5-Chloro-5''-[4-(di-methyl-amino)-benzyl-idene]-4'-[4-(di-methyl-amino)-phen-yl]-1',1''-di-methyl-dispiro-[indoline-3,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione.

The title compound, C34H38ClN5O2, has spiro links connecting the pyrrolidine ring and indole residue, as well as the piperidine and pyrrolidine rings. A half-chair conformation is found for the piperidine ring with the C atom connected to the spiro-C atom lying 0.738 (4) Å out of the plane of the remaining five atoms (r.m.s. deviation = 0.0407 Å). The methyl-ene C atom is the flap in the envelope conformation for the pyrrolidine ring. In the crystal, supra-molecular chains are sustained by alternating eight-membered {⋯HNCO}2 and 14-membered {⋯HC5O}2 synthons. Chains are connected into a three-dimensional network by (pyrrolidine-bound phenyl-meth-yl)C-H⋯π(pyrrolidine-bound phen-yl) edge-to-face inter-actions.

Related literature

For the biological activity of related spiro pyrrolidine analogues, see: Girgis et al. (2012 ▶); Kumar et al. (2008 ▶). For related structural studies, see: Ahmed Farag et al. (2013a ▶,b ▶). For the synthesis of the precursor mol­ecule, see: Al-Omary et al. (2012 ▶).

Experimental

Crystal data

C34H38ClN5O2

M = 584.14

Triclinic,

a = 11.5458 (5) Å

b = 12.2357 (5) Å

c = 12.5267 (7) Å

α = 64.341 (2)°

β = 84.286 (2)°

γ = 83.467 (2)°

V = 1582.29 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 293 K

0.31 × 0.18 × 0.13 mm

Data collection

Enraf–Nonius 590 KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.782, T max = 0.927

13814 measured reflections

7127 independent reflections

2244 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.165

S = 0.91

7127 reflections

385 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶), DIAMOND (Brandenburg, 2006 ▶) and Qmol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536813033771/hg5368sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033771/hg5368Isup2.hkl

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

C34H38ClN5O2	Z = 2
Mr = 584.14	F(000) = 620
Triclinic, P1	Dx = 1.226 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.5458 (5) Å	Cell parameters from 5831 reflections
b = 12.2357 (5) Å	θ = 2.9–27.5°
c = 12.5267 (7) Å	µ = 0.16 mm−1
α = 64.341 (2)°	T = 293 K
β = 84.286 (2)°	Block, orange
γ = 83.467 (2)°	0.31 × 0.18 × 0.13 mm
V = 1582.29 (13) Å3

Enraf–Nonius 590 KappaCCD diffractometer	7127 independent reflections
Radiation source: fine-focus sealed tube	2244 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
φ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.782, Tmax = 0.927	k = −15→15
13814 measured reflections	l = −16→10

