Diethyl 1-(4-methyl-phen-yl)-3-phenyl-5-oxopyrrolidine-2,2-dicarboxyl-ate.

In the title compound, C(23)H(25)NO(5), the lactam ring adopts an envelope conformation and both eth-oxy-carbonyl side chains show an s-cis conformation: one is nearly planar, the dihedral angle between CO(2) and OCH(2)CH(3) groups being 7.95 (14)° and the other is almost orthogonal, the C-O-C-C torsion angle being 85.33 (9)°. Dimers related by inversion symmetry are stabilized by C-H⋯O hydrogen bonds. The crystal structure is consolidated by weak intermolecular C-H⋯O inter-actions. Weak intra-molecular inter-actions of the same kind also occur.

Related literature

The title compound may show anti­bacterial activity as has been found in other γ-lactam derivatives. For related structures see: Nigam et al. (1989 ▶); Ray et al. (1994 ▶, 1998 ▶, 2004 ▶, 2010 ▶); Kandasamy et al. (1995 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶); Rao et al. (1981 ▶). For hydrogen bonding, see: Desiraju (2005 ▶).

Experimental

Crystal data

C23H25NO5

M = 395.44

Triclinic,

a = 9.4905 (2) Å

b = 10.6167 (2) Å

c = 10.8198 (2) Å

α = 93.014 (1)°

β = 95.167 (1)°

γ = 110.537 (1)°

V = 1012.60 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.42 × 0.30 × 0.12 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.964, T max = 0.996

14991 measured reflections

3672 independent reflections

3331 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.091

S = 1.87

3672 reflections

362 parameters

All H-atom parameters refined

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028552/rn2065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028552/rn2065Isup2.hkl

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

C23H25NO5	Z = 2
Mr = 395.44	F(000) = 420
Triclinic, P1	Dx = 1.297 Mg m−3
Hall symbol: -P 1	Melting point: 401 K
a = 9.4905 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6167 (2) Å	Cell parameters from 9079 reflections
c = 10.8198 (2) Å	θ = 2.5–28.2°
α = 93.014 (1)°	µ = 0.09 mm−1
β = 95.167 (1)°	T = 100 K
γ = 110.537 (1)°	Block, colourless
V = 1012.60 (3) Å3	0.42 × 0.30 × 0.12 mm

Bruker APEXII area-detector diffractometer	3672 independent reflections
Radiation source: fine-focus sealed tube	3331 reflections with I > 2σ(I)
graphite	Rint = 0.020
phi and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.964, Tmax = 0.996	k = −12→12
14991 measured reflections	l = −13→13

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	All H-atom parameters refined
S = 1.87	w = 1/[σ2(Fo2) + (0.0352P)2] where P = (Fo2 + 2Fc2)/3
3672 reflections	(Δ/σ)max = 0.001
362 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. Data was collected using a X8 APEX II BRUKER-Nonius diffractometer equipped with an KRYOFLEX low-temperature apparatus operating at 100 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.5° per frame for 10 s, such that a total of 2870 frames were collected in a optimized strategy and with a final resolution of 0.75 Å. Data integration and reduction was performed using the APEX2 (Bruker, 2009) software suite. Absorption corrections were applied using SADABS (Bruker, 2009). The structures are solved by direct methods using the SHELX97 program and refined by least squares on F2SHELXL97, incorporated in the Apex2 software suite.

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.All non-hydrogen atoms were refined anisotropically. Hydrogen were found in subsequent difference Fourier maps and included as isotropic atoms.

