(R,S)-Methyl 3-methyl-5-oxo-1-phenyl­cyclo­hex-3-ene-1-carboxylate

The title compound, C₁₅H₁₆O₃, has two molecules in the asymmetric unit. The cyclo­hex-2-enone ring has an envelope conformation in both molecules. The crystal exhibits twinning. The mol­ecular packing in the crystal structure is determined by weak inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.122
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C14     ..       6.26 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C29     ..       5.14 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C29

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(R,S)-5-Carboxymethyl-5-phenyl-3-methylcyclohex-2-enone

Crystal data

C15H16O3	Z = 4
Mr = 244.29	F(000) = 520.00
Triclinic, P1	Dx = 1.247 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 9.317 (4) Å	Cell parameters from 9544 reflections
b = 12.332 (5) Å	θ = 3.3–27.5°
c = 12.734 (5) Å	µ = 0.09 mm^−1
α = 67.495 (16)°	T = 298 K
β = 84.826 (16)°	Block, colourless
γ = 74.278 (16)°	0.27 × 0.26 × 0.17 mm
V = 1300.9 (9) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.023
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°
ω scans	h = −12→12
12919 measured reflections	k = −15→15
5900 independent reflections	l = −14→16
3491 reflections with F^2 > 2.0σ(F^2)

Refinement

Refinement on F^2	w = 1/[0.0008Fo^2 + 1.0000σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.046	(Δ/σ)max < 0.001
wR(F^2) = 0.122	Δρmax = 0.22 e Å^−3
S = 1.02	Δρmin = −0.15 e Å^−3
5900 reflections	Extinction correction: Larson (1970) Crystallographic Computing eq. 22
336 parameters	Extinction coefficient: 66 (15)
H-atom parameters constrained

Special details

Geometry. The crystal is a twin. It has a chiral centre at the position 5 of the cyclohex-2-enone ring.

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.56135 (14)	0.83556 (11)	0.81733 (12)	0.0776 (4)
O2	0.20420 (14)	0.77551 (12)	0.89822 (10)	0.0824 (4)
O3	0.04497 (12)	0.79912 (11)	0.76893 (10)	0.0634 (3)
O4	0.47407 (14)	0.22112 (12)	0.60890 (11)	0.0744 (4)
O5	0.86986 (13)	0.23755 (12)	0.59558 (10)	0.0812 (4)
O6	0.98248 (12)	0.18918 (10)	0.75794 (9)	0.0604 (3)
C1	0.29760 (14)	0.70313 (12)	0.74777 (11)	0.0377 (3)
C2	0.27651 (14)	0.57566 (12)	0.77622 (12)	0.0409 (3)
C3	0.22295 (17)	0.54393 (12)	0.69685 (12)	0.0475 (4)
C4	0.20191 (19)	0.42869 (14)	0.72653 (16)	0.0595 (5)
C5	0.2357 (2)	0.34468 (14)	0.83414 (17)	0.0658 (5)
C6	0.2890 (2)	0.37448 (16)	0.91324 (16)	0.0681 (5)
