5-Benzyl­idene-1-phenyl-2′′,3′′-dihydro­piperidine-3-spiro-2′-pyrrolizidine-3′-spiro-3′′-1H-indole-4,2′′-dione

In the pyrrolizidine unit of the title compound, C₃₂H₃₁N₃O₂, one pyrrolidine ring adopts an envelope conformation and the other adopts a twist conformation. The mol­ecular conformation is stabilized by weak C—H...O intra­molecular inter­actions and the crystal packing is stabil­ized by N—H...O and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.052
• wR factor = 0.142
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C20

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G 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
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 5 Informative message, check

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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, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

5-Benzylidene-1-phenyl-2'',3''-dihydropiperidine-3-spiro-2'-pyrrolizidine- 3'-spiro-3''-1H-indole-4,2''-dione

Crystal data

C32H31N3O2	F(000) = 1040
Mr = 489.60	Dx = 1.230 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3086 reflections
a = 8.7120 (4) Å	θ = 1.7–25.0°
b = 20.5711 (10) Å	µ = 0.08 mm^−1
c = 14.9467 (7) Å	T = 293 K
β = 99.322 (1)°	Block, yellow
V = 2643.3 (2) Å^3	0.25 × 0.24 × 0.22 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4738 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 28.0°, θmin = 1.7°
ω scans	h = −11→11
30223 measured reflections	k = −26→27
6227 independent reflections	l = −19→19

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0727P)^2 + 0.4654P] where P = (Fo^2 + 2Fc^2)/3
6227 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.14 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
C1	0.20282 (15)	0.55435 (6)	0.32367 (9)	0.0414 (3)
C2	0.26593 (16)	0.59794 (6)	0.24794 (9)	0.0408 (3)
C3	0.18083 (17)	0.66480 (7)	0.25224 (9)	0.0463 (3)
H3	0.0838	0.6624	0.2088	0.056*
C4	0.13622 (18)	0.66347 (7)	0.34642 (10)	0.0482 (3)
H4	0.2277	0.6716	0.3925	0.058*
C5	−0.0043 (2)	0.69940 (9)	0.36999 (12)	0.0668 (5)
H5A	−0.0845	0.7041	0.3172	0.080*
H5B	0.0244	0.7421	0.3947	0.080*
C6	−0.0591 (2)	0.65503 (9)	0.44173 (12)	0.0648 (4)
H6A	−0.0304	0.6735	0.5019	0.078*
H6B	−0.1712	0.6497	0.4294	0.078*
C7	0.02285 (18)	0.58926 (8)	0.43503 (10)	0.0532 (4)
H7A	0.1049	0.5825	0.4863	0.064*
H7B	−0.0502	0.5534	0.4312	0.064*
