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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o635.
Published online 2009 February 28. doi:  10.1107/S160053680900587X
PMCID: PMC2968525

2-Bromo-5,7-dimeth­oxy-4-phenyl­quinoline

Abstract

The title compound, C17H14BrNO2, was synthesized by the treatment of 5,7-dimeth­oxy-4-phenyl­quinolin-2-one with phosphoryl bromide in a Vilsmeier-type reaction. There are two independent mol­ecules (A and B) in the asymmetric unit which differ by 11.2° in the orientation of the 4-phenyl ring with respect to the planar quinoline ring system [dihedral angles = 55.15 (8) and 66.34 (8)° in mol­ecules A and B, respectively]. In the crystal structure, the independent mol­ecules are linked via C—H(...)N and C—H(...)O hydrogen bonds, forming centrosymmetric tetra­meric units which are cross-linked through C—H(...)π and C—Br(...)π inter­actions with Br(...)centroid distances of 3.4289 (8) and 3.5967 (8) Å.

Related literature

For a study of the anti­tumor activity of some 5,7-dimethoxy­quinolinlone analogues, see: Joseph et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o635-scheme1.jpg

Experimental

Crystal data

  • C17H14BrNO2
  • M r = 344.20
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o635-efi1.jpg
  • a = 9.7698 (2) Å
  • b = 9.9799 (3) Å
  • c = 14.8076 (4) Å
  • α = 93.499 (1)°
  • β = 95.154 (1)°
  • γ = 91.838 (1)°
  • V = 1434.22 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.87 mm−1
  • T = 150 K
  • 0.39 × 0.19 × 0.18 mm

Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.401, T max = 0.626
  • 27207 measured reflections
  • 5008 independent reflections
  • 4648 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.100
  • S = 0.87
  • 5008 reflections
  • 491 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: SHELXTL-Plus (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900587X/ci2767sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900587X/ci2767Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound is a precursor to 2-arylquinolines, which are analogues of flavones such as chrysin. The consumption of flavones has been linked to lower incidences of hormone-dependent cancers, diabetes, obesity and cardiovascular diseases. The title compound was synthesized by the treatment of 5,7-dimethoxy-4-phenylquinolin-2-one with phosphoryl bromide.

The crystals contain two crystallographically independent molecules in the asymmetric unit (Fig. 1) which differ by 11.19 ° in the orientation of the 4-phenyl ring with respect to the planar quinoline moeity. The dihedral angle between the quinoline ring system and phenyl ring is 55.15 (8)° in molecule A and 66.34 (8)° in molecule B.

In the crystal structure, the two independent molecules are linked via C—H···N and C—H···O hydrogen bonds (Table 1) to form centrosymmetric tetrameric units (Fig. 2). The tetramers are cross-linked via C—H···π interactions (Table 1) involving the C12A—H12A group and the N1B/C2B—C4B/C9B/C10B ring. In addition, intermolecular C—Br···π interactions involving each independent molecule are observed between tetramers. The Br1A···Cg2 distance (Cg2 is the centroid of the C11A—C16A ring at -x, 1 - y, 1 - z) and C2A—Br1A···Cg2 angle are 3.5967 (8) Å and 135.59 (6)°, respectively, whereas, the Br1B···Cg3 distance (Cg3 is the centroid of the C11B—C16B ring at 1 - x, 1 - y, 2 - z) and C2B—Br1B···Cg3 angle are 3.4289 (8) Å and 149.71 (6) °, respectively.

Experimental

To a solution of 5,7-dimethoxy-4-phenylquinolin-2-one (2.01 g, 7.1 mmol) in 1,2-dichloroethane (20 ml) was added dropwise a solution of phosphoryl bromide (6.32 g, 22.2 mmol) in 1,2-dichloroethane (20 ml) and the mixture was refluxed for 4 h. The crude product was purified by chromatography on silica gel (50% dichloromethane/hexane). Recrystallization from dichloromethane-hexane (2:3 v/v) afforded the title compound as light yellow needles (1.09 g, 44%).

Refinement

All H atoms were located in a difference Fourier map and their positions and isotropic displacement parameters were refined freely [C—H = 0.87 (3) Å - 1.05 (3) Å].

Figures

Fig. 1.
A view of two molecules in the asymmetric unit along with labelling of atoms. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A view of the tetrameric unit formed by C—H···N and C—H···O hydrogen bonds (dashed lines).

