2,2'-Bis(4-nitro-phen-oxy)-1,1'-binaphth-yl.

The title compound, C(32)H(20)N(2)O(6), was synthesized by the reaction of 1,1'-binaphthyl-2,2'-diol and 4-nitro-phenol in the presence of K(2)CO(3). The two naphthalene systems make a dihedral angle of 73.70 (5)°. The crystal packing involves mol-ecules connected by C-H⋯O hydrogen bonds into a chain along the c axis.

Related literature

For the chemistry of 1,1′-binaphthyl-2,2′-diol, see: Hiroshi et al. (2005 ▶); Minatti & Dötz (2005 ▶); Pu (1998 ▶); Periasamy et al. (1998 ▶).

Experimental

Crystal data

C32H20N2O6

M = 528.50

Monoclinic,

a = 7.6159 (9) Å

b = 24.810 (3) Å

c = 13.5022 (15) Å

β = 95.790 (3)°

V = 2538.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 (2) K

0.03 × 0.03 × 0.02 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.988, T max = 0.990

13574 measured reflections

4971 independent reflections

2521 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.114

S = 0.85

4971 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016061/kp2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016061/kp2173Isup2.hkl

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

C32H20N2O6	F(000) = 1096
Mr = 528.50	Dx = 1.383 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1979 reflections
a = 7.6159 (9) Å	θ = 3.1–27.3°
b = 24.810 (3) Å	µ = 0.10 mm−1
c = 13.5022 (15) Å	T = 296 K
β = 95.790 (3)°	Block, colourless
V = 2538.3 (5) Å3	0.03 × 0.03 × 0.02 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4971 independent reflections
Radiation source: fine-focus sealed tube	2521 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.988, Tmax = 0.990	k = −23→30
13574 measured reflections	l = −16→14