C8	0.33208 (16)	0.53665 (7)	0.40410 (9)	0.0440 (3)
C9	0.22127 (18)	0.44122 (7)	0.35166 (10)	0.0502 (3)
C10	0.1873 (2)	0.37586 (8)	0.34179 (14)	0.0693 (5)
H10	0.2451	0.3450	0.3782	0.083*
C11	0.0651 (3)	0.35793 (10)	0.27642 (17)	0.0845 (6)
H11	0.0408	0.3141	0.2683	0.101*
C12	−0.0222 (3)	0.40324 (11)	0.22271 (16)	0.0819 (6)
H12	−0.1054	0.3898	0.1797	0.098*
C13	0.01343 (19)	0.46950 (9)	0.23231 (12)	0.0628 (4)
H13	−0.0456	0.5004	0.1965	0.075*
C14	0.13785 (16)	0.48778 (7)	0.29603 (10)	0.0472 (3)
C15	0.22386 (16)	0.56632 (7)	0.15425 (9)	0.0464 (3)
C16	0.32465 (16)	0.51203 (7)	0.13114 (9)	0.0446 (3)
C17	0.25985 (18)	0.47060 (7)	0.06710 (10)	0.0514 (3)
H17	0.1578	0.4803	0.0416	0.062*
C18	0.32430 (19)	0.41232 (7)	0.03070 (10)	0.0527 (4)
C19	0.2215 (2)	0.36360 (10)	−0.00361 (15)	0.0833 (6)
H19	0.1158	0.3691	−0.0028	0.100*
C20	0.2726 (3)	0.30731 (12)	−0.0389 (2)	0.1058 (8)
H20	0.2018	0.2750	−0.0608	0.127*
C21	0.4278 (3)	0.29898 (10)	−0.04152 (16)	0.0892 (7)
H21	0.4626	0.2610	−0.0654	0.107*
C22	0.5312 (2)	0.34658 (10)	−0.00905 (12)	0.0701 (5)
H22	0.6365	0.3408	−0.0110	0.084*
C23	0.4812 (2)	0.40299 (8)	0.02658 (11)	0.0584 (4)
H23	0.5529	0.4351	0.0481	0.070*
C24	0.48794 (16)	0.50663 (7)	0.18188 (10)	0.0473 (3)
H24A	0.5164	0.4611	0.1884	0.057*
H24B	0.5587	0.5275	0.1470	0.057*
C25	0.44360 (16)	0.60216 (7)	0.26579 (10)	0.0457 (3)
H25A	0.4801	0.6257	0.2171	0.055*
H25B	0.4783	0.6250	0.3222	0.055*
C26	0.66638 (17)	0.53358 (9)	0.31590 (12)	0.0627 (4)
H26A	0.6754	0.5535	0.3746	0.094*
H26B	0.7310	0.5564	0.2800	0.094*
H26C	0.6991	0.4890	0.3226	0.094*
C27	0.26661 (19)	0.72455 (7)	0.22827 (10)	0.0509 (4)
C28	0.2254 (2)	0.75305 (8)	0.14355 (11)	0.0613 (4)
H28	0.1479	0.7342	0.1014	0.074*
C29	0.2985 (3)	0.80923 (10)	0.12091 (15)	0.0770 (6)
H29	0.2687	0.8278	0.0640	0.092*
C30	0.4128 (3)	0.83739 (9)	0.18068 (16)	0.0801 (6)
H30	0.4609	0.8751	0.1650	0.096*
C31	0.4566 (3)	0.80986 (9)	0.26419 (15)	0.0832 (6)
H31	0.5363	0.8285	0.3051	0.100*
C32	0.3827 (2)	0.75426 (8)	0.28803 (12)	0.0705 (5)
H32	0.4121	0.7366	0.3456	0.085*
N1	0.08561 (14)	0.59674 (6)	0.35120 (8)	0.0462 (3)
N2	0.33219 (15)	0.47137 (6)	0.41599 (8)	0.0507 (3)
H2	0.3930	0.4511	0.4579	0.061*
N3	0.50515 (13)	0.53636 (6)	0.27116 (8)	0.0449 (3)
O1	0.41189 (12)	0.57530 (5)	0.45415 (7)	0.0527 (3)
O2	0.11484 (15)	0.58529 (6)	0.10030 (8)	0.0723 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0422 (7)	0.0377 (7)	0.0441 (7)	0.0032 (5)	0.0058 (5)	0.0003 (5)
