Synthesis, crystal structure and biological activity of 2-[2-(quinolin-2-yl)vinyl]-8-hydroxyquinoline and 2-[2-(quinolin-4-yl)vinyl]-8-hydroxyquinoline

Two new isomeric 8-hydroxyquinoline derivatives with quinoline groups have been synthesized by Perkin condensation. Their structures were characterized by EI-MS, ¹H NMR spectroscopy, elemental analysis and FT-IR spectroscopy; crystal structures were determined by X-ray crystallography. 2-[2-(Quinolin-2-yl)vinyl]-8-hydroxyquinoline crystallizes in the tetragonal space group I4₁/a and 2-[2-(quinolin-4-yl)vinyl]-8-hydroxyquinoline crystallizes in the monoclinic space group P2₁/n. Hydrogen bonds and intermolecular interactions are observed in the compounds and stabilize their structures. The biological activities were investigated by MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay and flow cytometry analysis, and the results revealed that the two compounds had effects on the proliferation of rat mesenchymal stem cells.

Computing details

For both compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

Figures

(3a)

Crystal data

C20H14N2O	Dx = 1.294 Mg m^−3
Mr = 298.33	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 2975 reflections
Hall symbol: -I4ad	θ = 2.7–20.7°
a = 21.5111 (7) Å	µ = 0.08 mm^−1
c = 13.2377 (9) Å	T = 298 K
V = 6125.4 (5) Å^3	Prism, yellow
Z = 16	0.16 × 0.13 × 0.10 mm
F(000) = 2496

Data collection

CCD area detector diffractometer	1932 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 27.6°, θmin = 1.8°
phi and ω scans	h = −28→24
25513 measured reflections	k = −25→28
3576 independent reflections	l = −17→15

