Aqua­[4-(1H-benzimidazol-2-yl)benzoato]triphenyl­tin(IV) dioxane solvate

The title complex, [Sn(C₆H₅)₃(C₁₄H₉N₂O₂)(H₂O)]·C₄H₈O₂, is composed of a triphenyl­tin carboxyl­ate with a coordinated water mol­ecule and a free dioxane mol­ecule. The Sn^IV atom is five-coordinate and has a trans-C₃SnO₂ trigonal–bipyramidal geometry, with the three phenyl groups occupying the equatorial plane, the 4-(1H-benzimidazol-2-yl)benzoate ligand coordinating in a monodentate manner and a water mol­ecule in the axial positions. Strong inter­molecular O—H...O and N—H...O hydrogen bonds link the mol­ecules into an infinite two-dimensional network, with these networks held together by van der Waals forces to generate a layer structure. π–π Stacking inter­actions also exist in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.055
• wR factor = 0.177
• Data-to-parameter ratio = 23.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C29
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: APEX2; program(s) used to refine structure: APEX2; molecular graphics: APEX2 and Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: APEX2.

Aqua[4-(1H-benzimidazol-2-yl)benzoato]triphenyltin(IV) dioxane solvate

Crystal data

[Sn(C6H5)3(C14H9N2O2)(H2O)]·C4H8O2	F(000) = 1416
Mr = 693.34	Dx = 1.410 Mg m^−3
Monoclinic, P21/c	Melting point > 573 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.233 (3) Å	Cell parameters from 9781 reflections
b = 11.580 (2) Å	θ = 2.2–22.8°
c = 19.047 (4) Å	µ = 0.83 mm^−1
β = 103.617 (2)°	T = 296 K
V = 3265 (1) Å^3	Block, pale-yellow
Z = 4	0.34 × 0.32 × 0.22 mm

