3,4-Dimeth-oxy-4'-nitro-1,1'-biphen-yl.

The title compound, C(14)H(13)NO(4), was prepared through a palladium-catalysed Suzuki-Miyaura coupling reaction. The asymmetric unit comprises two mol-ecules related by pseudo-inversion symmetry. The dihedral angles between the benzene rings in the two mol-ecules are 44.30 (6) and 48.50 (6)° while those between the benzene ring and the nitro group are 6.54 (13) and 5.73 (10)°. The crystal packing is defined only by Van der Waals inter-actions.

Related literature

For general background to the synthesis and properties of 3,4-dimeth­oxy-4′-nitro-1,1′-biphenyl, see: Suzuki (1999 ▶); Razler et al. (2009 ▶); Hou et al. (2011 ▶); Li et al. (2012 ▶). For the biological activity of biphenyl derivatives, see: Kimpe et al. (1996 ▶).

Experimental

Crystal data

C14H13NO4

M = 259.25

Monoclinic,

a = 16.2714 (14) Å

b = 7.6529 (7) Å

c = 20.2448 (18) Å

β = 91.691 (1)°

V = 2519.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T min = 0.972, T max = 0.978

15429 measured reflections

4401 independent reflections

3201 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.05

4401 reflections

348 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013657/kp2400sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812013657/kp2400Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013657/kp2400Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812013657/kp2400Isup4.cml

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

C14H13NO4	F(000) = 1088
Mr = 259.25	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3878 reflections
a = 16.2714 (14) Å	θ = 2.3–24.0°
b = 7.6529 (7) Å	µ = 0.10 mm−1
c = 20.2448 (18) Å	T = 295 K
β = 91.691 (1)°	Block, colourless
V = 2519.9 (4) Å3	0.28 × 0.24 × 0.22 mm
Z = 8

Bruker APEXII CCD detector diffractometer	4401 independent reflections
Radiation source: fine-focus sealed tube	3201 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
phi and ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.972, Tmax = 0.978	k = −9→8
15429 measured reflections	l = −24→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.050P)2 + 0.2279P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4401 reflections	Δρmax = 0.13 e Å−3
348 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (7)

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.

