Acenapthene-2-spiro-5′-perhydrodipyrrolo[1,2-a;2′,1′-c]pyrazine-6′-spiro-2′′-acenapthene-1,1′′-dione

The five-membered ring in the acenapthene ring system of the title compound, C₃₂H₂₆N₂O₂, slightly deviates from planarity. The two pyrrolidine rings adopt half-chair conformations and the piperazine ring adopts a chair conformation. The mol­ecular structure is stabilized by weak C—H...O intra­molecular inter­actions and the crystal packing is stabilized by C—H...O inter­molecular inter­actions forming a chain running along (011).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.128
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Acenapthene-2-spiro-5'-perhydrodipyrrole[1,2 - a;2',1'-c]pyrazine-6'- spiro-2''-acenapthene-1,1''-dione

Crystal data

C32H26N2O2	Z = 2
Mr = 470.55	F(000) = 496
Triclinic, P1	Dx = 1.302 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8721 (7) Å	Cell parameters from 2635 reflections
b = 10.7042 (8) Å	θ = 1.6–25.0°
c = 14.2846 (11) Å	µ = 0.08 mm^−1
α = 109.418 (1)°	T = 293 K
β = 100.584 (1)°	Block, colorless
γ = 102.447 (1)°	0.24 × 0.23 × 0.21 mm
V = 1200.37 (16) Å^3

Data collection

Bruker SMART APEX CCD area detector diffractometer	4621 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 28.0°, θmin = 1.6°
ω scans	h = −11→11
13844 measured reflections	k = −14→13
5468 independent reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.068P)^2 + 0.217P] where P = (Fo^2 + 2Fc^2)/3
5468 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	1.20128 (12)	0.73893 (11)	0.34162 (8)	0.0405 (2)
N2	0.88722 (12)	0.56861 (10)	0.26268 (8)	0.0388 (2)
O1	0.93123 (13)	0.83443 (10)	0.44283 (7)	0.0528 (3)
O2	1.12021 (13)	0.55941 (9)	0.11471 (7)	0.0524 (3)
C1	0.88698 (14)	0.81798 (12)	0.35332 (9)	0.0384 (3)
C2	0.78277 (14)	0.88773 (12)	0.30958 (10)	0.0399 (3)
C3	0.72907 (17)	0.99867 (14)	0.35429 (12)	0.0490 (3)
H3	0.7625	1.0491	0.4253	0.059*
C4	0.62161 (18)	1.03264 (15)	0.28818 (14)	0.0572 (4)
H4	0.5858	1.1084	0.3167	0.069*
C5	0.56748 (18)	0.95874 (16)	0.18340 (13)	0.0565 (4)
H5	0.4949	0.9843	0.1432	0.068*
C6	0.62052 (15)	0.84406 (14)	0.13558 (11)	0.0467 (3)
C7	0.57400 (17)	0.75505 (16)	0.02976 (12)	0.0541 (4)
H7	0.4995	0.7692	−0.0176	0.065*
C8	0.63816 (17)	0.64832 (16)	−0.00299 (11)	0.0525 (3)
H8	0.6053	0.5908	−0.0727	0.063*
C9	0.75307 (16)	0.62217 (14)	0.06551 (10)	0.0441 (3)
H9	0.7950	0.5490	0.0411	0.053*
