Molecular structures and conformations of three 3-azabicyclononanes

The structure, conformation, molecular geometry and the mode of packing of 7-tert-butyl-N-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonane (C₂₅H₃₃N; MTABN), N-acetyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonane (C₂₂H₂₅NO; AABN) and N-methyl-2,4-bis(2-methylphenyl)-3-azabicyclo[3.3.1]nonan-9-ol (C₂₃H₂₉NO; MHABN) are presented. The compounds MTABN and MHABN crystallize in monoclinic space groups, whereas AABN is orthorhombic. In each of the three structures, the bicyclic ring system adopts a chair–chair conformation and the phenyl rings are in equatorial orientation with respect to the piperidine ring. In AABN, apart from the van der Waals forces, weak intermolecular C—H...O type interactions are involved in the packing.

Computing details

For all compounds, data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PARST (Nardelli, 1983; 1995).

Figures

(MTABN) N-Methyl-2,4-diphenyl-7-tertiary butyl 3-azabicyclo[3.3.1]nonane

Crystal data

C25H33N	F(000) = 760
Mr = 347.52	Dx = 1.097 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.667 (1) Å	Cell parameters from 40 reflections
b = 16.414 (2) Å	θ = 6.2–13.0°
c = 9.409 (1) Å	µ = 0.06 mm^−1
β = 94.54 (1)°	T = 293 K
V = 2104.1 (4) Å^3	Plate, pale yellow
Z = 4	0.67 × 0.58 × 0.45 mm

Data collection

Siemens P4 diffractometer	Rint = 0.034
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.5°
Graphite monochromator	h = −16→16
θ/2θ scans	k = −19→1
4714 measured reflections	l = −1→11
3669 independent reflections	3 standard reflections every 100 reflections
2255 reflections with I > 2σ(I)	intensity decay: <1%

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) = 0.185	All H-atom parameters refined
S = 0.93	Calculated w = 1/[σ^2(Fo^2) + (0.1151P)^2] where P = (Fo^2 + 2Fc^2)/3
3649 reflections	(Δ/σ)max = 0.013
368 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.17 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 on F² for ALL reflections except for 20 with very negative F²

or 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
C1	0.11854 (11)	0.45720 (10)	0.2068 (2)	0.0636 (5)
C2	0.19282 (12)	0.51444 (10)	0.1427 (2)	0.0594 (4)
N3	0.29617 (9)	0.49279 (8)	0.1848 (2)	0.0588 (4)
C4	0.31556 (12)	0.40523 (10)	0.1638 (2)	0.0605 (5)
C5	0.24034 (12)	0.34913 (10)	0.2269 (2)	0.0648 (5)
C6	0.24121 (12)	0.34877 (10)	0.3881 (2)	0.0636 (5)
C7	0.20941 (11)	0.42982 (9)	0.4516 (2)	0.0551 (4)
C8	0.11627 (11)	0.46092 (10)	0.3680 (2)	0.0609 (5)
C9	0.13846 (13)	0.37053 (12)	0.1597 (2)	0.0733 (6)
C10	0.17040 (11)	0.60231 (10)	0.1769 (2)	0.0553 (4)
C11	0.21512 (12)	0.64257 (11)	0.2941 (2)	0.0632 (5)
C12	0.18830 (13)	0.72145 (11)	0.3242 (2)	0.0691 (5)
C13	0.11632 (13)	0.76033 (12)	0.2392 (2)	0.0758 (6)
C14	0.07042 (14)	0.72073 (12)	0.1246 (2)	0.0775 (6)
C15	0.09753 (14)	0.64204 (12)	0.0942 (2)	0.0697 (5)
C16	0.41887 (12)	0.38136 (10)	0.2197 (2)	0.0600 (5)
C17	0.46496 (12)	0.41270 (12)	0.3422 (2)	0.0696 (5)
C18	0.55508 (14)	0.38407 (13)	0.3977 (3)	0.0834 (6)
C19	0.60096 (15)	0.32262 (14)	0.3291 (3)	0.0943 (7)
C20	0.5565 (2)	0.29156 (14)	0.2076 (3)	0.0995 (8)
C21	0.46592 (14)	0.31970 (13)	0.1507 (3)	0.0834 (6)
C22	0.36094 (15)	0.54133 (13)	0.1018 (3)	0.0788 (6)
C23	0.20254 (13)	0.42777 (10)	0.6145 (2)	0.0659 (5)
C24	0.1785 (2)	0.51353 (13)	0.6671 (3)	0.0833 (6)
C25	0.3014 (2)	0.40214 (15)	0.6888 (2)	0.0833 (6)
C26	0.1228 (2)	0.36937 (15)	0.6594 (3)	0.0900 (7)
H1	0.0588 (13)	0.4743 (11)	0.1518 (18)	0.073 (5)*
H2	0.1816 (12)	0.5111 (10)	0.0326 (17)	0.061 (5)*
