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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1688.
Published online 2009 June 27. doi:  10.1107/S1600536809021175
PMCID: PMC2969414

2-p-Tolyl-1-p-tolyl­methyl-1H-benzimidazole

Abstract

The asymmetric unit of the title compound, C22H20N2, contains two crystallographically independent mol­ecules in which the planar benzimidazole ring systems are oriented with respect to the adjacent tolyl rings at dihedral angles of 47.08 (8)/76.85 (8) and 39.52 (9)/87.49 (9)°, while the dihedral angles between the tolyl rings are 73.99 (3) and 81.51 (9)°. In the crystal structure, pairs of inter­molecular C—H(...)N inter­actions link one of the asymmetric mol­ecules into centrosymmetric dimers through R 2 2(8) ring motifs.

Related literature

For general background to the biological and pharmaceutical activities of benzimidazole derivatives, see: Matsuno et al. (2000 [triangle]). Garuti et al. (1999 [triangle]). For related structures, see: Tlahuext et al. (2007 [triangle]); Chen & Ruan (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For ring-motifs, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o1688-scheme1.jpg

Experimental

Crystal data

  • C22H20N2
  • M r = 312.40
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1688-efi1.jpg
  • a = 9.7046 (19) Å
  • b = 10.457 (2) Å
  • c = 17.825 (4) Å
  • α = 84.12 (3)°
  • β = 81.44 (3)°
  • γ = 75.87 (3)°
  • V = 1730.4 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 294 K
  • 0.20 × 0.18 × 0.15 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.984, T max = 0.988
  • 16221 measured reflections
  • 6773 independent reflections
  • 3812 reflections with I > 2σ(I)
  • R int = 0.057

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.173
  • S = 1.01
  • 6773 reflections
  • 434 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (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/S1600536809021175/hk2704sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021175/hk2704Isup2.hkl

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

supplementary crystallographic information

Comment

Benzimidazole derivatives have attracted considerable attention because of their biological and pharmaceutical activities (Matsuno et al., 2000; Garuti et al., 1999). In addition, they play an important role in the development of coordination chemistry. Many derivatives of benzimidazole have been prepared and their complexes have been studied (Tlahuext et al., 2007; Chen & Ruan, 2007). We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (N1/N2/C8/C9/C14), C (C9-C14), D (C16-C21) and E (C23-C28), F (N3/N4/C30/C31/C36), G (C31-C36), H (C38-C43) are, of course, planar. The planar benzimidazole ring systems, (N1/N2/C8-C14) and (N3/N4/C30-C36), are oriented with respect to the adjacent rings, A, D and E, H, at dihedral angles of 47.08 (8), 76.85 (8) ° and 39.52 (9), 87.49 (9) °, respectively, while the dihedral angles between rings A, D and E, H are 73.99 (3) and 81.51 (9) °, respectively.

In the crystal structure, intermolecular C-H···N interactions (Table 1) link the molecules into centrosymmetric dimers through R22(8) ring motifs (Bernstein et al., 1995) (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, 4-methylbenzaldehyde(0.96 g, 8 mmol) was added to a solution of o-phenylenediamine (0.432 g, 4 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for 4 h. When cooled to room temperature, the resultant solution was filtered and allowed to evaporate slowly. Crystals suitable for X-ray analysis were obtained after several weeks.

Refinement

H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C22H20N2Z = 4
Mr = 312.40F(000) = 664
Triclinic, P1Dx = 1.199 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7046 (19) ÅCell parameters from 2562 reflections
b = 10.457 (2) Åθ = 3.0–27.5°
c = 17.825 (4) ŵ = 0.07 mm1
α = 84.12 (3)°T = 294 K
β = 81.44 (3)°Prism, yellow
γ = 75.87 (3)°0.20 × 0.18 × 0.15 mm
V = 1730.4 (7) Å3

Data collection

Rigaku SCXmini diffractometer6773 independent reflections
Radiation source: fine-focus sealed tube3812 reflections with I > 2σ(I)
graphiteRint = 0.057
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 3.0°
ω scansh = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −12→12
Tmin = 0.984, Tmax = 0.988l = −21→21
16221 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.173w = 1/[σ2(Fo2) + (0.0746P)2 + 0.1986P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6773 reflectionsΔρmax = 0.23 e Å3
434 parametersΔρmin = −0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0175 (19)

