Methyl 9-hy-droxy-15-methyl-2-oxo-11-(pyren-1-yl)-10-oxa-15-aza-tetra-cyclo-[7.6.0.0(1,12).0(3,8)]penta-deca-3(8),4,6-triene-12-carboxyl-ate.

In the title compound, C32H25NO5, the furan and pyrrole rings each adopt an envelope conformation, the respective flap atoms being the C atom bearing the pyrene substituent and the CH2 atom adjacent to the N atom. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond. In the crystal, C-H⋯O contacts link the mol-ecules, forming a two-dimensional network parallel to (001).

Related literature

For the solid–state structures of pyrenes, see: Robertson & White (1947 ▶); Camerman & Trotter (1965 ▶); Allmann (1970 ▶); Hazell et al. (1972 ▶); Kai et al. (1978 ▶). For a related structure, see: Gruber et al. (2010 ▶). For the use of pyrenes in fluorescence sensors, see: Bren (2001 ▶).

Experimental

Crystal data

C32H25NO5

M = 503.53

Monoclinic,

a = 31.6964 (6) Å

b = 11.0325 (2) Å

c = 14.1965 (3) Å

β = 96.503 (1)°

V = 4932.44 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.979, T max = 0.983

20953 measured reflections

4661 independent reflections

3280 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.04

4661 reflections

347 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, 2R. DOI: 10.1107/S1600536813024951/bt6925sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024951/bt6925Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024951/bt6925Isup3.cml

