PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2751.
Published online 2009 October 17. doi:  10.1107/S1600536809041257
PMCID: PMC2971027

N-(3,4-Dimethyl­phen­yl)-4-methyl­benzamide

Abstract

The title compound, C16H17NO, crystallizes with two mol­ecules in the asymmetric unit. The conformation of the N—H bond is anti to the meta-methyl substituent in the aniline ring in the first mol­ecule and syn in the second mol­ecule. The dihedral angles between the two benzene rings are 52.6 (1) and 10.5 (1)° in the first and second mol­ecules, respectively. Inter­molecular N—H(...)O hydrogen bonds link the mol­ecules into chains running along the b axis of the crystal.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 [triangle]). For related structures, see: Bowes et al. (2003 [triangle]); Gowda et al. (2008 [triangle], 2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2751-scheme1.jpg

Experimental

Crystal data

  • C16H17NO
  • M r = 239.31
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2751-efi1.jpg
  • a = 9.4186 (3) Å
  • b = 9.55915 (18) Å
  • c = 15.8813 (4) Å
  • α = 74.361 (2)°
  • β = 79.696 (2)°
  • γ = 88.1582 (18)°
  • V = 1354.51 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 295 K
  • 0.51 × 0.41 × 0.22 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector
  • Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 [triangle]) T min = 0.943, T max = 0.981
  • 24655 measured reflections
  • 5130 independent reflections
  • 3880 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.126
  • S = 1.09
  • 5130 reflections
  • 332 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; 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 DIAMOND (Brandenburg, 2002 [triangle]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 [triangle]) and WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041257/bt5089sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041257/bt5089Isup2.hkl

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

Acknowledgments

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the crystal structures of benzanilides (Gowda, Tokarčík et al., 2008, 2009), the structure of N-(3,4-dimethylphenyl)4-methylbenzamide (I) has been determined. In the structure, the conformations of the N—H and C=O bonds are anti to each other (Fig. 1), similar to those observed in N-(3,4-dimethylphenyl)benzamide (Gowda, Tokarčík et al., 2008), N-(2,6-dimethylphenyl)4-methylbenzamide (Gowda, Tokarčík et al., 2009) and the parent benzanilide (Bowes et al., 2003).

The asymmetric unit of the cell in (I) contains two independent molecules. In the first molecule, the conformation of the N—H bond is anti to the meta-methyl-substituent in the disubstituted phenyl ring, while in the second molecule this conformation is syn. The dihedral angles between the two benzene rings are 52.6 (1)° and 10.5 (1)° in the first and second molecules, respectively. The central amido group –NH—C(=O)- forms dihedral angles of 22.2 (2)° and 31.2 (1)° with the benzoyl ring, and 30.6 (1)° and 25.5 (1)° with the disubstituted phenyl ring, in the two independent molecules.

The packing diagram of molecules in (I) showing the intermolecular N–H···O hydrogen bonds (Table 1) involved in the formation of molecular chains running along the b-axis is shown in Fig. 2.

Experimental

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of its ethanolic solution at room temperature.

Refinement

H atoms were placed in calculated positions with N–H distances of 0.86 Å and C–H distances in the range 0.93–0.96 Å. All hydrogen atoms were constrained to ride on their parent atoms. The Uiso(H) values were set at 1.2Ueq(C aromatic, N) and 1.5 Ueq(Cmethyl). The U values of the atom pairs C23—C34 and C7—O1 were subject to a rigid bond restraint (DELU instruction), i.e. the components of the displacement parameters in the direction of the bond were restrained to be equal within an effective standard deviation 0.004. The C16 and C36 methyl group exhibit orientational disorder in the hydrogen atom positions. The two sets of methyl hydrogen atoms were refined with equal occupancy.

Figures

Fig. 1.
Molecular structure of of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
Part of the crystal structure of the title compound. Molecular chains running along the b-axis are generated by N–H···O hydrogen bonds, shown as dashed lines. Symmetry codes (i): -x + 1,-y,-z + 1; (ii) -x + 1,-y + 1,-z ...

