Spiro-[2-3′]­ox­indole-spiro-[3-3′′]­ox­indole-4[p-methyl­benzyl]­pyrrolidizine

The ox­indole moieties of the title compound, C₂₉H₂₅N₃O₃, are planar. The pyrrolidine ring adopts a half-chair conformation. The structure is stabilized by C—H...O intramol­ecular interactions. It is remarkable that only one of the two NH groups forms a hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.155
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.92

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.00
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               5057
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5512
           Completeness (_total/calc)             91.75%
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

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

   1 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 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: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Spiro- [2 - 3'] oxindole - spiro -[3- 3"] oxindole - 4[p-methyl benzydy] pyrolidizine.

Crystal data

C29H25N3O3	Z = 2
Mr = 463.52	F(000) = 488
Triclinic, P1	Dx = 1.348 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7632 (6) Å	Cell parameters from 3128 reflections
b = 10.3841 (7) Å	θ = 2.6–27.5°
c = 11.6874 (8) Å	µ = 0.09 mm^−1
α = 99.735 (1)°	T = 293 K
β = 96.480 (1)°	Block, colourless
γ = 98.892 (1)°	0.40 × 0.30 × 0.20 mm
V = 1141.98 (13) Å^3

Data collection

CCD Area Detector diffractometer	5057 independent reflections
Radiation source: fine-focus sealed tube	4178 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→12
Tmin = 0.966, Tmax = 0.983	k = −13→5
7283 measured reflections	l = −14→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.106P)^2 + 0.1974P] where P = (Fo^2 + 2Fc^2)/3
5057 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.20 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	0.47061 (14)	0.87861 (14)	0.36014 (13)	0.0434 (3)
H1	0.3906	0.8975	0.3740	0.052*
C2	0.50070 (15)	0.75446 (15)	0.34976 (12)	0.0349 (3)
O3	0.42241 (12)	0.65750 (12)	0.36220 (11)	0.0482 (3)
C4	0.65378 (14)	0.76396 (14)	0.32510 (12)	0.0301 (3)
C5	0.69521 (15)	0.90992 (14)	0.32391 (12)	0.0325 (3)
C6	0.58304 (16)	0.97256 (15)	0.34598 (13)	0.0379 (3)
C7	0.5914 (2)	1.10778 (17)	0.35435 (17)	0.0507 (4)
H7	0.5153	1.1485	0.3695	0.061*
C8	0.7168 (2)	1.18050 (17)	0.33946 (17)	0.0538 (5)
