4-(3-Phenyl-3,3a,4,5-tetra-hydro-2H-benzo[g]indazol-2-yl)benzene-sulfonamide ethanol monosolvate.

In the title compound ethanol monosolvate, C(23)H(21)N(3)O(2)S·C(2)H(5)OH, the dihydro-pyrazole ring is twisted about the Csp(3)-Csp(3) bond. Nevertheless, the ring approximates a plane (r.m.s. deviation for the fitted atoms = 0.132 Å) and forms dihedral angles of 5.80 (13) and 12.29 (12)°, respectively, with the fused- and sulfonamide-benzene rings. As the dihydro-pyrazole C-bound phenyl group is roughly perpendicular to the dihydro-pyrazole ring [dihedral angle = 74.04 (15)°; the amino group is orientated to the same side of the mol-ecule], to a first approximation, the mol-ecule has a stunted T-shape. The cyclo-hexene ring adopts a half-chair conformation with the methyl-ene C atom connected to the dihydro-pyrazole ring lying 0.665 (4) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.050 Å). The components of the asymmetric unit are connected by an O-H⋯O hydrogen bond. Further links between mol-ecules leading to a three-dimensional architecture are of the type N-H⋯O.

Related literature

For a previous synthesis, see: Faidallah & Makki (1994 ▶). For the biological activity of related compounds, see: Faidallah et al. (2011 ▶). For the structure of the methyl analogue, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C23H21N3O2S·C2H6O

M = 449.56

Monoclinic,

a = 15.7556 (9) Å

b = 9.1789 (4) Å

c = 16.7515 (10) Å

β = 111.718 (7)°

V = 2250.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.761, T max = 1.000

15054 measured reflections

5196 independent reflections

3971 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.156

S = 1.04

5196 reflections

301 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028474/xu5573sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028474/xu5573Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028474/xu5573Isup3.cml

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

C23H21N3O2S·C2H6O	F(000) = 952
Mr = 449.56	Dx = 1.327 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4495 reflections
a = 15.7556 (9) Å	θ = 2.5–27.5°
b = 9.1789 (4) Å	µ = 0.18 mm−1
c = 16.7515 (10) Å	T = 100 K
β = 111.718 (7)°	Prsim, light-brown
V = 2250.6 (2) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	5196 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3971 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scan	h = −20→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −11→11
Tmin = 0.761, Tmax = 1.000	l = −17→21
15054 measured reflections

