Charge density of the biologically active molecule (2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid

Wang, A.; Ashurov, J.; Ibragimov, A.; Wang, R.; Mouhib, H.; Mukhamedov, N.; Englert, U.

doi:10.1107/S2052520615023690

Charge density of the biologically active molecule (2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid

A. Wang, J. Ashurov, A. Ibragimov, R. Wang, H. Mouhib, N. Mukhamedov and U. Englert

(2-Oxo-1,3-benzoxazol-3(2H)-yl)acetic acid is a member of a biologically active class of compounds. Its molecular structure in the crystal has been determined by X-ray diffraction, and its gas phase structure was obtained by quantum chemical calculations at the B3LYP/6-311++G(d,p) level of theory. In order to understand the dynamics of the molecule, two presumably soft degrees of freedom associated with the relative orientation of the planar benzoxazolone system and its substituent at the N atom were varied systematically. Five conformers have been identified as local minima on the resulting two-dimensional potential energy surface within an energy window of 27 kJ mol⁻¹. The energetically most favourable minimum closely matches the conformation observed in the crystal. Based on high-resolution diffraction data collected at low temperature, the experimental electron density of the compound was determined. Comparison with the electron density established by theory for the isolated molecule allowed the effect of intermolecular interactions to be addressed, in particular a moderately strong O—H

O hydrogen bond with a donor

acceptor distance of 2.6177 (9) Å: the oxygen acceptor is clearly polarized in the extended solid. The hydrogen bond connects consecutive molecules to chains, and the pronounced charge separation leads to stacking between neighburs with antiparallel dipole moments perpendicular to the chain direction.

Keywords: experimental electron density; multipole refinement; potential energy surface; conformational degrees of freedom; intermolecular interactions and polarization.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615023690/pi5027sup1.cif Contains datablocks global, iam
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520615023690/pi5027iamsup2.hkl Contains datablock iam
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520615023690/pi5027mmsup3.hkl Contains datablock mm
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615023690/pi5027sup4.pdf Supporting tables and figures

CCDC reference: 1426002

Computing details top

Data collection: Bruker SMART for iam; SMART (Bruker, 2001) for mm. Cell refinement: Bruker SAINT for iam; SMART for mm. Data reduction: Bruker SAINT for iam; SAINT (Bruker, 1999) for mm. Program(s) used to solve structure: SHELXS97 for iam; SHELXS97 (Sheldrick, 2013) for mm. Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013) for iam; Volkov et al., (2006) for mm. Molecular graphics: Volkov et al., (2006) for mm. Software used to prepare material for publication: Volkov et al., (2006) for mm.

Figures top

(iam) top

Crystal data top

C₉H₇NO₄	F(000) = 800
M_r = 193.16	D_x = 1.547 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7600 (2) Å	Cell parameters from 9898 reflections
b = 8.0593 (1) Å	θ = 2.5–50.7°
c = 16.6668 (2) Å	µ = 0.12 mm⁻¹
β = 104.6104 (5)°	T = 100 K
V = 1658.53 (4) Å³	Block, colourless
Z = 8	0.23 × 0.21 × 0.17 mm

Data collection top

CCD area detector diffractometer	9043 independent reflections
Radiation source: Incoatec microsource	6814 reflections with I > 2σ(I)
Multilayer optics monochromator	R_int = 0.043
ω scans	θ_max = 50.9°, θ_min = 2.5°
Absorption correction: multi-scan SADABS	h = −27→27
T_min = 0.972, T_max = 0.979	k = −17→17
58565 measured reflections	l = −36→36

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0732P)² + 0.2714P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
9043 reflections	Δρ_max = 0.80 e Å⁻³
130 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₉H₇NO₄	V = 1658.53 (4) Å³
M_r = 193.16	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.7600 (2) Å	µ = 0.12 mm⁻¹
b = 8.0593 (1) Å	T = 100 K
c = 16.6668 (2) Å	0.23 × 0.21 × 0.17 mm
β = 104.6104 (5)°

