Ethyl N-phenyl­oxamate

The oxamate group in the title compound, C₁₀H₁₁NO₃, is almost coplanar with the phenyl ring because of intramol­ecular hydrogen-bonding interactions, and the structure can be described as an anilide single bonded to an ethyl carboxyl­ate group. The supramolecular structure is achieved through intermolecular hard N—H...O and soft C—H...X (X = O and phenyl) hydrogen-bonding interactions.

S1. Comment

Ethyl oxamates have been used as intermediates in the synthesis of oxamide compounds (Martínez-Martínez et al., 1988) and more recently they have been used to design molecular clefts (Padilla-Martínez et al., 2003). In spite of the growing importance of such compounds, there are few known? examples of crystalline structures bearing aromatic oxamates and those that are known are at least disubstituted. We analyse here the crystalline structure of the title compound, (I), which bears an ethyl oxamate group as the only substituent.

Compound (I) crystallizes in the triclinic system (P-1, Z = 4), and two independent molecules, which are labelled A and B (Fig. 1), are found in the asymmetric unit. These differ slightly, as evidenced by the O8—C8—C9—O9 torsion angles, which are −174.99 (13) and 171.89 (13)° for molecules A and B, respectively. The geometric features caused by the presence of? the ethyl oxamate group are listed in Table 1. The two carbonyl groups are almost antiperiplanar, with a mean O8—C8—C9—O9 torsion angle of 173.3 (15)°, in agreement with the conformation most frequently adopted by open systems. The C6—C1—N7—C8 mean torsion angle is of 15.0 (1.6)°, showing that the ethyl oxamate group is almost in the mean phenyl-ring plane, in contrast to the out-of-plane conformation adopted by 1,2- (Martin et al., 2002) and 1,3-phenyl dioxamates (Padilla-Martínez et al., 2003). In spite of the planarity exhibited by the oxamate group [mean O8—C8—C9—O9 = 175.5 (15)°], the mean CO—CO distance of 1.543 (3) Å is close to the value for a Csp³—Csp³ single bond (Dewar & Schmeizing, 1968), indicating the absence of conjugation.

The mean N7—CO and N7—Ph distances of 1.348 (3) and 1.418 (3) Å are very similar to those values measured for acetanilide [1.354 (3) and 1.413 (3) Å, respectively; Brown & Corbridge, 1954; Brown, 1966]. Thus, (I) can be described as being composed of an anilide group single bonded to an ethyl carboxylate group, in accordance with the observed chemical reactivity of these systems (Padilla-Martínez et al., 2001). As a result of the lack of conjugation along the ethyl oxamate group, intramolecular hydrogen bonding should contribute to the planarity of the system, allowing the formation of two adjacent S(5) (N7—H7···O9) and S(6) (C6—H6···O8) ring motifs (Bernstein et al., 1995).

The hydrogen-bonding geometry is listed in Table 2. The two types of molecules can form A···B pairs through intermoleular three-centered O8···H5···O10 hydrogen bonds, thus forming R²₁(6)[D_aD_b] and R²₁(6)[D_cD_d] rings. Alternatively, two molecules of the same kind can form A···A' and B···B' pairs through intermolecular hydrogen bonding in the form of soft C2—H2···O9 and hard N7—H7···O9 (Desiraju, 1996) interactions, thus forming R¹₂(6)[D_eD_f] and R¹₂(6)[D_gD_h] ring motifs. By symmetry, the self-complementary R²₂(10)[D_e] and R²₂(10)[D_g] ring motifs appear (Fig. 2). The R¹₂(6) ring motif seems to be the characteristic motif for these systems, since it has been found for other non-substituted aromatic oxamates (García-Báez et al., 2003), whereas the R²₁(6) motif is typical for aliphatic oxamides (Nguyen, et al., 2001). The resulting paralell layers [1 2 − 3] are interlinked through CH···π(arene) interactions (Umezawa et al., 1998). The CH₃ (molecule A) and CH₂ (molecule B) moieties are hydrogen bonded to the phenyl ring of molecule A [C12A—H12B···Cg(1) and C11B—H11D···Cg(1), respectively], thus forming a staircase motif that completes the three-dimensional structure along the (0 1 2) direction (Fig. 3).