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

C32H25NO5	F(000) = 2112
Mr = 503.53	Dx = 1.356 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8834 reflections
a = 31.6964 (6) Å	θ = 2.1–31.2°
b = 11.0325 (2) Å	µ = 0.09 mm−1
c = 14.1965 (3) Å	T = 293 K
β = 96.503 (1)°	Block, colourless
V = 4932.44 (17) Å3	0.25 × 0.20 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	4661 independent reflections
Radiation source: fine-focus sealed tube	3280 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scan	θmax = 25.7°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −38→37
Tmin = 0.979, Tmax = 0.983	k = −11→13
20953 measured reflections	l = −17→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0547P)2 + 1.507P] where P = (Fo2 + 2Fc2)/3
4661 reflections	(Δ/σ)max < 0.001
347 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.18 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
O1	0.06963 (4)	0.02788 (10)	0.10712 (8)	0.0468 (3)
O3	0.08806 (4)	0.40608 (11)	−0.02173 (8)	0.0555 (3)
O2	0.00524 (4)	0.11622 (12)	0.06940 (10)	0.0499 (3)
N	0.03715 (5)	0.18310 (13)	−0.08500 (9)	0.0468 (4)
C17	0.11197 (5)	0.04084 (15)	0.08207 (11)	0.0396 (4)
H17	0.1286	0.0899	0.1304	0.048*
C16	0.13183 (5)	−0.08345 (15)	0.07916 (11)	0.0412 (4)
O4	0.16465 (4)	0.24317 (13)	0.03901 (10)	0.0647 (4)
C1	0.23651 (5)	−0.24458 (17)	0.12311 (11)	0.0453 (4)
C2	0.19242 (5)	−0.22187 (16)	0.09870 (11)	0.0408 (4)
C3	0.17562 (5)	−0.10230 (15)	0.10426 (10)	0.0396 (4)
O5	0.15453 (5)	0.19027 (15)	−0.11231 (10)	0.0828 (5)
C23	0.05729 (5)	0.23187 (15)	0.16533 (11)	0.0387 (4)
C25	0.07807 (5)	0.32732 (16)	0.03066 (11)	0.0402 (4)
C10	0.25291 (6)	−0.36313 (19)	0.11528 (12)	0.0532 (5)
C13	0.16523 (6)	−0.31982 (16)	0.06926 (12)	0.0452 (4)
C15	0.10609 (6)	−0.18228 (16)	0.05246 (13)	0.0496 (5)
H15	0.0771	−0.1702	0.0375	0.060*
C22	0.04826 (5)	0.14005 (15)	0.08771 (11)	0.0396 (4)
C18	0.10582 (5)	0.11345 (15)	−0.01307 (11)	0.0391 (4)
C29	0.05082 (5)	0.22207 (18)	0.25959 (11)	0.0484 (5)
H29	0.0407	0.1504	0.2832	0.058*
C24	0.07323 (5)	0.33856 (16)	0.13185 (11)	0.0419 (4)
C14	0.12230 (6)	−0.29750 (16)	0.04743 (13)	0.0510 (5)
H14	0.1041	−0.3614	0.0290	0.061*
C4	0.20465 (6)	−0.00815 (18)	0.13747 (12)	0.0491 (5)
