Crystal structure of 1',1''-dimethyl-4'-(4-cholorophen-yl)di-spiro-[11H-indeno[1,2-b]quinoxaline-11,2'-pyrrolidine-3',3''-piperidin]-4''-one.

In the title compound, C30H27ClN4O, the central pyrrolidine ring adopts an envelope conformation with the methyl-ene C atom being the flap. The quinoxaline and indane rings are each essentially planar, with r.m.s. deviations of 0.027 (1) and 0.0417 (1) Å, respectively. The pyrrolidine ring forms dihedral angles of 88.25 (1) and 83.76 (1)° with the quinoxaline and indane rings, respectively. A weak intra-molecular C-H⋯N inter-action is observed. In the crystal, C-H⋯π inter-actions lead to supra-molecular chains along [101] that assemble in the ac plane. Connections along the b axis are of the type Cl⋯Cl [3.6538 (16) Å].

Related literature

For the importance of quinoxaline derivatives, see: Abasolo et al. (1987 ▸); Kleim et al. (1995 ▸); Dailey et al. (2001 ▸); Rodrigo et al. (2002 ▸); Seitz et al. (2002 ▸). For a related structure, see: Selvanayagam et al. (2011 ▸).

Experimental

Crystal data

C30H27ClN4O

M = 495.00

Monoclinic,

a = 22.4220 (13) Å

b = 14.3498 (9) Å

c = 17.2811 (9) Å

β = 116.847 (2)°

V = 4960.9 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.19 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

18093 measured reflections

3791 independent reflections

2758 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.116

S = 1.05

3791 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.26 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: SHELXL2014 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027698/zq2230sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027698/zq2230Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014027698/zq2230Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014027698/zq2230fig1.tif

The mol­ecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H-atoms are omitted for clarity.

Click here for additional data file.

. DOI: 10.1107/S2056989014027698/zq2230fig2.tif

The partial packing diagram showing C—H⋯π inter­actions as dashed lines. All H-atoms are omitted for clarity except for the H atom involved in the inter­molecular inter­action.

CCDC reference: 1040368

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

C30H27ClN4O	F(000) = 2080
Mr = 495.00	Dx = 1.326 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.4220 (13) Å	Cell parameters from 2000 reflections
b = 14.3498 (9) Å	θ = 2–31°
c = 17.2811 (9) Å	µ = 0.19 mm−1
β = 116.847 (2)°	T = 293 K
V = 4960.9 (5) Å3	Block, colourless
Z = 8	0.21 × 0.19 × 0.18 mm

Bruker Kappa APEXII diffractometer	2758 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
ω and φ scans	θmax = 23.8°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→25
Tmin = 0.967, Tmax = 0.974	k = −16→16
18093 measured reflections	l = −19→13
3791 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.052P)2 + 2.7359P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3791 reflections	Δρmax = 0.22 e Å−3
325 parameters	Δρmin = −0.26 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.

