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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2282–o2283.
Published online 2010 August 11. doi:  10.1107/S1600536810031223
PMCID: PMC3008119

Ethyl 1,5-diphenyl-1H-pyrazole-4-carboxyl­ate

Abstract

The asymmetric unit of the title compound, C18H16N2O2, contains two independent mol­ecules (A and B). In mol­ecule A, the pyrazole ring is inclined at angles of 48.86 (6) and 60.80 (6)° with respect to the two phenyl rings; the corresponding angles for mol­ecule B are 46.86 (6) and 58.63 (6)°. In the crystal, mol­ecules of type A are linked into sheets parallel to (001) via weak C—H(...)O hydrogen bonds, whereas the mol­ecules of type B are linked into chains along [010] via weak C—H(...)O hydrogen bonds.

Related literature

For general background to and the biological activity of pyrazole derivatives, see: Isloor et al. (2009 [triangle]); Lambert & Fowler (2005 [triangle]); Lan et al. (1999 [triangle]). For related structures, see: Fun et al. (2009 [triangle]; 2010 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]). For standard bond-length data, see: Allen et al. (1987 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2282-scheme1.jpg

Experimental

Crystal data

  • C18H16N2O2
  • M r = 292.33
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2282-efi1.jpg
  • a = 9.2015 (8) Å
  • b = 10.4638 (9) Å
  • c = 16.9332 (15) Å
  • α = 97.515 (2)°
  • β = 104.605 (2)°
  • γ = 104.578 (2)°
  • V = 1493.7 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.24 × 0.23 × 0.21 mm

Data collection

  • Bruker SMART APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.980, T max = 0.983
  • 35429 measured reflections
  • 10300 independent reflections
  • 7846 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.128
  • S = 1.03
  • 10300 reflections
  • 399 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.28 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031223/lh5108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031223/lh5108Isup2.hkl

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

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). CKQ also thanks USM for the award of a USM fellowship. AMI is thankful to the Director of the National Institute of Technology–Karnataka, Surathkal, India, for providing research facilities and encouragement.

supplementary crystallographic information

Comment

Pyrazole and its derivatives represent one of the most active classes of compounds possessing a wide spectrum of biological activities. During the past years, considerable evidences have been accumulated to demonstrate the efficacy of pyrazole derivatives including antibacterial (Isloor et al., 2009), antifungal (Lambert & Fowler, 2005), herbicidal (Lan et al., 1999), insecticidal and other biological activities. In view of the potential importance of pyrazole derivatives, we have synthesized the title compound and its crystal structure is presented herein.

The title compound (Fig. 1) contains two indpendent molecules (A and B) in the asymmetric unit, with similar geometries. Each molecule consists of two phenyl rings and an ethyl carboxylate moiety attached to the pyrazole ring. In molecule A, the pyrazole ring (N1A/N2A/C7A-C9A) is inclined at angles of 48.86 (6) and 60.80 (6)° with respect to the C1A-C6A and C10A-C15A phenyl rings, respectively. The correspondening angles for molecule B are 46.86 (6) and 58.63 (6)°. Bond lengths and angles are within normal ranges, and comparable to closely related structures (Fun et al., 2009; 2010).

In the crystal packing (Fig. 2), molecules of type A are linked into sheets (Fig. 3) parallel to (001) via C3A–H3AA···O2Ai and C13A–H13A···O2Aii hydrogen bonds whereas the molecules B are linked into one-dimensional chains along [010] via a C3B–H3BA···O2Bi hydrogen bonds.

Experimental

A mixture of ethyl-3-(dimethylamino)-2-(phenylcarbonyl)prop-2-enoate (2.0 g, 0.0080 mol) and phenyl hydrazine (0.95 g, 0.0088 mol) in absolute ethanol (20 ml) was refluxed for 2 h. Reaction completion was monitored through thin layer chromatography and the reaction mixture was evaporated under reduced pressure. The residue was stirred with 1.5N HCl and the solid separated was filtered and dried under vacuum. The solid obtained was purified by column chromatography using silica gel 60-120 mesh size and petroleum ether: ethyl acetate as eluent to afford title compound as colourless crystals (2.0g, 86.9 %); melting point: 400-405 K.

