Structural insights into methyl- or meth­oxy-substituted 1-(α-amino­benz­yl)-2-naphthol structures: the role of C—H...π inter­actions

Amino­benzyl­naphthols are a class of compounds containing a large aromatic mol­ecular surface which makes them suitable candidates to study the role of C—H...π inter­actions. We have investigated the effect of methyl or meth­oxy substituents on the assembling of aromatic units by preparing and determining the crystal structures of (S,S)-1-{(4-methyl­phen­yl)[(1-phenyl­eth­yl)amino]­meth­yl}naphthalen-2-ol, C₂₆H₂₅NO, and (S,S)-1-{(4-meth­oxy­phen­yl)[(1-phenyl­eth­yl)amino]­meth­yl}naphthalen-2-ol, C₂₆H₂₅NO₂. The methyl group influ­enced the overall crystal packing even if the H atoms of the methyl group did not participate directly either in hydrogen bonding or C—H...π inter­actions. The introduction of the meth­oxy moiety caused the formation of new hydrogen bonds, in which the O atom of the methoxy group was directly involved. Moreover, the meth­oxy group promoted the formation of an inter­esting C—H...π inter­action which altered the orientation of an aromatic unit.

Computing details

For both structures, data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia,2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015).

(S,S)-1-{(4-Methylphenyl)[(1-phenylethyl)amino]methyl}naphthalen-2-ol (4)

Crystal data

C26H25NO	Dx = 1.177 Mg m^−3
Mr = 367.47	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8050 reflections
a = 9.6571 (2) Å	θ = 2.5–29.1°
b = 13.0874 (3) Å	µ = 0.07 mm^−1
c = 16.4113 (4) Å	T = 296 K
V = 2074.16 (8) Å^3	Irregular block, colourless
Z = 4	0.4 × 0.36 × 0.12 mm
F(000) = 784

Data collection

Bruker APEXII CCD diffractometer	6385 independent reflections
Radiation source: fine-focus sealed tube	5093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 30.6°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
Tmin = 0.709, Tmax = 0.746	k = −17→18
25559 measured reflections	l = −20→23

