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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3170.
Published online 2010 November 13. doi:  10.1107/S1600536810045630
PMCID: PMC3011511

1,3-Diphenyl-1H-pyrazole-4-carbaldehyde

Abstract

There are four mol­ecules in the asymmetric unit of the title compound, C16H12N2O. The dihedral angle between the phenyl rings in the mol­ecules are 22.2 (2), 22.4 (2), 25.1 (3) and 41.9 (2)°. In the crystal, mol­ecules form dimers due to inter­molecular C—H(...)O hydrogen bonds, which result in one R 2 2(10) and two R 2 1(7) ring motifs. Weak aromatic π–π stacking [centroid–centroid separation = 3.788 (3) Å] and C—H(...)π inter­actions may also consolidate the packing.

Related literature

For background and related structures, see: Ather et al. (2010a [triangle],b [triangle],c [triangle],d [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3170-scheme1.jpg

Experimental

Crystal data

  • C16H12N2O
  • M r = 248.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3170-efi1.jpg
  • a = 10.1367 (9) Å
  • b = 15.5952 (16) Å
  • c = 16.7550 (15) Å
  • α = 95.932 (6)°
  • β = 90.135 (5)°
  • γ = 107.991 (6)°
  • V = 2504.1 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 K
  • 0.32 × 0.16 × 0.14 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.982, T max = 0.988
  • 34716 measured reflections
  • 8912 independent reflections
  • 4643 reflections with I > 2σ(I)
  • R int = 0.092

Refinement

  • R[F 2 > 2σ(F 2)] = 0.090
  • wR(F 2) = 0.259
  • S = 1.04
  • 8912 reflections
  • 671 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.26 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/S1600536810045630/hb5729sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045630/hb5729Isup2.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. The authors also acknowledge the technical support provided by Bana Inter­national, Karachi, Pakistan.

supplementary crystallographic information

Comment

In continuation of our studies of pyrazole derivatives (Ather et al., 2010a,b,c,d), the title compound (I, Fig. 1) is being reported here.

The title compound consists of four molecules in the crystallographic asymmetric unit which differ from each other geometrically. In one molecule, the phenyl rings A (C1—C6), B (C11—C16) and pyrazole moiety C (C7—C11/N1/N2/O1) are planar with r. m. s. deviation of 0.0048, 0.0057 and 0.0178 Å, respectively. The dihedral angle between A/B, A/C and B/C is 41.93 (22), 43.62 (21)° and 1.97 (31)°, respectively. In second molecule, the phenyl rings D (C17—C22), E (C27—C32) and pyrazole moiety F (C23—C26/N3/N4/O2) are planar with r. m. s. deviation of 0.0046, 0.0067 and 0.0330 Å, respectively. The dihedral angle between D/E, D/F and E/F is 22.38 (22), 34.73 (15)° and 17.24 (25)°, respectively. These two molecules form dimers due to intermolecular H-bondings of C—H···O type with two R21(7) and an R22(10) (Table 1, Fig. 2) ring motifs (Bernstein et al., 1995). In third molecule, the phenyl rings G (C33—C38), H (C43—C48) and pyrazole moiety I (C39—C42/N5/N6/O3) are planar with r. m. s. deviation of 0.0099, 0.0021 and 0.0292 Å, respectively. The dihedral angle between G/H, G/I and H/I is 25.07 (28), 27.78 (27)° and 3.81 (33)°, respectively. In fourth molecule, the phenyl rings J (C49—C54), K (C59—C64) and pyrazole moiety L (C55—C58/N7/N8/O4) are planar with r. m. s. deviation of 0.0049, 0.0029 and 0.0339 Å, respectively. The dihedral angle between J/K, J/L and K/L is 22.16 (24), 37.81 (18)° and 22.27 (25)°, respectively. Third and fourth molecules also form dimers due to intermolecular H-bondings of C—H···O type with two R21(7) and an R22(10) (Table 1, Fig. 2). π···π interactions occurs between the pyrazole and benzene rings in each dimer. The separations between the centroids of pyrazole and benzene rings have values of 3.788 (3)Å. These π···π and C—H···π (Table 1) interactions may help to consolidate the packing.

Experimental

Phosphoryl chloride (5 ml) was added drop wise to cold N,N-dimethylformamide (DMF) (15 ml) with continuous stirring at 273–278 K for about 30 min. Acetophenon phenylhydrazone (3.15 g, 15 mmol) was separately dissolved in 5 ml of DMF and was added drop wise to the former cold mixture with the continuous stirring at 273–278 K for an hour. The resulting mixture was further stirred at 323–333 K for 5–6 h and cooled to room temperature. The crude product was poured into crushed ice which resulted into white precipitate. These precipitate were recrystallized in ethanol to obtain colorless needles of (I).

Refinement

The H-atoms were positioned geometrically (C–H = 0.93 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.2 for all H-atoms.

Figures

Fig. 1.
View of the title compound with displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
Packing diagram of the title compound, showing that molecules are dimerized.