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 0.86	w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3
4971 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
O4	1.3508 (2)	0.39839 (7)	0.26199 (13)	0.0562 (5)
O1	0.9879 (2)	0.43838 (7)	0.17323 (12)	0.0553 (5)
N1	0.4540 (3)	0.59046 (10)	0.10343 (16)	0.0583 (7)
C25	1.0230 (4)	0.40498 (9)	0.44518 (18)	0.0446 (7)
C8	1.0031 (3)	0.36017 (9)	0.27505 (17)	0.0397 (6)
C24	1.1008 (3)	0.39169 (9)	0.35680 (17)	0.0399 (6)
C11	0.8489 (4)	0.47360 (10)	0.15533 (17)	0.0448 (7)
C17	1.2690 (4)	0.40833 (9)	0.34837 (19)	0.0448 (7)
C23	0.8491 (4)	0.39068 (10)	0.46109 (19)	0.0529 (7)
H23A	0.7797	0.3720	0.4118	0.063*
C12	0.6795 (4)	0.46179 (10)	0.17407 (18)	0.0535 (7)
H12A	0.6527	0.4279	0.1980	0.064*
C7	1.0293 (4)	0.27455 (11)	0.37128 (19)	0.0553 (8)
H7A	1.0782	0.2931	0.4273	0.066*
O3	0.4934 (3)	0.63407 (8)	0.07056 (14)	0.0734 (6)
C9	0.9767 (3)	0.30318 (10)	0.28363 (18)	0.0445 (7)
C14	0.5925 (4)	0.54981 (11)	0.12233 (18)	0.0479 (7)
C3	0.8464 (4)	0.30174 (12)	0.1116 (2)	0.0641 (8)
H3A	0.7937	0.2828	0.0570	0.077*
C1	0.9496 (3)	0.38393 (10)	0.18595 (19)	0.0467 (7)
C27	1.3749 (3)	0.34527 (11)	0.23632 (19)	0.0462 (7)
N2	1.4260 (4)	0.18672 (11)	0.1414 (2)	0.0768 (8)
C15	0.7607 (4)	0.56203 (11)	0.10407 (18)	0.0558 (8)
H15A	0.7872	0.5961	0.0808	0.067*
C2	0.8700 (4)	0.35544 (12)	0.10426 (19)	0.0608 (8)
H2A	0.8336	0.3733	0.0452	0.073*
C22	0.7803 (4)	0.40373 (11)	0.5478 (2)	0.0671 (9)
H22A	0.6655	0.3937	0.5571	0.081*
C32	1.4198 (3)	0.30571 (11)	0.30582 (19)	0.0531 (7)
H32A	1.4369	0.3143	0.3732	0.064*
O2	0.3041 (3)	0.57870 (8)	0.12092 (16)	0.0825 (7)
C10	0.9002 (4)	0.27407 (11)	0.2002 (2)	0.0526 (7)
C16	0.8915 (4)	0.52370 (11)	0.12019 (17)	0.0540 (7)
H16A	1.0066	0.5315	0.1076	0.065*
C26	1.1244 (4)	0.43468 (10)	0.52074 (19)	0.0528 (7)
C18	1.3671 (4)	0.43793 (10)	0.4217 (2)	0.0601 (8)
H18A	1.4807	0.4491	0.4122	0.072*
C13	0.5496 (4)	0.50002 (11)	0.15740 (19)	0.0578 (8)
H13A	0.4343	0.4923	0.1696	0.069*
C31	1.4392 (4)	0.25318 (11)	0.27459 (19)	0.0539 (7)
H31A	1.4698	0.2259	0.3203	0.065*
C19	1.2974 (4)	0.45038 (11)	0.5068 (2)	0.0663 (9)
H19A	1.3642	0.4695	0.5564	0.080*
C30	1.4125 (4)	0.24221 (11)	0.1749 (2)	0.0527 (7)
C4	0.8843 (4)	0.21737 (12)	0.2078 (2)	0.0721 (9)
H4A	0.8363	0.1978	0.1529	0.086*
O5	1.4527 (3)	0.15122 (9)	0.20191 (16)	0.0954 (8)
C20	1.0481 (5)	0.44692 (12)	0.6088 (2)	0.0767 (10)
H20A	1.1141	0.4658	0.6591	0.092*
C29	1.3761 (4)	0.28167 (12)	0.10560 (19)	0.0634 (8)
H29A	1.3643	0.2733	0.0381	0.076*
C28	1.3571 (3)	0.33380 (11)	0.13642 (19)	0.0564 (8)
H28A	1.3323	0.3611	0.0900	0.068*
C5	0.9374 (5)	0.19142 (12)	0.2932 (3)	0.0820 (10)
H5A	0.9256	0.1542	0.2969	0.098*
O6	1.4102 (4)	0.17823 (9)	0.05245 (17)	0.1275 (11)
C6	1.0096 (4)	0.22003 (12)	0.3755 (2)	0.0680 (9)
H6A	1.0451	0.2018	0.4344	0.082*
C21	0.8817 (5)	0.43195 (13)	0.6221 (2)	0.0774 (11)
H21A	0.8347	0.4405	0.6811	0.093*

