Synthesis, crystal structure and Hirshfeld surface analysis of naphthalene-2,3-diyl bis­(3-benz­yl­oxy)benzoate

In the title compound, C₃₈H₂₈O₆, the dihedral angles between the naphthalene ring system and its pendant benz­yloxy rings A and B are 88.05 (7) and 80.84 (7)°, respectively. The dihedral angles between the A and B rings and their attached phenyl rings are 49.15 (8) and 80.78 (8)°, respectively. In the extended structure, the mol­ecules are linked by weak C—H...O and C—H...π bonds and π–π stacking inter­actions, which variously generate C(11) chains and (12) loops as part of a three-dimensional network. The Hirshfeld surface [fingerprint contributions = H...H (42.3%), C...H/H...C (40.3%) and O...H/H...O (15.7%)] and inter­molecular inter­action energies are reported, with dispersion, E_dis at −428.6 kJ mol⁻¹ being the major contributor.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 302 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.142
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full value (too) Low ......      25.26 Degree

Author Response: we obtained the expected molecular structre. this may be due to neglecting lower angle data.

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5853
PLAT048_ALERT_1_C MoietyFormula Not Given (or Incomplete) ........     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.585        149 Report

Alert level G
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        79% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.1 Low
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   1 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL (Sheldrick, 2015b).

Naphthalene-2,3-diyl bis(3-benzyloxy)benzoate

Crystal data

C38H28O6	Prism
Mr = 580.60	Dx = 1.315 Mg m^−3
Monoclinic, P21/n	Melting point: 417 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 9.5219 (2) Å	Cell parameters from 4775 reflections
b = 10.1010 (2) Å	θ = 0.3–25°
c = 30.7050 (8) Å	µ = 0.72 mm^−1
β = 96.666 (1)°	T = 302 K
V = 2933.26 (11) Å^3	Rod, colourless
Z = 4	0.32 × 0.28 × 0.21 mm
F(000) = 1216

Data collection

Bruker SMART APEXII CCD diffractometer	4298 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 64.5°, θmin = 4.6°
Detector resolution: 2.06 pixels mm^-1	h = −11→10
ω scans	k = −11→7
14741 measured reflections	l = −32→35
4775 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0997P)^2 + 0.5664P] where P = (Fo^2 + 2Fc^2)/3
4775 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3
1 constraint