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 0.0702P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.115	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.17 e Å^−3
6385 reflections	Δρmin = −0.16 e Å^−3
260 parameters	Absolute structure: Flack x determined using 1885 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.6 (6)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C11	0.76319 (17)	0.43689 (12)	0.48474 (9)	0.0325 (3)
H11	0.815665	0.494052	0.507855	0.039*
C19	0.77755 (19)	0.37333 (13)	0.62733 (10)	0.0373 (3)
H19	0.696122	0.415889	0.638191	0.045*
C10	0.57671 (18)	0.57166 (13)	0.45560 (9)	0.0348 (3)
C5	0.4353 (2)	0.59950 (15)	0.44372 (11)	0.0434 (4)
C9	0.6765 (2)	0.64958 (14)	0.44489 (12)	0.0449 (4)
H9	0.769699	0.634327	0.452324	0.054*
C2	0.50493 (18)	0.39871 (13)	0.48665 (10)	0.0371 (4)
H2	0.851 (2)	0.3152 (16)	0.5297 (12)	0.038 (5)*
C3	0.36515 (19)	0.42810 (16)	0.47607 (13)	0.0472 (4)
H3	0.295238	0.380264	0.484040	0.057*
C21	0.90423 (17)	0.43092 (13)	0.65697 (9)	0.0337 (3)
C1	0.61122 (16)	0.46893 (13)	0.47721 (9)	0.0319 (3)
C12	0.82430 (18)	0.41055 (14)	0.40225 (10)	0.0375 (4)
C26	1.0341 (2)	0.42097 (17)	0.62176 (12)	0.0483 (5)
H26	1.044452	0.382118	0.574699	0.058*
C4	0.3319 (2)	0.52411 (17)	0.45466 (13)	0.0511 (5)
H4	0.239350	0.541309	0.446912	0.061*
C22	0.89314 (19)	0.49056 (16)	0.72639 (11)	0.0467 (4)
H22	0.806937	0.499174	0.750702	0.056*
C24	1.1355 (2)	0.52631 (18)	0.72494 (13)	0.0522 (5)
H24	1.212509	0.557936	0.747808	0.063*
C17	0.7791 (2)	0.32630 (17)	0.35845 (11)	0.0490 (5)
H17	0.710229	0.284640	0.380006	0.059*
C6	0.4018 (2)	0.70028 (18)	0.42078 (15)	0.0602 (6)
H6	0.309510	0.717513	0.412192	0.072*
C8	0.6390 (3)	0.74720 (16)	0.42379 (15)	0.0589 (5)
H8	0.706961	0.797000	0.418014	0.071*
C25	1.1489 (2)	0.46830 (19)	0.65590 (14)	0.0558 (5)
H25	1.235360	0.460595	0.631760	0.067*
C14	0.9797 (2)	0.4485 (3)	0.29086 (14)	0.0656 (7)
H14	1.046760	0.490989	0.268405	0.079*
C23	1.0072 (2)	0.5373 (2)	0.76006 (12)	0.0552 (5)
H23	0.997417	0.576593	0.806916	0.066*
C13	0.9266 (2)	0.47088 (19)	0.36760 (13)	0.0526 (5)
H13	0.960163	0.527102	0.396063	0.063*
C7	0.5010 (3)	0.77289 (19)	0.41091 (17)	0.0679 (7)
H7	0.476832	0.838987	0.395707	0.082*
C20	0.7614 (3)	0.27401 (18)	0.67573 (14)	0.0663 (7)
H20A	0.840690	0.231248	0.666678	0.099*
H20B	0.679349	0.238973	0.658115	0.099*
H20C	0.754025	0.289540	0.732733	0.099*
C15	0.9353 (2)	0.3653 (2)	0.24776 (12)	0.0646 (7)
C16	0.8353 (3)	0.3035 (2)	0.28301 (13)	0.0622 (6)