Data collection

Bruker APEXII area-detector diffractometer	7464 independent reflections
Radiation source: fine-focus sealed tube	4923 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.091
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −19→19
Tmin = 0.75, Tmax = 0.83	k = −15→15
27888 measured reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.082P)^2 + 3.11P] where P = (Fo^2 + 2Fc^2)/3
7464 reflections	(Δ/σ)max = 0.001
325 parameters	Δρmax = 1.15 e Å^−3
99 restraints	Δρmin = −0.67 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.26655 (2)	0.32391 (3)	0.107297 (19)	0.06205 (15)
O1	0.0916 (2)	0.2188 (4)	0.1520 (2)	0.0796 (11)
O2	0.2406 (2)	0.1946 (3)	0.1787 (2)	0.0721 (10)
O3	0.3181 (3)	0.4657 (4)	0.0316 (2)	0.0796 (11)
O4	0.4250 (5)	0.3270 (5)	0.9634 (4)	0.143 (2)
O5	0.5291 (5)	0.1405 (7)	0.9354 (5)	0.165 (3)
N1	0.2220 (3)	−0.1649 (3)	0.4685 (2)	0.0620 (10)
N2	0.0797 (3)	−0.2184 (4)	0.4187 (2)	0.0653 (10)
C1	0.19399 (12)	−0.24521 (14)	0.51209 (8)	0.0626 (12)
C2	0.10479 (12)	−0.27521 (13)	0.48170 (8)	0.0649 (12)
C3	0.06090 (14)	−0.35456 (15)	0.51627 (9)	0.0754 (15)
H3	0.0012	−0.3746	0.4959	0.090*
C4	0.10623 (15)	−0.40390 (16)	0.58124 (10)	0.0805 (16)
H4	0.0769	−0.4570	0.6044	0.097*
C5	0.19544 (15)	−0.37390 (17)	0.61163 (9)	0.0835 (16)
H5	0.2258	−0.4069	0.6551	0.100*
C6	0.23932 (14)	−0.29456 (17)	0.57705 (8)	0.0759 (15)
H6	0.2990	−0.2745	0.5974	0.091*
C8	0.15059 (9)	−0.07534 (11)	0.35031 (6)	0.0542 (10)
C9	0.23461 (8)	−0.03605 (11)	0.34214 (6)	0.0607 (12)
H9	0.2879	−0.0622	0.3725	0.073*
C10	0.23627 (8)	0.04325 (10)	0.28733 (6)	0.0587 (11)
H10	0.2914	0.0703	0.2811	0.070*
C11	0.15644 (8)	0.08235 (10)	0.24191 (6)	0.0522 (10)
C12	0.07385 (8)	0.03775 (12)	0.24994 (7)	0.0597 (11)
H12	0.0204	0.0619	0.2188	0.072*
C13	0.07060 (8)	−0.04128 (12)	0.30325 (7)	0.0605 (11)
H13	0.0156	−0.0715	0.3077	0.073*
C27	0.21328 (11)	0.23387 (15)	0.01004 (7)	0.0684 (13)
C28	0.23141 (13)	0.11429 (15)	0.00666 (7)	0.096 (2)
H28	0.2663	0.0775	0.0471	0.116*
C29	0.19819 (17)	0.05082 (18)	−0.05586 (6)	0.116 (2)
H29	0.2084	−0.0283	−0.0563	0.139*
C30	0.14940 (18)	0.1062 (2)	−0.11801 (6)	0.100 (2)
H30	0.1301	0.0657	−0.1611	0.120*
C31	0.13073 (15)	0.2211 (2)	−0.11406 (7)	0.100 (2)
H31	0.0947	0.2572	−0.1543	0.119*
C32	0.16385 (13)	0.28640 (18)	−0.05169 (7)	0.0839 (16)