	x	y	z	Uiso*/Ueq
C1	0.30822 (11)	0.05687 (16)	0.33108 (14)	0.0608 (6)
H1A	0.3191	0.0297	0.2883	0.091*
H1B	0.3481	0.0807	0.3781	0.091*
H1C	0.2888	0.0103	0.3526	0.091*
C2	0.23954 (11)	0.18035 (15)	0.34879 (13)	0.0523 (5)
H2A	0.2767	0.2104	0.3965	0.063*
H2B	0.2174	0.1385	0.3717	0.063*
C3	0.19136 (10)	0.25089 (14)	0.28740 (12)	0.0459 (5)
H3	0.2184	0.2962	0.2746	0.055*
C4	0.15164 (10)	0.19405 (14)	0.20256 (12)	0.0457 (5)
C5	0.20122 (9)	0.10932 (14)	0.21204 (12)	0.0439 (5)
C6	0.22053 (10)	0.09623 (14)	0.13862 (12)	0.0466 (5)
C7	0.19965 (10)	0.01074 (15)	0.09751 (12)	0.0492 (5)
C8	0.21358 (12)	−0.01455 (18)	0.03003 (14)	0.0630 (6)
H8	0.1994	−0.0717	0.0024	0.076*
C9	0.24862 (13)	0.0464 (2)	0.00475 (16)	0.0714 (7)
H9	0.2575	0.0308	−0.0413	0.086*
C10	0.27083 (12)	0.13009 (18)	0.04655 (14)	0.0650 (6)
H10	0.2953	0.1699	0.0292	0.078*
C11	0.25718 (10)	0.15583 (16)	0.11420 (13)	0.0556 (6)
H11	0.2725	0.2124	0.1426	0.067*
C12	0.17122 (9)	0.01365 (14)	0.21185 (12)	0.0447 (5)
C13	0.16878 (10)	−0.04160 (14)	0.14202 (12)	0.0462 (5)
C14	0.12375 (10)	−0.15970 (15)	0.18401 (13)	0.0513 (5)
C15	0.12990 (10)	−0.10743 (15)	0.25619 (13)	0.0506 (5)
C16	0.11002 (11)	−0.14672 (17)	0.31511 (15)	0.0628 (6)
H16	0.1147	−0.1130	0.3635	0.075*
C17	0.08385 (12)	−0.23439 (19)	0.30153 (17)	0.0719 (7)
H17	0.0710	−0.2604	0.3410	0.086*
C18	0.07626 (12)	−0.28531 (18)	0.22925 (18)	0.0737 (7)
H18	0.0576	−0.3446	0.2202	0.088*
C19	0.09589 (11)	−0.24923 (16)	0.17162 (15)	0.0623 (6)
H19	0.0908	−0.2842	0.1237	0.075*
C31	0.15093 (10)	0.30600 (14)	0.32168 (13)	0.0483 (5)
C32	0.14179 (12)	0.27914 (17)	0.39179 (14)	0.0640 (6)
H32	0.1598	0.2228	0.4188	0.077*
C33	0.10678 (13)	0.3330 (2)	0.42345 (15)	0.0742 (7)
H33	0.1012	0.3126	0.4709	0.089*
C34	0.08049 (13)	0.4154 (2)	0.38554 (17)	0.0752 (7)
C35	0.08847 (17)	0.4439 (2)	0.3162 (2)	0.1013 (10)
H35	0.0704	0.5005	0.2898	0.122*
C36	0.12311 (15)	0.38969 (18)	0.28474 (18)	0.0839 (8)
H36	0.1278	0.4104	0.2368	0.101*
C41	0.08396 (10)	0.16135 (16)	0.19371 (13)	0.0539 (5)
H41A	0.0908	0.1229	0.2432	0.065*
H41B	0.0576	0.2151	0.1934	0.065*
C42	−0.00945 (13)	0.0602 (2)	0.1155 (2)	0.0974 (10)
H42A	0.0060	0.0193	0.1647	0.146*
H42B	−0.0396	0.1053	0.1193	0.146*
H42C	−0.0322	0.0244	0.0632	0.146*
C43	0.02670 (14)	0.1710 (2)	0.04037 (16)	0.0857 (9)
H43A	−0.0012	0.2199	0.0455	0.103*
H43B	0.0004	0.1369	−0.0128	0.103*
C44	0.08668 (14)	0.2140 (2)	0.03617 (14)	0.0824 (8)
H44A	0.1079	0.1672	0.0164	0.099*
H44B	0.0716	0.2639	−0.0063	0.099*
C45	0.13753 (13)	0.25230 (18)	0.12140 (14)	0.0612 (6)
N1	0.26100 (8)	0.13210 (12)	0.29228 (10)	0.0486 (4)
N2	0.04763 (9)	0.10806 (14)	0.11417 (12)	0.0668 (5)
N3	0.15437 (8)	−0.01733 (12)	0.27018 (10)	0.0499 (4)
N4	0.14498 (8)	−0.12662 (12)	0.12568 (11)	0.0532 (5)
O1	0.16569 (11)	0.32522 (13)	0.12566 (11)	0.0874 (6)
