4-Hydr-oxy-3-(1'-methyl-2-oxo-4'-phenyl-spiro-[indoline-3,2'-pyrrolidine]-3'-yl-carbon-yl)quinolin-2(1H)-one.

In the title compound, C(28)H(23)N(3)O(4), the dihedral angle between the quinoline and indole ring systems is 29.30 (5)°. The pyrrolidine ring adopts a twist conformation. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. A weak intra-molecular C3-H3⋯O3 inter-action is also observed. In the crystal, mol-ecules are linked by two sets of N-H⋯O hydrogen bonds, forming centrosymmetric dimers containing two R(2) (2)(8) ring motifs. The dimers are linked via C-H⋯π inter-actions.

Related literature

For general background to indole, quinoline and pyrrolidine derivatives, see: Amalraj et al. (2003 ▶); Cordell (1981 ▶); Suzuki et al. (1994 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H23N3O4

M = 465.49

Triclinic,

a = 9.6918 (3) Å

b = 11.0258 (3) Å

c = 12.9663 (4) Å

α = 69.111 (1)°

β = 72.044 (2)°

γ = 66.410 (1)°

V = 1163.93 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.982, T max = 0.982

21655 measured reflections

5795 independent reflections

4635 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.119

S = 1.03

5795 reflections

329 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010500/ci5061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010500/ci5061Isup2.hkl

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

C28H23N3O4	Z = 2
Mr = 465.49	F(000) = 488
Triclinic, P1	Dx = 1.328 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6918 (3) Å	Cell parameters from 1865 reflections
b = 11.0258 (3) Å	θ = 1.7–28.4°
c = 12.9663 (4) Å	µ = 0.09 mm−1
α = 69.111 (1)°	T = 293 K
β = 72.044 (2)°	Block, colourless
γ = 66.410 (1)°	0.20 × 0.20 × 0.20 mm
V = 1163.93 (6) Å3

