4-[Bis(4-fluorophenyl)methyl]piperazin-1-ium picrate.

The title compound {systematic name: 4-[bis(4-fluorophenyl)methyl]piperazin-1-ium 2,4,6-tri-nitro-phenolate}, C(17)H(19)F(2)N(2) (+)·C(6)H(2)N(3)O(7) (-), is the picrate salt of a piperazine-supported amine bearing a benzhydryl substituent on one of its N atoms. During co-crystallisation, protonation took place on the N atom of the secondary amine functionality. The non-aromatic six-membered heterocycle adopts a chair conformation. In the crystal, N-H⋯O hydrogen bonds as well as C-H⋯O contacts connect the components into a three-dimensional network.

Related literature

For background to the biological activity of piperazines, see: Brockunier et al. (2004 ▶); Bogatcheva et al. (2006 ▶). For related structures, see: Jasinski et al. (2010 ▶, 2011 ▶); Dutkiewicz et al. (2011 ▶). 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

C17H19F2N2 +·C6H2N3O7 −

M = 517.45

Monoclinic,

a = 8.9425 (2) Å

b = 11.8286 (2) Å

c = 23.0922 (4) Å

β = 105.720 (1)°

V = 2351.27 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 200 K

0.52 × 0.49 × 0.41 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS: Bruker, 2008 ▶) T min = 0.928, T max = 1.000

20823 measured reflections

5842 independent reflections

5041 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.03

5842 reflections

342 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.31 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: ORTEPIII (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/S160053681103580X/hg5090sup1.cif

Supplementary material file. DOI: 10.1107/S160053681103580X/hg5090Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103580X/hg5090Isup3.hkl

Supplementary material file. DOI: 10.1107/S160053681103580X/hg5090Isup4.cml

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

C17H19F2N2+·C6H2N3O7−	F(000) = 1072
Mr = 517.45	Dx = 1.462 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9984 reflections
a = 8.9425 (2) Å	θ = 2.5–28.3°
b = 11.8286 (2) Å	µ = 0.12 mm−1
c = 23.0922 (4) Å	T = 200 K
β = 105.720 (1)°	Block, yellow
V = 2351.27 (8) Å3	0.52 × 0.49 × 0.41 mm
Z = 4

Bruker APEXII CCD diffractometer	5842 independent reflections
Radiation source: fine-focus sealed tube	5041 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 = −10→11
Tmin = 0.928, Tmax = 1.000	k = −15→13
20823 measured reflections	l = −30→30

