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The racemic title compound, C25H18Cl2N2·0.25CH2Cl2, contains two pyrazoline mol­ecules in the asymmetric unit, with similar conformations. A disordered dichloro­methane solvent mol­ecule completes the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604877X/hb2203sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604877X/hb2203Isup2.hkl
Contains datablock I

CCDC reference: 629889

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in solvent or counterion
  • R factor = 0.052
  • wR factor = 0.142
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.25 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C51 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

(dl)-5-(2,4-dichlorophenyl)-3-(2-naphthyl)-1-phenyl-2-pyrazoline dicholromethane 0.25-solvate top
Crystal data top
C25H18Cl2N2·0.25(CH2Cl2)Z = 4
Mr = 438.55F(000) = 906
Triclinic, P1Dx = 1.342 Mg m3
Hall symbol: -P 1Melting point = 382–38 K
a = 11.171 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.464 (4) ÅCell parameters from 2022 reflections
c = 15.414 (4) Åθ = 2.4–20.9°
α = 69.656 (5)°µ = 0.38 mm1
β = 86.978 (5)°T = 294 K
γ = 88.595 (6)°Prism, colourless
V = 2170.7 (11) Å30.26 × 0.22 × 0.18 mm
Data collection top
Bruker SMART1000 CCD
diffractometer
7622 independent reflections
Radiation source: fine-focus sealed tube3525 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1312
Tmin = 0.898, Tmax = 0.936k = 1510
11102 measured reflectionsl = 1813
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0554P)2]
where P = (Fo2 + 2Fc2)/3
7622 reflections(Δ/σ)max = 0.001
550 parametersΔρmax = 0.30 e Å3
21 restraintsΔρmin = 0.32 e Å3
Special details top

Experimental. 1H NMR (CDCl3): δ 8.17 (d, 1H), 7.86–7.81 (m, 4H), 7.50 (dd, 3H), 7.27–7.15 (m, 4H), 7.03 (dd, 2H), 6.85 (s, 1H), 5.65–5.62 (m, 1H), 4.09–4.02 (m, 1H), 3.19–3.13 (m, 1H).

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*/UeqOcc. (<1)
Cl10.55040 (8)0.10181 (8)0.05143 (7)0.0638 (3)
Cl20.88905 (10)0.15764 (8)0.01307 (7)0.0771 (4)
Cl30.41043 (12)0.37483 (13)0.99286 (9)0.1137 (5)
Cl40.31405 (10)0.24571 (9)0.71135 (8)0.0828 (4)
N10.7948 (3)0.1410 (3)0.2569 (2)0.0584 (9)
N20.7924 (3)0.0746 (3)0.3490 (2)0.0557 (8)
N30.0124 (3)0.4531 (3)0.6782 (2)0.0637 (9)
N40.0211 (3)0.5536 (2)0.6125 (2)0.0567 (9)
C10.8639 (3)0.0009 (3)0.1619 (2)0.0535 (10)
H10.91040.00990.20690.064*
C20.9068 (3)0.0618 (3)0.1131 (3)0.0582 (11)
H20.98130.09490.12500.070*