H4	0.3082 (11)	0.3939 (9)	0.0598 (16)	0.055 (4)*
H5	0.2577 (12)	0.2936 (10)	0.2013 (17)	0.064 (5)*
H6A	0.1955 (13)	0.3065 (10)	0.4183 (17)	0.065 (5)*
H6B	0.3024 (13)	0.3318 (10)	0.4313 (17)	0.064 (5)*
H7	0.2585 (11)	0.4696 (9)	0.4392 (15)	0.054 (4)*
H8A	0.1082 (10)	0.5171 (9)	0.3946 (14)	0.047 (4)*
H8B	0.0623 (14)	0.4248 (11)	0.3942 (18)	0.077 (5)*
H9A	0.0896 (14)	0.3329 (12)	0.1877 (19)	0.079 (6)*
H9B	0.1363 (12)	0.3661 (10)	0.0558 (17)	0.060 (5)*
H11	0.2615 (12)	0.6143 (9)	0.3556 (15)	0.054 (4)*
H12	0.2156 (13)	0.7421 (11)	0.4093 (18)	0.069 (5)*
H13	0.1019 (13)	0.8167 (11)	0.2651 (18)	0.076 (5)*
H14	0.0192 (16)	0.7507 (14)	0.064 (2)	0.101 (7)*
H15	0.0733 (16)	0.6232 (12)	0.003 (2)	0.092 (7)*
H17	0.4349 (15)	0.4568 (12)	0.396 (2)	0.087 (6)*
H18	0.5852 (16)	0.4025 (12)	0.495 (2)	0.094 (6)*
H19A	0.6658 (19)	0.3019 (14)	0.372 (3)	0.119 (8)*
H20	0.5875 (17)	0.2526 (15)	0.163 (2)	0.105 (7)*
H21	0.4382 (16)	0.3064 (12)	0.054 (2)	0.097 (7)*
H22A	0.3498 (16)	0.5326 (14)	0.001 (3)	0.104 (7)*
H22B	0.3532 (16)	0.6048 (14)	0.116 (2)	0.103 (7)*
H22C	0.4258 (17)	0.5305 (12)	0.127 (2)	0.089 (6)*
H24A	0.1825 (16)	0.5146 (13)	0.775 (2)	0.098 (7)*
H24B	0.2238 (16)	0.5541 (12)	0.641 (2)	0.093 (7)*
H24C	0.1134 (17)	0.5363 (13)	0.632 (2)	0.100 (7)*
H25A	0.3202 (16)	0.3409 (15)	0.666 (2)	0.104 (7)*
H25B	0.2975 (15)	0.4034 (13)	0.793 (2)	0.093 (6)*
H25C	0.3572 (19)	0.4401 (15)	0.666 (3)	0.119 (8)*
H26A	0.1382 (17)	0.3144 (14)	0.638 (2)	0.100 (7)*
H26B	0.1301 (18)	0.3688 (14)	0.768 (3)	0.115 (8)*
H26C	0.0601 (19)	0.3863 (15)	0.618 (3)	0.117 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0376 (8)	0.0566 (10)	0.0944 (13)	0.0005 (7)	−0.0086 (8)	−0.0008 (9)
C2	0.0484 (8)	0.0624 (10)	0.0659 (10)	0.0037 (8)	−0.0056 (8)	−0.0002 (8)
N3	0.0417 (7)	0.0540 (7)	0.0810 (9)	0.0023 (6)	0.0078 (6)	0.0010 (7)
C4	0.0509 (8)	0.0609 (10)	0.0692 (11)	0.0037 (8)	0.0014 (8)	−0.0114 (9)
C5	0.0487 (8)	0.0432 (8)	0.1017 (14)	−0.0005 (7)	0.0009 (9)	−0.0153 (9)
C6	0.0454 (8)	0.0408 (8)	0.1046 (14)	0.0006 (7)	0.0062 (9)	0.0036 (9)
C7	0.0401 (7)	0.0395 (8)	0.0866 (12)	−0.0022 (7)	0.0103 (8)	0.0055 (8)
C8	0.0395 (8)	0.0468 (9)	0.0974 (13)	0.0010 (7)	0.0111 (8)	0.0041 (9)
C9	0.0516 (10)	0.0626 (11)	0.1033 (15)	−0.0058 (8)	−0.0081 (10)	−0.0145 (10)
C10	0.0440 (8)	0.0575 (9)	0.0645 (10)	0.0019 (7)	0.0049 (7)	0.0084 (8)
C11	0.0485 (9)	0.0583 (10)	0.0818 (12)	0.0039 (8)	−0.0015 (9)	0.0066 (9)
C12	0.0567 (9)	0.0611 (10)	0.0896 (13)	−0.0044 (9)	0.0074 (10)	−0.0038 (10)
C13	0.0609 (10)	0.0556 (10)	0.114 (2)	0.0109 (9)	0.0297 (11)	0.0145 (10)
C14	0.0640 (11)	0.0738 (12)	0.0946 (14)	0.0191 (10)	0.0050 (11)	0.0205 (11)
C15	0.0645 (10)	0.0745 (12)	0.0692 (11)	0.0106 (9)	−0.0007 (9)	0.0129 (10)
C16	0.0454 (8)	0.0563 (9)	0.0796 (11)	0.0037 (7)	0.0124 (8)	−0.0094 (8)
C17	0.0465 (9)	0.0686 (11)	0.0939 (13)	0.0066 (8)	0.0069 (9)	−0.0159 (10)
C18	0.0516 (10)	0.0891 (14)	0.108 (2)	0.0077 (10)	−0.0047 (11)	−0.0134 (12)
C19	0.0530 (10)	0.0856 (14)	0.143 (2)	0.0177 (10)	−0.0001 (12)	−0.0091 (14)
C20	0.0656 (12)	0.0876 (15)	0.147 (2)	0.0255 (11)	0.0166 (13)	−0.0286 (15)
C21	0.0607 (11)	0.0838 (13)	0.107 (2)	0.0138 (10)	0.0133 (11)	−0.0271 (12)
C22	0.0604 (10)	0.0777 (13)	0.101 (2)	0.0034 (10)	0.0265 (11)	0.0118 (11)
C23	0.0598 (10)	0.0536 (9)	0.0863 (12)	0.0004 (8)	0.0184 (9)	0.0120 (9)
C24	0.0885 (14)	0.0734 (13)	0.0905 (15)	0.0076 (11)	0.0232 (12)	−0.0021 (11)
C25	0.0781 (13)	0.0915 (15)	0.0801 (14)	0.0089 (12)	0.0056 (11)	0.0127 (12)
C26	0.0778 (13)	0.0817 (14)	0.114 (2)	−0.0034 (11)	0.0307 (12)	0.0286 (13)