Cl1	0.03708 (5)	0.48362 (8)	0.42608 (6)	0.1348 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0526 (13)	0.0683 (16)	0.0540 (13)	0.0102 (11)	0.0175 (11)	0.0012 (11)
C2	0.0550 (13)	0.0562 (13)	0.0397 (11)	0.0015 (10)	0.0160 (10)	−0.0042 (10)
C3	0.0513 (12)	0.0446 (12)	0.0423 (11)	−0.0033 (9)	0.0215 (10)	−0.0010 (9)
C4	0.0502 (12)	0.0497 (13)	0.0360 (10)	0.0035 (10)	0.0185 (9)	0.0018 (9)
C5	0.0458 (11)	0.0479 (12)	0.0362 (10)	0.0004 (9)	0.0168 (9)	−0.0014 (9)
C6	0.0451 (11)	0.0539 (13)	0.0382 (11)	0.0029 (10)	0.0164 (9)	0.0037 (10)
C7	0.0484 (12)	0.0581 (14)	0.0380 (11)	0.0033 (10)	0.0167 (10)	−0.0017 (10)
C8	0.0732 (16)	0.0713 (16)	0.0464 (13)	−0.0009 (13)	0.0287 (12)	−0.0120 (11)
C9	0.0785 (17)	0.094 (2)	0.0515 (14)	0.0000 (15)	0.0383 (13)	−0.0059 (14)
C10	0.0638 (15)	0.0843 (19)	0.0534 (14)	−0.0014 (13)	0.0322 (12)	0.0078 (13)
C11	0.0566 (13)	0.0617 (15)	0.0488 (12)	−0.0004 (11)	0.0241 (11)	0.0025 (11)
C12	0.0424 (11)	0.0516 (13)	0.0371 (11)	0.0039 (9)	0.0153 (9)	0.0017 (9)
C13	0.0440 (11)	0.0480 (13)	0.0402 (11)	0.0032 (10)	0.0133 (9)	0.0003 (10)
C14	0.0428 (11)	0.0502 (14)	0.0500 (12)	0.0033 (10)	0.0112 (10)	0.0067 (10)
C15	0.0408 (11)	0.0565 (14)	0.0470 (12)	−0.0002 (10)	0.0133 (10)	0.0055 (10)
C16	0.0532 (13)	0.0751 (17)	0.0574 (14)	−0.0066 (12)	0.0226 (11)	0.0095 (12)
C17	0.0577 (15)	0.0799 (19)	0.0707 (17)	−0.0117 (13)	0.0223 (13)	0.0178 (14)
C18	0.0583 (15)	0.0604 (16)	0.0869 (19)	−0.0086 (12)	0.0190 (14)	0.0120 (15)
C19	0.0554 (14)	0.0506 (14)	0.0665 (15)	−0.0019 (11)	0.0149 (12)	0.0030 (11)
C31	0.0535 (12)	0.0455 (13)	0.0454 (12)	−0.0062 (10)	0.0218 (10)	−0.0037 (9)
C32	0.0822 (17)	0.0618 (15)	0.0521 (13)	0.0109 (13)	0.0339 (13)	0.0044 (11)
C33	0.0803 (17)	0.098 (2)	0.0518 (14)	0.0089 (16)	0.0364 (14)	−0.0049 (14)
C34	0.0730 (17)	0.085 (2)	0.0645 (16)	0.0170 (15)	0.0286 (14)	−0.0128 (14)
C35	0.143 (3)	0.0686 (19)	0.120 (3)	0.0444 (19)	0.084 (2)	0.0252 (18)
C36	0.122 (2)	0.0625 (17)	0.096 (2)	0.0280 (16)	0.0741 (19)	0.0268 (15)
C41	0.0477 (12)	0.0577 (14)	0.0505 (12)	0.0040 (10)	0.0170 (10)	−0.0077 (10)
C42	0.0565 (16)	0.100 (2)	0.111 (2)	−0.0149 (15)	0.0164 (16)	−0.0301 (18)
C43	0.0708 (18)	0.103 (2)	0.0537 (15)	0.0192 (16)	0.0022 (14)	−0.0080 (15)
C44	0.090 (2)	0.103 (2)	0.0409 (13)	0.0323 (17)	0.0177 (14)	0.0129 (13)
C45	0.0720 (16)	0.0648 (16)	0.0493 (13)	0.0192 (13)	0.0295 (12)	0.0092 (12)
N1	0.0462 (10)	0.0531 (11)	0.0410 (9)	0.0039 (8)	0.0148 (8)	−0.0023 (8)
N2	0.0516 (11)	0.0734 (14)	0.0582 (12)	0.0014 (10)	0.0096 (10)	−0.0157 (10)
N3	0.0496 (10)	0.0564 (12)	0.0424 (10)	−0.0024 (8)	0.0198 (8)	0.0016 (8)
N4	0.0516 (10)	0.0521 (11)	0.0475 (10)	0.0005 (9)	0.0151 (9)	−0.0010 (9)
O1	0.1327 (17)	0.0656 (12)	0.0729 (12)	0.0032 (12)	0.0542 (12)	0.0171 (10)
Cl1	0.1370 (8)	0.1672 (9)	0.1083 (7)	0.0676 (7)	0.0626 (6)	−0.0185 (6)

