2-Hydr­oxy-N′-(2-methoxy­naphthyl­idene)benzohydrazide

Qiu, X.-Y.

doi:10.1107/S1600536808026962

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1829-o1830

doi:10.1107/S1600536808026962

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2-Hydroxy-N′-(2-methoxynaphthylidene)benzohydrazide

Xiao-Yang Qiu ^a ^*

^aDepartment of Chemistry, Shangqiu Normal University, Shangqiu 476000, People's Republic of China
^*Correspondence e-mail: xiaoyang_qiu@126.com

(Received 13 August 2008; accepted 21 August 2008; online 23 August 2008)

The title Schiff base compound, C₁₉H₁₆N₂O₃, prepared by the reaction of 2-methoxy-1-naphthylaldehyde and 2-hydroxybenzohydrazide, crystallizes with two independent molecules in the asymmetric unit. Each molecule exists in a trans configuration with respect to the methylidene group. The naphthyl ring system make dihedral angles of 65.0 (2)° and 55.8 (2)° with the planes of the benzene rings. Intramolecular N—H⋯O and O—H⋯O hydrogen bonds help to stabilize the molecular conformations. In the crystal structure, molecules are linked into one-dimensional chains parallel to the c axis by intermolecular O—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For the biological properties of hydrazones, see: Bedia et al. (2006 ); Rollas et al. (2002 ); Fun et al. (2008 ). For our previous reports on hydrazones, see: Qiu, Fang et al. (2006 ); Qiu, Luo et al. (2006a ,b ); Qiu, Xu et al. (2006 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Singh et al. (2007 ); Narayana et al. (2007 ); Cui et al. (2007 ); Diao et al. (2008 ).

Experimental

Crystal data

C₁₉H₁₆N₂O₃
M_r = 320.34
Monoclinic, P 2₁ /c
a = 15.186 (3) Å
b = 9.059 (2) Å
c = 24.135 (3) Å
β = 108.331 (3)°
V = 3151.8 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.10 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.991, T_max = 0.994
17807 measured reflections
6805 independent reflections
4792 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.120
S = 1.03
6805 reflections
443 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N3ⁱ	0.82	2.24	3.0049 (18)	155
O3—H3⋯O5ⁱ	0.82	2.30	2.914 (2)	133
O6—H6⋯O2	0.82	1.87	2.6683 (17)	164
N2—H2⋯O3	0.918 (19)	1.942 (16)	2.6518 (18)	132.7 (17)
N4—H4A⋯O6	0.895 (9)	1.948 (16)	2.6581 (19)	135.0 (18)
N4—H4A⋯O4	0.895 (9)	2.38 (2)	2.877 (2)	114.9 (16)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026962/at2612sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026962/at2612Isup2.hkl

checkCIF report

Comment top

Hyrazone compounds, which derived from the reaction of aldehydes with hydrazides, have been widely studied due to their excellent biological properties (Bedia et al., 2006; Rollas et al., 2002; Fun et al., 2008). Recently, we have reported a few Schiff hydrazone compounds (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006a,b; Qiu, Xu et al., 2006), we report herein the crystal structure of the title new compound, (I).

Compound (I) crystallizes with two independent molecules in the asymmetric unit (Fig. 1). Each molecule exists in a trans configuration with respect to the methylidene group. The naphthyl rings make dihedral angles of 65.0 (2)° and 55.8 (2)° with the planes of the benzene rings. The bond lengths and angles in (I) are found to have normal values (Allen et al., 1987) and comparable to the values in the similar compounds (Singh et al., 2007; Narayana et al., 2007; Cui et al., 2007; Diao et al., 2008). Intramolecular O–H···O and N–H···O hydrogen bonds (Table 1) help to stabilize the molecular conformations. In the crystal structure, molecules are linked into one-dimensional chains parallel to the c axis by intermolecular O–H···N and O–H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the biological properties of hydrazones, see: Bedia et al. (2006); Rollas et al. (2002); Fun et al. (2008). For our previous reports on hydrazones, see: Qiu, Fang et al. (2006); Qiu, Luo et al. (2006a,b); Qiu, Xu et al. (2006). For bond-length data, see: Allen et al. (1987). For related structures, see: Singh et al. (2007); Narayana et al. (2007); Cui et al. (2007); Diao et al. (2008).

