Di-tert-butyl 2,2'-[9H-fluorene-9,9-diylbis(p-phenyl-ene-oxy)]diacetate.

In the title mol-ecule, C(37)H(38)O(6), the non-fused C atom belonging to the five-membered ring of the fluorene system is connected to two p-phenyl-ene rings, the rings opening up the C(ar-yl)-C-C(ar-yl) angle to 113.1 (1)°. The four-atom -O-CH(2)-C(=O)-O- chain between the p-phenyl-ene ring and the tert-butyl group assumes a more regular W-shaped conformation for one substituent [O-C-C-C torsion angle = 171.9 (2)°] but a less regular W-shaped conformation for the other [torsion angle = 147.4 (2)°].

Related literature

For the application of the title compound as a dissolution inhibitor for protecting photosensitive poly-benzoxazoles, see: Ogura et al. (2009 ▶).

Experimental

Crystal data

C37H38O6

M = 578.67

Monoclinic,

a = 15.6527 (8) Å

b = 11.9466 (6) Å

c = 17.8218 (9) Å

β = 107.109 (1)°

V = 3185.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.45 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

21641 measured reflections

7322 independent reflections

4525 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.161

S = 1.00

7322 reflections

388 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022579/zs2047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022579/zs2047Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C37H38O6	F(000) = 1232
Mr = 578.67	Dx = 1.207 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3717 reflections
a = 15.6527 (8) Å	θ = 2.2–21.9°
b = 11.9466 (6) Å	µ = 0.08 mm−1
c = 17.8218 (9) Å	T = 293 K
β = 107.109 (1)°	Block, colorless
V = 3185.1 (3) Å3	0.45 × 0.25 × 0.15 mm
Z = 4