C7	0.3085 (2)	0.48899 (13)	0.88477 (12)	0.0574 (5)
C8	0.45087 (17)	0.69681 (12)	0.78720 (13)	0.0514 (4)
C9	0.47753 (18)	0.81977 (13)	0.75878 (14)	0.0536 (4)
C10	0.40459 (18)	0.91716 (13)	0.65692 (13)	0.0525 (4)
C11	0.31618 (17)	0.90070 (12)	0.59109 (12)	0.0476 (4)
C12	0.28085 (18)	0.78065 (12)	0.62072 (12)	0.0462 (4)
C13	0.2476 (2)	0.99865 (14)	0.48327 (13)	0.0695 (5)
C14	0.17923 (16)	0.76294 (12)	0.81404 (11)	0.0420 (4)
C15	−0.0752 (2)	0.8486 (2)	0.8312 (2)	0.0875 (7)
C16	0.73419 (16)	0.31345 (12)	0.73434 (11)	0.0400 (3)
C17	0.76983 (16)	0.43231 (12)	0.72063 (12)	0.0440 (4)
C18	0.81498 (17)	0.45133 (13)	0.81127 (13)	0.0514 (4)
C19	0.84956 (19)	0.55841 (16)	0.79571 (17)	0.0624 (5)
C20	0.8394 (2)	0.64751 (16)	0.69083 (18)	0.0675 (5)
C21	0.7930 (2)	0.63127 (18)	0.60140 (18)	0.0886 (7)
C22	0.7588 (2)	0.52464 (17)	0.61592 (14)	0.0775 (6)
C23	0.59465 (17)	0.33725 (13)	0.66544 (12)	0.0490 (4)
C24	0.54867 (18)	0.22373 (14)	0.68188 (13)	0.0508 (4)
C25	0.59101 (18)	0.12138 (13)	0.78781 (12)	0.0528 (4)
C26	0.66125 (18)	0.12660 (12)	0.87171 (12)	0.0486 (4)
C27	0.70954 (18)	0.23752 (12)	0.85852 (12)	0.0469 (4)
C28	0.6949 (2)	0.02476 (14)	0.98382 (13)	0.0692 (5)
C29	0.86691 (16)	0.24303 (12)	0.68704 (12)	0.0424 (4)
C30	1.1155 (2)	0.12498 (18)	0.71811 (16)	0.0750 (6)
H3	0.2009	0.6003	0.6231	0.057*
H4	0.1647	0.4086	0.6730	0.071*
H5	0.2225	0.2673	0.8536	0.079*
H6	0.3121	0.3172	0.9865	0.082*
H7	0.3439	0.5084	0.9395	0.069*
H10	0.4203	0.9938	0.6370	0.063*
H18	0.8221	0.3912	0.8836	0.062*
H19	0.8801	0.5696	0.8576	0.075*
H20	0.8641	0.7191	0.6805	0.081*
H21	0.7842	0.6926	0.5296	0.106*
H22	0.7275	0.5150	0.5535	0.093*
H25	0.5683	0.0491	0.7978	0.063*
H81	0.4590	0.6540	0.8690	0.062*
H82	0.5267	0.6522	0.7509	0.062*
H121	0.1788	0.7956	0.5973	0.055*
H122	0.3479	0.7360	0.5797	0.055*
H131	0.2742	0.9708	0.4216	0.083*
H132	0.2833	1.0691	0.4687	0.083*
H133	0.1411	1.0192	0.4901	0.083*
H151	−0.0590	0.8024	0.9112	0.105*
H152	−0.1682	0.8443	0.8082	0.105*
H153	−0.0780	0.9317	0.8155	0.105*
H231	0.6144	0.3762	0.5855	0.059*
H232	0.5130	0.3913	0.6882	0.059*
H271	0.8022	0.2122	0.9007	0.056*
H272	0.6332	0.2876	0.8895	0.056*
H281	0.7998	0.0026	1.0003	0.083*
H282	0.6668	−0.0438	0.9818	0.083*
H283	0.6399	0.0497	1.0418	0.083*
H301	1.0888	0.0789	0.6804	0.090*
H302	1.1806	0.0710	0.7816	0.090*
H303	1.1655	0.1823	0.6659	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0721 (8)	0.0675 (8)	0.1041 (10)	−0.0249 (6)	−0.0267 (7)	−0.0330 (7)
O2	0.0799 (9)	0.1225 (11)	0.0564 (7)	−0.0104 (8)	−0.0045 (6)	−0.0554 (8)