C30.8378 (4)0.0750 (3)0.0465 (2)0.0512 (10)
C40.7282 (3)0.0255 (3)0.0268 (2)0.0510 (10)
H40.68230.03410.01870.061*
C50.6887 (3)0.0372 (3)0.0770 (2)0.0450 (9)
C60.7535 (3)0.0510 (3)0.1461 (2)0.0430 (9)
C70.7024 (3)0.1137 (3)0.2052 (2)0.0527 (10)
H70.66080.17750.16690.063*
C80.6179 (3)0.0449 (3)0.2842 (2)0.0567 (10)
H8A0.54670.08410.29220.068*
H8B0.59430.01850.27350.068*
C90.6961 (4)0.0188 (3)0.3663 (3)0.0526 (10)
C100.6641 (4)0.0585 (3)0.4577 (3)0.0551 (10)
C110.5576 (4)0.1112 (3)0.4742 (3)0.0627 (11)
H110.50590.09840.42610.075*
C120.5237 (4)0.1853 (3)0.5631 (3)0.0640 (11)
C130.4112 (4)0.2361 (4)0.5829 (3)0.0808 (13)
H130.35680.22210.53640.097*
C140.3812 (5)0.3058 (4)0.6699 (4)0.0942 (16)
H140.30640.33790.68250.113*
C150.4645 (6)0.3285 (4)0.7401 (4)0.0985 (18)
H150.44490.37750.79840.118*
C160.5721 (5)0.2801 (4)0.7239 (3)0.0887 (15)
H160.62520.29540.77140.106*
C170.6046 (4)0.2061 (3)0.6352 (3)0.0684 (12)
C180.7141 (4)0.1503 (4)0.6161 (3)0.0758 (13)
H180.76780.16320.66300.091*
C190.7430 (4)0.0780 (3)0.5307 (3)0.0676 (12)
H190.81490.04140.52040.081*
C200.8842 (4)0.2153 (3)0.2196 (3)0.0530 (10)
C210.9671 (4)0.2364 (3)0.2749 (3)0.0610 (11)
H210.96350.20060.33850.073*
C221.0546 (4)0.3107 (4)0.2345 (4)0.0746 (13)
H221.10930.32480.27210.089*
C231.0642 (4)0.3647 (4)0.1407 (4)0.0769 (13)
H231.12520.41350.11500.092*
C240.9818 (4)0.3451 (3)0.0861 (3)0.0694 (12)
H240.98600.38190.02260.083*
C250.8925 (4)0.2714 (3)0.1240 (3)0.0605 (11)
H250.83750.25880.08590.073*
C260.1598 (3)0.4593 (3)0.8066 (3)0.0614 (11)
H260.09630.50730.79270.074*
C270.2300 (4)0.4542 (3)0.8790 (3)0.0656 (11)
H270.21390.49810.91340.079*
C280.3238 (4)0.3836 (4)0.8996 (3)0.0679 (12)
C290.3499 (3)0.3200 (3)0.8490 (3)0.0664 (12)
H290.41440.27300.86310.080*
C300.2792 (3)0.3263 (3)0.7763 (3)0.0564 (11)
C310.1808 (3)0.3950 (3)0.7537 (3)0.0523 (10)
C320.1046 (3)0.4029 (3)0.6738 (2)0.0596 (11)
H320.09340.33230.67070.072*
C330.1592 (3)0.4776 (3)0.5802 (2)0.0668 (12)
H33A0.24010.49810.58640.080*
H33B0.16010.44490.53320.080*
C340.0749 (3)0.5706 (3)0.5580 (3)0.0552 (10)
C350.0945 (3)0.6728 (3)0.4842 (2)0.0556 (10)
C360.1947 (3)0.6885 (3)0.4253 (3)0.0614 (11)
H360.24740.63220.43120.074*
C370.2202 (4)0.7878 (3)0.3559 (2)0.0572 (11)
C380.3257 (4)0.8040 (4)0.2968 (3)0.0758 (13)
H380.37840.74790.30190.091*
C390.3497 (4)0.9012 (4)0.2330 (3)0.0826 (14)
H390.41910.91080.19500.099*
C400.2728 (5)0.9858 (4)0.2234 (3)0.0771 (13)
H400.29131.05200.18000.092*