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.58939 (11)	0.43382 (12)	0.05018 (3)	0.0232 (3)
O2	0.77634 (11)	0.38287 (13)	0.09926 (3)	0.0272 (3)
O3	0.58453 (11)	0.47609 (13)	0.24604 (3)	0.0268 (3)
O4	0.50928 (11)	0.18476 (12)	0.02981 (3)	0.0225 (3)
O5	0.34497 (11)	0.27300 (12)	−0.02087 (3)	0.0248 (3)
O6	0.25879 (11)	0.13423 (13)	0.16475 (3)	0.0253 (3)
C1	0.61513 (15)	0.23968 (17)	0.00711 (5)	0.0201 (4)
C2	0.67835 (16)	0.16830 (17)	−0.02259 (5)	0.0213 (4)
H2	0.649084	0.082186	−0.029440	0.026*
C3	0.78971 (15)	0.22628 (17)	−0.04315 (5)	0.0204 (4)
C4	0.86373 (17)	0.15418 (18)	−0.07275 (5)	0.0243 (4)
H4	0.838208	0.067021	−0.079451	0.029*
C5	0.97232 (17)	0.21079 (18)	−0.09165 (5)	0.0254 (4)
H5	1.021228	0.161481	−0.110563	0.031*
C6	1.01010 (16)	0.34325 (18)	−0.08256 (5)	0.0237 (4)
H6	1.083712	0.381211	−0.095640	0.028*
C7	0.93960 (15)	0.41691 (18)	−0.05465 (5)	0.0212 (4)
H7	0.963984	0.505156	−0.049498	0.025*
C8	0.82939 (15)	0.35947 (17)	−0.03349 (4)	0.0187 (3)
C9	0.76033 (15)	0.43085 (17)	−0.00204 (5)	0.0194 (3)
H9	0.785118	0.518167	0.004687	0.023*
C10	0.65814 (15)	0.37016 (17)	0.01796 (4)	0.0200 (4)
C11	0.65782 (15)	0.42547 (17)	0.09173 (5)	0.0199 (4)
C12	0.56915 (16)	0.47090 (16)	0.12536 (5)	0.0203 (4)
C13	0.62360 (16)	0.45161 (17)	0.16931 (5)	0.0213 (4)
H13	0.712355	0.413805	0.176414	0.026*
C14	0.54323 (16)	0.48970 (17)	0.20201 (5)	0.0216 (4)
C15	0.40898 (17)	0.54473 (18)	0.19114 (5)	0.0266 (4)
H15	0.354379	0.568536	0.213113	0.032*
C16	0.35781 (17)	0.5636 (2)	0.14761 (5)	0.0307 (4)
H16	0.269350	0.601978	0.140482	0.037*
C17	0.43662 (17)	0.52605 (19)	0.11437 (5)	0.0272 (4)
H17	0.400928	0.537764	0.085129	0.033*
C18	0.72408 (17)	0.42395 (19)	0.25874 (5)	0.0265 (4)
H18A	0.793380	0.474299	0.244862	0.032*
H18B	0.728805	0.332338	0.249542	0.032*
C19	0.75487 (16)	0.43351 (18)	0.30777 (5)	0.0234 (4)
C20	0.73388 (16)	0.55202 (18)	0.32920 (5)	0.0250 (4)
H20	0.696094	0.624617	0.313295	0.030*
C21	0.76914 (16)	0.56235 (19)	0.37426 (5)	0.0262 (4)
H21	0.754780	0.641792	0.388404	0.031*
C22	0.82545 (17)	0.45503 (19)	0.39814 (5)	0.0282 (4)
H22	0.849553	0.462230	0.428278	0.034*
C23	0.84571 (19)	0.3374 (2)	0.37712 (5)	0.0316 (4)
H23	0.883045	0.264814	0.393102	0.038*