Bruker SMART APEXII area-detector diffractometer	5795 independent reflections
Radiation source: fine-focus sealed tube	4635 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.982, Tmax = 0.982	k = −14→14
21655 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.2023P] where P = (Fo2 + 2Fc2)/3
5795 reflections	(Δ/σ)max = 0.008
329 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 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 > 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
O1	−0.12393 (11)	0.84110 (9)	0.20477 (8)	0.0513 (2)
O2	0.31591 (12)	0.88012 (10)	0.35337 (8)	0.0540 (2)
O3	0.17428 (11)	0.93755 (10)	0.06203 (7)	0.0489 (2)
O4	0.43677 (12)	1.06028 (12)	0.24273 (9)	0.0577 (3)
N1	−0.11028 (12)	0.89412 (11)	0.41897 (8)	0.0438 (2)
C2	−0.03598 (13)	0.94481 (12)	0.30309 (9)	0.0377 (2)
C3	0.13212 (13)	0.83758 (11)	0.29618 (9)	0.0362 (2)
H3	0.1534	0.7989	0.2334	0.043*
C4	0.12577 (14)	0.72173 (12)	0.40670 (9)	0.0398 (3)
H4	0.1635	0.7380	0.4609	0.048*
C5	−0.04598 (15)	0.74471 (13)	0.44758 (10)	0.0451 (3)
H5A	−0.0828	0.7067	0.4086	0.054*
H5B	−0.0702	0.7047	0.5280	0.054*
C6	−0.27726 (17)	0.95032 (17)	0.44161 (13)	0.0608 (4)
H6A	−0.3175	0.9223	0.3981	0.091*
H6B	−0.3085	1.0488	0.4214	0.091*
H6C	−0.3159	0.9170	0.5202	0.091*
C7	−0.10803 (14)	0.94192 (12)	0.21255 (9)	0.0405 (3)
N8	−0.15228 (13)	1.07050 (11)	0.14433 (9)	0.0465 (3)
C9	−0.11390 (14)	1.16162 (12)	0.17404 (10)	0.0437 (3)
C10	−0.13151 (19)	1.29824 (14)	0.12047 (13)	0.0604 (4)
H10	−0.1705	1.3416	0.0546	0.072*
C11	−0.0888 (2)	1.36838 (15)	0.16859 (15)	0.0669 (4)
H11	−0.0970	1.4600	0.1332	0.080*
C12	−0.03449 (19)	1.30537 (14)	0.26777 (14)	0.0594 (4)
H12	−0.0103	1.3559	0.2997	0.071*
C13	−0.01539 (15)	1.16707 (13)	0.32065 (11)	0.0480 (3)
H13	0.0216	1.1243	0.3874	0.058*
C14	−0.05276 (14)	1.09499 (12)	0.27148 (9)	0.0395 (2)
C15	0.25320 (13)	0.90191 (11)	0.27531 (9)	0.0378 (2)
C16	0.29296 (13)	0.99495 (11)	0.16590 (9)	0.0363 (2)
C17	0.24039 (13)	1.01026 (11)	0.06679 (9)	0.0377 (2)
N18	0.26902 (12)	1.11132 (10)	−0.02685 (8)	0.0419 (2)
C19	0.34942 (13)	1.19400 (12)	−0.03571 (10)	0.0408 (3)
C20	0.37500 (16)	1.29242 (13)	−0.13735 (12)	0.0515 (3)
H20	0.3361	1.3035	−0.1986	0.062*
C21	0.45814 (18)	1.37192 (15)	−0.14509 (13)	0.0597 (4)
H21	0.4756	1.4372	−0.2122	0.072*
C22	0.51668 (19)	1.35655 (16)	−0.05436 (14)	0.0624 (4)
H22	0.5725	1.4117	−0.0613	0.075*
C23	0.49284 (16)	1.26065 (15)	0.04533 (13)	0.0533 (3)
H23	0.5326	1.2506	0.1058	0.064*
C24	0.40805 (13)	1.17747 (12)	0.05590 (10)	0.0412 (3)
C25	0.37906 (13)	1.07426 (12)	0.15761 (10)	0.0403 (3)
C26	0.22252 (15)	0.58092 (12)	0.38987 (10)	0.0435 (3)
C27	0.33649 (18)	0.49550 (14)	0.45126 (13)	0.0590 (4)
H27	0.3503	0.5229	0.5064	0.071*
C28	0.4310 (2)	0.36850 (16)	0.43128 (17)	0.0739 (5)
H28	0.5078	0.3124	0.4726	0.089*
C29	0.4112 (2)	0.32639 (15)	0.35130 (16)	0.0695 (4)
H29	0.4755	0.2426	0.3373	0.083*
C30	0.29633 (18)	0.40778 (15)	0.29184 (14)	0.0594 (4)
