N,N'-Bis(2-chloro-benz-yl)-N''-(2,2,2-trichloro-acet-yl)phospho-ric triamide.

The P atom in the title compound, C(16)H(15)Cl(5)N(3)O(2)P, exhibits a tetra-hedral coordination geometry and the phosphoryl and carbonyl groups are anti with respect to one another. The dihedral angle between the benzene rings is 44.90 (15)°. One of the 2-chloro-benzyl-amido fragments is disordered over two sets of sites with occupancies of 0.8823 (17) and 0.1177 (17). In the crystal, adjacent mol-ecules are linked via N-H⋯O(P) and N-H⋯O(C) hydrogen bonds into an extended chain running parallel to the a axis.

Related literature

For details of compounds having a C(O)NHP(O) skeleton, see: Toghraee et al. (2011 ▶). For bond lengths in related structures, see: Pourayoubi et al. (2011 ▶); Rudd et al. (1996 ▶).

Experimental

Crystal data

C16H15Cl5N3O2P

M = 489.53

Triclinic,

a = 9.9789 (2) Å

b = 10.6058 (3) Å

c = 10.8386 (3) Å

α = 75.8920 (13)°

β = 72.2250 (15)°

γ = 69.6050 (15)°

V = 1011.66 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.81 mm−1

T = 173 K

0.18 × 0.14 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer with APEXII CCD detector

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.867, T max = 0.909

8947 measured reflections

4638 independent reflections

4083 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.129

S = 1.05

4638 reflections

245 parameters

H-atom parameters constrained

Δρmax = 1.42 e Å−3

Δρmin = −0.68 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027681/sj5176sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027681/sj5176Isup2.hkl

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

C16H15Cl5N3O2P	Z = 2
Mr = 489.53	F(000) = 496
Triclinic, P1	Dx = 1.607 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9789 (2) Å	Cell parameters from 4567 reflections
b = 10.6058 (3) Å	θ = 1.0–27.5°
c = 10.8386 (3) Å	µ = 0.81 mm−1
α = 75.8920 (13)°	T = 173 K
β = 72.2250 (15)°	Prism, colorless
γ = 69.6050 (15)°	0.18 × 0.14 × 0.12 mm
V = 1011.66 (4) Å3

Nonius KappaCCD diffractometer with APEXII CCD detector	4638 independent reflections
Radiation source: fine-focus sealed tube	4083 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω and φ scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −12→12
Tmin = 0.867, Tmax = 0.909	k = −13→13
8947 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.043P)2 + 2.0234P] where P = (Fo2 + 2Fc2)/3
4638 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 1.42 e Å−3
0 restraints	Δρmin = −0.68 e Å−3

Experimental. IR (KBr, cm-1): 3371, 3061, 2875, 1692, 1448, 1257, 1224, 1076, 1043, 885, 837, 751, 675.

