8-(4-Methoxy­phenyl)-3,5-bis­[(E)-1-(4-methoxy­phenyl)­methyl­idene]-1,2,3,5,6,7-hexa­hydro­di­cyclo­penta­[b,e]­pyridine

At 150 K, the tricyclic core of the title compound, C₃₄H₃₁NO₃, is close to planar. One of the three 4-methoxy­phenyl substituents is twisted out of the plane of the tricyclic core due to steric congestion.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.055
• wR factor = 0.144
• Data-to-parameter ratio = 25.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99

   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
   0 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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: X-STEP32 (Stoe & Cie, 2001) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX.

8-(4-Methoxyphenyl)-3,5-bis[(E)-1-(4-methoxyphenyl)methylidene]- 1,2,3,5,6,7-hexahydrodicyclopenta[b,e]pyridine

Crystal data

C34H31NO3	Z = 2
Mr = 501.60	F(000) = 532
Triclinic, P1	Dx = 1.320 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8866 (7) Å	Cell parameters from 13469 reflections
b = 10.8186 (12) Å	θ = 2.0–32.3°
c = 20.898 (2) Å	µ = 0.08 mm^−1
α = 75.096 (9)°	T = 150 K
β = 85.572 (10)°	Needle, yellow
γ = 78.964 (10)°	0.60 × 0.20 × 0.20 mm
V = 1261.8 (2) Å^3

Data collection

Stoe IPDS-II area-detector diffractometer	4469 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
Graphite monochromator	θmax = 32.3°, θmin = 2.0°
ω scans	h = −7→8
27584 measured reflections	k = −16→16
8874 independent reflections	l = −31→31

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)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0619P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max = 0.001
8874 reflections	Δρmax = 0.33 e Å^−3
347 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (3)

Special details

Experimental. The crystal was mounted under the perfluoro-polyether PFO-XR75 (Lancaster Synthesis). A total of 320 frames (2 minute exposure) were collected (phi/omega: 25/20–160, 125/10–170, 175/160–180, delta-omega = 1 °.)

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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807).

Plane 1

Atom d s d/s (d/s)**2 N1 * 0.0126 0.0015 8.442 71.269 C1 * 0.0107 0.0017 6.232 38.833 C2 * -0.0310 0.0017 - 18.266 333.641 C3 * 0.0252 0.0017 15.257 232.783 C4 * -0.0014 0.0017 - 0.819 0.671 C5 * -0.0214 0.0017 - 12.448 154.964 C6 0.1347 0.0017 78.282 6128.098 C7 0.1294 0.0018 72.389 5240.132 C8 - 0.0841 0.0018 - 47.713 2276.567 C18 0.3010 0.0018 168.388 28354.436 C9 - 0.0565 0.0018 - 31.839 1013.737 C10 - 0.2595 0.0019 - 136.974 18761.881 C11 - 0.0250 0.0020 - 12.570 158.004 C25 0.1115 0.0018 61.450 3776.120 C12 0.1801 0.0017 108.859 11850.194 ============ Sum((d/s)**2) for starred atoms 832.160 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Plane 2

Atom d s d/s (d/s)**2 C12 * -0.0047 0.0016 - 2.857 8.161 C13 * 0.0026 0.0017 1.553 2.410 C14 * 0.0034 0.0017 2.023 4.093 C15 * -0.0070 0.0017 - 4.250 18.065 C16 * 0.0047 0.0016 2.846 8.097 C17 * 0.0012 0.0016 0.702 0.493 O1 - 0.0218 0.0012 - 17.528 307.235 C3 0.0639 0.0016 39.092 1528.187 ============ Sum((d/s)**2) for starred atoms 41.321 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Plane 3