H30	0.2814	0.3783	0.2385	0.071*
C31	0.20241 (16)	0.53399 (13)	0.31095 (11)	0.0492 (3)
H31	0.1245	0.5883	0.2703	0.059*
H4A	0.405 (3)	0.985 (2)	0.301 (2)	0.106 (7)*
H8	−0.1719 (19)	1.0831 (17)	0.0782 (15)	0.065 (5)*
H18	0.2265 (18)	1.1249 (15)	−0.0844 (14)	0.054 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0677 (6)	0.0516 (5)	0.0457 (5)	−0.0282 (4)	−0.0212 (4)	−0.0070 (4)
O2	0.0656 (6)	0.0651 (6)	0.0408 (5)	−0.0325 (5)	−0.0224 (4)	−0.0019 (4)
O3	0.0688 (6)	0.0569 (5)	0.0340 (4)	−0.0363 (5)	−0.0133 (4)	−0.0061 (4)
O4	0.0679 (6)	0.0729 (7)	0.0496 (5)	−0.0398 (5)	−0.0200 (5)	−0.0094 (5)
N1	0.0470 (6)	0.0469 (6)	0.0327 (5)	−0.0145 (4)	−0.0058 (4)	−0.0078 (4)
C2	0.0430 (6)	0.0406 (6)	0.0306 (5)	−0.0140 (5)	−0.0105 (4)	−0.0075 (4)
C3	0.0437 (6)	0.0344 (5)	0.0303 (5)	−0.0128 (4)	−0.0101 (4)	−0.0060 (4)
C4	0.0495 (6)	0.0391 (6)	0.0311 (5)	−0.0170 (5)	−0.0125 (4)	−0.0029 (4)
C5	0.0527 (7)	0.0478 (6)	0.0328 (5)	−0.0211 (5)	−0.0077 (5)	−0.0036 (5)
C6	0.0495 (8)	0.0672 (9)	0.0528 (8)	−0.0153 (7)	−0.0008 (6)	−0.0134 (7)
C7	0.0427 (6)	0.0456 (6)	0.0346 (5)	−0.0155 (5)	−0.0099 (4)	−0.0088 (5)
N8	0.0553 (6)	0.0470 (6)	0.0392 (5)	−0.0141 (5)	−0.0214 (5)	−0.0065 (4)
C9	0.0465 (6)	0.0416 (6)	0.0411 (6)	−0.0093 (5)	−0.0138 (5)	−0.0102 (5)
C10	0.0755 (10)	0.0439 (7)	0.0574 (8)	−0.0109 (7)	−0.0311 (7)	−0.0028 (6)
C11	0.0842 (11)	0.0372 (7)	0.0783 (11)	−0.0144 (7)	−0.0298 (9)	−0.0087 (7)
C12	0.0701 (9)	0.0455 (7)	0.0703 (9)	−0.0146 (6)	−0.0219 (7)	−0.0222 (7)
C13	0.0535 (7)	0.0459 (7)	0.0469 (7)	−0.0106 (5)	−0.0150 (5)	−0.0169 (5)
C14	0.0420 (6)	0.0387 (6)	0.0355 (5)	−0.0098 (4)	−0.0089 (4)	−0.0100 (4)
C15	0.0423 (6)	0.0371 (5)	0.0345 (5)	−0.0112 (4)	−0.0100 (4)	−0.0097 (4)
C16	0.0380 (6)	0.0364 (5)	0.0350 (5)	−0.0115 (4)	−0.0076 (4)	−0.0102 (4)
C17	0.0409 (6)	0.0386 (6)	0.0331 (5)	−0.0138 (4)	−0.0059 (4)	−0.0093 (4)
N18	0.0495 (6)	0.0438 (5)	0.0344 (5)	−0.0199 (4)	−0.0101 (4)	−0.0058 (4)
C19	0.0386 (6)	0.0362 (5)	0.0431 (6)	−0.0114 (4)	−0.0028 (5)	−0.0110 (5)
C20	0.0535 (8)	0.0456 (7)	0.0473 (7)	−0.0178 (6)	−0.0058 (6)	−0.0046 (5)
C21	0.0603 (8)	0.0479 (7)	0.0601 (8)	−0.0249 (6)	0.0001 (7)	−0.0038 (6)
C22	0.0618 (9)	0.0573 (8)	0.0727 (10)	−0.0348 (7)	−0.0006 (7)	−0.0157 (7)
C23	0.0503 (7)	0.0564 (8)	0.0598 (8)	−0.0265 (6)	−0.0044 (6)	−0.0179 (6)
C24	0.0374 (6)	0.0399 (6)	0.0462 (6)	−0.0137 (5)	−0.0034 (5)	−0.0142 (5)
C25	0.0389 (6)	0.0436 (6)	0.0408 (6)	−0.0134 (5)	−0.0077 (5)	−0.0142 (5)
C26	0.0488 (7)	0.0377 (6)	0.0413 (6)	−0.0192 (5)	−0.0094 (5)	−0.0012 (5)
C27	0.0668 (9)	0.0463 (7)	0.0622 (9)	−0.0177 (6)	−0.0276 (7)	−0.0006 (6)
C28	0.0695 (10)	0.0471 (8)	0.0905 (12)	−0.0093 (7)	−0.0319 (9)	0.0010 (8)
C29	0.0670 (10)	0.0402 (7)	0.0916 (12)	−0.0172 (7)	−0.0074 (9)	−0.0137 (7)
C30	0.0652 (9)	0.0512 (8)	0.0671 (9)	−0.0294 (7)	−0.0005 (7)	−0.0204 (7)
C31	0.0530 (7)	0.0451 (7)	0.0511 (7)	−0.0209 (6)	−0.0090 (6)	−0.0102 (5)