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) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0701P)2 + 1.7118P] where P = (Fo2 + 2Fc2)/3
5196 reflections	(Δ/σ)max = 0.001
301 parameters	Δρmax = 0.81 e Å−3
3 restraints	Δρmin = −0.45 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
S1	0.56232 (4)	0.84182 (6)	0.60754 (4)	0.02401 (16)
O1	0.62832 (11)	0.73972 (19)	0.66013 (11)	0.0328 (4)
O2	0.52421 (11)	0.82084 (18)	0.51577 (10)	0.0295 (4)
O3	0.78024 (13)	0.5436 (2)	0.69624 (13)	0.0455 (5)
N1	0.17020 (12)	0.91470 (19)	0.67783 (11)	0.0199 (4)
N2	0.25282 (13)	0.8494 (2)	0.72722 (12)	0.0251 (4)
N3	0.61120 (13)	0.9993 (2)	0.62362 (14)	0.0275 (4)
C1	0.11176 (15)	0.8807 (3)	0.71164 (14)	0.0243 (5)
C2	0.01730 (15)	0.9315 (2)	0.68075 (14)	0.0220 (5)
C3	−0.02015 (15)	1.0140 (2)	0.60582 (14)	0.0235 (5)
H3	0.0168	1.0402	0.5743	0.028*
C4	−0.10982 (16)	1.0577 (3)	0.57728 (16)	0.0283 (5)
H4	−0.1348	1.1142	0.5264	0.034*
C5	−0.16410 (16)	1.0184 (3)	0.62350 (17)	0.0315 (5)
H5	−0.2264	1.0472	0.6037	0.038*
C6	−0.12745 (17)	0.9380 (3)	0.69772 (17)	0.0310 (5)
H6	−0.1652	0.9116	0.7284	0.037*
C7	−0.03598 (16)	0.8944 (3)	0.72900 (16)	0.0272 (5)
C8	0.00372 (18)	0.8092 (3)	0.81182 (17)	0.0358 (6)
H8A	−0.0152	0.7060	0.8002	0.043*
H8B	−0.0223	0.8472	0.8532	0.043*
C9	0.10743 (18)	0.8158 (3)	0.85304 (17)	0.0360 (6)
H9A	0.1270	0.9154	0.8749	0.043*
H9B	0.1295	0.7473	0.9021	0.043*
C10	0.14749 (17)	0.7754 (3)	0.78660 (16)	0.0302 (5)
H10	0.1262	0.6752	0.7650	0.036*
C11	0.25155 (16)	0.7839 (3)	0.80769 (15)	0.0262 (5)
H11	0.2768	0.6828	0.8135	0.031*
C12	0.30768 (16)	0.8718 (2)	0.88630 (15)	0.0263 (5)
C13	0.3217 (2)	1.0205 (3)	0.88187 (17)	0.0360 (6)
H13	0.2957	1.0694	0.8283	0.043*
C14	0.3723 (2)	1.0976 (3)	0.95360 (19)	0.0465 (7)
H14	0.3820	1.1990	0.9492	0.056*
C15	0.4096 (2)	1.0290 (3)	1.0325 (2)	0.0509 (8)
H15	0.4447	1.0828	1.0822	0.061*
C16	0.3952 (2)	0.8806 (3)	1.03832 (19)	0.0480 (7)
H16	0.4194	0.8330	1.0924	0.058*
C17	0.34566 (19)	0.8023 (3)	0.96556 (17)	0.0363 (6)
H17	0.3375	0.7004	0.9696	0.044*
C18	0.32543 (14)	0.8521 (2)	0.70087 (14)	0.0192 (4)
C19	0.31803 (14)	0.9196 (2)	0.62303 (14)	0.0208 (4)
H19	0.2631	0.9679	0.5895	0.025*
C20	0.39002 (15)	0.9158 (2)	0.59542 (14)	0.0223 (5)
H20	0.3844	0.9610	0.5427	0.027*
C21	0.47139 (14)	0.8456 (2)	0.64448 (14)	0.0210 (4)
C22	0.48012 (15)	0.7814 (2)	0.72190 (15)	0.0236 (5)
H22	0.5356	0.7347	0.7556	0.028*
C23	0.40790 (15)	0.7853 (2)	0.75024 (14)	0.0236 (5)
H23	0.4145	0.7420	0.8037	0.028*
C24	0.7520 (3)	0.4101 (4)	0.6419 (2)	0.0558 (8)
H24A	0.8069	0.3642	0.6373	0.067*
H24B	0.7250	0.3397	0.6706	0.067*
C25	0.6861 (3)	0.4394 (4)	0.5558 (3)	0.0666 (10)
H25A	0.6701	0.3481	0.5234	0.100*
H25B	0.7128	0.5071	0.5264	0.100*
H25C	0.6309	0.4829	0.5597	0.100*
H1n	0.6416 (19)	1.014 (4)	0.6783 (8)	0.054 (10)*
H2n	0.5739 (14)	1.066 (2)	0.5919 (14)	0.028 (7)*
H3o	0.7383 (16)	0.605 (3)	0.687 (2)	0.054 (10)*

