(SR)-5-(2,6-Dichloro­phen­yl)-3-(2-naphth­yl)-1-phenyl-2-pyrazoline trichloro­methane hemisolvate

In the title compound, C₂₅H₁₈Cl₂N₂·0.5CHCl₃, the mean planes of the dichloro­benzene ring, the phenyl ring, and the naphthalene ring system make dihedral angles of 85.1 (3), 7.2 (3) and 3.2 (3)°, respectively, with the mean plane of the pyrazoline ring. A disordered solvent mol­ecule completes the structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
Some non-H atoms missing
• Disorder in solvent or counterion
• R factor = 0.051
• wR factor = 0.138
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A
ABSMU01_ALERT_1_A  The ratio of given/expected absorption coefficient lies
               outside the range 0.90 <> 1.10
            Calculated value of mu =     0.238
            Value of mu given      =     0.477
CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.90 <> 1.10
           From the CIF: _cell_formula_units_Z                    2
           From the CIF: _chemical_formula_weight           477.00
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   51.00  612.56
           H         1.01   37.00   37.30
           N        14.01    4.00   56.03
           Cl       35.45    7.00  248.17
           Calculated formula weight              954.06
DENSD01_ALERT_1_A  The ratio of the submitted crystal density and that
            calculated from the formula is outside the range 0.90 <> 1.10
            Crystal density given    =      1.390
            Calculated crystal density =      0.695
PLAT043_ALERT_1_A Check Reported Molecular Weight ................     477.00
PLAT046_ALERT_1_A Reported Z, MW and D(calc) are Inconsistent ....       0.69

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C26
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C26'
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.21 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.90 Deg.
              CL4' -C26' -CL3'    3.666   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.20 Deg.
              CL4' -C26' -CL3'    1.555   1.555   3.666
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.70 Deg.
              CL3  -C26  -CL4     3.666   1.555   1.555

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C25.5 H18.5 Cl3.5 N2
            Atom count from the _atom_site data:  C51 H37 Cl7 N4
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C25.5 H18.5 Cl3.5 N2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         51.00    102.00  -51.00
           H         37.00     74.00  -37.00
           Cl         7.00     14.00   -7.00
           N          4.00      8.00   -4.00

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

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

---

Computing details

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.

(S)-5-(2,6-Dichlorophenyl)-3-(2-naphthyl)-1-phenyl-2-pyrazoline trichloromethane hemisolvate

