Crystal structure of obscurine: a natural product isolated from the stem bark of B. obscura.

The title compound, C24H31NO3 {systematic name: (E)-3-[(1R*,2S*,4aS*,8aR*)-2-(benzo[d][1,3]dioxol-5-yl)-1,2,4a,5,6,7,8,8a-octa-hydro-naphthalen-1-yl]-N-iso-butyl-acryl-amide}, is a natural product isolated from the stem bark of B. obscura. It is composed of an octa-hydro-naphthalene ring system substituted with an essentially planar benzodioxole ring system [r.m.s. deviation = 0.012 Å] and an extended iso-butyl-acryl-amide group. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains propagating along [100]. The chains are linked by pairs of C-H⋯O hydrogen bonds, involving inversion-related benzodioxole ring systems, forming ribbons lying parallel to (010). There are also C-H⋯π inter-actions present within the ribbons.

Related literature

For background to the Beilschmiedia genus, medicinal plants used in Cameroon, see: Chouna et al. (2009 ▸, 2010 ▸, 2011 ▸); Lenta et al. (2009 ▸, 2011 ▸). For related structures, see: Balawsnt et al. (1975 ▸).

Experimental

Crystal data

C24H31NO3

M = 381.50

Triclinic,

a = 5.14153 (16) Å

b = 9.7449 (3) Å

c = 20.4639 (5) Å

α = 98.839 (2)°

β = 90.946 (2)°

γ = 100.237 (3)°

V = 996.00 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.66 mm−1

T = 100 K

0.36 × 0.03 × 0.02 mm

Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer

Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013 ▸) T min = 0.798, T max = 1.000

13324 measured reflections

3892 independent reflections

3425 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.04

3892 reflections

377 parameters

All H-atom parameters refined

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015010567/su5126sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010567/su5126Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015010567/su5126fig1.tif

A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probabilityl evel.

Click here for additional data file.

b . DOI: 10.1107/S2056989015010567/su5126fig2.tif

A view along the b axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1404418

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

C24H31NO3	Z = 2
Mr = 381.50	F(000) = 412
Triclinic, P1	Dx = 1.272 Mg m−3
a = 5.14153 (16) Å	Cu Kα radiation, λ = 1.5418 Å
b = 9.7449 (3) Å	Cell parameters from 7209 reflections
c = 20.4639 (5) Å	θ = 4.7–76.2°
α = 98.839 (2)°	µ = 0.66 mm−1
β = 90.946 (2)°	T = 100 K
γ = 100.237 (3)°	Needle, clear colourless
V = 996.00 (5) Å3	0.36 × 0.03 × 0.02 mm

