1′-Methyl-4′-(3,4,5-tri­methoxy­phenyl)­di­spiro­[indene-2,3′-pyrrolidine-2′,3′′-indole]-1,2′',3(1′′H)-trione

The pyrrolidine ring of the title compound, C₂₉H₂₆N₂O₆, adopts a twist conformation. The structure is stabilized by weak intramolecular C—H...O interactions as well as by intermolecular C—H...O, N—H...O and N—H...N interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.170
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.94

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.40 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.81 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O32    -   C18     ..       6.27 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O32    -   C33     ..       6.91 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C26    -   C27     ..       5.51 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C27

   1 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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

41'-Methyl-4'-(3,4,5-trimethoxyphenyl)dispiro[indene-2,3'-pyrrolidine- 2',3''-indole]-1,2'',3(1''H)-trione

Crystal data

C29H26N2O6	F(000) = 1048
Mr = 498.52	Dx = 1.295 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3201 reflections
a = 10.3884 (7) Å	θ = 2.4–23.0°
b = 23.2621 (14) Å	µ = 0.09 mm^−1
c = 11.1685 (7) Å	T = 293 K
β = 108.633 (1)°	Block, yellow
V = 2557.5 (3) Å^3	0.20 × 0.19 × 0.19 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5915 independent reflections
Radiation source: fine-focus sealed tube	3919 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −13→13
Tmin = 0.982, Tmax = 0.983	k = −30→26
15973 measured reflections	l = −14→14

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
5915 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.34 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	0.27323 (16)	0.24465 (7)	0.64746 (15)	0.0410 (4)
H1	0.3411	0.2319	0.7082	0.049*
C2	0.26530 (19)	0.24283 (8)	0.52460 (17)	0.0346 (4)
O3	0.34184 (14)	0.21743 (6)	0.48055 (13)	0.0469 (4)
C4	0.13461 (17)	0.27605 (8)	0.44713 (17)	0.0307 (4)
C5	0.06873 (19)	0.28680 (8)	0.54813 (18)	0.0337 (4)
C6	−0.0571 (2)	0.30832 (8)	0.5414 (2)	0.0438 (5)
H6	−0.1188	0.3192	0.4642	0.053*
C7	−0.0898 (2)	0.31343 (9)	0.6524 (2)	0.0522 (6)
H7	−0.1745	0.3277	0.6491	0.063*
C8	0.0012 (3)	0.29775 (10)	0.7667 (2)	0.0558 (6)
H8	−0.0225	0.3020	0.8398	0.067*
