p-Cumyl­calix­[4]­arene-para-xyl­ene (1/1)

In the complex between p-cumyl­calix­[4]­arene and para-xyl­ene [systematic name: 4-(2-phenyl­iso­propyl)­calix­[4]­arene-1,4-di­methyl­benzene (1/1)], C₆₄H₆₄O₄·C₈H₁₀, the macrocycle has a cone conformation, which is stabilized by intramolecular hydrogen bonds. The guest para-xyl­ene mol­ecule is situated inside the cavity, giving an endo-calix complex. The host and guest molecules both have twofold rotation symmetry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 95%
• R factor = 0.055
• wR factor = 0.155
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.41
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT128_ALERT_4_C Non-standard setting of Space group P2/c    ....    P2/n
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C501
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.01
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........        O13
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........        O14
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C64 H60 O4

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:C72 H74 O4
            Atom count from the _atom_site data:  C72 H70 O4
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C72 H74 O4
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        144.00    144.00    0.00
           H        148.00    140.00    8.00
           O          8.00      8.00    0.00

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

   6 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
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: Collect (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

4-(2-Phenylisopropyl)calix[4]arene–1,4-dimethylbenzene (1/1)

Crystal data

C64H64O4·C8H10	Z = 2
Mr = 1003.31	F(000) = 1076
Monoclinic, P2/n	Dx = 1.198 Mg m^−3
a = 14.66 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.62 (3) Å	µ = 0.07 mm^−1
c = 15.14 (3) Å	T = 293 K
β = 96.62 (3)°	Plate, colorless
V = 2782 (10) Å^3	0.80 × 0.50 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer	4031 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Horizonally mounted graphite crystal monochromator	θmax = 27.5°, θmin = 3.2°
Detector resolution: 9 pixels mm^-1	h = −18→19
φ or ω scans	k = −16→16
12312 measured reflections	l = −19→19
6372 independent reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0771P)^2 + 0.6028P] where P = (Fo^2 + 2Fc^2)/3
6372 reflections	(Δ/σ)max = 0.001
351 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Experimental. Diffractometer equiped with an area detector. phi scans and omega scans during 20 s with 2 ° steps Crystal to detector distance: 30 mm

