An enantiomerically pure potential toxaphene congener: (1R,2S,3S,4R,7S)-2-endo,3-exo,5,5-tetra­chloro-7-(chloro­methyl)-1,7-bis­(di­chloro­methyl)­bi­cyclo­[2.2.1]­heptane

A new enantiomerically pure potential toxaphene congener (C₁₀H₉Cl₉) has been isolated from a reaction mixture obtained by the free radical chlorination of (1S)-2-endo-chloro­bornane and its absolute configuration determined. It crystallizes in the monoclinic space group C2 with two mol­ecules in the asymmetric unit. This is the first report of the preparation of a single enantiomer of a synthetic poly­chloro­terpene on a multi-milligram scale.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.025
• wR factor = 0.065
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C12    ..  CL12    ..      82.00 Deg.
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C16    ..  CL14    ..      87.00 Deg.
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C16    ..  CL13    ..      87.00 Deg.
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C22    ..  CL22    ..      85.00 Deg.
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C23    ..  CL21    ..      88.00 Deg.
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C24    ..  CL22    ..      80.00 Deg.
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C26    ..  CL23    ..      82.00 Deg.
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C26    ..  CL24    ..      89.00 Deg.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C13    -   H13    ...       0.83 Ang.
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C24    -   H24    ...       0.82 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H22    ..  H282    ..       1.94 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl13   ..  Cl13    ..       3.45 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl14   ..  Cl27    ..       3.38 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl15   ..  Cl26    ..       3.28 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl15   ..  Cl19    ..       3.35 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl21   ..  Cl25    ..       3.24 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H161   ..  CL19    ..       2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H181   ..  CL18    ..       2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H261   ..  CL29    ..       2.84 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H281   ..  