Geometric parameters (Å, º)

C1—C8	1.521 (3)	C13—C14	1.368 (3)
C1—C9	1.521 (2)	C13—H13	0.98 (2)
C1—C2	1.540 (2)	C14—C15	1.380 (3)
C1—H1	0.97 (2)	C14—H14	1.00 (2)
C2—N3	1.480 (2)	C15—H15	0.95 (2)
C2—C10	1.514 (2)	C16—C17	1.370 (3)
C2—H2	1.04 (2)	C16—C21	1.388 (3)
N3—C22	1.462 (2)	C17—C18	1.382 (3)
N3—C4	1.477 (2)	C17—H17	0.99 (2)
C4—C16	1.518 (2)	C18—C19	1.375 (3)
C4—C5	1.534 (2)	C18—H18	1.02 (2)
C4—H4	0.994 (15)	C19—C20	1.351 (3)
C5—C6	1.516 (3)	C19—H19A	1.00 (2)
C5—C9	1.524 (2)	C20—C21	1.388 (3)
C5—H5	0.98 (2)	C20—H20	0.89 (2)
C6—C7	1.535 (2)	C21—H21	0.98 (2)
C6—H6A	0.99 (2)	C22—H22A	0.96 (2)
C6—H6B	0.94 (2)	C22—H22B	1.06 (2)
C7—C8	1.530 (2)	C22—H22C	0.92 (2)
C7—C23	1.543 (3)	C23—C25	1.531 (3)
C7—H7	0.95 (2)	C23—C26	1.535 (3)
C8—H8A	0.964 (15)	C23—C24	1.536 (3)
C8—H8B	0.99 (2)	C24—H24A	1.01 (2)
C9—H9A	0.96 (2)	C24—H24B	0.96 (2)
C9—H9B	0.98 (2)	C24—H24C	1.00 (2)
C10—C15	1.378 (2)	C25—H25A	1.06 (2)
C10—C11	1.385 (2)	C25—H25B	0.98 (2)
C11—C12	1.381 (3)	C25—H25C	1.02 (3)
C11—H11	0.945 (15)	C26—H26A	0.95 (2)
C12—C13	1.375 (3)	C26—H26B	1.02 (2)
C12—H12	0.92 (2)	C26—H26C	0.96 (2)
C8—C1—C9	110.3 (2)	C11—C12—H12	115.3 (11)
C8—C1—C2	115.58 (14)	C14—C13—C12	120.0 (2)
C9—C1—C2	108.5 (2)	C14—C13—H13	123.8 (10)
C8—C1—H1	115.8 (10)	C12—C13—H13	116.2 (10)
C9—C1—H1	106.1 (10)	C13—C14—C15	119.6 (2)
C2—C1—H1	99.7 (11)	C13—C14—H14	118.3 (13)
N3—C2—C10	112.14 (13)	C15—C14—H14	122.1 (13)
N3—C2—C1	113.18 (13)	C10—C15—C14	121.3 (2)
C10—C2—C1	110.31 (14)	C10—C15—H15	122.9 (13)
N3—C2—H2	108.4 (9)	C14—C15—H15	114.3 (12)
C10—C2—H2	104.3 (9)	C17—C16—C21	117.9 (2)
C1—C2—H2	108.0 (9)	C17—C16—C4	123.2 (2)
C22—N3—C4	109.66 (14)	C21—C16—C4	118.6 (2)
C22—N3—C2	109.39 (14)	C16—C17—C18	121.8 (2)
C4—N3—C2	112.06 (13)	C16—C17—H17	121.5 (11)
N3—C4—C16	112.12 (13)	C18—C17—H17	116.7 (11)
N3—C4—C5	113.55 (14)	C19—C18—C17	119.9 (2)
C16—C4—C5	110.15 (14)	C19—C18—H18	118.2 (12)
N3—C4—H4	108.0 (9)	C17—C18—H18	121.5 (13)
C16—C4—H4	108.1 (9)	C20—C19—C18	118.8 (2)
C5—C4—H4	104.5 (9)	C20—C19—H19A	122.4 (14)
C6—C5—C9	110.5 (2)	C18—C19—H19A	118.8 (14)
C6—C5—C4	115.91 (14)	C19—C20—C21	121.9 (2)
C9—C5—C4	108.6 (2)	C19—C20—H20	118.2 (15)
C6—C5—H5	105.1 (9)	C21—C20—H20	119.9 (15)
C9—C5—H5	110.1 (10)	C20—C21—C16	119.6 (2)
C4—C5—H5	106.4 (10)	C20—C21—H21	123.4 (13)
C5—C6—C7	113.96 (14)	C16—C21—H21	115.8 (13)
C5—C6—H6A	109.5 (9)	N3—C22—H22A	113.1 (14)
C7—C6—H6A	106.9 (10)	N3—C22—H22B	113.4 (12)
C5—C6—H6B	111.6 (10)	H22A—C22—H22B	105.4 (17)
C7—C6—H6B	110.9 (10)	N3—C22—H22C	111.8 (13)
H6A—C6—H6B	103.2 (14)	H22A—C22—H22C	107.5 (18)
C8—C7—C6	109.79 (14)	H22B—C22—H22C	105.2 (17)
C8—C7—C23	113.86 (14)	C25—C23—C26	108.8 (2)
C6—C7—C23	114.14 (14)	C25—C23—C24	108.0 (2)
C8—C7—H7	106.0 (9)	C26—C23—C24	108.0 (2)