Atom d s d/s (d/s)**2 C19 * 0.0011 0.0017 0.673 0.454 C20 * -0.0034 0.0018 - 1.911 3.650 C21 * 0.0029 0.0018 1.604 2.574 C22 * -0.0002 0.0017 - 0.120 0.014 C23 * -0.0019 0.0018 - 1.043 1.088 C24 * 0.0014 0.0018 0.770 0.593 O2 0.0097 0.0013 7.694 59.195 C18 0.0373 0.0018 20.914 437.377 ============ Sum((d/s)**2) for starred atoms 8.373 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Plane 4

Atom d s d/s (d/s)**2 C26 * -0.0092 0.0018 - 5.122 26.234 C27 * 0.0067 0.0020 3.344 11.185 C28 * 0.0067 0.0020 3.313 10.977 C29 * -0.0124 0.0018 - 6.827 46.610 C30 * 0.0098 0.0020 4.954 24.545 C31 * 0.0030 0.0020 1.545 2.388 O3 - 0.0561 0.0014 - 40.486 1639.150 C25 - 0.1045 0.0018 - 57.651 3323.681 ============ Sum((d/s)**2) for starred atoms 121.938 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Plane 5

Atom d s d/s (d/s)**2 N1 * -0.0006 0.0015 - 0.417 0.174 C1 * -0.0220 0.0017 - 12.764 162.921 C2 * -0.0389 0.0017 - 22.932 525.860 C3 * 0.0668 0.0017 40.436 1635.053 C4 * 0.0608 0.0017 34.809 1211.643 C5 * 0.0127 0.0017 7.365 54.241 C6 * 0.0506 0.0017 29.399 864.273 C7 * 0.0378 0.0018 21.133 446.609 C8 * -0.1261 0.0018 - 71.449 5104.913 C9 * 0.0070 0.0018 3.940 15.527 C10 * -0.1454 0.0019 - 76.749 5890.418 C11 * 0.0889 0.0020 44.621 1991.057 C18 0.1864 0.0018 104.125 10841.912 C25 0.1571 0.0018 86.511 7484.086 C12 0.2499 0.0017 151.265 22881.100 ============ Sum((d/s)**2) for starred atoms 17902.688 Chi-squared at 95% for 9 degrees of freedom: 16.90 The group of atoms deviates significantly from planarity

Plane 6

Atom d s d/s (d/s)**2 C1 * 0.0302 0.0017 17.666 312.077 C7 * 0.0049 0.0018 2.759 7.614 C6 * -0.0334 0.0017 - 19.501 380.289 C18 * -0.0345 0.0018 - 19.309 372.844 C19 * 0.0302 0.0017 17.679 312.548 ============ Sum((d/s)**2) for starred atoms 1385.373 Chi-squared at 95% for 2 degrees of freedom: 5.99 The group of atoms deviates significantly from planarity

Plane 7

Atom d s d/s (d/s)**2 C5 * -0.0140 0.0017 - 8.210 67.399 C9 * -0.0023 0.0018 - 1.328 1.764 C10 * 0.0066 0.0019 3.545 12.570 C25 * 0.0358 0.0018 19.778 391.158 C26 * -0.0232 0.0018 - 12.994 168.844 ============ Sum((d/s)**2) for starred atoms 641.734 Chi-squared at 95% for 2 degrees of freedom: 5.99 The group of atoms deviates significantly from planarity

Dihedral angles formed by LSQ-planes

Plane - plane angle (s.u.) angle (s.u.) 1 2 43.65 (0.05) 136.35 (0.05) 1 3 12.56 (0.05) 167.44 (0.05) 1 4 18.24 (0.05) 161.76 (0.05) 1 5 2.02 (0.04) 177.98 (0.04) 1 6 8.28 (0.05) 171.72 (0.05) 1 7 8.05 (0.05) 171.95 (0.05) 2 3 53.26 (0.05) 126.74 (0.05) 2 4 60.30 (0.06) 119.70 (0.06) 2 5 45.52 (0.04) 134.48 (0.04) 2 6 50.03 (0.06) 129.97 (0.06) 2 7 49.70 (0.06) 130.30 (0.06) 3 4 7.12 (0.06) 172.88 (0.06) 3 5 10.70 (0.04) 169.30 (0.04) 3 6 4.29 (0.05) 175.71 (0.05) 3 7 4.51 (0.05) 175.49 (0.05) 4 5 16.23 (0.04) 163.77 (0.04) 4 6 10.44 (0.06) 169.56 (0.06) 4 7 10.76 (0.07) 169.24 (0.07) 5 6 6.41 (0.04) 173.59 (0.04) 5 7 6.21 (0.04) 173.79 (0.04) 6 7 0.34 (0.07) 179.66 (0.07)

