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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2104–o2105.
Published online 2010 July 24. doi:  10.1107/S1600536810028552
PMCID: PMC3007313

Diethyl 1-(4-methyl­phen­yl)-3-phenyl-5-oxopyrrolidine-2,2-dicarboxyl­ate

Abstract

In the title compound, C23H25NO5, the lactam ring adopts an envelope conformation and both eth­oxy­carbonyl side chains show an s-cis conformation: one is nearly planar, the dihedral angle between CO2 and OCH2CH3 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 inter­actions. Weak intra­molecular inter­actions 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 [triangle]); Ray et al. (1994 [triangle], 1998 [triangle], 2004 [triangle], 2010 [triangle]); Kandasamy et al. (1995 [triangle]). For conformational analysis, see: Cremer & Pople (1975 [triangle]); Rao et al. (1981 [triangle]). For hydrogen bonding, see: Desiraju (2005 [triangle]).

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Object name is e-66-o2104-scheme1.jpg

Experimental

Crystal data

  • C23H25NO5
  • M r = 395.44
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2104-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

JKR thanks the Ministerio de Educación y Ciencia for funding a short sabbatical visit (SAB2006–0199) to the Universidade da Coruña. The authors wish to thank Dr Ana Isabel Balana Gracia (SAI-UDC technician) for her helpful comments and are indebted to the CESGA (Xunta de Galicia - Spain) for the use of the Cambridge Structural Database. Funds were provided by the Xunta de Galicia through the project PGIDIT05TAM10301PR.

supplementary crystallographic information

Comment

In addition to the γ-lactam unit (N1/C1—C4), the title compound contains two phenyl rings (C5—C10) and (C12—C17), and two ethoxycarbonyl side chains, with bond distances and angles within typical values. The asymmetric unit of the title compound with our numbering scheme is in Figure 1. The γ-lactam unit (N1/C1—C4) adopts an envelope conformation. Atom C3 deviates 0.4804 (11)Å from the mean plane passing through the remaining atoms in the ring (r.m.s. 0.026 Å). In the envelope the atom C3 is the flap, with puckering parameters q2 = 0.3030 (12)Å and [var phi]2 = 291.9 (2)° (Cremer & Pople, 1975), and a pseudo-rotation angle P = 90.0 (1)°, and a maximum torsion angle τm = 30.6 (1)° (Rao et al., 1981) when the bond reference is N1—C1. The planar portion of the γ-lactam unit (N1—C1—C2—C4) forms dihedral angles of 69.53 (7)° and 67.61 (7)° with rings (C5—C10) and (C12—C17) respectively, and the dihedral angle between them is 56.66 (6)°. The ethoxycarbonyl side chain involving O2—C18—O3—C19—C20 adopts a s-cis conformation, with atoms of the group being nearly co-planar, the dihedral angle between CO2 and OCH2CH3 moieties being 7.95 (14)°; the other ethoxycarbonyl chain (O4—C21—O5—C22—C23) is also s-cis, the ethyl and the carboxylate moieties in a gauche relationship, the torsion angle of C21—O5—C22—C23 being 85.33 (9)°. The geometry of the title compound is similar to that of pirrolidinones (Nigam et al. 1989), (Ray et al., 2004), (Ray et al., 2010), (Kandasamy et al., 1995). The crystal structure contains van der Waals and C—H···O weak interactions, the latter are listed in Table 1. Carbonyl O atoms O1, O2 and O4 interact with two H atoms; such intermolecular interactions could be classified as supportive (Desiraju, 2005). Inversion dimers are formed involving oxygen atoms O2 and O4; in the first case, the same pair of molecules are linked, each oxygen O2 of one molecule interacting with H atoms H2a and H13 of the other (symmetry code: -x, 1 - y, 2 - z). When oxygen O4 is considered, three molecules participate; there is an inversion dimer due to the intermolecular interactions between oxygen O4 and hydrogen H2b (symmetry code: -x, 1 - y, 1 - z), and the same applies for O4 and H22b (symmetry code: 1 - x, 1 - y, 1 - z). In addition to those dimers, the interaction of oxygen O1 with H atoms H15 (symmetry code: x, 1 + y, z) and H22a (symmetry code: -1 + x, y, z) results in sheets propagating in the ab plane. The angle between the two C—H..O hydrogen bonds bifurcated at O1 (C15—H15—O1 and C22—H22a—O1) is almost a right angle (86.7°).