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	Occ. (<1)
Cl1	0.58102 (9)	−0.04802 (11)	1.36183 (8)	0.0547 (3)
Cl2	0.87488 (8)	−0.22348 (7)	1.35952 (8)	0.03998 (19)
Cl3	0.68228 (12)	−0.30242 (9)	1.26210 (11)	0.0590 (3)
P1	0.72798 (7)	0.04068 (7)	0.90391 (6)	0.02507 (16)
O1	0.9079 (2)	−0.0722 (2)	1.1030 (2)	0.0386 (5)
O2	0.60042 (19)	0.0572 (2)	0.85370 (18)	0.0317 (4)
N1	0.6903 (2)	−0.0446 (2)	1.0605 (2)	0.0262 (4)
H1	0.6044	−0.0605	1.0925	0.031*
C1	0.7866 (3)	−0.0882 (3)	1.1360 (3)	0.0259 (5)
C2	0.7338 (3)	−0.1636 (3)	1.2751 (3)	0.0301 (5)
N2	0.8865 (2)	−0.0463 (3)	0.8250 (2)	0.0352 (6)
H2	0.9630	−0.0151	0.8031	0.042*	0.8823 (17)
C3	0.9024 (3)	−0.1740 (3)	0.7909 (3)	0.0335 (7)	0.8823 (17)
H3A	0.8074	−0.1713	0.7779	0.040*	0.8823 (17)
H3B	0.9247	−0.2470	0.8649	0.040*	0.8823 (17)
C4	1.0236 (2)	−0.2094 (2)	0.66667 (18)	0.0269 (7)	0.8823 (17)
C5	1.0496 (2)	−0.3322 (2)	0.6261 (2)	0.0362 (7)	0.8823 (17)
C6	1.1578 (3)	−0.3675 (2)	0.5135 (2)	0.0476 (10)	0.8823 (17)
H6	1.1755	−0.4515	0.4858	0.057*	0.8823 (17)
C7	1.2401 (3)	−0.2800 (3)	0.4415 (2)	0.0501 (11)	0.8823 (17)
H7	1.3141	−0.3041	0.3645	0.060*	0.8823 (17)
C8	1.2141 (2)	−0.1572 (2)	0.4820 (2)	0.0467 (9)	0.8823 (17)
H8	1.2704	−0.0973	0.4328	0.056*	0.8823 (17)
C9	1.1059 (2)	−0.12185 (18)	0.5946 (2)	0.0342 (7)	0.8823 (17)
H9	1.0882	−0.0379	0.6223	0.041*	0.8823 (17)
Cl4	0.94994 (12)	−0.44175 (10)	0.71412 (13)	0.0605 (3)	0.8823 (17)
H2'	0.9162	−0.1096	0.8886	0.042*	0.1177 (17)
C3'	0.993 (3)	−0.079 (2)	0.730 (2)	0.0335 (7)	0.1177 (17)
H3'1	1.0801	−0.0997	0.7645	0.040*	0.1177 (17)
H3'2	0.9892	0.0079	0.6686	0.040*	0.1177 (17)
C4'	1.036 (2)	−0.1806 (18)	0.6432 (18)	0.0269 (7)	0.1177 (17)
C5'	1.148 (2)	−0.1813 (19)	0.529 (2)	0.0362 (7)	0.1177 (17)
C6'	1.199 (2)	−0.289 (2)	0.4586 (18)	0.0476 (10)	0.1177 (17)
H6'	1.2753	−0.2892	0.3808	0.057*	0.1177 (17)
C7'	1.137 (2)	−0.395 (2)	0.501 (2)	0.0501 (11)	0.1177 (17)
H7'	1.1711	−0.4687	0.4529	0.060*	0.1177 (17)
C8'	1.024 (2)	−0.3946 (17)	0.6152 (19)	0.0467 (9)	0.1177 (17)
H8'	0.9819	−0.4675	0.6445	0.056*	0.1177 (17)
C9'	0.9738 (19)	−0.287 (2)	0.6861 (15)	0.0342 (7)	0.1177 (17)
H9'	0.8970	−0.2867	0.7638	0.041*	0.1177 (17)
Cl4'	1.2278 (9)	−0.0556 (8)	0.4817 (10)	0.0605 (3)	0.1177 (17)
N3	0.7555 (2)	0.1823 (2)	0.9050 (2)	0.0309 (5)
H3	0.8465	0.1849	0.8889	0.037*
C10	0.6334 (3)	0.3062 (3)	0.9322 (3)	0.0356 (6)
H10A	0.5478	0.3027	0.9065	0.043*
H10B	0.6632	0.3860	0.8773	0.043*
C11	0.5868 (3)	0.3256 (3)	1.0740 (3)	0.0322 (6)
C12	0.6657 (4)	0.3724 (3)	1.1291 (3)	0.0409 (7)
C13	0.6224 (5)	0.3866 (4)	1.2614 (4)	0.0529 (9)
H13	0.6780	0.4188	1.2971	0.064*
C14	0.4988 (5)	0.3535 (4)	1.3393 (4)	0.0584 (10)
H14	0.4689	0.3624	1.4296	0.070*
C15	0.4189 (4)	0.3081 (4)	1.2880 (4)	0.0559 (9)
H15	0.3331	0.2856	1.3424	0.067*
C16	0.4620 (4)	0.2945 (3)	1.1571 (3)	0.0437 (7)
H16	0.4047	0.2629	1.1228	0.052*