O3	0.0399 (6)	0.0862 (8)	0.0786 (8)	−0.0071 (5)	0.0000 (5)	−0.0524 (7)
O4	0.0795 (9)	0.0811 (8)	0.0747 (8)	−0.0286 (7)	−0.0189 (6)	−0.0325 (7)
O5	0.0715 (8)	0.1235 (11)	0.0515 (7)	0.0004 (7)	−0.0036 (5)	−0.0522 (7)
O6	0.0539 (6)	0.0713 (7)	0.0514 (6)	0.0056 (5)	−0.0088 (5)	−0.0305 (5)
C1	0.0397 (7)	0.0364 (7)	0.0381 (7)	−0.0108 (5)	0.0002 (5)	−0.0142 (6)
C2	0.0385 (7)	0.0390 (7)	0.0451 (8)	−0.0102 (6)	0.0041 (6)	−0.0162 (6)
C3	0.0487 (8)	0.0449 (8)	0.0502 (8)	−0.0132 (6)	0.0003 (7)	−0.0182 (7)
C4	0.0603 (10)	0.0516 (9)	0.0786 (12)	−0.0205 (8)	0.0035 (9)	−0.0338 (9)
C5	0.0684 (11)	0.0425 (9)	0.0863 (13)	−0.0221 (8)	0.0109 (10)	−0.0207 (9)
C6	0.0797 (13)	0.0483 (9)	0.0628 (11)	−0.0205 (9)	−0.0008 (9)	−0.0032 (8)
C7	0.0691 (11)	0.0509 (9)	0.0496 (9)	−0.0206 (8)	−0.0035 (8)	−0.0114 (7)
C8	0.0432 (8)	0.0446 (8)	0.0655 (10)	−0.0110 (7)	−0.0067 (7)	−0.0183 (7)
C9	0.0420 (8)	0.0507 (9)	0.0731 (11)	−0.0127 (7)	−0.0017 (7)	−0.0276 (8)
C10	0.0509 (9)	0.0432 (8)	0.0672 (10)	−0.0180 (7)	0.0092 (7)	−0.0226 (8)
C11	0.0522 (9)	0.0417 (8)	0.0464 (8)	−0.0137 (6)	0.0109 (7)	−0.0149 (7)
C12	0.0560 (9)	0.0474 (8)	0.0390 (7)	−0.0181 (7)	0.0059 (6)	−0.0181 (6)
C13	0.0901 (14)	0.0534 (10)	0.0558 (10)	−0.0222 (9)	0.0024 (9)	−0.0084 (8)
C14	0.0481 (8)	0.0410 (7)	0.0383 (7)	−0.0145 (6)	0.0005 (6)	−0.0142 (6)
C15	0.0498 (11)	0.1063 (16)	0.1244 (18)	−0.0131 (10)	0.0252 (11)	−0.0724 (15)
C16	0.0472 (8)	0.0384 (7)	0.0353 (7)	−0.0121 (6)	0.0015 (5)	−0.0141 (6)
C17	0.0461 (8)	0.0406 (7)	0.0468 (8)	−0.0126 (6)	0.0019 (6)	−0.0174 (7)
C18	0.0548 (9)	0.0464 (8)	0.0545 (9)	−0.0138 (7)	−0.0052 (7)	−0.0187 (7)
C19	0.0580 (10)	0.0601 (10)	0.0800 (12)	−0.0174 (8)	−0.0080 (9)	−0.0345 (10)
C20	0.0632 (11)	0.0489 (10)	0.0943 (14)	−0.0233 (8)	−0.0060 (10)	−0.0232 (10)
C21	0.135 (2)	0.0626 (12)	0.0674 (12)	−0.0527 (13)	−0.0118 (12)	−0.0018 (10)
C22	0.1237 (18)	0.0644 (11)	0.0501 (10)	−0.0479 (11)	−0.0086 (10)	−0.0094 (9)
C23	0.0485 (9)	0.0469 (8)	0.0497 (8)	−0.0108 (7)	−0.0026 (7)	−0.0162 (7)
C24	0.0481 (9)	0.0561 (9)	0.0554 (9)	−0.0155 (7)	0.0021 (7)	−0.0275 (8)
C25	0.0592 (10)	0.0477 (9)	0.0594 (9)	−0.0217 (7)	0.0080 (7)	−0.0247 (8)
C26	0.0566 (9)	0.0450 (8)	0.0446 (8)	−0.0169 (7)	0.0121 (7)	−0.0173 (7)
C27	0.0590 (9)	0.0475 (8)	0.0384 (7)	−0.0163 (7)	0.0064 (6)	−0.0199 (6)
C28	0.0930 (15)	0.0577 (10)	0.0511 (10)	−0.0259 (10)	0.0081 (9)	−0.0110 (8)
C29	0.0487 (8)	0.0433 (8)	0.0361 (7)	−0.0144 (6)	−0.0004 (6)	−0.0139 (6)
