(E)-5-(2-Chloro-phen-yl)-7-ethyl-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-4-ium 2,4,6-trinitro-phenolate.

In the title molecular salt, C(15)H(14)ClN(2)OS(+)·C(6)H(2)N(3)O(7) (-), protonation occurred on the double-bonded N atom. One of the nitro groups shows slight disorder over two orientations, with an occupancy ratio of 0.91:0.09. In the crystal, classical N-H⋯O hydrogen bonds, as well as C-H⋯O contacts connect the components into a three-dimensional network. The seven-membered ring adopts a boat-like conformation. The least-squares plane defined by its non-H atoms encloses an angle of 38.99 (6)° with the benzene ring bonded to it.

Related literature

For pharmaceutical background to benzodiazepines, see: Robol et al. (1996 ▶); Evans et al. (2001 ▶). For related structures, see: Scammells et al. (2001 ▶); Jasinski et al. (2010 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H14ClN2OS+·C6H2N3O7 −

M = 533.90

Monoclinic,

a = 10.5704 (2) Å

b = 20.0667 (5) Å

c = 11.3741 (2) Å

β = 110.666 (1)°

V = 2257.35 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 200 K

0.59 × 0.49 × 0.36 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶). T min = 0.807, T max = 0.892

21254 measured reflections

5607 independent reflections

5073 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.05

5607 reflections

343 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); 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 Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002607/pk2384sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812002607/pk2384Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002607/pk2384Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812002607/pk2384Isup4.cml

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

C15H14ClN2OS+·C6H2N3O7−	F(000) = 1096
Mr = 533.90	Dx = 1.571 Mg m−3
Monoclinic, P21/c	Melting point: 518 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.5704 (2) Å	Cell parameters from 9909 reflections
b = 20.0667 (5) Å	θ = 2.9–28.3°
c = 11.3741 (2) Å	µ = 0.32 mm−1
β = 110.666 (1)°	T = 200 K
V = 2257.35 (8) Å3	Block, brown
Z = 4	0.59 × 0.49 × 0.36 mm

Bruker APEXII CCD diffractometer	5607 independent reflections
Radiation source: fine-focus sealed tube	5073 reflections with I > 2σ(I)
graphite	Rint = 0.013
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008).	h = −13→14
Tmin = 0.807, Tmax = 0.892	k = −26→26
21254 measured reflections	l = −15→15