C10	0.80085 (14)	0.70636 (12)	0.16782 (9)	0.0366 (3)
C11	0.73210 (14)	0.81465 (12)	0.20214 (10)	0.0387 (3)
C12	0.91854 (14)	0.70607 (12)	0.25984 (8)	0.0348 (2)
C13	1.09847 (14)	0.75716 (12)	0.25847 (8)	0.0350 (2)
C14	1.14204 (14)	0.90671 (12)	0.26590 (9)	0.0374 (3)
C15	1.16731 (16)	1.02998 (13)	0.34522 (10)	0.0463 (3)
H15	1.1642	1.0329	0.4106	0.056*
C16	1.19837 (18)	1.15353 (15)	0.32628 (13)	0.0562 (4)
H16	1.2150	1.2374	0.3804	0.067*
C17	1.20488 (19)	1.15439 (15)	0.23167 (13)	0.0571 (4)
H17	1.2241	1.2376	0.2222	0.069*
C18	1.18233 (16)	1.02853 (14)	0.14794 (11)	0.0467 (3)
C19	1.18662 (18)	1.00925 (17)	0.04555 (12)	0.0563 (4)
H19	1.2033	1.0854	0.0269	0.068*
C20	1.16662 (19)	0.88028 (17)	−0.02647 (12)	0.0567 (4)
H20	1.1695	0.8715	−0.0931	0.068*
C21	1.14197 (17)	0.76071 (15)	−0.00353 (10)	0.0486 (3)
H21	1.1307	0.6743	−0.0531	0.058*
C22	1.13520 (14)	0.77648 (13)	0.09519 (9)	0.0398 (3)
C23	1.15329 (14)	0.90764 (13)	0.16880 (9)	0.0385 (3)
C24	1.11555 (14)	0.67750 (12)	0.14728 (9)	0.0384 (3)
C25	1.37471 (17)	0.78453 (17)	0.35572 (12)	0.0556 (4)
H25A	1.4160	0.8850	0.3831	0.067*
H25B	1.4009	0.7464	0.2911	0.067*
C26	1.4416 (2)	0.7268 (2)	0.43320 (14)	0.0721 (5)
H26A	1.5237	0.6857	0.4127	0.086*
H26B	1.4882	0.7999	0.5016	0.086*
C27	1.2991 (2)	0.61722 (19)	0.43276 (13)	0.0660 (4)
H27A	1.3244	0.5310	0.4241	0.079*
H27B	1.2691	0.6489	0.4966	0.079*
C28	1.16447 (17)	0.59791 (14)	0.34102 (10)	0.0457 (3)
H28	1.1757	0.5334	0.2773	0.055*
C29	0.99523 (17)	0.55459 (14)	0.34736 (10)	0.0447 (3)
H29	0.9865	0.6143	0.4138	0.054*
C30	0.9210 (2)	0.40269 (16)	0.32806 (13)	0.0609 (4)
H30A	0.9432	0.3874	0.3918	0.073*
H30B	0.9623	0.3427	0.2786	0.073*
C31	0.7407 (2)	0.37578 (18)	0.28484 (14)	0.0669 (4)
H31A	0.6971	0.2928	0.2218	0.080*
H31B	0.6838	0.3642	0.3347	0.080*
C32	0.72517 (18)	0.50312 (15)	0.26331 (12)	0.0546 (3)
H32A	0.6484	0.4769	0.1971	0.065*
H32B	0.6919	0.5646	0.3170	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0390 (5)	0.0480 (6)	0.0365 (5)	0.0164 (4)	0.0095 (4)	0.0174 (4)
N2	0.0440 (6)	0.0379 (5)	0.0369 (5)	0.0132 (4)	0.0129 (4)	0.0157 (4)
O1	0.0672 (6)	0.0583 (6)	0.0334 (5)	0.0275 (5)	0.0164 (4)	0.0117 (4)
O2	0.0760 (7)	0.0439 (5)	0.0434 (5)	0.0272 (5)	0.0251 (5)	0.0140 (4)
C1	0.0392 (6)	0.0379 (6)	0.0370 (6)	0.0118 (5)	0.0146 (5)	0.0107 (5)
C2	0.0367 (6)	0.0387 (6)	0.0460 (7)	0.0126 (5)	0.0163 (5)	0.0151 (5)
C3	0.0485 (7)	0.0423 (7)	0.0599 (8)	0.0178 (6)	0.0239 (6)	0.0169 (6)
