1',1''-Dimethyl-4'-phenyl-dispiro-[11H-indeno-[1,2-b]quinoxaline-11,2'-pyrrolidine-3',3''-piperidin]-4''-one.

In the title compound, C30H28N4O, the central pyrrolidine ring adopts an envelope conformation with the CH2 C atom as the flap. The quinoxaline and indene ring systems are planar, with r.m.s. deviations of 0.0165 and 0.0181 Å, respectively. The pyrrolidine ring mean plane forms dihedral angles of 88.84 (1) and 86.14 (1)° with the quinoxaline and indene ring systems, respectively. A weak intra-molecular C-H⋯N inter-action is observed. In the crystal, C-H⋯O inter-actions lead to helical supra-molecular chains along the b axis having a C(9) motif.

Related literature

For the importance of spiro compounds, see: Kobayashi et al. (1991 ▶); James et al. (1991 ▶). For the importance of pyrrolidine derivatives, see: Amal Raj et al. (2003 ▶). For conformation analysis, see: Cremer & Pople (1975 ▶). For a related structure, see: Selvanayagam et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C30H28N4O

M = 460.56

Monoclinic,

a = 13.4470 (6) Å

b = 8.4557 (4) Å

c = 20.8580 (9) Å

β = 90.195 (2)°

V = 2371.62 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.21 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.974

28395 measured reflections

6662 independent reflections

4394 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.138

S = 1.02

6662 reflections

316 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681302223X/tk5246sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302223X/tk5246Isup2.hkl

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

C30H28N4O	F(000) = 976
Mr = 460.56	Dx = 1.290 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 13.4470 (6) Å	θ = 2–31°
b = 8.4557 (4) Å	µ = 0.08 mm−1
c = 20.8580 (9) Å	T = 293 K
β = 90.195 (2)°	Block, green
V = 2371.62 (19) Å3	0.21 × 0.19 × 0.18 mm
Z = 4

Bruker Kappa APEXII diffractometer	6662 independent reflections
Radiation source: fine-focus sealed tube	4394 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 0 pixels mm-1	θmax = 29.7°, θmin = 2.5°
ω and φ scans	h = −18→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.967, Tmax = 0.974	l = −18→28
28395 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.385P] where P = (Fo2 + 2Fc2)/3
6662 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.23 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.

