11-Phenyl-7,8,9,10,10a,11,12,13,14,15-deca­hydro-5H-3,1-benzoxazino[2,1-e]acridine

2-Hydr­oxy-8-phenyl­tricyclo­[7.3.1.0^2,7]tridecan-13-one reacts with 2-amino­benzyl alcohol to form the title compound, C₂₆H₂₉NO, which crystallizes with two independent mol­ecules in the asymmetric unit. The N atom shows a nearly planar coordination owing to the strain imposed on the fused-ring compound.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.133
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

11-Phenyl-7,8,9,10,10a,11,12,13,14,15-decaydro-5H-3,1-benzoxazino[2,1-e]acridine

Crystal data

C26H29NO	Z = 4
Mr = 371.50	F(000) = 800
Triclinic, P1	Dx = 1.211 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.653 (1) Å	Cell parameters from 956 reflections
b = 11.427 (1) Å	θ = 2.4–27.6°
c = 17.337 (2) Å	µ = 0.07 mm^−1
α = 91.124 (2)°	T = 295 K
β = 100.810 (2)°	Prism, colorless
γ = 100.191 (2)°	0.40 × 0.35 × 0.25 mm
V = 2037.4 (4) Å^3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	6699 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
Detector resolution: 8.33 pixels mm^-1	h = −13→13
φ and ω scans	k = −14→14
25549 measured reflections	l = −22→22
9331 independent reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.6554P] where P = (Fo^2 + 2Fc^2)/3
9331 reflections	(Δ/σ)max = 0.001
505 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4373 (1)	0.8526 (1)	0.3996 (1)	0.0411 (3)
O2	0.4923 (1)	0.3376 (1)	0.0851 (1)	0.0403 (2)
N1	0.6470 (1)	0.8029 (1)	0.4069 (1)	0.0381 (3)
N2	0.7213 (1)	0.3528 (1)	0.1259 (1)	0.0355 (3)
C1	0.4363 (2)	0.8574 (2)	0.3168 (1)	0.0416 (3)
C2	0.5644 (2)	0.9261 (1)	0.3069 (1)	0.0372 (3)
C3	0.5818 (2)	1.0165 (2)	0.2563 (1)	0.0458 (4)
C4	0.7045 (2)	1.0807 (2)	0.2553 (1)	0.0552 (4)
C5	0.8094 (2)	1.0561 (2)	0.3082 (1)	0.0561 (4)
C6	0.7938 (2)	0.9683 (2)	0.3614 (1)	0.0465 (4)
C7	0.6713 (1)	0.8995 (1)	0.3596 (1)	0.0368 (3)
C8	0.7535 (1)	0.7594 (1)	0.4522 (1)	0.0380 (3)
C9	0.8404 (2)	0.7106 (2)	0.4049 (1)	0.0502 (4)
C10	0.9685 (2)	0.6987 (2)	0.4557 (1)	0.0732 (6)
C11	0.9516 (2)	0.6382 (2)	0.5289 (1)	0.0643 (5)
C12	0.8738 (2)	0.6972 (2)	0.5772 (1)	0.0471 (4)
C13	0.7663 (1)	0.7511 (1)	0.5296 (1)	0.0353 (3)
C14	0.6715 (1)	0.7889 (1)	0.5759 (1)	0.0339 (3)
C15	0.7421 (1)	0.8772 (1)	0.6435 (1)	0.0366 (3)
C16	0.8169 (2)	0.9839 (2)	0.6293 (1)	0.0517 (4)
C17	0.8853 (2)	1.0628 (2)	0.6904 (1)	0.0672 (6)
C18	0.8814 (2)	1.0369 (2)	0.7667 (1)	0.0710 (6)
C19	0.8069 (2)	0.9330 (2)	0.7821 (1)	0.0731 (7)
C20	0.7368 (2)	0.8532 (2)	0.7206 (1)	0.0551 (5)