Experimental

The title compound was synthesized via an intermolecular Michael addition reaction, followed by an intramolecular amidification reaction, between diethyl 4-methylanilinomalonate (synthesized by the condensation reaction between 4-methylaniline and diethyl bromomalonate) in the presence of triethylamine, using dry benzene as solvent. Single crystals were grown by slow evaporation at room temperature of a solution of the resulting compound in 2-propanol. Yield 79%. Colourless solid [m.p. 401–402 K (ethyl acetate-petroleum ether)]; νmax(liquid film)/cm-1 1727.75, 1638.76; δH (200 MHz; CDCl3; Me4Si) 0.79 (3H, t, J 7.04, OCH2CH3), 0.94 (3H, t, J 7.24, OCH2CH3), 2.34 (3H, s, ArCH3), 2.98–3.05 (2H, dd, J 5.2 and J 9.15, NCOCH2), 3.47–3.56 (1H, m, OCH2CH3), 3.81–4.16 (3H, m, OCH2CH3), 4.6 (1H, t, J 9.44, C(3)HPh), 7.19–7.25 (4H, m, ArH), 7.3–7.37 (5H, m, ArH). δC (100 MHz; CDCl3; Me4Si) 13.36, 13.47 (2× OCH2CH3), 21.18 (ArCH3), 35.12 (C(4)H2), 45.21 (C(3)HPh), 61.80, 62.28 (2×OCH2CH3), 79.34 (C(2)), 128.12 (CP), 128.45(2Cb), 128.49 (2Cn), 128.54 (2Co), 129.62 (2Cc), 134.17 (Cd), 136.65 (Ca), 138.29 (Cm), 167.06, 167.31 (2× COOCH2CH3), 174.90 (NCO).

Refinement

Hydrogen atoms were found in subsequent difference Fourier maps and included in observed positions and refined as free isotropic atoms.

ALERTs all level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low. 0.98 RESPONSE: REason unknown. Optimized strategy by the software in order to get high completeness to resolution=0.75 A and enough redundancy and cut off in the refinement at 2theta=51, optimizing the the ratio parameters/data.

PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 20 A ng. RESPONSE: It is not a mistake.

PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 100 Deg. RESPONSE: It is not a mistake.

PLAT793_ALERT_4_G The Model has Chirality at C3 (Verify) ···. R RESPONSE: The compound is in a racemic mixture.

Figures

Fig. 1.
View of the title compound showing the atomic numbering and 50% probability displacement ellipsoids. H atoms are not shown for clarity.

Crystal data

C23H25NO5Z = 2
Mr = 395.44F(000) = 420
Triclinic, P1Dx = 1.297 Mg m3
Hall symbol: -P 1Melting point: 401 K
a = 9.4905 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.6167 (2) ÅCell parameters from 9079 reflections
c = 10.8198 (2) Åθ = 2.5–28.2°
α = 93.014 (1)°µ = 0.09 mm1
β = 95.167 (1)°T = 100 K
γ = 110.537 (1)°Block, colourless
V = 1012.60 (3) Å30.42 × 0.30 × 0.12 mm

