5′′-Benzyl­idene-1′,1′′-dimethyl-4′-phenylacenapthene-2-spiro-2′-pyrrolidine-3′-spiro-3′′-piperidine-1,4′′-dione

In the title compound, C₃₄H₃₀N₂O₂, the pyrrolidine and piperidinone rings each adopt a half-chair conformation. The dihedral angle between the two phenyl-ring substituents is 70.4 (1)°. Intramolecular C—H...O hydrogen bonds are observed in the crystal structure. In addition to these interactions, C—H...π interactions also play a role in stabilizing the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.070
• wR factor = 0.167
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93
PLAT480_ALERT_4_A Long H...A H-Bond Reported H12    ..  CGF     ..       3.09 Ang.

Alert level C
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  CGA     ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H36B   ..  CGG     ..       2.58 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7     ..  CGA     ..       3.54 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C12    ..  CGF     ..       3.82 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C36    ..  CGG     ..       3.43 Ang.

   4 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion

---

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: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

5''-Benzylidene-1',1''-dimethyl-4'-phenyl-acenapthene-2-spiro-2'- pyrrolidine-3'-spiro-3''-piperidine-1,4''-dione

Crystal data

C34H30N2O2	F(000) = 1056
Mr = 498.60	Dx = 1.219 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2836 reflections
a = 16.6609 (1) Å	θ = 2.3–25.4°
b = 10.4558 (9) Å	µ = 0.08 mm^−1
c = 17.4457 (2) Å	T = 273 K
β = 116.589 (1)°	Block, colourless
V = 2717.7 (2) Å^3	0.21 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer	4068 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 28.0°, θmin = 1.4°
ω scans	h = −21→21
16066 measured reflections	k = −13→12
6130 independent reflections	l = −22→22

