5-[(E)-2-(4-Methoxy­carbonyl­phen­yl)ethen­yl]-1,1,3,3-tetra­methyl­isoindolin-2-ylox­yl

The asymmetric unit of the title compound, C₂₂H₂₄NO₃, comprises two mol­ecules with an E stereochemical configuration at the ethyl­ene groups.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.042
• wR factor = 0.114
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and WinGX32 (Farrugia, 1999); software used to prepare material for publication: enCIFer (Allen et al., 2004).

5-[(E)-2-(4-Methoxycarbonylphenyl)ethenyl]-1,1,3,3-tetramethylisoindolin- 2-yloxyl

Crystal data

C22H24NO3	F(000) = 1496
Mr = 350.42	Dx = 1.222 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11050 reflections
a = 11.6300 (19) Å	θ = 2.4–28.1°
b = 13.432 (2) Å	µ = 0.08 mm^−1
c = 24.407 (4) Å	T = 150 K
β = 91.976 (3)°	Prism, orange
V = 3810.5 (11) Å^3	0.41 × 0.37 × 0.19 mm
Z = 8

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	9218 independent reflections
Radiation source: sealed tube	7037 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −15→15
Tmin = 0.91, Tmax = 0.99	k = −17→17
37652 measured reflections	l = −31→31

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 0.9099P] where P = (Fo^2 + 2Fc^2)/3
9218 reflections	(Δ/σ)max < 0.001
479 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.23 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
C1	0.74238 (13)	0.12505 (10)	0.01326 (6)	0.0394 (3)
H1A	0.7086	0.0798	0.0398	0.059*
H1B	0.8264	0.1193	0.0157	0.059*
H1C	0.7146	0.1074	−0.0238	0.059*
C2	0.60044 (11)	0.24054 (9)	0.04040 (5)	0.0253 (3)
C3	0.57677 (10)	0.34646 (8)	0.05318 (5)	0.0234 (2)
C4	0.65291 (10)	0.42168 (9)	0.03975 (5)	0.0259 (3)
H4	0.7221	0.4058	0.0221	0.031*
C5	0.62778 (11)	0.51969 (9)	0.05206 (5)	0.0264 (3)
H5	0.6797	0.5707	0.0422	0.032*
C6	0.52751 (10)	0.54518 (9)	0.07876 (5)	0.0233 (2)
C7	0.45158 (10)	0.46872 (9)	0.09206 (5)	0.0259 (3)
H7	0.3829	0.4842	0.1103	0.031*
C8	0.47530 (11)	0.37104 (9)	0.07902 (5)	0.0262 (3)
H8	0.4222	0.3201	0.0877	0.031*
C9	0.50773 (11)	0.64986 (9)	0.09150 (5)	0.0261 (3)
H9	0.5530	0.6970	0.0728	0.031*
C10	0.43308 (11)	0.68659 (9)	0.12646 (5)	0.0268 (3)
H10	0.3871	0.6404	0.1455	0.032*
C11	0.41639 (10)	0.79283 (9)	0.13784 (5)	0.0249 (2)
C12	0.45656 (11)	0.86724 (9)	0.10279 (5)	0.0271 (3)
