(2RS,3SR)-Diethyl 2,3-bis­(3,4,5-trimethoxy­benzo­yl)succinate

The title compound, C₂₈H₃₄O₁₂, is the meso isomer of a 2,3-disubstituted succinate derivative. Mol­ecules are weakly linked via C—H...π inter­actions, forming layers parallel to the (100) plane.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H17B   ..  CG2     ..       3.31 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H18B   ..  CG2     ..       3.37 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.66 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27B   ..  CG1     ..       3.23 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C18    ..  CG2     ..       4.03 Ang.

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           27.00
           From the CIF: _reflns_number_total               3139
           Count of symmetry unique reflns         3149
           Completeness (_total/calc)             99.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 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
   1 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
   5 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

According to the literature (Wu et al., 1998), we have synthesized the title compound, (I), and its crystal structure is reported here. The molecular structure of (I) is illustrated in Fig. 1, and selected geometric parameters are given in Table 1. The chiral atoms C11 and C15 possess different configurations, indicating that (I) is the meso isomer. PLATON (Spek, 2003) shows that intermolecular hydrogen bonds and π–π interactions are absent; however, molecules are weakly linked together by C—H···π interactions (Fig. 2 and Table 2). Cg1 and Cg2 are the centroids of the C4–C9 and C20–C25 phenyl rings, respectively.

S2. Experimental

Compound (I) was synthesized according to the literature procedure (Wu et al., 1998). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution at room temperature.

S3. Refinement

All H atoms were placed in idealized positions [C—H(methyl) = 0.96 Å, C—H(methylene) = 0.97 Å, C—H(methylidyne) = 0.98 Å, and C—H(aromatic) = 0.93 Å] and included in the refinement in the riding-model approximation, with U_iso(methyl H) = 1.5U_eq(C) and U_iso(methylene, methylidyne and aromatic H) = 1.2U_eq(C). Friedel pairs were merged, since anormalous scattering effects were negligible.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures

	Fig. 1. Molecular structure of (I), showing 30% probability displacement ellipsoids.
	Fig. 2. Plot of the crystal packing, showing the linkage of the molecules by C—H···π interactions (dashed lines). [Symmtry codes: (a) 1 − x, 1 − y, 1/2 + z; (b) x, y − 1, z; (c) 1 − x, 2 − y, z − 1/2.]

(2RS,3SR)-Diethyl 2,3-bis(3,4,5-trimethoxybenzoyl)succinate

Crystal data

C28H34O12	F(000) = 1192
Mr = 562.55	Dx = 1.330 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2977 reflections
a = 14.8730 (14) Å	θ = 2.7–22.3°
b = 7.9521 (8) Å	µ = 0.10 mm^−1
c = 23.763 (2) Å	T = 292 K
V = 2810.5 (5) Å^3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART Apex CCD area-detector diffractometer	2404 reflections with I > 2σ(I)
Radiation source: fine focus sealed Siemens Mo tube	Rint = 0.051
Graphite monochromator	θmax = 27.0°, θmin = 1.7°
0.3° wide ω exposures scans	h = −19→16
18080 measured reflections	k = −10→10
3139 independent reflections	l = −30→30

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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.2925P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.005
3139 reflections	Δρmax = 0.19 e Å^−3
369 parameters	Δρmin = −0.14 e Å^−3
1 restraint	Absolute structure: see text
Primary atom site location: structure-invariant direct methods

