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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2373.
Published online 2010 August 21. doi:  10.1107/S1600536810033325
PMCID: PMC3008038

[2-(2,3-Dimethyl­anilino)phen­yl]methanol

Abstract

In the title compound, C15H17NO, the 2,3-dimethyl­phenyl group is disordered over two sites with an occupancy ratio of 0.869 (3):0.131 (3). The major and minor components of the 2,3-dimethyl­anilino group are planar, with r.m.s. deviations of 0.0214 and 0.0303 Å, respectively, and are oriented at a dihedral angle of 2.6 (6)°. The phenyl­methanol–benzene ring is oriented at dihedral angles of 83.16 (6) and 81.0 (3)° with respect to the major and minor components of the 2,3-dimethyl­anilino group, respectively. An S(6) ring motif is present due to intra­molecular N—H(...)O hydrogen bonding. In the crystal, mol­ecules are connected into supra­molecular chains via O—H(...)O hydrogen bonding along the b axis. C—H(...)π inter­actions help to stabilize the crystal structure.

Related literature

For a related structure, see: Nawaz et al. (2007 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

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Object name is e-66-o2373-scheme1.jpg

Experimental

Crystal data

  • C15H17NO
  • M r = 227.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2373-efi1.jpg
  • a = 26.819 (2) Å
  • b = 5.0317 (4) Å
  • c = 21.4156 (15) Å
  • β = 118.198 (3)°
  • V = 2547.0 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 296 K
  • 0.34 × 0.25 × 0.22 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.966, T max = 0.975
  • 9889 measured reflections
  • 2298 independent reflections
  • 1342 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.150
  • S = 1.03
  • 2298 reflections
  • 160 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.16 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 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033325/tk2701sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033325/tk2701Isup2.hkl

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) is an important intermediate in our research related to the synthesis of pharmaceutically important derivatives of commonly used drugs. In this context, the crystal structure of a compound related to (I), i.e. methyl 2-(2,3-dimethylanilino)benzoate (Nawaz et al., 2007), has been published recently.

In (I), the 2,3-dimethylphenyl group is disordered over two sites with an occupancy ratio of 0.869 (3):0.131 (3). The (2,3-dimethylphenyl)amino groups A (C1A—C8A/N1) and B (C1B—C8B/N1) are each planar with r. m. s. deviation of 0.0214 and 0.0303 Å, respectively. The dihedral angle between A/B is 2.4 (6) °. The dihedral angles between A/C and B/C are 83.16 (6) and 81.0 (3) °, respectively; C is the least-square plane through the benzene ring. An S(6) ring motif (Bernstein et al., 1995) is formed due to intramolecular H-bond of the type N—H···O (Fig. 1). The molecules associate into supramolecular chains (Fig. 2) via H-bonding of the type O—H···O along the b axis. The presence of C—H···π interactions (Table 1) also play an important role in stabilizing the crystal structure.

Experimental

A solution of mefenamic acid (8.2 mmol) in THF (20 ml) was slowly added to a suspension of NaBH4 (10 mmol) in THF (20 ml), at room temperature. The mixture was stirred until evolution of hydrogen ceased. Iodine (4.1 mmol) in THF (20 ml) was added drop wise to this mixture. When the addition of iodine was complete, the reaction mixture was refluxed for 8 h and cooled to room temperature. Then, 2 N HCl (10 ml) was added and the mixture was extracted with ether. The ether layer was washed with 2 N NaOH (20 ml) and then with brine. Finally, the ether layer was dried over MgSO4. Evaporation of solvent yielded a mixture of mefenamic acid and an alcohol. The pure product was obtained by passing the mixture over silica gel column (eluent: n-hexane and ethyl acetate). The product, (I), was recrystallized from ethyl acetate and n-hexane. The yield of reaction was 73%; m.pt. 337 K.

Refinement

The H atoms were positioned geometrically (O—H = 0.82, N—H = 0.86 and C–H = 0.93–0.97 Å) and refined as riding with Uiso(H) = xUeq(C, N, O), where x = 1.5 for methyl H atoms and x = 1.2 for all other H atoms. The 2,3-dimethylphenyl ring was found to be disordered and was resolved over two positions with an occupancy ratio of 0.869 (3):0.131 (3). Each ring was treated as a regular hexagon and the anisotropic displacement parameters for equivalent atoms were constrained to be equivalent.