Cl5	0.82320 (12)	0.41376 (12)	1.03083 (12)	0.0672 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0395 (4)	0.0749 (6)	0.0293 (4)	0.0045 (4)	−0.0024 (3)	−0.0105 (4)
Cl2	0.0424 (4)	0.0350 (4)	0.0463 (4)	−0.0098 (3)	−0.0260 (3)	0.0039 (3)
Cl3	0.0763 (6)	0.0416 (5)	0.0793 (7)	−0.0360 (4)	−0.0472 (5)	0.0180 (4)
P1	0.0178 (3)	0.0380 (4)	0.0204 (3)	−0.0100 (3)	−0.0013 (2)	−0.0080 (3)
O1	0.0246 (10)	0.0590 (14)	0.0358 (11)	−0.0193 (9)	−0.0083 (8)	−0.0023 (10)
O2	0.0199 (9)	0.0517 (12)	0.0251 (9)	−0.0139 (8)	−0.0036 (7)	−0.0063 (8)
N1	0.0195 (10)	0.0363 (12)	0.0235 (10)	−0.0118 (9)	−0.0025 (8)	−0.0042 (9)
C1	0.0224 (12)	0.0282 (13)	0.0269 (13)	−0.0077 (10)	−0.0050 (10)	−0.0049 (10)
C2	0.0302 (13)	0.0271 (13)	0.0333 (14)	−0.0094 (10)	−0.0119 (11)	0.0013 (10)
N2	0.0201 (10)	0.0533 (15)	0.0354 (13)	−0.0106 (10)	0.0012 (9)	−0.0232 (11)
C3	0.0285 (15)	0.0314 (16)	0.0339 (16)	−0.0083 (12)	0.0032 (12)	−0.0078 (13)
C4	0.0245 (13)	0.0277 (16)	0.0247 (15)	−0.0021 (12)	−0.0062 (11)	−0.0053 (12)
C5	0.0303 (16)	0.0358 (17)	0.0444 (19)	−0.0038 (13)	−0.0142 (14)	−0.0117 (14)
C6	0.039 (2)	0.052 (2)	0.050 (2)	0.0103 (17)	−0.0210 (17)	−0.0285 (19)
C7	0.040 (2)	0.068 (3)	0.0244 (17)	0.0100 (19)	−0.0069 (15)	−0.0146 (17)
C8	0.0312 (17)	0.061 (2)	0.0269 (17)	0.0004 (16)	−0.0008 (14)	0.0019 (16)
C9	0.0285 (15)	0.0358 (17)	0.0307 (16)	−0.0046 (13)	−0.0026 (12)	−0.0050 (13)
Cl4	0.0475 (5)	0.0380 (5)	0.0988 (9)	−0.0148 (4)	−0.0086 (5)	−0.0240 (5)
N2'	0.0201 (10)	0.0533 (15)	0.0354 (13)	−0.0106 (10)	0.0012 (9)	−0.0232 (11)
C3'	0.0285 (15)	0.0314 (16)	0.0339 (16)	−0.0083 (12)	0.0032 (12)	−0.0078 (13)
C4'	0.0245 (13)	0.0277 (16)	0.0247 (15)	−0.0021 (12)	−0.0062 (11)	−0.0053 (12)
C5'	0.0303 (16)	0.0358 (17)	0.0444 (19)	−0.0038 (13)	−0.0142 (14)	−0.0117 (14)
C6'	0.039 (2)	0.052 (2)	0.050 (2)	0.0103 (17)	−0.0210 (17)	−0.0285 (19)
C7'	0.040 (2)	0.068 (3)	0.0244 (17)	0.0100 (19)	−0.0069 (15)	−0.0146 (17)
C8'	0.0312 (17)	0.061 (2)	0.0269 (17)	0.0004 (16)	−0.0008 (14)	0.0019 (16)
C9'	0.0285 (15)	0.0358 (17)	0.0307 (16)	−0.0046 (13)	−0.0026 (12)	−0.0050 (13)
Cl4'	0.0475 (5)	0.0380 (5)	0.0988 (9)	−0.0148 (4)	−0.0086 (5)	−0.0240 (5)
N3	0.0251 (11)	0.0398 (13)	0.0293 (12)	−0.0138 (10)	−0.0051 (9)	−0.0035 (10)
C10	0.0399 (15)	0.0336 (15)	0.0342 (15)	−0.0088 (12)	−0.0169 (12)	0.0002 (11)
C11	0.0369 (14)	0.0232 (13)	0.0353 (15)	−0.0020 (11)	−0.0174 (12)	−0.0017 (11)
C12	0.0452 (17)	0.0320 (15)	0.0484 (18)	−0.0072 (13)	−0.0219 (14)	−0.0041 (13)
C13	0.073 (3)	0.0379 (18)	0.054 (2)	0.0001 (16)	−0.038 (2)	−0.0127 (15)
C14	0.063 (2)	0.050 (2)	0.0396 (19)	0.0104 (18)	−0.0097 (17)	−0.0114 (16)
C15	0.048 (2)	0.053 (2)	0.048 (2)	−0.0016 (16)	−0.0025 (16)	−0.0043 (17)
C16	0.0402 (17)	0.0381 (17)	0.0478 (19)	−0.0070 (13)	−0.0101 (14)	−0.0053 (14)
Cl5	0.0632 (6)	0.0785 (7)	0.0774 (7)	−0.0424 (5)	−0.0238 (5)	−0.0030 (5)

