N′-[1-(2-Hy­droxy­phen­yl)ethyl­idene]-2-meth­oxy­benzohydrazide

Yue, S.-Y.; Lu, J.-F.

doi:10.1107/S1600536810020477

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1550

doi:10.1107/S1600536810020477

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N′-[1-(2-Hydroxyphenyl)ethylidene]-2-methoxybenzohydrazide

Si-Yu Yue ^a and Jiu-Fu Lu ^a ^*

^aSchool of Chemistry and Environmental Science, Shaanxi University of Technology, Hanzhong 723000, People's Republic of China
^*Correspondence e-mail: jiufulu@163.com

(Received 27 May 2010; accepted 29 May 2010; online 5 June 2010)

There are two independent molecules in the asymmetric unit of the title compound, C₁₆H₁₆N₂O₃, in which the dihedral angles between the two aromatic rings are 13.0 (3) and 6.4 (3)°. Intramolecular O—H⋯N and N—H⋯O hydrogen bonds are observed in both molecules, forming S(6) rings in all cases.

Related literature

For related structures, see: Lu et al. (2008a ,b ,c ); Xiao & Wei (2009 ); He (2008 ); Shi et al. (2007 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₃
M_r = 284.31
Monoclinic, P 2₁ /n
a = 11.5610 (12) Å
b = 10.8074 (11) Å
c = 22.544 (2) Å
β = 92.244 (5)°
V = 2814.6 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.17 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.981, T_max = 0.984
16351 measured reflections
6065 independent reflections
3390 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.146
S = 1.01
6065 reflections
391 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.535 (2)	144
O4—H4⋯N3	0.82	1.82	2.541 (2)	145
N2—H2⋯O3	0.90 (1)	1.83 (2)	2.591 (2)	141 (2)
N4—H4B⋯O6	0.90 (1)	1.88 (2)	2.619 (2)	138 (2)

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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 global, I. DOI: 10.1107/S1600536810020477/wn2390sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020477/wn2390Isup2.hkl

checkCIF report

Comment top

Recently we have reported a number of Schiff bases derived from the condensation of aldehydes or ketones with benzohydrazides (Lu et al., 2008a,b,c) We report here the crystal structure of the new title Schiff base compound.

In the crystal structure of the title compound, Fig. 1, there are two independent molecules in the asymmetric unit. The bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Xiao & Wei, 2009; He, 2008; Shi et al., 2007). The dihedral angles between the two aromatic rings in molecules A and B are 13.0 (3) and 6.4 (3)°, respectively. Intramolecular O—H···N and N—H···O hydrogen bonds are observed in the molecules (Table 1).

Related literature top

For related structures, see: Lu et al. (2008a,b,c); Xiao & Wei (2009); He (2008); Shi et al. (2007). For reference bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the Schiff base condensation of 1-(2-hydroxyphenyl)ethanone (0.1 mol, 13.6 g) and 2-methoxybenzohydrazide (0.1 mol, 16.6 g) in 95% ethanol (70 ml). The excess ethanol was removed by distillation. The resulting colourless solid was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a 95% ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 the asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The dashed lines indicate hydrogen bonds.

N'-[1-(2-Hydroxyphenyl)ethylidene]-2-methoxybenzohydrazide top

Crystal data top

C₁₆H₁₆N₂O₃	F(000) = 1200
M_r = 284.31	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.5610 (12) Å	Cell parameters from 3247 reflections
b = 10.8074 (11) Å	θ = 2.5–24.5°
c = 22.544 (2) Å	µ = 0.09 mm⁻¹
β = 92.244 (5)°	T = 298 K
V = 2814.6 (5) Å³	Block, colourless
Z = 8	0.20 × 0.17 × 0.17 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	6065 independent reflections
Radiation source: fine-focus sealed tube	3390 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
T_min = 0.981, T_max = 0.984	k = −13→13
16351 measured reflections	l = −28→28

