A dinuclear chloro­(triphenyl­phosphito)copper(I) complex, di-μ₂-chloro-bis­[bis­(triphenyl­phosphito)copper(I)]

The title compound, [Cu₂Cl₂(C₁₈H₁₅O₃P)₄], is a centrosymmetric dinuclear complex, where each Cu^I atom has a distorted tetra­hedral coordination involving two triphenyl­phosphite ligands and two bridging Cl⁻ anions. The mol­ecular structure and packing are stabilized by C—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.052
• wR factor = 0.146
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C33
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C31    -C36           1.36 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.47 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   Cl1     ..       8.10 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   P2      ..       5.08 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   Cl1_a   ..       7.49 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C29
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C34
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C1     -C6            1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C7     -C12           1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C25    -C30           1.37 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

di-µ₂-chloro-bis[bis(triphenylphosphito)copper(I)]

Crystal data

[Cu2Cl2(C18H15O3P)4]	F(000) = 2960
Mr = 1439.06	Dx = 1.396 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -c 2yc	Cell parameters from 25 reflections
a = 28.455 (6) Å	θ = 4–26°
b = 13.737 (3) Å	µ = 0.85 mm^−1
c = 19.396 (4) Å	T = 295 K
β = 115.46 (3)°	Block, blue
V = 6845 (3) Å^3	0.35 × 0.25 × 0.20 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.065
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 1.6°
Graphite monochromator	h = −36→36
ω scans	k = −16→0
14736 measured reflections	l = −23→23
7383 independent reflections	3 standard reflections every 100 reflections
4751 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.146	w = 1/[σ^2(Fo^2) + (0.0719P)^2 + 0.8853P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
7383 reflections	Δρmax = 1.11 e Å^−3
416 parameters	Δρmin = −0.61 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00067 (10)