	x	y	z	Uiso*/Ueq
O3	0.22448 (7)	0.63104 (14)	0.23783 (5)	0.0571 (3)
O4	0.27112 (7)	0.37343 (14)	0.31153 (5)	0.0574 (3)
C7	0.46025 (9)	0.64220 (19)	0.32340 (7)	0.0426 (4)
N2	0.54229 (9)	0.36706 (18)	−0.07790 (8)	0.0591 (4)
C15	0.62073 (9)	0.37383 (19)	−0.04093 (8)	0.0472 (4)
O8	1.05775 (7)	0.44259 (16)	0.18817 (6)	0.0669 (4)
C12	0.40531 (9)	0.50427 (19)	0.33426 (7)	0.0435 (4)
H12	0.4216	0.4118	0.3614	0.052*
C11	0.32767 (9)	0.50402 (19)	0.30529 (7)	0.0427 (4)
C19	0.69556 (9)	0.3404 (2)	0.06001 (7)	0.0500 (4)
H19	0.6968	0.3150	0.1050	0.060*
C21	0.84677 (9)	0.3872 (2)	0.06898 (7)	0.0463 (4)
C18	0.76892 (9)	0.37979 (19)	0.02932 (7)	0.0448 (4)
C5	0.56002 (10)	0.5714 (2)	0.41620 (7)	0.0494 (4)
H5	0.5166	0.5268	0.4399	0.059*
C22	0.90164 (9)	0.5261 (2)	0.06122 (7)	0.0483 (4)
H22	0.8909	0.6094	0.0287	0.058*
C8	0.43361 (10)	0.7800 (2)	0.28437 (7)	0.0511 (4)
H8	0.4688	0.8733	0.2771	0.061*
O7	1.02683 (7)	0.67505 (15)	0.09849 (6)	0.0657 (3)
C4	0.54441 (9)	0.63894 (18)	0.35348 (7)	0.0435 (4)
N1	0.78555 (10)	0.6281 (2)	0.43826 (9)	0.0682 (4)
C10	0.30184 (9)	0.6445 (2)	0.26520 (7)	0.0455 (4)
C26	0.86516 (10)	0.2620 (2)	0.11649 (8)	0.0551 (4)
H26	0.8296	0.1683	0.1219	0.066*
O6	0.48073 (7)	0.31992 (18)	−0.04893 (7)	0.0762 (4)
C23	0.97134 (9)	0.5411 (2)	0.10119 (7)	0.0488 (4)
C1	0.70214 (10)	0.6327 (2)	0.40854 (8)	0.0518 (4)
C6	0.63842 (10)	0.5688 (2)	0.44434 (8)	0.0551 (4)
H6A	0.6478	0.5246	0.4867	0.066*
C2	0.68964 (10)	0.7008 (2)	0.34608 (8)	0.0551 (4)
H2	0.7335	0.7436	0.3225	0.066*
C16	0.69146 (10)	0.4127 (2)	−0.07351 (8)	0.0532 (4)
H16	0.6896	0.4359	−0.1186	0.064*
C24	0.98862 (9)	0.4140 (2)	0.14981 (8)	0.0519 (4)
C20	0.62188 (10)	0.3381 (2)	0.02565 (8)	0.0513 (4)
H20	0.5734	0.3128	0.0469	0.062*
C9	0.35498 (10)	0.7815 (2)	0.25574 (7)	0.0522 (4)
H9	0.3381	0.8760	0.2299	0.063*
C3	0.61105 (10)	0.7044 (2)	0.31925 (8)	0.0515 (4)
H3	0.6020	0.7516	0.2773	0.062*
C17	0.76529 (10)	0.4165 (2)	−0.03812 (7)	0.0525 (4)
H17	0.8133	0.4440	−0.0596	0.063*
O5	0.54103 (9)	0.4053 (2)	−0.13626 (7)	0.0922 (5)
O2	0.79437 (9)	0.5829 (2)	0.49556 (8)	0.0999 (5)
C25	0.93586 (10)	0.2746 (2)	0.15612 (8)	0.0579 (4)
H25	0.9478	0.1881	0.1872	0.069*
C13	0.19155 (11)	0.7810 (2)	0.20433 (9)	0.0650 (5)
H13A	0.1897	0.8775	0.2346	0.097*
H13B	0.1370	0.7556	0.1877	0.097*
H13C	0.2259	0.8108	0.1682	0.097*
C14	0.29085 (11)	0.2330 (2)	0.35539 (9)	0.0687 (5)
H14A	0.3397	0.1754	0.3412	0.103*
H14B	0.2461	0.1511	0.3552	0.103*
H14C	0.3000	0.2778	0.3993	0.103*
O1	0.84249 (9)	0.6716 (2)	0.40461 (9)	0.1068 (6)
C27	1.00852 (12)	0.8142 (2)	0.05341 (10)	0.0764 (6)
H27A	1.0046	0.7688	0.0092	0.115*
H27B	1.0515	0.9000	0.0563	0.115*
H27C	0.9572	0.8671	0.0644	0.115*
C28	1.07699 (12)	0.3182 (3)	0.23870 (9)	0.0782 (6)
H28A	1.0325	0.3122	0.2688	0.117*
H28B	1.1264	0.3532	0.2623	0.117*
H28C	1.0850	0.2055	0.2191	0.117*