H32	0.1525	0.3653	−0.0518	0.101*
C15	0.20097 (13)	0.46388 (12)	0.14462 (10)	0.0753 (15)
C16	0.12498 (14)	0.51638 (14)	0.10172 (11)	0.098 (2)
H16	0.0997	0.4904	0.0551	0.118*
C17	0.08653 (17)	0.61342 (14)	0.13253 (14)	0.122 (3)
H17	0.0366	0.6528	0.1057	0.146*
C18	0.1274 (2)	0.64667 (11)	0.20482 (14)	0.131 (3)
H18	0.1018	0.7080	0.2245	0.158*
C19	0.19753 (19)	0.59743 (10)	0.24489 (12)	0.126 (3)
H19	0.2225	0.6242	0.2913	0.152*
C20	0.23511 (15)	0.50292 (11)	0.21686 (10)	0.100 (2)
H20	0.2838	0.4644	0.2462	0.120*
C21	0.40574 (9)	0.30563 (15)	0.15804 (9)	0.0695 (13)
C22	0.45803 (11)	0.40131 (17)	0.17968 (10)	0.0925 (19)
H22	0.4335	0.4746	0.1690	0.111*
C23	0.55093 (11)	0.3892 (2)	0.21892 (11)	0.121 (3)
H23	0.5850	0.4542	0.2364	0.145*
C24	0.58872 (9)	0.2811 (2)	0.23023 (12)	0.113 (3)
H24	0.6497	0.2733	0.2526	0.136*
C25	0.53773 (8)	0.1853 (2)	0.20900 (11)	0.118 (3)
H25	0.5632	0.1123	0.2187	0.142*
C26	0.44386 (9)	0.19695 (17)	0.17129 (9)	0.0915 (19)
H26	0.4092	0.1315	0.1560	0.110*
C7	0.1519 (3)	−0.1530 (4)	0.4129 (3)	0.0586 (11)
C14	0.1602 (3)	0.1714 (4)	0.1865 (3)	0.0611 (12)
C33	0.4388 (8)	0.1431 (10)	0.9064 (7)	0.173 (4)
H33A	0.4077	0.1037	0.9384	0.208*
H33B	0.4256	0.1026	0.8605	0.208*
C34	0.4064 (8)	0.2609 (10)	0.8954 (6)	0.165 (4)
H34A	0.3418	0.2602	0.8747	0.197*
H34B	0.4353	0.2988	0.8614	0.197*
C35	0.5484 (8)	0.1948 (10)	1.0027 (6)	0.153 (3)
H35A	0.6129	0.1913	1.0236	0.184*
H35B	0.5180	0.1541	1.0348	0.184*
C36	0.5188 (7)	0.3175 (9)	0.9969 (7)	0.151 (3)
H36A	0.5305	0.3515	1.0447	0.181*
H36B	0.5534	0.3600	0.9687	0.181*
H2	0.023 (2)	−0.226 (7)	0.383 (3)	0.11 (2)*
H3A	0.288 (4)	0.523 (4)	0.011 (4)	0.12 (3)*
H3B	0.355 (3)	0.438 (5)	0.009 (3)	0.09 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0566 (2)	0.0604 (2)	0.0700 (2)	0.00251 (15)	0.01675 (15)	0.01358 (16)
O1	0.062 (2)	0.085 (3)	0.087 (3)	0.0090 (19)	0.0075 (18)	0.030 (2)
O2	0.063 (2)	0.077 (2)	0.078 (2)	−0.0032 (17)	0.0191 (17)	0.0204 (19)
O3	0.084 (3)	0.066 (2)	0.096 (3)	0.013 (2)	0.037 (2)	0.030 (2)
O4	0.138 (4)	0.125 (4)	0.180 (5)	0.021 (3)	0.068 (4)	−0.007 (4)
O5	0.139 (4)	0.155 (5)	0.196 (6)	0.023 (4)	0.033 (4)	−0.026 (5)
N1	0.061 (2)	0.066 (3)	0.059 (2)	−0.0081 (19)	0.0120 (18)	0.0082 (19)
N2	0.062 (2)	0.070 (3)	0.061 (2)	−0.013 (2)	0.0084 (19)	0.008 (2)
C1	0.070 (3)	0.057 (3)	0.059 (3)	−0.007 (2)	0.009 (2)	0.004 (2)