C24	0.81042 (18)	0.32703 (19)	0.33198 (5)	0.0286 (4)
H24	0.824505	0.247257	0.318000	0.034*
C25	0.37343 (15)	0.22511 (16)	0.01482 (5)	0.0192 (3)
C26	0.27380 (16)	0.20240 (16)	0.04756 (5)	0.0194 (3)
C27	0.32213 (16)	0.17695 (16)	0.09144 (5)	0.0199 (3)
H27	0.418421	0.168975	0.100463	0.024*
C28	0.22447 (16)	0.16371 (17)	0.12146 (5)	0.0204 (4)
C29	0.08046 (16)	0.17887 (18)	0.10773 (5)	0.0235 (4)
H29	0.015499	0.173477	0.128056	0.028*
C30	0.03403 (16)	0.20179 (18)	0.06419 (5)	0.0250 (4)
H30	−0.062326	0.209607	0.055252	0.030*
C31	0.12965 (16)	0.21333 (17)	0.03353 (5)	0.0233 (4)
H31	0.098083	0.228097	0.004124	0.028*
C32	0.40533 (16)	0.1048 (2)	0.17832 (5)	0.0267 (4)
H32A	0.462305	0.183689	0.176271	0.032*
H32B	0.438343	0.037409	0.159440	0.032*
C33	0.41890 (16)	0.05652 (19)	0.22477 (5)	0.0247 (4)
C34	0.39745 (18)	−0.0760 (2)	0.23388 (5)	0.0311 (4)
H34	0.369988	−0.134322	0.211041	0.037*
C35	0.41657 (19)	−0.1225 (2)	0.27679 (6)	0.0350 (4)
H35	0.401233	−0.211366	0.282630	0.042*
C36	0.45865 (18)	−0.0357 (2)	0.31084 (5)	0.0331 (4)
H36	0.473278	−0.066367	0.339563	0.040*
C37	0.47870 (18)	0.0964 (2)	0.30192 (5)	0.0330 (4)
H37	0.506345	0.154630	0.324773	0.040*
C38	0.45797 (17)	0.1431 (2)	0.25914 (5)	0.0281 (4)
H38	0.470290	0.232544	0.253504	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0207 (5)	0.0346 (7)	0.0141 (5)	0.0060 (5)	0.0012 (4)	−0.0030 (4)
O2	0.0200 (6)	0.0404 (8)	0.0207 (6)	0.0065 (5)	−0.0001 (4)	−0.0027 (5)
O3	0.0203 (6)	0.0440 (8)	0.0159 (5)	0.0045 (5)	0.0003 (4)	−0.0018 (5)
O4	0.0168 (5)	0.0302 (7)	0.0212 (5)	0.0025 (4)	0.0048 (4)	0.0067 (5)
O5	0.0230 (6)	0.0345 (7)	0.0167 (6)	0.0007 (5)	0.0013 (4)	0.0025 (5)
O6	0.0190 (6)	0.0417 (8)	0.0151 (5)	0.0018 (5)	0.0023 (4)	0.0017 (5)
C1	0.0150 (7)	0.0286 (10)	0.0167 (7)	0.0005 (6)	0.0015 (5)	0.0053 (6)
C2	0.0201 (8)	0.0218 (9)	0.0217 (8)	−0.0004 (6)	0.0013 (6)	0.0019 (6)
C3	0.0181 (7)	0.0276 (10)	0.0151 (7)	0.0010 (6)	−0.0002 (6)	0.0012 (6)
C4	0.0255 (8)	0.0243 (10)	0.0233 (8)	−0.0003 (7)	0.0036 (6)	−0.0029 (7)
C5	0.0225 (8)	0.0342 (11)	0.0203 (8)	0.0023 (7)	0.0050 (6)	−0.0025 (7)
C6	0.0182 (7)	0.0352 (11)	0.0176 (7)	−0.0031 (7)	0.0021 (6)	0.0023 (7)
C7	0.0198 (8)	0.0247 (9)	0.0179 (7)	−0.0027 (6)	−0.0025 (6)	0.0027 (6)
