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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2569.
Published online 2010 September 15. doi:  10.1107/S1600536810035713
PMCID: PMC2983162

2-(4-Chloro­phen­yl)-4-[1-(4-chloro­phen­yl)-3-methyl-1H-pyrazol-5-yl]-5-methyl-1H-pyrazol-3(2H)-one

Abstract

The title compound, C20H16Cl2N4O, has two mol­ecules in the asymmetric unit. The two five-membered rings form a dihedral angle of 54.2 (3)° in one mol­ecule and 56.8 (3)° in the other independent mol­ecule. The amino group of the dihydro­pyrazolone unit of one mol­ecule acts as a hydrogen-bond donor to the carbonyl group of the dihydro­pyrazolone system of the other mol­ecule. The resulting N—H(...)O hydrogen bonds generate a chain running along the c axis. The crystal selected was a pseudo-merohedral twin with a 44.9 (3)% twin component.

Related literature

For the crystal structure of the parent compound without the chlorine-atom substitutents, see: Bertolasi et al. (1995 [triangle]); Kumar et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2569-scheme1.jpg

Experimental

Crystal data

  • C20H16Cl2N4O
  • M r = 399.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2569-efi1.jpg
  • a = 7.8095 (2) Å
  • b = 20.2827 (6) Å
  • c = 11.5304 (3) Å
  • β = 90.075 (2)°
  • V = 1826.39 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.37 mm−1
  • T = 100 K
  • 0.32 × 0.08 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.890, T max = 0.985
  • 14055 measured reflections
  • 6328 independent reflections
  • 5280 reflections with I > 2σ(I)
  • R int = 0.090

Refinement

  • R[F 2 > 2σ(F 2)] = 0.081
  • wR(F 2) = 0.207
  • S = 1.03
  • 6328 reflections
  • 445 parameters
  • 31 restraints
  • H-atom parameters constrained
  • Δρmax = 0.85 e Å−3
  • Δρmin = −0.65 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3812 Friedel pairs
  • Flack parameter: 0.0 (1)

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035713/im2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035713/im2224Isup2.hkl

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

Acknowledgments

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We are interested in studying the biological properties of derivatives of 1-phenyl-3-methyl-4(1-phenyl-3-methyl-1H-pyrazol-5-yl)-2H-3-pyrazolin-5-one. The crystal structure of the parent compound was reported in the context of understanding how amino as well as carbonyl groups connected to a π-system influence hydrogen bonding (Bertolasi et al., 1995; Kumar et al., 1995). The chloro-substituted compound (Scheme I, Fig. 1) crystallizes with two independant molecules in the asymmetric unit that display similar bond dimensions. Molecules are linked by N—H···O hydrogen bonds to generate a linear chain running along the c-axis of the monoclinic unit cell (Fig. 2).

The crystal studied is a racemic twin; the monoclinic unit cell, having a β-angle that is almost a right angle, emulates an orthorhombic unit cell.

Experimental

1-[1-(4-Chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]butane-1,3-dione (0.20 g, 0.7 mmol) and 4-chlorophenylhydrazine (0.20 g, 0.14 mmol) were heated in dimethoxyethane and dilute hydrochloric acid for 4 h (synthesis of the dione will be reported elsewhere.). The reaction was quenched by 1 M potassium carbonate. The aqueous layer was extracted with ethyl acetate. The combined organic phases were concentrated and the crude product recrystallized from dichloromethane to give 0.19 g of the title compound in 70% yield.

Refinement

The refinement initially converged at an R index of about 20%. As the space group is not a centric space group, the structure was refined as a combination of general and racemic twinning, with the TWIN law of (-1 0 0 0 - 1 0 0 0 1) being used. The refinement on 3812 Friedel pairs gave a Flack parameter of 0.029; the portion of the twin component was 44.9%.

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). Amino H-atoms were similarly generated.