H12	0.4961	0.8484	0.0710	0.032*
C13	0.43990 (11)	0.96711 (9)	0.11353 (5)	0.0264 (3)
H13	0.4671	1.0166	0.0894	0.032*
C14	0.38257 (10)	0.99384 (8)	0.16044 (5)	0.0228 (2)
C15	0.34330 (10)	0.92137 (9)	0.19593 (5)	0.0222 (2)
C16	0.35867 (10)	0.82133 (9)	0.18466 (5)	0.0248 (2)
H16	0.3301	0.7722	0.2087	0.030*
C17	0.35312 (10)	1.09736 (9)	0.17893 (5)	0.0252 (3)
C18	0.28657 (10)	0.96697 (9)	0.24446 (5)	0.0233 (2)
C19	0.45937 (11)	1.15927 (10)	0.19520 (6)	0.0344 (3)
H19A	0.4352	1.2217	0.2121	0.052*
H19B	0.5029	1.1740	0.1625	0.052*
H19C	0.5081	1.1217	0.2214	0.052*
C20	0.27628 (12)	1.15185 (10)	0.13674 (6)	0.0350 (3)
H20A	0.2077	1.1116	0.1281	0.052*
H20B	0.3188	1.1628	0.1033	0.052*
H20C	0.2530	1.2162	0.1517	0.052*
C21	0.35830 (12)	0.95505 (11)	0.29766 (5)	0.0340 (3)
H21A	0.4363	0.9801	0.2924	0.051*
H21B	0.3619	0.8845	0.3078	0.051*
H21C	0.3227	0.9929	0.3269	0.051*
C22	0.16318 (10)	0.93211 (10)	0.25168 (5)	0.0294 (3)
H22A	0.1270	0.9735	0.2793	0.044*
H22B	0.1635	0.8625	0.2637	0.044*
H22C	0.1198	0.9379	0.2167	0.044*
C23	0.24493 (13)	0.16217 (11)	−0.01483 (7)	0.0428 (4)
H23A	0.2141	0.1069	0.0064	0.064*
H23B	0.3292	0.1591	−0.0134	0.064*
H23C	0.2166	0.1572	−0.0530	0.064*
C24	0.10243 (11)	0.25675 (9)	0.02896 (5)	0.0273 (3)
C25	0.07198 (10)	0.35591 (9)	0.05109 (5)	0.0251 (2)
C26	0.14768 (11)	0.43643 (9)	0.05096 (5)	0.0282 (3)
H26	0.2220	0.4284	0.0366	0.034*
C27	0.11552 (11)	0.52776 (9)	0.07154 (5)	0.0297 (3)
H27	0.1679	0.5820	0.0710	0.036*
C28	0.00655 (11)	0.54129 (9)	0.09313 (5)	0.0264 (3)
C29	−0.06735 (11)	0.45933 (10)	0.09407 (5)	0.0296 (3)
H29	−0.1408	0.4664	0.1095	0.036*
C30	−0.03586 (11)	0.36821 (9)	0.07311 (5)	0.0293 (3)
H30	−0.0880	0.3138	0.0737	0.035*
C31	−0.03247 (11)	0.63669 (9)	0.11476 (5)	0.0288 (3)
H31	−0.0976	0.6350	0.1372	0.035*
C32	0.01421 (11)	0.72544 (9)	0.10610 (5)	0.0301 (3)
H32	0.0794	0.7276	0.0837	0.036*
C33	−0.02650 (11)	0.82043 (9)	0.12817 (5)	0.0271 (3)
C34	0.00864 (11)	0.91006 (10)	0.10448 (5)	0.0308 (3)
H34	0.0593	0.9081	0.0748	0.037*
C35	−0.02868 (11)	1.00158 (9)	0.12331 (5)	0.0293 (3)
H35	−0.0049	1.0615	0.1064	0.035*
C36	−0.10130 (10)	1.00399 (9)	0.16718 (5)	0.0245 (2)
C37	−0.13699 (10)	0.91561 (9)	0.19101 (5)	0.0226 (2)
C38	−0.10091 (10)	0.82427 (9)	0.17215 (5)	0.0248 (2)
H38	−0.1262	0.7646	0.1888	0.030*