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)
O13	0.20582 (9)	0.05806 (9)	0.12855 (8)	0.0319 (3)
O14	0.37116 (9)	0.05843 (10)	0.22388 (8)	0.0322 (3)
C1	0.46942 (12)	−0.04090 (15)	0.38132 (11)	0.0298 (4)
H1A	0.5280	−0.0590	0.4143	0.036*
H1B	0.4657	0.0358	0.3779	0.036*
C12	0.10702 (12)	−0.08123 (14)	0.06803 (11)	0.0279 (4)
C2	0.46639 (12)	−0.08547 (14)	0.28743 (11)	0.0273 (4)
C14	0.41867 (12)	−0.03496 (13)	0.21413 (11)	0.0265 (4)
C4	0.51245 (12)	−0.22371 (14)	0.18862 (11)	0.0279 (4)
C13	0.19330 (12)	−0.03252 (13)	0.07701 (11)	0.0271 (4)
C8	0.26570 (12)	−0.07218 (14)	0.03461 (11)	0.0272 (4)
C6	0.41743 (12)	−0.07599 (14)	0.12830 (11)	0.0273 (4)
C7	0.36111 (12)	−0.02468 (15)	0.04960 (11)	0.0289 (4)
H7A	0.3917	−0.0345	−0.0033	0.035*
H7B	0.3565	0.0508	0.0602	0.035*
C11	0.09466 (13)	−0.16916 (15)	0.01280 (11)	0.0301 (4)
H11	0.0372	−0.2012	0.0050	0.036*
C5	0.46495 (12)	−0.16913 (14)	0.11760 (11)	0.0290 (4)
H5	0.4652	−0.1964	0.0606	0.035*
C40	0.56323 (13)	−0.32533 (15)	0.16955 (12)	0.0327 (4)
C10	0.16468 (13)	−0.21173 (14)	−0.03157 (11)	0.0308 (4)
C9	0.24929 (13)	−0.16218 (15)	−0.01818 (11)	0.0303 (4)
H9	0.2975	−0.1902	−0.0457	0.036*
C3	0.51190 (12)	−0.17956 (15)	0.27293 (11)	0.0285 (4)
H3	0.5432	−0.2144	0.3214	0.034*
C100	0.14674 (14)	−0.30593 (15)	−0.09561 (12)	0.0349 (4)
C103	0.10026 (13)	−0.26560 (16)	−0.18622 (12)	0.0334 (4)
C42	0.60837 (15)	−0.37815 (16)	0.25528 (13)	0.0394 (5)
H42A	0.6526	−0.3306	0.2856	0.059*
H42B	0.6385	−0.4422	0.2405	0.059*
H42C	0.5622	−0.3945	0.2932	0.059*
C43	0.64065 (13)	−0.29801 (16)	0.11258 (12)	0.0358 (5)
C104	0.12549 (14)	−0.16827 (17)	−0.21980 (12)	0.0392 (5)
H104	0.1679	−0.1258	−0.1857	0.047*
C41	0.49366 (15)	−0.40372 (17)	0.12225 (14)	0.0440 (5)
H41A	0.4433	−0.4129	0.1569	0.066*
H41B	0.5231	−0.4708	0.1157	0.066*
H41C	0.4711	−0.3765	0.0646	0.066*
C47	0.76271 (16)	−0.1811 (2)	0.07941 (17)	0.0596 (7)
H47	0.7949	−0.1180	0.0899	0.071*
C106	0.02546 (15)	−0.1950 (2)	−0.35440 (13)	0.0480 (6)
H106	0.0002	−0.1715	−0.4101	0.058*
C102	0.23694 (16)	−0.35996 (17)	−0.11306 (14)	0.0467 (5)
H10A	0.2704	−0.3807	−0.0575	0.070*
H10B	0.2733	−0.3114	−0.1431	0.070*
H10C	0.2235	−0.4215	−0.1495	0.070*
C105	0.08829 (15)	−0.13408 (19)	−0.30310 (13)	0.0454 (5)
H105	0.1061	−0.0691	−0.3245	0.055*
C107	0.00033 (16)	−0.2909 (2)	−0.32280 (14)	0.0509 (6)
H107	−0.0421	−0.3328	−0.3574	0.061*
C48	0.69013 (14)	−0.20482 (18)	0.12696 (14)	0.0443 (5)
H48	0.6742	−0.1572	0.1695	0.053*
C101	0.08758 (19)	−0.38921 (18)	−0.05491 (14)	0.0531 (6)
H10D	0.0274	−0.3608	−0.0512	0.080*
H10E	0.1156	−0.4075	0.0036	0.080*
H10F	0.0828	−0.4514	−0.0917	0.080*
C108	0.03761 (14)	−0.32626 (18)	−0.23939 (13)	0.0424 (5)
H108	0.0201	−0.3919	−0.2191	0.051*
C44	0.66673 (17)	−0.3675 (2)	0.04907 (14)	0.0520 (6)
H44	0.6350	−0.4308	0.0379	0.062*
C46	0.78700 (19)	−0.2512 (3)	0.01654 (18)	0.0702 (9)
H46	0.8355	−0.2356	−0.0158	0.084*
C45	0.7399 (2)	−0.3432 (3)	0.00206 (17)	0.0716 (9)
H45	0.7569	−0.3907	−0.0400	0.086*
C504	0.2500	0.6358 (2)	0.2500	0.0326 (6)
C503	0.18099 (14)	0.58012 (17)	0.20100 (13)	0.0404 (5)
H503	0.1338	0.6166	0.1677	0.048*
C501	0.2500	0.4130 (2)	0.2500	0.0485 (8)
C502	0.18112 (17)	0.46990 (19)	0.20075 (15)	0.0499 (6)
H502	0.1341	0.4337	0.1669	0.060*
C506	0.2500	0.7552 (2)	0.2500	0.0493 (8)