Crystal data

C17H14BrNO2Z = 4
Mr = 344.20F(000) = 696
Triclinic, P1Dx = 1.594 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7698 (2) ÅCell parameters from 9202 reflections
b = 9.9799 (3) Åθ = 2.4–28.0°
c = 14.8076 (4) ŵ = 2.87 mm1
α = 93.499 (1)°T = 150 K
β = 95.154 (1)°Needle, light yellow
γ = 91.838 (1)°0.39 × 0.19 × 0.18 mm
V = 1434.22 (7) Å3

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer5008 independent reflections
Radiation source: fine-focus sealed tube4648 reflections with I > 2σ(I)
graphiteRint = 0.060
[var phi] scans, and ω scans with κ offsetsθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −11→11
Tmin = 0.401, Tmax = 0.626k = −11→11
27207 measured reflectionsl = −17→17

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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 0.87w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
5008 reflections(Δ/σ)max = 0.002
491 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.55 e Å3

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 (Å2)

xyzUiso*/Ueq
Br1A−0.09830 (2)0.72553 (2)0.551387 (13)0.02782 (11)
N1A0.06082 (17)0.81444 (17)0.42221 (11)0.0205 (4)
C2A−0.0207 (2)0.7146 (2)0.43692 (13)0.0202 (4)
C3A−0.0501 (2)0.5984 (2)0.38082 (14)0.0223 (4)
C4A0.01131 (19)0.5845 (2)0.29994 (13)0.0185 (4)
C5A0.15706 (19)0.70379 (19)0.19273 (13)0.0176 (4)
C6A0.24532 (19)0.8091 (2)0.18021 (13)0.0182 (4)
C7A0.27300 (19)0.91362 (19)0.24867 (13)0.0197 (4)
C8A0.2096 (2)0.9153 (2)0.32701 (13)0.0204 (4)
C9A0.11985 (19)0.80637 (19)0.34132 (13)0.0186 (4)
C10A0.09499 (19)0.69426 (19)0.27681 (13)0.0178 (4)
C11A−0.0078 (2)0.4498 (2)0.25100 (13)0.0190 (4)
C12A−0.1389 (2)0.3890 (2)0.23443 (13)0.0220 (4)
C13A−0.1566 (2)0.2565 (2)0.20000 (15)0.0265 (5)
C14A−0.0440 (2)0.1825 (2)0.18294 (14)0.0265 (5)
C15A0.0871 (2)0.2423 (2)0.19786 (13)0.0236 (4)
C16A0.1057 (2)0.3744 (2)0.23107 (13)0.0196 (4)
C17A0.1870 (2)0.6020 (3)0.04572 (15)0.0267 (5)
C18A0.4127 (2)1.1078 (2)0.29986 (15)0.0262 (5)
O1A0.11992 (14)0.60380 (14)0.12739 (9)0.0216 (3)
O2A0.36495 (15)1.01016 (14)0.22783 (10)0.0231 (3)
Br1B0.55112 (2)0.694767 (19)0.898615 (13)0.02541 (11)
N1B0.54825 (17)0.51735 (17)0.74864 (11)0.0187 (4)
C2B0.50047 (19)0.53079 (19)0.82786 (13)0.0183 (4)
C3B0.4198 (2)0.4360 (2)0.86636 (14)0.0191 (4)
C4B0.38014 (19)0.3180 (2)0.81667 (13)0.0169 (4)
C5B0.37631 (19)0.19046 (19)0.66232 (13)0.0183 (4)
C6B0.4281 (2)0.1790 (2)0.57944 (14)0.0205 (4)