Refinement

All H atoms were positioned geometrically and refined using a riding model with C-H = 0.93-0.97 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
Fig. 2.
Part of the crystal structure of the title compound, viewed approximately along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
Fig. 3.
The crystal packing of molecules of type A, viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

Crystal data

C18H16N2O2Z = 4
Mr = 292.33F(000) = 616
Triclinic, P1Dx = 1.300 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2015 (8) ÅCell parameters from 9846 reflections
b = 10.4638 (9) Åθ = 2.5–31.9°
c = 16.9332 (15) ŵ = 0.09 mm1
α = 97.515 (2)°T = 100 K
β = 104.605 (2)°Block, colourless
γ = 104.578 (2)°0.24 × 0.23 × 0.21 mm
V = 1493.7 (2) Å3

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer10300 independent reflections
Radiation source: fine-focus sealed tube7846 reflections with I > 2σ(I)
graphiteRint = 0.044
[var phi] and ω scansθmax = 32.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.980, Tmax = 0.983k = −15→15
35429 measured reflectionsl = −25→25

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0568P)2 + 0.3537P] where P = (Fo2 + 2Fc2)/3
10300 reflections(Δ/σ)max = 0.001
399 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Å2)

xyzUiso*/Ueq
O1A0.35565 (9)0.55673 (8)0.40840 (5)0.02192 (16)
O2A0.10538 (10)0.56385 (8)0.36818 (6)0.02587 (18)
N1A0.45702 (10)0.94866 (9)0.36135 (5)0.01681 (16)
N2A0.30699 (11)0.95931 (9)0.34270 (6)0.01975 (17)
C1A0.59279 (14)1.18876 (11)0.40504 (7)0.0206 (2)
H1AA0.52141.19830.43400.025*
C2A0.71181 (15)1.30011 (11)0.40425 (7)0.0244 (2)
H2AA0.71951.38510.43250.029*
C3A0.81991 (14)1.28608 (12)0.36156 (7)0.0241 (2)
H3AA0.90001.36110.36190.029*
C4A0.80757 (13)1.15950 (12)0.31842 (7)0.0236 (2)
H4AA0.87941.14990.28970.028*
C5A0.68803 (13)1.04687 (11)0.31798 (7)0.0205 (2)
H5AA0.67900.96210.28880.025*
C6A0.58225 (12)1.06269 (10)0.36174 (6)0.01680 (18)
C7A0.21906 (13)0.83992 (11)0.34605 (7)0.01922 (19)
H7AA0.11060.81700.33600.023*
C8A0.30951 (12)0.75140 (10)0.36682 (6)0.01709 (18)
C9A0.46399 (12)0.82515 (10)0.37630 (6)0.01586 (18)
C10A0.61394 (12)0.79251 (10)0.39942 (6)0.01714 (18)
C11A0.73369 (13)0.86837 (11)0.47083 (7)0.0213 (2)
H11A0.71820.93830.50440.026*
C12A0.87630 (14)0.83944 (13)0.49183 (8)0.0270 (2)
H12A0.95540.88920.54000.032*
C13A0.90112 (15)0.73682 (14)0.44132 (8)0.0299 (3)
H13A0.99710.71850.45530.036*
C14A0.78255 (16)0.66135 (13)0.36982 (8)0.0287 (3)