H16	0.805379	0.245476	0.255416	0.075*
C18	0.9915 (3)	0.3419 (4)	0.16420 (15)	0.0999 (12)
H18A	1.024472	0.272672	0.162806	0.150*
H18B	1.066485	0.387592	0.152084	0.150*
H18C	0.919501	0.350370	0.124463	0.150*
O1	0.52696 (15)	0.29898 (10)	0.50527 (9)	0.0480 (3)
H1	0.609285	0.290086	0.515243	0.072*
N1	0.77733 (16)	0.34748 (10)	0.53991 (8)	0.0349 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0320 (7)	0.0323 (7)	0.0330 (7)	−0.0024 (6)	−0.0028 (6)	0.0023 (6)
C19	0.0373 (8)	0.0417 (8)	0.0327 (7)	−0.0011 (7)	0.0010 (6)	0.0017 (6)
C10	0.0378 (8)	0.0372 (8)	0.0295 (7)	0.0034 (7)	0.0010 (6)	0.0005 (6)
C5	0.0404 (9)	0.0488 (10)	0.0410 (9)	0.0103 (8)	0.0014 (7)	0.0005 (7)
C9	0.0451 (9)	0.0398 (9)	0.0498 (10)	0.0018 (8)	0.0056 (8)	0.0061 (8)
C2	0.0358 (8)	0.0383 (9)	0.0372 (8)	−0.0044 (7)	0.0011 (6)	−0.0044 (6)
C3	0.0335 (9)	0.0533 (11)	0.0548 (11)	−0.0065 (8)	0.0040 (7)	−0.0083 (8)
C21	0.0353 (8)	0.0374 (8)	0.0285 (7)	0.0040 (6)	−0.0009 (6)	0.0017 (6)
C1	0.0308 (7)	0.0344 (7)	0.0304 (7)	−0.0004 (6)	−0.0006 (5)	−0.0015 (6)
C12	0.0307 (7)	0.0470 (9)	0.0348 (8)	0.0054 (7)	−0.0017 (6)	0.0060 (7)
C26	0.0430 (10)	0.0570 (12)	0.0447 (9)	0.0029 (8)	0.0060 (8)	−0.0162 (9)
C4	0.0325 (8)	0.0641 (12)	0.0567 (11)	0.0086 (8)	0.0010 (8)	−0.0051 (10)
C22	0.0380 (9)	0.0644 (12)	0.0377 (8)	0.0018 (8)	0.0062 (7)	−0.0104 (8)
C24	0.0410 (10)	0.0652 (13)	0.0503 (10)	−0.0037 (9)	−0.0070 (8)	−0.0099 (9)
C17	0.0535 (11)	0.0575 (11)	0.0358 (9)	0.0003 (9)	0.0035 (8)	0.0001 (8)
C6	0.0540 (12)	0.0610 (13)	0.0655 (13)	0.0220 (10)	0.0032 (10)	0.0108 (11)
C8	0.0660 (14)	0.0403 (10)	0.0705 (14)	0.0005 (10)	0.0115 (11)	0.0126 (10)
C25	0.0344 (10)	0.0708 (14)	0.0623 (13)	0.0021 (9)	0.0072 (8)	−0.0172 (11)
C14	0.0368 (10)	0.106 (2)	0.0541 (12)	0.0056 (12)	0.0112 (9)	0.0142 (13)
C23	0.0502 (11)	0.0763 (15)	0.0391 (9)	−0.0037 (10)	0.0015 (8)	−0.0193 (9)
C13	0.0325 (9)	0.0707 (13)	0.0548 (11)	−0.0031 (9)	0.0043 (8)	0.0050 (10)
C7	0.0761 (16)	0.0493 (12)	0.0784 (15)	0.0210 (11)	0.0126 (13)	0.0198 (11)
C20	0.0880 (17)	0.0647 (13)	0.0460 (11)	−0.0284 (13)	−0.0052 (11)	0.0191 (10)
C15	0.0435 (11)	0.111 (2)	0.0396 (10)	0.0237 (13)	0.0046 (8)	0.0084 (12)
C16	0.0682 (14)	0.0807 (16)	0.0376 (10)	0.0130 (13)	−0.0006 (9)	−0.0076 (10)
C18	0.0747 (19)	0.182 (4)	0.0432 (12)	0.024 (2)	0.0143 (12)	0.0014 (18)
O1	0.0443 (7)	0.0363 (6)	0.0632 (8)	−0.0087 (5)	−0.0034 (6)	−0.0007 (6)
N1	0.0390 (7)	0.0329 (6)	0.0328 (7)	0.0030 (6)	−0.0031 (5)	0.0012 (5)