C6—C7—H7	108.8 (9)	C25—C23—C7	109.78 (15)
C23—C7—H7	103.6 (9)	C26—C23—C7	112.8 (2)
C1—C8—C7	114.69 (14)	C24—C23—C7	109.34 (15)
C1—C8—H8A	108.0 (8)	C23—C24—H24A	110.0 (12)
C7—C8—H8A	107.1 (8)	C23—C24—H24B	113.3 (13)
C1—C8—H8B	107.3 (10)	H24A—C24—H24B	105.3 (18)
C7—C8—H8B	106.1 (10)	C23—C24—H24C	116.5 (13)
H8A—C8—H8B	113.8 (14)	H24A—C24—H24C	107.5 (18)
C1—C9—C5	105.87 (14)	H24B—C24—H24C	103.5 (17)
C1—C9—H9A	112.1 (11)	C23—C25—H25A	112.7 (12)
C5—C9—H9A	111.7 (11)	C23—C25—H25B	109.4 (13)
C1—C9—H9B	111.6 (10)	H25A—C25—H25B	104.7 (17)
C5—C9—H9B	110.6 (10)	C23—C25—H25C	112.5 (14)
H9A—C9—H9B	105.0 (14)	H25A—C25—H25C	109.7 (19)
C15—C10—C11	118.5 (2)	H25B—C25—H25C	107.3 (19)
C15—C10—C2	118.7 (2)	C23—C26—H26A	111.1 (14)
C11—C10—C2	122.64 (14)	C23—C26—H26B	105.5 (14)
C12—C11—C10	120.2 (2)	H26A—C26—H26B	101.5 (19)
C12—C11—H11	120.7 (9)	C23—C26—H26C	109.8 (15)
C10—C11—H11	119.0 (9)	H26A—C26—H26C	113 (2)
C13—C12—C11	120.4 (2)	H26B—C26—H26C	115 (2)
C13—C12—H12	123.8 (11)
C8—C1—C2—N3	66.4 (2)	C1—C2—C10—C15	−81.2 (2)
C9—C1—C2—N3	−58.1 (2)	N3—C2—C10—C11	−33.1 (2)
C8—C1—C2—C10	−60.2 (2)	C1—C2—C10—C11	94.0 (2)
C9—C1—C2—C10	175.37 (14)	C15—C10—C11—C12	−1.6 (3)
C10—C2—N3—C22	−63.5 (2)	C2—C10—C11—C12	−176.8 (2)
C1—C2—N3—C22	170.9 (2)	C10—C11—C12—C13	0.7 (3)
C10—C2—N3—C4	174.65 (13)	C11—C12—C13—C14	0.4 (3)
C1—C2—N3—C4	49.1 (2)	C12—C13—C14—C15	−0.6 (3)
C22—N3—C4—C16	63.7 (2)	C11—C10—C15—C14	1.3 (3)
C2—N3—C4—C16	−174.66 (14)	C2—C10—C15—C14	176.7 (2)
C22—N3—C4—C5	−170.7 (2)	C13—C14—C15—C10	−0.2 (3)
C2—N3—C4—C5	−49.0 (2)	N3—C4—C16—C17	38.3 (2)
N3—C4—C5—C6	−67.4 (2)	C5—C4—C16—C17	−89.2 (2)
C16—C4—C5—C6	59.3 (2)	N3—C4—C16—C21	−147.5 (2)
N3—C4—C5—C9	57.7 (2)	C5—C4—C16—C21	85.0 (2)
C16—C4—C5—C9	−175.61 (14)	C21—C16—C17—C18	−0.6 (3)
C9—C5—C6—C7	−57.6 (2)	C4—C16—C17—C18	173.6 (2)
C4—C5—C6—C7	66.5 (2)	C16—C17—C18—C19	0.2 (3)
C5—C6—C7—C8	46.3 (2)	C17—C18—C19—C20	0.2 (4)
C5—C6—C7—C23	175.56 (13)	C18—C19—C20—C21	−0.2 (4)
C9—C1—C8—C7	56.7 (2)	C19—C20—C21—C16	−0.2 (4)
C2—C1—C8—C7	−66.8 (2)	C17—C16—C21—C20	0.5 (3)
C6—C7—C8—C1	−46.1 (2)	C4—C16—C21—C20	−173.9 (2)
C23—C7—C8—C1	−175.45 (13)	C8—C7—C23—C25	−175.71 (15)
C8—C1—C9—C5	−63.0 (2)	C6—C7—C23—C25	57.1 (2)
C2—C1—C9—C5	64.5 (2)	C8—C7—C23—C26	62.7 (2)
C6—C5—C9—C1	63.9 (2)	C6—C7—C23—C26	−64.4 (2)
C4—C5—C9—C1	−64.3 (2)	C8—C7—C23—C24	−57.4 (2)
N3—C2—C10—C15	151.7 (2)	C6—C7—C23—C24	175.42 (15)

(AABN) N-Acetyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonane

Crystal data

C22H25NO	F(000) = 1376
Mr = 319.43	Dx = 1.204 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 42 reflections
a = 14.687 (1) Å	θ = 7.0–14.0°
b = 12.931 (1) Å	µ = 0.07 mm^−1
c = 18.564 (1) Å	T = 293 K
V = 3525.6 (4) Å^3	Needle, pale yellow
Z = 8	0.59 × 0.47 × 0.30 mm