Data collection top

CCD area detector diffractometer	9043 independent reflections
Absorption correction: multi-scan SADABS	6814 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.979	R_int = 0.043
58565 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	1 restraint
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.80 e Å⁻³
9043 reflections	Δρ_min = −0.25 e Å⁻³
130 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.18601 (3)	0.58635 (5)	0.47510 (2)	0.01809 (6)
O2	0.27404 (3)	0.47052 (6)	0.59703 (3)	0.02161 (7)
O3	0.22896 (4)	0.83705 (6)	0.70231 (3)	0.02142 (7)
O4	0.13927 (4)	0.74431 (7)	0.79363 (3)	0.02593 (9)
H4O	0.1764 (10)	0.8181 (14)	0.8237 (8)	0.031*
N1	0.11396 (3)	0.61857 (6)	0.58221 (3)	0.01629 (6)
C1	0.09240 (4)	0.68007 (6)	0.44917 (3)	0.01628 (7)
C2	0.04911 (4)	0.74467 (7)	0.37141 (3)	0.01941 (8)
H2C	0.0824	0.7294	0.3270	0.023*
C3	−0.04724 (5)	0.83432 (7)	0.36200 (4)	0.02120 (8)
H3C	−0.0807	0.8817	0.3096	0.025*
C4	−0.09540 (4)	0.85577 (8)	0.42782 (4)	0.02125 (8)
H4C	−0.1610	0.9168	0.4190	0.026*
C5	−0.04946 (4)	0.78967 (7)	0.50654 (3)	0.01943 (8)
H5C	−0.0820	0.8043	0.5514	0.023*
C6	0.04597 (4)	0.70179 (6)	0.51543 (3)	0.01583 (6)
C7	0.19795 (4)	0.55086 (6)	0.55707 (3)	0.01668 (7)
C8	0.10322 (4)	0.60853 (7)	0.66614 (3)	0.01780 (7)
H8A	0.1303	0.4994	0.6898	0.021*
H8B	0.0256	0.6159	0.6655	0.021*
C9	0.16468 (4)	0.74452 (6)	0.72125 (3)	0.01656 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.01698 (12)	0.02261 (15)	0.01679 (12)	0.00194 (11)	0.00816 (10)	0.00047 (11)
O2	0.01789 (14)	0.02561 (17)	0.02278 (16)	0.00358 (12)	0.00784 (12)	0.00523 (13)
O3	0.02152 (15)	0.02524 (17)	0.01893 (14)	−0.00654 (13)	0.00774 (12)	−0.00121 (12)
O4	0.02630 (18)	0.0376 (2)	0.01687 (14)	−0.01154 (17)	0.01093 (13)	−0.00784 (14)
N1	0.01552 (12)	0.02000 (15)	0.01481 (12)	−0.00030 (11)	0.00653 (10)	−0.00183 (10)
C1	0.01534 (14)	0.01867 (16)	0.01590 (14)	−0.00089 (12)	0.00591 (11)	−0.00162 (12)
C2	0.01994 (17)	0.02230 (19)	0.01651 (16)	−0.00084 (14)	0.00557 (13)	−0.00066 (13)
C3	0.02066 (18)	0.0221 (2)	0.01944 (18)	−0.00002 (15)	0.00241 (14)	−0.00119 (14)
C4	0.01751 (16)	0.02202 (19)	0.0233 (2)	0.00138 (15)	0.00347 (14)	−0.00293 (15)
C5	0.01667 (15)	0.02150 (18)	0.02109 (18)	0.00061 (14)	0.00655 (13)	−0.00435 (14)
C6	0.01461 (13)	0.01768 (15)	0.01605 (14)	−0.00124 (12)	0.00541 (11)	−0.00316 (11)
C7	0.01537 (14)	0.01917 (16)	0.01708 (15)	−0.00049 (12)	0.00704 (11)	−0.00006 (12)
C8	0.01847 (15)	0.02076 (17)	0.01618 (15)	−0.00315 (13)	0.00807 (12)	−0.00182 (12)
C9	0.01485 (13)	0.02116 (17)	0.01447 (14)	−0.00069 (12)	0.00519 (11)	−0.00093 (12)