C7B0.5251 (2)0.2767 (2)0.55562 (13)0.0200 (4)
C8B0.5642 (2)0.3868 (2)0.61213 (14)0.0193 (4)
C9B0.51012 (19)0.40097 (19)0.69749 (13)0.0175 (4)
C10B0.42110 (19)0.30043 (19)0.72675 (13)0.0173 (4)
C11B0.30626 (19)0.2160 (2)0.86651 (12)0.0161 (4)
C12B0.1834 (2)0.2501 (2)0.90227 (13)0.0185 (4)
C13B0.1267 (2)0.1686 (2)0.96236 (14)0.0223 (4)
C14B0.1912 (2)0.0542 (2)0.98908 (14)0.0228 (4)
C15B0.3122 (2)0.0188 (2)0.95183 (14)0.0218 (4)
C16B0.36828 (19)0.0984 (2)0.89061 (13)0.0192 (4)
C17B0.2224 (2)0.0005 (2)0.62431 (15)0.0236 (4)
C18B0.6704 (2)0.3438 (2)0.44447 (16)0.0266 (5)
O1B0.28035 (15)0.10469 (14)0.68888 (9)0.0238 (3)
O2B0.57054 (16)0.25043 (15)0.47225 (9)0.0276 (3)
H3A−0.102 (3)0.527 (3)0.3972 (17)0.030 (7)*
H6A0.290 (2)0.816 (2)0.1237 (16)0.020 (5)*
H8A0.220 (2)0.987 (3)0.3705 (16)0.026 (6)*
H16A0.193 (2)0.414 (2)0.2432 (15)0.021 (6)*
H14A−0.053 (2)0.098 (3)0.1641 (16)0.027 (6)*
H13A−0.241 (3)0.218 (3)0.1921 (19)0.038 (7)*
H15A0.163 (3)0.187 (3)0.1838 (16)0.033 (6)*
H3B0.394 (2)0.452 (2)0.9274 (17)0.027 (6)*
H8B0.622 (2)0.455 (2)0.5995 (15)0.021 (6)*
H12B0.140 (2)0.327 (2)0.8887 (13)0.010 (5)*
H13B0.051 (3)0.194 (3)0.9858 (18)0.038 (7)*
H16B0.451 (2)0.079 (2)0.8690 (15)0.020 (5)*
H15B0.363 (2)−0.057 (3)0.9700 (16)0.026 (6)*
H6B0.406 (2)0.113 (2)0.5367 (17)0.024 (6)*
H12A−0.217 (3)0.436 (2)0.2490 (15)0.029 (6)*
H1810.480 (3)1.150 (3)0.2743 (19)0.038 (7)*
H1820.340 (3)1.171 (3)0.3149 (17)0.033 (7)*
H1830.444 (2)1.058 (2)0.3530 (17)0.027 (6)*
H1710.163 (2)0.683 (2)0.0128 (16)0.022 (5)*
H1720.152 (3)0.531 (3)0.012 (2)0.042 (7)*
H1730.283 (3)0.593 (3)0.0583 (17)0.028 (6)*
H2820.748 (3)0.348 (3)0.4829 (18)0.032 (7)*
H2810.634 (2)0.429 (3)0.4422 (15)0.023 (6)*
H2830.688 (3)0.308 (3)0.3863 (19)0.032 (7)*
H2730.156 (3)−0.042 (3)0.6514 (19)0.043 (8)*
H2720.298 (3)−0.065 (3)0.6064 (16)0.034 (6)*
H2710.177 (2)0.035 (2)0.5686 (17)0.027 (6)*
H14B0.151 (2)0.000 (2)1.0286 (16)0.022 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br1A0.03787 (17)0.02967 (17)0.01893 (16)0.00803 (11)0.01470 (11)0.00473 (11)
N1A0.0251 (9)0.0211 (9)0.0169 (8)0.0059 (7)0.0071 (7)0.0031 (7)
C2A0.0236 (10)0.0240 (11)0.0147 (9)0.0077 (8)0.0072 (8)0.0052 (8)
C3A0.0243 (10)0.0216 (11)0.0231 (11)0.0050 (8)0.0082 (8)0.0065 (9)
C4A0.0174 (9)0.0207 (10)0.0183 (10)0.0042 (7)0.0030 (7)0.0039 (8)
C5A0.0183 (9)0.0176 (10)0.0175 (9)0.0043 (7)0.0037 (7)0.0011 (8)
C6A0.0209 (9)0.0200 (10)0.0150 (10)0.0042 (8)0.0056 (8)0.0034 (8)