Some of the diffraction spots of the second and third domain are quite close to those of the main domain affecting the refinement so that the ellipsoids of some atoms are observed to be significantly elongated. The anisotropic temperature factors of five carbon atoms (C1, C3, C10, C21 and C21) were therefore tightly restrained to be nearly isotropic. We have used a very tight restraint (ISOR 0.005). Even with ISOR 0.01, these atoms turn non-positive definite. Phenylene rings were restrained as rigid hexagons with carbon carbon bonds of 1.39 Å each.

A somewhat large WGHT was used that is almost the default value; the Goodness-of-Fit was not much different from the default value of 1.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) plot of the two molecules of C20H16ClN4O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Thermal ellipsoid plot (Barbour, 2001) of the hydrogen-bonded chain structure.

Crystal data

C20H16Cl2N4OF(000) = 824
Mr = 399.27Dx = 1.452 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2188 reflections
a = 7.8095 (2) Åθ = 2.6–22.1°
b = 20.2827 (6) ŵ = 0.37 mm1
c = 11.5304 (3) ÅT = 100 K
β = 90.075 (2)°Plate, colorless
V = 1826.39 (9) Å30.32 × 0.08 × 0.04 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer6328 independent reflections
Radiation source: fine-focus sealed tube5280 reflections with I > 2σ(I)
graphiteRint = 0.090
ω scansθmax = 25.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.890, Tmax = 0.985k = −24→24
14055 measured reflectionsl = −13→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.081H-atom parameters constrained
wR(F2) = 0.207w = 1/[σ2(Fo2) + (0.1148P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6328 reflectionsΔρmax = 0.85 e Å3
445 parametersΔρmin = −0.65 e Å3
31 restraintsAbsolute structure: Flack (1983), 3812 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.0 (1)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.7639 (3)0.50000 (12)1.1115 (2)0.0254 (5)
Cl20.2433 (3)0.73300 (12)0.5009 (2)0.0276 (5)
Cl30.6738 (3)0.50272 (11)0.6071 (2)0.0279 (5)
Cl41.3049 (3)0.73174 (12)−0.0046 (2)0.0236 (5)