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) = 0.165	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.055P)2] where P = (Fo2 + 2Fc2)/3
7127 reflections	(Δ/σ)max < 0.001
385 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.00842 (11)	0.90513 (9)	0.33316 (9)	0.1119 (5)
O1	0.3446 (2)	0.59561 (19)	0.5160 (2)	0.0750 (8)
O2	0.1064 (2)	0.4073 (2)	0.9448 (2)	0.0704 (7)
N1	0.2654 (2)	0.6453 (2)	0.8157 (2)	0.0469 (7)
N2	0.1139 (3)	0.4251 (3)	0.6910 (2)	0.0662 (9)
N3	0.3573 (3)	1.3398 (2)	0.3237 (2)	0.0652 (8)
N4	0.0072 (3)	0.5930 (3)	0.8421 (3)	0.0668 (9)
H4n	−0.0348	0.5979	0.9008	0.080*
N5	0.6847 (3)	0.0837 (3)	1.0145 (3)	0.0800 (10)
C1	0.2785 (3)	0.5106 (3)	0.7211 (3)	0.0504 (9)
C2	0.3223 (3)	0.5320 (3)	0.8207 (2)	0.0482 (9)
H2A	0.3038	0.4658	0.8968	0.058*
H2B	0.4063	0.5362	0.8108	0.058*
C3	0.3109 (3)	0.7505 (3)	0.7153 (2)	0.0494 (9)
H3A	0.3852	0.7653	0.7346	0.059*
H3B	0.2575	0.8215	0.7032	0.059*
C4	0.3277 (3)	0.7353 (3)	0.6021 (3)	0.0452 (8)
C5	0.3213 (3)	0.6136 (3)	0.6040 (3)	0.0507 (9)
C6	0.1383 (3)	0.5203 (3)	0.7259 (3)	0.0560 (10)
C7	0.1985 (3)	0.3228 (3)	0.7457 (3)	0.0749 (12)
H7A	0.2022	0.2669	0.7090	0.090*
H7B	0.1794	0.2792	0.8300	0.090*
C8	0.3149 (3)	0.3828 (3)	0.7230 (3)	0.0613 (10)
H8	0.3435	0.3973	0.6420	0.074*
C9	0.2653 (3)	0.6588 (3)	0.9254 (3)	0.0725 (11)
H9A	0.2272	0.5934	0.9884	0.109*
H9B	0.2244	0.7350	0.9160	0.109*
H9C	0.3443	0.6570	0.9443	0.109*
C10	−0.0077 (4)	0.3941 (3)	0.7112 (4)	0.1041 (15)
H10A	−0.0166	0.3365	0.6800	0.156*
H10B	−0.0579	0.4663	0.6721	0.156*
H10C	−0.0283	0.3590	0.7948	0.156*
C11	0.3454 (2)	0.8291 (3)	0.4941 (3)	0.0490 (9)
H11	0.3555	0.8061	0.4318	0.059*
C12	0.3515 (3)	0.9578 (3)	0.4575 (3)	0.0474 (9)
C13	0.3543 (3)	1.0342 (3)	0.3361 (3)	0.0551 (9)
H13	0.3540	0.9997	0.2830	0.066*