C8	0.0165 (7)	0.0250 (9)	0.0135 (7)	−0.0003 (6)	−0.0025 (5)	0.0008 (6)
C9	0.0184 (7)	0.0223 (9)	0.0163 (7)	0.0014 (6)	−0.0023 (6)	−0.0015 (6)
C10	0.0172 (7)	0.0293 (10)	0.0127 (7)	0.0045 (6)	−0.0011 (5)	−0.0018 (6)
C11	0.0191 (8)	0.0226 (9)	0.0174 (7)	−0.0012 (6)	−0.0003 (6)	−0.0003 (6)
C12	0.0196 (8)	0.0224 (9)	0.0187 (7)	−0.0014 (6)	0.0014 (6)	−0.0019 (6)
C13	0.0170 (7)	0.0244 (9)	0.0222 (8)	−0.0001 (6)	0.0005 (6)	−0.0021 (6)
C14	0.0221 (8)	0.0272 (9)	0.0154 (7)	−0.0031 (7)	0.0010 (6)	−0.0021 (6)
C15	0.0213 (8)	0.0364 (11)	0.0226 (8)	0.0026 (7)	0.0041 (6)	−0.0051 (7)
C16	0.0202 (8)	0.0458 (12)	0.0256 (8)	0.0096 (7)	0.0008 (6)	−0.0015 (7)
C17	0.0243 (8)	0.0377 (11)	0.0185 (7)	0.0042 (7)	−0.0015 (6)	−0.0001 (7)
C18	0.0207 (8)	0.0391 (11)	0.0197 (8)	0.0048 (7)	0.0015 (6)	−0.0025 (7)
C19	0.0159 (7)	0.0341 (10)	0.0200 (8)	−0.0002 (7)	0.0018 (6)	−0.0012 (7)
C20	0.0219 (8)	0.0292 (10)	0.0236 (8)	0.0039 (7)	0.0013 (6)	0.0014 (7)
C21	0.0205 (8)	0.0339 (11)	0.0244 (8)	0.0000 (7)	0.0035 (6)	−0.0071 (7)
C22	0.0235 (8)	0.0430 (12)	0.0180 (8)	−0.0026 (7)	0.0015 (6)	−0.0003 (7)
C23	0.0358 (10)	0.0349 (11)	0.0235 (8)	0.0033 (8)	0.0011 (7)	0.0057 (7)
C24	0.0312 (9)	0.0290 (10)	0.0258 (8)	0.0025 (7)	0.0046 (7)	−0.0029 (7)
C25	0.0188 (7)	0.0207 (9)	0.0178 (7)	−0.0004 (6)	0.0013 (6)	−0.0023 (6)
C26	0.0193 (8)	0.0200 (9)	0.0190 (8)	0.0004 (6)	0.0027 (6)	−0.0011 (6)
C27	0.0160 (7)	0.0235 (9)	0.0199 (8)	−0.0003 (6)	0.0010 (6)	−0.0016 (6)
C28	0.0222 (8)	0.0231 (9)	0.0157 (7)	−0.0009 (6)	0.0017 (6)	−0.0018 (6)
C29	0.0187 (8)	0.0291 (10)	0.0234 (8)	0.0019 (6)	0.0054 (6)	−0.0003 (7)
C30	0.0156 (7)	0.0333 (10)	0.0258 (8)	0.0033 (7)	0.0017 (6)	0.0023 (7)
C31	0.0217 (8)	0.0277 (10)	0.0198 (7)	0.0013 (7)	−0.0004 (6)	0.0019 (6)
C32	0.0186 (8)	0.0416 (11)	0.0195 (8)	−0.0022 (7)	0.0006 (6)	0.0021 (7)
C33	0.0176 (7)	0.0379 (11)	0.0188 (8)	−0.0019 (7)	0.0025 (6)	0.0009 (7)
C34	0.0296 (9)	0.0386 (12)	0.0250 (9)	−0.0057 (8)	0.0032 (7)	−0.0028 (7)
C35	0.0330 (9)	0.0406 (12)	0.0319 (9)	−0.0028 (8)	0.0064 (7)	0.0098 (8)
C36	0.0279 (9)	0.0519 (13)	0.0195 (8)	0.0004 (8)	0.0030 (6)	0.0083 (8)
C37	0.0308 (9)	0.0491 (13)	0.0189 (8)	−0.0036 (8)	0.0021 (7)	−0.0025 (8)
C38	0.0247 (8)	0.0362 (11)	0.0235 (8)	−0.0024 (7)	0.0034 (6)	0.0006 (7)