C9	0.1269 (2)	0.27587 (10)	0.7750 (2)	0.0504 (6)
H9	0.1888	0.2656	0.8525	0.060*
C10	0.1581 (2)	0.26960 (8)	0.66414 (18)	0.0377 (4)
C11	0.17435 (18)	0.33083 (8)	0.38703 (17)	0.0323 (4)
C12	0.21546 (18)	0.30387 (8)	0.27629 (17)	0.0342 (4)
H12	0.3065	0.2876	0.3138	0.041*
C13	0.1172 (2)	0.25281 (8)	0.23542 (18)	0.0372 (4)
H13A	0.0487	0.2607	0.1549	0.045*
H13B	0.1661	0.2183	0.2271	0.045*
N14	0.05371 (15)	0.24537 (6)	0.33518 (14)	0.0322 (4)
C15	0.0218 (2)	0.18586 (9)	0.3564 (2)	0.0457 (5)
H15A	−0.0311	0.1689	0.2776	0.069*
H15B	−0.0290	0.1849	0.4146	0.069*
H15C	0.1046	0.1646	0.3908	0.069*
C16	0.22447 (19)	0.34583 (8)	0.17526 (17)	0.0355 (4)
C17	0.3523 (2)	0.36244 (9)	0.1742 (2)	0.0431 (5)
H17	0.4294	0.3469	0.2327	0.052*
C18	0.3654 (2)	0.40219 (9)	0.0859 (2)	0.0468 (5)
C19	0.2506 (2)	0.42559 (8)	−0.0010 (2)	0.0445 (5)
C20	0.1228 (2)	0.40955 (9)	0.00143 (18)	0.0400 (5)
C21	0.1098 (2)	0.36930 (9)	0.08835 (18)	0.0383 (5)
H21	0.0239	0.3580	0.0883	0.046*
C22	0.0561 (2)	0.37356 (8)	0.33986 (18)	0.0363 (4)
O23	−0.06103 (14)	0.36244 (6)	0.28168 (14)	0.0473 (4)
C24	0.1101 (3)	0.43149 (9)	0.3765 (2)	0.0481 (5)
C25	0.0441 (3)	0.48397 (10)	0.3421 (3)	0.0719 (8)
H25	−0.0455	0.4857	0.2894	0.086*
C26	0.1157 (5)	0.53260 (12)	0.3884 (3)	0.0990 (12)
H26	0.0743	0.5682	0.3661	0.119*
C27	0.2482 (5)	0.53022 (13)	0.4676 (3)	0.1042 (13)
H27	0.2933	0.5643	0.4989	0.125*
C28	0.3160 (4)	0.47835 (12)	0.5019 (3)	0.0778 (9)
H28	0.4057	0.4770	0.5544	0.093*
C29	0.2440 (3)	0.42852 (9)	0.4544 (2)	0.0509 (6)
C30	0.2893 (2)	0.36801 (9)	0.47120 (19)	0.0432 (5)
O31	0.39896 (17)	0.35094 (8)	0.53611 (16)	0.0663 (5)
O32	0.48996 (18)	0.42167 (8)	0.07800 (19)	0.0687 (5)
C33	0.6057 (3)	0.40054 (13)	0.1605 (3)	0.0715 (8)
H33A	0.6826	0.4177	0.1444	0.107*
H33B	0.6083	0.3596	0.1505	0.107*
H33C	0.6083	0.4093	0.2453	0.107*
O34	0.26109 (18)	0.46638 (6)	−0.08768 (16)	0.0611 (5)
C35	0.2986 (4)	0.44398 (14)	−0.1886 (3)	0.1043 (13)
H35A	0.3045	0.4747	−0.2441	0.156*
H35B	0.2316	0.4167	−0.2344	0.156*
H35C	0.3852	0.4253	−0.1563	0.156*
O36	0.01580 (16)	0.43510 (7)	−0.08718 (15)	0.0557 (4)
C37	−0.1133 (2)	0.43092 (11)	−0.0708 (3)	0.0621 (7)
H37A	−0.1793	0.4506	−0.1386	0.093*
H37B	−0.1100	0.4481	0.0083	0.093*
H37C	−0.1384	0.3912	−0.0710	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0364 (9)	0.0576 (11)	0.0278 (8)	0.0062 (8)	0.0085 (7)	0.0085 (8)
