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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1444.
Published online 2008 July 9. doi:  10.1107/S1600536808017959
PMCID: PMC2962075

2-{4-[5-(3-Pyrid­yl)-2H-tetra­zol-2-ylmeth­yl]phen­yl}benzonitrile

Abstract

In the title compound, C20H14N6, there are two mol­ecules with similar conformations in the asymmetric unit. The pyridine and tetra­zole rings are nearly coplanar; they are twisted from each other by dihedral angles of only 8.7 (2) and 7.4 (2)°. The nearer benzene ring makes dihedral angles of 69.9 (2) and 88.5 (2)° with the tetra­zole ring in the two mol­ecules.

Related literature

For the use of tetra­zole derivatives in coordination chemistry, see: Arp et al. (2000 [triangle]); Hu et al. (2007 [triangle]); Wang et al. (2005 [triangle]); Xiong et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1444-scheme1.jpg

Experimental

Crystal data

  • C20H14N6
  • M r = 338.37
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1444-efi1.jpg
  • a = 10.2096 (9) Å
  • b = 13.3071 (16) Å
  • c = 13.709 (2) Å
  • α = 77.24 (2)°
  • β = 69.08 (2)°
  • γ = 83.52 (3)°
  • V = 1695.6 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.4 × 0.35 × 0.35 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.958, T max = 0.969
  • 18012 measured reflections
  • 8011 independent reflections
  • 3834 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.079
  • wR(F 2) = 0.239
  • S = 1.02
  • 8011 reflections
  • 469 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.21 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017959/dn2354sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017959/dn2354Isup2.hkl

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

Acknowledgments

This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong, and by the Excellent Doctor Degree Foundation from Southeast University to D-WF.

supplementary crystallographic information

Comment

In the past five years, our work have been focused on the chemistry of tetrazole derivatives because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Wang, et al. 2005; Xiong, et al. 2002). We report here the crystal structure of the title compound, 4-(4-((5-(pyridin-3-yl)-2H-tetrazol-2-yl)methyl)phenyl)benzonitrile.

The title compound contains two molecules with similar conformation in the asymmetrric unit. Each molecule is built up by four different rings (Fig.1). The pyridine and tetrazole rings are nearly coplanar and are only twisted from each other by a dihedral angle of 8.7 (2)° [7.4 (2)° for the second molecule]. The benzene ring makes a dihedral angle of 69.9 (2)° [88.5 (2)°] with the tetrazole ring owing to the methylene bridge which forces the two rings to be twisted from each other. The benzonitrile and the phenyl ring attached to it are twisted and make a dihedral angle of 46.5 (1)° [48.1 (2)°]. The C1—N1 and C21—N7 bond length of 1.153Å and 1.124Å conforms to the value for a C[equivalent]N bond. The bond distances and bond angles of the tetrazole rings are in the usual ranges (Wang et al., 2005; Arp et al., 2000; Hu et al., 2007).

Experimental

4-(4-((5-(Pyridin-3-yl)-2H-tetrazol-2-yl)methyl) phenyl)benzonitrile (3 mmol) was dissolved in ethanol (20 ml) and evaporated in the air affording colorless block crystals of this compound suitable for X-ray analysis were obtained.

Refinement

All H atoms were fixed geometrically and treated as riding with C–H = 0.93Å (methine), 0.97 Å(methylene), with Uiso(H) =1.2Ueq(C).

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. H atoms were omitted for clarity.