H4	0.1947	0.0708	0.1417	0.059*
C5	0.24608 (6)	−0.0317 (2)	0.16270 (13)	0.0575 (5)
H5	0.2638	0.0315	0.1855	0.069*
C28	0.05960 (6)	0.3202 (2)	0.31740 (13)	0.0608 (6)
H28	0.0545	0.3153	0.3805	0.073*
C21	0.08922 (6)	0.03972 (17)	−0.10085 (12)	0.0496 (5)
H21A	0.1123	0.0165	−0.1366	0.059*
H21B	0.0747	−0.0329	−0.0831	0.059*
C6	0.26386 (6)	−0.1491 (2)	0.15595 (13)	0.0541 (5)
C20	0.05868 (6)	0.12456 (18)	−0.15795 (12)	0.0550 (5)
H20A	0.0737	0.1832	−0.1926	0.066*
H20B	0.0388	0.0801	−0.2022	0.066*
C26	0.08287 (6)	0.43730 (18)	0.19105 (13)	0.0558 (5)
H26	0.0937	0.5085	0.1682	0.067*
C30	0.14512 (6)	0.18882 (16)	−0.02412 (13)	0.0461 (4)
C12	0.18277 (7)	−0.43904 (19)	0.06394 (14)	0.0593 (5)
H12	0.1650	−0.5037	0.0452	0.071*
C11	0.22455 (7)	−0.4587 (2)	0.08562 (14)	0.0637 (6)
H11	0.2351	−0.5368	0.0811	0.076*
C19	0.06708 (5)	0.19699 (15)	0.00068 (10)	0.0375 (4)
C32	0.00976 (7)	0.28537 (19)	−0.11593 (14)	0.0617 (5)
H32A	−0.0029	0.3173	−0.0628	0.092*
H32B	−0.0122	0.2587	−0.1636	0.092*
H32C	0.0263	0.3474	−0.1418	0.092*
C9	0.29646 (7)	−0.3813 (2)	0.13888 (15)	0.0695 (6)
H9	0.3077	−0.4585	0.1332	0.083*
C27	0.07588 (7)	0.4264 (2)	0.28456 (13)	0.0642 (6)
H27	0.0821	0.4909	0.3259	0.077*
C7	0.30703 (7)	−0.1735 (3)	0.17972 (16)	0.0736 (7)
H7	0.3253	−0.1114	0.2023	0.088*
C8	0.32282 (7)	−0.2884 (3)	0.17003 (17)	0.0783 (7)
H8	0.3517	−0.3028	0.1848	0.094*
C31	0.18922 (11)	0.2689 (3)	−0.1309 (2)	0.1279 (13)
H31A	0.1935	0.2635	−0.1966	0.192*
H31B	0.2147	0.2442	−0.0925	0.192*
H31C	0.1825	0.3510	−0.1159	0.192*
H2	0.0041 (7)	0.110 (2)	0.0079 (16)	0.081 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0466 (7)	0.0380 (7)	0.0591 (7)	0.0011 (5)	0.0194 (5)	0.0090 (6)
O3	0.0785 (9)	0.0419 (7)	0.0462 (7)	−0.0123 (7)	0.0079 (6)	0.0074 (6)
O2	0.0402 (7)	0.0526 (8)	0.0577 (8)	−0.0076 (6)	0.0101 (6)	−0.0048 (6)
N	0.0519 (9)	0.0460 (9)	0.0407 (7)	−0.0009 (7)	−0.0024 (6)	−0.0036 (7)
C17	0.0378 (9)	0.0375 (10)	0.0445 (9)	−0.0044 (8)	0.0080 (7)	0.0011 (7)
C16	0.0433 (10)	0.0377 (10)	0.0426 (9)	−0.0018 (8)	0.0047 (7)	0.0027 (7)
O4	0.0629 (9)	0.0629 (9)	0.0671 (9)	−0.0265 (8)	0.0021 (7)	0.0046 (7)
C1	0.0426 (11)	0.0574 (12)	0.0365 (8)	0.0016 (9)	0.0074 (7)	0.0088 (8)