C39	−0.14744 (11)	1.09361 (9)	0.19647 (5)	0.0271 (3)
C40	−0.21380 (10)	0.93370 (9)	0.23844 (5)	0.0252 (3)
C41	−0.05240 (12)	1.15668 (10)	0.22393 (7)	0.0410 (3)
H41A	−0.0866	1.2044	0.2490	0.061*
H41B	−0.0109	1.1928	0.1958	0.061*
H41C	0.0012	1.1133	0.2446	0.061*
C42	−0.22777 (12)	1.15779 (10)	0.16052 (6)	0.0365 (3)
H42A	−0.2878	1.1158	0.1434	0.055*
H42B	−0.1837	1.1901	0.1320	0.055*
H42C	−0.2635	1.2087	0.1831	0.055*
C43	−0.16226 (12)	0.89458 (10)	0.29258 (5)	0.0343 (3)
H43A	−0.0851	0.9225	0.2988	0.051*
H43B	−0.1573	0.8218	0.2911	0.051*
H43C	−0.2113	0.9143	0.3226	0.051*
C44	−0.33550 (11)	0.89411 (10)	0.22772 (6)	0.0353 (3)
H44A	−0.3836	0.9121	0.2584	0.053*
H44B	−0.3331	0.8215	0.2241	0.053*
H44C	−0.3680	0.9233	0.1938	0.053*
N1	0.28650 (9)	1.07339 (7)	0.22797 (4)	0.0275 (2)
N2	−0.21517 (10)	1.04383 (8)	0.23898 (5)	0.0326 (3)
O1	0.70928 (8)	0.22629 (6)	0.02532 (4)	0.0329 (2)
O2	0.53100 (8)	0.17422 (6)	0.04366 (4)	0.0351 (2)
O3	0.24384 (8)	1.14092 (7)	0.25790 (4)	0.0365 (2)
O4	0.20795 (8)	0.25552 (7)	0.00813 (4)	0.0343 (2)
O5	0.04020 (8)	0.18485 (7)	0.02971 (4)	0.0367 (2)
O6	−0.27231 (10)	1.09305 (7)	0.27333 (4)	0.0453 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0393 (8)	0.0309 (7)	0.0478 (9)	0.0113 (6)	0.0009 (6)	−0.0128 (6)
C2	0.0286 (6)	0.0244 (6)	0.0229 (6)	0.0012 (5)	0.0010 (5)	−0.0003 (5)
C3	0.0268 (6)	0.0219 (5)	0.0213 (6)	0.0017 (5)	−0.0009 (5)	−0.0001 (4)
C4	0.0259 (6)	0.0267 (6)	0.0255 (6)	0.0013 (5)	0.0055 (5)	−0.0018 (5)
C5	0.0297 (6)	0.0240 (6)	0.0259 (6)	−0.0030 (5)	0.0059 (5)	0.0002 (5)
C6	0.0275 (6)	0.0223 (6)	0.0200 (6)	0.0018 (5)	0.0004 (5)	0.0002 (4)
C7	0.0246 (6)	0.0254 (6)	0.0276 (6)	0.0019 (5)	0.0034 (5)	−0.0007 (5)
C8	0.0264 (6)	0.0238 (6)	0.0283 (6)	−0.0022 (5)	0.0018 (5)	0.0009 (5)
C9	0.0314 (6)	0.0204 (6)	0.0265 (6)	−0.0008 (5)	0.0030 (5)	0.0007 (5)
C10	0.0331 (7)	0.0219 (6)	0.0255 (6)	−0.0005 (5)	0.0037 (5)	0.0002 (5)
C11	0.0293 (6)	0.0212 (6)	0.0242 (6)	0.0006 (5)	0.0012 (5)	−0.0013 (5)
C12	0.0318 (7)	0.0268 (6)	0.0229 (6)	0.0008 (5)	0.0061 (5)	−0.0013 (5)
C13	0.0306 (6)	0.0232 (6)	0.0255 (6)	−0.0009 (5)	0.0044 (5)	0.0019 (5)
C14	0.0224 (6)	0.0212 (5)	0.0248 (6)	0.0001 (4)	−0.0001 (5)	−0.0012 (4)
C15	0.0216 (6)	0.0243 (6)	0.0207 (5)	0.0014 (4)	0.0003 (4)	−0.0015 (4)