Crystal data

C20H14N6Z = 4
Mr = 338.37F000 = 704
Triclinic, P1Dx = 1.325 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.2096 (9) ÅCell parameters from 3792 reflections
b = 13.3071 (16) Åθ = 3.4–27.5º
c = 13.709 (2) ŵ = 0.08 mm1
α = 77.24 (2)ºT = 293 (2) K
β = 69.08 (2)ºBlock, colourless
γ = 83.52 (3)º0.4 × 0.35 × 0.35 mm
V = 1695.6 (4) Å3

Data collection

Rigaku Mercury2 (2x2 bin mode) diffractometer8011 independent reflections
Radiation source: fine-focus sealed tube3834 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.060
Detector resolution: 13.6612 pixels mm-1θmax = 27.9º
T = 293(2) Kθmin = 2.5º
ω scansh = −13→13
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −17→17
Tmin = 0.958, Tmax = 0.969l = −17→18
18012 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)] = 0.079H-atom parameters constrained
wR(F2) = 0.239  w = 1/[σ2(Fo2) + (0.1033P)2 + 0.086P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.033
8011 reflectionsΔρmax = 0.22 e Å3
469 parametersΔρmin = −0.21 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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 > 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
C10.2892 (3)0.4722 (3)−0.0251 (3)0.0493 (8)
C20.1973 (3)0.5487 (2)−0.0616 (3)0.0468 (8)
C30.1710 (4)0.5407 (3)−0.1523 (3)0.0607 (9)
H30.21880.4901−0.19060.073*
C40.0765 (4)0.6058 (3)−0.1859 (3)0.0666 (10)
H40.06100.6006−0.24740.080*
C50.0034 (4)0.6799 (3)−0.1279 (3)0.0651 (10)
H5−0.06440.7228−0.14870.078*
C60.0313 (4)0.6901 (3)−0.0390 (3)0.0573 (9)
H6−0.01720.7410−0.00150.069*
C70.1297 (3)0.6266 (2)−0.0042 (3)0.0452 (8)
C80.1637 (3)0.6414 (2)0.0893 (3)0.0454 (8)
C90.3033 (3)0.6420 (2)0.0825 (3)0.0457 (8)
H90.37480.63430.01930.055*
C100.3369 (3)0.6542 (2)0.1689 (3)0.0487 (8)
H100.43060.65380.16270.058*
C110.2337 (3)0.6667 (2)0.2634 (3)0.0461 (8)
C120.0941 (4)0.6678 (3)0.2696 (3)0.0547 (9)
H120.02270.67760.33210.066*
C130.0601 (3)0.6544 (3)0.1838 (3)0.0522 (8)
H13−0.03370.65420.19010.063*
C140.2711 (4)0.6775 (3)0.3571 (3)0.0555 (9)
H14A0.36180.70850.33110.067*
H14B0.20250.72390.39630.067*
C150.3401 (4)0.4363 (3)0.4950 (3)0.0514 (8)
C160.4180 (4)0.3383 (3)0.5131 (3)0.0513 (8)
C170.5540 (4)0.3219 (3)0.4464 (3)0.0570 (9)
H170.59500.37570.39100.068*
C180.5658 (5)0.1567 (3)0.5374 (4)0.0750 (12)
H180.61520.09400.54520.090*
C190.4333 (5)0.1661 (3)0.6073 (3)0.0731 (11)
H190.39410.11120.66190.088*
C200.3579 (4)0.2580 (3)0.5961 (3)0.0635 (10)
H200.26780.26620.64380.076*
C210.6865 (4)0.8056 (3)0.0890 (3)0.0586 (9)
C220.6915 (3)0.8914 (3)0.0020 (3)0.0507 (8)
C230.6572 (4)0.8719 (3)−0.0823 (3)0.0639 (10)