O1—C7	1.2232 (15)	C12—H12	0.93
O2—C15	1.2412 (14)	C13—C14	1.3797 (17)
O3—C17	1.2360 (14)	C13—H13	0.93
O4—C25	1.3210 (15)	C15—C16	1.4679 (15)
O4—H4A	0.99 (2)	C16—C25	1.3908 (16)
N1—C6	1.4572 (18)	C16—C17	1.4559 (15)
N1—C5	1.4577 (16)	C17—N18	1.3666 (15)
N1—C2	1.4645 (15)	N18—C19	1.3748 (16)
C2—C14	1.5092 (16)	N18—H18	0.900 (16)
C2—C7	1.5546 (16)	C19—C24	1.3950 (17)
C2—C3	1.5824 (16)	C19—C20	1.4035 (17)
C3—C15	1.5123 (16)	C20—C21	1.371 (2)
C3—C4	1.5466 (15)	C20—H20	0.93
C3—H3	0.98	C21—C22	1.388 (2)
C4—C26	1.5124 (17)	C21—H21	0.93
C4—C5	1.5265 (18)	C22—C23	1.371 (2)
C4—H4	0.98	C22—H22	0.93
C5—H5A	0.97	C23—C24	1.4068 (18)
C5—H5B	0.97	C23—H23	0.93
C6—H6A	0.96	C24—C25	1.4389 (17)
C6—H6B	0.96	C26—C27	1.3840 (18)
C6—H6C	0.96	C26—C31	1.3907 (18)
C7—N8	1.3526 (16)	C27—C28	1.397 (2)
N8—C9	1.3999 (17)	C27—H27	0.93
N8—H8	0.886 (18)	C28—C29	1.366 (3)
C9—C10	1.3791 (18)	C28—H28	0.93
C9—C14	1.3922 (16)	C29—C30	1.369 (2)
C10—C11	1.385 (2)	C29—H29	0.93
C10—H10	0.93	C30—C31	1.385 (2)
C11—C12	1.379 (2)	C30—H30	0.93
C11—H11	0.93	C31—H31	0.93
C12—C13	1.3915 (19)
C25—O4—H4A	102.8 (13)	C14—C13—H13	120.9
C6—N1—C5	115.61 (11)	C12—C13—H13	120.9
C6—N1—C2	115.01 (10)	C13—C14—C9	120.22 (11)
C5—N1—C2	106.72 (9)	C13—C14—C2	131.02 (10)
N1—C2—C14	113.47 (9)	C9—C14—C2	108.75 (10)
N1—C2—C7	113.94 (10)	O2—C15—C16	119.22 (11)
C14—C2—C7	101.31 (9)	O2—C15—C3	119.46 (10)
N1—C2—C3	102.76 (8)	C16—C15—C3	121.25 (9)
C14—C2—C3	117.72 (10)	C25—C16—C17	119.02 (10)
C7—C2—C3	107.99 (9)	C25—C16—C15	118.98 (10)
C15—C3—C4	114.61 (9)	C17—C16—C15	121.97 (10)
C15—C3—C2	112.81 (9)	O3—C17—N18	118.80 (10)
C4—C3—C2	105.06 (9)	O3—C17—C16	124.44 (10)
C15—C3—H3	108.0	N18—C17—C16	116.76 (10)
C4—C3—H3	108.0	N18—C19—C24	119.67 (11)
C2—C3—H3	108.0	N18—C19—C20	119.99 (12)
C26—C4—C5	115.35 (10)	C24—C19—C20	120.32 (12)
C26—C4—C3	112.53 (9)	C21—C20—C19	119.04 (14)
C5—C4—C3	102.87 (9)	C21—C20—H20	120.5
C26—C4—H4	108.6	C19—C20—H20	120.5
C5—C4—H4	108.6	C20—C21—C22	121.10 (13)
C3—C4—H4	108.6	C20—C21—H21	119.4
N1—C5—C4	102.03 (10)	C22—C21—H21	119.4
N1—C5—H5A	111.4	C23—C22—C21	120.47 (14)
C4—C5—H5A	111.4	C23—C22—H22	119.8