Cl1—C2	1.759 (3)	C3'—H3'2	0.9900
Cl2—C2	1.761 (3)	C4'—C5'	1.3900
Cl3—C2	1.768 (3)	C4'—C9'	1.3900
P1—O2	1.4724 (18)	C5'—C6'	1.3900
P1—N2	1.621 (2)	C5'—Cl4'	1.682 (17)
P1—N3	1.622 (2)	C6'—C7'	1.3900
P1—N1	1.715 (2)	C6'—H6'	0.9500
O1—C1	1.212 (3)	C7'—C8'	1.3900
N1—C1	1.339 (3)	C7'—H7'	0.9500
N1—H1	0.8800	C8'—C9'	1.3900
C1—C2	1.553 (4)	C8'—H8'	0.9500
N2—C3	1.434 (4)	C9'—H9'	0.9500
N2—H2	0.8800	N3—C10	1.467 (4)
C3—C4	1.534 (3)	N3—H3	0.8800
C3—H3A	0.9900	C10—C11	1.507 (4)
C3—H3B	0.9900	C10—H10A	0.9900
C4—C5	1.3900	C10—H10B	0.9900
C4—C9	1.3900	C11—C12	1.388 (4)
C5—C6	1.3900	C11—C16	1.389 (4)
C5—Cl4	1.713 (2)	C12—C13	1.395 (5)
C6—C7	1.3900	C12—Cl5	1.740 (4)
C6—H6	0.9500	C13—C14	1.371 (6)
C7—C8	1.3900	C13—H13	0.9500
C7—H7	0.9500	C14—C15	1.359 (6)
C8—C9	1.3900	C14—H14	0.9500
C8—H8	0.9500	C15—C16	1.380 (5)
C9—H9	0.9500	C15—H15	0.9500
C3'—C4'	1.47 (3)	C16—H16	0.9500
C3'—H3'1	0.9900
O2—P1—N2	116.10 (12)	H3'1—C3'—H3'2	105.4
O2—P1—N3	114.51 (12)	C5'—C4'—C9'	120.0
N2—P1—N3	103.26 (13)	C5'—C4'—C3'	121.6 (16)
O2—P1—N1	104.46 (11)	C9'—C4'—C3'	118.0 (16)
N2—P1—N1	108.13 (13)	C4'—C5'—C6'	120.0
N3—P1—N1	110.31 (11)	C4'—C5'—Cl4'	119.8 (12)
C1—N1—P1	122.56 (18)	C6'—C5'—Cl4'	120.1 (12)
C1—N1—H1	118.7	C5'—C6'—C7'	120.0
P1—N1—H1	118.7	C5'—C6'—H6'	120.0
O1—C1—N1	124.8 (2)	C7'—C6'—H6'	120.0
O1—C1—C2	119.8 (2)	C8'—C7'—C6'	120.0
N1—C1—C2	115.5 (2)	C8'—C7'—H7'	120.0
C1—C2—Cl1	108.21 (18)	C6'—C7'—H7'	120.0
C1—C2—Cl2	110.50 (18)	C7'—C8'—C9'	120.0
Cl1—C2—Cl2	109.24 (16)	C7'—C8'—H8'	120.0
C1—C2—Cl3	109.63 (19)	C9'—C8'—H8'	120.0
Cl1—C2—Cl3	109.77 (15)	C8'—C9'—C4'	120.0
Cl2—C2—Cl3	109.47 (15)	C8'—C9'—H9'	120.0
C3—N2—P1	120.0 (2)	C4'—C9'—H9'	120.0
C3—N2—H2	120.0	C10—N3—P1	122.06 (19)
P1—N2—H2	120.0	C10—N3—H3	119.0
N2—C3—C4	113.7 (2)	P1—N3—H3	119.0
N2—C3—H3A	108.8	N3—C10—C11	113.5 (2)
C4—C3—H3A	108.8	N3—C10—H10A	108.9
N2—C3—H3B	108.8	C11—C10—H10A	108.9
C4—C3—H3B	108.8	N3—C10—H10B	108.9
H3A—C3—H3B	107.7	C11—C10—H10B	108.9
C5—C4—C9	120.0	H10A—C10—H10B	107.7
C5—C4—C3	118.28 (18)	C12—C11—C16	116.5 (3)
C9—C4—C3	121.71 (18)	C12—C11—C10	122.8 (3)
C4—C5—C6	120.0	C16—C11—C10	120.7 (3)
C4—C5—Cl4	120.65 (14)	C11—C12—C13	121.7 (3)
C6—C5—Cl4	119.35 (14)	C11—C12—Cl5	119.1 (3)
