Racemic 5-(2,4-dichloro­phen­yl)-3-(2-naphth­yl)-1-phenyl-2-pyrazoline dichloromethane 0.25-solvate

Lu, Z.-K.; Yu, J.-F.; Huang, P.-M.

doi:10.1107/S160053680604877X

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Racemic 5-(2,4-dichlorophenyl)-3-(2-naphthyl)-1-phenyl-2-pyrazoline dichloromethane 0.25-solvate

Z.-K. Lu, J.-F. Yu and P.-M. Huang

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604877X/hb2203sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680604877X/hb2203Isup2.hkl Contains datablock I

CCDC reference: 629889

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (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
M_r = 438.55	F(000) = 906
Triclinic, P1	D_x = 1.342 Mg m⁻³
Hall symbol: -P 1	Melting point = 382–38 K
a = 11.171 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.464 (4) Å	Cell parameters from 2022 reflections
c = 15.414 (4) Å	θ = 2.4–20.9°
α = 69.656 (5)°	µ = 0.38 mm⁻¹
β = 86.978 (5)°	T = 294 K
γ = 88.595 (6)°	Prism, colourless
V = 2170.7 (11) Å³	0.26 × 0.22 × 0.18 mm

Data collection top

Bruker SMART1000 CCD diffractometer	7622 independent reflections
Radiation source: fine-focus sealed tube	3525 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→12
T_min = 0.898, T_max = 0.936	k = −15→10
11102 measured reflections	l = −18→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0554P)²] where P = (F_o² + 2F_c²)/3
7622 reflections	(Δ/σ)_max = 0.001
550 parameters	Δρ_max = 0.30 e Å⁻³
21 restraints	Δρ_min = −0.32 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.55040 (8)	0.10181 (8)	0.05143 (7)	0.0638 (3)
Cl2	0.88905 (10)	−0.15764 (8)	−0.01307 (7)	0.0771 (4)
Cl3	0.41043 (12)	0.37483 (13)	0.99286 (9)	0.1137 (5)
Cl4	0.31405 (10)	0.24571 (9)	0.71135 (8)	0.0828 (4)
N1	0.7948 (3)	0.1410 (3)	0.2569 (2)	0.0584 (9)
N2	0.7924 (3)	0.0746 (3)	0.3490 (2)	0.0557 (8)
N3	−0.0124 (3)	0.4531 (3)	0.6782 (2)	0.0637 (9)
N4	−0.0211 (3)	0.5536 (2)	0.6125 (2)	0.0567 (9)
C1	0.8639 (3)	0.0009 (3)	0.1619 (2)	0.0535 (10)
H1	0.9104	0.0099	0.2069	0.064*
C2	0.9068 (3)	−0.0618 (3)	0.1131 (3)	0.0582 (11)
H2	0.9813	−0.0949	0.1250	0.070*
C3	0.8378 (4)	−0.0750 (3)	0.0465 (2)	0.0512 (10)
C4	0.7282 (3)	−0.0255 (3)	0.0268 (2)	0.0510 (10)
H4	0.6823	−0.0341	−0.0187	0.061*
C5	0.6887 (3)	0.0372 (3)	0.0770 (2)	0.0450 (9)