Crystal data

C16H17NOZ = 4
Mr = 239.31F(000) = 512
Triclinic, P1Dx = 1.173 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4186 (3) ÅCell parameters from 13000 reflections
b = 9.55915 (18) Åθ = 2.2–29.3°
c = 15.8813 (4) ŵ = 0.07 mm1
α = 74.361 (2)°T = 295 K
β = 79.696 (2)°Block, colourless
γ = 88.1582 (18)°0.51 × 0.41 × 0.22 mm
V = 1354.51 (6) Å3

Data collection

Oxford Diffraction Xcalibur with a Ruby Gemini detector diffractometer5130 independent reflections
graphite3880 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1Rint = 0.016
ω scansθmax = 25.7°, θmin = 2.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)h = −11→11
Tmin = 0.943, Tmax = 0.981k = −11→11
24655 measured reflectionsl = −19→19

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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0705P)2 + 0.0954P] where P = (Fo2 + 2Fc2)/3
5130 reflections(Δ/σ)max < 0.001
332 parametersΔρmax = 0.19 e Å3
2 restraintsΔρmin = −0.13 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*/UeqOcc. (<1)
C10.10346 (14)0.30182 (13)0.21469 (9)0.0465 (3)
C20.11199 (14)0.43910 (14)0.15658 (9)0.0488 (3)
H20.19960.48990.13990.059*
C3−0.00845 (15)0.50305 (14)0.12241 (9)0.0502 (3)
C4−0.13954 (15)0.42676 (15)0.14676 (10)0.0536 (4)
C5−0.14410 (15)0.28750 (16)0.20304 (10)0.0571 (4)
H5−0.23030.23450.21840.069*
C6−0.02543 (15)0.22486 (15)0.23707 (10)0.0538 (4)
H6−0.03220.13130.27490.065*
C70.32980 (14)0.30304 (13)0.27355 (9)0.0483 (3)
C80.43956 (14)0.20801 (13)0.31706 (9)0.0464 (3)
C90.51877 (16)0.26395 (15)0.36612 (10)0.0569 (4)
H90.50380.35910.36950.068*
C100.61908 (16)0.18210 (16)0.40995 (10)0.0601 (4)
H100.66910.22190.44370.072*
C110.64706 (15)0.04163 (15)0.40481 (10)0.0549 (4)
C120.57052 (16)−0.01379 (15)0.35434 (11)0.0603 (4)
H120.5887−0.10760.34910.072*
C130.46711 (16)0.06721 (14)0.31119 (10)0.0554 (4)
H130.4160.0270.27820.067*
C140.00537 (19)0.65361 (16)0.06181 (11)0.0678 (4)
H14A0.10560.68050.04240.102*
H14B−0.04230.72010.09290.102*
H14C−0.03840.65690.01120.102*
C15−0.27382 (18)0.4940 (2)0.11380 (14)0.0790 (5)
H15A−0.2870.58820.12430.118*
H15B−0.35620.4330.14490.118*
H15C−0.26360.50340.05130.118*