C2	0.0328 (10)	0.0385 (10)	0.0320 (10)	0.0012 (8)	0.0099 (8)	0.0055 (8)
O3	0.0428 (8)	0.0608 (9)	0.0384 (8)	0.0195 (7)	0.0147 (7)	0.0073 (7)
C4	0.0288 (9)	0.0344 (10)	0.0289 (9)	0.0010 (7)	0.0090 (7)	0.0026 (8)
C5	0.0376 (10)	0.0303 (9)	0.0362 (10)	−0.0035 (8)	0.0158 (8)	0.0000 (8)
C6	0.0411 (11)	0.0407 (11)	0.0552 (13)	0.0032 (9)	0.0232 (10)	0.0056 (10)
C7	0.0574 (14)	0.0423 (12)	0.0743 (17)	0.0009 (11)	0.0453 (13)	−0.0005 (11)
C8	0.0765 (17)	0.0543 (14)	0.0539 (14)	−0.0091 (12)	0.0450 (14)	−0.0065 (11)
C9	0.0597 (14)	0.0588 (14)	0.0366 (11)	−0.0075 (11)	0.0212 (10)	−0.0010 (10)
C10	0.0426 (11)	0.0397 (10)	0.0334 (10)	−0.0052 (9)	0.0156 (9)	0.0002 (8)
C11	0.0315 (10)	0.0360 (10)	0.0284 (9)	−0.0009 (8)	0.0081 (8)	0.0035 (8)
C12	0.0291 (9)	0.0426 (11)	0.0306 (9)	0.0036 (8)	0.0092 (8)	0.0063 (8)
C13	0.0416 (11)	0.0388 (10)	0.0327 (10)	0.0036 (9)	0.0141 (9)	0.0014 (8)
N14	0.0344 (8)	0.0315 (8)	0.0292 (8)	−0.0010 (6)	0.0079 (7)	0.0008 (6)
C15	0.0545 (13)	0.0369 (11)	0.0439 (12)	−0.0059 (10)	0.0131 (10)	0.0022 (9)
C16	0.0370 (10)	0.0397 (10)	0.0319 (10)	−0.0013 (8)	0.0141 (8)	0.0017 (8)
C17	0.0383 (11)	0.0488 (12)	0.0431 (12)	0.0015 (9)	0.0145 (9)	0.0056 (10)
C18	0.0464 (13)	0.0450 (12)	0.0570 (14)	−0.0033 (10)	0.0278 (11)	0.0035 (10)
C19	0.0588 (14)	0.0376 (11)	0.0461 (12)	0.0030 (10)	0.0295 (11)	0.0086 (9)
C20	0.0471 (12)	0.0401 (11)	0.0331 (10)	0.0064 (9)	0.0131 (9)	0.0059 (8)
C21	0.0361 (11)	0.0459 (11)	0.0338 (10)	−0.0021 (9)	0.0125 (9)	0.0056 (9)
C22	0.0437 (12)	0.0367 (10)	0.0305 (10)	0.0023 (9)	0.0144 (9)	0.0044 (8)
O23	0.0392 (9)	0.0489 (9)	0.0505 (9)	0.0086 (7)	0.0098 (7)	0.0089 (7)
C24	0.0703 (16)	0.0378 (11)	0.0384 (11)	−0.0008 (10)	0.0203 (11)	0.0007 (9)
C25	0.112 (2)	0.0398 (13)	0.0645 (17)	0.0115 (14)	0.0283 (16)	0.0049 (12)
C26	0.174 (4)	0.0391 (15)	0.077 (2)	−0.002 (2)	0.030 (2)	0.0005 (15)
C27	0.195 (4)	0.0420 (16)	0.070 (2)	−0.043 (2)	0.035 (3)	−0.0116 (15)
C28	0.114 (2)	0.0646 (18)	0.0489 (15)	−0.0391 (17)	0.0184 (15)	−0.0046 (13)
C29	0.0779 (17)	0.0414 (12)	0.0351 (11)	−0.0188 (11)	0.0205 (11)	−0.0006 (9)
C30	0.0462 (12)	0.0519 (12)	0.0299 (10)	−0.0131 (10)	0.0099 (9)	0.0034 (9)
O31	0.0472 (10)	0.0770 (12)	0.0584 (11)	−0.0168 (9)	−0.0061 (8)	0.0087 (9)
O32	0.0609 (11)	0.0676 (11)	0.0905 (14)	0.0064 (9)	0.0422 (10)	0.0267 (10)
C33	0.0482 (15)	0.087 (2)	0.086 (2)	−0.0233 (14)	0.0309 (15)	−0.0101 (16)