C410.1698 (4)0.9725 (3)0.2777 (3)0.0702 (12)
H410.11771.02960.27000.084*
C420.1408 (4)0.8726 (3)0.3458 (2)0.0568 (10)
C430.0357 (4)0.8544 (3)0.4051 (3)0.0673 (12)
H430.01950.90920.39810.081*
C440.0141 (3)0.7583 (3)0.4721 (3)0.0655 (12)
H440.05500.74900.51040.079*
C450.1057 (3)0.4125 (3)0.7441 (2)0.0529 (10)
C460.2131 (3)0.4676 (3)0.7405 (3)0.0599 (11)
H460.22470.53170.69290.072*
C470.3025 (4)0.4266 (4)0.8079 (3)0.0781 (13)
H470.37420.46380.80590.094*
C480.2869 (4)0.3310 (4)0.8785 (3)0.0830 (14)
H480.34740.30430.92400.100*
C490.1823 (4)0.2760 (4)0.8811 (3)0.0750 (13)
H490.17210.21080.92760.090*
C500.0920 (4)0.3166 (3)0.8152 (3)0.0710 (12)
H500.02040.27900.81830.085*
C510.4930 (9)0.4203 (7)0.5152 (6)0.094 (3)0.50
H51A0.43410.36660.54370.113*0.50
H51B0.56670.38550.50740.113*0.50
Cl50.5164 (5)0.4855 (5)0.5926 (4)0.1128 (15)0.50
Cl60.4502 (9)0.4881 (8)0.4169 (7)0.276 (6)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0483 (6)0.0708 (7)0.0694 (7)0.0061 (5)0.0099 (5)0.0202 (6)
Cl20.0927 (9)0.0659 (8)0.0787 (7)0.0018 (6)0.0197 (6)0.0362 (6)
Cl30.0868 (10)0.1570 (14)0.1097 (10)0.0242 (9)0.0305 (8)0.0597 (10)
Cl40.0774 (8)0.0723 (8)0.0994 (9)0.0197 (6)0.0056 (6)0.0334 (7)
N10.062 (2)0.068 (2)0.050 (2)0.0130 (19)0.0045 (17)0.0253 (19)
N20.059 (2)0.058 (2)0.053 (2)0.0029 (18)0.0009 (17)0.0245 (19)
N30.046 (2)0.056 (2)0.067 (2)0.0058 (18)0.0043 (17)0.0039 (19)
N40.045 (2)0.059 (2)0.057 (2)0.0008 (17)0.0004 (17)0.0075 (18)
C10.046 (3)0.056 (3)0.060 (2)0.001 (2)0.0062 (19)0.021 (2)
C20.051 (3)0.050 (3)0.071 (3)0.001 (2)0.002 (2)0.018 (2)
C30.057 (3)0.044 (2)0.050 (2)0.003 (2)0.012 (2)0.016 (2)
C40.056 (3)0.053 (2)0.044 (2)0.008 (2)0.0007 (19)0.017 (2)
C50.042 (2)0.044 (2)0.044 (2)0.0061 (18)0.0016 (18)0.0094 (19)
C60.046 (2)0.039 (2)0.042 (2)0.0029 (18)0.0013 (18)0.0116 (18)
C70.049 (2)0.053 (3)0.058 (2)0.000 (2)0.002 (2)0.021 (2)
C80.051 (3)0.064 (3)0.061 (2)0.000 (2)0.005 (2)0.030 (2)
C90.052 (3)0.055 (3)0.055 (3)0.006 (2)0.007 (2)0.026 (2)
C100.056 (3)0.058 (3)0.056 (3)0.005 (2)0.002 (2)0.026 (2)
C110.065 (3)0.062 (3)0.064 (3)0.001 (2)0.004 (2)0.027 (2)
C120.074 (3)0.053 (3)0.069 (3)0.000 (2)0.014 (3)0.028 (3)
C130.088 (4)0.073 (3)0.083 (3)0.013 (3)0.020 (3)0.031 (3)
C140.099 (4)0.071 (4)0.109 (4)0.015 (3)0.040 (4)0.031 (3)
C150.126 (5)0.061 (4)0.089 (4)0.008 (4)0.036 (4)0.009 (3)
C160.105 (5)0.067 (3)0.076 (4)0.011 (3)0.014 (3)0.006 (3)
C170.079 (3)0.054 (3)0.066 (3)0.013 (3)0.010 (3)0.016 (3)
C180.077 (4)0.076 (3)0.069 (3)0.011 (3)0.012 (3)0.018 (3)