O10.8167 (9)0.8010 (3)0.8422 (5)0.0189 (14)
O20.7406 (9)0.8012 (3)0.3352 (6)0.0244 (16)
N10.7364 (10)0.7877 (4)1.0350 (6)0.0149 (16)
N20.6547 (9)0.8275 (4)1.1178 (7)0.0196 (16)
H20.62870.81631.18930.023*
N30.6031 (10)0.9429 (4)0.7631 (7)0.0177 (16)
N40.6322 (10)1.0009 (4)0.7076 (7)0.0225 (17)
N50.8150 (10)0.7850 (4)0.5275 (6)0.0166 (17)
N60.8991 (10)0.8225 (4)0.6125 (6)0.0188 (16)
H60.92500.80890.68290.023*
N70.9652 (10)0.9418 (3)0.2675 (7)0.0172 (16)
N80.9481 (10)1.0025 (4)0.2169 (7)0.0218 (17)
C10.7499 (13)0.8238 (5)0.9318 (8)0.021 (2)
C20.6771 (12)0.8870 (5)0.9542 (8)0.0174 (19)
C30.6235 (12)0.8862 (4)1.0671 (8)0.0157 (19)
C40.5388 (13)0.9395 (4)1.1409 (8)0.024 (2)
H4A0.43540.92151.17720.036*
H4B0.50790.97701.09160.036*
H4C0.61880.95401.20120.036*
C50.7512 (8)0.7199 (2)1.0537 (5)0.0164 (19)
C60.8415 (7)0.6801 (3)0.9770 (4)0.018 (2)
H6A0.89920.69930.91280.022*
C70.8476 (7)0.6124 (2)0.9944 (4)0.0188 (19)
H70.90930.58520.94200.023*
C80.7633 (8)0.5844 (2)1.0884 (5)0.020 (2)
C90.6729 (7)0.6242 (3)1.1650 (4)0.022 (2)
H90.61530.60511.22920.026*
C100.6669 (7)0.6920 (2)1.1476 (4)0.0184 (19)
H100.60510.71921.20000.022*
C110.6723 (11)0.9425 (4)0.8734 (8)0.0156 (19)
C120.7453 (12)1.0042 (5)0.8902 (8)0.021 (2)
H120.80111.02030.95770.026*
C130.7176 (13)1.0376 (4)0.7838 (8)0.020 (2)
C140.7813 (15)1.1062 (5)0.7499 (9)0.031 (3)
H14A0.73851.11740.67250.047*
H14B0.90681.10650.74950.047*
H14C0.73951.13860.80610.047*
C150.5111 (7)0.8935 (2)0.7027 (5)0.019 (2)
C160.5119 (7)0.8944 (3)0.5821 (5)0.025 (2)
H160.57090.92840.54200.030*
C170.4262 (8)0.8457 (3)0.5203 (4)0.020 (2)
H170.42680.84630.43790.024*
C180.3398 (8)0.7959 (3)0.5790 (5)0.022 (2)
C190.3391 (8)0.7950 (2)0.6995 (5)0.022 (2)
H190.28000.76100.73960.027*
C200.4247 (8)0.8437 (3)0.7614 (4)0.020 (2)
H200.42420.84310.84370.024*
C210.8081 (12)0.8223 (4)0.4247 (7)0.0133 (18)
C220.8897 (13)0.8838 (4)0.4551 (8)0.020 (2)
C230.9332 (12)0.8821 (4)0.5691 (8)0.017 (2)
C241.0216 (13)0.9322 (4)0.6447 (8)0.023 (2)
H24A0.98020.92800.72450.034*
H24B0.99670.97660.61580.034*
H24C1.14550.92460.64290.034*
C250.7768 (8)0.7182 (2)0.5441 (5)0.0152 (19)
C260.8020 (8)0.6725 (3)0.4558 (4)0.028 (2)
