(E)-4-[(1-Benzyl-4-benzyl-idene-2,5-di-oxopyrrolidin-3-yl)meth-yl]benzalde-hyde 0.25-hydrate.

The crystal structure of the title compound, C(26)H(21)NO(3)·0.25H(2)O, reveals one stereogenic centre in the mol-ecule. Nevertheless, due to the observed centrosymmetric space group, both enanti-omers are present in the crystal packing. The water molecule of crystallisation is located on a crystallographic inversion center. The mol-ecule contains one five-membered ring (A) and three six-membered rings (benzyl ring B, benzyl-idene ring C and formyl-benzyl ring D). All four rings are not coplanar: the dihedral angles between rings A and B, A and C, and A and D are 70.35 (9), 33.8 (1) and 60.30 (9)°, respectively. In the crystal, pairs of weak C-H⋯O inter-actions lead to the formation of centrosymmetric dimers. Additional C-H⋯O inter-actions link the dimers into chains along [011].

Related literature

For palladium-catalysed coupling reactions, see: Hu et al. (2011 ▶). For related active pharmaceutical compounds, see: Hu et al. (2009a ▶,b ▶). Ffor the physiological activity of dioxo­pyrrol­idinbenzaldehyde derivatives, see: Pitchumani & Vijaikumar (2010 ▶). F palladium-catalysed inter- and intra­molecular reactions, see: Hu et al. (2010a ▶,b ▶).

Experimental

Crystal data

C26H21NO3·0.25H2O

M = 399.94

Triclinic,

a = 7.7360 (15) Å

b = 12.441 (3) Å

c = 12.577 (3) Å

α = 64.14 (3)°

β = 81.14 (2)°

γ = 86.46 (3)°

V = 1076.2 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.28 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.978, T max = 0.984

8445 measured reflections

4224 independent reflections

3065 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.149

S = 1.09

4224 reflections

277 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012160/im2364sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012160/im2364Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012160/im2364Isup3.cml

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

C26H21NO3·0.25H2O	Z = 2
Mr = 399.94	F(000) = 421
Triclinic, P1	Dx = 1.234 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7360 (15) Å	Cell parameters from 3716 reflections
b = 12.441 (3) Å	θ = 2.1–24.7°
c = 12.577 (3) Å	µ = 0.08 mm−1
α = 64.14 (3)°	T = 291 K
β = 81.14 (2)°	Block, colourless
γ = 86.46 (3)°	0.28 × 0.22 × 0.20 mm
V = 1076.2 (4) Å3

Bruker SMART APEX CCD diffractometer	4224 independent reflections
Radiation source: sealed tube	3065 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
phi and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.978, Tmax = 0.984	k = −13→15
8445 measured reflections	l = 0→15