Geometric parameters (Å, º)

C11—N1	1.486 (2)	C22—H22	0.9300
C11—C12	1.516 (2)	C24—C25	1.370 (3)
C11—C1	1.531 (2)	C24—C23	1.374 (3)
C11—H11	0.9800	C24—H24	0.9300
C19—N1	1.474 (2)	C17—C16	1.384 (3)
C19—C21	1.517 (2)	C17—H17	0.9300
C19—C20	1.531 (3)	C6—C7	1.359 (4)
C19—H19	0.9800	C6—H6	0.9300
C10—C9	1.414 (3)	C8—C7	1.391 (4)
C10—C5	1.426 (2)	C8—H8	0.9300
C10—C1	1.430 (2)	C25—H25	0.9300
C5—C6	1.409 (3)	C14—C15	1.367 (4)
C5—C4	1.416 (3)	C14—C13	1.391 (3)
C9—C8	1.372 (3)	C14—H14	0.9300
C9—H9	0.9300	C23—H23	0.9300
C2—O1	1.357 (2)	C13—H13	0.9300
C2—C1	1.386 (2)	C7—H7	0.9300
C2—C3	1.414 (3)	C20—H20A	0.9600
C3—C4	1.344 (3)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C21—C22	1.385 (2)	C15—C16	1.386 (4)
C21—C26	1.387 (2)	C15—C18	1.507 (3)
C12—C13	1.387 (3)	C16—H16	0.9300
C12—C17	1.387 (3)	C18—H18A	0.9600
C26—C25	1.387 (3)	C18—H18B	0.9600
C26—H26	0.9300	C18—H18C	0.9600
C4—H4	0.9300	O1—H1	0.8200
C22—C23	1.376 (3)	N1—H2	0.84 (2)
N1—C11—C12	109.22 (13)	C23—C24—H24	120.3
N1—C11—C1	110.67 (13)	C16—C17—C12	120.8 (2)
C12—C11—C1	111.29 (12)	C16—C17—H17	119.6
N1—C11—H11	108.5	C12—C17—H17	119.6
C12—C11—H11	108.5	C7—C6—C5	121.6 (2)
C1—C11—H11	108.5	C7—C6—H6	119.2
N1—C19—C21	115.29 (14)	C5—C6—H6	119.2
N1—C19—C20	108.06 (15)	C9—C8—C7	121.1 (2)
C21—C19—C20	109.73 (15)	C9—C8—H8	119.5
N1—C19—H19	107.8	C7—C8—H8	119.5
C21—C19—H19	107.8	C24—C25—C26	120.42 (18)
C20—C19—H19	107.8	C24—C25—H25	119.8
C9—C10—C5	116.81 (16)	C26—C25—H25	119.8
C9—C10—C1	123.38 (15)	C15—C14—C13	121.4 (2)
C5—C10—C1	119.81 (15)	C15—C14—H14	119.3
C6—C5—C4	121.59 (19)	C13—C14—H14	119.3
C6—C5—C10	119.71 (19)	C24—C23—C22	120.47 (18)
C4—C5—C10	118.70 (17)	C24—C23—H23	119.8
C8—C9—C10	121.52 (19)	C22—C23—H23	119.8
C8—C9—H9	119.2	C12—C13—C14	120.9 (2)
C10—C9—H9	119.2	C12—C13—H13	119.5
O1—C2—C1	123.13 (16)	C14—C13—H13	119.5
O1—C2—C3	116.03 (16)	C6—C7—C8	119.2 (2)
C1—C2—C3	120.84 (17)	C6—C7—H7	120.4
C4—C3—C2	120.99 (18)	C8—C7—H7	120.4
C4—C3—H3	119.5	C19—C20—H20A	109.5
C2—C3—H3	119.5	C19—C20—H20B	109.5
C22—C21—C26	117.74 (16)	H20A—C20—H20B	109.5
C22—C21—C19	118.77 (15)	C19—C20—H20C	109.5
C26—C21—C19	123.31 (15)	H20A—C20—H20C	109.5