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0702P)^2 + 0.4469P] where P = (Fo^2 + 2Fc^2)/3
6130 reflections	(Δ/σ)max < 0.001
345 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.17 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	0.23376 (15)	0.6606 (2)	0.10662 (14)	0.0510 (6)
H1A	0.2115	0.6607	0.0449	0.061*
H1B	0.2670	0.5823	0.1299	0.061*
C2	0.29105 (13)	0.7776 (2)	0.14709 (12)	0.0399 (5)
H2	0.2610	0.8509	0.1105	0.048*
C3	0.28420 (13)	0.79555 (19)	0.23295 (12)	0.0347 (4)
C4	0.20154 (13)	0.70663 (19)	0.22197 (12)	0.0361 (5)
C5	0.13196 (13)	0.7627 (2)	0.24665 (12)	0.0377 (5)
C6	0.07054 (14)	0.8581 (2)	0.21173 (15)	0.0534 (6)
H6	0.0660	0.9025	0.1638	0.064*
C7	0.01405 (17)	0.8880 (3)	0.2497 (2)	0.0700 (8)
H7	−0.0273	0.9540	0.2263	0.084*
C8	0.01738 (19)	0.8244 (3)	0.3191 (2)	0.0740 (8)
H8	−0.0207	0.8482	0.3426	0.089*
C9	0.07786 (16)	0.7234 (2)	0.35551 (16)	0.0542 (6)
C10	0.0893 (2)	0.6449 (3)	0.42603 (18)	0.0709 (8)
H10	0.0554	0.6610	0.4552	0.085*
C11	0.1490 (2)	0.5467 (3)	0.45174 (17)	0.0706 (8)
H11	0.1552	0.4978	0.4986	0.085*
C12	0.20159 (16)	0.5167 (2)	0.41003 (15)	0.0572 (6)
H12	0.2411	0.4479	0.4277	0.069*
C13	0.19301 (13)	0.5921 (2)	0.34233 (14)	0.0430 (5)
C14	0.23447 (13)	0.5873 (2)	0.28347 (14)	0.0427 (5)
C15	0.13302 (13)	0.6946 (2)	0.31661 (13)	0.0403 (5)
C16	0.37031 (13)	0.7572 (2)	0.31125 (11)	0.0375 (5)
H16A	0.3881	0.6718	0.3034	0.045*
H16B	0.4183	0.8158	0.3185	0.045*
C17	0.34909 (16)	0.8911 (2)	0.41082 (13)	0.0503 (6)
H17A	0.4081	0.9301	0.4330	0.060*
H17B	0.3308	0.8911	0.4564	0.060*
C18	0.28365 (14)	0.9702 (2)	0.33710 (13)	0.0418 (5)
C19	0.26335 (14)	0.9330 (2)	0.24705 (13)	0.0406 (5)
C20	0.23871 (16)	1.0695 (2)	0.34647 (15)	0.0518 (6)
H20	0.1993	1.1098	0.2961	0.062*
C21	0.24319 (18)	1.1238 (2)	0.42600 (16)	0.0552 (6)
C22	0.1648 (2)	1.1621 (3)	0.42798 (19)	0.0701 (8)
H22	0.1104	1.1542	0.3791	0.084*
C23	0.1666 (3)	1.2124 (3)	0.5021 (3)	0.0900 (11)
H23	0.1133	1.2357	0.5032	0.108*
C24	0.2464 (3)	1.2279 (3)	0.5737 (2)	0.0964 (12)
H24	0.2474	1.2621	0.6233	0.116*
C25	0.3240 (3)	1.1932 (3)	0.5721 (2)	0.0958 (11)
H25	0.3784	1.2052	0.6206	0.115*
C26	0.3230 (2)	1.1407 (3)	0.49958 (18)	0.0759 (8)
H26	0.3768	1.1160	0.4998	0.091*
C27	0.38636 (14)	0.7750 (2)	0.15760 (11)	0.0398 (5)
C28	0.43052 (17)	0.8892 (3)	0.16288 (14)	0.0571 (7)
H28	0.4004	0.9661	0.1575	0.068*
C29	0.51937 (19)	0.8903 (3)	0.17618 (16)	0.0709 (9)
H29	0.5481	0.9681	0.1801	0.085*
C30	0.56498 (18)	0.7787 (4)	0.18352 (16)	0.0715 (8)
H30	0.6243	0.7799	0.1924	0.086*
C31	0.52196 (17)	0.6664 (3)	0.17762 (16)	0.0657 (7)
H31	0.5522	0.5898	0.1822	0.079*
C32	0.43352 (15)	0.6637 (2)	0.16492 (14)	0.0515 (6)
H32	0.4056	0.5854	0.1613	0.062*
C35	0.09733 (17)	0.5700 (3)	0.10341 (18)	0.0727 (8)
H35A	0.0708	0.5618	0.0422	0.109*
H35B	0.0512	0.5866	0.1208	0.109*
H35C	0.1279	0.4921	0.1294	0.109*
C36	0.42189 (16)	0.6880 (3)	0.45756 (13)	0.0607 (7)
H36A	0.4195	0.5998	0.4414	0.091*
H36B	0.4100	0.6948	0.5064	0.091*
H36C	0.4805	0.7217	0.4718	0.091*
N1	0.16106 (11)	0.67520 (19)	0.13035 (11)	0.0480 (5)
