Methyl 4-(4-methoxy-phen-yl)-1,2,3,3a,4,4a,5,12c-octa-hydro-benzo[f]chromeno[3,4-b]pyrrolizine-4a-carboxyl-ate.

In the title compound, C(27)H(27)NO(4), both the pyrrolidine rings in the pyrrolizine ring system adopt envelope conformations, whereas the dihydro-pyran ring adopts a half-chair conformation. The methoxy-phenyl group is oriented at an angle of 53.72 (4)° with respect to the naphthalene ring system. Intra-molecular C-H⋯O hydrogen bonds are observed. The crystal structure is stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For the biological activity of pyrrolizine derivatives, see: Amal Raj et al. (2003 ▶); Atal (1978 ▶); Denny (2001 ▶); Suzuki et al. (1994 ▶). For a related structure, see: Ramesh et al. (2007 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C27H27NO4

M = 429.50

Triclinic,

a = 8.7484 (4) Å

b = 11.4284 (5) Å

c = 11.4444 (6) Å

α = 104.127 (2)°

β = 91.824 (3)°

γ = 101.555 (2)°

V = 1083.19 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.974, T max = 0.983

22194 measured reflections

4310 independent reflections

2976 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.131

S = 1.03

4310 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.16 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027639/bt5001sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027639/bt5001Isup2.hkl

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

C27H27NO4	Z = 2
Mr = 429.50	F(000) = 456
Triclinic, P1	Dx = 1.317 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7484 (4) Å	Cell parameters from 6981 reflections
b = 11.4284 (5) Å	θ = 2.3–26.0°
c = 11.4444 (6) Å	µ = 0.09 mm−1
α = 104.127 (2)°	T = 293 K
β = 91.824 (3)°	Prism, yellow
γ = 101.555 (2)°	0.30 × 0.25 × 0.20 mm
V = 1083.19 (9) Å3