H50A	0.2144	0.7806	0.1970	0.074*	0.50
H50B	0.3119	0.7806	0.2518	0.074*	0.50
H50C	0.2236	0.7806	0.3012	0.074*	0.50
C505	0.2500	0.2936 (3)	0.2500	0.0852 (15)
H50D	0.2642	0.2682	0.1934	0.128*	0.50
H50E	0.1905	0.2682	0.2606	0.128*	0.50
H50F	0.2953	0.2682	0.2960	0.128*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O13	0.0414 (7)	0.0257 (7)	0.0295 (7)	−0.0011 (6)	0.0081 (5)	−0.0008 (5)
O14	0.0367 (7)	0.0267 (7)	0.0339 (7)	0.0011 (6)	0.0073 (5)	−0.0013 (5)
C1	0.0283 (9)	0.0336 (10)	0.0270 (9)	−0.0029 (8)	0.0015 (7)	−0.0048 (7)
C12	0.0316 (9)	0.0312 (10)	0.0204 (8)	0.0035 (8)	0.0011 (7)	0.0077 (7)
C2	0.0247 (9)	0.0307 (10)	0.0267 (9)	−0.0058 (8)	0.0044 (7)	−0.0023 (7)
C14	0.0268 (9)	0.0240 (9)	0.0294 (9)	−0.0030 (7)	0.0063 (7)	−0.0009 (7)
C4	0.0277 (9)	0.0296 (10)	0.0271 (9)	−0.0025 (8)	0.0064 (7)	−0.0018 (7)
C13	0.0354 (10)	0.0243 (9)	0.0211 (8)	0.0013 (8)	0.0015 (7)	0.0034 (7)
C8	0.0316 (10)	0.0292 (9)	0.0207 (8)	−0.0009 (8)	0.0028 (7)	0.0041 (7)
C6	0.0272 (9)	0.0297 (9)	0.0256 (9)	−0.0054 (8)	0.0060 (7)	−0.0002 (7)
C7	0.0333 (10)	0.0301 (10)	0.0244 (9)	−0.0008 (8)	0.0082 (7)	0.0012 (7)
C11	0.0319 (10)	0.0331 (10)	0.0242 (9)	−0.0036 (8)	−0.0015 (7)	0.0051 (7)
C5	0.0329 (10)	0.0311 (10)	0.0238 (9)	−0.0027 (8)	0.0067 (7)	−0.0022 (7)
C40	0.0375 (11)	0.0314 (10)	0.0297 (9)	0.0027 (8)	0.0063 (8)	−0.0004 (8)
C10	0.0402 (11)	0.0300 (10)	0.0217 (9)	−0.0002 (8)	0.0016 (7)	0.0016 (7)
C9	0.0354 (10)	0.0335 (10)	0.0225 (9)	0.0019 (8)	0.0050 (7)	0.0006 (7)
C3	0.0273 (9)	0.0333 (10)	0.0248 (9)	−0.0019 (8)	0.0018 (7)	0.0017 (7)
C100	0.0416 (11)	0.0343 (10)	0.0277 (9)	−0.0044 (9)	−0.0001 (8)	−0.0016 (8)
C103	0.0350 (10)	0.0400 (11)	0.0256 (9)	0.0052 (9)	0.0054 (8)	−0.0038 (8)
C42	0.0512 (13)	0.0332 (11)	0.0348 (11)	0.0065 (9)	0.0095 (9)	0.0054 (8)
C43	0.0383 (11)	0.0407 (11)	0.0289 (10)	0.0134 (9)	0.0060 (8)	0.0072 (8)
C104	0.0424 (11)	0.0446 (12)	0.0311 (10)	0.0026 (10)	0.0058 (8)	0.0005 (9)
C41	0.0520 (13)	0.0351 (11)	0.0452 (12)	−0.0017 (10)	0.0065 (10)	−0.0057 (9)
C47	0.0386 (13)	0.0684 (16)	0.0734 (17)	0.0102 (12)	0.0140 (12)	0.0378 (14)
C106	0.0524 (14)	0.0647 (16)	0.0265 (10)	0.0279 (12)	0.0030 (9)	−0.0020 (10)
C102	0.0559 (14)	0.0386 (12)	0.0425 (12)	0.0109 (10)	−0.0080 (10)	−0.0086 (9)
C105	0.0525 (13)	0.0537 (13)	0.0316 (11)	0.0151 (11)	0.0115 (10)	0.0055 (9)
C107	0.0469 (13)	0.0644 (16)	0.0383 (12)	0.0144 (12)	−0.0083 (9)	−0.0161 (11)
C48	0.0382 (12)	0.0474 (13)	0.0485 (12)	0.0078 (10)	0.0106 (9)	0.0129 (10)
C101	0.0836 (17)	0.0420 (13)	0.0339 (11)	−0.0195 (12)	0.0077 (11)	−0.0028 (9)
C108	0.0436 (12)	0.0441 (12)	0.0383 (11)	0.0020 (10)	−0.0009 (9)	−0.0071 (9)
C44	0.0605 (15)	0.0594 (15)	0.0385 (12)	0.0199 (12)	0.0158 (10)	0.0029 (10)
C46	0.0535 (16)	0.100 (2)	0.0630 (17)	0.0333 (16)	0.0311 (13)	0.0481 (16)
C45	0.0779 (19)	0.093 (2)	0.0501 (15)	0.0377 (18)	0.0355 (14)	0.0156 (14)
C504	0.0364 (15)	0.0330 (14)	0.0299 (13)	0.000	0.0107 (11)	0.000
C503	0.0405 (11)	0.0458 (12)	0.0349 (10)	−0.0010 (9)	0.0043 (8)	−0.0045 (9)
C501	0.077 (2)	0.0316 (16)	0.0425 (17)	0.000	0.0315 (17)	0.000
C502	0.0571 (14)	0.0500 (14)	0.0454 (12)	−0.0144 (11)	0.0177 (10)	−0.0117 (10)
C506	0.056 (2)	0.0351 (16)	0.057 (2)	0.000	0.0055 (15)	0.000
C505	0.146 (4)	0.0334 (19)	0.086 (3)	0.000	0.056 (3)	0.000