C6	0.7535 (3)	0.0510 (3)	0.1461 (2)	0.0430 (9)
C7	0.7024 (3)	0.1137 (3)	0.2052 (2)	0.0527 (10)
H7	0.6608	0.1775	0.1669	0.063*
C8	0.6179 (3)	0.0449 (3)	0.2842 (2)	0.0567 (10)
H8A	0.5467	0.0841	0.2922	0.068*
H8B	0.5943	−0.0185	0.2735	0.068*
C9	0.6961 (4)	0.0188 (3)	0.3663 (3)	0.0526 (10)
C10	0.6641 (4)	−0.0585 (3)	0.4577 (3)	0.0551 (10)
C11	0.5576 (4)	−0.1112 (3)	0.4742 (3)	0.0627 (11)
H11	0.5059	−0.0984	0.4261	0.075*
C12	0.5237 (4)	−0.1853 (3)	0.5631 (3)	0.0640 (11)
C13	0.4112 (4)	−0.2361 (4)	0.5829 (3)	0.0808 (13)
H13	0.3568	−0.2221	0.5364	0.097*
C14	0.3812 (5)	−0.3058 (4)	0.6699 (4)	0.0942 (16)
H14	0.3064	−0.3379	0.6825	0.113*
C15	0.4645 (6)	−0.3285 (4)	0.7401 (4)	0.0985 (18)
H15	0.4449	−0.3775	0.7984	0.118*
C16	0.5721 (5)	−0.2801 (4)	0.7239 (3)	0.0887 (15)
H16	0.6252	−0.2954	0.7714	0.106*
C17	0.6046 (4)	−0.2061 (3)	0.6352 (3)	0.0684 (12)
C18	0.7141 (4)	−0.1503 (4)	0.6161 (3)	0.0758 (13)
H18	0.7678	−0.1632	0.6630	0.091*
C19	0.7430 (4)	−0.0780 (3)	0.5307 (3)	0.0676 (12)
H19	0.8149	−0.0414	0.5204	0.081*
C20	0.8842 (4)	0.2153 (3)	0.2196 (3)	0.0530 (10)
C21	0.9671 (4)	0.2364 (3)	0.2749 (3)	0.0610 (11)
H21	0.9635	0.2006	0.3385	0.073*
C22	1.0546 (4)	0.3107 (4)	0.2345 (4)	0.0746 (13)
H22	1.1093	0.3248	0.2721	0.089*
C23	1.0642 (4)	0.3647 (4)	0.1407 (4)	0.0769 (13)
H23	1.1252	0.4135	0.1150	0.092*
C24	0.9818 (4)	0.3451 (3)	0.0861 (3)	0.0694 (12)
H24	0.9860	0.3819	0.0226	0.083*
C25	0.8925 (4)	0.2714 (3)	0.1240 (3)	0.0605 (11)
H25	0.8375	0.2588	0.0859	0.073*
C26	0.1598 (3)	0.4593 (3)	0.8066 (3)	0.0614 (11)
H26	0.0963	0.5073	0.7927	0.074*
C27	0.2300 (4)	0.4542 (3)	0.8790 (3)	0.0656 (11)
H27	0.2139	0.4981	0.9134	0.079*
C28	0.3238 (4)	0.3836 (4)	0.8996 (3)	0.0679 (12)
C29	0.3499 (3)	0.3200 (3)	0.8490 (3)	0.0664 (12)
H29	0.4144	0.2730	0.8631	0.080*
C30	0.2792 (3)	0.3263 (3)	0.7763 (3)	0.0564 (11)
C31	0.1808 (3)	0.3950 (3)	0.7537 (3)	0.0523 (10)
C32	0.1046 (3)	0.4029 (3)	0.6738 (2)	0.0596 (11)
H32	0.0934	0.3323	0.6707	0.072*
C33	0.1592 (3)	0.4776 (3)	0.5802 (2)	0.0668 (12)
H33A	0.2401	0.4981	0.5864	0.080*
H33B	0.1601	0.4449	0.5332	0.080*
C34	0.0749 (3)	0.5706 (3)	0.5580 (3)	0.0552 (10)
C35	0.0945 (3)	0.6728 (3)	0.4842 (2)	0.0556 (10)
C36	0.1947 (3)	0.6885 (3)	0.4253 (3)	0.0614 (11)
H36	0.2474	0.6322	0.4312	0.074*
C37	0.2202 (4)	0.7878 (3)	0.3559 (2)	0.0572 (11)
C38	0.3257 (4)	0.8040 (4)	0.2968 (3)	0.0758 (13)