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0349P)2 + 1.1718P] where P = (Fo2 + 2Fc2)/3
5607 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.57956 (3)	0.230591 (16)	0.27567 (3)	0.03062 (8)
S1	0.08122 (3)	0.038903 (15)	−0.15866 (3)	0.02327 (8)
O1	0.53537 (10)	0.04170 (5)	−0.16774 (10)	0.0361 (2)
O31	0.75141 (9)	0.09665 (4)	0.21426 (8)	0.02763 (19)
O321	0.75835 (10)	0.21026 (6)	0.09075 (9)	0.0377 (2)
O322	0.96274 (13)	0.23796 (7)	0.11380 (11)	0.0495 (3)
O341	1.27262 (12)	0.24856 (6)	0.54001 (12)	0.0505 (3)
O342	1.25204 (13)	0.17919 (7)	0.67751 (12)	0.0607 (4)
N36	0.84539 (12)	0.04459 (6)	0.46335 (11)	0.0328 (3)
O361	0.8483 (2)	0.04566 (12)	0.57264 (12)	0.0591 (7)	0.913 (5)
O362	0.79227 (19)	−0.00036 (7)	0.39045 (12)	0.0432 (5)	0.913 (5)
O363	0.8925 (12)	0.0218 (6)	0.5586 (12)	0.023 (3)*	0.087 (5)
O364	0.7289 (16)	0.0258 (8)	0.3784 (12)	0.037 (4)*	0.087 (5)
N1	0.49406 (10)	0.12534 (5)	0.07439 (9)	0.01965 (19)
H71	0.5767 (19)	0.1274 (9)	0.1273 (17)	0.040 (5)*
N2	0.34466 (10)	0.03182 (5)	−0.12197 (9)	0.0216 (2)
H72	0.3224 (17)	−0.0023 (9)	−0.1669 (16)	0.033 (4)*
N32	0.87981 (11)	0.21070 (6)	0.15093 (10)	0.0277 (2)
N34	1.21470 (12)	0.20290 (6)	0.57125 (12)	0.0375 (3)
C1	0.45809 (12)	0.06515 (6)	−0.12171 (11)	0.0229 (2)
C2	0.47774 (12)	0.13264 (6)	−0.05765 (11)	0.0228 (2)
H2A	0.5588	0.1545	−0.0645	0.027*
H2B	0.3985	0.1613	−0.1002	0.027*
C3	0.39456 (11)	0.11469 (5)	0.11481 (10)	0.0186 (2)
C4	−0.11953 (12)	0.08838 (7)	−0.07592 (13)	0.0272 (3)
H4A	−0.1330	0.1015	0.0028	0.033*
H4B	−0.1627	0.0444	−0.1017	0.033*
C5	−0.18803 (14)	0.13922 (8)	−0.17752 (15)	0.0399 (3)
H5A	−0.1502	0.1835	−0.1498	0.060*
H5B	−0.2854	0.1397	−0.1933	0.060*
H5C	−0.1727	0.1273	−0.2549	0.060*
C11	0.24806 (11)	0.05778 (6)	−0.07911 (10)	0.0194 (2)
C12	0.26416 (11)	0.09611 (6)	0.02726 (10)	0.0198 (2)
C13	0.13619 (12)	0.10916 (6)	0.04104 (11)	0.0230 (2)
H13	0.1277	0.1342	0.1088	0.028*
C14	0.02920 (12)	0.08249 (6)	−0.05130 (11)	0.0232 (2)
C21	0.42065 (11)	0.11893 (6)	0.25106 (11)	0.0210 (2)
C22	0.50465 (12)	0.16687 (6)	0.33080 (11)	0.0243 (2)
C23	0.52897 (15)	0.16634 (8)	0.45900 (13)	0.0368 (3)
H23	0.5859	0.1992	0.5119	0.044*
C24	0.47029 (17)	0.11802 (9)	0.50923 (13)	0.0428 (4)
H24	0.4878	0.1174	0.5971	0.051*
C25	0.38611 (16)	0.07037 (8)	0.43273 (14)	0.0377 (3)
H25	0.3456	0.0373	0.4678	0.045*
C26	0.36134 (13)	0.07120 (7)	0.30489 (12)	0.0283 (3)
H26	0.3028	0.0387	0.2526	0.034*
C31	0.85448 (11)	0.12197 (6)	0.29523 (11)	0.0208 (2)
C32	0.92952 (12)	0.17741 (6)	0.27217 (11)	0.0225 (2)
C33	1.04736 (12)	0.20209 (6)	0.35838 (12)	0.0256 (2)
H33	1.0953	0.2371	0.3363	0.031*
C34	1.09452 (12)	0.17498 (6)	0.47757 (12)	0.0267 (3)
C35	1.02603 (13)	0.12448 (6)	0.51186 (12)	0.0280 (3)
H35	1.0569	0.1080	0.5955	0.034*
C36	0.91220 (12)	0.09847 (6)	0.42255 (11)	0.0244 (2)