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
N10.6191 (2)1.6298 (2)−0.44528 (12)0.0553 (6)
N20.6780 (2)1.57278 (19)−0.32714 (11)0.0453 (5)
N30.1316 (2)1.0170 (2)0.07446 (11)0.0479 (5)
N40.2184 (2)0.98105 (19)0.18661 (11)0.0424 (5)
C10.8163 (3)1.4336 (2)−0.43273 (14)0.0464 (6)
C20.9553 (3)1.4080 (3)−0.41494 (14)0.0542 (7)
H2A0.97741.4587−0.38060.065*
C31.0614 (3)1.3078 (3)−0.44762 (15)0.0586 (8)
H3B1.15431.2925−0.43550.070*
C41.0298 (3)1.2301 (3)−0.49837 (16)0.0588 (8)
C50.8919 (3)1.2560 (3)−0.51599 (16)0.0650 (8)
H5A0.86991.2052−0.55040.078*
C60.7857 (3)1.3558 (3)−0.48363 (15)0.0576 (7)
H6A0.69301.3710−0.49600.069*
C71.1466 (3)1.1202 (3)−0.53379 (19)0.0848 (10)
H7A1.23521.1176−0.51520.127*
H7B1.15781.1364−0.58810.127*
H7C1.12061.0371−0.52050.127*
C80.7038 (3)1.5452 (2)−0.40265 (14)0.0466 (6)
C90.5663 (3)1.6844 (3)−0.32230 (15)0.0479 (6)
C100.4940 (3)1.7545 (3)−0.26059 (17)0.0612 (8)
H10A0.51741.7295−0.21160.073*
C110.3857 (3)1.8631 (3)−0.2755 (2)0.0767 (9)
H11A0.33431.9126−0.23570.092*
C120.3519 (3)1.9000 (3)−0.3491 (2)0.0804 (10)
H12A0.27921.9744−0.35750.096*
C130.4237 (3)1.8291 (3)−0.40956 (19)0.0700 (9)
H13A0.40021.8542−0.45850.084*
C140.5320 (3)1.7190 (3)−0.39567 (16)0.0523 (7)
C150.7380 (3)1.4943 (3)−0.26301 (14)0.0507 (7)
H15A0.78551.4068−0.27900.061*
H15B0.65991.4847−0.22360.061*
C160.8433 (2)1.5486 (2)−0.22885 (13)0.0437 (6)
C170.9021 (3)1.4811 (3)−0.16589 (15)0.0618 (8)
H17A0.87571.4037−0.14570.074*
C180.9984 (3)1.5259 (3)−0.13277 (17)0.0718 (9)
H18A1.03681.4775−0.09090.086*
C191.0397 (3)1.6404 (3)−0.15976 (19)0.0659 (8)
C200.9818 (3)1.7078 (3)−0.22217 (19)0.0662 (8)
H20A1.00781.7857−0.24170.079*
C210.8854 (3)1.6627 (3)−0.25690 (16)0.0554 (7)
H21A0.84891.7101−0.29950.066*
C221.1441 (4)1.6895 (4)−0.1216 (2)0.1041 (13)
H22A1.17211.6294−0.07910.156*
H22B1.09921.7755−0.10410.156*
H22C1.22721.6948−0.15730.156*
C230.3362 (3)1.1114 (2)0.07900 (13)0.0431 (6)
C240.4795 (3)1.0759 (3)0.09004 (14)0.0495 (7)
H24A0.51191.00320.12280.059*
C250.5746 (3)1.1477 (3)0.05280 (14)0.0541 (7)
H25A0.67021.12260.06110.065*
C260.5304 (3)1.2565 (3)0.00336 (14)0.0518 (7)
C270.3868 (3)1.2908 (3)−0.00714 (15)0.0581 (7)
H27A0.35431.3637−0.03970.070*
C280.2916 (3)1.2198 (3)0.02942 (15)0.0532 (7)
H28A0.19621.24470.02080.064*
C290.6345 (3)1.3335 (3)−0.03835 (17)0.0734 (9)