Crystal data

C25H18Cl2N2·0.5CHCl3	F(000) = 980
Mr = 477.00	Dx = 1.390 Mg m^−3
Monoclinic, P21/c	Melting point = 442–443 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.494 (3) Å	Cell parameters from 2253 reflections
b = 10.616 (2) Å	θ = 2.4–21.0°
c = 15.573 (3) Å	µ = 0.48 mm^−1
β = 107.910 (4)°	T = 294 K
V = 2280.1 (8) Å^3	Block, colourless
Z = 2	0.28 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer	4032 independent reflections
Radiation source: fine-focus sealed tube	2298 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −17→15
Tmin = 0.878, Tmax = 0.911	k = −9→12
11344 measured reflections	l = −17→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0572P)^2 + 0.7045P] where P = (Fo^2 + 2Fc^2)/3
4032 reflections	(Δ/σ)max = 0.005
334 parameters	Δρmax = 0.37 e Å^−3
110 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃): δ 8.18 (d, 1H), 7.85–7.78 (m, 4H), 7.48 (dd, 2H), 7.46 (dd, 1H), 7.25 (d, 1H), 7.23–7.13 (m, 3H), 7.04 (dd, 2H), 6.80 (dd, 1H), 6.09 (dd, 1H), 3.87 (dd, 1H), 3.45 (dd, 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.83034 (7)	0.78548 (9)	0.00551 (6)	0.0708 (3)
Cl2	0.78912 (8)	0.49430 (9)	0.28148 (6)	0.0789 (3)
N1	0.63598 (19)	0.3974 (2)	0.09493 (16)	0.0477 (7)
N2	0.71732 (19)	0.4434 (2)	0.07828 (17)	0.0494 (7)
C1	0.8679 (2)	0.7299 (3)	0.1162 (2)	0.0495 (8)
C2	0.9518 (3)	0.7822 (4)	0.1744 (3)	0.0676 (11)
H2	0.9853	0.8442	0.1540	0.081*
C3	0.9852 (3)	0.7414 (4)	0.2626 (3)	0.0766 (12)
H3	1.0417	0.7753	0.3017	0.092*
C4	0.9352 (3)	0.6514 (4)	0.2923 (3)	0.0695 (11)
H4	0.9578	0.6239	0.3518	0.083*
C5	0.8510 (2)	0.6010 (3)	0.2344 (2)	0.0542 (9)
C6	0.8146 (2)	0.6372 (3)	0.1438 (2)	0.0433 (8)
C7	0.7212 (2)	0.5829 (3)	0.0790 (2)	0.0442 (8)
H7	0.7144	0.6127	0.0178	0.053*
C8	0.6288 (2)	0.6174 (3)	0.1029 (2)	0.0476 (8)
H8A	0.6443	0.6637	0.1592	0.057*
H8B	0.5848	0.6672	0.0555	0.057*
C9	0.5859 (2)	0.4904 (3)	0.1112 (2)	0.0447 (8)
C10	0.4983 (2)	0.4709 (3)	0.13736 (19)	0.0430 (8)
C11	0.4476 (2)	0.5712 (3)	0.15551 (19)	0.0470 (8)
H11	0.4694	0.6523	0.1500	0.056*
C12	0.3636 (2)	0.5561 (3)	0.18226 (19)	0.0451 (8)
C13	0.3125 (2)	0.6591 (3)	0.2032 (2)	0.0563 (9)
H13	0.3342	0.7407	0.1993	0.068*
C14	0.2322 (3)	0.6407 (4)	0.2291 (2)	0.0666 (10)
H14	0.2003	0.7095	0.2438	0.080*
C15	0.1969 (3)	0.5185 (4)	0.2336 (3)	0.0719 (11)
H15	0.1408	0.5069	0.2499	0.086*
C16	0.2445 (3)	0.4170 (4)	0.2144 (2)	0.0626 (10)
H16	0.2207	0.3365	0.2181	0.075*
C17	0.3294 (2)	0.4315 (3)	0.1888 (2)	0.0476 (8)
C18	0.3829 (2)	0.3292 (3)	0.1701 (2)	0.0531 (9)
H18	0.3613	0.2475	0.1740	0.064*
C19	0.4649 (2)	0.3468 (3)	0.1466 (2)	0.0498 (8)
H19	0.4994	0.2775	0.1364	0.060*
C20	0.7763 (2)	0.3633 (3)	0.04780 (18)	0.0418 (8)
C21	0.8525 (2)	0.4103 (3)	0.0205 (2)	0.0528 (9)
H21	0.8636	0.4966	0.0216	0.063*
C22	0.9120 (3)	0.3294 (3)	−0.0083 (2)	0.0615 (10)
H22	0.9626	0.3617	−0.0266	0.074*
C23	0.8965 (3)	0.2009 (4)	−0.0100 (2)	0.0650 (10)
H23	0.9366	0.1465	−0.0290	0.078*
C24	0.8220 (3)	0.1548 (3)	0.0165 (2)	0.0662 (10)
H24	0.8111	0.0684	0.0147	0.079*
C25	0.7620 (3)	0.2340 (3)	0.0461 (2)	0.0547 (9)
H25	0.7121	0.2004	0.0648	0.066*
Cl3'	0.3908 (4)	0.4413 (5)	0.4506 (5)	0.105 (2)	0.30
Cl4'	0.5573 (6)	0.5354 (8)	0.5856 (5)	0.150 (3)	0.30
Cl5'	0.5598 (5)	0.4870 (7)	0.3983 (4)	0.143 (3)	0.30
C26'	0.5230 (7)	0.4357 (12)	0.4896 (6)	0.094 (4)	0.30
H26B	0.5382	0.3502	0.5087	0.112*	0.30
Cl3	0.3965 (6)	0.4476 (9)	0.5046 (6)	0.126 (2)	0.20
Cl4	0.5982 (7)	0.5234 (10)	0.5732 (6)	0.092 (3)	0.20
Cl5	0.5238 (8)	0.4450 (10)	0.3966 (6)	0.128 (3)	0.20
C26	0.4898 (8)	0.5339 (15)	0.4789 (8)	0.097 (7)	0.20
H26A	0.4634	0.6165	0.4620	0.117*	0.20