Crystal data

C16H12N2OZ = 8
Mr = 248.28F(000) = 1040
Triclinic, P1Dx = 1.317 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1367 (9) ÅCell parameters from 4643 reflections
b = 15.5952 (16) Åθ = 1.2–25.1°
c = 16.7550 (15) ŵ = 0.08 mm1
α = 95.932 (6)°T = 296 K
β = 90.135 (5)°Needle, colorless
γ = 107.991 (6)°0.32 × 0.16 × 0.14 mm
V = 2504.1 (4) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer8912 independent reflections
Radiation source: fine-focus sealed tube4643 reflections with I > 2σ(I)
graphiteRint = 0.092
Detector resolution: 8.3 pixels mm-1θmax = 25.1°, θmin = 1.2°
ω scansh = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −18→18
Tmin = 0.982, Tmax = 0.988l = −20→20
34716 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)] = 0.090H-atom parameters constrained
wR(F2) = 0.259w = 1/[σ2(Fo2) + (0.0599P)2 + 5.7411P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
8912 reflectionsΔρmax = 0.26 e Å3
671 parametersΔρmin = −0.25 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: 0.0043 (7)

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*/Ueq
O10.6324 (5)0.4151 (3)0.5760 (3)0.0706 (16)
N10.8394 (4)0.2089 (3)0.4618 (3)0.0490 (17)
N20.8812 (4)0.2918 (3)0.4319 (2)0.0428 (14)
C10.6788 (5)0.1383 (3)0.5612 (3)0.0446 (17)
C20.7562 (6)0.0892 (3)0.5903 (3)0.0493 (17)
C30.6934 (6)0.0185 (4)0.6334 (3)0.061 (2)
C40.5531 (7)−0.0053 (4)0.6477 (4)0.065 (2)
C50.4758 (7)0.0432 (4)0.6173 (4)0.076 (3)
C60.5391 (6)0.1157 (4)0.5744 (4)0.062 (2)
C70.7457 (5)0.2158 (3)0.5157 (3)0.0436 (17)
C80.7289 (5)0.3034 (3)0.5215 (3)0.0429 (17)
C90.6454 (6)0.3399 (4)0.5749 (3)0.053 (2)
C100.8163 (5)0.3480 (3)0.4661 (3)0.0470 (17)
C110.9833 (5)0.3067 (3)0.3719 (3)0.0437 (17)
C121.0281 (6)0.3897 (4)0.3421 (3)0.055 (2)
C131.1282 (7)0.4025 (4)0.2846 (4)0.068 (2)
C141.1816 (6)0.3351 (4)0.2571 (3)0.061 (2)
C151.1377 (6)0.2537 (4)0.2883 (3)0.061 (2)
C161.03802 (19)0.23882 (12)0.34566 (11)0.0506 (17)
O20.09209 (19)0.44158 (12)0.58037 (11)0.0644 (16)
N30.33043 (19)0.24537 (12)0.48630 (11)0.0433 (16)
N40.36575 (19)0.32530 (12)0.45286 (11)0.0405 (14)
C170.17474 (19)0.17575 (12)0.58564 (11)0.0384 (17)
C180.15852 (19)0.08767 (12)0.55248 (11)0.0502 (19)
C190.1044 (6)0.0147 (4)0.5952 (3)0.055 (2)
C200.0655 (5)0.0274 (3)0.6720 (3)0.0508 (19)
C210.0812 (6)0.1139 (4)0.7069 (3)0.0531 (19)
C220.1365 (5)0.1882 (3)0.6647 (3)0.0484 (17)
C230.2357 (5)0.2514 (3)0.5386 (3)0.0396 (17)
C240.2102 (5)0.3372 (3)0.5403 (3)0.0393 (17)
C250.1049 (5)0.3669 (4)0.5811 (3)0.0469 (17)
C260.2954 (5)0.3806 (3)0.4830 (3)0.0438 (17)
C270.4626 (5)0.3384 (3)0.3899 (3)0.0402 (17)
C280.4935 (6)0.2652 (4)0.3532 (4)0.061 (2)
C290.5852 (7)0.2762 (4)0.2916 (4)0.069 (3)
C300.6470 (6)0.3599 (4)0.2681 (3)0.060 (2)
C310.6156 (6)0.4331 (4)0.3051 (3)0.056 (2)
C320.5242 (5)0.4236 (4)0.3679 (3)0.0517 (19)
O30.4419 (4)0.5710 (3)−0.0773 (3)0.0691 (16)
N50.8514 (4)0.7740 (3)0.0322 (3)0.0502 (17)
N60.8115 (4)0.6927 (3)0.0632 (2)0.0444 (14)
C330.7671 (5)0.8451 (3)−0.0696 (3)0.0460 (17)
C340.6511 (6)0.8609 (4)−0.1006 (3)0.061 (2)
C350.6656 (7)0.9337 (4)−0.1449 (4)0.064 (2)
C360.7956 (7)0.9910 (4)−0.1562 (4)0.066 (3)
C370.9105 (7)0.9786 (4)−0.1242 (4)0.069 (3)
C380.8963 (6)0.9042 (4)−0.0818 (3)0.057 (2)
C390.7537 (5)0.7677 (3)−0.0235 (3)0.0455 (17)
C400.6495 (5)0.6820 (3)−0.0279 (3)0.0435 (17)
C410.5301 (6)0.6432 (4)−0.0824 (3)0.055 (2)
C420.6925 (5)0.6367 (4)0.0296 (3)0.0494 (17)
C430.9001 (5)0.6761 (4)0.1228 (3)0.0466 (17)
C440.8628 (6)0.5944 (4)0.1538 (3)0.059 (2)
C450.9511 (7)0.5794 (5)0.2108 (4)0.069 (3)