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.07P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3
4224 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.20 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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)1.5177 (0.0088) x + 12.2930 (0.0068) y + 6.4535 (0.0131) z = 7.8343 (0.0042)* 0.0161 (0.0015) N1 * -0.0035 (0.0014) C8 * -0.0090 (0.0014) C9 * 0.0172 (0.0014) C10 * -0.0208 (0.0015) C11Rms deviation of fitted atoms = 0.01473.2207 (0.0064) x + 4.3390 (0.0100) y - 6.9725 (0.0098) z = 0.3855 (0.0095)Angle to previous plane (with approximate e.s.d.) = 70.35 (0.09)* 0.0022 (0.0016) C1 * -0.0017 (0.0015) C2 * 0.0004 (0.0014) C3 * 0.0003 (0.0014) C4 * 0.0002 (0.0014) C5 * -0.0015 (0.0015) C6Rms deviation of fitted atoms = 0.00131.5177 (0.0088) x + 12.2930 (0.0068) y + 6.4535 (0.0131) z = 7.8343 (0.0042)Angle to previous plane (with approximate e.s.d.) = 70.35 (0.09)* 0.0161 (0.0015) N1 * -0.0035 (0.0014) C8 * -0.0090 (0.0014) C9 * 0.0172 (0.0014) C10 * -0.0208 (0.0015) C11Rms deviation of fitted atoms = 0.01474.8630 (0.0064) x + 9.1574 (0.0092) y + 8.8027 (0.0100) z = 5.4849 (0.0080)Angle to previous plane (with approximate e.s.d.) = 33.76 (0.10)* 0.0019 (0.0017) C13 * -0.0066 (0.0017) C14 * 0.0011 (0.0016) C15 * 0.0093 (0.0016) C16 * -0.0141 (0.0016) C17 * 0.0086 (0.0017) C18Rms deviation of fitted atoms = 0.00821.5177 (0.0088) x + 12.2930 (0.0068) y + 6.4535 (0.0131) z = 7.8343 (0.0042)Angle to previous plane (with approximate e.s.d.) = 33.76 (0.10)* 0.0161 (0.0015) N1 * -0.0035 (0.0014) C8 * -0.0090 (0.0014) C9 * 0.0172 (0.0014) C10 * -0.0208 (0.0015) C11Rms deviation of fitted atoms = 0.01476.5252 (0.0054) x + 5.2018 (0.0111) y - 0.7915 (0.0119) z = 6.7075 (0.0096)Angle to previous plane (with approximate e.s.d.) = 60.30 (0.09)* -0.0090 (0.0016) C20 * 0.0056 (0.0016) C21 * -0.0033 (0.0016) C22 * 0.0043 (0.0018) C23 * -0.0082 (0.0018) C24 * 0.0105 (0.0016) C25Rms deviation of fitted atoms = 0.0073