S2. Experimental

The compound was prepared from aniline (9.8 ml, 0.1 mol) and ethyl chlorooxoacetate (12.0 m, 0.1 mol) according to reported procedures (Martínez-Martínez et al., 1998), yielding, after crystallization from hexane, a white solid (11.8 g; yield 60%; m.p. 347 K). IR (KBr, cm⁻¹): 3345 (NH), 1708 (CO); ¹H NMR (300.08 MHz, DMSO-d₆, p.p.m.): 7.86 (d, 2H), 7.48 (t, 2H), 7.26 (t, 1H), 4.40 (q, 2H), 1.43 (t, 3H); ¹³C NMR (75.46 MHz, DMSO-d₆, p.p.m.): 161.4 (COO), 156.2 (CON), 138.2 (C_i), 129.5 (C_m), 125.4 (C_p), 121.2 (C_o), 63.0 (CH₂), 14.5 (CH₃). Crystals suitable for X-ray analysis were obtained after slow crystallization from toluene. The melting point was measured on an electrothermal IA 9100 apparatus and is uncorrected. The IR spectrum was recorded using a Perkin–Elmer 16 F PC IR spectrophotometer, and the NMR spectra were recorded using a Varian Mercury 300 MHz instrument.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).

Figures

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level. Two molecules are present in the asymmetric unit.
	Fig. 2. The supramolecular arrangement of the title compound, showing the hydrogen-bonding network along the (1 2 − 3) direction.
	Fig. 3. Assembly of parallel layers [1 2 − 3] along the (0 1 2) direction.

Ethyl N-phenyloxamate

Crystal data

C10H11NO3	Z = 4
Mr = 193.20	F(000) = 408
Triclinic, P1	Dx = 1.351 Mg m^−3
Hall symbol: -P 1	Melting point: 347 K
a = 7.8033 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6424 (7) Å	Cell parameters from 600 reflections
c = 13.2432 (9) Å	θ = 20–25°
α = 108.491 (1)°	µ = 0.10 mm^−1
β = 96.081 (1)°	T = 100 K
γ = 110.165 (1)°	Rhombohedron, colourless
V = 950.03 (11) Å^3	0.50 × 0.47 × 0.43 mm

Data collection

Bruker Smart area-detector diffractometer	4107 independent reflections
Radiation source: fine-focus sealed tube	3637 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 3 pixels mm^-1	θmax = 27.0°, θmin = 1.7°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.952, Tmax = 0.967	l = −16→16
10719 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 0.3757P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4107 reflections	Δρmax = 0.35 e Å^−3
256 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0054 (13)