H260.84120.68680.38190.034*
C270.7700 (9)0.6061 (2)0.4755 (4)0.025 (2)
H270.78720.57490.41520.030*
C280.7126 (9)0.5852 (2)0.5836 (5)0.019 (2)
C290.6874 (9)0.6308 (3)0.6718 (4)0.024 (2)
H290.64820.61660.74570.029*
C300.7194 (8)0.6973 (3)0.6521 (4)0.024 (2)
H300.70220.72850.71240.029*
C310.8965 (12)0.9420 (5)0.3771 (8)0.019 (2)
C320.8358 (13)1.0035 (5)0.3962 (8)0.024 (2)
H320.78261.01890.46510.029*
C330.8663 (12)1.0403 (5)0.2950 (8)0.023 (2)
C340.8278 (15)1.1108 (5)0.2670 (9)0.029 (2)
H34A0.82281.11650.18270.044*
H34B0.91811.13910.29910.044*
H34C0.71741.12310.30110.044*
C351.0548 (7)0.8927 (2)0.2047 (4)0.0170 (19)
C361.0520 (7)0.8956 (2)0.0843 (5)0.020 (2)
H360.99620.93120.04620.024*
C371.1310 (8)0.8465 (3)0.0195 (3)0.021 (2)
H371.12900.8484−0.06280.026*
C381.2127 (7)0.7945 (3)0.0752 (4)0.0174 (19)
C391.2155 (8)0.7916 (2)0.1957 (5)0.026 (2)
H391.27140.75600.23370.031*
C401.1366 (9)0.8407 (3)0.2604 (3)0.021 (2)
H401.13850.83870.34270.025*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0274 (13)0.0186 (11)0.0301 (14)−0.0004 (12)0.0030 (11)0.0032 (11)
Cl20.0312 (13)0.0280 (12)0.0238 (12)−0.0023 (13)−0.0073 (12)−0.0023 (12)
Cl30.0309 (14)0.0219 (12)0.0307 (13)−0.0064 (13)−0.0026 (11)0.0031 (11)
Cl40.0220 (12)0.0288 (11)0.0202 (11)0.0040 (12)0.0030 (11)−0.0016 (10)
O10.021 (3)0.026 (3)0.010 (3)0.002 (3)0.000 (3)0.001 (3)
O20.033 (4)0.024 (4)0.016 (3)−0.002 (3)0.001 (3)−0.003 (3)
N10.016 (4)0.019 (4)0.010 (4)0.006 (3)−0.002 (3)−0.004 (3)
N20.018 (4)0.027 (4)0.014 (4)0.001 (3)0.006 (3)−0.005 (3)
N30.010 (4)0.021 (4)0.022 (4)0.002 (3)0.005 (3)0.001 (4)
N40.023 (4)0.019 (4)0.025 (4)0.001 (4)−0.008 (3)0.001 (4)
N50.021 (4)0.020 (4)0.008 (4)0.007 (3)−0.004 (3)−0.003 (3)
N60.022 (4)0.029 (4)0.006 (4)0.001 (3)−0.006 (3)−0.004 (3)
N70.012 (4)0.018 (4)0.022 (4)0.002 (3)0.001 (3)−0.007 (3)
N80.017 (4)0.021 (4)0.027 (4)−0.001 (4)−0.001 (3)0.001 (4)
C10.028 (4)0.023 (4)0.013 (4)−0.005 (3)−0.003 (3)0.002 (3)
C20.011 (5)0.026 (5)0.015 (4)−0.004 (4)−0.002 (4)0.002 (4)
C30.013 (4)0.019 (3)0.015 (4)0.000 (3)0.007 (3)−0.003 (3)
C40.022 (5)0.024 (5)0.025 (5)0.002 (4)0.004 (4)−0.002 (4)