Experimental top

The title compound was prepared by the Schiff base condensation of equimolar (0.5 mmol each) 2-methoxy-1-naphthylaldehyde and 2-hydroxybenzohydrazide in methanol (20 ml). Excess methanol was removed from the reaction mixture with distillation. The colourless solid was filtered and dried in air. Colourless block-shaped crystals suitable for X-ray diffraction were obtained from a methanol solution.

Computing details top

Data collection: SMART (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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing and hydrogen bonding of (I), viewed along the b axis.

(I) top

Crystal data top

C₁₉H₁₆N₂O₃	F(000) = 1344
M_r = 320.34	D_x = 1.350 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5815 reflections
a = 15.186 (3) Å	θ = 2.4–28.1°
b = 9.059 (2) Å	µ = 0.09 mm⁻¹
c = 24.135 (3) Å	T = 298 K
β = 108.331 (3)°	Block, colourless
V = 3151.8 (10) Å³	0.10 × 0.08 × 0.07 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	6805 independent reflections
Radiation source: fine-focus sealed tube	4792 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→19
T_min = 0.991, T_max = 0.994	k = −11→11
17807 measured reflections	l = −30→30

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0503P)² + 0.6715P] where P = (F_o² + 2F_c²)/3
6805 reflections	(Δ/σ)_max < 0.001
443 parameters	Δρ_max = 0.20 e Å⁻³
2 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O₃	V = 3151.8 (10) Å³
M_r = 320.34	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.186 (3) Å	µ = 0.09 mm⁻¹
b = 9.059 (2) Å	T = 298 K
c = 24.135 (3) Å	0.10 × 0.08 × 0.07 mm
β = 108.331 (3)°

Data collection top

Bruker SMART CCD diffractometer	6805 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4792 reflections with I > 2σ(I)
T_min = 0.991, T_max = 0.994	R_int = 0.021
17807 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	2 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
6805 reflections	Δρ_min = −0.21 e Å⁻³
443 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.

