(Z)-N-[2-(N'-Hy-droxy-carbamimido-yl)phen-yl]acetamide.

The asymmetric unit of the title compound, C9H11N3O2, contains two mol-ecules (A and B), which exist in Z conformations with respect to their C=N double bond. The dihedral angles between the benzene ring and the pendant hy-droxy-carbamimidoyl and acetamide groups are 28.58 (7) and 1.30 (5)°, respectively, in mol-ecule A and 25.04 (7) and 27.85 (9)°, respectively, in mol-ecule B. An intra-molecular N-H⋯N hydrogen bond generates an S(6) ring in both mol-ecules. Mol-ecule A also features an intra-molecular C-H⋯O inter-action, which closes an S(6) ring. In the crystal, the mol-ecules are linked by N-H⋯O, N-H⋯N, O-H⋯O, O-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds and C-H⋯π inter-actions, generating a three-dimensional network.

Related literature

For background and applications of amidoximes, see: Clapp (1976 ▶, 1984 ▶); Jochims (1996 ▶); Fylaktakidou et al. (2008 ▶); Mansuy & Boucher (2004 ▶); Kontogiorgis & Hadjipavlou-Litina (2002 ▶); Wang et al. (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C9H11N3O2

M = 193.21

Triclinic,

a = 8.7813 (12) Å

b = 9.5432 (13) Å

c = 11.9770 (15) Å

α = 80.722 (2)°

β = 78.531 (2)°

γ = 70.181 (2)°

V = 920.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.35 × 0.20 × 0.05 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.965, T max = 0.995

12849 measured reflections

4680 independent reflections

3815 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.07

4680 reflections

287 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813003371/hb7034sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003371/hb7034Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003371/hb7034Isup3.cml

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

C9H11N3O2	Z = 4
Mr = 193.21	F(000) = 408
Triclinic, P1	Dx = 1.394 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7813 (12) Å	Cell parameters from 3493 reflections
b = 9.5432 (13) Å	θ = 2.3–28.5°
c = 11.9770 (15) Å	µ = 0.10 mm−1
α = 80.722 (2)°	T = 100 K
β = 78.531 (2)°	Plate, colourless
γ = 70.181 (2)°	0.35 × 0.20 × 0.05 mm
V = 920.6 (2) Å3

Bruker APEX DUO CCD diffractometer	4680 independent reflections
Radiation source: fine-focus sealed tube	3815 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 28.6°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→7
Tmin = 0.965, Tmax = 0.995	k = −12→12
12849 measured reflections	l = −16→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.261P] where P = (Fo2 + 2Fc2)/3
4680 reflections	(Δ/σ)max < 0.001
287 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100 (1) K.