C50.014 (4)0.027 (5)0.008 (4)−0.003 (4)0.001 (3)−0.003 (4)
C60.017 (5)0.028 (5)0.010 (5)0.003 (4)−0.003 (4)−0.006 (4)
C70.011 (4)0.031 (5)0.014 (4)−0.001 (4)0.001 (4)0.001 (4)
C80.005 (4)0.036 (5)0.018 (5)−0.002 (4)0.000 (4)−0.009 (4)
C90.017 (5)0.028 (5)0.021 (5)0.005 (4)0.000 (4)−0.005 (4)
C100.013 (3)0.028 (4)0.014 (4)−0.002 (3)0.005 (3)−0.001 (3)
C110.014 (5)0.023 (5)0.010 (4)0.001 (4)0.003 (4)0.001 (4)
C120.023 (5)0.026 (5)0.015 (5)0.009 (5)0.008 (4)0.003 (4)
C130.027 (5)0.015 (4)0.019 (5)0.000 (4)0.001 (4)−0.003 (4)
C140.040 (7)0.023 (5)0.031 (6)−0.001 (4)−0.009 (5)0.001 (4)
C150.030 (6)0.015 (4)0.013 (4)0.010 (4)0.009 (4)0.006 (4)
C160.023 (5)0.030 (5)0.021 (5)0.002 (4)−0.005 (4)0.008 (5)
C170.018 (5)0.034 (5)0.007 (4)0.006 (4)0.003 (4)0.001 (4)
C180.022 (5)0.028 (5)0.015 (5)−0.002 (4)−0.005 (4)0.003 (4)
C190.020 (5)0.019 (4)0.027 (5)−0.004 (4)−0.002 (4)0.005 (4)
C200.013 (5)0.032 (5)0.015 (5)0.003 (4)0.001 (4)−0.002 (4)
C210.017 (4)0.015 (3)0.008 (3)0.002 (3)0.004 (3)0.000 (3)
C220.025 (6)0.011 (4)0.023 (5)0.008 (4)0.009 (4)0.004 (4)
C230.019 (5)0.010 (4)0.023 (5)0.006 (4)−0.004 (4)0.006 (4)
C240.020 (5)0.038 (6)0.011 (5)−0.003 (4)−0.002 (4)−0.005 (4)
C250.018 (4)0.017 (4)0.011 (3)0.005 (3)−0.001 (3)0.005 (3)
C260.031 (6)0.026 (6)0.028 (6)0.008 (4)0.000 (5)−0.004 (4)
C270.028 (5)0.025 (5)0.022 (5)0.006 (4)0.005 (4)0.001 (4)
C280.017 (5)0.025 (5)0.017 (5)0.004 (4)−0.002 (4)0.003 (4)
C290.028 (5)0.024 (5)0.021 (5)0.003 (4)0.002 (4)0.000 (4)
C300.016 (5)0.039 (6)0.017 (5)−0.001 (4)0.004 (4)−0.012 (4)
C310.019 (5)0.027 (5)0.012 (5)−0.004 (4)−0.004 (4)0.005 (4)
C320.032 (5)0.024 (5)0.015 (5)0.007 (5)−0.002 (4)−0.004 (4)
C330.017 (5)0.033 (5)0.019 (5)−0.008 (4)0.003 (4)−0.009 (4)
C340.038 (6)0.022 (5)0.027 (6)0.005 (5)0.000 (5)0.001 (4)
C350.015 (5)0.024 (5)0.012 (4)0.000 (4)0.008 (4)−0.005 (4)
C360.020 (5)0.022 (5)0.018 (5)−0.006 (4)−0.001 (4)0.003 (4)
C370.015 (5)0.031 (5)0.018 (5)−0.003 (4)0.006 (4)0.002 (4)
C380.010 (4)0.027 (5)0.015 (5)−0.001 (4)0.003 (3)0.000 (4)
C390.027 (6)0.032 (6)0.018 (5)0.006 (5)0.000 (4)0.004 (4)
C400.030 (6)0.026 (5)0.008 (4)0.011 (4)0.001 (4)0.003 (4)