H38	0.3784	0.7479	0.3019	0.091*
C39	0.3497 (4)	0.9012 (4)	0.2330 (3)	0.0826 (14)
H39	0.4191	0.9108	0.1950	0.099*
C40	0.2728 (5)	0.9858 (4)	0.2234 (3)	0.0771 (13)
H40	0.2913	1.0520	0.1800	0.092*
C41	0.1698 (4)	0.9725 (3)	0.2777 (3)	0.0702 (12)
H41	0.1177	1.0296	0.2700	0.084*
C42	0.1408 (4)	0.8726 (3)	0.3458 (2)	0.0568 (10)
C43	0.0357 (4)	0.8544 (3)	0.4051 (3)	0.0673 (12)
H43	−0.0195	0.9092	0.3981	0.081*
C44	0.0141 (3)	0.7583 (3)	0.4721 (3)	0.0655 (12)
H44	−0.0550	0.7490	0.5104	0.079*
C45	−0.1057 (3)	0.4125 (3)	0.7441 (2)	0.0529 (10)
C46	−0.2131 (3)	0.4676 (3)	0.7405 (3)	0.0599 (11)
H46	−0.2247	0.5317	0.6929	0.072*
C47	−0.3025 (4)	0.4266 (4)	0.8079 (3)	0.0781 (13)
H47	−0.3742	0.4638	0.8059	0.094*
C48	−0.2869 (4)	0.3310 (4)	0.8785 (3)	0.0830 (14)
H48	−0.3474	0.3043	0.9240	0.100*
C49	−0.1823 (4)	0.2760 (4)	0.8811 (3)	0.0750 (13)
H49	−0.1721	0.2108	0.9276	0.090*
C50	−0.0920 (4)	0.3166 (3)	0.8152 (3)	0.0710 (12)
H50	−0.0204	0.2790	0.8183	0.085*
C51	0.4930 (9)	0.4203 (7)	0.5152 (6)	0.094 (3)	0.50
H51A	0.4341	0.3666	0.5437	0.113*	0.50
H51B	0.5667	0.3855	0.5074	0.113*	0.50
Cl5	0.5164 (5)	0.4855 (5)	0.5926 (4)	0.1128 (15)	0.50
Cl6	0.4502 (9)	0.4881 (8)	0.4169 (7)	0.276 (6)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0483 (6)	0.0708 (7)	0.0694 (7)	0.0061 (5)	−0.0099 (5)	−0.0202 (6)
Cl2	0.0927 (9)	0.0659 (8)	0.0787 (7)	0.0018 (6)	0.0197 (6)	−0.0362 (6)
Cl3	0.0868 (10)	0.1570 (14)	0.1097 (10)	0.0242 (9)	−0.0305 (8)	−0.0597 (10)
Cl4	0.0774 (8)	0.0723 (8)	0.0994 (9)	0.0197 (6)	0.0056 (6)	−0.0334 (7)
N1	0.062 (2)	0.068 (2)	0.050 (2)	−0.0130 (19)	−0.0045 (17)	−0.0253 (19)
N2	0.059 (2)	0.058 (2)	0.053 (2)	−0.0029 (18)	−0.0009 (17)	−0.0245 (19)
N3	0.046 (2)	0.056 (2)	0.067 (2)	0.0058 (18)	0.0043 (17)	0.0039 (19)
N4	0.045 (2)	0.059 (2)	0.057 (2)	0.0008 (17)	−0.0004 (17)	−0.0075 (18)
C1	0.046 (3)	0.056 (3)	0.060 (2)	0.001 (2)	−0.0062 (19)	−0.021 (2)
C2	0.051 (3)	0.050 (3)	0.071 (3)	0.001 (2)	0.002 (2)	−0.018 (2)
C3	0.057 (3)	0.044 (2)	0.050 (2)	−0.003 (2)	0.012 (2)	−0.016 (2)
C4	0.056 (3)	0.053 (2)	0.044 (2)	−0.008 (2)	0.0007 (19)	−0.017 (2)
C5	0.042 (2)	0.044 (2)	0.044 (2)	−0.0061 (18)	0.0016 (18)	−0.0094 (19)
C6	0.046 (2)	0.039 (2)	0.042 (2)	−0.0029 (18)	0.0013 (18)	−0.0116 (18)
C7	0.049 (2)	0.053 (3)	0.058 (2)	0.000 (2)	−0.002 (2)	−0.021 (2)