C7A0.0202 (9)0.0173 (9)0.0223 (10)0.0031 (7)0.0022 (8)0.0047 (8)
C8A0.0244 (10)0.0185 (10)0.0183 (10)0.0025 (8)0.0038 (8)−0.0015 (8)
C9A0.0211 (9)0.0199 (10)0.0157 (10)0.0074 (8)0.0035 (7)0.0037 (8)
C10A0.0184 (9)0.0188 (10)0.0171 (10)0.0055 (7)0.0021 (7)0.0034 (8)
C11A0.0224 (10)0.0219 (11)0.0137 (10)0.0018 (8)0.0039 (8)0.0047 (8)
C12A0.0190 (10)0.0286 (11)0.0192 (10)0.0026 (9)0.0026 (8)0.0062 (9)
C13A0.0233 (11)0.0311 (12)0.0242 (11)−0.0072 (9)−0.0001 (9)0.0030 (9)
C14A0.0390 (12)0.0202 (12)0.0192 (11)−0.0047 (9)0.0023 (9)−0.0030 (9)
C15A0.0283 (11)0.0273 (11)0.0156 (10)0.0055 (9)0.0042 (8)−0.0002 (8)
C16A0.0187 (10)0.0246 (11)0.0159 (10)0.0008 (8)0.0035 (8)0.0028 (8)
C17A0.0328 (13)0.0314 (13)0.0165 (10)0.0019 (10)0.0095 (9)−0.0040 (9)
C18A0.0297 (11)0.0227 (11)0.0252 (12)−0.0050 (9)−0.0003 (9)0.0021 (9)
O1A0.0274 (7)0.0233 (7)0.0146 (7)−0.0021 (6)0.0081 (5)−0.0027 (6)
O2A0.0268 (7)0.0205 (7)0.0226 (8)−0.0052 (6)0.0074 (6)0.0002 (6)
Br1B0.03604 (17)0.01914 (16)0.01965 (16)−0.00615 (10)−0.00020 (10)−0.00227 (10)
N1B0.0190 (8)0.0197 (9)0.0170 (8)−0.0013 (6)0.0007 (6)0.0009 (7)
C2B0.0220 (9)0.0152 (9)0.0165 (10)0.0003 (7)−0.0026 (8)−0.0009 (7)
C3B0.0219 (10)0.0200 (10)0.0157 (10)0.0011 (8)0.0026 (8)0.0021 (8)
C4B0.0147 (9)0.0182 (10)0.0176 (10)0.0021 (7)0.0004 (7)0.0012 (8)
C5B0.0190 (9)0.0167 (10)0.0191 (10)0.0010 (7)0.0000 (7)0.0032 (8)
C6B0.0237 (10)0.0191 (10)0.0183 (10)0.0003 (8)0.0031 (8)−0.0027 (8)
C7B0.0236 (10)0.0236 (11)0.0140 (10)0.0046 (8)0.0053 (8)0.0031 (8)
C8B0.0202 (10)0.0204 (10)0.0185 (10)−0.0003 (8)0.0048 (8)0.0059 (8)
C9B0.0169 (9)0.0179 (10)0.0176 (9)0.0012 (7)−0.0011 (7)0.0028 (8)
C10B0.0170 (9)0.0196 (10)0.0157 (9)0.0028 (7)0.0011 (7)0.0033 (8)
C11B0.0183 (9)0.0190 (10)0.0105 (9)−0.0033 (7)0.0009 (7)−0.0017 (7)
C12B0.0188 (9)0.0184 (11)0.0179 (10)0.0019 (8)0.0013 (8)−0.0023 (8)
C13B0.0180 (10)0.0284 (11)0.0208 (10)−0.0014 (8)0.0071 (8)−0.0035 (8)
C14B0.0274 (10)0.0226 (11)0.0182 (10)−0.0087 (8)0.0057 (8)0.0003 (8)
C15B0.0255 (10)0.0180 (10)0.0216 (10)0.0010 (8)0.0012 (8)0.0007 (8)
C16B0.0180 (10)0.0205 (10)0.0189 (10)−0.0003 (8)0.0046 (8)−0.0032 (8)
C17B0.0263 (11)0.0195 (11)0.0238 (11)−0.0040 (9)0.0018 (9)−0.0044 (9)
C18B0.0319 (12)0.0260 (12)0.0246 (12)0.0037 (10)0.0134 (10)0.0073 (9)
O1B0.0283 (7)0.0234 (7)0.0192 (7)−0.0094 (6)0.0055 (6)−0.0020 (6)
O2B0.0366 (8)0.0284 (8)0.0195 (8)−0.0021 (6)0.0152 (6)−0.0023 (6)