O34	0.0813 (12)	0.0467 (9)	0.0724 (11)	0.0110 (8)	0.0486 (10)	0.0212 (8)
C35	0.169 (4)	0.088 (2)	0.095 (2)	0.050 (2)	0.096 (3)	0.0450 (19)
O36	0.0579 (10)	0.0618 (10)	0.0477 (9)	0.0128 (8)	0.0171 (8)	0.0211 (8)
C37	0.0503 (14)	0.0647 (16)	0.0668 (16)	0.0151 (12)	0.0123 (12)	0.0172 (13)

Geometric parameters (Å, º)

N1—C2	1.349 (2)	C17—H17	0.9300
N1—C10	1.394 (2)	C18—C19	1.387 (3)
N1—H1	0.8600	C18—O32	1.400 (2)
C2—O3	1.214 (2)	C19—C20	1.387 (3)
C2—C4	1.562 (3)	C19—O34	1.385 (2)
C4—N14	1.452 (2)	C20—O36	1.366 (2)
C4—C5	1.515 (2)	C20—C21	1.386 (3)
C4—C11	1.556 (2)	C21—H21	0.9300
C5—C6	1.379 (3)	C22—O23	1.210 (2)
C5—C10	1.390 (3)	C22—C24	1.467 (3)
C6—C7	1.391 (3)	C24—C29	1.387 (3)
C6—H6	0.9300	C24—C25	1.393 (3)
C7—C8	1.373 (4)	C25—C26	1.362 (4)
C7—H7	0.9300	C25—H25	0.9300
C8—C9	1.377 (3)	C26—C27	1.379 (5)
C8—H8	0.9300	C26—H26	0.9300
C9—C10	1.384 (3)	C27—C28	1.388 (5)
C9—H9	0.9300	C27—H27	0.9300
C11—C30	1.530 (3)	C28—C29	1.389 (3)
C11—C22	1.537 (3)	C28—H28	0.9300
C11—C12	1.563 (2)	C29—C30	1.477 (3)
C12—C16	1.517 (2)	C30—O31	1.205 (3)
C12—C13	1.537 (3)	O32—C33	1.352 (3)
C12—H12	0.9800	C33—H33A	0.9600
C13—N14	1.475 (2)	C33—H33B	0.9600
C13—H13A	0.9700	C33—H33C	0.9600
C13—H13B	0.9700	O34—C35	1.405 (3)
N14—C15	1.460 (2)	C35—H35A	0.9600
C15—H15A	0.9600	C35—H35B	0.9600
C15—H15B	0.9600	C35—H35C	0.9600
C15—H15C	0.9600	O36—C37	1.414 (3)
C16—C17	1.386 (3)	C37—H37A	0.9600
C16—C21	1.386 (3)	C37—H37B	0.9600
C17—C18	1.390 (3)	C37—H37C	0.9600
C2—N1—C10	111.9 (2)	C16—C17—C18	120.22 (19)
C2—N1—H1	124.1	C16—C17—H17	119.9
C10—N1—H1	124.1	C18—C17—H17	119.9
O3—C2—N1	126.4 (2)	C17—C18—C19	120.00 (18)
O3—C2—C4	125.6 (2)	C17—C18—O32	124.2 (2)
N1—C2—C4	107.93 (15)	C19—C18—O32	115.8 (2)
N14—C4—C5	116.57 (14)	C20—C19—O34	119.2 (2)
N14—C4—C11	101.0 (1)	C20—C19—C18	119.69 (18)
C5—C4—C11	115.54 (14)	O34—C19—C18	121.1 (2)
N14—C4—C2	113.3 (2)	O36—C20—C19	115.5 (2)
C5—C4—C2	100.88 (14)	O36—C20—C21	124.2 (2)
C11—C4—C2	109.92 (14)	C19—C20—C21	120.25 (19)
C6—C5—C10	119.65 (18)	C20—C21—C16	120.13 (18)
C6—C5—C4	131.67 (18)	C20—C21—H21	119.9
C10—C5—C4	108.67 (16)	C16—C21—H21	119.9
C5—C6—C7	118.7 (2)	O23—C22—C24	125.1 (2)
C5—C6—H6	120.7	O23—C22—C11	127.0 (2)
C7—C6—H6	120.7	C24—C22—C11	107.83 (17)
C8—C7—C6	120.9 (2)	C29—C24—C25	121.6 (2)
C8—C7—H7	119.5	C29—C24—C22	110.29 (19)
C6—C7—H7	119.5	C25—C24—C22	128.1 (2)
C9—C8—C7	121.1 (2)	C26—C25—C24	117.5 (3)
C9—C8—H8	119.4	C26—C25—H25	121.2