C2	0.0437 (10)	0.0452 (10)	0.0337 (8)	0.0001 (8)	0.0060 (7)	0.0025 (7)
C3	0.0414 (10)	0.0424 (10)	0.0350 (8)	−0.0039 (8)	0.0050 (7)	0.0010 (7)
O5	0.1044 (13)	0.0818 (11)	0.0715 (9)	−0.0397 (9)	0.0505 (9)	−0.0140 (8)
C23	0.0334 (9)	0.0427 (10)	0.0402 (9)	0.0039 (8)	0.0045 (7)	0.0027 (7)
C25	0.0447 (10)	0.0365 (10)	0.0392 (8)	−0.0012 (8)	0.0035 (7)	0.0026 (7)
C10	0.0522 (12)	0.0634 (13)	0.0451 (10)	0.0141 (10)	0.0103 (8)	0.0123 (9)
C13	0.0527 (11)	0.0380 (10)	0.0440 (9)	0.0029 (9)	0.0013 (8)	0.0020 (8)
C15	0.0415 (10)	0.0410 (11)	0.0646 (11)	−0.0031 (9)	−0.0018 (8)	0.0034 (9)
C22	0.0370 (10)	0.0358 (10)	0.0468 (9)	−0.0008 (7)	0.0085 (7)	0.0041 (7)
C18	0.0414 (10)	0.0371 (10)	0.0397 (8)	−0.0041 (8)	0.0087 (7)	−0.0025 (7)
C29	0.0442 (10)	0.0612 (12)	0.0399 (9)	0.0072 (9)	0.0046 (7)	0.0085 (9)
C24	0.0469 (10)	0.0391 (10)	0.0393 (8)	0.0012 (8)	0.0035 (7)	−0.0036 (8)
C14	0.0511 (12)	0.0347 (10)	0.0642 (11)	−0.0068 (8)	−0.0061 (9)	0.0029 (9)
C4	0.0476 (11)	0.0477 (11)	0.0517 (10)	−0.0047 (9)	0.0039 (8)	−0.0019 (8)
C5	0.0487 (12)	0.0633 (14)	0.0594 (11)	−0.0167 (10)	0.0009 (9)	0.0015 (10)
C28	0.0600 (13)	0.0856 (16)	0.0369 (9)	0.0064 (12)	0.0066 (8)	−0.0028 (10)
C21	0.0592 (12)	0.0443 (11)	0.0462 (9)	−0.0039 (9)	0.0103 (8)	−0.0077 (8)
C6	0.0433 (11)	0.0684 (14)	0.0510 (10)	−0.0006 (10)	0.0075 (8)	0.0128 (10)
C20	0.0718 (13)	0.0519 (12)	0.0400 (9)	−0.0019 (10)	0.0009 (9)	−0.0079 (8)
C26	0.0668 (13)	0.0486 (12)	0.0515 (11)	−0.0036 (10)	0.0039 (9)	−0.0078 (9)
C30	0.0496 (11)	0.0405 (10)	0.0505 (10)	−0.0034 (9)	0.0153 (9)	0.0007 (8)
C12	0.0681 (14)	0.0445 (12)	0.0634 (12)	0.0053 (10)	−0.0009 (10)	−0.0007 (9)
C11	0.0729 (15)	0.0534 (13)	0.0647 (12)	0.0182 (12)	0.0071 (11)	0.0018 (10)
C19	0.0424 (10)	0.0343 (9)	0.0358 (8)	−0.0038 (7)	0.0040 (7)	−0.0005 (7)
C32	0.0629 (13)	0.0666 (14)	0.0523 (11)	0.0053 (11)	−0.0078 (9)	−0.0007 (10)
C9	0.0585 (14)	0.0812 (17)	0.0708 (13)	0.0222 (13)	0.0164 (11)	0.0211 (12)
C27	0.0731 (14)	0.0703 (15)	0.0484 (11)	0.0027 (12)	0.0027 (10)	−0.0226 (10)
C7	0.0442 (13)	0.0909 (19)	0.0843 (15)	−0.0056 (12)	0.0016 (11)	0.0195 (13)
C8	0.0431 (13)	0.103 (2)	0.0890 (16)	0.0141 (14)	0.0087 (11)	0.0327 (15)
C31	0.152 (3)	0.123 (3)	0.126 (2)	−0.074 (2)	0.091 (2)	−0.015 (2)