Bruker SMART APEX CCD diffractometer	4525 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 27.5°, θmin = 2.1°
ω scans	h = −12→20
21641 measured reflections	k = −15→15
7322 independent reflections	l = −23→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0795P)2 + 0.3146P] where P = (Fo2 + 2Fc2)/3
7322 reflections	(Δ/σ)max = 0.001
388 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.96192 (9)	0.50272 (11)	0.17980 (8)	0.0660 (4)
O2	0.90616 (13)	0.40493 (15)	0.26336 (10)	0.0924 (5)
O3	0.74271 (9)	0.40436 (10)	0.14068 (8)	0.0602 (4)
O4	0.18694 (9)	0.79726 (14)	0.01378 (8)	0.0684 (4)
O5	0.02575 (10)	0.72090 (14)	−0.06079 (10)	0.0831 (5)
O6	−0.03695 (9)	0.82951 (14)	0.01154 (9)	0.0735 (4)
C1	1.05054 (14)	0.53058 (19)	0.23489 (14)	0.0734 (6)
C2	1.10416 (18)	0.4244 (2)	0.25468 (17)	0.0992 (9)
H2A	1.1106	0.3917	0.2075	0.149*
H2B	1.0740	0.3728	0.2794	0.149*
H2C	1.1622	0.4411	0.2898	0.149*
C3	1.08798 (19)	0.6088 (3)	0.18602 (19)	0.1086 (10)
H3A	1.0953	0.5692	0.1414	0.163*
H3B	1.1449	0.6367	0.2172	0.163*
H3C	1.0476	0.6704	0.1684	0.163*
C4	1.0403 (2)	0.5896 (3)	0.30693 (18)	0.1131 (10)
H4A	1.0070	0.6575	0.2914	0.170*
H4B	1.0983	0.6070	0.3418	0.170*
H4C	1.0090	0.5417	0.3332	0.170*
C5	0.90208 (14)	0.43879 (17)	0.19930 (13)	0.0614 (5)
C6	0.82649 (13)	0.41483 (17)	0.12614 (12)	0.0610 (5)
H6A	0.8231	0.4748	0.0887	0.073*
H6B	0.8393	0.3460	0.1026	0.073*
C7	0.70189 (12)	0.50185 (14)	0.15283 (10)	0.0462 (4)
C8	0.74248 (12)	0.60625 (14)	0.16529 (11)	0.0502 (4)
H8	0.8018	0.6143	0.1659	0.060*
C9	0.69411 (12)	0.69830 (14)	0.17677 (10)	0.0475 (4)
H9	0.7217	0.7680	0.1845	0.057*
C10	0.60613 (11)	0.69016 (13)	0.17709 (9)	0.0416 (4)
C11	0.56757 (12)	0.58392 (14)	0.16520 (10)	0.0481 (4)
H11	0.5089	0.5751	0.1662	0.058*
C12	0.61385 (12)	0.49206 (14)	0.15200 (10)	0.0483 (4)
H12	0.5856	0.4228	0.1424	0.058*
C13	0.55467 (11)	0.79052 (13)	0.19559 (9)	0.0425 (4)
C14	0.59517 (12)	0.90292 (14)	0.18369 (11)	0.0479 (4)
C15	0.60298 (15)	0.94869 (17)	0.11487 (13)	0.0653 (5)