Data collection

Bruker APEXII area-detector diffractometer3672 independent reflections
Radiation source: fine-focus sealed tube3331 reflections with I > 2σ(I)
graphiteRint = 0.020
phi and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −11→11
Tmin = 0.964, Tmax = 0.996k = −12→12
14991 measured reflectionsl = −13→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091All H-atom parameters refined
S = 1.87w = 1/[σ2(Fo2) + (0.0352P)2] where P = (Fo2 + 2Fc2)/3
3672 reflections(Δ/σ)max = 0.001
362 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O1−0.06859 (8)0.71231 (8)0.72064 (8)0.0250 (2)
O20.19397 (9)0.56920 (8)0.97081 (7)0.0205 (2)
O30.28043 (8)0.41475 (7)0.88942 (6)0.01674 (18)
O40.27852 (9)0.49468 (9)0.55611 (7)0.0247 (2)
O50.43697 (8)0.59245 (8)0.72998 (6)0.01664 (18)
N10.13851 (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)*
C30.02044 (11)0.41224 (11)0.69452 (10)0.0150 (2)
H30.0252 (13)0.4114 (12)0.6039 (12)0.017 (3)*
C40.17508 (11)0.52637 (10)0.74648 (9)0.0140 (2)
C50.24744 (11)0.78151 (11)0.73057 (9)0.0146 (2)
C60.34323 (13)0.85116 (12)0.83513 (10)0.0215 (3)
H60.3365 (15)0.8085 (14)0.9110 (14)0.035 (4)*
C70.44489 (13)0.98064 (12)0.82749 (11)0.0244 (3)
H70.5146 (15)1.0322 (14)0.8986 (13)0.031 (3)*
C80.45132 (12)1.04361 (11)0.71799 (10)0.0204 (3)
C90.35414 (12)0.97144 (12)0.61366 (10)0.0218 (3)
H90.3578 (15)1.0138 (14)0.5335 (13)0.033 (4)*
C100.25387 (12)0.84142 (11)0.61952 (10)0.0196 (3)
H100.1856 (16)0.7897 (14)0.5467 (13)0.030 (3)*
C110.55881 (16)1.18611 (13)0.71308 (13)0.0290 (3)
H11A0.6210 (17)1.2226 (15)0.7902 (14)0.037 (4)*
H11B0.5053 (18)1.2474 (17)0.6996 (15)0.048 (4)*
H11C0.6186 (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)*
C160.00369 (14)0.04957 (13)0.69484 (12)0.0277 (3)
H160.0251 (16)−0.0136 (15)0.6414 (13)0.035 (4)*
C170.02681 (13)0.17826 (12)0.65939 (11)0.0216 (3)
H170.0627 (15)0.2023 (13)0.5821 (13)0.029 (3)*
C180.21958 (11)0.50969 (10)0.88294 (9)0.0140 (2)
C190.30418 (13)0.37111 (12)1.01290 (10)0.0198 (3)
H19A0.2082 (14)0.3496 (12)1.0498 (11)0.019 (3)*
H19B0.3819 (13)0.4486 (13)1.0648 (11)0.017 (3)*
C200.35183 (15)0.25173 (13)0.99354 (12)0.0266 (3)
H20A0.2751 (19)0.1811 (17)0.9407 (15)0.045 (4)*
H20B0.3660 (15)0.2159 (14)1.0749 (13)0.034 (4)*
H20C0.4514 (17)0.2762 (14)0.9584 (13)0.037 (4)*