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
O1	0.7314 (2)	1.01598 (12)	0.23447 (6)	0.0319 (3)
O2	−0.1203 (2)	0.14767 (11)	−0.09353 (6)	0.0288 (3)
O3	−0.7949 (2)	0.11222 (12)	0.60361 (6)	0.0371 (3)
N1	0.0200 (3)	0.38806 (13)	0.25660 (7)	0.0259 (3)
C1	0.1620 (3)	0.43140 (15)	0.20572 (8)	0.0237 (3)
C2	0.3031 (3)	0.52305 (15)	0.20334 (8)	0.0233 (3)
C3	0.2900 (3)	0.58466 (14)	0.25541 (8)	0.0233 (3)
C4	0.1463 (3)	0.53824 (15)	0.30935 (8)	0.0254 (3)
C5	0.0203 (3)	0.44155 (15)	0.30790 (8)	0.0247 (3)
C6	0.1780 (3)	0.39250 (15)	0.14231 (8)	0.0239 (3)
C7	0.3504 (3)	0.46440 (16)	0.09759 (8)	0.0265 (3)
H7A	0.2738	0.5241	0.0579	0.032*
H7B	0.4776	0.4024	0.0831	0.032*
C8	0.4456 (3)	0.54194 (16)	0.13940 (8)	0.0255 (3)
H8A	0.6117	0.5078	0.1481	0.031*
H8B	0.4270	0.6352	0.1161	0.031*
C9	−0.1173 (3)	0.40760 (15)	0.37004 (8)	0.0261 (3)
C10	−0.0436 (3)	0.47758 (16)	0.41707 (8)	0.0295 (4)
H10A	0.0510	0.4152	0.4526	0.035*
H10B	−0.1808	0.5229	0.4376	0.035*
C11	0.0998 (4)	0.57619 (17)	0.37476 (8)	0.0340 (4)
H11A	0.0117	0.6660	0.3680	0.041*
H11B	0.2467	0.5705	0.3963	0.041*
C12	0.4092 (3)	0.69600 (14)	0.25195 (8)	0.0229 (3)
C13	0.6333 (3)	0.69971 (16)	0.22592 (8)	0.0255 (3)
H13	0.7175	0.6269	0.2117	0.031*
C14	0.7363 (3)	0.80699 (16)	0.22028 (8)	0.0266 (3)
H14	0.8893	0.8074	0.2022	0.032*
C15	0.6153 (3)	0.91455 (15)	0.24111 (8)	0.0252 (3)
C16	0.3906 (3)	0.91426 (15)	0.26637 (8)	0.0253 (3)
H16	0.3061	0.9878	0.2799	0.030*
C17	0.2898 (3)	0.80583 (15)	0.27184 (8)	0.0245 (3)
H17	0.1362	0.8060	0.2895	0.029*
C18	0.0445 (3)	0.31384 (16)	0.13100 (8)	0.0264 (3)
H18	−0.0467	0.2791	0.1684	0.032*
C19	0.0120 (3)	0.27094 (15)	0.07160 (8)	0.0247 (3)
C20	−0.1558 (3)	0.19454 (16)	0.07515 (8)	0.0279 (4)
H20	−0.2390	0.1709	0.1159	0.033*
C21	−0.2071 (3)	0.15130 (16)	0.02190 (8)	0.0280 (4)
H21	−0.3242	0.1000	0.0262	0.034*
C22	−0.0851 (3)	0.18395 (15)	−0.03786 (8)	0.0244 (3)
C23	0.0850 (3)	0.25993 (16)	−0.04293 (8)	0.0270 (4)
H23	0.1690	0.2824	−0.0836	0.032*