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
C1	0.9139 (3)	0.2526 (7)	1.0339 (2)	0.0719 (13)
H1A	0.8828	0.1507	1.0244	0.108*
H1B	0.9756	0.2276	1.0423	0.108*
H1C	0.9112	0.3290	1.0026	0.108*
C2	0.7979 (4)	0.3502 (7)	1.21690 (19)	0.0761 (14)
H2A	0.7392	0.3515	1.2337	0.114*
H2B	0.8420	0.3806	1.2446	0.114*
H2C	0.8107	0.2394	1.2029	0.114*
C3	0.5295 (3)	0.5472 (6)	1.18634 (18)	0.0622 (12)
H3A	0.5067	0.6159	1.1563	0.093*
H3B	0.5175	0.6006	1.2218	0.093*
H3C	0.5006	0.4393	1.1854	0.093*
C4	0.7278 (2)	0.3222 (5)	1.03294 (14)	0.0442 (8)
H4	0.7523	0.2768	1.0003	0.053*
C5	0.7832 (2)	0.3578 (5)	1.07911 (15)	0.0449 (9)
C6	0.7458 (3)	0.4269 (4)	1.12755 (14)	0.0443 (8)
C7	0.6536 (2)	0.4599 (5)	1.13031 (14)	0.0414 (8)
C8	0.5993 (2)	0.4241 (5)	1.08482 (14)	0.0417 (8)
H8	0.5379	0.4459	1.0866	0.050*
C9	0.6364 (2)	0.3551 (4)	1.03614 (13)	0.0384 (7)
C10	0.5738 (2)	0.3190 (5)	0.98917 (14)	0.0490 (9)
C11	0.6050 (2)	0.2219 (5)	0.93729 (13)	0.0400 (8)
H11	0.6653	0.2594	0.9263	0.048*
C12	0.6067 (2)	0.0349 (5)	0.95082 (14)	0.0445 (8)
C13	0.6968 (3)	−0.2021 (6)	0.9707 (2)	0.0667 (11)
H13A	0.6687	−0.2637	0.9402	0.080*
H13B	0.6677	−0.2337	1.0056	0.080*
C14	0.7932 (4)	−0.2420 (7)	0.9733 (3)	0.107 (2)
H14A	0.8208	−0.2159	0.9378	0.160*
H14B	0.8008	−0.3595	0.9813	0.160*
H14C	0.8209	−0.1766	1.0025	0.160*
C15	0.5389 (2)	0.2507 (5)	0.88855 (13)	0.0389 (8)
H15	0.4785	0.2148	0.8998	0.047*
C16	0.5374 (3)	0.4351 (5)	0.87268 (16)	0.0491 (9)
C17	0.4459 (4)	0.6665 (6)	0.8471 (3)	0.0884 (17)
H17A	0.4875	0.7343	0.8689	0.106*
H17B	0.4587	0.6831	0.8075	0.106*
C18	0.3538 (4)	0.7157 (8)	0.8595 (4)	0.115 (2)
H18A	0.3133	0.6507	0.8367	0.172*
H18B	0.3461	0.8330	0.8512	0.172*
H18C	0.3413	0.6959	0.8985	0.172*
C19	0.5698 (2)	0.1485 (5)	0.83742 (13)	0.0403 (8)
C20	0.5042 (2)	0.1032 (4)	0.79246 (13)	0.0386 (7)
C21	0.5370 (2)	0.0187 (4)	0.74549 (14)	0.0410 (8)
H21	0.5978	−0.0081	0.7431	0.049*
C22	0.4792 (2)	−0.0251 (4)	0.70248 (14)	0.0419 (8)
C23	0.3882 (2)	0.0166 (4)	0.70603 (14)	0.0420 (8)
C24	0.3549 (2)	0.1024 (4)	0.75271 (14)	0.0407 (8)
C25	0.4132 (2)	0.1444 (4)	0.79624 (14)	0.0397 (8)
H25	0.3916	0.2000	0.8279	0.048*
C26	0.5971 (3)	−0.1306 (7)	0.64448 (19)	0.0697 (13)
H26A	0.6271	−0.0237	0.6447	0.105*
H26B	0.6053	−0.1834	0.6085	0.105*
H26C	0.6219	−0.2009	0.6734	0.105*
C27	0.3330 (3)	0.0638 (7)	0.61492 (18)	0.0694 (13)
H27A	0.3129	0.1763	0.6225	0.104*
H27B	0.2949	0.0137	0.5869	0.104*
H27C	0.3938	0.0667	0.6014	0.104*
C28	0.2330 (3)	0.2444 (6)	0.7950 (2)	0.0731 (13)
H28A	0.2425	0.1915	0.8309	0.110*
H28B	0.1698	0.2628	0.7895	0.110*
H28C	0.2640	0.3502	0.7941	0.110*
O1	0.87265 (17)	0.3276 (4)	1.08144 (12)	0.0650 (8)
O2	0.80067 (17)	0.4667 (4)	1.17185 (11)	0.0563 (7)
O3	0.62390 (17)	0.5260 (4)	1.17970 (11)	0.0556 (7)
O4	0.4954 (2)	0.3631 (6)	0.99176 (14)	0.0982 (14)
O5	0.5406 (2)	−0.0511 (4)	0.95170 (16)	0.0795 (10)
O6	0.68778 (17)	−0.0223 (3)	0.96140 (13)	0.0549 (7)
O7	0.6036 (2)	0.5195 (4)	0.87003 (18)	0.0853 (11)
O8	0.45585 (19)	0.4893 (3)	0.86184 (14)	0.0657 (8)
O9	0.64777 (18)	0.1089 (5)	0.83304 (12)	0.0700 (9)
O10	0.50436 (18)	−0.1066 (4)	0.65448 (10)	0.0576 (7)