C2	0.0460 (7)	0.0364 (6)	0.0395 (6)	0.0055 (5)	0.0055 (5)	0.0027 (5)
C3	0.0555 (8)	0.0394 (7)	0.0433 (7)	0.0093 (6)	0.0054 (6)	0.0025 (6)
C4	0.0566 (8)	0.0405 (7)	0.0483 (8)	0.0080 (6)	0.0106 (6)	0.0003 (6)
C5	0.0781 (11)	0.0560 (9)	0.0701 (10)	0.0208 (8)	0.0237 (9)	−0.0008 (8)
C6	0.0616 (10)	0.0646 (10)	0.0728 (11)	0.0075 (8)	0.0246 (8)	−0.0072 (8)
C7	0.0509 (8)	0.0566 (9)	0.0537 (8)	−0.0004 (7)	0.0132 (7)	−0.0004 (7)
C8	0.0486 (7)	0.0414 (7)	0.0429 (7)	0.0065 (6)	0.0097 (6)	0.0047 (6)
C9	0.0573 (8)	0.0404 (7)	0.0584 (8)	−0.0004 (6)	0.0260 (7)	0.0020 (6)
C10	0.0881 (13)	0.0407 (8)	0.0878 (13)	−0.0055 (8)	0.0409 (11)	0.0005 (8)
C11	0.0983 (15)	0.0548 (11)	0.1101 (17)	−0.0276 (11)	0.0461 (13)	−0.0193 (11)
C12	0.0712 (12)	0.0847 (14)	0.0939 (15)	−0.0338 (11)	0.0259 (11)	−0.0329 (12)
C13	0.0509 (9)	0.0688 (11)	0.0699 (11)	−0.0101 (8)	0.0137 (8)	−0.0140 (8)
C14	0.0463 (7)	0.0442 (7)	0.0538 (8)	−0.0029 (6)	0.0165 (6)	−0.0047 (6)
C15	0.0488 (8)	0.0461 (8)	0.0430 (7)	0.0072 (6)	0.0032 (6)	0.0007 (6)
C16	0.0490 (7)	0.0456 (7)	0.0397 (7)	0.0061 (6)	0.0088 (6)	0.0028 (6)
C17	0.0526 (8)	0.0534 (8)	0.0474 (8)	0.0085 (7)	0.0058 (6)	−0.0009 (6)
C18	0.0612 (9)	0.0513 (8)	0.0449 (7)	0.0084 (7)	0.0061 (7)	−0.0033 (6)
C19	0.0636 (11)	0.0762 (13)	0.1055 (16)	0.0082 (10)	−0.0006 (10)	−0.0339 (12)
C20	0.0877 (15)	0.0764 (14)	0.150 (2)	0.0027 (12)	0.0082 (15)	−0.0549 (15)
C21	0.0982 (16)	0.0661 (12)	0.1053 (16)	0.0167 (11)	0.0230 (13)	−0.0278 (11)
C22	0.0736 (11)	0.0757 (12)	0.0664 (10)	0.0174 (9)	0.0269 (9)	−0.0024 (9)
C23	0.0657 (10)	0.0615 (9)	0.0519 (8)	0.0027 (8)	0.0209 (7)	−0.0037 (7)
C24	0.0453 (7)	0.0482 (8)	0.0491 (8)	0.0057 (6)	0.0104 (6)	0.0015 (6)
C25	0.0486 (8)	0.0429 (7)	0.0456 (7)	−0.0021 (6)	0.0075 (6)	0.0021 (6)
C26	0.0424 (8)	0.0761 (11)	0.0668 (10)	0.0039 (7)	0.0004 (7)	−0.0020 (8)
C27	0.0685 (9)	0.0375 (7)	0.0491 (8)	0.0119 (7)	0.0166 (7)	0.0026 (6)
C28	0.0703 (10)	0.0584 (9)	0.0582 (9)	0.0223 (8)	0.0196 (8)	0.0144 (7)
C29	0.0944 (14)	0.0668 (11)	0.0786 (12)	0.0272 (11)	0.0404 (11)	0.0329 (10)
C30	0.1067 (16)	0.0460 (9)	0.1007 (15)	0.0079 (10)	0.0562 (14)	0.0089 (10)
C31	0.1148 (17)	0.0531 (10)	0.0870 (14)	−0.0187 (10)	0.0326 (12)	−0.0150 (10)
C32	0.1057 (14)	0.0497 (9)	0.0565 (9)	−0.0111 (9)	0.0147 (9)	−0.0019 (7)
N1	0.0475 (6)	0.0425 (6)	0.0497 (6)	0.0064 (5)	0.0106 (5)	0.0011 (5)