C7—C8—H8	119.4	C24—C25—H25	121.2
C8—C9—C10	117.9 (2)	C27—C26—C25	121.5 (3)
C8—C9—H9	121.1	C27—C26—H26	119.3
C10—C9—H9	121.1	C25—C26—H26	119.3
C5—C10—N1	110.0 (2)	C26—C27—C28	121.8 (3)
C5—C10—C9	121.7 (2)	C26—C27—H27	119.1
N1—C10—C9	128.3 (2)	C28—C27—H27	119.1
C30—C11—C22	103.10 (16)	C29—C28—C27	117.1 (3)
C30—C11—C4	117.42 (15)	C29—C28—H28	121.4
C22—C11—C4	112.61 (14)	C27—C28—H28	121.4
C30—C11—C12	110.85 (15)	C28—C29—C24	120.5 (2)
C22—C11—C12	112.26 (14)	C28—C29—C30	129.5 (3)
C4—C11—C12	101.0 (1)	C24—C29—C30	110.02 (18)
C16—C12—C13	117.98 (15)	O31—C30—C29	126.3 (2)
C16—C12—C11	115.32 (15)	O31—C30—C11	125.8 (2)
C13—C12—C11	102.8 (1)	C29—C30—C11	107.82 (18)
C16—C12—H12	106.7	C33—O32—C18	118.5 (2)
C13—C12—H12	106.7	O32—C33—H33A	109.5
C11—C12—H12	106.7	O32—C33—H33B	109.5
N14—C13—C12	106.3 (1)	H33A—C33—H33B	109.5
N14—C13—H13A	110.5	O32—C33—H33C	109.5
C12—C13—H13A	110.5	H33A—C33—H33C	109.5
N14—C13—H13B	110.5	H33B—C33—H33C	109.5
C12—C13—H13B	110.5	C19—O34—C35	114.3 (2)
H13A—C13—H13B	108.7	O34—C35—H35A	109.5
C4—N14—C15	115.2 (2)	O34—C35—H35B	109.5
C4—N14—C13	108.5 (1)	H35A—C35—H35B	109.5
C15—N14—C13	114.39 (15)	O34—C35—H35C	109.5
N14—C15—H15A	109.5	H35A—C35—H35C	109.5
N14—C15—H15B	109.5	H35B—C35—H35C	109.5
H15A—C15—H15B	109.5	C20—O36—C37	117.6 (2)
N14—C15—H15C	109.5	O36—C37—H37A	109.5
H15A—C15—H15C	109.5	O36—C37—H37B	109.5
H15B—C15—H15C	109.5	H37A—C37—H37B	109.5
C17—C16—C21	119.70 (17)	O36—C37—H37C	109.5
C17—C16—C12	118.20 (17)	H37A—C37—H37C	109.5
C21—C16—C12	122.06 (16)	H37B—C37—H37C	109.5
C10—N1—C2—O3	−170.32 (19)	C11—C12—C16—C21	−73.2 (2)
C10—N1—C2—C4	6.2 (2)	C21—C16—C17—C18	−0.4 (3)
O3—C2—C4—N14	43.1 (3)	C12—C16—C17—C18	−178.0 (2)
N1—C2—C4—N14	−133.39 (16)	C16—C17—C18—C19	0.3 (3)
O3—C2—C4—C5	168.50 (19)	C16—C17—C18—O32	179.7 (2)
N1—C2—C4—C5	−8.03 (19)	C17—C18—C19—C20	0.6 (3)
O3—C2—C4—C11	−69.1 (2)	O32—C18—C19—C20	−178.82 (19)
N1—C2—C4—C11	114.42 (17)	C17—C18—C19—O34	178.29 (19)
N14—C4—C5—C6	−48.4 (3)	O32—C18—C19—O34	−1.1 (3)
C11—C4—C5—C6	70.1 (3)	O34—C19—C20—O36	1.9 (3)
C2—C4—C5—C6	−171.50 (19)	C18—C19—C20—O36	179.60 (19)
N14—C4—C5—C10	130.35 (17)	O34—C19—C20—C21	−179.24 (18)
C11—C4—C5—C10	−111.22 (17)	C18—C19—C20—C21	−1.5 (3)
C2—C4—C5—C10	7.23 (19)	O36—C20—C21—C16	−179.72 (19)
C10—C5—C6—C7	1.5 (3)	C19—C20—C21—C16	1.5 (3)
C4—C5—C6—C7	−179.92 (18)	C17—C16—C21—C20	−0.5 (3)
C5—C6—C7—C8	0.4 (3)	C12—C16—C21—C20	177.0 (2)