C190.061 (3)0.070 (3)0.069 (3)0.003 (2)0.000 (2)0.021 (3)
C200.052 (3)0.047 (3)0.068 (3)0.001 (2)0.002 (2)0.030 (2)
C210.058 (3)0.057 (3)0.072 (3)0.002 (2)0.007 (2)0.027 (2)
C220.054 (3)0.065 (3)0.115 (4)0.001 (2)0.013 (3)0.041 (3)
C230.066 (3)0.063 (3)0.099 (4)0.008 (2)0.013 (3)0.027 (3)
C240.080 (3)0.050 (3)0.076 (3)0.004 (2)0.014 (3)0.023 (3)
C250.068 (3)0.055 (3)0.060 (3)0.002 (2)0.004 (2)0.024 (2)
C260.046 (3)0.051 (3)0.079 (3)0.007 (2)0.002 (2)0.014 (2)
C270.056 (3)0.061 (3)0.080 (3)0.003 (2)0.005 (2)0.027 (2)
C280.051 (3)0.076 (3)0.071 (3)0.005 (2)0.002 (2)0.019 (3)
C290.046 (3)0.067 (3)0.071 (3)0.010 (2)0.003 (2)0.007 (3)
C300.044 (2)0.048 (3)0.067 (3)0.004 (2)0.011 (2)0.010 (2)
C310.042 (2)0.045 (2)0.059 (3)0.0011 (19)0.007 (2)0.006 (2)
C320.048 (3)0.054 (3)0.067 (3)0.007 (2)0.002 (2)0.009 (2)
C330.055 (3)0.073 (3)0.061 (3)0.007 (2)0.002 (2)0.009 (2)
C340.045 (3)0.058 (3)0.055 (2)0.003 (2)0.002 (2)0.009 (2)
C350.051 (3)0.063 (3)0.047 (2)0.003 (2)0.000 (2)0.013 (2)
C360.054 (3)0.065 (3)0.059 (3)0.005 (2)0.001 (2)0.015 (2)
C370.054 (3)0.064 (3)0.045 (2)0.006 (2)0.001 (2)0.008 (2)
C380.068 (3)0.083 (4)0.063 (3)0.002 (3)0.012 (2)0.011 (3)
C390.077 (4)0.095 (4)0.060 (3)0.016 (3)0.013 (2)0.008 (3)
C400.094 (4)0.073 (4)0.053 (3)0.020 (3)0.004 (3)0.009 (3)
C410.086 (4)0.063 (3)0.055 (3)0.000 (3)0.014 (3)0.011 (2)
C420.060 (3)0.060 (3)0.045 (2)0.002 (2)0.006 (2)0.011 (2)
C430.068 (3)0.066 (3)0.059 (3)0.014 (2)0.006 (2)0.010 (2)
C440.052 (3)0.073 (3)0.062 (3)0.005 (2)0.007 (2)0.014 (3)
C450.044 (3)0.055 (3)0.053 (2)0.007 (2)0.001 (2)0.010 (2)
C460.048 (3)0.052 (3)0.070 (3)0.005 (2)0.001 (2)0.009 (2)
C470.048 (3)0.080 (4)0.099 (3)0.004 (3)0.011 (3)0.024 (3)
C480.062 (3)0.086 (4)0.083 (3)0.017 (3)0.018 (3)0.010 (3)
C490.062 (3)0.067 (3)0.075 (3)0.014 (3)0.002 (3)0.002 (2)
C500.051 (3)0.063 (3)0.079 (3)0.000 (2)0.002 (2)0.000 (3)
C510.087 (6)0.101 (7)0.107 (6)0.003 (5)0.015 (5)0.052 (6)
Cl50.096 (2)0.114 (3)0.132 (3)0.019 (2)0.012 (2)0.047 (2)
Cl60.294 (9)0.269 (8)0.311 (8)0.101 (7)0.007 (6)0.167 (7)
Geometric parameters (Å, º) top
Cl1—C51.749 (3)C23—H230.9300
Cl2—C31.741 (4)C24—C251.380 (5)
Cl3—C281.743 (4)C24—H240.9300
Cl4—C301.739 (4)C25—H250.9300
N1—C201.384 (5)C26—C271.379 (5)
N1—N21.389 (4)C26—C311.388 (5)
N1—C71.465 (4)C26—H260.9300
N2—C91.290 (4)C27—C281.371 (5)
N3—N41.384 (4)C27—H270.9300
N3—C451.396 (4)C28—C291.363 (5)
N3—C321.465 (4)C29—C301.382 (5)
N4—C341.301 (4)C29—H290.9300