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.058P)2 + 0.8015P] where P = (Fo2 + 2Fc2)/3
5842 reflections	(Δ/σ)max < 0.001
342 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq
F1	0.59114 (13)	0.42083 (9)	0.07691 (4)	0.0571 (3)
F2	−0.17242 (8)	0.30044 (8)	0.27076 (4)	0.0414 (2)
N1	0.53229 (10)	0.45389 (8)	0.34157 (4)	0.02357 (19)
N2	0.77494 (11)	0.44880 (8)	0.45221 (4)	0.02322 (19)
H721	0.8435 (19)	0.4073 (14)	0.4805 (7)	0.036 (4)*
H722	0.7972 (18)	0.5235 (14)	0.4633 (7)	0.035 (4)*
C1	0.41152 (13)	0.49894 (9)	0.28976 (5)	0.0243 (2)
H1	0.4030	0.5824	0.2952	0.029*
C2	0.49947 (13)	0.48107 (10)	0.39896 (5)	0.0256 (2)
H2A	0.3914	0.4593	0.3972	0.031*
H2B	0.5104	0.5635	0.4064	0.031*
C3	0.61166 (12)	0.41795 (10)	0.44964 (5)	0.0252 (2)
H3A	0.5902	0.4370	0.4884	0.030*
H3B	0.5970	0.3355	0.4431	0.030*
C4	0.80775 (12)	0.43290 (10)	0.39261 (5)	0.0259 (2)
H4A	0.8047	0.3514	0.3826	0.031*
H4B	0.9129	0.4618	0.3945	0.031*
C5	0.68813 (12)	0.49562 (10)	0.34431 (5)	0.0254 (2)
H5A	0.6942	0.5776	0.3534	0.030*
H5B	0.7098	0.4844	0.3049	0.030*
C11	0.45589 (13)	0.47782 (10)	0.23136 (5)	0.0255 (2)
C12	0.48205 (16)	0.56737 (11)	0.19670 (6)	0.0357 (3)
H12	0.4681	0.6426	0.2087	0.043*
C13	0.52840 (18)	0.54931 (12)	0.14453 (6)	0.0423 (3)
H13	0.5465	0.6111	0.1210	0.051*
C14	0.54715 (16)	0.44020 (13)	0.12803 (5)	0.0369 (3)
C15	0.51902 (18)	0.34899 (12)	0.16014 (6)	0.0417 (3)
H15	0.5313	0.2741	0.1473	0.050*
C16	0.47223 (17)	0.36882 (11)	0.21181 (6)	0.0372 (3)
H16	0.4509	0.3065	0.2343	0.045*
C21	0.25510 (12)	0.44523 (9)	0.28664 (5)	0.0241 (2)
C22	0.24318 (14)	0.33552 (10)	0.30656 (6)	0.0303 (2)
H22	0.3351	0.2936	0.3238	0.036*
C23	0.09940 (14)	0.28616 (11)	0.30173 (6)	0.0321 (3)
H23	0.0917	0.2115	0.3158	0.039*
C24	−0.03126 (13)	0.34853 (11)	0.27601 (5)	0.0304 (2)
C25	−0.02518 (14)	0.45697 (12)	0.25579 (6)	0.0335 (3)
H25	−0.1178	0.4978	0.2381	0.040*
C26	0.11954 (14)	0.50573 (11)	0.26174 (5)	0.0298 (2)
H26	0.1260	0.5813	0.2487	0.036*
O1	0.04838 (9)	0.14124 (7)	0.02412 (4)	0.02909 (18)
O31	0.31391 (13)	0.16472 (9)	−0.00959 (5)	0.0496 (3)
O32	0.30392 (17)	0.32242 (10)	−0.05643 (6)	0.0588 (3)
O41	0.22278 (14)	0.65139 (8)	0.05559 (5)	0.0485 (3)
O42	0.08126 (16)	0.63785 (9)	0.11771 (6)	0.0578 (3)
O51	−0.12687 (16)	0.26580 (12)	0.15001 (5)	0.0641 (4)
O52	−0.20063 (15)	0.17435 (12)	0.06807 (5)	0.0598 (4)
N3	0.27271 (13)	0.26325 (9)	−0.01814 (5)	0.0323 (2)
N4	0.14537 (14)	0.59644 (9)	0.08192 (5)	0.0380 (3)
N5	−0.11622 (13)	0.24272 (10)	0.10035 (5)	0.0349 (2)
C31	0.07480 (12)	0.24316 (9)	0.03909 (5)	0.0233 (2)
C32	0.18288 (13)	0.31337 (10)	0.01940 (5)	0.0258 (2)
C33	0.20463 (14)	0.42683 (10)	0.03198 (5)	0.0284 (2)
H33	0.2723	0.4702	0.0154	0.034*
C34	0.12583 (14)	0.47641 (10)	0.06937 (5)	0.0299 (2)
C35	0.02432 (14)	0.41477 (10)	0.09322 (5)	0.0307 (2)
H35	−0.0260	0.4491	0.1201	0.037*
C36	−0.00186 (13)	0.30330 (10)	0.07723 (5)	0.0270 (2)

