0083 (9)	0.0018 (9)
C17	0.0390 (9)	0.0407 (10)	0.0398 (10)	−0.0011 (8)	0.0036 (8)	0.0007 (8)
C18	0.0430 (10)	0.0432 (11)	0.0369 (9)	0.0013 (8)	0.0071 (8)	−0.0018 (8)
C19	0.0483 (11)	0.0366 (10)	0.0425 (10)	0.0043 (8)	0.0060 (8)	0.0009 (8)
C20	0.0732 (15)	0.0443 (12)	0.0520 (12)	0.0069 (11)	0.0256 (11)	0.0078 (10)
C21	0.0726 (15)	0.0502 (13)	0.0488 (12)	0.0104 (11)	0.0241 (11)	0.0028 (10)
C22	0.0454 (10)	0.0399 (11)	0.0462 (11)	0.0052 (8)	0.0051 (8)	−0.0023 (8)
C23	0.0732 (16)	0.0530 (14)	0.0616 (14)	0.0132 (12)	0.0150 (12)	−0.0079 (11)
C24	0.0545 (11)	0.0334 (10)	0.0416 (10)	0.0005 (9)	0.0123 (9)	0.0024 (8)
C25	0.0614 (13)	0.0672 (15)	0.0401 (11)	−0.0117 (11)	0.0156 (10)	−0.0138 (10)
C26	0.0577 (13)	0.0688 (16)	0.0536 (13)	−0.0105 (12)	0.0191 (10)	−0.0163 (11)
C27	0.0633 (13)	0.0449 (12)	0.0459 (11)	−0.0046 (10)	0.0091 (10)	−0.0046 (9)
C28	0.0758 (16)	0.0758 (17)	0.0386 (11)	0.0001 (13)	0.0127 (11)	−0.0094 (11)
C29	0.0641 (14)	0.0699 (16)	0.0439 (12)	0.0031 (12)	0.0214 (11)	−0.0026 (11)
C30	0.0760 (17)	0.0789 (18)	0.0556 (14)	−0.0116 (14)	0.0068 (12)	−0.0109 (13)
N1	0.0536 (10)	0.0516 (11)	0.0473 (10)	0.0013 (8)	0.0073 (8)	−0.0106 (8)
N2	0.0667 (12)	0.0454 (10)	0.0483 (10)	0.0062 (9)	0.0057 (9)	−0.0097 (8)
N3	0.0577 (11)	0.0457 (10)	0.0506 (10)	−0.0035 (8)	0.0112 (8)	−0.0002 (8)
N4	0.0585 (11)	0.0412 (10)	0.0533 (10)	0.0038 (8)	0.0107 (8)	−0.0025 (8)
N5	0.0547 (10)	0.0414 (10)	0.0574 (11)	−0.0030 (8)	0.0083 (8)	−0.0002 (8)
N6	0.0656 (11)	0.0393 (9)	0.0410 (9)	0.0040 (8)	0.0126 (8)	0.0009 (7)
O1	0.0602 (11)	0.1231 (18)	0.0819 (13)	−0.0364 (11)	0.0190 (9)	−0.0040 (12)
O2	0.0652 (11)	0.0982 (15)	0.0771 (12)	0.0316 (10)	0.0148 (9)	−0.0131 (11)
O3	0.0635 (9)	0.0352 (7)	0.0582 (9)	−0.0032 (7)	0.0131 (7)	−0.0004 (6)
O4	0.0609 (9)	0.0524 (9)	0.0629 (10)	−0.0027 (7)	0.0257 (8)	0.0083 (7)
S1	0.0431 (3)	0.0763 (4)	0.0573 (3)	−0.0024 (3)	0.0130 (2)	−0.0057 (3)
S2	0.0526 (3)	0.0346 (3)	0.0478 (3)	−0.0019 (2)	0.0143 (2)	0.0037 (2)
Cl1	0.0885 (5)	0.0726 (5)	0.1041 (6)	0.0191 (4)	0.0319 (4)	−0.0360 (4)