C1—C21.376 (5)C30—C311.397 (5)
C1—C61.382 (4)C31—C321.506 (5)
C1—H10.9300C32—C331.547 (5)
C2—C31.378 (5)C32—H320.9800
C2—H20.9300C33—C341.500 (5)
C3—C41.375 (5)C33—H33A0.9700
C4—C51.381 (4)C33—H33B0.9700
C4—H40.9300C34—C351.461 (5)
C5—C61.384 (4)C35—C361.376 (5)
C6—C71.524 (5)C35—C441.409 (5)
C7—C81.539 (5)C36—C371.415 (5)
C7—H70.9800C36—H360.9300
C8—C91.510 (5)C37—C421.399 (5)
C8—H8A0.9700C37—C381.424 (5)
C8—H8B0.9700C38—C391.359 (5)
C9—C101.463 (5)C38—H380.9300
C10—C111.367 (5)C39—C401.380 (6)
C10—C191.413 (5)C39—H390.9300
C11—C121.426 (5)C40—C411.364 (5)
C11—H110.9300C40—H400.9300
C12—C131.412 (6)C41—C421.421 (5)
C12—C171.417 (6)C41—H410.9300
C13—C141.373 (6)C42—C431.422 (5)
C13—H130.9300C43—C441.364 (5)
C14—C151.411 (7)C43—H430.9300
C14—H140.9300C44—H440.9300
C15—C161.351 (7)C45—C501.384 (5)
C15—H150.9300C45—C461.388 (5)
C16—C171.419 (6)C46—C471.379 (5)
C16—H160.9300C46—H460.9300
C17—C181.414 (6)C47—C481.381 (5)
C18—C191.367 (5)C47—H470.9300
C18—H180.9300C48—C491.363 (5)
C19—H190.9300C48—H480.9300
C20—C211.388 (5)C49—C501.371 (5)
C20—C251.402 (5)C49—H490.9300
C21—C221.377 (5)C50—H500.9300
C21—H210.9300C51—Cl61.566 (8)
C22—C231.374 (5)C51—Cl51.741 (8)
C22—H220.9300C51—H51A0.9600
C23—C241.369 (6)C51—H51B0.9600
C20—N1—N2121.7 (3)C20—C25—H25119.7
C20—N1—C7125.9 (3)C27—C26—C31122.2 (4)
N2—N1—C7112.0 (3)C27—C26—H26118.9
C9—N2—N1108.5 (3)C31—C26—H26118.9
N4—N3—C45120.4 (3)C28—C27—C26119.1 (4)
N4—N3—C32113.0 (3)C28—C27—H27120.4
C45—N3—C32126.4 (3)C26—C27—H27120.4
C34—N4—N3108.2 (3)C29—C28—C27121.2 (4)
C2—C1—C6121.9 (4)C29—C28—Cl3119.6 (3)
C2—C1—H1119.0C27—C28—Cl3119.2 (4)
C6—C1—H1119.0C28—C29—C30119.1 (4)
C1—C2—C3119.0 (4)C28—C29—H29120.5
C1—C2—H2120.5C30—C29—H29120.5
C3—C2—H2120.5C29—C30—C31122.1 (4)
C4—C3—C2121.4 (3)C29—C30—Cl4118.7 (3)
C4—C3—Cl2119.2 (3)C31—C30—Cl4119.2 (3)
C2—C3—Cl2119.4 (3)C26—C31—C30116.4 (4)
C3—C4—C5117.7 (3)C26—C31—C32121.5 (3)
C3—C4—H4121.1C30—C31—C32122.1 (4)
C5—C4—H4121.1N3—C32—C31113.5 (3)
C4—C5—C6123.0 (3)N3—C32—C33101.4 (3)
C4—C5—Cl1118.0 (3)C31—C32—C33112.4 (3)
C6—C5—Cl1119.0 (3)N3—C32—H32109.8
C1—C6—C5116.9 (3)C31—C32—H32109.8
C1—C6—C7121.6 (3)C33—C32—H32109.8
C5—C6—C7121.4 (3)C34—C33—C32102.1 (3)
N1—C7—C6112.1 (3)C34—C33—H33A111.3
N1—C7—C8101.5 (3)C32—C33—H33A111.3
C6—C7—C8111.1 (3)C34—C33—H33B111.3
N1—C7—H7110.6C32—C33—H33B111.3
C6—C7—H7110.6H33A—C33—H33B109.2
C8—C7—H7110.6N4—C34—C35121.0 (3)
C9—C8—C7101.6 (3)N4—C34—C33113.5 (3)
C9—C8—H8A111.4C35—C34—C33125.5 (3)
C7—C8—H8A111.4C36—C35—C44118.0 (4)