	U11	U22	U33	U12	U13	U23
F1	0.0726 (6)	0.0721 (7)	0.0364 (4)	0.0016 (5)	0.0315 (4)	−0.0020 (4)
F2	0.0245 (4)	0.0574 (5)	0.0434 (4)	−0.0087 (3)	0.0112 (3)	−0.0072 (4)
N1	0.0199 (4)	0.0306 (5)	0.0207 (4)	−0.0002 (3)	0.0064 (3)	0.0021 (3)
N2	0.0215 (4)	0.0250 (5)	0.0227 (4)	0.0005 (3)	0.0052 (3)	0.0024 (3)
C1	0.0248 (5)	0.0242 (5)	0.0238 (5)	0.0009 (4)	0.0064 (4)	0.0029 (4)
C2	0.0218 (5)	0.0334 (6)	0.0230 (5)	0.0022 (4)	0.0081 (4)	0.0020 (4)
C3	0.0226 (5)	0.0306 (5)	0.0238 (5)	−0.0013 (4)	0.0086 (4)	0.0034 (4)
C4	0.0219 (5)	0.0315 (6)	0.0258 (5)	0.0015 (4)	0.0090 (4)	−0.0003 (4)
C5	0.0224 (5)	0.0311 (6)	0.0241 (5)	−0.0019 (4)	0.0089 (4)	0.0024 (4)
C11	0.0241 (5)	0.0297 (5)	0.0219 (5)	−0.0011 (4)	0.0045 (4)	0.0023 (4)
C12	0.0472 (7)	0.0301 (6)	0.0318 (6)	−0.0115 (5)	0.0144 (5)	−0.0011 (5)
C13	0.0555 (8)	0.0427 (7)	0.0331 (6)	−0.0150 (6)	0.0195 (6)	0.0033 (5)
C14	0.0366 (6)	0.0519 (8)	0.0244 (5)	−0.0009 (6)	0.0118 (5)	−0.0008 (5)
C15	0.0556 (8)	0.0374 (7)	0.0349 (7)	0.0105 (6)	0.0171 (6)	0.0008 (5)
C16	0.0530 (8)	0.0298 (6)	0.0321 (6)	0.0081 (6)	0.0173 (6)	0.0077 (5)
C21	0.0227 (5)	0.0270 (5)	0.0222 (5)	0.0013 (4)	0.0054 (4)	0.0008 (4)
C22	0.0242 (5)	0.0278 (6)	0.0371 (6)	0.0017 (4)	0.0053 (4)	0.0045 (5)
C23	0.0303 (6)	0.0304 (6)	0.0359 (6)	−0.0034 (5)	0.0091 (5)	0.0006 (5)
C24	0.0230 (5)	0.0428 (7)	0.0267 (5)	−0.0046 (5)	0.0091 (4)	−0.0067 (5)
C25	0.0243 (5)	0.0453 (7)	0.0308 (6)	0.0085 (5)	0.0076 (4)	0.0042 (5)
C26	0.0292 (6)	0.0319 (6)	0.0292 (5)	0.0064 (5)	0.0094 (4)	0.0058 (4)
O1	0.0264 (4)	0.0238 (4)	0.0361 (4)	−0.0003 (3)	0.0067 (3)	−0.0050 (3)
O31	0.0572 (7)	0.0395 (5)	0.0658 (7)	0.0152 (5)	0.0400 (6)	0.0056 (5)
O32	0.0885 (9)	0.0463 (6)	0.0618 (7)	−0.0101 (6)	0.0547 (7)	0.0002 (5)
O41	0.0624 (7)	0.0266 (5)	0.0541 (6)	−0.0054 (4)	0.0115 (5)	0.0024 (4)
O42	0.0807 (9)	0.0339 (5)	0.0635 (7)	0.0032 (5)	0.0279 (6)	−0.0179 (5)
O51	0.0808 (9)	0.0832 (9)	0.0408 (6)	−0.0316 (7)	0.0379 (6)	−0.0244 (6)
O52	0.0595 (7)	0.0789 (8)	0.0511 (6)	−0.0385 (6)	0.0324 (5)	−0.0295 (6)
N3	0.0350 (5)	0.0328 (5)	0.0340 (5)	−0.0041 (4)	0.0176 (4)	−0.0032 (4)
N4	0.0454 (6)	0.0256 (5)	0.0375 (6)	0.0030 (4)	0.0016 (5)	−0.0041 (4)
N5	0.0383 (6)	0.0413 (6)	0.0293 (5)	−0.0061 (5)	0.0162 (4)	−0.0088 (4)
C31	0.0234 (5)	0.0244 (5)	0.0208 (5)	0.0014 (4)	0.0038 (4)	−0.0010 (4)
C32	0.0263 (5)	0.0277 (5)	0.0239 (5)	0.0007 (4)	0.0078 (4)	−0.0014 (4)
C33	0.0295 (5)	0.0268 (5)	0.0272 (5)	−0.0020 (4)	0.0045 (4)	0.0011 (4)
C34	0.0345 (6)	0.0227 (5)	0.0287 (5)	0.0015 (4)	0.0019 (4)	−0.0036 (4)
C35	0.0335 (6)	0.0321 (6)	0.0255 (5)	0.0033 (5)	0.0064 (4)	−0.0067 (4)
C36	0.0277 (5)	0.0315 (6)	0.0223 (5)	−0.0015 (4)	0.0078 (4)	−0.0036 (4)