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	3892 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3425 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 5.3114 pixels mm-1	θmax = 72.1°, θmin = 4.4°
ω scans	h = −6→5
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013)	k = −11→12
Tmin = 0.798, Tmax = 1.000	l = −24→24
13324 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	All H-atom parameters refined
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0424P)2 + 0.3477P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3892 reflections	Δρmax = 0.24 e Å−3
377 parameters	Δρmin = −0.22 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
O3	0.99052 (16)	0.81354 (9)	0.86676 (4)	0.01947 (19)
O1	0.32116 (17)	0.81350 (9)	0.50886 (4)	0.0198 (2)
O2	0.26950 (17)	0.59230 (9)	0.54145 (4)	0.0211 (2)
N1	0.5440 (2)	0.79089 (11)	0.87047 (5)	0.0177 (2)
C7	0.7117 (2)	0.92262 (12)	0.58231 (6)	0.0155 (2)
C6	0.8900 (2)	0.89637 (12)	0.62993 (6)	0.0149 (2)
C14	0.9558 (2)	1.40385 (13)	0.81143 (6)	0.0189 (3)
C18	0.9906 (2)	1.00932 (12)	0.77808 (6)	0.0161 (2)
C19	0.7706 (2)	0.94294 (12)	0.80006 (6)	0.0172 (2)
C4	0.6528 (2)	0.65272 (13)	0.62212 (6)	0.0183 (2)
C16	1.2263 (2)	1.23586 (12)	0.74705 (6)	0.0152 (2)
C17	1.0186 (2)	1.10091 (12)	0.72506 (6)	0.0147 (2)
C2	0.5136 (2)	0.81316 (12)	0.55642 (6)	0.0154 (2)
C22	0.4536 (2)	0.77083 (13)	0.98764 (6)	0.0195 (3)
C8	1.1097 (2)	1.01511 (12)	0.66128 (6)	0.0150 (2)
C3	0.4823 (2)	0.68151 (12)	0.57583 (6)	0.0162 (2)
C5	0.8593 (2)	0.76299 (12)	0.64871 (6)	0.0174 (2)
C20	0.7803 (2)	0.84434 (12)	0.84886 (6)	0.0161 (2)
C21	0.5080 (2)	0.69546 (13)	0.91942 (6)	0.0182 (3)
C12	1.0346 (2)	1.41782 (12)	0.69190 (6)	0.0174 (2)
C13	1.0029 (3)	1.50233 (13)	0.75965 (6)	0.0192 (3)
C9	1.2170 (2)	1.11024 (13)	0.61238 (6)	0.0163 (2)
C11	1.2589 (2)	1.33271 (12)	0.69369 (6)	0.0153 (2)
C10	1.2835 (2)	1.24957 (13)	0.62661 (6)	0.0166 (2)
C23	0.3498 (3)	0.66495 (16)	1.03273 (7)	0.0293 (3)
C15	1.1801 (2)	1.32087 (13)	0.81431 (6)	0.0178 (2)
C1	0.1586 (2)	0.67567 (13)	0.49990 (6)	0.0186 (3)
C24	0.6991 (3)	0.87158 (15)	1.01892 (7)	0.0260 (3)
H16	1.402 (3)	1.2038 (15)	0.7515 (7)	0.016 (3)*
H11	1.426 (3)	1.4037 (15)	0.7059 (7)	0.015 (3)*
H17	0.844 (3)	1.1256 (15)	0.7138 (7)	0.015 (3)*
H21A	0.670 (3)	0.6545 (15)	0.9203 (7)	0.019 (4)*
H15A	1.345 (3)	1.3876 (15)	0.8301 (7)	0.017 (3)*
H4	0.633 (3)	0.5592 (17)	0.6353 (8)	0.026 (4)*
H9	1.238 (3)	1.0624 (15)	0.5679 (7)	0.018 (3)*
H5	0.986 (3)	0.7444 (16)	0.6806 (8)	0.023 (4)*
H12A	0.862 (3)	1.3498 (16)	0.6770 (7)	0.019 (4)*
H18	1.159 (3)	0.9934 (15)	0.7974 (7)	0.020 (4)*
H7	0.730 (3)	1.0156 (17)	0.5680 (7)	0.022 (4)*
H13A	1.169 (3)	1.5731 (16)	0.7739 (8)	0.023 (4)*
H14A	0.942 (3)	1.4596 (16)	0.8555 (8)	0.023 (4)*
H21B	0.354 (3)	0.6183 (16)	0.9026 (7)	0.022 (4)*
H1	0.399 (3)	0.8194 (16)	0.8567 (7)	0.022 (4)*
H1A	0.160 (3)	0.6301 (16)	0.4528 (8)	0.023 (4)*
H8	1.260 (3)	0.9720 (15)	0.6758 (7)	0.019 (4)*
H12B	1.068 (3)	1.4823 (16)	0.6573 (8)	0.021 (4)*
H14B	0.780 (3)	1.3357 (16)	0.7997 (8)	0.023 (4)*
H1B	−0.020 (3)	0.6828 (15)	0.5137 (7)	0.021 (4)*
H22	0.313 (3)	0.8255 (15)	0.9805 (7)	0.018 (3)*
H10	1.350 (3)	1.3042 (16)	0.5915 (8)	0.023 (4)*
H15B	1.146 (3)	1.2548 (17)	0.8489 (8)	0.025 (4)*
H13B	0.851 (3)	1.5540 (17)	0.7578 (8)	0.026 (4)*
H24A	0.841 (3)	0.8171 (19)	1.0287 (9)	0.036 (5)*
H24B	0.660 (3)	0.9237 (19)	1.0614 (9)	0.037 (5)*
H23A	0.483 (4)	0.609 (2)	1.0412 (9)	0.041 (5)*
H19	0.599 (3)	0.9535 (17)	0.7834 (8)	0.029 (4)*
H24C	0.775 (3)	0.9404 (19)	0.9890 (9)	0.036 (5)*
H23B	0.304 (4)	0.717 (2)	1.0772 (10)	0.043 (5)*
H23C	0.187 (4)	0.601 (2)	1.0128 (9)	0.043 (5)*

	U11	U22	U33	U12	U13	U23
O3	0.0158 (4)	0.0234 (4)	0.0221 (4)	0.0068 (3)	0.0012 (3)	0.0090 (3)
O1	0.0191 (4)	0.0170 (4)	0.0230 (4)	0.0005 (3)	−0.0059 (3)	0.0060 (3)
O2	0.0198 (4)	0.0153 (4)	0.0277 (5)	−0.0001 (3)	−0.0058 (4)	0.0058 (3)
N1	0.0154 (5)	0.0214 (5)	0.0187 (5)	0.0052 (4)	0.0010 (4)	0.0087 (4)
C7	0.0162 (6)	0.0148 (5)	0.0173 (6)	0.0050 (4)	0.0025 (4)	0.0048 (4)
C6	0.0153 (5)	0.0152 (5)	0.0152 (5)	0.0049 (4)	0.0034 (4)	0.0031 (4)
C14	0.0176 (6)	0.0216 (6)	0.0169 (6)	0.0042 (5)	0.0017 (5)	0.0007 (5)
C18	0.0175 (6)	0.0160 (5)	0.0157 (6)	0.0054 (4)	−0.0008 (4)	0.0029 (4)
C19	0.0161 (6)	0.0199 (6)	0.0176 (6)	0.0060 (5)	0.0000 (4)	0.0059 (4)
C4	0.0207 (6)	0.0143 (6)	0.0218 (6)	0.0047 (5)	0.0027 (5)	0.0069 (4)
C16	0.0134 (5)	0.0160 (5)	0.0171 (6)	0.0040 (4)	−0.0006 (4)	0.0038 (4)
C17	0.0134 (5)	0.0166 (6)	0.0154 (6)	0.0048 (4)	−0.0001 (4)	0.0041 (4)
C2	0.0153 (5)	0.0175 (6)	0.0150 (5)	0.0059 (4)	0.0018 (4)	0.0043 (4)
C22	0.0195 (6)	0.0213 (6)	0.0200 (6)	0.0066 (5)	0.0031 (5)	0.0070 (5)
C8	0.0138 (5)	0.0154 (5)	0.0170 (6)	0.0049 (4)	0.0006 (4)	0.0038 (4)
C3	0.0147 (5)	0.0146 (5)	0.0188 (6)	0.0020 (4)	0.0022 (4)	0.0019 (4)
C5	0.0187 (6)	0.0172 (6)	0.0185 (6)	0.0067 (5)	0.0006 (5)	0.0056 (4)
C20	0.0175 (6)	0.0158 (5)	0.0156 (6)	0.0043 (4)	0.0004 (4)	0.0027 (4)
C21	0.0194 (6)	0.0169 (6)	0.0193 (6)	0.0027 (5)	0.0008 (5)	0.0068 (4)
C12	0.0185 (6)	0.0172 (6)	0.0181 (6)	0.0060 (5)	−0.0004 (5)	0.0045 (4)
C13	0.0198 (6)	0.0172 (6)	0.0218 (6)	0.0070 (5)	0.0003 (5)	0.0022 (5)
C9	0.0141 (6)	0.0189 (6)	0.0164 (6)	0.0039 (4)	0.0017 (4)	0.0032 (4)
C11	0.0135 (5)	0.0154 (5)	0.0171 (6)	0.0025 (4)	0.0006 (4)	0.0033 (4)
C10	0.0145 (6)	0.0187 (6)	0.0176 (6)	0.0031 (4)	0.0021 (4)	0.0061 (4)
C23	0.0335 (8)	0.0297 (7)	0.0245 (7)	−0.0006 (6)	0.0050 (6)	0.0109 (6)
C15	0.0181 (6)	0.0186 (6)	0.0164 (6)	0.0026 (5)	−0.0014 (5)	0.0026 (4)
C1	0.0181 (6)	0.0167 (6)	0.0203 (6)	0.0012 (5)	−0.0015 (5)	0.0037 (4)
C24	0.0296 (7)	0.0235 (7)	0.0233 (7)	0.0028 (6)	−0.0010 (6)	0.0018 (5)

O3—C20	1.2363 (15)	C2—C3	1.3838 (16)
O1—C2	1.3772 (14)	C22—C21	1.5289 (17)
O1—C1	1.4341 (15)	C22—C23	1.5213 (18)
O2—C3	1.3772 (14)	C22—C24	1.5189 (18)
O2—C1	1.4386 (15)	C22—H22	0.991 (15)
N1—C20	1.3443 (16)	C8—C9	1.5120 (16)
N1—C21	1.4606 (15)	C8—H8	1.006 (15)
N1—H1	0.894 (16)	C5—H5	0.973 (16)
C7—C6	1.4093 (16)	C21—H21A	0.987 (16)
C7—C2	1.3705 (17)	C21—H21B	1.004 (16)
C7—H7	0.984 (16)	C12—C13	1.5269 (16)
C6—C8	1.5199 (16)	C12—C11	1.5384 (16)
C6—C5	1.3945 (16)	C12—H12A	1.020 (15)
C14—C13	1.5300 (17)	C12—H12B	1.014 (16)
C14—C15	1.5270 (17)	C13—H13A	1.007 (16)
C14—H14A	0.988 (16)	C13—H13B	1.003 (17)
C14—H14B	1.021 (16)	C9—C10	1.3250 (17)
C18—C19	1.3216 (18)	C9—H9	0.973 (15)
C18—C17	1.5007 (16)	C11—C10	1.5024 (16)
C18—H18	0.994 (15)	C11—H11	1.006 (15)
C19—C20	1.4944 (16)	C10—H10	0.988 (16)
C19—H19	0.970 (17)	C23—H23A	0.98 (2)
C4—C3	1.3732 (17)	C23—H23B	1.025 (19)
C4—C5	1.4050 (17)	C23—H23C	0.99 (2)
C4—H4	0.978 (16)	C15—H15A	0.990 (15)
C16—C17	1.5411 (16)	C15—H15B	1.025 (16)
C16—C11	1.5421 (16)	C1—H1A	0.997 (16)
C16—C15	1.5385 (16)	C1—H1B	0.978 (16)
C16—H16	1.016 (15)	C24—H24A	1.010 (18)
C17—C8	1.5640 (16)	C24—H24B	0.980 (18)
C17—H17	1.002 (14)	C24—H24C	1.010 (19)
C2—O1—C1	106.11 (9)	C4—C5—H5	118.5 (9)
C3—O2—C1	105.76 (9)	O3—C20—N1	123.23 (11)
C20—N1—C21	124.03 (10)	O3—C20—C19	121.94 (11)
C20—N1—H1	119.1 (10)	N1—C20—C19	114.83 (10)
C21—N1—H1	116.7 (10)	N1—C21—C22	112.10 (10)
C6—C7—H7	121.2 (9)	N1—C21—H21A	106.5 (9)
C2—C7—C6	117.32 (11)	N1—C21—H21B	106.8 (9)
C2—C7—H7	121.5 (9)	C22—C21—H21A	112.0 (9)
C7—C6—C8	119.41 (10)	C22—C21—H21B	110.2 (9)
C5—C6—C7	119.69 (11)	H21A—C21—H21B	109.0 (12)
C5—C6—C8	120.89 (10)	C13—C12—C11	111.67 (10)
C13—C14—H14A	109.7 (9)	C13—C12—H12A	109.2 (8)
C13—C14—H14B	108.9 (9)	C13—C12—H12B	110.8 (9)
C15—C14—C13	111.11 (10)	C11—C12—H12A	108.9 (8)
C15—C14—H14A	109.2 (9)	C11—C12—H12B	110.0 (9)
C15—C14—H14B	109.8 (9)	H12A—C12—H12B	106.0 (12)
H14A—C14—H14B	108.0 (12)	C14—C13—H13A	107.7 (9)
C19—C18—C17	128.07 (11)	C14—C13—H13B	109.8 (9)
C19—C18—H18	116.3 (9)	C12—C13—C14	110.15 (10)
C17—C18—H18	115.5 (9)	C12—C13—H13A	110.0 (9)
C18—C19—C20	120.79 (11)	C12—C13—H13B	110.4 (9)
C18—C19—H19	120.9 (10)	H13A—C13—H13B	108.8 (12)
C20—C19—H19	118.3 (10)	C8—C9—H9	115.5 (9)
C3—C4—C5	116.89 (11)	C10—C9—C8	124.58 (11)
C3—C4—H4	121.4 (9)	C10—C9—H9	119.9 (9)
C5—C4—H4	121.7 (9)	C16—C11—H11	107.0 (8)
C17—C16—C11	111.83 (9)	C12—C11—C16	112.87 (10)
C17—C16—H16	106.3 (8)	C12—C11—H11	106.4 (8)
C11—C16—H16	106.0 (8)	C10—C11—C16	110.93 (9)
C15—C16—C17	114.84 (10)	C10—C11—C12	110.45 (10)
C15—C16—C11	110.08 (9)	C10—C11—H11	109.0 (8)
C15—C16—H16	107.2 (8)	C9—C10—C11	123.82 (11)
C18—C17—C16	110.54 (9)	C9—C10—H10	119.5 (9)
C18—C17—C8	108.26 (9)	C11—C10—H10	116.7 (9)
C18—C17—H17	110.5 (8)	C22—C23—H23A	110.8 (11)
C16—C17—C8	109.30 (9)	C22—C23—H23B	110.0 (11)
C16—C17—H17	110.5 (8)	C22—C23—H23C	110.8 (11)
C8—C17—H17	107.6 (8)	H23A—C23—H23B	108.3 (15)
O1—C2—C3	109.80 (10)	H23A—C23—H23C	109.1 (16)
C7—C2—O1	127.48 (10)	H23B—C23—H23C	107.8 (15)
C7—C2—C3	122.71 (11)	C14—C15—C16	113.29 (10)
C21—C22—H22	106.4 (8)	C14—C15—H15A	108.9 (8)
C23—C22—C21	110.96 (11)	C14—C15—H15B	110.5 (9)
C23—C22—H22	108.2 (9)	C16—C15—H15A	108.7 (8)
C24—C22—C21	111.12 (11)	C16—C15—H15B	109.8 (9)
C24—C22—C23	110.86 (11)	H15A—C15—H15B	105.3 (12)
C24—C22—H22	109.2 (9)	O1—C1—O2	108.07 (9)
C6—C8—C17	111.47 (9)	O1—C1—H1A	109.5 (9)
C6—C8—H8	108.3 (8)	O1—C1—H1B	109.9 (9)
C17—C8—H8	106.4 (8)	O2—C1—H1A	108.7 (9)
C9—C8—C6	111.81 (9)	O2—C1—H1B	108.4 (9)
C9—C8—C17	111.61 (9)	H1A—C1—H1B	112.2 (12)
C9—C8—H8	107.0 (9)	C22—C24—H24A	110.3 (10)
O2—C3—C2	110.17 (10)	C22—C24—H24B	110.8 (11)
C4—C3—O2	128.50 (11)	C22—C24—H24C	112.1 (10)
C4—C3—C2	121.32 (11)	H24A—C24—H24B	106.4 (14)
C6—C5—C4	122.06 (11)	H24A—C24—H24C	107.5 (14)
C6—C5—H5	119.5 (9)	H24B—C24—H24C	109.5 (14)
O1—C2—C3—O2	0.14 (14)	C3—O2—C1—O1	2.82 (12)
O1—C2—C3—C4	178.82 (11)	C3—C4—C5—C6	0.73 (18)
C7—C6—C8—C17	89.64 (12)	C5—C6—C8—C17	−88.97 (13)
C7—C6—C8—C9	−36.07 (14)	C5—C6—C8—C9	145.33 (11)
C7—C6—C5—C4	−0.73 (18)	C5—C4—C3—O2	178.46 (11)
C7—C2—C3—O2	−179.54 (11)	C5—C4—C3—C2	0.05 (18)
C7—C2—C3—C4	−0.87 (19)	C20—N1—C21—C22	103.43 (13)
C6—C7—C2—O1	−178.77 (11)	C21—N1—C20—O3	2.70 (18)
C6—C7—C2—C3	0.86 (17)	C21—N1—C20—C19	−178.39 (10)
C6—C8—C9—C10	140.17 (12)	C12—C11—C10—C9	−109.46 (13)
C18—C19—C20—O3	−5.24 (18)	C13—C14—C15—C16	−55.96 (13)
C18—C19—C20—N1	175.83 (11)	C13—C12—C11—C16	54.57 (13)
C18—C17—C8—C6	70.41 (12)	C13—C12—C11—C10	179.40 (10)
C18—C17—C8—C9	−163.77 (10)	C11—C16—C17—C18	−179.76 (9)
C19—C18—C17—C16	135.66 (13)	C11—C16—C17—C8	61.18 (12)
C19—C18—C17—C8	−104.64 (14)	C11—C16—C15—C14	52.15 (13)
C16—C17—C8—C6	−169.12 (9)	C11—C12—C13—C14	−56.40 (13)
C16—C17—C8—C9	−43.30 (12)	C23—C22—C21—N1	165.79 (11)
C16—C11—C10—C9	16.46 (16)	C15—C14—C13—C12	56.89 (13)
C17—C18—C19—C20	173.97 (11)	C15—C16—C17—C18	−53.39 (13)
C17—C16—C11—C12	77.81 (12)	C15—C16—C17—C8	−172.45 (9)
C17—C16—C11—C10	−46.76 (13)	C15—C16—C11—C12	−51.11 (13)
C17—C16—C15—C14	−75.12 (13)	C15—C16—C11—C10	−175.68 (10)
C17—C8—C9—C10	14.53 (16)	C1—O1—C2—C7	−178.70 (12)
C2—O1—C1—O2	−2.74 (12)	C1—O1—C2—C3	1.63 (13)
C2—C7—C6—C8	−178.69 (10)	C1—O2—C3—C4	179.60 (12)
C2—C7—C6—C5	−0.07 (17)	C1—O2—C3—C2	−1.84 (13)
C8—C6—C5—C4	177.87 (11)	C24—C22—C21—N1	−70.39 (13)
C8—C9—C10—C11	−0.56 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.896 (16)	2.105 (16)	2.8938 (13)	146.3 (13)
C7—H7···O1ii	0.984 (16)	2.503 (16)	3.4264 (15)	156.3 (12)
C1—H1B···Cg2i	0.978 (16)	2.595 (15)	3.4578 (12)	147.4 (11)

Table 1

Hydrogen-bond geometry (, )

Cg2 is the centroid of the benzene ring C2C7.

DHA	DH	HA	D A	DHA
N1H1O3i	0.896(16)	2.105(16)	2.8938(13)	146.3(13)
C7H7O1ii	0.984(16)	2.503(16)	3.4264(15)	156.3(12)
C1H1B Cg2i	0.978(16)	2.595(15)	3.4578(12)	147.4(11)

Symmetry codes: (i) ; (ii) .