Cl2	0.0874 (5)	0.0592 (4)	0.0663 (4)	−0.0082 (3)	0.0308 (3)	0.0107 (3)

C1—N2	1.309 (3)	C18—C19	1.367 (3)
C1—C2	1.415 (3)	C18—H18	0.9300
C1—Cl1	1.713 (2)	C19—C20	1.413 (3)
C2—C3	1.396 (3)	C19—N6	1.428 (3)
C2—C7	1.401 (3)	C20—C21	1.366 (3)
C3—C4	1.373 (3)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.390 (3)
C4—C5	1.418 (3)	C21—H21	0.9300
C4—N3	1.429 (3)	C22—N4	1.367 (3)
C5—C6	1.365 (3)	C23—N4	1.450 (3)
C5—H5	0.9300	C23—H23A	0.9600
C6—C7	1.404 (3)	C23—H23B	0.9600
C6—H6	0.9300	C23—H23C	0.9600
C7—N1	1.361 (3)	C24—C29	1.380 (3)
C8—N1	1.447 (3)	C24—C25	1.383 (3)
C8—H8A	0.9600	C24—S2	1.758 (2)
C8—H8B	0.9600	C25—C26	1.379 (3)
C8—H8C	0.9600	C25—H25	0.9300
C9—C10	1.380 (3)	C26—C27	1.379 (3)
C9—C14	1.386 (3)	C26—H26	0.9300
C9—S1	1.754 (2)	C27—C28	1.382 (3)
C10—C11	1.370 (3)	C27—C30	1.505 (3)
C10—H10	0.9300	C28—C29	1.374 (4)
C11—C12	1.385 (4)	C28—H28	0.9300
C11—H11	0.9300	C29—H29	0.9300
C12—C13	1.379 (4)	C30—H30A	0.9600
C12—C15	1.509 (4)	C30—H30B	0.9600
C13—C14	1.376 (4)	C30—H30C	0.9600
C13—H13	0.9300	N1—N2	1.356 (2)
C14—H14	0.9300	N3—S1	1.630 (2)
C15—H15A	0.9600	N3—H3N	0.8039
C15—H15B	0.9600	N4—N5	1.360 (3)
C15—H15C	0.9600	N6—S2	1.6321 (17)
C16—N5	1.314 (3)	N6—H6N	0.8114
C16—C17	1.409 (3)	O1—S1	1.430 (2)
C16—Cl2	1.712 (2)	O2—S1	1.429 (2)
C17—C22	1.403 (3)	O3—S2	1.4325 (15)
C17—C18	1.407 (3)	O4—S2	1.4256 (15)
N2—C1—C2	113.42 (18)	C21—C20—H20	119.0
N2—C1—Cl1	120.72 (17)	C19—C20—H20	119.0
C2—C1—Cl1	125.85 (18)	C20—C21—C22	117.6 (2)
C3—C2—C7	120.60 (18)	C20—C21—H21	121.2
C3—C2—C1	136.53 (19)	C22—C21—H21	121.2
C7—C2—C1	102.86 (19)	N4—C22—C21	131.7 (2)
C4—C3—C2	118.20 (18)	N4—C22—C17	106.89 (18)
C4—C3—H3	120.9	C21—C22—C17	121.34 (19)
C2—C3—H3	120.9	N4—C23—H23A	109.5
C3—C4—C5	120.68 (19)	N4—C23—H23B	109.5
C3—C4—N3	120.20 (18)	H23A—C23—H23B	109.5
C5—C4—N3	119.08 (18)	N4—C23—H23C	109.5
C6—C5—C4	122.01 (19)	H23A—C23—H23C	109.5
C6—C5—H5	119.0	H23B—C23—H23C	109.5
C4—C5—H5	119.0	C29—C24—C25	119.7 (2)
C5—C6—C7	117.16 (19)	C29—C24—S2	120.19 (17)
C5—C6—H6	121.4	C25—C24—S2	120.06 (16)
C7—C6—H6	121.4	C26—C25—C24	119.5 (2)
N1—C7—C2	106.86 (17)	C26—C25—H25	120.3