	U11	U22	U33	U12	U13	U23
O3	0.0494 (7)	0.0586 (7)	0.0624 (7)	−0.0024 (5)	−0.0154 (5)	0.0107 (5)
O4	0.0507 (7)	0.0524 (7)	0.0685 (7)	−0.0100 (5)	−0.0097 (5)	0.0158 (5)
C7	0.0435 (9)	0.0446 (9)	0.0396 (8)	0.0001 (7)	−0.0006 (6)	−0.0010 (6)
N2	0.0560 (9)	0.0477 (9)	0.0725 (10)	0.0013 (7)	−0.0162 (7)	−0.0033 (7)
C15	0.0448 (9)	0.0403 (9)	0.0560 (9)	−0.0006 (7)	−0.0089 (7)	−0.0033 (7)
O8	0.0516 (7)	0.0705 (8)	0.0772 (8)	−0.0084 (6)	−0.0228 (6)	0.0150 (6)
C12	0.0463 (9)	0.0415 (9)	0.0426 (8)	0.0017 (7)	−0.0024 (7)	0.0031 (6)
C11	0.0432 (9)	0.0425 (9)	0.0423 (8)	−0.0033 (7)	−0.0002 (6)	−0.0006 (6)
C19	0.0486 (10)	0.0551 (10)	0.0461 (8)	−0.0081 (8)	−0.0011 (7)	−0.0007 (7)
C21	0.0414 (9)	0.0483 (10)	0.0493 (9)	−0.0022 (7)	−0.0006 (7)	−0.0012 (7)
C18	0.0436 (9)	0.0405 (9)	0.0502 (9)	−0.0035 (7)	−0.0016 (7)	−0.0034 (7)
C5	0.0462 (9)	0.0523 (10)	0.0496 (9)	−0.0051 (7)	−0.0016 (7)	0.0054 (7)
C22	0.0430 (9)	0.0499 (10)	0.0517 (9)	−0.0015 (7)	−0.0019 (7)	0.0047 (7)
C8	0.0527 (10)	0.0487 (10)	0.0516 (9)	−0.0075 (8)	−0.0047 (7)	0.0076 (7)
O7	0.0504 (7)	0.0627 (8)	0.0830 (8)	−0.0178 (6)	−0.0166 (6)	0.0186 (6)
C4	0.0456 (9)	0.0389 (9)	0.0460 (8)	0.0002 (7)	0.0003 (7)	−0.0022 (6)
N1	0.0514 (10)	0.0587 (10)	0.0934 (12)	0.0013 (8)	−0.0146 (9)	−0.0039 (8)
C10	0.0435 (9)	0.0501 (10)	0.0424 (8)	0.0009 (7)	−0.0054 (7)	−0.0001 (7)
C26	0.0484 (10)	0.0533 (11)	0.0632 (10)	−0.0087 (8)	−0.0033 (8)	0.0056 (8)
O6	0.0476 (7)	0.0842 (10)	0.0961 (10)	−0.0051 (6)	−0.0101 (6)	−0.0093 (7)
C23	0.0391 (9)	0.0491 (10)	0.0582 (9)	−0.0053 (7)	−0.0010 (7)	0.0010 (7)
C1	0.0425 (9)	0.0426 (9)	0.0698 (11)	0.0013 (7)	−0.0076 (8)	−0.0072 (8)
C6	0.0570 (11)	0.0499 (10)	0.0575 (10)	−0.0012 (8)	−0.0116 (8)	0.0039 (8)
C2	0.0462 (10)	0.0527 (10)	0.0667 (11)	−0.0029 (8)	0.0064 (8)	−0.0004 (8)
C16	0.0598 (11)	0.0509 (10)	0.0486 (9)	−0.0040 (8)	−0.0051 (8)	0.0041 (7)
C24	0.0410 (9)	0.0563 (10)	0.0579 (10)	−0.0006 (8)	−0.0062 (7)	0.0037 (8)
C20	0.0432 (9)	0.0510 (10)	0.0598 (10)	−0.0082 (7)	0.0012 (7)	−0.0054 (8)
C9	0.0558 (10)	0.0487 (10)	0.0514 (9)	−0.0024 (8)	−0.0086 (8)	0.0114 (7)
C3	0.0512 (10)	0.0537 (10)	0.0495 (9)	−0.0013 (8)	0.0023 (7)	0.0029 (7)
C17	0.0487 (10)	0.0553 (10)	0.0535 (9)	−0.0068 (8)	0.0019 (7)	0.0019 (7)
O5	0.0848 (10)	0.1121 (12)	0.0778 (9)	−0.0064 (9)	−0.0319 (8)	0.0203 (9)
O2	0.0747 (10)	0.1221 (13)	0.1007 (12)	−0.0039 (9)	−0.0361 (9)	0.0143 (10)
C25	0.0542 (11)	0.0555 (11)	0.0633 (10)	−0.0028 (8)	−0.0086 (8)	0.0128 (8)
C13	0.0570 (11)	0.0665 (12)	0.0703 (11)	0.0061 (9)	−0.0153 (9)	0.0138 (9)
C14	0.0677 (12)	0.0608 (12)	0.0773 (12)	−0.0131 (9)	−0.0041 (10)	0.0217 (9)
O1	0.0442 (8)	0.1423 (15)	0.1336 (14)	−0.0050 (9)	−0.0012 (9)	0.0187 (11)
C27	0.0659 (13)	0.0623 (13)	0.1000 (15)	−0.0166 (10)	−0.0141 (11)	0.0240 (11)
C28	0.0622 (12)	0.0906 (15)	0.0804 (13)	−0.0033 (11)	−0.0239 (10)	0.0238 (11)