H14A0.79960.59290.33570.034*
C15A0.63871 (14)0.68781 (11)0.34916 (7)0.0223 (2)
H15A0.55880.63590.30190.027*
C16A0.24476 (12)0.61555 (10)0.38013 (6)0.01793 (19)
C17A0.29923 (14)0.41764 (11)0.41795 (7)0.0229 (2)
H17A0.20710.40690.43740.027*
H17B0.38010.39790.45940.027*
C18A0.25821 (16)0.32054 (13)0.33655 (8)0.0295 (3)
H18A0.23550.22980.34560.044*
H18B0.34530.33870.31390.044*
H18C0.16760.33090.29810.044*
O1B−0.03838 (10)0.61507 (8)0.09374 (5)0.02177 (16)
O2B−0.23012 (11)0.65343 (9)0.14598 (6)0.0317 (2)
N1B0.11226 (10)1.04064 (9)0.13619 (5)0.01698 (16)
N2B−0.01563 (11)1.06169 (9)0.15725 (6)0.02083 (18)
C1B0.18999 (13)1.25412 (11)0.09434 (7)0.0210 (2)
H1BA0.08491.24240.06680.025*
C2B0.30546 (15)1.37023 (12)0.09588 (8)0.0253 (2)
H2BA0.27721.43700.06980.030*
C3B0.46273 (14)1.38736 (12)0.13605 (7)0.0248 (2)
H3BA0.53961.46510.13690.030*
C4B0.50423 (13)1.28742 (12)0.17498 (7)0.0234 (2)
H4BA0.60951.29800.20130.028*
C5B0.38976 (13)1.17171 (11)0.17499 (7)0.0202 (2)
H5BA0.41781.10560.20190.024*
C6B0.23336 (12)1.15597 (10)0.13444 (6)0.01708 (18)
C7B−0.10204 (13)0.93979 (11)0.15709 (7)0.0208 (2)
H7BA−0.19700.92250.16960.025*
C8B−0.03368 (12)0.83895 (10)0.13579 (6)0.01782 (19)
C9B0.10638 (12)0.90767 (10)0.12275 (6)0.01598 (18)
C10B0.22948 (12)0.86100 (10)0.09737 (6)0.01613 (18)
C11B0.26595 (13)0.89043 (11)0.02510 (7)0.0201 (2)
H11B0.21100.9379−0.00750.024*
C12B0.38418 (14)0.84894 (12)0.00174 (7)0.0251 (2)
H12B0.40640.8671−0.04700.030*
C13B0.46887 (14)0.78059 (12)0.05093 (8)0.0268 (2)
H13B0.54920.75440.03580.032*
C14B0.43344 (14)0.75128 (12)0.12286 (8)0.0245 (2)
H14B0.49030.70550.15590.029*
C15B0.31331 (13)0.79004 (11)0.14585 (7)0.0199 (2)
H15B0.28890.76870.19350.024*
C16B−0.11071 (13)0.69496 (11)0.12682 (7)0.0197 (2)
C17B−0.10723 (15)0.47049 (11)0.08556 (7)0.0235 (2)
H17C−0.07730.42120.04280.028*
H17E−0.22100.44860.06830.028*
C18B−0.05319 (17)0.42793 (13)0.16657 (8)0.0311 (3)
H18G−0.09180.33150.15830.047*
H18D−0.09280.46900.20730.047*
H18E0.05970.45600.18590.047*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0188 (4)0.0176 (3)0.0286 (4)0.0037 (3)0.0057 (3)0.0084 (3)
O2A0.0173 (4)0.0204 (4)0.0391 (5)0.0021 (3)0.0108 (3)0.0055 (3)
N1A0.0150 (4)0.0155 (4)0.0214 (4)0.0049 (3)0.0070 (3)0.0050 (3)
N2A0.0159 (4)0.0206 (4)0.0254 (4)0.0074 (3)0.0081 (3)0.0060 (3)
C1A0.0236 (5)0.0179 (5)0.0218 (5)0.0057 (4)0.0093 (4)0.0046 (4)
C2A0.0277 (6)0.0175 (5)0.0249 (5)0.0028 (4)0.0074 (4)0.0025 (4)