N1—C5—H5B	111.4	C21—C22—H22	119.8
C4—C5—H5B	111.4	C22—C23—C24	119.78 (14)
H5A—C5—H5B	109.2	C22—C23—H23	120.1
N1—C6—H6A	109.5	C24—C23—H23	120.1
N1—C6—H6B	109.5	C19—C24—C23	119.28 (12)
H6A—C6—H6B	109.5	C19—C24—C25	117.81 (11)
N1—C6—H6C	109.5	C23—C24—C25	122.91 (12)
H6A—C6—H6C	109.5	O4—C25—C16	121.98 (11)
H6B—C6—H6C	109.5	O4—C25—C24	116.49 (11)
O1—C7—N8	125.56 (11)	C16—C25—C24	121.52 (11)
O1—C7—C2	126.01 (10)	C27—C26—C31	117.78 (13)
N8—C7—C2	108.42 (10)	C27—C26—C4	120.84 (12)
C7—N8—C9	111.31 (10)	C31—C26—C4	121.36 (11)
C7—N8—H8	119.7 (11)	C26—C27—C28	120.68 (15)
C9—N8—H8	125.8 (11)	C26—C27—H27	119.7
C10—C9—C14	121.77 (12)	C28—C27—H27	119.7
C10—C9—N8	128.28 (12)	C29—C28—C27	120.29 (15)
C14—C9—N8	109.94 (10)	C29—C28—H28	119.9
C9—C10—C11	117.42 (13)	C27—C28—H28	119.9
C9—C10—H10	121.3	C28—C29—C30	119.90 (15)
C11—C10—H10	121.3	C28—C29—H29	120.0
C12—C11—C10	121.45 (14)	C30—C29—H29	120.0
C12—C11—H11	119.3	C29—C30—C31	120.13 (15)
C10—C11—H11	119.3	C29—C30—H30	119.9
C11—C12—C13	120.76 (13)	C31—C30—H30	119.9
C11—C12—H12	119.6	C30—C31—C26	121.18 (13)
C13—C12—H12	119.6	C30—C31—H31	119.4
C14—C13—C12	118.27 (12)	C26—C31—H31	119.4
C6—N1—C2—C14	67.51 (14)	C4—C3—C15—O2	−14.08 (15)
C5—N1—C2—C14	−162.83 (10)	C2—C3—C15—O2	106.11 (12)
C6—N1—C2—C7	−47.74 (15)	C4—C3—C15—C16	168.83 (10)
C5—N1—C2—C7	81.91 (12)	C2—C3—C15—C16	−70.98 (13)
C6—N1—C2—C3	−164.29 (11)	O2—C15—C16—C25	−10.92 (17)
C5—N1—C2—C3	−34.63 (11)	C3—C15—C16—C25	166.18 (10)
N1—C2—C3—C15	−116.48 (10)	O2—C15—C16—C17	171.31 (11)
C14—C2—C3—C15	9.00 (13)	C3—C15—C16—C17	−11.59 (16)
C7—C2—C3—C15	122.80 (10)	C25—C16—C17—O3	173.82 (11)
N1—C2—C3—C4	9.05 (11)	C15—C16—C17—O3	−8.41 (18)
C14—C2—C3—C4	134.53 (10)	C25—C16—C17—N18	−5.28 (16)
C7—C2—C3—C4	−111.68 (10)	C15—C16—C17—N18	172.49 (10)
C15—C3—C4—C26	−93.05 (12)	O3—C17—N18—C19	−175.84 (11)
C2—C3—C4—C26	142.55 (10)	C16—C17—N18—C19	3.31 (17)
C15—C3—C4—C5	142.18 (10)	C17—N18—C19—C24	−0.20 (18)
C2—C3—C4—C5	17.79 (11)	C17—N18—C19—C20	178.42 (11)
C6—N1—C5—C4	176.30 (10)	N18—C19—C20—C21	−178.69 (12)
C2—N1—C5—C4	46.99 (11)	C24—C19—C20—C21	−0.08 (19)
C26—C4—C5—N1	−161.42 (9)	C19—C20—C21—C22	−0.1 (2)