	U11	U22	U33	U12	U13	U23
O4	0.0586 (14)	0.0454 (12)	0.0676 (12)	−0.0072 (9)	0.0207 (10)	0.0062 (10)
O1	0.0477 (13)	0.0515 (12)	0.0657 (12)	−0.0035 (10)	0.0005 (10)	0.0137 (10)
N1	0.0579 (19)	0.0617 (18)	0.0550 (15)	0.0040 (15)	0.0045 (14)	0.0064 (14)
C25	0.0507 (19)	0.0348 (15)	0.0473 (16)	0.0051 (13)	0.0006 (14)	0.0039 (13)
C8	0.0376 (17)	0.0417 (16)	0.0406 (15)	−0.0034 (12)	0.0087 (12)	−0.0034 (13)
C24	0.0422 (18)	0.0337 (15)	0.0429 (15)	−0.0030 (12)	−0.0007 (13)	0.0037 (12)
C11	0.0453 (19)	0.0494 (17)	0.0387 (15)	−0.0052 (14)	−0.0014 (13)	0.0036 (13)
C17	0.0462 (19)	0.0353 (15)	0.0519 (17)	−0.0057 (13)	−0.0001 (15)	0.0033 (13)
C23	0.055 (2)	0.0523 (18)	0.0518 (17)	0.0060 (14)	0.0094 (15)	0.0038 (14)
C12	0.050 (2)	0.0451 (18)	0.0666 (19)	−0.0043 (15)	0.0126 (16)	0.0111 (15)
C7	0.060 (2)	0.0493 (18)	0.0572 (18)	−0.0070 (15)	0.0095 (15)	0.0004 (15)
O3	0.0901 (18)	0.0586 (14)	0.0727 (13)	0.0070 (12)	0.0136 (12)	0.0199 (12)
C9	0.0418 (18)	0.0441 (17)	0.0490 (16)	−0.0071 (13)	0.0113 (13)	−0.0053 (14)
C14	0.049 (2)	0.0480 (18)	0.0461 (16)	−0.0017 (15)	0.0038 (14)	0.0031 (14)
C3	0.058 (2)	0.077 (2)	0.0542 (19)	−0.0067 (18)	−0.0057 (16)	−0.0206 (18)
C1	0.0399 (18)	0.0475 (18)	0.0529 (17)	−0.0023 (14)	0.0056 (14)	−0.0026 (15)
C27	0.0383 (17)	0.0463 (18)	0.0551 (17)	−0.0013 (13)	0.0094 (14)	0.0056 (15)
N2	0.093 (2)	0.067 (2)	0.0689 (19)	0.0145 (17)	0.0008 (17)	−0.0064 (17)
C15	0.057 (2)	0.0519 (18)	0.0573 (18)	−0.0111 (16)	0.0026 (16)	0.0150 (15)
C2	0.055 (2)	0.075 (2)	0.0502 (17)	0.0011 (17)	−0.0048 (15)	−0.0006 (17)
C22	0.071 (2)	0.069 (2)	0.065 (2)	0.0214 (18)	0.0218 (19)	0.0203 (18)
C32	0.056 (2)	0.0562 (19)	0.0463 (16)	−0.0008 (15)	0.0037 (14)	0.0003 (15)
O2	0.0545 (16)	0.0778 (16)	0.1164 (18)	0.0085 (12)	0.0148 (14)	0.0156 (13)
C10	0.0457 (19)	0.0504 (18)	0.0618 (18)	−0.0079 (14)	0.0058 (15)	−0.0147 (16)
C16	0.0465 (19)	0.0599 (19)	0.0551 (17)	−0.0085 (15)	0.0030 (14)	0.0144 (15)
C26	0.072 (2)	0.0379 (16)	0.0467 (17)	0.0052 (15)	−0.0054 (16)	−0.0045 (14)
C18	0.051 (2)	0.0488 (19)	0.079 (2)	−0.0140 (15)	−0.0049 (17)	0.0064 (17)
C13	0.049 (2)	0.0567 (19)	0.0702 (19)	−0.0057 (16)	0.0164 (16)	0.0074 (16)
C31	0.059 (2)	0.0557 (19)	0.0471 (17)	0.0056 (15)	0.0070 (14)	0.0049 (15)
C19	0.082 (3)	0.0444 (19)	0.068 (2)	−0.0130 (17)	−0.0175 (19)	−0.0091 (16)
C30	0.053 (2)	0.0541 (19)	0.0516 (17)	0.0122 (15)	0.0069 (15)	−0.0025 (16)
C4	0.073 (3)	0.053 (2)	0.089 (2)	−0.0150 (17)	0.007 (2)	−0.0250 (19)
O5	0.144 (2)	0.0593 (15)	0.0822 (16)	0.0152 (15)	0.0077 (15)	−0.0012 (13)
C20	0.117 (3)	0.061 (2)	0.050 (2)	0.012 (2)	0.002 (2)	−0.0108 (16)
C29	0.072 (2)	0.075 (2)	0.0436 (16)	0.0157 (18)	0.0068 (15)	0.0045 (17)
C28	0.059 (2)	0.061 (2)	0.0503 (18)	0.0101 (16)	0.0105 (15)	0.0154 (16)
C5	0.094 (3)	0.042 (2)	0.111 (3)	−0.0168 (19)	0.017 (2)	−0.007 (2)
O6	0.220 (3)	0.098 (2)	0.0606 (14)	0.0392 (19)	−0.0073 (17)	−0.0251 (14)
C6	0.086 (3)	0.048 (2)	0.072 (2)	−0.0035 (17)	0.0167 (19)	0.0086 (18)
C21	0.114 (3)	0.072 (2)	0.050 (2)	0.031 (2)	0.022 (2)	0.0027 (18)