C461.0713 (7)0.6456 (5)0.2354 (3)0.066 (3)
C471.1076 (6)0.7277 (4)0.2040 (4)0.063 (2)
C481.0217 (6)0.7430 (4)0.1472 (3)0.054 (2)
O4−0.0749 (4)0.5732 (3)−0.0812 (3)0.0707 (17)
N70.3455 (4)0.7707 (3)0.0177 (3)0.0483 (17)
N80.3045 (4)0.6894 (3)0.0502 (3)0.0463 (17)
C490.2593 (5)0.8414 (3)−0.0837 (3)0.0439 (17)
C500.2157 (5)0.8280 (4)−0.1632 (3)0.0493 (17)
C510.2342 (6)0.9014 (4)−0.2059 (3)0.060 (2)
C520.2942 (6)0.9890 (4)−0.1697 (4)0.065 (2)
C530.3354 (7)1.0013 (4)−0.0901 (4)0.067 (2)
C540.3184 (6)0.9292 (4)−0.0465 (3)0.0577 (19)
C550.2457 (5)0.7637 (3)−0.0361 (3)0.0435 (17)
C560.1416 (5)0.6776 (3)−0.0397 (3)0.0440 (17)
C570.0096 (6)0.6466 (4)−0.0828 (3)0.0523 (19)
C580.1845 (5)0.6332 (3)0.0175 (3)0.0442 (17)
C590.3854 (5)0.6767 (4)0.1152 (3)0.0456 (17)
C600.3706 (6)0.5903 (4)0.1348 (3)0.0546 (19)
C610.4465 (6)0.5811 (4)0.1997 (3)0.060 (2)
C620.5361 (6)0.6533 (4)0.2435 (4)0.065 (2)
C630.5492 (7)0.7385 (4)0.2227 (4)0.075 (3)
C640.4736 (6)0.7498 (4)0.1583 (4)0.066 (2)
H20.850510.103890.580870.0589*
H30.74626−0.014260.653530.0725*
H40.51177−0.053270.677330.0771*
H50.380940.027360.625410.0908*
H60.486830.149080.554690.0745*
H90.596620.303090.612230.0640*
H100.828200.406890.454410.0562*
H120.991970.435960.360190.0659*
H131.159770.458230.264270.0811*
H141.247210.344400.217580.0732*
H151.175380.208020.270710.0726*
H161.008090.183260.366460.0602*
H180.184840.077710.500080.0602*
H190.09443−0.043690.571470.0659*
H200.02851−0.022000.700700.0608*
H210.054530.122680.759420.0637*
H220.148050.246390.689240.0584*
H250.042120.325930.610090.0562*
H260.302790.437680.468080.0525*
H280.452950.207970.369670.0730*
H290.604990.226100.265890.0828*
H300.710080.367230.227170.0725*
H310.655750.490070.288130.0670*
H320.505460.473780.394330.0623*
H340.563040.82262−0.091780.0732*
H350.587680.94349−0.166750.0761*
H360.805141.03927−0.186390.0786*
H370.997771.01937−0.130510.0830*
H380.975020.89429−0.061350.0687*
H410.520260.67578−0.124270.0654*
H420.646840.578380.042220.0596*
H440.780010.549740.137150.0712*
H450.927840.524160.232150.0822*
H461.129590.635300.273720.0791*
H471.189890.772590.221110.0760*
H481.045650.798060.125590.0653*
H500.173920.76955−0.187980.0593*
H510.206030.89206−0.259770.0727*
H520.306421.03845−0.198690.0782*
H530.375661.05987−0.065170.0802*
H540.346150.938880.007460.0697*
H57−0.012060.68650−0.114230.0629*
H580.138510.575310.030840.0530*
H600.310620.539660.104900.0657*
H610.435860.523250.213800.0720*
H620.587530.645590.286710.0772*
H630.609790.789070.252410.0903*
H640.483430.807690.144660.0791*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.099 (3)0.045 (2)0.077 (3)0.034 (2)0.024 (2)0.012 (2)
N10.057 (3)0.042 (3)0.049 (3)0.016 (2)0.005 (2)0.008 (2)
N20.054 (3)0.036 (2)0.039 (2)0.013 (2)0.006 (2)0.0093 (19)
C10.049 (3)0.043 (3)0.040 (3)0.012 (3)0.000 (2)0.004 (2)
C20.051 (3)0.047 (3)0.050 (3)0.015 (3)0.001 (3)0.007 (3)
C30.071 (4)0.059 (4)0.060 (4)0.027 (3)0.006 (3)0.022 (3)
C40.076 (4)0.055 (4)0.066 (4)0.020 (3)0.014 (3)0.024 (3)
C50.053 (4)0.078 (5)0.101 (5)0.019 (3)0.021 (4)0.035 (4)
C60.057 (4)0.063 (4)0.075 (4)0.025 (3)0.012 (3)0.023 (3)
C70.046 (3)0.040 (3)0.044 (3)0.012 (2)−0.001 (2)0.006 (2)
C80.050 (3)0.033 (3)0.047 (3)0.015 (2)0.003 (2)0.004 (2)
C90.066 (4)0.048 (4)0.050 (3)0.021 (3)0.010 (3)0.014 (3)
C100.060 (3)0.040 (3)0.043 (3)0.017 (3)0.002 (3)0.009 (2)
C110.042 (3)0.047 (3)0.040 (3)0.010 (2)−0.003 (2)0.008 (2)
C120.066 (4)0.048 (3)0.057 (4)0.022 (3)0.016 (3)0.017 (3)
C130.072 (4)0.065 (4)0.070 (4)0.020 (3)0.018 (3)0.031 (3)