C3A0.0209 (5)0.0214 (5)0.0268 (5)0.0005 (4)0.0055 (4)0.0085 (4)
C4A0.0188 (5)0.0248 (5)0.0293 (5)0.0050 (4)0.0107 (4)0.0092 (4)
C5A0.0197 (5)0.0193 (5)0.0242 (5)0.0056 (4)0.0092 (4)0.0055 (4)
C6A0.0166 (5)0.0155 (4)0.0182 (4)0.0042 (4)0.0047 (4)0.0054 (3)
C7A0.0155 (5)0.0208 (5)0.0225 (5)0.0056 (4)0.0072 (4)0.0049 (4)
C8A0.0159 (4)0.0163 (4)0.0190 (4)0.0040 (4)0.0059 (4)0.0036 (3)
C9A0.0160 (4)0.0149 (4)0.0170 (4)0.0045 (3)0.0056 (3)0.0033 (3)
C10A0.0162 (4)0.0170 (4)0.0206 (4)0.0056 (4)0.0072 (4)0.0072 (3)
C11A0.0188 (5)0.0211 (5)0.0235 (5)0.0046 (4)0.0059 (4)0.0067 (4)
C12A0.0166 (5)0.0333 (6)0.0309 (6)0.0055 (5)0.0047 (4)0.0148 (5)
C13A0.0202 (5)0.0411 (7)0.0404 (7)0.0161 (5)0.0152 (5)0.0234 (6)
C14A0.0319 (6)0.0323 (6)0.0357 (6)0.0201 (5)0.0199 (5)0.0140 (5)
C15A0.0230 (5)0.0224 (5)0.0244 (5)0.0093 (4)0.0095 (4)0.0051 (4)
C16A0.0174 (5)0.0169 (4)0.0189 (4)0.0038 (4)0.0063 (4)0.0026 (3)
C17A0.0258 (6)0.0164 (5)0.0259 (5)0.0041 (4)0.0070 (4)0.0078 (4)
C18A0.0352 (7)0.0243 (6)0.0296 (6)0.0108 (5)0.0096 (5)0.0034 (4)
O1B0.0222 (4)0.0157 (3)0.0279 (4)0.0037 (3)0.0112 (3)0.0026 (3)
O2B0.0239 (4)0.0226 (4)0.0545 (6)0.0052 (3)0.0226 (4)0.0100 (4)
N1B0.0144 (4)0.0150 (4)0.0222 (4)0.0043 (3)0.0071 (3)0.0031 (3)
N2B0.0163 (4)0.0199 (4)0.0289 (5)0.0067 (3)0.0101 (4)0.0041 (3)
C1B0.0177 (5)0.0192 (5)0.0256 (5)0.0055 (4)0.0050 (4)0.0049 (4)
C2B0.0264 (6)0.0192 (5)0.0312 (6)0.0053 (4)0.0096 (5)0.0088 (4)
C3B0.0229 (5)0.0205 (5)0.0293 (5)0.0005 (4)0.0120 (4)0.0023 (4)
C4B0.0157 (5)0.0252 (5)0.0259 (5)0.0027 (4)0.0063 (4)0.0003 (4)
C5B0.0172 (5)0.0203 (5)0.0220 (5)0.0053 (4)0.0045 (4)0.0033 (4)
C6B0.0157 (4)0.0148 (4)0.0197 (4)0.0026 (3)0.0064 (4)0.0014 (3)
C7B0.0176 (5)0.0202 (5)0.0259 (5)0.0056 (4)0.0094 (4)0.0033 (4)
C8B0.0160 (5)0.0162 (4)0.0217 (5)0.0040 (4)0.0071 (4)0.0037 (3)
C9B0.0156 (4)0.0152 (4)0.0171 (4)0.0050 (3)0.0045 (3)0.0030 (3)
C10B0.0140 (4)0.0140 (4)0.0194 (4)0.0029 (3)0.0058 (3)0.0012 (3)
C11B0.0202 (5)0.0190 (5)0.0210 (5)0.0043 (4)0.0078 (4)0.0035 (4)
C12B0.0239 (5)0.0238 (5)0.0267 (5)0.0017 (4)0.0142 (4)−0.0002 (4)
C13B0.0179 (5)0.0253 (5)0.0347 (6)0.0045 (4)0.0110 (4)−0.0052 (4)
C14B0.0196 (5)0.0240 (5)0.0290 (6)0.0102 (4)0.0042 (4)0.0005 (4)
C15B0.0195 (5)0.0196 (5)0.0213 (5)0.0071 (4)0.0062 (4)0.0034 (4)
C16B0.0168 (5)0.0181 (5)0.0247 (5)0.0045 (4)0.0075 (4)0.0046 (4)
C17B0.0270 (6)0.0147 (4)0.0274 (5)0.0030 (4)0.0095 (4)0.0028 (4)
C18B0.0393 (7)0.0271 (6)0.0311 (6)0.0134 (5)0.0127 (5)0.0093 (5)