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0661P)² + 0.2197P] where P = (F_o² + 2F_c²)/3
6065 reflections	(Δ/σ)_max < 0.001
391 parameters	Δρ_max = 0.18 e Å⁻³
2 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₃	V = 2814.6 (5) Å³
M_r = 284.31	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.5610 (12) Å	µ = 0.09 mm⁻¹
b = 10.8074 (11) Å	T = 298 K
c = 22.544 (2) Å	0.20 × 0.17 × 0.17 mm
β = 92.244 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	6065 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3390 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.984	R_int = 0.032
16351 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	2 restraints
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.18 e Å⁻³
6065 reflections	Δρ_min = −0.22 e Å⁻³
391 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
N1	0.32094 (13)	0.29578 (16)	0.92231 (7)	0.0578 (4)
N2	0.34893 (13)	0.35212 (17)	0.97530 (7)	0.0597 (4)
N3	0.16718 (12)	0.07857 (14)	0.00747 (7)	0.0541 (4)
N4	0.17677 (13)	0.16075 (15)	0.05364 (7)	0.0563 (4)
O1	0.17630 (13)	0.27945 (15)	0.83520 (7)	0.0765 (5)
H1	0.2056	0.3111	0.8652	0.115*
O2	0.21621 (14)	0.50002 (16)	0.95829 (7)	0.0969 (6)
O3	0.47037 (12)	0.36530 (14)	1.07416 (6)	0.0750 (4)
O4	0.23773 (13)	−0.12009 (15)	−0.03935 (7)	0.0826 (5)
H4	0.2346	−0.0665	−0.0137	0.124*
O5	0.31539 (14)	0.04667 (16)	0.10021 (7)	0.0888 (5)
O6	0.11005 (11)	0.36046 (13)	0.10849 (6)	0.0684 (4)
C1	0.33944 (15)	0.14134 (19)	0.85116 (8)	0.0549 (5)
C2	0.24499 (17)	0.1865 (2)	0.81688 (9)	0.0602 (5)
C3	0.2162 (2)	0.1340 (2)	0.76206 (10)	0.0767 (6)
H3	0.1532	0.1645	0.7397	0.092*
C4	0.2791 (2)	0.0384 (2)	0.74065 (10)	0.0797 (7)
H4A	0.2583	0.0035	0.7041	0.096*
C5	0.3730 (2)	−0.0064 (2)	0.77297 (10)	0.0780 (6)
H5	0.4165	−0.0709	0.7581	0.094*
C6	0.40240 (18)	0.0440 (2)	0.82710 (10)	0.0710 (6)
H6	0.4662	0.0127	0.8486	0.085*
C7	0.37168 (15)	0.1933 (2)	0.90977 (8)	0.0563 (5)
C8	0.45543 (18)	0.1287 (2)	0.95166 (9)	0.0759 (6)
H8A	0.5221	0.1802	0.9590	0.114*
H8B	0.4789	0.0519	0.9344	0.114*
H8C	0.4190	0.1126	0.9884	0.114*
C9	0.29454 (16)	0.4577 (2)	0.98954 (9)	0.0606 (5)
C10	0.33544 (15)	0.52031 (19)	1.04600 (8)	0.0569 (5)
C11	0.41947 (15)	0.4758 (2)	1.08692 (8)	0.0577 (5)
C12	0.44709 (18)	0.5422 (2)	1.13798 (9)	0.0729 (6)
H12	0.5020	0.5115	1.1654	0.087*
C13	0.3940 (2)	0.6530 (3)	1.14833 (11)	0.0827 (7)
H13	0.4127	0.6967	1.1829	0.099*
C14	0.3136 (2)	0.6999 (2)	1.10817 (12)	0.0865 (7)