CL28    ..       2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19    ..  CL26    ..       2.89 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C13    ..  CL11    ..      90.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C16    ..  CL19    ..      92.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C26    ..  CL29    ..      93.00 Deg.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10 H9 Cl9

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.96
           From the CIF: _reflns_number_total               6925
           Count of symmetry unique reflns         3614
           Completeness (_total/calc)            191.62%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3311
           Fraction of Friedel pairs measured     0.916
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   8 ALERT level B = Potentially serious problem
  20 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
  21 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (Version 9; McArdle, 1993).

(I)

Crystal data

C10H9Cl9	F(000) = 1776
Mr = 448.22	Dx = 1.871 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71069 Å
a = 14.891 (3) Å	Cell parameters from 25 reflections
b = 13.416 (3) Å	θ = 14–18°
c = 15.936 (3) Å	µ = 1.56 mm^−1
β = 91.781 (16)°	T = 298 K
V = 3182.1 (11) Å^3	Block, colourless
Z = 8	0.50 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	6151 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.009
Graphite monochromator	θmax = 27.0°, θmin = 1.3°
ω–2θ scans	h = −18→18
Absorption correction: ψ scan (ABSCALC in OSCAIL; McArdle & Daly, 1999; North et al, 1968)	k = −17→17
Tmin = 0.508, Tmax = 0.651	l = −20→20
7713 measured reflections	3 standard reflections every 120 min
6925 independent reflections	intensity decay: 10%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	All H-atom parameters refined
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.0349P)^2 + 1.5524P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
6925 reflections	Δρmax = 0.35 e Å^−3
415 parameters	Δρmin = −0.27 e Å^−3
1 restraint	Absolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (5)

Special details

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
Cl12	0.83412 (5)	0.69312 (5)	0.72010 (4)	0.04790 (15)
Cl14	0.85565 (5)	0.37192 (5)	0.79666 (5)	0.04939 (16)
Cl22	1.13253 (6)	0.47848 (8)	0.43603 (5)	0.0683 (2)
Cl16	0.70289 (5)	0.66666 (6)	1.07442 (4)	0.05403 (17)