Geometric parameters (Å, °)

O1A—C16A1.3402 (13)O1B—C16B1.3420 (13)
O1A—C17A1.4620 (13)O1B—C17B1.4587 (13)
O2A—C16A1.2123 (13)O2B—C16B1.2156 (13)
N1A—C9A1.3630 (13)N1B—C9B1.3651 (13)
N1A—N2A1.3728 (12)N1B—N2B1.3719 (12)
N1A—C6A1.4330 (13)N1B—C6B1.4311 (13)
N2A—C7A1.3235 (14)N2B—C7B1.3216 (14)
C1A—C2A1.3879 (15)C1B—C6B1.3882 (15)
C1A—C6A1.3906 (14)C1B—C2B1.3905 (16)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.3935 (17)C2B—C3B1.3893 (18)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.3893 (17)C3B—C4B1.3887 (18)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.3927 (15)C4B—C5B1.3905 (15)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.3917 (14)C5B—C6B1.3865 (15)
C5A—H5AA0.9300C5B—H5BA0.9300
C7A—C8A1.4142 (15)C7B—C8B1.4100 (14)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—C9A1.3936 (14)C8B—C9B1.3947 (14)
C8A—C16A1.4668 (14)C8B—C16B1.4643 (14)
C9A—C10A1.4743 (15)C9B—C10B1.4749 (14)
C10A—C11A1.3940 (15)C10B—C15B1.3959 (15)
C10A—C15A1.3986 (14)C10B—C11B1.3996 (14)
C11A—C12A1.3903 (16)C11B—C12B1.3922 (15)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.3851 (19)C12B—C13B1.3862 (19)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.389 (2)C13B—C14B1.3898 (18)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.3882 (17)C14B—C15B1.3926 (15)
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9300C15B—H15B0.9300
C17A—C18A1.5010 (16)C17B—C18B1.5015 (17)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17E0.9700
C18A—H18A0.9600C18B—H18G0.9600
C18A—H18B0.9600C18B—H18D0.9600
C18A—H18C0.9600C18B—H18E0.9600
C16A—O1A—C17A116.10 (9)C16B—O1B—C17B115.69 (8)
C9A—N1A—N2A112.87 (8)C9B—N1B—N2B112.76 (8)
C9A—N1A—C6A128.77 (9)C9B—N1B—C6B129.09 (9)
N2A—N1A—C6A118.36 (8)N2B—N1B—C6B118.10 (8)
C7A—N2A—N1A104.39 (9)C7B—N2B—N1B104.38 (8)
C2A—C1A—C6A118.80 (10)C6B—C1B—C2B119.22 (10)
C2A—C1A—H1AA120.6C6B—C1B—H1BA120.4
C6A—C1A—H1AA120.6C2B—C1B—H1BA120.4
C1A—C2A—C3A120.78 (10)C3B—C2B—C1B120.56 (11)
C1A—C2A—H2AA119.6C3B—C2B—H2BA119.7
C3A—C2A—H2AA119.6C1B—C2B—H2BA119.7
C4A—C3A—C2A119.73 (10)C4B—C3B—C2B119.46 (11)
C4A—C3A—H3AA120.1C4B—C3B—H3BA120.3
C2A—C3A—H3AA120.1C2B—C3B—H3BA120.3
C3A—C4A—C5A120.24 (10)C3B—C4B—C5B120.59 (11)
C3A—C4A—H4AA119.9C3B—C4B—H4BA119.7
C5A—C4A—H4AA119.9C5B—C4B—H4BA119.7
C6A—C5A—C4A119.18 (10)C6B—C5B—C4B119.24 (10)
C6A—C5A—H5AA120.4C6B—C5B—H5BA120.4