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
Cu1	0.033959 (14)	0.40213 (3)	0.02275 (2)	0.04495 (14)
Cl1	0.02051 (3)	0.52106 (6)	−0.07159 (5)	0.0497 (2)
P1	0.11996 (3)	0.38329 (6)	0.08638 (4)	0.0413 (2)
P2	−0.01061 (3)	0.26602 (6)	−0.02949 (5)	0.0467 (2)
O1	0.15219 (8)	0.42129 (17)	0.04144 (12)	0.0486 (5)
O2	0.13247 (8)	0.26903 (17)	0.09156 (14)	0.0553 (6)
O3	0.15809 (8)	0.42532 (19)	0.16930 (12)	0.0517 (6)
O4	0.00690 (10)	0.16445 (18)	0.01680 (15)	0.0609 (6)
O5	−0.07057 (8)	0.27603 (17)	−0.04611 (14)	0.0549 (6)
O6	−0.01843 (9)	0.2270 (2)	−0.11153 (14)	0.0626 (7)
C1	0.19000 (11)	0.4949 (2)	0.06324 (17)	0.0426 (7)
C2	0.17575 (14)	0.5901 (3)	0.0552 (2)	0.0567 (9)
H2A	0.1410	0.6075	0.0387	0.068*
C3	0.21374 (17)	0.6610 (3)	0.0721 (2)	0.0725 (11)
H3A	0.2043	0.7264	0.0668	0.087*
C4	0.26454 (18)	0.6361 (4)	0.0963 (3)	0.0783 (12)
H4A	0.2899	0.6839	0.1073	0.094*
C5	0.27794 (16)	0.5402 (4)	0.1044 (3)	0.0896 (15)
H5A	0.3127	0.5232	0.1211	0.107*
C6	0.24110 (13)	0.4676 (3)	0.0884 (2)	0.0677 (11)
H6A	0.2506	0.4023	0.0944	0.081*
C7	0.18215 (12)	0.2279 (2)	0.1148 (2)	0.0474 (8)
C8	0.20983 (14)	0.2022 (3)	0.1894 (2)	0.0608 (9)
H8A	0.1965	0.2136	0.2248	0.073*
C9	0.25827 (16)	0.1589 (3)	0.2117 (3)	0.0723 (11)
H9A	0.2773	0.1406	0.2624	0.087*
C10	0.27780 (15)	0.1434 (3)	0.1610 (3)	0.0728 (12)
H10A	0.3107	0.1162	0.1769	0.087*
C11	0.24989 (17)	0.1672 (3)	0.0866 (3)	0.0727 (11)
H11A	0.2635	0.1547	0.0516	0.087*
C12	0.20087 (15)	0.2104 (3)	0.0618 (2)	0.0613 (9)
H12A	0.1815	0.2267	0.0107	0.074*
C13	0.14326 (12)	0.4340 (3)	0.22902 (19)	0.0482 (8)
C14	0.17537 (15)	0.3927 (3)	0.2980 (2)	0.0610 (9)
H14A	0.2048	0.3580	0.3034	0.073*
C15	0.1631 (2)	0.4037 (4)	0.3589 (3)	0.0804 (13)
H15A	0.1851	0.3779	0.4062	0.097*
C16	0.1196 (2)	0.4514 (4)	0.3511 (3)	0.0926 (16)
H16A	0.1111	0.4565	0.3922	0.111*
C17	0.08808 (17)	0.4923 (5)	0.2821 (3)	0.0980 (19)
H17A	0.0580	0.5249	0.2766	0.118*
C18	0.10018 (15)	0.4859 (3)	0.2205 (2)	0.0745 (12)
H18A	0.0795	0.5162	0.1744	0.089*
C19	0.03286 (13)	0.1600 (3)	0.0960 (2)	0.0555 (9)
C20	0.06839 (18)	0.0865 (3)	0.1271 (3)	0.0795 (13)
H20A	0.0741	0.0415	0.0957	0.095*
C21	0.0952 (2)	0.0800 (5)	0.2046 (4)	0.1067 (19)
H21A	0.1186	0.0291	0.2258	0.128*
C22	0.0883 (2)	0.1469 (5)	0.2515 (3)	0.0952 (16)
H22A	0.1074	0.1426	0.3041	0.114*
C23	0.05312 (18)	0.2200 (4)	0.2201 (3)	0.0791 (12)
H23A	0.0482	0.2655	0.2519	0.095*
C24	0.02479 (15)	0.2276 (3)	0.1423 (2)	0.0636 (10)
H24A	0.0006	0.2774	0.1214	0.076*
C25	−0.10675 (13)	0.1992 (3)	−0.0720 (2)	0.0599 (10)
C26	−0.13707 (15)	0.1912 (4)	−0.1479 (3)	0.0778 (12)
H26A	−0.1326	0.2323	−0.1828	0.093*
C27	−0.17550 (19)	0.1184 (5)	−0.1720 (4)	0.110 (2)
H27A	−0.1970	0.1102	−0.2237	0.132*
C28	−0.1811 (2)	0.0604 (5)	−0.1199 (6)	0.127 (3)
H28A	−0.2071	0.0133	−0.1363	0.152*
C29	−0.1502 (3)	0.0690 (5)	−0.0454 (5)	0.127 (3)
H29A	−0.1544	0.0274	−0.0106	0.152*
C30	−0.11211 (18)	0.1396 (4)	−0.0199 (3)	0.0918 (15)
H30A	−0.0905	0.1463	0.0319	0.110*
C31	0.02399 (14)	0.2040 (3)	−0.1267 (2)	0.0588 (9)
C32	0.0342 (3)	0.1092 (4)	−0.1327 (4)	0.113 (2)
H32A	0.0147	0.0607	−0.1236	0.136*
C33	0.0739 (3)	0.0852 (5)	−0.1524 (5)	0.148 (3)
H33A	0.0810	0.0203	−0.1577	0.178*
C34	0.1029 (2)	0.1571 (5)	−0.1641 (3)	0.1078 (19)
H34A	0.1298	0.1411	−0.1774	0.129*
C35	0.0927 (2)	0.2498 (5)	−0.1566 (3)	0.1026 (17)
H35A	0.1129	0.2983	−0.1638	0.123*