C30	0.0547 (11)	0.0817 (13)	0.0786 (13)	0.0045 (9)	0.0004 (9)	−0.0342 (11)

Geometric parameters (Å, º)

O1—C9	1.226 (2)	C25—C26	1.332 (2)
O2—C14	1.191 (2)	C26—C27	1.499 (2)
O3—C14	1.3132 (18)	C26—C28	1.4861 (18)
O3—C15	1.447 (2)	C3—H3	0.930
O4—C24	1.224 (2)	C4—H4	0.930
O5—C29	1.190 (2)	C5—H5	0.930
O6—C29	1.3207 (17)	C6—H6	0.930
O6—C30	1.443 (2)	C7—H7	0.930
C1—C2	1.536 (2)	C8—H81	0.970
C1—C8	1.528 (2)	C8—H82	0.970
C1—C12	1.5286 (17)	C10—H10	0.930
C1—C14	1.530 (2)	C12—H121	0.970
C2—C3	1.387 (2)	C12—H122	0.970
C2—C7	1.3830 (18)	C13—H131	0.960
C3—C4	1.388 (2)	C13—H132	0.960
C4—C5	1.365 (2)	C13—H133	0.960
C5—C6	1.367 (3)	C15—H151	0.960
C6—C7	1.376 (2)	C15—H152	0.960
C8—C9	1.503 (2)	C15—H153	0.960
C9—C10	1.4529 (19)	C18—H18	0.930
C10—C11	1.330 (2)	C19—H19	0.930
C11—C12	1.502 (2)	C20—H20	0.930
C11—C13	1.4910 (19)	C21—H21	0.930
C16—C17	1.532 (2)	C22—H22	0.930
C16—C23	1.532 (2)	C23—H231	0.970
C16—C27	1.5322 (17)	C23—H232	0.970
C16—C29	1.526 (2)	C25—H25	0.930
C17—C18	1.383 (2)	C27—H271	0.970
C17—C22	1.3726 (19)	C27—H272	0.970
C18—C19	1.380 (2)	C28—H281	0.960
C19—C20	1.358 (2)	C28—H282	0.960
C20—C21	1.354 (3)	C28—H283	0.960
C21—C22	1.377 (3)	C30—H301	0.960
C23—C24	1.507 (2)	C30—H302	0.960
C24—C25	1.4461 (19)	C30—H303	0.960
O1···C6	3.539 (2)	H20···C3	3.428
O1···C15	3.457 (2)	H20···C13	3.228
O1···C25	3.484 (2)	H20···C15	3.096
O2···C27	3.204 (2)	H20···H3	3.231
O3···C20	3.444 (2)	H20···H82	3.420
O4···C12	3.547 (2)	H20···H121	3.283
O4···C21	3.419 (2)	H20···H131	3.436
O5···C12	3.309 (2)	H20···H132	2.655
C3···C19	3.573 (2)	H20···H133	3.116
C3···C20	3.451 (2)	H20···H152	2.590
C4···C19	3.438 (2)	H21···O4	2.824
C6···O1	3.539 (2)	H21···C30	3.326
C10···C30	3.441 (2)	H21···H4	3.219
C12···O4	3.547 (2)	H21···H82	3.506
C12···O5	3.309 (2)	H21···H132	2.842
C15···O1	3.457 (2)	H21···H301	3.458
C19···C3	3.573 (2)	H21···H303	2.458
C19···C4	3.438 (2)	H22···O4	3.261
C20···O3	3.444 (2)	H22···C3	3.497
C20···C3	3.451 (2)	H22···C4	3.399
C21···O4	3.419 (2)	H22···H3	3.031
C25···O1	3.484 (2)	H22···H4	2.850
C27···O2	3.204 (2)	H22···H231	3.459
C30···C10	3.441 (2)	H22···H232	3.598
O1···H6	2.628	H25···O1	2.567
O1···H20	3.448	H25···C9	3.378
O1···H25	2.567	H25···C10	3.502
O1···H131	3.590	H25···C15	3.511
O1···H152	2.541	H25···C28	3.553
O1···H282	3.334	H25···H10	2.940
O1···H283	2.939	H25···H131	3.100
O2···H18	2.790	H25···H152	2.977
O2···H271	2.616	H25···H153	3.210
O2···H272	2.949	H25···H282	3.393
O2···H281	3.436	H25···H283	2.844
O2···H283	3.240	H25···H302	3.568
O2···H302	3.319	H81···C7	3.543
O3···H19	3.353	H81···H6	3.111