	U11	U22	U33	U12	U13	U23
S1	0.0220 (3)	0.0289 (3)	0.0241 (3)	0.0055 (2)	0.0119 (2)	−0.0008 (2)
O1	0.0288 (9)	0.0381 (9)	0.0339 (10)	0.0136 (7)	0.0143 (8)	0.0045 (8)
O2	0.0310 (9)	0.0369 (9)	0.0238 (9)	0.0034 (7)	0.0139 (7)	−0.0061 (7)
O3	0.0360 (10)	0.0508 (12)	0.0452 (12)	0.0167 (9)	0.0099 (9)	0.0101 (10)
N1	0.0223 (9)	0.0203 (9)	0.0189 (9)	−0.0011 (7)	0.0099 (8)	−0.0027 (7)
N2	0.0226 (9)	0.0339 (10)	0.0204 (10)	0.0037 (8)	0.0099 (8)	0.0090 (8)
N3	0.0221 (10)	0.0343 (11)	0.0283 (12)	0.0009 (9)	0.0119 (9)	0.0002 (9)
C1	0.0266 (11)	0.0293 (11)	0.0203 (11)	−0.0045 (9)	0.0125 (9)	−0.0027 (9)
C2	0.0235 (11)	0.0227 (10)	0.0236 (11)	−0.0061 (9)	0.0131 (9)	−0.0055 (9)
C3	0.0234 (10)	0.0259 (11)	0.0237 (12)	−0.0062 (9)	0.0115 (9)	−0.0047 (9)
C4	0.0258 (11)	0.0299 (12)	0.0283 (13)	−0.0035 (10)	0.0088 (10)	−0.0022 (10)
C5	0.0230 (11)	0.0333 (12)	0.0415 (15)	−0.0031 (10)	0.0155 (11)	−0.0056 (11)
C6	0.0302 (12)	0.0310 (12)	0.0409 (15)	−0.0044 (10)	0.0236 (12)	−0.0030 (11)
C7	0.0313 (12)	0.0257 (11)	0.0318 (13)	−0.0033 (10)	0.0201 (11)	−0.0033 (10)
C8	0.0378 (14)	0.0435 (14)	0.0380 (15)	0.0015 (12)	0.0276 (13)	0.0073 (12)
C9	0.0399 (14)	0.0433 (14)	0.0336 (14)	0.0112 (12)	0.0239 (12)	0.0132 (12)
C10	0.0352 (13)	0.0294 (12)	0.0313 (13)	0.0011 (10)	0.0187 (11)	0.0038 (10)
C11	0.0290 (12)	0.0305 (11)	0.0229 (12)	0.0030 (10)	0.0141 (10)	0.0065 (9)
C12	0.0333 (12)	0.0255 (11)	0.0243 (12)	0.0089 (10)	0.0158 (10)	0.0044 (9)
C13	0.0557 (17)	0.0276 (12)	0.0300 (14)	0.0099 (12)	0.0220 (13)	0.0045 (10)
C14	0.071 (2)	0.0300 (13)	0.0424 (17)	−0.0030 (14)	0.0262 (16)	−0.0046 (12)
C15	0.068 (2)	0.0465 (17)	0.0341 (16)	−0.0026 (15)	0.0144 (15)	−0.0128 (13)
C16	0.064 (2)	0.0488 (17)	0.0250 (14)	0.0069 (15)	0.0094 (14)	0.0021 (12)
C17	0.0504 (16)	0.0290 (12)	0.0283 (13)	0.0059 (12)	0.0132 (12)	0.0062 (10)
C18	0.0219 (10)	0.0179 (10)	0.0195 (11)	−0.0021 (8)	0.0095 (9)	−0.0024 (8)
C19	0.0193 (10)	0.0249 (11)	0.0171 (11)	0.0006 (8)	0.0056 (9)	0.0003 (8)
C20	0.0234 (11)	0.0264 (11)	0.0182 (11)	0.0006 (9)	0.0088 (9)	0.0012 (9)
C21	0.0207 (10)	0.0217 (10)	0.0215 (11)	0.0011 (8)	0.0090 (9)	−0.0030 (8)
C22	0.0228 (10)	0.0220 (10)	0.0256 (12)	0.0038 (9)	0.0083 (9)	0.0023 (9)
C23	0.0265 (11)	0.0246 (11)	0.0204 (11)	0.0040 (9)	0.0095 (9)	0.0048 (9)
C24	0.071 (2)	0.0537 (19)	0.052 (2)	0.0154 (17)	0.0332 (18)	−0.0003 (15)
C25	0.067 (2)	0.071 (2)	0.064 (3)	−0.0048 (19)	0.027 (2)	−0.0164 (19)

