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Acta Cryst. (2007). E63, o4410
https://doi.org/10.1107/S1600536807051537
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5-(4'-Methyl­biphenyl-2-yl)-2-triphenyl­methyl-2H-tetra­zole

G.-X. Wang and H.-Y. Ye
The title compound, C33H26N4, was synthesized in two steps from 2-phenyl­benzonitrile. Geometric parameters are in the usual ranges. The tetra­zole ring encloses dihedral angles of 45.76 (9), 71.44 (8) and 72.38 (6)° with the three phenyl rings of the triphenyl­methyl group. The dihedral angle between the tetrazole ring and the benzene ring directly attached to it is 49.13 (8)° and the dihedral angle between the aromatic rings of the biphenyl group is 54.29 (8)°.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051537/bt2551sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051537/bt2551Isup2.hkl
Contains datablock I

CCDC reference: 667422

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.060
  • wR factor = 0.148
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found




Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.816     1.000
            Tmin(prime) and Tmax expected:      0.985     0.994
            RR(prime) =      0.824
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C33 H26 N4


Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.994
            Tmax scaled      0.994 Tmin scaled      0.812
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Studies on compounds containing a tetrazole ring were in recent years highly stimulated by its a wide range of applications in coordination chemistry as ligands, in medicinal chemistry as a metabolically stable surrogate for a carboxylic acid group, and in materials science as high density energy materials (Hu, et al., 2007, Wang, et al., 2005; Dunica, et al., 1991; Wittenberger et al., 1993). We report here the crystal structure of 2-triphenylmethyl-5-(2-(4-methyl-phenyl)-benzyl)-tetrazole.

The tetrazole moiety is substituted by a triphenyl-methyl group in the position of N2 and a 2-(4-methyl-phenyl)-benzyl group in the position of C1. The bond distances and bond angles of tetrazole functional group are similar to those found in other tetrazole-containing compounds (Wang, et al., 2005; ARP et al., 2000; Hu, et al., 2007). Geometric parameters are in the usual ranges. The tetrazole rings encloses dihedral angles of 45.76 (9)°, 71.44 (8)° and 72.38 (6)° with the three phenyl rings of the triphenylmethyl residue. The dihedral angle between the phenyl ring directly attached to the tetrazole ring is 49.13 (8)° and the dihedral angle between the aromatic rings of the biphenyl moiety is 54.29 (8)°.

Related literature top

For the chemisty of tetrazole, see: ARP et al. (2000); Dunica et al. (1991); Wang et al. (2005); Wittenberger & Donner (1993).

For related literature, see: Hu et al. (2007).

Experimental top

5-(2-(4-methyl-phenyl)-benzyl)-tetrazole was synthesized by reaction of 2-(4-methyl-phenyl)-benzonitrile and sodium azide in the presence of zinc(II) choride according to the procedure described in the literature method (Dunica, et al., 1991). To a toluene solution (50 ml) containing 5-(2-phenyl-benzyl)-tetrazole (112 mg, 0.5 mmol) and chlorotriphenylmethane (161 mg, 0.5 mmol) was added 5 ml of an aqueous solution of NaOH (22 mg, 0.55 mol). The mixture was stirred for 8 h until a precipitation was observed. After filtration and washing with 2 ml e thanol, the crude product was collected and re-crystallized by slowly evaporating its ethyl acetate solution to obtain colorless block shaped crystals.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl).

Structure description top

Studies on compounds containing a tetrazole ring were in recent years highly stimulated by its a wide range of applications in coordination chemistry as ligands, in medicinal chemistry as a metabolically stable surrogate for a carboxylic acid group, and in materials science as high density energy materials (Hu, et al., 2007, Wang, et al., 2005; Dunica, et al., 1991; Wittenberger et al., 1993). We report here the crystal structure of 2-triphenylmethyl-5-(2-(4-methyl-phenyl)-benzyl)-tetrazole.

The tetrazole moiety is substituted by a triphenyl-methyl group in the position of N2 and a 2-(4-methyl-phenyl)-benzyl group in the position of C1. The bond distances and bond angles of tetrazole functional group are similar to those found in other tetrazole-containing compounds (Wang, et al., 2005; ARP et al., 2000; Hu, et al., 2007). Geometric parameters are in the usual ranges. The tetrazole rings encloses dihedral angles of 45.76 (9)°, 71.44 (8)° and 72.38 (6)° with the three phenyl rings of the triphenylmethyl residue. The dihedral angle between the phenyl ring directly attached to the tetrazole ring is 49.13 (8)° and the dihedral angle between the aromatic rings of the biphenyl moiety is 54.29 (8)°.

