[2-Benzyl-3-(naphthalen-1-yl)-2,3-di-hydro-1,2-oxazole-4,5-di-yl]bis-(phenyl-methanone).

In the title compound, C34H25NO3, the five-membered heterocyclic ring adopts an envelope conformation with the N atom as the flap. The plane through the four basal atoms of this ring makes dihedral angles of 69.78 (13), 53.15 (12) and 86.42 (13)°, respectively, with the benzene rings of the benzyl group and the two phenyl-methanone groups at the 4 and 5 positions, and of 78.60 (11)° with the naphthalenyl system. In the crystal, the mol-ecules are linked through C-H⋯O and C-H⋯π contacts into layers parallel to (101).

Related literature

For background to isoxazoline dervatives and their applications, see: Gahlot et al. (2003 ▶); Kiss et al. (2009 ▶); Norman et al. (2007 ▶); Shi et al. (2012 ▶); Habeeb et al. (2001 ▶). For the synthesis of related compounds, see: Chakraborty et al. (2012 ▶). For a related structure, see: Sandhya et al. (2013 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C34H25NO3

M = 495.55

Monoclinic,

a = 14.4105 (10) Å

b = 10.9408 (9) Å

c = 16.0924 (13) Å

β = 94.235 (4)°

V = 2530.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS, Bruker, 2007 ▶) T min = 0.968, T max = 0.976

12772 measured reflections

5822 independent reflections

3603 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.181

S = 1.02

6092 reflections

343 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536814003250/yk2103sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003250/yk2103Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C34H25NO3	F(000) = 1040
Mr = 495.55	Dx = 1.301 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3803 reflections
a = 14.4105 (10) Å	θ = 2.3–27.8°
b = 10.9408 (9) Å	µ = 0.08 mm−1
c = 16.0924 (13) Å	T = 296 K
β = 94.235 (4)°	Block, colourless
V = 2530.2 (3) Å3	0.40 × 0.35 × 0.30 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	5822 independent reflections
Radiation source: fine-focus sealed tube	3603 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS, Bruker, 2007)	h = −16→18
Tmin = 0.968, Tmax = 0.976	k = −6→14
12772 measured reflections	l = −19→20

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) = 0.181	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0908P)2 + 0.7195P] where P = (Fo2 + 2Fc2)/3
6092 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