H29A0.58471.4046−0.06990.110*
H29B0.70841.2761−0.06950.110*
H29C0.67681.3690−0.00220.110*
C300.2308 (2)1.0356 (2)0.11300 (14)0.0438 (6)
C310.1011 (2)0.9250 (2)0.19544 (14)0.0423 (6)
C320.0355 (3)0.8616 (2)0.25793 (15)0.0526 (7)
H32A0.07000.84770.30480.063*
C33−0.0839 (3)0.8205 (3)0.24641 (17)0.0615 (8)
H33A−0.13110.77740.28670.074*
C34−0.1361 (3)0.8413 (3)0.17649 (18)0.0608 (8)
H34A−0.21710.81200.17140.073*
C35−0.0707 (3)0.9041 (2)0.11474 (16)0.0538 (7)
H35A−0.10550.91720.06800.065*
C360.0495 (3)0.9472 (2)0.12493 (14)0.0447 (6)
C370.2984 (3)0.9895 (2)0.24814 (13)0.0471 (6)
H37A0.23101.01580.29290.056*
H37B0.35071.05820.23360.056*
C380.4024 (2)0.8630 (2)0.26853 (13)0.0428 (6)
C390.4396 (3)0.8375 (3)0.34111 (15)0.0651 (8)
H39A0.39760.89750.37770.078*
C400.5393 (3)0.7230 (3)0.36022 (16)0.0699 (9)
H40A0.56230.70760.40970.084*
C410.6042 (3)0.6326 (3)0.30811 (16)0.0539 (7)
C420.5665 (3)0.6578 (3)0.23607 (16)0.0546 (7)
H42A0.60860.59740.19970.065*
C430.4675 (3)0.7708 (2)0.21636 (14)0.0483 (6)
H43A0.44420.78510.16700.058*
C440.7142 (3)0.5098 (3)0.3292 (2)0.0820 (10)
H44A0.72740.50950.38150.123*
H44B0.80350.50900.29750.123*
H44C0.68160.43290.32190.123*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0517 (13)0.0609 (14)0.0511 (14)−0.0031 (11)−0.0162 (11)−0.0040 (12)
N20.0463 (12)0.0466 (12)0.0433 (12)−0.0079 (10)−0.0098 (9)−0.0052 (10)
N30.0442 (12)0.0577 (13)0.0432 (12)−0.0158 (10)−0.0102 (10)0.0059 (11)
N40.0433 (12)0.0450 (12)0.0383 (12)−0.0096 (10)−0.0078 (9)0.0019 (10)
C10.0471 (15)0.0490 (15)0.0415 (14)−0.0080 (12)−0.0083 (11)0.0000 (12)
C20.0547 (17)0.0587 (17)0.0478 (16)−0.0087 (14)−0.0081 (13)−0.0055 (14)
C30.0518 (17)0.0625 (18)0.0529 (17)−0.0027 (14)−0.0039 (13)0.0059 (15)
C40.067 (2)0.0468 (16)0.0526 (17)−0.0016 (14)0.0037 (14)0.0008 (14)
C50.074 (2)0.0587 (18)0.0642 (19)−0.0117 (16)−0.0110 (16)−0.0164 (16)
C60.0547 (17)0.0605 (18)0.0587 (17)−0.0118 (14)−0.0110 (13)−0.0079 (15)
C70.088 (2)0.068 (2)0.082 (2)0.0055 (18)0.0055 (19)−0.0086 (18)
C80.0438 (15)0.0521 (16)0.0460 (15)−0.0111 (13)−0.0110 (12)−0.0054 (13)
C90.0412 (14)0.0506 (15)0.0553 (17)−0.0136 (12)−0.0069 (12)−0.0109 (13)
C100.0611 (18)0.0663 (19)0.0587 (18)−0.0145 (16)−0.0080 (14)−0.0167 (16)
C110.062 (2)0.075 (2)0.090 (3)−0.0025 (17)−0.0051 (18)−0.035 (2)
C120.058 (2)0.072 (2)0.106 (3)0.0082 (16)−0.0221 (19)−0.023 (2)