Geometric parameters (Å, º) top

O1—C7	1.3662 (6)	C2—C3	1.4003 (8)
O1—C1	1.3869 (6)	C2—H2C	0.9500
O2—C7	1.2163 (6)	C3—C4	1.3968 (9)
O3—C9	1.2080 (6)	C3—H3C	0.9500
O4—C9	1.3259 (6)	C4—C5	1.4002 (8)
O4—H4O	0.842 (8)	C4—H4C	0.9500
N1—C7	1.3595 (6)	C5—C6	1.3839 (7)
N1—C6	1.3979 (7)	C5—H5C	0.9500
N1—C8	1.4419 (6)	C8—C9	1.5154 (7)
C1—C2	1.3765 (7)	C8—H8A	0.9900
C1—C6	1.3898 (6)	C8—H8B	0.9900

C7—O1—C1	107.19 (4)	C6—C5—H5C	121.8
C9—O4—H4O	108.1 (10)	C4—C5—H5C	121.8
C7—N1—C6	109.05 (4)	C5—C6—C1	121.29 (5)
C7—N1—C8	123.49 (4)	C5—C6—N1	133.11 (4)
C6—N1—C8	127.41 (4)	C1—C6—N1	105.59 (4)
C2—C1—O1	127.51 (4)	O2—C7—N1	128.85 (5)
C2—C1—C6	123.38 (5)	O2—C7—O1	122.09 (4)
O1—C1—C6	109.11 (4)	N1—C7—O1	109.05 (4)
C1—C2—C3	115.67 (5)	N1—C8—C9	112.71 (4)
C1—C2—H2C	122.2	N1—C8—H8A	109.0
C3—C2—H2C	122.2	C9—C8—H8A	109.0
C4—C3—C2	121.57 (5)	N1—C8—H8B	109.0
C4—C3—H3C	119.2	C9—C8—H8B	109.0
C2—C3—H3C	119.2	H8A—C8—H8B	107.8
C3—C4—C5	121.72 (5)	O3—C9—O4	125.21 (5)
C3—C4—H4C	119.1	O3—C9—C8	124.74 (4)
C5—C4—H4C	119.1	O4—C9—C8	110.03 (4)
C6—C5—C4	116.37 (5)

(mm) top

Crystal data top

C₉H₇NO₄	F(000) = 800
M_r = 193.16	D_x = 1.547 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7600 (2) Å	Cell parameters from 9898 reflections
b = 8.0593 (1) Å	θ = 2.5–50.7°
c = 16.6668 (2) Å	µ = 0.12 mm⁻¹
β = 104.6104 (5)°	T = 100 K
V = 1658.53 (4) Å³	Block, colourless
Z = 8	0.23 × 0.21 × 0.17 mm

Data collection top

CCD area detector diffractometer	9043 independent reflections
Radiation source: Incoatec microsource	6814 reflections with I > 2σ(I)
Multilayer optics monochromator	R_int = 0.043
ω scans	θ_max = 50.9°, θ_min = 2.5°
Absorption correction: multi-scan SADABS	h = −27→27
T_min = 0.972, T_max = 0.979	k = −17→17
58565 measured reflections	l = −36→36

Refinement top

Refinement on F²	539 parameters
Least-squares matrix: full	0 restraints
R[F² > 2σ(F²)] = 0.051	w2 = q/[s²(F_o²) + (0.04 P)² + 0.00 P + 0.00 + 0.00 sin(th)] where P = (0.3333 F_o² + 0.6667 F_c²) q = 1.0
wR(F²) = 0.091	(Δ/σ)_max < 0.001
S = 1.61	Δρ_max = 0.23 e Å⁻³
8742 reflections	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₉H₇NO₄	V = 1658.53 (4) Å³
M_r = 193.16	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.7600 (2) Å	µ = 0.12 mm⁻¹
b = 8.0593 (1) Å	T = 100 K
c = 16.6668 (2) Å	0.23 × 0.21 × 0.17 mm
β = 104.6104 (5)°