Geometric parameters (Å, º)

O13—C13	1.384 (3)	C104—C105	1.384 (4)
O14—C14	1.386 (3)	C104—H104	0.9300
C1—C12^i	1.517 (3)	C41—H41A	0.9600
C1—C2	1.525 (4)	C41—H41B	0.9600
C1—H1A	0.9700	C41—H41C	0.9600
C1—H1B	0.9700	C47—C46	1.377 (5)
C12—C11	1.389 (3)	C47—C48	1.385 (4)
C12—C13	1.399 (3)	C47—H47	0.9300
C12—C1^i	1.517 (3)	C106—C107	1.366 (4)
C2—C3	1.392 (4)	C106—C105	1.371 (4)
C2—C14	1.396 (3)	C106—H106	0.9300
C14—C6	1.397 (3)	C102—H10A	0.9600
C4—C3	1.394 (3)	C102—H10B	0.9600
C4—C5	1.394 (3)	C102—H10C	0.9600
C4—C40	1.527 (4)	C105—H105	0.9300
C13—C8	1.395 (3)	C107—C108	1.391 (4)
C8—C9	1.394 (3)	C107—H107	0.9300
C8—C7	1.515 (4)	C48—H48	0.9300
C6—C5	1.385 (4)	C101—H10D	0.9600
C6—C7	1.514 (3)	C101—H10E	0.9600
C7—H7A	0.9700	C101—H10F	0.9600
C7—H7B	0.9700	C108—H108	0.9300
C11—C10	1.397 (3)	C44—C45	1.389 (4)
C11—H11	0.9300	C44—H44	0.9300
C5—H5	0.9300	C46—C45	1.354 (5)
C40—C41	1.537 (3)	C46—H46	0.9300
C40—C42	1.539 (3)	C45—H45	0.9300
C40—C43	1.542 (3)	C504—C503^i	1.376 (3)
C10—C9	1.383 (4)	C504—C503	1.376 (3)
C10—C100	1.537 (4)	C504—C506	1.507 (5)
C9—H9	0.9300	C503—C502	1.391 (5)
C3—H3	0.9300	C503—H503	0.9300
C100—C101	1.536 (4)	C501—C502^i	1.384 (3)
C100—C102	1.537 (4)	C501—C502	1.384 (3)
C100—C103	1.546 (3)	C501—C505	1.507 (6)
C103—C108	1.381 (3)	C502—H502	0.9300
C103—C104	1.395 (4)	C506—H50A	0.9600
C42—H42A	0.9600	C506—H50B	0.9600
C42—H42B	0.9600	C506—H50C	0.9600
C42—H42C	0.9600	C505—H50D	0.9600
C43—C48	1.386 (4)	C505—H50E	0.9600
C43—C44	1.387 (3)	C505—H50F	0.9600
C12^i—C1—C2	113.81 (17)	C105—C104—C103	120.9 (2)
C12^i—C1—H1A	108.8	C105—C104—H104	119.6
C2—C1—H1A	108.8	C103—C104—H104	119.6
C12^i—C1—H1B	108.8	C40—C41—H41A	109.5
C2—C1—H1B	108.8	C40—C41—H41B	109.5
H1A—C1—H1B	107.7	H41A—C41—H41B	109.5
C11—C12—C13	117.61 (17)	C40—C41—H41C	109.5
C11—C12—C1^i	121.31 (18)	H41A—C41—H41C	109.5
C13—C12—C1^i	121.1 (2)	H41B—C41—H41C	109.5
C3—C2—C14	118.01 (18)	C46—C47—C48	119.7 (3)
C3—C2—C1	119.93 (16)	C46—C47—H47	120.1
C14—C2—C1	122.1 (2)	C48—C47—H47	120.1
O14—C14—C2	121.05 (17)	C107—C106—C105	119.3 (2)
O14—C14—C6	117.50 (16)	C107—C106—H106	120.4
C2—C14—C6	121.5 (2)	C105—C106—H106	120.4
C3—C4—C5	117.0 (2)	C100—C102—H10A	109.5
C3—C4—C40	124.28 (17)	C100—C102—H10B	109.5
C5—C4—C40	118.70 (18)	H10A—C102—H10B	109.5
O13—C13—C8	119.82 (17)	C100—C102—H10C	109.5