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
C1A	0.40793 (18)	0.29510 (14)	0.66506 (11)	0.0165 (3)
C1B	0.42640 (18)	1.03245 (14)	0.16072 (11)	0.0165 (3)
C2A	0.54894 (19)	0.31794 (15)	0.75122 (11)	0.0188 (3)
H2A	0.6094	0.2528	0.7426	0.023*
C2B	0.41705 (19)	1.14896 (15)	0.24227 (11)	0.0197 (3)
H2B	0.3206	1.1812	0.2293	0.024*
C3A	0.6012 (2)	0.43530 (15)	0.84940 (11)	0.0208 (3)
H3A	0.6969	0.4501	0.9079	0.025*
C3B	0.5482 (2)	1.21782 (15)	0.34224 (11)	0.0215 (3)
H3B	0.5418	1.2977	0.3975	0.026*
C4A	0.5140 (2)	0.53132 (15)	0.86238 (12)	0.0212 (3)
H4A	0.5489	0.6113	0.9298	0.025*
C4B	0.68898 (19)	1.17088 (15)	0.36227 (11)	0.0204 (3)
H4B	0.7777	1.2172	0.4313	0.025*
C5A	0.3757 (2)	0.50951 (15)	0.77606 (12)	0.0207 (3)
H5A	0.3166	0.5755	0.7847	0.025*
C5B	0.69862 (19)	1.05583 (15)	0.28059 (12)	0.0202 (3)
H5B	0.7956	1.0241	0.2938	0.024*
C6A	0.32219 (19)	0.39249 (15)	0.67704 (11)	0.0195 (3)
H6A	0.2282	0.3791	0.6182	0.023*
C6B	0.56872 (19)	0.98586 (15)	0.17942 (11)	0.0187 (3)
H6B	0.5770	0.9073	0.1238	0.022*
C8A	0.20469 (19)	0.11137 (15)	0.48511 (11)	0.0180 (3)
C8B	0.24118 (19)	0.83553 (15)	−0.01844 (11)	0.0187 (3)
C9A	0.19617 (18)	−0.02827 (15)	0.39766 (11)	0.0170 (3)
C9B	0.07352 (19)	0.79890 (15)	−0.11143 (11)	0.0174 (3)
C11A	0.03962 (19)	−0.20379 (15)	0.22040 (11)	0.0185 (3)
H11A	0.0101	−0.2880	0.2425	0.022*
H11B	0.1595	−0.1860	0.1972	0.022*
C11B	−0.10753 (19)	0.63731 (15)	−0.28904 (11)	0.0200 (3)
H11C	−0.0853	0.7170	−0.3160	0.024*
H11D	−0.2303	0.6143	−0.2691	0.024*
C12A	−0.1163 (2)	−0.23230 (16)	0.12800 (11)	0.0219 (3)
H12A	−0.2353	−0.2551	0.1506	0.033*
H12B	−0.1265	−0.3142	0.0635	0.033*
H12C	−0.0886	−0.1462	0.1097	0.033*
C12B	−0.1064 (2)	0.50599 (16)	−0.37594 (12)	0.0254 (3)
H12D	0.0175	0.5293	−0.3927	0.038*
H12E	−0.2027	0.4763	−0.4425	0.038*
H12F	−0.1333	0.4269	−0.3492	0.038*
N7A	0.35830 (16)	0.17034 (12)	0.56864 (9)	0.0177 (2)
H7A	0.4363	0.1267	0.5627	0.021*
N7B	0.28635 (16)	0.96634 (12)	0.06075 (9)	0.0176 (3)
H7B	0.2220	1.0161	0.0492	0.021*
O8A	0.08365 (15)	0.15708 (11)	0.47463 (8)	0.0270 (3)
O8B	0.31572 (16)	0.75229 (12)	−0.02031 (9)	0.0305 (3)
O9A	0.30585 (13)	−0.08283 (10)	0.40773 (8)	0.0203 (2)