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.43570 (8)	0.65866 (12)	0.40673 (6)	0.0577 (3)
O2	0.24611 (8)	0.06121 (13)	0.35547 (5)	0.0573 (3)
O3	0.15519 (9)	0.28893 (15)	0.47890 (6)	0.0654 (4)
H3	0.1503	0.2849	0.5117	0.098*
O4	0.16698 (9)	−0.14482 (14)	0.15763 (6)	0.0652 (4)
O5	0.23207 (9)	0.34100 (14)	0.09458 (6)	0.0665 (4)
O6	0.26324 (9)	0.11903 (14)	0.25093 (5)	0.0636 (3)
H6	0.2693	0.1034	0.2854	0.095*
N1	0.36544 (9)	0.26155 (15)	0.41827 (6)	0.0483 (3)
N2	0.27814 (9)	0.24269 (15)	0.42336 (6)	0.0466 (3)
N3	0.10594 (10)	0.13486 (16)	0.08670 (6)	0.0521 (4)
N4	0.17195 (9)	0.16834 (16)	0.13899 (6)	0.0490 (3)
C1	0.49640 (10)	0.42352 (17)	0.43517 (7)	0.0413 (4)
C2	0.51078 (11)	0.56729 (17)	0.41994 (7)	0.0442 (4)
C3	0.59831 (12)	0.61341 (19)	0.41810 (8)	0.0530 (4)
H3A	0.6072	0.7102	0.4082	0.064*
C4	0.66957 (12)	0.5156 (2)	0.43086 (8)	0.0556 (5)
H4	0.7270	0.5469	0.4291	0.067*
C5	0.65964 (11)	0.36863 (19)	0.44667 (7)	0.0483 (4)
C6	0.73541 (13)	0.2690 (2)	0.46050 (8)	0.0613 (5)
H6A	0.7926	0.3010	0.4586	0.074*
C7	0.72615 (15)	0.1284 (2)	0.47645 (9)	0.0696 (5)
H7	0.7763	0.0640	0.4854	0.084*
C8	0.64025 (14)	0.0810 (2)	0.47939 (9)	0.0699 (6)
H8	0.6341	−0.0155	0.4908	0.084*
C9	0.56529 (13)	0.1723 (2)	0.46597 (8)	0.0576 (5)
H9	0.5090	0.1366	0.4680	0.069*
C10	0.57139 (11)	0.32084 (18)	0.44889 (7)	0.0439 (4)
C11	0.40275 (10)	0.38697 (18)	0.43631 (7)	0.0434 (4)
H11	0.3698	0.4561	0.4504	0.052*
C12	0.22305 (11)	0.13587 (17)	0.39171 (7)	0.0436 (4)
C13	0.13277 (10)	0.11120 (17)	0.40235 (7)	0.0421 (4)
C14	0.10236 (11)	0.18085 (18)	0.44498 (7)	0.0470 (4)
C15	0.01809 (12)	0.1424 (2)	0.45176 (8)	0.0574 (5)
H15	−0.0014	0.1890	0.4802	0.069*
C16	−0.03670 (13)	0.0369 (2)	0.41726 (9)	0.0644 (5)
H16	−0.0929	0.0114	0.4225	0.077*
C17	−0.00877 (13)	−0.0316 (2)	0.37477 (9)	0.0654 (5)
H17	−0.0464	−0.1026	0.3509	0.078*
C18	0.07502 (12)	0.00486 (19)	0.36748 (8)	0.0535 (4)
H18	0.0934	−0.0425	0.3387	0.064*
C19	0.44208 (15)	0.8020 (2)	0.38459 (12)	0.0814 (7)
H19A	0.4892	0.8573	0.4129	0.122*
H19B	0.3835	0.8515	0.3767	0.122*
H19C	0.4579	0.7942	0.3492	0.122*
C20	0.02531 (11)	−0.02550 (18)	0.13957 (7)	0.0456 (4)
C21	0.08806 (12)	−0.12555 (18)	0.17276 (8)	0.0496 (4)
C22	0.06931 (13)	−0.2047 (2)	0.21794 (8)	0.0573 (5)
H22	0.1128	−0.2708	0.2405	0.069*
C23	−0.01255 (13)	−0.1841 (2)	0.22840 (8)	0.0568 (5)
H23	−0.0247	−0.2383	0.2579	0.068*
C24	−0.07948 (11)	−0.08342 (18)	0.19611 (7)	0.0476 (4)