Figures

Fig. 1.
View of (I) with the atom numbering scheme showing atoms of the major component of the disorder. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii. The dotted line represent the intramolecular ...
Fig. 2.
View of (I) with the atom numbering scheme showing atoms of the minor component of the disorder. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii. The dotted line represent the intramolecular ...
Fig. 3.
The partial packing (PLATON; Spek, 2009) showing that molecules are interlinked and form supramolecular chains via O–H···O hydrogen bonding (dashed lines). The intramolecular S(6) ring motifs are also illustrated (dashed ...

Crystal data

C15H17NOF(000) = 976
Mr = 227.30Dx = 1.186 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1342 reflections
a = 26.819 (2) Åθ = 3.1–25.2°
b = 5.0317 (4) ŵ = 0.07 mm1
c = 21.4156 (15) ÅT = 296 K
β = 118.198 (3)°Prism, dark-red
V = 2547.0 (3) Å30.34 × 0.25 × 0.22 mm
Z = 8

Data collection

Bruker Kappa APEXII CCD diffractometer2298 independent reflections
Radiation source: fine-focus sealed tube1342 reflections with I > 2σ(I)
graphiteRint = 0.051
Detector resolution: 8.10 pixels mm-1θmax = 25.2°, θmin = 3.1°
ω scansh = −32→32
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −6→4
Tmin = 0.966, Tmax = 0.975l = −25→25
9889 measured reflections