C160.75981 (18)−0.04604 (19)0.45196 (12)0.0738 (5)
H16A0.8190.01740.46940.111*0.5
H16B0.819−0.0940.41270.111*0.5
H16C0.7132−0.11730.50380.111*0.5
H16D0.7484−0.14660.45460.111*0.5
H16E0.7484−0.03530.51120.111*0.5
H16F0.8542−0.0120.42010.111*0.5
N10.22333 (12)0.23479 (11)0.25316 (8)0.0522 (3)
H1N0.22770.14170.26430.063*
O10.33726 (11)0.43667 (9)0.25845 (7)0.0638 (3)
C210.74411 (15)0.18251 (13)0.82751 (10)0.0510 (3)
C220.64037 (16)0.22586 (15)0.88897 (10)0.0549 (4)
H220.57950.30120.86880.066*
C230.62458 (16)0.16037 (16)0.97944 (10)0.0585 (4)
C240.71696 (18)0.04716 (15)1.00955 (10)0.0626 (4)
C250.81944 (19)0.00514 (16)0.94732 (11)0.0651 (4)
H250.8804−0.07040.96710.078*
C260.83512 (17)0.07014 (15)0.85765 (11)0.0605 (4)
H260.90560.03930.81780.073*
C270.81041 (15)0.21391 (14)0.66478 (10)0.0513 (3)
C280.81065 (15)0.32107 (14)0.57693 (9)0.0490 (3)
C290.91799 (16)0.31421 (16)0.50555 (11)0.0575 (4)
H290.9870.24230.51340.069*
C300.92379 (17)0.41186 (17)0.42359 (11)0.0621 (4)
H300.99810.40650.37740.074*
C310.82068 (18)0.51821 (16)0.40875 (10)0.0598 (4)
C320.71185 (18)0.52273 (16)0.47904 (10)0.0612 (4)
H320.64030.59180.47030.073*
C330.70702 (16)0.42699 (15)0.56190 (10)0.0567 (4)
H330.63340.43350.60820.068*
C340.5104 (2)0.2114 (2)1.04295 (12)0.0811 (5)
H34A0.55440.23911.08630.122*
H34B0.44130.13431.07240.122*
H34C0.46270.29341.01080.122*
C350.7065 (2)−0.0265 (2)1.10752 (12)0.0877 (6)
H35A0.7735−0.10471.11540.132*
H35B0.6102−0.06411.13190.132*
H35C0.7290.04271.13740.132*
C360.8276 (2)0.6250 (2)0.31868 (12)0.0885 (6)
H36A0.91050.60560.27880.133*0.5
H36B0.83490.7220.3240.133*0.5
H36C0.74180.61520.29590.133*0.5
H36D0.74760.68960.32030.133*0.5
H36E0.82320.57320.27510.133*0.5
H36F0.91640.680.30330.133*0.5
N20.75630 (13)0.26110 (11)0.73672 (8)0.0549 (3)
H2N0.72570.34880.72640.066*
O20.85769 (12)0.09069 (10)0.67005 (7)0.0667 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0471 (7)0.0423 (7)0.0512 (8)0.0065 (6)−0.0090 (6)−0.0149 (6)
C20.0438 (7)0.0467 (7)0.0571 (8)−0.0020 (6)−0.0106 (6)−0.0144 (6)
C30.0564 (8)0.0446 (7)0.0529 (8)0.0033 (6)−0.0142 (7)−0.0158 (6)
C40.0478 (8)0.0568 (8)0.0618 (9)0.0048 (6)−0.0153 (7)−0.0223 (7)