O11	0.32913 (17)	−0.0312 (3)	0.66433 (11)	0.0555 (7)
O12	0.26617 (17)	0.1394 (3)	0.75192 (11)	0.0553 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.046 (2)	0.094 (3)	0.075 (3)	0.006 (2)	0.001 (2)	−0.023 (3)
C2	0.088 (3)	0.086 (4)	0.054 (3)	0.008 (3)	−0.026 (2)	0.003 (2)
C3	0.050 (2)	0.085 (3)	0.052 (2)	0.005 (2)	0.0010 (18)	−0.027 (2)
C4	0.047 (2)	0.051 (2)	0.0344 (16)	−0.0030 (16)	−0.0015 (15)	−0.0071 (15)
C5	0.041 (2)	0.051 (2)	0.0429 (19)	−0.0016 (16)	−0.0031 (15)	−0.0011 (16)
C6	0.046 (2)	0.047 (2)	0.0398 (18)	−0.0002 (16)	−0.0137 (15)	−0.0056 (16)
C7	0.049 (2)	0.040 (2)	0.0354 (17)	−0.0029 (16)	−0.0029 (14)	−0.0043 (15)
C8	0.0410 (19)	0.047 (2)	0.0373 (17)	−0.0008 (16)	−0.0046 (14)	−0.0023 (15)
C9	0.0425 (19)	0.0392 (19)	0.0334 (15)	−0.0015 (15)	−0.0058 (13)	−0.0022 (14)
C10	0.041 (2)	0.065 (3)	0.0406 (19)	0.0064 (18)	−0.0071 (15)	−0.0087 (17)
C11	0.0347 (18)	0.051 (2)	0.0342 (15)	−0.0040 (15)	−0.0019 (13)	−0.0018 (14)
C12	0.043 (2)	0.057 (2)	0.0339 (17)	−0.0003 (17)	−0.0015 (14)	0.0025 (16)
C13	0.078 (3)	0.054 (3)	0.069 (3)	0.010 (2)	−0.005 (2)	−0.002 (2)
C14	0.084 (4)	0.083 (4)	0.103 (6)	0.029 (3)	0.000 (4)	0.018 (4)
C15	0.0380 (19)	0.047 (2)	0.0322 (15)	−0.0059 (15)	−0.0024 (13)	−0.0010 (14)
C16	0.052 (2)	0.051 (2)	0.0450 (19)	−0.0055 (19)	−0.0028 (16)	0.0000 (17)
C17	0.090 (4)	0.050 (3)	0.125 (5)	0.008 (3)	−0.003 (3)	0.018 (3)
C18	0.098 (5)	0.079 (4)	0.157 (7)	0.022 (3)	−0.014 (5)	0.026 (4)
C19	0.039 (2)	0.048 (2)	0.0340 (17)	0.0003 (16)	−0.0016 (13)	−0.0017 (15)
C20	0.0428 (19)	0.0409 (19)	0.0321 (15)	−0.0057 (15)	−0.0035 (13)	0.0035 (14)
C21	0.0401 (19)	0.045 (2)	0.0385 (17)	−0.0005 (15)	−0.0028 (14)	0.0008 (15)
C22	0.046 (2)	0.041 (2)	0.0391 (17)	−0.0028 (15)	−0.0020 (15)	−0.0034 (15)
C23	0.041 (2)	0.047 (2)	0.0373 (18)	−0.0134 (15)	−0.0046 (14)	0.0026 (15)
C24	0.0382 (19)	0.043 (2)	0.0406 (17)	−0.0049 (15)	−0.0023 (14)	0.0037 (16)
C25	0.041 (2)	0.045 (2)	0.0332 (16)	−0.0041 (15)	0.0016 (13)	−0.0028 (14)
C26	0.065 (3)	0.087 (3)	0.058 (2)	0.002 (2)	0.005 (2)	−0.026 (2)
C27	0.073 (3)	0.088 (4)	0.047 (2)	−0.017 (2)	−0.022 (2)	0.001 (2)
C28	0.045 (2)	0.078 (3)	0.097 (3)	0.004 (2)	−0.006 (2)	−0.037 (3)
O1	0.0362 (15)	0.101 (2)	0.0573 (16)	0.0059 (14)	−0.0088 (12)	−0.0225 (16)
O2	0.0535 (16)	0.0706 (18)	0.0447 (14)	−0.0073 (13)	−0.0168 (12)	−0.0088 (13)
O3	0.0520 (15)	0.0713 (19)	0.0434 (14)	0.0057 (13)	−0.0048 (11)	−0.0193 (13)
O4	0.0518 (19)	0.172 (4)	0.0704 (19)	0.034 (2)	−0.0210 (16)	−0.064 (2)
O5	0.0553 (19)	0.072 (2)	0.111 (3)	−0.0143 (15)	−0.0044 (17)	0.025 (2)
O6	0.0519 (16)	0.0505 (16)	0.0622 (17)	0.0055 (12)	−0.0074 (13)	−0.0012 (13)
O7	0.062 (2)	0.065 (2)	0.129 (3)	−0.0137 (16)	0.004 (2)	0.021 (2)
O8	0.0566 (18)	0.0468 (16)	0.094 (2)	0.0032 (13)	−0.0190 (16)	0.0059 (15)
O9	0.0446 (17)	0.113 (3)	0.0527 (16)	0.0150 (16)	−0.0113 (13)	−0.0290 (16)
O10	0.0518 (16)	0.075 (2)	0.0456 (14)	0.0021 (13)	−0.0023 (12)	−0.0246 (14)
O11	0.0542 (16)	0.0678 (18)	0.0445 (14)	−0.0198 (13)	−0.0112 (12)	−0.0084 (13)
O12	0.0399 (15)	0.0699 (18)	0.0562 (15)	−0.0041 (12)	−0.0035 (12)	−0.0111 (14)