C21	0.5572 (1)	0.8365 (1)	0.5256 (1)	0.0348 (3)
C22	0.4347 (2)	0.8117 (2)	0.5619 (1)	0.0484 (4)
C23	0.3706 (2)	0.6807 (2)	0.5540 (1)	0.0579 (5)
C24	0.3427 (2)	0.6316 (2)	0.4689 (1)	0.0561 (5)
C25	0.4649 (2)	0.6532 (1)	0.4336 (1)	0.0440 (4)
C26	0.5268 (1)	0.7853 (1)	0.4404 (1)	0.0345 (3)
C27	0.4948 (2)	0.2136 (1)	0.0716 (1)	0.0432 (4)
C28	0.5995 (2)	0.2075 (1)	0.0264 (1)	0.0382 (3)
C29	0.5858 (2)	0.1387 (2)	−0.0427 (1)	0.0487 (4)
C30	0.6863 (2)	0.1492 (2)	−0.0837 (1)	0.0599 (5)
C31	0.7982 (2)	0.2312 (2)	−0.0570 (1)	0.0589 (5)
C32	0.8131 (2)	0.3026 (2)	0.0108 (1)	0.0471 (4)
C33	0.7144 (1)	0.2890 (1)	0.0542 (1)	0.0355 (3)
C34	0.8430 (1)	0.4232 (1)	0.1625 (1)	0.0361 (3)
C35	0.9496 (2)	0.3537 (2)	0.1910 (1)	0.0482 (4)
C36	1.0825 (2)	0.4332 (2)	0.2084 (1)	0.0597 (5)
C37	1.0802 (2)	0.5395 (2)	0.2611 (1)	0.0607 (5)
C38	0.9826 (2)	0.6132 (2)	0.2222 (1)	0.0466 (4)
C39	0.8568 (1)	0.5404 (1)	0.1771 (1)	0.0358 (3)
C40	0.7463 (1)	0.6084 (1)	0.1546 (1)	0.0348 (3)
C41	0.7844 (1)	0.7158 (1)	0.1075 (1)	0.0398 (3)
C42	0.8297 (2)	0.7019 (2)	0.0387 (1)	0.0542 (4)
C43	0.8641 (2)	0.7992 (2)	−0.0048 (1)	0.0684 (6)
C44	0.8522 (2)	0.9110 (2)	0.0198 (1)	0.0693 (6)
C45	0.8069 (2)	0.9264 (2)	0.0875 (1)	0.0654 (6)
C46	0.7732 (2)	0.8293 (2)	0.1318 (1)	0.0510 (4)
C47	0.6178 (1)	0.5304 (1)	0.1109 (1)	0.0336 (3)
C48	0.4991 (2)	0.5829 (1)	0.1228 (1)	0.0418 (3)
C49	0.4738 (2)	0.5717 (2)	0.2064 (1)	0.0482 (4)
C50	0.4654 (2)	0.4442 (2)	0.2314 (1)	0.0484 (4)
C51	0.5852 (2)	0.3931 (1)	0.2215 (1)	0.0404 (3)
C52	0.6047 (1)	0.4020 (1)	0.1363 (1)	0.0334 (3)
H1a	0.3666	0.8961	0.2916	0.050*
H1b	0.4228	0.7775	0.2930	0.050*
H3	0.5101	1.0346	0.2224	0.055*
H4	0.7160	1.1395	0.2196	0.066*
H5	0.8921	1.0993	0.3082	0.067*
H6	0.8649	0.9553	0.3982	0.056*
H9a	0.7966	0.6332	0.3808	0.060*
H9b	0.8563	0.7632	0.3632	0.060*
H10a	1.0146	0.6539	0.4260	0.088*
H10b	1.0212	0.7773	0.4693	0.088*
H11a	1.0366	0.6369	0.5606	0.077*
H11b	0.9084	0.5563	0.5153	0.077*
H12a	0.9325	0.7593	0.6118	0.057*
H12b	0.8358	0.6386	0.6100	0.057*
H14	0.6332	0.7174	0.5996	0.041*
H16	0.8209	1.0026	0.5778	0.062*
H17	0.9345	1.1340	0.6796	0.081*
H18	0.9290	1.0895	0.8077	0.085*
H19	0.8029	0.9153	0.8338	0.088*
H20	0.6860	0.7830	0.7317	0.066*
H21	0.5831	0.9230	0.5247	0.042*
H22a	0.4578	0.8375	0.6171	0.058*
H22b	0.3726	0.8583	0.5363	0.058*
H23a	0.2899	0.6715	0.5733	0.069*
H23b	0.4273	0.6353	0.5861	0.069*
H24a	0.3089	0.5467	0.4667	0.067*
H24b	0.2769	0.6694	0.4380	0.067*
H25a	0.4430	0.6255	0.3787	0.053*
H25b	0.5271	0.6079	0.4607	0.053*
