4-p-Anisyl-1,2′-diphenyl-3-p-tolyl-2′,3′-dihydrospiro­[2-pyrazoline-5,3′-isoquinolin]-4′(1′H)-one

In the title compound, C₃₇H₃₁N₃O₂, the piperidine ring adopts a half-chair conformation. The mol­ecule is stabilized by intra­molecular C—H...N bonds and mol­ecules are connected via C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.112
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C13    -   C14     ..       7.66 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 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
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Each author has made a unique and important contribution to this study. We ask that each author be listed as given.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: X-AREA (Stoe, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(3)

Crystal data

C37H31N3O2	F(000) = 1160
Mr = 549.65	Dx = 1.272 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 43585 reflections
a = 11.6063 (7) Å	θ = 1.8–28.0°
b = 14.8988 (6) Å	µ = 0.08 mm^−1
c = 19.4799 (11) Å	T = 296 K
β = 121.552 (4)°	Prism, yellow
V = 2870.5 (3) Å^3	0.53 × 0.43 × 0.27 mm
Z = 4

Data collection

STOE IPDS 2 diffractometer	6765 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	4450 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.069
Detector resolution: 6.67 pixels mm^-1	θmax = 27.9°, θmin = 1.8°
ω scans	h = −15→15
Absorption correction: integration (XRED32; Stoe, 2002)	k = −19→19
Tmin = 0.959, Tmax = 0.979	l = −25→25
44195 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0609P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
6765 reflections	Δρmax = 0.27 e Å^−3
381 parameters	Δρmin = −0.16 e Å^−3
1 restraint	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0072 (9)

Special details

Experimental. IR (KBr, cm^-1): 1689 (CO). Analysis found: C 79.06, H 5.60, N 7.35%; C₃₇H₃₁N₃O₂ requires: C 80.87, H 5.64, N 7.65%. ¹H-NMR (CDCl₃, δ p.p.m., J Hz): 2.30 (s, 3H), 3.75 (s, 3H), 4.40, 4.55 (2d, 2H, J = 16.35), 5.30 (s, 1H), 6.50–7.65 (m, 21H), 8.05 (dd, 1H, J¹ = 7.85 and J² = 1.25). ¹³C-NMR (CDCl₃): 21.40 (CH₃), 50.40 (NCH₂), 55.25 (OCH₃), 63.70 (CH), 91.40 (C^5:3'), 126.10, 129.10, 129.65, 138.30, 140.85, 144.35, 147.70, 148.05, 159.30, 113.55, 113.65, 115.45, 120.30, 121.65, 121.95, 125.90, 128.00, 128.15, 128.35, 128.85, 132.15, 134.65; 195.20 (CO). MS m/z calculated for C₃₇H₃₁N₃O₂: [M] = 549 g mol^-1, found: 77 (100%), 118 (22%), 165 (10%), 208 (35%), 237 (23%), 341 (75%), 531 (17%), 549 (28%).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	0.32642 (13)	0.61063 (10)	0.42060 (8)	0.0802 (5)