	x	y	z	Uiso*/Ueq
O1	−0.06859 (8)	0.71231 (8)	0.72064 (8)	0.0250 (2)
O2	0.19397 (9)	0.56920 (8)	0.97081 (7)	0.0205 (2)
O3	0.28043 (8)	0.41475 (7)	0.88942 (6)	0.01674 (18)
O4	0.27852 (9)	0.49468 (9)	0.55611 (7)	0.0247 (2)
O5	0.43697 (8)	0.59245 (8)	0.72998 (6)	0.01664 (18)
N1	0.13851 (9)	0.64837 (9)	0.73404 (8)	0.0144 (2)
C1	−0.01411 (11)	0.62475 (11)	0.72555 (9)	0.0162 (2)
C2	−0.09624 (12)	0.47497 (11)	0.72503 (11)	0.0169 (2)
H2A	−0.1303 (14)	0.4554 (13)	0.8076 (13)	0.026 (3)*
H2B	−0.1846 (14)	0.4437 (13)	0.6609 (12)	0.022 (3)*
C3	0.02044 (11)	0.41224 (11)	0.69452 (10)	0.0150 (2)
H3	0.0252 (13)	0.4114 (12)	0.6039 (12)	0.017 (3)*
C4	0.17508 (11)	0.52637 (10)	0.74648 (9)	0.0140 (2)
C5	0.24744 (11)	0.78151 (11)	0.73057 (9)	0.0146 (2)
C6	0.34323 (13)	0.85116 (12)	0.83513 (10)	0.0215 (3)
H6	0.3365 (15)	0.8085 (14)	0.9110 (14)	0.035 (4)*
C7	0.44489 (13)	0.98064 (12)	0.82749 (11)	0.0244 (3)
H7	0.5146 (15)	1.0322 (14)	0.8986 (13)	0.031 (3)*
C8	0.45132 (12)	1.04361 (11)	0.71799 (10)	0.0204 (3)
C9	0.35414 (12)	0.97144 (12)	0.61366 (10)	0.0218 (3)
H9	0.3578 (15)	1.0138 (14)	0.5335 (13)	0.033 (4)*
C10	0.25387 (12)	0.84142 (11)	0.61952 (10)	0.0196 (3)
H10	0.1856 (16)	0.7897 (14)	0.5467 (13)	0.030 (3)*
C11	0.55881 (16)	1.18611 (13)	0.71308 (13)	0.0290 (3)
H11A	0.6210 (17)	1.2226 (15)	0.7902 (14)	0.037 (4)*
H11B	0.5053 (18)	1.2474 (17)	0.6996 (15)	0.048 (4)*
H11C	0.6186 (19)	1.1952 (16)	0.6448 (15)	0.048 (4)*
C12	−0.00523 (11)	0.27271 (11)	0.73582 (10)	0.0163 (2)
C13	−0.06002 (12)	0.23452 (11)	0.84876 (11)	0.0197 (2)
H13	−0.0828 (14)	0.2983 (13)	0.9043 (12)	0.025 (3)*
C14	−0.08302 (13)	0.10562 (12)	0.88368 (12)	0.0247 (3)
H14	−0.1211 (16)	0.0818 (14)	0.9631 (13)	0.033 (4)*
C15	−0.05170 (14)	0.01258 (12)	0.80671 (12)	0.0283 (3)
H15	−0.0677 (15)	−0.0789 (15)	0.8318 (12)	0.033 (4)*
C16	0.00369 (14)	0.04957 (13)	0.69484 (12)	0.0277 (3)
H16	0.0251 (16)	−0.0136 (15)	0.6414 (13)	0.035 (4)*
C17	0.02681 (13)	0.17826 (12)	0.65939 (11)	0.0216 (3)
H17	0.0627 (15)	0.2023 (13)	0.5821 (13)	0.029 (3)*
C18	0.21958 (11)	0.50969 (10)	0.88294 (9)	0.0140 (2)
C19	0.30418 (13)	0.37111 (12)	1.01290 (10)	0.0198 (3)
H19A	0.2082 (14)	0.3496 (12)	1.0498 (11)	0.019 (3)*
H19B	0.3819 (13)	0.4486 (13)	1.0648 (11)	0.017 (3)*
C20	0.35183 (15)	0.25173 (13)	0.99354 (12)	0.0266 (3)
H20A	0.2751 (19)	0.1811 (17)	0.9407 (15)	0.045 (4)*
H20B	0.3660 (15)	0.2159 (14)	1.0749 (13)	0.034 (4)*
H20C	0.4514 (17)	0.2762 (14)	0.9584 (13)	0.037 (4)*
C21	0.30183 (11)	0.53278 (11)	0.66516 (9)	0.0148 (2)
