Structural, spectroscopic and first-principles studies of new aminocoumarin derivatives

The new aminocoumarin derivatives 3-[1-(3-hy­droxy­anilino)ethyl­idene]-3H-chromene-2,4-dione, (1), 3-[1-(4-hy­droxy­anilino)ethyl­idene]-3H-chromene-2,4-dione, (2), and 3-[1-(2-hy­droxy­anilino)ethyl­idene]-3H-chromene-2,4-dione, (3), all C₁₇H₁₃NO₄, were synthesized by reacting an equimolar amount of 3-acetyl-4-hy­droxy­coumarin and the corresponding amino­phenol in absolute ethanol. Structural and spectroscopic analysis of these phases revealed that derivatives (1) and (2) are isomers of previously reported (3) [Brahmia et al. (2013). Acta Cryst. E69, o1296]. The crystal structures of meta derivative (1) and para deri­vative (2) were ab initio determined from powder X-ray diffraction data using the direct-space approach. Both (1) and (2) adopt the ortho­rhom­bic space group P2₁2₁2₁. These isomers show hydrogen bonds and rich π–π stacking, together with π...H inter­actions, which are built by conjugated systems of coumarin and phenol rings. In the crystalline lattice, the packing of (1) and (3) are mainly stabilized through O—H...O hydrogen bonding between neighbouring coumarin mol­ecules, while hydrogen bonds between coumarin and water mol­ecules build the stable crystal structure of derivative (2). A big similarity in the skeletons of the IR spectra of these isomers was noticed. Derivative (2) exhibits two weak bands which were not present in the spectra of the other two derivatives, at 2370 and 2948 cm⁻¹, which can be assigned to the O—H vibrations of the solvent (H₂O) trapped in the structure of (2). These amino­coumarin derivatives display absorption maxima in the visible region, attributed to π–π delocalization involving the whole electronic system of the com­pounds with a considerable charge-transfer character originating from the amino­phenyl ring and pointing towards the coumarin system which is characterized by a high electron-accepting character. Additionally, the isolated mol­ecular ground-state geometries were optimized at the PBE0/TZP level and the electronic properties, mol­ecular electrostatic potential and Hirshfeld charges were determined.

Computing details

Data collection: SMART for (3). Cell refinement: SMART for (3). Data reduction: SAINT for (3). Program(s) used to solve structure: SHELXS97 for (3). Program(s) used to refine structure: SHELXL97 for (3). Molecular graphics: ORTEP-3 for Windows for (3). Software used to prepare material for publication: WinGX for (3).

3-[1-(3-Hydroxyanilino)ethylidene]-3H-chromene-2,4-dione (1)

Crystal data

C17H13NO4	V = 1383.93 (4) Å^3
Mr = 295.3	Z = 4
Orthorhombic, P212121	F(000) = 616
Hall symbol: P 2ac 2ab	Dx = 1.417 Mg m^−3
a = 25.8641 (5) Å	Cu Kα1 radiation
b = 13.2022 (2) Å	T = 293 K
c = 4.05295 (5) Å	white

Data collection

PANalytical Empyrean detector diffractometer

2θmin = 4.007°, 2θmax = 79.99°, 2θstep = 0.013°

Refinement

Rp = 0.018	73 constraints
Rwp = 0.026	H-atom parameters constrained
Rexp = 0.010	Weighting scheme based on measured s.u.'s
R(F) = 0.039	(Δ/σ)max = 0.050
Profile function: Pseudo-Voigt	Background function: 30 Legendre polynoms
107 parameters	Preferred orientation correction: March & Dollase
50 restraints