C3—C4—C5—N1	−38.53 (11)	C20—C21—C22—C23	0.2 (2)
N1—C2—C7—O1	−56.11 (16)	C21—C22—C23—C24	−0.2 (2)
C14—C2—C7—O1	−178.34 (12)	N18—C19—C24—C23	178.72 (11)
C3—C2—C7—O1	57.35 (15)	C20—C19—C24—C23	0.10 (18)
N1—C2—C7—N8	123.09 (11)	N18—C19—C24—C25	−0.94 (16)
C14—C2—C7—N8	0.87 (12)	C20—C19—C24—C25	−179.56 (11)
C3—C2—C7—N8	−123.44 (11)	C22—C23—C24—C19	0.0 (2)
O1—C7—N8—C9	−178.42 (12)	C22—C23—C24—C25	179.67 (13)
C2—C7—N8—C9	2.37 (14)	C17—C16—C25—O4	−176.49 (11)
C7—N8—C9—C10	175.61 (14)	C15—C16—C25—O4	5.67 (17)
C7—N8—C9—C14	−5.01 (15)	C17—C16—C25—C24	4.40 (17)
C14—C9—C10—C11	−1.3 (2)	C15—C16—C25—C24	−173.44 (10)
N8—C9—C10—C11	178.02 (15)	C19—C24—C25—O4	179.58 (11)
C9—C10—C11—C12	−1.6 (3)	C23—C24—C25—O4	−0.07 (18)
C10—C11—C12—C13	2.4 (3)	C19—C24—C25—C16	−1.26 (17)
C11—C12—C13—C14	−0.2 (2)	C23—C24—C25—C16	179.10 (12)
C12—C13—C14—C9	−2.6 (2)	C5—C4—C26—C27	−118.66 (13)
C12—C13—C14—C2	175.60 (13)	C3—C4—C26—C27	123.74 (13)
C10—C9—C14—C13	3.5 (2)	C5—C4—C26—C31	62.68 (15)
N8—C9—C14—C13	−175.95 (11)	C3—C4—C26—C31	−54.92 (15)
C10—C9—C14—C2	−175.11 (13)	C31—C26—C27—C28	2.1 (2)
N8—C9—C14—C2	5.46 (14)	C4—C26—C27—C28	−176.58 (14)
N1—C2—C14—C13	55.29 (17)	C26—C27—C28—C29	−0.6 (3)
C7—C2—C14—C13	177.84 (13)	C27—C28—C29—C30	−1.2 (3)
C3—C2—C14—C13	−64.72 (17)	C28—C29—C30—C31	1.4 (2)
N1—C2—C14—C9	−126.32 (11)	C29—C30—C31—C26	0.2 (2)
C7—C2—C14—C9	−3.78 (12)	C27—C26—C31—C30	−2.0 (2)
C3—C2—C14—C9	113.66 (11)	C4—C26—C31—C30	176.74 (12)

Cg6 is the centroid of the C26–C31 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2	0.99 (2)	1.56 (2)	2.4840 (14)	155 (2)
N8—H8···O3i	0.89 (2)	1.92 (2)	2.7837 (13)	165 (2)
N18—H18···O1i	0.90 (2)	1.95 (2)	2.8497 (14)	177 (2)
C3—H3···O3	0.98	2.21	2.7944 (13)	117
C21—H21···Cg6ii	0.93	2.72	3.5360 (18)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of the C26–C31 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2	0.99 (2)	1.56 (2)	2.4840 (14)	155 (2)
N8—H8⋯O3i	0.89 (2)	1.92 (2)	2.7837 (13)	165 (2)
N18—H18⋯O1i	0.90 (2)	1.95 (2)	2.8497 (14)	177 (2)
C3—H3⋯O3	0.98	2.21	2.7944 (13)	117
C21—H21⋯Cg6ii	0.93	2.72	3.5360 (18)	147

Symmetry codes: (i) ; (ii) .