C1—N1	1.447 (3)	C15—C16	1.401 (3)
C1—H1A	0.9600	C16—C17	1.363 (3)
C1—H1B	0.9600	C16—H16	0.9300
C1—H1C	0.9600	C17—C18	1.390 (4)
C2—N1	1.445 (2)	C17—H17	0.9300
C2—C3	1.511 (3)	C18—C19	1.360 (3)
C2—H2A	0.9700	C18—H18	0.9300
C2—H2B	0.9700	C19—H19	0.9300
C3—C31	1.511 (3)	C31—C36	1.371 (3)
C3—C4	1.558 (3)	C31—C32	1.372 (3)
C3—H3	0.9800	C32—C33	1.379 (3)
C4—C41	1.529 (3)	C32—H32	0.9300
C4—C45	1.538 (3)	C33—C34	1.352 (4)
C4—C5	1.605 (3)	C33—H33	0.9300
C5—N1	1.466 (2)	C34—C35	1.352 (4)
C5—C6	1.526 (3)	C34—Cl1	1.736 (2)
C5—C12	1.528 (3)	C35—C36	1.374 (4)
C6—C11	1.378 (3)	C35—H35	0.9300
C6—C7	1.389 (3)	C36—H36	0.9300
C7—C8	1.385 (3)	C41—N2	1.458 (3)
C7—C13	1.455 (3)	C41—H41A	0.9700
C8—C9	1.372 (3)	C41—H41B	0.9700
C8—H8	0.9300	C42—N2	1.462 (3)
C9—C10	1.374 (3)	C42—H42A	0.9600
C9—H9	0.9300	C42—H42B	0.9600
C10—C11	1.386 (3)	C42—H42C	0.9600
C10—H10	0.9300	C43—N2	1.457 (3)
C11—H11	0.9300	C43—C44	1.511 (4)
C12—N3	1.304 (2)	C43—H43A	0.9700
C12—C13	1.424 (3)	C43—H43B	0.9700
C13—N4	1.310 (3)	C44—C45	1.501 (4)
C14—N4	1.379 (3)	C44—H44A	0.9700
C14—C19	1.402 (3)	C44—H44B	0.9700
C14—C15	1.408 (3)	C45—O1	1.207 (3)
C15—N3	1.382 (3)
N1—C1—H1A	109.5	C16—C17—C18	120.6 (2)
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	120.6 (2)
H1A—C1—H1C	109.5	C19—C18—H18	119.7
H1B—C1—H1C	109.5	C17—C18—H18	119.7
N1—C2—C3	101.37 (15)	C18—C19—C14	120.4 (2)
N1—C2—H2A	111.5	C18—C19—H19	119.8
C3—C2—H2A	111.5	C14—C19—H19	119.8
N1—C2—H2B	111.5	C36—C31—C32	116.1 (2)
C3—C2—H2B	111.5	C36—C31—C3	120.23 (19)
H2A—C2—H2B	109.3	C32—C31—C3	123.67 (19)
C2—C3—C31	116.15 (16)	C31—C32—C33	122.1 (2)
C2—C3—C4	103.51 (15)	C31—C32—H32	118.9
C31—C3—C4	116.98 (16)	C33—C32—H32	118.9
C2—C3—H3	106.5	C34—C33—C32	120.0 (2)
C31—C3—H3	106.5	C34—C33—H33	120.0
C4—C3—H3	106.5	C32—C33—H33	120.0
C41—C4—C45	106.83 (17)	C35—C34—C33	119.4 (2)
C41—C4—C3	112.00 (15)	C35—C34—Cl1	120.6 (2)
C45—C4—C3	111.62 (17)	C33—C34—Cl1	119.9 (2)
C41—C4—C5	112.83 (16)	C34—C35—C36	120.3 (3)
C45—C4—C5	110.64 (15)	C34—C35—H35	119.9
C3—C4—C5	103.02 (15)	C36—C35—H35	119.9
N1—C5—C6	109.41 (15)	C31—C36—C35	122.1 (2)
N1—C5—C12	114.58 (15)	C31—C36—H36	118.9
C6—C5—C12	100.23 (15)	C35—C36—H36	118.9