C22	0.56966 (12)	0.61488 (13)	0.66233 (10)	0.0194 (3)
H22A	0.6495 (14)	0.6216 (12)	0.7267 (11)	0.017 (3)*
H22B	0.5482 (13)	0.5336 (13)	0.6052 (11)	0.018 (3)*
C23	0.60496 (15)	0.74321 (15)	0.60006 (13)	0.0299 (3)
H23A	0.6205 (15)	0.8196 (15)	0.6628 (13)	0.030 (4)*
H23B	0.6949 (17)	0.7600 (15)	0.5572 (13)	0.038 (4)*
H23C	0.5222 (17)	0.7335 (15)	0.5358 (14)	0.042 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0162 (4)	0.0157 (4)	0.0452 (5)	0.0083 (3)	0.0031 (3)	0.0041 (4)
O2	0.0276 (4)	0.0211 (4)	0.0159 (4)	0.0115 (3)	0.0066 (3)	0.0013 (3)
O3	0.0205 (4)	0.0187 (4)	0.0145 (4)	0.0108 (3)	0.0027 (3)	0.0044 (3)
O4	0.0195 (4)	0.0374 (5)	0.0148 (4)	0.0078 (4)	0.0034 (3)	−0.0028 (3)
O5	0.0119 (4)	0.0237 (4)	0.0151 (4)	0.0070 (3)	0.0034 (3)	0.0015 (3)
N1	0.0122 (4)	0.0123 (5)	0.0191 (5)	0.0048 (4)	0.0016 (3)	0.0026 (4)
C1	0.0141 (5)	0.0177 (6)	0.0177 (5)	0.0067 (4)	0.0021 (4)	0.0019 (4)
C2	0.0129 (5)	0.0153 (6)	0.0224 (6)	0.0048 (4)	0.0014 (4)	0.0027 (4)
C3	0.0144 (5)	0.0148 (5)	0.0150 (5)	0.0047 (4)	0.0013 (4)	0.0007 (4)
C4	0.0142 (5)	0.0139 (5)	0.0150 (5)	0.0063 (4)	0.0025 (4)	0.0008 (4)
C5	0.0122 (5)	0.0130 (5)	0.0200 (5)	0.0057 (4)	0.0033 (4)	0.0021 (4)
C6	0.0264 (6)	0.0183 (6)	0.0170 (6)	0.0048 (5)	0.0007 (5)	0.0038 (5)
C7	0.0267 (6)	0.0198 (6)	0.0200 (6)	0.0017 (5)	−0.0030 (5)	0.0003 (5)
C8	0.0178 (6)	0.0171 (6)	0.0253 (6)	0.0045 (5)	0.0037 (4)	0.0037 (5)
C9	0.0216 (6)	0.0214 (6)	0.0211 (6)	0.0052 (5)	0.0022 (5)	0.0072 (5)
C10	0.0177 (6)	0.0191 (6)	0.0189 (6)	0.0036 (5)	−0.0017 (4)	0.0022 (5)
C11	0.0287 (7)	0.0215 (7)	0.0289 (7)	−0.0006 (6)	0.0007 (6)	0.0051 (5)
C12	0.0122 (5)	0.0143 (6)	0.0210 (5)	0.0036 (4)	−0.0006 (4)	0.0002 (4)
C13	0.0186 (6)	0.0172 (6)	0.0241 (6)	0.0070 (5)	0.0035 (4)	0.0020 (5)
C14	0.0234 (6)	0.0208 (6)	0.0300 (7)	0.0070 (5)	0.0043 (5)	0.0079 (5)
C15	0.0283 (7)	0.0149 (6)	0.0410 (7)	0.0080 (5)	−0.0018 (5)	0.0044 (5)
C16	0.0297 (7)	0.0191 (6)	0.0353 (7)	0.0125 (5)	−0.0013 (5)	−0.0066 (5)
C17	0.0206 (6)	0.0216 (6)	0.0228 (6)	0.0088 (5)	0.0011 (5)	−0.0024 (5)
C18	0.0112 (5)	0.0135 (5)	0.0169 (5)	0.0030 (4)	0.0038 (4)	0.0026 (4)
C19	0.0224 (6)	0.0224 (6)	0.0147 (5)	0.0077 (5)	0.0005 (5)	0.0058 (5)
C20	0.0312 (7)	0.0267 (7)	0.0259 (7)	0.0152 (6)	0.0003 (5)	0.0081 (5)
C21	0.0156 (5)	0.0148 (5)	0.0156 (5)	0.0070 (4)	0.0022 (4)	0.0032 (4)
C22	0.0128 (5)	0.0298 (7)	0.0181 (6)	0.0094 (5)	0.0058 (4)	0.0041 (5)
C23	0.0211 (6)	0.0374 (8)	0.0338 (7)	0.0104 (6)	0.0099 (6)	0.0143 (6)