C9—C8—H8B111.4C36—C35—C34120.3 (4)
C7—C8—H8B111.4C44—C35—C34121.7 (4)
H8A—C8—H8B109.3C35—C36—C37122.1 (4)
N2—C9—C10123.0 (4)C35—C36—H36119.0
N2—C9—C8113.2 (3)C37—C36—H36119.0
C10—C9—C8123.8 (4)C42—C37—C36119.3 (4)
C11—C10—C19119.2 (4)C42—C37—C38119.0 (4)
C11—C10—C9120.8 (4)C36—C37—C38121.6 (4)
C19—C10—C9119.9 (4)C39—C38—C37120.2 (4)
C10—C11—C12121.8 (4)C39—C38—H38119.9
C10—C11—H11119.1C37—C38—H38119.9
C12—C11—H11119.1C38—C39—C40121.2 (4)
C13—C12—C17118.8 (4)C38—C39—H39119.4
C13—C12—C11122.6 (4)C40—C39—H39119.4
C17—C12—C11118.5 (4)C41—C40—C39120.1 (4)
C14—C13—C12120.8 (5)C41—C40—H40120.0
C14—C13—H13119.6C39—C40—H40120.0
C12—C13—H13119.6C40—C41—C42120.9 (4)
C13—C14—C15119.7 (5)C40—C41—H41119.5
C13—C14—H14120.2C42—C41—H41119.5
C15—C14—H14120.2C37—C42—C41118.5 (4)
C16—C15—C14121.0 (5)C37—C42—C43118.1 (4)
C16—C15—H15119.5C41—C42—C43123.4 (4)
C14—C15—H15119.5C44—C43—C42121.3 (4)
C15—C16—C17120.5 (5)C44—C43—H43119.4
C15—C16—H16119.7C42—C43—H43119.4
C17—C16—H16119.7C43—C44—C35121.2 (4)
C18—C17—C12118.4 (4)C43—C44—H44119.4
C18—C17—C16122.5 (5)C35—C44—H44119.4
C12—C17—C16119.0 (5)C50—C45—C46118.7 (4)
C19—C18—C17121.7 (4)C50—C45—N3120.3 (4)
C19—C18—H18119.2C46—C45—N3121.0 (4)
C17—C18—H18119.2C47—C46—C45119.6 (4)
C18—C19—C10120.3 (4)C47—C46—H46120.2
C18—C19—H19119.8C45—C46—H46120.2
C10—C19—H19119.8C46—C47—C48120.8 (4)
N1—C20—C21121.5 (4)C46—C47—H47119.6
N1—C20—C25120.1 (4)C48—C47—H47119.6
C21—C20—C25118.4 (4)C49—C48—C47119.6 (4)
C22—C21—C20119.4 (4)C49—C48—H48120.2
C22—C21—H21120.3C47—C48—H48120.2
C20—C21—H21120.3C48—C49—C50120.2 (4)
C23—C22—C21122.4 (4)C48—C49—H49119.9
C23—C22—H22118.8C50—C49—H49119.9
C21—C22—H22118.8C49—C50—C45121.1 (4)
C24—C23—C22118.4 (4)C49—C50—H50119.4
C24—C23—H23120.8C45—C50—H50119.4
C22—C23—H23120.8Cl6—C51—Cl5117.7 (7)
C23—C24—C25120.9 (4)Cl6—C51—H51A107.6
C23—C24—H24119.6Cl5—C51—H51A107.5
C25—C24—H24119.6Cl6—C51—H51B108.2
C24—C25—C20120.5 (4)Cl5—C51—H51B107.7
C24—C25—H25119.7H51A—C51—H51B107.7
C20—N1—N2—C9176.0 (3)N1—C20—C25—C24179.6 (3)
C7—N1—N2—C910.7 (4)C21—C20—C25—C240.5 (5)
C45—N3—N4—C34177.8 (3)C31—C26—C27—C280.1 (6)
C32—N3—N4—C346.9 (4)C26—C27—C28—C291.1 (6)
C6—C1—C2—C30.1 (5)C26—C27—C28—Cl3178.4 (3)
C1—C2—C3—C41.0 (5)C27—C28—C29—C300.8 (6)
C1—C2—C3—Cl2177.9 (3)Cl3—C28—C29—C30178.8 (3)
C2—C3—C4—C50.7 (5)C28—C29—C30—C310.8 (6)
Cl2—C3—C4—C5178.3 (2)C28—C29—C30—Cl4179.4 (3)
C3—C4—C5—C60.8 (5)C27—C26—C31—C301.6 (5)
C3—C4—C5—Cl1179.1 (3)C27—C26—C31—C32178.9 (3)