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
O1A	1.06478 (11)	0.25713 (11)	0.46170 (9)	0.0183 (2)
O2A	0.37005 (11)	0.17841 (12)	0.55131 (8)	0.0200 (2)
N1A	0.91075 (13)	0.26562 (12)	0.43516 (9)	0.0136 (2)
N2A	0.91118 (15)	0.50889 (14)	0.36926 (11)	0.0188 (3)
N3A	0.59696 (13)	0.25477 (13)	0.50343 (9)	0.0132 (2)
C1A	0.55777 (15)	0.36511 (14)	0.41114 (11)	0.0125 (2)
C2A	0.40471 (16)	0.41035 (15)	0.37477 (11)	0.0149 (3)
H2AA	0.3247	0.3646	0.4118	0.018*
C3A	0.36921 (16)	0.52204 (15)	0.28463 (12)	0.0168 (3)
H3AA	0.2645	0.5525	0.2613	0.020*
C4A	0.48421 (17)	0.58940 (15)	0.22839 (11)	0.0167 (3)
H4AA	0.4596	0.6644	0.1661	0.020*
C5A	0.63585 (16)	0.54578 (15)	0.26423 (11)	0.0146 (3)
H5AA	0.7146	0.5924	0.2261	0.018*
C6A	0.67591 (15)	0.43462 (14)	0.35539 (11)	0.0121 (2)
C7A	0.83924 (15)	0.39970 (14)	0.39030 (11)	0.0125 (2)
C8A	0.50778 (15)	0.16825 (14)	0.56596 (11)	0.0134 (3)
C9A	0.59175 (17)	0.05670 (16)	0.65623 (12)	0.0185 (3)
H9AA	0.6019	−0.0446	0.6420	0.028*
H9AB	0.5271	0.0779	0.7318	0.028*
H9AC	0.7010	0.0641	0.6537	0.028*
O1B	1.10383 (11)	0.00132 (11)	0.61515 (8)	0.0152 (2)
O2B	0.71673 (13)	−0.21124 (12)	1.05408 (8)	0.0231 (2)
N1B	0.97720 (13)	0.02967 (12)	0.71262 (9)	0.0141 (2)
N2B	1.14247 (14)	0.15404 (13)	0.75828 (11)	0.0161 (2)
N3B	0.79291 (14)	−0.06646 (13)	0.89487 (10)	0.0159 (2)
C1B	0.78846 (16)	0.06046 (15)	0.94314 (11)	0.0149 (3)
C2B	0.68093 (17)	0.10631 (16)	1.04286 (12)	0.0197 (3)
H2BA	0.6093	0.0513	1.0793	0.024*
C3B	0.67802 (19)	0.23181 (17)	1.08911 (13)	0.0234 (3)
H3BA	0.6063	0.2608	1.1580	0.028*
C4B	0.77935 (18)	0.31493 (17)	1.03513 (13)	0.0223 (3)
H4BA	0.7768	0.4011	1.0665	0.027*
C5B	0.88416 (17)	0.27147 (15)	0.93527 (12)	0.0180 (3)
H5BA	0.9524	0.3295	0.8983	0.022*
C6B	0.89229 (15)	0.14440 (14)	0.88740 (11)	0.0139 (3)
C7B	1.01102 (15)	0.10389 (14)	0.78082 (11)	0.0126 (2)
C8B	0.76306 (17)	−0.19266 (16)	0.95037 (12)	0.0179 (3)
C9B	0.7947 (2)	−0.31289 (18)	0.87350 (13)	0.0274 (3)
H9BA	0.7122	−0.3641	0.8981	0.041*
H9BB	0.9041	−0.3853	0.8780	0.041*
H9BC	0.7886	−0.2676	0.7944	0.041*
H3NA	0.696 (2)	0.235 (2)	0.5204 (15)	0.030 (5)*
H3NB	0.840 (2)	−0.069 (2)	0.8244 (17)	0.028 (5)*
H1NA	0.998 (2)	0.488 (2)	0.3996 (15)	0.024 (5)*
H1NB	1.181 (2)	0.165 (2)	0.8176 (18)	0.036 (5)*
H2NA	0.851 (2)	0.602 (3)	0.3617 (17)	0.038 (5)*
H2NB	1.218 (2)	0.116 (2)	0.6985 (17)	0.030 (5)*
H1OA	1.085 (2)	0.168 (2)	0.5101 (17)	0.038 (5)*
H1OB	1.095 (2)	−0.089 (2)	0.5974 (17)	0.037 (5)*