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 > 2sigma(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
C1	0.36237 (14)	0.57618 (18)	0.06530 (9)	0.0608 (4)
H1A	0.3764	0.5501	0.1092	0.091*
H1B	0.4125	0.5310	0.0383	0.091*
H1C	0.2985	0.5346	0.0535	0.091*
C2	0.34240 (11)	0.80537 (17)	−0.00602 (7)	0.0444 (3)
H2A	0.2771	0.7738	−0.0212	0.053*
H2B	0.3924	0.7701	−0.0362	0.053*
C3	0.34818 (10)	0.98182 (15)	0.00505 (6)	0.0367 (3)
H3	0.4176	1.0048	0.0159	0.044*
C4	0.28798 (9)	1.00430 (14)	0.06781 (6)	0.0329 (3)
C5	0.30193 (10)	0.83818 (15)	0.10348 (6)	0.0355 (3)
C6	0.35593 (10)	0.84200 (15)	0.16788 (6)	0.0393 (3)
C7	0.30027 (11)	0.77358 (16)	0.21664 (6)	0.0408 (3)
C8	0.33822 (13)	0.75968 (19)	0.27843 (7)	0.0529 (4)
H8	0.3010	0.7129	0.3108	0.063*
C9	0.43177 (13)	0.8165 (2)	0.29050 (8)	0.0597 (4)
H9	0.4581	0.8091	0.3317	0.072*
C10	0.48776 (13)	0.8847 (2)	0.24228 (8)	0.0584 (4)
H10	0.5509	0.9232	0.2516	0.070*
C11	0.45123 (11)	0.89637 (18)	0.18041 (8)	0.0491 (4)
H11	0.4898	0.9398	0.1479	0.059*
C12	0.20533 (10)	0.75594 (14)	0.12273 (6)	0.0363 (3)
C13	0.20671 (10)	0.71782 (15)	0.18953 (6)	0.0392 (3)
C14	0.05869 (11)	0.59550 (16)	0.17986 (7)	0.0458 (3)
C15	0.05754 (11)	0.63118 (16)	0.11364 (7)	0.0431 (3)
C16	−0.02353 (12)	0.58276 (19)	0.07619 (9)	0.0541 (4)
H16	−0.0262	0.6090	0.0329	0.065*
C17	−0.09862 (13)	0.4972 (2)	0.10312 (10)	0.0672 (5)
H17	−0.1520	0.4645	0.0779	0.081*
C18	−0.09591 (14)	0.4583 (2)	0.16794 (11)	0.0701 (5)
H18	−0.1470	0.3981	0.1854	0.084*
C19	−0.02015 (13)	0.5068 (2)	0.20580 (9)	0.0600 (4)
H19	−0.0200	0.4815	0.2492	0.072*
C31	0.32246 (11)	1.08677 (18)	−0.05113 (6)	0.0436 (3)
C32	0.25500 (13)	1.0445 (2)	−0.09802 (7)	0.0615 (4)
H32	0.2198	0.9503	−0.0943	0.074*
C33	0.23919 (18)	1.1419 (3)	−0.15091 (9)	0.0826 (7)
H33	0.1942	1.1119	−0.1826	0.099*
C34	0.2896 (2)	1.2812 (3)	−0.15630 (9)	0.0873 (7)
H34	0.2787	1.3462	−0.1916	0.105*
C35	0.35562 (18)	1.3253 (3)	−0.11021 (10)	0.0787 (6)
H35	0.3894	1.4209	−0.1138	0.094*
C36	0.37261 (13)	1.2288 (2)	−0.05827 (8)	0.0594 (4)
H36	0.4187	1.2594	−0.0273	0.071*
C41	0.17892 (10)	1.04422 (16)	0.05398 (6)	0.0379 (3)
H41A	0.1758	1.1387	0.0277	0.045*
H41B	0.1490	0.9583	0.0299	0.045*
C42	0.01616 (12)	1.0763 (2)	0.09830 (9)	0.0662 (5)
H42A	−0.0039	0.9799	0.0777	0.099*
H42B	0.0028	1.1641	0.0704	0.099*
H42C	−0.0203	1.0891	0.1375	0.099*
C43	0.15684 (14)	1.21341 (18)	0.14362 (8)	0.0576 (4)
H43A	0.1172	1.2339	0.1815	0.069*
H43B	0.1493	1.3024	0.1147	0.069*
C44	0.26476 (14)	1.19575 (19)	0.16236 (7)	0.0571 (4)
H44A	0.2894	1.2966	0.1779	0.069*
H44B	0.2700	1.1201	0.1972	0.069*
C45	0.32857 (11)	1.14165 (16)	0.10784 (6)	0.0419 (3)
N1	0.36204 (9)	0.74661 (13)	0.05769 (6)	0.0422 (3)
N2	0.12222 (9)	1.07001 (14)	0.11253 (5)	0.0457 (3)