N2	0.35469 (11)	0.76036 (17)	0.38628 (10)	0.0404 (4)
O1	0.23082 (12)	1.00882 (16)	0.18866 (10)	0.0608 (5)
O2	0.28038 (11)	0.50218 (16)	0.27697 (12)	0.0645 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0510 (13)	0.0636 (16)	0.0424 (12)	−0.0152 (11)	0.0245 (10)	−0.0183 (11)
C2	0.0462 (11)	0.0447 (13)	0.0297 (10)	−0.0037 (10)	0.0179 (9)	−0.0008 (9)
C3	0.0383 (10)	0.0370 (12)	0.0297 (9)	−0.0044 (9)	0.0160 (8)	−0.0007 (8)
C4	0.0349 (10)	0.0369 (12)	0.0368 (10)	−0.0011 (9)	0.0162 (8)	−0.0009 (8)
C5	0.0346 (10)	0.0379 (12)	0.0386 (10)	−0.0001 (9)	0.0145 (9)	−0.0020 (9)
C6	0.0440 (12)	0.0533 (15)	0.0567 (14)	0.0102 (11)	0.0171 (11)	0.0074 (12)
C7	0.0520 (15)	0.0642 (19)	0.091 (2)	0.0218 (13)	0.0294 (15)	0.0002 (15)
C8	0.0723 (18)	0.076 (2)	0.094 (2)	0.0092 (16)	0.0559 (17)	−0.0143 (17)
C9	0.0589 (14)	0.0551 (16)	0.0583 (14)	−0.0065 (12)	0.0349 (12)	−0.0129 (12)
C10	0.094 (2)	0.077 (2)	0.0651 (17)	−0.0188 (18)	0.0555 (16)	−0.0160 (15)
C11	0.098 (2)	0.069 (2)	0.0511 (15)	−0.0220 (17)	0.0387 (15)	0.0035 (14)
C12	0.0588 (14)	0.0479 (15)	0.0539 (14)	−0.0111 (12)	0.0153 (12)	0.0100 (11)
C13	0.0402 (11)	0.0379 (13)	0.0476 (12)	−0.0060 (9)	0.0167 (10)	0.0021 (10)
C14	0.0333 (10)	0.0361 (13)	0.0570 (13)	0.0000 (9)	0.0187 (10)	0.0014 (10)
C15	0.0377 (11)	0.0405 (13)	0.0431 (11)	−0.0069 (9)	0.0184 (9)	−0.0061 (9)
C16	0.0374 (10)	0.0456 (13)	0.0324 (10)	−0.0058 (9)	0.0183 (9)	−0.0013 (9)
C17	0.0582 (14)	0.0593 (16)	0.0348 (11)	−0.0064 (12)	0.0220 (10)	−0.0083 (10)
C18	0.0511 (12)	0.0383 (13)	0.0397 (11)	−0.0088 (10)	0.0236 (10)	−0.0063 (9)
C19	0.0461 (11)	0.0389 (13)	0.0384 (11)	−0.0047 (10)	0.0204 (9)	0.0016 (10)
C20	0.0624 (14)	0.0451 (15)	0.0482 (13)	−0.0040 (12)	0.0250 (11)	−0.0039 (11)
C21	0.0758 (17)	0.0394 (14)	0.0584 (15)	−0.0011 (12)	0.0370 (13)	−0.0080 (11)
C22	0.088 (2)	0.0530 (18)	0.0822 (19)	0.0024 (15)	0.0497 (17)	−0.0088 (14)
C23	0.134 (3)	0.060 (2)	0.117 (3)	0.007 (2)	0.093 (3)	−0.0101 (19)
C24	0.178 (4)	0.059 (2)	0.080 (2)	0.004 (2)	0.082 (3)	−0.0127 (17)
C25	0.137 (3)	0.079 (2)	0.0633 (19)	0.007 (2)	0.038 (2)	−0.0252 (16)
C26	0.091 (2)	0.067 (2)	0.0673 (18)	−0.0032 (16)	0.0333 (16)	−0.0259 (15)
C27	0.0507 (12)	0.0482 (14)	0.0256 (9)	−0.0119 (10)	0.0216 (9)	−0.0059 (9)
C28	0.0772 (17)	0.0556 (16)	0.0513 (14)	−0.0216 (13)	0.0404 (13)	−0.0174 (11)
C29	0.0752 (18)	0.090 (2)	0.0599 (16)	−0.0488 (18)	0.0417 (15)	−0.0288 (15)
C30	0.0518 (15)	0.114 (3)	0.0531 (15)	−0.0182 (17)	0.0275 (13)	−0.0131 (16)
C31	0.0529 (15)	0.089 (2)	0.0586 (15)	0.0062 (15)	0.0276 (13)	0.0066 (14)
C32	0.0541 (14)	0.0564 (16)	0.0494 (13)	−0.0032 (12)	0.0279 (11)	0.0037 (11)
C35	0.0523 (14)	0.091 (2)	0.0761 (18)	−0.0301 (15)	0.0298 (14)	−0.0358 (16)
C36	0.0640 (15)	0.083 (2)	0.0320 (11)	0.0123 (14)	0.0190 (11)	0.0102 (11)
N1	0.0406 (10)	0.0605 (13)	0.0412 (10)	−0.0129 (9)	0.0169 (8)	−0.0150 (9)
N2	0.0428 (9)	0.0493 (11)	0.0298 (8)	0.0008 (8)	0.0169 (7)	0.0015 (8)
O1	0.0951 (13)	0.0440 (10)	0.0471 (9)	0.0063 (9)	0.0353 (9)	0.0081 (8)
O2	0.0585 (10)	0.0447 (10)	0.0982 (14)	0.0142 (8)	0.0422 (10)	0.0069 (9)