O9B	−0.01593 (14)	0.87252 (11)	−0.10624 (8)	0.0221 (2)
O10A	0.05531 (13)	−0.07642 (10)	0.31163 (8)	0.0194 (2)
O10B	0.04368 (14)	0.67911 (10)	−0.19398 (7)	0.0199 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0156 (6)	0.0167 (6)	0.0155 (6)	0.0055 (5)	0.0038 (5)	0.0050 (5)
C1B	0.0151 (6)	0.0174 (6)	0.0157 (6)	0.0047 (5)	0.0020 (5)	0.0072 (5)
C2A	0.0173 (7)	0.0185 (7)	0.0214 (7)	0.0090 (5)	0.0040 (5)	0.0066 (5)
C2B	0.0186 (7)	0.0197 (7)	0.0211 (7)	0.0096 (6)	0.0021 (5)	0.0068 (6)
C3A	0.0176 (7)	0.0226 (7)	0.0186 (7)	0.0071 (6)	−0.0004 (5)	0.0058 (6)
C3B	0.0230 (7)	0.0185 (7)	0.0183 (7)	0.0078 (6)	0.0028 (6)	0.0023 (5)
C4A	0.0211 (7)	0.0177 (7)	0.0195 (7)	0.0054 (6)	0.0050 (6)	0.0030 (5)
C4B	0.0179 (7)	0.0218 (7)	0.0174 (7)	0.0040 (6)	−0.0006 (5)	0.0081 (6)
C5A	0.0216 (7)	0.0181 (7)	0.0242 (7)	0.0105 (6)	0.0068 (6)	0.0071 (6)
C5B	0.0165 (7)	0.0225 (7)	0.0239 (7)	0.0091 (6)	0.0033 (5)	0.0110 (6)
C6A	0.0188 (7)	0.0223 (7)	0.0187 (7)	0.0097 (6)	0.0029 (5)	0.0085 (6)
C6B	0.0187 (7)	0.0195 (7)	0.0190 (7)	0.0093 (5)	0.0047 (5)	0.0069 (5)
C8A	0.0168 (7)	0.0198 (7)	0.0167 (6)	0.0085 (5)	0.0028 (5)	0.0053 (5)
C8B	0.0196 (7)	0.0210 (7)	0.0162 (6)	0.0105 (6)	0.0034 (5)	0.0056 (5)
C9A	0.0149 (6)	0.0198 (7)	0.0162 (6)	0.0071 (5)	0.0031 (5)	0.0066 (5)
C9B	0.0185 (7)	0.0187 (6)	0.0153 (6)	0.0084 (5)	0.0045 (5)	0.0057 (5)
C11A	0.0179 (7)	0.0174 (6)	0.0167 (6)	0.0068 (5)	0.0027 (5)	0.0028 (5)
C11B	0.0185 (7)	0.0220 (7)	0.0150 (6)	0.0070 (6)	−0.0005 (5)	0.0040 (5)
C12A	0.0186 (7)	0.0240 (7)	0.0180 (7)	0.0072 (6)	0.0008 (5)	0.0042 (6)
C12B	0.0254 (8)	0.0249 (7)	0.0189 (7)	0.0094 (6)	0.0020 (6)	0.0010 (6)
N7A	0.0170 (6)	0.0195 (6)	0.0166 (6)	0.0106 (5)	0.0022 (4)	0.0038 (5)
N7B	0.0182 (6)	0.0188 (6)	0.0156 (6)	0.0100 (5)	0.0003 (5)	0.0045 (5)
O8A	0.0241 (6)	0.0288 (6)	0.0244 (5)	0.0173 (5)	−0.0031 (4)	0.0007 (4)
O8B	0.0363 (6)	0.0281 (6)	0.0240 (5)	0.0221 (5)	−0.0056 (5)	−0.0001 (4)
O9A	0.0192 (5)	0.0226 (5)	0.0188 (5)	0.0116 (4)	0.0019 (4)	0.0049 (4)
O9B	0.0229 (5)	0.0240 (5)	0.0188 (5)	0.0139 (4)	0.0008 (4)	0.0036 (4)
O10A	0.0185 (5)	0.0203 (5)	0.0160 (5)	0.0093 (4)	−0.0002 (4)	0.0021 (4)
O10B	0.0217 (5)	0.0212 (5)	0.0141 (5)	0.0107 (4)	−0.0001 (4)	0.0022 (4)