O3—C10	1.3640 (17)	C4—C3	1.397 (2)
O3—C13	1.4295 (19)	N1—O1	1.213 (2)
O4—C11	1.3668 (17)	N1—O2	1.215 (2)
O4—C14	1.4248 (19)	N1—C1	1.469 (2)
C7—C8	1.380 (2)	C10—C9	1.376 (2)
C7—C12	1.405 (2)	C26—C25	1.386 (2)
C7—C4	1.482 (2)	C26—H26	0.9300
N2—O5	1.2167 (18)	C23—C24	1.406 (2)
N2—O6	1.2297 (18)	C1—C6	1.373 (2)
N2—C15	1.461 (2)	C1—C2	1.377 (2)
C15—C20	1.375 (2)	C6—H6A	0.9300
C15—C16	1.376 (2)	C2—C3	1.375 (2)
O8—C24	1.3655 (18)	C2—H2	0.9300
O8—C28	1.425 (2)	C16—C17	1.381 (2)
C12—C11	1.3770 (19)	C16—H16	0.9300
C12—H12	0.9300	C24—C25	1.378 (2)
C11—C10	1.404 (2)	C20—H20	0.9300
C19—C20	1.368 (2)	C9—H9	0.9300
C19—C18	1.395 (2)	C3—H3	0.9300
C19—H19	0.9300	C17—H17	0.9300
C21—C26	1.384 (2)	C25—H25	0.9300
C21—C22	1.400 (2)	C13—H13A	0.9600
C21—C18	1.481 (2)	C13—H13B	0.9600
C18—C17	1.394 (2)	C13—H13C	0.9600
C5—C6	1.382 (2)	C14—H14A	0.9600
C5—C4	1.387 (2)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C22—C23	1.378 (2)	C27—H27A	0.9600
C22—H22	0.9300	C27—H27B	0.9600
C8—C9	1.389 (2)	C27—H27C	0.9600
C8—H8	0.9300	C28—H28A	0.9600
O7—C23	1.3681 (18)	C28—H28B	0.9600
O7—C27	1.428 (2)	C28—H28C	0.9600
C10—O3—C13	117.44 (12)	C6—C1—N1	118.57 (16)
C11—O4—C14	118.00 (12)	C2—C1—N1	119.67 (16)
C8—C7—C12	118.24 (14)	C1—C6—C5	118.66 (15)
C8—C7—C4	121.26 (14)	C1—C6—H6A	120.7
C12—C7—C4	120.50 (13)	C5—C6—H6A	120.7
O5—N2—O6	122.89 (15)	C3—C2—C1	118.73 (15)
O5—N2—C15	118.57 (15)	C3—C2—H2	120.6
O6—N2—C15	118.52 (15)	C1—C2—H2	120.6
C20—C15—C16	121.71 (14)	C15—C16—C17	118.90 (14)
C20—C15—N2	118.78 (14)	C15—C16—H16	120.6
C16—C15—N2	119.50 (14)	C17—C16—H16	120.6
C24—O8—C28	117.46 (13)	O8—C24—C25	125.20 (14)
C11—C12—C7	120.96 (13)	O8—C24—C23	115.57 (14)
C11—C12—H12	119.5	C25—C24—C23	119.23 (14)
C7—C12—H12	119.5	C19—C20—C15	118.83 (15)
O4—C11—C12	124.98 (13)	C19—C20—H20	120.6
O4—C11—C10	114.99 (13)	C15—C20—H20	120.6
C12—C11—C10	120.03 (13)	C10—C9—C8	120.71 (14)
C20—C19—C18	121.65 (14)	C10—C9—H9	119.6
C20—C19—H19	119.2	C8—C9—H9	119.6
C18—C19—H19	119.2	C2—C3—C4	121.56 (15)
C26—C21—C22	118.55 (14)	C2—C3—H3	119.2
C26—C21—C18	120.96 (14)	C4—C3—H3	119.2
C22—C21—C18	120.43 (14)	C16—C17—C18	121.00 (15)
C17—C18—C19	117.91 (14)	C16—C17—H17	119.5
C17—C18—C21	122.30 (14)	C18—C17—H17	119.5
C19—C18—C21	119.76 (13)	C24—C25—C26	120.57 (15)
C6—C5—C4	121.64 (15)	C24—C25—H25	119.7
C6—C5—H5	119.2	C26—C25—H25	119.7
C4—C5—H5	119.2	O3—C13—H13A	109.5
C23—C22—C21	120.93 (14)	O3—C13—H13B	109.5
C23—C22—H22	119.5	H13A—C13—H13B	109.5
C21—C22—H22	119.5	O3—C13—H13C	109.5
C7—C8—C9	121.01 (15)	H13A—C13—H13C	109.5