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	−0.1529 (3)	0.6731 (2)	0.2926 (2)	0.0327 (5)
H1A	−0.2385	0.6692	0.2499	0.039*
C2	−0.1659 (3)	0.75660 (19)	0.33915 (19)	0.0304 (5)
H2A	−0.2607	0.8082	0.3280	0.036*
C3	−0.0374 (3)	0.76321 (19)	0.40232 (19)	0.0316 (5)
H3A	−0.0460	0.8194	0.4331	0.038*
C4	0.1036 (3)	0.6858 (2)	0.4193 (2)	0.0338 (5)
H4A	0.1894	0.6901	0.4616	0.041*
C5	0.1169 (3)	0.6020 (2)	0.3733 (2)	0.0331 (5)
H5A	0.2116	0.5502	0.3847	0.040*
C6	−0.0119 (3)	0.59562 (19)	0.3101 (2)	0.0310 (5)
C7	0.0065 (3)	0.50546 (19)	0.25793 (19)	0.0283 (4)
H7A	0.0740	0.4380	0.3057	0.034*
H7B	−0.1087	0.4762	0.2616	0.034*
C8	0.0049 (3)	0.6167 (2)	0.0375 (2)	0.0294 (5)
C9	0.1367 (3)	0.6566 (2)	−0.0702 (2)	0.0323 (5)
C10	0.3144 (3)	0.61565 (19)	−0.03003 (19)	0.0294 (5)
H10A	0.3642	0.5601	−0.0627	0.035*
C11	0.2696 (3)	0.5479 (2)	0.1037 (2)	0.0323 (5)
C12	0.0939 (3)	0.7234 (2)	−0.1780 (2)	0.0386 (5)
H12A	−0.0244	0.7411	−0.1801	0.046*
C13	0.2048 (3)	0.7736 (2)	−0.2946 (2)	0.0360 (5)
C14	0.1571 (3)	0.88196 (19)	−0.38198 (19)	0.0292 (5)
H14A	0.0555	0.9198	−0.3665	0.035*
C15	0.2610 (3)	0.9338 (2)	−0.49241 (19)	0.0305 (5)
H15A	0.2292	1.0066	−0.5506	0.037*
C16	0.4072 (3)	0.87893 (19)	−0.51516 (19)	0.0282 (5)
H16A	0.4773	0.9147	−0.5887	0.034*
C17	0.4552 (3)	0.76828 (19)	−0.42925 (19)	0.0312 (5)
H17A	0.5542	0.7296	−0.4472	0.037*
C18	0.3577 (3)	0.71743 (18)	−0.31989 (18)	0.0259 (4)
H18A	0.3922	0.6455	−0.2619	0.031*
C19	0.4489 (3)	0.71377 (19)	−0.0610 (2)	0.0308 (5)
H19A	0.5544	0.6773	−0.0277	0.037*
H19B	0.4791	0.7545	−0.1470	0.037*
C20	0.3842 (3)	0.8034 (2)	−0.01497 (19)	0.0305 (5)
C21	0.4122 (3)	0.7882 (2)	0.09694 (19)	0.0324 (5)
H21A	0.4734	0.7216	0.1432	0.039*
C22	0.3524 (3)	0.8682 (2)	0.14121 (19)	0.0294 (5)
H22A	0.3711	0.8542	0.2175	0.035*
C23	0.2649 (3)	0.9694 (2)	0.0748 (2)	0.0384 (5)
C24	0.2369 (3)	0.9850 (2)	−0.0369 (2)	0.0380 (5)
H24A	0.1751	1.0515	−0.0828	0.046*
C25	0.2971 (3)	0.9064 (2)	−0.0814 (2)	0.0347 (5)
H25A	0.2797	0.9217	−0.1582	0.042*
C26	0.2021 (3)	1.0583 (2)	0.1198 (2)	0.0314 (5)
H26A	0.1412	1.1233	0.0706	0.038*
N1	0.0911 (2)	0.55614 (17)	0.13566 (17)	0.0330 (4)
O1	−0.15018 (18)	0.62882 (12)	0.04401 (13)	0.0257 (3)
O2	0.36924 (18)	0.49511 (13)	0.17642 (13)	0.0280 (3)
O3	0.22208 (19)	1.05470 (13)	0.21319 (13)	0.0301 (4)
O1W	0.5000	0.5000	0.5000	0.0428 (12)	0.50
H1X	0.4981	0.4401	0.5675	0.051*	0.25
H1Y	0.5958	0.5191	0.4527	0.051*	0.25