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0780 (7)	0.0635 (6)	0.0747 (6)	−0.0146 (5)	0.0290 (5)	0.0068 (5)
Cl2	0.0957 (8)	0.0770 (7)	0.0581 (5)	−0.0070 (6)	0.0148 (5)	0.0143 (5)
N1	0.0509 (17)	0.0424 (15)	0.0528 (15)	−0.0044 (13)	0.0202 (13)	−0.0049 (13)
N2	0.0504 (16)	0.0398 (15)	0.0650 (17)	−0.0052 (13)	0.0279 (14)	−0.0076 (13)
C1	0.046 (2)	0.048 (2)	0.059 (2)	−0.0025 (16)	0.0217 (16)	−0.0108 (16)
C2	0.052 (2)	0.072 (3)	0.085 (3)	−0.0190 (19)	0.030 (2)	−0.030 (2)
C3	0.044 (2)	0.109 (3)	0.071 (3)	−0.008 (2)	0.009 (2)	−0.036 (2)
C4	0.054 (2)	0.089 (3)	0.058 (2)	0.007 (2)	0.006 (2)	−0.017 (2)
C5	0.051 (2)	0.051 (2)	0.060 (2)	0.0072 (17)	0.0163 (18)	−0.0072 (17)
C6	0.0411 (18)	0.0401 (18)	0.0475 (18)	0.0039 (14)	0.0120 (15)	−0.0060 (15)
C7	0.0436 (19)	0.0424 (18)	0.0456 (17)	−0.0022 (15)	0.0121 (15)	−0.0022 (15)
C8	0.0443 (19)	0.0431 (19)	0.0552 (19)	0.0023 (15)	0.0150 (16)	−0.0022 (15)
C9	0.0434 (18)	0.0442 (19)	0.0438 (17)	−0.0009 (16)	0.0092 (14)	−0.0019 (15)
C10	0.0392 (18)	0.0444 (19)	0.0440 (17)	−0.0022 (15)	0.0107 (15)	−0.0007 (14)
C11	0.048 (2)	0.0418 (19)	0.0508 (19)	−0.0061 (15)	0.0146 (16)	0.0008 (15)
C12	0.0416 (19)	0.050 (2)	0.0415 (17)	−0.0029 (16)	0.0100 (15)	0.0014 (15)
C13	0.053 (2)	0.053 (2)	0.065 (2)	0.0040 (17)	0.0216 (18)	0.0010 (17)
C14	0.061 (2)	0.071 (3)	0.075 (2)	0.012 (2)	0.031 (2)	0.001 (2)
C15	0.057 (2)	0.088 (3)	0.079 (3)	0.003 (2)	0.034 (2)	0.008 (2)
C16	0.058 (2)	0.067 (2)	0.065 (2)	−0.006 (2)	0.0222 (19)	0.0155 (19)
C17	0.045 (2)	0.055 (2)	0.0412 (17)	−0.0041 (17)	0.0101 (15)	0.0053 (16)
C18	0.057 (2)	0.043 (2)	0.057 (2)	−0.0098 (17)	0.0152 (17)	0.0062 (16)
C19	0.051 (2)	0.0459 (19)	0.054 (2)	0.0001 (16)	0.0181 (17)	0.0005 (16)
C20	0.0432 (18)	0.0447 (19)	0.0362 (16)	0.0051 (15)	0.0101 (14)	−0.0053 (14)
C21	0.057 (2)	0.051 (2)	0.055 (2)	0.0015 (17)	0.0231 (17)	−0.0065 (16)
C22	0.060 (2)	0.069 (3)	0.062 (2)	0.0031 (19)	0.0282 (18)	−0.0050 (19)
C23	0.066 (3)	0.072 (3)	0.058 (2)	0.017 (2)	0.0202 (19)	−0.0104 (19)
C24	0.078 (3)	0.045 (2)	0.075 (2)	0.007 (2)	0.023 (2)	−0.0119 (19)
C25	0.059 (2)	0.044 (2)	0.063 (2)	−0.0033 (17)	0.0217 (18)	−0.0061 (17)
Cl3'	0.118 (4)	0.060 (3)	0.116 (4)	0.003 (2)	0.005 (3)	−0.021 (3)
Cl4'	0.154 (5)	0.155 (4)	0.118 (4)	−0.002 (4)	0.011 (4)	−0.019 (3)
Cl5'	0.153 (4)	0.128 (4)	0.135 (4)	0.003 (3)	0.024 (3)	0.028 (3)
C26'	0.097 (6)	0.089 (6)	0.090 (6)	0.013 (5)	0.022 (4)	0.011 (5)
Cl3	0.127 (2)	0.126 (2)	0.127 (2)	0.0017 (11)	0.0395 (12)	0.0006 (11)
Cl4	0.096 (5)	0.094 (5)	0.082 (4)	0.014 (4)	0.019 (3)	−0.002 (3)
Cl5	0.137 (5)	0.125 (5)	0.110 (4)	−0.007 (4)	0.019 (4)	−0.014 (4)
C26	0.103 (8)	0.087 (8)	0.095 (8)	−0.003 (5)	0.020 (5)	−0.007 (5)