C36	0.05253 (17)	0.2752 (3)	−0.1382 (3)	0.0802 (13)
H36A	0.0452	0.3403	−0.1339	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0334 (2)	0.0427 (2)	0.0524 (2)	0.00235 (16)	0.01230 (17)	0.00010 (18)
Cl1	0.0445 (4)	0.0512 (5)	0.0554 (5)	0.0106 (3)	0.0235 (4)	0.0086 (4)
P1	0.0307 (4)	0.0438 (5)	0.0426 (4)	−0.0007 (3)	0.0095 (3)	0.0008 (4)
P2	0.0355 (4)	0.0427 (5)	0.0579 (5)	−0.0013 (3)	0.0164 (4)	−0.0037 (4)
O1	0.0439 (12)	0.0525 (14)	0.0431 (12)	−0.0088 (10)	0.0128 (10)	−0.0039 (10)
O2	0.0343 (11)	0.0418 (13)	0.0808 (17)	0.0023 (9)	0.0161 (11)	0.0075 (12)
O3	0.0391 (11)	0.0704 (16)	0.0414 (12)	−0.0084 (11)	0.0133 (10)	−0.0036 (11)
O4	0.0584 (15)	0.0396 (14)	0.0777 (17)	0.0021 (11)	0.0226 (13)	−0.0001 (12)
O5	0.0380 (11)	0.0465 (14)	0.0776 (16)	−0.0065 (10)	0.0225 (11)	−0.0095 (12)
O6	0.0455 (12)	0.0750 (18)	0.0629 (15)	−0.0052 (12)	0.0190 (11)	−0.0153 (14)
C1	0.0383 (15)	0.0480 (19)	0.0407 (16)	−0.0041 (13)	0.0161 (13)	−0.0020 (14)
C2	0.0531 (19)	0.049 (2)	0.067 (2)	0.0021 (16)	0.0253 (18)	−0.0002 (18)
C3	0.083 (3)	0.048 (2)	0.091 (3)	−0.010 (2)	0.042 (2)	−0.008 (2)
C4	0.068 (3)	0.071 (3)	0.102 (3)	−0.027 (2)	0.042 (3)	−0.019 (3)
C5	0.044 (2)	0.086 (4)	0.132 (4)	−0.012 (2)	0.031 (2)	−0.024 (3)
C6	0.0436 (19)	0.050 (2)	0.099 (3)	0.0016 (16)	0.021 (2)	−0.004 (2)
C7	0.0380 (16)	0.0376 (18)	0.062 (2)	−0.0004 (13)	0.0175 (15)	0.0031 (15)
C8	0.059 (2)	0.055 (2)	0.062 (2)	0.0091 (18)	0.0209 (18)	0.0063 (18)
C9	0.057 (2)	0.062 (3)	0.073 (3)	0.011 (2)	0.005 (2)	0.006 (2)
C10	0.047 (2)	0.051 (2)	0.113 (4)	0.0072 (17)	0.027 (2)	0.010 (2)
C11	0.076 (3)	0.063 (3)	0.098 (3)	0.012 (2)	0.055 (3)	0.009 (2)
C12	0.068 (2)	0.053 (2)	0.059 (2)	0.0127 (18)	0.0245 (19)	0.0102 (18)
C13	0.0417 (16)	0.051 (2)	0.0493 (18)	−0.0081 (14)	0.0174 (15)	−0.0102 (16)
C14	0.064 (2)	0.066 (3)	0.051 (2)	0.0082 (19)	0.0228 (18)	0.0011 (18)
C15	0.097 (3)	0.093 (3)	0.057 (2)	0.000 (3)	0.038 (2)	−0.002 (2)
C16	0.085 (3)	0.127 (5)	0.076 (3)	−0.018 (3)	0.043 (3)	−0.034 (3)
C17	0.053 (2)	0.146 (5)	0.093 (3)	0.003 (3)	0.030 (2)	−0.061 (4)
C18	0.050 (2)	0.087 (3)	0.064 (2)	0.006 (2)	0.0027 (18)	−0.025 (2)
C19	0.0480 (18)	0.0416 (19)	0.076 (2)	0.0002 (15)	0.0256 (18)	0.0136 (18)
C20	0.085 (3)	0.057 (3)	0.105 (4)	0.019 (2)	0.049 (3)	0.025 (2)
C21	0.101 (4)	0.102 (4)	0.116 (5)	0.045 (3)	0.045 (4)	0.058 (4)
C22	0.083 (3)	0.113 (4)	0.082 (3)	0.017 (3)	0.029 (3)	0.046 (3)
C23	0.084 (3)	0.082 (3)	0.073 (3)	0.005 (3)	0.036 (2)	0.016 (3)
C24	0.058 (2)	0.056 (2)	0.075 (3)	0.0058 (18)	0.026 (2)	0.012 (2)
C25	0.0366 (17)	0.048 (2)	0.094 (3)	−0.0051 (15)	0.0266 (19)	−0.012 (2)
C26	0.047 (2)	0.079 (3)	0.095 (3)	−0.006 (2)	0.019 (2)	−0.023 (3)
C27	0.055 (3)	0.104 (5)	0.142 (5)	−0.010 (3)	0.016 (3)	−0.054 (4)
C28	0.066 (3)	0.067 (4)	0.239 (9)	−0.025 (3)	0.056 (5)	−0.036 (5)
C29	0.088 (4)	0.081 (4)	0.213 (8)	−0.020 (3)	0.066 (5)	0.022 (5)
C30	0.069 (3)	0.082 (3)	0.126 (4)	−0.012 (2)	0.043 (3)	0.018 (3)
C31	0.052 (2)	0.065 (2)	0.057 (2)	−0.0020 (18)	0.0222 (17)	−0.0136 (19)
C32	0.141 (5)	0.064 (3)	0.178 (6)	−0.012 (3)	0.110 (5)	−0.025 (4)
C33	0.199 (8)	0.088 (5)	0.224 (9)	0.035 (5)	0.154 (8)	−0.009 (5)
C34	0.101 (4)	0.129 (5)	0.118 (4)	0.040 (4)	0.069 (4)	0.006 (4)
C35	0.093 (4)	0.113 (5)	0.129 (5)	0.003 (3)	0.074 (4)	0.008 (4)
C36	0.083 (3)	0.065 (3)	0.112 (4)	0.006 (2)	0.059 (3)	0.006 (3)