H8	0.7255	1.2718	0.3447	0.065*
C9	0.8293 (2)	1.11983 (17)	0.31696 (16)	0.0485 (4)
H9	0.9130	1.1706	0.3075	0.058*
C10	0.81922 (17)	0.98411 (16)	0.30831 (14)	0.0402 (3)
H10	0.8951	0.9434	0.2922	0.048*
C11	0.68194 (15)	0.67199 (14)	0.21279 (12)	0.0335 (3)
H11	0.6300	0.5822	0.2084	0.040*
C12	0.64155 (17)	0.71810 (17)	0.09900 (13)	0.0407 (4)
O13	0.72920 (14)	0.75169 (18)	0.03922 (12)	0.0706 (5)
C14	0.49214 (16)	0.72518 (16)	0.06388 (13)	0.0397 (4)
C15	0.38187 (19)	0.64363 (19)	0.09421 (15)	0.0501 (4)
H15	0.3996	0.5775	0.1355	0.060*
C16	0.24597 (19)	0.6595 (2)	0.06375 (16)	0.0580 (5)
H16	0.1730	0.6028	0.0839	0.070*
C17	0.21551 (19)	0.7578 (2)	0.00391 (15)	0.0545 (5)
C18	0.3256 (2)	0.8371 (2)	−0.02897 (17)	0.0560 (5)
H18	0.3075	0.9024	−0.0711	0.067*
C19	0.46184 (19)	0.82088 (19)	−0.00046 (16)	0.0493 (4)
H19	0.5343	0.8745	−0.0245	0.059*
C20	0.74599 (14)	0.71611 (14)	0.42183 (12)	0.0312 (3)
C21	0.67600 (16)	0.57623 (15)	0.44078 (14)	0.0368 (3)
O22	0.64199 (14)	0.47576 (11)	0.36676 (11)	0.0489 (3)
N23	0.66531 (15)	0.58586 (14)	0.55606 (12)	0.0438 (3)
H23	0.6321	0.5203	0.5869	0.053*
C24	0.71408 (16)	0.71406 (17)	0.61920 (13)	0.0396 (3)
C25	0.71806 (19)	0.7587 (2)	0.73810 (15)	0.0530 (5)
H25	0.6866	0.7016	0.7866	0.064*
C26	0.7705 (2)	0.8913 (2)	0.78193 (15)	0.0575 (5)
H26	0.7736	0.9244	0.8614	0.069*
C27	0.81832 (18)	0.97537 (19)	0.71017 (16)	0.0506 (4)
H27	0.8519	1.0646	0.7417	0.061*
C28	0.81707 (16)	0.92871 (16)	0.59059 (14)	0.0400 (4)
H28	0.8516	0.9854	0.5428	0.048*
C29	0.76368 (14)	0.79693 (15)	0.54495 (12)	0.0333 (3)
N30	0.87489 (13)	0.71261 (12)	0.37002 (10)	0.0343 (3)
C31	0.97147 (19)	0.62994 (19)	0.41402 (15)	0.0486 (4)
H31A	0.9241	0.5678	0.4563	0.058*
H31B	1.0514	0.6849	0.4659	0.058*
C32	1.0173 (2)	0.5570 (2)	0.30558 (17)	0.0612 (5)
H32A	1.0382	0.4715	0.3174	0.073*
H32B	1.0995	0.6085	0.2852	0.073*
C33	0.89170 (19)	0.54006 (18)	0.21023 (15)	0.0488 (4)
H33A	0.8210	0.4649	0.2142	0.059*
H33B	0.9198	0.5287	0.1327	0.059*
C34	0.83894 (16)	0.67102 (15)	0.24069 (12)	0.0356 (3)
H34	0.8907	0.7372	0.2035	0.043*
C35	0.0676 (2)	0.7769 (3)	−0.0270 (2)	0.0804 (7)
H35A	0.0049	0.7134	0.0020	0.121*
H35B	0.0450	0.7644	−0.1107	0.121*
H35C	0.0581	0.8650	0.0079	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0341 (6)	0.0512 (8)	0.0521 (8)	0.0192 (6)	0.0131 (6)	0.0146 (6)
C2	0.0317 (7)	0.0447 (8)	0.0308 (7)	0.0089 (6)	0.0033 (5)	0.0132 (6)