C8	0.051 (3)	0.064 (3)	0.061 (2)	0.000 (2)	0.005 (2)	−0.030 (2)
C9	0.052 (3)	0.055 (3)	0.055 (3)	0.006 (2)	0.007 (2)	−0.026 (2)
C10	0.056 (3)	0.058 (3)	0.056 (3)	0.005 (2)	0.002 (2)	−0.026 (2)
C11	0.065 (3)	0.062 (3)	0.064 (3)	−0.001 (2)	0.004 (2)	−0.027 (2)
C12	0.074 (3)	0.053 (3)	0.069 (3)	0.000 (2)	0.014 (3)	−0.028 (3)
C13	0.088 (4)	0.073 (3)	0.083 (3)	−0.013 (3)	0.020 (3)	−0.031 (3)
C14	0.099 (4)	0.071 (4)	0.109 (4)	−0.015 (3)	0.040 (4)	−0.031 (3)
C15	0.126 (5)	0.061 (4)	0.089 (4)	0.008 (4)	0.036 (4)	−0.009 (3)
C16	0.105 (5)	0.067 (3)	0.076 (4)	0.011 (3)	0.014 (3)	−0.006 (3)
C17	0.079 (3)	0.054 (3)	0.066 (3)	0.013 (3)	0.010 (3)	−0.016 (3)
C18	0.077 (4)	0.076 (3)	0.069 (3)	0.011 (3)	−0.012 (3)	−0.018 (3)
C19	0.061 (3)	0.070 (3)	0.069 (3)	0.003 (2)	0.000 (2)	−0.021 (3)
C20	0.052 (3)	0.047 (3)	0.068 (3)	0.001 (2)	0.002 (2)	−0.030 (2)
C21	0.058 (3)	0.057 (3)	0.072 (3)	0.002 (2)	−0.007 (2)	−0.027 (2)
C22	0.054 (3)	0.065 (3)	0.115 (4)	−0.001 (2)	−0.013 (3)	−0.041 (3)
C23	0.066 (3)	0.063 (3)	0.099 (4)	−0.008 (2)	0.013 (3)	−0.027 (3)
C24	0.080 (3)	0.050 (3)	0.076 (3)	−0.004 (2)	0.014 (3)	−0.023 (3)
C25	0.068 (3)	0.055 (3)	0.060 (3)	−0.002 (2)	0.004 (2)	−0.024 (2)
C26	0.046 (3)	0.051 (3)	0.079 (3)	0.007 (2)	0.002 (2)	−0.014 (2)
C27	0.056 (3)	0.061 (3)	0.080 (3)	0.003 (2)	0.005 (2)	−0.027 (2)
C28	0.051 (3)	0.076 (3)	0.071 (3)	0.005 (2)	0.002 (2)	−0.019 (3)
C29	0.046 (3)	0.067 (3)	0.071 (3)	0.010 (2)	0.003 (2)	−0.007 (3)
C30	0.044 (2)	0.048 (3)	0.067 (3)	0.004 (2)	0.011 (2)	−0.010 (2)
C31	0.042 (2)	0.045 (2)	0.059 (3)	−0.0011 (19)	0.007 (2)	−0.006 (2)
C32	0.048 (3)	0.054 (3)	0.067 (3)	0.007 (2)	0.002 (2)	−0.009 (2)
C33	0.055 (3)	0.073 (3)	0.061 (3)	0.007 (2)	0.002 (2)	−0.009 (2)
C34	0.045 (3)	0.058 (3)	0.055 (2)	0.003 (2)	−0.002 (2)	−0.009 (2)
C35	0.051 (3)	0.063 (3)	0.047 (2)	0.003 (2)	0.000 (2)	−0.013 (2)
C36	0.054 (3)	0.065 (3)	0.059 (3)	0.005 (2)	−0.001 (2)	−0.015 (2)
C37	0.054 (3)	0.064 (3)	0.045 (2)	−0.006 (2)	−0.001 (2)	−0.008 (2)
C38	0.068 (3)	0.083 (4)	0.063 (3)	−0.002 (3)	0.012 (2)	−0.011 (3)
C39	0.077 (4)	0.095 (4)	0.060 (3)	−0.016 (3)	0.013 (2)	−0.008 (3)
C40	0.094 (4)	0.073 (4)	0.053 (3)	−0.020 (3)	0.004 (3)	−0.009 (3)
C41	0.086 (4)	0.063 (3)	0.055 (3)	0.000 (3)	−0.014 (3)	−0.011 (2)
C42	0.060 (3)	0.060 (3)	0.045 (2)	−0.002 (2)	−0.006 (2)	−0.011 (2)