Geometric parameters (Å, º)

O8A—C8A	1.2165 (16)	C3B—H3B	0.9500
O9A—C9A	1.2063 (16)	C4A—C5A	1.387 (2)
O10A—C9A	1.3209 (16)	C4A—H4A	0.9500
O10A—C11A	1.4586 (16)	C4B—C5B	1.384 (2)
N7A—C1A	1.4173 (17)	C4B—H4B	0.9500
N7A—C8A	1.3470 (17)	C5A—C6A	1.391 (2)
C8A—C9A	1.5421 (19)	C5A—H5A	0.9500
O8B—C8B	1.2116 (17)	C5B—C6B	1.3915 (19)
O9B—C9B	1.2078 (16)	C5B—H5B	0.9500
O10B—C9B	1.3161 (16)	C6A—H6A	0.9500
O10B—C11B	1.4639 (16)	C6B—H6B	0.9500
N7B—C1B	1.4193 (17)	C11A—C12A	1.5048 (19)
N7B—C8B	1.3488 (17)	C11A—H11A	0.9900
C8B—C9B	1.5436 (19)	C11A—H11B	0.9900
C1A—C6A	1.3941 (19)	C11B—C12B	1.5060 (19)
C1A—C2A	1.3948 (19)	C11B—H11C	0.9900
C1B—C2B	1.3924 (19)	C11B—H11D	0.9900
C1B—C6B	1.3928 (19)	C12A—H12A	0.9800
C2A—C3A	1.3868 (19)	C12A—H12B	0.9800
C2A—H2A	0.9500	C12A—H12C	0.9800
C2B—C3B	1.3848 (19)	C12B—H12D	0.9800
C2B—H2B	0.9500	C12B—H12E	0.9800
C3A—C4A	1.389 (2)	C12B—H12F	0.9800
C3A—H3A	0.9500	N7A—H7A	0.8800
C3B—C4B	1.388 (2)	N7B—H7B	0.8800
C6A—C1A—C2A	119.76 (12)	O8B—C8B—C9B	121.71 (12)
C6A—C1A—N7A	123.31 (12)	N7B—C8B—C9B	111.28 (11)
C2A—C1A—N7A	116.93 (12)	O9A—C9A—O10A	125.86 (12)
C2B—C1B—C6B	119.95 (12)	O9A—C9A—C8A	123.70 (12)
C2B—C1B—N7B	116.98 (12)	O10A—C9A—C8A	110.43 (11)
C6B—C1B—N7B	123.07 (12)	O9B—C9B—O10B	126.03 (12)
C3A—C2A—C1A	120.27 (13)	O9B—C9B—C8B	123.01 (12)
C3A—C2A—H2A	119.9	O10B—C9B—C8B	110.96 (11)
C1A—C2A—H2A	119.9	O10A—C11A—C12A	107.04 (11)
C3B—C2B—C1B	120.07 (13)	O10A—C11A—H11A	110.3
C3B—C2B—H2B	120.0	C12A—C11A—H11A	110.3
C1B—C2B—H2B	120.0	O10A—C11A—H11B	110.3
C2A—C3A—C4A	120.18 (13)	C12A—C11A—H11B	110.3
C2A—C3A—H3A	119.9	H11A—C11A—H11B	108.6
C4A—C3A—H3A	119.9	O10B—C11B—C12B	106.60 (11)
C2B—C3B—C4B	120.42 (13)	O10B—C11B—H11C	110.4
C2B—C3B—H3B	119.8	C12B—C11B—H11C	110.4
C4B—C3B—H3B	119.8	O10B—C11B—H11D	110.4
C5A—C4A—C3A	119.45 (13)	C12B—C11B—H11D	110.4
C5A—C4A—H4A	120.3	H11C—C11B—H11D	108.6
C3A—C4A—H4A	120.3	C11A—C12A—H12A	109.5
C5B—C4B—C3B	119.27 (13)	C11A—C12A—H12B	109.5
C5B—C4B—H4B	120.4	H12A—C12A—H12B	109.5
C3B—C4B—H4B	120.4	C11A—C12A—H12C	109.5
C4A—C5A—C6A	120.99 (13)	H12A—C12A—H12C	109.5
C4A—C5A—H5A	119.5	H12B—C12A—H12C	109.5
C6A—C5A—H5A	119.5	C11B—C12B—H12D	109.5
C4B—C5B—C6B	121.11 (13)	C11B—C12B—H12E	109.5
C4B—C5B—H5B	119.4	H12D—C12B—H12E	109.5