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

	x	y	z	Uiso*/Ueq
O1	0.14551 (8)	0.4986 (2)	0.2632 (10)	0.0519 (10)*
O3	0.03421 (13)	0.2876 (3)	0.4458 (13)	0.0519 (10)*
O2	0.09381 (12)	0.5974 (3)	−0.0066 (15)	0.0519 (10)*
O4	−0.172416 (8)	0.22456 (3)	−0.33975 (18)	0.0519 (10)*
N1	−0.03190 (9)	0.39866 (18)	0.1547 (10)	0.0519 (10)*
C8	0.18466 (11)	0.2431 (3)	0.7948 (15)	0.0519 (10)*
C7	0.22114 (12)	0.3173 (3)	0.723 (2)	0.0519 (10)*
C6	0.20755 (10)	0.4026 (4)	0.552 (2)	0.0519 (10)*
C5	0.15687 (7)	0.4138 (3)	0.4455 (14)	0.0519 (10)*
C4	0.12001 (8)	0.3410 (3)	0.5128 (19)	0.0519 (10)*
C9	0.13480 (8)	0.2549 (3)	0.6841 (15)	0.0519 (10)*
C1	0.09647 (13)	0.5191 (4)	0.153 (2)	0.0519 (10)*
C2	0.05548 (9)	0.4479 (4)	0.219 (2)	0.0519 (10)*
C3	0.06659 (11)	0.3567 (4)	0.400 (3)	0.0519 (10)*
C10	0.00459 (10)	0.4661 (4)	0.0923 (18)	0.0519 (10)*
C11	−0.00855 (10)	0.5561 (4)	−0.117 (2)	0.0519 (10)*
C12	−0.08390 (8)	0.39898 (16)	0.0379 (8)	0.0519 (10)*
C17	−0.11579 (12)	0.4802 (3)	0.106 (2)	0.0519 (10)*
C16	−0.16764 (10)	0.4745 (3)	0.035 (2)	0.0519 (10)*
C15	−0.18768 (10)	0.3884 (3)	−0.104 (2)	0.0519 (10)*
C14	−0.15596 (4)	0.30807 (8)	−0.1732 (3)	0.0519 (10)*
C13	−0.10389 (5)	0.31315 (13)	−0.0974 (5)	0.0519 (10)*
H1c8	0.194209	0.184291	0.920176	0.0622*
H1c7	0.256249	0.308612	0.794203	0.0622*
H1c6	0.232781	0.453989	0.505601	0.0622*
H1c9	0.109821	0.202654	0.726119	0.0622*
H1c11	0.020929	0.600101	−0.131502	0.0622*
H2c11	−0.018015	0.533775	−0.334403	0.0622*
H3c11	−0.036967	0.592135	−0.020003	0.0622*
H1n1	−0.023189	0.348319	0.281616	0.0622*
H1c17	−0.101717	0.540673	0.201715	0.0622*
H1c16	−0.189858	0.530852	0.083618	0.0622*
H1c15	−0.223949	0.38438	−0.152453	0.0622*
H1c13	−0.081851	0.256148	−0.140296	0.0622*
H1o4	−0.147815	0.186809	−0.373869	0.0622*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
?	?	?	?	?	?	?

Geometric parameters (Å, º)