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0769P)^2 + 2.3111P] where P = (Fo^2 + 2Fc^2)/3
3576 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.19 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
O1	0.98766 (8)	0.43660 (8)	0.22082 (12)	0.0798 (5)
H1	0.9615	0.4642	0.2251	0.120*
N1	0.90921 (8)	0.48603 (8)	0.08379 (12)	0.0559 (5)
N2	0.74190 (8)	0.65311 (8)	0.12063 (12)	0.0559 (4)
C1	0.94769 (9)	0.43967 (9)	0.05313 (15)	0.0520 (5)
C2	0.98875 (10)	0.41431 (10)	0.12548 (16)	0.0574 (6)
C3	1.02810 (11)	0.36736 (11)	0.10049 (18)	0.0690 (6)
H3	1.0553	0.3514	0.1485	0.083*
C4	1.02754 (12)	0.34306 (12)	0.00223 (19)	0.0753 (7)
H4	1.0544	0.3107	−0.0141	0.090*
C5	0.98868 (11)	0.36573 (11)	−0.06935 (18)	0.0691 (6)
H5	0.9889	0.3487	−0.1339	0.083*
C6	0.94782 (10)	0.41518 (10)	−0.04633 (15)	0.0575 (5)
C7	0.90691 (11)	0.44311 (12)	−0.11538 (16)	0.0714 (7)
H7	0.9055	0.4293	−0.1819	0.086*
C8	0.86941 (12)	0.49024 (12)	−0.08526 (17)	0.0736 (7)
H8	0.8427	0.5089	−0.1313	0.088*
C9	0.87084 (10)	0.51109 (10)	0.01616 (15)	0.0582 (5)
C10	0.82756 (11)	0.55910 (11)	0.05060 (17)	0.0665 (6)
H10	0.8035	0.5795	0.0025	0.080*
C11	0.82074 (11)	0.57513 (11)	0.14698 (17)	0.0656 (6)
H11	0.8477	0.5573	0.1936	0.079*
C12	0.77402 (10)	0.61880 (10)	0.18570 (16)	0.0579 (5)
C13	0.76375 (11)	0.62140 (11)	0.29078 (17)	0.0683 (6)
H13	0.7873	0.5967	0.3339	0.082*
C14	0.71975 (11)	0.65964 (11)	0.32903 (16)	0.0686 (6)
H14	0.7129	0.6614	0.3983	0.082*
C15	0.68429 (10)	0.69691 (10)	0.26286 (15)	0.0551 (5)
C16	0.63792 (11)	0.73834 (11)	0.29527 (18)	0.0691 (6)
H16	0.6288	0.7416	0.3637	0.083*
C17	0.60639 (11)	0.77350 (12)	0.22773 (18)	0.0723 (7)
H17	0.5757	0.8007	0.2502	0.087*
C18	0.61954 (11)	0.76925 (11)	0.12414 (17)	0.0681 (6)
H18	0.5979	0.7939	0.0785	0.082*
C19	0.66387 (10)	0.72916 (10)	0.09005 (16)	0.0591 (6)
H19	0.6719	0.7263	0.0212	0.071*
C20	0.69748 (9)	0.69212 (9)	0.15827 (14)	0.0504 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0864 (13)	0.0916 (13)	0.0612 (10)	0.0231 (9)	−0.0134 (8)	−0.0112 (8)
N1	0.0569 (11)	0.0568 (11)	0.0540 (9)	0.0025 (9)	0.0015 (8)	−0.0010 (8)
N2	0.0576 (11)	0.0594 (11)	0.0507 (9)	0.0033 (9)	−0.0015 (8)	−0.0041 (8)
C1	0.0512 (12)	0.0507 (12)	0.0542 (11)	−0.0004 (10)	0.0062 (9)	0.0021 (9)
C2	0.0581 (13)	0.0620 (13)	0.0521 (12)	0.0000 (11)	0.0018 (10)	−0.0034 (10)
C3	0.0645 (14)	0.0732 (16)	0.0693 (15)	0.0148 (12)	−0.0005 (11)	−0.0011 (12)
C4	0.0780 (17)	0.0712 (16)	0.0766 (16)	0.0172 (13)	0.0150 (13)	−0.0038 (13)
C5	0.0752 (16)	0.0729 (16)	0.0593 (13)	0.0093 (13)	0.0115 (12)	−0.0082 (12)
C6	0.0598 (13)	0.0624 (13)	0.0503 (11)	−0.0022 (11)	0.0074 (10)	−0.0002 (9)
C7	0.0794 (16)	0.0861 (17)	0.0488 (12)	0.0087 (14)	0.0012 (11)	−0.0065 (11)
C8	0.0766 (16)	0.0900 (18)	0.0542 (13)	0.0176 (14)	−0.0051 (12)	0.0022 (12)
C9	0.0588 (13)	0.0631 (14)	0.0527 (11)	0.0053 (11)	0.0015 (10)	0.0023 (10)
C10	0.0672 (15)	0.0714 (15)	0.0609 (13)	0.0158 (12)	−0.0024 (11)	0.0037 (11)
C11	0.0675 (15)	0.0668 (14)	0.0625 (13)	0.0125 (12)	−0.0072 (11)	−0.0008 (11)
C12	0.0606 (13)	0.0558 (13)	0.0572 (12)	0.0013 (11)	−0.0041 (10)	−0.0027 (10)
C13	0.0774 (16)	0.0732 (16)	0.0542 (12)	0.0107 (13)	−0.0055 (11)	0.0041 (11)
C14	0.0808 (16)	0.0790 (16)	0.0460 (11)	0.0027 (13)	−0.0001 (11)	−0.0022 (11)
C15	0.0578 (13)	0.0570 (13)	0.0506 (11)	−0.0030 (10)	−0.0013 (9)	−0.0058 (9)
C16	0.0729 (16)	0.0774 (16)	0.0572 (13)	0.0066 (13)	0.0053 (11)	−0.0148 (12)
C17	0.0711 (16)	0.0721 (16)	0.0736 (16)	0.0162 (13)	0.0046 (13)	−0.0101 (12)
C18	0.0670 (15)	0.0706 (15)	0.0666 (14)	0.0111 (12)	−0.0027 (12)	0.0004 (12)
C19	0.0580 (13)	0.0640 (14)	0.0552 (12)	0.0043 (11)	−0.0027 (10)	−0.0012 (10)
C20	0.0508 (12)	0.0509 (12)	0.0495 (11)	−0.0041 (10)	−0.0010 (9)	−0.0064 (9)