C50.0457 (8)0.0577 (8)0.0681 (10)−0.0055 (7)−0.0070 (7)−0.0183 (7)
C60.0537 (8)0.0452 (7)0.0590 (9)−0.0006 (6)−0.0042 (7)−0.0115 (6)
C70.0518 (8)0.0403 (6)0.0518 (8)0.0060 (6)−0.0073 (6)−0.0123 (6)
C80.0447 (7)0.0406 (7)0.0491 (8)0.0056 (6)−0.0035 (6)−0.0078 (6)
C90.0590 (9)0.0468 (7)0.0689 (10)0.0088 (7)−0.0138 (7)−0.0215 (7)
C100.0569 (9)0.0615 (9)0.0638 (10)0.0040 (7)−0.0158 (7)−0.0171 (7)
C110.0454 (8)0.0547 (8)0.0542 (8)0.0054 (6)−0.0045 (6)−0.0004 (7)
C120.0628 (9)0.0410 (7)0.0742 (10)0.0126 (7)−0.0124 (8)−0.0114 (7)
C130.0561 (8)0.0461 (7)0.0661 (9)0.0083 (6)−0.0155 (7)−0.0162 (7)
C140.0778 (11)0.0526 (8)0.0736 (11)0.0044 (8)−0.0314 (9)−0.0069 (8)
C150.0593 (10)0.0817 (11)0.1008 (14)0.0088 (9)−0.0308 (9)−0.0226 (10)
C160.0613 (10)0.0733 (10)0.0743 (11)0.0121 (8)−0.0174 (8)0.0035 (9)
N10.0549 (7)0.0350 (5)0.0658 (8)0.0044 (5)−0.0144 (6)−0.0101 (5)
O10.0730 (7)0.0377 (4)0.0875 (8)0.0087 (5)−0.0319 (6)−0.0175 (5)
C210.0560 (8)0.0375 (6)0.0605 (9)−0.0002 (6)−0.0165 (7)−0.0106 (6)
C220.0542 (8)0.0464 (7)0.0659 (10)0.0028 (6)−0.0163 (7)−0.0148 (7)
C230.0608 (9)0.0524 (8)0.0644 (10)−0.0087 (7)−0.0128 (7)−0.0168 (7)
C240.0765 (10)0.0475 (8)0.0630 (10)−0.0104 (7)−0.0211 (8)−0.0063 (7)
C250.0776 (11)0.0451 (8)0.0720 (11)0.0081 (7)−0.0262 (9)−0.0072 (7)
C260.0673 (10)0.0451 (7)0.0689 (10)0.0092 (7)−0.0175 (8)−0.0124 (7)
C270.0501 (8)0.0401 (7)0.0668 (9)0.0054 (6)−0.0163 (7)−0.0163 (6)
C280.0500 (8)0.0417 (7)0.0604 (9)0.0033 (6)−0.0162 (7)−0.0185 (6)
C290.0523 (8)0.0555 (8)0.0726 (10)0.0107 (7)−0.0161 (7)−0.0287 (8)
C300.0642 (10)0.0676 (9)0.0596 (9)−0.0015 (8)−0.0054 (8)−0.0291 (8)
C310.0743 (10)0.0550 (8)0.0552 (9)0.0011 (7)−0.0147 (8)−0.0215 (7)
C320.0705 (10)0.0540 (8)0.0600 (9)0.0164 (7)−0.0172 (8)−0.0152 (7)
C330.0595 (9)0.0520 (8)0.0577 (9)0.0122 (7)−0.0082 (7)−0.0157 (7)
C340.0821 (12)0.0884 (12)0.0752 (12)−0.0012 (10)−0.0092 (9)−0.0289 (10)
C350.1162 (16)0.0751 (11)0.0675 (11)−0.0026 (11)−0.0260 (11)−0.0052 (9)
C360.1194 (16)0.0842 (12)0.0585 (11)0.0085 (11)−0.0133 (10)−0.0158 (9)
N20.0663 (8)0.0392 (6)0.0596 (7)0.0121 (5)−0.0157 (6)−0.0123 (5)
O20.0815 (7)0.0407 (5)0.0802 (7)0.0160 (5)−0.0193 (6)−0.0187 (5)