Cl11	0.64399 (5)	0.49068 (6)	0.71292 (4)	0.05484 (17)
Cl13	0.88831 (5)	0.41210 (5)	0.96839 (5)	0.04776 (15)
Cl15	0.85973 (5)	0.80140 (5)	0.91133 (5)	0.05377 (17)
Cl18	0.54616 (5)	0.68902 (6)	0.88755 (6)	0.05916 (19)
Cl19	0.51464 (5)	0.47749 (7)	0.88036 (6)	0.0666 (2)
Cl17	0.89105 (5)	0.63636 (6)	1.05151 (4)	0.05540 (18)
Cl21	1.33784 (6)	0.65696 (8)	0.47537 (5)	0.0715 (2)
Cl29	1.44041 (5)	0.65486 (6)	0.66603 (6)	0.0636 (2)
Cl27	1.04265 (5)	0.50466 (7)	0.75861 (5)	0.0656 (2)
Cl25	1.08023 (6)	0.35132 (6)	0.61525 (7)	0.0706 (3)
Cl28	1.40410 (5)	0.44375 (6)	0.64595 (6)	0.0648 (2)
Cl26	1.22465 (6)	0.45262 (6)	0.80639 (4)	0.05683 (18)
Cl24	1.12139 (7)	0.78901 (7)	0.53517 (7)	0.0822 (3)
Cl23	1.07002 (6)	0.73506 (6)	0.69752 (7)	0.0713 (2)
H22	1.293 (2)	0.501 (3)	0.5164 (19)	0.050 (8)*
H23	1.165 (2)	0.630 (3)	0.465 (2)	0.050 (8)*
H262	1.249 (2)	0.697 (2)	0.707 (2)	0.050 (8)*
H261	1.272 (2)	0.737 (2)	0.6128 (19)	0.043 (8)*
H24	1.070 (2)	0.570 (2)	0.5827 (18)	0.045 (8)*
H282	1.215 (2)	0.407 (3)	0.571 (2)	0.059 (9)*
H281	1.2216 (19)	0.382 (2)	0.6582 (18)	0.033 (7)*
H29	1.163 (2)	0.601 (3)	0.7623 (19)	0.050 (8)*
H210	1.3456 (19)	0.562 (2)	0.7374 (18)	0.041 (7)*
H12	0.664 (2)	0.646 (3)	0.7656 (18)	0.050 (8)*
H14	0.8939 (17)	0.5842 (18)	0.8695 (14)	0.021 (5)*
H181	0.720 (2)	0.760 (2)	0.939 (2)	0.047 (8)*
H13	0.8118 (17)	0.540 (2)	0.7371 (16)	0.026 (6)*
H161	0.6938 (18)	0.399 (2)	0.8563 (17)	0.033 (7)*
H19	0.7760 (17)	0.534 (2)	1.0256 (16)	0.032 (7)*
H182	0.7357 (18)	0.748 (2)	0.8434 (18)	0.035 (7)*
H162	0.710 (2)	0.424 (2)	0.950 (2)	0.048 (8)*
H110	0.597 (2)	0.567 (3)	0.967 (2)	0.051 (9)*
C11	0.68617 (15)	0.55493 (17)	0.87733 (14)	0.0320 (5)
C12	0.69481 (16)	0.57900 (19)	0.78264 (15)	0.0345 (5)
C13	0.79737 (17)	0.58265 (19)	0.77156 (15)	0.0339 (5)
C14	0.83749 (15)	0.56618 (17)	0.86089 (14)	0.0303 (4)
C15	0.82215 (16)	0.45343 (18)	0.87968 (15)	0.0350 (5)
C16	0.71987 (16)	0.44712 (19)	0.89310 (17)	0.0369 (5)
C17	0.76772 (14)	0.61948 (16)	0.91693 (13)	0.0287 (4)
C18	0.75774 (17)	0.73198 (18)	0.89983 (17)	0.0364 (5)
C19	0.78277 (16)	0.6015 (2)	1.01270 (15)	0.0359 (5)
C21	1.27029 (15)	0.58521 (19)	0.62614 (14)	0.0338 (5)
C22	1.27171 (18)	0.5686 (2)	0.52961 (16)	0.0441 (6)
C23	1.1718 (2)	0.5786 (3)	0.50235 (18)	0.0499 (7)
C24	1.12279 (18)	0.5880 (2)	0.58561 (17)	0.0408 (6)
C25	1.14139 (18)	0.6966 (2)	0.6159 (2)	0.0491 (7)
C26	1.24097 (17)	0.6935 (2)	0.64407 (19)	0.0436 (6)
C27	1.18195 (15)	0.52301 (17)	0.64710 (15)	0.0319 (5)