S1—O1	1.4345 (17)	C10—C11	1.546 (3)
S1—O2	1.4414 (17)	C10—H10	1.0000
S1—N3	1.613 (2)	C11—C12	1.518 (3)
S1—C21	1.759 (2)	C11—H11	1.0000
O3—C24	1.493 (4)	C12—C17	1.393 (3)
O3—H3o	0.839 (10)	C12—C13	1.389 (3)
N1—C1	1.285 (3)	C13—C14	1.368 (4)
N1—N2	1.393 (3)	C13—H13	0.9500
N2—C18	1.370 (3)	C14—C15	1.384 (4)
N2—C11	1.483 (3)	C14—H14	0.9500
N3—H1n	0.873 (10)	C15—C16	1.390 (4)
N3—H2n	0.877 (10)	C15—H15	0.9500
C1—C2	1.459 (3)	C16—C17	1.381 (4)
C1—C10	1.518 (3)	C16—H16	0.9500
C2—C3	1.396 (3)	C17—H17	0.9500
C2—C7	1.406 (3)	C18—C23	1.398 (3)
C3—C4	1.373 (3)	C18—C19	1.409 (3)
C3—H3	0.9500	C19—C20	1.375 (3)
C4—C5	1.397 (3)	C19—H19	0.9500
C4—H4	0.9500	C20—C21	1.398 (3)
C5—C6	1.375 (4)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.384 (3)
C6—C7	1.398 (3)	C22—C23	1.386 (3)
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.512 (3)	C23—H23	0.9500
C8—C9	1.522 (4)	C24—C25	1.457 (5)
C8—H8A	0.9900	C24—H24A	0.9900
C8—H8B	0.9900	C24—H24B	0.9900
C9—C10	1.515 (3)	C25—H25A	0.9800
C9—H9A	0.9900	C25—H25B	0.9800
C9—H9B	0.9900	C25—H25C	0.9800
O1—S1—O2	119.27 (10)	N2—C11—C10	100.52 (18)
O1—S1—N3	106.86 (11)	C12—C11—C10	116.95 (19)
O2—S1—N3	106.42 (11)	N2—C11—H11	109.0
O1—S1—C21	107.25 (10)	C12—C11—H11	109.0
O2—S1—C21	107.81 (10)	C10—C11—H11	109.0
N3—S1—C21	108.93 (10)	C17—C12—C13	118.7 (2)
C24—O3—H3o	114 (2)	C17—C12—C11	119.3 (2)
C1—N1—N2	107.35 (18)	C13—C12—C11	121.9 (2)
C18—N2—N1	120.57 (17)	C14—C13—C12	120.9 (2)
C18—N2—C11	126.45 (18)	C14—C13—H13	119.5
N1—N2—C11	112.97 (16)	C12—C13—H13	119.5
S1—N3—H1n	111 (2)	C13—C14—C15	120.5 (3)
S1—N3—H2n	110.5 (17)	C13—C14—H14	119.8
H1n—N3—H2n	121 (3)	C15—C14—H14	119.8
N1—C1—C2	124.7 (2)	C14—C15—C16	119.4 (3)
N1—C1—C10	114.3 (2)	C14—C15—H15	120.3
C2—C1—C10	120.91 (19)	C16—C15—H15	120.3
C3—C2—C7	120.3 (2)	C17—C16—C15	120.1 (3)
C3—C2—C1	121.89 (19)	C17—C16—H16	119.9
C7—C2—C1	117.8 (2)	C15—C16—H16	119.9
C4—C3—C2	120.6 (2)	C16—C17—C12	120.4 (3)
C4—C3—H3	119.7	C16—C17—H17	119.8
C2—C3—H3	119.7	C12—C17—H17	119.8
C3—C4—C5	119.6 (2)	N2—C18—C23	120.35 (19)
C3—C4—H4	120.2	N2—C18—C19	120.88 (19)
C5—C4—H4	120.2	C23—C18—C19	118.76 (19)
C6—C5—C4	120.1 (2)	C20—C19—C18	120.3 (2)
C6—C5—H5	120.0	C20—C19—H19	119.9
C4—C5—H5	120.0	C18—C19—H19	119.9
C5—C6—C7	121.5 (2)	C19—C20—C21	120.4 (2)
C5—C6—H6	119.3	C19—C20—H20	119.8
C7—C6—H6	119.3	C21—C20—H20	119.8
C6—C7—C2	117.9 (2)	C22—C21—C20	119.90 (19)
C6—C7—C8	120.8 (2)	C22—C21—S1	120.66 (17)
C2—C7—C8	121.4 (2)	C20—C21—S1	119.44 (16)
C7—C8—C9	113.95 (19)	C21—C22—C23	120.0 (2)
C7—C8—H8A	108.8	C21—C22—H22	120.0
C9—C8—H8A	108.8	C23—C22—H22	120.0
C7—C8—H8B	108.8	C22—C23—C18	120.6 (2)