O2	0.86050 (10)	0.64777 (8)	0.23758 (6)	0.0590 (4)
N1	0.91056 (11)	0.59746 (7)	0.39964 (6)	0.0438 (3)
N2	0.83569 (11)	0.53688 (7)	0.33787 (6)	0.0425 (3)
N3	0.59822 (11)	0.51617 (7)	0.23192 (7)	0.0436 (3)
C1	0.84012 (13)	0.66814 (9)	0.38911 (8)	0.0417 (4)
C2	0.89273 (13)	0.74210 (9)	0.44758 (8)	0.0461 (4)
C3	1.01085 (18)	0.73224 (12)	0.52184 (10)	0.0699 (6)
C4	1.0576 (2)	0.80016 (14)	0.57803 (11)	0.0799 (7)
C5	0.98957 (18)	0.88028 (12)	0.56310 (11)	0.0643 (6)
C6	0.87523 (19)	0.89085 (12)	0.48854 (11)	0.0697 (6)
C7	0.82625 (16)	0.82344 (11)	0.43129 (10)	0.0598 (5)
C8	1.0351 (2)	0.95175 (15)	0.62749 (14)	0.0948 (8)
C9	0.69743 (13)	0.66269 (9)	0.31717 (8)	0.0411 (4)
C10	0.59668 (13)	0.65279 (9)	0.34362 (8)	0.0428 (4)
C11	0.62633 (14)	0.60016 (10)	0.41041 (8)	0.0483 (4)
C12	0.53525 (16)	0.58839 (11)	0.43427 (9)	0.0565 (5)
C13	0.41015 (16)	0.62831 (11)	0.39209 (10)	0.0565 (5)
C14	0.37776 (15)	0.68241 (11)	0.32733 (10)	0.0575 (5)
C15	0.47212 (14)	0.69492 (10)	0.30365 (9)	0.0510 (4)
C16	0.1975 (2)	0.64880 (18)	0.38076 (17)	0.1020 (10)
C17	0.71262 (12)	0.57897 (9)	0.27229 (8)	0.0404 (4)
C18	0.56251 (14)	0.45962 (9)	0.27800 (8)	0.0471 (4)
C19	0.65413 (17)	0.39875 (10)	0.33423 (9)	0.0568 (5)
C20	0.6181 (2)	0.34453 (11)	0.37783 (11)	0.0693 (6)
C21	0.4896 (2)	0.34731 (13)	0.36491 (12)	0.0759 (7)
C22	0.39666 (19)	0.40395 (13)	0.30687 (12)	0.0709 (7)
C23	0.43180 (16)	0.45968 (11)	0.26385 (10)	0.0597 (5)
C24	0.48142 (14)	0.55256 (11)	0.15872 (8)	0.0510 (4)
C25	0.51443 (14)	0.59058 (9)	0.10011 (8)	0.0482 (4)
C26	0.41476 (17)	0.59810 (12)	0.01910 (9)	0.0633 (5)
C27	0.4450 (2)	0.63548 (13)	−0.03441 (10)	0.0708 (6)
C28	0.57247 (19)	0.66568 (12)	−0.00955 (10)	0.0658 (6)
C29	0.67271 (17)	0.65896 (10)	0.07063 (9)	0.0551 (5)
C30	0.64294 (14)	0.62191 (9)	0.12540 (8)	0.0447 (4)
C31	0.74737 (14)	0.61785 (9)	0.21131 (8)	0.0433 (4)
C32	0.91231 (14)	0.47409 (9)	0.32366 (9)	0.0464 (4)
C33	0.85933 (16)	0.43253 (11)	0.24942 (10)	0.0612 (5)
C34	0.93508 (19)	0.37109 (12)	0.23692 (12)	0.0696 (6)
C35	1.06288 (19)	0.34922 (12)	0.29733 (13)	0.0756 (7)
C36	1.1145 (2)	0.38839 (14)	0.37121 (13)	0.0834 (7)
C37	1.04051 (17)	0.45045 (12)	0.38475 (11)	0.0662 (5)
H3	1.05930	0.67890	0.53390	0.0840*
H4	1.13730	0.79170	0.62740	0.0960*
H6	0.82900	0.94520	0.47600	0.0840*
H7	0.74800	0.83290	0.38140	0.0720*
H8A	1.00330	1.00930	0.60250	0.1420*