C16	0.0280 (6)	0.0224 (6)	0.0242 (6)	0.0000 (5)	0.0029 (5)	0.0011 (4)
C17	0.0247 (6)	0.0209 (6)	0.0304 (6)	0.0004 (5)	0.0056 (5)	−0.0013 (5)
C18	0.0232 (6)	0.0225 (6)	0.0242 (6)	0.0013 (4)	0.0023 (5)	−0.0015 (4)
C19	0.0310 (7)	0.0280 (6)	0.0446 (8)	−0.0063 (5)	0.0082 (6)	−0.0092 (6)
C20	0.0356 (7)	0.0284 (6)	0.0411 (8)	0.0058 (5)	0.0035 (6)	0.0051 (6)
C21	0.0320 (7)	0.0460 (8)	0.0239 (6)	0.0055 (6)	−0.0002 (5)	−0.0043 (6)
C22	0.0254 (6)	0.0294 (6)	0.0337 (7)	−0.0009 (5)	0.0047 (5)	−0.0004 (5)
C23	0.0375 (8)	0.0380 (8)	0.0531 (9)	0.0079 (6)	0.0037 (7)	−0.0147 (7)
C24	0.0284 (6)	0.0292 (6)	0.0241 (6)	0.0009 (5)	−0.0005 (5)	0.0014 (5)
C25	0.0274 (6)	0.0266 (6)	0.0211 (6)	0.0002 (5)	0.0007 (5)	0.0012 (5)
C26	0.0261 (6)	0.0298 (6)	0.0291 (6)	−0.0009 (5)	0.0063 (5)	−0.0014 (5)
C27	0.0294 (6)	0.0285 (6)	0.0317 (7)	−0.0046 (5)	0.0062 (5)	−0.0019 (5)
C28	0.0292 (6)	0.0278 (6)	0.0223 (6)	0.0016 (5)	0.0016 (5)	−0.0012 (5)
C29	0.0240 (6)	0.0351 (7)	0.0300 (7)	−0.0001 (5)	0.0048 (5)	−0.0026 (5)
C30	0.0281 (6)	0.0294 (6)	0.0305 (7)	−0.0054 (5)	0.0031 (5)	−0.0004 (5)
C31	0.0275 (6)	0.0328 (7)	0.0263 (6)	0.0024 (5)	0.0040 (5)	−0.0040 (5)
C32	0.0335 (7)	0.0315 (7)	0.0258 (6)	0.0030 (5)	0.0074 (5)	−0.0022 (5)
C33	0.0277 (6)	0.0282 (6)	0.0253 (6)	0.0003 (5)	0.0022 (5)	−0.0015 (5)
C34	0.0315 (7)	0.0350 (7)	0.0265 (6)	−0.0027 (5)	0.0078 (5)	0.0006 (5)
C35	0.0294 (6)	0.0282 (6)	0.0305 (7)	−0.0043 (5)	0.0033 (5)	0.0045 (5)
C36	0.0232 (6)	0.0229 (6)	0.0274 (6)	−0.0011 (5)	−0.0014 (5)	0.0009 (5)
C37	0.0215 (6)	0.0239 (6)	0.0223 (6)	0.0002 (4)	−0.0004 (4)	0.0008 (4)
C38	0.0264 (6)	0.0236 (6)	0.0245 (6)	−0.0014 (5)	0.0017 (5)	0.0015 (5)
C39	0.0264 (6)	0.0218 (6)	0.0332 (7)	0.0002 (5)	0.0009 (5)	0.0009 (5)
C40	0.0267 (6)	0.0216 (6)	0.0275 (6)	0.0026 (5)	0.0047 (5)	−0.0001 (5)
C41	0.0359 (8)	0.0280 (7)	0.0584 (10)	0.0003 (6)	−0.0083 (7)	−0.0099 (6)
C42	0.0338 (7)	0.0311 (7)	0.0445 (8)	0.0055 (6)	−0.0014 (6)	0.0066 (6)
C43	0.0410 (8)	0.0360 (7)	0.0260 (7)	0.0061 (6)	0.0050 (6)	0.0022 (5)
C44	0.0253 (6)	0.0365 (7)	0.0445 (8)	0.0015 (5)	0.0075 (6)	0.0000 (6)
N1	0.0287 (5)	0.0227 (5)	0.0317 (6)	0.0007 (4)	0.0076 (4)	−0.0041 (4)
N2	0.0412 (6)	0.0220 (5)	0.0352 (6)	0.0045 (5)	0.0100 (5)	−0.0018 (4)
O1	0.0297 (5)	0.0261 (4)	0.0433 (6)	0.0042 (4)	0.0045 (4)	−0.0064 (4)