C2—C1—C10	118.59 (15)	H20B—C20—H20C	109.5
C2—C1—C11	121.27 (15)	C14—C15—C16	117.9 (2)
C10—C1—C11	120.06 (14)	C14—C15—C18	121.3 (3)
C13—C12—C17	117.66 (18)	C16—C15—C18	120.8 (3)
C13—C12—C11	120.93 (17)	C17—C16—C15	121.4 (2)
C17—C12—C11	121.40 (16)	C17—C16—H16	119.3
C21—C26—C25	120.80 (17)	C15—C16—H16	119.3
C21—C26—H26	119.6	C15—C18—H18A	109.5
C25—C26—H26	119.6	C15—C18—H18B	109.5
C3—C4—C5	121.06 (18)	H18A—C18—H18B	109.5
C3—C4—H4	119.5	C15—C18—H18C	109.5
C5—C4—H4	119.5	H18A—C18—H18C	109.5
C23—C22—C21	121.26 (17)	H18B—C18—H18C	109.5
C23—C22—H22	119.4	C2—O1—H1	109.5
C21—C22—H22	119.4	C19—N1—C11	114.37 (13)
C25—C24—C23	119.32 (19)	C19—N1—H2	107.9 (14)
C25—C24—H24	120.3	C11—N1—H2	110.6 (14)
C9—C10—C5—C6	1.3 (3)	C19—C21—C26—C25	−174.10 (19)
C1—C10—C5—C6	−178.70 (18)	C2—C3—C4—C5	−1.4 (3)
C9—C10—C5—C4	−179.34 (17)	C6—C5—C4—C3	179.6 (2)
C1—C10—C5—C4	0.7 (2)	C10—C5—C4—C3	0.2 (3)
C5—C10—C9—C8	−0.2 (3)	C26—C21—C22—C23	−0.9 (3)
C1—C10—C9—C8	179.72 (19)	C19—C21—C22—C23	174.29 (19)
O1—C2—C3—C4	−177.60 (18)	C13—C12—C17—C16	0.4 (3)
C1—C2—C3—C4	1.6 (3)	C11—C12—C17—C16	179.65 (18)
N1—C19—C21—C22	156.02 (16)	C4—C5—C6—C7	179.5 (2)
C20—C19—C21—C22	−81.7 (2)	C10—C5—C6—C7	−1.2 (3)
N1—C19—C21—C26	−29.1 (2)	C10—C9—C8—C7	−1.0 (3)
C20—C19—C21—C26	93.1 (2)	C23—C24—C25—C26	−0.1 (4)
O1—C2—C1—C10	178.49 (15)	C21—C26—C25—C24	−0.4 (4)
C3—C2—C1—C10	−0.7 (2)	C25—C24—C23—C22	0.0 (4)
O1—C2—C1—C11	2.0 (2)	C21—C22—C23—C24	0.5 (4)
C3—C2—C1—C11	−177.21 (16)	C17—C12—C13—C14	1.3 (3)
C9—C10—C1—C2	179.60 (16)	C11—C12—C13—C14	−178.04 (19)
C5—C10—C1—C2	−0.4 (2)	C15—C14—C13—C12	−1.4 (4)
C9—C10—C1—C11	−3.8 (2)	C5—C6—C7—C8	0.0 (4)
C5—C10—C1—C11	176.11 (14)	C9—C8—C7—C6	1.1 (4)
N1—C11—C1—C2	−28.1 (2)	C13—C14—C15—C16	−0.1 (4)
C12—C11—C1—C2	93.51 (17)	C13—C14—C15—C18	179.2 (2)
N1—C11—C1—C10	155.40 (14)	C12—C17—C16—C15	−1.9 (3)
C12—C11—C1—C10	−82.96 (18)	C14—C15—C16—C17	1.7 (3)
N1—C11—C12—C13	−124.92 (17)	C18—C15—C16—C17	−177.6 (2)
C1—C11—C12—C13	112.60 (18)	C21—C19—N1—C11	−68.79 (19)
N1—C11—C12—C17	55.8 (2)	C20—C19—N1—C11	168.07 (16)
C1—C11—C12—C17	−66.7 (2)	C12—C11—N1—C19	155.82 (14)
C22—C21—C26—C25	0.8 (3)	C1—C11—N1—C19	−81.33 (17)