	U11	U22	U33	U12	U13	U23
Cl1	0.03397 (16)	0.02676 (15)	0.03248 (16)	−0.01114 (12)	0.01341 (13)	−0.00916 (11)
S1	0.01661 (13)	0.02786 (15)	0.02118 (14)	−0.00278 (10)	0.00153 (10)	−0.00509 (10)
O1	0.0307 (5)	0.0438 (6)	0.0402 (5)	−0.0040 (4)	0.0204 (4)	−0.0127 (4)
O31	0.0212 (4)	0.0225 (4)	0.0289 (4)	−0.0008 (3)	−0.0038 (3)	−0.0028 (3)
O321	0.0293 (5)	0.0464 (6)	0.0305 (5)	0.0064 (4)	0.0020 (4)	0.0102 (4)
O322	0.0465 (6)	0.0593 (7)	0.0426 (6)	−0.0143 (6)	0.0155 (5)	0.0147 (5)
O341	0.0336 (6)	0.0361 (6)	0.0629 (8)	−0.0136 (5)	−0.0065 (5)	−0.0026 (5)
O342	0.0493 (7)	0.0693 (9)	0.0367 (6)	−0.0165 (6)	−0.0183 (5)	0.0039 (6)
N36	0.0317 (6)	0.0376 (6)	0.0242 (5)	−0.0089 (5)	0.0037 (4)	0.0028 (5)
O361	0.0699 (12)	0.0805 (14)	0.0235 (6)	−0.0390 (11)	0.0124 (6)	−0.0028 (7)
O362	0.0621 (11)	0.0307 (7)	0.0354 (6)	−0.0185 (7)	0.0154 (6)	−0.0032 (5)
N1	0.0162 (4)	0.0225 (5)	0.0180 (4)	−0.0010 (4)	0.0032 (4)	−0.0027 (3)
N2	0.0201 (5)	0.0224 (5)	0.0212 (5)	−0.0016 (4)	0.0061 (4)	−0.0056 (4)
N32	0.0303 (5)	0.0265 (5)	0.0250 (5)	0.0003 (4)	0.0082 (4)	0.0009 (4)
N34	0.0264 (6)	0.0322 (6)	0.0397 (7)	−0.0035 (5)	−0.0060 (5)	−0.0066 (5)
C1	0.0205 (5)	0.0290 (6)	0.0179 (5)	−0.0004 (4)	0.0052 (4)	−0.0012 (4)
C2	0.0228 (5)	0.0253 (5)	0.0201 (5)	−0.0040 (4)	0.0074 (4)	−0.0002 (4)
C3	0.0166 (5)	0.0174 (5)	0.0194 (5)	0.0000 (4)	0.0035 (4)	−0.0028 (4)
C4	0.0158 (5)	0.0295 (6)	0.0344 (6)	−0.0011 (4)	0.0065 (5)	−0.0028 (5)
C5	0.0244 (6)	0.0466 (8)	0.0456 (8)	0.0098 (6)	0.0083 (6)	0.0099 (7)
C11	0.0168 (5)	0.0203 (5)	0.0185 (5)	−0.0011 (4)	0.0030 (4)	−0.0006 (4)
C12	0.0163 (5)	0.0213 (5)	0.0199 (5)	−0.0009 (4)	0.0041 (4)	−0.0025 (4)
C13	0.0186 (5)	0.0248 (5)	0.0247 (5)	0.0001 (4)	0.0066 (4)	−0.0043 (4)
C14	0.0177 (5)	0.0242 (5)	0.0263 (6)	0.0001 (4)	0.0059 (4)	−0.0011 (4)
C21	0.0184 (5)	0.0240 (5)	0.0195 (5)	−0.0013 (4)	0.0052 (4)	−0.0040 (4)
C22	0.0218 (5)	0.0271 (6)	0.0237 (6)	−0.0050 (4)	0.0077 (4)	−0.0051 (4)
C23	0.0376 (7)	0.0466 (8)	0.0237 (6)	−0.0133 (6)	0.0077 (5)	−0.0128 (6)
C24	0.0486 (9)	0.0593 (10)	0.0206 (6)	−0.0123 (8)	0.0125 (6)	−0.0044 (6)
C25	0.0406 (8)	0.0459 (8)	0.0302 (7)	−0.0110 (6)	0.0168 (6)	0.0014 (6)
C26	0.0278 (6)	0.0305 (6)	0.0267 (6)	−0.0073 (5)	0.0099 (5)	−0.0036 (5)
C31	0.0171 (5)	0.0210 (5)	0.0218 (5)	0.0022 (4)	0.0037 (4)	−0.0029 (4)
C32	0.0212 (5)	0.0226 (5)	0.0215 (5)	0.0022 (4)	0.0049 (4)	−0.0002 (4)
C33	0.0204 (5)	0.0226 (5)	0.0317 (6)	−0.0009 (4)	0.0065 (5)	−0.0029 (5)
C34	0.0185 (5)	0.0257 (6)	0.0283 (6)	−0.0011 (4)	−0.0014 (5)	−0.0056 (5)
C35	0.0260 (6)	0.0291 (6)	0.0223 (5)	−0.0002 (5)	0.0005 (5)	−0.0009 (5)
C36	0.0227 (5)	0.0246 (6)	0.0231 (5)	−0.0023 (4)	0.0044 (5)	−0.0004 (4)