O2	0.0372 (5)	0.0236 (4)	0.0450 (6)	−0.0024 (4)	0.0084 (4)	−0.0036 (4)
O3	0.0396 (5)	0.0268 (5)	0.0441 (6)	0.0023 (4)	0.0147 (4)	−0.0105 (4)
O4	0.0297 (5)	0.0300 (5)	0.0437 (6)	0.0011 (4)	0.0067 (4)	−0.0079 (4)
O5	0.0393 (5)	0.0280 (5)	0.0433 (6)	−0.0053 (4)	0.0075 (4)	−0.0031 (4)
O6	0.0600 (7)	0.0317 (5)	0.0455 (6)	0.0114 (5)	0.0214 (5)	−0.0057 (4)

Geometric parameters (Å, º)

C1—O1	1.4464 (15)	C23—H23A	0.9800
C1—H1A	0.9800	C23—H23B	0.9800
C1—H1B	0.9800	C23—H23C	0.9800
C1—H1C	0.9800	C24—O5	1.2075 (15)
C2—O2	1.2069 (15)	C24—O4	1.3445 (15)
C2—O1	1.3440 (15)	C24—C25	1.4848 (17)
C2—C3	1.4842 (16)	C25—C30	1.3912 (17)
C3—C4	1.3901 (17)	C25—C26	1.3946 (17)
C3—C8	1.3967 (17)	C26—C27	1.3821 (17)
C4—C5	1.3838 (17)	C26—H26	0.9500
C4—H4	0.9500	C27—C28	1.4010 (17)
C5—C6	1.3979 (16)	C27—H27	0.9500
C5—H5	0.9500	C28—C29	1.3973 (18)
C6—C7	1.3999 (17)	C28—C31	1.4639 (17)
C6—C9	1.4599 (16)	C29—C30	1.3809 (18)
C7—C8	1.3802 (17)	C29—H29	0.9500
C7—H7	0.9500	C30—H30	0.9500
C8—H8	0.9500	C31—C32	1.3297 (18)
C9—C10	1.3328 (17)	C31—H31	0.9500
C9—H9	0.9500	C32—C33	1.4697 (17)
C10—C11	1.4680 (16)	C32—H32	0.9500
C10—H10	0.9500	C33—C34	1.4024 (17)
C11—C16	1.3985 (17)	C33—C38	1.4029 (17)
C11—C12	1.4060 (17)	C34—C35	1.3872 (18)
C12—C13	1.3819 (17)	C34—H34	0.9500
C12—H12	0.9500	C35—C36	1.3869 (17)
C13—C14	1.3916 (16)	C35—H35	0.9500
C13—H13	0.9500	C36—C37	1.3915 (16)
C14—C15	1.3906 (16)	C36—C39	1.5081 (17)
C14—C17	1.5051 (16)	C37—C38	1.3807 (16)
C15—C16	1.3844 (16)	C37—C40	1.5061 (16)
C15—C18	1.5059 (16)	C38—H38	0.9500
C16—H16	0.9500	C39—N2	1.4833 (16)
C17—N1	1.4834 (15)	C39—C42	1.5262 (18)
C17—C20	1.5269 (18)	C39—C41	1.5289 (18)
C17—C19	1.5305 (17)	C40—N2	1.4795 (16)
C18—N1	1.4850 (15)	C40—C43	1.5255 (18)
C18—C22	1.5255 (17)	C40—C44	1.5262 (18)
C18—C21	1.5273 (17)	C41—H41A	0.9800
C19—H19A	0.9800	C41—H41B	0.9800
C19—H19B	0.9800	C41—H41C	0.9800
C19—H19C	0.9800	C42—H42A	0.9800
C20—H20A	0.9800	C42—H42B	0.9800
C20—H20B	0.9800	C42—H42C	0.9800
C20—H20C	0.9800	C43—H43A	0.9800
C21—H21A	0.9800	C43—H43B	0.9800
C21—H21B	0.9800	C43—H43C	0.9800
C21—H21C	0.9800	C44—H44A	0.9800
C22—H22A	0.9800	C44—H44B	0.9800
C22—H22B	0.9800	C44—H44C	0.9800
C22—H22C	0.9800	N1—O3	1.2758 (13)
C23—O4	1.4450 (16)	N2—O6	1.2728 (14)
O1—C1—H1A	109.5	H23A—C23—H23C	109.5
O1—C1—H1B	109.5	H23B—C23—H23C	109.5