C25	−0.16522 (13)	−0.0609 (2)	0.20663 (8)	0.0592 (5)
H25	−0.1784	−0.1142	0.2360	0.071*
C26	−0.22817 (13)	0.0369 (2)	0.17457 (9)	0.0642 (5)
H26	−0.2843	0.0499	0.1819	0.077*
C27	−0.20917 (13)	0.1186 (2)	0.13057 (9)	0.0630 (5)
H27	−0.2526	0.1860	0.1089	0.076*
C28	−0.12729 (12)	0.1001 (2)	0.11913 (8)	0.0546 (4)
H28	−0.1154	0.1559	0.0899	0.066*
C29	−0.06034 (11)	−0.00243 (17)	0.15091 (7)	0.0442 (4)
C30	0.04095 (12)	0.0481 (2)	0.08884 (8)	0.0521 (4)
H30	−0.0033	0.0281	0.0531	0.063*
C31	0.23628 (12)	0.27271 (18)	0.13895 (8)	0.0480 (4)
C32	0.31301 (12)	0.29697 (18)	0.19424 (8)	0.0497 (4)
C33	0.32713 (12)	0.22094 (19)	0.24690 (8)	0.0521 (4)
C34	0.40499 (14)	0.2494 (2)	0.29426 (9)	0.0671 (5)
H34	0.4144	0.1974	0.3289	0.080*
C35	0.46828 (16)	0.3539 (3)	0.29042 (10)	0.0822 (7)
H35	0.5207	0.3714	0.3223	0.099*
C36	0.45451 (17)	0.4331 (3)	0.23953 (11)	0.0847 (7)
H36	0.4967	0.5056	0.2373	0.102*
C37	0.37807 (15)	0.4044 (2)	0.19212 (10)	0.0672 (5)
H37	0.3694	0.4575	0.1578	0.081*
C38	0.23682 (15)	−0.2434 (3)	0.19098 (11)	0.0880 (7)
H38A	0.2578	−0.2118	0.2310	0.132*
H38B	0.2881	−0.2436	0.1757	0.132*
H38C	0.2116	−0.3413	0.1887	0.132*
H2	0.2587 (14)	0.302 (2)	0.4481 (8)	0.080*
H4A	0.1781 (14)	0.116 (2)	0.1714 (6)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0480 (7)	0.0460 (7)	0.0824 (9)	−0.0025 (5)	0.0255 (6)	0.0106 (6)
O2	0.0597 (8)	0.0567 (7)	0.0590 (8)	−0.0150 (6)	0.0236 (6)	−0.0042 (6)
O3	0.0675 (8)	0.0794 (9)	0.0541 (8)	−0.0345 (7)	0.0264 (7)	−0.0193 (7)
O4	0.0550 (7)	0.0666 (8)	0.0763 (9)	0.0205 (6)	0.0238 (7)	0.0149 (7)
O5	0.0687 (8)	0.0665 (8)	0.0698 (9)	0.0089 (7)	0.0296 (7)	0.0261 (7)
O6	0.0772 (9)	0.0642 (8)	0.0499 (7)	−0.0102 (7)	0.0206 (7)	0.0054 (6)
N1	0.0416 (7)	0.0511 (8)	0.0539 (8)	−0.0098 (6)	0.0173 (6)	0.0013 (7)
N2	0.0391 (7)	0.0490 (8)	0.0520 (8)	−0.0114 (6)	0.0147 (6)	−0.0003 (6)
N3	0.0466 (8)	0.0639 (9)	0.0484 (8)	0.0113 (7)	0.0186 (7)	0.0105 (7)
N4	0.0476 (8)	0.0555 (9)	0.0464 (8)	0.0072 (7)	0.0184 (7)	0.0101 (7)
C1	0.0385 (8)	0.0446 (8)	0.0400 (8)	−0.0099 (7)	0.0111 (6)	−0.0020 (7)
C2	0.0409 (8)	0.0443 (9)	0.0486 (9)	−0.0065 (7)	0.0157 (7)	−0.0011 (7)
C3	0.0491 (10)	0.0491 (10)	0.0649 (11)	−0.0122 (8)	0.0236 (8)	0.0033 (8)
C4	0.0408 (9)	0.0646 (11)	0.0652 (12)	−0.0126 (8)	0.0220 (8)	0.0004 (9)
C5	0.0419 (9)	0.0572 (10)	0.0454 (9)	−0.0044 (8)	0.0133 (7)	−0.0042 (8)
C6	0.0471 (10)	0.0761 (13)	0.0607 (12)	0.0048 (9)	0.0171 (9)	−0.0025 (10)