H27a	0.4116	0.1728	0.0419	0.052*
H27b	0.5128	0.1762	0.1212	0.052*
H29	0.5087	0.0854	−0.0614	0.058*
H30	0.6784	0.1013	−0.1289	0.072*
H31	0.8653	0.2388	−0.0850	0.071*
H32	0.8884	0.3591	0.0272	0.056*
H35a	0.9484	0.2924	0.1511	0.058*
H35b	0.9332	0.3147	0.2382	0.058*
H36a	1.1466	0.3886	0.2340	0.072*
H36b	1.1068	0.4601	0.1596	0.072*
H37a	1.1661	0.5888	0.2731	0.073*
H37b	1.0574	0.5122	0.3102	0.073*
H38a	0.9628	0.6633	0.2624	0.056*
H38b	1.0225	0.6651	0.1864	0.056*
H40	0.7287	0.6395	0.2038	0.042*
H42	0.8372	0.6264	0.0213	0.065*
H43	0.8951	0.7886	−0.0507	0.082*
H44	0.8748	0.9761	−0.0094	0.083*
H45	0.7985	1.0020	0.1041	0.078*
H46	0.7431	0.8407	0.1779	0.061*
H47	0.6194	0.5289	0.0546	0.040*
H48a	0.5129	0.6663	0.1111	0.050*
H48b	0.4230	0.5422	0.0861	0.050*
H49a	0.5432	0.6231	0.2424	0.058*
H49b	0.3930	0.5980	0.2092	0.058*
H50a	0.3884	0.3949	0.2002	0.058*
H50b	0.4567	0.4419	0.2861	0.058*
H51a	0.5741	0.3104	0.2351	0.048*
H51b	0.6615	0.4369	0.2567	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0355 (5)	0.0538 (6)	0.0381 (6)	0.0193 (5)	0.0073 (4)	0.0061 (5)
O2	0.0305 (5)	0.0399 (6)	0.0482 (6)	0.0071 (4)	0.0016 (4)	−0.0038 (5)
N1	0.0338 (6)	0.0470 (7)	0.0386 (7)	0.0169 (5)	0.0103 (5)	0.0089 (6)
N2	0.0292 (6)	0.0370 (6)	0.0393 (7)	0.0080 (5)	0.0030 (5)	−0.0026 (5)
C1	0.037 (1)	0.051 (1)	0.037 (1)	0.014 (1)	0.002 (1)	0.003 (1)
C2	0.040 (1)	0.040 (1)	0.033 (1)	0.013 (1)	0.006 (1)	0.000 (1)
C3	0.050 (1)	0.048 (1)	0.041 (1)	0.018 (1)	0.007 (1)	0.007 (1)
C4	0.061 (1)	0.047 (1)	0.062 (1)	0.014 (1)	0.017 (1)	0.016 (1)
C5	0.048 (1)	0.051 (1)	0.069 (1)	0.002 (1)	0.015 (1)	0.009 (1)
C6	0.038 (1)	0.051 (1)	0.050 (1)	0.011 (1)	0.005 (1)	0.004 (1)
C7	0.038 (1)	0.040 (1)	0.035 (1)	0.012 (1)	0.008 (1)	0.001 (1)
C8	0.034 (1)	0.040 (1)	0.043 (1)	0.014 (1)	0.009 (1)	0.004 (1)
C9	0.048 (1)	0.059 (1)	0.052 (1)	0.026 (1)	0.017 (1)	0.005 (1)
C10	0.056 (1)	0.100 (2)	0.078 (1)	0.044 (1)	0.022 (1)	0.017 (1)
C11	0.054 (1)	0.077 (1)	0.071 (1)	0.039 (1)	0.010 (1)	0.013 (1)
C12	0.045 (1)	0.048 (1)	0.048 (1)	0.019 (1)	−0.002 (1)	0.000 (1)
C13	0.034 (1)	0.031 (1)	0.040 (1)	0.009 (1)	0.003 (1)	0.000 (1)
C14	0.035 (1)	0.031 (1)	0.035 (1)	0.005 (1)	0.006 (1)	0.001 (1)
C15	0.034 (1)	0.038 (1)	0.038 (1)	0.009 (1)	0.004 (1)	−0.002 (1)
C16	0.047 (1)	0.049 (1)	0.057 (1)	−0.005 (1)	0.019 (1)	−0.012 (1)
C17	0.044 (1)	0.063 (1)	0.090 (2)	−0.008 (1)	0.020 (1)	−0.032 (1)
C18	0.050 (1)	0.079 (2)	0.075 (2)	0.021 (1)	−0.016 (1)	−0.037 (1)
C19	0.102 (2)	0.081 (2)	0.036 (1)	0.044 (1)	−0.009 (1)	−0.008 (1)