Cl1—C22	1.7337 (13)	C4—C5	1.5199 (19)
S1—C11	1.7164 (11)	C4—H4A	0.9900
S1—C14	1.7415 (12)	C4—H4B	0.9900
O1—C1	1.2102 (15)	C5—H5A	0.9800
O31—C31	1.2590 (14)	C5—H5B	0.9800
O321—N32	1.2234 (15)	C5—H5C	0.9800
O322—N32	1.2277 (15)	C11—C12	1.3925 (15)
O341—N34	1.2222 (18)	C12—C13	1.4396 (15)
O342—N34	1.2273 (18)	C13—C14	1.3528 (16)
N36—O363	1.118 (12)	C13—H13	0.9500
N36—O362	1.2196 (16)	C21—C26	1.3985 (17)
N36—O361	1.2330 (19)	C21—C22	1.4029 (16)
N36—O364	1.323 (14)	C22—C23	1.3885 (18)
N36—C36	1.4542 (16)	C23—C24	1.379 (2)
N1—C3	1.3056 (15)	C23—H23	0.9500
N1—C2	1.4574 (15)	C24—C25	1.384 (2)
N1—H71	0.870 (19)	C24—H24	0.9500
N2—C1	1.3720 (15)	C25—C26	1.3836 (18)
N2—C11	1.3795 (15)	C25—H25	0.9500
N2—H72	0.836 (18)	C26—H26	0.9500
N32—C32	1.4534 (15)	C31—C36	1.4380 (16)
N34—C34	1.4519 (15)	C31—C32	1.4431 (16)
C1—C2	1.5170 (17)	C32—C33	1.3771 (16)
C2—H2A	0.9900	C33—C34	1.3803 (18)
C2—H2B	0.9900	C33—H33	0.9500
C3—C12	1.4358 (15)	C34—C35	1.3793 (18)
C3—C21	1.4776 (15)	C35—C36	1.3745 (17)
C4—C14	1.5011 (16)	C35—H35	0.9500
C11—S1—C14	92.26 (5)	C12—C11—S1	111.57 (8)
O363—N36—O362	107.3 (6)	C11—C12—C3	122.62 (10)
O362—N36—O361	122.68 (13)	C11—C12—C13	111.32 (10)
O363—N36—O364	124.9 (9)	C3—C12—C13	125.89 (10)
O361—N36—O364	115.2 (6)	C14—C13—C12	113.81 (10)
O363—N36—C36	120.9 (6)	C14—C13—H13	123.1
O362—N36—C36	119.46 (11)	C12—C13—H13	123.1
O361—N36—C36	117.83 (12)	C13—C14—C4	130.33 (11)
O364—N36—C36	114.2 (6)	C13—C14—S1	111.02 (9)
C3—N1—C2	124.21 (10)	C4—C14—S1	118.55 (9)
C3—N1—H71	120.1 (12)	C26—C21—C22	117.76 (11)
C2—N1—H71	115.7 (12)	C26—C21—C3	118.24 (10)
C1—N2—C11	124.78 (10)	C22—C21—C3	123.97 (11)
C1—N2—H72	117.2 (11)	C23—C22—C21	120.93 (12)
C11—N2—H72	116.2 (11)	C23—C22—Cl1	116.52 (10)
O321—N32—O322	123.13 (12)	C21—C22—Cl1	122.52 (9)
O321—N32—C32	118.95 (11)	C24—C23—C22	119.79 (13)
O322—N32—C32	117.92 (11)	C24—C23—H23	120.1
O341—N34—O342	123.85 (12)	C22—C23—H23	120.1