Geometric parameters (Å, º)

C1—O1	1.418 (5)	C15—C16	1.514 (5)
C1—H1A	0.9600	C15—C19	1.532 (5)
C1—H1B	0.9600	C15—H15	0.9800
C1—H1C	0.9600	C16—O7	1.193 (5)
C2—O2	1.417 (5)	C16—O8	1.313 (4)
C2—H2A	0.9600	C17—C18	1.454 (8)
C2—H2B	0.9600	C17—O8	1.460 (5)
C2—H2C	0.9600	C17—H17A	0.9700
C3—O3	1.423 (4)	C17—H17B	0.9700
C3—H3A	0.9600	C18—H18A	0.9600
C3—H3B	0.9600	C18—H18B	0.9600
C3—H3C	0.9600	C18—H18C	0.9600
C4—C9	1.387 (5)	C19—O9	1.206 (4)
C4—C5	1.400 (5)	C19—C20	1.491 (5)
C4—H4	0.9300	C20—C21	1.391 (5)
C5—O1	1.354 (4)	C20—C25	1.395 (5)
C5—C6	1.392 (5)	C21—C22	1.380 (5)
C6—O2	1.369 (4)	C21—H21	0.9300
C6—C7	1.397 (5)	C22—O10	1.364 (4)
C7—O3	1.360 (4)	C22—C23	1.396 (5)
C7—C8	1.380 (5)	C23—O11	1.378 (4)
C8—C9	1.394 (5)	C23—C24	1.393 (5)
C8—H8	0.9300	C24—O12	1.353 (4)
C9—C10	1.481 (5)	C24—C25	1.390 (5)
C10—O4	1.220 (4)	C25—H25	0.9300
C10—C11	1.527 (5)	C26—O10	1.412 (5)
C11—C12	1.521 (6)	C26—H26A	0.9600
C11—C15	1.537 (4)	C26—H26B	0.9600
C11—H11	0.9800	C26—H26C	0.9600
C12—O5	1.197 (5)	C27—O11	1.398 (5)
C12—O6	1.314 (4)	C27—H27A	0.9600
C13—O6	1.453 (5)	C27—H27B	0.9600
C13—C14	1.469 (6)	C27—H27C	0.9600
C13—H13A	0.9700	C28—O12	1.411 (5)
C13—H13B	0.9700	C28—H28A	0.9600
C14—H14A	0.9600	C28—H28B	0.9600
C14—H14B	0.9600	C28—H28C	0.9600
C14—H14C	0.9600
O1—C1—H1A	109.5	C19—C15—H15	109.7
O1—C1—H1B	109.5	C11—C15—H15	109.7
H1A—C1—H1B	109.5	O7—C16—O8	124.6 (4)
O1—C1—H1C	109.5	O7—C16—C15	123.1 (4)
H1A—C1—H1C	109.5	O8—C16—C15	112.3 (3)
H1B—C1—H1C	109.5	C18—C17—O8	107.9 (4)
O2—C2—H2A	109.5	C18—C17—H17A	110.1
O2—C2—H2B	109.5	O8—C17—H17A	110.1
H2A—C2—H2B	109.5	C18—C17—H17B	110.1
O2—C2—H2C	109.5	O8—C17—H17B	110.1
H2A—C2—H2C	109.5	H17A—C17—H17B	108.4
H2B—C2—H2C	109.5	C17—C18—H18A	109.5
O3—C3—H3A	109.5	C17—C18—H18B	109.5
O3—C3—H3B	109.5	H18A—C18—H18B	109.5
H3A—C3—H3B	109.5	C17—C18—H18C	109.5
O3—C3—H3C	109.5	H18A—C18—H18C	109.5
H3A—C3—H3C	109.5	H18B—C18—H18C	109.5
H3B—C3—H3C	109.5	O9—C19—C20	120.3 (3)
C9—C4—C5	119.7 (3)	O9—C19—C15	119.7 (3)
C9—C4—H4	120.2	C20—C19—C15	120.0 (3)