O3	0.0369 (6)	0.0559 (7)	0.0545 (7)	0.0026 (5)	0.0062 (5)	0.0234 (6)
C4	0.0304 (6)	0.0324 (7)	0.0295 (6)	0.0081 (5)	0.0037 (5)	0.0092 (5)
C5	0.0360 (7)	0.0330 (7)	0.0304 (7)	0.0103 (6)	0.0028 (5)	0.0088 (5)
C6	0.0392 (8)	0.0412 (8)	0.0367 (7)	0.0154 (6)	0.0043 (6)	0.0096 (6)
C7	0.0581 (10)	0.0422 (9)	0.0570 (10)	0.0255 (8)	0.0076 (8)	0.0094 (8)
C8	0.0727 (12)	0.0316 (8)	0.0575 (11)	0.0137 (8)	0.0024 (9)	0.0102 (7)
C9	0.0549 (10)	0.0376 (8)	0.0513 (10)	0.0011 (7)	0.0029 (8)	0.0129 (7)
C10	0.0393 (8)	0.0384 (8)	0.0446 (8)	0.0072 (6)	0.0078 (6)	0.0110 (7)
C11	0.0363 (7)	0.0348 (7)	0.0294 (7)	0.0085 (6)	0.0031 (6)	0.0056 (6)
C12	0.0417 (8)	0.0507 (9)	0.0303 (7)	0.0100 (7)	0.0035 (6)	0.0091 (6)
O13	0.0479 (7)	0.1299 (14)	0.0484 (7)	0.0229 (8)	0.0143 (6)	0.0455 (8)
C14	0.0401 (8)	0.0485 (9)	0.0281 (7)	0.0068 (7)	−0.0013 (6)	0.0057 (6)
C15	0.0491 (9)	0.0608 (11)	0.0366 (8)	−0.0010 (8)	−0.0045 (7)	0.0153 (8)
C16	0.0417 (9)	0.0858 (14)	0.0394 (9)	−0.0052 (9)	−0.0016 (7)	0.0120 (9)
C17	0.0436 (9)	0.0780 (13)	0.0365 (8)	0.0141 (9)	−0.0025 (7)	−0.0020 (8)
C18	0.0545 (10)	0.0639 (12)	0.0514 (10)	0.0193 (9)	−0.0044 (8)	0.0160 (9)
C19	0.0444 (9)	0.0593 (11)	0.0458 (9)	0.0087 (8)	0.0009 (7)	0.0191 (8)
C20	0.0327 (7)	0.0327 (7)	0.0299 (7)	0.0099 (5)	0.0034 (5)	0.0077 (5)
C21	0.0386 (7)	0.0348 (8)	0.0397 (8)	0.0111 (6)	0.0022 (6)	0.0126 (6)
O22	0.0645 (8)	0.0326 (6)	0.0491 (7)	0.0082 (5)	0.0045 (6)	0.0092 (5)
N23	0.0494 (8)	0.0452 (8)	0.0405 (7)	0.0064 (6)	0.0068 (6)	0.0201 (6)
C24	0.0339 (7)	0.0535 (9)	0.0345 (7)	0.0127 (7)	0.0045 (6)	0.0127 (7)
C25	0.0501 (10)	0.0782 (13)	0.0348 (8)	0.0159 (9)	0.0096 (7)	0.0155 (8)
C26	0.0472 (9)	0.0904 (15)	0.0316 (8)	0.0164 (9)	0.0060 (7)	−0.0022 (9)
C27	0.0401 (8)	0.0594 (11)	0.0447 (9)	0.0113 (8)	0.0014 (7)	−0.0104 (8)
C28	0.0342 (7)	0.0460 (9)	0.0378 (8)	0.0105 (6)	0.0022 (6)	0.0009 (6)
C29	0.0291 (6)	0.0419 (8)	0.0307 (7)	0.0135 (6)	0.0034 (5)	0.0065 (6)
N30	0.0330 (6)	0.0412 (7)	0.0304 (6)	0.0143 (5)	0.0036 (5)	0.0052 (5)
C31	0.0469 (9)	0.0624 (11)	0.0414 (9)	0.0297 (8)	0.0011 (7)	0.0092 (8)
C32	0.0626 (12)	0.0760 (13)	0.0518 (10)	0.0438 (10)	0.0047 (9)	0.0042 (9)
C33	0.0537 (10)	0.0529 (10)	0.0419 (9)	0.0262 (8)	0.0067 (7)	−0.0003 (7)
C34	0.0379 (7)	0.0403 (8)	0.0302 (7)	0.0128 (6)	0.0055 (6)	0.0052 (6)
C35	0.0468 (11)	0.127 (2)	0.0626 (13)	0.0271 (13)	−0.0016 (10)	0.0011 (14)