C14	0.3575 (3)	1.1582 (3)	0.2919 (3)	0.0561 (10)
H14	0.3596	1.2047	0.2102	0.067*
C15	0.3576 (3)	1.2159 (3)	0.3670 (3)	0.0500 (9)
C16	0.3594 (3)	1.1397 (3)	0.4884 (3)	0.0530 (9)
H16	0.3623	1.1737	0.5415	0.064*
C17	0.3571 (3)	1.0161 (3)	0.5311 (3)	0.0543 (10)
H17	0.3593	0.9690	0.6125	0.065*
C18	0.3406 (3)	1.3962 (3)	0.4056 (3)	0.0846 (13)
H18A	0.2661	1.3786	0.4480	0.127*
H18B	0.3435	1.4826	0.3621	0.127*
H18C	0.4013	1.3646	0.4607	0.127*
C19	0.3349 (3)	1.4166 (3)	0.2012 (3)	0.0779 (12)
H19A	0.3928	1.3961	0.1509	0.117*
H19B	0.3382	1.5002	0.1859	0.117*
H19C	0.2588	1.4047	0.1852	0.117*
C20	0.0856 (3)	0.4990 (4)	0.8513 (3)	0.0599 (10)
C21	0.0032 (3)	0.6814 (3)	0.7249 (3)	0.0568 (10)
C22	−0.0627 (3)	0.7898 (4)	0.6808 (4)	0.0724 (11)
H22	−0.1086	0.8163	0.7316	0.087*
C23	−0.0601 (3)	0.8595 (4)	0.5598 (4)	0.0775 (12)
H23	−0.1035	0.9342	0.5283	0.093*
C24	0.0067 (4)	0.8180 (3)	0.4863 (3)	0.0696 (11)
C25	0.0755 (3)	0.7089 (3)	0.5291 (3)	0.0667 (11)
H25	0.1204	0.6821	0.4780	0.080*
C26	0.0748 (3)	0.6413 (3)	0.6511 (3)	0.0545 (9)
C27	0.4107 (4)	0.3056 (3)	0.8031 (3)	0.0573 (10)
C28	0.5228 (4)	0.2936 (3)	0.7547 (3)	0.0693 (11)
H28	0.5377	0.3369	0.6735	0.083*
C29	0.6123 (4)	0.2206 (3)	0.8222 (4)	0.0689 (11)
H29	0.6851	0.2146	0.7852	0.083*
C30	0.5965 (4)	0.1550 (3)	0.9452 (4)	0.0645 (11)
C31	0.4844 (4)	0.1671 (3)	0.9943 (3)	0.0681 (11)
H31	0.4694	0.1245	1.0756	0.082*
C32	0.3959 (3)	0.2404 (3)	0.9255 (3)	0.0669 (11)
H32	0.3231	0.2467	0.9623	0.080*
C33	0.6631 (4)	0.0129 (3)	1.1413 (4)	0.0925 (13)
H33A	0.6249	0.0649	1.1757	0.139*
H33B	0.7360	−0.0223	1.1773	0.139*
H33C	0.6142	−0.0506	1.1545	0.139*
C34	0.7943 (4)	0.0575 (4)	0.9629 (4)	0.1278 (18)
H34A	0.7817	0.0180	0.9139	0.192*
H34B	0.8444	0.0049	1.0247	0.192*
H34C	0.8301	0.1318	0.9155	0.192*