C2	0.068 (3)	0.064 (3)	0.062 (3)	−0.011 (2)	0.012 (2)	0.004 (2)
C3	0.080 (4)	0.069 (3)	0.077 (3)	−0.016 (3)	0.018 (3)	0.007 (3)
C4	0.101 (4)	0.064 (3)	0.076 (3)	−0.014 (3)	0.020 (3)	0.016 (3)
C5	0.103 (5)	0.074 (4)	0.069 (3)	−0.004 (3)	0.011 (3)	0.018 (3)
C6	0.080 (4)	0.079 (4)	0.064 (3)	−0.006 (3)	0.008 (3)	0.009 (3)
C8	0.061 (3)	0.055 (3)	0.047 (2)	−0.003 (2)	0.0153 (19)	0.0019 (19)
C9	0.056 (3)	0.072 (3)	0.051 (2)	−0.001 (2)	0.006 (2)	0.011 (2)
C10	0.051 (2)	0.073 (3)	0.055 (2)	−0.003 (2)	0.018 (2)	0.002 (2)
C11	0.053 (2)	0.054 (2)	0.050 (2)	−0.0006 (19)	0.0135 (19)	−0.0039 (19)
C12	0.050 (2)	0.065 (3)	0.062 (3)	−0.002 (2)	0.008 (2)	0.003 (2)
C13	0.055 (3)	0.068 (3)	0.059 (3)	−0.008 (2)	0.015 (2)	0.005 (2)
C27	0.061 (3)	0.075 (3)	0.071 (3)	−0.005 (3)	0.019 (2)	0.011 (3)
C28	0.109 (5)	0.080 (4)	0.087 (4)	0.002 (4)	−0.003 (4)	0.014 (4)
C29	0.134 (7)	0.084 (5)	0.125 (6)	−0.008 (4)	0.024 (5)	0.000 (5)
C30	0.101 (5)	0.110 (6)	0.087 (4)	−0.014 (4)	0.018 (4)	−0.004 (4)
C31	0.091 (5)	0.123 (6)	0.079 (4)	−0.001 (4)	0.008 (3)	0.018 (4)
C32	0.089 (4)	0.079 (4)	0.083 (4)	0.006 (3)	0.018 (3)	0.018 (3)
C15	0.076 (3)	0.070 (3)	0.089 (4)	−0.003 (3)	0.038 (3)	0.010 (3)
C16	0.094 (4)	0.081 (4)	0.132 (6)	0.024 (3)	0.049 (4)	0.030 (4)
C17	0.107 (5)	0.105 (5)	0.170 (6)	0.034 (4)	0.067 (5)	0.038 (5)
C18	0.165 (9)	0.085 (5)	0.175 (9)	−0.011 (5)	0.101 (8)	0.001 (6)
C19	0.145 (8)	0.109 (7)	0.141 (7)	−0.014 (6)	0.065 (6)	−0.014 (6)
C20	0.108 (5)	0.095 (5)	0.101 (5)	−0.007 (4)	0.034 (4)	−0.015 (4)
C21	0.065 (3)	0.069 (3)	0.072 (3)	0.002 (2)	0.013 (2)	0.014 (3)
C22	0.073 (4)	0.085 (4)	0.119 (5)	−0.016 (3)	0.023 (3)	−0.007 (4)
C23	0.072 (4)	0.143 (8)	0.143 (7)	−0.026 (5)	0.014 (4)	−0.032 (6)
C24	0.071 (4)	0.157 (8)	0.102 (5)	0.006 (5)	0.001 (4)	−0.002 (5)
C25	0.079 (5)	0.115 (6)	0.147 (7)	0.028 (4)	−0.001 (5)	0.037 (5)
C26	0.080 (4)	0.075 (4)	0.112 (5)	0.009 (3)	0.007 (4)	0.025 (4)
C7	0.060 (3)	0.060 (3)	0.056 (3)	−0.008 (2)	0.014 (2)	0.001 (2)
C14	0.058 (3)	0.066 (3)	0.061 (3)	−0.001 (2)	0.017 (2)	0.002 (2)
C33	0.150 (6)	0.158 (6)	0.199 (8)	0.012 (6)	0.018 (6)	−0.046 (6)
C34	0.150 (6)	0.172 (7)	0.157 (6)	0.030 (6)	0.008 (5)	0.008 (6)
C35	0.131 (6)	0.186 (7)	0.139 (6)	0.024 (5)	0.025 (5)	0.013 (6)
C36	0.127 (5)	0.160 (6)	0.178 (7)	−0.039 (5)	0.060 (5)	−0.040 (5)