Data collection

Siemens P4 diffractometer	Rint = 0.018
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.2°
Graphite monochromator	h = −1→19
θ/2θ scans	k = −1→16
4946 measured reflections	l = −24→1
4005 independent reflections	3 standard reflections every 100 reflections
2454 reflections with I > 2σ(I)	intensity decay: <1%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	All H-atom parameters refined
S = 0.89	Calculated w = 1/[σ^2(Fo^2) + (0.0619P)^2] where P = (Fo^2 + 2Fc^2)/3
4005 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.18 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 on F² for ALL reflections except for 0 with very negative F²

or 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
C1	1.01007 (11)	−0.01440 (13)	0.86986 (8)	0.0475 (4)
C2	0.91554 (10)	0.02789 (11)	0.84692 (7)	0.0398 (3)
N3	0.89455 (8)	0.01638 (8)	0.76856 (6)	0.0362 (3)
C4	0.96464 (9)	−0.01304 (11)	0.71401 (7)	0.0383 (3)
C5	1.05542 (10)	−0.05195 (13)	0.74545 (9)	0.0489 (4)
C6	1.06025 (13)	−0.16735 (14)	0.76229 (11)	0.0597 (5)
C7	0.99810 (14)	−0.19791 (14)	0.82338 (10)	0.0597 (5)
C8	1.01328 (14)	−0.12905 (14)	0.88846 (9)	0.0564 (4)
C9	1.07897 (12)	0.0118 (2)	0.81177 (9)	0.0554 (4)
C10	0.82807 (10)	0.07946 (10)	0.73987 (7)	0.0411 (3)
O11	0.82232 (8)	0.09191 (9)	0.67475 (5)	0.0567 (3)
C12	0.76209 (13)	0.13388 (14)	0.78858 (10)	0.0522 (4)
C13	0.84082 (10)	−0.01299 (11)	0.89586 (7)	0.0413 (3)
C14	0.78392 (11)	−0.09435 (12)	0.87867 (8)	0.0467 (4)
C15	0.71867 (12)	−0.1294 (2)	0.92690 (9)	0.0575 (4)
C16	0.70969 (13)	−0.0838 (2)	0.99332 (9)	0.0635 (5)
C17	0.76487 (14)	−0.0028 (2)	1.01111 (9)	0.0678 (5)
C18	0.82954 (13)	0.0331 (2)	0.96321 (8)	0.0565 (4)
C19	0.92943 (9)	−0.08596 (10)	0.65658 (7)	0.0387 (3)
C20	0.85792 (11)	−0.15441 (11)	0.66670 (8)	0.0441 (3)
C21	0.83427 (12)	−0.22551 (13)	0.61398 (9)	0.0541 (4)
C22	0.88165 (13)	−0.22872 (15)	0.55048 (9)	0.0639 (5)
C23	0.95165 (14)	−0.1598 (2)	0.53879 (9)	0.0667 (5)
C24	0.97504 (12)	−0.08899 (14)	0.59118 (8)	0.0539 (4)
H1	1.0239 (10)	0.0263 (12)	0.9151 (9)	0.052 (4)*
H2	0.9212 (10)	0.1028 (12)	0.8562 (8)	0.043 (4)*
H4	0.9784 (10)	0.0513 (12)	0.6881 (7)	0.042 (4)*
H5	1.1012 (11)	−0.0352 (12)	0.7075 (8)	0.052 (4)*
H6A	1.1223 (13)	−0.1817 (13)	0.7770 (9)	0.066 (5)*
H6B	1.0447 (12)	−0.2078 (14)	0.7181 (9)	0.067 (5)*
H7A	0.9324 (12)	−0.1922 (12)	0.8079 (8)	0.055 (4)*
H7B	1.0093 (13)	−0.2689 (16)	0.8372 (9)	0.080 (6)*
H8A	1.0730 (13)	−0.1431 (13)	0.9075 (9)	0.064 (5)*
H8B	0.9703 (12)	−0.1467 (12)	0.9267 (9)	0.057 (5)*
H9A	1.1379 (14)	−0.0026 (14)	0.8304 (9)	0.067 (5)*
H9B	1.0747 (11)	0.0897 (14)	0.8010 (8)	0.061 (5)*
H12A	0.7221 (15)	0.1730 (15)	0.7589 (10)	0.086 (6)*
H12B	0.7922 (15)	0.1783 (16)	0.8247 (10)	0.090 (6)*
H12C	0.7247 (16)	0.0880 (17)	0.8181 (11)	0.094 (7)*
H14	0.7876 (11)	−0.1273 (12)	0.8327 (8)	0.050 (4)*
H15	0.6770 (13)	−0.1844 (15)	0.9132 (9)	0.071 (6)*
H16	0.6645 (13)	−0.1098 (14)	1.0265 (10)	0.072 (5)*
H17	0.7579 (12)	0.0316 (14)	1.0564 (10)	0.074 (5)*
H18	0.8692 (12)	0.0888 (14)	0.9753 (9)	0.064 (5)*
H20	0.8227 (10)	−0.1514 (11)	0.7091 (8)	0.041 (4)*
H21	0.7830 (12)	−0.2733 (13)	0.6232 (8)	0.064 (5)*
H22	0.8679 (13)	−0.2776 (16)	0.5140 (10)	0.081 (6)*
H23	0.9871 (13)	−0.1583 (15)	0.4949 (10)	0.079 (6)*
H24	1.0226 (12)	−0.0396 (14)	0.5837 (9)	0.062 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0468 (8)	0.0543 (9)	0.0414 (8)	−0.0040 (7)	−0.0126 (7)	−0.0048 (7)
C2	0.0495 (8)	0.0358 (7)	0.0341 (7)	−0.0012 (6)	−0.0072 (6)	−0.0061 (6)
N3	0.0417 (6)	0.0343 (5)	0.0325 (5)	−0.0001 (5)	−0.0047 (5)	−0.0025 (5)
C4	0.0419 (7)	0.0358 (7)	0.0374 (7)	−0.0057 (6)	0.0017 (6)	−0.0005 (6)
C5	0.0376 (7)	0.0592 (9)	0.0497 (9)	−0.0020 (7)	0.0020 (7)	−0.0049 (7)
C6	0.0510 (10)	0.0613 (11)	0.0670 (11)	0.0186 (9)	−0.0092 (9)	−0.0094 (9)
C7	0.0657 (12)	0.0422 (9)	0.0712 (11)	0.0109 (8)	−0.0099 (9)	0.0032 (8)
C8	0.0534 (10)	0.0618 (11)	0.0539 (10)	0.0108 (9)	−0.0100 (9)	0.0090 (8)
C9	0.0415 (9)	0.0669 (11)	0.0577 (10)	−0.0089 (9)	−0.0100 (8)	−0.0047 (9)
C10	0.0482 (8)	0.0331 (7)	0.0419 (8)	−0.0024 (6)	−0.0081 (6)	−0.0010 (6)
O11	0.0720 (8)	0.0569 (7)	0.0413 (6)	0.0132 (6)	−0.0109 (5)	0.0039 (5)
C12	0.0572 (10)	0.0452 (9)	0.0543 (9)	0.0125 (8)	−0.0071 (9)	−0.0028 (8)
C13	0.0461 (8)	0.0454 (8)	0.0326 (7)	0.0085 (7)	−0.0063 (6)	−0.0044 (6)
C14	0.0522 (9)	0.0513 (9)	0.0366 (7)	0.0019 (8)	0.0027 (7)	−0.0053 (7)
C15	0.0532 (10)	0.0690 (11)	0.0504 (9)	−0.0006 (9)	0.0052 (8)	0.0035 (9)
C16	0.0538 (10)	0.0920 (14)	0.0447 (9)	0.0133 (10)	0.0081 (8)	0.0087 (10)
C17	0.0718 (12)	0.0975 (15)	0.0341 (8)	0.0226 (12)	0.0018 (9)	−0.0110 (9)
C18	0.0641 (11)	0.0678 (11)	0.0378 (8)	0.0077 (9)	−0.0081 (8)	−0.0127 (8)
C19	0.0424 (7)	0.0366 (7)	0.0369 (7)	−0.0013 (6)	0.0005 (6)	−0.0016 (6)
C20	0.0525 (9)	0.0428 (8)	0.0370 (7)	−0.0094 (7)	0.0026 (7)	−0.0005 (6)
C21	0.0636 (11)	0.0482 (9)	0.0504 (9)	−0.0170 (8)	−0.0016 (8)	−0.0065 (7)
C22	0.0746 (12)	0.0638 (11)	0.0534 (10)	−0.0106 (10)	0.0020 (9)	−0.0240 (9)
C23	0.0715 (12)	0.0799 (13)	0.0488 (9)	−0.0114 (11)	0.0153 (9)	−0.0203 (9)
C24	0.0544 (10)	0.0594 (10)	0.0478 (8)	−0.0136 (9)	0.0107 (8)	−0.0081 (8)