C6—C7—C8—C9	−0.8 (3)	C30—C11—C22—O23	−170.99 (19)
C7—C8—C9—C10	−0.7 (3)	C4—C11—C22—O23	−43.5 (3)
C6—C5—C10—N1	174.68 (17)	C12—C11—C22—O23	69.7 (2)
C4—C5—C10—N1	−4.2 (2)	C30—C11—C22—C24	9.67 (19)
C6—C5—C10—C9	−3.0 (3)	C4—C11—C22—C24	137.20 (16)
C4—C5—C10—C9	178.10 (17)	C12—C11—C22—C24	−109.67 (17)
C2—N1—C10—C5	−1.4 (2)	O23—C22—C24—C29	173.13 (19)
C2—N1—C10—C9	176.1 (2)	C11—C22—C24—C29	−7.5 (2)
C8—C9—C10—C5	2.6 (3)	O23—C22—C24—C25	−7.2 (4)
C8—C9—C10—N1	−174.6 (2)	C11—C22—C24—C25	172.2 (2)
N14—C4—C11—C30	−165.21 (16)	C29—C24—C25—C26	−0.4 (4)
C5—C4—C11—C30	68.0 (2)	C22—C24—C25—C26	179.9 (2)
C2—C4—C11—C30	−45.3 (2)	C24—C25—C26—C27	−0.7 (5)
N14—C4—C11—C22	75.28 (17)	C25—C26—C27—C28	1.4 (6)
C5—C4—C11—C22	−51.5 (2)	C26—C27—C28—C29	−0.9 (5)
C2—C4—C11—C22	−164.77 (15)	C27—C28—C29—C24	−0.2 (4)
N14—C4—C11—C12	−44.63 (15)	C27—C28—C29—C30	178.2 (2)
C5—C4—C11—C12	−171.37 (15)	C25—C24—C29—C28	0.9 (4)
C2—C4—C11—C12	75.32 (16)	C22—C24—C29—C28	−179.4 (2)
C30—C11—C12—C16	−70.6 (2)	C25—C24—C29—C30	−177.8 (2)
C22—C11—C12—C16	44.1 (2)	C22—C24—C29—C30	1.9 (2)
C4—C11—C12—C16	164.26 (15)	C28—C29—C30—O31	3.6 (4)
C30—C11—C12—C13	159.62 (16)	C24—C29—C30—O31	−177.8 (2)
C22—C11—C12—C13	−85.68 (17)	C28—C29—C30—C11	−174.0 (2)
C4—C11—C12—C13	34.48 (17)	C24—C29—C30—C11	4.6 (2)
C16—C12—C13—N14	−140.49 (16)	C22—C11—C30—O31	173.8 (2)
C11—C12—C13—N14	−12.37 (18)	C4—C11—C30—O31	49.3 (3)
C5—C4—N14—C15	−65.6 (2)	C12—C11—C30—O31	−65.9 (2)
C11—C4—N14—C15	168.33 (15)	C22—C11—C30—C29	−8.60 (19)
C2—C4—N14—C15	50.8 (2)	C4—C11—C30—C29	−133.03 (17)
C5—C4—N14—C13	164.72 (15)	C12—C11—C30—C29	111.72 (18)
C11—C4—N14—C13	38.66 (17)	C17—C18—O32—C33	0.4 (3)
C2—C4—N14—C13	−78.85 (17)	C19—C18—O32—C33	179.8 (2)
C12—C13—N14—C4	−16.75 (19)	C20—C19—O34—C35	−106.6 (3)
C12—C13—N14—C15	−146.84 (16)	C18—C19—O34—C35	75.7 (3)
C13—C12—C16—C17	−133.71 (19)	C19—C20—O36—C37	−165.57 (19)
C11—C12—C16—C17	104.4 (2)	C21—C20—O36—C37	15.6 (3)
C13—C12—C16—C21	48.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O23	0.93	2.51	3.150 (3)	126
C12—H12···O3	0.98	2.41	3.010 (2)	119
C21—H21···O23	0.93	2.58	3.207 (3)	125
C35—H35C···O32	0.96	2.49	3.050 (4)	117
N1—H1···O23^i	0.86	2.45	3.125 (2)	136
N1—H1···N14^i	0.86	2.27	3.006 (2)	143
C8—H8···O3^ii	0.93	2.47	3.331 (3)	155
C13—H13A···O3^iii	0.97	2.45	3.400 (2)	167
C21—H21···O3^iii	0.93	2.58	3.336 (3)	139

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