Geometric parameters (Å, º)

O1—C11	1.3662 (18)	C18—C19	1.503 (2)
O1—C10	1.4040 (18)	C18—H18A	0.9700
O2—C11	1.2049 (19)	C18—H18B	0.9700
O3—C14	1.3702 (18)	C19—C24	1.378 (3)
O3—C18	1.4404 (19)	C19—C20	1.392 (2)
O4—C25	1.3831 (18)	C20—C21	1.389 (2)
O4—C1	1.4045 (18)	C20—H20	0.9300
O5—C25	1.1998 (18)	C21—C22	1.382 (3)
O6—C28	1.3642 (18)	C21—H21	0.9300
O6—C32	1.4401 (18)	C22—C23	1.376 (3)
C1—C2	1.357 (2)	C22—H22	0.9300
C1—C10	1.409 (2)	C23—C24	1.392 (2)
C2—C3	1.422 (2)	C23—H23	0.9300
C2—H2	0.9300	C24—H24	0.9300
C3—C4	1.415 (2)	C25—C26	1.478 (2)
C3—C8	1.419 (2)	C26—C31	1.394 (2)
C4—C5	1.368 (2)	C26—C27	1.396 (2)
C4—H4	0.9300	C27—C28	1.390 (2)
C5—C6	1.405 (3)	C27—H27	0.9300
C5—H5	0.9300	C28—C29	1.395 (2)
C6—C7	1.368 (2)	C29—C30	1.378 (2)
C6—H6	0.9300	C29—H29	0.9300
C7—C8	1.421 (2)	C30—C31	1.388 (2)
C7—H7	0.9300	C30—H30	0.9300
C8—C9	1.425 (2)	C31—H31	0.9300
C9—C10	1.356 (2)	C32—C33	1.498 (2)
C9—H9	0.9300	C33—C34	1.387 (3)
C11—C12	1.480 (2)	C33—C38	1.388 (2)
C12—C17	1.385 (2)	C34—C35	1.391 (2)
C12—C13	1.402 (2)	C34—H34	0.9300
C13—C14	1.386 (2)	C35—C36	1.388 (3)
C13—H13	0.9300	C35—H35	0.9300
C14—C15	1.398 (2)	C36—C37	1.379 (3)
C15—C16	1.382 (2)	C36—H36	0.9300
C15—H15	0.9300	C37—C38	1.388 (2)
C16—C17	1.388 (2)	C37—H37	0.9300
C16—H16	0.9300	C38—H38	0.9300
C17—H17	0.9300
C11—O1—C10	114.77 (11)	H18A—C18—H18B	108.4
C14—O3—C18	116.99 (12)	C24—C19—C20	118.91 (14)
C25—O4—C1	114.56 (11)	C24—C19—C18	120.55 (16)
C28—O6—C32	116.20 (11)	C20—C19—C18	120.46 (15)
C2—C1—C10	121.11 (14)	C21—C20—C19	120.28 (16)
C2—C1—O4	121.57 (15)	C21—C20—H20	119.9
C10—C1—O4	117.25 (13)	C19—C20—H20	119.9
C2—C1—O4	121.57 (15)	C22—C21—C20	120.24 (17)
C10—C1—O4	117.25 (13)	C22—C21—H21	119.9
C1—C2—C3	119.43 (15)	C20—C21—H21	119.9
C1—C2—H2	120.3	C21—C22—C23	119.68 (15)
C3—C2—H2	120.3	C21—C22—H22	120.2
C4—C3—C2	121.73 (15)	C23—C22—H22	120.2
C4—C3—C8	118.80 (14)	C22—C23—C24	120.11 (17)
C2—C3—C8	119.46 (14)	C22—C23—H23	119.9
C5—C4—C3	120.97 (16)	C24—C23—H23	119.9
C5—C4—H4	119.5	C19—C24—C23	120.77 (17)
C3—C4—H4	119.5	C19—C24—H24	119.6
C4—C5—C6	120.16 (15)	C23—C24—H24	119.6
C4—C5—H5	119.9	O5—C25—O4	121.75 (13)
C6—C5—H5	119.9	O5—C25—O4	121.75 (13)
C5—C6—C7	120.62 (15)	O5—C25—C26	126.09 (14)
C5—C6—H6	119.7	O4—C25—C26	112.15 (12)
C7—C6—H6	119.7	O4—C25—C26	112.15 (12)
C6—C7—C8	120.43 (16)	C31—C26—C27	121.00 (14)