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 > 2sigma(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	0.39550 (11)	0.44858 (16)	0.08868 (12)	0.0624 (5)
O2	0.19673 (10)	0.34089 (13)	0.03919 (9)	0.0432 (4)
O3	0.26338 (13)	0.62696 (16)	0.20136 (11)	0.0630 (5)
N1	0.10514 (11)	0.30910 (15)	0.07285 (10)	0.0390 (4)
C3	0.2856 (2)	0.7599 (3)	−0.12462 (16)	0.0723 (8)
H3	0.2782	0.8197	−0.1656	0.087*
C4	0.3717 (2)	0.7075 (3)	−0.10706 (16)	0.0686 (8)
H4	0.4219	0.7315	−0.1363	0.082*
C5	0.38332 (17)	0.6192 (2)	−0.04588 (15)	0.0537 (6)
H5	0.4416	0.5848	−0.0331	0.064*
C6	0.30779 (14)	0.58189 (18)	−0.00355 (13)	0.0402 (5)
C7	0.32028 (14)	0.48646 (19)	0.06095 (13)	0.0409 (5)
C8	0.23384 (13)	0.42734 (18)	0.09116 (12)	0.0381 (4)
C9	0.19231 (13)	0.44248 (18)	0.16161 (12)	0.0366 (4)
C17	0.11552 (13)	0.34732 (18)	0.16270 (12)	0.0364 (4)
H17	0.1356	0.2781	0.1983	0.044*
C18	0.02157 (13)	0.39606 (18)	0.18652 (12)	0.0384 (4)
C19	−0.02994 (13)	0.3363 (2)	0.24645 (12)	0.0398 (5)
C20	−0.00101 (16)	0.2282 (2)	0.28950 (14)	0.0478 (5)
H20	0.0561	0.1934	0.2798	0.057*
C21	−0.05523 (18)	0.1743 (3)	0.34471 (15)	0.0602 (6)
H21	−0.0346	0.1035	0.3723	0.072*
C22	−0.14162 (19)	0.2239 (3)	0.36060 (16)	0.0702 (8)
H22	−0.1784	0.1854	0.3979	0.084*
C1	0.22138 (16)	0.6349 (2)	−0.02256 (15)	0.0523 (6)
H1	0.1704	0.6096	0.0052	0.063*
C2	0.2108 (2)	0.7250 (3)	−0.08236 (17)	0.0677 (7)
H2	0.1532	0.7620	−0.0940	0.081*
C28	0.09503 (15)	0.17655 (19)	0.06203 (13)	0.0446 (5)
H28A	0.0495	0.1464	0.0985	0.054*
H28B	0.1540	0.1372	0.0779	0.054*
C29	0.06476 (14)	0.14371 (18)	−0.02659 (12)	0.0388 (5)
C34	0.11531 (16)	0.0652 (2)	−0.07236 (15)	0.0540 (6)
H34	0.1706	0.0321	−0.0488	0.065*
C33	0.08423 (19)	0.0350 (3)	−0.15369 (17)	0.0665 (7)
H33	0.1192	−0.0182	−0.1839	0.080*
C32	0.0036 (2)	0.0818 (3)	−0.18963 (16)	0.0656 (7)
H32	−0.0161	0.0619	−0.2443	0.079*
C31	−0.0483 (2)	0.1589 (3)	−0.14438 (17)	0.0718 (8)
H31	−0.1041	0.1905	−0.1680	0.086*
C30	−0.01775 (18)	0.1895 (2)	−0.06364 (16)	0.0586 (6)
H30	−0.0534	0.2419	−0.0335	0.070*
C10	0.21642 (14)	0.53967 (19)	0.22180 (13)	0.0413 (5)
C11	0.18224 (13)	0.53279 (19)	0.30646 (12)	0.0388 (5)
C16	0.15152 (16)	0.6376 (2)	0.34411 (14)	0.0511 (6)
H16	0.1521	0.7120	0.3161	0.061*
C15	0.12022 (18)	0.6322 (3)	0.42265 (16)	0.0612 (7)
H15	0.0991	0.7026	0.4475	0.073*
C14	0.12018 (18)	0.5226 (3)	0.46435 (16)	0.0630 (7)
H14	0.0988	0.5192	0.5174	0.076*
C13	0.15140 (19)	0.4183 (3)	0.42821 (15)	0.0616 (7)
H13	0.1521	0.3446	0.4571	0.074*
C12	0.18182 (16)	0.4228 (2)	0.34900 (13)	0.0481 (5)
H12	0.2021	0.3519	0.3241	0.058*
C23	−0.17159 (18)	0.3275 (3)	0.32192 (16)	0.0673 (8)
H23	−0.2288	0.3603	0.3333	0.081*
C24	−0.11730 (15)	0.3873 (2)	0.26426 (14)	0.0497 (6)
C25	−0.14949 (17)	0.4948 (3)	0.22237 (17)	0.0617 (7)
H25	−0.2066	0.5278	0.2339	0.074*
C26	−0.09828 (18)	0.5506 (2)	0.16541 (17)	0.0613 (7)
H26	−0.1197	0.6217	0.1388	0.074*
C27	−0.01301 (16)	0.4992 (2)	0.14757 (15)	0.0495 (5)
H27	0.0213	0.5365	0.1079	0.059*