C28	1.18685 (18)	0.4120 (2)	0.62245 (18)	0.0382 (5)
C29	1.15740 (18)	0.5321 (2)	0.74048 (17)	0.0408 (5)
C110	0.59323 (17)	0.5709 (2)	0.91294 (19)	0.0434 (6)
C210	1.35729 (17)	0.5598 (2)	0.67503 (18)	0.0422 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl12	0.0521 (4)	0.0492 (4)	0.0428 (3)	−0.0083 (3)	0.0092 (3)	0.0139 (3)
Cl14	0.0557 (4)	0.0373 (3)	0.0559 (4)	0.0008 (3)	0.0112 (3)	−0.0088 (3)
Cl22	0.0703 (5)	0.0922 (6)	0.0415 (4)	−0.0267 (5)	−0.0113 (3)	−0.0073 (4)
Cl16	0.0637 (4)	0.0593 (4)	0.0397 (3)	0.0162 (3)	0.0120 (3)	−0.0038 (3)
Cl11	0.0514 (4)	0.0649 (4)	0.0475 (3)	−0.0152 (3)	−0.0100 (3)	−0.0100 (3)
Cl13	0.0462 (3)	0.0425 (3)	0.0541 (4)	0.0080 (3)	−0.0065 (3)	0.0084 (3)
Cl15	0.0537 (4)	0.0414 (3)	0.0657 (4)	−0.0185 (3)	−0.0053 (3)	0.0028 (3)
Cl18	0.0365 (3)	0.0621 (4)	0.0790 (5)	0.0115 (3)	0.0030 (3)	−0.0021 (4)
Cl19	0.0377 (3)	0.0743 (5)	0.0882 (6)	−0.0239 (3)	0.0091 (3)	−0.0050 (4)
Cl17	0.0501 (4)	0.0686 (5)	0.0465 (3)	−0.0055 (3)	−0.0153 (3)	0.0012 (3)
Cl21	0.0684 (5)	0.0956 (6)	0.0511 (4)	−0.0371 (5)	0.0106 (3)	0.0144 (4)
Cl29	0.0391 (3)	0.0612 (5)	0.0895 (5)	−0.0150 (3)	−0.0133 (3)	−0.0009 (4)
Cl27	0.0552 (4)	0.0774 (5)	0.0659 (5)	−0.0170 (4)	0.0294 (4)	−0.0149 (4)
Cl25	0.0532 (4)	0.0463 (4)	0.1136 (7)	−0.0203 (3)	0.0251 (4)	−0.0278 (4)
Cl28	0.0438 (4)	0.0528 (4)	0.0971 (6)	0.0112 (3)	−0.0107 (4)	−0.0118 (4)
Cl26	0.0886 (5)	0.0449 (4)	0.0369 (3)	0.0043 (4)	0.0007 (3)	0.0080 (3)
Cl24	0.0727 (6)	0.0553 (5)	0.1166 (8)	−0.0009 (4)	−0.0288 (5)	0.0398 (5)
Cl23	0.0539 (4)	0.0454 (4)	0.1153 (7)	0.0108 (3)	0.0137 (4)	−0.0112 (4)
C11	0.0289 (11)	0.0328 (12)	0.0344 (11)	−0.0047 (9)	0.0031 (9)	0.0025 (9)
C12	0.0311 (11)	0.0375 (13)	0.0348 (11)	−0.0057 (9)	−0.0016 (9)	−0.0007 (10)
C13	0.0393 (12)	0.0321 (11)	0.0306 (11)	−0.0031 (9)	0.0072 (9)	0.0011 (10)
C14	0.0272 (11)	0.0297 (11)	0.0341 (11)	−0.0037 (9)	0.0021 (9)	0.0005 (9)
C15	0.0364 (12)	0.0305 (11)	0.0381 (11)	0.0014 (9)	0.0018 (9)	0.0022 (9)
C16	0.0376 (12)	0.0303 (11)	0.0429 (13)	−0.0071 (10)	0.0052 (10)	0.0026 (10)
C17	0.0296 (10)	0.0276 (10)	0.0289 (10)	−0.0018 (8)	0.0010 (8)	0.0030 (8)
C18	0.0363 (12)	0.0304 (12)	0.0423 (13)	−0.0036 (10)	0.0001 (10)	0.0035 (10)
C19	0.0384 (12)	0.0377 (13)	0.0318 (11)	0.0038 (10)	0.0029 (9)	0.0018 (9)
C21	0.0296 (11)	0.0370 (12)	0.0345 (11)	−0.0051 (9)	−0.0028 (9)	0.0026 (10)
C22	0.0394 (13)	0.0565 (17)	0.0364 (13)	−0.0138 (12)	0.0018 (10)	0.0040 (12)
C23	0.0472 (15)	0.0612 (18)	0.0405 (14)	−0.0155 (13)	−0.0103 (11)	0.0087 (13)