H14	0.2788	0.7759	1.1150	0.104*
C15	0.28485 (19)	0.6335 (2)	1.05760 (11)	0.0733 (6)
H15	0.2300	0.6655	1.0305	0.088*
C16	0.56308 (19)	0.3193 (3)	1.11158 (10)	0.0882 (8)
H16A	0.6237	0.3799	1.1146	0.132*
H16B	0.5926	0.2444	1.0950	0.132*
H16C	0.5353	0.3026	1.1504	0.132*
C17	0.08689 (14)	0.00942 (18)	−0.08365 (8)	0.0505 (5)
C18	0.15800 (15)	−0.09596 (19)	−0.08333 (9)	0.0607 (5)
C19	0.14807 (18)	−0.1806 (2)	−0.12944 (11)	0.0790 (7)
H19	0.1947	−0.2508	−0.1284	0.095*
C20	0.07172 (17)	−0.1636 (2)	−0.17628 (10)	0.0748 (6)
H20	0.0673	−0.2208	−0.2071	0.090*
C21	0.00145 (18)	−0.0615 (2)	−0.17773 (10)	0.0701 (6)
H21	−0.0511	−0.0493	−0.2095	0.084*
C22	0.00875 (16)	0.0225 (2)	−0.13226 (9)	0.0627 (5)
H22	−0.0401	0.0909	−0.1337	0.075*
C23	0.09365 (15)	0.10144 (17)	−0.03562 (8)	0.0516 (5)
C24	0.01927 (17)	0.2152 (2)	−0.03747 (10)	0.0704 (6)
H24A	−0.0360	0.2105	−0.0069	0.106*
H24B	−0.0208	0.2209	−0.0755	0.106*
H24C	0.0670	0.2871	−0.0313	0.106*
C25	0.25190 (16)	0.1365 (2)	0.09986 (9)	0.0572 (5)
C26	0.25187 (15)	0.22604 (17)	0.15067 (8)	0.0524 (5)
C27	0.18211 (15)	0.33129 (18)	0.15560 (9)	0.0552 (5)
C28	0.18812 (18)	0.4015 (2)	0.20709 (10)	0.0680 (6)
H28	0.1409	0.4706	0.2105	0.082*
C29	0.2635 (2)	0.3694 (2)	0.25311 (10)	0.0747 (6)
H29	0.2664	0.4168	0.2876	0.090*
C30	0.33427 (19)	0.2686 (2)	0.24897 (10)	0.0744 (6)
H30	0.3862	0.2483	0.2800	0.089*
C31	0.32742 (17)	0.1977 (2)	0.19816 (9)	0.0640 (6)
H31	0.3749	0.1286	0.1956	0.077*
C32	0.0333 (2)	0.4636 (2)	0.11268 (11)	0.0884 (7)
H32A	−0.0163	0.4512	0.1453	0.133*
H32B	−0.0129	0.4708	0.0765	0.133*
H32C	0.0776	0.5379	0.1190	0.133*
H2	0.4078 (13)	0.330 (2)	1.0002 (8)	0.080*
H4B	0.1314 (15)	0.2279 (14)	0.0561 (9)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0546 (9)	0.0627 (11)	0.0555 (10)	0.0014 (8)	−0.0037 (8)	0.0059 (8)
N2	0.0567 (10)	0.0669 (11)	0.0546 (10)	0.0094 (9)	−0.0078 (8)	0.0061 (9)
N3	0.0520 (9)	0.0543 (10)	0.0559 (10)	0.0033 (8)	0.0014 (8)	0.0039 (8)
N4	0.0548 (9)	0.0540 (10)	0.0599 (10)	0.0068 (8)	−0.0006 (8)	0.0027 (9)
O1	0.0811 (10)	0.0791 (11)	0.0680 (10)	0.0200 (9)	−0.0146 (8)	0.0047 (8)
O2	0.0924 (11)	0.0879 (12)	0.1065 (12)	0.0312 (10)	−0.0459 (10)	−0.0091 (10)
O3	0.0696 (9)	0.0887 (11)	0.0652 (9)	0.0255 (8)	−0.0161 (7)	0.0016 (8)
O4	0.0723 (9)	0.0714 (10)	0.1018 (12)	0.0242 (8)	−0.0265 (9)	−0.0125 (9)
O5	0.0913 (11)	0.0879 (11)	0.0855 (11)	0.0431 (10)	−0.0196 (9)	−0.0160 (9)
O6	0.0639 (8)	0.0594 (9)	0.0810 (10)	0.0151 (7)	−0.0093 (7)	0.0014 (8)