H8B	1.13210	0.95230	0.66000	0.1420*
H8C	0.99880	0.93890	0.66080	0.1420*
H9	0.67670	0.71660	0.28390	0.0490*
H11	0.71030	0.57230	0.43950	0.0580*
H12	0.55820	0.55330	0.47910	0.0680*
H14	0.29390	0.71060	0.29930	0.0690*
H15	0.45040	0.73230	0.26020	0.0610*
H16A	0.15050	0.63090	0.40700	0.1530*
H16B	0.14820	0.62870	0.32580	0.1530*
H16C	0.20520	0.71300	0.38210	0.1530*
H19	0.74060	0.39440	0.34270	0.0680*
H20	0.68170	0.30560	0.41640	0.0830*
H21	0.46640	0.31150	0.39490	0.0910*
H22	0.30870	0.40500	0.29620	0.0850*
H23	0.36710	0.49780	0.22490	0.0720*
H24A	0.44050	0.59930	0.17380	0.0610*
H24B	0.41500	0.50520	0.13230	0.0610*
H26	0.32760	0.57790	0.00090	0.0760*
H27	0.37740	0.64030	−0.08850	0.0850*
H28	0.59130	0.69050	−0.04640	0.0790*
H29	0.75970	0.67900	0.08810	0.0660*
H33	0.77210	0.44620	0.20780	0.0730*
H34	0.89880	0.34410	0.18670	0.0840*
H35	1.11410	0.30830	0.28830	0.0910*
H36	1.20080	0.37290	0.41290	0.1000*
H37	1.07720	0.47650	0.43540	0.0790*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0674 (8)	0.1032 (10)	0.0871 (9)	−0.0007 (7)	0.0523 (7)	0.0081 (7)
O2	0.0490 (6)	0.0728 (7)	0.0542 (6)	−0.0135 (5)	0.0263 (5)	0.0036 (5)
N1	0.0375 (6)	0.0476 (6)	0.0401 (6)	−0.0032 (5)	0.0160 (5)	−0.0016 (5)
N2	0.0372 (5)	0.0425 (6)	0.0406 (6)	−0.0007 (4)	0.0154 (5)	−0.0013 (4)
N3	0.0383 (6)	0.0474 (6)	0.0396 (6)	−0.0070 (5)	0.0165 (5)	0.0010 (5)
C1	0.0381 (6)	0.0460 (7)	0.0392 (7)	−0.0022 (5)	0.0189 (6)	0.0019 (5)
C2	0.0422 (7)	0.0500 (7)	0.0442 (7)	−0.0063 (6)	0.0214 (6)	−0.0025 (6)
C3	0.0590 (10)	0.0646 (10)	0.0559 (10)	0.0015 (8)	0.0092 (8)	−0.0079 (8)
C4	0.0675 (11)	0.0835 (13)	0.0554 (10)	−0.0098 (10)	0.0090 (9)	−0.0169 (9)
C5	0.0655 (10)	0.0679 (10)	0.0640 (10)	−0.0196 (8)	0.0370 (9)	−0.0207 (8)
C6	0.0714 (11)	0.0581 (9)	0.0742 (11)	0.0013 (8)	0.0343 (10)	−0.0156 (8)
C7	0.0538 (9)	0.0579 (9)	0.0554 (9)	0.0019 (7)	0.0201 (7)	−0.0074 (7)
C8	0.1004 (15)	0.0953 (15)	0.0880 (14)	−0.0319 (12)	0.0489 (13)	−0.0437 (12)
C9	0.0402 (6)	0.0416 (7)	0.0387 (6)	−0.0006 (5)	0.0188 (6)	0.0032 (5)
C10	0.0388 (6)	0.0466 (7)	0.0395 (7)	−0.0015 (5)	0.0180 (6)	−0.0030 (5)
C11	0.0447 (7)	0.0526 (8)	0.0441 (7)	−0.0021 (6)	0.0209 (6)	0.0018 (6)
C12	0.0570 (9)	0.0636 (9)	0.0509 (8)	−0.0060 (7)	0.0297 (7)	0.0024 (7)
C13	0.0532 (9)	0.0661 (9)	0.0567 (9)	−0.0077 (7)	0.0332 (8)	−0.0070 (7)
C14	0.0406 (7)	0.0633 (9)	0.0617 (9)	0.0060 (7)	0.0219 (7)	−0.0050 (7)
C15	0.0438 (7)	0.0572 (8)	0.0453 (8)	0.0054 (6)	0.0187 (6)	0.0008 (6)