O341—N34—C34	118.31 (12)	C23—C24—C25	120.57 (13)
O342—N34—C34	117.84 (13)	C23—C24—H24	119.7
O1—C1—N2	122.16 (12)	C25—C24—H24	119.7
O1—C1—C2	123.78 (11)	C26—C25—C24	119.56 (13)
N2—C1—C2	114.05 (10)	C26—C25—H25	120.2
N1—C2—C1	110.59 (10)	C24—C25—H25	120.2
N1—C2—H2A	109.5	C25—C26—C21	121.37 (12)
C1—C2—H2A	109.5	C25—C26—H26	119.3
N1—C2—H2B	109.5	C21—C26—H26	119.3
C1—C2—H2B	109.5	O31—C31—C36	123.67 (11)
H2A—C2—H2B	108.1	O31—C31—C32	124.57 (11)
N1—C3—C12	119.59 (10)	C36—C31—C32	111.76 (10)
N1—C3—C21	118.98 (10)	C33—C32—C31	124.39 (11)
C12—C3—C21	121.36 (10)	C33—C32—N32	116.33 (11)
C14—C4—C5	112.41 (11)	C31—C32—N32	119.27 (10)
C14—C4—H4A	109.1	C32—C33—C34	118.69 (12)
C5—C4—H4A	109.1	C32—C33—H33	120.7
C14—C4—H4B	109.1	C34—C33—H33	120.7
C5—C4—H4B	109.1	C35—C34—C33	121.57 (11)
H4A—C4—H4B	107.9	C35—C34—N34	119.12 (12)
C4—C5—H5A	109.5	C33—C34—N34	119.21 (12)
C4—C5—H5B	109.5	C36—C35—C34	118.68 (12)
H5A—C5—H5B	109.5	C36—C35—H35	120.7
C4—C5—H5C	109.5	C34—C35—H35	120.7
H5A—C5—H5C	109.5	C35—C36—C31	124.71 (11)
H5B—C5—H5C	109.5	C35—C36—N36	116.33 (11)
N2—C11—C12	129.56 (10)	C31—C36—N36	118.94 (10)
N2—C11—S1	118.77 (8)
C11—N2—C1—O1	−175.18 (12)	C22—C23—C24—C25	−0.7 (3)
C11—N2—C1—C2	5.61 (16)	C23—C24—C25—C26	0.3 (3)
C3—N1—C2—C1	−77.66 (14)	C24—C25—C26—C21	0.6 (2)
O1—C1—C2—N1	−117.45 (13)	C22—C21—C26—C25	−1.1 (2)
N2—C1—C2—N1	61.75 (13)	C3—C21—C26—C25	177.14 (13)
C2—N1—C3—C12	12.62 (17)	O31—C31—C32—C33	−175.40 (12)
C2—N1—C3—C21	−170.29 (10)	C36—C31—C32—C33	4.22 (17)
C1—N2—C11—C12	−41.65 (19)	O31—C31—C32—N32	4.86 (18)
C1—N2—C11—S1	142.17 (10)	C36—C31—C32—N32	−175.52 (10)
C14—S1—C11—N2	177.15 (10)	O321—N32—C32—C33	−152.12 (12)
C14—S1—C11—C12	0.32 (9)	O322—N32—C32—C33	28.00 (17)
N2—C11—C12—C3	−0.8 (2)	O321—N32—C32—C31	27.64 (17)
S1—C11—C12—C3	175.59 (9)	O322—N32—C32—C31	−152.24 (12)
N2—C11—C12—C13	−176.29 (12)	C31—C32—C33—C34	−3.70 (19)
S1—C11—C12—C13	0.10 (13)	N32—C32—C33—C34	176.05 (11)