H15	0.5828	0.9100	0.0677	0.078*
C16	0.64175 (17)	1.05427 (19)	0.11778 (17)	0.0792 (7)
H16	0.6484	1.0859	0.0721	0.095*
C17	0.67034 (16)	1.11222 (18)	0.18756 (18)	0.0803 (7)
H17	0.6949	1.1832	0.1881	0.096*
C18	0.66323 (14)	1.06687 (17)	0.25624 (16)	0.0695 (6)
H18	0.6832	1.1063	0.3031	0.083*
C19	0.62587 (11)	0.96158 (15)	0.25474 (11)	0.0510 (4)
C20	0.60928 (11)	0.89381 (15)	0.31708 (10)	0.0487 (4)
C21	0.62633 (13)	0.91414 (19)	0.39751 (12)	0.0648 (6)
H21	0.6534	0.9805	0.4196	0.078*
C22	0.60246 (15)	0.8344 (2)	0.44319 (12)	0.0739 (7)
H22	0.6131	0.8474	0.4966	0.089*
C23	0.56317 (14)	0.7359 (2)	0.41104 (12)	0.0706 (6)
H23	0.5476	0.6829	0.4430	0.085*
C24	0.54639 (13)	0.71426 (17)	0.33173 (10)	0.0564 (5)
H24	0.5206	0.6469	0.3105	0.068*
C25	0.56844 (11)	0.79406 (15)	0.28465 (9)	0.0450 (4)
C26	0.45506 (12)	0.79041 (13)	0.14816 (9)	0.0432 (4)
C27	0.42460 (12)	0.74664 (15)	0.07270 (10)	0.0492 (4)
H27	0.4653	0.7141	0.0503	0.059*
C28	0.33544 (13)	0.75042 (16)	0.03025 (10)	0.0525 (4)
H28	0.3167	0.7195	−0.0198	0.063*
C29	0.27377 (12)	0.79966 (15)	0.06131 (10)	0.0496 (4)
C30	0.30209 (13)	0.84633 (17)	0.13524 (11)	0.0575 (5)
H30	0.2614	0.8809	0.1567	0.069*
C31	0.39187 (13)	0.84105 (16)	0.17724 (11)	0.0539 (5)
H31	0.4104	0.8729	0.2270	0.065*
C32	0.11751 (13)	0.8322 (2)	0.04370 (12)	0.0643 (5)
H32A	0.1150	0.9132	0.0449	0.077*
H32B	0.1277	0.8044	0.0968	0.077*
C33	0.03097 (14)	0.78602 (18)	−0.00918 (12)	0.0592 (5)
C34	−0.12991 (15)	0.7891 (2)	−0.02384 (14)	0.0750 (6)
C35	−0.16201 (17)	0.8197 (2)	−0.10832 (14)	0.0878 (7)
H35A	−0.1587	0.8994	−0.1137	0.132*
H35B	−0.2228	0.7957	−0.1300	0.132*
H35C	−0.1253	0.7838	−0.1359	0.132*
C36	−0.13214 (19)	0.6639 (3)	−0.0107 (2)	0.1187 (11)
H36A	−0.0988	0.6264	−0.0407	0.178*
H36B	−0.1930	0.6383	−0.0272	0.178*
H36C	−0.1061	0.6478	0.0441	0.178*
C37	−0.18185 (19)	0.8536 (3)	0.02153 (19)	0.1255 (13)
H37A	−0.1788	0.9322	0.0114	0.188*
H37B	−0.1565	0.8396	0.0767	0.188*
H37C	−0.2431	0.8298	0.0052	0.188*