C16	0.0759 (13)	0.1125 (17)	0.148 (2)	0.0137 (12)	0.0796 (16)	0.0211 (16)
C17	0.0364 (6)	0.0427 (7)	0.0384 (7)	−0.0026 (5)	0.0170 (6)	0.0013 (5)
C18	0.0497 (8)	0.0459 (7)	0.0463 (7)	−0.0124 (6)	0.0256 (7)	−0.0058 (6)
C19	0.0614 (9)	0.0503 (8)	0.0591 (9)	−0.0062 (7)	0.0319 (8)	0.0036 (7)
C20	0.0885 (13)	0.0546 (9)	0.0694 (11)	−0.0093 (9)	0.0446 (10)	0.0066 (8)
C21	0.1040 (15)	0.0649 (11)	0.0792 (12)	−0.0315 (10)	0.0620 (12)	−0.0084 (9)
C22	0.0713 (11)	0.0761 (11)	0.0794 (12)	−0.0276 (9)	0.0492 (10)	−0.0117 (10)
C23	0.0537 (9)	0.0660 (10)	0.0621 (9)	−0.0157 (7)	0.0321 (8)	−0.0076 (7)
C24	0.0398 (7)	0.0619 (9)	0.0422 (7)	−0.0045 (6)	0.0152 (6)	−0.0002 (6)
C25	0.0489 (8)	0.0480 (7)	0.0410 (7)	0.0034 (6)	0.0188 (6)	0.0002 (6)
C26	0.0563 (9)	0.0694 (10)	0.0466 (9)	−0.0007 (8)	0.0147 (7)	0.0038 (7)
C27	0.0780 (12)	0.0756 (11)	0.0401 (8)	0.0080 (9)	0.0179 (8)	0.0099 (8)
C28	0.0799 (12)	0.0723 (11)	0.0489 (9)	0.0094 (9)	0.0363 (9)	0.0108 (8)
C29	0.0645 (9)	0.0574 (8)	0.0507 (8)	0.0047 (7)	0.0352 (8)	0.0042 (7)
C30	0.0495 (8)	0.0438 (7)	0.0422 (7)	0.0048 (6)	0.0249 (6)	0.0006 (5)
C31	0.0431 (7)	0.0432 (7)	0.0445 (7)	−0.0024 (5)	0.0235 (6)	−0.0001 (5)
C32	0.0445 (7)	0.0409 (7)	0.0524 (8)	−0.0008 (5)	0.0243 (6)	0.0014 (6)
C33	0.0520 (9)	0.0592 (9)	0.0621 (10)	0.0021 (7)	0.0228 (8)	−0.0110 (7)
C34	0.0720 (11)	0.0617 (10)	0.0764 (11)	−0.0020 (8)	0.0397 (10)	−0.0185 (9)
C35	0.0682 (11)	0.0581 (10)	0.1035 (15)	0.0112 (8)	0.0470 (11)	−0.0075 (10)
C36	0.0617 (11)	0.0787 (12)	0.0859 (14)	0.0248 (9)	0.0221 (10)	−0.0072 (10)
C37	0.0562 (9)	0.0657 (10)	0.0591 (9)	0.0152 (8)	0.0179 (8)	−0.0021 (8)

Geometric parameters (Å, º)

O1—C13	1.374 (3)	C29—C30	1.396 (2)
O1—C16	1.396 (3)	C30—C31	1.4665 (19)
O2—C31	1.217 (2)	C32—C33	1.387 (2)
N1—N2	1.3868 (15)	C32—C37	1.379 (3)
N1—C1	1.2821 (19)	C33—C34	1.376 (3)
N2—C17	1.4683 (18)	C34—C35	1.365 (3)
N2—C32	1.414 (2)	C35—C36	1.367 (3)
N3—C17	1.4711 (19)	C36—C37	1.378 (3)
N3—C18	1.441 (2)	C3—H3	0.9300
N3—C24	1.4635 (19)	C4—H4	0.9300
C1—C2	1.4685 (19)	C6—H6	0.9300
C1—C9	1.511 (2)	C7—H7	0.9300
C2—C3	1.385 (2)	C8—H8A	0.9600
C2—C7	1.382 (2)	C8—H8B	0.9600
C3—C4	1.377 (3)	C8—H8C	0.9600
C4—C5	1.376 (3)	C9—H9	0.9800
C5—C6	1.371 (3)	C11—H11	0.9300
C5—C8	1.514 (3)	C12—H12	0.9300
C6—C7	1.383 (2)	C14—H14	0.9300
C9—C10	1.512 (2)	C15—H15	0.9300
C9—C17	1.585 (2)	C16—H16A	0.9600
C10—C11	1.399 (2)	C16—H16B	0.9600
C10—C15	1.383 (2)	C16—H16C	0.9600
C11—C12	1.371 (3)	C19—H19	0.9300
C12—C13	1.374 (3)	C20—H20	0.9300
C13—C14	1.373 (2)	C21—H21	0.9300