Bruker Kappa APEXII area-detector diffractometer	4310 independent reflections
Radiation source: fine-focus sealed tube	2976 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω and φ scans	θmax = 26.2°, θmin = 2.3°
Absorption correction: multi-scan (Blessing, 1995)	h = −10→10
Tmin = 0.974, Tmax = 0.983	k = −14→14
22194 measured reflections	l = −14→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0551P)2 + 0.3082P] where P = (Fo2 + 2Fc2)/3
4310 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.16 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
C1	0.3428 (2)	0.57705 (16)	0.31111 (15)	0.0445 (4)
H1	0.2866	0.5752	0.3836	0.053*
C2	0.26413 (19)	0.64642 (15)	0.23992 (15)	0.0431 (4)
C3	0.2290 (2)	0.76283 (16)	0.29772 (16)	0.0464 (4)
C4	0.2730 (2)	0.82056 (17)	0.42105 (17)	0.0548 (5)
H4	0.3284	0.7834	0.4669	0.066*
C5	0.2352 (3)	0.93069 (19)	0.4741 (2)	0.0657 (6)
H5	0.2634	0.9668	0.5559	0.079*
C6	0.1550 (3)	0.9895 (2)	0.4072 (2)	0.0716 (6)
H6	0.1308	1.0648	0.4441	0.086*
C7	0.1123 (2)	0.93691 (19)	0.2880 (2)	0.0661 (6)
H7	0.0594	0.9770	0.2437	0.079*
C8	0.1466 (2)	0.82244 (17)	0.23017 (18)	0.0521 (5)
C9	0.0967 (2)	0.76322 (19)	0.10731 (19)	0.0582 (5)
H9	0.0404	0.8008	0.0627	0.070*
C10	0.1295 (2)	0.65353 (18)	0.05396 (17)	0.0538 (5)
H10	0.0945	0.6155	−0.0266	0.065*
C11	0.2164 (2)	0.59630 (16)	0.11972 (16)	0.0462 (4)
C12	0.3576 (2)	0.43780 (17)	0.10894 (15)	0.0479 (4)
H12A	0.4615	0.4851	0.1043	0.057*
H12B	0.3522	0.3530	0.0643	0.057*
C13	0.3321 (2)	0.44172 (15)	0.23988 (14)	0.0425 (4)
C14	0.4659 (2)	0.40757 (17)	0.30803 (15)	0.0477 (4)
H14	0.4235	0.3968	0.3839	0.057*
C15	0.5928 (2)	0.52759 (18)	0.34653 (17)	0.0546 (5)
H15	0.6344	0.5349	0.4291	0.066*
C16	0.7312 (2)	0.5558 (2)	0.2738 (2)	0.0688 (6)
H16A	0.8211	0.5289	0.3014	0.083*
H16B	0.7050	0.5168	0.1882	0.083*
C17	0.7619 (3)	0.6949 (2)	0.2989 (3)	0.0855 (8)
H17A	0.8176	0.7342	0.3778	0.103*
H17B	0.8215	0.7239	0.2376	0.103*
C18	0.5994 (3)	0.7186 (2)	0.2943 (3)	0.0773 (7)
H18A	0.5985	0.8025	0.3386	0.093*
H18B	0.5579	0.7056	0.2114	0.093*
C19	0.5143 (2)	0.28744 (16)	0.25383 (15)	0.0454 (4)
C20	0.5936 (2)	0.26369 (18)	0.15102 (17)	0.0542 (5)
H20	0.6166	0.3239	0.1085	0.065*
C21	0.6397 (2)	0.15321 (18)	0.10964 (18)	0.0570 (5)
H21	0.6940	0.1404	0.0407	0.068*
C22	0.6059 (2)	0.06275 (17)	0.16960 (19)	0.0562 (5)
C23	0.5197 (3)	0.0811 (2)	0.2683 (2)	0.0646 (6)
H23	0.4905	0.0184	0.3071	0.077*
C24	0.4769 (2)	0.19191 (19)	0.30954 (18)	0.0570 (5)
H24	0.4206	0.2034	0.3775	0.068*
C25	0.7526 (3)	−0.0636 (2)	0.0442 (2)	0.0881 (8)
H25A	0.7767	−0.1440	0.0309	0.132*
H25B	0.8476	−0.0015	0.0663	0.132*
H25C	0.7019	−0.0565	−0.0286	0.132*
C26	0.1780 (2)	0.35504 (17)	0.24530 (17)	0.0488 (4)
C27	−0.0206 (3)	0.3004 (3)	0.3694 (3)	0.0902 (8)
H27A	−0.0501	0.3283	0.4498	0.135*