N3	0.13447 (9)	0.71125 (13)	0.08434 (5)	0.0408 (3)
N4	0.13632 (9)	0.63976 (14)	0.21868 (6)	0.0469 (3)
O1	0.40639 (9)	1.20595 (13)	0.09512 (5)	0.0567 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0738 (11)	0.0356 (8)	0.0732 (11)	0.0120 (8)	0.0169 (9)	−0.0021 (7)
C2	0.0490 (8)	0.0435 (8)	0.0408 (7)	0.0026 (6)	0.0096 (6)	−0.0072 (6)
C3	0.0359 (7)	0.0398 (7)	0.0344 (6)	−0.0005 (5)	0.0027 (5)	−0.0005 (5)
C4	0.0381 (7)	0.0314 (6)	0.0292 (6)	0.0015 (5)	0.0004 (5)	−0.0012 (5)
C5	0.0388 (7)	0.0328 (6)	0.0348 (6)	0.0028 (5)	0.0014 (5)	0.0003 (5)
C6	0.0426 (7)	0.0342 (6)	0.0411 (7)	0.0081 (6)	−0.0034 (6)	0.0007 (6)
C7	0.0473 (8)	0.0370 (7)	0.0382 (7)	0.0111 (6)	−0.0002 (6)	0.0027 (6)
C8	0.0624 (10)	0.0552 (9)	0.0411 (8)	0.0167 (8)	−0.0013 (7)	0.0061 (7)
C9	0.0654 (11)	0.0668 (10)	0.0466 (9)	0.0209 (9)	−0.0182 (8)	−0.0010 (8)
C10	0.0520 (9)	0.0629 (10)	0.0604 (10)	0.0118 (8)	−0.0172 (8)	−0.0023 (8)
C11	0.0458 (8)	0.0481 (8)	0.0535 (9)	0.0051 (7)	−0.0059 (7)	0.0022 (7)
C12	0.0424 (7)	0.0292 (6)	0.0374 (7)	0.0040 (5)	0.0036 (5)	−0.0002 (5)
C13	0.0474 (8)	0.0326 (6)	0.0378 (7)	0.0073 (6)	0.0062 (6)	0.0019 (5)
C14	0.0480 (8)	0.0351 (7)	0.0545 (9)	0.0054 (6)	0.0139 (7)	0.0006 (6)
C15	0.0430 (8)	0.0329 (7)	0.0534 (8)	0.0008 (6)	0.0091 (6)	−0.0055 (6)
C16	0.0509 (9)	0.0466 (8)	0.0648 (10)	−0.0048 (7)	0.0039 (7)	−0.0112 (7)
C17	0.0481 (10)	0.0606 (11)	0.0930 (14)	−0.0111 (8)	0.0067 (9)	−0.0129 (10)
C18	0.0543 (10)	0.0594 (11)	0.0969 (15)	−0.0102 (8)	0.0240 (10)	0.0029 (10)
C19	0.0561 (10)	0.0533 (9)	0.0707 (11)	−0.0002 (8)	0.0227 (8)	0.0073 (8)
C31	0.0459 (8)	0.0520 (8)	0.0330 (7)	0.0083 (6)	0.0100 (6)	0.0015 (6)
C32	0.0652 (11)	0.0785 (12)	0.0406 (8)	0.0092 (9)	−0.0033 (7)	−0.0034 (8)
C33	0.0974 (16)	0.1114 (18)	0.0389 (9)	0.0342 (14)	−0.0113 (9)	−0.0023 (10)
C34	0.1221 (19)	0.0938 (17)	0.0461 (11)	0.0480 (15)	0.0199 (12)	0.0228 (11)
C35	0.1013 (16)	0.0702 (12)	0.0647 (12)	0.0143 (11)	0.0216 (11)	0.0275 (10)
C36	0.0686 (11)	0.0565 (10)	0.0534 (9)	0.0014 (8)	0.0094 (8)	0.0130 (8)
C41	0.0420 (7)	0.0379 (7)	0.0338 (6)	0.0058 (6)	0.0033 (5)	0.0028 (5)
C42	0.0499 (10)	0.0749 (12)	0.0741 (11)	0.0191 (9)	0.0175 (8)	0.0087 (9)
C43	0.0811 (12)	0.0435 (8)	0.0485 (9)	0.0169 (7)	0.0164 (8)	−0.0054 (6)
C44	0.0888 (13)	0.0429 (8)	0.0396 (8)	0.0051 (8)	−0.0033 (8)	−0.0118 (6)
C45	0.0560 (9)	0.0333 (7)	0.0363 (7)	0.0012 (6)	−0.0102 (6)	0.0011 (5)
N1	0.0483 (7)	0.0334 (6)	0.0450 (6)	0.0073 (5)	0.0081 (5)	−0.0017 (5)
N2	0.0499 (7)	0.0447 (6)	0.0426 (6)	0.0114 (5)	0.0118 (5)	0.0014 (5)
N3	0.0451 (7)	0.0362 (6)	0.0410 (6)	−0.0024 (5)	0.0037 (5)	−0.0034 (5)
N4	0.0512 (7)	0.0441 (7)	0.0456 (7)	0.0052 (6)	0.0114 (6)	0.0063 (5)
O1	0.0632 (7)	0.0481 (6)	0.0586 (7)	−0.0154 (5)	−0.0148 (5)	0.0004 (5)