C130.0563 (18)0.070 (2)0.079 (2)0.0031 (16)−0.0216 (16)−0.0095 (18)
C140.0415 (15)0.0579 (17)0.0590 (17)−0.0085 (13)−0.0117 (13)−0.0104 (14)
C150.0563 (17)0.0509 (16)0.0454 (15)−0.0164 (13)−0.0041 (13)−0.0002 (13)
C160.0439 (15)0.0468 (15)0.0385 (14)−0.0067 (12)−0.0059 (11)−0.0026 (12)
C170.0648 (19)0.0699 (19)0.0512 (17)−0.0202 (16)−0.0081 (14)0.0060 (15)
C180.068 (2)0.093 (2)0.0534 (18)−0.0091 (18)−0.0245 (15)−0.0008 (18)
C190.0518 (18)0.069 (2)0.079 (2)−0.0039 (15)−0.0170 (16)−0.0234 (18)
C200.0556 (18)0.0503 (17)0.096 (2)−0.0115 (14)−0.0193 (17)−0.0082 (17)
C210.0542 (17)0.0454 (16)0.0666 (19)−0.0085 (13)−0.0171 (14)0.0017 (14)
C220.074 (2)0.120 (3)0.132 (3)−0.016 (2)−0.045 (2)−0.043 (3)
C230.0431 (14)0.0497 (15)0.0377 (14)−0.0132 (12)−0.0056 (11)−0.0029 (12)
C240.0519 (16)0.0528 (16)0.0457 (15)−0.0136 (13)−0.0119 (12)−0.0001 (13)
C250.0463 (16)0.0699 (19)0.0513 (17)−0.0203 (14)−0.0062 (13)−0.0114 (15)
C260.0608 (18)0.0561 (17)0.0439 (15)−0.0262 (14)0.0004 (13)−0.0080 (14)
C270.0647 (19)0.0566 (17)0.0536 (17)−0.0194 (15)−0.0102 (14)0.0100 (14)
C280.0463 (16)0.0592 (17)0.0540 (16)−0.0144 (13)−0.0101 (13)0.0069 (14)
C290.083 (2)0.083 (2)0.067 (2)−0.0471 (19)−0.0051 (16)−0.0010 (17)
C300.0393 (14)0.0464 (15)0.0436 (15)−0.0065 (12)−0.0057 (11)−0.0020 (12)
C310.0412 (14)0.0371 (13)0.0452 (15)−0.0057 (11)−0.0039 (11)0.0017 (12)
C320.0537 (17)0.0460 (15)0.0538 (17)−0.0070 (13)−0.0056 (13)0.0035 (13)
C330.0564 (18)0.0562 (17)0.067 (2)−0.0160 (14)0.0065 (15)0.0066 (15)
C340.0439 (16)0.0567 (17)0.081 (2)−0.0146 (13)−0.0078 (15)0.0048 (16)
C350.0448 (16)0.0552 (17)0.0631 (18)−0.0140 (13)−0.0148 (13)0.0045 (14)
C360.0419 (14)0.0452 (15)0.0446 (15)−0.0061 (12)−0.0080 (11)0.0027 (12)
C370.0542 (16)0.0481 (15)0.0392 (14)−0.0089 (13)−0.0113 (12)−0.0044 (12)
C380.0414 (14)0.0524 (15)0.0370 (14)−0.0163 (12)−0.0063 (11)0.0002 (12)
C390.0653 (19)0.083 (2)0.0389 (16)0.0035 (16)−0.0135 (13)−0.0090 (15)
C400.0641 (19)0.097 (2)0.0414 (16)−0.0047 (18)−0.0168 (14)0.0069 (17)
C410.0436 (15)0.0598 (18)0.0582 (18)−0.0130 (13)−0.0142 (13)0.0097 (15)
C420.0530 (17)0.0521 (17)0.0584 (18)−0.0104 (13)−0.0087 (13)−0.0052 (14)
C430.0586 (17)0.0500 (16)0.0391 (14)−0.0144 (13)−0.0142 (12)0.0000 (13)
C440.070 (2)0.075 (2)0.095 (3)−0.0042 (17)−0.0285 (18)0.0143 (19)