	U11	U22	U33	U12	U13	U23
C1	0.0355 (12)	0.0359 (12)	0.0290 (11)	0.0174 (9)	−0.0162 (9)	−0.0146 (10)
C2	0.0302 (11)	0.0283 (11)	0.0261 (10)	0.0184 (9)	0.0041 (8)	−0.0107 (9)
C3	0.0320 (11)	0.0265 (11)	0.0258 (11)	−0.0154 (9)	0.0149 (9)	−0.0056 (9)
C4	0.0251 (11)	0.0360 (12)	0.0379 (12)	−0.0185 (9)	0.0152 (9)	−0.0176 (10)
C5	0.0315 (12)	0.0270 (11)	0.0308 (11)	−0.0142 (9)	0.0196 (9)	−0.0093 (9)
C6	0.0268 (11)	0.0245 (10)	0.0327 (11)	−0.0018 (8)	0.0168 (9)	−0.0108 (9)
C7	0.0262 (10)	0.0274 (10)	0.0261 (10)	−0.0055 (8)	0.0002 (8)	−0.0073 (9)
C8	0.0240 (11)	0.0340 (11)	0.0323 (11)	0.0104 (8)	−0.0104 (8)	−0.0156 (10)
C9	0.0280 (11)	0.0380 (12)	0.0297 (11)	0.0019 (9)	−0.0111 (9)	−0.0115 (10)
C10	0.0274 (11)	0.0283 (11)	0.0298 (11)	0.0118 (8)	−0.0133 (9)	−0.0086 (9)
C11	0.0296 (11)	0.0326 (11)	0.0293 (11)	0.0095 (9)	−0.0086 (9)	−0.0083 (9)
C12	0.0445 (14)	0.0367 (13)	0.0304 (12)	0.0091 (10)	−0.0099 (10)	−0.0103 (10)
C13	0.0341 (12)	0.0338 (12)	0.0347 (12)	0.0122 (10)	−0.0040 (9)	−0.0117 (10)
C14	0.0268 (11)	0.0302 (11)	0.0269 (11)	0.0112 (8)	−0.0063 (8)	−0.0096 (9)
C15	0.0331 (12)	0.0318 (11)	0.0217 (10)	0.0157 (9)	−0.0106 (9)	−0.0068 (9)
C16	0.0264 (10)	0.0260 (10)	0.0240 (10)	−0.0024 (8)	0.0000 (8)	−0.0040 (8)
C17	0.0322 (11)	0.0299 (11)	0.0286 (11)	0.0208 (9)	−0.0078 (9)	−0.0115 (9)
C18	0.0287 (10)	0.0203 (9)	0.0275 (11)	0.0146 (8)	−0.0162 (8)	−0.0070 (8)
C19	0.0325 (12)	0.0286 (11)	0.0287 (11)	0.0041 (9)	−0.0116 (9)	−0.0083 (9)
C20	0.0235 (10)	0.0394 (12)	0.0277 (11)	−0.0015 (9)	−0.0025 (8)	−0.0139 (10)
C21	0.0262 (11)	0.0437 (13)	0.0241 (11)	0.0082 (9)	−0.0086 (8)	−0.0113 (10)
C22	0.0263 (10)	0.0330 (11)	0.0286 (11)	−0.0021 (9)	−0.0093 (8)	−0.0110 (9)
C23	0.0428 (13)	0.0369 (13)	0.0304 (12)	0.0062 (10)	−0.0019 (10)	−0.0118 (10)
C24	0.0416 (13)	0.0356 (12)	0.0324 (12)	0.0098 (10)	−0.0174 (10)	−0.0081 (10)
C25	0.0294 (11)	0.0355 (12)	0.0326 (12)	−0.0022 (9)	−0.0094 (9)	−0.0068 (10)
C26	0.0240 (11)	0.0283 (11)	0.0368 (13)	0.0026 (8)	0.0029 (9)	−0.0119 (10)
N1	0.0298 (10)	0.0319 (10)	0.0277 (10)	0.0010 (8)	−0.0048 (7)	−0.0041 (8)
O1	0.0227 (7)	0.0253 (7)	0.0284 (8)	0.0028 (5)	−0.0112 (6)	−0.0088 (6)
O2	0.0210 (7)	0.0247 (7)	0.0334 (8)	0.0082 (6)	−0.0069 (6)	−0.0079 (6)
O3	0.0245 (7)	0.0294 (8)	0.0292 (8)	0.0100 (6)	0.0058 (6)	−0.0103 (6)
O1W	0.024 (2)	0.036 (3)	0.054 (3)	0.0020 (19)	−0.016 (2)	−0.003 (2)