	U11	U22	U33	U12	U13	U23
O1	0.0422 (9)	0.0586 (11)	0.0866 (13)	0.0009 (7)	0.0058 (8)	0.0176 (9)
O2	0.0480 (8)	0.0400 (8)	0.0431 (8)	−0.0091 (6)	0.0131 (6)	−0.0046 (6)
O3	0.0778 (12)	0.0517 (10)	0.0607 (10)	−0.0289 (9)	0.0140 (9)	−0.0076 (8)
N1	0.0434 (9)	0.0356 (9)	0.0388 (9)	−0.0078 (7)	0.0088 (7)	−0.0023 (7)
C3	0.104 (2)	0.0635 (18)	0.0487 (14)	−0.0184 (16)	−0.0017 (14)	0.0174 (13)
C4	0.086 (2)	0.0664 (18)	0.0564 (16)	−0.0176 (15)	0.0268 (14)	0.0029 (13)
C5	0.0564 (13)	0.0514 (14)	0.0556 (14)	−0.0056 (11)	0.0204 (11)	−0.0035 (11)
C6	0.0467 (11)	0.0341 (11)	0.0405 (11)	−0.0041 (8)	0.0083 (9)	−0.0034 (9)
C7	0.0389 (10)	0.0365 (11)	0.0485 (12)	−0.0032 (8)	0.0111 (9)	−0.0024 (9)
C8	0.0386 (10)	0.0314 (10)	0.0442 (11)	−0.0030 (8)	0.0037 (8)	0.0012 (8)
C9	0.0358 (10)	0.0336 (10)	0.0404 (10)	−0.0049 (8)	0.0035 (8)	−0.0021 (8)
C17	0.0396 (10)	0.0331 (10)	0.0369 (10)	−0.0041 (8)	0.0040 (8)	−0.0008 (8)
C18	0.0389 (10)	0.0355 (11)	0.0404 (11)	−0.0026 (8)	−0.0001 (8)	−0.0042 (9)
C19	0.0402 (10)	0.0440 (12)	0.0350 (10)	−0.0045 (9)	0.0024 (8)	−0.0094 (9)
C20	0.0496 (12)	0.0472 (13)	0.0465 (12)	−0.0027 (10)	0.0033 (10)	0.0005 (10)
C21	0.0656 (15)	0.0671 (17)	0.0486 (13)	−0.0081 (13)	0.0085 (12)	0.0088 (12)
C22	0.0658 (17)	0.098 (2)	0.0493 (15)	−0.0126 (15)	0.0192 (13)	0.0066 (15)
C1	0.0514 (13)	0.0501 (14)	0.0553 (13)	−0.0036 (10)	0.0037 (10)	0.0066 (11)
C2	0.0729 (17)	0.0639 (18)	0.0640 (16)	−0.0023 (13)	−0.0105 (13)	0.0147 (13)
C28	0.0518 (12)	0.0354 (11)	0.0465 (12)	−0.0080 (9)	0.0027 (9)	0.0000 (9)
C29	0.0430 (11)	0.0315 (10)	0.0422 (11)	−0.0090 (8)	0.0054 (9)	0.0015 (8)
C34	0.0439 (12)	0.0585 (15)	0.0599 (14)	−0.0020 (10)	0.0050 (10)	−0.0097 (12)
C33	0.0683 (17)	0.0738 (19)	0.0587 (15)	−0.0083 (14)	0.0132 (13)	−0.0241 (14)
C32	0.0844 (19)	0.0665 (18)	0.0447 (13)	−0.0212 (15)	−0.0026 (13)	−0.0066 (13)
C31	0.0698 (17)	0.073 (2)	0.0683 (17)	0.0023 (14)	−0.0215 (14)	0.0094 (15)
C30	0.0627 (15)	0.0543 (15)	0.0584 (15)	0.0121 (12)	0.0015 (12)	−0.0016 (12)
C10	0.0419 (11)	0.0340 (11)	0.0475 (12)	−0.0049 (8)	0.0011 (9)	−0.0014 (9)
C11	0.0394 (10)	0.0360 (11)	0.0402 (11)	−0.0039 (8)	−0.0030 (8)	−0.0035 (8)
C16	0.0616 (14)	0.0389 (12)	0.0522 (13)	0.0008 (10)	−0.0001 (11)	−0.0040 (10)
C15	0.0645 (15)	0.0602 (17)	0.0593 (15)	0.0035 (12)	0.0077 (12)	−0.0161 (13)
C14	0.0679 (16)	0.0777 (19)	0.0441 (13)	−0.0106 (14)	0.0084 (11)	−0.0074 (13)
C13	0.0794 (17)	0.0563 (16)	0.0475 (14)	−0.0108 (13)	−0.0069 (12)	0.0084 (12)
C12	0.0613 (14)	0.0392 (12)	0.0425 (12)	−0.0001 (10)	−0.0035 (10)	−0.0020 (9)
C23	0.0542 (14)	0.095 (2)	0.0547 (15)	0.0045 (14)	0.0191 (12)	−0.0079 (15)
C24	0.0451 (12)	0.0604 (15)	0.0439 (12)	0.0026 (10)	0.0055 (9)	−0.0119 (11)
C25	0.0494 (13)	0.0660 (17)	0.0698 (16)	0.0146 (12)	0.0064 (12)	−0.0136 (14)
C26	0.0595 (15)	0.0477 (15)	0.0758 (17)	0.0142 (11)	−0.0016 (13)	0.0008 (13)
C27	0.0504 (12)	0.0413 (12)	0.0566 (13)	0.0013 (10)	0.0019 (10)	0.0037 (10)

O1—C7	1.214 (3)	C28—C29	1.504 (3)
O2—C8	1.347 (2)	C28—H28A	0.9700
O2—N1	1.504 (2)	C28—H28B	0.9700
O3—C10	1.229 (2)	C29—C34	1.375 (3)
N1—C28	1.467 (3)	C29—C30	1.384 (3)
N1—C17	1.502 (2)	C34—C33	1.392 (3)
C3—C2	1.371 (4)	C34—H34	0.9300
C3—C4	1.376 (4)	C33—C32	1.359 (4)
C3—H3	0.9300	C33—H33	0.9300
C4—C5	1.381 (4)	C32—C31	1.372 (4)
C4—H4	0.9300	C32—H32	0.9300
C5—C6	1.387 (3)	C31—C30	1.382 (4)
C5—H5	0.9300	C31—H31	0.9300
C6—C1	1.387 (3)	C30—H30	0.9300
C6—C7	1.474 (3)	C10—C11	1.484 (3)
C7—C8	1.515 (3)	C11—C12	1.385 (3)
C8—C9	1.331 (3)	C11—C16	1.385 (3)
C9—C10	1.463 (3)	C16—C15	1.374 (3)
C9—C17	1.520 (3)	C16—H16	0.9300
C17—C18	1.530 (3)	C15—C14	1.374 (4)
C17—H17	0.9800	C15—H15	0.9300
C18—C27	1.367 (3)	C14—C13	1.372 (4)
C18—C19	1.419 (3)	C14—H14	0.9300
C19—C20	1.418 (3)	C13—C12	1.379 (3)
C19—C24	1.425 (3)	C13—H13	0.9300
C20—C21	1.360 (3)	C12—H12	0.9300
C20—H20	0.9300	C23—C24	1.417 (4)
C21—C22	1.399 (4)	C23—H23	0.9300
C21—H21	0.9300	C24—C25	1.416 (4)
C22—C23	1.349 (4)	C25—C26	1.363 (4)
C22—H22	0.9300	C25—H25	0.9300
C1—C2	1.378 (3)	C26—C27	1.400 (3)
C1—H1	0.9300	C26—H26	0.9300
C2—H2	0.9300	C27—H27	0.9300
C8—O2—N1	104.92 (13)	C29—C28—H28B	109.3
C28—N1—C17	113.05 (16)	H28A—C28—H28B	108.0
C28—N1—O2	105.55 (14)	C34—C29—C30	117.9 (2)
C17—N1—O2	104.76 (13)	C34—C29—C28	122.0 (2)
C2—C3—C4	120.8 (3)	C30—C29—C28	120.1 (2)
C2—C3—H3	119.6	C29—C34—C33	120.4 (2)
C4—C3—H3	119.6	C29—C34—H34	119.8
C3—C4—C5	119.9 (2)	C33—C34—H34	119.8
C3—C4—H4	120.1	C32—C33—C34	121.1 (3)
C5—C4—H4	120.1	C32—C33—H33	119.5
C4—C5—C6	119.8 (2)	C34—C33—H33	119.5
C4—C5—H5	120.1	C33—C32—C31	119.2 (2)
C6—C5—H5	120.1	C33—C32—H32	120.4
C5—C6—C1	119.5 (2)	C31—C32—H32	120.4
C5—C6—C7	119.6 (2)	C32—C31—C30	120.0 (3)
C1—C6—C7	120.83 (19)	C32—C31—H31	120.0
O1—C7—C6	124.05 (19)	C30—C31—H31	120.0
O1—C7—C8	117.97 (19)	C31—C30—C29	121.4 (2)
C6—C7—C8	117.89 (17)	C31—C30—H30	119.3
C9—C8—O2	115.69 (17)	C29—C30—H30	119.3
C9—C8—C7	130.71 (18)	O3—C10—C9	119.74 (19)
O2—C8—C7	113.49 (16)	O3—C10—C11	120.77 (19)
C8—C9—C10	123.70 (18)	C9—C10—C11	119.48 (17)
C8—C9—C17	107.34 (17)	C12—C11—C16	119.3 (2)
C10—C9—C17	128.87 (17)	C12—C11—C10	120.78 (19)
N1—C17—C9	101.55 (15)	C16—C11—C10	119.87 (19)
N1—C17—C18	108.13 (15)	C15—C16—C11	120.3 (2)
C9—C17—C18	114.99 (16)	C15—C16—H16	119.9
N1—C17—H17	110.6	C11—C16—H16	119.9
C9—C17—H17	110.6	C14—C15—C16	119.9 (2)
C18—C17—H17	110.6	C14—C15—H15	120.0
C27—C18—C19	120.04 (19)	C16—C15—H15	120.0
C27—C18—C17	118.18 (18)	C13—C14—C15	120.5 (2)
C19—C18—C17	121.78 (18)	C13—C14—H14	119.8
C20—C19—C18	124.51 (19)	C15—C14—H14	119.8
C20—C19—C24	117.42 (19)	C14—C13—C12	119.9 (2)
C18—C19—C24	118.1 (2)	C14—C13—H13	120.0
C21—C20—C19	121.2 (2)	C12—C13—H13	120.0
C21—C20—H20	119.4	C13—C12—C11	120.1 (2)
C19—C20—H20	119.4	C13—C12—H12	120.0
C20—C21—C22	120.9 (3)	C11—C12—H12	120.0
C20—C21—H21	119.6	C22—C23—C24	121.1 (2)
C22—C21—H21	119.6	C22—C23—H23	119.4
C23—C22—C21	120.1 (2)	C24—C23—H23	119.4
C23—C22—H22	120.0	C25—C24—C23	121.2 (2)
C21—C22—H22	120.0	C25—C24—C19	119.5 (2)
C2—C1—C6	120.3 (2)	C23—C24—C19	119.3 (2)
C2—C1—H1	119.9	C26—C25—C24	121.2 (2)
C6—C1—H1	119.9	C26—C25—H25	119.4
C3—C2—C1	119.7 (3)	C24—C25—H25	119.4
C3—C2—H2	120.2	C25—C26—C27	119.0 (2)
C1—C2—H2	120.2	C25—C26—H26	120.5
N1—C28—C29	111.61 (17)	C27—C26—H26	120.5
N1—C28—H28A	109.3	C18—C27—C26	122.2 (2)
C29—C28—H28A	109.3	C18—C27—H27	118.9
N1—C28—H28B	109.3	C26—C27—H27	118.9
C8—O2—N1—C28	−141.69 (16)	C6—C1—C2—C3	1.7 (4)
C8—O2—N1—C17	−22.12 (18)	C17—N1—C28—C29	167.93 (16)
C2—C3—C4—C5	−0.4 (4)	O2—N1—C28—C29	−78.14 (19)
C3—C4—C5—C6	1.3 (4)	N1—C28—C29—C34	123.4 (2)
C4—C5—C6—C1	−0.7 (3)	N1—C28—C29—C30	−58.8 (3)
C4—C5—C6—C7	179.2 (2)	C30—C29—C34—C33	0.9 (4)
C5—C6—C7—O1	10.7 (3)	C28—C29—C34—C33	178.7 (2)
C1—C6—C7—O1	−169.4 (2)	C29—C34—C33—C32	−0.1 (4)
C5—C6—C7—C8	−165.92 (19)	C34—C33—C32—C31	−0.9 (4)
C1—C6—C7—C8	14.0 (3)	C33—C32—C31—C30	1.0 (4)
N1—O2—C8—C9	12.1 (2)	C32—C31—C30—C29	−0.2 (4)
N1—O2—C8—C7	−171.20 (15)	C34—C29—C30—C31	−0.8 (4)
O1—C7—C8—C9	78.7 (3)	C28—C29—C30—C31	−178.7 (2)
C6—C7—C8—C9	−104.5 (3)	C8—C9—C10—O3	15.1 (3)
O1—C7—C8—O2	−97.4 (2)	C17—C9—C10—O3	−161.0 (2)
C6—C7—C8—O2	79.4 (2)	C8—C9—C10—C11	−166.10 (19)
O2—C8—C9—C10	−173.65 (18)	C17—C9—C10—C11	17.8 (3)
C7—C8—C9—C10	10.3 (3)	O3—C10—C11—C12	−140.3 (2)
O2—C8—C9—C17	3.2 (2)	C9—C10—C11—C12	40.9 (3)
C7—C8—C9—C17	−172.8 (2)	O3—C10—C11—C16	38.8 (3)
C28—N1—C17—C9	137.38 (16)	C9—C10—C11—C16	−140.0 (2)
O2—N1—C17—C9	22.96 (18)	C12—C11—C16—C15	−0.5 (3)
C28—N1—C17—C18	−101.25 (19)	C10—C11—C16—C15	−179.7 (2)
O2—N1—C17—C18	144.34 (15)	C11—C16—C15—C14	0.6 (4)
C8—C9—C17—N1	−16.8 (2)	C16—C15—C14—C13	0.1 (4)
C10—C9—C17—N1	159.83 (19)	C15—C14—C13—C12	−0.9 (4)
C8—C9—C17—C18	−133.25 (18)	C14—C13—C12—C11	1.0 (4)
C10—C9—C17—C18	43.4 (3)	C16—C11—C12—C13	−0.3 (3)
N1—C17—C18—C27	−64.1 (2)	C10—C11—C12—C13	178.8 (2)
C9—C17—C18—C27	48.5 (3)	C21—C22—C23—C24	0.6 (4)
N1—C17—C18—C19	115.07 (19)	C22—C23—C24—C25	178.7 (3)
C9—C17—C18—C19	−132.28 (19)	C22—C23—C24—C19	0.5 (4)
C27—C18—C19—C20	179.1 (2)	C20—C19—C24—C25	−179.5 (2)
C17—C18—C19—C20	−0.1 (3)	C18—C19—C24—C25	−0.2 (3)
C27—C18—C19—C24	−0.2 (3)	C20—C19—C24—C23	−1.3 (3)
C17—C18—C19—C24	−179.36 (18)	C18—C19—C24—C23	178.1 (2)
C18—C19—C20—C21	−178.4 (2)	C23—C24—C25—C26	−178.4 (2)
C24—C19—C20—C21	0.9 (3)	C19—C24—C25—C26	−0.2 (4)
C19—C20—C21—C22	0.2 (4)	C24—C25—C26—C27	0.9 (4)
C20—C21—C22—C23	−1.0 (4)	C19—C18—C27—C26	0.9 (3)
C5—C6—C1—C2	−0.8 (3)	C17—C18—C27—C26	−179.9 (2)
C7—C6—C1—C2	179.3 (2)	C25—C26—C27—C18	−1.3 (4)
C4—C3—C2—C1	−1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.93	2.60	3.392 (3)	144
C12—H12···O3ii	0.93	2.55	3.443 (3)	161
C13—H13···Cg1ii	0.93	2.63	3.523 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.60	3.392 (3)	144
C12—H12⋯O3ii	0.93	2.55	3.443 (3)	161
C13—H13⋯Cg1ii	0.93	2.63	3.523 (3)	161

Symmetry codes: (i) ; (ii) .