O1—C1	1.2132 (13)	C9—H9	0.996 (14)
O2—C18	1.2035 (12)	C10—H10	0.977 (15)
O3—C18	1.3278 (12)	C11—H11A	0.955 (16)
O3—C19	1.4611 (12)	C11—H11B	0.965 (17)
O4—C21	1.2019 (13)	C11—H11C	0.960 (17)
O5—C21	1.3264 (13)	C12—C13	1.3952 (15)
O5—C22	1.4671 (12)	C12—C17	1.3978 (16)
N1—C1	1.3741 (13)	C13—C14	1.3867 (16)
N1—C5	1.4337 (13)	C13—H13	0.974 (13)
N1—C4	1.4633 (13)	C14—C15	1.3862 (18)
C1—C2	1.5049 (15)	C14—H14	0.974 (14)
C2—C3	1.5294 (14)	C15—C16	1.3840 (18)
C2—H2A	0.985 (13)	C15—H15	0.986 (14)
C2—H2B	0.985 (13)	C16—C17	1.3862 (17)
C3—C12	1.5131 (15)	C16—H16	0.949 (15)
C3—C4	1.5716 (14)	C17—H17	0.945 (14)
C3—H3	0.985 (12)	C19—C20	1.4987 (17)
C4—C18	1.5353 (14)	C19—H19A	0.985 (13)
C4—C21	1.5380 (14)	C19—H19B	0.994 (13)
C5—C6	1.3813 (15)	C20—H20A	0.957 (17)
C5—C10	1.3851 (15)	C20—H20B	0.994 (14)
C6—C7	1.3867 (16)	C20—H20C	1.004 (15)
C6—H6	0.955 (15)	C22—C23	1.4964 (17)
C7—C8	1.3865 (16)	C22—H22A	0.963 (12)
C7—H7	0.969 (14)	C22—H22B	0.983 (13)
C8—C9	1.3920 (16)	C23—H23A	0.990 (15)
C8—C11	1.5059 (16)	C23—H23B	0.974 (15)
C9—C10	1.3833 (16)	C23—H23C	0.974 (16)
C18—O3—C19	116.52 (8)	H11B—C11—H11C	104.4 (13)
C21—O5—C22	117.09 (8)	C13—C12—C17	118.39 (10)
C1—N1—C5	121.50 (9)	C13—C12—C3	122.07 (9)
C1—N1—C4	113.50 (8)	C17—C12—C3	119.54 (10)
C5—N1—C4	125.00 (8)	C14—C13—C12	120.68 (11)
O1—C1—N1	124.33 (10)	C14—C13—H13	119.0 (8)
O1—C1—C2	127.73 (9)	C12—C13—H13	120.3 (8)
N1—C1—C2	107.93 (9)	C15—C14—C13	120.39 (12)
C1—C2—C3	104.67 (8)	C15—C14—H14	120.7 (8)
C1—C2—H2A	108.8 (8)	C13—C14—H14	118.9 (8)
C3—C2—H2A	112.7 (7)	C16—C15—C14	119.46 (11)
C1—C2—H2B	110.5 (8)	C16—C15—H15	120.2 (8)
C3—C2—H2B	110.7 (7)	C14—C15—H15	120.3 (8)
H2A—C2—H2B	109.5 (10)	C15—C16—C17	120.41 (11)
C12—C3—C2	116.32 (9)	C15—C16—H16	120.0 (9)
C12—C3—C4	116.64 (8)	C17—C16—H16	119.6 (9)
C2—C3—C4	102.81 (8)	C16—C17—C12	120.67 (11)
C12—C3—H3	110.1 (7)	C16—C17—H17	120.0 (8)
C2—C3—H3	107.7 (7)	C12—C17—H17	119.3 (8)
C4—C3—H3	102.0 (7)	O2—C18—O3	125.34 (9)