C1	0.0500 (10)	0.0588 (12)	0.0562 (11)	−0.0027 (9)	0.0049 (9)	0.0117 (10)
C2	0.0605 (12)	0.0613 (13)	0.0590 (13)	0.0002 (11)	0.0038 (10)	0.0109 (10)
C3	0.0808 (15)	0.0853 (17)	0.0629 (14)	0.0030 (14)	−0.0124 (12)	0.0035 (13)
C4	0.0867 (16)	0.0848 (17)	0.0674 (14)	−0.0089 (14)	−0.0005 (13)	−0.0085 (13)
C5	0.0758 (15)	0.0801 (16)	0.0784 (15)	0.0034 (13)	0.0076 (13)	−0.0091 (13)
C6	0.0620 (12)	0.0771 (16)	0.0738 (15)	0.0055 (12)	0.0013 (11)	0.0023 (13)
C7	0.0484 (10)	0.0649 (13)	0.0557 (12)	0.0010 (10)	0.0036 (9)	0.0140 (10)
C8	0.0722 (14)	0.0903 (17)	0.0645 (13)	0.0219 (13)	−0.0069 (11)	0.0079 (12)
C9	0.0521 (11)	0.0626 (13)	0.0665 (13)	0.0036 (10)	−0.0057 (10)	0.0109 (11)
C10	0.0504 (10)	0.0592 (13)	0.0611 (12)	−0.0015 (10)	0.0018 (9)	0.0094 (10)
C11	0.0492 (11)	0.0680 (14)	0.0560 (12)	−0.0017 (10)	0.0051 (9)	0.0073 (10)
C12	0.0639 (13)	0.0939 (18)	0.0607 (13)	−0.0043 (13)	−0.0005 (10)	0.0002 (13)
C13	0.0853 (16)	0.0885 (19)	0.0746 (16)	−0.0078 (15)	0.0056 (13)	−0.0140 (14)
C14	0.0950 (18)	0.0719 (16)	0.0931 (18)	0.0080 (14)	0.0084 (15)	−0.0084 (15)
C15	0.0737 (14)	0.0649 (15)	0.0810 (16)	0.0070 (12)	−0.0010 (12)	0.0020 (12)
C16	0.0708 (14)	0.109 (2)	0.0834 (16)	0.0260 (14)	−0.0206 (12)	0.0132 (15)
C17	0.0426 (9)	0.0536 (11)	0.0557 (11)	−0.0009 (9)	0.0060 (8)	0.0085 (9)
C18	0.0443 (10)	0.0618 (13)	0.0758 (14)	0.0031 (10)	−0.0020 (10)	0.0009 (11)
C19	0.0604 (13)	0.0698 (15)	0.1064 (18)	0.0114 (12)	−0.0043 (13)	−0.0211 (14)
C20	0.0588 (13)	0.0823 (17)	0.0833 (16)	−0.0042 (12)	0.0015 (12)	−0.0186 (13)
C21	0.0653 (13)	0.0808 (16)	0.0640 (13)	−0.0014 (12)	−0.0014 (10)	0.0029 (12)
C22	0.0615 (12)	0.0649 (13)	0.0615 (12)	0.0060 (11)	0.0022 (10)	0.0097 (11)
C23	0.0459 (10)	0.0524 (11)	0.0569 (11)	0.0018 (9)	0.0082 (9)	0.0099 (9)
C24	0.0713 (13)	0.0676 (14)	0.0717 (14)	0.0174 (11)	−0.0035 (11)	0.0031 (11)
C25	0.0501 (11)	0.0600 (13)	0.0614 (12)	0.0036 (10)	−0.0003 (9)	0.0036 (10)
C26	0.0461 (10)	0.0505 (11)	0.0605 (12)	−0.0033 (9)	0.0023 (9)	0.0054 (10)
C27	0.0477 (10)	0.0529 (12)	0.0647 (12)	−0.0042 (9)	0.0003 (9)	0.0055 (10)
C28	0.0673 (13)	0.0553 (13)	0.0815 (15)	−0.0005 (11)	0.0033 (12)	−0.0061 (12)
C29	0.0824 (15)	0.0703 (15)	0.0708 (15)	−0.0098 (13)	−0.0035 (12)	−0.0101 (12)
C30	0.0778 (14)	0.0761 (16)	0.0679 (14)	−0.0004 (13)	−0.0138 (11)	0.0008 (13)
C31	0.0610 (12)	0.0641 (13)	0.0663 (13)	0.0025 (10)	−0.0038 (10)	0.0064 (11)
C32	0.0823 (15)	0.0685 (15)	0.113 (2)	0.0279 (13)	−0.0103 (14)	0.0000 (14)