O13—C13—C12	118.51 (16)	H10A—C102—H10C	109.5
C8—C13—C12	121.7 (2)	H10B—C102—H10C	109.5
C9—C8—C13	117.79 (18)	C106—C105—C104	120.6 (2)
C9—C8—C7	120.26 (16)	C106—C105—H105	119.7
C13—C8—C7	121.8 (2)	C104—C105—H105	119.7
C5—C6—C14	118.07 (17)	C106—C107—C108	120.6 (2)
C5—C6—C7	120.44 (18)	C106—C107—H107	119.7
C14—C6—C7	121.4 (2)	C108—C107—H107	119.7
C6—C7—C8	111.03 (17)	C47—C48—C43	121.4 (2)
C6—C7—H7A	109.4	C47—C48—H48	119.3
C8—C7—H7A	109.4	C43—C48—H48	119.3
C6—C7—H7B	109.4	C100—C101—H10D	109.5
C8—C7—H7B	109.4	C100—C101—H10E	109.5
H7A—C7—H7B	108.0	H10D—C101—H10E	109.5
C12—C11—C10	123.00 (19)	C100—C101—H10F	109.5
C12—C11—H11	118.5	H10D—C101—H10F	109.5
C10—C11—H11	118.5	H10E—C101—H10F	109.5
C6—C5—C4	122.83 (18)	C103—C108—C107	121.1 (2)
C6—C5—H5	118.6	C103—C108—H108	119.5
C4—C5—H5	118.6	C107—C108—H108	119.5
C4—C40—C41	108.5 (2)	C43—C44—C45	120.4 (3)
C4—C40—C42	112.08 (18)	C43—C44—H44	119.8
C41—C40—C42	108.2 (2)	C45—C44—H44	119.8
C4—C40—C43	108.93 (18)	C45—C46—C47	119.7 (3)
C41—C40—C43	112.0 (2)	C45—C46—H46	120.2
C42—C40—C43	107.2 (2)	C47—C46—H46	120.2
C9—C10—C11	116.9 (2)	C46—C45—C44	121.0 (3)
C9—C10—C100	121.83 (17)	C46—C45—H45	119.5
C11—C10—C100	121.25 (19)	C44—C45—H45	119.5
C10—C9—C8	123.03 (18)	C503^i—C504—C503	118.6 (3)
C10—C9—H9	118.5	C503^i—C504—C506	120.70 (15)
C8—C9—H9	118.5	C503—C504—C506	120.70 (15)
C2—C3—C4	122.62 (17)	C504—C503—C502	120.7 (2)
C2—C3—H3	118.7	C504—C503—H503	119.6
C4—C3—H3	118.7	C502—C503—H503	119.6
C101—C100—C10	109.8 (2)	C502^i—C501—C502	117.6 (3)
C101—C100—C102	107.6 (2)	C502^i—C501—C505	121.22 (16)
C10—C100—C102	111.30 (18)	C502—C501—C505	121.22 (16)
C101—C100—C103	111.7 (2)	C501—C502—C503	121.2 (2)
C10—C100—C103	109.3 (2)	C501—C502—H502	119.4
C102—C100—C103	107.06 (18)	C503—C502—H502	119.4
C108—C103—C104	117.5 (2)	C504—C506—H50A	109.5
C108—C103—C100	122.0 (2)	C504—C506—H50B	109.5
C104—C103—C100	120.32 (18)	H50A—C506—H50B	109.5
C40—C42—H42A	109.5	C504—C506—H50C	109.5
C40—C42—H42B	109.5	H50A—C506—H50C	109.5
H42A—C42—H42B	109.5	H50B—C506—H50C	109.5
C40—C42—H42C	109.5	C501—C505—H50D	109.5
H42A—C42—H42C	109.5	C501—C505—H50E	109.5
H42B—C42—H42C	109.5	H50D—C505—H50E	109.5
C48—C43—C44	117.7 (2)	C501—C505—H50F	109.5
C48—C43—C40	120.50 (18)	H50D—C505—H50F	109.5
C44—C43—C40	121.7 (2)	H50E—C505—H50F	109.5

Symmetry code: (i) −x+1/2, y, −z+1/2.