N2	0.0611 (7)	0.0410 (6)	0.0504 (7)	0.0082 (5)	0.0101 (6)	0.0103 (5)
N3	0.0393 (6)	0.0471 (6)	0.0473 (6)	0.0037 (5)	0.0041 (5)	0.0024 (5)
O1	0.0608 (6)	0.0474 (6)	0.0463 (5)	0.0055 (5)	−0.0018 (5)	−0.0003 (4)
O2	0.0743 (8)	0.0787 (8)	0.0556 (7)	0.0328 (6)	−0.0148 (6)	−0.0138 (6)

Geometric parameters (Å, º)

C1—N1	1.452 (2)	C16—C17	1.336 (2)
C1—C14	1.514 (2)	C16—C24	1.504 (2)
C1—C8	1.552 (2)	C17—C18	1.465 (2)
C1—C2	1.609 (2)	C17—H17	0.9300
C2—C25	1.530 (2)	C18—C19	1.386 (2)
C2—C15	1.534 (2)	C18—C23	1.392 (2)
C2—C3	1.569 (2)	C19—C20	1.375 (3)
C3—C27	1.511 (2)	C19—H19	0.9300
C3—C4	1.520 (2)	C20—C21	1.370 (3)
C3—H3	0.9800	C20—H20	0.9300
C4—N1	1.447 (2)	C21—C22	1.366 (3)
C4—C5	1.520 (2)	C21—H21	0.9300
C4—H4	0.9800	C22—C23	1.377 (2)
C5—C6	1.541 (2)	C22—H22	0.9300
C5—H5A	0.9700	C23—H23	0.9300
C5—H5B	0.9700	C24—N3	1.453 (2)
C6—C7	1.541 (2)	C24—H24A	0.9700
C6—H6A	0.9700	C24—H24B	0.9700
C6—H6B	0.9700	C25—N3	1.453 (2)
C7—N1	1.454 (2)	C25—H25A	0.9700
C7—H7A	0.9700	C25—H25B	0.9700
C7—H7B	0.9700	C26—N3	1.456 (2)
C8—O1	1.228 (2)	C26—H26A	0.9600
C8—N2	1.355 (2)	C26—H26B	0.9600
C9—C10	1.379 (2)	C26—H26C	0.9600
C9—C14	1.393 (2)	C27—C32	1.379 (2)
C9—N2	1.394 (2)	C27—C28	1.389 (2)
C10—C11	1.373 (3)	C28—C29	1.388 (3)
C10—H10	0.9300	C28—H28	0.9300
C11—C12	1.376 (3)	C29—C30	1.355 (3)
C11—H11	0.9300	C29—H29	0.9300
C12—C13	1.400 (3)	C30—C31	1.368 (3)
C12—H12	0.9300	C30—H30	0.9300
C13—C14	1.374 (2)	C31—C32	1.387 (3)
C13—H13	0.9300	C31—H31	0.9300
C15—O2	1.207 (2)	C32—H32	0.9300
C15—C16	1.495 (2)	N2—H2	0.8600
N1—C1—C14	111.82 (11)	C15—C16—C24	118.79 (12)
N1—C1—C8	112.14 (11)	C16—C17—C18	130.15 (14)
C14—C1—C8	101.03 (11)	C16—C17—H17	114.9
N1—C1—C2	101.59 (10)	C18—C17—H17	114.9
C14—C1—C2	117.87 (11)	C19—C18—C23	117.67 (15)
C8—C1—C2	112.83 (11)	C19—C18—C17	117.74 (15)
C25—C2—C15	105.58 (11)	C23—C18—C17	124.57 (15)
C25—C2—C3	114.49 (11)	C20—C19—C18	121.39 (19)
C15—C2—C3	111.38 (11)	C20—C19—H19	119.3
C25—C2—C1	111.12 (10)	C18—C19—H19	119.3
C15—C2—C1	110.35 (11)	C21—C20—C19	119.9 (2)
C3—C2—C1	104.01 (10)	C21—C20—H20	120.1
C27—C3—C4	116.40 (12)	C19—C20—H20	120.1
C27—C3—C2	116.62 (12)	C22—C21—C20	119.84 (18)
C4—C3—C2	102.45 (10)	C22—C21—H21	120.1
C27—C3—H3	106.9	C20—C21—H21	120.1
C4—C3—H3	106.9	C21—C22—C23	120.66 (17)
C2—C3—H3	106.9	C21—C22—H22	119.7
N1—C4—C5	100.75 (12)	C23—C22—H22	119.7
N1—C4—C3	100.86 (11)	C22—C23—C18	120.53 (17)