C9—C8—H8B	108.8	C22—C23—H23	119.7
H8A—C8—H8B	107.7	C18—C23—H23	119.7
C10—C9—C8	109.0 (2)	C25—C24—O3	113.2 (3)
C10—C9—H9A	109.9	C25—C24—H24A	108.9
C8—C9—H9A	109.9	O3—C24—H24A	108.9
C10—C9—H9B	109.9	C25—C24—H24B	108.9
C8—C9—H9B	109.9	O3—C24—H24B	108.9
H9A—C9—H9B	108.3	H24A—C24—H24B	107.7
C9—C10—C1	108.90 (19)	C24—C25—H25A	109.5
C9—C10—C11	121.0 (2)	C24—C25—H25B	109.5
C1—C10—C11	101.19 (17)	H25A—C25—H25B	109.5
C9—C10—H10	108.4	C24—C25—H25C	109.5
C1—C10—H10	108.4	H25A—C25—H25C	109.5
C11—C10—H10	108.4	H25B—C25—H25C	109.5
N2—C11—C12	111.94 (19)
C1—N1—N2—C18	172.3 (2)	C9—C10—C11—C12	−16.4 (3)
C1—N1—N2—C11	−8.9 (2)	C1—C10—C11—C12	103.9 (2)
N2—N1—C1—C2	177.9 (2)	N2—C11—C12—C17	−153.5 (2)
N2—N1—C1—C10	−4.5 (3)	C10—C11—C12—C17	91.3 (3)
N1—C1—C2—C3	5.3 (3)	N2—C11—C12—C13	27.2 (3)
C10—C1—C2—C3	−172.2 (2)	C10—C11—C12—C13	−88.0 (3)
N1—C1—C2—C7	−174.8 (2)	C17—C12—C13—C14	0.5 (4)
C10—C1—C2—C7	7.8 (3)	C11—C12—C13—C14	179.8 (2)
C7—C2—C3—C4	−1.3 (3)	C12—C13—C14—C15	−1.0 (4)
C1—C2—C3—C4	178.6 (2)	C13—C14—C15—C16	0.1 (5)
C2—C3—C4—C5	−0.3 (3)	C14—C15—C16—C17	1.3 (5)
C3—C4—C5—C6	0.8 (4)	C15—C16—C17—C12	−1.8 (5)
C4—C5—C6—C7	0.3 (4)	C13—C12—C17—C16	0.9 (4)
C5—C6—C7—C2	−1.9 (4)	C11—C12—C17—C16	−178.5 (2)
C5—C6—C7—C8	178.5 (2)	N1—N2—C18—C23	−179.40 (19)
C3—C2—C7—C6	2.3 (3)	C11—N2—C18—C23	2.0 (3)
C1—C2—C7—C6	−177.6 (2)	N1—N2—C18—C19	−0.6 (3)
C3—C2—C7—C8	−178.0 (2)	C11—N2—C18—C19	−179.3 (2)
C1—C2—C7—C8	2.1 (3)	N2—C18—C19—C20	−177.0 (2)
C6—C7—C8—C9	−159.6 (2)	C23—C18—C19—C20	1.8 (3)
C2—C7—C8—C9	20.8 (3)	C18—C19—C20—C21	−0.3 (3)
C7—C8—C9—C10	−51.6 (3)	C19—C20—C21—C22	−0.9 (3)
C8—C9—C10—C1	58.8 (3)	C19—C20—C21—S1	179.81 (17)
C8—C9—C10—C11	175.3 (2)	O1—S1—C21—C22	12.3 (2)
N1—C1—C10—C9	143.4 (2)	O2—S1—C21—C22	141.86 (18)
C2—C1—C10—C9	−38.9 (3)	N3—S1—C21—C22	−103.05 (19)
N1—C1—C10—C11	14.9 (3)	O1—S1—C21—C20	−168.51 (17)
C2—C1—C10—C11	−167.4 (2)	O2—S1—C21—C20	−38.9 (2)
C18—N2—C11—C12	71.2 (3)	N3—S1—C21—C20	76.2 (2)
N1—N2—C11—C12	−107.5 (2)	C20—C21—C22—C23	0.7 (3)
C18—N2—C11—C10	−163.9 (2)	S1—C21—C22—C23	179.98 (17)
N1—N2—C11—C10	17.4 (2)	C21—C22—C23—C18	0.7 (3)
C9—C10—C11—N2	−137.8 (2)	N2—C18—C23—C22	176.8 (2)
C1—C10—C11—N2	−17.5 (2)	C19—C18—C23—C22	−2.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O1	0.84 (1)	2.04 (1)	2.875 (2)	175 (3)
N3—H1n···O3i	0.87 (1)	2.02 (1)	2.894 (3)	176 (3)
N3—H2n···O2ii	0.88 (1)	2.16 (1)	3.007 (3)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O1	0.84 (1)	2.04 (1)	2.875 (2)	175 (3)
N3—H1n⋯O3i	0.87 (1)	2.02 (1)	2.894 (3)	176 (3)
N3—H2n⋯O2ii	0.88 (1)	2.16 (1)	3.007 (3)	163 (2)

Symmetry codes: (i) ; (ii) .