Geometric parameters (Å, º)

Cl1—C1	1.742 (3)	C21—C22	1.386 (4)
Cl2—C5	1.741 (4)	C21—H21	0.9300
N1—C9	1.295 (4)	C22—C23	1.381 (5)
N1—N2	1.373 (3)	C22—H22	0.9300
N2—C20	1.389 (4)	C23—C24	1.361 (5)
N2—C7	1.481 (4)	C23—H23	0.9300
C1—C2	1.390 (4)	C24—C25	1.386 (5)
C1—C6	1.398 (4)	C24—H24	0.9300
C2—C3	1.377 (5)	C25—H25	0.9300
C2—H2	0.9300	Cl3'—Cl4'^i	1.098 (11)
C3—C4	1.364 (5)	Cl3'—C26'	1.825 (9)
C3—H3	0.9300	Cl3'—C26'^i	1.848 (12)
C4—C5	1.382 (5)	Cl3'—Cl5'^i	2.365 (9)
C4—H4	0.9300	Cl4'—Cl3'^i	1.098 (11)
C5—C6	1.400 (4)	Cl4'—C26'^i	1.408 (12)
C6—C7	1.531 (4)	Cl4'—C26'	1.773 (9)
C7—C8	1.540 (4)	Cl4'—Cl5'^i	1.807 (11)
C7—H7	0.9800	Cl5'—C26'	1.752 (9)
C8—C9	1.507 (4)	Cl5'—Cl4'^i	1.807 (11)
C8—H8A	0.9700	Cl5'—Cl3'^i	2.365 (9)
C8—H8B	0.9700	C26'—Cl4'^i	1.408 (12)
C9—C10	1.463 (4)	C26'—C26'^i	1.59 (2)
C10—C11	1.371 (4)	C26'—Cl3'^i	1.848 (12)
C10—C19	1.426 (4)	C26'—H26B	0.9600
C11—C12	1.413 (4)	Cl3—Cl4^i	1.275 (13)
C11—H11	0.9300	Cl3—C26^i	1.600 (16)
C12—C13	1.414 (4)	Cl3—C26	1.778 (10)
C12—C17	1.428 (4)	Cl3—Cl5^i	1.977 (12)
C13—C14	1.358 (5)	Cl4—Cl3^i	1.275 (13)
C13—H13	0.9300	Cl4—C26^i	1.421 (16)
C14—C15	1.404 (5)	Cl4—C26	1.794 (10)
C14—H14	0.9300	Cl4—Cl5^i	1.994 (15)
C15—C16	1.362 (5)	Cl5—C26	1.780 (11)
C15—H15	0.9300	Cl5—Cl3^i	1.977 (12)
C16—C17	1.413 (5)	Cl5—Cl4^i	1.994 (15)
C16—H16	0.9300	Cl5—C26^i	2.021 (18)
C17—C18	1.416 (4)	C26—C26^i	0.96 (3)
C18—C19	1.361 (4)	C26—Cl4^i	1.421 (16)
C18—H18	0.9300	C26—Cl3^i	1.600 (16)
C19—H19	0.9300	C26—Cl5^i	2.021 (18)
C20—C25	1.387 (4)	C26—H26A	0.9601
C20—C21	1.392 (4)
C9—N1—N2	109.3 (2)	C25—C20—N2	120.5 (3)
N1—N2—C20	120.1 (2)	C25—C20—C21	118.5 (3)
N1—N2—C7	112.8 (2)	N2—C20—C21	121.0 (3)
C20—N2—C7	126.1 (3)	C22—C21—C20	120.5 (3)
C2—C1—C6	122.4 (3)	C22—C21—H21	119.7
C2—C1—Cl1	117.0 (3)	C20—C21—H21	119.7
C6—C1—Cl1	120.6 (2)	C23—C22—C21	120.3 (3)
C3—C2—C1	119.6 (4)	C23—C22—H22	119.9
C3—C2—H2	120.2	C21—C22—H22	119.9
C1—C2—H2	120.2	C24—C23—C22	119.3 (3)
C4—C3—C2	119.9 (3)	C24—C23—H23	120.4
C4—C3—H3	120.1	C22—C23—H23	120.4