N1—C5—C4	102.88 (14)	N2—C41—C4	111.24 (16)
C6—C5—C4	116.86 (15)	N2—C41—H41A	109.4
C12—C5—C4	113.36 (15)	C4—C41—H41A	109.4
C11—C6—C7	120.10 (18)	N2—C41—H41B	109.4
C11—C6—C5	127.65 (19)	C4—C41—H41B	109.4
C7—C6—C5	112.17 (17)	H41A—C41—H41B	108.0
C8—C7—C6	120.7 (2)	N2—C42—H42A	109.5
C8—C7—C13	130.7 (2)	N2—C42—H42B	109.5
C6—C7—C13	108.46 (17)	H42A—C42—H42B	109.5
C9—C8—C7	118.7 (2)	N2—C42—H42C	109.5
C9—C8—H8	120.6	H42A—C42—H42C	109.5
C7—C8—H8	120.6	H42B—C42—H42C	109.5
C8—C9—C10	120.9 (2)	N2—C43—C44	110.7 (2)
C8—C9—H9	119.6	N2—C43—H43A	109.5
C10—C9—H9	119.6	C44—C43—H43A	109.5
C9—C10—C11	120.7 (2)	N2—C43—H43B	109.5
C9—C10—H10	119.6	C44—C43—H43B	109.5
C11—C10—H10	119.6	H43A—C43—H43B	108.1
C6—C11—C10	118.9 (2)	C45—C44—C43	113.6 (2)
C6—C11—H11	120.6	C45—C44—H44A	108.8
C10—C11—H11	120.6	C43—C44—H44A	108.8
N3—C12—C13	123.48 (19)	C45—C44—H44B	108.8
N3—C12—C5	125.84 (17)	C43—C44—H44B	108.8
C13—C12—C5	110.51 (16)	H44A—C44—H44B	107.7
N4—C13—C12	123.85 (18)	O1—C45—C44	121.4 (2)
N4—C13—C7	127.70 (18)	O1—C45—C4	121.9 (2)
C12—C13—C7	108.38 (18)	C44—C45—C4	116.6 (2)
N4—C14—C19	118.7 (2)	C2—N1—C1	116.20 (16)
N4—C14—C15	122.43 (19)	C2—N1—C5	107.75 (15)
C19—C14—C15	118.8 (2)	C1—N1—C5	115.92 (16)
N3—C15—C16	118.7 (2)	C43—N2—C41	108.79 (19)
N3—C15—C14	121.71 (18)	C43—N2—C42	111.5 (2)
C16—C15—C14	119.6 (2)	C41—N2—C42	110.65 (19)
C17—C16—C15	120.0 (2)	C12—N3—C15	114.47 (17)
C17—C16—H16	120.0	C13—N4—C14	113.86 (17)
C15—C16—H16	120.0
N1—C2—C3—C31	171.55 (16)	C14—C15—C16—C17	−1.1 (3)
N1—C2—C3—C4	41.92 (19)	C15—C16—C17—C18	−0.4 (4)
C2—C3—C4—C41	98.92 (19)	C16—C17—C18—C19	1.2 (4)
C31—C3—C4—C41	−30.2 (2)	C17—C18—C19—C14	−0.4 (4)
C2—C3—C4—C45	−141.35 (17)	N4—C14—C19—C18	178.0 (2)
C31—C3—C4—C45	89.5 (2)	C15—C14—C19—C18	−1.1 (3)
C2—C3—C4—C5	−22.61 (18)	C2—C3—C31—C36	158.8 (2)
C31—C3—C4—C5	−151.73 (16)	C4—C3—C31—C36	−78.4 (3)
C41—C4—C5—N1	−125.30 (16)	C2—C3—C31—C32	−18.6 (3)
C45—C4—C5—N1	115.08 (18)	C4—C3—C31—C32	104.2 (2)
C3—C4—C5—N1	−4.34 (18)	C36—C31—C32—C33	−0.1 (4)
C41—C4—C5—C6	114.83 (18)	C3—C31—C32—C33	177.4 (2)
C45—C4—C5—C6	−4.8 (2)	C31—C32—C33—C34	−0.4 (4)
C3—C4—C5—C6	−124.21 (17)	C32—C33—C34—C35	0.5 (4)
C41—C4—C5—C12	−1.0 (2)	C32—C33—C34—Cl1	−179.4 (2)