F1—C14	1.3610 (14)	C15—H15	0.9500
F2—C24	1.3597 (13)	C16—H16	0.9500
N1—C5	1.4636 (13)	C21—C22	1.3905 (16)
N1—C2	1.4686 (13)	C21—C26	1.3909 (15)
N1—C1	1.4770 (14)	C22—C23	1.3888 (17)
N2—C3	1.4906 (14)	C22—H22	0.9500
N2—C4	1.4947 (14)	C23—C24	1.3734 (18)
N2—H721	0.909 (17)	C23—H23	0.9500
N2—H722	0.926 (16)	C24—C25	1.3711 (19)
C1—C21	1.5202 (15)	C25—C26	1.3893 (18)
C1—C11	1.5258 (15)	C25—H25	0.9500
C1—H1	1.0000	C26—H26	0.9500
C2—C3	1.5158 (15)	O1—C31	1.2587 (13)
C2—H2A	0.9900	O31—N3	1.2221 (15)
C2—H2B	0.9900	O32—N3	1.2179 (14)
C3—H3A	0.9900	O41—N4	1.2245 (16)
C3—H3B	0.9900	O42—N4	1.2282 (16)
C4—C5	1.5140 (15)	O51—N5	1.2073 (14)
C4—H4A	0.9900	O52—N5	1.2143 (15)
C4—H4B	0.9900	N3—C32	1.4580 (14)
C5—H5A	0.9900	N4—C34	1.4501 (15)
C5—H5B	0.9900	N5—C36	1.4630 (15)
C11—C12	1.3854 (16)	C31—C32	1.4383 (15)
C11—C16	1.3869 (17)	C31—C36	1.4418 (15)
C12—C13	1.3926 (18)	C32—C33	1.3757 (16)
C12—H12	0.9500	C33—C34	1.3841 (17)
C13—C14	1.369 (2)	C33—H33	0.9500
C13—H13	0.9500	C34—C35	1.3891 (18)
C14—C15	1.370 (2)	C35—C36	1.3721 (17)
C15—C16	1.3870 (18)	C35—H35	0.9500
C5—N1—C2	107.93 (8)	C14—C15—C16	118.33 (13)
C5—N1—C1	113.08 (8)	C14—C15—H15	120.8
C2—N1—C1	111.77 (8)	C16—C15—H15	120.8
C3—N2—C4	111.54 (8)	C11—C16—C15	121.35 (12)
C3—N2—H721	111.0 (10)	C11—C16—H16	119.3
C4—N2—H721	109.4 (10)	C15—C16—H16	119.3
C3—N2—H722	112.3 (10)	C22—C21—C26	118.73 (11)
C4—N2—H722	107.0 (10)	C22—C21—C1	121.76 (10)
H721—N2—H722	105.3 (14)	C26—C21—C1	119.49 (10)
N1—C1—C21	110.43 (8)	C23—C22—C21	121.20 (11)
N1—C1—C11	110.40 (9)	C23—C22—H22	119.4
C21—C1—C11	110.24 (9)	C21—C22—H22	119.4
N1—C1—H1	108.6	C24—C23—C22	118.01 (12)
C21—C1—H1	108.6	C24—C23—H23	121.0
C11—C1—H1	108.6	C22—C23—H23	121.0
N1—C2—C3	109.67 (9)	F2—C24—C25	118.85 (11)
N1—C2—H2A	109.7	F2—C24—C23	118.32 (12)
C3—C2—H2A	109.7	C25—C24—C23	122.84 (11)
N1—C2—H2B	109.7	C24—C25—C26	118.46 (11)
C3—C2—H2B	109.7	C24—C25—H25	120.8
H2A—C2—H2B	108.2	C26—C25—H25	120.8