Geometric parameters (Å, °)

Br1A—C2A1.9168 (19)Br1B—C2B1.9147 (19)
N1A—C2A1.296 (3)N1B—C2B1.302 (3)
N1A—C9A1.374 (3)N1B—C9B1.370 (3)
C2A—C3A1.392 (3)C2B—C3B1.393 (3)
C3A—C4A1.388 (3)C3B—C4B1.376 (3)
C3A—H3A0.92 (3)C3B—H3B0.97 (3)
C4A—C10A1.422 (3)C4B—C10B1.427 (3)
C4A—C11A1.487 (3)C4B—C11B1.497 (3)
C5A—O1A1.364 (2)C5B—O1B1.350 (2)
C5A—C6A1.370 (3)C5B—C6B1.369 (3)
C5A—C10A1.440 (3)C5B—C10B1.440 (3)
C6A—C7A1.412 (3)C6B—C7B1.419 (3)
C6A—H6A0.98 (2)C6B—H6B0.89 (3)
C7A—C8A1.363 (3)C7B—O2B1.362 (2)
C7A—O2A1.364 (2)C7B—C8B1.363 (3)
C8A—C9A1.413 (3)C8B—C9B1.414 (3)
C8A—H8A0.93 (3)C8B—H8B0.91 (2)
C9A—C10A1.426 (3)C9B—C10B1.420 (3)
C11A—C12A1.395 (3)C11B—C16B1.389 (3)
C11A—C16A1.402 (3)C11B—C12B1.399 (3)
C12A—C13A1.387 (3)C12B—C13B1.382 (3)
C12A—H12A0.95 (3)C12B—H12B0.92 (2)
C13A—C14A1.379 (3)C13B—C14B1.383 (3)
C13A—H13A0.89 (3)C13B—H13B0.89 (3)
C14A—C15A1.389 (3)C14B—C15B1.395 (3)
C14A—H14A0.87 (3)C14B—H14B0.92 (2)
C15A—C16A1.379 (3)C15B—C16B1.380 (3)
C15A—H15A0.97 (3)C15B—H15B0.96 (3)
C16A—H16A0.93 (2)C16B—H16B0.92 (2)
C17A—O1A1.426 (2)C17B—O1B1.435 (2)
C17A—H1710.99 (2)C17B—H2730.90 (3)
C17A—H1720.88 (3)C17B—H2721.05 (3)
C17A—H1730.95 (3)C17B—H2710.99 (2)
C18A—O2A1.435 (3)C18B—O2B1.432 (3)
C18A—H1810.90 (3)C18B—H2820.91 (3)
C18A—H1821.00 (3)C18B—H2810.94 (3)
C18A—H1830.99 (3)C18B—H2830.95 (3)
C2A—N1A—C9A116.40 (17)C2B—N1B—C9B116.28 (17)
N1A—C2A—C3A126.61 (18)N1B—C2B—C3B126.12 (18)
N1A—C2A—Br1A115.79 (15)N1B—C2B—Br1B116.34 (14)
C3A—C2A—Br1A117.47 (15)C3B—C2B—Br1B117.52 (14)
C4A—C3A—C2A118.63 (19)C4B—C3B—C2B118.86 (18)
C4A—C3A—H3A118.2 (16)C4B—C3B—H3B120.4 (15)
C2A—C3A—H3A123.0 (16)C2B—C3B—H3B120.7 (15)
C3A—C4A—C10A117.62 (18)C3B—C4B—C10B117.97 (18)
C3A—C4A—C11A115.29 (18)C3B—C4B—C11B115.31 (17)
C10A—C4A—C11A126.82 (17)C10B—C4B—C11B126.54 (17)
O1A—C5A—C6A123.19 (17)O1B—C5B—C6B123.94 (18)
O1A—C5A—C10A115.72 (16)O1B—C5B—C10B115.64 (16)
C6A—C5A—C10A121.07 (18)C6B—C5B—C10B120.40 (18)
C5A—C6A—C7A120.33 (17)C5B—C6B—C7B120.30 (19)
C5A—C6A—H6A122.2 (13)C5B—C6B—H6B125.0 (15)
C7A—C6A—H6A117.5 (13)C7B—C6B—H6B114.7 (15)
C8A—C7A—O2A124.71 (18)O2B—C7B—C8B124.74 (19)
C8A—C7A—C6A121.31 (18)O2B—C7B—C6B113.86 (18)
O2A—C7A—C6A113.98 (16)C8B—C7B—C6B121.38 (19)
C7A—C8A—C9A118.89 (18)C7B—C8B—C9B118.94 (19)
C7A—C8A—H8A122.6 (14)C7B—C8B—H8B125.6 (15)
C9A—C8A—H8A118.5 (14)C9B—C8B—H8B115.4 (15)
N1A—C9A—C8A115.57 (17)N1B—C9B—C8B115.72 (17)
N1A—C9A—C10A122.43 (17)N1B—C9B—C10B122.91 (17)