C7	0.0623 (13)	0.0728 (14)	0.0696 (13)	0.0173 (11)	0.0147 (10)	0.0008 (11)
C8	0.0721 (14)	0.0506 (11)	0.0779 (14)	0.0060 (10)	0.0107 (11)	0.0091 (10)
C9	0.0511 (10)	0.0521 (10)	0.0656 (12)	−0.0050 (8)	0.0127 (9)	0.0063 (9)
C10	0.0418 (9)	0.0471 (9)	0.0402 (9)	−0.0058 (7)	0.0094 (7)	−0.0032 (7)
C11	0.0387 (8)	0.0466 (9)	0.0437 (9)	−0.0078 (7)	0.0114 (7)	0.0038 (7)
C12	0.0473 (9)	0.0400 (8)	0.0396 (9)	−0.0079 (7)	0.0079 (7)	0.0058 (7)
C13	0.0431 (8)	0.0412 (8)	0.0379 (8)	−0.0087 (7)	0.0068 (6)	0.0089 (7)
C14	0.0487 (9)	0.0484 (9)	0.0398 (9)	−0.0128 (7)	0.0079 (7)	0.0032 (7)
C15	0.0545 (10)	0.0672 (12)	0.0537 (11)	−0.0150 (9)	0.0216 (8)	0.0020 (9)
C16	0.0521 (11)	0.0772 (13)	0.0647 (12)	−0.0234 (10)	0.0198 (9)	0.0046 (10)
C17	0.0616 (12)	0.0699 (12)	0.0619 (12)	−0.0324 (10)	0.0155 (10)	−0.0068 (10)
C18	0.0577 (11)	0.0516 (10)	0.0491 (10)	−0.0160 (8)	0.0138 (8)	−0.0034 (8)
C19	0.0717 (14)	0.0544 (12)	0.123 (2)	0.0039 (10)	0.0378 (13)	0.0286 (12)
C20	0.0449 (9)	0.0469 (9)	0.0435 (9)	−0.0001 (7)	0.0118 (7)	−0.0018 (7)
C21	0.0484 (9)	0.0473 (9)	0.0519 (10)	0.0037 (8)	0.0139 (8)	−0.0013 (8)
C22	0.0642 (12)	0.0476 (10)	0.0541 (11)	0.0044 (8)	0.0102 (9)	0.0064 (8)
C23	0.0714 (12)	0.0505 (10)	0.0500 (10)	−0.0098 (9)	0.0212 (9)	0.0014 (8)
C24	0.0513 (10)	0.0445 (9)	0.0467 (9)	−0.0120 (7)	0.0150 (8)	−0.0108 (7)
C25	0.0604 (11)	0.0633 (11)	0.0596 (11)	−0.0223 (10)	0.0270 (9)	−0.0171 (9)
C26	0.0452 (10)	0.0747 (13)	0.0742 (13)	−0.0112 (10)	0.0211 (10)	−0.0234 (11)
C27	0.0462 (10)	0.0645 (12)	0.0744 (13)	0.0003 (9)	0.0133 (9)	−0.0095 (10)
C28	0.0449 (10)	0.0568 (10)	0.0591 (11)	−0.0014 (8)	0.0117 (8)	−0.0015 (9)
C29	0.0429 (9)	0.0427 (8)	0.0453 (9)	−0.0057 (7)	0.0113 (7)	−0.0083 (7)
C30	0.0458 (9)	0.0649 (11)	0.0446 (9)	0.0091 (9)	0.0126 (7)	0.0049 (8)
C31	0.0503 (10)	0.0434 (9)	0.0595 (11)	0.0140 (8)	0.0307 (8)	0.0099 (8)
C32	0.0547 (10)	0.0458 (9)	0.0576 (10)	0.0058 (8)	0.0304 (8)	−0.0035 (8)
C33	0.0587 (11)	0.0502 (9)	0.0544 (11)	0.0022 (8)	0.0281 (9)	−0.0053 (8)
C34	0.0711 (13)	0.0813 (14)	0.0524 (11)	−0.0015 (11)	0.0246 (10)	−0.0123 (10)
C35	0.0760 (15)	0.1089 (19)	0.0671 (14)	−0.0206 (14)	0.0304 (12)	−0.0308 (13)
C36	0.0874 (16)	0.0939 (17)	0.0848 (17)	−0.0348 (13)	0.0443 (14)	−0.0277 (14)
C37	0.0785 (14)	0.0622 (12)	0.0746 (14)	−0.0090 (10)	0.0436 (12)	−0.0052 (10)
C38	0.0680 (14)	0.0909 (16)	0.1037 (19)	0.0353 (12)	0.0250 (13)	0.0250 (14)