C1—C2	1.389 (3)	C13—C18	1.402 (3)
C1—C6	1.388 (3)	C14—C15	1.389 (3)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.392 (3)	C15—C16	1.343 (3)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.387 (3)	C16—C17	1.401 (3)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.389 (3)	C17—C18	1.357 (3)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.393 (4)	C18—H18A	0.9300
C5—H5A	0.9300	C19—C20	1.495 (3)
C6—C7	1.517 (3)	C19—H19A	0.9700
C7—N1	1.444 (3)	C19—H19B	0.9700
C7—H7A	0.9700	C20—C21	1.386 (3)
C7—H7B	0.9700	C20—C25	1.388 (3)
C8—O1	1.195 (3)	C21—C22	1.365 (3)
C8—N1	1.384 (3)	C21—H21A	0.9300
C8—C9	1.474 (3)	C22—C23	1.376 (3)
C9—C12	1.326 (3)	C22—H22A	0.9300
C9—C10	1.519 (3)	C23—C24	1.382 (3)
C10—C11	1.510 (3)	C23—C26	1.476 (3)
C10—C19	1.531 (3)	C24—C25	1.351 (4)
C10—H10A	0.9800	C24—H24A	0.9300
C11—O2	1.222 (3)	C25—H25A	0.9300
C11—N1	1.388 (3)	C26—O3	1.189 (3)
C12—C13	1.468 (3)	C26—H26A	0.9300
C12—H12A	0.9300	O1W—H1X	0.8500
C13—C14	1.390 (3)	O1W—H1Y	0.8500
C2—C1—C6	119.8 (2)	C15—C14—H14A	119.9
C2—C1—H1A	120.1	C13—C14—H14A	119.9
C6—C1—H1A	120.1	C16—C15—C14	120.0 (2)
C1—C2—C3	120.17 (19)	C16—C15—H15A	120.0
C1—C2—H2A	119.9	C14—C15—H15A	120.0
C3—C2—H2A	119.9	C15—C16—C17	120.7 (2)
C4—C3—C2	119.9 (2)	C15—C16—H16A	119.6
C4—C3—H3A	120.1	C17—C16—H16A	119.6
C2—C3—H3A	120.1	C18—C17—C16	120.16 (19)
C3—C4—C5	120.2 (2)	C18—C17—H17A	119.9
C3—C4—H4A	119.9	C16—C17—H17A	119.9
C5—C4—H4A	119.9	C17—C18—C13	119.79 (19)
C4—C5—C6	119.8 (2)	C17—C18—H18A	120.1
C4—C5—H5A	120.1	C13—C18—H18A	120.1
C6—C5—H5A	120.1	C20—C19—C10	112.94 (19)
C1—C6—C5	120.2 (2)	C20—C19—H19A	109.0
C1—C6—C7	120.6 (2)	C10—C19—H19A	109.0
C5—C6—C7	119.22 (19)	C20—C19—H19B	109.0
N1—C7—C6	112.17 (18)	C10—C19—H19B	109.0
N1—C7—H7A	109.2	H19A—C19—H19B	107.8
C6—C7—H7A	109.2	C21—C20—C25	116.5 (2)
N1—C7—H7B	109.2	C21—C20—C19	120.9 (2)
C6—C7—H7B	109.2	C25—C20—C19	122.6 (2)
H7A—C7—H7B	107.9	C22—C21—C20	121.8 (2)
O1—C8—N1	123.6 (2)	C22—C21—H21A	119.1
O1—C8—C9	128.5 (2)	C20—C21—H21A	119.1
N1—C8—C9	107.90 (18)	C21—C22—C23	121.0 (2)
C12—C9—C8	121.6 (2)	C21—C22—H22A	119.5
C12—C9—C10	130.6 (2)	C23—C22—H22A	119.5
C8—C9—C10	107.59 (18)	C22—C23—C24	117.3 (2)
C11—C10—C9	102.93 (18)	C22—C23—C26	122.0 (2)
C11—C10—C19	110.13 (18)	C24—C23—C26	120.7 (2)
C9—C10—C19	116.51 (18)	C25—C24—C23	121.8 (2)