C1—N1	1.4499 (18)	C15—C16	1.400 (2)
C1—H1A	0.9600	C16—C17	1.365 (2)
C1—H1B	0.9600	C16—H16	0.9300
C1—H1C	0.9600	C17—C18	1.392 (3)
C2—N1	1.4423 (18)	C17—H17	0.9300
C2—C3	1.5117 (19)	C18—C19	1.351 (3)
C2—H2A	0.9700	C18—H18	0.9300
C2—H2B	0.9700	C19—H19	0.9300
C3—C31	1.5091 (18)	C31—C32	1.379 (2)
C3—C4	1.5531 (17)	C31—C36	1.385 (2)
C3—H3	0.9800	C32—C33	1.393 (3)
C4—C45	1.5301 (18)	C32—H32	0.9300
C4—C41	1.5312 (18)	C33—C34	1.364 (3)
C4—C5	1.6003 (17)	C33—H33	0.9300
C5—N1	1.4731 (17)	C34—C35	1.359 (3)
C5—C6	1.5252 (18)	C34—H34	0.9300
C5—C12	1.5284 (19)	C35—C36	1.375 (2)
C6—C11	1.386 (2)	C35—H35	0.9300
C6—C7	1.3908 (19)	C36—H36	0.9300
C7—C8	1.389 (2)	C41—N2	1.4582 (17)
C7—C13	1.456 (2)	C41—H41A	0.9700
C8—C9	1.369 (2)	C41—H41B	0.9700
C8—H8	0.9300	C42—N2	1.457 (2)
C9—C10	1.384 (3)	C42—H42A	0.9600
C9—H9	0.9300	C42—H42B	0.9600
C10—C11	1.383 (2)	C42—H42C	0.9600
C10—H10	0.9300	C43—N2	1.451 (2)
C11—H11	0.9300	C43—C44	1.509 (2)
C12—N3	1.2986 (17)	C43—H43A	0.9700
C12—C13	1.4302 (19)	C43—H43B	0.9700
C13—N4	1.3058 (18)	C44—C45	1.498 (2)
C14—N4	1.371 (2)	C44—H44A	0.9700
C14—C19	1.408 (2)	C44—H44B	0.9700
C14—C15	1.414 (2)	C45—O1	1.2095 (18)
C15—N3	1.3807 (18)
N1—C1—H1A	109.5	C16—C17—C18	120.53 (17)
N1—C1—H1B	109.5	C16—C17—H17	119.7
H1A—C1—H1B	109.5	C18—C17—H17	119.7
N1—C1—H1C	109.5	C19—C18—C17	120.90 (17)
H1A—C1—H1C	109.5	C19—C18—H18	119.5
H1B—C1—H1C	109.5	C17—C18—H18	119.5
N1—C2—C3	100.96 (11)	C18—C19—C14	120.29 (17)
N1—C2—H2A	111.6	C18—C19—H19	119.9
C3—C2—H2A	111.6	C14—C19—H19	119.9
N1—C2—H2B	111.6	C32—C31—C36	117.89 (15)
C3—C2—H2B	111.6	C32—C31—C3	123.14 (14)
H2A—C2—H2B	109.4	C36—C31—C3	118.87 (13)
C31—C3—C2	116.76 (11)	C31—C32—C33	120.5 (2)
C31—C3—C4	117.63 (11)	C31—C32—H32	119.8
C2—C3—C4	102.87 (10)	C33—C32—H32	119.8
C31—C3—H3	106.2	C34—C33—C32	120.1 (2)
C2—C3—H3	106.2	C34—C33—H33	119.9
C4—C3—H3	106.2	C32—C33—H33	119.9
C45—C4—C41	105.97 (10)	C35—C34—C33	120.16 (18)
C45—C4—C3	111.52 (11)	C35—C34—H34	119.9
C41—C4—C3	111.71 (10)	C33—C34—H34	119.9
C45—C4—C5	111.80 (10)	C34—C35—C36	120.1 (2)
C41—C4—C5	113.06 (10)	C34—C35—H35	120.0
C3—C4—C5	102.93 (9)	C36—C35—H35	120.0
N1—C5—C6	108.76 (10)	C35—C36—C31	121.31 (19)
N1—C5—C12	113.57 (11)	C35—C36—H36	119.3