C4	0.0557 (8)	0.0485 (8)	0.0826 (11)	0.0279 (7)	0.0314 (8)	0.0299 (8)
C5	0.0470 (8)	0.0619 (9)	0.0801 (11)	0.0270 (7)	0.0218 (7)	0.0425 (8)
C6	0.0369 (6)	0.0531 (7)	0.0582 (8)	0.0142 (5)	0.0141 (6)	0.0306 (6)
C7	0.0419 (7)	0.0697 (9)	0.0547 (8)	0.0144 (6)	0.0054 (6)	0.0348 (7)
C8	0.0479 (7)	0.0628 (9)	0.0392 (7)	0.0092 (6)	0.0041 (6)	0.0192 (6)
C9	0.0443 (7)	0.0459 (7)	0.0386 (6)	0.0121 (5)	0.0100 (5)	0.0137 (5)
C10	0.0351 (6)	0.0390 (6)	0.0373 (6)	0.0108 (5)	0.0110 (5)	0.0163 (5)
C11	0.0336 (6)	0.0403 (6)	0.0452 (6)	0.0108 (5)	0.0133 (5)	0.0192 (5)
C12	0.0383 (6)	0.0363 (6)	0.0304 (5)	0.0132 (5)	0.0113 (4)	0.0112 (4)
C13	0.0379 (6)	0.0372 (6)	0.0307 (5)	0.0142 (5)	0.0112 (4)	0.0114 (4)
C14	0.0348 (6)	0.0387 (6)	0.0390 (6)	0.0123 (5)	0.0112 (5)	0.0140 (5)
C15	0.0477 (7)	0.0423 (7)	0.0434 (7)	0.0127 (5)	0.0126 (5)	0.0102 (5)
C16	0.0579 (9)	0.0381 (7)	0.0633 (9)	0.0142 (6)	0.0135 (7)	0.0102 (6)
C17	0.0583 (8)	0.0433 (7)	0.0750 (10)	0.0174 (6)	0.0183 (7)	0.0282 (7)
C18	0.0410 (7)	0.0489 (7)	0.0579 (8)	0.0164 (5)	0.0141 (6)	0.0280 (6)
C19	0.0557 (8)	0.0654 (9)	0.0675 (9)	0.0225 (7)	0.0220 (7)	0.0445 (8)
C20	0.0619 (9)	0.0755 (10)	0.0489 (8)	0.0264 (8)	0.0223 (7)	0.0368 (7)
C21	0.0516 (8)	0.0592 (8)	0.0407 (7)	0.0198 (6)	0.0178 (6)	0.0217 (6)
C22	0.0386 (6)	0.0468 (7)	0.0383 (6)	0.0156 (5)	0.0141 (5)	0.0181 (5)
C23	0.0334 (6)	0.0431 (6)	0.0418 (6)	0.0135 (5)	0.0112 (5)	0.0185 (5)
C24	0.0407 (6)	0.0419 (6)	0.0338 (6)	0.0152 (5)	0.0136 (5)	0.0127 (5)
C25	0.0397 (7)	0.0710 (9)	0.0563 (8)	0.0188 (6)	0.0107 (6)	0.0248 (7)
C26	0.0508 (9)	0.1046 (14)	0.0677 (10)	0.0349 (9)	0.0094 (7)	0.0383 (10)
C27	0.0667 (10)	0.0833 (11)	0.0602 (9)	0.0348 (9)	0.0097 (8)	0.0391 (9)
C28	0.0544 (8)	0.0506 (7)	0.0402 (6)	0.0263 (6)	0.0135 (6)	0.0208 (6)
C29	0.0580 (8)	0.0459 (7)	0.0371 (6)	0.0206 (6)	0.0159 (6)	0.0199 (5)
C30	0.0810 (11)	0.0528 (8)	0.0606 (9)	0.0227 (8)	0.0220 (8)	0.0334 (7)
C31	0.0748 (11)	0.0573 (9)	0.0707 (10)	0.0081 (8)	0.0213 (8)	0.0342 (8)
C32	0.0505 (8)	0.0511 (8)	0.0627 (9)	0.0080 (6)	0.0179 (7)	0.0260 (7)

Geometric parameters (Å, º)

N1—C13	1.454 (1)	C16—C17	1.366 (2)
N1—C25	1.464 (2)	C16—H16	0.9300
N1—C28	1.471 (2)	C17—C18	1.418 (2)
N2—C12	1.453 (2)	C17—H17	0.9300
N2—C32	1.461 (2)	C18—C23	1.4037 (18)
N2—C29	1.470 (2)	C18—C19	1.416 (2)
O1—C1	1.207 (2)	C19—C20	1.371 (2)
O2—C24	1.206 (2)	C19—H19	0.9300