C14—C15	1.406 (3)	C22—H22	0.9300
C17—C31	1.553 (2)	C23—H23	0.9300
C18—C19	1.391 (2)	C24—H24A	0.9700
C18—C23	1.393 (3)	C24—H24B	0.9700
C19—C20	1.386 (3)	C26—H26	0.9300
C20—C21	1.377 (4)	C27—H27	0.9300
C21—C22	1.370 (3)	C28—H28	0.9300
C22—C23	1.384 (3)	C29—H29	0.9300
C24—C25	1.493 (2)	C33—H33	0.9300
C25—C26	1.389 (2)	C34—H34	0.9300
C25—C30	1.384 (2)	C35—H35	0.9300
C26—C27	1.379 (3)	C36—H36	0.9300
C27—C28	1.370 (3)	C37—H37	0.9300
C28—C29	1.379 (2)
O2···N1	2.9910 (15)	C19···H15^viii	2.9400
O2···N2	2.6866 (16)	C20···H15^viii	2.9000
O2···C1	3.0971 (19)	C23···H24A	2.7600
O2···C16^i	3.415 (3)	C23···H24B	2.5600
O2···C32	2.9688 (18)	C24···H23	2.4200
O2···C33	3.216 (2)	C29···H21^ix	3.0600
O2···C35^ii	3.301 (2)	C30···H33	3.0300
O2···H16B^i	2.8600	C30···H21^ix	3.0400
O2···H29	2.5500	C31···H33	2.5800
O2···H9	2.9000	C32···H19	2.5100
O2···H35^ii	2.4900	C33···H27^x	3.0900
N1···O2	2.9910 (15)	C33···H19	2.8500
N1···C11	3.414 (2)	C35···H22^i	2.9800
N2···O2	2.6866 (16)	C37···H16A^i	2.9100
N2···C19	2.920 (2)	C37···H3^iii	3.0800
N3···C33	3.126 (2)	H3···N1	2.5600
N1···H37	2.4600	H3···C37^iii	3.0800
N1···H11	2.8300	H3···H19^iii	2.5500
N1···H16A^i	2.7600	H4···H8B	2.4800
N1···H3	2.5600	H6···H8A	2.4200
N2···H19	2.4200	H7···C9	2.7500
N3···H33	2.5200	H7···C10	3.0800
C1···O2	3.0971 (19)	H7···H9	2.3800
C2···C11	3.495 (2)	H8A···H6	2.4200
C3···C37^iii	3.494 (3)	H8B···H4	2.4800
C3···C36^iii	3.586 (3)	H8B···H23^xi	2.4500
C6···C29^iv	3.545 (3)	H9···O2	2.9000
C7···C10	3.423 (2)	H9···C7	2.9300
C10···C24	3.457 (2)	H9···H7	2.3800
C10···C18	3.0893 (19)	H9···H15	2.4300
C10···C23	3.353 (2)	H11···N1	2.8300
C10···C7	3.423 (2)	H11···C1	2.6100
C11···C2	3.495 (2)	H11···H37^iii	2.5000
C11···C19	3.437 (2)	H12···H12^xii	2.4800
C11···C23	3.299 (2)	H14···C16	2.5400
C11···N1	3.414 (2)	H14···H16B	2.3500
C11···C18	3.096 (2)	H14···H16C	2.3200
C12···C22	3.481 (3)	H15···H9	2.4300
C12···C23	3.460 (2)	H15···H24A	2.5600
C13···C28^iv	3.587 (2)	H15···C19^ix	2.9400
C14···C28^iv	3.579 (2)	H15···C20^ix	2.9000
C15···C24	3.578 (2)	H16A···N1^v	2.7600
C15···C23	3.567 (2)	H16A···C37^v	2.9100
C16···O2^v	3.415 (3)	H16B···O2^v	2.8600
C16···C37^v	3.494 (3)	H16B···C14	2.7700
C18···C10	3.0893 (19)	H16B···H14	2.3500
C18···C11	3.096 (2)	H16C···C14	2.7600
C19···C32	3.306 (3)	H16C···H14	2.3200
C19···C33	3.574 (3)	H16C···H34^ix	2.3200
C19···C11	3.437 (2)	H19···N2	2.4200
C19···N2	2.920 (2)	H19···C17	3.0100
C22···C12	3.481 (3)	H19···C32	2.5100
C23···C12	3.460 (2)	H19···C33	2.8500