Data collection top

CCD area detector diffractometer	9043 independent reflections
Absorption correction: multi-scan SADABS	6814 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.979	R_int = 0.043
58565 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	539 parameters
wR(F²) = 0.091	0 restraints
S = 1.61	Δρ_max = 0.23 e Å⁻³
8742 reflections	Δρ_min = −0.18 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O(1)	0.18590 (4)	0.58647 (7)	0.47507 (3)	0.018
O(2)	0.27395 (4)	0.47069 (7)	0.59700 (3)	0.021
O(3)	0.22911 (7)	0.83703 (13)	0.70230 (6)	0.021
O(4)	0.13950 (5)	0.74428 (10)	0.79371 (3)	0.025
N(1)	0.11393 (3)	0.61865 (5)	0.58223 (2)	0.016
C(1)	0.09246 (3)	0.68002 (5)	0.44917 (2)	0.016
C(2)	0.04909 (4)	0.74472 (6)	0.37133 (3)	0.019
C(3)	−0.04728 (4)	0.83441 (6)	0.36193 (3)	0.021
C(4)	−0.09549 (4)	0.85591 (6)	0.42780 (3)	0.021
C(5)	−0.04948 (3)	0.78970 (6)	0.50660 (3)	0.019
C(6)	0.04595 (3)	0.70183 (5)	0.51542 (2)	0.015
C(7)	0.19788 (3)	0.55090 (5)	0.55703 (2)	0.016
C(8)	0.10319 (3)	0.60868 (5)	0.66611 (2)	0.017
C(9)	0.16471 (3)	0.74458 (5)	0.72130 (2)	0.016
H(4O)	0.18139	0.833839	0.830799	0.027
H(2C)	0.0887 (14)	0.723 (2)	0.3242 (12)	0.022 (4)
H(3C)	−0.0840 (17)	0.886 (2)	0.3050 (15)	0.034 (5)
H(4C)	−0.168 (2)	0.922 (3)	0.4219 (15)	0.044 (7)
H(5C)	−0.0852 (13)	0.811 (2)	0.5573 (11)	0.015 (4)
H(8A)	0.1379 (16)	0.493 (3)	0.6925 (12)	0.016 (5)
H(8B)	0.020 (2)	0.614 (2)	0.6657 (12)	0.029 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O(1)	0.01659 (14)	0.02184 (17)	0.01661 (15)	0.00188 (14)	0.00796 (12)	0.00027 (14)
O(2)	0.01765 (14)	0.02477 (18)	0.02217 (16)	0.00376 (14)	0.00765 (12)	0.00535 (14)
O(3)	0.0212 (3)	0.0251 (3)	0.0178 (3)	−0.0072 (3)	0.0071 (2)	−0.0017 (2)
O(4)	0.0260 (2)	0.0364 (3)	0.01663 (17)	−0.0117 (2)	0.01071 (15)	−0.00789 (18)
N(1)	0.01518 (11)	0.01964 (13)	0.01442 (11)	−0.00024 (10)	0.00632 (9)	−0.00183 (10)
C(1)	0.01505 (11)	0.01864 (13)	0.01531 (13)	−0.00070 (10)	0.00583 (10)	−0.00146 (10)
C(2)	0.01963 (14)	0.02226 (16)	0.01578 (13)	−0.00028 (13)	0.00538 (11)	−0.00022 (12)
C(3)	0.02013 (15)	0.02198 (17)	0.01913 (16)	0.00062 (13)	0.00248 (12)	−0.00110 (13)
C(4)	0.01739 (14)	0.02189 (16)	0.02261 (17)	0.00191 (13)	0.00328 (12)	−0.00273 (13)
C(5)	0.01635 (13)	0.02146 (16)	0.02045 (15)	0.00092 (12)	0.00651 (11)	−0.00409 (12)
C(6)	0.01422 (11)	0.01747 (13)	0.01561 (12)	−0.00085 (10)	0.00533 (10)	−0.00304 (10)
C(7)	0.01479 (11)	0.01902 (14)	0.01665 (13)	0.00034 (11)	0.00673 (10)	0.00033 (11)
C(8)	0.01809 (13)	0.02026 (15)	0.01605 (13)	−0.00307 (12)	0.00783 (10)	−0.00167 (11)
C(9)	0.01474 (11)	0.02093 (14)	0.01414 (11)	−0.00144 (11)	0.00540 (9)	−0.00107 (10)