C20	0.077 (1)	0.049 (1)	0.040 (1)	0.018 (1)	0.006 (1)	0.005 (1)
C21	0.034 (1)	0.034 (1)	0.037 (1)	0.008 (1)	0.006 (1)	−0.002 (1)
C22	0.040 (1)	0.066 (1)	0.042 (1)	0.014 (1)	0.011 (1)	−0.006 (1)
C23	0.040 (1)	0.078 (1)	0.054 (1)	−0.002 (1)	0.017 (1)	0.007 (1)
C24	0.044 (1)	0.055 (1)	0.062 (1)	−0.008 (1)	0.007 (1)	−0.001 (1)
C25	0.045 (1)	0.042 (1)	0.043 (1)	0.006 (1)	0.004 (1)	−0.005 (1)
C26	0.031 (1)	0.040 (1)	0.035 (1)	0.012 (1)	0.006 (1)	0.002 (1)
C27	0.039 (1)	0.036 (1)	0.051 (1)	0.002 (1)	0.004 (1)	0.001 (1)
C28	0.039 (1)	0.032 (1)	0.043 (1)	0.010 (1)	0.002 (1)	0.003 (1)
C29	0.050 (1)	0.041 (1)	0.052 (1)	0.014 (1)	−0.003 (1)	−0.005 (1)
C30	0.065 (1)	0.067 (1)	0.048 (1)	0.025 (1)	0.003 (1)	−0.016 (1)
C31	0.057 (1)	0.076 (1)	0.050 (1)	0.023 (1)	0.018 (1)	−0.004 (1)
C32	0.040 (1)	0.054 (1)	0.049 (1)	0.011 (1)	0.011 (1)	0.000 (1)
C33	0.036 (1)	0.034 (1)	0.038 (1)	0.012 (1)	0.005 (1)	0.003 (1)
C34	0.031 (1)	0.040 (1)	0.037 (1)	0.007 (1)	0.003 (1)	0.002 (1)
C35	0.038 (1)	0.050 (1)	0.055 (1)	0.015 (1)	−0.002 (1)	0.002 (1)
C36	0.035 (1)	0.070 (1)	0.071 (1)	0.015 (1)	−0.002 (1)	0.002 (1)
C37	0.042 (1)	0.065 (1)	0.064 (1)	0.006 (1)	−0.012 (1)	0.000 (1)
C38	0.041 (1)	0.047 (1)	0.046 (1)	0.000 (1)	−0.001 (1)	0.003 (1)
C39	0.033 (1)	0.039 (1)	0.033 (1)	0.004 (1)	0.003 (1)	0.005 (1)
C40	0.037 (1)	0.034 (1)	0.034 (1)	0.006 (1)	0.006 (1)	0.003 (1)
C41	0.033 (1)	0.039 (1)	0.046 (1)	0.006 (1)	0.004 (1)	0.010 (1)
C42	0.053 (1)	0.059 (1)	0.060 (1)	0.021 (1)	0.021 (1)	0.022 (1)
C43	0.050 (1)	0.091 (2)	0.075 (1)	0.023 (1)	0.026 (1)	0.045 (1)
C44	0.040 (1)	0.066 (1)	0.095 (2)	−0.001 (1)	0.003 (1)	0.045 (1)
C45	0.056 (1)	0.038 (1)	0.090 (2)	−0.001 (1)	−0.009 (1)	0.015 (1)
C46	0.051 (1)	0.039 (1)	0.058 (1)	0.004 (1)	0.000 (1)	0.004 (1)
C47	0.034 (1)	0.037 (1)	0.031 (1)	0.009 (1)	0.006 (1)	0.006 (1)
C48	0.039 (1)	0.040 (1)	0.048 (1)	0.014 (1)	0.007 (1)	0.007 (1)
C49	0.045 (1)	0.051 (1)	0.054 (1)	0.017 (1)	0.017 (1)	−0.001 (1)
C50	0.051 (1)	0.056 (1)	0.045 (1)	0.013 (1)	0.022 (1)	0.008 (1)
C51	0.044 (1)	0.040 (1)	0.040 (1)	0.009 (1)	0.011 (1)	0.009 (1)
C52	0.029 (1)	0.035 (1)	0.036 (7)	0.007 (1)	0.005 (1)	0.001 (1)

Geometric parameters (Å, º)

O1—C26	1.424 (2)	C48—C49	1.526 (2)
O1—C1	1.436 (2)	C49—C50	1.521 (2)
O2—C52	1.423 (2)	C50—C51	1.530 (2)
O2—C27	1.438 (2)	C51—C52	1.533 (2)
N1—C7	1.404 (2)	C1—H1a	0.97
N1—C8	1.425 (2)	C1—H1b	0.97
N1—C26	1.487 (2)	C3—H3	0.93
N2—C33	1.413 (2)	C4—H4	0.93
N2—C34	1.426 (2)	C5—H5	0.93
N2—C52	1.489 (2)	C6—H6	0.93
C1—C2	1.490 (2)	C9—H9a	0.97