Geometric parameters (Å, º) top

O1—C2	1.3631 (19)	C15—H15	0.9300
O1—C19	1.419 (2)	C16—C17	1.375 (3)
O2—C12	1.2401 (19)	C16—H16	0.9300
O3—C14	1.3635 (19)	C17—C18	1.378 (2)
O3—H3	0.8200	C17—H17	0.9300
O4—C21	1.370 (2)	C18—H18	0.9300
O4—C38	1.426 (2)	C19—H19A	0.9600
O5—C31	1.2208 (19)	C19—H19B	0.9600
O6—C33	1.365 (2)	C19—H19C	0.9600
O6—H6	0.8200	C20—C21	1.375 (2)
N1—C11	1.283 (2)	C20—C29	1.426 (2)
N1—N2	1.3801 (18)	C20—C30	1.477 (2)
N2—C12	1.348 (2)	C21—C22	1.407 (2)
N2—H2	0.918 (19)	C22—C23	1.357 (3)
N3—C30	1.275 (2)	C22—H22	0.9300
N3—N4	1.376 (2)	C23—C24	1.405 (2)
N4—C31	1.360 (2)	C23—H23	0.9300
N4—H4A	0.895 (9)	C24—C25	1.418 (2)
C1—C2	1.389 (2)	C24—C29	1.419 (2)
C1—C10	1.426 (2)	C25—C26	1.354 (3)
C1—C11	1.469 (2)	C25—H25	0.9300
C2—C3	1.407 (2)	C26—C27	1.397 (3)
C3—C4	1.357 (2)	C26—H26	0.9300
C3—H3A	0.9300	C27—C28	1.366 (2)
C4—C5	1.406 (2)	C27—H27	0.9300
C4—H4	0.9300	C28—C29	1.412 (2)
C5—C6	1.417 (2)	C28—H28	0.9300
C5—C10	1.425 (2)	C30—H30	0.9300
C6—C7	1.351 (3)	C31—C32	1.486 (3)
C6—H6A	0.9300	C32—C37	1.399 (3)
C7—C8	1.396 (3)	C32—C33	1.401 (2)
C7—H7	0.9300	C33—C34	1.386 (3)
C8—C9	1.361 (3)	C34—C35	1.373 (3)
C8—H8	0.9300	C34—H34	0.9300
C9—C10	1.419 (2)	C35—C36	1.381 (3)
C9—H9	0.9300	C35—H35	0.9300
C11—H11	0.9300	C36—C37	1.374 (3)
C12—C13	1.489 (2)	C36—H36	0.9300
C13—C18	1.393 (2)	C37—H37	0.9300
C13—C14	1.403 (2)	C38—H38A	0.9600
C14—C15	1.385 (2)	C38—H38B	0.9600
C15—C16	1.365 (3)	C38—H38C	0.9600

