N′-(3-Eth­oxy-2-hy­droxy­benzyl­idene)-2-hy­droxy-3-methyl­benzohydrazide

Zhu, Z.-F.; Shao, L.-J.; Shen, X.-H.

doi:10.1107/S1600536812002127

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o500

doi:10.1107/S1600536812002127

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N′-(3-Ethoxy-2-hydroxybenzylidene)-2-hydroxy-3-methylbenzohydrazide

Zhao-Fu Zhu,^a Li-Juen Shao ^a and Xi-Hai Shen ^a ^*

^aDepartment of Chemistry, Hebei Normal University of Science and Technology, Qinhuangdao 066600, People's Republic of China
^*Correspondence e-mail: zhaofu_zhu@163.com

(Received 8 January 2012; accepted 17 January 2012; online 21 January 2012)

The title compound, C₁₇H₁₈N₂O₄, crystallizes with two independent molecules in the asymmetric unit. The two benzene rings in each molecule make dihedral angles of 7.6 (3) and 3.9 (3)°. Intramolecular O—H⋯N and O—H⋯O hydrogen bonds are present in each molecule. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains propagating in [010]. The are also a number of C—H⋯O and π–π interactions present [centroid–centroid distances = 3.874 (4) and 3.904 (3) Å], that result in the formation of a three-dimensional network.

Related literature

For the crystal structures of similar hydrazone compounds, see: Fun et al. (2011 ); Horkaew et al. (2011 ); Zhi et al. (2011 ); Huang & Wu (2010 ); Shen et al. (2012 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₄
M_r = 314.33
Monoclinic, P 2₁
a = 7.7661 (17) Å
b = 22.148 (3) Å
c = 9.7002 (16) Å
β = 100.382 (2)°
V = 1641.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.982, T_max = 0.984
8061 measured reflections
3436 independent reflections
1592 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.113
S = 0.97
3436 reflections
431 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.15 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	1.84	2.558 (5)	145
O4—H4B⋯O3	0.82	1.83	2.549 (5)	145
O5—H5⋯N3	0.82	1.87	2.585 (6)	145
O8—H8⋯O6	0.85 (3)	1.75 (4)	2.536 (6)	152 (5)
N2—H2⋯O5ⁱ	0.90 (2)	2.22 (2)	3.035 (6)	150 (4)
N2—H2⋯O7ⁱ	0.90 (2)	2.52 (4)	3.218 (6)	134 (3)
N4—H4⋯O1	0.90 (4)	2.26 (3)	3.027 (5)	144 (5)
C7—H7⋯O5ⁱ	0.93	2.59	3.353 (7)	140
C14—H14⋯O5ⁱ	0.93	2.60	3.516 (7)	169
C24—H24⋯O1	0.93	2.45	3.261 (6)	145
C33—H33A⋯O6ⁱⁱ	0.97	2.58	3.420 (7)	145
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536812002127/su2365sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002127/su2365Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002127/su2365Isup3.cml

checkCIF report

Comment top

In the last few years, the crystal structures of a number of hydrazone compounds have been reported (Fun et al., 2011; Horkaew et al., 2011; Zhi et al., 2011; Huang & Wu, 2010). However, compounds derived from 2-hydroxy-3-methylbenzohydrazide have seldom been reported. As an extension of our work on such compounds (Shen et al., 2012), we report herein on the crystal structure of the title compound, prepared by condensing 3-ethoxy-2-hydroxybenzaldehyde and 2-hydroxy-3-methylbenzohydrazide in methanol.

The asymmetric unit of the title compound contains two independent molecules (A & B), Fig. 1. In both molecules there are intramoleculoar O-H···N and O-H···O hydrogen bonds (Table 1).

In molecule A the (C1—C6) and (C9—C14) benzene rings make a dihedral angle of 7.6 (3)°. In molecule B the (C18—C23) and (C26—C31) benzene rings make a dihedral angle of 3.9 (3)°. All the bond values are within normal ranges and are comparable with those in the similar compounds reported on by (Fun et al., 2011; Horkaew et al., 2011; Zhi et al., 2011; Huang & Wu, 2010; Shen et al., 2012).

In the crystal, there are intermolecular N—H···O hydrogen bonds linking the molecules to form -A-B-A-B- chains propagating along the b axis direction. The are a number of C-H···O interactions present (Table 1), and some π–π interactions involving symmetry related A/A molecules and neighbouring B/B molecules [Cg1—Cg2ⁱ 3.874 (4) Å; symmetry code: (i) -x, y+172, -z+1; Cg3—Cg4ⁱⁱ 3.904 (3) Å; symmetry code: (ii) x-1, y, z; where Cg1, Cg2, Cg3, and Cg4 are the centroids of the (C1-C6), (C9-C14), (C18-C23) and (C26-C31) benzene rings, respectively]. The sum of these interactions results in the formation of a three-dimensional network.

Related literature top

For the crystal structures of similar hydrazone compounds, see: Fun et al. (2011); Horkaew et al. (2011); Zhi et al. (2011); Huang & Wu (2010); Shen et al. (2012).