	U11	U22	U33	U12	U13	U23
Cl1	0.1734 (13)	0.0715 (7)	0.0785 (8)	−0.0019 (7)	−0.0476 (8)	−0.0139 (6)
O1	0.128 (2)	0.0533 (14)	0.0436 (15)	−0.0158 (14)	0.0206 (15)	−0.0242 (12)
O2	0.0789 (19)	0.0616 (16)	0.0541 (16)	−0.0088 (14)	0.0129 (14)	−0.0119 (13)
N1	0.067 (2)	0.0403 (16)	0.0340 (16)	−0.0073 (14)	0.0040 (14)	−0.0171 (13)
N2	0.084 (2)	0.0508 (19)	0.070 (2)	−0.0043 (19)	−0.0158 (18)	−0.0298 (16)
N3	0.098 (2)	0.0430 (18)	0.0476 (19)	−0.0053 (16)	−0.0090 (17)	−0.0116 (16)
N4	0.065 (2)	0.065 (2)	0.063 (2)	−0.0093 (18)	0.0162 (17)	−0.0227 (18)
N5	0.086 (3)	0.078 (2)	0.075 (3)	0.005 (2)	−0.002 (2)	−0.035 (2)
C1	0.070 (3)	0.041 (2)	0.039 (2)	−0.0017 (18)	0.0080 (19)	−0.0191 (16)
C2	0.062 (2)	0.041 (2)	0.038 (2)	−0.0047 (17)	0.0013 (17)	−0.0141 (16)
C3	0.061 (2)	0.0426 (19)	0.041 (2)	−0.0002 (17)	−0.0038 (17)	−0.0146 (16)
C4	0.054 (2)	0.045 (2)	0.039 (2)	−0.0054 (17)	0.0056 (17)	−0.0213 (17)
C5	0.064 (2)	0.046 (2)	0.040 (2)	−0.0014 (18)	0.0042 (19)	−0.0183 (18)
C6	0.071 (3)	0.050 (2)	0.052 (2)	−0.010 (2)	0.000 (2)	−0.0258 (19)
C7	0.108 (3)	0.054 (2)	0.071 (3)	−0.011 (3)	−0.009 (2)	−0.032 (2)
C8	0.089 (3)	0.051 (2)	0.045 (2)	0.001 (2)	0.006 (2)	−0.0245 (18)
C9	0.118 (3)	0.058 (2)	0.042 (2)	−0.017 (2)	0.008 (2)	−0.0220 (19)
C10	0.102 (4)	0.086 (3)	0.140 (4)	−0.029 (3)	−0.031 (3)	−0.053 (3)
C11	0.055 (2)	0.049 (2)	0.041 (2)	−0.0022 (18)	0.0066 (17)	−0.0208 (17)
C12	0.053 (2)	0.045 (2)	0.041 (2)	−0.0061 (17)	0.0014 (17)	−0.0155 (18)
C13	0.071 (3)	0.054 (2)	0.042 (2)	−0.0079 (19)	0.0039 (18)	−0.0218 (18)
C14	0.068 (3)	0.055 (2)	0.035 (2)	−0.0096 (19)	0.0049 (18)	−0.0099 (18)
C15	0.056 (2)	0.046 (2)	0.045 (2)	−0.0046 (18)	−0.0027 (18)	−0.0161 (19)
C16	0.067 (3)	0.048 (2)	0.042 (2)	−0.0052 (19)	−0.0084 (18)	−0.0173 (18)
C17	0.066 (3)	0.049 (2)	0.042 (2)	−0.0083 (19)	−0.0037 (18)	−0.0116 (18)
C18	0.123 (4)	0.053 (2)	0.076 (3)	−0.010 (2)	0.002 (3)	−0.027 (2)
C19	0.100 (3)	0.045 (2)	0.069 (3)	−0.010 (2)	−0.015 (2)	−0.003 (2)
C20	0.063 (3)	0.058 (3)	0.059 (3)	−0.015 (2)	0.006 (2)	−0.025 (2)
C21	0.052 (3)	0.053 (2)	0.065 (3)	−0.007 (2)	−0.002 (2)	−0.023 (2)
C22	0.060 (3)	0.070 (3)	0.088 (3)	0.000 (2)	0.000 (2)	−0.037 (3)
C23	0.070 (3)	0.065 (3)	0.097 (4)	0.001 (2)	−0.024 (3)	−0.031 (3)
C24	0.087 (3)	0.050 (3)	0.068 (3)	−0.009 (2)	−0.022 (3)	−0.017 (2)
C25	0.085 (3)	0.060 (3)	0.060 (3)	−0.010 (2)	−0.015 (2)	−0.026 (2)
C26	0.063 (3)	0.047 (2)	0.055 (3)	−0.0063 (19)	−0.006 (2)	−0.021 (2)
C27	0.083 (3)	0.041 (2)	0.041 (2)	0.005 (2)	0.007 (2)	−0.0154 (18)
C28	0.096 (3)	0.051 (2)	0.052 (3)	−0.011 (2)	0.020 (3)	−0.017 (2)
C29	0.075 (3)	0.066 (3)	0.064 (3)	−0.005 (2)	0.014 (2)	−0.030 (2)
C30	0.081 (3)	0.047 (2)	0.066 (3)	0.006 (2)	−0.007 (3)	−0.026 (2)
C31	0.094 (3)	0.052 (2)	0.048 (3)	0.010 (2)	0.004 (3)	−0.017 (2)
C32	0.087 (3)	0.058 (2)	0.047 (3)	0.002 (2)	0.019 (2)	−0.021 (2)
C33	0.122 (4)	0.071 (3)	0.085 (3)	0.016 (3)	−0.029 (3)	−0.035 (3)
C34	0.095 (4)	0.143 (5)	0.135 (5)	0.033 (3)	−0.008 (4)	−0.060 (4)