H1A—C1—H1B	109.5	O5—C24—O4	123.46 (12)
O1—C1—H1C	109.5	O5—C24—C25	124.15 (12)
H1A—C1—H1C	109.5	O4—C24—C25	112.39 (10)
H1B—C1—H1C	109.5	C30—C25—C26	119.11 (11)
O2—C2—O1	123.47 (11)	C30—C25—C24	118.46 (11)
O2—C2—C3	124.35 (11)	C26—C25—C24	122.42 (11)
O1—C2—C3	112.17 (10)	C27—C26—C25	120.57 (11)
C4—C3—C8	119.31 (11)	C27—C26—H26	119.7
C4—C3—C2	121.53 (11)	C25—C26—H26	119.7
C8—C3—C2	119.16 (11)	C26—C27—C28	120.77 (12)
C5—C4—C3	119.95 (11)	C26—C27—H27	119.6
C5—C4—H4	120.0	C28—C27—H27	119.6
C3—C4—H4	120.0	C29—C28—C27	117.96 (11)
C4—C5—C6	121.34 (11)	C29—C28—C31	119.03 (11)
C4—C5—H5	119.3	C27—C28—C31	123.01 (11)
C6—C5—H5	119.3	C30—C29—C28	121.41 (12)
C5—C6—C7	118.12 (11)	C30—C29—H29	119.3
C5—C6—C9	118.38 (11)	C28—C29—H29	119.3
C7—C6—C9	123.49 (11)	C29—C30—C25	120.16 (12)
C8—C7—C6	120.75 (11)	C29—C30—H30	119.9
C8—C7—H7	119.6	C25—C30—H30	119.9
C6—C7—H7	119.6	C32—C31—C28	126.44 (12)
C7—C8—C3	120.50 (11)	C32—C31—H31	116.8
C7—C8—H8	119.7	C28—C31—H31	116.8
C3—C8—H8	119.7	C31—C32—C33	125.57 (12)
C10—C9—C6	127.14 (11)	C31—C32—H32	117.2
C10—C9—H9	116.4	C33—C32—H32	117.2
C6—C9—H9	116.4	C34—C33—C38	118.69 (11)
C9—C10—C11	125.05 (11)	C34—C33—C32	119.48 (11)
C9—C10—H10	117.5	C38—C33—C32	121.82 (11)
C11—C10—H10	117.5	C35—C34—C33	121.68 (12)
C16—C11—C12	118.79 (11)	C35—C34—H34	119.2
C16—C11—C10	119.40 (11)	C33—C34—H34	119.2
C12—C11—C10	121.81 (11)	C36—C35—C34	118.84 (11)
C13—C12—C11	121.53 (11)	C36—C35—H35	120.6
C13—C12—H12	119.2	C34—C35—H35	120.6
C11—C12—H12	119.2	C35—C36—C37	120.08 (11)
C12—C13—C14	118.74 (11)	C35—C36—C39	128.36 (11)
C12—C13—H13	120.6	C37—C36—C39	111.52 (10)
C14—C13—H13	120.6	C38—C37—C36	121.35 (11)
C15—C14—C13	120.59 (11)	C38—C37—C40	126.49 (10)
C15—C14—C17	112.14 (10)	C36—C37—C40	112.14 (10)
C13—C14—C17	127.26 (11)	C37—C38—C33	119.36 (11)
C16—C15—C14	120.55 (11)	C37—C38—H38	120.3
C16—C15—C18	127.89 (11)	C33—C38—H38	120.3
C14—C15—C18	111.56 (10)	N2—C39—C36	100.25 (9)
C15—C16—C11	119.79 (11)	N2—C39—C42	109.11 (10)
C15—C16—H16	120.1	C36—C39—C42	113.53 (11)
C11—C16—H16	120.1	N2—C39—C41	109.66 (11)
N1—C17—C14	99.91 (9)	C36—C39—C41	112.73 (11)
N1—C17—C20	109.78 (10)	C42—C39—C41	110.97 (11)
C14—C17—C20	112.00 (10)	N2—C40—C37	100.08 (9)
N1—C17—C19	110.36 (10)	N2—C40—C43	109.93 (10)
C14—C17—C19	112.94 (10)	C37—C40—C43	112.62 (10)