Geometric parameters (Å, º) top

O(1)—C(1)	1.3845 (6)	C(2)—C(3)	1.4006 (6)
O(1)—C(7)	1.3660 (6)	C(2)—H(2C)	1.05 (2)
O(2)—C(7)	1.2156 (6)	C(3)—C(4)	1.3981 (7)
O(3)—C(9)	1.2091 (9)	C(3)—H(3C)	1.03 (3)
O(4)—C(9)	1.3251 (6)	C(4)—C(5)	1.4019 (7)
O(4)—H(4O)	1.0110 (6)	C(4)—H(4C)	1.05 (3)
N(1)—C(6)	1.3981 (5)	C(5)—C(6)	1.3840 (6)
N(1)—C(7)	1.3598 (5)	C(5)—H(5C)	1.07 (2)
N(1)—C(8)	1.4409 (5)	C(8)—C(9)	1.5158 (6)
C(1)—C(2)	1.3781 (6)	C(8)—H(8A)	1.08 (2)
C(1)—C(6)	1.3903 (5)	C(8)—H(8B)	1.06 (3)

C(1)—O(1)—C(7)	107.24 (4)	C(4)—C(5)—H(5C)	121.2 (8)
C(9)—O(4)—H(4O)	110.07 (5)	C(6)—C(5)—H(5C)	122.5 (8)
C(6)—N(1)—C(7)	108.98 (3)	N(1)—C(6)—C(1)	105.58 (3)
C(6)—N(1)—C(8)	127.43 (3)	N(1)—C(6)—C(5)	133.03 (4)
C(7)—N(1)—C(8)	123.53 (4)	C(1)—C(6)—C(5)	121.38 (4)
O(1)—C(1)—C(2)	127.54 (4)	O(1)—C(7)—O(2)	122.15 (4)
O(1)—C(1)—C(6)	109.13 (4)	O(1)—C(7)—N(1)	109.06 (4)
C(2)—C(1)—C(6)	123.32 (4)	O(2)—C(7)—N(1)	128.80 (4)
C(1)—C(2)—C(3)	115.68 (4)	N(1)—C(8)—C(9)	112.77 (3)
C(1)—C(2)—H(2C)	119.0 (9)	N(1)—C(8)—H(8A)	108.4 (10)
C(3)—C(2)—H(2C)	125.3 (9)	N(1)—C(8)—H(8B)	109.3 (10)
C(2)—C(3)—C(4)	121.60 (4)	C(9)—C(8)—H(8A)	106.3 (10)
C(2)—C(3)—H(3C)	119.4 (11)	C(9)—C(8)—H(8B)	109.7 (10)
C(4)—C(3)—H(3C)	119.0 (11)	H(8A)—C(8)—H(8B)	110.4 (14)
C(3)—C(4)—C(5)	121.69 (4)	O(3)—C(9)—O(4)	125.22 (6)
C(3)—C(4)—H(4C)	122.8 (13)	O(3)—C(9)—C(8)	124.65 (5)
C(5)—C(4)—H(4C)	115.5 (13)	O(4)—C(9)—C(8)	110.11 (4)
C(4)—C(5)—C(6)	116.33 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D—H···A
O(4)—H(4O)···O(2)ⁱ	1.01 (1)	1.63 (1)	166 (1)

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Experimental details

	(iam)	(mm)
Crystal data
Chemical formula	C₉H₇NO₄	C₉H₇NO₄
M_r	193.16	193.16
Crystal system, space group	Monoclinic, C2/c	Monoclinic, C2/c
Temperature (K)	100	100
a, b, c (Å)	12.7600 (2), 8.0593 (1), 16.6668 (2)	12.7600 (2), 8.0593 (1), 16.6668 (2)
β (°)	104.6104 (5)	104.6104 (5)
V (Å³)	1658.53 (4)	1658.53 (4)
Z	8	8
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.12	0.12
Crystal size (mm)	0.23 × 0.21 × 0.17	0.23 × 0.21 × 0.17