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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0649P)2 + 0.7177P] where P = (Fo2 + 2Fc2)/3
2298 reflections(Δ/σ)max < 0.001
160 parametersΔρmax = 0.21 e Å3
3 restraintsΔρmin = −0.16 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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*/UeqOcc. (<1)
O10.22429 (7)−0.0427 (3)0.23258 (9)0.0696 (7)
N10.14081 (10)0.0565 (5)0.08648 (10)0.0804 (9)
C1A0.12806 (11)0.1206 (6)0.01625 (9)0.0610 (11)0.869 (3)
C2A0.16207 (10)0.3042 (5)0.00568 (9)0.0595 (11)0.869 (3)
C3A0.15111 (10)0.3693 (4)−0.06272 (11)0.0649 (12)0.869 (3)
C4A0.10612 (11)0.2509 (5)−0.12053 (8)0.0717 (13)0.869 (3)
C5A0.07211 (10)0.0673 (6)−0.10996 (10)0.0792 (14)0.869 (3)
C6A0.08307 (11)0.0022 (5)−0.04157 (12)0.0756 (16)0.869 (3)
C7A0.20928 (14)0.4464 (7)0.06895 (17)0.0812 (12)0.869 (3)
C8A0.18663 (15)0.5678 (7)−0.07597 (18)0.0871 (16)0.869 (3)
C90.11296 (10)0.1723 (5)0.12023 (12)0.0553 (8)
C100.12760 (10)0.0941 (5)0.18928 (12)0.0528 (8)
C110.09907 (11)0.2087 (6)0.22200 (13)0.0679 (10)
C120.05732 (12)0.3965 (6)0.18848 (15)0.0765 (11)
C130.04389 (11)0.4728 (6)0.12102 (14)0.0737 (11)
C140.07117 (10)0.3638 (5)0.08703 (13)0.0658 (10)
C150.17026 (11)−0.1194 (5)0.22527 (13)0.0637 (10)
C6B0.1812 (8)0.377 (4)0.0253 (7)0.0610 (11)0.131 (3)
C7B0.0593 (8)−0.096 (4)−0.0260 (10)0.0610 (11)0.131 (3)
C1B0.1440 (9)0.194 (4)0.0291 (8)0.0610 (11)0.131 (3)
C2B0.1000 (8)0.091 (4)−0.0326 (10)0.0610 (11)0.131 (3)
C3B0.0933 (7)0.172 (4)−0.0982 (8)0.0610 (11)0.131 (3)
C4B0.1305 (7)0.355 (3)−0.1021 (7)0.0610 (11)0.131 (3)
C5B0.1745 (6)0.457 (3)−0.0404 (8)0.0610 (11)0.131 (3)
C8B0.0445 (7)0.065 (4)−0.1661 (9)0.0610 (11)0.131 (3)
H10.16684−0.058780.109220.0964*
H1A0.24482−0.173710.242380.0836*
H8C0.225830.52079−0.048780.1304*0.869 (3)
H110.108320.157630.267940.0813*
H120.038570.470200.211400.0918*
H130.015930.599910.098080.0884*
H140.061710.418250.041270.0790*
H15A0.17367−0.153380.271720.0764*
H15B0.15780−0.282130.197860.0764*
H4A0.098790.29446−0.166290.0860*0.869 (3)
H5A0.04201−0.01196−0.148640.0953*0.869 (3)
H6A0.06032−0.12068−0.034490.0906*0.869 (3)
H7A0.245310.387240.074930.1218*0.869 (3)
H7B0.206350.406680.110940.1218*0.869 (3)
H7C0.205880.634700.060780.1218*0.869 (3)
H8A0.180570.74134−0.062200.1304*0.869 (3)
H8B0.176270.56839−0.125450.1304*0.869 (3)
H4B0.126040.40865−0.146000.0732*0.131 (3)
H5B0.199420.57989−0.042930.0732*0.131 (3)
H6B0.210640.445400.066590.0732*0.131 (3)
H7D0.04522−0.22049−0.064580.0914*0.131 (3)
H7E0.028230.00255−0.027090.0914*0.131 (3)
H7F0.07823−0.191120.018070.0914*0.131 (3)
H8D0.04325−0.12510−0.163490.0914*0.131 (3)
H8E0.049810.11462−0.205810.0914*0.131 (3)
H8F0.009530.13853−0.171750.0914*0.131 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0578 (11)0.0489 (11)0.0796 (12)0.0012 (8)0.0139 (9)0.0087 (9)
N10.0957 (17)0.0923 (18)0.0569 (14)0.0498 (14)0.0392 (13)0.0256 (11)
C1A0.066 (2)0.064 (2)0.0521 (19)0.0178 (16)0.0271 (18)0.0012 (15)
C2A0.065 (2)0.059 (2)0.0446 (17)0.0215 (16)0.0177 (15)−0.0045 (14)
C3A0.077 (2)0.064 (2)0.050 (2)0.0204 (17)0.0270 (18)0.0003 (15)
C4A0.088 (3)0.075 (2)0.0440 (18)0.0262 (19)0.0245 (18)0.0037 (16)
C5A0.072 (2)0.092 (3)0.052 (2)0.0098 (19)0.0116 (19)−0.0105 (18)
C6A0.070 (3)0.085 (3)0.065 (2)0.0081 (19)0.0263 (19)−0.0012 (19)
C7A0.081 (2)0.079 (2)0.072 (2)0.0014 (18)0.0267 (19)−0.0118 (18)
C8A0.101 (3)0.084 (3)0.085 (2)0.014 (2)0.051 (2)0.0154 (19)
C90.0571 (14)0.0540 (16)0.0499 (14)0.0065 (12)0.0212 (12)0.0020 (11)
C100.0545 (14)0.0471 (15)0.0481 (14)−0.0076 (11)0.0171 (12)−0.0010 (11)
C110.0721 (18)0.078 (2)0.0509 (15)−0.0144 (15)0.0268 (14)−0.0061 (13)
C120.0680 (19)0.091 (2)0.073 (2)0.0069 (16)0.0353 (16)−0.0131 (16)
C130.0614 (17)0.082 (2)0.0659 (18)0.0188 (14)0.0204 (14)−0.0078 (14)
C140.0661 (17)0.0721 (19)0.0509 (15)0.0180 (14)0.0208 (13)0.0061 (12)
C150.0654 (17)0.0543 (17)0.0579 (16)−0.0070 (13)0.0181 (13)0.0070 (12)
C6B0.066 (2)0.064 (2)0.0521 (19)0.0178 (16)0.0271 (18)0.0012 (15)
C7B0.066 (2)0.064 (2)0.0521 (19)0.0178 (16)0.0271 (18)0.0012 (15)
C1B0.066 (2)0.064 (2)0.0521 (19)0.0178 (16)0.0271 (18)0.0012 (15)
C2B0.066 (2)0.064 (2)0.0521 (19)0.0178 (16)0.0271 (18)0.0012 (15)
C3B0.066 (2)0.064 (2)0.0521 (19)0.0178 (16)0.0271 (18)0.0012 (15)
C4B0.066 (2)0.064 (2)0.0521 (19)0.0178 (16)0.0271 (18)0.0012 (15)
C5B0.066 (2)0.064 (2)0.0521 (19)0.0178 (16)0.0271 (18)0.0012 (15)
C8B0.066 (2)0.064 (2)0.0521 (19)0.0178 (16)0.0271 (18)0.0012 (15)