C210.30183 (11)0.53278 (11)0.66516 (9)0.0148 (2)
C220.56966 (12)0.61488 (13)0.66233 (10)0.0194 (3)
H22A0.6495 (14)0.6216 (12)0.7267 (11)0.017 (3)*
H22B0.5482 (13)0.5336 (13)0.6052 (11)0.018 (3)*
C230.60496 (15)0.74321 (15)0.60006 (13)0.0299 (3)
H23A0.6205 (15)0.8196 (15)0.6628 (13)0.030 (4)*
H23B0.6949 (17)0.7600 (15)0.5572 (13)0.038 (4)*
H23C0.5222 (17)0.7335 (15)0.5358 (14)0.042 (4)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0162 (4)0.0157 (4)0.0452 (5)0.0083 (3)0.0031 (3)0.0041 (4)
O20.0276 (4)0.0211 (4)0.0159 (4)0.0115 (3)0.0066 (3)0.0013 (3)
O30.0205 (4)0.0187 (4)0.0145 (4)0.0108 (3)0.0027 (3)0.0044 (3)
O40.0195 (4)0.0374 (5)0.0148 (4)0.0078 (4)0.0034 (3)−0.0028 (3)
O50.0119 (4)0.0237 (4)0.0151 (4)0.0070 (3)0.0034 (3)0.0015 (3)
N10.0122 (4)0.0123 (5)0.0191 (5)0.0048 (4)0.0016 (3)0.0026 (4)
C10.0141 (5)0.0177 (6)0.0177 (5)0.0067 (4)0.0021 (4)0.0019 (4)
C20.0129 (5)0.0153 (6)0.0224 (6)0.0048 (4)0.0014 (4)0.0027 (4)
C30.0144 (5)0.0148 (5)0.0150 (5)0.0047 (4)0.0013 (4)0.0007 (4)
C40.0142 (5)0.0139 (5)0.0150 (5)0.0063 (4)0.0025 (4)0.0008 (4)
C50.0122 (5)0.0130 (5)0.0200 (5)0.0057 (4)0.0033 (4)0.0021 (4)
C60.0264 (6)0.0183 (6)0.0170 (6)0.0048 (5)0.0007 (5)0.0038 (5)
C70.0267 (6)0.0198 (6)0.0200 (6)0.0017 (5)−0.0030 (5)0.0003 (5)
C80.0178 (6)0.0171 (6)0.0253 (6)0.0045 (5)0.0037 (4)0.0037 (5)
C90.0216 (6)0.0214 (6)0.0211 (6)0.0052 (5)0.0022 (5)0.0072 (5)
C100.0177 (6)0.0191 (6)0.0189 (6)0.0036 (5)−0.0017 (4)0.0022 (5)
C110.0287 (7)0.0215 (7)0.0289 (7)−0.0006 (6)0.0007 (6)0.0051 (5)
C120.0122 (5)0.0143 (6)0.0210 (5)0.0036 (4)−0.0006 (4)0.0002 (4)
C130.0186 (6)0.0172 (6)0.0241 (6)0.0070 (5)0.0035 (4)0.0020 (5)
C140.0234 (6)0.0208 (6)0.0300 (7)0.0070 (5)0.0043 (5)0.0079 (5)
C150.0283 (7)0.0149 (6)0.0410 (7)0.0080 (5)−0.0018 (5)0.0044 (5)
C160.0297 (7)0.0191 (6)0.0353 (7)0.0125 (5)−0.0013 (5)−0.0066 (5)
C170.0206 (6)0.0216 (6)0.0228 (6)0.0088 (5)0.0011 (5)−0.0024 (5)
C180.0112 (5)0.0135 (5)0.0169 (5)0.0030 (4)0.0038 (4)0.0026 (4)
C190.0224 (6)0.0224 (6)0.0147 (5)0.0077 (5)0.0005 (5)0.0058 (5)
C200.0312 (7)0.0267 (7)0.0259 (7)0.0152 (6)0.0003 (5)0.0081 (5)
C210.0156 (5)0.0148 (5)0.0156 (5)0.0070 (4)0.0022 (4)0.0032 (4)
C220.0128 (5)0.0298 (7)0.0181 (6)0.0094 (5)0.0058 (4)0.0041 (5)
C230.0211 (6)0.0374 (8)0.0338 (7)0.0104 (6)0.0099 (6)0.0143 (6)