C43	0.068 (3)	0.066 (3)	0.059 (3)	0.014 (2)	−0.006 (2)	−0.010 (2)
C44	0.052 (3)	0.073 (3)	0.062 (3)	0.005 (2)	0.007 (2)	−0.014 (3)
C45	0.044 (3)	0.055 (3)	0.053 (2)	−0.007 (2)	0.001 (2)	−0.010 (2)
C46	0.048 (3)	0.052 (3)	0.070 (3)	−0.005 (2)	−0.001 (2)	−0.009 (2)
C47	0.048 (3)	0.080 (4)	0.099 (3)	−0.004 (3)	0.011 (3)	−0.024 (3)
C48	0.062 (3)	0.086 (4)	0.083 (3)	−0.017 (3)	0.018 (3)	−0.010 (3)
C49	0.062 (3)	0.067 (3)	0.075 (3)	−0.014 (3)	0.002 (3)	0.002 (2)
C50	0.051 (3)	0.063 (3)	0.079 (3)	0.000 (2)	−0.002 (2)	0.000 (3)
C51	0.087 (6)	0.101 (7)	0.107 (6)	0.003 (5)	−0.015 (5)	−0.052 (6)
Cl5	0.096 (2)	0.114 (3)	0.132 (3)	0.019 (2)	−0.012 (2)	−0.047 (2)
Cl6	0.294 (9)	0.269 (8)	0.311 (8)	0.101 (7)	0.007 (6)	−0.167 (7)

Geometric parameters (Å, º) top

Cl1—C5	1.749 (3)	C23—H23	0.9300
Cl2—C3	1.741 (4)	C24—C25	1.380 (5)
Cl3—C28	1.743 (4)	C24—H24	0.9300
Cl4—C30	1.739 (4)	C25—H25	0.9300
N1—C20	1.384 (5)	C26—C27	1.379 (5)
N1—N2	1.389 (4)	C26—C31	1.388 (5)
N1—C7	1.465 (4)	C26—H26	0.9300
N2—C9	1.290 (4)	C27—C28	1.371 (5)
N3—N4	1.384 (4)	C27—H27	0.9300
N3—C45	1.396 (4)	C28—C29	1.363 (5)
N3—C32	1.465 (4)	C29—C30	1.382 (5)
N4—C34	1.301 (4)	C29—H29	0.9300
C1—C2	1.376 (5)	C30—C31	1.397 (5)
C1—C6	1.382 (4)	C31—C32	1.506 (5)
C1—H1	0.9300	C32—C33	1.547 (5)
C2—C3	1.378 (5)	C32—H32	0.9800
C2—H2	0.9300	C33—C34	1.500 (5)
C3—C4	1.375 (5)	C33—H33A	0.9700
C4—C5	1.381 (4)	C33—H33B	0.9700
C4—H4	0.9300	C34—C35	1.461 (5)
C5—C6	1.384 (4)	C35—C36	1.376 (5)
C6—C7	1.524 (5)	C35—C44	1.409 (5)
C7—C8	1.539 (5)	C36—C37	1.415 (5)
C7—H7	0.9800	C36—H36	0.9300
C8—C9	1.510 (5)	C37—C42	1.399 (5)
C8—H8A	0.9700	C37—C38	1.424 (5)
C8—H8B	0.9700	C38—C39	1.359 (5)
C9—C10	1.463 (5)	C38—H38	0.9300
C10—C11	1.367 (5)	C39—C40	1.380 (6)
C10—C19	1.413 (5)	C39—H39	0.9300
C11—C12	1.426 (5)	C40—C41	1.364 (5)
C11—H11	0.9300	C40—H40	0.9300
C12—C13	1.412 (6)	C41—C42	1.421 (5)
C12—C17	1.417 (6)	C41—H41	0.9300
C13—C14	1.373 (6)	C42—C43	1.422 (5)
C13—H13	0.9300	C43—C44	1.364 (5)
C14—C15	1.411 (7)	C43—H43	0.9300
C14—H14	0.9300	C44—H44	0.9300
C15—C16	1.351 (7)	C45—C50	1.384 (5)
C15—H15	0.9300	C45—C46	1.388 (5)
C16—C17	1.419 (6)	C46—C47	1.379 (5)
C16—H16	0.9300	C46—H46	0.9300
C17—C18	1.414 (6)	C47—C48	1.381 (5)
C18—C19	1.367 (5)	C47—H47	0.9300
C18—H18	0.9300	C48—C49	1.363 (5)
C19—H19	0.9300	C48—H48	0.9300