C11—C10—H10A	109.0	C25—C24—H24A	119.1
C9—C10—H10A	109.0	C23—C24—H24A	119.1
C19—C10—H10A	109.0	C24—C25—C20	121.5 (2)
O2—C11—N1	123.0 (2)	C24—C25—H25A	119.2
O2—C11—C10	127.8 (2)	C20—C25—H25A	119.2
N1—C11—C10	109.08 (18)	O3—C26—C23	126.1 (2)
C9—C12—C13	129.9 (2)	O3—C26—H26A	117.0
C9—C12—H12A	115.0	C23—C26—H26A	117.0
C13—C12—H12A	115.0	C8—N1—C11	112.37 (18)
C14—C13—C18	119.1 (2)	C8—N1—C7	124.44 (19)
C14—C13—C12	118.4 (2)	C11—N1—C7	123.18 (19)
C18—C13—C12	122.4 (2)	H1X—O1W—H1Y	118.8
C15—C14—C13	120.1 (2)
C6—C1—C2—C3	0.5 (3)	C15—C16—C17—C18	−2.6 (4)
C1—C2—C3—C4	−0.3 (3)	C16—C17—C18—C13	2.5 (4)
C2—C3—C4—C5	0.1 (3)	C14—C13—C18—C17	−1.0 (4)
C3—C4—C5—C6	−0.1 (3)	C12—C13—C18—C17	−179.8 (2)
C2—C1—C6—C5	−0.4 (3)	C11—C10—C19—C20	−60.7 (2)
C2—C1—C6—C7	−178.8 (2)	C9—C10—C19—C20	56.0 (3)
C4—C5—C6—C1	0.3 (3)	C10—C19—C20—C21	90.7 (3)
C4—C5—C6—C7	178.63 (18)	C10—C19—C20—C25	−90.6 (3)
C1—C6—C7—N1	84.9 (2)	C25—C20—C21—C22	2.0 (3)
C5—C6—C7—N1	−93.5 (2)	C19—C20—C21—C22	−179.2 (2)
O1—C8—C9—C12	6.1 (4)	C20—C21—C22—C23	−1.5 (4)
N1—C8—C9—C12	−176.0 (2)	C21—C22—C23—C24	1.4 (4)
O1—C8—C9—C10	−178.2 (2)	C21—C22—C23—C26	−178.8 (2)
N1—C8—C9—C10	−0.3 (2)	C22—C23—C24—C25	−1.9 (4)
C12—C9—C10—C11	177.4 (3)	C26—C23—C24—C25	178.3 (2)
C8—C9—C10—C11	2.2 (2)	C23—C24—C25—C20	2.5 (4)
C12—C9—C10—C19	56.8 (4)	C21—C20—C25—C24	−2.5 (3)
C8—C9—C10—C19	−118.4 (2)	C19—C20—C25—C24	178.7 (2)
C9—C10—C11—O2	178.1 (2)	C22—C23—C26—O3	1.7 (4)
C19—C10—C11—O2	−57.0 (3)	C24—C23—C26—O3	−178.5 (2)
C9—C10—C11—N1	−3.5 (2)	O1—C8—N1—C11	176.0 (2)
C19—C10—C11—N1	121.4 (2)	C9—C8—N1—C11	−2.0 (3)
C8—C9—C12—C13	178.6 (2)	O1—C8—N1—C7	−3.3 (4)
C10—C9—C12—C13	4.0 (5)	C9—C8—N1—C7	178.7 (2)
C9—C12—C13—C14	−148.5 (3)	O2—C11—N1—C8	−177.9 (2)
C9—C12—C13—C18	30.4 (4)	C10—C11—N1—C8	3.6 (3)
C18—C13—C14—C15	−0.5 (4)	O2—C11—N1—C7	1.4 (4)
C12—C13—C14—C15	178.4 (2)	C10—C11—N1—C7	−177.16 (19)
C13—C14—C15—C16	0.4 (4)	C6—C7—N1—C8	−86.5 (3)
C14—C15—C16—C17	1.2 (4)	C6—C7—N1—C11	94.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2i	0.98	2.56	3.419 (3)	147
C18—H18A···O2i	0.93	2.49	3.322 (3)	149
C19—H19A···O1ii	0.97	2.53	3.481 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O2i	0.98	2.56	3.419 (3)	147
C18—H18A⋯O2i	0.93	2.49	3.322 (3)	149
C19—H19A⋯O1ii	0.97	2.53	3.481 (3)	168

Symmetry codes: (i) ; (ii) .