O1—C22	1.423 (2)	C18—C21	1.531 (2)
O1—C17	1.4340 (18)	C18—C19	1.565 (2)
O3—C25	1.2090 (19)	C29—C28	1.368 (3)
O2—C22	1.384 (2)	C29—H29	0.9300
O2—H2	0.87 (2)	C24—C26	1.389 (2)
N—C20	1.455 (2)	C14—H14	0.9300
N—C32	1.460 (2)	C4—C5	1.347 (3)
N—C19	1.464 (2)	C4—H4	0.9300
C17—C16	1.511 (2)	C5—C6	1.420 (3)
C17—C18	1.563 (2)	C5—H5	0.9300
C17—H17	0.9800	C28—C27	1.382 (3)
C16—C15	1.389 (2)	C28—H28	0.9300
C16—C3	1.409 (2)	C21—C20	1.514 (3)
O4—C30	1.192 (2)	C21—H21A	0.9700
C1—C6	1.410 (3)	C21—H21B	0.9700
C1—C10	1.416 (3)	C6—C7	1.398 (3)
C1—C2	1.423 (2)	C20—H20A	0.9700
C2—C13	1.415 (2)	C20—H20B	0.9700
C2—C3	1.428 (2)	C26—C27	1.376 (3)
C3—C4	1.432 (2)	C26—H26	0.9300
O5—C30	1.319 (2)	C12—C11	1.343 (3)
O5—C31	1.448 (3)	C12—H12	0.9300
C23—C29	1.381 (2)	C11—H11	0.9300
C23—C24	1.386 (2)	C32—H32A	0.9600
C23—C22	1.500 (2)	C32—H32B	0.9600
C25—C24	1.467 (2)	C32—H32C	0.9600
C25—C19	1.529 (2)	C9—C8	1.364 (3)
C10—C9	1.398 (3)	C9—H9	0.9300
C10—C11	1.418 (3)	C27—H27	0.9300
C13—C14	1.383 (2)	C7—C8	1.375 (3)
C13—C12	1.433 (3)	C7—H7	0.9300
C15—C14	1.376 (3)	C8—H8	0.9300
C15—H15	0.9300	C31—H31A	0.9600
C22—C19	1.563 (2)	C31—H31B	0.9600
C18—C30	1.521 (2)	C31—H31C	0.9600
C22—O1—C17	107.67 (12)	C4—C5—C6	122.74 (19)
C22—O2—H2	97.4 (15)	C4—C5—H5	118.6
C20—N—C32	116.09 (14)	C6—C5—H5	118.6
C20—N—C19	109.02 (14)	C29—C28—C27	121.79 (17)
C32—N—C19	118.45 (14)	C29—C28—H28	119.1
O1—C17—C16	108.71 (13)	C27—C28—H28	119.1
O1—C17—C18	103.69 (12)	C20—C21—C18	104.32 (14)
C16—C17—C18	116.93 (13)	C20—C21—H21A	110.9
O1—C17—H17	109.1	C18—C21—H21A	110.9
C16—C17—H17	109.1	C20—C21—H21B	110.9
C18—C17—H17	109.1	C18—C21—H21B	110.9
C15—C16—C3	118.99 (16)	H21A—C21—H21B	108.9
C15—C16—C17	119.09 (15)	C7—C6—C1	119.0 (2)
C3—C16—C17	121.91 (15)	C7—C6—C5	123.0 (2)
C6—C1—C10	119.89 (17)	C1—C6—C5	118.03 (17)
C6—C1—C2	119.93 (17)	N—C20—C21	102.50 (13)
C10—C1—C2	120.17 (17)	N—C20—H20A	111.3
C13—C2—C1	119.05 (16)	C21—C20—H20A	111.3
C13—C2—C3	120.21 (15)	N—C20—H20B	111.3
C1—C2—C3	120.74 (16)	C21—C20—H20B	111.3
C16—C3—C2	119.03 (15)	H20A—C20—H20B	109.2
C16—C3—C4	123.66 (16)	C27—C26—C24	117.84 (19)
C2—C3—C4	117.30 (15)	C27—C26—H26	121.1
C30—O5—C31	115.97 (18)	C24—C26—H26	121.1
C29—C23—C24	119.91 (16)	O4—C30—O5	123.62 (17)
C29—C23—C22	128.47 (16)	O4—C30—C18	124.01 (15)
C24—C23—C22	111.60 (13)	O5—C30—C18	112.35 (16)
O3—C25—C24	127.25 (16)	C11—C12—C13	120.96 (19)
O3—C25—C19	124.89 (14)	C11—C12—H12	119.5
C24—C25—C19	107.84 (13)	C13—C12—H12	119.5