Geometric parameters (Å, °)

Cl1—C81.732 (5)C14—H14B0.9800
Cl2—C181.734 (5)C14—H14C0.9800
Cl3—C281.722 (5)C15—C161.3900
Cl4—C381.728 (4)C15—C201.3900
O1—C11.247 (11)C16—C171.3900
O2—C211.234 (10)C16—H160.9500
N1—C51.395 (9)C17—C181.3900
N1—C11.401 (12)C17—H170.9500
N1—N21.405 (10)C18—C191.3900
N2—C31.348 (12)C19—C201.3900
N2—H20.8800C19—H190.9500
N3—N41.358 (11)C20—H200.9500
N3—C111.381 (12)C21—C221.445 (13)
N3—C151.417 (8)C22—C231.358 (12)
N4—C131.330 (12)C22—C311.485 (12)
N5—C251.402 (9)C23—C241.506 (12)
N5—N61.403 (10)C24—H24A0.9800
N5—C211.407 (11)C24—H24B0.9800
N6—C231.337 (11)C24—H24C0.9800
N6—H60.8800C25—C261.3900
N7—N81.368 (11)C25—C301.3900
N7—C311.373 (12)C26—C271.3900
N7—C351.416 (8)C26—H260.9500
N8—C331.345 (12)C27—C281.3900
C1—C21.426 (14)C27—H270.9500
C2—C31.367 (12)C28—C291.3900
C2—C111.462 (13)C29—C301.3900
C3—C41.527 (12)C29—H290.9500
C4—H4A0.9800C30—H300.9500
C4—H4B0.9800C31—C321.352 (14)
C4—H4C0.9800C32—C331.406 (14)
C5—C61.3900C32—H320.9500
C5—C101.3900C33—C341.496 (13)
C6—C71.3900C34—H34A0.9800
C6—H6A0.9500C34—H34B0.9800
C7—C81.3900C34—H34C0.9800
C7—H70.9500C35—C361.3900
C8—C91.3900C35—C401.3900
C9—C101.3900C36—C371.3900
C9—H90.9500C36—H360.9500
C10—H100.9500C37—C381.3900
C11—C121.387 (15)C37—H370.9500
C12—C131.418 (13)C38—C391.3900
C12—H120.9500C39—C401.3900
C13—C141.527 (13)C39—H390.9500
C14—H14A0.9800C40—H400.9500
C5—N1—C1129.8 (7)C16—C17—H17120.0
C5—N1—N2119.9 (7)C17—C18—C19120.0
C1—N1—N2108.1 (7)C17—C18—Cl2119.5 (3)
C3—N2—N1107.2 (7)C19—C18—Cl2120.4 (3)
C3—N2—H2126.4C18—C19—C20120.0
N1—N2—H2126.4C18—C19—H19120.0
N4—N3—C11111.9 (8)C20—C19—H19120.0
N4—N3—C15117.8 (7)C19—C20—C15120.0
C11—N3—C15130.3 (7)C19—C20—H20120.0
C13—N4—N3104.9 (7)C15—C20—H20120.0
C25—N5—N6121.9 (6)O2—C21—N5122.3 (8)
C25—N5—C21128.8 (6)O2—C21—C22133.6 (8)
N6—N5—C21108.4 (7)N5—C21—C22104.1 (7)
C23—N6—N5108.7 (7)C23—C22—C21108.8 (8)
C23—N6—H6125.6C23—C22—C31126.7 (9)
N5—N6—H6125.6C21—C22—C31123.8 (8)
N8—N7—C31110.6 (7)N6—C23—C22109.7 (8)
N8—N7—C35117.5 (7)N6—C23—C24119.0 (8)
C31—N7—C35131.8 (7)C22—C23—C24131.1 (9)
C33—N8—N7105.9 (8)C23—C24—H24A109.5
O1—C1—N1122.8 (8)C23—C24—H24B109.5
O1—C1—C2130.6 (9)H24A—C24—H24B109.5
N1—C1—C2106.6 (8)C23—C24—H24C109.5
C3—C2—C1106.5 (8)H24A—C24—H24C109.5
C3—C2—C11127.5 (9)H24B—C24—H24C109.5
C1—C2—C11125.9 (8)C26—C25—C30120.0
N2—C3—C2111.6 (8)C26—C25—N5120.9 (5)
N2—C3—C4117.5 (8)C30—C25—N5119.0 (4)
C2—C3—C4130.9 (9)C25—C26—C27120.0