Geometric parameters (Å, º) top

N1—C7	1.290 (2)	C12—H12	0.9300
N1—N2	1.368 (2)	C13—C14	1.369 (3)
N2—C9	1.347 (3)	C13—H13	0.9300
N2—H2	0.896 (9)	C14—C15	1.377 (3)
N3—C23	1.289 (2)	C14—H14	0.9300
N3—N4	1.370 (2)	C15—H15	0.9300
N4—C25	1.356 (2)	C16—H16A	0.9600
N4—H4B	0.899 (9)	C16—H16B	0.9600
O1—C2	1.355 (2)	C16—H16C	0.9600
O1—H1	0.8200	C17—C22	1.400 (2)
O2—C9	1.215 (2)	C17—C18	1.405 (3)
O3—C11	1.367 (2)	C17—C23	1.470 (3)
O3—C16	1.427 (2)	C18—C19	1.386 (3)
O4—C18	1.352 (2)	C19—C20	1.362 (3)
O4—H4	0.8200	C19—H19	0.9300
O5—C25	1.217 (2)	C20—C21	1.370 (3)
O6—C27	1.361 (2)	C20—H20	0.9300
O6—C32	1.430 (2)	C21—C22	1.369 (3)
C1—C2	1.401 (3)	C21—H21	0.9300
C1—C6	1.401 (3)	C22—H22	0.9300
C1—C7	1.470 (3)	C23—C24	1.500 (3)
C2—C3	1.388 (3)	C24—H24A	0.9600
C3—C4	1.363 (3)	C24—H24B	0.9600
C3—H3	0.9300	C24—H24C	0.9600
C4—C5	1.372 (3)	C25—C26	1.499 (3)
C4—H4A	0.9300	C26—C31	1.389 (3)
C5—C6	1.367 (3)	C26—C27	1.401 (3)
C5—H5	0.9300	C27—C28	1.386 (3)
C6—H6	0.9300	C28—C29	1.373 (3)
C7—C8	1.498 (3)	C28—H28	0.9300
C8—H8A	0.9600	C29—C30	1.367 (3)
C8—H8B	0.9600	C29—H29	0.9300
C8—H8C	0.9600	C30—C31	1.378 (3)
C9—C10	1.502 (3)	C30—H30	0.9300
C10—C15	1.386 (3)	C31—H31	0.9300
C10—C11	1.399 (3)	C32—H32A	0.9600
C11—C12	1.383 (3)	C32—H32B	0.9600
C12—C13	1.370 (3)	C32—H32C	0.9600