C24	0.0303 (12)	0.0429 (14)	0.0487 (14)	−0.0057 (10)	−0.0064 (10)	0.0047 (11)
C25	0.0396 (14)	0.0381 (14)	0.0690 (18)	0.0009 (11)	−0.0090 (12)	0.0130 (13)
C26	0.0373 (13)	0.0342 (13)	0.0589 (16)	−0.0054 (11)	−0.0029 (12)	0.0066 (12)
C27	0.0295 (11)	0.0296 (11)	0.0367 (11)	−0.0030 (9)	0.0027 (9)	−0.0009 (9)
C28	0.0362 (12)	0.0340 (12)	0.0448 (14)	−0.0040 (10)	0.0061 (11)	−0.0043 (11)
C29	0.0436 (13)	0.0378 (13)	0.0412 (13)	−0.0015 (10)	0.0057 (10)	−0.0009 (10)
C110	0.0303 (12)	0.0504 (16)	0.0498 (16)	−0.0056 (11)	0.0039 (11)	0.0003 (12)
C210	0.0330 (12)	0.0414 (14)	0.0517 (15)	−0.0023 (10)	−0.0071 (11)	−0.0004 (11)

Geometric parameters (Å, º)

Cl12—C13	1.788 (2)	C17—C18	1.540 (3)
Cl14—C15	1.799 (3)	C17—C19	1.554 (3)
Cl22—C23	1.796 (3)	C18—H181	0.94 (3)
Cl16—C19	1.794 (2)	C18—H182	0.97 (3)
Cl11—C12	1.777 (2)	C19—H19	0.93 (3)
Cl13—C15	1.786 (2)	C21—C210	1.529 (3)
Cl15—C18	1.786 (3)	C21—C26	1.546 (4)
Cl18—C110	1.774 (3)	C21—C22	1.555 (3)
Cl19—C110	1.781 (3)	C21—C27	1.602 (3)
Cl17—C19	1.772 (3)	C22—C23	1.542 (4)
Cl21—C22	1.782 (3)	C22—H22	0.98 (4)
Cl29—C210	1.786 (3)	C23—C24	1.540 (4)
Cl27—C29	1.780 (3)	C23—H23	0.92 (3)
Cl25—C28	1.785 (3)	C24—C25	1.557 (4)
Cl28—C210	1.773 (3)	C24—C27	1.563 (3)
Cl26—C29	1.783 (3)	C24—H24	0.82 (3)
Cl24—C25	1.805 (3)	C25—C26	1.536 (4)
Cl23—C25	1.781 (3)	C26—H262	1.01 (3)
C11—C110	1.527 (3)	C26—H261	0.91 (3)
C11—C16	1.549 (3)	C27—C28	1.543 (3)
C11—C12	1.552 (3)	C27—C29	1.548 (3)
C11—C17	1.605 (3)	C28—H282	0.94 (4)
C12—C13	1.544 (3)	C28—H281	0.85 (3)
C12—H12	1.04 (3)	C29—H29	0.98 (3)
C13—C14	1.543 (3)	C110—H110	0.86 (3)
C13—H13	0.83 (3)	C210—H210	1.02 (3)
C14—C15	1.560 (3)	Cl14—Cl27	3.376 (1)
C14—C17	1.564 (3)	Cl13—Cl13^i	3.446 (1)
C14—H14	0.88 (2)	Cl15—Cl26^ii	3.279 (1)
C15—C16	1.547 (3)	Cl15—Cl19^iii	3.349 (1)
C16—H161	0.95 (3)	Cl21—Cl25^iv	3.238 (1)
C16—H162	0.97 (3)
C110—C11—C16	111.3 (2)	C23—C22—H22	109.5 (18)
C110—C11—C12	115.8 (2)	C21—C22—H22	111.0 (18)
C16—C11—C12	108.4 (2)	Cl21—C22—H22	108.6 (19)
C110—C11—C17	117.5 (2)	C24—C23—C22	104.1 (2)
C16—C11—C17	101.70 (18)	C24—C23—Cl22	114.5 (2)
C12—C11—C17	100.69 (16)	C22—C23—Cl22	113.3 (2)
C13—C12—C11	103.29 (18)	C24—C23—H23	117 (2)
C13—C12—Cl11	110.68 (17)	C22—C23—H23	109 (2)
C11—C12—Cl11	114.99 (16)	Cl22—C23—H23	99 (2)
C13—C12—H12	112.3 (17)	C23—C24—C25	105.1 (2)
C11—C12—H12	112.5 (16)	C23—C24—C27	102.8 (2)
Cl11—C12—H12	103.4 (17)	C25—C24—C27	103.68 (19)
C14—C13—C12	104.24 (18)	C23—C24—H24	114 (2)