C24	0.1330 (3)	0.30310 (16)	0.01062 (8)	0.0262 (3)
H24	0.2492	0.3551	0.0061	0.031*
C25	−0.2776 (3)	0.33193 (16)	0.37777 (8)	0.0274 (4)
H25	−0.3039	0.3060	0.3393	0.033*
C26	−0.4191 (3)	0.28281 (16)	0.43637 (8)	0.0267 (3)
C27	−0.5851 (3)	0.21051 (18)	0.43041 (9)	0.0329 (4)
H27	−0.6098	0.2000	0.3879	0.039*
C28	−0.7155 (3)	0.15340 (18)	0.48404 (9)	0.0343 (4)
H28	−0.8273	0.1050	0.4780	0.041*
C29	−0.6818 (3)	0.16739 (16)	0.54668 (8)	0.0292 (4)
C30	−0.5228 (4)	0.24175 (17)	0.55399 (9)	0.0330 (4)
H30	−0.5028	0.2544	0.5964	0.040*
C31	−0.3927 (3)	0.29779 (17)	0.50004 (9)	0.0317 (4)
H31	−0.2832	0.3475	0.5062	0.038*
C32	0.6106 (4)	1.12520 (18)	0.25725 (10)	0.0403 (5)
H32A	0.5579	1.0959	0.3034	0.048*
H32B	0.4766	1.1673	0.2296	0.048*
H32C	0.7146	1.1873	0.2544	0.048*
C33	−0.2935 (3)	0.06996 (17)	−0.08976 (9)	0.0305 (4)
H33A	−0.4441	0.1178	−0.0788	0.037*
H33B	−0.2548	−0.0109	−0.0553	0.037*
H33C	−0.3006	0.0496	−0.1325	0.037*
C34	−0.9445 (4)	0.02613 (19)	0.59883 (11)	0.0382 (4)
H34C	−0.9987	−0.0152	0.6433	0.046*
H34B	−0.8601	−0.0408	0.5776	0.046*
H34A	−1.0777	0.0752	0.5723	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0409 (7)	0.0314 (6)	0.0303 (6)	−0.0187 (5)	0.0064 (5)	−0.0132 (5)
O2	0.0367 (7)	0.0322 (6)	0.0226 (6)	−0.0117 (5)	0.0003 (5)	−0.0118 (5)
O3	0.0442 (8)	0.0362 (7)	0.0328 (7)	−0.0168 (6)	0.0095 (6)	−0.0081 (5)
N1	0.0340 (8)	0.0229 (6)	0.0240 (7)	−0.0076 (6)	0.0021 (6)	−0.0104 (5)
C1	0.0290 (9)	0.0214 (7)	0.0229 (7)	−0.0040 (6)	0.0001 (6)	−0.0100 (6)
C2	0.0255 (8)	0.0217 (7)	0.0235 (7)	−0.0030 (6)	0.0002 (6)	−0.0082 (6)
C3	0.0274 (8)	0.0204 (7)	0.0236 (7)	−0.0046 (6)	−0.0015 (6)	−0.0076 (6)
C4	0.0324 (9)	0.0231 (7)	0.0226 (7)	−0.0061 (7)	0.0002 (7)	−0.0086 (6)
C5	0.0300 (9)	0.0230 (7)	0.0230 (7)	−0.0053 (6)	−0.0002 (6)	−0.0088 (6)
C6	0.0286 (8)	0.0213 (7)	0.0231 (7)	−0.0036 (6)	0.0021 (6)	−0.0094 (6)
C7	0.0303 (9)	0.0256 (7)	0.0265 (8)	−0.0061 (7)	0.0020 (7)	−0.0117 (6)