C5—C4—C3	122.85 (13)	C22—C23—H23	119.7
N1—C4—H4	110.3	C18—C23—H23	119.7
C5—C4—H4	110.3	N3—C24—C16	112.36 (11)
C3—C4—H4	110.3	N3—C24—H24A	109.1
C4—C5—C6	103.01 (13)	C16—C24—H24A	109.1
C4—C5—H5A	111.2	N3—C24—H24B	109.1
C6—C5—H5A	111.2	C16—C24—H24B	109.1
C4—C5—H5B	111.2	H24A—C24—H24B	107.9
C6—C5—H5B	111.2	N3—C25—C2	108.09 (11)
H5A—C5—H5B	109.1	N3—C25—H25A	110.1
C7—C6—C5	106.01 (12)	C2—C25—H25A	110.1
C7—C6—H6A	110.5	N3—C25—H25B	110.1
C5—C6—H6A	110.5	C2—C25—H25B	110.1
C7—C6—H6B	110.5	H25A—C25—H25B	108.4
C5—C6—H6B	110.5	N3—C26—H26A	109.5
H6A—C6—H6B	108.7	N3—C26—H26B	109.5
N1—C7—C6	101.88 (12)	H26A—C26—H26B	109.5
N1—C7—H7A	111.4	N3—C26—H26C	109.5
C6—C7—H7A	111.4	H26A—C26—H26C	109.5
N1—C7—H7B	111.4	H26B—C26—H26C	109.5
C6—C7—H7B	111.4	C32—C27—C28	117.23 (15)
H7A—C7—H7B	109.3	C32—C27—C3	123.08 (14)
O1—C8—N2	125.02 (13)	C28—C27—C3	119.66 (15)
O1—C8—C1	126.05 (12)	C29—C28—C27	120.87 (19)
N2—C8—C1	108.63 (12)	C29—C28—H28	119.6
C10—C9—C14	121.60 (16)	C27—C28—H28	119.6
C10—C9—N2	128.35 (16)	C30—C29—C28	120.81 (18)
C14—C9—N2	110.01 (12)	C30—C29—H29	119.6
C11—C10—C9	117.78 (19)	C28—C29—H29	119.6
C11—C10—H10	121.1	C29—C30—C31	119.44 (18)
C9—C10—H10	121.1	C29—C30—H30	120.3
C10—C11—C12	121.62 (18)	C31—C30—H30	120.3
C10—C11—H11	119.2	C30—C31—C32	120.2 (2)
C12—C11—H11	119.2	C30—C31—H31	119.9
C11—C12—C13	120.49 (19)	C32—C31—H31	119.9
C11—C12—H12	119.8	C27—C32—C31	121.42 (18)
C13—C12—H12	119.8	C27—C32—H32	119.3
C14—C13—C12	118.30 (18)	C31—C32—H32	119.3
C14—C13—H13	120.9	C4—N1—C1	108.8 (1)
C12—C13—H13	120.9	C4—N1—C7	107.6 (1)
C13—C14—C9	120.14 (15)	C1—N1—C7	124.1 (1)
C13—C14—C1	130.90 (14)	C8—N2—C9	111.4 (1)
C9—C14—C1	108.87 (13)	C8—N2—H2	124.3
O2—C15—C16	121.01 (13)	C9—N2—H2	124.3
O2—C15—C2	121.25 (12)	C26—N3—C25	112.5 (1)
C16—C15—C2	117.73 (11)	C26—N3—C24	110.7 (1)
C17—C16—C15	116.49 (13)	C25—N3—C24	111.0 (1)
C17—C16—C24	124.71 (13)
N1—C1—C2—C25	129.57 (11)	C2—C15—C16—C17	156.69 (13)
C14—C1—C2—C25	−107.91 (13)	O2—C15—C16—C24	156.82 (15)
C8—C1—C2—C25	9.32 (15)	C2—C15—C16—C24	−21.91 (19)
N1—C1—C2—C15	−113.66 (12)	C15—C16—C17—C18	−178.42 (15)
C14—C1—C2—C15	8.86 (16)	C24—C16—C17—C18	0.1 (3)
C8—C1—C2—C15	126.10 (12)	C16—C17—C18—C19	152.25 (18)
N1—C1—C2—C3	5.90 (13)	C16—C17—C18—C23	−29.0 (3)
C14—C1—C2—C3	128.42 (12)	C23—C18—C19—C20	1.3 (3)
C8—C1—C2—C3	−114.34 (12)	C17—C18—C19—C20	−179.9 (2)
C25—C2—C3—C27	28.38 (17)	C18—C19—C20—C21	−0.8 (4)