H230.63670.8058−0.08310.077*
C240.6545 (4)0.9530 (3)−0.1641 (3)0.0659 (10)
H240.63510.9412−0.22180.079*
C250.6802 (4)1.0505 (3)−0.1611 (3)0.0653 (10)
H250.67481.1047−0.21560.078*
C260.7141 (4)1.0698 (3)−0.0781 (3)0.0577 (9)
H260.73221.1366−0.07780.069*
C270.7215 (3)0.9901 (3)0.0050 (3)0.0465 (8)
C280.7665 (3)1.0123 (2)0.0908 (2)0.0457 (8)
C290.7080 (3)1.0970 (3)0.1394 (3)0.0510 (8)
H290.63911.13930.11950.061*
C300.7528 (3)1.1180 (2)0.2172 (3)0.0477 (8)
H300.71151.17320.25030.057*
C310.8579 (3)1.0579 (2)0.2462 (3)0.0478 (8)
C320.9173 (4)0.9740 (3)0.1969 (3)0.0523 (8)
H320.98820.93300.21530.063*
C330.8711 (4)0.9519 (3)0.1210 (3)0.0534 (9)
H330.91070.89540.08950.064*
C340.9099 (4)1.0827 (2)0.3284 (3)0.0540 (9)
H34A1.00231.11120.29350.065*
H34B0.84691.13370.36430.065*
C350.8588 (4)0.8580 (2)0.5220 (3)0.0466 (8)
C360.7784 (4)0.7789 (2)0.6086 (2)0.0457 (8)
C370.8411 (4)0.6860 (3)0.6409 (3)0.0571 (9)
H370.93640.67260.60830.068*
C380.7600 (4)0.6138 (3)0.7220 (3)0.0641 (10)
H380.80000.55120.74590.077*
C390.6189 (4)0.6359 (3)0.7673 (3)0.0646 (10)
H390.56460.58570.82040.078*
C400.6352 (4)0.7937 (3)0.6600 (3)0.0538 (9)
H400.59270.85550.63730.065*
N10.3591 (3)0.4065 (3)0.0031 (3)0.0677 (9)
N20.3825 (3)0.5112 (2)0.4104 (2)0.0522 (7)
N30.2766 (3)0.5798 (2)0.4296 (2)0.0531 (7)
N40.1736 (3)0.5504 (3)0.5198 (3)0.0775 (10)
N50.2121 (3)0.4598 (3)0.5637 (3)0.0717 (9)
N60.6296 (4)0.2346 (3)0.4563 (3)0.0729 (9)
N70.6834 (4)0.7392 (3)0.1563 (3)0.0806 (10)
N80.8039 (3)0.9433 (2)0.4788 (2)0.0511 (7)
N90.9167 (3)0.9889 (2)0.4062 (2)0.0499 (7)
N101.0358 (3)0.9351 (2)0.4026 (2)0.0596 (8)
N111.0016 (3)0.8513 (2)0.4766 (2)0.0554 (7)
N120.5550 (3)0.7260 (2)0.7389 (2)0.0621 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0432 (18)0.058 (2)0.052 (2)−0.0010 (16)−0.0159 (17)−0.0213 (17)
C20.0494 (19)0.0420 (17)0.049 (2)−0.0119 (15)−0.0147 (16)−0.0065 (14)
C30.060 (2)0.072 (2)0.054 (2)−0.0023 (19)−0.0214 (19)−0.0159 (18)
C40.075 (3)0.071 (3)0.062 (2)−0.016 (2)−0.034 (2)−0.004 (2)
C50.063 (2)0.063 (2)0.073 (3)−0.014 (2)−0.037 (2)0.011 (2)
C60.057 (2)0.048 (2)0.069 (2)−0.0036 (17)−0.026 (2)−0.0077 (17)
C70.0377 (17)0.0425 (17)0.054 (2)−0.0041 (14)−0.0156 (16)−0.0054 (15)
C80.0473 (18)0.0410 (17)0.050 (2)0.0017 (14)−0.0193 (16)−0.0112 (14)
C90.0398 (17)0.0434 (18)0.051 (2)−0.0025 (14)−0.0103 (15)−0.0126 (15)
C100.0397 (17)0.0470 (18)0.059 (2)−0.0007 (14)−0.0155 (17)−0.0130 (16)
C110.0501 (19)0.0379 (17)0.051 (2)−0.0005 (15)−0.0190 (17)−0.0081 (14)
C120.048 (2)0.061 (2)0.052 (2)0.0051 (17)−0.0118 (17)−0.0169 (17)
C130.0389 (18)0.058 (2)0.062 (2)0.0042 (15)−0.0169 (17)−0.0194 (17)