(S,S)-1-{(4-Methoxyphenyl)[(1-phenylethyl)amino]methyl}naphthalen-2-ol (5)

Crystal data

C26H25NO2	Dx = 1.240 Mg m^−3
Mr = 383.47	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2502 reflections
a = 11.740 (3) Å	θ = 3.4–26.2°
b = 11.933 (3) Å	µ = 0.08 mm^−1
c = 14.662 (4) Å	T = 100 K
V = 2054.0 (9) Å^3	Block, colourless
Z = 4	0.08 × 0.06 × 0.06 mm
F(000) = 816

Data collection

Bruker APEXII CCD diffractometer	6032 independent reflections
Radiation source: fine-focus sealed tube	4110 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ and ω scans	θmax = 30.1°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.687, Tmax = 0.746	k = −16→14
14384 measured reflections	l = −20→15

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.0395P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.104	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.20 e Å^−3
6032 reflections	Δρmin = −0.20 e Å^−3
269 parameters	Absolute structure: Flack x determined using 1348 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.4 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.1062 (2)	0.52051 (19)	0.57247 (17)	0.0207 (5)
C2	0.0389 (2)	0.5187 (2)	0.65293 (19)	0.0253 (6)
H2	−0.017558	0.572363	0.661193	0.030*
C3	0.0559 (2)	0.4398 (2)	0.71758 (19)	0.0263 (6)
H3	0.011362	0.440334	0.770022	0.032*
C4	0.1409 (2)	0.3562 (2)	0.70665 (18)	0.0207 (5)
H4	0.253 (3)	0.521 (2)	0.354 (2)	0.034 (8)*
C5	0.1634 (2)	0.2770 (2)	0.77580 (18)	0.0268 (6)
H5	0.120181	0.278093	0.828972	0.032*
C6	0.2470 (3)	0.1990 (2)	0.76612 (19)	0.0300 (6)
H6	0.261290	0.147784	0.812549	0.036*
C7	0.3111 (2)	0.1963 (2)	0.6860 (2)	0.0281 (6)
H7	0.367709	0.142427	0.679225	0.034*
C8	0.2922 (2)	0.2718 (2)	0.61723 (18)	0.0218 (5)
H8	0.336122	0.268220	0.564547	0.026*
C9	0.2064 (2)	0.3555 (2)	0.62498 (17)	0.0177 (5)
C10	0.18835 (19)	0.4392 (2)	0.55647 (16)	0.0172 (5)
C11	0.25973 (19)	0.4371 (2)	0.47002 (16)	0.0174 (5)
H11	0.267183	0.358719	0.450891	0.021*
C12	0.1123 (2)	0.4324 (2)	0.34783 (17)	0.0212 (5)
H12	0.052793	0.414290	0.392351	0.025*
C13	0.0598 (2)	0.5079 (2)	0.27549 (19)	0.0281 (6)
H13A	0.118297	0.533485	0.234720	0.042*
H13B	0.024464	0.571153	0.304344	0.042*
H13C	0.003697	0.466613	0.241762	0.042*
C14	0.1589 (2)	0.3230 (2)	0.31054 (18)	0.0211 (5)
C15	0.2367 (2)	0.3237 (2)	0.23891 (18)	0.0269 (6)
H15	0.254658	0.391081	0.210486	0.032*
C16	0.2879 (2)	0.2259 (2)	0.2093 (2)	0.0315 (6)
H16	0.340004	0.227766	0.161607	0.038*
C17	0.2610 (2)	0.1247 (2)	0.25117 (18)	0.0292 (6)
H17	0.295386	0.058721	0.231693	0.035*
C18	0.1834 (2)	0.1226 (2)	0.32152 (19)	0.0268 (6)
H18	0.164826	0.054920	0.349238	0.032*
C19	0.1329 (2)	0.2211 (2)	0.35117 (18)	0.0242 (6)
H19	0.080846	0.218874	0.398952	0.029*
C20	0.37925 (19)	0.4846 (2)	0.48108 (16)	0.0182 (5)
C21	0.4719 (2)	0.4265 (2)	0.44731 (17)	0.0226 (5)
H21	0.460227	0.357829	0.418728	0.027*
C22	0.5826 (2)	0.4683 (2)	0.45508 (18)	0.0255 (6)