Geometric parameters (Å, º)

Cu1—P1	2.2321 (11)	C14—H14A	0.9300
Cu1—P2	2.2420 (11)	C15—C16	1.350 (7)
Cu1—Cl1	2.3584 (10)	C15—H15A	0.9300
Cu1—Cl1^i	2.3822 (9)	C16—C17	1.371 (7)
Cl1—Cu1^i	2.3822 (9)	C16—H16A	0.9300
P1—O1	1.600 (2)	C17—C18	1.381 (6)
P1—O2	1.603 (2)	C17—H17A	0.9300
P1—O3	1.612 (2)	C18—H18A	0.9300
P2—O5	1.600 (2)	C19—C20	1.372 (5)
P2—O6	1.601 (3)	C19—C24	1.379 (5)
P2—O4	1.618 (3)	C20—C21	1.364 (7)
O1—C1	1.403 (4)	C20—H20A	0.9300
O2—C7	1.405 (4)	C21—C22	1.365 (8)
O3—C13	1.398 (4)	C21—H21A	0.9300
O4—C19	1.390 (4)	C22—C23	1.362 (7)
O5—C25	1.408 (4)	C22—H22A	0.9300
O6—C31	1.396 (4)	C23—C24	1.376 (6)
C1—C2	1.359 (5)	C23—H23A	0.9300
C1—C6	1.372 (4)	C24—H24A	0.9300
C2—C3	1.385 (5)	C25—C26	1.354 (6)
C2—H2A	0.9300	C25—C30	1.359 (6)
C3—C4	1.358 (6)	C26—C27	1.406 (7)
C3—H3A	0.9300	C26—H26A	0.9300
C4—C5	1.361 (7)	C27—C28	1.349 (10)
C4—H4A	0.9300	C27—H27A	0.9300
C5—C6	1.382 (6)	C28—C29	1.335 (10)
C5—H5A	0.9300	C28—H28A	0.9300
C6—H6A	0.9300	C29—C30	1.378 (8)
C7—C8	1.363 (5)	C29—H29A	0.9300
C7—C12	1.367 (5)	C30—H30A	0.9300
C8—C9	1.388 (5)	C31—C36	1.350 (6)
C8—H8A	0.9300	C31—C32	1.351 (6)
C9—C10	1.339 (6)	C32—C33	1.380 (8)
C9—H9A	0.9300	C32—H32A	0.9300
C10—C11	1.355 (6)	C33—C34	1.367 (9)
C10—H10A	0.9300	C33—H33A	0.9300
C11—C12	1.397 (5)	C34—C35	1.328 (8)
C11—H11A	0.9300	C34—H34A	0.9300
C12—H12A	0.9300	C35—C36	1.380 (6)
C13—C18	1.365 (5)	C35—H35A	0.9300
C13—C14	1.377 (5)	C36—H36A	0.9300
C14—C15	1.377 (5)
P1—Cu1—P2	115.21 (4)	C16—C15—C14	121.0 (4)
P1—Cu1—Cl1	106.44 (4)	C16—C15—H15A	119.5
P2—Cu1—Cl1	110.82 (4)	C14—C15—H15A	119.5
P1—Cu1—Cl1^i	125.28 (4)	C15—C16—C17	119.4 (4)
P2—Cu1—Cl1^i	102.17 (3)	C15—C16—H16A	120.3
Cl1—Cu1—Cl1^i	94.90 (3)	C17—C16—H16A	120.3
Cu1—Cl1—Cu1^i	85.10 (3)	C16—C17—C18	121.1 (4)
O1—P1—O2	100.94 (12)	C16—C17—H17A	119.4
O1—P1—O3	97.42 (11)	C18—C17—H17A	119.4
O2—P1—O3	104.61 (14)	C13—C18—C17	118.2 (4)
O1—P1—Cu1	114.20 (9)	C13—C18—H18A	120.9
O2—P1—Cu1	108.02 (9)	C17—C18—H18A	120.9
O3—P1—Cu1	128.17 (9)	C20—C19—C24	120.4 (4)
O5—P2—O6	98.51 (13)	C20—C19—O4	117.4 (4)
O5—P2—O4	103.49 (13)	C24—C19—O4	122.2 (3)
O6—P2—O4	98.11 (14)	C21—C20—C19	119.3 (5)
O5—P2—Cu1	111.49 (9)	C21—C20—H20A	120.3
O6—P2—Cu1	122.55 (11)	C19—C20—H20A	120.3