O4—C27	1.380 (3)	N2—O5	1.205 (3)
O4—C17	1.398 (3)	N2—O6	1.213 (3)
O1—C11	1.375 (3)	N2—C30	1.456 (3)
O1—C1	1.396 (3)	C15—C16	1.378 (3)
N1—O3	1.218 (2)	C15—H15A	0.9300
N1—O2	1.224 (3)	C2—H2A	0.9300
N1—C14	1.463 (3)	C22—C21	1.391 (4)
C25—C23	1.408 (3)	C22—H22A	0.9300
C25—C26	1.422 (3)	C32—C31	1.382 (3)
C25—C24	1.423 (3)	C32—H32A	0.9300
C8—C1	1.365 (3)	C10—C4	1.416 (3)
C8—C9	1.434 (3)	C16—H16A	0.9300
C8—C24	1.489 (3)	C26—C19	1.405 (4)
C24—C17	1.361 (3)	C26—C20	1.408 (3)
C11—C12	1.371 (3)	C18—C19	1.349 (3)
C11—C16	1.381 (3)	C18—H18A	0.9300
C17—C18	1.389 (3)	C13—H13A	0.9300
C23—C22	1.369 (3)	C31—C30	1.368 (3)
C23—H23A	0.9300	C31—H31A	0.9300
C12—C13	1.373 (3)	C19—H19A	0.9300
C12—H12A	0.9300	C30—C29	1.364 (3)
C7—C6	1.363 (3)	C4—C5	1.347 (4)
C7—C9	1.403 (3)	C4—H4A	0.9300
C7—H7A	0.9300	C20—C21	1.350 (4)
C9—C10	1.413 (3)	C20—H20A	0.9300
C14—C15	1.363 (3)	C29—C28	1.371 (3)
C14—C13	1.374 (3)	C29—H29A	0.9300
C3—C2	1.349 (3)	C28—H28A	0.9300
C3—C10	1.405 (3)	C5—C6	1.385 (4)
C3—H3A	0.9300	C5—H5A	0.9300
C1—C2	1.396 (3)	C6—H6A	0.9300
C27—C28	1.372 (3)	C21—H21A	0.9300
C27—C32	1.377 (3)
C27—O4—C17	117.38 (19)	C1—C2—H2A	120.2
C11—O1—C1	118.0 (2)	C23—C22—C21	120.2 (3)
O3—N1—O2	123.4 (3)	C23—C22—H22A	119.9
O3—N1—C14	118.4 (3)	C21—C22—H22A	119.9
O2—N1—C14	118.2 (2)	C27—C32—C31	119.4 (2)
C23—C25—C26	118.2 (3)	C27—C32—H32A	120.3
C23—C25—C24	123.2 (2)	C31—C32—H32A	120.3
C26—C25—C24	118.7 (3)	C3—C10—C9	119.4 (2)
C1—C8—C9	117.7 (2)	C3—C10—C4	121.8 (3)
C1—C8—C24	120.6 (2)	C9—C10—C4	118.8 (3)
C9—C8—C24	121.4 (2)	C15—C16—C11	119.0 (3)
C17—C24—C25	118.3 (2)	C15—C16—H16A	120.5
C17—C24—C8	120.1 (2)	C11—C16—H16A	120.5
C25—C24—C8	121.6 (2)	C19—C26—C20	121.7 (3)
C12—C11—O1	123.6 (2)	C19—C26—C25	119.7 (3)
C12—C11—C16	120.9 (3)	C20—C26—C25	118.5 (3)
O1—C11—C16	115.4 (2)	C19—C18—C17	119.9 (3)
C24—C17—C18	123.0 (3)	C19—C18—H18A	120.1