H27B	−0.0039	0.2179	0.3572	0.135*
H27C	−0.1026	0.3010	0.3119	0.135*
N1	0.50894 (18)	0.62899 (14)	0.35141 (14)	0.0554 (4)
O1	0.24421 (15)	0.48642 (12)	0.05440 (10)	0.0547 (3)
O2	0.12217 (17)	0.38163 (14)	0.35295 (13)	0.0697 (4)
O3	0.11479 (19)	0.27038 (15)	0.16475 (14)	0.0831 (5)
O4	0.6519 (2)	−0.04732 (14)	0.13839 (16)	0.0803 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0434 (10)	0.0490 (10)	0.0396 (9)	0.0085 (8)	0.0057 (7)	0.0093 (8)
C2	0.0397 (10)	0.0457 (10)	0.0450 (9)	0.0063 (7)	0.0072 (7)	0.0155 (8)
C3	0.0380 (10)	0.0458 (10)	0.0550 (11)	0.0044 (7)	0.0110 (8)	0.0152 (8)
C4	0.0537 (12)	0.0510 (11)	0.0574 (11)	0.0113 (9)	0.0083 (9)	0.0091 (9)
C5	0.0664 (14)	0.0559 (12)	0.0688 (13)	0.0131 (10)	0.0135 (11)	0.0036 (10)
C6	0.0648 (14)	0.0525 (12)	0.0970 (18)	0.0187 (10)	0.0201 (12)	0.0112 (12)
C7	0.0532 (13)	0.0577 (12)	0.0948 (17)	0.0188 (10)	0.0131 (11)	0.0267 (12)
C8	0.0374 (10)	0.0532 (11)	0.0698 (13)	0.0089 (8)	0.0118 (9)	0.0232 (10)
C9	0.0466 (11)	0.0692 (13)	0.0683 (13)	0.0148 (9)	0.0059 (9)	0.0331 (11)
C10	0.0493 (11)	0.0649 (12)	0.0495 (10)	0.0084 (9)	0.0026 (8)	0.0223 (9)
C11	0.0451 (10)	0.0483 (10)	0.0458 (10)	0.0061 (8)	0.0076 (8)	0.0160 (8)
C12	0.0557 (11)	0.0494 (10)	0.0404 (9)	0.0138 (8)	0.0082 (8)	0.0124 (8)
C13	0.0447 (10)	0.0469 (10)	0.0368 (9)	0.0104 (8)	0.0062 (7)	0.0117 (7)
C14	0.0511 (11)	0.0567 (11)	0.0381 (9)	0.0156 (8)	0.0078 (8)	0.0135 (8)
C15	0.0521 (11)	0.0636 (12)	0.0447 (10)	0.0167 (9)	−0.0008 (8)	0.0046 (9)
C16	0.0547 (13)	0.0684 (14)	0.0753 (14)	0.0125 (10)	0.0114 (10)	0.0036 (11)
C17	0.0533 (14)	0.0721 (15)	0.118 (2)	−0.0002 (11)	0.0134 (13)	0.0102 (14)
C18	0.0553 (14)	0.0623 (13)	0.1104 (19)	0.0004 (10)	0.0123 (12)	0.0241 (13)
C19	0.0459 (10)	0.0520 (10)	0.0412 (9)	0.0129 (8)	0.0048 (8)	0.0154 (8)
C20	0.0625 (12)	0.0548 (11)	0.0531 (11)	0.0183 (9)	0.0173 (9)	0.0220 (9)
C21	0.0614 (13)	0.0594 (12)	0.0546 (11)	0.0225 (10)	0.0146 (9)	0.0140 (10)
C22	0.0542 (12)	0.0509 (11)	0.0652 (12)	0.0184 (9)	−0.0026 (10)	0.0135 (10)
C23	0.0704 (14)	0.0618 (13)	0.0744 (14)	0.0199 (11)	0.0102 (11)	0.0362 (11)
C24	0.0590 (12)	0.0685 (13)	0.0535 (11)	0.0206 (10)	0.0137 (9)	0.0273 (10)
C25	0.0778 (17)	0.0780 (16)	0.105 (2)	0.0431 (13)	−0.0010 (14)	−0.0032 (14)
C26	0.0499 (11)	0.0510 (11)	0.0488 (10)	0.0124 (9)	0.0060 (8)	0.0175 (9)
C27	0.0667 (16)	0.1030 (19)	0.111 (2)	0.0060 (14)	0.0337 (14)	0.0537 (17)
N1	0.0495 (9)	0.0541 (9)	0.0567 (9)	0.0097 (7)	0.0010 (7)	0.0046 (8)
O1	0.0679 (9)	0.0583 (8)	0.0383 (6)	0.0175 (6)	−0.0014 (6)	0.0105 (6)
O2	0.0631 (9)	0.0799 (10)	0.0636 (9)	0.0022 (7)	0.0239 (7)	0.0222 (8)
O3	0.0781 (11)	0.0744 (10)	0.0743 (10)	−0.0156 (8)	0.0073 (8)	0.0027 (9)
O4	0.0883 (12)	0.0606 (9)	0.1009 (12)	0.0360 (8)	0.0093 (9)	0.0210 (9)

C1—N1	1.468 (2)	C15—C16	1.517 (3)
C1—C2	1.505 (2)	C15—H15	0.9800
C1—C13	1.545 (2)	C16—C17	1.511 (3)
C1—H1	0.9800	C16—H16A	0.9700
C2—C11	1.370 (2)	C16—H16B	0.9700
C2—C3	1.432 (2)	C17—C18	1.501 (3)
C3—C4	1.409 (3)	C17—H17A	0.9700
C3—C8	1.414 (3)	C17—H17B	0.9700
C4—C5	1.367 (3)	C18—N1	1.462 (3)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.391 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—C20	1.383 (2)
C6—C7	1.355 (3)	C19—C24	1.384 (3)
C6—H6	0.9300	C20—C21	1.380 (2)
C7—C8	1.410 (3)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.365 (3)
C8—C9	1.415 (3)	C21—H21	0.9300
C9—C10	1.344 (3)	C22—O4	1.366 (2)
C9—H9	0.9300	C22—C23	1.375 (3)
C10—C11	1.405 (3)	C23—C24	1.369 (3)
C10—H10	0.9300	C23—H23	0.9300
C11—O1	1.368 (2)	C24—H24	0.9300
C12—O1	1.426 (2)	C25—O4	1.415 (3)
C12—C13	1.513 (2)	C25—H25A	0.9600
C12—H12A	0.9700	C25—H25B	0.9600
C12—H12B	0.9700	C25—H25C	0.9600
C13—C26	1.518 (3)	C26—O3	1.187 (2)
C13—C14	1.550 (2)	C26—O2	1.328 (2)
C14—C19	1.511 (2)	C27—O2	1.447 (3)
C14—C15	1.540 (3)	C27—H27A	0.9600
C14—H14	0.9800	C27—H27B	0.9600
C15—N1	1.482 (2)	C27—H27C	0.9600
N1—C1—C2	116.27 (15)	C14—C15—H15	107.5
N1—C1—C13	106.30 (14)	C17—C16—C15	102.37 (17)
C2—C1—C13	111.88 (14)	C17—C16—H16A	111.3
N1—C1—H1	107.3	C15—C16—H16A	111.3
C2—C1—H1	107.3	C17—C16—H16B	111.3
C13—C1—H1	107.3	C15—C16—H16B	111.3
C11—C2—C3	118.40 (16)	H16A—C16—H16B	109.2
C11—C2—C1	120.71 (15)	C18—C17—C16	102.44 (18)
C3—C2—C1	120.79 (15)	C18—C17—H17A	111.3
C4—C3—C8	118.32 (17)	C16—C17—H17A	111.3
C4—C3—C2	122.10 (17)	C18—C17—H17B	111.3
C8—C3—C2	119.58 (17)	C16—C17—H17B	111.3
C5—C4—C3	120.65 (19)	H17A—C17—H17B	109.2
C5—C4—H4	119.7	N1—C18—C17	104.1 (2)
C3—C4—H4	119.7	N1—C18—H18A	110.9
C4—C5—C6	120.9 (2)	C17—C18—H18A	110.9
C4—C5—H5	119.6	N1—C18—H18B	110.9
C6—C5—H5	119.6	C17—C18—H18B	110.9
C7—C6—C5	119.9 (2)	H18A—C18—H18B	109.0
C7—C6—H6	120.1	C20—C19—C24	116.18 (17)
C5—C6—H6	120.1	C20—C19—C14	125.22 (16)
C6—C7—C8	121.1 (2)	C24—C19—C14	118.60 (15)
C6—C7—H7	119.4	C21—C20—C19	121.92 (18)
C8—C7—H7	119.4	C21—C20—H20	119.0
C7—C8—C3	119.12 (19)	C19—C20—H20	119.0
C7—C8—C9	122.01 (19)	C22—C21—C20	120.22 (18)
C3—C8—C9	118.83 (17)	C22—C21—H21	119.9
C10—C9—C8	121.16 (18)	C20—C21—H21	119.9
C10—C9—H9	119.4	C21—C22—O4	124.41 (19)
C8—C9—H9	119.4	C21—C22—C23	119.14 (18)
C9—C10—C11	120.08 (18)	O4—C22—C23	116.45 (19)
C9—C10—H10	120.0	C24—C23—C22	119.95 (19)
C11—C10—H10	120.0	C24—C23—H23	120.0
O1—C11—C2	123.82 (16)	C22—C23—H23	120.0
O1—C11—C10	114.28 (15)	C23—C24—C19	122.43 (18)
C2—C11—C10	121.87 (17)	C23—C24—H24	118.8
O1—C12—C13	112.03 (14)	C19—C24—H24	118.8
O1—C12—H12A	109.2	O4—C25—H25A	109.5
C13—C12—H12A	109.2	O4—C25—H25B	109.5
O1—C12—H12B	109.2	H25A—C25—H25B	109.5
C13—C12—H12B	109.2	O4—C25—H25C	109.5
H12A—C12—H12B	107.9	H25A—C25—H25C	109.5
C12—C13—C26	108.88 (15)	H25B—C25—H25C	109.5
C12—C13—C1	109.10 (14)	O3—C26—O2	122.82 (18)
C26—C13—C1	114.22 (14)	O3—C26—C13	124.82 (17)
C12—C13—C14	113.80 (14)	O2—C26—C13	112.33 (16)
C26—C13—C14	109.63 (14)	O2—C27—H27A	109.5
C1—C13—C14	101.16 (13)	O2—C27—H27B	109.5
C19—C14—C15	118.94 (15)	H27A—C27—H27B	109.5
C19—C14—C13	118.49 (14)	O2—C27—H27C	109.5
C15—C14—C13	104.79 (14)	H27A—C27—H27C	109.5
C19—C14—H14	104.3	H27B—C27—H27C	109.5
C15—C14—H14	104.3	C18—N1—C1	119.67 (16)
C13—C14—H14	104.3	C18—N1—C15	108.60 (15)
N1—C15—C16	105.10 (16)	C1—N1—C15	109.70 (14)
N1—C15—C14	105.46 (14)	C11—O1—C12	116.10 (13)
C16—C15—C14	122.97 (16)	C26—O2—C27	116.63 (18)
N1—C15—H15	107.5	C22—O4—C25	117.36 (18)
C16—C15—H15	107.5
N1—C1—C2—C11	111.83 (18)	C13—C14—C15—N1	24.27 (17)
C13—C1—C2—C11	−10.5 (2)	C19—C14—C15—C16	39.4 (3)
N1—C1—C2—C3	−72.0 (2)	C13—C14—C15—C16	−95.8 (2)
C13—C1—C2—C3	165.67 (14)	N1—C15—C16—C17	28.2 (2)
C11—C2—C3—C4	179.67 (17)	C14—C15—C16—C17	148.5 (2)
C1—C2—C3—C4	3.4 (3)	C15—C16—C17—C18	−40.8 (2)
C11—C2—C3—C8	0.1 (2)	C16—C17—C18—N1	38.3 (3)
C1—C2—C3—C8	−176.21 (16)	C15—C14—C19—C20	−58.3 (2)
C8—C3—C4—C5	0.8 (3)	C13—C14—C19—C20	70.9 (2)
C2—C3—C4—C5	−178.80 (17)	C15—C14—C19—C24	121.98 (19)
C3—C4—C5—C6	−1.2 (3)	C13—C14—C19—C24	−108.8 (2)
C4—C5—C6—C7	0.6 (3)	C24—C19—C20—C21	−3.1 (3)
C5—C6—C7—C8	0.5 (3)	C14—C19—C20—C21	177.25 (18)
C6—C7—C8—C3	−0.9 (3)	C19—C20—C21—C22	0.7 (3)
C6—C7—C8—C9	177.03 (19)	C20—C21—C22—O4	−177.28 (18)
C4—C3—C8—C7	0.2 (3)	C20—C21—C22—C23	2.8 (3)
C2—C3—C8—C7	179.84 (16)	C21—C22—C23—C24	−3.8 (3)
C4—C3—C8—C9	−177.72 (17)	O4—C22—C23—C24	176.24 (19)
C2—C3—C8—C9	1.9 (2)	C22—C23—C24—C19	1.4 (3)
C7—C8—C9—C10	−179.41 (18)	C20—C19—C24—C23	2.0 (3)
C3—C8—C9—C10	−1.5 (3)	C14—C19—C24—C23	−178.29 (18)
C8—C9—C10—C11	−0.9 (3)	C12—C13—C26—O3	22.6 (3)
C3—C2—C11—O1	179.38 (15)	C1—C13—C26—O3	144.8 (2)
C1—C2—C11—O1	−4.3 (3)	C14—C13—C26—O3	−102.5 (2)
C3—C2—C11—C10	−2.5 (3)	C12—C13—C26—O2	−159.46 (15)
C1—C2—C11—C10	173.79 (16)	C1—C13—C26—O2	−37.2 (2)
C9—C10—C11—O1	−178.78 (16)	C14—C13—C26—O2	75.45 (18)
C9—C10—C11—C2	3.0 (3)	C17—C18—N1—C1	−147.84 (18)
O1—C12—C13—C26	65.72 (19)	C17—C18—N1—C15	−20.9 (2)
O1—C12—C13—C1	−59.54 (19)	C2—C1—N1—C18	−17.6 (2)
O1—C12—C13—C14	−171.67 (14)	C13—C1—N1—C18	107.66 (18)
N1—C1—C13—C12	−87.59 (17)	C2—C1—N1—C15	−144.03 (15)
C2—C1—C13—C12	40.32 (19)	C13—C1—N1—C15	−18.77 (18)
N1—C1—C13—C26	150.32 (15)	C16—C15—N1—C18	−4.7 (2)
C2—C1—C13—C26	−81.77 (18)	C14—C15—N1—C18	−136.01 (17)
N1—C1—C13—C14	32.66 (17)	C16—C15—N1—C1	127.72 (16)
C2—C1—C13—C14	160.56 (14)	C14—C15—N1—C1	−3.54 (19)
C12—C13—C14—C19	−53.0 (2)	C2—C11—O1—C12	−14.2 (2)
C26—C13—C14—C19	69.19 (19)	C10—C11—O1—C12	167.62 (15)
C1—C13—C14—C19	−169.85 (14)	C13—C12—O1—C11	46.8 (2)
C12—C13—C14—C15	82.45 (17)	O3—C26—O2—C27	1.0 (3)
C26—C13—C14—C15	−155.35 (14)	C13—C26—O2—C27	−176.96 (17)
C1—C13—C14—C15	−34.40 (16)	C21—C22—O4—C25	5.7 (3)
C19—C14—C15—N1	159.48 (15)	C23—C22—O4—C25	−174.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2	0.98	2.32	2.792 (2)	108
C23—H23···Cg1i	0.93	2.92	3.633 (3)	135
C25—H25C···Cg2ii	0.96	2.90	3.715 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2	0.98	2.32	2.792 (2)	108
C23—H23⋯Cg1i	0.93	2.92	3.633 (3)	135
C25—H25C⋯Cg2ii	0.96	2.90	3.715 (3)	143

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C3–C8 ring and Cg2 is the centroid of the C19–C24 ring.