C1—C2	1.4826 (17)	C20—C21	1.406 (2)
C1—C12	1.586 (2)	C20—H20	0.9300
C2—C3	1.3772 (17)	C21—C22	1.3777 (17)
C2—C11	1.4021 (18)	C21—H21	0.9300
C3—C4	1.407 (2)	C22—C23	1.4006 (17)
C3—H3	0.9300	C22—C24	1.4828 (17)
C4—C5	1.372 (2)	C25—C26	1.526 (2)
C4—H4	0.9300	C25—H25A	0.9700
C5—C6	1.416 (2)	C25—H25B	0.9700
C5—H5	0.9300	C26—C27	1.526 (3)
C6—C11	1.4038 (17)	C26—H26A	0.9700
C6—C7	1.417 (2)	C26—H26B	0.9700
C7—C8	1.368 (2)	C27—C28	1.5247 (19)
C7—H7	0.9300	C27—H27A	0.9700
C8—C9	1.4190 (18)	C27—H27B	0.9700
C8—H8	0.9300	C28—C29	1.5019 (19)
C9—C10	1.3638 (17)	C28—H28	0.9800
C9—H9	0.9300	C29—C30	1.5254 (19)
C10—C11	1.4117 (16)	C29—H29	0.9800
C10—C12	1.522 (2)	C30—C31	1.531 (2)
C12—C13	1.578 (2)	C30—H30A	0.9700
C13—C14	1.526 (2)	C30—H30B	0.9700
C13—C24	1.586 (2)	C31—C32	1.522 (2)
C14—C15	1.3638 (17)	C31—H31A	0.9700
C14—C23	1.4119 (17)	C31—H31B	0.9700
C15—C16	1.417 (2)	C32—H32A	0.9700
C15—H15	0.9300	C32—H32B	0.9700
C13—N1—C25	117.0 (1)	C20—C19—C18	121.14 (13)
C13—N1—C28	116.0 (1)	C20—C19—H19	119.4
C25—N1—C28	105.9 (1)	C18—C19—H19	119.4
C12—N2—C32	116.8 (1)	C19—C20—C21	122.53 (13)
C12—N2—C29	116.3 (1)	C19—C20—H20	118.7
C32—N2—C29	105.2 (1)	C21—C20—H20	118.7
O1—C1—C2	127.02 (11)	C22—C21—C20	117.43 (13)
O1—C1—C12	125.08 (11)	C22—C21—H21	121.3
C2—C1—C12	107.69 (10)	C20—C21—H21	121.3
C3—C2—C11	120.15 (12)	C21—C22—C23	120.36 (12)
C3—C2—C1	132.65 (12)	C21—C22—C24	132.56 (12)
C11—C2—C1	107.16 (10)	C23—C22—C24	107.05 (10)
C2—C3—C4	117.31 (13)	C22—C23—C18	122.89 (12)
C2—C3—H3	121.3	C22—C23—C14	113.65 (11)
C4—C3—H3	121.3	C18—C23—C14	123.45 (12)
C5—C4—C3	122.81 (13)	O2—C24—C22	127.00 (11)
C5—C4—H4	118.6	O2—C24—C13	125.01 (11)
C3—C4—H4	118.6	C22—C24—C13	107.88 (10)
C4—C5—C6	120.96 (13)	N1—C25—C26	103.03 (12)
C4—C5—H5	119.5	N1—C25—H25A	111.2
C6—C5—H5	119.5	C26—C25—H25A	111.2
C11—C6—C5	115.48 (13)	N1—C25—H25B	111.2
C11—C6—C7	116.29 (12)	C26—C25—H25B	111.2
C5—C6—C7	128.22 (13)	H25A—C25—H25B	109.1
C8—C7—C6	120.25 (12)	C27—C26—C25	105.89 (12)
C8—C7—H7	119.9	C27—C26—H26A	110.6
C6—C7—H7	119.9	C25—C26—H26A	110.6
C7—C8—C9	122.44 (13)	C27—C26—H26B	110.6
C7—C8—H8	118.8	C25—C26—H26B	110.6
C9—C8—H8	118.8	H26A—C26—H26B	108.7
C10—C9—C8	118.73 (12)	C28—C27—C26	104.57 (12)
C10—C9—H9	120.6	C28—C27—H27A	110.8
C8—C9—H9	120.6	C26—C27—H27A	110.8
C9—C10—C11	118.91 (11)	C28—C27—H27B	110.8
C9—C10—C12	131.78 (11)	C26—C27—H27B	110.8
C11—C10—C12	109.29 (10)	H27A—C27—H27B	108.9
C2—C11—C6	123.19 (12)	N1—C28—C29	108.90 (10)