C140.056 (4)0.071 (4)0.056 (4)0.019 (3)0.012 (3)0.008 (3)
C150.065 (4)0.057 (4)0.056 (4)0.017 (3)0.005 (3)−0.005 (3)
C160.057 (3)0.041 (3)0.050 (3)0.012 (3)0.001 (3)−0.002 (3)
O20.086 (3)0.046 (2)0.070 (3)0.032 (2)0.015 (2)0.010 (2)
N30.050 (3)0.034 (2)0.047 (3)0.0119 (19)0.005 (2)0.013 (2)
N40.050 (3)0.034 (2)0.038 (2)0.012 (2)0.004 (2)0.0101 (19)
C170.043 (3)0.027 (3)0.045 (3)0.010 (2)0.000 (2)0.006 (2)
C180.061 (4)0.043 (3)0.045 (3)0.014 (3)0.004 (3)0.004 (3)
C190.070 (4)0.034 (3)0.060 (4)0.014 (3)0.007 (3)0.008 (3)
C200.058 (3)0.036 (3)0.058 (4)0.010 (3)0.006 (3)0.018 (3)
C210.065 (4)0.049 (3)0.048 (3)0.019 (3)0.014 (3)0.014 (3)
C220.062 (3)0.040 (3)0.044 (3)0.017 (3)0.007 (3)0.005 (2)
C230.042 (3)0.038 (3)0.038 (3)0.010 (2)−0.001 (2)0.008 (2)
C240.044 (3)0.033 (3)0.041 (3)0.011 (2)0.002 (2)0.007 (2)
C250.057 (3)0.043 (3)0.041 (3)0.016 (3)0.005 (3)0.005 (2)
C260.050 (3)0.035 (3)0.048 (3)0.015 (2)0.000 (2)0.006 (2)
C270.044 (3)0.042 (3)0.036 (3)0.014 (2)0.003 (2)0.008 (2)
C280.070 (4)0.044 (3)0.071 (4)0.019 (3)0.023 (3)0.015 (3)
C290.087 (5)0.058 (4)0.067 (4)0.028 (3)0.031 (4)0.009 (3)
C300.062 (4)0.077 (4)0.045 (3)0.023 (3)0.018 (3)0.015 (3)
C310.058 (4)0.053 (4)0.058 (4)0.015 (3)0.011 (3)0.024 (3)
C320.058 (3)0.043 (3)0.054 (4)0.014 (3)0.008 (3)0.010 (3)
O30.072 (3)0.046 (2)0.075 (3)−0.002 (2)−0.005 (2)0.005 (2)
N50.056 (3)0.045 (3)0.047 (3)0.009 (2)0.005 (2)0.014 (2)
N60.050 (3)0.040 (2)0.038 (2)0.005 (2)0.007 (2)0.008 (2)
C330.053 (3)0.042 (3)0.038 (3)0.006 (3)0.006 (2)0.009 (2)
C340.060 (4)0.054 (4)0.063 (4)0.006 (3)0.004 (3)0.014 (3)
C350.072 (4)0.052 (4)0.063 (4)0.014 (3)−0.010 (3)0.007 (3)
C360.084 (5)0.051 (4)0.054 (4)0.006 (3)0.001 (3)0.019 (3)
C370.064 (4)0.058 (4)0.076 (5)−0.002 (3)0.009 (3)0.026 (3)
C380.054 (3)0.056 (4)0.058 (4)0.008 (3)0.002 (3)0.019 (3)
C390.054 (3)0.036 (3)0.045 (3)0.011 (2)0.010 (3)0.007 (2)
C400.056 (3)0.033 (3)0.039 (3)0.009 (2)0.006 (2)0.007 (2)
C410.062 (4)0.047 (3)0.052 (4)0.012 (3)−0.002 (3)0.008 (3)
C420.052 (3)0.041 (3)0.051 (3)0.007 (3)0.006 (3)0.009 (3)
C430.055 (3)0.049 (3)0.036 (3)0.017 (3)0.005 (2)0.003 (2)
C440.062 (4)0.056 (4)0.055 (4)0.010 (3)0.000 (3)0.012 (3)
C450.082 (5)0.072 (4)0.059 (4)0.029 (4)0.001 (4)0.022 (3)
C460.069 (4)0.089 (5)0.046 (4)0.037 (4)−0.007 (3)0.000 (3)
C470.059 (4)0.068 (4)0.059 (4)0.018 (3)−0.004 (3)−0.005 (3)
C480.055 (4)0.056 (4)0.051 (4)0.017 (3)0.003 (3)0.001 (3)
O40.064 (3)0.059 (3)0.072 (3)−0.006 (2)−0.014 (2)0.008 (2)
N70.051 (3)0.045 (3)0.046 (3)0.008 (2)0.002 (2)0.013 (2)
N80.044 (3)0.050 (3)0.042 (3)0.009 (2)0.004 (2)0.010 (2)
C490.044 (3)0.044 (3)0.043 (3)0.013 (2)0.002 (2)0.004 (2)
C500.055 (3)0.046 (3)0.046 (3)0.013 (3)0.001 (3)0.010 (3)
C510.069 (4)0.074 (4)0.040 (3)0.024 (3)−0.004 (3)0.009 (3)
C520.076 (4)0.053 (4)0.069 (4)0.019 (3)0.000 (3)0.021 (3)
C530.088 (5)0.043 (3)0.063 (4)0.011 (3)−0.011 (3)0.002 (3)
C540.075 (4)0.047 (3)0.043 (3)0.009 (3)−0.006 (3)0.000 (3)
C550.047 (3)0.048 (3)0.035 (3)0.015 (3)0.002 (2)0.001 (2)
C560.045 (3)0.040 (3)0.045 (3)0.011 (2)0.005 (2)0.003 (2)
C570.053 (3)0.054 (4)0.043 (3)0.007 (3)−0.001 (3)0.004 (3)
C580.046 (3)0.040 (3)0.041 (3)0.005 (2)0.002 (2)0.005 (2)
C590.041 (3)0.053 (3)0.039 (3)0.008 (3)0.002 (2)0.009 (3)
C600.055 (3)0.045 (3)0.059 (4)0.008 (3)−0.005 (3)0.008 (3)
C610.067 (4)0.058 (4)0.057 (4)0.018 (3)0.001 (3)0.022 (3)
C620.065 (4)0.065 (4)0.060 (4)0.012 (3)−0.009 (3)0.015 (3)
C630.091 (5)0.051 (4)0.071 (5)0.006 (3)−0.032 (4)0.003 (3)
C640.072 (4)0.048 (4)0.067 (4)0.002 (3)−0.021 (3)0.012 (3)