C23···C15	3.567 (2)	H19···H3^iii	2.5500
C23···C11	3.299 (2)	H21···C29^viii	3.0600
C23···C10	3.353 (2)	H21···C30^viii	3.0400
C24···C15	3.578 (2)	H22···C35^v	2.9800
C24···C10	3.457 (2)	H23···C24	2.4200
C28···C14^vi	3.579 (2)	H23···H24A	2.2100
C28···C13^vi	3.587 (2)	H23···H24B	2.1500
C29···C6^vi	3.545 (3)	H23···H8B^xiii	2.4500
C31···C33	2.976 (2)	H24A···C9	2.9800
C32···O2	2.9688 (18)	H24A···C10	2.9300
C32···C19	3.306 (3)	H24A···C15	2.7600
C33···O2	3.216 (2)	H24A···C23	2.7600
C33···N3	3.126 (2)	H24A···H15	2.5600
C33···C31	2.976 (2)	H24A···H23	2.2100
C33···C19	3.574 (3)	H24B···C23	2.5600
C35···O2^vii	3.301 (2)	H24B···H23	2.1500
C36···C3^iii	3.586 (3)	H24B···H26	2.4600
C37···C16^i	3.494 (3)	H26···H24B	2.4600
C37···C3^iii	3.494 (3)	H27···C33^x	3.0900
C1···H11	2.6100	H27···H33^x	2.4200
C5···H29^iv	3.0800	H28···C7^vi	2.9800
C6···H29^iv	3.0600	H28···C14^vi	3.0700
C7···H9	2.9300	H28···C15^vi	3.0200
C7···H28^iv	2.9800	H29···O2	2.5500
C9···H7	2.7500	H29···C5^vi	3.0800
C9···H24A	2.9800	H29···C6^vi	3.0600
C10···H7	3.0800	H33···N3	2.5200
C10···H24A	2.9300	H33···C17	2.6200
C11···H36^iii	2.9700	H33···C30	3.0300
C12···H36^iii	3.0100	H33···C31	2.5800
C14···H28^iv	3.0700	H33···H27^x	2.4200
C14···H16B	2.7700	H34···H16C^viii	2.3200
C14···H16C	2.7600	H35···O2^vii	2.4900
C15···H28^iv	3.0200	H36···C11^iii	2.9700
C15···H24A	2.7600	H36···C12^iii	3.0100
C16···H14	2.5400	H37···N1	2.4600
C17···H33	2.6200	H37···H11^iii	2.5000
C17···H19	3.0100
C13—O1—C16	118.44 (17)	C34—C35—C36	119.1 (2)
N2—N1—C1	109.76 (12)	C35—C36—C37	121.0 (2)
N1—N2—C17	111.07 (10)	C32—C37—C36	120.35 (17)
N1—N2—C32	115.32 (12)	C2—C3—H3	119.00
C17—N2—C32	122.50 (11)	C4—C3—H3	120.00
C17—N3—C18	120.81 (11)	C3—C4—H4	119.00
C17—N3—C24	113.70 (11)	C5—C4—H4	119.00
C18—N3—C24	113.69 (13)	C5—C6—H6	119.00
N1—C1—C2	121.38 (13)	C7—C6—H6	119.00
N1—C1—C9	113.69 (12)	C2—C7—H7	120.00
C2—C1—C9	124.66 (13)	C6—C7—H7	120.00
C1—C2—C3	120.87 (14)	C5—C8—H8A	109.00
C1—C2—C7	121.64 (13)	C5—C8—H8B	109.00
C3—C2—C7	117.49 (14)	C5—C8—H8C	109.00
C2—C3—C4	121.03 (17)	H8A—C8—H8B	110.00
C3—C4—C5	121.73 (18)	H8A—C8—H8C	109.00
C4—C5—C6	117.01 (17)	H8B—C8—H8C	109.00
C4—C5—C8	121.48 (18)	C1—C9—H9	110.00
C6—C5—C8	121.45 (18)	C10—C9—H9	110.00
C5—C6—C7	122.19 (18)	C17—C9—H9	110.00
C2—C7—C6	120.49 (16)	C10—C11—H11	119.00
C1—C9—C10	110.91 (12)	C12—C11—H11	119.00
C1—C9—C17	99.76 (12)	C11—C12—H12	120.00
C10—C9—C17	116.13 (12)	C13—C12—H12	120.00
C9—C10—C11	120.93 (14)	C13—C14—H14	120.00
C9—C10—C15	122.08 (13)	C15—C14—H14	120.00