C6—C5—C12	100.41 (10)	C31—C36—H36	119.3
N1—C5—C4	102.92 (10)	N2—C41—C4	112.24 (10)
C6—C5—C4	116.47 (10)	N2—C41—H41A	109.2
C12—C5—C4	115.03 (10)	C4—C41—H41A	109.2
C11—C6—C7	119.99 (13)	N2—C41—H41B	109.2
C11—C6—C5	127.61 (13)	C4—C41—H41B	109.2
C7—C6—C5	112.30 (12)	H41A—C41—H41B	107.9
C8—C7—C6	121.10 (14)	N2—C42—H42A	109.5
C8—C7—C13	130.31 (14)	N2—C42—H42B	109.5
C6—C7—C13	108.49 (11)	H42A—C42—H42B	109.5
C9—C8—C7	118.38 (16)	N2—C42—H42C	109.5
C9—C8—H8	120.8	H42A—C42—H42C	109.5
C7—C8—H8	120.8	H42B—C42—H42C	109.5
C8—C9—C10	120.94 (14)	N2—C43—C44	109.87 (12)
C8—C9—H9	119.5	N2—C43—H43A	109.7
C10—C9—H9	119.5	C44—C43—H43A	109.7
C11—C10—C9	121.03 (16)	N2—C43—H43B	109.7
C11—C10—H10	119.5	C44—C43—H43B	109.7
C9—C10—H10	119.5	H43A—C43—H43B	108.2
C10—C11—C6	118.53 (15)	C45—C44—C43	112.72 (12)
C10—C11—H11	120.7	C45—C44—H44A	109.0
C6—C11—H11	120.7	C43—C44—H44A	109.0
N3—C12—C13	122.84 (13)	C45—C44—H44B	109.0
N3—C12—C5	126.36 (12)	C43—C44—H44B	109.0
C13—C12—C5	110.50 (11)	H44A—C44—H44B	107.8
N4—C13—C12	124.08 (13)	O1—C45—C44	121.83 (13)
N4—C13—C7	127.56 (13)	O1—C45—C4	121.92 (13)
C12—C13—C7	108.29 (12)	C44—C45—C4	116.22 (13)
N4—C14—C19	119.42 (15)	C2—N1—C1	116.35 (12)
N4—C14—C15	121.63 (13)	C2—N1—C5	108.49 (10)
C19—C14—C15	118.90 (15)	C1—N1—C5	116.94 (12)
N3—C15—C16	118.66 (14)	C43—N2—C42	111.90 (13)
N3—C15—C14	122.10 (13)	C43—N2—C41	109.35 (12)
C16—C15—C14	119.24 (14)	C42—N2—C41	110.44 (12)
C17—C16—C15	120.08 (17)	C12—N3—C15	114.77 (12)
C17—C16—H16	120.0	C13—N4—C14	114.51 (12)
C15—C16—H16	120.0
N1—C2—C3—C31	−174.91 (11)	N3—C15—C16—C17	177.03 (14)
N1—C2—C3—C4	−44.52 (13)	C14—C15—C16—C17	−2.4 (2)
C31—C3—C4—C45	−82.17 (14)	C15—C16—C17—C18	0.5 (3)
C2—C3—C4—C45	147.97 (11)	C16—C17—C18—C19	1.3 (3)
C31—C3—C4—C41	36.21 (16)	C17—C18—C19—C14	−1.2 (3)
C2—C3—C4—C41	−93.65 (12)	N4—C14—C19—C18	−178.14 (15)
C31—C3—C4—C5	157.82 (11)	C15—C14—C19—C18	−0.7 (2)
C2—C3—C4—C5	27.95 (12)	C2—C3—C31—C32	30.6 (2)
C45—C4—C5—N1	−121.60 (11)	C4—C3—C31—C32	−92.51 (16)
C41—C4—C5—N1	118.90 (11)	C2—C3—C31—C36	−145.75 (14)
C3—C4—C5—N1	−1.78 (12)	C4—C3—C31—C36	91.18 (16)
C45—C4—C5—C6	−2.74 (15)	C36—C31—C32—C33	0.6 (2)
C41—C4—C5—C6	−122.24 (12)	C3—C31—C32—C33	−175.77 (15)