C6B—C5B—H5B	119.4	C11B—C12B—H12F	109.5
C5A—C6A—C1A	119.34 (13)	H12D—C12B—H12F	109.5
C5A—C6A—H6A	120.3	H12E—C12B—H12F	109.5
C1A—C6A—H6A	120.3	C8A—N7A—C1A	127.05 (11)
C5B—C6B—C1B	119.16 (13)	C8A—N7A—H7A	116.5
C5B—C6B—H6B	120.4	C1A—N7A—H7A	116.5
C1B—C6B—H6B	120.4	C8B—N7B—C1B	127.06 (11)
O8A—C8A—N7A	127.25 (13)	C8B—N7B—H7B	116.5
O8A—C8A—C9A	121.34 (12)	C1B—N7B—H7B	116.5
N7A—C8A—C9A	111.41 (11)	C9A—O10A—C11A	115.48 (10)
O8B—C8B—N7B	127.01 (13)	C9B—O10B—C11B	115.62 (10)
O8A—C8A—C9A—O9A	−174.99 (13)	C2B—C1B—C6B—C5B	0.9 (2)
N7A—C1A—C2A—C3A	−178.05 (12)	N7A—C8A—C9A—O9A	5.38 (19)
C6A—C1A—N7A—C8A	−13.6 (2)	O8A—C8A—C9A—O10A	5.86 (18)
N7A—C1A—C6A—C5A	177.86 (12)	N7A—C8A—C9A—O10A	−173.78 (11)
O8B—C8B—C9B—O9B	171.89 (13)	N7B—C8B—C9B—O9B	−7.37 (19)
N7B—C1B—C2B—C3B	179.44 (12)	O8B—C8B—C9B—O10B	−7.84 (19)
C6B—C1B—N7B—C8B	16.2 (2)	N7B—C8B—C9B—O10B	172.90 (11)
N7B—C1B—C6B—C5B	−179.07 (12)	O8A—C8A—N7A—C1A	3.1 (2)
C6A—C1A—C2A—C3A	1.4 (2)	C9A—C8A—N7A—C1A	−177.27 (12)
C6B—C1B—C2B—C3B	−0.5 (2)	C2A—C1A—N7A—C8A	165.85 (13)
C1A—C2A—C3A—C4A	−0.3 (2)	O8B—C8B—N7B—C1B	−2.4 (2)
C1B—C2B—C3B—C4B	−0.4 (2)	C9B—C8B—N7B—C1B	176.79 (11)
C2A—C3A—C4A—C5A	−0.6 (2)	C2B—C1B—N7B—C8B	−163.77 (13)
C2B—C3B—C4B—C5B	1.0 (2)	O9A—C9A—O10A—C11A	−2.57 (19)
C3A—C4A—C5A—C6A	0.4 (2)	C8A—C9A—O10A—C11A	176.56 (10)
C3B—C4B—C5B—C6B	−0.6 (2)	C12A—C11A—O10A—C9A	−174.86 (11)
C4A—C5A—C6A—C1A	0.6 (2)	O9B—C9B—O10B—C11B	2.8 (2)
C2A—C1A—C6A—C5A	−1.5 (2)	C8B—C9B—O10B—C11B	−177.49 (10)
C4B—C5B—C6B—C1B	−0.3 (2)	C12B—C11B—O10B—C9B	175.49 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7A—H7A···O9A^i	0.88	2.24	3.0867 (17)	161
N7B—H7B···O9B^ii	0.88	2.36	3.1410 (18)	148
N7A—H7A···O9A	0.88	2.30	2.7168 (16)	109
N7B—H7B···O9B	0.88	2.29	2.7059 (16)	109
C6A—H6A···O8A	0.95	2.31	2.8974 (18)	120
C6B—H6B···O8B	0.95	2.32	2.9004 (18)	119
C5A—H5A···O8B^iii	0.95	2.67	3.294 (2)	124
C5B—H5B···O8A^iv	0.95	2.70	3.3418 (18)	125
C5A—H5A···O10B^iii	0.95	2.72	3.622 (2)	160
C5B—H5B···O10A^iv	0.95	2.62	3.5669 (19)	175
C2A—H2A···O9A^i	0.95	2.55	3.3309 (19)	140
C2B—H2B···O9B^ii	0.95	2.51	3.3385 (19)	146
C11B—H11D···Cg1^v	0.99	2.79	3.6719 (17)	149
C12A—H12A···Cg1^vi	0.98	2.62	3.4703 (18)	146

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