C20—C21	1.388 (5)	C49—C50	1.371 (5)
C20—C25	1.402 (5)	C49—H49	0.9300
C21—C22	1.377 (5)	C50—H50	0.9300
C21—H21	0.9300	C51—Cl6	1.566 (8)
C22—C23	1.374 (5)	C51—Cl5	1.741 (8)
C22—H22	0.9300	C51—H51A	0.9600
C23—C24	1.369 (6)	C51—H51B	0.9600

C20—N1—N2	121.7 (3)	C20—C25—H25	119.7
C20—N1—C7	125.9 (3)	C27—C26—C31	122.2 (4)
N2—N1—C7	112.0 (3)	C27—C26—H26	118.9
C9—N2—N1	108.5 (3)	C31—C26—H26	118.9
N4—N3—C45	120.4 (3)	C28—C27—C26	119.1 (4)
N4—N3—C32	113.0 (3)	C28—C27—H27	120.4
C45—N3—C32	126.4 (3)	C26—C27—H27	120.4
C34—N4—N3	108.2 (3)	C29—C28—C27	121.2 (4)
C2—C1—C6	121.9 (4)	C29—C28—Cl3	119.6 (3)
C2—C1—H1	119.0	C27—C28—Cl3	119.2 (4)
C6—C1—H1	119.0	C28—C29—C30	119.1 (4)
C1—C2—C3	119.0 (4)	C28—C29—H29	120.5
C1—C2—H2	120.5	C30—C29—H29	120.5
C3—C2—H2	120.5	C29—C30—C31	122.1 (4)
C4—C3—C2	121.4 (3)	C29—C30—Cl4	118.7 (3)
C4—C3—Cl2	119.2 (3)	C31—C30—Cl4	119.2 (3)
C2—C3—Cl2	119.4 (3)	C26—C31—C30	116.4 (4)
C3—C4—C5	117.7 (3)	C26—C31—C32	121.5 (3)
C3—C4—H4	121.1	C30—C31—C32	122.1 (4)
C5—C4—H4	121.1	N3—C32—C31	113.5 (3)
C4—C5—C6	123.0 (3)	N3—C32—C33	101.4 (3)
C4—C5—Cl1	118.0 (3)	C31—C32—C33	112.4 (3)
C6—C5—Cl1	119.0 (3)	N3—C32—H32	109.8
C1—C6—C5	116.9 (3)	C31—C32—H32	109.8
C1—C6—C7	121.6 (3)	C33—C32—H32	109.8
C5—C6—C7	121.4 (3)	C34—C33—C32	102.1 (3)
N1—C7—C6	112.1 (3)	C34—C33—H33A	111.3
N1—C7—C8	101.5 (3)	C32—C33—H33A	111.3
C6—C7—C8	111.1 (3)	C34—C33—H33B	111.3
N1—C7—H7	110.6	C32—C33—H33B	111.3
C6—C7—H7	110.6	H33A—C33—H33B	109.2
C8—C7—H7	110.6	N4—C34—C35	121.0 (3)
C9—C8—C7	101.6 (3)	N4—C34—C33	113.5 (3)
C9—C8—H8A	111.4	C35—C34—C33	125.5 (3)
C7—C8—H8A	111.4	C36—C35—C44	118.0 (4)
C9—C8—H8B	111.4	C36—C35—C34	120.3 (4)
C7—C8—H8B	111.4	C44—C35—C34	121.7 (4)
H8A—C8—H8B	109.3	C35—C36—C37	122.1 (4)
N2—C9—C10	123.0 (4)	C35—C36—H36	119.0
N2—C9—C8	113.2 (3)	C37—C36—H36	119.0
C10—C9—C8	123.8 (4)	C42—C37—C36	119.3 (4)
C11—C10—C19	119.2 (4)	C42—C37—C38	119.0 (4)
C11—C10—C9	120.8 (4)	C36—C37—C38	121.6 (4)
C19—C10—C9	119.9 (4)	C39—C38—C37	120.2 (4)
C10—C11—C12	121.8 (4)	C39—C38—H38	119.9
C10—C11—H11	119.1	C37—C38—H38	119.9
C12—C11—H11	119.1	C38—C39—C40	121.2 (4)
C13—C12—C17	118.8 (4)	C38—C39—H39	119.4
C13—C12—C11	122.6 (4)	C40—C39—H39	119.4
C17—C12—C11	118.5 (4)	C41—C40—C39	120.1 (4)
C14—C13—C12	120.8 (5)	C41—C40—H40	120.0
C14—C13—H13	119.6	C39—C40—H40	120.0
C12—C13—H13	119.6	C40—C41—C42	120.9 (4)