C2—C11—C10	113.46 (11)	N1—C28—C27	101.02 (11)
C6—C11—C10	123.33 (12)	C29—C28—C27	117.20 (12)
N2—C12—C10	111.23 (9)	N1—C28—H28	109.8
N2—C12—C13	108.82 (9)	C29—C28—H28	109.8
C10—C12—C13	111.92 (9)	C27—C28—H28	109.8
N2—C12—C1	114.08 (9)	N2—C29—C28	108.59 (10)
C10—C12—C1	101.44 (9)	N2—C29—C30	101.03 (11)
C13—C12—C1	109.24 (9)	C28—C29—C30	117.76 (12)
N1—C13—C14	112.79 (9)	N2—C29—H29	109.7
N1—C13—C12	108.39 (9)	C28—C29—H29	109.7
C14—C13—C12	110.81 (9)	C30—C29—H29	109.7
N1—C13—C24	114.08 (9)	C29—C30—C31	104.25 (12)
C14—C13—C24	101.22 (9)	C29—C30—H30A	110.9
C12—C13—C24	109.41 (9)	C31—C30—H30A	110.9
C15—C14—C23	118.67 (12)	C29—C30—H30B	110.9
C15—C14—C13	132.18 (11)	C31—C30—H30B	110.9
C23—C14—C13	109.14 (10)	H30A—C30—H30B	108.9
C14—C15—C16	118.85 (13)	C32—C31—C30	105.51 (12)
C14—C15—H15	120.6	C32—C31—H31A	110.6
C16—C15—H15	120.6	C30—C31—H31A	110.6
C17—C16—C15	122.61 (13)	C32—C31—H31B	110.6
C17—C16—H16	118.7	C30—C31—H31B	110.6
C15—C16—H16	118.7	H31A—C31—H31B	108.8
C16—C17—C18	120.09 (13)	N2—C32—C31	103.42 (12)
C16—C17—H17	120.0	N2—C32—H32A	111.1
C18—C17—H17	120.0	C31—C32—H32A	111.1
C23—C18—C19	115.62 (13)	N2—C32—H32B	111.1
C23—C18—C17	116.28 (13)	C31—C32—H32B	111.1
C19—C18—C17	128.11 (13)	H32A—C32—H32B	109.0
O1—C1—C2—C3	11.1 (2)	C24—C13—C14—C15	−172.23 (13)
C12—C1—C2—C3	−173.99 (13)	N1—C13—C14—C23	131.25 (10)
O1—C1—C2—C11	−166.31 (13)	C12—C13—C14—C23	−107.04 (10)
C12—C1—C2—C11	8.62 (13)	C24—C13—C14—C23	8.92 (12)
C11—C2—C3—C4	0.85 (19)	C23—C14—C15—C16	2.14 (19)
C1—C2—C3—C4	−176.27 (13)	C13—C14—C15—C16	−176.62 (12)
C2—C3—C4—C5	1.3 (2)	C14—C15—C16—C17	−0.3 (2)
C3—C4—C5—C6	−1.2 (2)	C15—C16—C17—C18	−0.9 (2)
C4—C5—C6—C11	−1.1 (2)	C16—C17—C18—C23	0.2 (2)
C4—C5—C6—C7	178.22 (14)	C16—C17—C18—C19	−179.22 (14)
C11—C6—C7—C8	−0.66 (19)	C23—C18—C19—C20	−1.3 (2)
C5—C6—C7—C8	−179.94 (14)	C17—C18—C19—C20	178.20 (15)
C6—C7—C8—C9	−0.5 (2)	C18—C19—C20—C21	−0.4 (2)
C7—C8—C9—C10	0.2 (2)	C19—C20—C21—C22	1.2 (2)
C8—C9—C10—C11	1.19 (18)	C20—C21—C22—C23	−0.31 (19)
C8—C9—C10—C12	179.50 (12)	C20—C21—C22—C24	−178.21 (13)
C3—C2—C11—C6	−3.29 (19)	C21—C22—C23—C18	−1.46 (19)
C1—C2—C11—C6	174.49 (11)	C24—C22—C23—C18	176.92 (11)
C3—C2—C11—C10	178.34 (11)	C21—C22—C23—C14	179.47 (11)
C1—C2—C11—C10	−3.88 (14)	C24—C22—C23—C14	−2.15 (14)
C5—C6—C11—C2	3.31 (18)	C19—C18—C23—C22	2.21 (18)
C7—C6—C11—C2	−176.06 (12)	C17—C18—C23—C22	−177.32 (12)