O1—C5	1.373 (5)	C9—H1c9	0.9604
O1—C1	1.371 (4)	C1—C2	1.442 (6)
O3—C3	1.253 (6)	C2—C3	1.439 (10)
O2—C1	1.222 (7)	C2—C10	1.433 (5)
O4—C14	1.3609 (12)	C10—C11	1.498 (9)
O4—H1o4	0.82	C11—H1c11	0.9593
N1—C10	1.322 (5)	C11—H2c11	0.9612
N1—C12	1.426 (3)	C11—H3c11	0.9607
N1—H1n1	0.8698	C12—C17	1.381 (5)
C8—C7	1.390 (5)	C12—C13	1.361 (3)
C8—C9	1.376 (4)	C17—C16	1.372 (4)
C8—H1c8	0.9595	C17—H1c17	0.9595
C7—C6	1.368 (8)	C16—C15	1.371 (7)
C7—H1c7	0.9607	C16—H1c16	0.9611
C6—C5	1.390 (4)	C15—C14	1.370 (4)
C6—H1c6	0.9591	C15—H1c15	0.9594
C5—C4	1.382 (5)	C14—C13	1.3830 (17)
C4—C9	1.385 (7)	C13—H1c13	0.9605
C4—C3	1.470 (6)
C5—O1—C1	122.3 (3)	O3—C3—C2	123.5 (5)
C14—O4—H1o4	109.48	C4—C3—C2	117.7 (4)
C10—N1—C12	127.4 (4)	N1—C10—C2	118.3 (5)
C10—N1—H1n1	116.34	N1—C10—C11	118.8 (3)
C12—N1—H1n1	116.28	C2—C10—C11	122.9 (4)
C7—C8—C9	119.2 (4)	C10—C11—H1c11	109.6
C7—C8—H1c8	120.52	C10—C11—H2c11	109.45
C9—C8—H1c8	120.33	C10—C11—H3c11	109.56
C8—C7—C6	120.9 (3)	H1c11—C11—H2c11	109.43
C8—C7—H1c7	119.59	H1c11—C11—H3c11	109.47
C6—C7—H1c7	119.48	H2c11—C11—H3c11	109.31
C7—C6—C5	119.1 (4)	N1—C12—C17	119.9 (3)
C7—C6—H1c6	120.56	N1—C12—C13	119.4 (2)
C5—C6—H1c6	120.31	C17—C12—C13	120.0 (2)
O1—C5—C6	117.2 (3)	C12—C17—C16	119.9 (4)
O1—C5—C4	121.8 (3)	C12—C17—H1c17	120
C6—C5—C4	121.0 (4)	C16—C17—H1c17	120.07
C5—C4—C9	118.7 (3)	C17—C16—C15	120.1 (4)
C5—C4—C3	119.2 (5)	C17—C16—H1c16	119.95
C9—C4—C3	122.1 (4)	C15—C16—H1c16	119.93
C8—C9—C4	121.0 (3)	C16—C15—C14	119.9 (3)
C8—C9—H1c9	119.45	C16—C15—H1c15	120.04
C4—C9—H1c9	119.51	C14—C15—H1c15	120.05
O1—C1—O2	113.1 (3)	O4—C14—C15	122.8 (2)
O1—C1—C2	119.4 (5)	O4—C14—C13	117.02 (10)
O2—C1—C2	127.4 (4)	C15—C14—C13	120.0 (2)
C1—C2—C3	119.5 (3)	C12—C13—C14	120.02 (14)
C1—C2—C10	120.0 (5)	C12—C13—H1c13	120.02
C3—C2—C10	120.5 (4)	C14—C13—H1c13	119.95
O3—C3—C4	118.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H1c11···O2	0.96	1.95	2.738 (4)	137.68
N1—H1n1···O3	0.87	1.81	2.543 (4)	140.06
N1—H1n1···C3	0.87	2.37	2.790 (6)	109.69
O4—H1o4···O2^i	0.82	1.89	2.709 (3)	174.53

Symmetry code: (i) −x, y−1/2, −z−1/2.

3-[1-(4-Hydroxyanilino)ethylidene]-3H-chromene-2,4-dione monohydrate (2)

Crystal data

C17H13NO4·H2O	V = 1469.89 (4) Å^3
Mr = 313.3	Z = 4
Orthorhombic, P212121	F(000) = 648
Hall symbol: P 2ac 2ab	Dx = 1.416 Mg m^−3
a = 25.2195 (4) Å	Cu Kα radiation
b = 12.8116 (2) Å	T = 293 K
c = 4.54932 (4) Å	yellow

Data collection

PANalytical Empyrean detector diffractometer

2θmin = 4.007°, 2θmax = 79.99°, 2θstep = 0.013°

Refinement

Rp = 0.027	73 constraints
Rwp = 0.036	H-atom parameters constrained
Rexp = 0.011	Weighting scheme based on measured s.u.'s
R(F) = 0.044	(Δ/σ)max = 0.049
Profile function: Pseudo-Voigt	Background function: 30 Legendre polynoms
106 parameters	Preferred orientation correction: March & Dollase
50 restraints