C13—C14—C15	119.7 (5)	C40—C41—H41	119.5
C13—C14—H14	120.2	C42—C41—H41	119.5
C15—C14—H14	120.2	C37—C42—C41	118.5 (4)
C16—C15—C14	121.0 (5)	C37—C42—C43	118.1 (4)
C16—C15—H15	119.5	C41—C42—C43	123.4 (4)
C14—C15—H15	119.5	C44—C43—C42	121.3 (4)
C15—C16—C17	120.5 (5)	C44—C43—H43	119.4
C15—C16—H16	119.7	C42—C43—H43	119.4
C17—C16—H16	119.7	C43—C44—C35	121.2 (4)
C18—C17—C12	118.4 (4)	C43—C44—H44	119.4
C18—C17—C16	122.5 (5)	C35—C44—H44	119.4
C12—C17—C16	119.0 (5)	C50—C45—C46	118.7 (4)
C19—C18—C17	121.7 (4)	C50—C45—N3	120.3 (4)
C19—C18—H18	119.2	C46—C45—N3	121.0 (4)
C17—C18—H18	119.2	C47—C46—C45	119.6 (4)
C18—C19—C10	120.3 (4)	C47—C46—H46	120.2
C18—C19—H19	119.8	C45—C46—H46	120.2
C10—C19—H19	119.8	C46—C47—C48	120.8 (4)
N1—C20—C21	121.5 (4)	C46—C47—H47	119.6
N1—C20—C25	120.1 (4)	C48—C47—H47	119.6
C21—C20—C25	118.4 (4)	C49—C48—C47	119.6 (4)
C22—C21—C20	119.4 (4)	C49—C48—H48	120.2
C22—C21—H21	120.3	C47—C48—H48	120.2
C20—C21—H21	120.3	C48—C49—C50	120.2 (4)
C23—C22—C21	122.4 (4)	C48—C49—H49	119.9
C23—C22—H22	118.8	C50—C49—H49	119.9
C21—C22—H22	118.8	C49—C50—C45	121.1 (4)
C24—C23—C22	118.4 (4)	C49—C50—H50	119.4
C24—C23—H23	120.8	C45—C50—H50	119.4
C22—C23—H23	120.8	Cl6—C51—Cl5	117.7 (7)
C23—C24—C25	120.9 (4)	Cl6—C51—H51A	107.6
C23—C24—H24	119.6	Cl5—C51—H51A	107.5
C25—C24—H24	119.6	Cl6—C51—H51B	108.2
C24—C25—C20	120.5 (4)	Cl5—C51—H51B	107.7
C24—C25—H25	119.7	H51A—C51—H51B	107.7

C20—N1—N2—C9	176.0 (3)	N1—C20—C25—C24	−179.6 (3)
C7—N1—N2—C9	−10.7 (4)	C21—C20—C25—C24	0.5 (5)
C45—N3—N4—C34	−177.8 (3)	C31—C26—C27—C28	0.1 (6)
C32—N3—N4—C34	6.9 (4)	C26—C27—C28—C29	1.1 (6)
C6—C1—C2—C3	0.1 (5)	C26—C27—C28—Cl3	−178.4 (3)
C1—C2—C3—C4	1.0 (5)	C27—C28—C29—C30	−0.8 (6)
C1—C2—C3—Cl2	−177.9 (3)	Cl3—C28—C29—C30	178.8 (3)
C2—C3—C4—C5	−0.7 (5)	C28—C29—C30—C31	−0.8 (6)
Cl2—C3—C4—C5	178.3 (2)	C28—C29—C30—Cl4	179.4 (3)
C3—C4—C5—C6	−0.8 (5)	C27—C26—C31—C30	−1.6 (5)
C3—C4—C5—Cl1	179.1 (3)	C27—C26—C31—C32	−178.9 (3)
C2—C1—C6—C5	−1.4 (5)	C29—C30—C31—C26	1.9 (5)
C2—C1—C6—C7	175.4 (3)	Cl4—C30—C31—C26	−178.3 (3)
C4—C5—C6—C1	1.8 (5)	C29—C30—C31—C32	179.2 (3)
Cl1—C5—C6—C1	−178.1 (3)	Cl4—C30—C31—C32	−0.9 (5)
C4—C5—C6—C7	−175.0 (3)	N4—N3—C32—C31	108.4 (3)
Cl1—C5—C6—C7	5.1 (4)	C45—N3—C32—C31	−66.5 (5)
C20—N1—C7—C6	71.7 (4)	N4—N3—C32—C33	−12.4 (4)
N2—N1—C7—C6	−101.3 (3)	C45—N3—C32—C33	172.7 (4)