C14—C13—Cl12	115.26 (17)	C25—C24—H24	117 (2)
C12—C13—Cl12	113.38 (18)	C27—C24—H24	113 (2)
C14—C13—H13	114.2 (17)	C26—C25—C24	103.1 (2)
C12—C13—H13	109.4 (18)	C26—C25—Cl23	112.8 (2)
Cl12—C13—H13	100.6 (18)	C24—C25—Cl23	113.1 (2)
C13—C14—C15	105.14 (19)	C26—C25—Cl24	111.3 (2)
C13—C14—C17	102.49 (18)	C24—C25—Cl24	113.4 (2)
C15—C14—C17	103.30 (17)	Cl23—C25—Cl24	103.46 (15)
C13—C14—H14	116.4 (15)	C25—C26—C21	104.3 (2)
C15—C14—H14	112.3 (16)	C25—C26—H262	112.2 (17)
C17—C14—H14	115.7 (15)	C21—C26—H262	101.9 (19)
C16—C15—C14	103.31 (19)	C25—C26—H261	109.4 (19)
C16—C15—Cl13	113.25 (17)	C21—C26—H261	110.6 (19)
C14—C15—Cl13	111.87 (17)	H262—C26—H261	117 (3)
C16—C15—Cl14	111.42 (17)	C28—C27—C29	109.6 (2)
C14—C15—Cl14	113.75 (16)	C28—C27—C24	114.2 (2)
Cl13—C15—Cl14	103.57 (13)	C29—C27—C24	114.4 (2)
C15—C16—C11	104.00 (18)	C28—C27—C21	113.85 (19)
C15—C16—H161	109.7 (16)	C29—C27—C21	112.29 (19)
C11—C16—H161	114.3 (16)	C24—C27—C21	91.66 (18)
C15—C16—H162	109.0 (18)	C27—C28—Cl25	114.06 (18)
C11—C16—H162	112.7 (18)	C27—C28—H282	109 (2)
H161—C16—H162	107 (2)	Cl25—C28—H282	110 (2)
C18—C17—C19	109.63 (19)	C27—C28—H281	108.1 (19)
C18—C17—C14	114.16 (19)	Cl25—C28—H281	110.5 (19)
C19—C17—C14	114.30 (18)	H282—C28—H281	105 (3)
C18—C17—C11	113.06 (18)	C27—C29—Cl27	113.34 (18)
C19—C17—C11	112.75 (17)	C27—C29—Cl26	111.96 (18)
C14—C17—C11	92.10 (16)	Cl27—C29—Cl26	107.76 (15)
C17—C18—Cl15	114.56 (17)	C27—C29—H29	113.1 (18)
C17—C18—H181	110 (2)	Cl27—C29—H29	102.1 (18)
Cl15—C18—H181	104.0 (19)	Cl26—C29—H29	107.9 (18)
C17—C18—H182	114.1 (17)	C11—C110—Cl18	113.38 (19)
Cl15—C18—H182	104.0 (16)	C11—C110—Cl19	112.8 (2)
H181—C18—H182	110 (2)	Cl18—C110—Cl19	108.10 (14)
C17—C19—Cl17	113.81 (16)	C11—C110—H110	109 (2)
C17—C19—Cl16	112.63 (16)	Cl18—C110—H110	107 (2)
Cl17—C19—Cl16	106.96 (14)	Cl19—C110—H110	105 (2)
C17—C19—H19	110.8 (16)	C21—C210—Cl28	113.34 (19)
Cl17—C19—H19	106.4 (16)	C21—C210—Cl29	112.22 (19)
Cl16—C19—H19	105.8 (16)	Cl28—C210—Cl29	109.08 (14)
C210—C21—C26	110.8 (2)	C21—C210—H210	108.8 (16)
C210—C21—C22	115.8 (2)	Cl28—C210—H210	111.6 (17)
C26—C21—C22	109.3 (2)	Cl29—C210—H210	101.2 (17)
C210—C21—C27	117.8 (2)	C15—Cl14—Cl27	93.5 (1)
C26—C21—C27	102.27 (19)	C15—Cl13—Cl13^i	137.3 (1)
C22—C21—C27	99.68 (18)	C18—Cl15—Cl26^ii	76.4 (1)
C23—C22—C21	102.9 (2)	C18—Cl15—Cl19^iii	160.1 (1)
C23—C22—Cl21	110.4 (2)	C22—Cl21—Cl25^iv	166.8 (1)
C21—C22—Cl21	114.16 (19)
C110—C11—C12—C13	165.8 (2)	C21—C22—C23—C24	−6.0 (3)