C4A—C5A—H5AA120.4C4B—C5B—H5BA120.4
C1A—C6A—C5A121.27 (10)C5B—C6B—C1B120.92 (10)
C1A—C6A—N1A118.48 (9)C5B—C6B—N1B120.56 (9)
C5A—C6A—N1A120.24 (9)C1B—C6B—N1B118.47 (9)
N2A—C7A—C8A111.99 (9)N2B—C7B—C8B112.23 (9)
N2A—C7A—H7AA124.0N2B—C7B—H7BA123.9
C8A—C7A—H7AA124.0C8B—C7B—H7BA123.9
C9A—C8A—C7A105.26 (9)C9B—C8B—C7B105.21 (9)
C9A—C8A—C16A130.70 (10)C9B—C8B—C16B131.97 (9)
C7A—C8A—C16A123.90 (9)C7B—C8B—C16B122.74 (9)
N1A—C9A—C8A105.49 (9)N1B—C9B—C8B105.43 (9)
N1A—C9A—C10A122.05 (9)N1B—C9B—C10B122.19 (9)
C8A—C9A—C10A132.43 (9)C8B—C9B—C10B132.36 (9)
C11A—C10A—C15A119.52 (10)C15B—C10B—C11B119.26 (9)
C11A—C10A—C9A119.93 (9)C15B—C10B—C9B120.66 (9)
C15A—C10A—C9A120.52 (10)C11B—C10B—C9B120.06 (9)
C12A—C11A—C10A120.01 (11)C12B—C11B—C10B120.32 (11)
C12A—C11A—H11A120.0C12B—C11B—H11B119.8
C10A—C11A—H11A120.0C10B—C11B—H11B119.8
C13A—C12A—C11A120.29 (12)C13B—C12B—C11B120.14 (11)
C13A—C12A—H12A119.9C13B—C12B—H12B119.9
C11A—C12A—H12A119.9C11B—C12B—H12B119.9
C12A—C13A—C14A119.96 (11)C12B—C13B—C14B119.81 (10)
C12A—C13A—H13A120.0C12B—C13B—H13B120.1
C14A—C13A—H13A120.0C14B—C13B—H13B120.1
C15A—C14A—C13A120.17 (11)C13B—C14B—C15B120.44 (11)
C15A—C14A—H14A119.9C13B—C14B—H14B119.8
C13A—C14A—H14A119.9C15B—C14B—H14B119.8
C14A—C15A—C10A120.02 (11)C14B—C15B—C10B120.00 (10)
C14A—C15A—H15A120.0C14B—C15B—H15B120.0
C10A—C15A—H15A120.0C10B—C15B—H15B120.0
O2A—C16A—O1A123.97 (10)O2B—C16B—O1B124.08 (10)
O2A—C16A—C8A123.00 (10)O2B—C16B—C8B122.69 (10)
O1A—C16A—C8A113.02 (9)O1B—C16B—C8B113.22 (9)
O1A—C17A—C18A110.68 (9)O1B—C17B—C18B111.06 (10)
O1A—C17A—H17A109.5O1B—C17B—H17C109.4
C18A—C17A—H17A109.5C18B—C17B—H17C109.4
O1A—C17A—H17B109.5O1B—C17B—H17E109.4
C18A—C17A—H17B109.5C18B—C17B—H17E109.4
H17A—C17A—H17B108.1H17C—C17B—H17E108.0
C17A—C18A—H18A109.5C17B—C18B—H18G109.5
C17A—C18A—H18B109.5C17B—C18B—H18D109.5
H18A—C18A—H18B109.5H18G—C18B—H18D109.5
C17A—C18A—H18C109.5C17B—C18B—H18E109.5
H18A—C18A—H18C109.5H18G—C18B—H18E109.5
H18B—C18A—H18C109.5H18D—C18B—H18E109.5
C9A—N1A—N2A—C7A−0.07 (11)C9B—N1B—N2B—C7B0.18 (12)
C6A—N1A—N2A—C7A179.13 (9)C6B—N1B—N2B—C7B−177.38 (9)
C6A—C1A—C2A—C3A−0.58 (17)C6B—C1B—C2B—C3B0.86 (17)
C1A—C2A—C3A—C4A0.76 (18)C1B—C2B—C3B—C4B−0.09 (17)
C2A—C3A—C4A—C5A−0.20 (18)C2B—C3B—C4B—C5B−0.87 (17)
C3A—C4A—C5A—C6A−0.50 (17)C3B—C4B—C5B—C6B1.04 (16)
C2A—C1A—C6A—C5A−0.14 (16)C4B—C5B—C6B—C1B−0.24 (15)