C24—C17—O4	121.2 (2)	C17—C18—H18A	120.1
C18—C17—O4	115.8 (3)	C12—C13—C14	119.0 (3)
C22—C23—C25	121.2 (3)	C12—C13—H13A	120.5
C22—C23—H23A	119.4	C14—C13—H13A	120.5
C25—C23—H23A	119.4	C30—C31—C32	118.5 (3)
C11—C12—C13	119.9 (2)	C30—C31—H31A	120.7
C11—C12—H12A	120.1	C32—C31—H31A	120.7
C13—C12—H12A	120.1	C18—C19—C26	120.4 (3)
C6—C7—C9	121.0 (3)	C18—C19—H19A	119.8
C6—C7—H7A	119.5	C26—C19—H19A	119.8
C9—C7—H7A	119.5	C29—C30—C31	122.2 (3)
C7—C9—C10	118.2 (2)	C29—C30—N2	118.8 (3)
C7—C9—C8	122.4 (2)	C31—C30—N2	119.1 (3)
C10—C9—C8	119.3 (2)	C5—C4—C10	121.1 (3)
C15—C14—C13	121.5 (3)	C5—C4—H4A	119.5
C15—C14—N1	119.3 (3)	C10—C4—H4A	119.5
C13—C14—N1	119.2 (3)	C21—C20—C26	121.7 (3)
C2—C3—C10	121.0 (3)	C21—C20—H20A	119.1
C2—C3—H3A	119.5	C26—C20—H20A	119.1
C10—C3—H3A	119.5	C30—C29—C28	119.3 (3)
C8—C1—C2	123.0 (2)	C30—C29—H29A	120.3
C8—C1—O1	118.6 (2)	C28—C29—H29A	120.3
C2—C1—O1	118.2 (2)	C29—C28—C27	119.4 (3)
C28—C27—C32	121.0 (3)	C29—C28—H28A	120.3
C28—C27—O4	116.3 (2)	C27—C28—H28A	120.3
C32—C27—O4	122.7 (2)	C4—C5—C6	120.2 (3)
O5—N2—O6	122.5 (3)	C4—C5—H5A	119.9
O5—N2—C30	119.5 (3)	C6—C5—H5A	119.9
O6—N2—C30	118.0 (3)	C7—C6—C5	120.8 (3)
C14—C15—C16	119.7 (3)	C7—C6—H6A	119.6
C14—C15—H15A	120.2	C5—C6—H6A	119.6
C16—C15—H15A	120.2	C20—C21—C22	120.2 (3)
C3—C2—C1	119.5 (3)	C20—C21—H21A	119.9
C3—C2—H2A	120.2	C22—C21—H21A	119.9
C23—C25—C24—C17	178.9 (2)	C28—C27—C32—C31	−3.0 (4)
C26—C25—C24—C17	−0.3 (3)	O4—C27—C32—C31	179.0 (2)
C23—C25—C24—C8	−1.5 (4)	C2—C3—C10—C9	1.4 (4)
C26—C25—C24—C8	179.3 (2)	C2—C3—C10—C4	−176.9 (3)
C1—C8—C24—C17	−69.6 (3)	C7—C9—C10—C3	180.0 (2)
C9—C8—C24—C17	104.5 (3)	C8—C9—C10—C3	−2.0 (4)
C1—C8—C24—C25	110.8 (3)	C7—C9—C10—C4	−1.7 (4)
C9—C8—C24—C25	−75.1 (3)	C8—C9—C10—C4	176.3 (2)
C1—O1—C11—C12	17.3 (3)	C14—C15—C16—C11	−0.4 (4)
C1—O1—C11—C16	−165.2 (2)	C12—C11—C16—C15	0.0 (4)
C25—C24—C17—C18	−0.5 (4)	O1—C11—C16—C15	−177.5 (2)