C11—C10—C15	117.00 (16)	C10—C15—H15	119.00
C10—C11—C12	121.94 (15)	C14—C15—H15	119.00
C11—C12—C13	120.20 (15)	O1—C16—H16A	109.00
O1—C13—C12	115.15 (15)	O1—C16—H16B	109.00
O1—C13—C14	124.92 (18)	O1—C16—H16C	109.00
C12—C13—C14	119.93 (19)	H16A—C16—H16B	110.00
C13—C14—C15	119.57 (17)	H16A—C16—H16C	109.00
C10—C15—C14	121.30 (14)	H16B—C16—H16C	109.00
N2—C17—N3	112.86 (11)	C18—C19—H19	120.00
N2—C17—C9	101.22 (10)	C20—C19—H19	120.00
N2—C17—C31	107.52 (13)	C19—C20—H20	119.00
N3—C17—C9	117.75 (13)	C21—C20—H20	119.00
N3—C17—C31	110.58 (11)	C20—C21—H21	121.00
C9—C17—C31	106.07 (11)	C22—C21—H21	121.00
N3—C18—C19	121.42 (16)	C21—C22—H22	120.00
N3—C18—C23	120.99 (13)	C23—C22—H22	119.00
C19—C18—C23	117.46 (15)	C18—C23—H23	120.00
C18—C19—C20	120.8 (2)	C22—C23—H23	119.00
C19—C20—C21	121.05 (18)	N3—C24—H24A	109.00
C20—C21—C22	118.6 (2)	N3—C24—H24B	109.00
C21—C22—C23	121.0 (2)	C25—C24—H24A	109.00
C18—C23—C22	121.02 (17)	C25—C24—H24B	109.00
N3—C24—C25	114.09 (14)	H24A—C24—H24B	108.00
C24—C25—C26	120.32 (16)	C25—C26—H26	120.00
C24—C25—C30	121.04 (13)	C27—C26—H26	120.00
C26—C25—C30	118.60 (15)	C26—C27—H27	119.00
C25—C26—C27	120.07 (19)	C28—C27—H27	119.00
C26—C27—C28	121.35 (16)	C27—C28—H28	120.00
C27—C28—C29	119.45 (18)	C29—C28—H28	120.00
C28—C29—C30	119.67 (19)	C28—C29—H29	120.00
C25—C30—C29	120.86 (14)	C30—C29—H29	120.00
C25—C30—C31	119.04 (14)	C32—C33—H33	120.00
C29—C30—C31	120.08 (16)	C34—C33—H33	120.00
O2—C31—C17	118.03 (12)	C33—C34—H34	120.00
O2—C31—C30	122.02 (14)	C35—C34—H34	120.00
C17—C31—C30	119.87 (14)	C34—C35—H35	120.00
N2—C32—C33	121.23 (15)	C36—C35—H35	120.00
N2—C32—C37	120.34 (14)	C35—C36—H36	119.00
C33—C32—C37	118.39 (16)	C37—C36—H36	120.00
C32—C33—C34	120.39 (17)	C32—C37—H37	120.00
C33—C34—C35	120.84 (18)	C36—C37—H37	120.00
C16—O1—C13—C12	−179.93 (17)	C1—C9—C17—C31	−92.73 (13)
C16—O1—C13—C14	1.1 (3)	C1—C9—C10—C15	141.99 (13)
C1—N1—N2—C17	11.63 (17)	C10—C9—C17—N3	23.69 (17)
N2—N1—C1—C9	3.25 (18)	C9—C10—C11—C12	−178.33 (14)
C1—N1—N2—C32	156.64 (13)	C9—C10—C15—C14	177.70 (14)
N2—N1—C1—C2	177.48 (13)	C15—C10—C11—C12	1.8 (2)
C32—N2—C17—C31	−50.98 (16)	C11—C10—C15—C14	−2.4 (2)
C32—N2—C17—N3	71.24 (18)	C10—C11—C12—C13	0.4 (2)
C17—N2—C32—C37	166.51 (15)	C11—C12—C13—C14	−2.0 (2)
N1—N2—C17—N3	−146.69 (12)	C11—C12—C13—O1	178.92 (15)
N1—N2—C17—C31	91.10 (13)	C12—C13—C14—C15	1.4 (2)
N1—N2—C32—C37	25.9 (2)	O1—C13—C14—C15	−179.66 (15)
N1—N2—C17—C9	−19.91 (15)	C13—C14—C15—C10	0.9 (2)
C32—N2—C17—C9	−161.99 (13)	N2—C17—C31—O2	−34.32 (17)