C2—C3	1.378 (2)	C9—H9b	0.97
C2—C7	1.403 (2)	C10—H10a	0.97
C3—C4	1.385 (2)	C10—H10b	0.97
C4—C5	1.381 (3)	C11—H11a	0.97
C5—C6	1.385 (2)	C11—H11b	0.97
C6—C7	1.394 (2)	C12—H12a	0.97
C8—C13	1.331 (2)	C12—H12b	0.97
C8—C9	1.514 (2)	C14—H14	0.98
C9—C10	1.509 (3)	C16—H16	0.93
C10—C11	1.483 (3)	C17—H17	0.93
C11—C12	1.509 (2)	C18—H18	0.93
C12—C13	1.511 (2)	C19—H19	0.93
C13—C14	1.514 (2)	C20—H20	0.93
C14—C15	1.521 (2)	C21—H21	0.98
C14—C21	1.547 (2)	C22—H22a	0.97
C15—C20	1.379 (2)	C22—H22b	0.97
C15—C16	1.386 (2)	C23—H23a	0.97
C16—C17	1.381 (3)	C23—H23b	0.97
C17—C18	1.368 (3)	C24—H24a	0.97
C18—C19	1.368 (3)	C24—H24b	0.97
C19—C20	1.396 (3)	C25—H25a	0.97
C21—C26	1.533 (2)	C25—H25b	0.97
C21—C22	1.537 (2)	C27—H27a	0.97
C22—C23	1.523 (3)	C27—H27b	0.97
C23—C24	1.524 (3)	C29—H29	0.93
C24—C25	1.523 (2)	C30—H30	0.93
C25—C26	1.529 (2)	C31—H31	0.93
C27—C28	1.489 (2)	C32—H32	0.93
C28—C29	1.389 (2)	C35—H35a	0.97
C28—C33	1.398 (2)	C35—H35b	0.97
C29—C30	1.382 (3)	C36—H36a	0.97
C30—C31	1.376 (3)	C36—H36b	0.97
C31—C32	1.385 (2)	C37—H37a	0.97
C32—C33	1.392 (2)	C37—H37b	0.97
C34—C39	1.335 (2)	C38—H38a	0.97
C34—C35	1.513 (2)	C38—H38b	0.97
C35—C36	1.514 (2)	C40—H40	0.98
C36—C37	1.513 (3)	C42—H42	0.93
C37—C38	1.522 (2)	C43—H43	0.93
C38—C39	1.511 (2)	C44—H44	0.93
C39—C40	1.518 (2)	C45—H45	0.93
C40—C41	1.525 (2)	C46—H46	0.93
C40—C47	1.548 (2)	C47—H47	0.98
C41—C42	1.385 (2)	C48—H48a	0.97
C41—C46	1.388 (2)	C48—H48b	0.97
C42—C43	1.390 (3)	C49—H49a	0.97
C43—C44	1.374 (3)	C49—H49b	0.97
C44—C45	1.369 (3)	C50—H50a	0.97
C45—C46	1.394 (3)	C50—H50b	0.97
C47—C52	1.530 (2)	C51—H51a	0.97
C47—C48	1.536 (2)	C51—H51b	0.97
C26—O1—C1	114.3 (1)	C11—C10—H10b	109.1
C52—O2—C27	114.4 (1)	C9—C10—H10b	109.1
C7—N1—C8	119.5 (1)	H10a—C10—H10b	107.9
C7—N1—C26	119.0 (1)	C10—C11—H11a	108.9
C8—N1—C26	115.0 (1)	C12—C11—H11a	108.9
C33—N2—C34	118.3 (1)	C10—C11—H11b	108.9
C33—N2—C52	117.3 (1)	C12—C11—H11b	108.9
C34—N2—C52	115.2 (1)	H11a—C11—H11b	107.7
O1—C1—C2	107.8 (1)	C11—C12—H12a	108.6
C3—C2—C7	120.1 (2)	C13—C12—H12a	108.6
C3—C2—C1	125.3 (1)	C11—C12—H12b	108.6
C7—C2—C1	114.3 (1)	C13—C12—H12b	108.6
C2—C3—C4	121.0 (2)	H12a—C12—H12b	107.6
C5—C4—C3	118.9 (1)	C13—C14—H14	106.6
C4—C5—C6	121.2 (2)	C15—C14—H14	106.6
C5—C6—C7	119.9 (2)	C21—C14—H14	106.6
C6—C7—N1	124.2 (1)	C17—C16—H16	119.4
C6—C7—C2	118.8 (1)	C15—C16—H16	119.4
N1—C7—C2	116.9 (1)	C18—C17—H17	119.7
C13—C8—N1	121.7 (1)	C16—C17—H17	119.7
C13—C8—C9	122.8 (1)	C19—C18—H18	120.3
N1—C8—C9	115.1 (1)	C17—C18—H18	120.3
C10—C9—C8	111.6 (2)	C18—C19—H19	119.8