N1—C4—C18	111.92 (8)	O2—C18—C4	124.12 (9)
N1—C4—C21	108.16 (8)	O3—C18—C4	110.40 (8)
C18—C4—C21	111.84 (8)	O3—C19—C20	106.36 (9)
N1—C4—C3	101.81 (8)	O3—C19—H19A	107.5 (7)
C18—C4—C3	110.42 (8)	C20—C19—H19A	113.3 (7)
C21—C4—C3	112.27 (8)	O3—C19—H19B	107.9 (7)
C6—C5—C10	119.81 (10)	C20—C19—H19B	113.4 (7)
C6—C5—N1	121.64 (9)	H19A—C19—H19B	108.1 (10)
C10—C5—N1	118.54 (9)	C19—C20—H20A	110.4 (9)
C5—C6—C7	119.44 (10)	C19—C20—H20B	109.6 (8)
C5—C6—H6	118.6 (9)	H20A—C20—H20B	107.7 (12)
C7—C6—H6	122.0 (9)	C19—C20—H20C	112.2 (8)
C8—C7—C6	121.76 (11)	H20A—C20—H20C	110.3 (12)
C8—C7—H7	116.5 (8)	H20B—C20—H20C	106.5 (11)
C6—C7—H7	121.8 (8)	O4—C21—O5	125.77 (10)
C7—C8—C9	117.84 (10)	O4—C21—C4	123.35 (9)
C7—C8—C11	120.84 (10)	O5—C21—C4	110.77 (8)
C9—C8—C11	121.31 (10)	O5—C22—C23	110.51 (9)
C10—C9—C8	120.96 (10)	O5—C22—H22A	103.6 (7)
C10—C9—H9	119.6 (8)	C23—C22—H22A	110.8 (7)
C8—C9—H9	119.4 (8)	O5—C22—H22B	106.9 (7)
C9—C10—C5	120.17 (10)	C23—C22—H22B	114.4 (7)
C9—C10—H10	121.6 (8)	H22A—C22—H22B	109.9 (10)
C5—C10—H10	118.2 (8)	C22—C23—H23A	109.7 (8)
C8—C11—H11A	112.6 (9)	C22—C23—H23B	110.8 (9)
C8—C11—H11B	111.6 (10)	H23A—C23—H23B	110.0 (12)
H11A—C11—H11B	103.5 (13)	C22—C23—H23C	108.9 (9)
C8—C11—H11C	112.7 (10)	H23A—C23—H23C	111.5 (12)
H11A—C11—H11C	111.4 (13)	H23B—C23—H23C	106.0 (12)
C5—N1—C1—O1	−3.65 (16)	C6—C5—C10—C9	−1.04 (16)
C4—N1—C1—O1	176.36 (10)	N1—C5—C10—C9	177.92 (10)
C5—N1—C1—C2	176.93 (9)	C2—C3—C12—C13	−38.01 (14)
C4—N1—C1—C2	−3.06 (11)	C4—C3—C12—C13	83.65 (12)
O1—C1—C2—C3	163.95 (11)	C2—C3—C12—C17	142.13 (10)
N1—C1—C2—C3	−16.65 (11)	C4—C3—C12—C17	−96.21 (12)
C1—C2—C3—C12	156.77 (9)	C17—C12—C13—C14	−0.44 (16)
C1—C2—C3—C4	28.05 (10)	C3—C12—C13—C14	179.69 (10)
C1—N1—C4—C18	−97.26 (10)	C12—C13—C14—C15	0.05 (17)
C5—N1—C4—C18	82.75 (11)	C13—C14—C15—C16	0.39 (18)
C1—N1—C4—C21	139.09 (9)	C14—C15—C16—C17	−0.44 (18)
C5—N1—C4—C21	−40.89 (12)	C15—C16—C17—C12	0.04 (18)