Geometric parameters (Å, °)

O1—C151.435 (4)C12—C131.368 (4)
O1—H1A0.8200C13—C141.367 (4)
N1—C1A1.413 (3)C4A—H4A0.9300
N1—C1B1.448 (19)C4B—H4B0.9300
N1—C91.389 (4)C5A—H5A0.9300
N1—H10.8600C5B—H5B0.9300
C1A—C2A1.390 (4)C6A—H6A0.9300
C1A—C6A1.390 (3)C6B—H6B0.9300
C1B—C6B1.39 (3)C7A—H7B0.9600
C1B—C2B1.39 (3)C7A—H7A0.9600
C2A—C3A1.390 (3)C7A—H7C0.9600
C2A—C7A1.526 (4)C7B—H7F0.9600
C2B—C7B1.50 (3)C7B—H7D0.9600
C2B—C3B1.39 (3)C7B—H7E0.9600
C3A—C8A1.497 (5)C8A—H8B0.9600
C3A—C4A1.390 (3)C8A—H8A0.9600
C3B—C8B1.52 (2)C8A—H8C0.9600
C3B—C4B1.39 (3)C8B—H8D0.9600
C4A—C5A1.390 (4)C8B—H8F0.9600
C4B—C5B1.39 (2)C8B—H8E0.9600
C5A—C6A1.390 (3)C11—H110.9300
C5B—C6B1.39 (2)C12—H120.9300
C9—C141.392 (4)C13—H130.9300
C9—C101.395 (3)C14—H140.9300
C10—C151.491 (4)C15—H15B0.9700
C10—C111.384 (4)C15—H15A0.9700
C11—C121.379 (4)
O1···N12.904 (3)H1A···H1Ai2.5400
O1···C15i3.307 (3)H1A···C15ii3.0300
O1···O1ii2.796 (2)H4A···H8B2.2900
O1···O1i2.796 (2)H4B···H8E2.3500
O1···H12.3500H5A···C12iv3.0700
O1···H1Ai2.0000H6A···C13iv3.0800
N1···O12.904 (3)H7A···C8A2.9900
N1···H7B2.3700H7A···H8Cviii2.3500
N1···H15B2.7900H7A···C8Aviii2.9200
N1···H7E2.8600H7A···H8C2.5400
N1···H7F2.0500H7B···N12.3700
C2B···C143.30 (2)H7B···H12.5600
C6A···C143.439 (4)H7B···C92.8600
C7A···C93.530 (5)H7C···C1Avi3.0600
C7B···C93.073 (19)H7C···C8A2.7400
C7B···C14iii3.55 (2)H7C···H1vi2.3600
C7B···C143.25 (2)H7C···H8A2.4500
C7B···C13iv3.17 (2)H7D···H13iv2.4000
C7B···C14iv3.38 (2)H7D···C14iv3.0100
C8B···C12iv3.44 (2)H7D···H8D2.1500
C8B···C8Bv3.24 (2)H7D···C12iv2.9100
C9···C7B3.073 (19)H7D···C8B2.6000
C9···C7A3.530 (5)H7D···C13iv2.4600
C12···C8Biv3.44 (2)H7E···C142.8200
C13···C7Biv3.17 (2)H7E···H142.4700
C14···C7B3.25 (2)H7E···C93.0100
C14···C7Biv3.38 (2)H7E···N12.8600
C14···C7Bvi3.55 (2)H7E···C14iv2.9900
C14···C6A3.439 (4)H7E···H13vii2.4500
C14···C2B3.30 (2)H7E···C7Biv3.0900
C15···O1ii3.307 (3)H7E···H7Eiv2.3000
C1A···H7Ciii3.0600H7F···C92.6600
C1A···H142.5700H7F···C14iii2.7400
C1B···H142.6000H7F···N12.0500
C2B···H142.7900H7F···H12.3500
C5A···H13vii3.0000H7F···H14iii2.1200
C5A···H8Aiii3.0600H8A···H7C2.4500
C6A···H13vii3.0800H8A···C5Avi3.0600
C6A···H142.9700H8A···C7A2.9400
C7A···H8C2.7800H8B···H4A2.2900
C7A···H13.0700H8B···H11xi2.5500
C7A···H8Cviii3.0700H8C···C7A2.7800
C7A···H8A2.9400H8C···H7A2.5400