C7—C6—C5	120.0	C13—C12—Cl5	119.1 (3)
C7—C6—H6	120.0	C14—C13—C12	119.3 (3)
C5—C6—H6	120.0	C14—C13—H13	120.3
C6—C7—C8	120.0	C12—C13—H13	120.3
C6—C7—H7	120.0	C15—C14—C13	120.3 (4)
C8—C7—H7	120.0	C15—C14—H14	119.9
C9—C8—C7	120.0	C13—C14—H14	119.9
C9—C8—H8	120.0	C14—C15—C16	120.1 (4)
C7—C8—H8	120.0	C14—C15—H15	119.9
C8—C9—C4	120.0	C16—C15—H15	119.9
C8—C9—H9	120.0	C15—C16—C11	121.9 (3)
C4—C9—H9	120.0	C15—C16—H16	119.0
C4'—C3'—H3'1	103.9	C11—C16—H16	119.0
C4'—C3'—H3'2	103.9
O2—P1—N1—C1	174.8 (2)	C9'—C4'—C5'—C6'	0.0
N2—P1—N1—C1	50.6 (2)	C3'—C4'—C5'—C6'	172 (2)
N3—P1—N1—C1	−61.6 (2)	C9'—C4'—C5'—Cl4'	−177.3 (15)
P1—N1—C1—O1	0.2 (4)	C3'—C4'—C5'—Cl4'	−5(2)
P1—N1—C1—C2	−179.98 (18)	C4'—C5'—C6'—C7'	0.0
O1—C1—C2—Cl1	116.0 (3)	Cl4'—C5'—C6'—C7'	177.2 (16)
N1—C1—C2—Cl1	−63.9 (3)	C5'—C6'—C7'—C8'	0.0
O1—C1—C2—Cl2	−3.6 (3)	C6'—C7'—C8'—C9'	0.0
N1—C1—C2—Cl2	176.56 (19)	C7'—C8'—C9'—C4'	0.0
O1—C1—C2—Cl3	−124.3 (2)	C5'—C4'—C9'—C8'	0.0
N1—C1—C2—Cl3	55.8 (3)	C3'—C4'—C9'—C8'	−172 (2)
O2—P1—N2—C3	−47.0 (3)	O2—P1—N3—C10	34.9 (2)
N3—P1—N2—C3	−173.2 (2)	N2—P1—N3—C10	162.0 (2)
N1—P1—N2—C3	69.9 (3)	N1—P1—N3—C10	−82.6 (2)
P1—N2—C3—C4	151.5 (2)	P1—N3—C10—C11	94.5 (3)
N2—C3—C4—C5	179.0 (2)	N3—C10—C11—C12	77.3 (3)
N2—C3—C4—C9	−1.5 (4)	N3—C10—C11—C16	−101.5 (3)
C9—C4—C5—C6	0.0	C16—C11—C12—C13	0.4 (4)
C3—C4—C5—C6	179.5 (2)	C10—C11—C12—C13	−178.5 (3)
C9—C4—C5—Cl4	179.67 (18)	C16—C11—C12—Cl5	−179.9 (2)
C3—C4—C5—Cl4	−0.8 (2)	C10—C11—C12—Cl5	1.2 (4)
C4—C5—C6—C7	0.0	C11—C12—C13—C14	0.0 (5)
Cl4—C5—C6—C7	−179.67 (18)	Cl5—C12—C13—C14	−179.7 (3)
C5—C6—C7—C8	0.0	C12—C13—C14—C15	−0.3 (5)
C6—C7—C8—C9	0.0	C13—C14—C15—C16	0.2 (6)
C7—C8—C9—C4	0.0	C14—C15—C16—C11	0.2 (5)
C5—C4—C9—C8	0.0	C12—C11—C16—C15	−0.5 (5)
C3—C4—C9—C8	−179.5 (3)	C10—C11—C16—C15	178.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88	1.94	2.804 (3)	168.
N2—H2···O1ii	0.88	2.38	3.106 (3)	141.
N2'—H2'···O1	0.88	2.42	3.025 (3)	126.
N3—H3···O1ii	0.88	2.34	3.129 (3)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.88	1.94	2.804 (3)	168
N2—H2⋯O1ii	0.88	2.38	3.106 (3)	141
N2′—H2′⋯O1	0.88	2.42	3.025 (3)	126
N3—H3⋯O1ii	0.88	2.34	3.129 (3)	149

Symmetry codes: (i) ; (ii) .