N1—C3—C12—C11	32.88 (17)	C32—C33—C34—C35	−0.45 (19)
C21—C3—C12—C11	−144.13 (12)	C32—C33—C34—N34	−176.78 (12)
N1—C3—C12—C13	−152.30 (12)	O341—N34—C34—C35	−178.51 (13)
C21—C3—C12—C13	30.68 (18)	O342—N34—C34—C35	1.4 (2)
C11—C12—C13—C14	−0.65 (15)	O341—N34—C34—C33	−2.1 (2)
C3—C12—C13—C14	−175.96 (11)	O342—N34—C34—C33	177.82 (14)
C12—C13—C14—C4	−175.42 (12)	C33—C34—C35—C36	3.5 (2)
C12—C13—C14—S1	0.88 (14)	N34—C34—C35—C36	179.86 (12)
C5—C4—C14—C13	99.93 (17)	C34—C35—C36—C31	−2.8 (2)
C5—C4—C14—S1	−76.14 (14)	C34—C35—C36—N36	178.98 (12)
C11—S1—C14—C13	−0.69 (10)	O31—C31—C36—C35	178.71 (12)
C11—S1—C14—C4	176.10 (10)	C32—C31—C36—C35	−0.92 (17)
N1—C3—C21—C26	−138.62 (12)	O31—C31—C36—N36	−3.08 (18)
C12—C3—C21—C26	38.41 (16)	C32—C31—C36—N36	177.29 (11)
N1—C3—C21—C22	39.47 (17)	O363—N36—C36—C35	−7.5 (9)
C12—C3—C21—C22	−143.50 (12)	O362—N36—C36—C35	−144.83 (16)
C26—C21—C22—C23	0.68 (19)	O361—N36—C36—C35	33.3 (2)
C3—C21—C22—C23	−177.42 (12)	O364—N36—C36—C35	173.3 (8)
C26—C21—C22—Cl1	−177.61 (10)	O363—N36—C36—C31	174.1 (8)
C3—C21—C22—Cl1	4.29 (17)	O362—N36—C36—C31	36.8 (2)
C21—C22—C23—C24	0.2 (2)	O361—N36—C36—C31	−145.06 (19)
Cl1—C22—C23—C24	178.56 (13)	O364—N36—C36—C31	−5.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H71···O31	0.870 (19)	1.865 (19)	2.6847 (13)	156.3 (17)
N2—H72···O31i	0.836 (18)	2.047 (18)	2.8331 (13)	156.4 (16)
N2—H72···O362i	0.836 (18)	2.400 (17)	2.9495 (16)	123.9 (14)
C2—H2A···O321	0.99	2.49	3.2465 (16)	133
C2—H2B···O342ii	0.99	2.48	3.2505 (17)	134
C23—H23···O321iii	0.95	2.51	3.4193 (18)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H71⋯O31	0.870 (19)	1.865 (19)	2.6847 (13)	156.3 (17)
N2—H72⋯O31i	0.836 (18)	2.047 (18)	2.8331 (13)	156.4 (16)
N2—H72⋯O362i	0.836 (18)	2.400 (17)	2.9495 (16)	123.9 (14)
C2—H2A⋯O321	0.99	2.49	3.2465 (16)	133
C2—H2B⋯O342ii	0.99	2.48	3.2505 (17)	134
C23—H23⋯O321iii	0.95	2.51	3.4193 (18)	161

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