C8	0.0272 (8)	0.0263 (7)	0.0258 (8)	−0.0073 (6)	0.0028 (7)	−0.0107 (6)
C9	0.0351 (9)	0.0224 (7)	0.0224 (7)	−0.0063 (7)	0.0012 (7)	−0.0082 (6)
C10	0.0432 (11)	0.0270 (8)	0.0220 (8)	−0.0122 (7)	0.0039 (7)	−0.0099 (6)
C11	0.0516 (12)	0.0332 (9)	0.0255 (8)	−0.0207 (8)	0.0072 (8)	−0.0151 (7)
C12	0.0277 (8)	0.0219 (7)	0.0211 (7)	−0.0063 (6)	−0.0013 (6)	−0.0078 (6)
C13	0.0272 (8)	0.0267 (7)	0.0247 (8)	−0.0022 (6)	−0.0026 (6)	−0.0115 (6)
C14	0.0246 (8)	0.0342 (8)	0.0237 (8)	−0.0097 (7)	0.0020 (6)	−0.0095 (6)
C15	0.0325 (9)	0.0265 (7)	0.0205 (7)	−0.0127 (7)	−0.0005 (6)	−0.0074 (6)
C16	0.0312 (9)	0.0239 (7)	0.0234 (7)	−0.0071 (6)	0.0017 (7)	−0.0095 (6)
C17	0.0275 (8)	0.0258 (7)	0.0228 (7)	−0.0073 (6)	0.0024 (6)	−0.0095 (6)
C18	0.0329 (9)	0.0271 (7)	0.0224 (7)	−0.0083 (7)	0.0050 (7)	−0.0110 (6)
C19	0.0294 (9)	0.0227 (7)	0.0251 (8)	−0.0064 (6)	0.0017 (7)	−0.0107 (6)
C20	0.0335 (9)	0.0296 (8)	0.0233 (8)	−0.0111 (7)	0.0058 (7)	−0.0095 (6)
C21	0.0286 (9)	0.0295 (8)	0.0301 (8)	−0.0114 (7)	0.0040 (7)	−0.0118 (7)
C22	0.0275 (8)	0.0231 (7)	0.0247 (8)	−0.0034 (6)	−0.0009 (6)	−0.0103 (6)
C23	0.0309 (9)	0.0289 (8)	0.0232 (8)	−0.0072 (7)	0.0041 (7)	−0.0100 (6)
C24	0.0280 (9)	0.0272 (8)	0.0274 (8)	−0.0094 (7)	0.0033 (7)	−0.0117 (6)
C25	0.0343 (9)	0.0289 (8)	0.0225 (8)	−0.0078 (7)	0.0022 (7)	−0.0117 (6)
C26	0.0308 (9)	0.0248 (7)	0.0262 (8)	−0.0054 (7)	0.0011 (7)	−0.0096 (6)
C27	0.0364 (10)	0.0390 (9)	0.0299 (9)	−0.0124 (8)	0.0024 (8)	−0.0173 (7)
C28	0.0356 (10)	0.0370 (9)	0.0375 (10)	−0.0161 (8)	0.0050 (8)	−0.0168 (8)
C29	0.0331 (9)	0.0255 (8)	0.0283 (8)	−0.0059 (7)	0.0059 (7)	−0.0071 (6)
C30	0.0452 (11)	0.0344 (9)	0.0224 (8)	−0.0130 (8)	0.0015 (8)	−0.0086 (7)
C31	0.0405 (10)	0.0314 (8)	0.0285 (8)	−0.0162 (8)	0.0007 (8)	−0.0100 (7)
C32	0.0589 (14)	0.0329 (9)	0.0372 (10)	−0.0218 (9)	0.0122 (9)	−0.0170 (8)
C33	0.0361 (10)	0.0301 (8)	0.0297 (9)	−0.0098 (7)	−0.0053 (7)	−0.0110 (7)
C34	0.0350 (10)	0.0338 (9)	0.0465 (11)	−0.0124 (8)	0.0105 (9)	−0.0101 (8)