C11—C10—C9	112.3 (2)	C20—C19—H19	119.8
C10—C11—C12	113.3 (2)	C15—C20—H20	119.6
C11—C12—C13	114.7 (1)	C19—C20—H20	119.6
C8—C13—C12	122.0 (1)	C26—C21—H21	107.7
C8—C13—C14	122.8 (1)	C22—C21—H21	107.7
C12—C13—C14	115.2 (1)	C14—C21—H21	107.7
C13—C14—C15	110.9 (1)	C23—C22—H22a	109.0
C13—C14—C21	114.6 (1)	C21—C22—H22a	109.0
C15—C14—C21	111.1 (1)	C23—C22—H22b	109.0
C20—C15—C16	117.8 (2)	C21—C22—H22b	109.0
C20—C15—C14	121.5 (2)	H22a—C22—H22b	107.8
C16—C15—C14	120.6 (1)	C22—C23—H23a	109.3
C17—C16—C15	121.1 (2)	C24—C23—H23a	109.3
C18—C17—C16	120.5 (2)	C22—C23—H23b	109.3
C19—C18—C17	119.4 (2)	C24—C23—H23b	109.3
C18—C19—C20	120.3 (2)	H23a—C23—H23b	107.9
C15—C20—C19	120.8 (2)	C25—C24—H24a	109.4
C26—C21—C22	110.3 (1)	C23—C24—H24a	109.4
C26—C21—C14	111.9 (1)	C25—C24—H24b	109.4
C22—C21—C14	111.5 (1)	C23—C24—H24b	109.4
C23—C22—C21	113.0 (1)	H24a—C24—H24b	108.0
C22—C23—C24	111.7 (2)	C24—C25—H25a	109.4
C25—C24—C23	111.3 (1)	C26—C25—H25a	109.4
C24—C25—C26	111.3 (1)	C24—C25—H25b	109.4
O1—C26—N1	109.8 (1)	C26—C25—H25b	109.4
O1—C26—C25	109.9 (1)	H25a—C25—H25b	108.0
N1—C26—C25	109.9 (1)	O2—C27—H27a	110.3
O1—C26—C21	104.8 (1)	C28—C27—H27a	110.3
N1—C26—C21	110.2 (1)	O2—C27—H27b	110.3
C25—C26—C21	112.1 (1)	C28—C27—H27b	110.3
O2—C27—C28	106.9 (1)	H27a—C27—H27b	108.6
C29—C28—C33	120.2 (2)	C30—C29—H29	119.9
C29—C28—C27	125.5 (1)	C28—C29—H29	119.9
C33—C28—C27	114.0 (1)	C31—C30—H30	120.3
C30—C29—C28	120.2 (2)	C29—C30—H30	120.3
C31—C30—C29	119.5 (2)	C30—C31—H31	119.3
C30—C31—C32	121.5 (2)	C32—C31—H31	119.3
C31—C32—C33	119.3 (2)	C31—C32—H32	120.3
C32—C33—C28	119.3 (1)	C33—C32—H32	120.3
C32—C33—N2	124.3 (1)	C34—C35—H35a	109.3
C28—C33—N2	116.4 (1)	C36—C35—H35a	109.3
C39—C34—N2	121.8 (1)	C34—C35—H35b	109.3
C39—C34—C35	122.9 (1)	C36—C35—H35b	109.3
N2—C34—C35	115.1 (1)	H35a—C35—H35b	107.9
C34—C35—C36	111.8 (1)	C37—C36—H36a	109.7
C37—C36—C35	109.9 (2)	C35—C36—H36a	109.7
C36—C37—C38	111.3 (2)	C37—C36—H36b	109.7
C39—C38—C37	114.3 (1)	C35—C36—H36b	109.7
C34—C39—C38	121.7 (1)	H36a—C36—H36b	108.2
C34—C39—C40	122.8 (1)	C36—C37—H37a	109.4
C38—C39—C40	115.4 (1)	C38—C37—H37a	109.4
C39—C40—C41	111.9 (1)	C36—C37—H37b	109.4
C39—C40—C47	114.0 (1)	C38—C37—H37b	109.4
C41—C40—C47	110.3 (1)	H37a—C37—H37b	108.0
C42—C41—C46	118.4 (2)	C39—C38—H38a	108.7
C42—C41—C40	120.5 (1)	C37—C38—H38a	108.7
C46—C41—C40	121.1 (2)	C39—C38—H38b	108.7
C41—C42—C43	120.9 (2)	C37—C38—H38b	108.7
C44—C43—C42	120.1 (2)	H38a—C38—H38b	107.6
C45—C44—C43	119.8 (2)	C39—C40—H40	106.7
C44—C45—C46	120.4 (2)	C41—C40—H40	106.7