C7—N1—N2	118.64 (16)	O3—C16—H16A	109.5
C9—N2—N1	119.21 (16)	O3—C16—H16B	109.5
C9—N2—H2	115.1 (14)	H16A—C16—H16B	109.5
N1—N2—H2	125.2 (14)	O3—C16—H16C	109.5
C23—N3—N4	118.66 (15)	H16A—C16—H16C	109.5
C25—N4—N3	119.30 (16)	H16B—C16—H16C	109.5
C25—N4—H4B	117.8 (14)	C22—C17—C18	116.45 (18)
N3—N4—H4B	122.7 (14)	C22—C17—C23	121.50 (17)
C2—O1—H1	109.5	C18—C17—C23	122.05 (17)
C11—O3—C16	119.98 (17)	O4—C18—C19	117.16 (18)
C18—O4—H4	109.5	O4—C18—C17	122.82 (19)
C27—O6—C32	119.43 (17)	C19—C18—C17	120.02 (19)
C2—C1—C6	116.99 (19)	C20—C19—C18	121.6 (2)
C2—C1—C7	121.85 (18)	C20—C19—H19	119.2
C6—C1—C7	121.17 (18)	C18—C19—H19	119.2
O1—C2—C3	116.81 (19)	C19—C20—C21	119.6 (2)
O1—C2—C1	122.93 (19)	C19—C20—H20	120.2
C3—C2—C1	120.2 (2)	C21—C20—H20	120.2
C4—C3—C2	120.8 (2)	C22—C21—C20	119.8 (2)
C4—C3—H3	119.6	C22—C21—H21	120.1
C2—C3—H3	119.6	C20—C21—H21	120.1
C3—C4—C5	120.1 (2)	C21—C22—C17	122.6 (2)
C3—C4—H4A	119.9	C21—C22—H22	118.7
C5—C4—H4A	119.9	C17—C22—H22	118.7
C6—C5—C4	119.8 (2)	N3—C23—C17	116.08 (16)
C6—C5—H5	120.1	N3—C23—C24	122.58 (18)
C4—C5—H5	120.1	C17—C23—C24	121.34 (16)
C5—C6—C1	122.0 (2)	C23—C24—H24A	109.5
C5—C6—H6	119.0	C23—C24—H24B	109.5
C1—C6—H6	119.0	H24A—C24—H24B	109.5
N1—C7—C1	115.04 (17)	C23—C24—H24C	109.5
N1—C7—C8	123.38 (19)	H24A—C24—H24C	109.5
C1—C7—C8	121.56 (19)	H24B—C24—H24C	109.5
C7—C8—H8A	109.5	O5—C25—N4	121.80 (19)
C7—C8—H8B	109.5	O5—C25—C26	121.87 (17)
H8A—C8—H8B	109.5	N4—C25—C26	116.32 (17)
C7—C8—H8C	109.5	C31—C26—C27	117.67 (18)
H8A—C8—H8C	109.5	C31—C26—C25	115.32 (17)
H8B—C8—H8C	109.5	C27—C26—C25	126.98 (17)
O2—C9—N2	121.67 (19)	O6—C27—C28	122.40 (18)
O2—C9—C10	121.6 (2)	O6—C27—C26	117.57 (18)
N2—C9—C10	116.69 (17)	C28—C27—C26	120.03 (18)
C15—C10—C11	117.8 (2)	C29—C28—C27	120.3 (2)
C15—C10—C9	115.91 (18)	C29—C28—H28	119.9
C11—C10—C9	126.25 (19)	C27—C28—H28	119.9
O3—C11—C12	122.77 (18)	C30—C29—C28	120.9 (2)
O3—C11—C10	117.10 (18)	C30—C29—H29	119.6
C12—C11—C10	120.1 (2)	C28—C29—H29	119.6
C13—C12—C11	120.3 (2)	C29—C30—C31	119.0 (2)
C13—C12—H12	119.8	C29—C30—H30	120.5
C11—C12—H12	119.8	C31—C30—H30	120.5
C14—C13—C12	120.6 (2)	C30—C31—C26	122.1 (2)
C14—C13—H13	119.7	C30—C31—H31	118.9
C12—C13—H13	119.7	C26—C31—H31	118.9
C13—C14—C15	119.3 (2)	O6—C32—H32A	109.5
C13—C14—H14	120.3	O6—C32—H32B	109.5
C15—C14—H14	120.3	H32A—C32—H32B	109.5
C14—C15—C10	121.8 (2)	O6—C32—H32C	109.5
C14—C15—H15	119.1	H32A—C32—H32C	109.5
C10—C15—H15	119.1	H32B—C32—H32C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.535 (2)	144
O4—H4···N3	0.82	1.82	2.541 (2)	145
N2—H2···O3	0.90 (1)	1.83 (2)	2.591 (2)	141 (2)
N4—H4B···O6	0.90 (1)	1.88 (2)	2.619 (2)	138 (2)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₃
M_r	284.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.5610 (12), 10.8074 (11), 22.544 (2)
β (°)	92.244 (5)
V (Å³)	2814.6 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.17 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.981, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	16351, 6065, 3390
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.146, 1.01
No. of reflections	6065
No. of parameters	391
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)	0.18, −0.22

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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
O1—H1···N1	0.82	1.82	2.535 (2)	144.2
O4—H4···N3	0.82	1.82	2.541 (2)	145.4
N2—H2···O3	0.896 (9)	1.832 (15)	2.591 (2)	141.1 (19)
N4—H4B···O6	0.899 (9)	1.879 (16)	2.619 (2)	138.2 (19)

Acknowledgements

The authors thank the Scientific Research Foundation of Shaanxi University of Technology (project No. SLGQD0708) for financial support.

References

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