Geometric parameters (Å, º)

C1—C9	1.517 (2)	C10—C12	1.501 (2)
C1—C8	1.523 (2)	C12—H12A	0.95 (2)
C1—C2	1.552 (2)	C12—H12B	0.99 (2)
C1—H1	1.01 (2)	C12—H12C	0.98 (2)
C2—N3	1.494 (2)	C13—C14	1.381 (2)
C2—C13	1.520 (2)	C13—C18	1.395 (2)
C2—H2	0.987 (15)	C14—C15	1.388 (2)
N3—C10	1.379 (2)	C14—H14	0.955 (15)
N3—C4	1.493 (2)	C15—C16	1.373 (2)
C4—C19	1.514 (2)	C15—H15	0.97 (2)
C4—C5	1.540 (2)	C16—C17	1.365 (3)
C4—H4	0.98 (2)	C16—H16	0.97 (2)
C5—C9	1.522 (2)	C17—C18	1.381 (3)
C5—C6	1.526 (2)	C17—H17	0.96 (2)
C5—H5	1.00 (2)	C18—H18	0.95 (2)
C6—C7	1.509 (3)	C19—C20	1.386 (2)
C6—H6A	0.97 (2)	C19—C24	1.387 (2)
C6—H6B	1.00 (2)	C20—C21	1.387 (2)
C7—C8	1.517 (2)	C20—H20	0.943 (15)
C7—H7A	1.01 (2)	C21—C22	1.369 (2)
C7—H7B	0.97 (2)	C21—H21	0.99 (2)
C8—H8A	0.96 (2)	C22—C23	1.378 (3)
C8—H8B	0.98 (2)	C22—H22	0.95 (2)
C9—H9A	0.95 (2)	C23—C24	1.379 (2)
C9—H9B	1.03 (2)	C23—H23	0.97 (2)
C10—O11	1.223 (2)	C24—H24	0.96 (2)
C9—C1—C8	110.99 (15)	C1—C9—H9B	108.4 (9)
C9—C1—C2	108.84 (13)	C5—C9—H9B	111.1 (9)
C8—C1—C2	115.66 (14)	H9A—C9—H9B	108.5 (15)
C9—C1—H1	109.9 (9)	O11—C10—N3	120.57 (13)
C8—C1—H1	108.2 (9)	O11—C10—C12	119.31 (14)
C2—C1—H1	102.9 (9)	N3—C10—C12	120.12 (13)
N3—C2—C13	113.47 (11)	C10—C12—H12A	107.5 (12)
N3—C2—C1	114.62 (12)	C10—C12—H12B	113.1 (12)
C13—C2—C1	111.07 (12)	H12A—C12—H12B	111.1 (16)
N3—C2—H2	106.6 (8)	C10—C12—H12C	114.6 (12)
C13—C2—H2	107.3 (9)	H12A—C12—H12C	107.5 (18)
C1—C2—H2	102.9 (9)	H12B—C12—H12C	103.0 (15)
C10—N3—C4	112.14 (11)	C14—C13—C18	117.44 (15)
C10—N3—C2	117.58 (11)	C14—C13—C2	124.32 (12)
C4—N3—C2	122.90 (11)	C18—C13—C2	118.23 (14)
N3—C4—C19	113.62 (11)	C13—C14—C15	121.15 (15)
N3—C4—C5	115.03 (11)	C13—C14—H14	120.8 (9)
C19—C4—C5	111.04 (11)	C15—C14—H14	118.0 (10)
N3—C4—H4	105.0 (8)	C16—C15—C14	120.4 (2)
C19—C4—H4	104.6 (8)	C16—C15—H15	119.3 (11)
C5—C4—H4	106.5 (9)	C14—C15—H15	120.2 (11)
C9—C5—C6	110.71 (15)	C17—C16—C15	119.3 (2)
C9—C5—C4	109.04 (13)	C17—C16—H16	121.4 (11)
C6—C5—C4	115.93 (13)	C15—C16—H16	119.3 (11)
C9—C5—H5	107.5 (9)	C16—C17—C18	120.7 (2)
C6—C5—H5	109.0 (9)	C16—C17—H17	120.4 (11)
C4—C5—H5	104.2 (9)	C18—C17—H17	118.9 (11)
C7—C6—C5	112.45 (14)	C17—C18—C13	121.0 (2)
C7—C6—H6A	107.9 (10)	C17—C18—H18	121.5 (10)
C5—C6—H6A	106.8 (10)	C13—C18—H18	117.4 (11)
C7—C6—H6B	110.0 (10)	C20—C19—C24	117.81 (13)
C5—C6—H6B	109.5 (10)	C20—C19—C4	124.11 (12)
H6A—C6—H6B	110.2 (14)	C24—C19—C4	117.96 (13)
C6—C7—C8	110.9 (2)	C19—C20—C21	121.14 (14)
C6—C7—H7A	110.2 (9)	C19—C20—H20	120.2 (9)
C8—C7—H7A	108.9 (9)	C21—C20—H20	118.6 (9)
C6—C7—H7B	110.2 (11)	C22—C21—C20	120.0 (2)
C8—C7—H7B	108.7 (11)	C22—C21—H21	121.2 (9)
H7A—C7—H7B	107.9 (15)	C20—C21—H21	118.8 (9)
C7—C8—C1	112.72 (14)	C21—C22—C23	119.7 (2)
C7—C8—H8A	108.4 (10)	C21—C22—H22	121.8 (12)
C1—C8—H8A	107.2 (11)	C23—C22—H22	118.5 (12)
C7—C8—H8B	110.3 (10)	C22—C23—C24	120.3 (2)
C1—C8—H8B	111.8 (10)	C22—C23—H23	123.2 (12)
H8A—C8—H8B	106.1 (14)	C24—C23—H23	116.5 (12)
C1—C9—C5	107.60 (14)	C23—C24—C19	121.0 (2)
C1—C9—H9A	107.7 (11)	C23—C24—H24	121.5 (10)
C5—C9—H9A	113.3 (11)	C19—C24—H24	117.5 (10)
C9—C1—C2—N3	39.2 (2)	C2—N3—C10—O11	162.60 (13)
C8—C1—C2—N3	−86.5 (2)	C4—N3—C10—C12	−168.16 (13)
C9—C1—C2—C13	169.47 (12)	C2—N3—C10—C12	−17.2 (2)
C8—C1—C2—C13	43.8 (2)	N3—C2—C13—C14	30.9 (2)
C13—C2—N3—C10	71.4 (2)	C1—C2—C13—C14	−100.0 (2)
C1—C2—N3—C10	−159.53 (12)	N3—C2—C13—C18	−150.32 (13)
C13—C2—N3—C4	−140.98 (12)	C1—C2—C13—C18	78.8 (2)
C1—C2—N3—C4	−11.9 (2)	C18—C13—C14—C15	−0.6 (2)
C10—N3—C4—C19	−69.56 (14)	C2—C13—C14—C15	178.25 (14)
C2—N3—C4—C19	141.28 (12)	C13—C14—C15—C16	−0.4 (3)
C10—N3—C4—C5	160.90 (12)	C14—C15—C16—C17	0.8 (3)
C2—N3—C4—C5	11.7 (2)	C15—C16—C17—C18	−0.3 (3)
N3—C4—C5—C9	−38.7 (2)	C16—C17—C18—C13	−0.6 (3)
C19—C4—C5—C9	−169.53 (13)	C14—C13—C18—C17	1.1 (2)
N3—C4—C5—C6	87.0 (2)	C2—C13—C18—C17	−177.82 (15)
C19—C4—C5—C6	−43.8 (2)	N3—C4—C19—C20	−26.9 (2)
C9—C5—C6—C7	57.5 (2)	C5—C4—C19—C20	104.6 (2)
C4—C5—C6—C7	−67.3 (2)	N3—C4—C19—C24	157.14 (13)
C5—C6—C7—C8	−51.3 (2)	C5—C4—C19—C24	−71.3 (2)
C6—C7—C8—C1	50.8 (2)	C24—C19—C20—C21	1.7 (2)
C9—C1—C8—C7	−56.5 (2)	C4—C19—C20—C21	−174.21 (15)
C2—C1—C8—C7	68.1 (2)	C19—C20—C21—C22	−0.2 (3)
C8—C1—C9—C5	60.0 (2)	C20—C21—C22—C23	−1.2 (3)
C2—C1—C9—C5	−68.4 (2)	C21—C22—C23—C24	1.1 (3)
C6—C5—C9—C1	−60.4 (2)	C22—C23—C24—C19	0.5 (3)
C4—C5—C9—C1	68.3 (2)	C20—C19—C24—C23	−1.8 (2)
C4—N3—C10—O11	11.6 (2)	C4—C19—C24—C23	174.3 (2)