C9—C10—C1	118.4 (2)	C12—C11—C10	121.56 (19)
C9—C10—C11	122.7 (2)	C12—C11—H11	119.2
C1—C10—C11	118.93 (17)	C10—C11—H11	119.2
C14—C13—C2	118.74 (16)	N—C19—C25	115.83 (13)
C14—C13—C12	121.95 (17)	N—C19—C22	110.19 (13)
C2—C13—C12	119.31 (17)	C25—C19—C22	104.67 (12)
C14—C15—C16	121.89 (17)	N—C19—C18	106.18 (12)
C14—C15—H15	119.1	C25—C19—C18	115.56 (13)
C16—C15—H15	119.1	C22—C19—C18	103.71 (12)
O2—C22—O1	107.96 (13)	N—C32—H32A	109.5
O2—C22—C23	111.60 (13)	N—C32—H32B	109.5
O1—C22—C23	113.46 (13)	H32A—C32—H32B	109.5
O2—C22—C19	112.58 (13)	N—C32—H32C	109.5
O1—C22—C19	106.66 (12)	H32A—C32—H32C	109.5
C23—C22—C19	104.54 (13)	H32B—C32—H32C	109.5
C30—C18—C21	114.63 (14)	C8—C9—C10	121.4 (2)
C30—C18—C17	110.23 (13)	C8—C9—H9	119.3
C21—C18—C17	115.39 (14)	C10—C9—H9	119.3
C30—C18—C19	110.75 (13)	C26—C27—C28	120.44 (18)
C21—C18—C19	102.26 (13)	C26—C27—H27	119.8
C17—C18—C19	102.52 (12)	C28—C27—H27	119.8
C28—C29—C23	118.49 (18)	C8—C7—C6	120.7 (2)
C28—C29—H29	120.8	C8—C7—H7	119.6
C23—C29—H29	120.8	C6—C7—H7	119.6
C23—C24—C26	121.50 (15)	C9—C8—C7	120.6 (2)
C23—C24—C25	110.28 (15)	C9—C8—H8	119.7
C26—C24—C25	128.21 (16)	C7—C8—H8	119.7
C15—C14—C13	121.10 (17)	O5—C31—H31A	109.5
C15—C14—H14	119.5	O5—C31—H31B	109.5
C13—C14—H14	119.5	H31A—C31—H31B	109.5
C5—C4—C3	121.22 (18)	O5—C31—H31C	109.5
C5—C4—H4	119.4	H31A—C31—H31C	109.5
C3—C4—H4	119.4	H31B—C31—H31C	109.5
C22—O1—C17—C16	−166.42 (13)	C10—C1—C6—C7	0.4 (3)
C22—O1—C17—C18	−41.34 (15)	C2—C1—C6—C7	179.86 (16)
O1—C17—C16—C15	31.7 (2)	C10—C1—C6—C5	180.00 (16)
C18—C17—C16—C15	−85.17 (19)	C2—C1—C6—C5	−0.6 (2)
O1—C17—C16—C3	−147.21 (14)	C4—C5—C6—C7	178.29 (18)
C18—C17—C16—C3	95.89 (18)	C4—C5—C6—C1	−1.3 (3)
C6—C1—C2—C13	−177.65 (15)	C32—N—C20—C21	170.80 (15)
C10—C1—C2—C13	1.8 (2)	C19—N—C20—C21	33.93 (18)
C6—C1—C2—C3	2.0 (2)	C18—C21—C20—N	−40.11 (18)
C10—C1—C2—C3	−178.61 (14)	C23—C24—C26—C27	−0.4 (3)
C15—C16—C3—C2	1.9 (2)	C25—C24—C26—C27	−179.51 (18)
C17—C16—C3—C2	−179.16 (14)	C31—O5—C30—O4	−3.6 (3)
C15—C16—C3—C4	−176.69 (16)	C31—O5—C30—C18	174.6 (2)
C17—C16—C3—C4	2.3 (2)	C21—C18—C30—O4	−173.00 (18)
C13—C2—C3—C16	−0.6 (2)	C17—C18—C30—O4	−40.8 (2)
C1—C2—C3—C16	179.76 (14)	C19—C18—C30—O4	71.9 (2)
C13—C2—C3—C4	178.05 (14)	C21—C18—C30—O5	8.9 (2)
C1—C2—C3—C4	−1.6 (2)	C17—C18—C30—O5	141.05 (16)
C6—C1—C10—C9	−1.3 (2)	C19—C18—C30—O5	−106.19 (17)
C2—C1—C10—C9	179.25 (15)	C14—C13—C12—C11	−179.88 (18)
C6—C1—C10—C11	177.55 (16)	C2—C13—C12—C11	−0.6 (3)