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

	x	y	z	Uiso*/Ueq
O3	0.05252 (13)	0.0732 (2)	0.4974 (10)	0.0556 (7)*
O1	0.16509 (9)	0.29935 (18)	0.4000 (7)	0.0556 (7)*
O2	0.12876 (17)	0.4026 (3)	0.7147 (8)	0.0556 (7)*
N1	−0.00116 (8)	0.19544 (17)	0.8250 (7)	0.0556 (7)*
C9	0.13799 (14)	0.0382 (2)	0.1112 (10)	0.0556 (7)*
C8	0.18091 (13)	0.0252 (2)	−0.0716 (10)	0.0556 (7)*
C7	0.21750 (13)	0.1058 (2)	−0.0999 (9)	0.0556 (7)*
C6	0.21274 (12)	0.1950 (2)	0.0637 (10)	0.0556 (7)*
C5	0.16928 (13)	0.2068 (2)	0.2481 (11)	0.0556 (7)*
C4	0.13182 (16)	0.1286 (2)	0.2756 (12)	0.0556 (7)*
C3	0.08613 (15)	0.1446 (2)	0.4730 (12)	0.0556 (7)*
C2	0.08170 (15)	0.2438 (2)	0.6194 (15)	0.0556 (7)*
C1	0.12228 (15)	0.32191 (19)	0.5756 (11)	0.0556 (7)*
C10	0.03666 (16)	0.2666 (3)	0.8026 (13)	0.0556 (7)*
C11	0.03086 (14)	0.3667 (2)	0.9698 (10)	0.0556 (7)*
C12	−0.05027 (6)	0.2046 (2)	0.9772 (6)	0.0556 (7)*
C13	−0.06462 (10)	0.1218 (2)	1.1567 (10)	0.0556 (7)*
C14	−0.11312 (5)	0.12131 (11)	1.2972 (4)	0.0556 (7)*
C16	−0.13439 (9)	0.2851 (2)	1.0729 (8)	0.0556 (7)*
C17	−0.08565 (10)	0.2860 (3)	0.9341 (10)	0.0556 (7)*
O4	−0.195343 (14)	0.19915 (3)	1.40411 (14)	0.0556 (7)*
C15	−0.14766 (4)	0.20392 (7)	1.2610 (3)	0.0556 (7)*
Ow	0.28085 (18)	0.4814 (3)	0.2768 (10)	0.023 (2)*
H1c9	0.111884	−0.016125	0.125244	0.0667*
H1c8	0.185569	−0.038796	−0.178429	0.0667*
H1c11	0.042942	0.423732	0.850349	0.0667*
H2c11	−0.005743	0.377151	1.019755	0.0667*
H3c11	0.051657	0.363406	1.146238	0.0667*
H1c13	−0.040638	0.064372	1.183341	0.0667*
H1c14	−0.122834	0.063507	1.420249	0.0667*
H1c16	−0.159143	0.340717	1.039062	0.0667*
H1c17	−0.076278	0.343145	0.807745	0.0667*
H1c7	0.246427	0.098813	−0.235615	0.0667*
H1c6	0.239146	0.248832	0.051117	0.0667*
H1o4	−0.197124	0.144591	1.497817	0.0667*
H1n1	0.004714	0.135635	0.735534	0.0667*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
?	?	?	?	?	?	?

Geometric parameters (Å, º)

O3—C3	1.252 (5)	C2—C1	1.445 (5)
O1—C5	1.377 (4)	C2—C10	1.440 (7)
O1—C1	1.374 (4)	C10—C11	1.498 (5)