C3—C4—H4A109.5C25—C26—H26120.0
C3—C4—H4B109.5C27—C26—H26120.0
H4A—C4—H4B109.5C28—C27—C26120.0
C3—C4—H4C109.5C28—C27—H27120.0
H4A—C4—H4C109.5C26—C27—H27120.0
H4B—C4—H4C109.5C29—C28—C27120.0
C6—C5—C10120.0C29—C28—Cl3120.4 (3)
C6—C5—N1121.0 (4)C27—C28—Cl3119.6 (3)
C10—C5—N1118.9 (4)C28—C29—C30120.0
C5—C6—C7120.0C28—C29—H29120.0
C5—C6—H6A120.0C30—C29—H29120.0
C7—C6—H6A120.0C29—C30—C25120.0
C6—C7—C8120.0C29—C30—H30120.0
C6—C7—H7120.0C25—C30—H30120.0
C8—C7—H7120.0C32—C31—N7106.9 (8)
C7—C8—C9120.0C32—C31—C22128.4 (9)
C7—C8—Cl1121.5 (3)N7—C31—C22124.7 (8)
C9—C8—Cl1118.5 (3)C31—C32—C33107.2 (9)
C10—C9—C8120.0C31—C32—H32126.4
C10—C9—H9120.0C33—C32—H32126.4
C8—C9—H9120.0N8—C33—C32109.5 (9)
C9—C10—C5120.0N8—C33—C34119.8 (9)
C9—C10—H10120.0C32—C33—C34130.7 (9)
C5—C10—H10120.0C33—C34—H34A109.5
N3—C11—C12106.5 (8)C33—C34—H34B109.5
N3—C11—C2126.9 (8)H34A—C34—H34B109.5
C12—C11—C2126.5 (8)C33—C34—H34C109.5
C11—C12—C13104.4 (8)H34A—C34—H34C109.5
C11—C12—H12127.8H34B—C34—H34C109.5
C13—C12—H12127.8C36—C35—C40120.0
N4—C13—C12112.3 (8)C36—C35—N7118.3 (5)
N4—C13—C14120.3 (8)C40—C35—N7121.6 (5)
C12—C13—C14127.4 (9)C35—C36—C37120.0
C13—C14—H14A109.5C35—C36—H36120.0
C13—C14—H14B109.5C37—C36—H36120.0
H14A—C14—H14B109.5C38—C37—C36120.0
C13—C14—H14C109.5C38—C37—H37120.0
H14A—C14—H14C109.5C36—C37—H37120.0
H14B—C14—H14C109.5C37—C38—C39120.0
C16—C15—C20120.0C37—C38—Cl4120.3 (3)
C16—C15—N3118.6 (5)C39—C38—Cl4119.7 (3)
C20—C15—N3121.4 (5)C38—C39—C40120.0
C15—C16—C17120.0C38—C39—H39120.0
C15—C16—H16120.0C40—C39—H39120.0
C17—C16—H16120.0C39—C40—C35120.0
C18—C17—C16120.0C39—C40—H40120.0
C18—C17—H17120.0C35—C40—H40120.0
C5—N1—N2—C3−166.1 (7)Cl2—C18—C19—C20176.5 (5)
C1—N1—N2—C3−1.3 (9)C18—C19—C20—C150.0
C11—N3—N4—C13−1.0 (10)C16—C15—C20—C190.0
C15—N3—N4—C13179.3 (7)N3—C15—C20—C19−178.4 (6)
C25—N5—N6—C23174.0 (8)C25—N5—C21—O211.0 (15)
C21—N5—N6—C234.1 (10)N6—N5—C21—O2−180.0 (8)
C31—N7—N8—C33−0.8 (10)C25—N5—C21—C22−170.0 (8)
C35—N7—N8—C33−177.4 (7)N6—N5—C21—C22−1.0 (10)
C5—N1—C1—O1−16.9 (15)O2—C21—C22—C23176.4 (10)
N2—N1—C1—O1−179.7 (8)N5—C21—C22—C23−2.3 (11)
C5—N1—C1—C2163.7 (8)O2—C21—C22—C315.4 (17)
N2—N1—C1—C20.9 (10)N5—C21—C22—C31−173.3 (8)
O1—C1—C2—C3−179.5 (10)N5—N6—C23—C22−5.7 (10)
N1—C1—C2—C3−0.2 (10)N5—N6—C23—C24179.2 (8)
O1—C1—C2—C11−3.1 (17)C21—C22—C23—N65.0 (11)
N1—C1—C2—C11176.1 (8)C31—C22—C23—N6175.7 (9)
N1—N2—C3—C21.2 (10)C21—C22—C23—C24179.4 (9)
N1—N2—C3—C4−178.4 (7)C31—C22—C23—C24−9.9 (17)