Geometric parameters (Å, °)

O1—C91.218 (8)C20—H200.9300
O2—C251.212 (6)C21—H210.9300
O3—C411.214 (8)C22—H220.9300
O4—C571.202 (8)C25—H250.9300
N1—N21.378 (6)C26—H260.9300
N1—C71.333 (7)C28—H280.9300
N2—C101.336 (7)C29—H290.9300
N2—C111.428 (6)C30—H300.9300
N3—C231.320 (6)C31—H310.9300
N3—N41.366 (3)C32—H320.9300
N4—C261.341 (5)C33—C391.471 (7)
N4—C271.430 (5)C33—C381.379 (8)
N5—C391.333 (7)C33—C341.384 (8)
N5—N61.364 (6)C34—C351.390 (8)
N6—C421.334 (7)C35—C361.371 (10)
N6—C431.437 (7)C36—C371.356 (10)
N7—N81.377 (6)C37—C381.393 (8)
N7—C551.325 (7)C39—C401.419 (7)
N8—C591.428 (7)C40—C411.447 (8)
N8—C581.337 (7)C40—C421.395 (7)
C1—C71.479 (7)C43—C481.375 (8)
C1—C61.374 (8)C43—C441.370 (8)
C1—C21.373 (7)C44—C451.393 (9)
C2—C31.370 (7)C45—C461.361 (10)
C3—C41.383 (10)C46—C471.379 (9)
C4—C51.375 (10)C47—C481.376 (9)
C5—C61.389 (9)C34—H340.9300
C7—C81.422 (7)C35—H350.9300
C8—C101.374 (7)C36—H360.9300
C8—C91.427 (8)C37—H370.9300
C11—C121.379 (7)C38—H380.9300
C11—C161.375 (5)C41—H410.9300
C12—C131.385 (9)C42—H420.9300
C13—C141.365 (9)C44—H440.9300
C14—C151.368 (8)C45—H450.9300
C15—C161.380 (6)C46—H460.9300
C2—H20.9300C47—H470.9300
C3—H30.9300C48—H480.9300
C4—H40.9300C49—C501.377 (7)
C5—H50.9300C49—C541.392 (7)
C6—H60.9300C49—C551.490 (7)
C9—H90.9300C50—C511.377 (8)
C10—H100.9300C51—C521.385 (8)
C12—H120.9300C52—C531.373 (9)
C13—H130.9300C53—C541.371 (8)
C14—H140.9300C55—C561.424 (7)
C15—H150.9300C56—C571.439 (8)
C16—H160.9300C56—C581.381 (7)
C17—C181.387 (3)C59—C601.383 (8)
C17—C221.392 (5)C59—C641.348 (8)
C17—C231.463 (5)C60—C611.375 (8)
C18—C191.376 (6)C61—C621.351 (9)
C19—C201.360 (7)C62—C631.375 (9)
C20—C211.375 (7)C63—C641.379 (9)
C21—C221.388 (7)C50—H500.9300
C23—C241.437 (7)C51—H510.9300
C24—C251.437 (7)C52—H520.9300
C24—C261.379 (7)C53—H530.9300
C27—C281.362 (8)C54—H540.9300
C27—C321.372 (7)C57—H570.9300
C28—C291.379 (10)C58—H580.9300
C29—C301.362 (8)C60—H600.9300
C30—C311.367 (8)C61—H610.9300
C31—C321.393 (8)C62—H620.9300
C18—H180.9300C63—H630.9300
C19—H190.9300C64—H640.9300
N2—N1—C7104.8 (4)C28—C29—H29120.00
N1—N2—C10111.8 (4)C30—C29—H29120.00
N1—N2—C11118.8 (4)C29—C30—H30120.00
C10—N2—C11129.4 (4)C31—C30—H30120.00
N4—N3—C23105.0 (2)C32—C31—H31119.00
N3—N4—C26112.5 (3)C30—C31—H31120.00
N3—N4—C27119.0 (2)C27—C32—H32121.00
C26—N4—C27128.5 (3)C31—C32—H32121.00
N6—N5—C39105.2 (4)C34—C33—C38118.7 (5)
N5—N6—C43118.9 (4)C34—C33—C39121.0 (5)
N5—N6—C42112.5 (4)C38—C33—C39120.3 (5)
C42—N6—C43128.6 (5)C33—C34—C35120.3 (6)