C7—C8—H8	119.5	H13B—C13—H13C	109.5
C9—C8—H8	119.5	O4—C14—H14A	109.5
C23—O7—C27	117.30 (12)	O4—C14—H14B	109.5
C5—C4—C3	117.64 (14)	H14A—C14—H14B	109.5
C5—C4—C7	121.61 (13)	O4—C14—H14C	109.5
C3—C4—C7	120.75 (13)	H14A—C14—H14C	109.5
O1—N1—O2	122.95 (17)	H14B—C14—H14C	109.5
O1—N1—C1	118.37 (17)	O7—C27—H27A	109.5
O2—N1—C1	118.67 (17)	O7—C27—H27B	109.5
O3—C10—C9	125.24 (14)	H27A—C27—H27B	109.5
O3—C10—C11	115.73 (13)	O7—C27—H27C	109.5
C9—C10—C11	119.03 (14)	H27A—C27—H27C	109.5
C21—C26—C25	120.87 (15)	H27B—C27—H27C	109.5
C21—C26—H26	119.6	O8—C28—H28A	109.5
C25—C26—H26	119.6	O8—C28—H28B	109.5
O7—C23—C22	124.86 (14)	H28A—C28—H28B	109.5
O7—C23—C24	115.32 (13)	O8—C28—H28C	109.5
C22—C23—C24	119.81 (14)	H28A—C28—H28C	109.5
C6—C1—C2	121.76 (15)	H28B—C28—H28C	109.5
O5—N2—C15—C20	177.20 (15)	C27—O7—C23—C24	−175.24 (15)
O6—N2—C15—C20	−4.1 (2)	C21—C22—C23—O7	−177.85 (15)
O5—N2—C15—C16	−3.9 (2)	C21—C22—C23—C24	1.0 (2)
O6—N2—C15—C16	174.84 (15)	O1—N1—C1—C6	174.19 (17)
C8—C7—C12—C11	1.8 (2)	O2—N1—C1—C6	−6.7 (2)
C4—C7—C12—C11	−178.45 (13)	O1—N1—C1—C2	−5.9 (2)
C14—O4—C11—C12	5.3 (2)	O2—N1—C1—C2	173.20 (17)
C14—O4—C11—C10	−175.43 (14)	C2—C1—C6—C5	0.8 (2)
C7—C12—C11—O4	178.05 (13)	N1—C1—C6—C5	−179.33 (14)
C7—C12—C11—C10	−1.2 (2)	C4—C5—C6—C1	−0.9 (2)
C20—C19—C18—C17	−0.3 (2)	C6—C1—C2—C3	0.0 (2)
C20—C19—C18—C21	177.71 (14)	N1—C1—C2—C3	−179.82 (14)
C26—C21—C18—C17	−139.08 (16)	C20—C15—C16—C17	−0.3 (2)
C22—C21—C18—C17	43.9 (2)	N2—C15—C16—C17	−179.21 (14)
C26—C21—C18—C19	43.0 (2)	C28—O8—C24—C25	0.1 (3)
C22—C21—C18—C19	−133.97 (16)	C28—O8—C24—C23	179.15 (15)
C26—C21—C22—C23	−1.8 (2)	O7—C23—C24—O8	0.8 (2)
C18—C21—C22—C23	175.24 (14)	C22—C23—C24—O8	−178.24 (14)
C12—C7—C8—C9	−0.9 (2)	O7—C23—C24—C25	179.87 (15)
C4—C7—C8—C9	179.31 (14)	C22—C23—C24—C25	0.9 (2)
C6—C5—C4—C3	0.2 (2)	C18—C19—C20—C15	0.7 (2)
C6—C5—C4—C7	−179.81 (14)	C16—C15—C20—C19	−0.4 (2)
C8—C7—C4—C5	143.17 (16)	N2—C15—C20—C19	178.48 (14)
C12—C7—C4—C5	−36.6 (2)	O3—C10—C9—C8	−178.02 (14)
C8—C7—C4—C3	−36.8 (2)	C11—C10—C9—C8	1.1 (2)
C12—C7—C4—C3	143.41 (15)	C7—C8—C9—C10	−0.5 (2)
C13—O3—C10—C9	−9.3 (2)	C1—C2—C3—C4	−0.8 (2)
C13—O3—C10—C11	171.54 (13)	C5—C4—C3—C2	0.7 (2)
O4—C11—C10—O3	−0.35 (19)	C7—C4—C3—C2	−179.31 (14)
C12—C11—C10—O3	178.96 (13)	C15—C16—C17—C18	0.8 (2)
O4—C11—C10—C9	−179.59 (13)	C19—C18—C17—C16	−0.5 (2)
C12—C11—C10—C9	−0.3 (2)	C21—C18—C17—C16	−178.42 (15)
C22—C21—C26—C25	0.7 (2)	O8—C24—C25—C26	177.02 (16)
C18—C21—C26—C25	−176.34 (15)	C23—C24—C25—C26	−2.0 (3)
C27—O7—C23—C22	3.7 (2)	C21—C26—C25—C24	1.2 (3)