C7A···H1vi3.0300H8C···C7Aviii3.0700
C7B···H12.9700H8C···H7Aviii2.3500
C7B···H8D2.7700H8D···C12iv2.8400
C7B···H7Eiv3.0900H8D···C7B2.7700
C7B···H14iii2.8200H8D···H7D2.1500
C7B···H142.9500H8D···H12iv2.6000
C7B···H8F3.0000H8E···H8Ev2.4400
C8A···H7Aviii2.9200H8E···H4B2.3500
C8A···H7C2.7400H8E···C8Bv2.7300
C8A···H7A2.9900H8E···C11ix2.9500
C8B···H8Fv3.0900H8E···H11ix2.3400
C8B···H11ix2.9100H8E···H8Fv2.3400
C8B···H12vii3.0500H8F···C12vii2.8700
C8B···H8Ev2.7300H8F···C13vii2.9200
C8B···H7D2.6000H8F···C7B3.0000
C9···H7B2.8600H8F···C8Bv3.0900
C9···H7E3.0100H8F···H8Ev2.3400
C9···H7F2.6600H8F···H12vii2.2900
C11···H8Ex2.9500H8F···H13vii2.3900
C12···H5Aiv3.0700H11···H15A2.3200
C12···H8Div2.8400H11···H8Ex2.3400
C12···H15Bvi3.0700H11···H8Bxii2.5500
C12···H7Div2.9100H11···C8Bx2.9100
C12···H8Fvii2.8700H12···H8Div2.6000
C13···H6Aiv3.0800H12···C8Bvii3.0500
C13···H8Fvii2.9200H12···H8Fvii2.2900
C13···H15Bvi2.9700H13···C5Avii3.0000
C13···H7Div2.4600H13···C6Avii3.0800
C14···H15Bvi3.0000H13···H8Fvii2.3900
C14···H7E2.8200H13···H7Div2.4000
C14···H7Fvi2.7400H13···H7Evii2.4500
C14···H7Div3.0100H14···C1A2.5700
C14···H7Eiv2.9900H14···C2B2.7900
C15···H12.4600H14···C6A2.9700
C15···H1Ai3.0300H14···C1B2.6000
H1···C152.4600H14···H7Fvi2.1200
H1···H7Ciii2.3600H14···H7E2.4700
H1···H15B2.3200H14···C7B2.9500
H1···H7B2.5600H14···C7Bvi2.8200
H1···H7F2.3500H15A···H112.3200
H1···C7Aiii3.0300H15B···C13iii2.9700
H1···C7A3.0700H15B···C14iii3.0000
H1···C7B2.9700H15B···H12.3200
H1···O12.3500H15B···C12iii3.0700
H1A···O1ii2.0000H15B···N12.7900
H1A···H1Aii2.5400
C15—O1—H1A109.00C4A—C5A—H5A120.00
C1B—N1—C9120.2 (9)C6A—C5A—H5A120.00
C1A—N1—C9122.6 (2)C4B—C5B—H5B120.00
C1B—N1—H1116.00C6B—C5B—H5B120.00
C1A—N1—H1119.00C5A—C6A—H6A120.00
C9—N1—H1119.00C1A—C6A—H6A120.00
N1—C1A—C6A121.5 (3)C1B—C6B—H6B120.00
C2A—C1A—C6A120.00 (19)C5B—C6B—H6B120.00
N1—C1A—C2A118.5 (2)C2A—C7A—H7C109.00
C2B—C1B—C6B120.2 (16)C2A—C7A—H7B109.00
N1—C1B—C2B105.3 (17)C2A—C7A—H7A109.00
N1—C1B—C6B134.4 (14)H7B—C7A—H7C109.00
C1A—C2A—C3A120.0 (2)H7A—C7A—H7B109.00
C3A—C2A—C7A119.9 (2)H7A—C7A—H7C109.00
C1A—C2A—C7A120.0 (2)C2B—C7B—H7D110.00
C1B—C2B—C7B118.3 (18)H7E—C7B—H7F109.00
C1B—C2B—C3B120 (2)C2B—C7B—H7E110.00
C3B—C2B—C7B121.8 (18)C2B—C7B—H7F110.00
C2A—C3A—C4A120.0 (2)H7D—C7B—H7E109.00
C4A—C3A—C8A118.7 (2)H7D—C7B—H7F109.00