Geometric parameters (Å, °)

C1—C61.3796 (19)C21—C261.3885 (19)
C1—C21.3812 (18)C21—C221.389 (2)
C1—N11.4309 (16)C21—N21.4209 (18)
C2—C31.3970 (18)C22—C231.387 (2)
C2—H20.93C22—H220.93
C3—C41.393 (2)C23—C241.402 (2)
C3—C141.495 (2)C23—C341.501 (2)
C4—C51.386 (2)C24—C251.385 (2)
C4—C151.513 (2)C24—C351.512 (2)
C5—C61.378 (2)C25—C261.375 (2)
C5—H50.93C25—H250.93
C6—H60.93C26—H260.93
C7—O11.2364 (15)C27—O21.2326 (15)
C7—N11.3448 (17)C27—N21.3502 (18)
C7—C81.4927 (18)C27—C281.491 (2)
C8—C91.3812 (19)C28—C331.3872 (19)
C8—C131.3871 (18)C28—C291.392 (2)
C9—C101.372 (2)C29—C301.375 (2)
C9—H90.93C29—H290.93
C10—C111.381 (2)C30—C311.386 (2)
C10—H100.93C30—H300.93
C11—C121.380 (2)C31—C321.383 (2)
C11—C161.510 (2)C31—C361.508 (2)
C12—C131.3863 (19)C32—C331.380 (2)
C12—H120.93C32—H320.93
C13—H130.93C33—H330.93
C14—H14A0.96C34—H34A0.96
C14—H14B0.96C34—H34B0.96
C14—H14C0.96C34—H34C0.96
C15—H15A0.96C35—H35A0.96
C15—H15B0.96C35—H35B0.96
C15—H15C0.96C35—H35C0.96
C16—H16A0.96C36—H36A0.96
C16—H16B0.96C36—H36B0.96
C16—H16C0.96C36—H36C0.96
C16—H16D0.96C36—H36D0.96
C16—H16E0.96C36—H36E0.96
C16—H16F0.96C36—H36F0.96
N1—H1N0.86N2—H2N0.86
C6—C1—C2119.20 (12)C26—C21—C22118.95 (14)
C6—C1—N1118.01 (11)C26—C21—N2123.14 (13)
C2—C1—N1122.79 (12)C22—C21—N2117.83 (12)
C1—C2—C3121.25 (12)C23—C22—C21122.13 (13)
C1—C2—H2119.4C23—C22—H22118.9
C3—C2—H2119.4C21—C22—H22118.9
C4—C3—C2119.52 (12)C22—C23—C24118.70 (14)
C4—C3—C14121.29 (13)C22—C23—C34119.93 (14)
C2—C3—C14119.17 (13)C24—C23—C34121.37 (15)
C5—C4—C3118.06 (12)C25—C24—C23118.36 (14)
C5—C4—C15120.72 (14)C25—C24—C35120.60 (15)
C3—C4—C15121.22 (13)C23—C24—C35121.03 (16)
C6—C5—C4122.34 (13)C26—C25—C24122.92 (14)
C6—C5—H5118.8C26—C25—H25118.5
C4—C5—H5118.8C24—C25—H25118.5
C5—C6—C1119.57 (13)C25—C26—C21118.94 (15)
C5—C6—H6120.2C25—C26—H26120.5
C1—C6—H6120.2C21—C26—H26120.5
O1—C7—N1122.74 (12)O2—C27—N2122.99 (13)
O1—C7—C8121.06 (12)O2—C27—C28121.21 (13)
N1—C7—C8116.20 (11)N2—C27—C28115.80 (11)
C9—C8—C13117.98 (12)C33—C28—C29117.72 (13)
C9—C8—C7117.90 (11)C33—C28—C27123.19 (13)
C13—C8—C7124.11 (12)C29—C28—C27119.08 (12)
C10—C9—C8121.37 (13)C30—C29—C28121.18 (13)
C10—C9—H9119.3C30—C29—H29119.4
C8—C9—H9119.3C28—C29—H29119.4
C9—C10—C11121.13 (14)C29—C30—C31121.05 (14)
C9—C10—H10119.4C29—C30—H30119.5
C11—C10—H10119.4C31—C30—H30119.5
C12—C11—C10117.77 (13)C32—C31—C30117.79 (14)
C12—C11—C16121.72 (14)C32—C31—C36121.41 (15)
C10—C11—C16120.50 (15)C30—C31—C36120.79 (15)
C11—C12—C13121.47 (13)C33—C32—C31121.46 (14)
C11—C12—H12119.3C33—C32—H32119.3
C13—C12—H12119.3C31—C32—H32119.3
C12—C13—C8120.26 (13)C32—C33—C28120.77 (14)
C12—C13—H13119.9C32—C33—H33119.6
C8—C13—H13119.9C28—C33—H33119.6
C3—C14—H14A109.5C23—C34—H34A109.5
C3—C14—H14B109.5C23—C34—H34B109.5
H14A—C14—H14B109.5H34A—C34—H34B109.5
C3—C14—H14C109.5C23—C34—H34C109.5
H14A—C14—H14C109.5H34A—C34—H34C109.5
H14B—C14—H14C109.5H34B—C34—H34C109.5
C4—C15—H15A109.5C24—C35—H35A109.5
C4—C15—H15B109.5C24—C35—H35B109.5
H15A—C15—H15B109.5H35A—C35—H35B109.5
C4—C15—H15C109.5C24—C35—H35C109.5