C45—C4—C5—C12	−120.61 (19)	C33—C34—C35—C36	−0.1 (5)
C3—C4—C5—C12	119.97 (16)	Cl1—C34—C35—C36	179.8 (3)
N1—C5—C6—C11	−51.1 (3)	C32—C31—C36—C35	0.4 (4)
C12—C5—C6—C11	−171.90 (19)	C3—C31—C36—C35	−177.1 (3)
C4—C5—C6—C11	65.2 (3)	C34—C35—C36—C31	−0.3 (5)
N1—C5—C6—C7	125.62 (18)	C45—C4—C41—N2	57.7 (2)
C12—C5—C6—C7	4.8 (2)	C3—C4—C41—N2	−179.81 (16)
C4—C5—C6—C7	−118.06 (19)	C5—C4—C41—N2	−64.1 (2)
C11—C6—C7—C8	−1.9 (3)	N2—C43—C44—C45	−47.8 (3)
C5—C6—C7—C8	−178.92 (18)	C43—C44—C45—O1	−139.5 (3)
C11—C6—C7—C13	173.82 (18)	C43—C44—C45—C4	40.4 (3)
C5—C6—C7—C13	−3.2 (2)	C41—C4—C45—O1	136.3 (2)
C6—C7—C8—C9	0.2 (3)	C3—C4—C45—O1	13.6 (3)
C13—C7—C8—C9	−174.4 (2)	C5—C4—C45—O1	−100.5 (2)
C7—C8—C9—C10	1.4 (4)	C41—C4—C45—C44	−43.6 (2)
C8—C9—C10—C11	−1.3 (4)	C3—C4—C45—C44	−166.30 (19)
C7—C6—C11—C10	2.0 (3)	C5—C4—C45—C44	79.6 (2)
C5—C6—C11—C10	178.47 (19)	C3—C2—N1—C1	−179.25 (17)
C9—C10—C11—C6	−0.4 (3)	C3—C2—N1—C5	−47.3 (2)
N1—C5—C12—N3	53.5 (3)	C6—C5—N1—C2	156.77 (16)
C6—C5—C12—N3	170.50 (18)	C12—C5—N1—C2	−91.62 (19)
C4—C5—C12—N3	−64.2 (2)	C4—C5—N1—C2	31.88 (19)
N1—C5—C12—C13	−121.80 (17)	C6—C5—N1—C1	−71.1 (2)
C6—C5—C12—C13	−4.8 (2)	C12—C5—N1—C1	40.5 (2)
C4—C5—C12—C13	120.51 (17)	C4—C5—N1—C1	164.01 (16)
N3—C12—C13—N4	5.1 (3)	C44—C43—N2—C41	62.2 (3)
C5—C12—C13—N4	−179.49 (18)	C44—C43—N2—C42	−175.5 (2)
N3—C12—C13—C7	−172.11 (18)	C4—C41—N2—C43	−69.7 (2)
C5—C12—C13—C7	3.3 (2)	C4—C41—N2—C42	167.5 (2)
C8—C7—C13—N4	−2.0 (4)	C13—C12—N3—C15	−3.6 (3)
C6—C7—C13—N4	−177.16 (19)	C5—C12—N3—C15	−178.36 (17)
C8—C7—C13—C12	175.1 (2)	C16—C15—N3—C12	−179.58 (18)
C6—C7—C13—C12	−0.1 (2)	C14—C15—N3—C12	−0.4 (3)
N4—C14—C15—N3	3.6 (3)	C12—C13—N4—C14	−1.7 (3)
C19—C14—C15—N3	−177.29 (19)	C7—C13—N4—C14	174.96 (18)
N4—C14—C15—C16	−177.21 (19)	C19—C14—N4—C13	178.54 (19)
C19—C14—C15—C16	1.9 (3)	C15—C14—N4—C13	−2.4 (3)
N3—C15—C16—C17	178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41A···N3	0.97	2.39	2.988 (3)	120
C11—H11···Cg1i	0.93	2.89	3.655 (2)	140

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C14C19 ring.

DHA	DH	HA	D A	DHA
C41H41AN3	0.97	2.39	2.988(3)	120
C11H11Cg1i	0.93	2.89	3.655(2)	140

Symmetry code: (i) .