C3—C4—C5—C6	117.08 (12)	C31—C32—C33—C34	−0.9 (3)
C45—C4—C5—C12	114.35 (13)	C32—C33—C34—C35	0.2 (3)
C41—C4—C5—C12	−5.15 (14)	C33—C34—C35—C36	0.6 (3)
C3—C4—C5—C12	−125.83 (11)	C34—C35—C36—C31	−0.9 (3)
N1—C5—C6—C11	56.97 (17)	C32—C31—C36—C35	0.3 (2)
C12—C5—C6—C11	176.43 (13)	C3—C31—C36—C35	176.80 (15)
C4—C5—C6—C11	−58.68 (18)	C45—C4—C41—N2	−56.74 (14)
N1—C5—C6—C7	−119.49 (12)	C3—C4—C41—N2	−178.38 (11)
C12—C5—C6—C7	−0.03 (13)	C5—C4—C41—N2	66.07 (13)
C4—C5—C6—C7	124.86 (12)	N2—C43—C44—C45	51.34 (18)
C11—C6—C7—C8	0.6 (2)	C43—C44—C45—O1	132.24 (15)
C5—C6—C7—C8	177.34 (12)	C43—C44—C45—C4	−45.70 (17)
C11—C6—C7—C13	−176.19 (12)	C41—C4—C45—O1	−131.69 (13)
C5—C6—C7—C13	0.57 (15)	C3—C4—C45—O1	−9.93 (17)
C6—C7—C8—C9	0.6 (2)	C5—C4—C45—O1	104.71 (14)
C13—C7—C8—C9	176.60 (14)	C41—C4—C45—C44	46.25 (14)
C7—C8—C9—C10	−0.7 (2)	C3—C4—C45—C44	168.01 (11)
C8—C9—C10—C11	−0.5 (3)	C5—C4—C45—C44	−77.35 (14)
C9—C10—C11—C6	1.7 (2)	C3—C2—N1—C1	−179.96 (13)
C7—C6—C11—C10	−1.7 (2)	C3—C2—N1—C5	45.72 (14)
C5—C6—C11—C10	−177.93 (13)	C6—C5—N1—C2	−151.26 (11)
N1—C5—C12—N3	−58.40 (17)	C12—C5—N1—C2	97.86 (13)
C6—C5—C12—N3	−174.31 (12)	C4—C5—N1—C2	−27.15 (13)
C4—C5—C12—N3	59.83 (17)	C6—C5—N1—C1	74.73 (16)
N1—C5—C12—C13	115.36 (12)	C12—C5—N1—C1	−36.15 (17)
C6—C5—C12—C13	−0.54 (13)	C4—C5—N1—C1	−161.16 (13)
C4—C5—C12—C13	−126.41 (11)	C44—C43—N2—C42	175.24 (13)
N3—C12—C13—N4	−2.3 (2)	C44—C43—N2—C41	−62.07 (16)
C5—C12—C13—N4	−176.31 (12)	C4—C41—N2—C43	67.73 (14)
N3—C12—C13—C7	174.93 (12)	C4—C41—N2—C42	−168.72 (12)
C5—C12—C13—C7	0.91 (14)	C13—C12—N3—C15	3.36 (18)
C8—C7—C13—N4	−0.2 (2)	C5—C12—N3—C15	176.41 (12)
C6—C7—C13—N4	176.18 (13)	C16—C15—N3—C12	178.09 (13)
C8—C7—C13—C12	−177.28 (14)	C14—C15—N3—C12	−2.53 (19)
C6—C7—C13—C12	−0.91 (15)	C12—C13—N4—C14	−0.02 (19)
N4—C14—C15—N3	0.5 (2)	C7—C13—N4—C14	−176.69 (13)
C19—C14—C15—N3	−176.95 (13)	C19—C14—N4—C13	178.22 (13)
N4—C14—C15—C16	179.83 (13)	C15—C14—N4—C13	0.82 (19)
C19—C14—C15—C16	2.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41B···N3	0.97	2.39	2.9475 (18)	116
C9—H9···O1i	0.93	2.53	3.3564 (18)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C41—H41B⋯N3	0.97	2.39	2.9475 (18)	116
C9—H9⋯O1i	0.93	2.53	3.3564 (18)	148

Symmetry code: (i) .