N8—N7—C55104.4 (4)C34—C35—C36119.5 (6)
N7—N8—C58112.6 (4)C35—C36—C37121.2 (6)
C58—N8—C59128.2 (5)C36—C37—C38119.3 (6)
N7—N8—C59119.0 (4)C33—C38—C37120.9 (6)
C2—C1—C7120.1 (5)N5—C39—C33118.9 (4)
C2—C1—C6120.1 (5)N5—C39—C40110.8 (4)
C6—C1—C7119.8 (5)C33—C39—C40130.3 (5)
C1—C2—C3119.5 (6)C39—C40—C41130.2 (5)
C2—C3—C4121.5 (6)C39—C40—C42104.4 (5)
C3—C4—C5118.8 (6)C41—C40—C42125.3 (5)
C4—C5—C6120.1 (6)O3—C41—C40124.5 (5)
C1—C6—C5120.1 (6)N6—C42—C40107.1 (5)
N1—C7—C8110.9 (4)N6—C43—C44119.8 (5)
N1—C7—C1119.7 (4)C44—C43—C48121.3 (5)
C1—C7—C8129.4 (5)N6—C43—C48118.9 (5)
C9—C8—C10126.7 (5)C43—C44—C45118.8 (6)
C7—C8—C10104.7 (4)C44—C45—C46120.1 (6)
C7—C8—C9128.6 (5)C45—C46—C47120.7 (6)
O1—C9—C8125.8 (5)C46—C47—C48119.8 (6)
N2—C10—C8107.9 (4)C43—C48—C47119.4 (5)
N2—C11—C12119.7 (5)C33—C34—H34120.00
C12—C11—C16120.7 (4)C35—C34—H34120.00
N2—C11—C16119.7 (4)C34—C35—H35120.00
C11—C12—C13118.4 (5)C36—C35—H35120.00
C12—C13—C14121.5 (6)C35—C36—H36119.00
C13—C14—C15119.4 (6)C37—C36—H36119.00
C14—C15—C16120.5 (5)C38—C37—H37120.00
C11—C16—C15119.6 (3)C36—C37—H37120.00
C1—C2—H2120.00C33—C38—H38120.00
C3—C2—H2120.00C37—C38—H38120.00
C2—C3—H3119.00C40—C41—H41118.00
C4—C3—H3119.00O3—C41—H41118.00
C5—C4—H4121.00C40—C42—H42127.00
C3—C4—H4121.00N6—C42—H42126.00
C4—C5—H5120.00C45—C44—H44121.00
C6—C5—H5120.00C43—C44—H44121.00
C5—C6—H6120.00C44—C45—H45120.00
C1—C6—H6120.00C46—C45—H45120.00
O1—C9—H9117.00C45—C46—H46120.00
C8—C9—H9117.00C47—C46—H46120.00
N2—C10—H10126.00C48—C47—H47120.00
C8—C10—H10126.00C46—C47—H47120.00
C11—C12—H12121.00C43—C48—H48120.00
C13—C12—H12121.00C47—C48—H48120.00
C12—C13—H13119.00C50—C49—C54119.8 (5)
C14—C13—H13119.00C50—C49—C55121.5 (4)
C13—C14—H14120.00C54—C49—C55118.8 (4)
C15—C14—H14120.00C49—C50—C51119.8 (5)
C16—C15—H15120.00C50—C51—C52120.9 (5)
C14—C15—H15120.00C51—C52—C53118.6 (6)
C15—C16—H16120.00C52—C53—C54121.5 (6)
C11—C16—H16120.00C49—C54—C53119.5 (5)
C18—C17—C22117.6 (2)N7—C55—C49118.2 (4)
C18—C17—C23119.7 (2)N7—C55—C56111.3 (4)
C22—C17—C23122.7 (3)C49—C55—C56130.5 (5)
C17—C18—C19121.6 (3)C55—C56—C57128.9 (5)
C18—C19—C20120.4 (5)C55—C56—C58104.7 (4)
C19—C20—C21119.5 (5)C57—C56—C58125.7 (5)
C20—C21—C22120.8 (5)O4—C57—C56125.1 (5)
C17—C22—C21120.2 (4)N8—C58—C56107.0 (4)
C17—C23—C24129.6 (4)N8—C59—C60120.2 (5)
N3—C23—C24111.1 (4)N8—C59—C64119.3 (5)
N3—C23—C17119.3 (4)C60—C59—C64120.5 (5)
C25—C24—C26126.2 (5)C59—C60—C61118.4 (5)
C23—C24—C26104.1 (4)C60—C61—C62122.1 (6)
C23—C24—C25129.0 (5)C61—C62—C63118.4 (6)