C41—C46—C45	120.4 (2)	C47—C40—H40	106.7
C52—C47—C48	110.3 (1)	C41—C42—H42	119.5
C52—C47—C40	111.5 (1)	C43—C42—H42	119.5
C48—C47—C40	111.5 (1)	C44—C43—H43	120.0
C49—C48—C47	112.6 (1)	C42—C43—H43	120.0
C50—C49—C48	111.7 (1)	C45—C44—H44	120.1
C49—C50—C51	112.1 (1)	C43—C44—H44	120.1
C50—C51—C52	110.0 (1)	C44—C45—H45	119.8
O2—C52—N2	109.8 (1)	C46—C45—H45	119.8
O2—C52—C47	105.5 (1)	C41—C46—H46	119.8
N2—C52—C47	109.9 (1)	C45—C46—H46	119.8
O2—C52—C51	109.3 (1)	C52—C47—H47	107.8
N2—C52—C51	110.5 (1)	C48—C47—H47	107.8
C47—C52—C51	111.8 (1)	C40—C47—H47	107.8
O1—C1—H1a	110.2	C49—C48—H48a	109.1
C2—C1—H1a	110.2	C47—C48—H48a	109.1
O1—C1—H1b	110.2	C49—C48—H48b	109.1
C2—C1—H1b	110.2	C47—C48—H48b	109.1
H1a—C1—H1b	108.5	H48a—C48—H48b	107.8
C2—C3—H3	119.5	C50—C49—H49a	109.3
C4—C3—H3	119.5	C48—C49—H49a	109.3
C5—C4—H4	120.6	C50—C49—H49b	109.3
C3—C4—H4	120.6	C48—C49—H49b	109.3
C4—C5—H5	119.4	H49a—C49—H49b	107.9
C6—C5—H5	119.4	C49—C50—H50a	109.2
C5—C6—H6	120.1	C51—C50—H50a	109.2
C7—C6—H6	120.1	C49—C50—H50b	109.2
C10—C9—H9a	109.3	C51—C50—H50b	109.2
C8—C9—H9a	109.3	H50a—C50—H50b	107.9
C10—C9—H9b	109.3	C50—C51—H51a	109.7
C8—C9—H9b	109.3	C52—C51—H51a	109.7
H9a—C9—H9b	108.0	C50—C51—H51b	109.7
C11—C10—H10a	109.1	C52—C51—H51b	109.7
C9—C10—H10a	109.1	H51a—C51—H51b	108.2
C26—O1—C1—C2	−66.6 (2)	C52—O2—C27—C28	−67.2 (2)
O1—C1—C2—C3	−132.7 (2)	O2—C27—C28—C29	−129.2 (2)
O1—C1—C2—C7	41.7 (2)	O2—C27—C28—C33	43.9 (2)
C7—C2—C3—C4	1.4 (2)	C33—C28—C29—C30	1.0 (2)
C1—C2—C3—C4	175.5 (2)	C27—C28—C29—C30	173.6 (2)
C2—C3—C4—C5	−2.6 (3)	C28—C29—C30—C31	−2.2 (3)
C3—C4—C5—C6	0.5 (3)	C29—C30—C31—C32	0.8 (3)
C4—C5—C6—C7	2.9 (3)	C30—C31—C32—C33	1.8 (3)
C5—C6—C7—N1	175.1 (2)	C31—C32—C33—C28	−3.1 (2)
C5—C6—C7—C2	−4.0 (2)	C31—C32—C33—N2	177.0 (2)
C8—N1—C7—C6	−9.2 (2)	C29—C28—C33—C32	1.7 (2)
C26—N1—C7—C6	141.1 (2)	C27—C28—C33—C32	−171.7 (1)
C8—N1—C7—C2	170.0 (1)	C29—C28—C33—N2	−178.3 (1)
C26—N1—C7—C2	−39.8 (2)	C27—C28—C33—N2	8.3 (2)
C3—C2—C7—C6	2.0 (2)	C34—N2—C33—C32	−9.3 (2)
C1—C2—C7—C6	−172.8 (1)	C52—N2—C33—C32	135.8 (2)
C3—C2—C7—N1	−177.2 (1)	C34—N2—C33—C28	170.7 (1)
C1—C2—C7—N1	8.1 (2)	C52—N2—C33—C28	−44.2 (2)
C7—N1—C8—C13	124.5 (2)	C33—N2—C34—C39	120.8 (2)
C26—N1—C8—C13	−26.9 (2)	C52—N2—C34—C39	−25.1 (2)
C7—N1—C8—C9	−62.4 (2)	C33—N2—C34—C35	−65.6 (2)
C26—N1—C8—C9	146.2 (1)	C52—N2—C34—C35	148.6 (1)
C13—C8—C9—C10	−22.9 (2)	C39—C34—C35—C36	−21.9 (2)
N1—C8—C9—C10	164.2 (2)	N2—C34—C35—C36	164.5 (1)
C8—C9—C10—C11	48.3 (2)	C34—C35—C36—C37	50.6 (2)
C9—C10—C11—C12	−55.4 (3)	C35—C36—C37—C38	−60.5 (2)