Cl1—C24	1.744 (4)	C11—H11	0.9300
O1—C5	1.214 (3)	C12—C13	1.398 (4)
O2—C20	1.244 (4)	C12—C17	1.397 (4)
N1—C2	1.444 (4)	C13—C14	1.375 (4)
N1—C9	1.453 (4)	C13—H13	0.9300
N1—C3	1.461 (3)	C14—C15	1.400 (4)
N2—C7	1.450 (4)	C14—H14	0.9300
N2—C10	1.465 (4)	C15—C16	1.399 (4)
N2—C6	1.472 (4)	C16—C17	1.371 (4)
N3—C15	1.370 (4)	C16—H16	0.9300
N3—C19	1.442 (4)	C17—H17	0.9300
N3—C18	1.452 (4)	C18—H18A	0.9600
N4—C20	1.350 (4)	C18—H18B	0.9600
N4—C21	1.398 (4)	C18—H18C	0.9600
N4—H4n	0.8600	C19—H19A	0.9600
N5—C30	1.368 (4)	C19—H19B	0.9600
N5—C34	1.430 (5)	C19—H19C	0.9600
N5—C33	1.453 (4)	C21—C22	1.365 (5)
C1—C2	1.523 (4)	C21—C26	1.388 (4)
C1—C5	1.542 (4)	C22—C23	1.379 (5)
C1—C8	1.563 (4)	C22—H22	0.9300
C1—C6	1.606 (4)	C23—C24	1.369 (5)
C2—H2A	0.9700	C23—H23	0.9300
C2—H2B	0.9700	C24—C25	1.387 (5)
C3—C4	1.499 (4)	C25—C26	1.387 (4)
C3—H3A	0.9700	C25—H25	0.9300
C3—H3B	0.9700	C27—C32	1.392 (4)
C4—C11	1.358 (4)	C27—C28	1.393 (4)
C4—C5	1.490 (4)	C28—C29	1.375 (5)
C6—C26	1.515 (4)	C28—H28	0.9300
C6—C20	1.549 (4)	C29—C30	1.399 (5)
C7—C8	1.547 (4)	C29—H29	0.9300
C7—H7A	0.9700	C30—C31	1.397 (5)
C7—H7B	0.9700	C31—C32	1.375 (4)
C8—C27	1.512 (4)	C31—H31	0.9300
C8—H8	0.9800	C32—H32	0.9300
C9—H9A	0.9600	C33—H33A	0.9600
C9—H9B	0.9600	C33—H33B	0.9600
C9—H9C	0.9600	C33—H33C	0.9600
C10—H10A	0.9600	C34—H34A	0.9600
C10—H10B	0.9600	C34—H34B	0.9600
C10—H10C	0.9600	C34—H34C	0.9600
C11—C12	1.446 (4)
C2—N1—C9	114.3 (3)	C12—C13—H13	118.6
C2—N1—C3	112.1 (2)	C13—C14—C15	121.5 (3)
C9—N1—C3	110.9 (2)	C13—C14—H14	119.2
C7—N2—C10	114.6 (3)	C15—C14—H14	119.2
C7—N2—C6	107.0 (3)	N3—C15—C16	122.1 (3)
C10—N2—C6	115.4 (3)	N3—C15—C14	121.8 (3)
C15—N3—C19	120.4 (3)	C16—C15—C14	116.1 (3)
C15—N3—C18	119.4 (3)	C17—C16—C15	121.7 (3)
C19—N3—C18	117.1 (3)	C17—C16—H16	119.2
C20—N4—C21	111.3 (3)	C15—C16—H16	119.2
C20—N4—H4n	124.4	C16—C17—C12	122.8 (3)
C21—N4—H4n	124.4	C16—C17—H17	118.6
C30—N5—C34	121.1 (4)	C12—C17—H17	118.6
C30—N5—C33	120.8 (4)	N3—C18—H18A	109.5
C34—N5—C33	116.9 (4)	N3—C18—H18B	109.5
C2—C1—C5	106.3 (2)	H18A—C18—H18B	109.5
C2—C1—C8	115.7 (3)	N3—C18—H18C	109.5
C5—C1—C8	111.4 (3)	H18A—C18—H18C	109.5
C2—C1—C6	111.1 (3)	H18B—C18—H18C	109.5
C5—C1—C6	108.0 (3)	N3—C19—H19A	109.5
C8—C1—C6	104.1 (2)	N3—C19—H19B	109.5
N1—C2—C1	107.8 (3)	H19A—C19—H19B	109.5
N1—C2—H2A	110.2	N3—C19—H19C	109.5
C1—C2—H2A	110.2	H19A—C19—H19C	109.5
N1—C2—H2B	110.2	H19B—C19—H19C	109.5
C1—C2—H2B	110.2	O2—C20—N4	125.1 (3)