C2—O1—C19	119.52 (13)	O1—C19—H19A	109.5
C14—O3—H3	109.5	O1—C19—H19B	109.5
C21—O4—C38	119.16 (15)	H19A—C19—H19B	109.5
C33—O6—H6	109.5	O1—C19—H19C	109.5
C11—N1—N2	114.42 (14)	H19A—C19—H19C	109.5
C12—N2—N1	118.72 (14)	H19B—C19—H19C	109.5
C12—N2—H2	121.3 (13)	C21—C20—C29	119.43 (15)
N1—N2—H2	120.0 (13)	C21—C20—C30	121.17 (15)
C30—N3—N4	116.65 (14)	C29—C20—C30	119.14 (14)
C31—N4—N3	117.96 (14)	O4—C21—C20	115.65 (15)
C31—N4—H4A	119.5 (14)	O4—C21—C22	123.30 (15)
N3—N4—H4A	122.0 (14)	C20—C21—C22	121.03 (16)
C2—C1—C10	119.50 (14)	C23—C22—C21	119.64 (17)
C2—C1—C11	116.74 (14)	C23—C22—H22	120.2
C10—C1—C11	123.76 (14)	C21—C22—H22	120.2
O1—C2—C1	116.21 (13)	C22—C23—C24	122.10 (16)
O1—C2—C3	122.76 (14)	C22—C23—H23	119.0
C1—C2—C3	121.02 (15)	C24—C23—H23	119.0
C4—C3—C2	119.53 (16)	C23—C24—C25	122.61 (17)
C4—C3—H3A	120.2	C23—C24—C29	118.35 (15)
C2—C3—H3A	120.2	C25—C24—C29	119.03 (16)
C3—C4—C5	122.26 (15)	C26—C25—C24	120.98 (18)
C3—C4—H4	118.9	C26—C25—H25	119.5
C5—C4—H4	118.9	C24—C25—H25	119.5
C4—C5—C6	121.23 (16)	C25—C26—C27	120.25 (18)
C4—C5—C10	118.70 (15)	C25—C26—H26	119.9
C6—C5—C10	120.07 (16)	C27—C26—H26	119.9
C7—C6—C5	121.20 (18)	C28—C27—C26	120.50 (19)
C7—C6—H6A	119.4	C28—C27—H27	119.8
C5—C6—H6A	119.4	C26—C27—H27	119.8
C6—C7—C8	119.15 (18)	C27—C28—C29	121.10 (18)
C6—C7—H7	120.4	C27—C28—H28	119.4
C8—C7—H7	120.4	C29—C28—H28	119.4
C9—C8—C7	121.74 (19)	C28—C29—C24	118.11 (15)
C9—C8—H8	119.1	C28—C29—C20	122.44 (15)
C7—C8—H8	119.1	C24—C29—C20	119.44 (15)
C8—C9—C10	121.28 (17)	N3—C30—C20	129.77 (16)
C8—C9—H9	119.4	N3—C30—H30	115.1
C10—C9—H9	119.4	C20—C30—H30	115.1
C9—C10—C5	116.55 (15)	O5—C31—N4	120.90 (17)
C9—C10—C1	124.44 (15)	O5—C31—C32	121.51 (16)
C5—C10—C1	118.99 (14)	N4—C31—C32	117.56 (15)
N1—C11—C1	121.33 (15)	C37—C32—C33	117.81 (18)
N1—C11—H11	119.3	C37—C32—C31	115.67 (17)
C1—C11—H11	119.3	C33—C32—C31	126.49 (16)
O2—C12—N2	121.91 (15)	O6—C33—C34	120.55 (17)
O2—C12—C13	121.29 (14)	O6—C33—C32	119.19 (16)
N2—C12—C13	116.80 (15)	C34—C33—C32	120.26 (17)
C18—C13—C14	117.65 (15)	C35—C34—C33	120.4 (2)
C18—C13—C12	116.01 (15)	C35—C34—H34	119.8
C14—C13—C12	126.31 (14)	C33—C34—H34	119.8
O3—C14—C15	120.06 (15)	C34—C35—C36	120.3 (2)
O3—C14—C13	119.73 (14)	C34—C35—H35	119.8
C15—C14—C13	120.20 (15)	C36—C35—H35	119.8
C16—C15—C14	120.86 (18)	C37—C36—C35	119.6 (2)
C16—C15—H15	119.6	C37—C36—H36	120.2
C14—C15—H15	119.6	C35—C36—H36	120.2
C15—C16—C17	119.94 (17)	C36—C37—C32	121.5 (2)
C15—C16—H16	120.0	C36—C37—H37	119.2
C17—C16—H16	120.0	C32—C37—H37	119.2
C16—C17—C18	120.04 (17)	O4—C38—H38A	109.5
C16—C17—H17	120.0	O4—C38—H38B	109.5
C18—C17—H17	120.0	H38A—C38—H38B	109.5
C17—C18—C13	121.31 (17)	O4—C38—H38C	109.5
C17—C18—H18	119.3	H38A—C38—H38C	109.5
C13—C18—H18	119.3	H38B—C38—H38C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3ⁱ	0.82	2.24	3.0049 (18)	155
O3—H3···O5ⁱ	0.82	2.30	2.914 (2)	133
O6—H6···O2	0.82	1.87	2.6683 (17)	164
N2—H2···O3	0.92 (2)	1.94 (2)	2.6518 (18)	133 (2)
N4—H4A···O6	0.90 (1)	1.95 (2)	2.6581 (19)	135 (2)
N4—H4A···O4	0.90 (1)	2.38 (2)	2.877 (2)	115 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₂O₃
M_r	320.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.186 (3), 9.059 (2), 24.135 (3)
β (°)	108.331 (3)
V (Å³)	3151.8 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.10 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.991, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	17807, 6805, 4792
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.120, 1.03
No. of reflections	6805
No. of parameters	443
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3ⁱ	0.82	2.24	3.0049 (18)	155.2
O3—H3···O5ⁱ	0.82	2.30	2.914 (2)	132.5
O6—H6···O2	0.82	1.87	2.6683 (17)	163.5
N2—H2···O3	0.918 (19)	1.942 (16)	2.6518 (18)	132.7 (17)
N4—H4A···O6	0.895 (9)	1.948 (16)	2.6581 (19)	135.0 (18)
N4—H4A···O4	0.895 (9)	2.38 (2)	2.877 (2)	114.9 (16)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The author acknowledges the Education Office of Anhui Province (project No. KJ2008B178).

References

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