Geometric parameters (Å, º)

C1—N1	1.453 (3)	C17—H17A	0.9700
C1—C2	1.518 (3)	C17—H17B	0.9700
C1—H1A	0.9700	C18—C20	1.332 (3)
C1—H1B	0.9700	C18—C19	1.503 (3)
C2—C27	1.515 (3)	C19—O1	1.211 (2)
C2—C3	1.564 (3)	C20—C21	1.470 (3)
C2—H2	0.9800	C20—H20	0.9300
C3—C19	1.524 (3)	C21—C22	1.381 (4)
C3—C16	1.527 (3)	C21—C26	1.386 (4)
C3—C4	1.601 (3)	C22—C23	1.384 (4)
C4—N1	1.467 (3)	C22—H22	0.9300
C4—C5	1.523 (3)	C23—C24	1.366 (5)
C4—C14	1.575 (3)	C23—H23	0.9300
C5—C6	1.362 (3)	C24—C25	1.355 (5)
C5—C15	1.406 (3)	C24—H24	0.9300
C6—C7	1.407 (4)	C25—C26	1.373 (4)
C6—H6	0.9300	C25—H25	0.9300
C7—C8	1.362 (4)	C26—H26	0.9300
C7—H7	0.9300	C27—C32	1.377 (3)
C8—C9	1.401 (4)	C27—C28	1.384 (3)
C8—H8	0.9300	C28—C29	1.392 (4)
C9—C15	1.398 (3)	C28—H28	0.9300
C9—C10	1.419 (4)	C29—C30	1.367 (4)
C10—C11	1.358 (4)	C29—H29	0.9300
C10—H10	0.9300	C30—C31	1.356 (4)
C11—C12	1.402 (4)	C30—H30	0.9300
C11—H11	0.9300	C31—C32	1.389 (3)
C12—C13	1.373 (3)	C31—H31	0.9300
C12—H12	0.9300	C32—H32	0.9300
C13—C15	1.396 (3)	C35—N1	1.453 (3)
C13—C14	1.473 (3)	C35—H35A	0.9600
C14—O2	1.212 (2)	C35—H35B	0.9600
C16—N2	1.445 (2)	C35—H35C	0.9600
C16—H16A	0.9700	C36—N2	1.458 (3)
C16—H16B	0.9700	C36—H36A	0.9600
C17—N2	1.448 (3)	C36—H36B	0.9600
C17—C18	1.507 (3)	C36—H36C	0.9600
N1—C1—C2	102.3 (2)	N2—C17—H17B	109.1
N1—C1—H1A	111.3	C18—C17—H17B	109.1
C2—C1—H1A	111.3	H17A—C17—H17B	107.8
N1—C1—H1B	111.3	C20—C18—C19	117.0 (2)
C2—C1—H1B	111.3	C20—C18—C17	123.7 (2)
H1A—C1—H1B	109.2	C19—C18—C17	119.3 (2)
C27—C2—C1	116.6 (2)	O1—C19—C18	121.1 (2)
C27—C2—C3	114.1 (2)	O1—C19—C3	122.0 (2)
C1—C2—C3	104.0 (2)	C18—C19—C3	116.9 (2)
C27—C2—H2	107.2	C18—C20—C21	128.5 (2)
C1—C2—H2	107.2	C18—C20—H20	115.7
C3—C2—H2	107.2	C21—C20—H20	115.7
C19—C3—C16	107.1 (2)	C22—C21—C26	117.8 (2)
C19—C3—C2	112.8 (2)	C22—C21—C20	119.1 (2)
C16—C3—C2	112.6 (2)	C26—C21—C20	123.1 (2)
C19—C3—C4	108.7 (2)	C21—C22—C23	120.6 (3)
C16—C3—C4	111.6 (2)	C21—C22—H22	119.7
C2—C3—C4	104.1 (2)	C23—C22—H22	119.7
N1—C4—C5	110.9 (2)	C24—C23—C22	120.3 (3)
N1—C4—C14	114.5 (2)	C24—C23—H23	119.9
C5—C4—C14	100.9 (2)	C22—C23—H23	119.9
N1—C4—C3	102.2 (2)	C25—C24—C23	119.8 (3)
C5—C4—C3	117.8 (2)	C25—C24—H24	120.1
C14—C4—C3	111.1 (2)	C23—C24—H24	120.1
C6—C5—C15	118.3 (2)	C24—C25—C26	120.5 (3)
C6—C5—C4	132.1 (2)	C24—C25—H25	119.8