Geometric parameters (Å, º)

O1—C2	1.350 (2)	C9—N1	1.332 (3)
O1—H1	0.8200	C9—C10	1.463 (3)
N1—N1	0.000 (6)	C10—C11	1.330 (3)
N1—C9	1.332 (3)	C10—H10	0.9300
N1—C1	1.358 (2)	C11—C12	1.468 (3)
N2—C12	1.328 (3)	C11—H11	0.9300
N2—C20	1.366 (2)	C12—C13	1.410 (3)
C1—N1	1.358 (2)	C13—C14	1.353 (3)
C1—C2	1.413 (3)	C13—H13	0.9300
C1—C6	1.418 (3)	C14—C15	1.411 (3)
C2—C3	1.359 (3)	C14—H14	0.9300
C3—C4	1.402 (3)	C15—C16	1.405 (3)
C3—H3	0.9300	C15—C20	1.417 (3)
C4—C5	1.354 (3)	C16—C17	1.353 (3)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.413 (3)	C17—C18	1.403 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.404 (3)	C18—C19	1.363 (3)
C7—C8	1.355 (3)	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.405 (3)
C8—C9	1.416 (3)	C19—H19	0.9300
C8—H8	0.9300
C2—O1—H1	109.5	N1—C9—C10	118.07 (19)
N1—N1—C9	0 (10)	C8—C9—C10	120.4 (2)
N1—N1—C1	0 (10)	C11—C10—C9	123.5 (2)
C9—N1—C1	118.29 (17)	C11—C10—H10	118.2
C12—N2—C20	117.96 (17)	C9—C10—H10	118.2
N1—C1—N1	0.0 (2)	C10—C11—C12	125.2 (2)
N1—C1—C2	117.52 (18)	C10—C11—H11	117.4
N1—C1—C2	117.52 (18)	C12—C11—H11	117.4
N1—C1—C6	123.48 (19)	N2—C12—C13	122.4 (2)
N1—C1—C6	123.48 (19)	N2—C12—C11	119.03 (19)
C2—C1—C6	119.00 (19)	C13—C12—C11	118.5 (2)
O1—C2—C3	120.2 (2)	C14—C13—C12	120.2 (2)
O1—C2—C1	119.06 (19)	C14—C13—H13	119.9
C3—C2—C1	120.8 (2)	C12—C13—H13	119.9
C2—C3—C4	119.9 (2)	C13—C14—C15	119.4 (2)
C2—C3—H3	120.1	C13—C14—H14	120.3
C4—C3—H3	120.1	C15—C14—H14	120.3
C5—C4—C3	121.3 (2)	C16—C15—C14	123.7 (2)
C5—C4—H4	119.3	C16—C15—C20	119.1 (2)
C3—C4—H4	119.3	C14—C15—C20	117.19 (19)
C4—C5—C6	120.3 (2)	C17—C16—C15	120.6 (2)
C4—C5—H5	119.9	C17—C16—H16	119.7
C6—C5—H5	119.9	C15—C16—H16	119.7
C7—C6—C5	124.9 (2)	C16—C17—C18	120.5 (2)
C7—C6—C1	116.4 (2)	C16—C17—H17	119.7
C5—C6—C1	118.8 (2)	C18—C17—H17	119.7
C8—C7—C6	120.1 (2)	C19—C18—C17	120.4 (2)