C6—C7—H7	119.8	C31—C26—C25	117.65 (14)
C8—C7—H7	119.8	C27—C26—C25	121.28 (13)
C7—C8—C9	121.77 (15)	C28—C27—C26	119.14 (14)
C7—C8—C3	118.97 (14)	C28—C27—H27	120.4
C9—C8—C3	119.24 (14)	C26—C27—H27	120.4
C10—C9—C8	119.32 (15)	O6—C28—C27	124.34 (13)
C10—C9—H9	120.3	O6—C28—C29	115.74 (13)
C8—C9—H9	120.3	C27—C28—C29	119.91 (14)
C9—C10—O1	121.99 (15)	C30—C29—C28	120.33 (14)
C9—C10—O1	121.99 (15)	C30—C29—H29	119.8
C9—C10—C1	121.34 (14)	C28—C29—H29	119.8
O1—C10—C1	116.66 (13)	C29—C30—C31	120.67 (14)
O1—C10—C1	116.66 (13)	C29—C30—H30	119.7
O2—C11—O1	122.40 (14)	C31—C30—H30	119.7
O2—C11—O1	122.40 (14)	C26—C31—C30	118.91 (14)
O2—C11—C12	125.04 (13)	C26—C31—H31	120.5
O1—C11—C12	112.55 (12)	C30—C31—H31	120.5
O1—C11—C12	112.55 (12)	O6—C32—C33	108.43 (12)
C17—C12—C13	121.00 (14)	O6—C32—H32A	110.0
C17—C12—C11	122.14 (13)	C33—C32—H32A	110.0
C13—C12—C11	116.82 (13)	O6—C32—H32B	110.0
C14—C13—C12	119.04 (14)	C33—C32—H32B	110.0
C14—C13—H13	120.5	H32A—C32—H32B	108.4
C12—C13—H13	120.5	C34—C33—C38	119.16 (15)
O3—C14—C13	124.59 (14)	C34—C33—C32	120.50 (16)
O3—C14—C15	115.16 (13)	C38—C33—C32	120.30 (17)
C13—C14—C15	120.25 (14)	C33—C34—C35	120.74 (17)
C16—C15—C14	119.72 (15)	C33—C34—H34	119.6
C16—C15—H15	120.1	C35—C34—H34	119.6
C14—C15—H15	120.1	C36—C35—C34	119.64 (19)
C15—C16—C17	120.90 (15)	C36—C35—H35	120.2
C15—C16—H16	119.5	C34—C35—H35	120.2
C17—C16—H16	119.5	C35—C36—C37	119.75 (16)
C12—C17—C16	119.08 (14)	C35—C36—H36	120.1
C12—C17—H17	120.5	C37—C36—H36	120.1
C16—C17—H17	120.5	C38—C37—C36	120.58 (17)
O3—C18—C19	108.31 (12)	C38—C37—H37	119.7
O3—C18—H18A	110.0	C36—C37—H37	119.7
C19—C18—H18A	110.0	C37—C38—C33	120.11 (19)
O3—C18—H18B	110.0	C37—C38—H38	119.9
C19—C18—H18B	110.0	C33—C38—H38	119.9
C25—O4—C1—C2	−103.88 (16)	C13—C14—C15—C16	−1.3 (3)
C25—O4—C1—C10	79.14 (16)	C14—C15—C16—C17	1.4 (3)
O4—C1—C2—C3	−176.96 (12)	C13—C12—C17—C16	0.6 (3)
O4—C1—C2—C3	−176.96 (12)	C11—C12—C17—C16	178.47 (16)
C1—C2—C3—C4	176.92 (14)	C15—C16—C17—C12	−1.0 (3)
C1—C2—C3—C8	−2.3 (2)	C14—O3—C18—C19	172.84 (14)
C2—C3—C4—C5	−178.84 (14)	O3—C18—C19—C24	132.87 (16)
C3—C4—C5—C6	−1.4 (2)	O3—C18—C19—C20	−50.1 (2)
C5—C6—C7—C8	1.7 (2)	C24—C19—C20—C21	0.3 (2)
C6—C7—C8—C9	175.77 (13)	C18—C19—C20—C21	−176.77 (14)
C6—C7—C8—C3	−2.6 (2)	C19—C20—C21—C22	0.1 (2)
C4—C3—C8—C7	1.5 (2)	C20—C21—C22—C23	−0.4 (2)
C2—C3—C8—C7	−179.20 (13)	C21—C22—C23—C24	0.4 (3)