O3···H20	2.679	H81···H7	2.899
O3···H133	3.489	H81···H272	3.405
O3···H301	3.324	H82···C17	3.154
O4···H4	3.425	H82···C18	3.042
O4···H10	2.863	H82···C19	2.938
O4···H21	2.824	H82···C20	2.936
O4···H22	3.261	H82···C21	3.004
O4···H122	2.754	H82···C22	3.108
O4···H131	2.964	H82···H18	3.559
O4···H303	3.021	H82···H19	3.414
O5···H3	2.746	H82···H20	3.420
O5···H121	2.735	H82···H21	3.506
O5···H122	3.018	H121···O5	2.735
O5···H131	3.286	H121···H20	3.283
O6···H4	3.361	H121···H133	3.209
O6···H5	3.157	H122···O4	2.754
O6···H153	3.170	H122···O5	3.018
O6···H281	3.484	H122···C23	3.528
C2···H232	3.173	H122···C24	3.269
C3···H20	3.428	H122···H231	2.880
C3···H22	3.497	H131···O1	3.590
C3···H232	2.864	H131···O4	2.964
C4···H22	3.399	H131···O5	3.286
C4···H232	2.836	H131···C10	3.537
C4···H303	3.514	H131···C15	3.480
C5···H151	3.559	H131···C24	3.177
C5···H232	3.095	H131···C25	3.305
C5···H282	3.463	H131···H10	2.981
C6···H19	3.406	H131···H20	3.436
C6···H151	3.505	H131···H25	3.100
C6···H232	3.363	H131···H152	2.989
C6···H272	3.120	H131···H153	3.306
C7···H19	3.494	H132···C9	3.562
C7···H81	3.543	H132···C10	3.204
C7···H232	3.398	H132···C20	3.235
C7···H272	3.342	H132···C21	3.335
C9···H6	3.518	H132···H10	3.001
C9···H25	3.378	H132···H20	2.655
C9···H132	3.562	H132···H21	2.842
C9···H152	3.527	H132···H152	3.450
C9···H283	3.452	H132···H301	3.133
C10···H25	3.502	H132···H303	3.289
C10···H131	3.537	H133···O3	3.489
C10···H132	3.204	H133···C30	3.577
C10···H301	3.137	H133···H20	3.116
C10···H302	3.168	H133···H121	3.209
C10···H303	3.458	H133···H133	2.767
C11···H301	3.093	H133···H152	3.534
C13···H10	3.335	H133···H301	2.759
C13···H20	3.228	H133···H303	3.591
C13···H152	3.506	H151···C5	3.559
C13···H301	3.148	H151···C6	3.505
C14···H18	3.583	H151···C28	3.432
C14···H301	3.492	H151···H5	3.154
C15···H6	3.511	H151···H6	3.048
C15···H19	3.462	H151···H18	3.287
C15···H20	3.096	H151···H19	3.389
C15···H25	3.511	H151···H271	3.459
C15···H131	3.480	H151···H281	3.038
C15···H281	3.329	H151···H282	3.033
C15···H282	3.257	H152···O1	2.541
C15···H301	3.426	H152···C9	3.527
C17···H82	3.154	H152···C13	3.506
C18···H4	3.569	H152···C19	3.549
C18···H7	3.531	H152···C20	3.286
C18···H82	3.042	H152···C25	3.471
C19···H4	3.594	H152···H6	3.070
C19···H7	3.589	H152···H19	3.110
C19···H82	2.938	H152···H20	2.590
C19···H152	3.549	H152···H25	2.977
C20···H3	3.350	H152···H131	2.989
C20···H82	2.936	H152···H132	3.450
C20···H132	3.235	H152···H133	3.534
C20···H152	3.286	H152···H282	3.118
C21···H82	3.004	H153···O6	3.170