C8—C7—H7	119.9	C19—C18—H18	119.8
C6—C7—H7	119.9	C17—C18—H18	119.8
C7—C8—C9	120.2 (2)	C18—C19—C20	120.4 (2)
C7—C8—H8	119.9	C18—C19—H19	119.8
C9—C8—H8	119.9	C20—C19—H19	119.8
N1—C9—N1	0.0 (2)	N2—C20—C19	118.30 (17)
N1—C9—C8	121.5 (2)	N2—C20—C15	122.76 (18)
N1—C9—C8	121.5 (2)	C19—C20—C15	118.94 (19)
N1—C9—C10	118.07 (19)
C9—N1—C1—N1	0 (95)	C1—N1—C9—C10	177.34 (19)
N1—N1—C1—C2	0.00 (10)	C7—C8—C9—N1	1.0 (4)
C9—N1—C1—C2	179.02 (19)	C7—C8—C9—N1	1.0 (4)
N1—N1—C1—C6	0.00 (7)	C7—C8—C9—C10	−175.9 (2)
C9—N1—C1—C6	−2.1 (3)	N1—C9—C10—C11	−6.1 (4)
N1—C1—C2—O1	0.5 (3)	N1—C9—C10—C11	−6.1 (4)
N1—C1—C2—O1	0.5 (3)	C8—C9—C10—C11	171.0 (2)
C6—C1—C2—O1	−178.5 (2)	C9—C10—C11—C12	−174.1 (2)
N1—C1—C2—C3	179.3 (2)	C20—N2—C12—C13	0.0 (3)
N1—C1—C2—C3	179.3 (2)	C20—N2—C12—C11	178.19 (18)
C6—C1—C2—C3	0.3 (3)	C10—C11—C12—N2	−11.4 (4)
O1—C2—C3—C4	177.9 (2)	C10—C11—C12—C13	166.9 (2)
C1—C2—C3—C4	−0.9 (3)	N2—C12—C13—C14	0.2 (4)
C2—C3—C4—C5	0.5 (4)	C11—C12—C13—C14	−177.9 (2)
C3—C4—C5—C6	0.5 (4)	C12—C13—C14—C15	−0.1 (4)
C4—C5—C6—C7	178.3 (2)	C13—C14—C15—C16	−179.5 (2)
C4—C5—C6—C1	−1.0 (3)	C13—C14—C15—C20	−0.3 (3)
N1—C1—C6—C7	2.4 (3)	C14—C15—C16—C17	178.9 (2)
N1—C1—C6—C7	2.4 (3)	C20—C15—C16—C17	−0.3 (3)
C2—C1—C6—C7	−178.7 (2)	C15—C16—C17—C18	−0.1 (4)
N1—C1—C6—C5	−178.3 (2)	C16—C17—C18—C19	0.6 (4)
N1—C1—C6—C5	−178.3 (2)	C17—C18—C19—C20	−0.8 (3)
C2—C1—C6—C5	0.6 (3)	C12—N2—C20—C19	179.18 (19)
C5—C6—C7—C8	179.7 (2)	C12—N2—C20—C15	−0.5 (3)
C1—C6—C7—C8	−0.9 (3)	C18—C19—C20—N2	−179.32 (19)
C6—C7—C8—C9	−0.7 (4)	C18—C19—C20—C15	0.3 (3)
C1—N1—C9—N1	0 (58)	C16—C15—C20—N2	179.8 (2)
N1—N1—C9—C8	0.00 (9)	C14—C15—C20—N2	0.6 (3)
C1—N1—C9—C8	0.3 (3)	C16—C15—C20—C19	0.2 (3)
N1—N1—C9—C10	0.00 (9)	C14—C15—C20—C19	−179.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	2.23	2.696 (2)	116
O1—H1···N2^i	0.82	2.49	3.099 (2)	133