O2—C1	1.222 (5)	C11—H1c11	0.9604
N1—C10	1.324 (5)	C11—H2c11	0.9608
N1—C12	1.424 (3)	C11—H3c11	0.9585
N1—H1n1	0.8797	C12—C13	1.387 (4)
C9—C8	1.375 (5)	C12—C17	1.387 (4)
C9—C4	1.389 (5)	C13—C14	1.380 (3)
C9—H1c9	0.9604	C13—H1c13	0.9596
C8—C7	1.391 (4)	C14—C15	1.3807 (16)
C8—H1c8	0.9594	C14—H1c14	0.96
C7—C6	1.370 (5)	C16—C17	1.381 (4)
C7—H1c7	0.9599	C16—C15	1.388 (3)
C6—C5	1.386 (5)	C16—H1c16	0.9597
C6—H1c6	0.9612	C17—H1c17	0.9604
C5—C4	1.384 (5)	O4—C15	1.3687 (11)
C4—C3	1.474 (7)	O4—H1o4	0.82
C3—C2	1.438 (4)
C5—O1—C1	122.3 (2)	O2—C1—C2	127.7 (4)
C10—N1—C12	127.4 (3)	N1—C10—C2	118.2 (3)
C10—N1—H1n1	116.31	N1—C10—C11	118.8 (4)
C12—N1—H1n1	116.33	C2—C10—C11	123.1 (4)
C8—C9—C4	121.1 (3)	C10—C11—H1c11	109.45
C8—C9—H1c9	119.51	C10—C11—H2c11	109.44
C4—C9—H1c9	119.38	C10—C11—H3c11	109.47
C9—C8—C7	119.2 (3)	H1c11—C11—H2c11	109.37
C9—C8—H1c8	120.37	H1c11—C11—H3c11	109.57
C7—C8—H1c8	120.46	H2c11—C11—H3c11	109.53
C8—C7—C6	120.7 (3)	N1—C12—C13	116.7 (2)
C8—C7—H1c7	119.59	N1—C12—C17	123.6 (3)
C6—C7—H1c7	119.67	C13—C12—C17	119.4 (2)
C7—C6—C5	119.3 (2)	C12—C13—C14	120.5 (2)
C7—C6—H1c6	120.27	C12—C13—H1c13	119.72
C5—C6—H1c6	120.43	C14—C13—H1c13	119.81
O1—C5—C6	117.3 (2)	C13—C14—C15	120.05 (17)
O1—C5—C4	121.7 (3)	C13—C14—H1c14	119.96
C6—C5—C4	121.1 (3)	C15—C14—H1c14	119.99
C9—C4—C5	118.5 (4)	C17—C16—C15	120.2 (2)
C9—C4—C3	122.2 (3)	C17—C16—H1c16	119.92
C5—C4—C3	119.3 (3)	C15—C16—H1c16	119.9
O3—C3—C4	118.7 (3)	C12—C17—C16	120.1 (3)
O3—C3—C2	123.6 (4)	C12—C17—H1c17	119.9
C4—C3—C2	117.6 (3)	C16—C17—H1c17	120
C3—C2—C1	119.6 (4)	C15—O4—H1o4	109.49
C3—C2—C10	120.6 (4)	C14—C15—C16	119.73 (14)
C1—C2—C10	119.8 (3)	C14—C15—O4	117.60 (10)
O1—C1—O2	111.9 (3)	C16—C15—O4	122.59 (12)
O1—C1—C2	119.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H1c11···O2	0.96	2.27	2.767 (6)	111.43
C11—H2c11···C12	0.96	2.49	2.916 (3)	106.98
C11—H2c11···C17	0.96	2.36	3.121 (4)	135.49
O4—H1o4···Ow^i	0.82	1.99	2.796 (4)	166.87
N1—H1n1···O3	0.88	1.81	2.551 (4)	140.80
N1—H1n1···C3	0.88	2.38	2.798 (5)	109.62