Geometric parameters (Å, º)

N1—C2	1.355 (2)	C19—H19	0.9300
N1—C6	1.396 (2)	C20—N30	1.460 (2)
N1—H1	0.8600	C20—C29	1.5151 (19)
C2—O3	1.206 (2)	C20—C21	1.569 (2)
C2—C4	1.5452 (19)	C21—O22	1.213 (2)
C4—C5	1.5100 (19)	C21—N23	1.351 (2)
C4—C20	1.5601 (19)	N23—C24	1.391 (2)
C4—C11	1.5650 (19)	N23—H23	0.8600
C5—C10	1.379 (2)	C24—C25	1.383 (2)
C5—C6	1.384 (2)	C24—C29	1.395 (2)
C6—C7	1.380 (2)	C25—C26	1.380 (3)
C7—C8	1.381 (3)	C25—H25	0.9300
C7—H7	0.9300	C26—C27	1.376 (3)
C8—C9	1.376 (3)	C26—H26	0.9300
C8—H8	0.9300	C27—C28	1.398 (2)
C9—C10	1.383 (2)	C27—H27	0.9300
C9—H9	0.9300	C28—C29	1.378 (2)
C10—H10	0.9300	C28—H28	0.9300
C11—C12	1.519 (2)	N30—C31	1.477 (2)
C11—C34	1.533 (2)	N30—C34	1.486 (2)
C11—H11	0.9800	C31—C32	1.513 (3)
C12—O13	1.211 (2)	C31—H31A	0.9700
C12—C14	1.487 (2)	C31—H31B	0.9700
C14—C15	1.381 (2)	C32—C33	1.528 (3)
C14—C19	1.391 (2)	C32—H32A	0.9700
C15—C16	1.377 (3)	C32—H32B	0.9700
C15—H15	0.9300	C33—C34	1.528 (2)
C16—C17	1.380 (3)	C33—H33A	0.9700
C16—H16	0.9300	C33—H33B	0.9700
C17—C18	1.381 (3)	C34—H34	0.9800
C17—C35	1.501 (3)	C35—H35A	0.9600
C18—C19	1.377 (3)	C35—H35B	0.9600
C18—H18	0.9300	C35—H35C	0.9600
C2—N1—C6	112.9 (1)	N30—C20—C21	112.81 (12)
C2—N1—H1	123.5	C29—C20—C21	101.21 (11)
C6—N1—H1	123.5	C4—C20—C21	110.76 (11)
O3—C2—N1	125.32 (14)	O22—C21—N23	125.63 (14)
O3—C2—C4	127.71 (14)	O22—C21—C20	126.60 (14)
N1—C2—C4	106.93 (12)	N23—C21—C20	107.72 (13)
C5—C4—C2	102.16 (11)	C21—N23—C24	112.3 (2)
C5—C4—C20	113.14 (11)	C21—N23—H23	123.9
C2—C4—C20	111.08 (11)	C24—N23—H23	123.9
C5—C4—C11	113.13 (11)	C25—C24—C29	122.4 (2)
C2—C4—C11	117.51 (12)	C25—C24—N23	127.46 (16)
C20—C4—C11	100.32 (11)	C29—C24—N23	110.10 (13)
C10—C5—C6	119.31 (14)	C26—C25—C24	117.4 (2)
C10—C5—C4	131.77 (13)	C26—C25—H25	121.3
C6—C5—C4	108.90 (13)	C24—C25—H25	121.3
C7—C6—C5	122.1 (1)	C27—C26—C25	121.2 (2)
C7—C6—N1	128.75 (15)	C27—C26—H26	119.4
C5—C6—N1	109.10 (13)	C25—C26—H26	119.4
C6—C7—C8	117.7 (2)	C26—C27—C28	121.0 (2)
C6—C7—H7	121.2	C26—C27—H27	119.5
C8—C7—H7	121.2	C28—C27—H27	119.5
C9—C8—C7	120.98 (16)	C29—C28—C27	118.7 (2)
C9—C8—H8	119.5	C29—C28—H28	120.7
C7—C8—H8	119.5	C27—C28—H28	120.7
C8—C9—C10	120.7 (2)	C28—C29—C24	119.28 (14)
C8—C9—H9	119.6	C28—C29—C20	132.05 (14)