C5—C4—H4	120.2	C21—C20—C25	120.4 (3)
O1—C5—C6	115.4 (3)	C21—C20—C19	117.5 (3)
O1—C5—C4	125.0 (3)	C25—C20—C19	122.1 (3)
C6—C5—C4	119.5 (3)	C22—C21—C20	119.8 (3)
O2—C6—C5	119.3 (3)	C22—C21—H21	120.1
O2—C6—C7	120.4 (3)	C20—C21—H21	120.1
C5—C6—C7	120.3 (3)	O10—C22—C21	124.6 (3)
O3—C7—C8	124.4 (3)	O10—C22—C23	115.4 (3)
O3—C7—C6	115.6 (3)	C21—C22—C23	120.0 (3)
C8—C7—C6	120.0 (3)	O11—C23—C24	118.8 (3)
C7—C8—C9	119.9 (3)	O11—C23—C22	120.6 (3)
C7—C8—H8	120.0	C24—C23—C22	120.6 (3)
C9—C8—H8	120.0	O12—C24—C25	124.5 (3)
C4—C9—C8	120.5 (3)	O12—C24—C23	116.2 (3)
C4—C9—C10	122.6 (3)	C25—C24—C23	119.3 (3)
C8—C9—C10	116.9 (3)	C24—C25—C20	120.0 (3)
O4—C10—C9	120.5 (3)	C24—C25—H25	120.0
O4—C10—C11	118.5 (3)	C20—C25—H25	120.0
C9—C10—C11	121.0 (3)	O10—C26—H26A	109.5
C12—C11—C10	109.2 (3)	O10—C26—H26B	109.5
C12—C11—C15	108.4 (3)	H26A—C26—H26B	109.5
C10—C11—C15	109.8 (3)	O10—C26—H26C	109.5
C12—C11—H11	109.8	H26A—C26—H26C	109.5
C10—C11—H11	109.8	H26B—C26—H26C	109.5
C15—C11—H11	109.8	O11—C27—H27A	109.5
O5—C12—O6	123.5 (4)	O11—C27—H27B	109.5
O5—C12—C11	123.3 (4)	H27A—C27—H27B	109.5
O6—C12—C11	113.2 (3)	O11—C27—H27C	109.5
O6—C13—C14	108.0 (4)	H27A—C27—H27C	109.5
O6—C13—H13A	110.1	H27B—C27—H27C	109.5
C14—C13—H13A	110.1	O12—C28—H28A	109.5
O6—C13—H13B	110.1	O12—C28—H28B	109.5
C14—C13—H13B	110.1	H28A—C28—H28B	109.5
H13A—C13—H13B	108.4	O12—C28—H28C	109.5
C13—C14—H14A	109.5	H28A—C28—H28C	109.5
C13—C14—H14B	109.5	H28B—C28—H28C	109.5
H14A—C14—H14B	109.5	C5—O1—C1	117.9 (3)
C13—C14—H14C	109.5	C6—O2—C2	114.4 (3)
H14A—C14—H14C	109.5	C7—O3—C3	117.5 (3)
H14B—C14—H14C	109.5	C12—O6—C13	117.1 (3)
C16—C15—C19	108.7 (3)	C16—O8—C17	117.2 (3)
C16—C15—C11	109.9 (3)	C22—O10—C26	118.2 (3)
C19—C15—C11	109.0 (3)	C23—O11—C27	115.4 (3)
C16—C15—H15	109.7	C24—O12—C28	117.4 (3)
C9—C4—C5—O1	178.4 (3)	C11—C15—C19—C20	158.1 (3)
C9—C4—C5—C6	−0.5 (5)	O9—C19—C20—C21	−1.7 (5)
O1—C5—C6—O2	3.3 (5)	C15—C19—C20—C21	176.4 (3)
C4—C5—C6—O2	−177.8 (3)	O9—C19—C20—C25	179.1 (4)