Symmetry code: (i) x−1/2, −y+1/2, −z+2.

3-[1-(2-Hydroxyanilino)ethylidene]-3H-chromene-2,4-dione (3)

Crystal data

C17H13NO4	F(000) = 616
Mr = 295.29	Dx = 1.440 Mg m^−3
Monoclinic, P21/n	Melting point: 446 K
Hall symbol: -P2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.5596 (4) Å	Cell parameters from 1721 reflections
b = 7.5870 (3) Å	θ = 2.0–40.0°
c = 14.3433 (6) Å	µ = 0.10 mm^−1
β = 94.660 (2)°	T = 293 K
V = 1362.25 (9) Å^3	Needle, yellow
Z = 4	0.16 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1721 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 29.8°, θmin = 2.1°
φ and ω scans	h = −14→17
11784 measured reflections	k = −9→10
3891 independent reflections	l = −19→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0922P)^2 + 0.2201P] where P = (Fo^2 + 2Fc^2)/3
3891 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.20 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	0.12600 (13)	0.1466 (2)	0.90032 (12)	0.0480 (5)
N1	0.22554 (16)	0.0473 (3)	1.22516 (14)	0.0375 (5)
C1	0.17836 (17)	0.0955 (3)	1.06478 (16)	0.0350 (5)
O3	0.34691 (12)	−0.0400 (2)	1.09988 (12)	0.0484 (5)
C2	0.27686 (18)	0.0180 (3)	1.04068 (17)	0.0378 (6)
C3	0.29714 (18)	0.0128 (3)	0.94130 (17)	0.0389 (6)
C4	0.21353 (18)	0.0298 (3)	1.32227 (17)	0.0368 (6)
O4	0.38154 (13)	0.1659 (2)	1.35092 (12)	0.0473 (5)
H12	0.4244	0.1965	1.3941	0.071*
C5	0.15554 (17)	0.1107 (3)	1.16048 (17)	0.0363 (6)
O2	0.01364 (14)	0.2201 (3)	1.00033 (13)	0.0556 (5)
C6	0.29532 (19)	0.0900 (3)	1.38614 (18)	0.0376 (6)
C7	0.22130 (19)	0.0795 (3)	0.87552 (18)	0.0417 (6)
C8	0.2850 (2)	0.0704 (3)	1.48055 (18)	0.0439 (6)
H4	0.3384	0.1118	1.5238	0.053*
C9	0.05868 (19)	0.2032 (4)	1.19047 (19)	0.0475 (7)
H5	0.0586	0.1977	1.2573	0.071*
H11	−0.0045	0.1470	1.1623	0.071*
H7	0.0598	0.3242	1.1710	0.071*
C10	0.2392 (2)	0.0838 (4)	0.78132 (19)	0.0546 (7)
H10	0.1871	0.1274	0.7375	0.065*
C11	0.10187 (19)	0.1569 (3)	0.99164 (18)	0.0416 (6)
C12	0.3922 (2)	−0.0510 (3)	0.9114 (2)	0.0481 (7)
H1	0.4431	−0.0990	0.9548	0.058*
C13	0.12623 (19)	−0.0559 (3)	1.35386 (19)	0.0451 (7)
H2	0.0735	−0.1007	1.3111	0.054*
C14	0.1168 (2)	−0.0752 (4)	1.4483 (2)	0.0503 (7)
H3	0.0575	−0.1314	1.4695	0.060*
C15	0.4121 (2)	−0.0446 (4)	0.8187 (2)	0.0545 (7)
H8	0.4768	−0.0848	0.7996	0.065*
C16	0.1960 (2)	−0.0104 (4)	1.51091 (19)	0.0497 (7)
H6	0.1893	−0.0214	1.5747	0.060*
C17	0.3343 (2)	0.0230 (4)	0.7537 (2)	0.0583 (8)
H9	0.3471	0.0268	0.6908	0.070*
H13	0.283 (2)	0.007 (4)	1.201 (2)	0.061 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0451 (10)	0.0600 (12)	0.0366 (10)	0.0120 (9)	−0.0099 (8)	0.0012 (9)
N1	0.0327 (11)	0.0452 (12)	0.0330 (11)	0.0007 (9)	−0.0072 (9)	−0.0010 (9)
C1	0.0327 (11)	0.0370 (13)	0.0335 (13)	0.0004 (10)	−0.0089 (10)	0.0011 (10)
O3	0.0378 (9)	0.0621 (12)	0.0433 (10)	0.0091 (8)	−0.0085 (8)	0.0041 (9)
C2	0.0347 (12)	0.0368 (13)	0.0398 (13)	−0.0011 (10)	−0.0104 (10)	0.0017 (11)
C3	0.0387 (13)	0.0355 (13)	0.0413 (14)	−0.0040 (11)	−0.0045 (11)	−0.0031 (11)
C4	0.0355 (12)	0.0391 (13)	0.0342 (13)	0.0009 (10)	−0.0057 (10)	−0.0007 (11)
O4	0.0390 (9)	0.0621 (12)	0.0390 (10)	−0.0135 (8)	−0.0080 (8)	0.0009 (9)
C5	0.0339 (12)	0.0330 (13)	0.0403 (14)	−0.0055 (10)	−0.0082 (10)	−0.0012 (10)
O2	0.0406 (10)	0.0748 (14)	0.0484 (11)	0.0151 (9)	−0.0141 (8)	0.0016 (10)
C6	0.0403 (13)	0.0340 (13)	0.0375 (13)	−0.0002 (10)	−0.0032 (10)	−0.0001 (11)
C7	0.0436 (14)	0.0406 (14)	0.0393 (14)	−0.0002 (11)	−0.0069 (11)	−0.0026 (11)
C8	0.0474 (14)	0.0477 (16)	0.0351 (14)	−0.0028 (12)	−0.0063 (11)	−0.0026 (12)
C9	0.0409 (13)	0.0541 (17)	0.0462 (16)	0.0054 (12)	−0.0047 (12)	−0.0015 (13)
C10	0.0630 (18)	0.0593 (18)	0.0395 (16)	0.0063 (15)	−0.0078 (13)	0.0033 (13)
C11	0.0399 (13)	0.0428 (15)	0.0400 (15)	−0.0012 (12)	−0.0094 (11)	0.0003 (12)
C12	0.0413 (13)	0.0493 (16)	0.0519 (17)	0.0012 (12)	−0.0073 (12)	−0.0047 (13)
C13	0.0377 (13)	0.0486 (16)	0.0475 (16)	−0.0029 (11)	−0.0056 (12)	−0.0019 (12)
C14	0.0471 (15)	0.0493 (16)	0.0554 (18)	−0.0022 (12)	0.0104 (13)	0.0016 (14)
C15	0.0489 (15)	0.0655 (19)	0.0492 (17)	−0.0035 (14)	0.0040 (13)	−0.0079 (15)
C16	0.0601 (17)	0.0510 (16)	0.0384 (14)	0.0040 (14)	0.0057 (13)	0.0006 (13)
C17	0.0656 (18)	0.067 (2)	0.0427 (16)	−0.0056 (16)	0.0035 (14)	−0.0031 (15)