	U11	U22	U33	U12	U13	U23
O1	0.0500 (8)	0.0662 (9)	0.0737 (9)	−0.0015 (7)	0.0056 (7)	0.0012 (7)
O2	0.0921 (13)	0.1007 (13)	0.0749 (11)	−0.0092 (10)	0.0100 (9)	0.0199 (9)
O3	0.0519 (8)	0.0475 (7)	0.0819 (10)	−0.0023 (6)	0.0205 (7)	−0.0109 (6)
O4	0.0434 (8)	0.1055 (11)	0.0512 (8)	−0.0002 (7)	0.0057 (6)	−0.0054 (7)
O5	0.0602 (10)	0.0932 (11)	0.0883 (11)	−0.0021 (8)	0.0097 (8)	−0.0280 (9)
O6	0.0460 (8)	0.1080 (12)	0.0651 (9)	−0.0146 (8)	0.0144 (7)	−0.0173 (8)
C1	0.0516 (12)	0.0665 (13)	0.0878 (16)	0.0021 (10)	−0.0014 (11)	−0.0100 (12)
C2	0.0738 (17)	0.0862 (18)	0.117 (2)	0.0229 (14)	−0.0044 (15)	−0.0026 (16)
C3	0.0646 (16)	0.107 (2)	0.139 (3)	−0.0204 (15)	0.0059 (16)	0.0190 (19)
C4	0.098 (2)	0.106 (2)	0.118 (2)	−0.0049 (17)	0.0063 (18)	−0.0490 (18)
C5	0.0571 (13)	0.0506 (11)	0.0729 (14)	0.0062 (10)	0.0137 (11)	−0.0025 (10)
C6	0.0518 (12)	0.0581 (12)	0.0717 (13)	0.0000 (9)	0.0158 (10)	−0.0133 (10)
C7	0.0487 (10)	0.0462 (10)	0.0432 (9)	−0.0006 (8)	0.0127 (8)	−0.0013 (7)
C8	0.0403 (9)	0.0505 (10)	0.0588 (11)	−0.0065 (8)	0.0130 (8)	−0.0034 (8)
C9	0.0445 (10)	0.0428 (9)	0.0535 (10)	−0.0077 (8)	0.0121 (8)	−0.0045 (7)
C10	0.0434 (9)	0.0458 (9)	0.0346 (8)	−0.0039 (7)	0.0101 (7)	−0.0002 (7)
C11	0.0443 (10)	0.0504 (10)	0.0522 (10)	−0.0075 (8)	0.0179 (8)	0.0018 (8)
C12	0.0520 (11)	0.0418 (9)	0.0515 (10)	−0.0110 (8)	0.0158 (8)	−0.0006 (8)
C13	0.0428 (9)	0.0464 (9)	0.0375 (8)	−0.0034 (7)	0.0106 (7)	−0.0009 (7)
C14	0.0430 (10)	0.0452 (9)	0.0550 (10)	0.0005 (8)	0.0136 (8)	0.0014 (8)
C15	0.0708 (14)	0.0592 (12)	0.0691 (13)	−0.0016 (11)	0.0255 (11)	0.0094 (10)
C16	0.0752 (16)	0.0629 (14)	0.107 (2)	0.0021 (12)	0.0389 (15)	0.0285 (14)
C17	0.0579 (14)	0.0453 (11)	0.135 (2)	−0.0059 (10)	0.0247 (15)	0.0053 (14)
C18	0.0500 (12)	0.0490 (11)	0.1032 (18)	−0.0006 (9)	0.0127 (11)	−0.0093 (12)
C19	0.0362 (9)	0.0443 (9)	0.0680 (12)	0.0031 (8)	0.0084 (8)	−0.0087 (8)
C20	0.0336 (9)	0.0602 (11)	0.0476 (10)	0.0085 (8)	0.0047 (7)	−0.0084 (8)
C21	0.0447 (11)	0.0813 (14)	0.0588 (12)	0.0109 (10)	0.0003 (9)	−0.0241 (11)
C22	0.0542 (13)	0.120 (2)	0.0421 (11)	0.0176 (13)	0.0060 (9)	−0.0052 (12)
C23	0.0563 (13)	0.1094 (18)	0.0446 (11)	0.0073 (12)	0.0125 (10)	0.0115 (12)
C24	0.0486 (11)	0.0740 (13)	0.0450 (10)	−0.0004 (9)	0.0113 (8)	0.0061 (9)
C25	0.0362 (9)	0.0572 (10)	0.0394 (9)	0.0049 (8)	0.0079 (7)	−0.0027 (7)
C26	0.0446 (10)	0.0449 (9)	0.0382 (8)	−0.0030 (7)	0.0094 (7)	0.0015 (7)
C27	0.0494 (10)	0.0599 (11)	0.0394 (9)	−0.0023 (9)	0.0150 (8)	−0.0008 (8)
C28	0.0520 (11)	0.0665 (12)	0.0357 (9)	−0.0071 (9)	0.0078 (8)	−0.0031 (8)
C29	0.0437 (10)	0.0577 (11)	0.0436 (9)	−0.0032 (8)	0.0069 (8)	0.0054 (8)
C30	0.0499 (11)	0.0670 (12)	0.0523 (11)	0.0094 (9)	0.0102 (9)	−0.0068 (9)
C31	0.0525 (11)	0.0610 (11)	0.0436 (10)	0.0021 (9)	0.0069 (8)	−0.0100 (8)
C32	0.0482 (11)	0.0828 (14)	0.0594 (12)	−0.0057 (10)	0.0122 (9)	−0.0034 (10)
C33	0.0505 (12)	0.0699 (13)	0.0542 (11)	−0.0048 (10)	0.0108 (9)	0.0029 (10)
C34	0.0485 (12)	0.1056 (19)	0.0681 (14)	−0.0184 (12)	0.0128 (10)	−0.0076 (12)
C35	0.0669 (15)	0.111 (2)	0.0733 (16)	0.0061 (14)	0.0012 (12)	−0.0057 (14)
C36	0.0694 (18)	0.135 (3)	0.134 (3)	−0.0339 (18)	0.0025 (17)	0.039 (2)
C37	0.0640 (17)	0.215 (4)	0.106 (2)	−0.024 (2)	0.0379 (17)	−0.049 (2)