C16—C11—C12—C13	−68.3 (2)	Cl21—C22—C23—C24	−128.2 (2)
C17—C11—C12—C13	38.0 (2)	C21—C22—C23—Cl22	−131.0 (2)
C110—C11—C12—Cl11	−73.5 (3)	Cl21—C22—C23—Cl22	106.8 (2)
C16—C11—C12—Cl11	52.4 (2)	C22—C23—C24—C25	75.8 (3)
C17—C11—C12—Cl11	158.65 (16)	Cl22—C23—C24—C25	−160.07 (19)
C11—C12—C13—C14	−2.9 (2)	C22—C23—C24—C27	−32.4 (3)
Cl11—C12—C13—C14	−126.52 (18)	Cl22—C23—C24—C27	91.7 (2)
C11—C12—C13—Cl12	−129.05 (18)	C23—C24—C25—C26	−72.1 (3)
Cl11—C12—C13—Cl12	107.36 (18)	C27—C24—C25—C26	35.4 (3)
C12—C13—C14—C15	73.3 (2)	C23—C24—C25—Cl23	165.79 (19)
Cl12—C13—C14—C15	−161.73 (16)	C27—C24—C25—Cl23	−86.7 (2)
C12—C13—C14—C17	−34.4 (2)	C23—C24—C25—Cl24	48.3 (3)
Cl12—C13—C14—C17	90.57 (19)	C27—C24—C25—Cl24	155.85 (18)
C13—C14—C15—C16	−72.7 (2)	C24—C25—C26—C21	0.9 (3)
C17—C14—C15—C16	34.4 (2)	Cl23—C25—C26—C21	123.2 (2)
C13—C14—C15—Cl13	165.16 (16)	Cl24—C25—C26—C21	−121.0 (2)
C17—C14—C15—Cl13	−87.73 (19)	C210—C21—C26—C25	−162.1 (2)
C13—C14—C15—Cl14	48.2 (2)	C22—C21—C26—C25	69.3 (3)
C17—C14—C15—Cl14	155.35 (15)	C27—C21—C26—C25	−35.7 (3)
C14—C15—C16—C11	2.2 (2)	C23—C24—C27—C28	−62.0 (3)
Cl13—C15—C16—C11	123.40 (19)	C25—C24—C27—C28	−171.3 (2)
Cl14—C15—C16—C11	−120.32 (18)	C23—C24—C27—C29	170.6 (2)
C110—C11—C16—C15	−162.8 (2)	C25—C24—C27—C29	61.3 (3)
C12—C11—C16—C15	68.7 (2)	C23—C24—C27—C21	55.1 (2)
C17—C11—C16—C15	−36.8 (2)	C25—C24—C27—C21	−54.1 (2)
C13—C14—C17—C18	−61.5 (2)	C210—C21—C27—C28	−66.7 (3)
C15—C14—C17—C18	−170.62 (19)	C26—C21—C27—C28	171.6 (2)
C13—C14—C17—C19	171.14 (19)	C22—C21—C27—C28	59.3 (3)
C15—C14—C17—C19	62.0 (2)	C210—C21—C27—C29	58.6 (3)
C13—C14—C17—C11	54.96 (19)	C26—C21—C27—C29	−63.1 (2)
C15—C14—C17—C11	−54.14 (19)	C22—C21—C27—C29	−175.4 (2)
C110—C11—C17—C18	−65.7 (3)	C210—C21—C27—C24	175.9 (2)
C16—C11—C17—C18	172.6 (2)	C26—C21—C27—C24	54.2 (2)
C12—C11—C17—C18	61.0 (2)	C22—C21—C27—C24	−58.1 (2)
C110—C11—C17—C19	59.4 (3)	C29—C27—C28—Cl25	71.3 (3)
C16—C11—C17—C19	−62.4 (2)	C24—C27—C28—Cl25	−58.5 (3)
C12—C11—C17—C19	−173.92 (18)	C21—C27—C28—Cl25	−161.96 (17)
C110—C11—C17—C14	176.9 (2)	C28—C27—C29—Cl27	−74.0 (2)
C16—C11—C17—C14	55.13 (19)	C24—C27—C29—Cl27	55.7 (3)
C12—C11—C17—C14	−56.41 (19)	C21—C27—C29—Cl27	158.40 (17)
C19—C17—C18—Cl15	72.6 (2)	C28—C27—C29—Cl26	48.1 (2)
C14—C17—C18—Cl15	−57.1 (2)	C24—C27—C29—Cl26	177.83 (17)
C11—C17—C18—Cl15	−160.65 (16)	C21—C27—C29—Cl26	−79.4 (2)
C18—C17—C19—Cl17	−73.1 (2)	C16—C11—C110—Cl18	−173.96 (18)
C14—C17—C19—Cl17	56.5 (2)	C12—C11—C110—Cl18	−49.5 (3)