C8—C24—C17—C18	179.9 (2)	C23—C25—C26—C19	−179.0 (2)
C25—C24—C17—O4	−177.6 (2)	C24—C25—C26—C19	0.2 (4)
C8—C24—C17—O4	2.8 (4)	C23—C25—C26—C20	1.9 (4)
C27—O4—C17—C24	−62.0 (3)	C24—C25—C26—C20	−178.9 (2)
C27—O4—C17—C18	120.7 (2)	C24—C17—C18—C19	1.4 (4)
C26—C25—C23—C22	−1.6 (4)	O4—C17—C18—C19	178.7 (2)
C24—C25—C23—C22	179.2 (2)	C11—C12—C13—C14	−0.2 (4)
O1—C11—C12—C13	177.6 (2)	C15—C14—C13—C12	−0.2 (4)
C16—C11—C12—C13	0.3 (4)	N1—C14—C13—C12	179.3 (2)
C6—C7—C9—C10	1.0 (4)	C27—C32—C31—C30	−0.2 (4)
C6—C7—C9—C8	−176.9 (2)	C17—C18—C19—C26	−1.5 (4)
C1—C8—C9—C7	179.0 (2)	C20—C26—C19—C18	179.8 (3)
C24—C8—C9—C7	4.7 (4)	C25—C26—C19—C18	0.7 (4)
C1—C8—C9—C10	1.1 (4)	C32—C31—C30—C29	3.3 (4)
C24—C8—C9—C10	−173.2 (2)	C32—C31—C30—N2	−177.7 (2)
O3—N1—C14—C15	0.9 (4)	O5—N2—C30—C29	−177.7 (3)
O2—N1—C14—C15	−179.6 (2)	O6—N2—C30—C29	2.5 (4)
O3—N1—C14—C13	−178.6 (2)	O5—N2—C30—C31	3.3 (4)
O2—N1—C14—C13	0.9 (4)	O6—N2—C30—C31	−176.5 (3)
C9—C8—C1—C2	0.5 (4)	C3—C10—C4—C5	179.6 (3)
C24—C8—C1—C2	174.8 (2)	C9—C10—C4—C5	1.3 (4)
C9—C8—C1—O1	−174.5 (2)	C19—C26—C20—C21	179.8 (3)
C24—C8—C1—O1	−0.2 (4)	C25—C26—C20—C21	−1.1 (4)
C11—O1—C1—C8	−117.7 (3)	C31—C30—C29—C28	−3.2 (4)
C11—O1—C1—C2	67.0 (3)	N2—C30—C29—C28	177.8 (3)
C17—O4—C27—C28	144.1 (2)	C30—C29—C28—C27	0.0 (4)
C17—O4—C27—C32	−37.9 (3)	C32—C27—C28—C29	3.1 (4)
C13—C14—C15—C16	0.5 (4)	O4—C27—C28—C29	−178.8 (2)
N1—C14—C15—C16	−179.0 (2)	C10—C4—C5—C6	−0.2 (5)
C10—C3—C2—C1	0.2 (4)	C9—C7—C6—C5	0.1 (4)
C8—C1—C2—C3	−1.2 (4)	C4—C5—C6—C7	−0.5 (5)
O1—C1—C2—C3	173.9 (2)	C26—C20—C21—C22	−0.1 (5)
C25—C23—C22—C21	0.5 (4)	C23—C22—C21—C20	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2i	0.93	2.54	3.425 (3)	159.
C32—H32A···O6ii	0.93	2.45	3.360 (3)	165.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2i	0.93	2.54	3.425 (3)	159
C32—H32A⋯O6ii	0.93	2.45	3.360 (3)	165

Symmetry codes: (i) ; (ii) .