O1—C5	1.331 (2)	C16—C17	1.378 (4)
O1—C1	1.482 (3)	C16—H16	0.9300
O2—C5	1.195 (2)	C17—C18	1.373 (3)
O3—C7	1.376 (2)	C17—H17	0.9300
O3—C6	1.415 (2)	C18—C19	1.384 (3)
O4—C29	1.374 (2)	C18—H18	0.9300
O4—C32	1.407 (2)	C19—C20	1.459 (3)
O5—C33	1.189 (2)	C20—C25	1.395 (2)
O6—C33	1.329 (2)	C20—C21	1.400 (3)
O6—C34	1.486 (3)	C21—C22	1.374 (3)
C1—C2	1.504 (3)	C21—H21	0.9300
C1—C3	1.509 (4)	C22—C23	1.373 (3)
C1—C4	1.514 (3)	C22—H22	0.9300
C2—H2A	0.9600	C23—C24	1.384 (3)
C2—H2B	0.9600	C23—H23	0.9300
C2—H2C	0.9600	C24—C25	1.379 (2)
C3—H3A	0.9600	C24—H24	0.9300
C3—H3B	0.9600	C26—C31	1.384 (2)
C3—H3C	0.9600	C26—C27	1.390 (2)
C4—H4A	0.9600	C27—C28	1.379 (3)
C4—H4B	0.9600	C27—H27	0.9300
C4—H4C	0.9600	C28—C29	1.378 (3)
C5—C6	1.508 (3)	C28—H28	0.9300
C6—H6A	0.9700	C29—C30	1.378 (3)
C6—H6B	0.9700	C30—C31	1.386 (3)
C7—C12	1.379 (3)	C30—H30	0.9300
C7—C8	1.388 (2)	C31—H31	0.9300
C8—C9	1.384 (2)	C32—C33	1.509 (3)
C8—H8	0.9300	C32—H32A	0.9700
C9—C10	1.382 (2)	C32—H32B	0.9700
C9—H9	0.9300	C34—C35	1.486 (3)
C10—C11	1.394 (2)	C34—C37	1.515 (4)
C10—C13	1.533 (2)	C34—C36	1.515 (4)
C11—C12	1.373 (2)	C35—H35A	0.9600
C11—H11	0.9300	C35—H35B	0.9600
C12—H12	0.9300	C35—H35C	0.9600
C13—C14	1.526 (2)	C36—H36A	0.9600
C13—C25	1.538 (2)	C36—H36B	0.9600
C13—C26	1.540 (2)	C36—H36C	0.9600
C14—C15	1.381 (3)	C37—H37A	0.9600
C14—C19	1.403 (2)	C37—H37B	0.9600
C15—C16	1.394 (3)	C37—H37C	0.9600
C15—H15	0.9300
C5—O1—C1	123.30 (17)	C17—C18—H18	120.5
C7—O3—C6	116.90 (14)	C19—C18—H18	120.5
C29—O4—C32	119.62 (15)	C18—C19—C14	120.14 (19)
C33—O6—C34	121.20 (17)	C18—C19—C20	131.20 (19)
O1—C1—C2	108.35 (18)	C14—C19—C20	108.65 (15)
O1—C1—C3	101.74 (19)	C25—C20—C21	119.90 (18)
C2—C1—C3	111.9 (2)	C25—C20—C19	108.74 (15)
O1—C1—C4	110.7 (2)	C21—C20—C19	131.35 (18)
C2—C1—C4	112.6 (2)	C22—C21—C20	118.9 (2)
C3—C1—C4	110.9 (2)	C22—C21—H21	120.5
C1—C2—H2A	109.5	C20—C21—H21	120.5
C1—C2—H2B	109.5	C23—C22—C21	120.89 (19)
H2A—C2—H2B	109.5	C23—C22—H22	119.6
C1—C2—H2C	109.5	C21—C22—H22	119.6
H2A—C2—H2C	109.5	C22—C23—C24	120.9 (2)
H2B—C2—H2C	109.5	C22—C23—H23	119.6
C1—C3—H3A	109.5	C24—C23—H23	119.6
C1—C3—H3B	109.5	C25—C24—C23	119.1 (2)
H3A—C3—H3B	109.5	C25—C24—H24	120.5
C1—C3—H3C	109.5	C23—C24—H24	120.5
H3A—C3—H3C	109.5	C24—C25—C20	120.31 (16)