O1—C5—C6—C7	−178.6 (3)	C15—C19—C20—C25	−2.9 (5)
C4—C5—C6—C7	0.3 (5)	C25—C20—C21—C22	−0.3 (5)
O2—C6—C7—O3	−2.5 (5)	C19—C20—C21—C22	−179.5 (3)
C5—C6—C7—O3	179.4 (3)	C20—C21—C22—O10	179.5 (3)
O2—C6—C7—C8	178.0 (3)	C20—C21—C22—C23	0.5 (5)
C5—C6—C7—C8	−0.1 (5)	O10—C22—C23—O11	3.1 (5)
O3—C7—C8—C9	−179.5 (3)	C21—C22—C23—O11	−177.8 (3)
C6—C7—C8—C9	−0.1 (5)	O10—C22—C23—C24	−179.0 (3)
C5—C4—C9—C8	0.3 (5)	C21—C22—C23—C24	0.1 (5)
C5—C4—C9—C10	−179.3 (4)	O11—C23—C24—O12	−3.1 (5)
C7—C8—C9—C4	−0.1 (5)	C22—C23—C24—O12	179.0 (3)
C7—C8—C9—C10	179.6 (3)	O11—C23—C24—C25	177.1 (3)
C4—C9—C10—O4	−173.6 (4)	C22—C23—C24—C25	−0.8 (5)
C8—C9—C10—O4	6.7 (6)	O12—C24—C25—C20	−178.8 (3)
C4—C9—C10—C11	8.1 (6)	C23—C24—C25—C20	1.1 (5)
C8—C9—C10—C11	−171.6 (3)	C21—C20—C25—C24	−0.5 (5)
O4—C10—C11—C12	−98.9 (4)	C19—C20—C25—C24	178.7 (3)
C9—C10—C11—C12	79.4 (4)	C6—C5—O1—C1	178.2 (4)
O4—C10—C11—C15	19.7 (5)	C4—C5—O1—C1	−0.7 (6)
C9—C10—C11—C15	−161.9 (3)	C5—C6—O2—C2	−102.8 (4)
C10—C11—C12—O5	78.7 (4)	C7—C6—O2—C2	79.1 (5)
C15—C11—C12—O5	−40.8 (5)	C8—C7—O3—C3	5.2 (6)
C10—C11—C12—O6	−101.3 (3)	C6—C7—O3—C3	−174.3 (3)
C15—C11—C12—O6	139.1 (3)	O5—C12—O6—C13	4.4 (5)
C12—C11—C15—C16	−178.3 (3)	C11—C12—O6—C13	−175.6 (3)
C10—C11—C15—C16	62.5 (4)	C14—C13—O6—C12	171.7 (4)
C12—C11—C15—C19	−59.3 (3)	O7—C16—O8—C17	−1.8 (7)
C10—C11—C15—C19	−178.4 (3)	C15—C16—O8—C17	178.8 (4)
C19—C15—C16—O7	−77.9 (5)	C18—C17—O8—C16	−156.9 (5)
C11—C15—C16—O7	41.4 (5)	C21—C22—O10—C26	−8.1 (6)
C19—C15—C16—O8	101.5 (4)	C23—C22—O10—C26	171.0 (4)
C11—C15—C16—O8	−139.3 (3)	C24—C23—O11—C27	105.5 (4)
C16—C15—C19—O9	96.0 (4)	C22—C23—O11—C27	−76.5 (5)
C11—C15—C19—O9	−23.8 (5)	C25—C24—O12—C28	7.7 (5)
C16—C15—C19—C20	−82.0 (4)	C23—C24—O12—C28	−172.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···Cg2^i	0.96	2.83 (1)	3.482 (1)	126
C17—H17B···Cg2^ii	0.97	3.31 (1)	3.899 (1)	121
C18—H18B···Cg2^ii	0.96	3.37 (1)	4.030 (1)	128
C27—H27B···Cg1^iii	0.96	3.23 (1)	3.718 (1)	114

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