C8A—C9A—C10A121.98 (17)C8B—C9B—C10B121.37 (17)
C4A—C10A—C9A118.10 (17)C9B—C10B—C4B117.57 (17)
C4A—C10A—C5A125.79 (18)C9B—C10B—C5B117.28 (17)
C9A—C10A—C5A116.11 (17)C4B—C10B—C5B125.13 (18)
C12A—C11A—C16A118.49 (19)C16B—C11B—C12B119.27 (18)
C12A—C11A—C4A120.08 (18)C16B—C11B—C4B120.99 (17)
C16A—C11A—C4A120.93 (17)C12B—C11B—C4B118.87 (17)
C13A—C12A—C11A120.8 (2)C13B—C12B—C11B119.92 (19)
C13A—C12A—H12A118.8 (14)C13B—C12B—H12B118.0 (13)
C11A—C12A—H12A120.3 (14)C11B—C12B—H12B122.0 (13)
C14A—C13A—C12A120.2 (2)C12B—C13B—C14B120.80 (19)
C14A—C13A—H13A120.2 (18)C12B—C13B—H13B118.1 (18)
C12A—C13A—H13A119.6 (18)C14B—C13B—H13B121.0 (18)
C13A—C14A—C15A119.7 (2)C13B—C14B—C15B119.15 (19)
C13A—C14A—H14A121.3 (15)C13B—C14B—H14B119.4 (14)
C15A—C14A—H14A119.1 (15)C15B—C14B—H14B121.4 (14)
C16A—C15A—C14A120.6 (2)C16B—C15B—C14B120.41 (19)
C16A—C15A—H15A122.8 (15)C16B—C15B—H15B117.0 (14)
C14A—C15A—H15A116.6 (15)C14B—C15B—H15B122.5 (14)
C15A—C16A—C11A120.26 (19)C15B—C16B—C11B120.38 (18)
C15A—C16A—H16A121.2 (14)C15B—C16B—H16B120.7 (14)
C11A—C16A—H16A118.4 (14)C11B—C16B—H16B118.7 (14)
O1A—C17A—H171109.2 (13)O1B—C17B—H273106.0 (19)
O1A—C17A—H172106.1 (18)O1B—C17B—H272110.5 (13)
H171—C17A—H172108 (2)H273—C17B—H272111 (2)
O1A—C17A—H173110.7 (15)O1B—C17B—H271113.2 (14)
H171—C17A—H173114 (2)H273—C17B—H271107 (2)
H172—C17A—H173109 (2)H272—C17B—H271108.9 (19)
O2A—C18A—H181100.4 (18)O2B—C18B—H282111.3 (16)
O2A—C18A—H182112.2 (15)O2B—C18B—H281110.0 (14)
H181—C18A—H182111 (2)H282—C18B—H281109 (2)
O2A—C18A—H183107.3 (14)O2B—C18B—H283103.4 (16)
H181—C18A—H183114 (2)H282—C18B—H283110 (2)
H182—C18A—H183111 (2)H281—C18B—H283112 (2)
C5A—O1A—C17A118.03 (16)C5B—O1B—C17B118.11 (16)
C7A—O2A—C18A116.35 (16)C7B—O2B—C18B116.83 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16A—H16A···N1Bi0.93 (2)2.59 (2)3.497 (3)167 (2)
C16B—H16B···O2Ai0.92 (2)2.54 (2)3.437 (2)163 (2)
C17B—H272···O2Bii1.04 (3)2.57 (3)3.580 (3)164 (2)
C12A—H12A···Cg1iii0.95 (3)2.87 (3)3.762 (2)158 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2767).

References

  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Joseph, B., Darro, F., Béhard, A., Lesur, B., Collingnon, F., Decaestecker, C., Frydman, A., Guillaumet, G. & Kiss, R. (2002). J. Med. Chem.45, 2543–2555. [PubMed]
  • Sheldrick, G. M. (2003). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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