Geometric parameters (Å, °)

N1—C81.315 (3)C21—C201.389 (4)
N1—C141.388 (3)C21—H21A0.9300
N2—C81.379 (3)C22—H22A0.9600
N2—C91.386 (3)C22—H22B0.9600
N2—C151.446 (3)C22—H22C0.9600
N3—C301.324 (3)C23—C241.388 (3)
N3—C361.383 (3)C23—C281.386 (3)
N4—C301.376 (3)C23—C301.467 (3)
N4—C311.384 (3)C24—C251.382 (3)
N4—C371.456 (3)C24—H24A0.9300
C1—C21.387 (3)C25—H25A0.9300
C1—C61.387 (3)C26—C251.387 (4)
C2—C31.384 (4)C26—C291.508 (4)
C2—H2A0.9300C27—C261.388 (4)
C3—H3B0.9300C27—H27A0.9300
C4—C31.388 (4)C28—C271.373 (3)
C4—C51.376 (4)C28—H28A0.9300
C4—C71.518 (4)C29—H29A0.9600
C5—H5A0.9300C29—H29B0.9600
C6—C51.381 (4)C29—H29C0.9600
C6—H6A0.9300C31—C321.389 (3)
C7—H7A0.9600C31—C361.398 (3)
C7—H7B0.9600C32—C331.378 (4)
C7—H7C0.9600C32—H32A0.9300
C8—C11.474 (3)C33—H33A0.9300
C9—C101.387 (4)C34—C331.391 (4)
C9—C141.388 (4)C34—C351.376 (4)
C10—C111.380 (4)C34—H34A0.9300
C10—H10A0.9300C35—H35A0.9300
C11—H11A0.9300C36—C351.390 (3)
C12—C111.393 (4)C37—C381.504 (3)
C12—H12A0.9300C37—H37A0.9700
C13—C121.373 (4)C37—H37B0.9700
C13—H13A0.9300C38—C391.377 (3)
C14—C131.385 (4)C38—C431.380 (3)
C15—H15A0.9700C39—C401.391 (4)
C15—H15B0.9700C39—H39A0.9300
C16—C151.509 (3)C40—H40A0.9300
C16—C171.384 (4)C41—C401.367 (4)
C16—C211.376 (3)C41—C441.510 (4)
C17—C181.369 (4)C42—C411.369 (4)
C17—H17A0.9300C42—H42A0.9300
C18—H18A0.9300C43—C421.380 (3)
C19—C181.373 (4)C43—H43A0.9300
C19—C221.511 (4)C44—H44A0.9600
C20—C191.372 (4)C44—H44B0.9600
C20—H20A0.9300C44—H44C0.9600
C8—N1—C14105.0 (2)C19—C22—H22C109.5
C8—N2—C15128.5 (2)H22A—C22—H22B109.5
C9—N2—C8105.8 (2)H22A—C22—H22C109.5
C9—N2—C15125.2 (2)H22B—C22—H22C109.5
C30—N3—C36105.4 (2)C24—C23—C30123.7 (2)
C30—N4—C31106.51 (19)C28—C23—C24118.3 (2)
C30—N4—C37129.1 (2)C28—C23—C30118.0 (2)
C31—N4—C37124.1 (2)C23—C24—H24A119.7
C2—C1—C8121.9 (2)C25—C24—C23120.6 (2)
C6—C1—C2118.5 (2)C25—C24—H24A119.7
C6—C1—C8119.5 (2)C24—C25—C26121.3 (2)
C1—C2—C3120.9 (3)C24—C25—H25A119.3
C1—C2—H2A119.5C26—C25—H25A119.3
C3—C2—H2A119.5C25—C26—C29121.4 (3)
C2—C3—C4120.3 (3)C27—C26—C25117.4 (2)
C2—C3—H3B119.9C27—C26—C29121.1 (3)
C4—C3—H3B119.9C26—C27—H27A119.2
C3—C4—C7120.0 (3)C28—C27—C26121.6 (3)
C5—C4—C3118.6 (3)C28—C27—H27A119.2
C5—C4—C7121.3 (3)C23—C28—H28A119.6
C4—C5—C6121.3 (3)C27—C28—C23120.7 (2)
C4—C5—H5A119.3C27—C28—H28A119.6
C6—C5—H5A119.3C26—C29—H29A109.5