C15—C5—C4	109.6 (2)	C26—C25—H25	119.8
C5—C6—C7	118.7 (2)	C25—C26—C21	121.1 (3)
C5—C6—H6	120.7	C25—C26—H26	119.5
C7—C6—H6	120.7	C21—C26—H26	119.5
C8—C7—C6	122.7 (2)	C32—C27—C28	117.3 (2)
C8—C7—H7	118.6	C32—C27—C2	123.4 (2)
C6—C7—H7	118.6	C28—C27—C2	119.3 (2)
C7—C8—C9	120.4 (2)	C27—C28—C29	120.9 (3)
C7—C8—H8	119.8	C27—C28—H28	119.6
C9—C8—H8	119.8	C29—C28—H28	119.6
C15—C9—C8	116.0 (2)	C30—C29—C28	120.9 (3)
C15—C9—C10	115.7 (2)	C30—C29—H29	119.6
C8—C9—C10	128.3 (2)	C28—C29—H29	119.6
C11—C10—C9	121.2 (2)	C31—C30—C29	118.7 (3)
C11—C10—H10	119.4	C31—C30—H30	120.7
C9—C10—H10	119.4	C29—C30—H30	120.7
C10—C11—C12	122.2 (2)	C30—C31—C32	121.1 (3)
C10—C11—H11	118.9	C30—C31—H31	119.4
C12—C11—H11	118.9	C32—C31—H31	119.4
C13—C12—C11	118.0 (2)	C27—C32—C31	121.2 (2)
C13—C12—H12	121.0	C27—C32—H32	119.4
C11—C12—H12	121.0	C31—C32—H32	119.4
C12—C13—C15	120.1 (2)	N1—C35—H35A	109.5
C12—C13—C14	132.8 (2)	N1—C35—H35B	109.5
C15—C13—C14	107.1 (2)	H35A—C35—H35B	109.5
O2—C14—C13	127.1 (2)	N1—C35—H35C	109.5
O2—C14—C4	124.1 (2)	H35A—C35—H35C	109.5
C13—C14—C4	108.6 (2)	H35B—C35—H35C	109.5
C13—C15—C9	122.8 (2)	N2—C36—H36A	109.5
C13—C15—C5	113.4 (2)	N2—C36—H36B	109.5
C9—C15—C5	123.8 (2)	H36A—C36—H36B	109.5
N2—C16—C3	109.1 (2)	N2—C36—H36C	109.5
N2—C16—H16A	109.9	H36A—C36—H36C	109.5
C3—C16—H16A	109.9	H36B—C36—H36C	109.5
N2—C16—H16B	109.9	C1—N1—C35	114.2 (2)
C3—C16—H16B	109.9	C1—N1—C4	107.4 (2)
H16A—C16—H16B	108.3	C35—N1—C4	115.8 (2)
N2—C17—C18	112.5 (2)	C16—N2—C17	110.6 (2)
N2—C17—H17A	109.1	C16—N2—C36	112.3 (2)
C18—C17—H17A	109.1	C17—N2—C36	111.4 (2)
N1—C1—C2—C27	162.77 (17)	C4—C5—C15—C13	−2.7 (2)
N1—C1—C2—C3	36.2 (2)	C6—C5—C15—C9	−3.5 (3)
C27—C2—C3—C19	99.7 (2)	C4—C5—C15—C9	179.09 (19)
C1—C2—C3—C19	−132.16 (18)	C19—C3—C16—N2	63.0 (2)
C27—C2—C3—C16	−21.6 (2)	C2—C3—C16—N2	−172.52 (16)
C1—C2—C3—C16	106.52 (19)	C4—C3—C16—N2	−55.9 (2)
C27—C2—C3—C4	−142.62 (18)	N2—C17—C18—C20	151.2 (2)
C1—C2—C3—C4	−14.5 (2)	N2—C17—C18—C19	−25.6 (3)
C19—C3—C4—N1	108.40 (17)	C20—C18—C19—O1	22.2 (3)
C16—C3—C4—N1	−133.68 (17)	C17—C18—C19—O1	−160.8 (2)
C2—C3—C4—N1	−12.03 (19)	C20—C18—C19—C3	−156.83 (19)
C19—C3—C4—C5	−13.4 (2)	C17—C18—C19—C3	20.2 (3)
C16—C3—C4—C5	104.5 (2)	C16—C3—C19—O1	144.1 (2)
C2—C3—C4—C5	−133.85 (18)	C2—C3—C19—O1	19.7 (3)