Geometric parameters (Å, º)

Sn1—C15	2.113 (2)	C28—C29	1.3894
Sn1—C27	2.114 (2)	C28—H28	0.9300
Sn1—O2	2.121 (3)	C29—C30	1.3964
Sn1—C21	2.123 (2)	C29—H29	0.9300
Sn1—O3	2.434 (4)	C30—C31	1.3668
O1—C14	1.226 (6)	C30—H30	0.9300
O2—C14	1.297 (6)	C31—C32	1.3984
O3—H3A	0.85 (5)	C31—H31	0.9300
O3—H3B	0.85 (5)	C32—H32	0.9300
O4—C36	1.425 (10)	C15—C16	1.3899
O4—C34	1.472 (11)	C15—C20	1.4251
O5—C33	1.356 (11)	C16—C17	1.4533
O5—C35	1.396 (11)	C16—H16	0.9300
N1—C7	1.323 (6)	C17—C18	1.4241
N1—C1	1.381 (4)	C17—H17	0.9300
N2—C2	1.342 (4)	C18—C19	1.2906
N2—C7	1.361 (6)	C18—H18	0.9300
N2—H2	0.97 (4)	C19—C20	1.3980
C1—C2	1.3900	C19—H19	0.9300
C1—C6	1.3900	C20—H20	0.9300
C2—C3	1.3900	C21—C22	1.3702
C3—C4	1.3900	C21—C26	1.3841
C3—H3	0.9300	C22—C23	1.4433
C4—C5	1.3900	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.3737
C5—C6	1.3900	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.3599
C6—H6	0.9300	C24—H24	0.9300
C8—C13	1.3890	C25—C26	1.4475
C8—C9	1.4011	C25—H25	0.9300
C8—C7	1.489 (5)	C26—H26	0.9300
C9—C10	1.3950	C33—C34	1.450 (12)
C9—H9	0.9300	C33—H33A	0.9700
C10—C11	1.3917	C33—H33B	0.9700
C10—H10	0.9300	C34—H34A	0.9700
C11—C12	1.4014	C34—H34B	0.9700
C11—C14	1.486 (5)	C35—C36	1.486 (11)
C12—C13	1.3765	C35—H35A	0.9700
C12—H12	0.9300	C35—H35B	0.9700
C13—H13	0.9300	C36—H36A	0.9700
C27—C32	1.3793	C36—H36B	0.9700
C27—C28	1.4164
C15—Sn1—C27	123.97 (7)	C32—C31—H31	118.8
C15—Sn1—O2	98.7 (2)	C27—C32—C31	120.1
C27—Sn1—O2	97.0 (2)	C27—C32—H32	120.0
C15—Sn1—C21	115.08 (8)	C31—C32—H32	120.0
C27—Sn1—C21	119.07 (8)	C16—C15—C20	119.5
O2—Sn1—C21	87.4 (2)	C16—C15—Sn1	122.14 (13)
C15—Sn1—O3	85.7 (2)	C20—C15—Sn1	118.31 (13)
C27—Sn1—O3	85.7 (2)	C15—C16—C17	117.4
O2—Sn1—O3	172.1 (2)	C15—C16—H16	121.3
C21—Sn1—O3	84.8 (2)	C17—C16—H16	121.3
C14—O2—Sn1	122.9 (3)	C18—C17—C16	118.3
Sn1—O3—H3A	126 (5)	C18—C17—H17	120.9
Sn1—O3—H3B	113 (4)	C16—C17—H17	120.9
H3A—O3—H3B	114 (7)	C19—C18—C17	124.4
C36—O4—C34	108.6 (7)	C19—C18—H18	117.8
C33—O5—C35	109.8 (9)	C17—C18—H18	117.8
C7—N1—C1	104.2 (3)	C18—C19—C20	118.5
C2—N2—C7	106.3 (4)	C18—C19—H19	120.8
C2—N2—H2	127 (4)	C20—C19—H19	120.8
C7—N2—H2	127 (4)	C19—C20—C15	121.9
N1—C1—C2	109.19 (18)	C19—C20—H20	119.1
N1—C1—C6	130.81 (18)	C15—C20—H20	119.1
C2—C1—C6	120.0	C22—C21—C26	119.4
N2—C2—C1	107.12 (19)	C22—C21—Sn1	120.25 (13)
N2—C2—C3	132.84 (19)	C26—C21—Sn1	120.31 (12)
C1—C2—C3	120.0	C21—C22—C23	120.5
C4—C3—C2	120.0	C21—C22—H22	119.8
C4—C3—H3	120.0	C23—C22—H22	119.8
C2—C3—H3	120.0	C24—C23—C22	119.6
C3—C4—C5	120.0	C24—C23—H23	120.2
C3—C4—H4	120.0	C22—C23—H23	120.2
C5—C4—H4	120.0	C25—C24—C23	120.5
C6—C5—C4	120.0	C25—C24—H24	119.7
C6—C5—H5	120.0	C23—C24—H24	119.7
C4—C5—H5	120.0	C24—C25—C26	120.0
C5—C6—C1	120.0	C24—C25—H25	120.0
C5—C6—H6	120.0	C26—C25—H25	120.0
C1—C6—H6	120.0	C21—C26—C25	119.9
C13—C8—C9	121.4	C21—C26—H26	120.1
C13—C8—C7	122.15 (19)	C25—C26—H26	120.1
C9—C8—C7	116.40 (19)	N1—C7—N2	113.1 (4)
C10—C9—C8	118.4	N1—C7—C8	124.0 (4)
C10—C9—H9	120.8	N2—C7—C8	122.9 (4)
C8—C9—H9	120.8	O1—C14—O2	123.7 (5)
C11—C10—C9	120.8	O1—C14—C11	121.4 (4)
C11—C10—H10	119.6	O2—C14—C11	114.9 (4)
C9—C10—H10	119.6	O5—C33—C34	111.0 (10)
C10—C11—C12	119.2	O5—C33—H33A	109.4
C10—C11—C14	119.5 (2)	C34—C33—H33A	109.4
C12—C11—C14	121.3 (2)	O5—C33—H33B	109.4
C13—C12—C11	121.0	C34—C33—H33B	109.4
C13—C12—H12	119.5	H33A—C33—H33B	108.0
C11—C12—H12	119.5	C33—C34—O4	112.0 (9)
C12—C13—C8	119.1	C33—C34—H34A	109.2
C12—C13—H13	120.4	O4—C34—H34A	109.2
C8—C13—H13	120.4	C33—C34—H34B	109.2
C32—C27—C28	117.8	O4—C34—H34B	109.2
C32—C27—Sn1	123.32 (13)	H34A—C34—H34B	107.9
C28—C27—Sn1	118.90 (10)	O5—C35—C36	111.5 (9)
C29—C28—C27	121.4	O5—C35—H35A	109.3
C29—C28—H28	119.3	C36—C35—H35A	109.3
C27—C28—H28	119.3	O5—C35—H35B	109.3
C28—C29—C30	119.8	C36—C35—H35B	109.3
C28—C29—H29	120.1	H35A—C35—H35B	108.0
C30—C29—H29	120.1	O4—C36—C35	111.2 (8)
C31—C30—C29	118.4	O4—C36—H36A	109.4
C31—C30—H30	120.8	C35—C36—H36A	109.4
C29—C30—H30	120.8	O4—C36—H36B	109.4
C30—C31—C32	122.4	C35—C36—H36B	109.4
C30—C31—H31	118.8	H36A—C36—H36B	108.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O4^i	0.85 (5)	2.00 (5)	2.814 (7)	162 (6)
N2—H2···O1^ii	0.97 (4)	1.83 (3)	2.738 (5)	155 (6)
O3—H3A···N1^iii	0.85 (5)	2.00 (6)	2.842 (6)	176 (8)

Symmetry codes: (i) x, y, z−1; (ii) −x, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2.