	U11	U22	U33	U12	U13	U23
O1A	0.0131 (5)	0.0187 (5)	0.0250 (5)	−0.0069 (4)	−0.0079 (4)	0.0030 (4)
O2A	0.0145 (5)	0.0259 (5)	0.0208 (5)	−0.0105 (4)	−0.0049 (4)	0.0061 (4)
N1A	0.0104 (5)	0.0155 (5)	0.0161 (5)	−0.0054 (4)	−0.0037 (4)	−0.0003 (4)
N2A	0.0166 (6)	0.0137 (6)	0.0280 (7)	−0.0070 (5)	−0.0077 (5)	0.0023 (5)
N3A	0.0103 (5)	0.0165 (5)	0.0125 (5)	−0.0049 (4)	−0.0020 (4)	0.0010 (4)
C1A	0.0138 (6)	0.0125 (6)	0.0101 (6)	−0.0029 (5)	−0.0008 (5)	−0.0017 (5)
C2A	0.0137 (6)	0.0172 (6)	0.0133 (6)	−0.0044 (5)	−0.0015 (5)	−0.0019 (5)
C3A	0.0141 (6)	0.0188 (7)	0.0164 (7)	−0.0019 (5)	−0.0056 (5)	−0.0023 (5)
C4A	0.0204 (7)	0.0149 (6)	0.0127 (6)	−0.0030 (5)	−0.0047 (5)	0.0011 (5)
C5A	0.0171 (6)	0.0141 (6)	0.0121 (6)	−0.0054 (5)	−0.0004 (5)	−0.0011 (5)
C6A	0.0128 (6)	0.0105 (6)	0.0123 (6)	−0.0020 (5)	−0.0015 (5)	−0.0031 (5)
C7A	0.0135 (6)	0.0137 (6)	0.0104 (6)	−0.0051 (5)	0.0007 (5)	−0.0033 (5)
C8A	0.0125 (6)	0.0145 (6)	0.0123 (6)	−0.0043 (5)	−0.0002 (5)	−0.0013 (5)
C9A	0.0165 (6)	0.0201 (7)	0.0183 (7)	−0.0079 (5)	−0.0039 (5)	0.0057 (5)
O1B	0.0169 (5)	0.0158 (5)	0.0129 (5)	−0.0068 (4)	0.0026 (4)	−0.0036 (4)
O2B	0.0321 (6)	0.0288 (6)	0.0148 (5)	−0.0197 (5)	−0.0053 (4)	0.0044 (4)
N1B	0.0142 (5)	0.0161 (5)	0.0112 (5)	−0.0051 (4)	0.0010 (4)	−0.0019 (4)
N2B	0.0182 (6)	0.0189 (6)	0.0138 (6)	−0.0093 (5)	−0.0020 (5)	−0.0020 (5)
N3B	0.0194 (6)	0.0171 (6)	0.0122 (6)	−0.0087 (5)	−0.0010 (4)	0.0008 (4)
C1B	0.0162 (6)	0.0146 (6)	0.0126 (6)	−0.0029 (5)	−0.0047 (5)	0.0015 (5)
C2B	0.0181 (7)	0.0214 (7)	0.0164 (7)	−0.0045 (5)	−0.0007 (5)	0.0013 (5)
C3B	0.0248 (7)	0.0228 (7)	0.0157 (7)	−0.0004 (6)	0.0016 (6)	−0.0039 (6)
C4B	0.0268 (7)	0.0184 (7)	0.0193 (7)	−0.0031 (6)	−0.0018 (6)	−0.0067 (6)
C5B	0.0199 (7)	0.0160 (6)	0.0175 (7)	−0.0047 (5)	−0.0034 (5)	−0.0012 (5)
C6B	0.0142 (6)	0.0139 (6)	0.0121 (6)	−0.0019 (5)	−0.0043 (5)	0.0001 (5)
C7B	0.0139 (6)	0.0102 (6)	0.0124 (6)	−0.0032 (5)	−0.0028 (5)	0.0020 (4)
C8B	0.0188 (6)	0.0210 (7)	0.0172 (7)	−0.0110 (5)	−0.0055 (5)	0.0030 (5)
C9B	0.0428 (9)	0.0228 (8)	0.0219 (8)	−0.0187 (7)	−0.0041 (7)	−0.0002 (6)