C10—C11—C12—C13	34.6 (3)	C36—C37—C38—C39	39.9 (2)
N1—C8—C13—C12	175.7 (1)	N2—C34—C39—C38	174.5 (1)
C9—C8—C13—C12	3.1 (2)	C35—C34—C39—C38	1.4 (2)
N1—C8—C13—C14	−1.3 (2)	N2—C34—C39—C40	−1.5 (2)
C9—C8—C13—C14	−173.8 (1)	C35—C34—C39—C40	−174.6 (1)
C11—C12—C13—C8	−8.6 (2)	C37—C38—C39—C34	−10.5 (2)
C11—C12—C13—C14	168.6 (2)	C37—C38—C39—C40	165.8 (2)
C8—C13—C14—C15	−126.0 (2)	C34—C39—C40—C41	−127.9 (2)
C12—C13—C14—C15	56.9 (2)	C38—C39—C40—C41	55.8 (2)
C8—C13—C14—C21	0.8 (2)	C34—C39—C40—C47	−1.8 (2)
C12—C13—C14—C21	−176.3 (1)	C38—C39—C40—C47	−178.1 (1)
C13—C14—C15—C20	−119.9 (2)	C39—C40—C41—C42	56.2 (2)
C21—C14—C15—C20	111.4 (2)	C47—C40—C41—C42	−71.9 (2)
C13—C14—C15—C16	58.5 (2)	C39—C40—C41—C46	−124.7 (2)
C21—C14—C15—C16	−70.2 (2)	C47—C40—C41—C46	107.3 (2)
C20—C15—C16—C17	0.9 (3)	C46—C41—C42—C43	0.5 (3)
C14—C15—C16—C17	−177.6 (2)	C40—C41—C42—C43	179.7 (2)
C15—C16—C17—C18	0.3 (3)	C41—C42—C43—C44	−0.7 (3)
C16—C17—C18—C19	−1.2 (3)	C42—C43—C44—C45	0.2 (3)
C17—C18—C19—C20	0.8 (3)	C43—C44—C45—C46	0.3 (3)
C16—C15—C20—C19	−1.3 (3)	C42—C41—C46—C45	0.0 (2)
C14—C15—C20—C19	177.1 (2)	C40—C41—C46—C45	−179.1 (2)
C18—C19—C20—C15	0.5 (3)	C44—C45—C46—C41	−0.4 (3)
C13—C14—C21—C26	26.1 (2)	C39—C40—C47—C52	29.9 (2)
C15—C14—C21—C26	152.8 (1)	C41—C40—C47—C52	156.9 (2)
C13—C14—C21—C22	150.2 (1)	C39—C40—C47—C48	153.8 (1)
C15—C14—C21—C22	−83.2 (2)	C41—C40—C47—C48	−79.3 (2)
C26—C21—C22—C23	53.0 (2)	C52—C47—C48—C49	53.5 (2)
C14—C21—C22—C23	−72.0 (2)	C40—C47—C48—C49	−71.0 (2)
C21—C22—C23—C24	−53.6 (2)	C47—C48—C49—C50	−52.8 (2)
C22—C23—C24—C25	54.2 (2)	C48—C49—C50—C51	54.0 (2)
C23—C24—C25—C26	−55.5 (2)	C49—C50—C51—C52	−55.9 (2)
C1—O1—C26—N1	36.7 (2)	C27—O2—C52—N2	33.3 (2)
C1—O1—C26—C25	−84.4 (2)	C27—O2—C52—C47	151.7 (1)
C1—O1—C26—C21	155.1 (1)	C27—O2—C52—C51	−88.0 (1)
C7—N1—C26—O1	16.7 (2)	C33—N2—C52—O2	22.3 (2)
C8—N1—C26—O1	168.2 (1)	C34—N2—C52—O2	168.5 (1)
C7—N1—C26—C25	137.7 (1)	C33—N2—C52—C47	−93.3 (1)
C8—N1—C26—C25	−70.8 (2)	C34—N2—C52—C47	52.9 (2)
C7—N1—C26—C21	−98.3 (2)	C33—N2—C52—C51	142.9 (1)
C8—N1—C26—C21	53.2 (2)	C34—N2—C52—C51	−70.9 (2)
C24—C25—C26—O1	−60.1 (2)	C48—C47—C52—O2	62.8 (1)
C24—C25—C26—N1	178.9 (1)	C40—C47—C52—O2	−172.8 (1)
C24—C25—C26—C21	56.0 (2)	C48—C47—C52—N2	−178.9 (1)
C22—C21—C26—O1	65.3 (2)	C40—C47—C52—N2	−54.4 (2)
C14—C21—C26—O1	−170.0 (1)	C48—C47—C52—C51	−55.9 (2)
C22—C21—C26—N1	−176.6 (1)	C40—C47—C52—C51	68.6 (2)
C14—C21—C26—N1	−51.9 (2)	C50—C51—C52—O2	−59.2 (2)
C22—C21—C26—C25	−53.9 (2)	C50—C51—C52—N2	179.9 (1)
C14—C21—C26—C25	70.8 (2)	C50—C51—C52—C47	57.2 (2)