C21···H132	3.335	H153···C25	3.281
C21···H303	3.358	H153···C26	3.167
C22···H4	3.499	H153···C28	3.184
C22···H82	3.108	H153···C29	3.457
C23···H122	3.528	H153···C30	3.182
C24···H122	3.269	H153···H25	3.210
C24···H131	3.177	H153···H131	3.306
C25···H10	3.593	H153···H281	2.856
C25···H131	3.305	H153···H282	3.070
C25···H152	3.471	H153···H301	2.707
C25···H153	3.281	H153···H302	3.229
C25···H283	3.450	H231···H3	2.993
C26···H153	3.167	H231···H22	3.459
C28···H5	3.305	H231···H122	2.880
C28···H25	3.553	H231···H231	3.291
C28···H151	3.432	H232···C2	3.173
C28···H153	3.184	H232···C3	2.864
C28···H282	3.314	H232···C4	2.836
C28···H283	3.556	H232···C5	3.095
C28···H302	2.975	H232···C6	3.363
C29···H153	3.457	H232···C7	3.398
C30···H4	3.473	H232···H3	3.244
C30···H5	3.260	H232···H4	3.212
C30···H10	3.164	H232···H5	3.584
C30···H21	3.326	H232···H22	3.598
C30···H133	3.577	H271···O2	2.616
C30···H153	3.182	H271···H151	3.459
C30···H281	3.387	H272···O2	2.949
C30···H283	3.569	H272···C6	3.120
H3···O5	2.746	H272···C7	3.342
H3···C20	3.350	H272···H6	3.114
H3···H20	3.231	H272···H7	3.482
H3···H22	3.031	H272···H81	3.405
H3···H231	2.993	H281···O2	3.436
H3···H232	3.244	H281···O6	3.484
H4···O4	3.425	H281···C15	3.329
H4···O6	3.361	H281···C30	3.387
H4···C18	3.569	H281···H5	3.185
H4···C19	3.594	H281···H151	3.038
H4···C22	3.499	H281···H153	2.856
H4···C30	3.473	H281···H302	2.578
H4···H21	3.219	H282···O1	3.334
H4···H22	2.850	H282···C5	3.463
H4···H232	3.212	H282···C15	3.257
H4···H303	2.826	H282···C28	3.314
H5···O6	3.157	H282···H5	2.735
H5···C28	3.305	H282···H6	3.191
H5···C30	3.260	H282···H25	3.393
H5···H151	3.154	H282···H151	3.033
H5···H232	3.584	H282···H152	3.118
H5···H281	3.185	H282···H153	3.070
H5···H282	2.735	H282···H282	3.056
H5···H283	3.508	H282···H283	2.923
H5···H302	3.021	H282···H302	3.310
H5···H303	3.089	H283···O1	2.939
H6···O1	2.628	H283···O2	3.240
H6···C9	3.518	H283···C9	3.452
H6···C15	3.511	H283···C25	3.450
H6···H19	3.037	H283···C28	3.556
H6···H81	3.111	H283···C30	3.569
H6···H151	3.048	H283···H5	3.508
H6···H152	3.070	H283···H25	2.844
H6···H272	3.114	H283···H282	2.923
H6···H282	3.191	H283···H283	3.558
H7···C18	3.531	H283···H302	2.615
H7···C19	3.589	H301···O3	3.324
H7···H7	3.332	H301···C10	3.137
H7···H18	3.076	H301···C11	3.093
H7···H19	3.189	H301···C13	3.148
H7···H81	2.899	H301···C14	3.492
H7···H272	3.482	H301···C15	3.426
H10···O4	2.863	H301···H10	3.054
H10···C13	3.335	H301···H21	3.458
H10···C25	3.593	H301···H132	3.133
H10···C30	3.164	H301···H133	2.759
H10···H25	2.940	H301···H153	2.707
H10···H131	2.981	H302···O2	3.319
H10···H132	3.001	H302···C10	3.168
H10···H301	3.054	H302···C28	2.975
H10···H302	2.955	H302···H5	3.021
H10···H303	2.946	H302···H10	2.955
H18···O2	2.790	H302···H25	3.568
H18···C14	3.583	H302···H153	3.229
H18···H7	3.076	H302···H281	2.578
H18···H82	3.559	H302···H282	3.310
H18···H151	3.287	H302···H283	2.615
H19···O3	3.353	H303···O4	3.021
H19···C6	3.406	H303···C4	3.514
H19···C7	3.494	H303···C10	3.458
H19···C15	3.462	H303···C21	3.358
H19···H6	3.037	H303···H4	2.826
H19···H7	3.189	H303···H5	3.089
H19···H82	3.414	H303···H10	2.946
H19···H151	3.389	H303···H21	2.458
H19···H152	3.110	H303···H132	3.289
H20···O1	3.448	H303···H133	3.591
H20···O3	2.679
C14—O3—C15	116.39 (15)	C7—C6—H6	119.9
C29—O6—C30	116.65 (13)	C2—C7—H7	119.4
C2—C1—C8	111.37 (10)	C6—C7—H7	119.4
C2—C1—C12	112.88 (14)	C1—C8—H81	108.5
C2—C1—C14	106.39 (11)	C1—C8—H82	108.5
C8—C1—C12	107.95 (12)	C9—C8—H81	108.5
C8—C1—C14	108.05 (13)	C9—C8—H82	108.5
C12—C1—C14	110.11 (9)	H81—C8—H82	109.5
C1—C2—C3	122.22 (11)	C9—C10—H10	118.8
C1—C2—C7	119.85 (15)	C11—C10—H10	118.8
C3—C2—C7	117.91 (15)	C1—C12—H121	108.6
C2—C3—C4	120.56 (13)	C1—C12—H122	108.6
C3—C4—C5	120.2 (2)	C11—C12—H121	108.6
C4—C5—C6	119.92 (18)	C11—C12—H122	108.6
C5—C6—C7	120.19 (15)	H121—C12—H122	109.5
C2—C7—C6	121.20 (18)	C11—C13—H131	109.5
C1—C8—C9	113.14 (11)	C11—C13—H132	109.5
O1—C9—C8	121.05 (13)	C11—C13—H133	109.5
O1—C9—C10	121.73 (16)	H131—C13—H132	109.5
C8—C9—C10	117.17 (17)	H131—C13—H133	109.5
C9—C10—C11	122.42 (16)	H132—C13—H133	109.5
C10—C11—C12	121.60 (12)	O3—C15—H151	109.5
C10—C11—C13	122.57 (16)	O3—C15—H152	109.5
C12—C11—C13	115.83 (16)	O3—C15—H153	109.5
C1—C12—C11	113.06 (14)	H151—C15—H152	109.5
O2—C14—O3	122.74 (14)	H151—C15—H153	109.5
O2—C14—C1	124.28 (13)	H152—C15—H153	109.5
O3—C14—C1	112.98 (13)	C17—C18—H18	119.6
C17—C16—C23	111.39 (10)	C19—C18—H18	119.6
C17—C16—C27	112.53 (13)	C18—C19—H19	119.7
C17—C16—C29	106.44 (12)	C20—C19—H19	119.7
C23—C16—C27	108.04 (12)	C19—C20—H20	120.3
C23—C16—C29	108.26 (13)	C21—C20—H20	120.3
C27—C16—C29	110.11 (10)	C20—C21—H21	119.7
C16—C17—C18	122.24 (11)	C22—C21—H21	119.7
C16—C17—C22	120.48 (17)	C17—C22—H22	119.3
C18—C17—C22	117.28 (17)	C21—C22—H22	119.3
C17—C18—C19	120.86 (14)	C16—C23—H231	108.4
C18—C19—C20	120.5 (2)	C16—C23—H232	108.4
C19—C20—C21	119.4 (2)	C24—C23—H231	108.4
C20—C21—C22	120.51 (17)	C24—C23—H232	108.4
C17—C22—C21	121.4 (2)	H231—C23—H232	109.5
C16—C23—C24	113.60 (11)	C24—C25—H25	118.7
O4—C24—C23	120.40 (13)	C26—C25—H25	118.7