N2—C3—C2	110.27 (9)	C25—C26—C21	120.76 (11)
N2—C3—H3A	109.6	C25—C26—H26	119.6
C2—C3—H3A	109.6	C21—C26—H26	119.6
N2—C3—H3B	109.6	O32—N3—O31	123.16 (11)
C2—C3—H3B	109.6	O32—N3—C32	118.00 (11)
H3A—C3—H3B	108.1	O31—N3—C32	118.83 (10)
N2—C4—C5	109.93 (9)	O41—N4—O42	123.52 (12)
N2—C4—H4A	109.7	O41—N4—C34	118.30 (11)
C5—C4—H4A	109.7	O42—N4—C34	118.16 (12)
N2—C4—H4B	109.7	O51—N5—O52	122.53 (12)
C5—C4—H4B	109.7	O51—N5—C36	118.60 (11)
H4A—C4—H4B	108.2	O52—N5—C36	118.81 (10)
N1—C5—C4	109.94 (9)	O1—C31—C32	123.95 (10)
N1—C5—H5A	109.7	O1—C31—C36	123.74 (10)
C4—C5—H5A	109.7	C32—C31—C36	112.31 (10)
N1—C5—H5B	109.7	C33—C32—C31	124.42 (10)
C4—C5—H5B	109.7	C33—C32—N3	116.94 (10)
H5A—C5—H5B	108.2	C31—C32—N3	118.60 (10)
C12—C11—C16	118.26 (11)	C32—C33—C34	118.57 (11)
C12—C11—C1	120.70 (11)	C32—C33—H33	120.7
C16—C11—C1	121.04 (10)	C34—C33—H33	120.7
C11—C12—C13	121.27 (12)	C33—C34—C35	121.51 (11)
C11—C12—H12	119.4	C33—C34—N4	119.03 (11)
C13—C12—H12	119.4	C35—C34—N4	119.41 (11)
C14—C13—C12	118.23 (12)	C36—C35—C34	118.68 (11)
C14—C13—H13	120.9	C36—C35—H35	120.7
C12—C13—H13	120.9	C34—C35—H35	120.7
F1—C14—C13	119.08 (12)	C35—C36—C31	124.32 (11)
F1—C14—C15	118.38 (13)	C35—C36—N5	117.23 (10)
C13—C14—C15	122.51 (12)	C31—C36—N5	118.45 (10)
C5—N1—C1—C21	175.43 (9)	C22—C23—C24—C25	−0.79 (19)
C2—N1—C1—C21	−62.52 (11)	F2—C24—C25—C26	179.53 (11)
C5—N1—C1—C11	53.26 (12)	C23—C24—C25—C26	−0.13 (18)
C2—N1—C1—C11	175.31 (9)	C24—C25—C26—C21	1.15 (18)
C5—N1—C2—C3	−63.90 (11)	C22—C21—C26—C25	−1.20 (17)
C1—N1—C2—C3	171.15 (9)	C1—C21—C26—C25	177.04 (11)
C4—N2—C3—C2	−53.24 (12)	O1—C31—C32—C33	175.18 (11)
N1—C2—C3—N2	58.60 (12)	C36—C31—C32—C33	−3.91 (16)
C3—N2—C4—C5	53.23 (12)	O1—C31—C32—N3	−2.65 (17)
C2—N1—C5—C4	64.26 (11)	C36—C31—C32—N3	178.26 (10)
C1—N1—C5—C4	−171.57 (9)	O32—N3—C32—C33	−32.04 (17)
N2—C4—C5—N1	−58.93 (12)	O31—N3—C32—C33	147.48 (12)
N1—C1—C11—C12	−116.94 (12)	O32—N3—C32—C31	145.96 (12)
C21—C1—C11—C12	120.78 (12)	O31—N3—C32—C31	−34.53 (17)