O2—C25—C24124.7 (5)C62—C63—C64120.8 (6)
N4—C26—C24107.3 (4)C59—C64—C63119.8 (6)
N4—C27—C28118.9 (4)C49—C50—H50120.00
C28—C27—C32120.9 (5)C51—C50—H50120.00
N4—C27—C32120.2 (4)C50—C51—H51120.00
C27—C28—C29119.8 (5)C52—C51—H51120.00
C28—C29—C30120.5 (6)C51—C52—H52121.00
C29—C30—C31119.5 (6)C53—C52—H52121.00
C30—C31—C32120.9 (5)C52—C53—H53119.00
C27—C32—C31118.4 (5)C54—C53—H53119.00
C17—C18—H18119.00C49—C54—H54120.00
C19—C18—H18119.00C53—C54—H54120.00
C20—C19—H19120.00O4—C57—H57118.00
C18—C19—H19120.00C56—C57—H57117.00
C19—C20—H20120.00N8—C58—H58127.00
C21—C20—H20120.00C56—C58—H58127.00
C22—C21—H21120.00C59—C60—H60121.00
C20—C21—H21120.00C61—C60—H60121.00
C17—C22—H22120.00C60—C61—H61119.00
C21—C22—H22120.00C62—C61—H61119.00
O2—C25—H25118.00C61—C62—H62121.00
C24—C25—H25118.00C63—C62—H62121.00
N4—C26—H26126.00C62—C63—H63120.00
C24—C26—H26126.00C64—C63—H63120.00
C29—C28—H28120.00C59—C64—H64120.00
C27—C28—H28120.00C63—C64—H64120.00
C7—N1—N2—C100.2 (5)C17—C18—C19—C20−0.2 (7)
C7—N1—N2—C11179.9 (4)C18—C19—C20—C21−0.3 (8)
N2—N1—C7—C1−179.3 (4)C19—C20—C21—C22−0.2 (9)
N2—N1—C7—C8−1.0 (6)C20—C21—C22—C171.1 (8)
N1—N2—C10—C80.7 (6)N3—C23—C24—C25171.9 (5)
C11—N2—C10—C8−178.9 (5)C17—C23—C24—C25−9.1 (9)
N1—N2—C11—C12−179.0 (5)C17—C23—C24—C26−179.5 (5)
N1—N2—C11—C16−0.4 (6)N3—C23—C24—C261.5 (6)
C10—N2—C11—C120.6 (8)C26—C24—C25—O2−12.8 (8)
C10—N2—C11—C16179.3 (4)C23—C24—C26—N4−1.4 (5)
N4—N3—C23—C24−0.9 (4)C23—C24—C25—O2178.7 (5)
N4—N3—C23—C17180.0 (3)C25—C24—C26—N4−172.2 (5)
C23—N3—N4—C260.0 (4)C28—C27—C32—C312.2 (8)
C23—N3—N4—C27−176.8 (3)N4—C27—C28—C29179.1 (5)
C27—N4—C26—C24177.4 (4)N4—C27—C32—C31−178.6 (4)
C26—N4—C27—C28−162.0 (5)C32—C27—C28—C29−1.7 (9)
N3—N4—C27—C2814.2 (6)C27—C28—C29—C301.2 (10)
N3—N4—C27—C32−165.0 (4)C28—C29—C30—C31−1.2 (10)
N3—N4—C26—C241.0 (5)C29—C30—C31—C321.8 (9)
C26—N4—C27—C3218.8 (7)C30—C31—C32—C27−2.3 (8)
C39—N5—N6—C42−0.6 (6)C38—C33—C34—C351.7 (8)
N6—N5—C39—C400.5 (6)C34—C33—C38—C370.2 (8)
N6—N5—C39—C33−179.3 (4)C39—C33—C38—C37−179.0 (5)
C39—N5—N6—C43176.9 (4)C39—C33—C34—C35−179.2 (5)
N5—N6—C43—C480.6 (7)C38—C33—C39—C40−152.4 (5)
N5—N6—C43—C44−179.1 (5)C38—C33—C39—N527.4 (7)
C42—N6—C43—C48177.7 (5)C34—C33—C39—N5−151.8 (5)
C42—N6—C43—C44−1.9 (8)C34—C33—C39—C4028.5 (8)
C43—N6—C42—C40−176.8 (5)C33—C34—C35—C36−1.4 (9)
N5—N6—C42—C400.5 (6)C34—C35—C36—C37−0.7 (10)
C55—N7—N8—C580.7 (6)C35—C36—C37—C382.6 (10)
C55—N7—N8—C59−175.6 (5)C36—C37—C38—C33−2.3 (9)
N8—N7—C55—C56−1.1 (6)N5—C39—C40—C41−175.4 (5)
N8—N7—C55—C49−179.3 (4)C33—C39—C40—C42179.5 (5)