H15A—C15—H15C109.5H35A—C35—H35C109.5
H15B—C15—H15C109.5H35B—C35—H35C109.5
C11—C16—H16A109.5C31—C36—H36A109.5
C11—C16—H16B109.5C31—C36—H36B109.5
H16A—C16—H16B109.5H36A—C36—H36B109.5
C11—C16—H16C109.5C31—C36—H36C109.5
H16A—C16—H16C109.5H36A—C36—H36C109.5
H16B—C16—H16C109.5H36B—C36—H36C109.5
C11—C16—H16D109.5C31—C36—H36D109.5
H16A—C16—H16D141.1H36A—C36—H36D141.1
H16B—C16—H16D56.3H36B—C36—H36D56.3
H16C—C16—H16D56.3H36C—C36—H36D56.3
C11—C16—H16E109.5C31—C36—H36E109.5
H16A—C16—H16E56.3H36A—C36—H36E56.3
H16B—C16—H16E141.1H36B—C36—H36E141.1
H16C—C16—H16E56.3H36C—C36—H36E56.3
H16D—C16—H16E109.5H36D—C36—H36E109.5
C11—C16—H16F109.5C31—C36—H36F109.5
H16A—C16—H16F56.3H36A—C36—H36F56.3
H16B—C16—H16F56.3H36B—C36—H36F56.3
H16C—C16—H16F141.1H36C—C36—H36F141.1
H16D—C16—H16F109.5H36D—C36—H36F109.5
H16E—C16—H16F109.5H36E—C36—H36F109.5
C7—N1—C1126.38 (10)C27—N2—C21127.45 (11)
C7—N1—H1N116.8C27—N2—H2N116.3
C1—N1—H1N116.8C21—N2—H2N116.3
C6—C1—C2—C32.1 (2)C26—C21—C22—C23−0.1 (2)
N1—C1—C2—C3−177.99 (11)N2—C21—C22—C23−177.00 (12)
C1—C2—C3—C4−0.5 (2)C21—C22—C23—C240.3 (2)
C1—C2—C3—C14178.23 (13)C21—C22—C23—C34−179.90 (14)
C2—C3—C4—C5−1.4 (2)C22—C23—C24—C25−0.4 (2)
C14—C3—C4—C5179.87 (14)C34—C23—C24—C25179.74 (15)
C2—C3—C4—C15177.87 (14)C22—C23—C24—C35178.91 (14)
C14—C3—C4—C15−0.8 (2)C34—C23—C24—C35−0.9 (2)
C3—C4—C5—C61.8 (2)C23—C24—C25—C260.5 (2)
C15—C4—C5—C6−177.47 (14)C35—C24—C25—C26−178.86 (15)
C4—C5—C6—C1−0.3 (2)C24—C25—C26—C21−0.3 (2)
C2—C1—C6—C5−1.7 (2)C22—C21—C26—C250.2 (2)
N1—C1—C6—C5178.37 (12)N2—C21—C26—C25176.86 (13)
O1—C7—C8—C921.3 (2)O2—C27—C28—C33148.70 (14)
N1—C7—C8—C9−157.96 (13)N2—C27—C28—C33−31.60 (19)
O1—C7—C8—C13−158.56 (14)O2—C27—C28—C29−30.15 (19)
N1—C7—C8—C1322.2 (2)N2—C27—C28—C29149.55 (13)
C13—C8—C9—C10−1.8 (2)C33—C28—C29—C302.0 (2)
C7—C8—C9—C10178.34 (13)C27—C28—C29—C30−179.12 (13)
C8—C9—C10—C111.6 (2)C28—C29—C30—C31−1.6 (2)
C9—C10—C11—C12−0.2 (2)C29—C30—C31—C320.0 (2)
C9—C10—C11—C16178.81 (14)C29—C30—C31—C36−179.97 (14)
C10—C11—C12—C13−1.0 (2)C30—C31—C32—C331.4 (2)
C16—C11—C12—C13180.00 (14)C36—C31—C32—C33−178.70 (16)
C11—C12—C13—C80.8 (2)C31—C32—C33—C28−1.0 (2)
C9—C8—C13—C120.6 (2)C29—C28—C33—C32−0.6 (2)
C7—C8—C13—C12−179.55 (13)C27—C28—C33—C32−179.50 (13)
O1—C7—N1—C1−1.9 (2)O2—C27—N2—C210.1 (2)
C8—C7—N1—C1177.33 (12)C28—C27—N2—C21−179.59 (12)
C6—C1—N1—C7−148.38 (14)C26—C21—N2—C2727.1 (2)
C2—C1—N1—C731.7 (2)C22—C21—N2—C27−156.12 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.862.293.0860 (14)154
N2—H2N···O1ii0.862.183.0101 (14)162

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5089).

References

  • Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1–o3. [PubMed]
  • Brandenburg, K. (2002). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230.
  • Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o340. [PMC free article] [PubMed]
  • Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2009). Acta Cryst. E65, o1612. [PMC free article] [PubMed]
  • Oxford Diffraction (2009). CrysAlis Pro Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography