Diethyl naphthalene-1,8-dicarboxyl­ate

The title compound, C₁₆H₁₆O₄, crystallizes with two mol­ecules in the asymmetric unit. The two mol­ecules differ in the orientations of the ethyl groups. The crystal packing is stabilized by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.106
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C12'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C28'
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C31    -   C32    ...       1.43 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Diethyl naphthalene-1,8-dicarboxylate

Crystal data

C16H16O4	F(000) = 1152
Mr = 272.29	Dx = 1.256 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 34 reflections
a = 10.210 (2) Å	θ = 3.0–14.3°
b = 9.672 (1) Å	µ = 0.09 mm^−1
c = 29.163 (4) Å	T = 295 K
β = 90.15 (1)°	Block, colourless
V = 2879.9 (8) Å^3	0.58 × 0.46 × 0.46 mm
Z = 8

Data collection

Bruker P4 diffractometer	Rint = 0.010
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 1.4°
Graphite monochromator	h = 0→12
ω scans	k = 0→11
5684 measured reflections	l = −35→35
5365 independent reflections	3 standard reflections every 97 reflections
2323 reflections with I > 2σ(I)	intensity decay: 6.2%

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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0526P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max = 0.001
5365 reflections	Δρmax = 0.13 e Å^−3
406 parameters	Δρmin = −0.12 e Å^−3
14 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: 0.0087 (6)

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	Occ. (<1)
O1	0.75532 (13)	0.35111 (14)	0.07430 (5)	0.0744 (4)
O2	0.64765 (16)	0.18191 (17)	0.03821 (5)	0.0970 (5)
O3	0.64319 (13)	0.18601 (14)	0.14723 (5)	0.0716 (4)
O4	0.78707 (16)	0.32191 (16)	0.18406 (5)	0.0907 (5)
C1	0.52801 (19)	0.3643 (2)	0.07341 (8)	0.0612 (6)
C2	0.4373 (2)	0.3763 (2)	0.03929 (8)	0.0808 (7)
H2	0.4463	0.3228	0.0130	0.097*
C3	0.3314 (3)	0.4666 (3)	0.04279 (11)	0.0992 (9)
H3	0.2695	0.4713	0.0194	0.119*
C4	0.3192 (2)	0.5466 (3)	0.08002 (11)	0.0940 (9)
H4	0.2514	0.6106	0.0815	0.113*
C5	0.3963 (3)	0.6212 (3)	0.15555 (12)	0.0984 (9)
H5	0.3307	0.6878	0.1558	0.118*
C6	0.4763 (3)	0.6107 (3)	0.19197 (10)	0.0983 (9)
H6	0.4683	0.6714	0.2165	0.118*
C7	0.5726 (2)	0.5067 (2)	0.19241 (8)	0.0813 (7)
H7	0.6259	0.4965	0.2181	0.098*
C8	0.5891 (2)	0.4202 (2)	0.15580 (8)	0.0603 (5)
C9	0.51134 (19)	0.4373 (2)	0.11554 (8)	0.0597 (5)
C10	0.4082 (2)	0.5353 (2)	0.11722 (9)	0.0735 (6)
C11	0.6474 (2)	0.2854 (2)	0.06095 (8)	0.0681 (6)
C14	0.6858 (2)	0.3075 (2)	0.16341 (7)	0.0669 (6)
C15	0.7293 (2)	0.0673 (2)	0.15400 (8)	0.0855 (7)
H15A	0.8191	0.0988	0.1572	0.103*
H15B	0.7246	0.0072	0.1274	0.103*
C16	0.6907 (3)	−0.0100 (3)	0.19529 (9)	0.1187 (10)
H16A	0.6966	0.0493	0.2216	0.142*
H16B	0.7480	−0.0877	0.1993	0.142*
H16C	0.6022	−0.0420	0.1919	0.142*
O5	0.15196 (14)	1.09045 (15)	0.15898 (6)	0.0855 (5)
O6	0.30660 (16)	0.96680 (18)	0.19536 (5)	0.0997 (6)
O7	0.26066 (13)	0.92182 (14)	0.08610 (5)	0.0704 (4)
O8	0.13836 (15)	1.08258 (17)	0.05099 (5)	0.0931 (5)
C17	0.10945 (19)	0.8563 (2)	0.17235 (8)	0.0618 (6)
C18	0.1011 (2)	0.7757 (3)	0.21054 (8)	0.0830 (7)
H18	0.1572	0.7931	0.2350	0.100*
C19	0.0109 (3)	0.6679 (3)	0.21409 (10)	0.0982 (8)
H19	0.0098	0.6119	0.2400	0.118*
C20	−0.0746 (3)	0.6459 (3)	0.17957 (11)	0.0934 (8)
H20	−0.1371	0.5765	0.1824	0.112*
C21	−0.1640 (2)	0.7041 (3)	0.10390 (11)	0.0962 (9)
H21	−0.2287	0.6374	0.1077	0.115*
C22	−0.1604 (3)	0.7783 (3)	0.06498 (11)	0.1004 (9)
H22	−0.2249	0.7667	0.0427	0.120*
C23	−0.0594 (2)	0.8727 (3)	0.05822 (8)	0.0836 (7)
H23	−0.0559	0.9213	0.0307	0.100*
C24	0.03450 (19)	0.8963 (2)	0.09048 (8)	0.0621 (5)
C25	0.02696 (18)	0.8292 (2)	0.13410 (8)	0.0581 (5)
C26	−0.0709 (2)	0.7259 (2)	0.13931 (9)	0.0725 (6)
C27	0.2017 (2)	0.9741 (3)	0.17646 (8)	0.0731 (6)
C30	0.1475 (2)	0.9805 (2)	0.07430 (7)	0.0677 (6)
C31	0.3787 (2)	0.9882 (2)	0.06782 (9)	0.0935 (8)
H31A	0.3657	1.0117	0.0358	0.112*
H31B	0.3970	1.0726	0.0846	0.112*
C32	0.4862 (2)	0.8940 (3)	0.07239 (9)	0.1030 (9)
H32A	0.5019	0.8758	0.1043	0.124*
H32B	0.5632	0.9341	0.0590	0.124*
H32C	0.4656	0.8091	0.0569	0.124*
C12	0.8740 (6)	0.2863 (12)	0.0537 (4)	0.076 (2)	0.598 (14)
H12A	0.8664	0.2804	0.0206	0.091*	0.598 (14)
H12B	0.8890	0.1945	0.0661	0.091*	0.598 (14)
C13	0.9814 (7)	0.3848 (9)	0.0677 (5)	0.117 (3)	0.598 (14)
H13A	0.9704	0.4710	0.0518	0.140*	0.598 (14)
H13B	1.0649	0.3457	0.0601	0.140*	0.598 (14)
H13C	0.9772	0.4006	0.1002	0.140*	0.598 (14)
C12'	0.8890 (10)	0.2897 (18)	0.0739 (4)	0.065 (3)	0.402 (14)
H12C	0.8856	0.1911	0.0679	0.078*	0.402 (14)
H12D	0.9339	0.3054	0.1027	0.078*	0.402 (14)
C13'	0.9554 (14)	0.3661 (13)	0.0350 (6)	0.104 (4)	0.402 (14)
H13D	0.9197	0.3356	0.0063	0.125*	0.402 (14)
H13E	1.0478	0.3475	0.0358	0.125*	0.402 (14)
H13F	0.9409	0.4636	0.0384	0.125*	0.402 (14)
C28	0.2390 (15)	1.2040 (11)	0.1747 (8)	0.109 (6)	0.363 (16)
H28A	0.3096	1.2192	0.1531	0.130*	0.363 (16)
H28B	0.2762	1.1834	0.2045	0.130*	0.363 (16)
C29	0.1496 (12)	1.3295 (11)	0.1771 (6)	0.094 (4)	0.363 (16)
H29A	0.1134	1.3476	0.1473	0.112*	0.363 (16)
H29B	0.1989	1.4084	0.1871	0.112*	0.363 (16)
H29C	0.0799	1.3118	0.1983	0.112*	0.363 (16)
C28'	0.2309 (10)	1.2187 (8)	0.1542 (3)	0.082 (2)	0.637 (16)
H28C	0.2018	1.2723	0.1279	0.099*	0.637 (16)
H28D	0.3230	1.1968	0.1505	0.099*	0.637 (16)
C29'	0.2083 (12)	1.2963 (11)	0.1979 (3)	0.126 (3)	0.637 (16)
H29D	0.1189	1.3268	0.1991	0.151*	0.637 (16)
H29E	0.2655	1.3751	0.1990	0.151*	0.637 (16)
H29F	0.2261	1.2369	0.2235	0.151*	0.637 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0506 (9)	0.0646 (9)	0.1080 (11)	0.0006 (8)	0.0175 (8)	−0.0062 (8)
O2	0.1152 (14)	0.0782 (12)	0.0976 (12)	0.0009 (10)	0.0058 (10)	−0.0237 (10)
O3	0.0730 (10)	0.0514 (9)	0.0905 (10)	0.0012 (8)	−0.0084 (8)	0.0029 (8)
O4	0.0794 (11)	0.0964 (12)	0.0964 (12)	0.0004 (10)	−0.0243 (9)	−0.0086 (10)
C1	0.0515 (13)	0.0532 (13)	0.0790 (16)	−0.0081 (11)	0.0050 (12)	0.0098 (12)
C2	0.0673 (16)	0.0838 (18)	0.0912 (17)	−0.0114 (14)	−0.0057 (14)	0.0111 (14)
C3	0.0670 (18)	0.102 (2)	0.129 (3)	−0.0058 (17)	−0.0155 (18)	0.0407 (19)
C4	0.0579 (16)	0.0799 (19)	0.144 (3)	0.0097 (14)	0.0151 (19)	0.0327 (19)
C5	0.090 (2)	0.0650 (17)	0.140 (3)	0.0117 (16)	0.0506 (19)	0.011 (2)
C6	0.115 (2)	0.0687 (18)	0.111 (2)	−0.0079 (18)	0.0508 (19)	−0.0167 (17)
C7	0.0882 (18)	0.0689 (16)	0.0868 (17)	−0.0113 (14)	0.0182 (14)	−0.0067 (14)
C8	0.0579 (13)	0.0497 (12)	0.0732 (15)	−0.0058 (11)	0.0125 (12)	−0.0016 (12)
C9	0.0466 (12)	0.0462 (12)	0.0864 (17)	−0.0063 (11)	0.0171 (12)	0.0092 (12)
C10	0.0589 (15)	0.0581 (15)	0.1035 (19)	−0.0009 (12)	0.0242 (14)	0.0156 (14)
C11	0.0725 (16)	0.0594 (15)	0.0725 (16)	−0.0034 (14)	0.0076 (13)	0.0041 (13)
C14	0.0687 (15)	0.0677 (15)	0.0643 (15)	−0.0063 (14)	0.0018 (12)	−0.0014 (13)
C15	0.0958 (18)	0.0699 (16)	0.0907 (18)	0.0179 (15)	−0.0036 (14)	0.0023 (14)
C16	0.158 (3)	0.091 (2)	0.107 (2)	0.0358 (19)	0.0181 (19)	0.0271 (18)
O5	0.0769 (11)	0.0579 (10)	0.1217 (13)	−0.0089 (9)	−0.0058 (9)	−0.0162 (10)
O6	0.0733 (11)	0.1228 (14)	0.1029 (12)	−0.0160 (11)	−0.0207 (10)	−0.0020 (11)
O7	0.0512 (9)	0.0644 (9)	0.0956 (10)	−0.0004 (8)	0.0093 (8)	0.0160 (8)
O8	0.0965 (12)	0.0754 (11)	0.1075 (13)	0.0038 (10)	−0.0080 (10)	0.0254 (10)
C17	0.0545 (13)	0.0595 (14)	0.0714 (15)	0.0020 (11)	0.0093 (12)	−0.0027 (12)
C18	0.0774 (17)	0.0892 (19)	0.0826 (18)	0.0047 (15)	0.0126 (14)	0.0009 (15)
C19	0.098 (2)	0.086 (2)	0.111 (2)	0.0049 (18)	0.0333 (18)	0.0213 (18)
C20	0.0785 (19)	0.0635 (17)	0.138 (3)	−0.0103 (15)	0.0396 (18)	−0.0018 (18)
C21	0.0624 (17)	0.082 (2)	0.144 (3)	−0.0162 (15)	0.0090 (19)	−0.039 (2)
C22	0.0677 (18)	0.107 (2)	0.126 (3)	−0.0018 (17)	−0.0196 (18)	−0.038 (2)
C23	0.0696 (16)	0.0907 (18)	0.0905 (17)	0.0038 (15)	−0.0151 (15)	−0.0157 (15)
C24	0.0535 (13)	0.0559 (13)	0.0768 (15)	0.0039 (11)	−0.0042 (12)	−0.0108 (12)
C25	0.0470 (12)	0.0493 (12)	0.0782 (15)	0.0033 (11)	0.0098 (11)	−0.0124 (12)
C26	0.0567 (14)	0.0564 (14)	0.1045 (19)	−0.0044 (12)	0.0197 (14)	−0.0175 (14)
C27	0.0658 (16)	0.0766 (17)	0.0769 (16)	−0.0076 (15)	−0.0013 (13)	−0.0065 (14)
C30	0.0666 (15)	0.0647 (15)	0.0717 (15)	0.0023 (14)	−0.0028 (12)	0.0005 (13)
C31	0.0693 (16)	0.0825 (18)	0.129 (2)	−0.0128 (15)	0.0254 (15)	0.0161 (16)
C32	0.0642 (16)	0.110 (2)	0.135 (2)	−0.0152 (16)	0.0177 (15)	0.0096 (18)
C12	0.065 (3)	0.082 (4)	0.080 (6)	0.019 (3)	0.012 (4)	0.002 (6)
C13	0.051 (3)	0.119 (5)	0.181 (9)	0.009 (4)	0.029 (5)	−0.017 (6)
C12'	0.052 (6)	0.083 (5)	0.060 (7)	0.013 (5)	0.014 (4)	−0.004 (7)
C13'	0.088 (7)	0.080 (7)	0.145 (9)	0.010 (5)	0.061 (8)	0.014 (7)
C28	0.144 (9)	0.064 (6)	0.117 (15)	−0.037 (6)	−0.031 (11)	−0.017 (8)
C29	0.107 (8)	0.057 (6)	0.117 (9)	−0.025 (5)	0.009 (6)	0.000 (6)
C28'	0.095 (5)	0.078 (4)	0.073 (5)	−0.038 (3)	0.006 (3)	−0.008 (3)
C29'	0.166 (8)	0.091 (5)	0.119 (5)	−0.048 (5)	0.024 (5)	−0.032 (4)

Geometric parameters (Å, º)

O1—C11	1.329 (2)	C19—C20	1.348 (3)
O1—C12'	1.489 (8)	C19—H19	0.93
O1—C12	1.492 (6)	C20—C26	1.407 (3)
O2—C11	1.201 (2)	C20—H20	0.93
O3—C14	1.338 (2)	C21—C22	1.343 (3)
O3—C15	1.459 (2)	C21—C26	1.418 (3)
O4—C14	1.203 (2)	C21—H21	0.93
C1—C2	1.363 (3)	C22—C23	1.392 (3)
C1—C9	1.428 (3)	C22—H22	0.93
C1—C11	1.484 (3)	C23—C24	1.361 (3)
C2—C3	1.394 (3)	C23—H23	0.93
C2—H2	0.93	C24—C25	1.430 (3)
C3—C4	1.339 (3)	C24—C30	1.490 (3)
C3—H3	0.93	C25—C26	1.421 (3)
C4—C10	1.418 (3)	C31—C32	1.432 (3)
C4—H4	0.93	C31—H31A	0.97
C5—C6	1.342 (3)	C31—H31B	0.97
C5—C10	1.398 (3)	C32—H32A	0.96
C5—H5	0.93	C32—H32B	0.96
C6—C7	1.406 (3)	C32—H32C	0.96
C6—H6	0.93	C12—C13	1.509 (8)
C7—C8	1.367 (3)	C12—H12A	0.97
C7—H7	0.93	C12—H12B	0.97
C8—C9	1.425 (3)	C13—H13A	0.96
C8—C14	1.488 (3)	C13—H13B	0.96
C9—C10	1.417 (3)	C13—H13C	0.96
C15—C16	1.472 (3)	C12'—C13'	1.514 (9)
C15—H15A	0.97	C12'—H12C	0.97
C15—H15B	0.97	C12'—H12D	0.97
C16—H16A	0.96	C13'—H13D	0.96
C16—H16B	0.96	C13'—H13E	0.96
C16—H16C	0.96	C13'—H13F	0.96
O5—C27	1.336 (2)	C28—C29	1.521 (9)
O5—C28	1.485 (9)	C28—H28A	0.97
O5—C28'	1.486 (6)	C28—H28B	0.97
O6—C27	1.205 (2)	C29—H29A	0.96
O7—C30	1.331 (2)	C29—H29B	0.96
O7—C31	1.467 (2)	C29—H29C	0.96
O8—C30	1.203 (2)	C28'—C29'	1.498 (7)
C17—C18	1.362 (3)	C28'—H28C	0.97
C17—C25	1.420 (3)	C28'—H28D	0.97
C17—C27	1.483 (3)	C29'—H29D	0.96
C18—C19	1.395 (3)	C29'—H29E	0.96
C18—H18	0.93	C29'—H29F	0.96
C11—O1—C12'	124.5 (8)	C21—C22—C23	119.5 (3)
C11—O1—C12	110.8 (4)	C21—C22—H22	120.3
C14—O3—C15	116.58 (17)	C23—C22—H22	120.3
C2—C1—C9	120.3 (2)	C24—C23—C22	122.2 (3)
C2—C1—C11	115.0 (2)	C24—C23—H23	118.9
C9—C1—C11	124.4 (2)	C22—C23—H23	118.9
C1—C2—C3	121.7 (2)	C23—C24—C25	120.0 (2)
C1—C2—H2	119.1	C23—C24—C30	114.7 (2)
C3—C2—H2	119.1	C25—C24—C30	124.96 (19)
C4—C3—C2	119.6 (3)	C17—C25—C26	117.5 (2)
C4—C3—H3	120.2	C17—C25—C24	125.56 (19)
C2—C3—H3	120.2	C26—C25—C24	117.0 (2)
C3—C4—C10	121.0 (3)	C20—C26—C21	120.5 (3)
C3—C4—H4	119.5	C20—C26—C25	119.7 (2)
C10—C4—H4	119.5	C21—C26—C25	119.8 (2)
C6—C5—C10	122.3 (3)	O6—C27—O5	124.1 (2)
C6—C5—H5	118.9	O6—C27—C17	123.8 (2)
C10—C5—H5	118.9	O5—C27—C17	112.1 (2)
C5—C6—C7	119.0 (3)	O8—C30—O7	124.2 (2)
C5—C6—H6	120.5	O8—C30—C24	124.7 (2)
C7—C6—H6	120.5	O7—C30—C24	110.95 (19)
C8—C7—C6	121.2 (2)	C32—C31—O7	108.56 (19)
C8—C7—H7	119.4	C32—C31—H31A	110.0
C6—C7—H7	119.4	O7—C31—H31A	110.0
C7—C8—C9	120.2 (2)	C32—C31—H31B	110.0
C7—C8—C14	114.5 (2)	O7—C31—H31B	110.0
C9—C8—C14	125.16 (19)	H31A—C31—H31B	108.4
C10—C9—C8	117.4 (2)	C31—C32—H32A	109.5
C10—C9—C1	116.8 (2)	C31—C32—H32B	109.5
C8—C9—C1	125.77 (19)	H32A—C32—H32B	109.5
C5—C10—C4	120.6 (3)	C31—C32—H32C	109.5
C5—C10—C9	119.4 (3)	H32A—C32—H32C	109.5
C4—C10—C9	120.0 (2)	H32B—C32—H32C	109.5
O2—C11—O1	123.9 (2)	O1—C12—C13	102.5 (6)
O2—C11—C1	124.5 (2)	O1—C12—H12A	111.3
O1—C11—C1	111.30 (19)	C13—C12—H12A	111.3
O4—C14—O3	123.8 (2)	O1—C12—H12B	111.3
O4—C14—C8	124.0 (2)	C13—C12—H12B	111.3
O3—C14—C8	112.07 (19)	H12A—C12—H12B	109.2
O3—C15—C16	110.3 (2)	O1—C12'—C13'	103.0 (8)
O3—C15—H15A	109.6	O1—C12'—H12C	111.2
C16—C15—H15A	109.6	C13'—C12'—H12C	111.2
O3—C15—H15B	109.6	O1—C12'—H12D	111.2
C16—C15—H15B	109.6	C13'—C12'—H12D	111.2
H15A—C15—H15B	108.1	H12C—C12'—H12D	109.1
C15—C16—H16A	109.5	C12'—C13'—H13D	109.5
C15—C16—H16B	109.5	C12'—C13'—H13E	109.5
H16A—C16—H16B	109.5	H13D—C13'—H13E	109.5
C15—C16—H16C	109.5	C12'—C13'—H13F	109.5
H16A—C16—H16C	109.5	H13D—C13'—H13F	109.5
H16B—C16—H16C	109.5	H13E—C13'—H13F	109.5
C27—O5—C28	106.2 (6)	O5—C28—C29	104.2 (9)
C27—O5—C28'	122.2 (5)	O5—C28—H28A	110.9
C30—O7—C31	115.65 (17)	C29—C28—H28A	110.9
C18—C17—C25	119.9 (2)	O5—C28—H28B	110.9
C18—C17—C27	114.5 (2)	C29—C28—H28B	110.9
C25—C17—C27	125.5 (2)	H28A—C28—H28B	108.9
C17—C18—C19	122.1 (2)	O5—C28'—C29'	104.7 (5)
C17—C18—H18	118.9	O5—C28'—H28C	110.8
C19—C18—H18	118.9	C29'—C28'—H28C	110.8
C20—C19—C18	119.3 (3)	O5—C28'—H28D	110.8
C20—C19—H19	120.4	C29'—C28'—H28D	110.8
C18—C19—H19	120.4	H28C—C28'—H28D	108.9
C19—C20—C26	121.2 (2)	C28'—C29'—H29D	109.5
C19—C20—H20	119.4	C28'—C29'—H29E	109.5
C26—C20—H20	119.4	H29D—C29'—H29E	109.5
C22—C21—C26	121.1 (3)	C28'—C29'—H29F	109.5
C22—C21—H21	119.5	H29D—C29'—H29F	109.5
C26—C21—H21	119.5	H29E—C29'—H29F	109.5
C9—C1—C2—C3	4.7 (3)	C26—C21—C22—C23	3.6 (4)
C11—C1—C2—C3	−168.58 (19)	C21—C22—C23—C24	−2.2 (4)
C1—C2—C3—C4	1.6 (4)	C22—C23—C24—C25	−3.8 (3)
C2—C3—C4—C10	−3.7 (4)	C22—C23—C24—C30	169.4 (2)
C10—C5—C6—C7	−2.4 (4)	C18—C17—C25—C26	6.1 (3)
C5—C6—C7—C8	2.6 (4)	C27—C17—C25—C26	−169.42 (19)
C6—C7—C8—C9	2.2 (3)	C18—C17—C25—C24	−173.37 (19)
C6—C7—C8—C14	−174.4 (2)	C27—C17—C25—C24	11.1 (3)
C7—C8—C9—C10	−7.0 (3)	C23—C24—C25—C17	−172.51 (19)
C14—C8—C9—C10	169.11 (18)	C30—C24—C25—C17	15.1 (3)
C7—C8—C9—C1	172.93 (18)	C23—C24—C25—C26	8.0 (3)
C14—C8—C9—C1	−10.9 (3)	C30—C24—C25—C26	−164.33 (18)
C2—C1—C9—C10	−8.6 (3)	C19—C20—C26—C21	−178.1 (2)
C11—C1—C9—C10	164.03 (18)	C19—C20—C26—C25	1.9 (3)
C2—C1—C9—C8	171.44 (19)	C22—C21—C26—C20	−179.0 (2)
C11—C1—C9—C8	−15.9 (3)	C22—C21—C26—C25	1.0 (3)
C6—C5—C10—C4	178.0 (2)	C17—C25—C26—C20	−6.2 (3)
C6—C5—C10—C9	−2.7 (3)	C24—C25—C26—C20	173.28 (19)
C3—C4—C10—C5	178.7 (2)	C17—C25—C26—C21	173.81 (19)
C3—C4—C10—C9	−0.6 (3)	C24—C25—C26—C21	−6.7 (3)
C8—C9—C10—C5	7.3 (3)	C28—O5—C27—O6	−9.3 (11)
C1—C9—C10—C5	−172.71 (18)	C28'—O5—C27—O6	10.5 (5)
C8—C9—C10—C4	−173.45 (18)	C28—O5—C27—C17	167.3 (10)
C1—C9—C10—C4	6.6 (3)	C28'—O5—C27—C17	−172.8 (3)
C12'—O1—C11—O2	−16.6 (6)	C18—C17—C27—O6	39.9 (3)
C12—O1—C11—O2	5.2 (6)	C25—C17—C27—O6	−144.4 (2)
C12'—O1—C11—C1	169.6 (5)	C18—C17—C27—O5	−136.7 (2)
C12—O1—C11—C1	−168.7 (6)	C25—C17—C27—O5	39.0 (3)
C2—C1—C11—O2	−40.4 (3)	C31—O7—C30—O8	−1.3 (3)
C9—C1—C11—O2	146.6 (2)	C31—O7—C30—C24	173.89 (18)
C2—C1—C11—O1	133.47 (19)	C23—C24—C30—O8	43.3 (3)
C9—C1—C11—O1	−39.5 (3)	C25—C24—C30—O8	−144.0 (2)
C15—O3—C14—O4	−2.5 (3)	C23—C24—C30—O7	−131.9 (2)
C15—O3—C14—C8	−178.45 (17)	C25—C24—C30—O7	40.8 (3)
C7—C8—C14—O4	−39.0 (3)	C30—O7—C31—C32	−164.0 (2)
C9—C8—C14—O4	144.7 (2)	C11—O1—C12—C13	173.0 (9)
C7—C8—C14—O3	136.92 (18)	C12'—O1—C12—C13	−57 (2)
C9—C8—C14—O3	−39.4 (3)	C11—O1—C12'—C13'	108.9 (15)
C14—O3—C15—C16	96.1 (2)	C12—O1—C12'—C13'	48.8 (18)
C25—C17—C18—C19	−1.7 (3)	C27—O5—C28—C29	−151.0 (15)
C27—C17—C18—C19	174.3 (2)	C28'—O5—C28—C29	73.6 (19)
C17—C18—C19—C20	−2.8 (4)	C27—O5—C28'—C29'	−91.5 (11)
C18—C19—C20—C26	2.7 (4)	C28—O5—C28'—C29'	−38.6 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O4	0.97	2.32	2.679 (3)	101
C18—H18···O4^i	0.93	2.44	3.307 (3)	155
C20—H20···O4^ii	0.93	2.58	3.440 (3)	154
C23—H23···O8^iii	0.93	2.52	3.312 (3)	142

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