H3B—C3—H3C	109.5	C24—C25—C13	128.64 (16)
C1—C4—H4A	109.5	C20—C25—C13	111.04 (15)
C1—C4—H4B	109.5	C31—C26—C27	116.57 (16)
H4A—C4—H4B	109.5	C31—C26—C13	120.93 (14)
C1—C4—H4C	109.5	C27—C26—C13	122.37 (15)
H4A—C4—H4C	109.5	C28—C27—C26	121.49 (17)
H4B—C4—H4C	109.5	C28—C27—H27	119.3
O2—C5—O1	126.8 (2)	C26—C27—H27	119.3
O2—C5—C6	124.7 (2)	C29—C28—C27	120.61 (16)
O1—C5—C6	108.45 (18)	C29—C28—H28	119.7
O3—C6—C5	113.08 (17)	C27—C28—H28	119.7
O3—C6—H6A	109.0	O4—C29—C28	115.23 (16)
C5—C6—H6A	109.0	O4—C29—C30	125.40 (17)
O3—C6—H6B	109.0	C28—C29—C30	119.37 (17)
C5—C6—H6B	109.0	C29—C30—C31	119.20 (17)
H6A—C6—H6B	107.8	C29—C30—H30	120.4
O3—C7—C12	115.82 (15)	C31—C30—H30	120.4
O3—C7—C8	125.03 (16)	C26—C31—C30	122.72 (16)
C12—C7—C8	119.15 (16)	C26—C31—H31	118.6
C9—C8—C7	119.55 (17)	C30—C31—H31	118.6
C9—C8—H8	120.2	O4—C32—C33	107.86 (17)
C7—C8—H8	120.2	O4—C32—H32A	110.1
C10—C9—C8	122.25 (16)	C33—C32—H32A	110.1
C10—C9—H9	118.9	O4—C32—H32B	110.1
C8—C9—H9	118.9	C33—C32—H32B	110.1
C9—C10—C11	116.78 (15)	H32A—C32—H32B	108.4
C9—C10—C13	122.20 (14)	O5—C33—O6	126.30 (19)
C11—C10—C13	120.87 (15)	O5—C33—C32	124.5 (2)
C12—C11—C10	121.80 (16)	O6—C33—C32	109.15 (18)
C12—C11—H11	119.1	O6—C34—C35	110.30 (19)
C10—C11—H11	119.1	O6—C34—C37	102.72 (19)
C11—C12—C7	120.43 (16)	C35—C34—C37	109.9 (2)
C11—C12—H12	119.8	O6—C34—C36	108.6 (2)
C7—C12—H12	119.8	C35—C34—C36	112.5 (2)
C14—C13—C10	113.09 (13)	C37—C34—C36	112.3 (3)
C14—C13—C25	100.45 (13)	C34—C35—H35A	109.5
C10—C13—C25	108.69 (13)	C34—C35—H35B	109.5
C14—C13—C26	108.63 (13)	H35A—C35—H35B	109.5
C10—C13—C26	113.10 (13)	C34—C35—H35C	109.5
C25—C13—C26	112.24 (13)	H35A—C35—H35C	109.5
C15—C14—C19	120.51 (17)	H35B—C35—H35C	109.5
C15—C14—C13	128.38 (17)	C34—C36—H36A	109.5
C19—C14—C13	111.11 (15)	C34—C36—H36B	109.5
C14—C15—C16	118.5 (2)	H36A—C36—H36B	109.5
C14—C15—H15	120.8	C34—C36—H36C	109.5
C16—C15—H15	120.8	H36A—C36—H36C	109.5
C17—C16—C15	120.7 (2)	H36B—C36—H36C	109.5
C17—C16—H16	119.7	C34—C37—H37A	109.5
C15—C16—H16	119.7	C34—C37—H37B	109.5
C18—C17—C16	121.1 (2)	H37A—C37—H37B	109.5
C18—C17—H17	119.5	C34—C37—H37C	109.5
C16—C17—H17	119.5	H37A—C37—H37C	109.5
C17—C18—C19	119.1 (2)	H37B—C37—H37C	109.5
C5—O1—C1—C2	65.4 (3)	C18—C19—C20—C21	−0.3 (3)
C5—O1—C1—C3	−176.6 (2)	C14—C19—C20—C21	−179.32 (18)