H22	0.644083	0.428133	0.432046	0.031*
C23	0.5992 (2)	0.5700 (2)	0.49737 (17)	0.0246 (6)
C24	0.5072 (2)	0.6312 (2)	0.52992 (18)	0.0253 (6)
H24	0.518854	0.700722	0.556944	0.030*
C25	0.3977 (2)	0.5882 (2)	0.52203 (18)	0.0222 (5)
H25	0.336197	0.629017	0.544302	0.027*
C26	0.8031 (2)	0.5560 (3)	0.4845 (2)	0.0392 (8)
H26A	0.800623	0.542804	0.419976	0.059*
H26B	0.804260	0.485582	0.516180	0.059*
H26C	0.870522	0.597747	0.499350	0.059*
N1	0.20138 (18)	0.49887 (18)	0.39540 (15)	0.0206 (4)
O1	0.08566 (15)	0.60723 (14)	0.51500 (14)	0.0290 (5)
H1	0.117998	0.595921	0.466289	0.044*
O2	0.70444 (15)	0.61855 (16)	0.51157 (13)	0.0332 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0176 (11)	0.0183 (13)	0.0261 (13)	−0.0022 (10)	−0.0031 (10)	−0.0002 (10)
C2	0.0165 (12)	0.0280 (14)	0.0316 (15)	0.0015 (11)	0.0020 (11)	−0.0093 (12)
C3	0.0207 (12)	0.0328 (15)	0.0253 (14)	−0.0065 (11)	0.0060 (11)	−0.0076 (13)
C4	0.0176 (12)	0.0251 (14)	0.0195 (13)	−0.0071 (10)	0.0011 (10)	−0.0020 (10)
C5	0.0319 (14)	0.0291 (15)	0.0195 (14)	−0.0118 (12)	0.0017 (11)	0.0021 (12)
C6	0.0364 (16)	0.0294 (15)	0.0241 (14)	−0.0057 (12)	−0.0049 (13)	0.0094 (11)
C7	0.0278 (14)	0.0253 (15)	0.0311 (15)	0.0022 (11)	−0.0043 (12)	0.0071 (12)
C8	0.0201 (12)	0.0237 (13)	0.0215 (13)	−0.0015 (11)	0.0013 (10)	0.0016 (11)
C9	0.0160 (11)	0.0189 (12)	0.0182 (12)	−0.0047 (10)	−0.0037 (10)	−0.0011 (10)
C10	0.0135 (10)	0.0191 (12)	0.0191 (12)	−0.0026 (9)	−0.0010 (9)	−0.0002 (10)
C11	0.0160 (11)	0.0186 (11)	0.0177 (12)	−0.0008 (9)	−0.0034 (10)	0.0020 (9)
C12	0.0164 (11)	0.0284 (14)	0.0188 (12)	−0.0040 (10)	−0.0036 (10)	0.0055 (11)
C13	0.0193 (12)	0.0376 (16)	0.0272 (15)	−0.0042 (11)	−0.0065 (11)	0.0092 (13)
C14	0.0171 (11)	0.0298 (14)	0.0165 (12)	−0.0062 (10)	−0.0058 (10)	0.0024 (10)
C15	0.0279 (14)	0.0321 (15)	0.0208 (14)	−0.0100 (12)	0.0014 (11)	0.0054 (11)
C16	0.0304 (15)	0.0388 (16)	0.0253 (15)	−0.0054 (13)	0.0041 (12)	−0.0020 (13)
C17	0.0297 (14)	0.0323 (15)	0.0256 (15)	−0.0022 (12)	−0.0062 (12)	−0.0043 (12)
C18	0.0266 (14)	0.0277 (15)	0.0260 (15)	−0.0067 (11)	−0.0076 (11)	0.0037 (12)
C19	0.0186 (12)	0.0345 (15)	0.0196 (13)	−0.0082 (11)	−0.0017 (10)	0.0046 (11)
C20	0.0151 (10)	0.0238 (13)	0.0158 (12)	−0.0017 (10)	−0.0028 (10)	0.0049 (10)
C21	0.0212 (12)	0.0275 (14)	0.0192 (13)	−0.0011 (11)	−0.0010 (10)	0.0003 (11)
C22	0.0181 (12)	0.0369 (16)	0.0216 (13)	0.0033 (11)	0.0006 (11)	0.0050 (11)
C23	0.0180 (11)	0.0386 (15)	0.0173 (13)	−0.0067 (11)	−0.0036 (10)	0.0080 (11)
C24	0.0261 (13)	0.0268 (14)	0.0229 (14)	−0.0063 (11)	−0.0025 (11)	0.0030 (11)
C25	0.0191 (11)	0.0248 (14)	0.0228 (13)	0.0002 (10)	0.0005 (11)	0.0029 (11)
C26	0.0153 (12)	0.070 (2)	0.0326 (17)	−0.0068 (13)	−0.0017 (12)	0.0093 (16)
N1	0.0169 (10)	0.0245 (11)	0.0206 (11)	−0.0041 (9)	−0.0045 (9)	0.0066 (9)
O1	0.0256 (10)	0.0236 (10)	0.0378 (12)	0.0061 (8)	0.0012 (9)	0.0051 (8)
O2	0.0180 (8)	0.0525 (12)	0.0291 (11)	−0.0119 (8)	−0.0030 (8)	0.0045 (9)