C2A—C3A—C8A121.4 (2)C3A—C8A—H8C109.00
C2B—C3B—C4B120.1 (16)H8A—C8A—H8B109.00
C2B—C3B—C8B120.2 (18)C3A—C8A—H8B109.00
C4B—C3B—C8B119.7 (14)C3A—C8A—H8A109.00
C3A—C4A—C5A120.01 (18)H8A—C8A—H8C109.00
C3B—C4B—C5B120.0 (14)H8B—C8A—H8C109.00
C4A—C5A—C6A120.0 (2)C3B—C8B—H8F109.00
C4B—C5B—C6B120.1 (16)C3B—C8B—H8D110.00
C1A—C6A—C5A120.0 (3)C3B—C8B—H8E110.00
C1B—C6B—C5B119.9 (15)H8E—C8B—H8F109.00
N1—C9—C10118.8 (2)H8D—C8B—H8F109.00
C10—C9—C14119.5 (2)H8D—C8B—H8E110.00
N1—C9—C14121.7 (2)C10—C11—H11119.00
C9—C10—C11118.2 (2)C12—C11—H11119.00
C11—C10—C15120.7 (2)C11—C12—H12120.00
C9—C10—C15120.9 (2)C13—C12—H12120.00
C10—C11—C12121.9 (2)C12—C13—H13120.00
C11—C12—C13119.1 (3)C14—C13—H13120.00
C12—C13—C14120.6 (3)C9—C14—H14120.00
C9—C14—C13120.7 (2)C13—C14—H14120.00
O1—C15—C10110.6 (2)O1—C15—H15B110.00
C3A—C4A—H4A120.00H15A—C15—H15B108.00
C5A—C4A—H4A120.00C10—C15—H15A110.00
C5B—C4B—H4B120.00C10—C15—H15B110.00
C3B—C4B—H4B120.00O1—C15—H15A110.00
C9—N1—C1A—C2A98.1 (3)C3A—C4A—C5A—C6A0.0 (4)
C9—N1—C1A—C6A−82.7 (4)C4A—C5A—C6A—C1A0.0 (4)
C1A—N1—C9—C10179.0 (3)N1—C9—C10—C11−179.3 (3)
C1A—N1—C9—C14−1.2 (4)N1—C9—C10—C15−3.0 (4)
N1—C1A—C2A—C3A179.2 (3)C14—C9—C10—C110.9 (4)
N1—C1A—C2A—C7A−4.4 (4)C14—C9—C10—C15177.2 (2)
C6A—C1A—C2A—C3A0.0 (4)N1—C9—C14—C13179.3 (3)
C6A—C1A—C2A—C7A176.4 (3)C10—C9—C14—C13−0.9 (4)
N1—C1A—C6A—C5A−179.2 (3)C9—C10—C11—C12−0.3 (4)
C2A—C1A—C6A—C5A0.0 (4)C15—C10—C11—C12−176.5 (3)
C1A—C2A—C3A—C4A0.0 (4)C9—C10—C15—O162.0 (3)
C1A—C2A—C3A—C8A179.5 (3)C11—C10—C15—O1−121.8 (3)
C7A—C2A—C3A—C4A−176.4 (3)C10—C11—C12—C13−0.3 (5)
C7A—C2A—C3A—C8A3.1 (4)C11—C12—C13—C140.4 (5)
C2A—C3A—C4A—C5A0.0 (4)C12—C13—C14—C90.3 (4)
C8A—C3A—C4A—C5A−179.5 (3)

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y−1, z; (iv) −x, −y, −z; (v) −x, y, −z−1/2; (vi) x, y+1, z; (vii) −x, −y+1, −z; (viii) −x+1/2, −y+1/2, −z; (ix) x, −y, z−1/2; (x) x, −y, z+1/2; (xi) x, −y+1, z−1/2; (xii) x, −y+1, z+1/2.

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A—C6A and C9—C14 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.352.904 (3)123
O1—H1A···O1ii0.822.002.796 (2)163
C8A—H8A···Cg1vi0.962.883.783 (4)157
C15—H15B···Cg2iii0.972.773.634 (3)148

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2701).

References

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