C20—N1—C7—C8	−169.7 (3)	C26—C31—C32—N3	−20.3 (5)
N2—N1—C7—C8	17.3 (4)	C30—C31—C32—N3	162.5 (3)
C1—C6—C7—N1	17.7 (5)	C26—C31—C32—C33	94.1 (4)
C5—C6—C7—N1	−165.7 (3)	C30—C31—C32—C33	−83.1 (4)
C1—C6—C7—C8	−95.1 (4)	N3—C32—C33—C34	12.2 (4)
C5—C6—C7—C8	81.6 (4)	C31—C32—C33—C34	−109.3 (3)
N1—C7—C8—C9	−16.3 (3)	N3—N4—C34—C35	−176.8 (3)
C6—C7—C8—C9	103.1 (3)	N3—N4—C34—C33	2.4 (4)
N1—N2—C9—C10	−179.0 (3)	C32—C33—C34—N4	−9.8 (4)
N1—N2—C9—C8	−1.5 (4)	C32—C33—C34—C35	169.4 (4)
C7—C8—C9—N2	11.9 (4)	N4—C34—C35—C36	−178.0 (4)
C7—C8—C9—C10	−170.7 (3)	C33—C34—C35—C36	3.0 (6)
N2—C9—C10—C11	176.0 (3)	N4—C34—C35—C44	3.3 (6)
C8—C9—C10—C11	−1.1 (5)	C33—C34—C35—C44	−175.7 (4)
N2—C9—C10—C19	−2.9 (5)	C44—C35—C36—C37	2.0 (6)
C8—C9—C10—C19	180.0 (3)	C34—C35—C36—C37	−176.8 (3)
C19—C10—C11—C12	0.1 (6)	C35—C36—C37—C42	−0.7 (6)
C9—C10—C11—C12	−178.8 (3)	C35—C36—C37—C38	178.4 (4)
C10—C11—C12—C13	176.3 (4)	C42—C37—C38—C39	1.3 (6)
C10—C11—C12—C17	−1.6 (6)	C36—C37—C38—C39	−177.7 (4)
C17—C12—C13—C14	−1.1 (6)	C37—C38—C39—C40	−0.3 (7)
C11—C12—C13—C14	−179.0 (4)	C38—C39—C40—C41	−1.0 (7)
C12—C13—C14—C15	−1.1 (7)	C39—C40—C41—C42	1.3 (6)
C13—C14—C15—C16	2.1 (8)	C36—C37—C42—C41	178.1 (3)
C14—C15—C16—C17	−0.9 (7)	C38—C37—C42—C41	−1.0 (5)
C13—C12—C17—C18	−176.4 (4)	C36—C37—C42—C43	−1.3 (5)
C11—C12—C17—C18	1.6 (6)	C38—C37—C42—C43	179.6 (4)
C13—C12—C17—C16	2.3 (6)	C40—C41—C42—C37	−0.3 (6)
C11—C12—C17—C16	−179.7 (3)	C40—C41—C42—C43	179.1 (4)
C15—C16—C17—C18	177.3 (4)	C37—C42—C43—C44	2.1 (6)
C15—C16—C17—C12	−1.3 (6)	C41—C42—C43—C44	−177.3 (4)
C12—C17—C18—C19	−0.2 (6)	C42—C43—C44—C35	−0.8 (6)
C16—C17—C18—C19	−178.8 (4)	C36—C35—C44—C43	−1.2 (6)
C17—C18—C19—C10	−1.3 (6)	C34—C35—C44—C43	177.5 (4)
C11—C10—C19—C18	1.3 (6)	N4—N3—C45—C50	−173.6 (3)
C9—C10—C19—C18	−179.8 (3)	C32—N3—C45—C50	1.1 (6)
N2—N1—C20—C21	−8.3 (5)	N4—N3—C45—C46	5.8 (5)
C7—N1—C20—C21	179.3 (3)	C32—N3—C45—C46	−179.6 (4)
N2—N1—C20—C25	171.8 (3)	C50—C45—C46—C47	0.9 (6)
C7—N1—C20—C25	−0.6 (5)	N3—C45—C46—C47	−178.4 (4)
N1—C20—C21—C22	179.8 (3)	C45—C46—C47—C48	−0.7 (6)
C25—C20—C21—C22	−0.4 (5)	C46—C47—C48—C49	−0.6 (7)
C20—C21—C22—C23	−0.6 (6)	C47—C48—C49—C50	1.5 (7)
C21—C22—C23—C24	1.4 (7)	C48—C49—C50—C45	−1.3 (7)
C22—C23—C24—C25	−1.2 (6)	C46—C45—C50—C49	0.0 (6)
C23—C24—C25—C20	0.3 (6)	N3—C45—C50—C49	179.4 (4)

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