C10—C9—H9	119.6	C24—C29—C20	108.67 (13)
C5—C10—C9	119.2 (2)	C20—N30—C31	117.2 (1)
C5—C10—H10	120.4	C20—N30—C34	109.1 (1)
C9—C10—H10	120.4	C31—N30—C34	109.2 (1)
C12—C11—C34	113.84 (12)	N30—C31—C32	105.06 (14)
C12—C11—C4	114.23 (12)	N30—C31—H31A	110.7
C34—C11—C4	101.96 (11)	C32—C31—H31A	110.7
C12—C11—H11	108.8	N30—C31—H31B	110.7
C34—C11—H11	108.8	C32—C31—H31B	110.7
C4—C11—H11	108.8	H31A—C31—H31B	108.8
O13—C12—C14	120.34 (14)	C31—C32—C33	104.19 (14)
O13—C12—C11	121.04 (14)	C31—C32—H32A	110.9
C14—C12—C11	118.60 (13)	C33—C32—H32A	110.9
C15—C14—C19	118.27 (16)	C31—C32—H32B	110.9
C15—C14—C12	123.37 (15)	C33—C32—H32B	110.9
C19—C14—C12	118.34 (15)	H32A—C32—H32B	108.9
C14—C15—C16	120.50 (17)	C32—C33—C34	102.12 (14)
C14—C15—H15	119.7	C32—C33—H33A	111.3
C16—C15—H15	119.7	C34—C33—H33A	111.3
C17—C16—C15	121.50 (18)	C32—C33—H33B	111.3
C17—C16—H16	119.3	C34—C33—H33B	111.3
C15—C16—H16	119.3	H33A—C33—H33B	109.2
C16—C17—C18	117.92 (17)	N30—C34—C33	105.47 (12)
C16—C17—C35	121.5 (2)	N30—C34—C11	106.04 (11)
C18—C17—C35	120.6 (2)	C33—C34—C11	118.77 (13)
C19—C18—C17	121.09 (18)	N30—C34—H34	108.7
C19—C18—H18	119.5	C33—C34—H34	108.7
C17—C18—H18	119.5	C11—C34—H34	108.7
C18—C19—C14	120.65 (17)	C17—C35—H35A	109.5
C18—C19—H19	119.7	C17—C35—H35B	109.5
C14—C19—H19	119.7	H35A—C35—H35B	109.5
N30—C20—C29	115.28 (12)	C17—C35—H35C	109.5
N30—C20—C4	100.76 (11)	H35A—C35—H35C	109.5
C29—C20—C4	116.48 (11)	H35B—C35—H35C	109.5
C6—N1—C2—O3	177.46 (15)	C5—C4—C20—C29	50.51 (16)
C6—N1—C2—C4	−0.07 (17)	C2—C4—C20—C29	−63.71 (16)
O3—C2—C4—C5	−177.79 (15)	C11—C4—C20—C29	171.30 (11)
N1—C2—C4—C5	−0.35 (14)	C5—C4—C20—C21	165.42 (12)
O3—C2—C4—C20	−56.87 (19)	C2—C4—C20—C21	51.20 (15)
N1—C2—C4—C20	120.57 (13)	C11—C4—C20—C21	−73.79 (13)
O3—C2—C4—C11	57.8 (2)	N30—C20—C21—O22	−55.5 (2)
N1—C2—C4—C11	−124.76 (13)	C29—C20—C21—O22	−179.25 (15)
C2—C4—C5—C10	178.87 (16)	C4—C20—C21—O22	56.61 (19)
C20—C4—C5—C10	59.4 (2)	N30—C20—C21—N23	122.02 (13)
C11—C4—C5—C10	−53.8 (2)	C29—C20—C21—N23	−1.74 (15)
C2—C4—C5—C6	0.65 (15)	C4—C20—C21—N23	−125.89 (13)
C20—C4—C5—C6	−118.84 (13)	O22—C21—N23—C24	179.44 (15)
C11—C4—C5—C6	127.94 (13)	C20—C21—N23—C24	1.91 (17)
C10—C5—C6—C7	−0.8 (2)	C21—N23—C24—C25	179.80 (15)