Geometric parameters (Å, º)

O1—C15	1.373 (2)	C15—C16	1.386 (2)
O1—C32	1.430 (2)	C16—C17	1.389 (2)
O2—C22	1.3617 (19)	C16—H16	0.9500
O2—C33	1.426 (2)	C17—H17	0.9500
O3—C29	1.371 (2)	C18—C19	1.470 (2)
O3—C34	1.425 (2)	C18—H18	0.9500
N1—C5	1.343 (2)	C19—C20	1.391 (2)
N1—C1	1.344 (2)	C19—C24	1.407 (2)
C1—C2	1.400 (2)	C20—C21	1.386 (2)
C1—C6	1.481 (2)	C20—H20	0.9500
C2—C3	1.405 (2)	C21—C22	1.390 (2)
C2—C8	1.511 (2)	C21—H21	0.9500
C3—C4	1.401 (2)	C22—C23	1.394 (2)
C3—C12	1.490 (2)	C23—C24	1.385 (2)
C4—C5	1.401 (2)	C23—H23	0.9500
C4—C11	1.517 (2)	C24—H24	0.9500
C5—C9	1.478 (2)	C25—C26	1.467 (2)
C6—C18	1.336 (2)	C25—H25	0.9500
C6—C7	1.513 (2)	C26—C27	1.394 (3)
C7—C8	1.554 (2)	C26—C31	1.405 (2)
C7—H7A	0.9900	C27—C28	1.385 (3)
C7—H7B	0.9900	C27—H27	0.9500
C8—H8A	0.9900	C28—C29	1.389 (3)
C8—H8B	0.9900	C28—H28	0.9500
C9—C25	1.339 (3)	C29—C30	1.386 (3)
C9—C10	1.517 (2)	C30—C31	1.385 (3)
C10—C11	1.541 (3)	C30—H30	0.9500
C10—H10A	0.9900	C31—H31	0.9500
C10—H10B	0.9900	C32—H32A	0.9800
C11—H11A	0.9900	C32—H32B	0.9800
C11—H11B	0.9900	C32—H32C	0.9800
C12—C13	1.391 (2)	C33—H33A	0.9800
C12—C17	1.403 (2)	C33—H33B	0.9800
C13—C14	1.384 (2)	C33—H33C	0.9800
C13—H13	0.9500	C34—H34C	0.9800
C14—C15	1.395 (2)	C34—H34B	0.9800
C14—H14	0.9500	C34—H34A	0.9800
C15—O1—C32	116.47 (14)	C16—C17—C12	121.65 (16)
C22—O2—C33	117.41 (13)	C16—C17—H17	119.2
C29—O3—C34	117.35 (15)	C12—C17—H17	119.2
C5—N1—C1	114.00 (14)	C6—C18—C19	132.16 (15)
N1—C1—C2	125.69 (14)	C6—C18—H18	113.9
N1—C1—C6	123.32 (15)	C19—C18—H18	113.9
C2—C1—C6	110.91 (14)	C20—C19—C24	116.90 (14)
C1—C2—C3	119.65 (15)	C20—C19—C18	117.61 (14)
C1—C2—C8	110.07 (13)	C24—C19—C18	125.47 (15)
C3—C2—C8	130.25 (15)	C21—C20—C19	122.99 (15)
C4—C3—C2	114.97 (14)	C21—C20—H20	118.5
C4—C3—C12	122.40 (13)	C19—C20—H20	118.5
C2—C3—C12	122.54 (14)	C20—C21—C22	119.16 (16)
C5—C4—C3	120.56 (14)	C20—C21—H21	120.4
C5—C4—C11	109.81 (15)	C22—C21—H21	120.4
C3—C4—C11	129.63 (15)	O2—C22—C21	124.53 (15)
N1—C5—C4	124.88 (15)	O2—C22—C23	116.22 (14)