C140.065 (2)0.0469 (19)0.058 (2)0.0020 (17)−0.0252 (19)−0.0119 (16)
C150.052 (2)0.059 (2)0.046 (2)−0.0031 (17)−0.0192 (17)−0.0123 (16)
C160.054 (2)0.058 (2)0.049 (2)0.0033 (17)−0.0238 (18)−0.0173 (16)
C170.056 (2)0.056 (2)0.064 (2)−0.0023 (18)−0.023 (2)−0.0172 (18)
C180.086 (3)0.061 (3)0.082 (3)0.010 (2)−0.034 (3)−0.019 (2)
C190.089 (3)0.057 (2)0.070 (3)0.001 (2)−0.029 (3)−0.005 (2)
C200.067 (2)0.060 (2)0.059 (2)−0.0051 (19)−0.016 (2)−0.0085 (18)
C210.068 (2)0.049 (2)0.064 (2)−0.0112 (19)−0.025 (2)−0.0147 (19)
C220.0447 (19)0.056 (2)0.052 (2)0.0004 (16)−0.0148 (16)−0.0159 (16)
C230.067 (2)0.065 (2)0.069 (3)−0.009 (2)−0.025 (2)−0.027 (2)
C240.070 (3)0.078 (3)0.061 (2)0.002 (2)−0.031 (2)−0.023 (2)
C250.075 (3)0.068 (3)0.059 (2)0.002 (2)−0.032 (2)−0.0097 (19)
C260.064 (2)0.053 (2)0.060 (2)0.0039 (18)−0.027 (2)−0.0118 (17)
C270.0409 (17)0.054 (2)0.048 (2)−0.0014 (15)−0.0146 (16)−0.0164 (15)
C280.0450 (18)0.0449 (18)0.0462 (19)−0.0030 (15)−0.0126 (16)−0.0112 (14)
C290.0481 (19)0.052 (2)0.055 (2)0.0070 (16)−0.0214 (17)−0.0124 (16)
C300.055 (2)0.0371 (17)0.051 (2)−0.0034 (15)−0.0159 (17)−0.0136 (14)
C310.0505 (19)0.0456 (18)0.0461 (19)−0.0065 (15)−0.0158 (16)−0.0051 (15)
C320.051 (2)0.0496 (19)0.061 (2)0.0011 (16)−0.0245 (18)−0.0132 (16)
C330.053 (2)0.050 (2)0.062 (2)0.0094 (16)−0.0221 (18)−0.0230 (17)
C340.068 (2)0.0457 (19)0.052 (2)−0.0100 (17)−0.0259 (19)−0.0027 (15)
C350.054 (2)0.0444 (18)0.050 (2)0.0071 (16)−0.0264 (17)−0.0157 (15)
C360.057 (2)0.0447 (18)0.0433 (19)0.0008 (15)−0.0248 (17)−0.0133 (14)
C370.059 (2)0.053 (2)0.062 (2)0.0093 (18)−0.0262 (19)−0.0112 (18)
C380.079 (3)0.048 (2)0.070 (3)0.007 (2)−0.037 (2)−0.0068 (18)
C390.075 (3)0.062 (2)0.058 (2)−0.006 (2)−0.027 (2)−0.0074 (18)
C400.062 (2)0.050 (2)0.053 (2)0.0082 (17)−0.0256 (19)−0.0136 (16)
N10.061 (2)0.078 (2)0.074 (2)0.0183 (17)−0.0294 (18)−0.0337 (18)
N20.0522 (17)0.0555 (17)0.0503 (18)0.0062 (14)−0.0181 (14)−0.0168 (14)
N30.0519 (17)0.0600 (18)0.0489 (18)0.0058 (15)−0.0190 (15)−0.0148 (14)
N40.061 (2)0.083 (2)0.067 (2)0.0175 (18)−0.0082 (19)−0.0046 (18)
N50.057 (2)0.072 (2)0.066 (2)0.0097 (17)−0.0089 (17)0.0003 (17)
N60.074 (2)0.073 (2)0.075 (2)0.0214 (19)−0.0280 (19)−0.0305 (19)
N70.112 (3)0.062 (2)0.076 (2)−0.022 (2)−0.039 (2)−0.0089 (18)
N80.0549 (17)0.0446 (15)0.0557 (18)0.0006 (13)−0.0225 (15)−0.0089 (13)
N90.0531 (17)0.0520 (16)0.0482 (17)0.0003 (14)−0.0219 (15)−0.0105 (13)
N100.0548 (18)0.072 (2)0.0533 (18)0.0049 (16)−0.0218 (15)−0.0122 (16)
N110.0589 (19)0.0517 (17)0.0562 (19)0.0051 (14)−0.0252 (16)−0.0062 (14)
N120.0614 (19)0.062 (2)0.058 (2)−0.0027 (16)−0.0157 (17)−0.0101 (16)