C15—C2—C3—C27	−91.31 (15)	C19—C20—C21—C22	0.1 (4)
C1—C2—C3—C27	149.83 (12)	C20—C21—C22—C23	0.1 (3)
C25—C2—C3—C4	−99.94 (13)	C21—C22—C23—C18	0.4 (3)
C15—C2—C3—C4	140.37 (12)	C19—C18—C23—C22	−1.1 (2)
C1—C2—C3—C4	21.51 (13)	C17—C18—C23—C22	−179.84 (16)
C27—C3—C4—N1	−169.76 (12)	C17—C16—C24—N3	−153.12 (14)
C2—C3—C4—N1	−41.30 (13)	C15—C16—C24—N3	25.36 (18)
C27—C3—C4—C5	79.76 (19)	C15—C2—C25—N3	−64.35 (13)
C2—C3—C4—C5	−151.78 (14)	C3—C2—C25—N3	172.77 (10)
N1—C4—C5—C6	36.54 (16)	C1—C2—C25—N3	55.31 (14)
C3—C4—C5—C6	147.08 (15)	C4—C3—C27—C32	41.3 (2)
C4—C5—C6—C7	−15.24 (18)	C2—C3—C27—C32	−79.90 (18)
C5—C6—C7—N1	−11.78 (17)	C4—C3—C27—C28	−136.53 (14)
N1—C1—C8—O1	−55.10 (18)	C2—C3—C27—C28	102.27 (16)
C14—C1—C8—O1	−174.31 (13)	C32—C27—C28—C29	−0.3 (2)
C2—C1—C8—O1	58.90 (17)	C3—C27—C28—C29	177.71 (14)
N1—C1—C8—N2	118.83 (12)	C27—C28—C29—C30	0.5 (3)
C14—C1—C8—N2	−0.38 (14)	C28—C29—C30—C31	0.2 (3)
C2—C1—C8—N2	−127.18 (12)	C29—C30—C31—C32	−1.2 (3)
C14—C9—C10—C11	−1.6 (2)	C28—C27—C32—C31	−0.8 (3)
N2—C9—C10—C11	175.80 (16)	C3—C27—C32—C31	−178.64 (17)
C9—C10—C11—C12	−0.6 (3)	C30—C31—C32—C27	1.5 (3)
C10—C11—C12—C13	1.2 (3)	C5—C4—N1—C1	175.83 (12)
C11—C12—C13—C14	0.4 (3)	C3—C4—N1—C1	49.07 (14)
C12—C13—C14—C9	−2.6 (2)	C5—C4—N1—C7	−47.35 (15)
C12—C13—C14—C1	−178.56 (15)	C3—C4—N1—C7	−174.12 (11)
C10—C9—C14—C13	3.2 (2)	C14—C1—N1—C4	−160.53 (12)
N2—C9—C14—C13	−174.59 (13)	C8—C1—N1—C4	86.79 (13)
C10—C9—C14—C1	−179.97 (13)	C2—C1—N1—C4	−33.94 (13)
N2—C9—C14—C1	2.20 (16)	C14—C1—N1—C7	71.41 (17)
N1—C1—C14—C13	55.8 (2)	C8—C1—N1—C7	−41.26 (18)
C8—C1—C14—C13	175.24 (15)	C2—C1—N1—C7	−162.00 (12)
C2—C1—C14—C13	−61.4 (2)	C6—C7—N1—C4	37.07 (15)
N1—C1—C14—C9	−120.54 (12)	C6—C7—N1—C1	165.59 (13)
C8—C1—C14—C9	−1.09 (14)	O1—C8—N2—C9	175.76 (13)
C2—C1—C14—C9	122.31 (12)	C1—C8—N2—C9	1.75 (15)
C25—C2—C15—O2	−139.18 (15)	C10—C9—N2—C8	179.82 (15)
C3—C2—C15—O2	−14.3 (2)	C14—C9—N2—C8	−2.53 (16)
C1—C2—C15—O2	100.65 (16)	C2—C25—N3—C26	−161.45 (12)
C25—C2—C15—C16	39.54 (16)	C2—C25—N3—C24	73.88 (14)
C3—C2—C15—C16	164.38 (12)	C16—C24—N3—C26	−176.62 (12)
C1—C2—C15—C16	−80.62 (15)	C16—C24—N3—C25	−50.97 (15)
O2—C15—C16—C17	−24.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.98	2.32	2.782 (2)	108
C17—H17···O2	0.93	2.38	2.759 (2)	104
C25—H25B···O1	0.97	2.38	2.926 (2)	116
N2—H2···O1^i	0.86	2.05	2.874 (2)	161
C19—H19···O2^ii	0.93	2.47	3.226 (2)	139

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