N1—C5—C9	124.14 (15)	C21—C22—C23	119.25 (15)
C4—C5—C9	110.97 (13)	C24—C23—C22	120.86 (15)
C18—C6—C1	121.67 (15)	C24—C23—H23	119.6
C18—C6—C7	130.96 (14)	C22—C23—H23	119.6
C1—C6—C7	107.23 (14)	C23—C24—C19	120.84 (16)
C6—C7—C8	106.11 (13)	C23—C24—H24	119.6
C6—C7—H7A	110.5	C19—C24—H24	119.6
C8—C7—H7A	110.5	C9—C25—C26	130.15 (15)
C6—C7—H7B	110.5	C9—C25—H25	114.9
C8—C7—H7B	110.5	C26—C25—H25	114.9
H7A—C7—H7B	108.7	C27—C26—C31	116.47 (16)
C2—C8—C7	105.14 (13)	C27—C26—C25	118.87 (15)
C2—C8—H8A	110.7	C31—C26—C25	124.59 (16)
C7—C8—H8A	110.7	C28—C27—C26	122.62 (16)
C2—C8—H8B	110.7	C28—C27—H27	118.7
C7—C8—H8B	110.7	C26—C27—H27	118.7
H8A—C8—H8B	108.8	C27—C28—C29	119.61 (17)
C25—C9—C5	122.91 (14)	C27—C28—H28	120.2
C25—C9—C10	130.43 (15)	C29—C28—H28	120.2
C5—C9—C10	106.62 (14)	O3—C29—C30	115.90 (15)
C9—C10—C11	106.07 (13)	O3—C29—C28	124.90 (17)
C9—C10—H10A	110.5	C30—C29—C28	119.20 (16)
C11—C10—H10A	110.5	C31—C30—C29	120.59 (16)
C9—C10—H10B	110.5	C31—C30—H30	119.7
C11—C10—H10B	110.5	C29—C30—H30	119.7
H10A—C10—H10B	108.7	C30—C31—C26	121.47 (17)
C4—C11—C10	104.92 (13)	C30—C31—H31	119.3
C4—C11—H11A	110.8	C26—C31—H31	119.3
C10—C11—H11A	110.8	O1—C32—H32A	109.5
C4—C11—H11B	110.8	O1—C32—H32B	109.5
C10—C11—H11B	110.8	H32A—C32—H32B	109.5
H11A—C11—H11B	108.8	O1—C32—H32C	109.5
C13—C12—C17	117.49 (15)	H32A—C32—H32C	109.5
C13—C12—C3	122.59 (13)	H32B—C32—H32C	109.5
C17—C12—C3	119.82 (15)	O2—C33—H33A	109.5
C14—C13—C12	121.52 (14)	O2—C33—H33B	109.5
C14—C13—H13	119.2	H33A—C33—H33B	109.5
C12—C13—H13	119.2	O2—C33—H33C	109.5
C13—C14—C15	120.01 (16)	H33A—C33—H33C	109.5
C13—C14—H14	120.0	H33B—C33—H33C	109.5
C15—C14—H14	120.0	O3—C34—H34C	109.5
O1—C15—C16	124.14 (14)	O3—C34—H34B	109.5
O1—C15—C14	116.16 (15)	H34C—C34—H34B	109.5
C16—C15—C14	119.70 (15)	O3—C34—H34A	109.5
C15—C16—C17	119.61 (14)	H34C—C34—H34A	109.5
C15—C16—H16	120.2	H34B—C34—H34A	109.5
C17—C16—H16	120.2
C5—N1—C1—C2	0.4 (2)	C3—C12—C13—C14	176.82 (15)
C5—N1—C1—C6	−175.83 (15)	C12—C13—C14—C15	0.2 (2)
N1—C1—C2—C3	−4.7 (3)	C32—O1—C15—C16	1.9 (2)