For the chemisty of tetrazole, see: ARP et al. (2000); Dunica et al. (1991); Wang et al. (2005); Wittenberger & Donner (1993).

For related literature, see: Hu et al. (2007).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 1999).

Figures top
[Figure 1] Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the b axis.
5-(4'-Methylbiphenyl-2-yl)-2-triphenylmethyl-2H-tetrazole top
Crystal data top
C33H26N4F(000) = 1008
Mr = 478.58Dx = 1.230 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 20885 reflections
a = 12.529 (3) Åθ = 3.0–27.5°
b = 12.710 (3) ŵ = 0.07 mm−1
c = 17.707 (7) ÅT = 293 K
β = 113.58 (2)°Blocck, colorless
V = 2584.3 (13) Å30.2 × 0.08 × 0.08 mm
Z = 4
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer		5925 independent reflections
Radiation source: fine-focus sealed tube3802 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = −16→16
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −16→16
Tmin = 0.816, Tmax = 1.000l = −22→22
26288 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0631P)2 + 0.3939P]
where P = (Fo2 + 2Fc2)/3
5925 reflections(Δ/σ)max < 0.001
335 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C33H26N4V = 2584.3 (13) Å3
Mr = 478.58Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.529 (3) ŵ = 0.07 mm−1
b = 12.710 (3) ÅT = 293 K
c = 17.707 (7) Å0.2 × 0.08 × 0.08 mm
β = 113.58 (2)°
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer		5925 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		3802 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 1.000Rint = 0.061
26288 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 1.04Δρmax = 0.20 e Å−3
5925 reflectionsΔρmin = −0.24 e Å−3
335 parameters
Special details top