O1A—N1A	1.4232 (13)	O1B—N1B	1.4333 (14)
O1A—H1OA	0.93 (2)	O1B—H1OB	0.95 (2)
O2A—C8A	1.2257 (16)	O2B—C8B	1.2315 (17)
N1A—C7A	1.2992 (17)	N1B—C7B	1.2972 (17)
N2A—C7A	1.3590 (16)	N2B—C7B	1.3577 (16)
N2A—H1NA	0.857 (19)	N2B—H1NB	0.88 (2)
N2A—H2NA	0.87 (2)	N2B—H2NB	0.90 (2)
N3A—C8A	1.3644 (16)	N3B—C8B	1.3593 (17)
N3A—C1A	1.4069 (16)	N3B—C1B	1.4098 (17)
N3A—H3NA	0.885 (19)	N3B—H3NB	0.863 (19)
C1A—C2A	1.4005 (18)	C1B—C2B	1.3962 (19)
C1A—C6A	1.4179 (17)	C1B—C6B	1.4140 (18)
C2A—C3A	1.3915 (18)	C2B—C3B	1.389 (2)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.3845 (19)	C3B—C4B	1.387 (2)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.3873 (19)	C4B—C5B	1.383 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.4027 (17)	C5B—C6B	1.3977 (19)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C7A	1.4874 (17)	C6B—C7B	1.4907 (18)
C8A—C9A	1.5031 (18)	C8B—C9B	1.505 (2)
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C9A—H9AB	0.9800	C9B—H9BB	0.9800
C9A—H9AC	0.9800	C9B—H9BC	0.9800
N1A—O1A—H1OA	99.4 (12)	N1B—O1B—H1OB	99.3 (12)
C7A—N1A—O1A	109.97 (10)	C7B—N1B—O1B	109.89 (10)
C7A—N2A—H1NA	114.6 (12)	C7B—N2B—H1NB	116.8 (13)
C7A—N2A—H2NA	119.9 (13)	C7B—N2B—H2NB	114.9 (12)
H1NA—N2A—H2NA	117.3 (18)	H1NB—N2B—H2NB	115.9 (17)
C8A—N3A—C1A	129.30 (11)	C8B—N3B—C1B	127.77 (12)
C8A—N3A—H3NA	115.5 (12)	C8B—N3B—H3NB	117.8 (12)
C1A—N3A—H3NA	115.1 (12)	C1B—N3B—H3NB	113.0 (12)
C2A—C1A—N3A	121.95 (11)	C2B—C1B—N3B	121.21 (12)
C2A—C1A—C6A	119.31 (12)	C2B—C1B—C6B	119.76 (12)
N3A—C1A—C6A	118.72 (11)	N3B—C1B—C6B	119.01 (12)
C3A—C2A—C1A	120.31 (12)	C3B—C2B—C1B	120.43 (13)
C3A—C2A—H2AA	119.8	C3B—C2B—H2BA	119.8
C1A—C2A—H2AA	119.8	C1B—C2B—H2BA	119.8
C4A—C3A—C2A	120.99 (12)	C4B—C3B—C2B	120.26 (13)
C4A—C3A—H3AA	119.5	C4B—C3B—H3BA	119.9
C2A—C3A—H3AA	119.5	C2B—C3B—H3BA	119.9
C3A—C4A—C5A	119.06 (12)	C5B—C4B—C3B	119.55 (13)
C3A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.2
C5A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.2
C4A—C5A—C6A	121.70 (12)	C4B—C5B—C6B	121.71 (13)
C4A—C5A—H5AA	119.1	C4B—C5B—H5BA	119.1
C6A—C5A—H5AA	119.1	C6B—C5B—H5BA	119.1
C5A—C6A—C1A	118.61 (11)	C5B—C6B—C1B	118.27 (12)
C5A—C6A—C7A	117.69 (11)	C5B—C6B—C7B	118.22 (12)
C1A—C6A—C7A	123.68 (11)	C1B—C6B—C7B	123.51 (12)
N1A—C7A—N2A	122.40 (12)	N1B—C7B—N2B	124.22 (12)
N1A—C7A—C6A	119.40 (11)	N1B—C7B—C6B	117.67 (11)
N2A—C7A—C6A	118.14 (12)	N2B—C7B—C6B	118.01 (11)
O2A—C8A—N3A	123.82 (12)	O2B—C8B—N3B	124.54 (13)
O2A—C8A—C9A	121.50 (11)	O2B—C8B—C9B	121.64 (13)
N3A—C8A—C9A	114.68 (11)	N3B—C8B—C9B	113.82 (12)
C8A—C9A—H9AA	109.5	C8B—C9B—H9BA	109.5
C8A—C9A—H9AB	109.5	C8B—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
C8A—C9A—H9AC	109.5	C8B—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