Geometric parameters (Å, °)

C1—N11.153 (4)C22—C231.404 (5)
C1—C21.437 (5)C23—C241.379 (5)
C2—C31.391 (4)C23—H230.9300
C2—C71.407 (4)C24—C251.364 (5)
C3—C41.359 (5)C24—H240.9300
C3—H30.9300C25—C261.382 (5)
C4—C51.385 (5)C25—H250.9300
C4—H40.9300C26—C271.392 (4)
C5—C61.384 (5)C26—H260.9300
C5—H50.9300C27—C281.501 (4)
C6—C71.387 (4)C28—C331.391 (4)
C6—H60.9300C28—C291.402 (4)
C7—C81.499 (4)C29—C301.391 (4)
C8—C131.381 (4)C29—H290.9300
C8—C91.395 (4)C30—C311.385 (4)
C9—C101.391 (4)C30—H300.9300
C9—H90.9300C31—C321.400 (4)
C10—C111.377 (4)C31—C341.513 (4)
C10—H100.9300C32—C331.382 (4)
C11—C121.395 (4)C32—H320.9300
C11—C141.505 (4)C33—H330.9300
C12—C131.391 (4)C34—N91.465 (4)
C12—H120.9300C34—H34A0.9700
C13—H130.9300C34—H34B0.9700
C14—N31.460 (4)C35—N81.324 (4)
C14—H14A0.9700C35—N111.366 (4)
C14—H14B0.9700C35—C361.462 (5)
C15—N21.324 (4)C36—C371.385 (4)
C15—N51.361 (4)C36—C401.390 (5)
C15—C161.469 (5)C37—C381.376 (5)
C16—C201.387 (5)C37—H370.9300
C16—C171.387 (5)C38—C391.376 (5)
C17—N61.329 (4)C38—H380.9300
C17—H170.9300C39—N121.346 (4)
C18—C191.361 (6)C39—H390.9300
C18—N61.364 (5)C40—N121.326 (4)
C18—H180.9300C40—H400.9300
C19—C201.379 (5)N2—N31.323 (3)
C19—H190.9300N3—N41.319 (4)
C20—H200.9300N4—N51.308 (4)
C21—N71.122 (4)N8—N91.326 (4)
C21—C221.448 (5)N9—N101.330 (4)
C22—C271.394 (4)N10—N111.316 (4)
N1—C1—C2176.0 (3)C25—C24—C23120.6 (4)
C3—C2—C7120.7 (3)C25—C24—H24119.7
C3—C2—C1118.2 (3)C23—C24—H24119.7
C7—C2—C1121.0 (3)C24—C25—C26120.9 (4)
C4—C3—C2120.9 (4)C24—C25—H25119.5
C4—C3—H3119.6C26—C25—H25119.5
C2—C3—H3119.6C25—C26—C27120.6 (3)
C3—C4—C5119.6 (4)C25—C26—H26119.7
C3—C4—H4120.2C27—C26—H26119.7
C5—C4—H4120.2C26—C27—C22117.7 (3)
C6—C5—C4119.9 (4)C26—C27—C28119.4 (3)
C6—C5—H5120.0C22—C27—C28122.9 (3)
C4—C5—H5120.0C33—C28—C29118.4 (3)
C5—C6—C7121.9 (4)C33—C28—C27120.8 (3)
C5—C6—H6119.0C29—C28—C27120.7 (3)
C7—C6—H6119.0C30—C29—C28120.1 (3)
C6—C7—C2116.9 (3)C30—C29—H29119.9
C6—C7—C8121.5 (3)C28—C29—H29119.9