C2—C1—C6—C51.4 (5)C29—C30—C31—C261.9 (5)
C2—C1—C6—C7175.4 (3)Cl4—C30—C31—C26178.3 (3)
C4—C5—C6—C11.8 (5)C29—C30—C31—C32179.2 (3)
Cl1—C5—C6—C1178.1 (3)Cl4—C30—C31—C320.9 (5)
C4—C5—C6—C7175.0 (3)N4—N3—C32—C31108.4 (3)
Cl1—C5—C6—C75.1 (4)C45—N3—C32—C3166.5 (5)
C20—N1—C7—C671.7 (4)N4—N3—C32—C3312.4 (4)
N2—N1—C7—C6101.3 (3)C45—N3—C32—C33172.7 (4)
C20—N1—C7—C8169.7 (3)C26—C31—C32—N320.3 (5)
N2—N1—C7—C817.3 (4)C30—C31—C32—N3162.5 (3)
C1—C6—C7—N117.7 (5)C26—C31—C32—C3394.1 (4)
C5—C6—C7—N1165.7 (3)C30—C31—C32—C3383.1 (4)
C1—C6—C7—C895.1 (4)N3—C32—C33—C3412.2 (4)
C5—C6—C7—C881.6 (4)C31—C32—C33—C34109.3 (3)
N1—C7—C8—C916.3 (3)N3—N4—C34—C35176.8 (3)
C6—C7—C8—C9103.1 (3)N3—N4—C34—C332.4 (4)
N1—N2—C9—C10179.0 (3)C32—C33—C34—N49.8 (4)
N1—N2—C9—C81.5 (4)C32—C33—C34—C35169.4 (4)
C7—C8—C9—N211.9 (4)N4—C34—C35—C36178.0 (4)
C7—C8—C9—C10170.7 (3)C33—C34—C35—C363.0 (6)
N2—C9—C10—C11176.0 (3)N4—C34—C35—C443.3 (6)
C8—C9—C10—C111.1 (5)C33—C34—C35—C44175.7 (4)
N2—C9—C10—C192.9 (5)C44—C35—C36—C372.0 (6)
C8—C9—C10—C19180.0 (3)C34—C35—C36—C37176.8 (3)
C19—C10—C11—C120.1 (6)C35—C36—C37—C420.7 (6)
C9—C10—C11—C12178.8 (3)C35—C36—C37—C38178.4 (4)
C10—C11—C12—C13176.3 (4)C42—C37—C38—C391.3 (6)
C10—C11—C12—C171.6 (6)C36—C37—C38—C39177.7 (4)
C17—C12—C13—C141.1 (6)C37—C38—C39—C400.3 (7)
C11—C12—C13—C14179.0 (4)C38—C39—C40—C411.0 (7)
C12—C13—C14—C151.1 (7)C39—C40—C41—C421.3 (6)
C13—C14—C15—C162.1 (8)C36—C37—C42—C41178.1 (3)
C14—C15—C16—C170.9 (7)C38—C37—C42—C411.0 (5)
C13—C12—C17—C18176.4 (4)C36—C37—C42—C431.3 (5)
C11—C12—C17—C181.6 (6)C38—C37—C42—C43179.6 (4)
C13—C12—C17—C162.3 (6)C40—C41—C42—C370.3 (6)
C11—C12—C17—C16179.7 (3)C40—C41—C42—C43179.1 (4)
C15—C16—C17—C18177.3 (4)C37—C42—C43—C442.1 (6)
C15—C16—C17—C121.3 (6)C41—C42—C43—C44177.3 (4)
C12—C17—C18—C190.2 (6)C42—C43—C44—C350.8 (6)
C16—C17—C18—C19178.8 (4)C36—C35—C44—C431.2 (6)
C17—C18—C19—C101.3 (6)C34—C35—C44—C43177.5 (4)
C11—C10—C19—C181.3 (6)N4—N3—C45—C50173.6 (3)
C9—C10—C19—C18179.8 (3)C32—N3—C45—C501.1 (6)
N2—N1—C20—C218.3 (5)N4—N3—C45—C465.8 (5)
C7—N1—C20—C21179.3 (3)C32—N3—C45—C46179.6 (4)
N2—N1—C20—C25171.8 (3)C50—C45—C46—C470.9 (6)
C7—N1—C20—C250.6 (5)N3—C45—C46—C47178.4 (4)
N1—C20—C21—C22179.8 (3)C45—C46—C47—C480.7 (6)
C25—C20—C21—C220.4 (5)C46—C47—C48—C490.6 (7)
C20—C21—C22—C230.6 (6)C47—C48—C49—C501.5 (7)
C21—C22—C23—C241.4 (7)C48—C49—C50—C451.3 (7)
C22—C23—C24—C251.2 (6)C46—C45—C50—C490.0 (6)
C23—C24—C25—C200.3 (6)N3—C45—C50—C49179.4 (4)
 

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