C5—O1—C1—C4	−58.6 (3)	C25—C20—C21—C22	0.2 (3)
C1—O1—C5—O2	8.0 (3)	C19—C20—C21—C22	179.34 (18)
C1—O1—C5—C6	−171.80 (16)	C20—C21—C22—C23	0.5 (3)
C7—O3—C6—C5	76.5 (2)	C21—C22—C23—C24	−0.1 (3)
O2—C5—C6—O3	32.7 (3)	C22—C23—C24—C25	−1.0 (3)
O1—C5—C6—O3	−147.43 (16)	C23—C24—C25—C20	1.7 (3)
C6—O3—C7—C12	168.15 (16)	C23—C24—C25—C13	−178.61 (17)
C6—O3—C7—C8	−11.7 (3)	C21—C20—C25—C24	−1.3 (3)
O3—C7—C8—C9	179.95 (16)	C19—C20—C25—C24	179.36 (16)
C12—C7—C8—C9	0.1 (3)	C21—C20—C25—C13	178.93 (15)
C7—C8—C9—C10	0.7 (3)	C19—C20—C25—C13	−0.38 (19)
C8—C9—C10—C11	0.0 (3)	C14—C13—C25—C24	−179.04 (17)
C8—C9—C10—C13	175.55 (15)	C10—C13—C25—C24	−60.1 (2)
C9—C10—C11—C12	−1.5 (2)	C26—C13—C25—C24	65.7 (2)
C13—C10—C11—C12	−177.08 (15)	C14—C13—C25—C20	0.67 (17)
C10—C11—C12—C7	2.3 (3)	C10—C13—C25—C20	119.58 (15)
O3—C7—C12—C11	178.61 (15)	C26—C13—C25—C20	−114.56 (15)
C8—C7—C12—C11	−1.5 (3)	C14—C13—C26—C31	−81.16 (19)
C9—C10—C13—C14	21.0 (2)	C10—C13—C26—C31	152.41 (16)
C11—C10—C13—C14	−163.57 (15)	C25—C13—C26—C31	29.0 (2)
C9—C10—C13—C25	−89.59 (18)	C14—C13—C26—C27	94.57 (18)
C11—C10—C13—C25	85.79 (18)	C10—C13—C26—C27	−31.9 (2)
C9—C10—C13—C26	145.05 (16)	C25—C13—C26—C27	−155.27 (16)
C11—C10—C13—C26	−39.6 (2)	C31—C26—C27—C28	−2.1 (3)
C10—C13—C14—C15	64.2 (2)	C13—C26—C27—C28	−177.98 (16)
C25—C13—C14—C15	179.82 (19)	C26—C27—C28—C29	1.0 (3)
C26—C13—C14—C15	−62.3 (2)	C32—O4—C29—C28	171.85 (18)
C10—C13—C14—C19	−116.39 (16)	C32—O4—C29—C30	−8.1 (3)
C25—C13—C14—C19	−0.75 (18)	C27—C28—C29—O4	−179.37 (16)
C26—C13—C14—C19	117.17 (15)	C27—C28—C29—C30	0.6 (3)
C19—C14—C15—C16	−0.2 (3)	O4—C29—C30—C31	178.94 (18)
C13—C14—C15—C16	179.23 (18)	C28—C29—C30—C31	−1.1 (3)
C14—C15—C16—C17	−1.0 (3)	C27—C26—C31—C30	1.6 (3)
C15—C16—C17—C18	1.4 (4)	C13—C26—C31—C30	177.61 (17)
C16—C17—C18—C19	−0.6 (3)	C29—C30—C31—C26	−0.1 (3)
C17—C18—C19—C14	−0.5 (3)	C29—O4—C32—C33	−161.50 (17)
C17—C18—C19—C20	−179.45 (19)	C34—O6—C33—O5	7.3 (3)
C15—C14—C19—C18	0.9 (3)	C34—O6—C33—C32	−172.50 (19)
C13—C14—C19—C18	−178.58 (16)	O4—C32—C33—O5	8.2 (3)
C15—C14—C19—C20	−179.94 (17)	O4—C32—C33—O6	−171.93 (16)
C13—C14—C19—C20	0.6 (2)	C33—O6—C34—C35	−67.6 (3)
C18—C19—C20—C25	178.91 (19)	C33—O6—C34—C37	175.2 (2)
C14—C19—C20—C25	−0.12 (19)	C33—O6—C34—C36	56.1 (3)