C11—C17—C19—Cl17	160.02 (16)	C17—C11—C110—Cl18	69.4 (3)
C18—C17—C19—Cl16	48.9 (2)	C16—C11—C110—Cl19	−50.7 (3)
C14—C17—C19—Cl16	178.51 (16)	C12—C11—C110—Cl19	73.7 (3)
C11—C17—C19—Cl16	−78.0 (2)	C17—C11—C110—Cl19	−167.32 (16)
C210—C21—C22—C23	168.4 (2)	C26—C21—C210—Cl28	−171.15 (18)
C26—C21—C22—C23	−65.7 (3)	C22—C21—C210—Cl28	−46.0 (3)
C27—C21—C22—C23	41.0 (3)	C27—C21—C210—Cl28	71.7 (3)
C210—C21—C22—Cl21	−72.0 (3)	C26—C21—C210—Cl29	−47.0 (3)
C26—C21—C22—Cl21	53.9 (3)	C22—C21—C210—Cl29	78.1 (3)
C27—C21—C22—Cl21	160.68 (18)	C27—C21—C210—Cl29	−164.21 (18)

Symmetry codes: (i) −x+2, y, −z+2; (ii) x−1/2, y+1/2, z; (iii) x+1/2, y+1/2, z; (iv) −x+5/2, y+1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl12	1.04 (4)	2.73 (3)	2.787 (3)	82 (2)
C12—H12···Cl18	1.04 (4)	2.72 (3)	3.179 (3)	107 (2)
C13—H13···Cl14	0.83 (4)	2.52 (3)	2.981 (3)	116 (2)
C13—H13···Cl11	0.83 (4)	2.60 (2)	2.735 (3)	90 (2)
C16—H161···Cl14	0.95 (4)	2.64 (3)	2.768 (3)	87 (2)
C16—H161···Cl11	0.95 (4)	2.68 (3)	3.108 (3)	108 (2)
C16—H161···Cl19	0.95 (4)	2.90 (3)	3.084 (3)	92 (2)
C16—H162···Cl13	0.97 (3)	2.67 (3)	2.787 (3)	87 (2)
C18—H181···Cl16	0.93 (3)	2.52 (3)	3.052 (3)	117 (2)
C18—H181···Cl18	0.93 (3)	2.86 (3)	3.203 (3)	104 (2)
C18—H182···Cl12	0.97 (3)	2.59 (3)	3.158 (3)	117 (2)
C18—H182···C12	0.97 (3)	2.53 (3)	2.910 (4)	103 (2)
C19—H19···Cl13	0.94 (3)	2.53 (3)	3.081 (3)	118 (2)
C19—H19···C16	0.94 (3)	2.53 (3)	2.948 (4)	107 (2)
C22—H22···Cl22	0.99 (4)	2.69 (3)	2.791 (3)	85 (2)
C22—H22···Cl28	0.99 (4)	2.72 (3)	3.147 (3)	107 (2)
C23—H23···Cl21	0.91 (4)	2.60 (3)	2.733 (3)	88 (2)
C23—H23···Cl24	0.91 (4)	2.50 (4)	2.972 (4)	112 (3)
C24—H24···Cl22	0.82 (3)	2.82 (3)	2.808 (3)	80 (2)
C26—H262···Cl23	1.01 (3)	2.71 (3)	2.766 (3)	82 (2)
C26—H261···Cl21	0.90 (3)	2.65 (3)	3.129 (3)	114 (2)
C26—H261···Cl29	0.90 (3)	2.84 (3)	3.024 (3)	93 (2)
C26—H261···Cl24	0.90 (3)	2.62 (3)	2.763 (3)	89 (2)
C28—H282···Cl22	0.94 (3)	2.62 (3)	3.182 (3)	119 (2)
C28—H282···C22	0.94 (3)	2.43 (4)	2.884 (4)	110 (2)
C28—H281···Cl28	0.86 (3)	2.85 (3)	3.273 (3)	112 (2)
C28—H281···Cl26	0.86 (3)	2.54 (3)	3.017 (3)	116 (2)
C29—H29···Cl23	0.99 (4)	2.48 (4)	3.086 (3)	119 (3)
C29—H29···C26	0.99 (4)	2.56 (3)	2.952 (4)	103 (2)
C110—H110···Cl16	0.86 (3)	2.65 (3)	3.268 (3)	129 (3)
C210—H210···Cl26	1.02 (3)	2.59 (3)	3.257 (3)	123 (2)
C19—H19···Cl26^i	0.94 (3)	2.89 (3)	3.512 (3)	125 (2)
C18—H182···Cl26^ii	0.97 (3)	2.81 (3)	3.343 (3)	115 (2)

Symmetry codes: (i) −x+2, y, −z+2; (ii) x−1/2, y+1/2, z.