C58—N8—C59—C6021.8 (8)N5—C39—C40—C42−0.2 (6)
N7—N8—C59—C60−162.6 (5)C33—C39—C40—C414.3 (9)
N7—N8—C59—C6419.0 (8)C39—C40—C41—O3−174.8 (6)
N7—N8—C58—C560.1 (6)C41—C40—C42—N6175.3 (5)
C58—N8—C59—C64−156.6 (6)C42—C40—C41—O310.9 (9)
C59—N8—C58—C56175.9 (5)C39—C40—C42—N6−0.2 (6)
C6—C1—C7—C843.6 (8)C44—C43—C48—C47−0.1 (9)
C7—C1—C2—C3179.0 (5)N6—C43—C48—C47−179.7 (5)
C2—C1—C7—C8−136.3 (6)N6—C43—C44—C45179.2 (5)
C6—C1—C7—N1−138.5 (6)C48—C43—C44—C45−0.4 (9)
C6—C1—C2—C3−0.9 (8)C43—C44—C45—C460.7 (9)
C2—C1—C6—C50.1 (9)C44—C45—C46—C47−0.5 (10)
C2—C1—C7—N141.7 (7)C45—C46—C47—C480.0 (10)
C7—C1—C6—C5−179.8 (5)C46—C47—C48—C430.3 (9)
C1—C2—C3—C40.7 (8)C54—C49—C50—C511.7 (8)
C2—C3—C4—C50.4 (9)C55—C49—C50—C51−177.9 (5)
C3—C4—C5—C6−1.2 (10)C50—C49—C54—C53−1.5 (9)
C4—C5—C6—C11.0 (10)C55—C49—C54—C53178.1 (6)
C1—C7—C8—C10179.5 (5)C50—C49—C55—N7143.5 (5)
N1—C7—C8—C9−176.1 (5)C50—C49—C55—C56−34.3 (8)
C1—C7—C8—C92.1 (9)C54—C49—C55—N7−36.1 (7)
N1—C7—C8—C101.4 (6)C54—C49—C55—C56146.2 (6)
C10—C8—C9—O14.9 (10)C49—C50—C51—C52−1.1 (9)
C9—C8—C10—N2176.3 (5)C50—C51—C52—C530.2 (10)
C7—C8—C9—O1−178.2 (6)C51—C52—C53—C540.1 (10)
C7—C8—C10—N2−1.2 (6)C52—C53—C54—C490.6 (10)
N2—C11—C12—C13179.3 (5)N7—C55—C56—C57172.2 (5)
C12—C11—C16—C15−0.7 (6)N7—C55—C56—C581.2 (6)
N2—C11—C16—C15−179.3 (4)C49—C55—C56—C57−10.0 (9)
C16—C11—C12—C130.7 (8)C49—C55—C56—C58179.1 (5)
C11—C12—C13—C140.4 (9)C55—C56—C57—O4−177.9 (6)
C12—C13—C14—C15−1.5 (10)C58—C56—C57—O4−8.7 (9)
C13—C14—C15—C161.5 (8)C55—C56—C58—N8−0.7 (6)
C14—C15—C16—C11−0.4 (7)C57—C56—C58—N8−172.1 (5)
C23—C17—C18—C19178.6 (4)N8—C59—C60—C61−177.6 (5)
C18—C17—C22—C21−1.5 (6)C64—C59—C60—C610.8 (9)
C22—C17—C18—C191.1 (5)N8—C59—C64—C63178.1 (6)
C22—C17—C23—N3145.3 (4)C60—C59—C64—C63−0.3 (9)
C22—C17—C23—C24−33.7 (7)C59—C60—C61—C62−1.2 (9)
C18—C17—C23—C24149.0 (4)C60—C61—C62—C631.1 (10)
C23—C17—C22—C21−178.9 (5)C61—C62—C63—C64−0.6 (10)
C18—C17—C23—N3−32.1 (5)C62—C63—C64—C590.2 (10)

Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C17–C22 ring.
D—H···AD—HH···AD···AD—H···A
C10—H10···O2i0.932.383.299 (5)168
C12—H12···O2i0.932.453.373 (6)175
C26—H26···O1i0.932.383.298 (6)169
C32—H32···O1i0.932.553.423 (7)156
C42—H42···O3ii0.932.363.287 (7)173
C44—H44···O3ii0.932.573.495 (8)175
C58—H58···O4iii0.932.443.353 (6)165
C60—H60···O4iii0.932.493.330 (8)150
C2—H2···Cg5iv0.932.863.689 (7)149

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5729).

References

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