C20—C17—C19	111.29 (11)	N2—C40—C44	109.86 (10)
N1—C18—C15	100.05 (9)	C37—C40—C44	112.53 (10)
N1—C18—C22	109.58 (10)	C43—C40—C44	111.28 (11)
C15—C18—C22	113.91 (10)	C39—C41—H41A	109.5
N1—C18—C21	109.06 (10)	C39—C41—H41B	109.5
C15—C18—C21	112.63 (10)	H41A—C41—H41B	109.5
C22—C18—C21	110.98 (10)	C39—C41—H41C	109.5
C17—C19—H19A	109.5	H41A—C41—H41C	109.5
C17—C19—H19B	109.5	H41B—C41—H41C	109.5
H19A—C19—H19B	109.5	C39—C42—H42A	109.5
C17—C19—H19C	109.5	C39—C42—H42B	109.5
H19A—C19—H19C	109.5	H42A—C42—H42B	109.5
H19B—C19—H19C	109.5	C39—C42—H42C	109.5
C17—C20—H20A	109.5	H42A—C42—H42C	109.5
C17—C20—H20B	109.5	H42B—C42—H42C	109.5
H20A—C20—H20B	109.5	C40—C43—H43A	109.5
C17—C20—H20C	109.5	C40—C43—H43B	109.5
H20A—C20—H20C	109.5	H43A—C43—H43B	109.5
H20B—C20—H20C	109.5	C40—C43—H43C	109.5
C18—C21—H21A	109.5	H43A—C43—H43C	109.5
C18—C21—H21B	109.5	H43B—C43—H43C	109.5
H21A—C21—H21B	109.5	C40—C44—H44A	109.5
C18—C21—H21C	109.5	C40—C44—H44B	109.5
H21A—C21—H21C	109.5	H44A—C44—H44B	109.5
H21B—C21—H21C	109.5	C40—C44—H44C	109.5
C18—C22—H22A	109.5	H44A—C44—H44C	109.5
C18—C22—H22B	109.5	H44B—C44—H44C	109.5
H22A—C22—H22B	109.5	O3—N1—C17	122.14 (10)
C18—C22—H22C	109.5	O3—N1—C18	121.72 (10)
H22A—C22—H22C	109.5	C17—N1—C18	115.61 (9)
H22B—C22—H22C	109.5	O6—N2—C40	122.09 (11)
O4—C23—H23A	109.5	O6—N2—C39	121.91 (10)
O4—C23—H23B	109.5	C40—N2—C39	116.00 (10)
H23A—C23—H23B	109.5	C2—O1—C1	116.71 (10)
O4—C23—H23C	109.5	C24—O4—C23	116.42 (10)
O2—C2—C3—C4	−168.72 (12)	C29—C28—C31—C32	−163.77 (13)
O1—C2—C3—C4	12.08 (16)	C27—C28—C31—C32	16.5 (2)
O2—C2—C3—C8	10.92 (19)	C28—C31—C32—C33	179.90 (12)
O1—C2—C3—C8	−168.27 (11)	C31—C32—C33—C34	−162.45 (13)
C8—C3—C4—C5	0.06 (18)	C31—C32—C33—C38	16.9 (2)
C2—C3—C4—C5	179.70 (11)	C38—C33—C34—C35	−0.27 (19)
C3—C4—C5—C6	1.06 (19)	C32—C33—C34—C35	179.07 (12)
C4—C5—C6—C7	−1.03 (18)	C33—C34—C35—C36	0.92 (19)
C4—C5—C6—C9	178.71 (11)	C34—C35—C36—C37	−1.01 (18)
C5—C6—C7—C8	−0.10 (18)	C34—C35—C36—C39	176.38 (12)
C9—C6—C7—C8	−179.83 (12)	C35—C36—C37—C38	0.48 (18)
C6—C7—C8—C3	1.20 (19)	C39—C36—C37—C38	−177.32 (11)
C4—C3—C8—C7	−1.18 (18)	C35—C36—C37—C40	179.14 (11)
C2—C3—C8—C7	179.17 (11)	C39—C36—C37—C40	1.34 (14)
C5—C6—C9—C10	−164.07 (13)	C36—C37—C38—C33	0.18 (18)
C7—C6—C9—C10	15.7 (2)	C40—C37—C38—C33	−178.28 (11)