Geometric parameters (Å, º)

O1—C7	1.374 (3)	C7—C10	1.388 (4)
O1—C11	1.370 (3)	C8—C16	1.376 (4)
N1—C5	1.316 (3)	C8—H4	0.9300
N1—C4	1.419 (3)	C9—H5	0.9600
N1—H13	0.88 (3)	C9—H11	0.9600
C1—C5	1.429 (3)	C9—H7	0.9600
C1—C2	1.437 (3)	C10—C17	1.369 (4)
C1—C11	1.441 (3)	C10—H10	0.9300
O3—C2	1.252 (3)	C12—C15	1.373 (4)
C2—C3	1.469 (3)	C12—H1	0.9300
C3—C7	1.381 (3)	C13—C14	1.376 (4)
C3—C12	1.388 (3)	C13—H2	0.9300
C4—C13	1.382 (3)	C14—C16	1.376 (4)
C4—C6	1.396 (3)	C14—H3	0.9300
O4—C6	1.359 (3)	C15—C17	1.393 (4)
O4—H12	0.8200	C15—H8	0.9300
C5—C9	1.498 (3)	C16—H6	0.9300
O2—C11	1.223 (3)	C17—H9	0.9300
C6—C8	1.379 (3)
C7—O1—C11	122.26 (19)	C5—C9—H11	109.5
C5—N1—C4	127.4 (2)	H5—C9—H11	109.5
C5—N1—H13	112 (2)	C5—C9—H7	109.5
C4—N1—H13	121 (2)	H5—C9—H7	109.5
C5—C1—C2	120.5 (2)	H11—C9—H7	109.5
C5—C1—C11	119.9 (2)	C17—C10—C7	119.2 (3)
C2—C1—C11	119.6 (2)	C17—C10—H10	120.4
O3—C2—C1	123.5 (2)	C7—C10—H10	120.4
O3—C2—C3	118.8 (2)	O2—C11—O1	113.1 (2)
C1—C2—C3	117.7 (2)	O2—C11—C1	127.5 (2)
C7—C3—C12	118.6 (2)	O1—C11—C1	119.4 (2)
C7—C3—C2	119.3 (2)	C15—C12—C3	121.0 (3)
C12—C3—C2	122.0 (2)	C15—C12—H1	119.5
C13—C4—C6	120.0 (2)	C3—C12—H1	119.5
C13—C4—N1	121.1 (2)	C4—C13—C14	120.4 (2)
C6—C4—N1	118.8 (2)	C4—C13—H2	119.8
C6—O4—H12	109.5	C14—C13—H2	119.8
N1—C5—C1	118.2 (2)	C13—C14—C16	119.3 (2)
N1—C5—C9	118.7 (2)	C13—C14—H3	120.4
C1—C5—C9	123.0 (2)	C16—C14—H3	120.4
O4—C6—C8	123.5 (2)	C12—C15—C17	119.3 (3)
O4—C6—C4	117.4 (2)	C12—C15—H8	120.4
C8—C6—C4	119.1 (2)	C17—C15—H8	120.4
O1—C7—C3	121.7 (2)	C8—C16—C14	121.0 (3)
O1—C7—C10	117.2 (2)	C8—C16—H6	119.5
C3—C7—C10	121.1 (2)	C14—C16—H6	119.5
C6—C8—C16	120.1 (2)	C10—C17—C15	120.7 (3)
C6—C8—H4	119.9	C10—C17—H9	119.6
C16—C8—H4	119.9	C15—C17—H9	119.6
C5—C9—H5	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H12···O2^i	0.82	1.92	2.742 (2)	175
N1—H13···O3	0.88 (3)	1.75 (3)	2.537 (3)	148 (3)
C8—H4···O2^i	0.93	2.59	3.274 (3)	131

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.