Geometric parameters (Å, º)

C1—O1	1.356 (3)	C14—C19	1.388 (4)
C1—C10	1.388 (3)	C14—C15	1.392 (4)
C1—C2	1.420 (4)	C15—C16	1.382 (4)
C2—C3	1.350 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.390 (4)
C3—C4	1.421 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.376 (4)
C4—C5	1.411 (4)	C17—H17	0.9300
C4—C9	1.423 (3)	C18—C19	1.387 (4)
C5—C6	1.360 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.395 (4)	C20—C21	1.382 (3)
C6—H6	0.9300	C20—C25	1.391 (3)
C7—C8	1.370 (3)	C21—C22	1.397 (3)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.423 (3)	C22—C23	1.377 (4)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.432 (3)	C23—O2	1.380 (3)
C10—C11	1.520 (3)	C23—C24	1.388 (4)
C11—N1	1.487 (3)	C24—C25	1.389 (3)
C11—C20	1.522 (3)	C24—H24	0.9300
C11—H11	0.9800	C25—H25	0.9300
C12—N1	1.486 (3)	C26—O2	1.434 (3)
C12—C14	1.518 (4)	C26—H26A	0.9600
C12—C13	1.521 (3)	C26—H26B	0.9600
C12—H12	0.9800	C26—H26C	0.9600
C13—H13A	0.9600	N1—H4	0.90 (3)
C13—H13B	0.9600	O1—H1	0.8200
C13—H13C	0.9600
O1—C1—C10	123.5 (2)	C19—C14—C15	118.3 (2)
O1—C1—C2	115.4 (2)	C19—C14—C12	121.3 (2)
C10—C1—C2	121.1 (2)	C15—C14—C12	120.2 (2)
C3—C2—C1	120.8 (2)	C16—C15—C14	121.1 (2)
C3—C2—H2	119.6	C16—C15—H15	119.4
C1—C2—H2	119.6	C14—C15—H15	119.4
C2—C3—C4	121.0 (2)	C15—C16—C17	119.8 (3)
C2—C3—H3	119.5	C15—C16—H16	120.1
C4—C3—H3	119.5	C17—C16—H16	120.1
C5—C4—C3	121.4 (2)	C18—C17—C16	119.8 (3)
C5—C4—C9	120.0 (2)	C18—C17—H17	120.1
C3—C4—C9	118.6 (2)	C16—C17—H17	120.1
C6—C5—C4	121.2 (3)	C17—C18—C19	120.2 (2)
C6—C5—H5	119.4	C17—C18—H18	119.9
C4—C5—H5	119.4	C19—C18—H18	119.9
C5—C6—C7	119.5 (2)	C18—C19—C14	120.9 (2)
C5—C6—H6	120.2	C18—C19—H19	119.5
C7—C6—H6	120.2	C14—C19—H19	119.5
C8—C7—C6	121.1 (3)	C21—C20—C25	118.6 (2)
C8—C7—H7	119.4	C21—C20—C11	120.0 (2)
C6—C7—H7	119.4	C25—C20—C11	121.4 (2)
C7—C8—C9	121.2 (2)	C20—C21—C22	121.6 (2)
C7—C8—H8	119.4	C20—C21—H21	119.2
C9—C8—H8	119.4	C22—C21—H21	119.2
C4—C9—C8	117.0 (2)	C23—C22—C21	118.9 (2)
C4—C9—C10	120.4 (2)	C23—C22—H22	120.5
C8—C9—C10	122.5 (2)	C21—C22—H22	120.5
C1—C10—C9	118.1 (2)	C22—C23—O2	124.4 (2)
C1—C10—C11	122.4 (2)	C22—C23—C24	120.5 (2)
C9—C10—C11	119.5 (2)	O2—C23—C24	115.1 (2)
N1—C11—C10	110.58 (19)	C23—C24—C25	119.9 (3)
N1—C11—C20	108.55 (19)	C23—C24—H24	120.1
C10—C11—C20	114.41 (19)	C25—C24—H24	120.1
N1—C11—H11	107.7	C24—C25—C20	120.5 (2)
C10—C11—H11	107.7	C24—C25—H25	119.7
C20—C11—H11	107.7	C20—C25—H25	119.7
N1—C12—C14	112.0 (2)	O2—C26—H26A	109.5
N1—C12—C13	107.22 (19)	O2—C26—H26B	109.5
C14—C12—C13	113.8 (2)	H26A—C26—H26B	109.5
N1—C12—H12	107.9	O2—C26—H26C	109.5
C14—C12—H12	107.9	H26A—C26—H26C	109.5
C13—C12—H12	107.9	H26B—C26—H26C	109.5
C12—C13—H13A	109.5	C12—N1—C11	113.89 (19)
C12—C13—H13B	109.5	C12—N1—H4	108.4 (19)
H13A—C13—H13B	109.5	C11—N1—H4	109.7 (19)
C12—C13—H13C	109.5	C1—O1—H1	109.5
H13A—C13—H13C	109.5	C23—O2—C26	117.6 (2)
H13B—C13—H13C	109.5
O1—C1—C2—C3	−176.4 (2)	N1—C12—C14—C15	−68.0 (3)
C10—C1—C2—C3	2.4 (4)	C13—C12—C14—C15	53.8 (3)
C1—C2—C3—C4	−0.5 (4)	C19—C14—C15—C16	−0.6 (4)
C2—C3—C4—C5	176.7 (2)	C12—C14—C15—C16	174.2 (2)
C2—C3—C4—C9	−1.4 (3)	C14—C15—C16—C17	0.3 (4)
C3—C4—C5—C6	−178.1 (2)	C15—C16—C17—C18	0.3 (4)
C9—C4—C5—C6	−0.1 (4)	C16—C17—C18—C19	−0.6 (4)
C4—C5—C6—C7	−0.7 (4)	C17—C18—C19—C14	0.3 (4)
C5—C6—C7—C8	0.7 (4)	C15—C14—C19—C18	0.3 (4)
C6—C7—C8—C9	0.0 (4)	C12—C14—C19—C18	−174.5 (2)
C5—C4—C9—C8	0.7 (3)	N1—C11—C20—C21	−103.3 (2)
C3—C4—C9—C8	178.8 (2)	C10—C11—C20—C21	132.7 (2)
C5—C4—C9—C10	−176.7 (2)	N1—C11—C20—C25	74.4 (3)
C3—C4—C9—C10	1.4 (3)	C10—C11—C20—C25	−49.6 (3)
C7—C8—C9—C4	−0.7 (3)	C25—C20—C21—C22	1.3 (4)
C7—C8—C9—C10	176.7 (2)	C11—C20—C21—C22	179.1 (2)
O1—C1—C10—C9	176.4 (2)	C20—C21—C22—C23	−0.1 (4)
C2—C1—C10—C9	−2.2 (3)	C21—C22—C23—O2	178.0 (2)
O1—C1—C10—C11	−2.9 (4)	C21—C22—C23—C24	−1.5 (4)
C2—C1—C10—C11	178.4 (2)	C22—C23—C24—C25	1.7 (4)
C4—C9—C10—C1	0.4 (3)	O2—C23—C24—C25	−177.8 (2)
C8—C9—C10—C1	−176.9 (2)	C23—C24—C25—C20	−0.5 (4)
C4—C9—C10—C11	179.7 (2)	C21—C20—C25—C24	−1.0 (4)
C8—C9—C10—C11	2.4 (3)	C11—C20—C25—C24	−178.8 (2)
C1—C10—C11—N1	−22.4 (3)	C14—C12—N1—C11	−55.6 (3)
C9—C10—C11—N1	158.3 (2)	C13—C12—N1—C11	178.9 (2)
C1—C10—C11—C20	100.5 (3)	C10—C11—N1—C12	−81.2 (2)
C9—C10—C11—C20	−78.8 (3)	C20—C11—N1—C12	152.5 (2)
N1—C12—C14—C19	106.6 (3)	C22—C23—O2—C26	−3.3 (4)
C13—C12—C14—C19	−131.6 (2)	C24—C23—O2—C26	176.2 (2)