C8A—N3A—C1A—C2A	5.0 (2)	C8B—N3B—C1B—C2B	−31.7 (2)
C8A—N3A—C1A—C6A	−176.47 (12)	C8B—N3B—C1B—C6B	149.88 (14)
N3A—C1A—C2A—C3A	178.69 (12)	N3B—C1B—C2B—C3B	−179.89 (13)
C6A—C1A—C2A—C3A	0.20 (19)	C6B—C1B—C2B—C3B	−1.5 (2)
C1A—C2A—C3A—C4A	0.7 (2)	C1B—C2B—C3B—C4B	1.5 (2)
C2A—C3A—C4A—C5A	−1.0 (2)	C2B—C3B—C4B—C5B	−0.4 (2)
C3A—C4A—C5A—C6A	0.4 (2)	C3B—C4B—C5B—C6B	−0.7 (2)
C4A—C5A—C6A—C1A	0.45 (19)	C4B—C5B—C6B—C1B	0.7 (2)
C4A—C5A—C6A—C7A	−177.74 (12)	C4B—C5B—C6B—C7B	−178.83 (12)
C2A—C1A—C6A—C5A	−0.76 (18)	C2B—C1B—C6B—C5B	0.42 (19)
N3A—C1A—C6A—C5A	−179.30 (12)	N3B—C1B—C6B—C5B	178.85 (12)
C2A—C1A—C6A—C7A	177.32 (12)	C2B—C1B—C6B—C7B	179.89 (12)
N3A—C1A—C6A—C7A	−1.22 (18)	N3B—C1B—C6B—C7B	−1.69 (19)
O1A—N1A—C7A—N2A	2.73 (17)	O1B—N1B—C7B—N2B	3.63 (17)
O1A—N1A—C7A—C6A	179.87 (10)	O1B—N1B—C7B—C6B	179.80 (10)
C5A—C6A—C7A—N1A	−150.83 (12)	C5B—C6B—C7B—N1B	−152.96 (12)
C1A—C6A—C7A—N1A	31.08 (18)	C1B—C6B—C7B—N1B	27.57 (18)
C5A—C6A—C7A—N2A	26.43 (17)	C5B—C6B—C7B—N2B	23.45 (18)
C1A—C6A—C7A—N2A	−151.66 (13)	C1B—C6B—C7B—N2B	−156.02 (12)
C1A—N3A—C8A—O2A	−2.2 (2)	C1B—N3B—C8B—O2B	4.6 (2)
C1A—N3A—C8A—C9A	177.71 (13)	C1B—N3B—C8B—C9B	−174.30 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3NA···N1A	0.883 (19)	2.048 (19)	2.7463 (18)	135.2 (15)
N3B—H3NB···N1B	0.86 (2)	1.963 (19)	2.6798 (17)	139.7 (17)
N2B—H1NB···O2Bi	0.88 (2)	2.10 (2)	2.9725 (17)	173.0 (17)
N2A—H2NA···O2Aii	0.87 (3)	2.53 (2)	3.3004 (17)	149.0 (17)
N2A—H2NA···N2Biii	0.87 (3)	2.54 (2)	3.2522 (18)	139.6 (17)
N2B—H2NB···O2Aiv	0.903 (19)	2.12 (2)	2.8900 (17)	142.1 (16)
O1A—H1OA···O1B	0.933 (19)	1.844 (19)	2.7733 (15)	173.9 (18)
O1B—H1OB···N1Av	0.951 (18)	1.809 (18)	2.7597 (15)	177.0 (17)
C2A—H2AA···O2A	0.95	2.22	2.8556 (17)	123
C5A—H5AA···O2Bvi	0.95	2.55	3.2773 (17)	133
C9A—H9AC···N1B	0.98	2.56	3.499 (2)	160
C4A—H4AA···Cg2ii	0.95	2.95	3.7524 (16)	143
C3B—H3BA···Cg1vii	0.95	2.88	3.6645 (17)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—H3NA⋯N1A	0.883 (19)	2.048 (19)	2.7463 (18)	135.2 (15)
N3B—H3NB⋯N1B	0.86 (2)	1.963 (19)	2.6798 (17)	139.7 (17)
N2B—H1NB⋯O2B i	0.88 (2)	2.10 (2)	2.9725 (17)	173.0 (17)
N2A—H2NA⋯O2A ii	0.87 (3)	2.53 (2)	3.3004 (17)	149.0 (17)
N2A—H2NA⋯N2B iii	0.87 (3)	2.54 (2)	3.2522 (18)	139.6 (17)
N2B—H2NB⋯O2A iv	0.903 (19)	2.12 (2)	2.8900 (17)	142.1 (16)
O1A—H1OA⋯O1B	0.933 (19)	1.844 (19)	2.7733 (15)	173.9 (18)
O1B—H1OB⋯N1A v	0.951 (18)	1.809 (18)	2.7597 (15)	177.0 (17)
C2A—H2AA⋯O2A	0.95	2.22	2.8556 (17)	123
C5A—H5AA⋯O2B vi	0.95	2.55	3.2773 (17)	133
C9A—H9AC⋯N1B	0.98	2.56	3.499 (2)	160
C4A—H4AA⋯Cg2ii	0.95	2.95	3.7524 (16)	143
C3B—H3BA⋯Cg1vii	0.95	2.88	3.6645 (17)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .