(4R,7S)-2-Amino-4-(3,4-dimeth-oxy-phen-yl)-5-oxo-7-phenyl-5,6,7,8-tetra-hydro-4H-chromene-3-carbonitrile monohydrate.

The title compound, C(24)H(22)N(2)O(4)·H(2)O, was obtained by the reaction of 3,4-dimeth-oxy-benzaldehyde, malononitrile and 5-phenyl-cyclo-hexane-1,3-dione. The cyclo-hexyl and pyran rings show half-boat and V-shaped conformations, respectively. The dihedral angle between the phenyl and benzene ring planes is 30.67 (9)°. The organic mol-ecules are packed in a two-dimensional network parallel to the bc plane stabilized by inter-molecular N-H⋯N and N-H⋯O hydrogen bonds.

Related literature

For background to 4-aryl-4H-chromene and its derivatives, see: Kemnitzer et al. (2004 ▶, 2005 ▶, 2007 ▶, 2008 ▶); Gourdeau et al. (2004 ▶); Foroumadi et al. (2007 ▶); Mahdavi et al. (2011 ▶). For the synthesis of 4-aryl-4H-chromene and its derivatives, see: Wen et al. (2006 ▶); Kidwai et al. (2005 ▶); Yadav et al. (2009 ▶); Li et al. (2008 ▶). For related compounds, see: Gourdeau et al. (2004 ▶); Foroumadi et al. (2007 ▶).

Experimental

Crystal data

C24H22N2O4·H2O

M = 420.45

Monoclinic,

a = 29.008 (16) Å

b = 16.146 (8) Å

c = 12.068 (6) Å

β = 110.486 (9)°

V = 5295 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 291 K

0.38 × 0.32 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.972, T max = 0.982

14295 measured reflections

5212 independent reflections

3266 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.132

S = 1.00

5212 reflections

305 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811056285/bx2390sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056285/bx2390Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811056285/bx2390Isup3.cml

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

C24H22N2O4·H2O	F(000) = 1776
Mr = 420.45	Dx = 1.055 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2449 reflections
a = 29.008 (16) Å	θ = 2.5–21.9°
b = 16.146 (8) Å	µ = 0.07 mm−1
c = 12.068 (6) Å	T = 291 K
β = 110.486 (9)°	Block, colorless
V = 5295 (5) Å3	0.38 × 0.32 × 0.24 mm
Z = 8

Bruker SMART APEX CCD diffractometer	5212 independent reflections
Radiation source: sealed tube	3266 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −35→28
Tmin = 0.972, Tmax = 0.982	k = −16→19
14295 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0629P)2] where P = (Fo2 + 2Fc2)/3
5212 reflections	(Δ/σ)max < 0.001
305 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)18.7999 (0.0253) x + 6.0274 (0.0140) y + 4.7668 (0.0109) z = 7.5153 (0.0082)* 0.0227 (0.0013) C4 * -0.0288 (0.0015) C5 * 0.0178 (0.0011) C6 * -0.0068 (0.0011) C8 * -0.0049 (0.0014) C9Rms deviation of fitted atoms = 0.0186- 0.7360 (0.0244) x + 15.4410 (0.0094) y - 3.1844 (0.0102) z = 8.2455 (0.0098)Angle to previous plane (with approximate e.s.d.) = 81.53 (8)* 0.0000 (0.0014) C10 * 0.0000 (0.0014) C11 * 0.0000 (0.0015) C12 * 0.0000 (0.0015) C13 * 0.0000 (0.0015) C14 * 0.0000 (0.0015) C15Rms deviation of fitted atoms = 0.00006.5144 (0.0251) x + 11.2780 (0.0120) y - 8.6296 (0.0089) z = 7.8493 (0.0106)Angle to previous plane (with approximate e.s.d.) = 30.67 (9)* 0.0000 (0.0015) C18 * 0.0000 (0.0015) C19 * 0.0000 (0.0015) C20 * 0.0000 (0.0015) C21 * 0.0000 (0.0015) C22 * 0.0000 (0.0016) C23Rms deviation of fitted atoms = 0.0000

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	Occ. (<1)
C1	0.21676 (7)	0.42190 (12)	0.10641 (17)	0.0398 (4)
C2	0.23258 (7)	0.43944 (11)	0.01610 (16)	0.0384 (4)
C3	0.23849 (7)	0.52781 (11)	−0.02193 (17)	0.0380 (4)
H3A	0.2253	0.5299	−0.1086	0.046*
C4	0.20768 (7)	0.58404 (12)	0.02376 (16)	0.0363 (4)
C5	0.19297 (7)	0.66544 (12)	−0.03195 (18)	0.0426 (5)
C6	0.16490 (8)	0.72255 (13)	0.01636 (17)	0.0467 (5)
H6A	0.1315	0.7258	−0.0399	0.056*
H6B	0.1793	0.7773	0.0216	0.056*
C7	0.16233 (7)	0.70135 (12)	0.13490 (18)	0.0432 (5)
H7A	0.1946	0.7191	0.1892	0.052*
C8	0.16176 (8)	0.61261 (13)	0.16256 (19)	0.0480 (5)
H8A	0.1280	0.5929	0.1333	0.058*
H8B	0.1744	0.6055	0.2478	0.058*
C9	0.19168 (7)	0.56133 (12)	0.10981 (16)	0.0378 (4)
C10	0.29243 (7)	0.55177 (11)	0.01855 (18)	0.0396 (4)
C11	0.31728 (7)	0.57684 (13)	0.13438 (17)	0.0443 (5)
H11A	0.3000	0.5865	0.1850	0.053*
C12	0.36802 (8)	0.58754 (13)	0.17454 (19)	0.0473 (5)
C13	0.39391 (8)	0.57317 (13)	0.0989 (2)	0.0505 (5)
C14	0.36906 (8)	0.54809 (14)	−0.0170 (2)	0.0544 (6)
H14A	0.3864	0.5385	−0.0676	0.065*
C15	0.31832 (8)	0.53739 (13)	−0.05712 (19)	0.0484 (5)
H15A	0.3017	0.5206	−0.1346	0.058*
C16	0.37141 (7)	0.65844 (12)	0.35114 (17)	0.0418 (5)
H16A	0.3953	0.6784	0.4234	0.063*
H16B	0.3489	0.6218	0.3691	0.063*
H16C	0.3536	0.7044	0.3056	0.063*
C17	0.47282 (7)	0.55420 (13)	0.08253 (18)	0.0442 (5)
H17A	0.5070	0.5570	0.1308	0.066*
H17B	0.4667	0.5891	0.0145	0.066*
H17C	0.4643	0.4981	0.0574	0.066*
C18	0.12798 (8)	0.75372 (13)	0.17207 (18)	0.0465 (5)
C19	0.15023 (8)	0.80989 (13)	0.26227 (18)	0.0444 (5)
H19A	0.1843	0.8140	0.2934	0.053*
C20	0.12148 (7)	0.85989 (12)	0.30591 (19)	0.0453 (5)
H20A	0.1364	0.8975	0.3663	0.054*
C21	0.07048 (7)	0.85373 (12)	0.25936 (17)	0.0425 (5)
H21C	0.0512	0.8872	0.2886	0.051*
C22	0.04824 (8)	0.79756 (12)	0.16916 (18)	0.0448 (5)
H22A	0.0141	0.7934	0.1380	0.054*
C23	0.07698 (7)	0.74756 (12)	0.12551 (18)	0.0459 (5)
H23A	0.0621	0.7100	0.0652	0.055*
C24	0.24929 (7)	0.37408 (12)	−0.03676 (18)	0.0424 (5)
N1	0.21337 (6)	0.34897 (10)	0.15312 (15)	0.0438 (4)
H1A	0.2221	0.3049	0.1256	0.053*
H1B	0.2025	0.3455	0.2108	0.053*
N2	0.26326 (6)	0.32244 (10)	−0.08241 (14)	0.0418 (4)
O1	0.20008 (5)	0.48364 (8)	0.16179 (11)	0.0403 (3)
O2	0.20311 (5)	0.68522 (9)	−0.11773 (12)	0.0473 (4)
O3	0.39552 (5)	0.61541 (9)	0.28562 (13)	0.0495 (4)
O4	0.44392 (5)	0.58132 (9)	0.14876 (12)	0.0461 (4)
O1W	1.0000	0.7117 (3)	0.7500	0.0600 (13)	0.50
H1X	1.0148	0.6920	0.7062	0.072*	0.25
H1Y	0.9771	0.7439	0.7095	0.072*	0.25
O2W	0.0778 (2)	0.4029 (3)	0.9183 (5)	0.0473 (14)	0.25
H2X	0.0654	0.3666	0.8652	0.057*	0.25
H2Y	0.1088	0.4040	0.9360	0.057*	0.25
O3W	0.0547 (2)	0.5322 (3)	0.9458 (5)	0.0514 (15)	0.25
H3X	0.0710	0.5671	0.9215	0.062*	0.25
H3Y	0.0242	0.5384	0.9073	0.062*	0.25
O6W	0.0707 (2)	0.4226 (4)	0.1806 (5)	0.0497 (14)	0.25
H6X	0.0635	0.3823	0.1323	0.060*	0.25
H6Y	0.0502	0.4617	0.1534	0.060*	0.25

	U11	U22	U33	U12	U13	U23
C1	0.0460 (10)	0.0365 (10)	0.0360 (10)	0.0014 (8)	0.0133 (9)	−0.0021 (8)
C2	0.0469 (10)	0.0295 (10)	0.0356 (10)	0.0015 (8)	0.0104 (8)	−0.0028 (8)
C3	0.0469 (11)	0.0321 (10)	0.0340 (10)	0.0026 (8)	0.0128 (8)	−0.0016 (7)
C4	0.0419 (10)	0.0344 (10)	0.0347 (9)	0.0029 (7)	0.0160 (8)	−0.0021 (7)
C5	0.0405 (11)	0.0430 (11)	0.0445 (11)	0.0090 (8)	0.0151 (8)	0.0079 (9)
C6	0.0482 (11)	0.0503 (12)	0.0446 (11)	0.0153 (10)	0.0201 (9)	0.0186 (10)
C7	0.0422 (11)	0.0415 (11)	0.0448 (11)	0.0168 (8)	0.0139 (8)	0.0143 (9)
C8	0.0563 (12)	0.0423 (11)	0.0430 (11)	0.0111 (10)	0.0143 (10)	−0.0020 (9)
C9	0.0457 (10)	0.0342 (10)	0.0344 (10)	0.0055 (8)	0.0150 (8)	0.0038 (8)
C10	0.0444 (10)	0.0297 (9)	0.0435 (11)	0.0058 (8)	0.0137 (8)	0.0020 (8)
C11	0.0492 (12)	0.0476 (11)	0.0361 (10)	0.0030 (9)	0.0148 (9)	0.0001 (9)
C12	0.0493 (12)	0.0464 (12)	0.0418 (11)	0.0014 (9)	0.0103 (9)	−0.0018 (9)
C13	0.0478 (12)	0.0436 (12)	0.0585 (13)	0.0009 (9)	0.0165 (10)	0.0011 (10)
C14	0.0521 (13)	0.0503 (13)	0.0574 (14)	0.0013 (10)	0.0150 (10)	−0.0005 (11)
C15	0.0556 (13)	0.0463 (12)	0.0424 (12)	0.0019 (10)	0.0158 (10)	−0.0002 (9)
C16	0.0407 (11)	0.0431 (11)	0.0379 (10)	−0.0079 (9)	0.0092 (8)	−0.0167 (9)
C17	0.0443 (11)	0.0435 (11)	0.0435 (11)	0.0085 (9)	0.0135 (8)	0.0054 (9)
C18	0.0489 (11)	0.0468 (12)	0.0452 (11)	0.0134 (9)	0.0181 (9)	0.0103 (9)
C19	0.0398 (10)	0.0470 (12)	0.0472 (11)	0.0114 (9)	0.0164 (8)	0.0038 (10)
C20	0.0440 (11)	0.0395 (11)	0.0494 (12)	0.0021 (9)	0.0128 (9)	−0.0149 (9)
C21	0.0437 (12)	0.0444 (12)	0.0411 (11)	0.0141 (9)	0.0172 (9)	−0.0048 (9)
C22	0.0438 (10)	0.0490 (12)	0.0429 (10)	0.0120 (9)	0.0170 (8)	−0.0163 (9)
C23	0.0494 (12)	0.0411 (10)	0.0467 (11)	0.0047 (8)	0.0160 (9)	−0.0200 (9)
C24	0.0502 (11)	0.0358 (10)	0.0411 (11)	0.0023 (9)	0.0156 (9)	−0.0006 (9)
N1	0.0407 (9)	0.0338 (9)	0.0551 (11)	0.0082 (7)	0.0145 (8)	0.0036 (8)
N2	0.0461 (10)	0.0416 (9)	0.0376 (9)	0.0023 (7)	0.0148 (7)	−0.0069 (7)
O1	0.0436 (7)	0.0341 (7)	0.0434 (8)	0.0108 (6)	0.0156 (6)	0.0040 (6)
O2	0.0504 (8)	0.0517 (9)	0.0410 (7)	0.0151 (7)	0.0176 (6)	0.0185 (7)
O3	0.0513 (8)	0.0417 (8)	0.0515 (9)	0.0009 (6)	0.0131 (7)	−0.0146 (7)
O4	0.0443 (8)	0.0452 (8)	0.0474 (8)	0.0000 (6)	0.0143 (6)	−0.0122 (7)
O1W	0.054 (2)	0.052 (3)	0.048 (2)	0.000	−0.0156 (19)	0.000
O2W	0.043 (3)	0.055 (4)	0.043 (3)	−0.021 (3)	0.014 (2)	−0.011 (3)
O3W	0.049 (3)	0.053 (3)	0.050 (3)	−0.016 (3)	0.013 (3)	−0.021 (3)
O6W	0.051 (3)	0.045 (3)	0.048 (3)	0.018 (3)	0.010 (3)	0.004 (3)

C1—N1	1.324 (3)	C15—H15A	0.9300
C1—C2	1.352 (3)	C16—O3	1.409 (2)
C1—O1	1.379 (2)	C16—H16A	0.9600
C2—C24	1.404 (3)	C16—H16B	0.9600
C2—C3	1.527 (3)	C16—H16C	0.9600
C3—C4	1.507 (3)	C17—O4	1.415 (3)
C3—C10	1.517 (3)	C17—H17A	0.9600
C3—H3A	0.9800	C17—H17B	0.9600
C4—C9	1.329 (3)	C17—H17C	0.9600
C4—C5	1.470 (3)	C18—C19	1.390 (3)
C5—O2	1.214 (3)	C18—C23	1.390 (3)
C5—C6	1.478 (3)	C19—C20	1.390 (3)
C6—C7	1.498 (3)	C19—H19A	0.9300
C6—H6A	0.9700	C20—C21	1.390 (3)
C6—H6B	0.9700	C20—H20A	0.9300
C7—C8	1.473 (3)	C21—C22	1.390 (3)
C7—C18	1.491 (3)	C21—H21C	0.9300
C7—H7A	0.9800	C22—C23	1.390 (3)
C8—C9	1.494 (3)	C22—H22A	0.9300
C8—H8A	0.9700	C23—H23A	0.9300
C8—H8B	0.9700	C24—N2	1.149 (3)
C9—O1	1.385 (2)	N1—H1A	0.8601
C10—C11	1.390 (3)	N1—H1B	0.8607
C10—C15	1.390 (3)	O1W—H1X	0.8500
C11—C12	1.390 (3)	O1W—H1Y	0.8500
C11—H11A	0.9300	O2W—H2X	0.8501
C12—O3	1.374 (2)	O2W—H2Y	0.8499
C12—C13	1.390 (3)	O3W—H3X	0.8499
C13—O4	1.369 (3)	O3W—H3Y	0.8500
C13—C14	1.390 (3)	O6W—H6X	0.8500
C14—C15	1.390 (3)	O6W—H6Y	0.8501
C14—H14A	0.9300
N1—C1—C2	128.76 (18)	O4—C13—C14	124.6 (2)
N1—C1—O1	110.24 (18)	C12—C13—C14	120.0 (2)
C2—C1—O1	120.99 (18)	C15—C14—C13	120.0 (2)
C1—C2—C24	118.50 (18)	C15—C14—H14A	120.0
C1—C2—C3	122.92 (17)	C13—C14—H14A	120.0
C24—C2—C3	118.22 (18)	C14—C15—C10	120.0 (2)
C4—C3—C10	113.91 (15)	C14—C15—H15A	120.0
C4—C3—C2	108.04 (17)	C10—C15—H15A	120.0
C10—C3—C2	110.68 (15)	O3—C16—H16A	109.5
C4—C3—H3A	108.0	O3—C16—H16B	109.5
C10—C3—H3A	108.0	H16A—C16—H16B	109.5
C2—C3—H3A	108.0	O3—C16—H16C	109.5
C9—C4—C5	118.64 (18)	H16A—C16—H16C	109.5
C9—C4—C3	122.25 (18)	H16B—C16—H16C	109.5
C5—C4—C3	119.06 (17)	O4—C17—H17A	109.5
O2—C5—C4	120.47 (18)	O4—C17—H17B	109.5
O2—C5—C6	120.24 (18)	H17A—C17—H17B	109.5
C4—C5—C6	119.28 (18)	O4—C17—H17C	109.5
C5—C6—C7	116.90 (16)	H17A—C17—H17C	109.5
C5—C6—H6A	108.1	H17B—C17—H17C	109.5
C7—C6—H6A	108.1	C19—C18—C23	120.00 (19)
C5—C6—H6B	108.1	C19—C18—C7	115.45 (19)
C7—C6—H6B	108.1	C23—C18—C7	124.5 (2)
H6A—C6—H6B	107.3	C20—C19—C18	120.0 (2)
C8—C7—C18	114.96 (19)	C20—C19—H19A	120.0
C8—C7—C6	116.55 (18)	C18—C19—H19A	120.0
C18—C7—C6	114.81 (16)	C19—C20—C21	120.00 (19)
C8—C7—H7A	102.5	C19—C20—H20A	120.0
C18—C7—H7A	102.5	C21—C20—H20A	120.0
C6—C7—H7A	102.5	C22—C21—C20	120.00 (18)
C7—C8—C9	112.86 (19)	C22—C21—H21C	120.0
C7—C8—H8A	109.0	C20—C21—H21C	120.0
C9—C8—H8A	109.0	C21—C22—C23	120.0 (2)
C7—C8—H8B	109.0	C21—C22—H22A	120.0
C9—C8—H8B	109.0	C23—C22—H22A	120.0
H8A—C8—H8B	107.8	C22—C23—C18	120.00 (19)
C4—C9—O1	123.35 (18)	C22—C23—H23A	120.0
C4—C9—C8	126.45 (18)	C18—C23—H23A	120.0
O1—C9—C8	110.19 (16)	N2—C24—C2	177.8 (2)
C11—C10—C15	120.00 (19)	C1—N1—H1A	119.7
C11—C10—C3	120.77 (19)	C1—N1—H1B	120.3
C15—C10—C3	118.65 (18)	H1A—N1—H1B	119.9
C12—C11—C10	120.0 (2)	C1—O1—C9	118.10 (15)
C12—C11—H11A	120.0	C12—O3—C16	118.45 (17)
C10—C11—H11A	120.0	C13—O4—C17	117.90 (16)
O3—C12—C11	124.3 (2)	H1X—O1W—H1Y	109.5
O3—C12—C13	115.7 (2)	H2X—O2W—H2Y	109.5
C11—C12—C13	120.0 (2)	H3X—O3W—H3Y	109.5
O4—C13—C12	115.35 (19)	H6X—O6W—H6Y	109.5
N1—C1—C2—C24	−1.8 (3)	C10—C11—C12—O3	177.15 (19)
O1—C1—C2—C24	179.83 (17)	C10—C11—C12—C13	0.0 (3)
N1—C1—C2—C3	−174.77 (19)	O3—C12—C13—O4	5.8 (3)
O1—C1—C2—C3	6.8 (3)	C11—C12—C13—O4	−176.76 (18)
C1—C2—C3—C4	−20.2 (2)	O3—C12—C13—C14	−177.39 (18)
C24—C2—C3—C4	166.75 (16)	C11—C12—C13—C14	0.0 (3)
C1—C2—C3—C10	105.1 (2)	O4—C13—C14—C15	176.4 (2)
C24—C2—C3—C10	−67.9 (2)	C12—C13—C14—C15	0.0 (3)
C10—C3—C4—C9	−105.4 (2)	C13—C14—C15—C10	0.0 (3)
C2—C3—C4—C9	18.0 (2)	C11—C10—C15—C14	0.0 (3)
C10—C3—C4—C5	77.3 (2)	C3—C10—C15—C14	−171.30 (18)
C2—C3—C4—C5	−159.31 (16)	C8—C7—C18—C19	112.6 (2)
C9—C4—C5—O2	−173.29 (19)	C6—C7—C18—C19	−108.0 (2)
C3—C4—C5—O2	4.1 (3)	C8—C7—C18—C23	−65.3 (3)
C9—C4—C5—C6	5.6 (3)	C6—C7—C18—C23	74.0 (3)
C3—C4—C5—C6	−176.94 (18)	C23—C18—C19—C20	0.0 (3)
O2—C5—C6—C7	−168.38 (19)	C7—C18—C19—C20	−178.03 (19)
C4—C5—C6—C7	12.7 (3)	C18—C19—C20—C21	0.0 (3)
C5—C6—C7—C8	−33.1 (3)	C19—C20—C21—C22	0.0 (3)
C5—C6—C7—C18	−171.76 (19)	C20—C21—C22—C23	0.0 (3)
C18—C7—C8—C9	172.45 (17)	C21—C22—C23—C18	0.0 (3)
C6—C7—C8—C9	33.8 (3)	C19—C18—C23—C22	0.0 (3)
C5—C4—C9—O1	174.74 (16)	C7—C18—C23—C22	177.85 (19)
C3—C4—C9—O1	−2.6 (3)	C1—C2—C24—N2	−180 (100)
C5—C4—C9—C8	−3.7 (3)	C3—C2—C24—N2	−6(6)
C3—C4—C9—C8	178.96 (18)	N1—C1—O1—C9	−167.40 (15)
C7—C8—C9—C4	−16.4 (3)	C2—C1—O1—C9	11.3 (3)
C7—C8—C9—O1	165.01 (15)	C4—C9—O1—C1	−13.7 (3)
C4—C3—C10—C11	41.8 (2)	C8—C9—O1—C1	165.00 (16)
C2—C3—C10—C11	−80.1 (2)	C11—C12—O3—C16	−19.5 (3)
C4—C3—C10—C15	−146.95 (18)	C13—C12—O3—C16	157.75 (19)
C2—C3—C10—C15	91.1 (2)	C12—C13—O4—C17	169.62 (18)
C15—C10—C11—C12	0.0 (3)	C14—C13—O4—C17	−7.0 (3)
C3—C10—C11—C12	171.12 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86	2.20	3.042 (3)	167.
N1—H1B···O2ii	0.86	2.12	2.935 (3)	158.
.—···..	.	.	.	.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.86	2.20	3.042 (3)	167
N1—H1B⋯O2ii	0.86	2.12	2.935 (3)	158

Symmetry codes: (i) ; (ii) .