(MHABN) N-Methyl-2,4-diorthomethyl phenyl-9-hydroxy 3-azabicyclo[3.3.1]nonane

Crystal data

C23H29NO	F(000) = 728
Mr = 335.47	Dx = 1.184 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.638 (1) Å	Cell parameters from 45 reflections
b = 13.188 (1) Å	θ = 7–15°
c = 18.865 (2) Å	µ = 0.07 mm^−1
β = 97.94 (1)°	T = 293 K
V = 1882.1 (3) Å^3	Plate, pale yellow
Z = 4	0.68 × 0.59 × 0.31 mm

Data collection

Siemens P4 diffractometer	Rint = 0.028
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.2°
Graphite monochromator	h = −1→9
θ/2θ scans	k = −1→17
5655 measured reflections	l = −24→24
4270 independent reflections	3 standard reflections every 100 reflections
3062 reflections with I > 2σ(I)	intensity decay: <1%

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)] = 0.043	All H-atom parameters refined
wR(F^2) = 0.135	Calculated w = 1/[σ^2(Fo^2) + (0.0705P)^2 + 0.0381P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
4269 reflections	Δρmax = 0.23 e Å^−3
343 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (16)

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 on F² for ALL reflections except for 1 with very negative F²

or 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
C1	0.1049 (2)	0.19893 (10)	0.19455 (7)	0.0414 (3)
C2	0.1187 (2)	0.08792 (9)	0.22148 (6)	0.0357 (3)
N3	0.00113 (14)	0.06656 (8)	0.27590 (5)	0.0355 (2)
C4	0.0204 (2)	0.14188 (10)	0.33440 (6)	0.0359 (3)
C5	0.0073 (2)	0.25244 (10)	0.30711 (7)	0.0411 (3)
C6	−0.1727 (2)	0.28536 (12)	0.26755 (8)	0.0487 (3)
C7	−0.2241 (2)	0.23019 (12)	0.19654 (8)	0.0495 (4)
C8	−0.0732 (2)	0.22895 (12)	0.15165 (7)	0.0497 (4)
C9	0.1468 (2)	0.27018 (11)	0.25812 (8)	0.0455 (3)
O10	0.32288 (14)	0.24968 (9)	0.29126 (7)	0.0576 (3)
C11	0.0464 (2)	−0.03323 (11)	0.30766 (8)	0.0457 (3)
C12	0.0850 (2)	0.01491 (9)	0.15865 (6)	0.0375 (3)
C13	0.2193 (2)	−0.00942 (11)	0.11756 (7)	0.0461 (3)
C14	0.1804 (2)	−0.07659 (12)	0.06059 (8)	0.0560 (4)
C15	0.0167 (3)	−0.12087 (12)	0.04425 (8)	0.0593 (4)
C16	−0.1152 (2)	−0.09646 (12)	0.08400 (8)	0.0540 (4)
C17	−0.0811 (2)	−0.02858 (11)	0.14029 (7)	0.0436 (3)
C18	0.4029 (2)	0.0345 (2)	0.13244 (13)	0.0691 (5)
C19	−0.1133 (2)	0.12445 (10)	0.38627 (6)	0.0376 (3)
C20	−0.0693 (2)	0.14465 (11)	0.45961 (7)	0.0448 (3)
C21	−0.2010 (2)	0.13675 (13)	0.50363 (8)	0.0573 (4)
C22	−0.3697 (2)	0.10757 (15)	0.47766 (10)	0.0652 (5)
C23	−0.4124 (2)	0.0855 (2)	0.40616 (10)	0.0654 (5)
C24	−0.2849 (2)	0.09382 (13)	0.36106 (9)	0.0536 (4)
C25	0.1156 (3)	0.1715 (2)	0.49312 (10)	0.0703 (6)
H1	0.199 (2)	0.2071 (12)	0.1621 (8)	0.047 (4)*
H2	0.2423 (18)	0.0781 (9)	0.2450 (7)	0.031 (3)*
H4	0.1423 (17)	0.1331 (10)	0.3627 (7)	0.031 (3)*
H5	0.0370 (19)	0.2940 (12)	0.3508 (8)	0.045 (4)*
H6A	−0.164 (2)	0.3607 (13)	0.2574 (8)	0.052 (4)*
H6B	−0.266 (2)	0.2754 (12)	0.2992 (8)	0.052 (4)*
H7A	−0.332 (2)	0.2610 (13)	0.1704 (9)	0.059 (5)*
H7B	−0.262 (2)	0.1596 (13)	0.2065 (8)	0.053 (4)*
H8A	−0.1016 (19)	0.1813 (12)	0.1106 (8)	0.050 (4)*
H8B	−0.057 (2)	0.2965 (15)	0.1325 (9)	0.062 (5)*
H9	0.1414 (18)	0.3412 (11)	0.2399 (7)	0.042 (4)*
H10	0.351 (3)	0.289 (2)	0.3265 (13)	0.099 (8)*
H11A	0.032 (2)	−0.0886 (12)	0.2698 (9)	0.054 (4)*
H11B	−0.033 (2)	−0.0505 (14)	0.3449 (9)	0.061 (5)*
H11C	0.169 (3)	−0.0316 (14)	0.3319 (10)	0.070 (5)*
H14	0.274 (3)	−0.0921 (15)	0.0325 (11)	0.075 (6)*
H15	−0.010 (2)	−0.1698 (14)	0.0025 (10)	0.067 (5)*
H16	−0.232 (2)	−0.1252 (13)	0.0731 (8)	0.055 (4)*
H17	−0.177 (2)	−0.0099 (12)	0.1698 (8)	0.053 (4)*
H18A	0.458 (4)	0.033 (3)	0.1831 (17)	0.135 (11)*
H18B	0.485 (3)	0.005 (2)	0.1051 (13)	0.104 (7)*
H18C	0.408 (4)	0.106 (3)	0.1213 (18)	0.151 (12)*
H21	−0.166 (2)	0.1544 (13)	0.5546 (10)	0.062 (5)*
H22	−0.457 (3)	0.0998 (15)	0.5079 (12)	0.083 (6)*
H23	−0.528 (3)	0.0601 (16)	0.3863 (11)	0.080 (6)*
H24	−0.318 (2)	0.0799 (13)	0.3110 (10)	0.057 (5)*
H25A	0.126 (3)	0.183 (2)	0.5402 (16)	0.122 (9)*
H25B	0.184 (3)	0.2215 (19)	0.4661 (13)	0.104 (7)*
H25C	0.200 (4)	0.112 (3)	0.4936 (17)	0.147 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0479 (7)	0.0386 (6)	0.0403 (7)	−0.0015 (6)	0.0149 (6)	0.0035 (5)
C2	0.0337 (6)	0.0382 (6)	0.0357 (6)	−0.0002 (5)	0.0063 (5)	0.0023 (5)
N3	0.0396 (5)	0.0355 (5)	0.0320 (5)	−0.0023 (4)	0.0067 (4)	0.0011 (4)
C4	0.0341 (6)	0.0413 (6)	0.0320 (6)	−0.0034 (5)	0.0029 (5)	−0.0008 (5)
C5	0.0487 (8)	0.0375 (6)	0.0377 (6)	−0.0043 (6)	0.0080 (6)	−0.0048 (5)
C6	0.0547 (8)	0.0462 (8)	0.0466 (7)	0.0103 (7)	0.0117 (7)	0.0004 (6)
C7	0.0493 (8)	0.0533 (9)	0.0439 (7)	0.0137 (7)	−0.0008 (6)	0.0033 (6)
C8	0.0641 (9)	0.0473 (8)	0.0372 (7)	0.0104 (7)	0.0058 (6)	0.0049 (6)
C9	0.0493 (8)	0.0386 (7)	0.0499 (7)	−0.0069 (6)	0.0109 (6)	0.0007 (6)
O10	0.0466 (6)	0.0592 (7)	0.0666 (7)	−0.0157 (5)	0.0067 (5)	−0.0081 (5)
C11	0.0566 (9)	0.0392 (7)	0.0417 (7)	−0.0001 (6)	0.0080 (7)	0.0064 (6)
C12	0.0417 (7)	0.0372 (6)	0.0346 (6)	0.0036 (5)	0.0080 (5)	0.0044 (5)
C13	0.0506 (8)	0.0434 (7)	0.0469 (7)	0.0102 (6)	0.0154 (6)	0.0065 (6)
C14	0.0770 (11)	0.0487 (8)	0.0465 (8)	0.0160 (8)	0.0238 (8)	0.0031 (6)
C15	0.0943 (13)	0.0457 (8)	0.0382 (7)	0.0036 (8)	0.0102 (8)	−0.0049 (6)
C16	0.0675 (10)	0.0515 (8)	0.0413 (7)	−0.0094 (8)	0.0010 (7)	−0.0019 (6)
C17	0.0465 (8)	0.0467 (7)	0.0383 (6)	−0.0021 (6)	0.0075 (6)	−0.0009 (6)
C18	0.0476 (10)	0.0729 (12)	0.093 (2)	0.0032 (9)	0.0303 (10)	−0.0031 (11)
C19	0.0365 (7)	0.0425 (7)	0.0341 (6)	−0.0008 (5)	0.0057 (5)	0.0026 (5)
C20	0.0528 (8)	0.0463 (7)	0.0352 (6)	−0.0010 (6)	0.0060 (6)	0.0033 (5)
C21	0.0743 (11)	0.0606 (9)	0.0397 (7)	0.0056 (8)	0.0172 (7)	0.0077 (7)
C22	0.0618 (11)	0.0762 (12)	0.0641 (10)	0.0072 (9)	0.0314 (9)	0.0170 (8)
C23	0.0395 (8)	0.0870 (13)	0.0710 (11)	−0.0036 (8)	0.0120 (8)	0.0160 (9)
C24	0.0417 (8)	0.0734 (10)	0.0451 (8)	−0.0071 (7)	0.0037 (6)	0.0060 (7)
C25	0.0697 (12)	0.098 (2)	0.0398 (8)	−0.0254 (12)	−0.0054 (8)	−0.0022 (9)

Geometric parameters (Å, º)