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) top
xyzUiso*/Ueq
N1−0.14908 (13)−0.37059 (12)−0.19321 (9)0.0394 (4)
N2−0.23004 (12)−0.32303 (11)−0.25762 (8)0.0329 (3)
N3−0.24932 (14)−0.22479 (12)−0.24201 (10)0.0449 (4)
N4−0.17693 (15)−0.20571 (13)−0.16526 (9)0.0483 (4)
C1−0.11690 (15)−0.29541 (14)−0.13699 (10)0.0345 (4)
C2−0.03109 (15)−0.31302 (14)−0.05191 (11)0.0377 (4)
C3−0.06098 (18)−0.28582 (17)0.01298 (12)0.0481 (5)
H3−0.1294−0.24870.00270.058*
C40.0102 (2)−0.31350 (18)0.09289 (12)0.0574 (6)
H4−0.0094−0.29400.13640.069*
C50.1101 (2)−0.37015 (18)0.10759 (12)0.0591 (6)
H50.1558−0.39280.16070.071*
C60.14280 (18)−0.39344 (16)0.04398 (12)0.0503 (5)
H60.2117−0.43010.05510.060*
C70.07479 (16)−0.36322 (14)−0.03679 (11)0.0387 (4)
C80.11918 (15)−0.37666 (14)−0.10199 (11)0.0369 (4)
C90.12820 (16)−0.28925 (15)−0.14663 (11)0.0418 (5)
H90.1028−0.2240−0.13670.050*
C100.17390 (17)−0.29793 (17)−0.20499 (12)0.0470 (5)
H100.1801−0.2381−0.23320.056*
C110.21097 (16)−0.39364 (18)−0.22289 (12)0.0472 (5)
C120.20315 (18)−0.48008 (17)−0.17856 (13)0.0509 (5)
H120.2282−0.5452−0.18910.061*
C130.15893 (17)−0.47219 (15)−0.11889 (13)0.0466 (5)
H130.1557−0.5318−0.08950.056*
C140.2569 (2)−0.4027 (2)−0.28951 (15)0.0754 (7)
H14A0.1971−0.3826−0.34150.113*
H14B0.2799−0.4741−0.29260.113*
H14C0.3229−0.3571−0.27680.113*
C15−0.39586 (15)−0.30452 (14)−0.39002 (10)0.0368 (4)
C16−0.51412 (17)−0.31788 (16)−0.41246 (12)0.0476 (5)
H16−0.5408−0.3732−0.39030.057*
C17−0.5932 (2)−0.2493 (2)−0.46775 (15)0.0654 (7)
H17−0.6726−0.2594−0.48270.078*
C18−0.5559 (2)−0.1677 (2)−0.50024 (15)0.0719 (8)
H18−0.6095−0.1219−0.53710.086*
C19−0.4384 (2)−0.15294 (17)−0.47857 (14)0.0660 (7)
H19−0.4127−0.0969−0.50070.079*
C20−0.35856 (18)−0.22107 (15)−0.42406 (12)0.0496 (5)
H20−0.2794−0.2110−0.41010.060*
C21−0.36339 (14)−0.47084 (14)−0.30304 (11)0.0365 (4)
C22−0.38884 (18)−0.56707 (16)−0.34185 (13)0.0516 (5)
H22−0.3672−0.5810−0.38530.062*
C23−0.4464 (2)−0.6433 (2)−0.31673 (18)0.0745 (7)
H23−0.4638−0.7076−0.34400.089*
C24−0.4779 (2)−0.6253 (2)−0.25255 (18)0.0770 (8)
H24−0.5163−0.6771−0.23590.092*
C25−0.4523 (2)−0.5303 (2)−0.21283 (16)0.0698 (7)
H25−0.4730−0.5177−0.16870.084*
C26−0.39603 (18)−0.45281 (18)−0.23792 (13)0.0528 (5)
H26−0.3800−0.3882−0.21100.063*
C27−0.23312 (15)−0.42746 (13)−0.37810 (11)0.0350 (4)
C28−0.11894 (16)−0.46003 (16)−0.33885 (13)0.0476 (5)
H28−0.0799−0.4502−0.28230.057*
C29−0.06194 (18)−0.50713 (17)−0.38280 (16)0.0586 (6)
H290.0153−0.5278−0.35540.070*
C30−0.1168 (2)−0.52379 (18)−0.46542 (16)0.0600 (6)
H30−0.0782−0.5564−0.49430.072*
C31−0.2307 (2)−0.4914 (2)−0.50548 (15)0.0653 (7)
H31−0.2691−0.5017−0.56200.078*
C32−0.28783 (19)−0.44413 (18)−0.46285 (12)0.0528 (5)
H32−0.3647−0.4228−0.49100.063*
C33−0.30591 (14)−0.38266 (13)−0.33318 (10)0.0323 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0336 (8)0.0400 (9)0.0327 (8)0.0066 (7)0.0009 (7)0.0007 (7)
N20.0294 (7)0.0319 (8)0.0302 (7)0.0043 (6)0.0046 (6)0.0003 (6)
N30.0479 (10)0.0372 (9)0.0380 (9)0.0071 (7)0.0049 (8)−0.0028 (7)
N40.0521 (10)0.0411 (9)0.0363 (9)0.0055 (8)0.0015 (8)−0.0055 (7)