Symmetry code: (i) y+1/4, −x+5/4, z+1/4.

(3b)

Crystal data

C20H14N2O	F(000) = 624
Mr = 298.33	Dx = 1.311 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 2512 reflections
a = 10.7240 (6) Å	θ = 2.5–25.1°
b = 8.9019 (5) Å	µ = 0.08 mm^−1
c = 16.1894 (8) Å	T = 298 K
β = 102.039 (4)°	Block, yellow
V = 1511.51 (14) Å^3	0.32 × 0.29 × 0.28 mm
Z = 4

Data collection

CCD area detector diffractometer	2376 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 27.6°, θmin = 2.1°
phi and ω scans	h = −10→13
13247 measured reflections	k = −11→10
3460 independent reflections	l = −21→20

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) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.1209P] where P = (Fo^2 + 2Fc^2)/3
3460 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.19 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
O1	0.28263 (10)	0.49707 (12)	0.16643 (7)	0.0578 (3)
H1	0.3032	0.5676	0.1396	0.087*
N1	0.50709 (11)	0.55344 (13)	0.11577 (7)	0.0430 (3)
N2	0.74000 (12)	1.22073 (14)	−0.08230 (7)	0.0502 (3)
C1	0.49795 (13)	0.42565 (15)	0.16041 (8)	0.0417 (3)
C2	0.38159 (14)	0.40009 (16)	0.18676 (9)	0.0464 (3)
C3	0.36949 (16)	0.27616 (18)	0.23504 (9)	0.0558 (4)
H3	0.2938	0.2600	0.2531	0.067*
C4	0.46986 (18)	0.17414 (18)	0.25717 (10)	0.0608 (4)
H4	0.4600	0.0912	0.2901	0.073*
C5	0.58216 (17)	0.19378 (17)	0.23135 (9)	0.0568 (4)
H5	0.6474	0.1238	0.2459	0.068*
C6	0.59899 (14)	0.32088 (15)	0.18237 (9)	0.0464 (3)
C7	0.71088 (15)	0.35195 (17)	0.15318 (10)	0.0538 (4)
H7	0.7789	0.2850	0.1642	0.065*
C8	0.71976 (14)	0.47981 (16)	0.10877 (10)	0.0513 (4)
H8	0.7937	0.5004	0.0894	0.062*
C9	0.61637 (13)	0.58097 (15)	0.09222 (9)	0.0431 (3)
C10	0.62348 (14)	0.72455 (16)	0.04910 (9)	0.0465 (3)
H10	0.5472	0.7652	0.0196	0.056*
C11	0.72883 (14)	0.80146 (15)	0.04840 (9)	0.0463 (3)
H11	0.8056	0.7607	0.0771	0.056*
C12	0.73372 (13)	0.94639 (15)	0.00569 (8)	0.0421 (3)
C13	0.64171 (15)	0.98503 (17)	−0.06289 (10)	0.0510 (4)
H13	0.5743	0.9198	−0.0823	0.061*
C14	0.64829 (15)	1.12191 (18)	−0.10403 (10)	0.0541 (4)
H14	0.5832	1.1445	−0.1500	0.065*
C15	0.83499 (13)	1.18596 (15)	−0.01465 (9)	0.0431 (3)