N1—C7—C6	131.81 (19)	C24—C25—H25	120.3
C2—C7—C6	121.33 (19)	C27—C26—C25	121.6 (2)
N1—C8—H8A	109.5	C27—C26—H26	119.2
N1—C8—H8B	109.5	C25—C26—H26	119.2
H8A—C8—H8B	109.5	C26—C27—C28	117.8 (2)
N1—C8—H8C	109.5	C26—C27—C30	121.1 (2)
H8A—C8—H8C	109.5	C28—C27—C30	121.1 (2)
H8B—C8—H8C	109.5	C29—C28—C27	121.6 (2)
C10—C9—C14	120.3 (2)	C29—C28—H28	119.2
C10—C9—S1	119.66 (18)	C27—C28—H28	119.2
C14—C9—S1	120.01 (19)	C28—C29—C24	119.7 (2)
C11—C10—C9	119.8 (2)	C28—C29—H29	120.1
C11—C10—H10	120.1	C24—C29—H29	120.1
C9—C10—H10	120.1	C27—C30—H30A	109.5
C10—C11—C12	121.1 (2)	C27—C30—H30B	109.5
C10—C11—H11	119.4	H30A—C30—H30B	109.5
C12—C11—H11	119.4	C27—C30—H30C	109.5
C13—C12—C11	118.2 (2)	H30A—C30—H30C	109.5
C13—C12—C15	121.3 (3)	H30B—C30—H30C	109.5
C11—C12—C15	120.5 (3)	N2—N1—C7	112.03 (17)
C14—C13—C12	121.9 (3)	N2—N1—C8	119.78 (19)
C14—C13—H13	119.0	C7—N1—C8	127.85 (19)
C12—C13—H13	119.0	C1—N2—N1	104.81 (17)
C13—C14—C9	118.8 (2)	C4—N3—S1	121.17 (15)
C13—C14—H14	120.6	C4—N3—H3N	114.9
C9—C14—H14	120.6	S1—N3—H3N	110.2
C12—C15—H15A	109.5	N5—N4—C22	111.42 (17)
C12—C15—H15B	109.5	N5—N4—C23	120.21 (18)
H15A—C15—H15B	109.5	C22—N4—C23	128.28 (19)
C12—C15—H15C	109.5	C16—N5—N4	105.25 (17)
H15A—C15—H15C	109.5	C19—N6—S2	124.46 (14)
H15B—C15—H15C	109.5	C19—N6—H6N	115.4
N5—C16—C17	113.14 (19)	S2—N6—H6N	113.2
N5—C16—Cl2	120.16 (16)	O2—S1—O1	120.36 (13)
C17—C16—Cl2	126.69 (16)	O2—S1—N3	107.83 (11)
C22—C17—C18	120.18 (18)	O1—S1—N3	104.45 (12)
C22—C17—C16	103.29 (18)	O2—S1—C9	107.82 (12)
C18—C17—C16	136.51 (19)	O1—S1—C9	108.55 (11)
C19—C18—C17	118.18 (18)	N3—S1—C9	107.12 (10)
C19—C18—H18	120.9	O4—S2—O3	118.79 (10)
C17—C18—H18	120.9	O4—S2—N6	108.81 (10)
C18—C19—C20	120.70 (19)	O3—S2—N6	104.71 (9)
C18—C19—N6	119.09 (18)	O4—S2—C24	107.30 (10)
C20—C19—N6	120.11 (18)	O3—S2—C24	109.65 (10)
C21—C20—C19	121.9 (2)	N6—S2—C24	107.03 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N5i	0.80	2.16	2.952 (3)	167
N6—H6N···O3ii	0.81	2.28	3.022 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N5i	0.80	2.16	2.952 (3)	167
N6—H6N⋯O3ii	0.81	2.28	3.022 (2)	152

Symmetry codes: (i) ; (ii) .