C2—C7—C8121.7 (3)C31—C30—C29121.1 (3)
C13—C8—C9118.1 (3)C31—C30—H30119.5
C13—C8—C7121.8 (3)C29—C30—H30119.5
C9—C8—C7120.1 (3)C30—C31—C32118.7 (3)
C10—C9—C8120.9 (3)C30—C31—C34121.1 (3)
C10—C9—H9119.6C32—C31—C34120.1 (3)
C8—C9—H9119.6C33—C32—C31120.3 (3)
C11—C10—C9121.1 (3)C33—C32—H32119.9
C11—C10—H10119.4C31—C32—H32119.9
C9—C10—H10119.4C32—C33—C28121.3 (3)
C10—C11—C12118.0 (3)C32—C33—H33119.3
C10—C11—C14120.7 (3)C28—C33—H33119.3
C12—C11—C14121.3 (3)N9—C34—C31109.9 (3)
C13—C12—C11121.1 (3)N9—C34—H34A109.7
C13—C12—H12119.5C31—C34—H34A109.7
C11—C12—H12119.5N9—C34—H34B109.7
C8—C13—C12120.8 (3)C31—C34—H34B109.7
C8—C13—H13119.6H34A—C34—H34B108.2
C12—C13—H13119.6N8—C35—N11112.3 (3)
N3—C14—C11113.6 (3)N8—C35—C36124.8 (3)
N3—C14—H14A108.8N11—C35—C36122.9 (3)
C11—C14—H14A108.8C37—C36—C40117.6 (3)
N3—C14—H14B108.8C37—C36—C35121.4 (3)
C11—C14—H14B108.8C40—C36—C35121.0 (3)
H14A—C14—H14B107.7C38—C37—C36119.0 (3)
N2—C15—N5111.6 (3)C38—C37—H37120.5
N2—C15—C16125.2 (3)C36—C37—H37120.5
N5—C15—C16123.2 (3)C39—C38—C37118.8 (3)
C20—C16—C17117.4 (3)C39—C38—H38120.6
C20—C16—C15121.5 (3)C37—C38—H38120.6
C17—C16—C15121.1 (3)N12—C39—C38123.7 (4)
N6—C17—C16124.4 (4)N12—C39—H39118.1
N6—C17—H17117.8C38—C39—H39118.1
C16—C17—H17117.8N12—C40—C36124.7 (3)
C19—C18—N6123.2 (4)N12—C40—H40117.7
C19—C18—H18118.4C36—C40—H40117.6
N6—C18—H18118.4C15—N2—N3102.3 (3)
C18—C19—C20119.2 (4)N4—N3—N2113.4 (3)
C18—C19—H19120.4N4—N3—C14122.7 (3)
C20—C19—H19120.4N2—N3—C14123.8 (3)
C19—C20—C16119.3 (4)N5—N4—N3106.7 (3)
C19—C20—H20120.3N4—N5—C15106.0 (3)
C16—C20—H20120.3C17—N6—C18116.4 (4)
N7—C21—C22179.6 (4)C35—N8—N9102.1 (3)
C27—C22—C23121.6 (3)N8—N9—N10113.6 (3)
C27—C22—C21121.3 (3)N8—N9—C34123.2 (3)
C23—C22—C21117.0 (3)N10—N9—C34122.8 (3)
C24—C23—C22118.5 (3)N11—N10—N9106.5 (3)
C24—C23—H23120.7N10—N11—C35105.6 (3)
C22—C23—H23120.7C40—N12—C39116.1 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2354).

References

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