C16	0.93575 (15)	1.28937 (16)	0.00899 (10)	0.0519 (4)
H16	0.9369	1.3767	−0.0224	0.062*
C17	1.03098 (15)	1.26297 (18)	0.07688 (11)	0.0589 (4)
H17	1.0966	1.3323	0.0919	0.071*
C18	1.03080 (15)	1.13168 (19)	0.12437 (11)	0.0598 (4)
H18	1.0961	1.1149	0.1712	0.072*
C19	0.93615 (14)	1.02835 (17)	0.10280 (10)	0.0511 (4)
H19	0.9378	0.9416	0.1350	0.061*
C20	0.83558 (12)	1.05068 (14)	0.03233 (8)	0.0405 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0494 (6)	0.0559 (6)	0.0713 (7)	−0.0055 (5)	0.0198 (5)	0.0106 (5)
N1	0.0423 (6)	0.0407 (6)	0.0451 (6)	−0.0055 (5)	0.0074 (5)	0.0011 (5)
N2	0.0531 (7)	0.0470 (7)	0.0514 (7)	−0.0005 (6)	0.0127 (6)	0.0067 (6)
C1	0.0478 (8)	0.0376 (7)	0.0379 (7)	−0.0084 (6)	0.0049 (6)	−0.0026 (6)
C2	0.0509 (9)	0.0445 (8)	0.0429 (7)	−0.0106 (7)	0.0080 (6)	−0.0026 (6)
C3	0.0658 (10)	0.0547 (9)	0.0477 (8)	−0.0169 (8)	0.0140 (8)	0.0011 (7)
C4	0.0851 (12)	0.0464 (9)	0.0479 (9)	−0.0158 (9)	0.0070 (9)	0.0066 (7)
C5	0.0707 (11)	0.0432 (8)	0.0503 (9)	−0.0018 (8)	−0.0016 (8)	0.0044 (7)
C6	0.0539 (9)	0.0393 (7)	0.0428 (7)	−0.0044 (7)	0.0025 (6)	−0.0031 (6)
C7	0.0527 (9)	0.0419 (8)	0.0645 (10)	0.0047 (7)	0.0066 (8)	−0.0041 (7)
C8	0.0459 (8)	0.0449 (8)	0.0652 (10)	−0.0020 (7)	0.0167 (7)	−0.0059 (7)
C9	0.0453 (8)	0.0391 (7)	0.0446 (7)	−0.0062 (6)	0.0086 (6)	−0.0029 (6)
C10	0.0457 (8)	0.0433 (8)	0.0513 (8)	−0.0005 (6)	0.0119 (7)	0.0021 (6)
C11	0.0458 (8)	0.0424 (8)	0.0508 (8)	−0.0035 (6)	0.0102 (7)	0.0018 (6)
C12	0.0430 (8)	0.0403 (7)	0.0451 (7)	−0.0019 (6)	0.0143 (6)	−0.0015 (6)
C13	0.0503 (8)	0.0510 (9)	0.0503 (8)	−0.0096 (7)	0.0074 (7)	0.0016 (7)
C14	0.0542 (9)	0.0564 (9)	0.0488 (8)	−0.0016 (8)	0.0041 (7)	0.0064 (7)
C15	0.0428 (8)	0.0397 (7)	0.0496 (8)	0.0015 (6)	0.0157 (6)	−0.0001 (6)
C16	0.0529 (9)	0.0399 (8)	0.0664 (10)	−0.0045 (7)	0.0202 (8)	0.0030 (7)
C17	0.0494 (9)	0.0481 (9)	0.0788 (11)	−0.0121 (7)	0.0124 (8)	−0.0031 (8)
C18	0.0493 (9)	0.0572 (10)	0.0674 (10)	−0.0059 (8)	−0.0004 (8)	0.0012 (8)
C19	0.0476 (8)	0.0465 (8)	0.0577 (9)	−0.0020 (7)	0.0075 (7)	0.0052 (7)
C20	0.0400 (7)	0.0373 (7)	0.0462 (8)	−0.0004 (6)	0.0133 (6)	−0.0015 (6)