N1—C1—C11—C16	62.58 (14)	C31—C32—C33—C34	4.57 (18)
C21—C1—C11—C16	−59.70 (14)	N3—C32—C33—C34	−177.56 (10)
C16—C11—C12—C13	−2.0 (2)	C32—C33—C34—C35	−1.18 (18)
C1—C11—C12—C13	177.51 (12)	C32—C33—C34—N4	−178.72 (11)
C11—C12—C13—C14	0.2 (2)	O41—N4—C34—C33	4.97 (17)
C12—C13—C14—F1	179.46 (13)	O42—N4—C34—C33	−176.16 (12)
C12—C13—C14—C15	1.4 (2)	O41—N4—C34—C35	−172.63 (12)
F1—C14—C15—C16	−179.17 (13)	O42—N4—C34—C35	6.24 (18)
C13—C14—C15—C16	−1.1 (2)	C33—C34—C35—C36	−2.44 (18)
C12—C11—C16—C15	2.3 (2)	N4—C34—C35—C36	175.09 (11)
C1—C11—C16—C15	−177.19 (12)	C34—C35—C36—C31	3.01 (18)
C14—C15—C16—C11	−0.8 (2)	C34—C35—C36—N5	−176.52 (11)
N1—C1—C21—C22	−30.91 (14)	O1—C31—C36—C35	−179.08 (11)
C11—C1—C21—C22	91.36 (12)	C32—C31—C36—C35	0.01 (16)
N1—C1—C21—C26	150.90 (10)	O1—C31—C36—N5	0.44 (17)
C11—C1—C21—C26	−86.83 (12)	C32—C31—C36—N5	179.53 (10)
C26—C21—C22—C23	0.24 (18)	O51—N5—C36—C35	−34.90 (18)
C1—C21—C22—C23	−177.96 (11)	O52—N5—C36—C35	142.36 (14)
C21—C22—C23—C24	0.73 (19)	O51—N5—C36—C31	145.55 (14)
C22—C23—C24—F2	179.55 (11)	O52—N5—C36—C31	−37.19 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H721···O1i	0.909 (17)	1.924 (17)	2.7696 (12)	154.0 (14)
N2—H721···O52i	0.909 (17)	2.369 (16)	3.0018 (14)	126.7 (12)
N2—H722···O1ii	0.926 (16)	1.927 (16)	2.7402 (13)	145.4 (14)
N2—H722···O31ii	0.926 (16)	2.345 (16)	3.0791 (15)	136.0 (13)
C3—H3A···O52i	0.99	2.60	3.0002 (16)	104.
C13—H13···O32iii	0.95	2.39	3.2159 (16)	145.
C23—H23···O42iv	0.95	2.61	3.2827 (17)	129.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H721⋯O1i	0.909 (17)	1.924 (17)	2.7696 (12)	154.0 (14)
N2—H721⋯O52i	0.909 (17)	2.369 (16)	3.0018 (14)	126.7 (12)
N2—H722⋯O1ii	0.926 (16)	1.927 (16)	2.7402 (13)	145.4 (14)
N2—H722⋯O31ii	0.926 (16)	2.345 (16)	3.0791 (15)	136.0 (13)
C3—H3A⋯O52i	0.99	2.60	3.0002 (16)	104
C13—H13⋯O32iii	0.95	2.39	3.2159 (16)	145
C23—H23⋯O42iv	0.95	2.61	3.2827 (17)	129

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