C4—C3—C8—C9	−176.86 (13)	C20—C19—C24—C23	−0.3 (2)
C2—C3—C8—C9	2.4 (2)	C18—C19—C24—C23	176.77 (15)
C7—C8—C9—C10	−178.40 (13)	C22—C23—C24—C19	−0.1 (3)
C8—C9—C10—O1	177.98 (12)	C1—O4—C25—O5	18.8 (2)
C8—C9—C10—O1	177.98 (12)	C1—O4—C25—O4	0 (22)
C8—C9—C10—C1	−2.4 (2)	C1—O4—C25—C26	−160.98 (13)
C11—O1—C10—C9	−85.49 (17)	O5—C25—C26—C31	13.0 (3)
C11—O1—C10—C1	94.88 (15)	O4—C25—C26—C31	−167.24 (14)
C2—C1—C10—C9	2.5 (2)	O4—C25—C26—C31	−167.24 (14)
O4—C1—C10—C9	179.53 (13)	O5—C25—C26—C27	−164.05 (16)
O4—C1—C10—C9	179.53 (13)	O4—C25—C26—C27	15.7 (2)
C2—C1—C10—O1	−177.83 (13)	O4—C25—C26—C27	15.7 (2)
O4—C1—C10—O1	−0.83 (18)	C31—C26—C27—C28	−0.6 (2)
O4—C1—C10—O1	−0.83 (18)	C25—C26—C27—C28	176.37 (15)
C2—C1—C10—O1	−177.83 (13)	C32—O6—C28—C27	−5.3 (2)
O4—C1—C10—O1	−0.83 (18)	C32—O6—C28—C29	173.76 (15)
O4—C1—C10—O1	−0.83 (18)	C26—C27—C28—O6	177.57 (15)
C10—O1—C11—O2	9.7 (2)	C26—C27—C28—C29	−1.5 (3)
C10—O1—C11—C12	−168.94 (14)	O6—C28—C29—C30	−176.56 (15)
O2—C11—C12—C17	176.16 (17)	C27—C28—C29—C30	2.6 (3)
O1—C11—C12—C17	−5.3 (2)	C28—C29—C30—C31	−1.6 (3)
O1—C11—C12—C17	−5.3 (2)	C27—C26—C31—C30	1.6 (3)
O2—C11—C12—C13	−5.9 (3)	C25—C26—C31—C30	−175.49 (15)
O1—C11—C12—C13	172.69 (14)	C29—C30—C31—C26	−0.5 (3)
O1—C11—C12—C13	172.69 (14)	C28—O6—C32—C33	−172.04 (14)
C17—C12—C13—C14	−0.6 (3)	O6—C32—C33—C34	85.55 (19)
C11—C12—C13—C14	−178.55 (15)	O6—C32—C33—C38	−96.72 (18)
C18—O3—C14—C13	2.9 (2)	C32—C33—C34—C35	176.88 (15)
C18—O3—C14—C15	−177.96 (15)	C34—C35—C36—C37	1.1 (3)
C12—C13—C14—O3	179.99 (15)	C36—C37—C38—C33	−1.0 (3)
C12—C13—C14—C15	0.9 (2)	C34—C33—C38—C37	1.6 (2)
O3—C14—C15—C16	179.51 (16)	C32—C33—C38—C37	−176.12 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O5^i	0.93	2.52	3.258 (2)	136
C21—H21···O2^ii	0.93	2.49	3.378 (2)	160
C4—H4···Cg5^iii	0.93	2.60	3.4949 (19)	163
C16—H16···Cg2^i	0.93	2.95	3.6955 (18)	139
C17—H17···Cg1^i	0.93	2.90	3.7480 (17)	152
C17—H17···Cg7^i	0.93	2.91	3.6342 (17)	135
C18—H18A···Cg6^ii	0.97	2.66	3.5201 (18)	148
C30—H30···Cg1^iv	0.93	2.90	3.7078 (17)	146
C31—H31···Cg2^iv	0.93	2.69	3.5449 (17)	154
C31—H31···Cg7^iv	0.93	2.95	3.6130 (16)	130
C32—H32A···Cg4^v	0.97	2.82	3.5525 (18)	133
C15—H15···Cg6^vi	0.93	2.97	3.6860 (18)	135

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1, −y, −z; (iv) x−1, y, z; (v) −x+3/2, y−1/2, −z+1/2; (vi) −x+1/2, y+1/2, −z+1/2.