C1—C6—H6A119.8C26—C29—H29B109.5
C5—C6—C1120.4 (3)C26—C29—H29C109.5
C5—C6—H6A119.8H29A—C29—H29B109.5
C4—C7—H7A109.5H29A—C29—H29C109.5
C4—C7—H7B109.5H29B—C29—H29C109.5
C4—C7—H7C109.5N3—C30—N4112.4 (2)
H7A—C7—H7B109.5N3—C30—C23121.6 (2)
H7A—C7—H7C109.5N4—C30—C23125.9 (2)
H7B—C7—H7C109.5N4—C31—C32131.9 (2)
N1—C8—N2113.1 (2)N4—C31—C36105.7 (2)
N1—C8—C1123.4 (2)C32—C31—C36122.4 (2)
N2—C8—C1123.5 (2)C31—C32—H32A122.0
N2—C9—C10131.3 (3)C33—C32—C31116.1 (3)
N2—C9—C14106.1 (2)C33—C32—H32A122.0
C10—C9—C14122.6 (3)C32—C33—C34122.2 (3)
C9—C10—H10A121.7C32—C33—H33A118.9
C11—C10—C9116.6 (3)C34—C33—H33A118.9
C11—C10—H10A121.7C33—C34—H34A119.2
C10—C11—C12121.3 (3)C35—C34—C33121.6 (3)
C10—C11—H11A119.4C35—C34—H34A119.2
C12—C11—H11A119.4C34—C35—C36117.4 (3)
C11—C12—H12A119.3C34—C35—H35A121.3
C13—C12—C11121.4 (3)C36—C35—H35A121.3
C13—C12—H12A119.3N3—C36—C35129.7 (2)
C12—C13—C14118.2 (3)N3—C36—C31109.9 (2)
C12—C13—H13A120.9C35—C36—C31120.4 (2)
C14—C13—H13A120.9N4—C37—C38114.20 (19)
N1—C14—C9110.0 (2)N4—C37—H37A108.7
C13—C14—N1130.1 (3)N4—C37—H37B108.7
C13—C14—C9119.9 (3)C38—C37—H37A108.7
N2—C15—C16115.6 (2)C38—C37—H37B108.7
N2—C15—H15A108.4H37A—C37—H37B107.6
N2—C15—H15B108.4C39—C38—C43117.4 (2)
C16—C15—H15A108.4C39—C38—C37119.9 (2)
C16—C15—H15B108.4C43—C38—C37122.6 (2)
H15A—C15—H15B107.4C38—C39—C40120.7 (3)
C17—C16—C15119.0 (2)C38—C39—H39A119.7
C21—C16—C17117.4 (2)C40—C39—H39A119.7
C21—C16—C15123.7 (2)C39—C40—H40A119.2
C16—C17—H17A119.3C41—C40—C39121.6 (3)
C18—C17—C16121.4 (3)C41—C40—H40A119.2
C18—C17—H17A119.3C40—C41—C44121.1 (3)
C17—C18—C19121.7 (3)C42—C41—C40117.6 (3)
C17—C18—H18A119.2C42—C41—C44121.2 (3)
C19—C18—H18A119.2C41—C42—C43121.4 (3)
C18—C19—C20117.2 (3)C41—C42—H42A119.3
C18—C19—C22120.9 (3)C43—C42—H42A119.3
C20—C19—C22121.8 (3)C38—C43—H43A119.4
C19—C20—C21121.7 (3)C42—C43—C38121.3 (2)
C19—C20—H20A119.2C42—C43—H43A119.4
C21—C20—H20A119.2C41—C44—H44A109.5
C16—C21—C20120.6 (3)C41—C44—H44B109.5
C16—C21—H21A119.7C41—C44—H44C109.5
C20—C21—H21A119.7H44A—C44—H44B109.5
C19—C22—H22A109.5H44A—C44—H44C109.5
C19—C22—H22B109.5H44B—C44—H44C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C35—H35A···N3i0.932.603.491 (3)162

Symmetry codes: (i) −x, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2704).

References

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