C17—N2—C32—C33	−15.8 (2)	C9—C17—C31—C30	−103.54 (14)
N1—N2—C32—C33	−156.43 (14)	C9—C17—C31—O2	73.33 (17)
C24—N3—C17—N2	−170.93 (12)	N3—C17—C31—O2	−157.94 (13)
C18—N3—C17—C9	−68.94 (17)	N3—C17—C31—C30	25.19 (18)
C18—N3—C17—N2	48.47 (18)	N2—C17—C31—C30	148.81 (12)
C18—N3—C24—C25	−164.79 (12)	C19—C18—C23—C22	2.8 (2)
C24—N3—C17—C9	71.66 (16)	C23—C18—C19—C20	−4.0 (2)
C24—N3—C17—C31	−50.45 (16)	N3—C18—C23—C22	178.57 (15)
C17—N3—C24—C25	51.74 (17)	N3—C18—C19—C20	−179.71 (14)
C17—N3—C18—C23	125.41 (15)	C18—C19—C20—C21	2.1 (3)
C24—N3—C18—C19	160.40 (13)	C19—C20—C21—C22	1.1 (3)
C24—N3—C18—C23	−15.19 (18)	C20—C21—C22—C23	−2.2 (3)
C18—N3—C17—C31	168.96 (13)	C21—C22—C23—C18	0.3 (3)
C17—N3—C18—C19	−59.00 (19)	N3—C24—C25—C26	157.23 (14)
C9—C1—C2—C7	−15.9 (2)	N3—C24—C25—C30	−25.1 (2)
C2—C1—C9—C17	171.02 (14)	C26—C25—C30—C29	−1.0 (2)
N1—C1—C9—C17	−14.97 (16)	C26—C25—C30—C31	177.39 (14)
C2—C1—C9—C10	−66.02 (18)	C30—C25—C26—C27	0.5 (2)
N1—C1—C2—C3	−10.2 (3)	C24—C25—C30—C29	−178.78 (14)
C9—C1—C2—C3	163.36 (17)	C24—C25—C26—C27	178.27 (16)
N1—C1—C2—C7	170.49 (16)	C24—C25—C30—C31	−0.3 (2)
N1—C1—C9—C10	107.99 (15)	C25—C26—C27—C28	0.1 (3)
C7—C2—C3—C4	1.9 (3)	C26—C27—C28—C29	−0.2 (3)
C3—C2—C7—C6	−1.8 (3)	C27—C28—C29—C30	−0.3 (3)
C1—C2—C7—C6	177.58 (18)	C28—C29—C30—C25	0.9 (2)
C1—C2—C3—C4	−177.40 (19)	C28—C29—C30—C31	−177.48 (15)
C2—C3—C4—C5	0.0 (3)	C25—C30—C31—C17	−0.1 (2)
C3—C4—C5—C8	174.9 (2)	C29—C30—C31—O2	1.6 (2)
C3—C4—C5—C6	−2.2 (3)	C29—C30—C31—C17	178.32 (13)
C8—C5—C6—C7	−174.7 (2)	C25—C30—C31—O2	−176.87 (14)
C4—C5—C6—C7	2.4 (3)	N2—C32—C33—C34	−179.51 (16)
C5—C6—C7—C2	−0.4 (3)	C37—C32—C33—C34	−1.8 (3)
C1—C9—C10—C11	−37.87 (17)	N2—C32—C37—C36	179.15 (17)
C10—C9—C17—N2	−99.81 (14)	C33—C32—C37—C36	1.4 (3)
C1—C9—C17—N3	142.88 (12)	C32—C33—C34—C35	0.7 (3)
C1—C9—C17—N2	19.39 (14)	C33—C34—C35—C36	0.9 (3)
C17—C9—C10—C15	−105.09 (15)	C34—C35—C36—C37	−1.3 (3)
C10—C9—C17—C31	148.07 (12)	C35—C36—C37—C32	0.1 (3)
C17—C9—C10—C11	75.05 (17)

Symmetry codes: (i) x+1, y, z; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+2, −y+1, −z+1; (iv) x, −y+3/2, z+1/2; (v) x−1, y, z; (vi) x, −y+3/2, z−1/2; (vii) −x+2, y−1/2, −z+1/2; (viii) −x+1, y−1/2, −z+1/2; (ix) −x+1, y+1/2, −z+1/2; (x) −x+1, −y+1, −z; (xi) x+1, −y+3/2, z+1/2; (xii) −x+1, −y+1, −z+1; (xiii) x−1, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N2	0.93	2.42	2.920 (2)	114
C33—H33···N3	0.93	2.52	3.126 (2)	123
C35—H35···O2^vii	0.93	2.49	3.301 (2)	145

Symmetry code: (vii) −x+2, y−1/2, −z+1/2.