C4—C5—C6—C7	177.71 (15)	C21—N23—C24—C29	−1.27 (18)
C10—C5—C6—N1	−179.21 (14)	C29—C24—C25—C26	1.6 (3)
C4—C5—C6—N1	−0.73 (17)	N23—C24—C25—C26	−179.63 (16)
C2—N1—C6—C7	−177.79 (16)	C24—C25—C26—C27	−0.6 (3)
C2—N1—C6—C5	0.51 (19)	C25—C26—C27—C28	−0.9 (3)
C5—C6—C7—C8	0.2 (3)	C26—C27—C28—C29	1.6 (2)
N1—C6—C7—C8	178.33 (16)	C27—C28—C29—C24	−0.7 (2)
C6—C7—C8—C9	0.1 (3)	C27—C28—C29—C20	179.44 (14)
C7—C8—C9—C10	0.2 (3)	C25—C24—C29—C28	−0.9 (2)
C6—C5—C10—C9	1.0 (2)	N23—C24—C29—C28	−179.90 (13)
C4—C5—C10—C9	−177.05 (15)	C25—C24—C29—C20	179.00 (14)
C8—C9—C10—C5	−0.8 (3)	N23—C24—C29—C20	0.01 (16)
C5—C4—C11—C12	−42.48 (17)	N30—C20—C29—C28	58.9 (2)
C2—C4—C11—C12	76.25 (16)	C4—C20—C29—C28	−58.9 (2)
C20—C4—C11—C12	−163.28 (12)	C21—C20—C29—C28	−179.09 (15)
C5—C4—C11—C34	80.77 (14)	N30—C20—C29—C24	−121.04 (13)
C2—C4—C11—C34	−160.50 (12)	C4—C20—C29—C24	121.18 (13)
C20—C4—C11—C34	−40.03 (13)	C21—C20—C29—C24	1.02 (14)
C34—C11—C12—O13	−0.8 (2)	C29—C20—N30—C31	74.11 (17)
C4—C11—C12—O13	115.72 (18)	C4—C20—N30—C31	−159.61 (13)
C34—C11—C12—C14	−179.03 (13)	C21—C20—N30—C31	−41.48 (17)
C4—C11—C12—C14	−62.5 (2)	C29—C20—N30—C34	−161.20 (12)
O13—C12—C14—C15	152.49 (19)	C4—C20—N30—C34	−34.92 (14)
C11—C12—C14—C15	−29.3 (2)	C21—C20—N30—C34	83.20 (14)
O13—C12—C14—C19	−29.1 (2)	C20—N30—C31—C32	136.28 (16)
C11—C12—C14—C19	149.12 (16)	C34—N30—C31—C32	11.67 (19)
C19—C14—C15—C16	−1.6 (3)	N30—C31—C32—C33	−30.7 (2)
C12—C14—C15—C16	176.82 (16)	C31—C32—C33—C34	37.5 (2)
C14—C15—C16—C17	−0.9 (3)	C20—N30—C34—C33	−117.26 (13)
C15—C16—C17—C18	2.5 (3)	C31—N30—C34—C33	11.99 (17)
C15—C16—C17—C35	−178.68 (18)	C20—N30—C34—C11	9.54 (15)
C16—C17—C18—C19	−1.6 (3)	C31—N30—C34—C11	138.79 (13)
C35—C17—C18—C19	179.62 (19)	C32—C33—C34—N30	−30.29 (18)
C17—C18—C19—C14	−0.9 (3)	C32—C33—C34—C11	−148.91 (15)
C15—C14—C19—C18	2.5 (3)	C12—C11—C34—N30	143.48 (13)
C12—C14—C19—C18	−175.97 (16)	C4—C11—C34—N30	19.96 (14)
C5—C4—C20—N30	−74.97 (13)	C12—C11—C34—C33	−98.20 (17)
C2—C4—C20—N30	170.81 (11)	C4—C11—C34—C33	138.28 (13)
C11—C4—C20—N30	45.82 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O22	0.98	2.31	2.949 (2)	122
C34—H34···O13	0.98	2.38	2.787 (2)	104
N23—H23···O3^i	0.86	2.05	2.892 (2)	168

Symmetry code: (i) −x+1, −y+1, −z+1.