C19—C3—C4—C14	−129.03 (17)	C4—C3—C19—O1	−95.2 (2)
C16—C3—C4—C14	−11.1 (2)	C16—C3—C19—C18	−36.9 (2)
C2—C3—C4—C14	110.54 (18)	C2—C3—C19—C18	−161.24 (17)
N1—C4—C5—C6	−49.6 (3)	C4—C3—C19—C18	83.8 (2)
C14—C4—C5—C6	−171.3 (2)	C19—C18—C20—C21	178.1 (2)
C3—C4—C5—C6	67.7 (3)	C17—C18—C20—C21	1.2 (4)
N1—C4—C5—C15	127.33 (18)	C18—C20—C21—C22	−139.0 (3)
C14—C4—C5—C15	5.6 (2)	C18—C20—C21—C26	42.1 (4)
C3—C4—C5—C15	−115.43 (19)	C26—C21—C22—C23	−1.8 (4)
C15—C5—C6—C7	3.0 (3)	C20—C21—C22—C23	179.3 (3)
C4—C5—C6—C7	179.7 (2)	C21—C22—C23—C24	1.8 (5)
C5—C6—C7—C8	−0.9 (4)	C22—C23—C24—C25	−0.4 (5)
C6—C7—C8—C9	−0.8 (5)	C23—C24—C25—C26	−1.1 (6)
C7—C8—C9—C15	0.4 (4)	C24—C25—C26—C21	1.1 (5)
C7—C8—C9—C10	−178.4 (3)	C22—C21—C26—C25	0.3 (4)
C15—C9—C10—C11	−1.5 (4)	C20—C21—C26—C25	179.2 (3)
C8—C9—C10—C11	177.4 (3)	C1—C2—C27—C32	−26.0 (3)
C9—C10—C11—C12	−0.6 (4)	C3—C2—C27—C32	95.3 (2)
C10—C11—C12—C13	1.5 (4)	C1—C2—C27—C28	156.01 (19)
C11—C12—C13—C15	−0.3 (3)	C3—C2—C27—C28	−82.6 (2)
C11—C12—C13—C14	−178.1 (2)	C32—C27—C28—C29	−0.8 (3)
C12—C13—C14—O2	9.1 (4)	C2—C27—C28—C29	177.26 (19)
C15—C13—C14—O2	−168.9 (2)	C27—C28—C29—C30	0.7 (4)
C12—C13—C14—C4	−176.6 (2)	C28—C29—C30—C31	0.0 (4)
C15—C13—C14—C4	5.4 (2)	C29—C30—C31—C32	−0.4 (4)
N1—C4—C14—O2	48.7 (3)	C28—C27—C32—C31	0.4 (3)
C5—C4—C14—O2	167.9 (2)	C2—C27—C32—C31	−177.60 (19)
C3—C4—C14—O2	−66.4 (3)	C30—C31—C32—C27	0.2 (4)
N1—C4—C14—C13	−125.81 (18)	C2—C1—N1—C35	−176.66 (19)
C5—C4—C14—C13	−6.6 (2)	C2—C1—N1—C4	−46.8 (2)
C3—C4—C14—C13	119.03 (17)	C5—C4—N1—C1	162.81 (18)
C12—C13—C15—C9	−1.9 (3)	C14—C4—N1—C1	−83.8 (2)
C14—C13—C15—C9	176.4 (2)	C3—C4—N1—C1	36.4 (2)
C12—C13—C15—C5	179.9 (2)	C5—C4—N1—C35	−68.3 (2)
C14—C13—C15—C5	−1.8 (2)	C14—C4—N1—C35	45.1 (3)
C8—C9—C15—C13	−176.2 (2)	C3—C4—N1—C35	165.34 (19)
C10—C9—C15—C13	2.7 (3)	C3—C16—N2—C17	−73.1 (2)
C8—C9—C15—C5	1.8 (3)	C3—C16—N2—C36	161.82 (18)
C10—C9—C15—C5	−179.3 (2)	C18—C17—N2—C16	51.3 (2)
C6—C5—C15—C13	174.6 (2)	C18—C17—N2—C36	176.95 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.98	2.33	2.834 (3)	111
C16—H16A···O2	0.97	2.42	2.985 (3)	117
C20—H20···O1	0.93	2.41	2.770 (3)	103
C7—H7···CgA^i	0.93	2.65	3.544 (3)	162
C12—H12···CgF^ii	0.93	3.09	3.824 (2)	137
C36—H36B···CgG^iii	0.96	2.58	3.426 (6)	147

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