C10.0291 (9)0.0390 (10)0.0319 (9)0.0004 (8)0.0085 (8)−0.0021 (8)
C20.0352 (10)0.0416 (10)0.0302 (9)−0.0024 (8)0.0067 (8)−0.0009 (8)
C30.0425 (11)0.0597 (13)0.0394 (11)−0.0014 (10)0.0136 (9)−0.0063 (9)
C40.0618 (14)0.0740 (15)0.0333 (11)−0.0070 (12)0.0158 (10)−0.0070 (10)
C50.0642 (15)0.0697 (15)0.0292 (11)−0.0002 (12)0.0039 (10)0.0040 (10)
C60.0480 (12)0.0539 (13)0.0365 (11)0.0048 (10)0.0037 (9)0.0019 (9)
C70.0374 (10)0.0380 (10)0.0319 (9)−0.0035 (8)0.0048 (8)−0.0013 (8)
C80.0284 (9)0.0396 (10)0.0329 (9)0.0014 (8)0.0020 (8)−0.0018 (8)
C90.0408 (11)0.0400 (10)0.0389 (10)0.0068 (8)0.0101 (9)−0.0006 (8)
C100.0464 (12)0.0515 (12)0.0398 (11)0.0008 (9)0.0140 (9)0.0052 (9)
C110.0346 (10)0.0639 (14)0.0371 (11)0.0026 (9)0.0080 (9)−0.0078 (10)
C120.0457 (12)0.0464 (12)0.0550 (13)0.0079 (9)0.0143 (10)−0.0102 (10)
C130.0439 (11)0.0388 (11)0.0500 (12)0.0028 (9)0.0114 (10)0.0006 (9)
C140.0712 (17)0.100 (2)0.0639 (16)0.0099 (15)0.0367 (14)−0.0083 (14)
C150.0346 (10)0.0393 (10)0.0274 (9)0.0052 (8)0.0028 (8)−0.0024 (8)
C160.0373 (11)0.0539 (12)0.0399 (11)0.0039 (9)0.0032 (9)−0.0009 (9)
C170.0441 (12)0.0670 (16)0.0613 (15)0.0172 (11)−0.0038 (11)0.0008 (12)
C180.0707 (17)0.0571 (15)0.0525 (14)0.0210 (13)−0.0124 (12)0.0052 (11)
C190.0801 (18)0.0462 (13)0.0487 (13)0.0027 (12)0.0015 (12)0.0124 (10)
C200.0472 (12)0.0462 (11)0.0419 (11)−0.0002 (9)0.0037 (9)0.0076 (9)
C210.0267 (9)0.0406 (10)0.0361 (10)0.0030 (8)0.0061 (8)0.0058 (8)
C220.0507 (12)0.0470 (12)0.0547 (13)−0.0096 (10)0.0187 (11)0.0001 (10)
C230.0743 (17)0.0569 (15)0.0890 (19)−0.0236 (13)0.0292 (16)0.0033 (14)
C240.0580 (16)0.0808 (19)0.0872 (19)−0.0175 (14)0.0237 (15)0.0308 (16)
C250.0540 (14)0.100 (2)0.0607 (15)−0.0031 (14)0.0281 (13)0.0201 (14)
C260.0462 (12)0.0638 (14)0.0501 (12)−0.0015 (10)0.0210 (11)0.0032 (10)
C270.0341 (9)0.0327 (9)0.0372 (10)−0.0033 (7)0.0134 (8)−0.0038 (7)
C280.0360 (10)0.0501 (12)0.0517 (12)0.0012 (9)0.0121 (9)−0.0096 (9)
C290.0392 (12)0.0577 (14)0.0823 (17)−0.0015 (10)0.0278 (12)−0.0174 (12)
C300.0631 (15)0.0585 (14)0.0770 (17)−0.0154 (12)0.0475 (14)−0.0203 (12)
C310.0685 (16)0.0843 (18)0.0489 (13)−0.0081 (13)0.0294 (12)−0.0165 (12)
C320.0494 (12)0.0671 (14)0.0413 (12)0.0015 (10)0.0177 (10)−0.0070 (10)
C330.0263 (8)0.0355 (9)0.0286 (9)0.0010 (7)0.0043 (7)0.0002 (7)
Geometric parameters (Å, º) top
N1—C11.321 (2)C15—C331.537 (2)
N1—N21.3301 (19)C16—C171.387 (3)
N2—N31.322 (2)C16—H160.9300
N2—C331.500 (2)C17—C181.357 (4)
N3—N41.320 (2)C17—H170.9300
N4—C11.347 (2)C18—C191.378 (4)
C1—C21.476 (2)C18—H180.9300
C2—C31.387 (3)C19—C201.382 (3)
C2—C71.398 (3)C19—H190.9300
C3—C41.383 (3)C20—H200.9300
C3—H30.9300C21—C221.376 (3)
C4—C51.376 (3)C21—C261.388 (3)
C4—H40.9300C21—C331.538 (2)
C5—C61.376 (3)C22—C231.383 (3)
C5—H50.9300C22—H220.9300
C6—C71.394 (3)C23—C241.363 (4)
C6—H60.9300C23—H230.9300
C7—C81.478 (3)C24—C251.370 (4)
C8—C131.390 (3)C24—H240.9300
C8—C91.394 (3)C25—C261.384 (3)
C9—C101.372 (3)C25—H250.9300
C9—H90.9300C26—H260.9300
C10—C111.383 (3)C27—C281.380 (3)
C10—H100.9300C27—C321.394 (3)
C11—C121.376 (3)C27—C331.539 (2)