Geometric parameters (Å, °)

O1—C11.2132 (13)C9—H90.996 (14)
O2—C181.2035 (12)C10—H100.977 (15)
O3—C181.3278 (12)C11—H11A0.955 (16)
O3—C191.4611 (12)C11—H11B0.965 (17)
O4—C211.2019 (13)C11—H11C0.960 (17)
O5—C211.3264 (13)C12—C131.3952 (15)
O5—C221.4671 (12)C12—C171.3978 (16)
N1—C11.3741 (13)C13—C141.3867 (16)
N1—C51.4337 (13)C13—H130.974 (13)
N1—C41.4633 (13)C14—C151.3862 (18)
C1—C21.5049 (15)C14—H140.974 (14)
C2—C31.5294 (14)C15—C161.3840 (18)
C2—H2A0.985 (13)C15—H150.986 (14)
C2—H2B0.985 (13)C16—C171.3862 (17)
C3—C121.5131 (15)C16—H160.949 (15)
C3—C41.5716 (14)C17—H170.945 (14)
C3—H30.985 (12)C19—C201.4987 (17)
C4—C181.5353 (14)C19—H19A0.985 (13)
C4—C211.5380 (14)C19—H19B0.994 (13)
C5—C61.3813 (15)C20—H20A0.957 (17)
C5—C101.3851 (15)C20—H20B0.994 (14)
C6—C71.3867 (16)C20—H20C1.004 (15)
C6—H60.955 (15)C22—C231.4964 (17)
C7—C81.3865 (16)C22—H22A0.963 (12)
C7—H70.969 (14)C22—H22B0.983 (13)
C8—C91.3920 (16)C23—H23A0.990 (15)
C8—C111.5059 (16)C23—H23B0.974 (15)
C9—C101.3833 (16)C23—H23C0.974 (16)
C18—O3—C19116.52 (8)H11B—C11—H11C104.4 (13)
C21—O5—C22117.09 (8)C13—C12—C17118.39 (10)
C1—N1—C5121.50 (9)C13—C12—C3122.07 (9)
C1—N1—C4113.50 (8)C17—C12—C3119.54 (10)
C5—N1—C4125.00 (8)C14—C13—C12120.68 (11)
O1—C1—N1124.33 (10)C14—C13—H13119.0 (8)
O1—C1—C2127.73 (9)C12—C13—H13120.3 (8)
N1—C1—C2107.93 (9)C15—C14—C13120.39 (12)
C1—C2—C3104.67 (8)C15—C14—H14120.7 (8)
C1—C2—H2A108.8 (8)C13—C14—H14118.9 (8)
C3—C2—H2A112.7 (7)C16—C15—C14119.46 (11)
C1—C2—H2B110.5 (8)C16—C15—H15120.2 (8)
C3—C2—H2B110.7 (7)C14—C15—H15120.3 (8)
H2A—C2—H2B109.5 (10)C15—C16—C17120.41 (11)
C12—C3—C2116.32 (9)C15—C16—H16120.0 (9)
C12—C3—C4116.64 (8)C17—C16—H16119.6 (9)
C2—C3—C4102.81 (8)C16—C17—C12120.67 (11)
C12—C3—H3110.1 (7)C16—C17—H17120.0 (8)
C2—C3—H3107.7 (7)C12—C17—H17119.3 (8)
C4—C3—H3102.0 (7)O2—C18—O3125.34 (9)
N1—C4—C18111.92 (8)O2—C18—C4124.12 (9)
N1—C4—C21108.16 (8)O3—C18—C4110.40 (8)
C18—C4—C21111.84 (8)O3—C19—C20106.36 (9)
N1—C4—C3101.81 (8)O3—C19—H19A107.5 (7)
C18—C4—C3110.42 (8)C20—C19—H19A113.3 (7)
C21—C4—C3112.27 (8)O3—C19—H19B107.9 (7)
C6—C5—C10119.81 (10)C20—C19—H19B113.4 (7)
C6—C5—N1121.64 (9)H19A—C19—H19B108.1 (10)
C10—C5—N1118.54 (9)C19—C20—H20A110.4 (9)
C5—C6—C7119.44 (10)C19—C20—H20B109.6 (8)
C5—C6—H6118.6 (9)H20A—C20—H20B107.7 (12)
C7—C6—H6122.0 (9)C19—C20—H20C112.2 (8)
C8—C7—C6121.76 (11)H20A—C20—H20C110.3 (12)
C8—C7—H7116.5 (8)H20B—C20—H20C106.5 (11)
C6—C7—H7121.8 (8)O4—C21—O5125.77 (10)
C7—C8—C9117.84 (10)O4—C21—C4123.35 (9)