C2—C1—C10—C11	−1.9 (2)	C13—C12—C11—C10	0.5 (3)
C1—C2—C13—C14	178.75 (15)	C9—C10—C11—C12	179.54 (18)
C3—C2—C13—C14	−0.9 (2)	C1—C10—C11—C12	0.7 (3)
C1—C2—C13—C12	−0.5 (2)	C20—N—C19—C25	115.29 (16)
C3—C2—C13—C12	179.85 (15)	C32—N—C19—C25	−20.4 (2)
C3—C16—C15—C14	−1.7 (3)	C20—N—C19—C22	−126.17 (15)
C17—C16—C15—C14	179.29 (16)	C32—N—C19—C22	98.12 (17)
C17—O1—C22—O2	153.13 (13)	C20—N—C19—C18	−14.48 (17)
C17—O1—C22—C23	−82.64 (15)	C32—N—C19—C18	−150.18 (15)
C17—O1—C22—C19	31.92 (16)	O3—C25—C19—N	−47.9 (2)
C29—C23—C22—O2	64.5 (2)	C24—C25—C19—N	130.74 (15)
C24—C23—C22—O2	−113.96 (16)	O3—C25—C19—C22	−169.45 (16)
C29—C23—C22—O1	−57.7 (2)	C24—C25—C19—C22	9.20 (17)
C24—C23—C22—O1	123.81 (15)	O3—C25—C19—C18	77.2 (2)
C29—C23—C22—C19	−173.51 (16)	C24—C25—C19—C18	−104.17 (15)
C24—C23—C22—C19	8.00 (18)	O2—C22—C19—N	−14.03 (19)
O1—C17—C18—C30	151.21 (13)	O1—C22—C19—N	104.20 (15)
C16—C17—C18—C30	−89.18 (17)	C23—C22—C19—N	−135.34 (14)
O1—C17—C18—C21	−76.99 (16)	O2—C22—C19—C25	111.15 (15)
C16—C17—C18—C21	42.6 (2)	O1—C22—C19—C25	−130.62 (13)
O1—C17—C18—C19	33.26 (15)	C23—C22—C19—C25	−10.16 (16)
C16—C17—C18—C19	152.87 (14)	O2—C22—C19—C18	−127.32 (14)
C24—C23—C29—C28	1.4 (3)	O1—C22—C19—C18	−9.09 (16)
C22—C23—C29—C28	−176.98 (17)	C23—C22—C19—C18	111.37 (13)
C29—C23—C24—C26	−0.2 (3)	C30—C18—C19—N	111.87 (15)
C22—C23—C24—C26	178.41 (16)	C21—C18—C19—N	−10.71 (16)
C29—C23—C24—C25	179.07 (15)	C17—C18—C19—N	−130.55 (13)
C22—C23—C24—C25	−2.3 (2)	C30—C18—C19—C25	−18.05 (18)
O3—C25—C24—C23	173.97 (17)	C21—C18—C19—C25	−140.62 (14)
C19—C25—C24—C23	−4.64 (19)	C17—C18—C19—C25	99.53 (14)
O3—C25—C24—C26	−6.8 (3)	C30—C18—C19—C22	−131.98 (14)
C19—C25—C24—C26	174.59 (18)	C21—C18—C19—C22	105.45 (14)
C16—C15—C14—C13	0.2 (3)	C17—C18—C19—C22	−14.40 (15)
C2—C13—C14—C15	1.1 (3)	C1—C10—C9—C8	0.9 (3)
C12—C13—C14—C15	−179.64 (17)	C11—C10—C9—C8	−177.93 (19)
C16—C3—C4—C5	178.38 (16)	C24—C26—C27—C28	−0.3 (3)
C2—C3—C4—C5	−0.2 (2)	C29—C28—C27—C26	1.5 (3)
C3—C4—C5—C6	1.7 (3)	C1—C6—C7—C8	0.9 (3)
C23—C29—C28—C27	−2.0 (3)	C5—C6—C7—C8	−178.6 (2)
C30—C18—C21—C20	−89.05 (18)	C10—C9—C8—C7	0.5 (3)
C17—C18—C21—C20	141.26 (15)	C6—C7—C8—C9	−1.4 (3)
C19—C18—C21—C20	30.85 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···O3i	0.93	2.43	3.299 (2)	155
O2—H2···N	0.87 (2)	1.95 (2)	2.6217 (19)	133 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯O3i	0.93	2.43	3.299 (2)	155
O2—H2⋯N	0.87 (2)	1.95 (2)	2.6217 (19)	133 (2)

Symmetry code: (i) .