H2A—C2—H2B	108.5	O2—C20—C6	125.9 (4)
N1—C3—C4	113.6 (2)	N4—C20—C6	108.9 (3)
N1—C3—H3A	108.9	C22—C21—C26	121.5 (4)
C4—C3—H3A	108.9	C22—C21—N4	128.7 (4)
N1—C3—H3B	108.9	C26—C21—N4	109.7 (3)
C4—C3—H3B	108.9	C21—C22—C23	119.1 (4)
H3A—C3—H3B	107.7	C21—C22—H22	120.4
C11—C4—C5	116.6 (3)	C23—C22—H22	120.4
C11—C4—C3	123.2 (3)	C24—C23—C22	119.6 (4)
C5—C4—C3	120.1 (2)	C24—C23—H23	120.2
O1—C5—C4	121.9 (3)	C22—C23—H23	120.2
O1—C5—C1	120.2 (3)	C23—C24—C25	122.3 (4)
C4—C5—C1	117.8 (3)	C23—C24—Cl1	119.6 (4)
N2—C6—C26	111.2 (3)	C25—C24—Cl1	118.1 (4)
N2—C6—C20	112.8 (3)	C26—C25—C24	117.6 (4)
C26—C6—C20	100.7 (3)	C26—C25—H25	121.2
N2—C6—C1	102.7 (3)	C24—C25—H25	121.2
C26—C6—C1	118.5 (3)	C25—C26—C21	119.8 (4)
C20—C6—C1	111.4 (3)	C25—C26—C6	131.0 (4)
N2—C7—C8	103.5 (3)	C21—C26—C6	109.1 (3)
N2—C7—H7A	111.1	C32—C27—C28	115.3 (4)
C8—C7—H7A	111.1	C32—C27—C8	124.8 (4)
N2—C7—H7B	111.1	C28—C27—C8	120.0 (3)
C8—C7—H7B	111.1	C29—C28—C27	122.7 (3)
H7A—C7—H7B	109.0	C29—C28—H28	118.6
C27—C8—C7	115.2 (3)	C27—C28—H28	118.6
C27—C8—C1	117.2 (3)	C28—C29—C30	121.6 (4)
C7—C8—C1	104.4 (3)	C28—C29—H29	119.2
C27—C8—H8	106.4	C30—C29—H29	119.2
C7—C8—H8	106.4	N5—C30—C31	121.3 (4)
C1—C8—H8	106.4	N5—C30—C29	122.7 (4)
N1—C9—H9A	109.5	C31—C30—C29	116.0 (4)
N1—C9—H9B	109.5	C32—C31—C30	121.6 (4)
H9A—C9—H9B	109.5	C32—C31—H31	119.2
N1—C9—H9C	109.5	C30—C31—H31	119.2
H9A—C9—H9C	109.5	C31—C32—C27	122.8 (4)
H9B—C9—H9C	109.5	C31—C32—H32	118.6
N2—C10—H10A	109.5	C27—C32—H32	118.6
N2—C10—H10B	109.5	N5—C33—H33A	109.5
H10A—C10—H10B	109.5	N5—C33—H33B	109.5
N2—C10—H10C	109.5	H33A—C33—H33B	109.5
H10A—C10—H10C	109.5	N5—C33—H33C	109.5
H10B—C10—H10C	109.5	H33A—C33—H33C	109.5
C4—C11—C12	132.2 (3)	H33B—C33—H33C	109.5
C4—C11—H11	113.9	N5—C34—H34A	109.5
C12—C11—H11	113.9	N5—C34—H34B	109.5
C13—C12—C17	115.1 (3)	H34A—C34—H34B	109.5
C13—C12—C11	118.0 (3)	N5—C34—H34C	109.5
C17—C12—C11	126.9 (3)	H34A—C34—H34C	109.5
C14—C13—C12	122.7 (3)	H34B—C34—H34C	109.5
C14—C13—H13	118.6

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4n···O2i	0.86	2.00	2.853 (4)	169
C28—H28···O1ii	0.93	2.47	3.337 (4)	156
C33—H33c···Cg1iii	0.96	2.88	3.807 (5)	163

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C27–C32 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4n⋯O2i	0.86	2.00	2.853 (4)	169
C28—H28⋯O1ii	0.93	2.47	3.337 (4)	156
C33—H33c⋯Cg1iii	0.96	2.88	3.807 (5)	163

Symmetry codes: (i) ; (ii) ; (iii) .