C6—C1—C2—C3	171.90 (15)	C32—O1—C15—C14	−178.49 (16)
N1—C1—C2—C8	177.35 (16)	C13—C14—C15—O1	179.24 (15)
C6—C1—C2—C8	−6.01 (19)	C13—C14—C15—C16	−1.1 (2)
C1—C2—C3—C4	5.5 (2)	O1—C15—C16—C17	−179.14 (15)
C8—C2—C3—C4	−177.02 (16)	C14—C15—C16—C17	1.2 (2)
C1—C2—C3—C12	−171.11 (15)	C15—C16—C17—C12	−0.5 (2)
C8—C2—C3—C12	6.3 (3)	C13—C12—C17—C16	−0.4 (2)
C2—C3—C4—C5	−2.7 (2)	C3—C12—C17—C16	−176.80 (15)
C12—C3—C4—C5	173.92 (15)	C1—C6—C18—C19	173.69 (17)
C2—C3—C4—C11	176.71 (18)	C7—C6—C18—C19	−1.6 (3)
C12—C3—C4—C11	−6.6 (3)	C6—C18—C19—C20	−175.42 (18)
C1—N1—C5—C4	2.7 (2)	C6—C18—C19—C24	3.0 (3)
C1—N1—C5—C9	−178.60 (16)	C24—C19—C20—C21	−0.5 (3)
C3—C4—C5—N1	−1.6 (3)	C18—C19—C20—C21	178.07 (16)
C11—C4—C5—N1	178.90 (17)	C19—C20—C21—C22	0.7 (3)
C3—C4—C5—C9	179.64 (15)	C33—O2—C22—C21	−0.5 (2)
C11—C4—C5—C9	0.1 (2)	C33—O2—C22—C23	−179.95 (15)
N1—C1—C6—C18	2.2 (3)	C20—C21—C22—O2	−179.78 (16)
C2—C1—C6—C18	−174.55 (16)	C20—C21—C22—C23	−0.4 (3)
N1—C1—C6—C7	178.44 (15)	O2—C22—C23—C24	179.38 (15)
C2—C1—C6—C7	1.71 (19)	C21—C22—C23—C24	−0.1 (2)
C18—C6—C7—C8	178.86 (17)	C22—C23—C24—C19	0.2 (3)
C1—C6—C7—C8	3.07 (18)	C20—C19—C24—C23	0.0 (2)
C1—C2—C8—C7	7.66 (18)	C18—C19—C24—C23	−178.42 (16)
C3—C2—C8—C7	−169.97 (17)	C5—C9—C25—C26	176.12 (17)
C6—C7—C8—C2	−6.35 (17)	C10—C9—C25—C26	−6.2 (3)
N1—C5—C9—C25	−8.7 (3)	C9—C25—C26—C27	176.47 (18)
C4—C5—C9—C25	170.16 (17)	C9—C25—C26—C31	−6.8 (3)
N1—C5—C9—C10	173.21 (16)	C31—C26—C27—C28	−1.3 (3)
C4—C5—C9—C10	−7.97 (19)	C25—C26—C27—C28	175.69 (17)
C25—C9—C10—C11	−165.60 (19)	C26—C27—C28—C29	−0.1 (3)
C5—C9—C10—C11	12.34 (19)	C34—O3—C29—C30	−174.69 (16)
C5—C4—C11—C10	7.6 (2)	C34—O3—C29—C28	5.1 (3)
C3—C4—C11—C10	−171.86 (18)	C27—C28—C29—O3	−177.87 (17)
C9—C10—C11—C4	−12.1 (2)	C27—C28—C29—C30	1.9 (3)
C4—C3—C12—C13	141.69 (17)	O3—C29—C30—C31	177.54 (17)
C2—C3—C12—C13	−41.9 (2)	C28—C29—C30—C31	−2.3 (3)
C4—C3—C12—C17	−42.1 (2)	C29—C30—C31—C26	0.8 (3)
C2—C3—C12—C17	134.26 (17)	C27—C26—C31—C30	0.9 (3)
C17—C12—C13—C14	0.6 (2)	C25—C26—C31—C30	−175.85 (17)