C6—C9—C10—C11	−179.98 (12)	C34—C33—C38—C37	−0.28 (18)
C9—C10—C11—C16	−163.58 (12)	C32—C33—C38—C37	−179.61 (11)
C9—C10—C11—C12	16.6 (2)	C35—C36—C39—N2	−178.59 (12)
C16—C11—C12—C13	−0.22 (19)	C37—C36—C39—N2	−1.02 (13)
C10—C11—C12—C13	179.56 (12)	C35—C36—C39—C42	65.20 (17)
C11—C12—C13—C14	0.42 (19)	C37—C36—C39—C42	−117.23 (12)
C12—C13—C14—C15	0.30 (18)	C35—C36—C39—C41	−62.08 (17)
C12—C13—C14—C17	−178.41 (12)	C37—C36—C39—C41	115.49 (13)
C13—C14—C15—C16	−1.22 (18)	C38—C37—C40—N2	177.59 (12)
C17—C14—C15—C16	177.67 (11)	C36—C37—C40—N2	−0.98 (13)
C13—C14—C15—C18	178.62 (10)	C38—C37—C40—C43	60.91 (16)
C17—C14—C15—C18	−2.49 (14)	C36—C37—C40—C43	−117.67 (12)
C14—C15—C16—C11	1.41 (18)	C38—C37—C40—C44	−65.84 (16)
C18—C15—C16—C11	−178.40 (11)	C36—C37—C40—C44	115.58 (12)
C12—C11—C16—C15	−0.70 (18)	C14—C17—N1—O3	179.41 (11)
C10—C11—C16—C15	179.52 (11)	C20—C17—N1—O3	−62.76 (14)
C15—C14—C17—N1	−2.90 (13)	C19—C17—N1—O3	60.27 (15)
C13—C14—C17—N1	175.90 (11)	C14—C17—N1—C18	7.67 (13)
C15—C14—C17—C20	−119.07 (12)	C20—C17—N1—C18	125.50 (11)
C13—C14—C17—C20	59.73 (16)	C19—C17—N1—C18	−111.47 (11)
C15—C14—C17—C19	114.32 (12)	C15—C18—N1—O3	179.23 (10)
C13—C14—C17—C19	−66.88 (16)	C22—C18—N1—O3	59.23 (14)
C16—C15—C18—N1	−173.55 (12)	C21—C18—N1—O3	−62.43 (14)
C14—C15—C18—N1	6.63 (12)	C15—C18—N1—C17	−8.99 (13)
C16—C15—C18—C22	−56.75 (16)	C22—C18—N1—C17	−128.99 (11)
C14—C15—C18—C22	123.43 (11)	C21—C18—N1—C17	109.35 (11)
C16—C15—C18—C21	70.79 (16)	C37—C40—N2—O6	179.36 (11)
C14—C15—C18—C21	−109.04 (12)	C43—C40—N2—O6	−61.97 (16)
O5—C24—C25—C30	−1.48 (19)	C44—C40—N2—O6	60.81 (16)
O4—C24—C25—C30	178.92 (11)	C37—C40—N2—C39	0.31 (13)
O5—C24—C25—C26	178.01 (13)	C43—C40—N2—C39	118.99 (12)
O4—C24—C25—C26	−1.59 (17)	C44—C40—N2—C39	−118.24 (12)
C30—C25—C26—C27	−1.08 (19)	C36—C39—N2—O6	−178.66 (12)
C24—C25—C26—C27	179.43 (12)	C42—C39—N2—O6	−59.18 (16)
C25—C26—C27—C28	0.2 (2)	C41—C39—N2—O6	62.55 (15)
C26—C27—C28—C29	1.14 (19)	C36—C39—N2—C40	0.39 (13)
C26—C27—C28—C31	−179.15 (12)	C42—C39—N2—C40	119.86 (12)
C27—C28—C29—C30	−1.72 (19)	C41—C39—N2—C40	−118.40 (12)
C31—C28—C29—C30	178.56 (12)	O2—C2—O1—C1	−0.71 (18)
C28—C29—C30—C25	0.9 (2)	C3—C2—O1—C1	178.49 (11)
C26—C25—C30—C29	0.51 (19)	O5—C24—O4—C23	0.87 (19)
C24—C25—C30—C29	−179.97 (11)	C25—C24—O4—C23	−179.53 (11)