C7—C8—C11120.84 (10)O5—C21—C4110.77 (8)
C9—C8—C11121.31 (10)O5—C22—C23110.51 (9)
C10—C9—C8120.96 (10)O5—C22—H22A103.6 (7)
C10—C9—H9119.6 (8)C23—C22—H22A110.8 (7)
C8—C9—H9119.4 (8)O5—C22—H22B106.9 (7)
C9—C10—C5120.17 (10)C23—C22—H22B114.4 (7)
C9—C10—H10121.6 (8)H22A—C22—H22B109.9 (10)
C5—C10—H10118.2 (8)C22—C23—H23A109.7 (8)
C8—C11—H11A112.6 (9)C22—C23—H23B110.8 (9)
C8—C11—H11B111.6 (10)H23A—C23—H23B110.0 (12)
H11A—C11—H11B103.5 (13)C22—C23—H23C108.9 (9)
C8—C11—H11C112.7 (10)H23A—C23—H23C111.5 (12)
H11A—C11—H11C111.4 (13)H23B—C23—H23C106.0 (12)
C5—N1—C1—O1−3.65 (16)C6—C5—C10—C9−1.04 (16)
C4—N1—C1—O1176.36 (10)N1—C5—C10—C9177.92 (10)
C5—N1—C1—C2176.93 (9)C2—C3—C12—C13−38.01 (14)
C4—N1—C1—C2−3.06 (11)C4—C3—C12—C1383.65 (12)
O1—C1—C2—C3163.95 (11)C2—C3—C12—C17142.13 (10)
N1—C1—C2—C3−16.65 (11)C4—C3—C12—C17−96.21 (12)
C1—C2—C3—C12156.77 (9)C17—C12—C13—C14−0.44 (16)
C1—C2—C3—C428.05 (10)C3—C12—C13—C14179.69 (10)
C1—N1—C4—C18−97.26 (10)C12—C13—C14—C150.05 (17)
C5—N1—C4—C1882.75 (11)C13—C14—C15—C160.39 (18)
C1—N1—C4—C21139.09 (9)C14—C15—C16—C17−0.44 (18)
C5—N1—C4—C21−40.89 (12)C15—C16—C17—C120.04 (18)
C1—N1—C4—C320.66 (10)C13—C12—C17—C160.40 (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—O26.15 (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—O216.45 (14)
C2—C3—C4—C1889.95 (9)C21—C4—C18—O2138.00 (10)
C12—C3—C4—C2186.98 (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—C6109.35 (12)C21—C4—C18—O3−46.09 (11)
C4—N1—C5—C6−70.67 (14)C3—C4—C18—O379.70 (10)
C1—N1—C5—C10−69.59 (13)C18—O3—C19—C20172.04 (9)
C4—N1—C5—C10110.40 (11)C22—O5—C21—O40.53 (16)
C10—C5—C6—C70.02 (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—C81.25 (18)C18—C4—C21—O4150.51 (10)
C6—C7—C8—C9−1.45 (17)C3—C4—C21—O425.74 (14)
C6—C7—C8—C11177.81 (12)N1—C4—C21—O590.53 (10)
C7—C8—C9—C100.40 (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—C50.83 (17)C21—O5—C22—C2384.62 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2A···O2i0.985 (14)2.529 (14)3.5096 (14)173.4 (10)
C3—H3···O40.984 (13)2.369 (13)2.8814 (14)111.7 (9)
C6—H6···O20.955 (15)2.573 (14)3.3143 (14)134.7 (11)
C13—H13···O2i0.975 (14)2.453 (14)3.4128 (14)168.3 (12)
C15—H15···O1ii0.987 (15)2.462 (15)3.2184 (15)133.2 (10)
C22—H22A···O1iii0.963 (13)2.513 (14)3.2100 (15)129.2 (9)
C22—H22B···O4iv0.983 (13)2.579 (13)3.2426 (14)124.9 (10)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2065).

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