O4—C24—C25	121.99 (18)	C16—C27—H271	108.6
C23—C24—C25	117.57 (16)	C16—C27—H272	108.6
C24—C25—C26	122.52 (17)	C26—C27—H271	108.6
C25—C26—C27	121.46 (12)	C26—C27—H272	108.6
C25—C26—C28	122.66 (16)	H271—C27—H272	109.5
C27—C26—C28	115.88 (15)	C26—C28—H281	109.5
C16—C27—C26	112.89 (14)	C26—C28—H282	109.5
O5—C29—O6	122.31 (13)	C26—C28—H283	109.5
O5—C29—C16	124.80 (12)	H281—C28—H282	109.5
O6—C29—C16	112.87 (13)	H281—C28—H283	109.5
C2—C3—H3	119.7	H282—C28—H283	109.5
C4—C3—H3	119.7	O6—C30—H301	109.5
C3—C4—H4	119.9	O6—C30—H302	109.5
C5—C4—H4	119.9	O6—C30—H303	109.5
C4—C5—H5	120.0	H301—C30—H302	109.5
C6—C5—H5	120.0	H301—C30—H303	109.5
C5—C6—H6	119.9	H302—C30—H303	109.5
C15—O3—C14—O2	−4.0 (2)	C10—C11—C12—C1	24.1 (2)
C15—O3—C14—C1	175.59 (14)	C13—C11—C12—C1	−156.62 (13)
C30—O6—C29—O5	1.5 (2)	C17—C16—C23—C24	−176.24 (12)
C30—O6—C29—C16	−177.29 (14)	C23—C16—C17—C18	138.26 (14)
C2—C1—C8—C9	178.77 (13)	C23—C16—C17—C22	−42.22 (19)
C8—C1—C2—C3	−131.95 (14)	C17—C16—C27—C26	174.86 (11)
C8—C1—C2—C7	49.37 (18)	C27—C16—C17—C18	16.75 (18)
C2—C1—C12—C11	−174.33 (11)	C27—C16—C17—C22	−163.73 (15)
C12—C1—C2—C3	−10.33 (18)	C17—C16—C29—O5	−100.91 (19)
C12—C1—C2—C7	170.99 (13)	C17—C16—C29—O6	77.80 (14)
C2—C1—C14—O2	104.06 (17)	C29—C16—C17—C18	−103.94 (15)
C2—C1—C14—O3	−75.56 (13)	C29—C16—C17—C22	75.58 (17)
C14—C1—C2—C3	110.54 (14)	C23—C16—C27—C26	51.47 (16)
C14—C1—C2—C7	−68.14 (16)	C27—C16—C23—C24	−52.15 (17)
C8—C1—C12—C11	−50.80 (16)	C23—C16—C29—O5	18.9 (2)
C12—C1—C8—C9	54.32 (18)	C23—C16—C29—O6	−162.36 (12)
C8—C1—C14—O2	−15.62 (18)	C29—C16—C23—C24	67.07 (15)
C8—C1—C14—O3	164.76 (11)	C27—C16—C29—O5	136.85 (17)
C14—C1—C8—C9	−64.73 (15)	C27—C16—C29—O6	−44.44 (19)
C12—C1—C14—O2	−133.30 (16)	C29—C16—C27—C26	−66.58 (17)
C12—C1—C14—O3	47.08 (18)	C16—C17—C18—C19	178.51 (13)
C14—C1—C12—C11	66.94 (17)	C16—C17—C22—C21	−178.77 (18)
C1—C2—C3—C4	−178.40 (13)	C18—C17—C22—C21	0.8 (2)
C1—C2—C7—C6	179.17 (14)	C22—C17—C18—C19	−1.0 (2)
C3—C2—C7—C6	0.4 (2)	C17—C18—C19—C20	0.2 (2)
C7—C2—C3—C4	0.3 (2)	C18—C19—C20—C21	0.9 (2)
C2—C3—C4—C5	−0.8 (2)	C19—C20—C21—C22	−1.1 (3)
C3—C4—C5—C6	0.7 (2)	C20—C21—C22—C17	0.3 (3)
C4—C5—C6—C7	0.1 (2)	C16—C23—C24—O4	−156.11 (15)
C5—C6—C7—C2	−0.6 (2)	C16—C23—C24—C25	26.2 (2)
C1—C8—C9—O1	151.74 (15)	O4—C24—C25—C26	−174.21 (16)
C1—C8—C9—C10	−30.6 (2)	C23—C24—C25—C26	3.5 (2)
O1—C9—C10—C11	178.37 (16)	C24—C25—C26—C27	−3.9 (2)
C8—C9—C10—C11	0.8 (2)	C24—C25—C26—C28	175.33 (15)
C9—C10—C11—C12	2.6 (2)	C25—C26—C27—C16	−25.3 (2)
C9—C10—C11—C13	−176.68 (15)	C28—C26—C27—C16	155.46 (13)