Data collection
Diffractometer	CCD area detector	CCD area detector
Absorption correction	Multi-scan SADABS	Multi-scan SADABS
T_min, T_max	0.972, 0.979	0.972, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	58565, 9043, 6814	58565, 9043, 6814
R_int	0.043	0.043
(sin θ/λ)_max (Å⁻¹)	1.092	1.092

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.145, 1.06	0.051, 0.091, 1.61
No. of reflections	9043	8742
No. of parameters	130	539
No. of restraints	1	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	?
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.25	0.23, −0.18

Computer programs: Bruker SMART, SMART (Bruker, 2001), Bruker SAINT, SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2013), SHELXL2013 (Sheldrick, 2013), Volkov et al., (2006).

Selected geometric parameters (Å, º) for (mm) top

O(1)—C(1)	1.3845 (6)	C(2)—C(3)	1.4006 (6)
O(1)—C(7)	1.3660 (6)	C(2)—H(2C)	1.05 (2)
O(2)—C(7)	1.2156 (6)	C(3)—C(4)	1.3981 (7)
O(3)—C(9)	1.2091 (9)	C(3)—H(3C)	1.03 (3)
O(4)—C(9)	1.3251 (6)	C(4)—C(5)	1.4019 (7)
O(4)—H(4O)	1.0110 (6)	C(4)—H(4C)	1.05 (3)
N(1)—C(6)	1.3981 (5)	C(5)—C(6)	1.3840 (6)
N(1)—C(7)	1.3598 (5)	C(5)—H(5C)	1.07 (2)
N(1)—C(8)	1.4409 (5)	C(8)—C(9)	1.5158 (6)
C(1)—C(2)	1.3781 (6)	C(8)—H(8A)	1.08 (2)
C(1)—C(6)	1.3903 (5)	C(8)—H(8B)	1.06 (3)

C(1)—O(1)—C(7)	107.24 (4)	C(4)—C(5)—H(5C)	121.2 (8)
C(9)—O(4)—H(4O)	110.07 (5)	C(6)—C(5)—H(5C)	122.5 (8)
C(6)—N(1)—C(7)	108.98 (3)	N(1)—C(6)—C(1)	105.58 (3)
C(6)—N(1)—C(8)	127.43 (3)	N(1)—C(6)—C(5)	133.03 (4)
C(7)—N(1)—C(8)	123.53 (4)	C(1)—C(6)—C(5)	121.38 (4)
O(1)—C(1)—C(2)	127.54 (4)	O(1)—C(7)—O(2)	122.15 (4)
O(1)—C(1)—C(6)	109.13 (4)	O(1)—C(7)—N(1)	109.06 (4)
C(2)—C(1)—C(6)	123.32 (4)	O(2)—C(7)—N(1)	128.80 (4)
C(1)—C(2)—C(3)	115.68 (4)	N(1)—C(8)—C(9)	112.77 (3)
C(1)—C(2)—H(2C)	119.0 (9)	N(1)—C(8)—H(8A)	108.4 (10)
C(3)—C(2)—H(2C)	125.3 (9)	N(1)—C(8)—H(8B)	109.3 (10)
C(2)—C(3)—C(4)	121.60 (4)	C(9)—C(8)—H(8A)	106.3 (10)
C(2)—C(3)—H(3C)	119.4 (11)	C(9)—C(8)—H(8B)	109.7 (10)
C(4)—C(3)—H(3C)	119.0 (11)	H(8A)—C(8)—H(8B)	110.4 (14)
C(3)—C(4)—C(5)	121.69 (4)	O(3)—C(9)—O(4)	125.22 (6)
C(3)—C(4)—H(4C)	122.8 (13)	O(3)—C(9)—C(8)	124.65 (5)
C(5)—C(4)—H(4C)	115.5 (13)	O(4)—C(9)—C(8)	110.11 (4)
C(4)—C(5)—C(6)	116.33 (4)

Hydrogen-bond geometry (Å, º) for (mm) top

D—H···A	D—H	H···A	D—H···A
O(4)—H(4O)···O(2)ⁱ	1.0110 (6)	1.6259 (5)	165.79 (3)

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

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