C2A—C1A—C6A—N1A−178.67 (10)C4B—C5B—C6B—N1B−177.47 (9)
C4A—C5A—C6A—C1A0.68 (16)C2B—C1B—C6B—C5B−0.70 (16)
C4A—C5A—C6A—N1A179.18 (10)C2B—C1B—C6B—N1B176.58 (10)
C9A—N1A—C6A—C1A−132.33 (11)C9B—N1B—C6B—C5B−46.46 (15)
N2A—N1A—C6A—C1A48.61 (13)N2B—N1B—C6B—C5B130.65 (10)
C9A—N1A—C6A—C5A49.12 (15)C9B—N1B—C6B—C1B136.25 (11)
N2A—N1A—C6A—C5A−129.93 (11)N2B—N1B—C6B—C1B−46.64 (13)
N1A—N2A—C7A—C8A0.13 (11)N1B—N2B—C7B—C8B−0.39 (12)
N2A—C7A—C8A—C9A−0.14 (12)N2B—C7B—C8B—C9B0.45 (13)
N2A—C7A—C8A—C16A175.97 (9)N2B—C7B—C8B—C16B−176.57 (10)
N2A—N1A—C9A—C8A−0.01 (11)N2B—N1B—C9B—C8B0.09 (12)
C6A—N1A—C9A—C8A−179.11 (9)C6B—N1B—C9B—C8B177.32 (10)
N2A—N1A—C9A—C10A−178.57 (9)N2B—N1B—C9B—C10B178.45 (9)
C6A—N1A—C9A—C10A2.33 (15)C6B—N1B—C9B—C10B−4.31 (16)
C7A—C8A—C9A—N1A0.09 (11)C7B—C8B—C9B—N1B−0.30 (11)
C16A—C8A—C9A—N1A−175.66 (10)C16B—C8B—C9B—N1B176.32 (11)
C7A—C8A—C9A—C10A178.43 (10)C7B—C8B—C9B—C10B−178.43 (11)
C16A—C8A—C9A—C10A2.68 (19)C16B—C8B—C9B—C10B−1.8 (2)
N1A—C9A—C10A—C11A59.02 (14)N1B—C9B—C10B—C15B121.72 (11)
C8A—C9A—C10A—C11A−119.10 (13)C8B—C9B—C10B—C15B−60.41 (16)
N1A—C9A—C10A—C15A−119.47 (11)N1B—C9B—C10B—C11B−56.76 (14)
C8A—C9A—C10A—C15A62.42 (15)C8B—C9B—C10B—C11B121.11 (13)
C15A—C10A—C11A—C12A−0.23 (16)C15B—C10B—C11B—C12B0.22 (16)
C9A—C10A—C11A—C12A−178.73 (10)C9B—C10B—C11B—C12B178.72 (10)
C10A—C11A—C12A—C13A1.08 (17)C10B—C11B—C12B—C13B−1.36 (17)
C11A—C12A—C13A—C14A−0.71 (18)C11B—C12B—C13B—C14B1.23 (17)
C12A—C13A—C14A—C15A−0.50 (18)C12B—C13B—C14B—C15B0.04 (17)
C13A—C14A—C15A—C10A1.35 (18)C13B—C14B—C15B—C10B−1.18 (17)
C11A—C10A—C15A—C14A−0.98 (16)C11B—C10B—C15B—C14B1.04 (16)
C9A—C10A—C15A—C14A177.51 (10)C9B—C10B—C15B—C14B−177.45 (10)
C17A—O1A—C16A—O2A5.26 (15)C17B—O1B—C16B—O2B−3.28 (16)
C17A—O1A—C16A—C8A−176.13 (8)C17B—O1B—C16B—C8B178.27 (9)
C9A—C8A—C16A—O2A−179.16 (11)C9B—C8B—C16B—O2B175.52 (12)
C7A—C8A—C16A—O2A5.79 (16)C7B—C8B—C16B—O2B−8.35 (18)
C9A—C8A—C16A—O1A2.22 (15)C9B—C8B—C16B—O1B−6.00 (17)
C7A—C8A—C16A—O1A−172.83 (9)C7B—C8B—C16B—O1B170.12 (10)
C16A—O1A—C17A—C18A83.99 (12)C16B—O1B—C17B—C18B−81.78 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3A—H3AA···O2Ai0.932.433.3591 (16)177
C3B—H3BA···O2Bi0.932.463.3829 (16)172
C13A—H13A···O2Aii0.932.593.2622 (17)129

Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5108).

References

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