O4—P2—Cu1	119.28 (10)	C20—C21—C22	121.2 (5)
C1—O1—P1	128.02 (19)	C20—C21—H21A	119.4
C7—O2—P1	125.4 (2)	C22—C21—H21A	119.4
C13—O3—P1	122.96 (19)	C23—C22—C21	119.2 (5)
C19—O4—P2	122.8 (2)	C23—C22—H22A	120.4
C25—O5—P2	124.1 (2)	C21—C22—H22A	120.4
C31—O6—P2	121.4 (2)	C22—C23—C24	121.1 (5)
C2—C1—C6	121.5 (3)	C22—C23—H23A	119.4
C2—C1—O1	120.5 (3)	C24—C23—H23A	119.4
C6—C1—O1	118.0 (3)	C23—C24—C19	118.8 (4)
C1—C2—C3	119.0 (3)	C23—C24—H24A	120.6
C1—C2—H2A	120.5	C19—C24—H24A	120.6
C3—C2—H2A	120.5	C26—C25—C30	122.5 (4)
C4—C3—C2	120.7 (4)	C26—C25—O5	118.4 (4)
C4—C3—H3A	119.6	C30—C25—O5	119.0 (4)
C2—C3—H3A	119.6	C25—C26—C27	117.4 (5)
C3—C4—C5	119.2 (4)	C25—C26—H26A	121.3
C3—C4—H4A	120.4	C27—C26—H26A	121.3
C5—C4—H4A	120.4	C28—C27—C26	119.8 (6)
C4—C5—C6	121.6 (4)	C28—C27—H27A	120.1
C4—C5—H5A	119.2	C26—C27—H27A	120.1
C6—C5—H5A	119.2	C29—C28—C27	121.6 (6)
C1—C6—C5	118.0 (4)	C29—C28—H28A	119.2
C1—C6—H6A	121.0	C27—C28—H28A	119.2
C5—C6—H6A	121.0	C28—C29—C30	120.0 (7)
C8—C7—C12	121.2 (3)	C28—C29—H29A	120.0
C8—C7—O2	119.2 (3)	C30—C29—H29A	120.0
C12—C7—O2	119.5 (3)	C25—C30—C29	118.7 (6)
C7—C8—C9	119.0 (4)	C25—C30—H30A	120.6
C7—C8—H8A	120.5	C29—C30—H30A	120.6
C9—C8—H8A	120.5	C36—C31—C32	121.2 (4)
C10—C9—C8	120.6 (4)	C36—C31—O6	120.5 (4)
C10—C9—H9A	119.7	C32—C31—O6	118.3 (4)
C8—C9—H9A	119.7	C31—C32—C33	119.1 (5)
C9—C10—C11	120.4 (4)	C31—C32—H32A	120.5
C9—C10—H10A	119.8	C33—C32—H32A	120.5
C11—C10—H10A	119.8	C34—C33—C32	120.0 (6)
C10—C11—C12	120.7 (4)	C34—C33—H33A	120.0
C10—C11—H11A	119.7	C32—C33—H33A	120.0
C12—C11—H11A	119.7	C35—C34—C33	119.8 (5)
C7—C12—C11	118.0 (4)	C35—C34—H34A	120.1
C7—C12—H12A	121.0	C33—C34—H34A	120.1
C11—C12—H12A	121.0	C34—C35—C36	121.1 (5)
C18—C13—C14	121.3 (3)	C34—C35—H35A	119.5
C18—C13—O3	121.3 (3)	C36—C35—H35A	119.5
C14—C13—O3	117.3 (3)	C31—C36—C35	118.9 (5)
C15—C14—C13	118.8 (4)	C31—C36—H36A	120.5
C15—C14—H14A	120.6	C35—C36—H36A	120.5
C13—C14—H14A	120.6

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···Cl1^i	0.93	2.73	3.408 (4)	130
C3—H3A···Cg1^i	0.93	2.84	3.640 (2)	145
C10—H10A···Cg2^ii	0.93	2.80	3.605 (2)	146
C28—H28A···Cg3^iii	0.93	2.80	3.605 (2)	146

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