Geometric parameters (Å, º)

O1—C2	1.3543 (18)	C9—C10	1.4660 (19)
O1—H1	0.8200	C10—C11	1.323 (2)
N1—C9	1.3286 (18)	C10—H10	0.9300
N1—C1	1.3621 (17)	C11—C12	1.4699 (19)
N2—C14	1.3117 (19)	C11—H11	0.9300
N2—C15	1.3667 (18)	C12—C13	1.367 (2)
C1—C6	1.418 (2)	C12—C20	1.4299 (19)
C1—C2	1.419 (2)	C13—C14	1.397 (2)
C2—C3	1.374 (2)	C13—H13	0.9300
C3—C4	1.397 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.410 (2)
C4—C5	1.366 (2)	C15—C20	1.4236 (19)
C4—H4	0.9300	C16—C17	1.356 (2)
C5—C6	1.415 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.399 (2)
C6—C7	1.406 (2)	C17—H17	0.9300
C7—C8	1.360 (2)	C18—C19	1.360 (2)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.410 (2)	C19—C20	1.411 (2)
C8—H8	0.9300	C19—H19	0.9300
C2—O1—H1	109.5	C9—C10—H10	117.1
C9—N1—C1	118.14 (12)	C10—C11—C12	124.92 (14)
C14—N2—C15	117.06 (12)	C10—C11—H11	117.5
N1—C1—C6	123.14 (13)	C12—C11—H11	117.5
N1—C1—C2	117.29 (13)	C13—C12—C20	117.28 (12)
C6—C1—C2	119.55 (13)	C13—C12—C11	120.83 (13)
O1—C2—C3	119.20 (14)	C20—C12—C11	121.87 (12)
O1—C2—C1	121.23 (12)	C12—C13—C14	120.47 (14)
C3—C2—C1	119.56 (14)	C12—C13—H13	119.8
C2—C3—C4	120.59 (15)	C14—C13—H13	119.8
C2—C3—H3	119.7	N2—C14—C13	124.50 (14)
C4—C3—H3	119.7	N2—C14—H14	117.7
C5—C4—C3	121.31 (15)	C13—C14—H14	117.7
C5—C4—H4	119.3	N2—C15—C16	118.06 (13)
C3—C4—H4	119.3	N2—C15—C20	122.63 (12)
C4—C5—C6	119.84 (15)	C16—C15—C20	119.30 (13)
C4—C5—H5	120.1	C17—C16—C15	120.78 (14)
C6—C5—H5	120.1	C17—C16—H16	119.6
C7—C6—C5	124.30 (15)	C15—C16—H16	119.6
C7—C6—C1	116.59 (13)	C16—C17—C18	120.21 (14)
C5—C6—C1	119.12 (14)	C16—C17—H17	119.9
C8—C7—C6	120.08 (14)	C18—C17—H17	119.9
C8—C7—H7	120.0	C19—C18—C17	120.68 (15)
C6—C7—H7	120.0	C19—C18—H18	119.7
C7—C8—C9	119.73 (14)	C17—C18—H18	119.7
C7—C8—H8	120.1	C18—C19—C20	121.05 (14)
C9—C8—H8	120.1	C18—C19—H19	119.5
N1—C9—C8	122.23 (13)	C20—C19—H19	119.5
N1—C9—C10	115.73 (12)	C19—C20—C15	117.94 (12)
C8—C9—C10	122.03 (13)	C19—C20—C12	124.01 (12)
C11—C10—C9	125.77 (14)	C15—C20—C12	118.04 (12)
C11—C10—H10	117.1
C9—N1—C1—C6	−0.34 (19)	C9—C10—C11—C12	−179.12 (13)
C9—N1—C1—C2	178.49 (12)	C10—C11—C12—C13	−26.6 (2)
N1—C1—C2—O1	1.63 (19)	C10—C11—C12—C20	155.01 (14)
C6—C1—C2—O1	−179.49 (12)	C20—C12—C13—C14	−0.4 (2)
N1—C1—C2—C3	−177.22 (12)	C11—C12—C13—C14	−178.87 (13)
C6—C1—C2—C3	1.7 (2)	C15—N2—C14—C13	0.0 (2)
O1—C2—C3—C4	−179.91 (13)	C12—C13—C14—N2	0.9 (2)
C1—C2—C3—C4	−1.0 (2)	C14—N2—C15—C16	178.94 (14)
C2—C3—C4—C5	−0.3 (2)	C14—N2—C15—C20	−1.2 (2)
C3—C4—C5—C6	1.1 (2)	N2—C15—C16—C17	178.27 (14)
C4—C5—C6—C7	179.56 (14)	C20—C15—C16—C17	−1.6 (2)
C4—C5—C6—C1	−0.4 (2)	C15—C16—C17—C18	0.3 (2)
N1—C1—C6—C7	−2.10 (19)	C16—C17—C18—C19	0.6 (3)
C2—C1—C6—C7	179.09 (13)	C17—C18—C19—C20	−0.2 (3)
N1—C1—C6—C5	177.87 (12)	C18—C19—C20—C15	−1.1 (2)
C2—C1—C6—C5	−0.93 (19)	C18—C19—C20—C12	179.48 (14)
C5—C6—C7—C8	−177.81 (14)	N2—C15—C20—C19	−177.91 (13)
C1—C6—C7—C8	2.2 (2)	C16—C15—C20—C19	1.95 (19)
C6—C7—C8—C9	0.0 (2)	N2—C15—C20—C12	1.56 (19)
C1—N1—C9—C8	2.76 (19)	C16—C15—C20—C12	−178.57 (13)
C1—N1—C9—C10	−176.27 (12)	C13—C12—C20—C19	178.75 (13)
C7—C8—C9—N1	−2.7 (2)	C11—C12—C20—C19	−2.8 (2)
C7—C8—C9—C10	176.30 (14)	C13—C12—C20—C15	−0.69 (19)
N1—C9—C10—C11	152.78 (15)	C11—C12—C20—C15	177.74 (12)
C8—C9—C10—C11	−26.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2^i	0.82	2.11	2.8438 (15)	149
O1—H1···N1	0.82	2.30	2.7463 (16)	115

Symmetry code: (i) −x+1, −y+2, −z.