C1—C9	1.522 (2)	C12—C17	1.392 (2)
C1—C8	1.536 (2)	C12—C13	1.406 (2)
C1—C2	1.548 (2)	C13—C14	1.393 (2)
C1—H1	1.01 (2)	C13—C18	1.507 (2)
C2—N3	1.482 (2)	C14—C15	1.376 (3)
C2—C12	1.521 (2)	C14—H14	0.97 (2)
C2—H2	0.994 (14)	C15—C16	1.375 (2)
N3—C11	1.467 (2)	C15—H15	1.02 (2)
N3—C4	1.477 (2)	C16—C17	1.386 (2)
C4—C19	1.526 (2)	C16—H16	0.96 (2)
C4—C5	1.545 (2)	C17—H17	1.01 (2)
C4—H4	1.014 (13)	C18—H18A	0.99 (3)
C5—C9	1.522 (2)	C18—H18B	0.95 (3)
C5—C6	1.534 (2)	C18—H18C	0.97 (3)
C5—H5	0.989 (15)	C19—C24	1.391 (2)
C6—C7	1.527 (2)	C19—C20	1.403 (2)
C6—H6A	1.02 (2)	C20—C21	1.394 (2)
C6—H6B	1.00 (2)	C20—C25	1.508 (2)
C7—C8	1.521 (2)	C21—C22	1.369 (3)
C7—H7A	0.99 (2)	C21—H21	0.99 (2)
C7—H7B	1.00 (2)	C22—C23	1.374 (3)
C8—H8A	1.00 (2)	C22—H22	0.94 (2)
C8—H8B	0.98 (2)	C23—C24	1.383 (2)
C9—O10	1.428 (2)	C23—H23	0.97 (2)
C9—H9	0.996 (15)	C24—H24	0.96 (2)
O10—H10	0.85 (3)	C25—H25A	0.90 (3)
C11—H11A	1.02 (2)	C25—H25B	1.02 (3)
C11—H11B	1.01 (2)	C25—H25C	1.02 (3)
C11—H11C	0.99 (2)
C9—C1—C8	109.31 (12)	N3—C11—H11B	110.8 (10)
C9—C1—C2	109.14 (11)	H11A—C11—H11B	108.0 (14)
C8—C1—C2	115.58 (12)	N3—C11—H11C	109.0 (11)
C9—C1—H1	108.8 (9)	H11A—C11—H11C	110.2 (14)
C8—C1—H1	107.6 (8)	H11B—C11—H11C	107.7 (14)
C2—C1—H1	106.2 (9)	C17—C12—C13	118.57 (12)
N3—C2—C12	111.46 (10)	C17—C12—C2	120.34 (11)
N3—C2—C1	112.75 (10)	C13—C12—C2	121.08 (12)
C12—C2—C1	110.27 (10)	C14—C13—C12	118.46 (14)
N3—C2—H2	107.1 (7)	C14—C13—C18	118.81 (14)
C12—C2—H2	108.2 (7)	C12—C13—C18	122.73 (14)
C1—C2—H2	106.7 (7)	C15—C14—C13	122.22 (14)
C11—N3—C4	107.72 (10)	C15—C14—H14	120.3 (11)
C11—N3—C2	108.80 (10)	C13—C14—H14	117.5 (11)
C4—N3—C2	112.48 (9)	C16—C15—C14	119.37 (14)
N3—C4—C19	111.79 (10)	C16—C15—H15	119.2 (10)
N3—C4—C5	112.99 (10)	C14—C15—H15	121.4 (10)
C19—C4—C5	109.71 (10)	C15—C16—C17	119.6 (2)
N3—C4—H4	107.8 (7)	C15—C16—H16	121.1 (10)
C19—C4—H4	107.0 (7)	C17—C16—H16	119.2 (10)
C5—C4—H4	107.2 (7)	C16—C17—C12	121.70 (14)
C9—C5—C6	108.46 (11)	C16—C17—H17	120.6 (9)
C9—C5—C4	109.19 (11)	C12—C17—H17	117.7 (9)
C6—C5—C4	116.23 (11)	C13—C18—H18A	115.5 (17)
C9—C5—H5	108.7 (9)	C13—C18—H18B	114.2 (15)
C6—C5—H5	109.6 (8)	H18A—C18—H18B	107 (2)
C4—C5—H5	104.3 (9)	C13—C18—H18C	113.3 (19)
C7—C6—C5	113.36 (12)	H18A—C18—H18C	102 (3)
C7—C6—H6A	108.4 (9)	H18B—C18—H18C	103 (2)
C5—C6—H6A	106.9 (9)	C24—C19—C20	118.55 (12)
C7—C6—H6B	110.0 (9)	C24—C19—C4	120.46 (11)
C5—C6—H6B	109.8 (9)	C20—C19—C4	120.89 (11)
H6A—C6—H6B	108.2 (12)	C21—C20—C19	118.64 (13)
C8—C7—C6	111.76 (13)	C21—C20—C25	118.62 (14)
C8—C7—H7A	111.6 (10)	C19—C20—C25	122.71 (13)
C6—C7—H7A	109.8 (10)	C22—C21—C20	121.91 (15)
C8—C7—H7B	110.7 (9)	C22—C21—H21	121.8 (10)
C6—C7—H7B	109.0 (9)	C20—C21—H21	116.3 (10)
H7A—C7—H7B	103.7 (13)	C21—C22—C23	119.66 (15)
C7—C8—C1	113.16 (11)	C21—C22—H22	121.6 (13)
C7—C8—H8A	109.8 (9)	C23—C22—H22	118.7 (13)
C1—C8—H8A	109.2 (9)	C22—C23—C24	119.7 (2)
C7—C8—H8B	110.0 (10)	C22—C23—H23	122.1 (12)
C1—C8—H8B	106.3 (10)	C24—C23—H23	118.1 (12)
H8A—C8—H8B	108.2 (13)	C23—C24—C19	121.53 (15)
O10—C9—C5	113.64 (11)	C23—C24—H24	118.6 (10)
O10—C9—C1	108.10 (12)	C19—C24—H24	119.9 (10)
C5—C9—C1	107.14 (11)	C20—C25—H25A	113.7 (17)
O10—C9—H9	108.7 (8)	C20—C25—H25B	117.2 (13)
C5—C9—H9	110.8 (8)	H25A—C25—H25B	114 (2)
C1—C9—H9	108.3 (8)	C20—C25—H25C	111.9 (18)
C9—O10—H10	110.6 (16)	H25A—C25—H25C	99 (2)
N3—C11—H11A	111.2 (9)	H25B—C25—H25C	98 (2)
C9—C1—C2—N3	57.07 (14)	N3—C2—C12—C17	27.9 (2)
C8—C1—C2—N3	−66.58 (14)	C1—C2—C12—C17	−98.14 (14)
C9—C1—C2—C12	−177.63 (10)	N3—C2—C12—C13	−152.71 (11)
C8—C1—C2—C12	58.72 (14)	C1—C2—C12—C13	81.26 (14)
C12—C2—N3—C11	65.71 (13)	C17—C12—C13—C14	−0.5 (2)
C1—C2—N3—C11	−169.64 (11)	C2—C12—C13—C14	−179.86 (12)
C12—C2—N3—C4	−175.03 (10)	C17—C12—C13—C18	179.3 (2)
C1—C2—N3—C4	−50.38 (14)	C2—C12—C13—C18	−0.1 (2)
C11—N3—C4—C19	−65.35 (13)	C12—C13—C14—C15	−1.2 (2)
C2—N3—C4—C19	174.76 (10)	C18—C13—C14—C15	179.1 (2)
C11—N3—C4—C5	170.31 (11)	C13—C14—C15—C16	1.7 (2)
C2—N3—C4—C5	50.42 (13)	C14—C15—C16—C17	−0.7 (2)
N3—C4—C5—C9	−57.07 (13)	C15—C16—C17—C12	−1.0 (2)
C19—C4—C5—C9	177.46 (10)	C13—C12—C17—C16	1.5 (2)
N3—C4—C5—C6	65.97 (14)	C2—C12—C17—C16	−179.07 (13)
C19—C4—C5—C6	−59.49 (14)	N3—C4—C19—C24	−38.0 (2)
C9—C5—C6—C7	57.5 (2)	C5—C4—C19—C24	88.19 (15)
C4—C5—C6—C7	−65.9 (2)	N3—C4—C19—C20	145.84 (12)
C5—C6—C7—C8	−47.5 (2)	C5—C4—C19—C20	−88.01 (14)
C6—C7—C8—C1	46.6 (2)	C24—C19—C20—C21	−2.3 (2)
C9—C1—C8—C7	−56.2 (2)	C4—C19—C20—C21	173.97 (13)
C2—C1—C8—C7	67.3 (2)	C24—C19—C20—C25	175.8 (2)
C6—C5—C9—O10	175.36 (11)	C4—C19—C20—C25	−7.9 (2)
C4—C5—C9—O10	−57.08 (14)	C19—C20—C21—C22	1.6 (2)
C6—C5—C9—C1	−65.29 (14)	C25—C20—C21—C22	−176.6 (2)
C4—C5—C9—C1	62.27 (13)	C20—C21—C22—C23	−0.2 (3)
C8—C1—C9—O10	−172.18 (11)	C21—C22—C23—C24	−0.5 (3)
C2—C1—C9—O10	60.53 (13)	C22—C23—C24—C19	−0.3 (3)
C8—C1—C9—C5	64.97 (14)	C20—C19—C24—C23	1.7 (2)
C2—C1—C9—C5	−62.31 (14)	C4—C19—C24—C23	−174.63 (15)