C2—C3—H3	120.1	C23—C24—C25	121.4 (3)
C3—C4—C5	120.3 (4)	C23—C24—H24	119.3
C3—C4—H4	119.9	C25—C24—H24	119.3
C5—C4—H4	119.9	C24—C25—C20	120.1 (3)
C4—C5—C6	122.4 (3)	C24—C25—H25	120.0
C4—C5—Cl2	116.3 (3)	C20—C25—H25	120.0
C6—C5—Cl2	121.3 (3)	Cl4'^i—C26'—C26'^i	72.1 (8)
C1—C6—C5	115.5 (3)	Cl4'^i—C26'—Cl5'	68.8 (6)
C1—C6—C7	121.5 (3)	C26'^i—C26'—Cl5'	98.6 (10)
C5—C6—C7	123.0 (3)	Cl4'^i—C26'—Cl4'	121.1 (9)
N2—C7—C6	113.9 (2)	C26'^i—C26'—Cl4'	49.1 (6)
N2—C7—C8	101.9 (2)	Cl5'—C26'—Cl4'	115.0 (7)
C6—C7—C8	114.2 (2)	Cl4'^i—C26'—Cl3'	36.9 (5)
N2—C7—H7	108.9	C26'^i—C26'—Cl3'	65.0 (6)
C6—C7—H7	108.9	Cl5'—C26'—Cl3'	105.7 (6)
C8—C7—H7	108.9	Cl4'—C26'—Cl3'	104.8 (6)
C9—C8—C7	102.7 (2)	Cl4'^i—C26'—Cl3'^i	121.5 (10)
C9—C8—H8A	111.2	C26'^i—C26'—Cl3'^i	63.5 (7)
C7—C8—H8A	111.2	Cl5'—C26'—Cl3'^i	82.1 (5)
C9—C8—H8B	111.2	Cl4'—C26'—Cl3'^i	35.2 (4)
C7—C8—H8B	111.2	Cl3'—C26'—Cl3'^i	128.5 (7)
H8A—C8—H8B	109.1	Cl4'^i—C26'—H26B	121.1
N1—C9—C10	122.2 (3)	C26'^i—C26'—H26B	144.8
N1—C9—C8	113.2 (3)	Cl5'—C26'—H26B	116.6
C10—C9—C8	124.5 (3)	Cl4'—C26'—H26B	109.0
C11—C10—C19	118.5 (3)	Cl3'—C26'—H26B	104.5
C11—C10—C9	120.9 (3)	Cl3'^i—C26'—H26B	117.2
C19—C10—C9	120.6 (3)	C26^i—C26—Cl4^i	95.9 (17)
C10—C11—C12	122.5 (3)	C26^i—C26—Cl3^i	84.1 (13)
C10—C11—H11	118.7	Cl4^i—C26—Cl3^i	147.5 (12)
C12—C11—H11	118.7	C26^i—C26—Cl3	63.5 (13)
C11—C12—C13	122.7 (3)	Cl4^i—C26—Cl3	45.3 (6)
C11—C12—C17	118.4 (3)	Cl3^i—C26—Cl3	147.6 (10)
C13—C12—C17	118.8 (3)	C26^i—C26—Cl5	90.0 (18)
C14—C13—C12	121.0 (3)	Cl4^i—C26—Cl5	76.1 (8)
C14—C13—H13	119.5	Cl3^i—C26—Cl5	71.4 (6)
C12—C13—H13	119.5	Cl3—C26—Cl5	106.7 (9)
C13—C14—C15	120.5 (4)	C26^i—C26—Cl4	52.0 (12)
C13—C14—H14	119.8	Cl4^i—C26—Cl4	147.9 (11)
C15—C14—H14	119.8	Cl3^i—C26—Cl4	43.7 (5)
C16—C15—C14	120.2 (4)	Cl3—C26—Cl4	108.6 (8)
C16—C15—H15	119.9	Cl5—C26—Cl4	100.9 (7)
C14—C15—H15	119.9	C26^i—C26—Cl5^i	61.7 (13)
C15—C16—C17	121.3 (3)	Cl4^i—C26—Cl5^i	105.1 (9)
C15—C16—H16	119.3	Cl3^i—C26—Cl5^i	103.4 (7)
C17—C16—H16	119.3	Cl3—C26—Cl5^i	62.3 (5)