C5—C6—C11—C10	−178.48 (12)	C19—C18—C23—C14	−178.82 (12)
C7—C6—C11—C10	2.15 (18)	C17—C18—C23—C14	1.65 (19)
C9—C10—C11—C2	175.91 (11)	C15—C14—C23—C22	176.17 (11)
C12—C10—C11—C2	−2.75 (14)	C13—C14—C23—C22	−4.81 (14)
C9—C10—C11—C6	−2.46 (18)	C15—C14—C23—C18	−2.89 (18)
C12—C10—C11—C6	178.88 (11)	C13—C14—C23—C18	176.14 (11)
C32—N2—C12—C10	−55.69 (13)	C21—C22—C24—O2	9.8 (2)
C29—N2—C12—C10	178.97 (9)	C23—C22—C24—O2	−168.33 (13)
C32—N2—C12—C13	−179.43 (10)	C21—C22—C24—C13	−173.98 (13)
C29—N2—C12—C13	55.2 (1)	C23—C22—C24—C13	7.91 (13)
C32—N2—C12—C1	58.31 (14)	N1—C13—C24—O2	44.79 (17)
C29—N2—C12—C1	−67.03 (13)	C14—C13—C24—O2	166.21 (12)
C9—C10—C12—N2	−49.21 (17)	C12—C13—C24—O2	−76.80 (15)
C11—C10—C12—N2	129.22 (10)	N1—C13—C24—C22	−131.55 (10)
C9—C10—C12—C13	72.76 (16)	C14—C13—C24—C22	−10.13 (12)
C11—C10—C12—C13	−108.82 (11)	C12—C13—C24—C22	106.87 (10)
C9—C10—C12—C1	−170.89 (13)	C13—N1—C25—C26	−169.92 (12)
C11—C10—C12—C1	7.53 (12)	C28—N1—C25—C26	−38.86 (14)
O1—C1—C12—N2	45.67 (16)	N1—C25—C26—C27	16.49 (17)
C2—C1—C12—N2	−129.39 (10)	C25—C26—C27—C28	10.32 (18)
O1—C1—C12—C10	165.34 (12)	C13—N1—C28—C29	−59.1 (1)
C2—C1—C12—C10	−9.71 (12)	C25—N1—C28—C29	169.22 (10)
O1—C1—C12—C13	−76.36 (15)	C13—N1—C28—C27	176.89 (11)
C2—C1—C12—C13	108.59 (10)	C25—N1—C28—C27	45.24 (13)
C25—N1—C13—C14	−55.07 (14)	C26—C27—C28—N1	−32.95 (15)
C28—N1—C13—C14	178.73 (9)	C26—C27—C28—C29	−151.05 (13)
C25—N1—C13—C12	−178.14 (10)	C12—N2—C29—C28	−58.3 (1)
C28—N1—C13—C12	55.7 (1)	C32—N2—C29—C28	170.65 (11)
C25—N1—C13—C24	59.71 (14)	C12—N2—C29—C30	177.2 (1)
C28—N1—C13—C24	−66.49 (13)	C32—N2—C29—C30	46.17 (13)
N2—C12—C13—N1	−50.3 (1)	N1—C28—C29—N2	55.1 (1)
C10—C12—C13—N1	−173.64 (9)	C27—C28—C29—N2	168.90 (12)
C1—C12—C13—N1	74.84 (11)	N1—C28—C29—C30	169.03 (11)
N2—C12—C13—C14	−174.57 (9)	C27—C28—C29—C30	−77.21 (17)
C10—C12—C13—C14	62.09 (12)	N2—C29—C30—C31	−33.49 (14)
C1—C12—C13—C14	−49.43 (12)	C28—C29—C30—C31	−151.49 (13)
N2—C12—C13—C24	74.66 (11)	C29—C30—C31—C32	10.17 (17)
C10—C12—C13—C24	−48.67 (12)	C12—N2—C32—C31	−170.69 (11)
C1—C12—C13—C24	−160.20 (9)	C29—N2—C32—C31	−39.96 (14)
N1—C13—C14—C15	−49.91 (17)	C30—C31—C32—N2	17.29 (16)
C12—C13—C14—C15	71.81 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···O2	0.98	2.41	3.058 (2)	124
C29—H29···O1	0.98	2.43	3.075 (2)	123
C9—H9···O2^i	0.93	2.48	3.217 (2)	136
C15—H15···O1^ii	0.93	2.51	3.261 (2)	138

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z+1.