C11—C141.509 (3)C28—C291.385 (3)
C12—C131.379 (3)C28—H280.9300
C12—H120.9300C29—C301.361 (3)
C13—H130.9300C29—H290.9300
C14—H14A0.9600C30—C311.378 (3)
C14—H14B0.9600C30—H300.9300
C14—H14C0.9600C31—C321.370 (3)
C15—C161.382 (3)C31—H310.9300
C15—C201.390 (3)C32—H320.9300
C1—N1—N2102.45 (14)C17—C16—H16119.8
N3—N2—N1112.98 (14)C18—C17—C16120.6 (2)
N3—N2—C33124.06 (13)C18—C17—H17119.7
N1—N2—C33121.93 (14)C16—C17—H17119.7
N4—N3—N2106.32 (14)C17—C18—C19119.8 (2)
N3—N4—C1106.18 (15)C17—C18—H18120.1
N1—C1—N4112.04 (15)C19—C18—H18120.1
N1—C1—C2122.50 (16)C18—C19—C20120.2 (2)
N4—C1—C2125.31 (16)C18—C19—H19119.9
C3—C2—C7120.34 (17)C20—C19—H19119.9
C3—C2—C1118.66 (17)C19—C20—C15120.4 (2)
C7—C2—C1120.83 (16)C19—C20—H20119.8
C4—C3—C2120.5 (2)C15—C20—H20119.8
C4—C3—H3119.8C22—C21—C26118.36 (18)
C2—C3—H3119.8C22—C21—C33121.42 (17)
C5—C4—C3119.5 (2)C26—C21—C33120.15 (17)
C5—C4—H4120.3C21—C22—C23120.6 (2)
C3—C4—H4120.3C21—C22—H22119.7
C4—C5—C6120.27 (19)C23—C22—H22119.7
C4—C5—H5119.9C24—C23—C22120.9 (2)
C6—C5—H5119.9C24—C23—H23119.6
C5—C6—C7121.4 (2)C22—C23—H23119.6
C5—C6—H6119.3C23—C24—C25119.3 (2)
C7—C6—H6119.3C23—C24—H24120.4
C6—C7—C2117.77 (18)C25—C24—H24120.4
C6—C7—C8120.18 (17)C24—C25—C26120.5 (2)
C2—C7—C8121.86 (15)C24—C25—H25119.8
C13—C8—C9117.19 (18)C26—C25—H25119.8
C13—C8—C7123.25 (17)C25—C26—C21120.4 (2)
C9—C8—C7119.47 (16)C25—C26—H26119.8
C10—C9—C8121.07 (18)C21—C26—H26119.8
C10—C9—H9119.5C28—C27—C32117.43 (18)
C8—C9—H9119.5C28—C27—C33124.04 (16)
C9—C10—C11121.53 (19)C32—C27—C33118.34 (16)
C9—C10—H10119.2C27—C28—C29120.7 (2)
C11—C10—H10119.2C27—C28—H28119.7
C12—C11—C10117.66 (19)C29—C28—H28119.7
C12—C11—C14121.4 (2)C30—C29—C28121.2 (2)
C10—C11—C14120.9 (2)C30—C29—H29119.4
C11—C12—C13121.40 (19)C28—C29—H29119.4
C11—C12—H12119.3C29—C30—C31118.7 (2)
C13—C12—H12119.3C29—C30—H30120.6
C12—C13—C8121.12 (19)C31—C30—H30120.6
C12—C13—H13119.4C32—C31—C30120.6 (2)
C8—C13—H13119.4C32—C31—H31119.7
C11—C14—H14A109.5C30—C31—H31119.7
C11—C14—H14B109.5C31—C32—C27121.3 (2)
H14A—C14—H14B109.5C31—C32—H32119.3
C11—C14—H14C109.5C27—C32—H32119.3
H14A—C14—H14C109.5N2—C33—C21106.03 (14)
H14B—C14—H14C109.5N2—C33—C15107.14 (13)
C16—C15—C20118.47 (17)C21—C33—C15112.06 (14)
C16—C15—C33121.99 (17)N2—C33—C27110.65 (13)
C20—C15—C33119.43 (16)C21—C33—C27111.47 (14)
C15—C16—C17120.4 (2)C15—C33—C27109.37 (14)
C15—C16—H16119.8

Experimental details

Crystal data
Chemical formulaC33H26N4
Mr478.58
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.529 (3), 12.710 (3), 17.707 (7)
β (°) 113.58 (2)
V (Å3)2584.3 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.2 × 0.08 × 0.08
Data collection
DiffractometerRigaku Mercury2 (2x2 bin mode)
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.816, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		26288, 5925, 3802
Rint0.061
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.148, 1.04
No. of reflections5925
No. of parameters335
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.20, −0.24

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1999).

 

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