C1—N1—C4—C3	20.66 (10)	C13—C12—C17—C16	0.40 (16)
C5—N1—C4—C3	−159.32 (9)	C3—C12—C17—C16	−179.73 (10)
C12—C3—C4—N1	−157.57 (8)	C19—O3—C18—O2	6.15 (14)
C2—C3—C4—N1	−29.05 (10)	C19—O3—C18—C4	−169.70 (8)
C12—C3—C4—C18	−38.57 (12)	N1—C4—C18—O2	16.45 (14)
C2—C3—C4—C18	89.95 (9)	C21—C4—C18—O2	138.00 (10)
C12—C3—C4—C21	86.98 (11)	C3—C4—C18—O2	−96.21 (12)
C2—C3—C4—C21	−144.51 (8)	N1—C4—C18—O3	−167.65 (8)
C1—N1—C5—C6	109.35 (12)	C21—C4—C18—O3	−46.09 (11)
C4—N1—C5—C6	−70.67 (14)	C3—C4—C18—O3	79.70 (10)
C1—N1—C5—C10	−69.59 (13)	C18—O3—C19—C20	172.04 (9)
C4—N1—C5—C10	110.40 (11)	C22—O5—C21—O4	0.53 (16)
C10—C5—C6—C7	0.02 (16)	C22—O5—C21—C4	−175.69 (8)
N1—C5—C6—C7	−178.91 (10)	N1—C4—C21—O4	−85.80 (12)
C5—C6—C7—C8	1.25 (18)	C18—C4—C21—O4	150.51 (10)
C6—C7—C8—C9	−1.45 (17)	C3—C4—C21—O4	25.74 (14)
C6—C7—C8—C11	177.81 (12)	N1—C4—C21—O5	90.53 (10)
C7—C8—C9—C10	0.40 (17)	C18—C4—C21—O5	−33.16 (12)
C11—C8—C9—C10	−178.86 (11)	C3—C4—C21—O5	−157.93 (8)
C8—C9—C10—C5	0.83 (17)	C21—O5—C22—C23	84.62 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.985 (14)	2.529 (14)	3.5096 (14)	173.4 (10)
C3—H3···O4	0.984 (13)	2.369 (13)	2.8814 (14)	111.7 (9)
C6—H6···O2	0.955 (15)	2.573 (14)	3.3143 (14)	134.7 (11)
C13—H13···O2i	0.975 (14)	2.453 (14)	3.4128 (14)	168.3 (12)
C15—H15···O1ii	0.987 (15)	2.462 (15)	3.2184 (15)	133.2 (10)
C22—H22A···O1iii	0.963 (13)	2.513 (14)	3.2100 (15)	129.2 (9)
C22—H22B···O4iv	0.983 (13)	2.579 (13)	3.2426 (14)	124.9 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.985 (14)	2.529 (14)	3.5096 (14)	173.4 (10)
C3—H3⋯O4	0.984 (13)	2.369 (13)	2.8814 (14)	111.7 (9)
C6—H6⋯O2	0.955 (15)	2.573 (14)	3.3143 (14)	134.7 (11)
C13—H13⋯O2i	0.975 (14)	2.453 (14)	3.4128 (14)	168.3 (12)
C15—H15⋯O1ii	0.987 (15)	2.462 (15)	3.2184 (15)	133.2 (10)
C22—H22A⋯O1iii	0.963 (13)	2.513 (14)	3.2100 (15)	129.2 (9)
C22—H22B⋯O4iv	0.983 (13)	2.579 (13)	3.2426 (14)	124.9 (10)

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