C16—C17—C18	123.6 (3)	Cl5—C26—Cl5^i	151.7 (10)
C16—C17—C12	118.2 (3)	Cl4—C26—Cl5^i	62.7 (5)
C18—C17—C12	118.2 (3)	C26^i—C26—H26A	152.5
C19—C18—C17	122.0 (3)	Cl4^i—C26—H26A	91.3
C19—C18—H18	119.0	Cl3^i—C26—H26A	103.6
C17—C18—H18	119.0	Cl3—C26—H26A	105.4
C18—C19—C10	120.4 (3)	Cl5—C26—H26A	117.5
C18—C19—H19	119.8	Cl4—C26—H26A	117.1
C10—C19—H19	119.8	Cl5^i—C26—H26A	90.8
C9—N1—N2—C20	−171.8 (3)	C8—C9—C10—C19	−177.8 (3)
C9—N1—N2—C7	−3.0 (3)	C19—C10—C11—C12	−0.4 (4)
C6—C1—C2—C3	0.5 (5)	C9—C10—C11—C12	−179.0 (3)
Cl1—C1—C2—C3	−179.7 (3)	C10—C11—C12—C13	178.4 (3)
C1—C2—C3—C4	−0.7 (6)	C10—C11—C12—C17	−1.2 (4)
C2—C3—C4—C5	−0.1 (6)	C11—C12—C13—C14	−179.7 (3)
C3—C4—C5—C6	1.2 (6)	C17—C12—C13—C14	−0.1 (5)
C3—C4—C5—Cl2	−176.0 (3)	C12—C13—C14—C15	−1.4 (5)
C2—C1—C6—C5	0.5 (5)	C13—C14—C15—C16	1.7 (6)
Cl1—C1—C6—C5	−179.3 (2)	C14—C15—C16—C17	−0.5 (5)
C2—C1—C6—C7	178.7 (3)	C15—C16—C17—C18	178.5 (3)
Cl1—C1—C6—C7	−1.0 (4)	C15—C16—C17—C12	−1.0 (5)
C4—C5—C6—C1	−1.4 (5)	C11—C12—C17—C16	−179.1 (3)
Cl2—C5—C6—C1	175.7 (2)	C13—C12—C17—C16	1.3 (4)
C4—C5—C6—C7	−179.6 (3)	C11—C12—C17—C18	1.4 (4)
Cl2—C5—C6—C7	−2.5 (4)	C13—C12—C17—C18	−178.2 (3)
N1—N2—C7—C6	125.5 (3)	C16—C17—C18—C19	−179.3 (3)
C20—N2—C7—C6	−66.5 (4)	C12—C17—C18—C19	0.2 (5)
N1—N2—C7—C8	2.1 (3)	C17—C18—C19—C10	−1.9 (5)
C20—N2—C7—C8	170.1 (3)	C11—C10—C19—C18	2.0 (4)
C1—C6—C7—N2	131.1 (3)	C9—C10—C19—C18	−179.4 (3)
C5—C6—C7—N2	−50.7 (4)	N1—N2—C20—C25	−9.2 (4)
C1—C6—C7—C8	−112.4 (3)	C7—N2—C20—C25	−176.4 (3)
C5—C6—C7—C8	65.7 (4)	N1—N2—C20—C21	172.4 (3)
N2—C7—C8—C9	−0.5 (3)	C7—N2—C20—C21	5.2 (4)
C6—C7—C8—C9	−123.7 (3)	C25—C20—C21—C22	0.5 (4)
N2—N1—C9—C10	−175.8 (2)	N2—C20—C21—C22	178.9 (3)
N2—N1—C9—C8	2.6 (3)	C20—C21—C22—C23	−0.2 (5)
C7—C8—C9—N1	−1.2 (3)	C21—C22—C23—C24	0.4 (5)
C7—C8—C9—C10	177.2 (3)	C22—C23—C24—C25	−0.7 (5)
N1—C9—C10—C11	179.0 (3)	C23—C24—C25—C20	1.0 (5)
C8—C9—C10—C11	0.7 (4)	N2—C20—C25—C24	−179.3 (3)
N1—C9—C10—C19	0.5 (4)	C21—C20—C25—C24	−0.9 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.