C1—C2—C3—N2−0.6 (11)N6—N5—C25—C26−137.2 (6)
C11—C2—C3—N2−176.9 (8)C21—N5—C25—C2630.5 (11)
C1—C2—C3—C4178.9 (9)N6—N5—C25—C3040.2 (10)
C11—C2—C3—C42.6 (16)C21—N5—C25—C30−152.1 (7)
C1—N1—C5—C623.4 (11)C30—C25—C26—C270.0
N2—N1—C5—C6−175.6 (5)N5—C25—C26—C27177.3 (7)
C1—N1—C5—C10−153.6 (8)C25—C26—C27—C280.0
N2—N1—C5—C107.5 (8)C26—C27—C28—C290.0
C10—C5—C6—C70.0C26—C27—C28—Cl3−179.9 (5)
N1—C5—C6—C7−176.9 (6)C27—C28—C29—C300.0
C5—C6—C7—C80.0Cl3—C28—C29—C30179.9 (5)
C6—C7—C8—C90.0C28—C29—C30—C250.0
C6—C7—C8—Cl1178.7 (5)C26—C25—C30—C290.0
C7—C8—C9—C100.0N5—C25—C30—C29−177.4 (6)
Cl1—C8—C9—C10−178.7 (4)N8—N7—C31—C32−0.2 (10)
C8—C9—C10—C50.0C35—N7—C31—C32175.7 (8)
C6—C5—C10—C90.0N8—N7—C31—C22178.5 (9)
N1—C5—C10—C9177.0 (6)C35—N7—C31—C22−5.6 (15)
N4—N3—C11—C121.7 (10)C23—C22—C31—C32−48.2 (16)
C15—N3—C11—C12−178.6 (8)C21—C22—C31—C32121.1 (11)
N4—N3—C11—C2−175.0 (8)C23—C22—C31—N7133.4 (10)
C15—N3—C11—C24.6 (14)C21—C22—C31—N7−57.3 (14)
C3—C2—C11—N3−128.0 (11)N7—C31—C32—C331.1 (10)
C1—C2—C11—N356.4 (14)C22—C31—C32—C33−177.5 (10)
C3—C2—C11—C1255.9 (14)N7—N8—C33—C321.5 (10)
C1—C2—C11—C12−119.7 (11)N7—N8—C33—C34179.6 (9)
N3—C11—C12—C13−1.6 (9)C31—C32—C33—N8−1.6 (11)
C2—C11—C12—C13175.2 (9)C31—C32—C33—C34−179.4 (10)
N3—N4—C13—C12−0.1 (10)N8—N7—C35—C36−28.8 (9)
N3—N4—C13—C14177.0 (9)C31—N7—C35—C36155.5 (8)
C11—C12—C13—N41.1 (11)N8—N7—C35—C40154.5 (6)
C11—C12—C13—C14−175.7 (10)C31—N7—C35—C40−21.1 (11)
N4—N3—C15—C1624.3 (9)C40—C35—C36—C370.0
C11—N3—C15—C16−155.4 (8)N7—C35—C36—C37−176.7 (6)
N4—N3—C15—C20−157.3 (6)C35—C36—C37—C380.0
C11—N3—C15—C2023.1 (11)C36—C37—C38—C390.0
C20—C15—C16—C170.0C36—C37—C38—Cl4177.8 (5)
N3—C15—C16—C17178.5 (6)C37—C38—C39—C400.0
C15—C16—C17—C180.0Cl4—C38—C39—C40−177.8 (5)
C16—C17—C18—C190.0C38—C39—C40—C350.0
C16—C17—C18—Cl2−176.6 (5)C36—C35—C40—C390.0
C17—C18—C19—C200.0N7—C35—C40—C39176.6 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.881.922.65 (1)139
N6—H6···O10.882.032.76 (1)140

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2224).

References

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  • Kumar, D., Singh, S. P., Martínez, A., Fruchier, A., Elguero, J., Martinez-Ripoll, M., Carrió, J. S. & Virgili, A. (1995). Tetrahedron, 51, 4891–4896.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
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  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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