Experimental top

3-Ethoxy-2-hydroxybenzaldehyde (166.2 mg, 1.0 mmol) and 2-hydroxy-3-methylbenzohydrazide (166.2 mg, 1.0 mmol) were mixed in methanol (60 ml), and refluxed for 30 min, then cooled to room temperature, yielding colourless solution. Colourless block-like crystals of the title compound were formed when the solution was evaporated in air for several days.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (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 two independent molecules (A and B) of the title compound, with atom numbering and displacement ellipsoids drawn at the 30% probability level. The intramolecular O—H···O and O—H···N hydrogen bonds are drawn as dashed lines - see Table 1 for details.
	Fig. 2. A partial view of the crystal packing of the title compound, viewed along the c axis. The O-H···O, O-H···N and N-H···O hydrogen bonds are drawn as dashed lines - see Table 1 for details.

N'-(3-Ethoxy-2-hydroxybenzylidene)-2-hydroxy-3-methylbenzohydrazide top

Crystal data top

C₁₇H₁₈N₂O₄	F(000) = 664
M_r = 314.33	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 756 reflections
a = 7.7661 (17) Å	θ = 2.3–24.1°
b = 22.148 (3) Å	µ = 0.09 mm⁻¹
c = 9.7002 (16) Å	T = 298 K
β = 100.382 (2)°	Block, colourless
V = 1641.1 (5) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3436 independent reflections
Radiation source: fine-focus sealed tube	1592 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ω scans	θ_max = 26.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→9
T_min = 0.982, T_max = 0.984	k = −26→27
8061 measured reflections	l = −11→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.033P)²] where P = (F_o² + 2F_c²)/3
3436 reflections	(Δ/σ)_max < 0.001
431 parameters	Δρ_max = 0.13 e Å⁻³
4 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₄	V = 1641.1 (5) Å³
M_r = 314.33	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 7.7661 (17) Å	µ = 0.09 mm⁻¹
b = 22.148 (3) Å	T = 298 K
c = 9.7002 (16) Å	0.20 × 0.20 × 0.18 mm
β = 100.382 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3436 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1592 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.984	R_int = 0.058
8061 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	4 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.13 e Å⁻³
3436 reflections	Δρ_min = −0.15 e Å⁻³
431 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.1824 (5)	0.21340 (14)	0.6459 (3)	0.0614 (14)
O2	0.2554 (5)	0.17087 (16)	0.9028 (4)	0.0698 (16)
O3	0.0043 (6)	0.24281 (18)	0.2650 (4)	0.0890 (19)
O4	−0.1208 (6)	0.23100 (17)	0.0048 (4)	0.0893 (17)
N1	0.1655 (6)	0.3042 (2)	0.4810 (5)	0.0631 (17)
N2	0.1167 (6)	0.3313 (2)	0.3504 (5)	0.0658 (19)
C1	0.2983 (7)	0.3115 (3)	0.7185 (6)	0.063 (2)
C2	0.2635 (6)	0.2517 (2)	0.7481 (5)	0.057 (2)
C3	0.3042 (7)	0.2287 (3)	0.8847 (6)	0.065 (2)
C4	0.3899 (9)	0.2654 (4)	0.9877 (7)	0.104 (3)
C5	0.4308 (10)	0.3244 (4)	0.9603 (8)	0.126 (4)
C6	0.3823 (9)	0.3481 (3)	0.8288 (8)	0.099 (3)
C7	0.2473 (7)	0.3374 (3)	0.5801 (6)	0.068 (3)
C8	0.0341 (8)	0.2960 (3)	0.2444 (6)	0.064 (2)
C9	−0.0216 (7)	0.3263 (2)	0.1074 (6)	0.057 (2)
C10	−0.0924 (7)	0.2907 (3)	−0.0083 (6)	0.069 (2)
C11	−0.1371 (8)	0.3159 (3)	−0.1414 (7)	0.080 (3)
C12	−0.1147 (9)	0.3763 (4)	−0.1557 (7)	0.097 (3)
C13	−0.0494 (9)	0.4132 (3)	−0.0452 (7)	0.094 (3)
C14	−0.0006 (8)	0.3884 (3)	0.0874 (6)	0.081 (3)
C15	−0.2122 (9)	0.2749 (3)	−0.2636 (7)	0.115 (3)
C16	0.2750 (8)	0.1487 (3)	1.0453 (6)	0.081 (3)
C17	0.1917 (9)	0.0870 (3)	1.0394 (6)	0.101 (3)
O5	−0.1527 (4)	−0.03370 (15)	0.5987 (4)	0.0601 (16)
O6	0.2365 (5)	0.00000 (16)	0.4276 (4)	0.0735 (17)
O7	−0.4309 (5)	−0.07716 (17)	0.6760 (4)	0.0754 (17)
O8	0.5012 (5)	−0.01235 (19)	0.3106 (4)	0.0801 (17)
N3	0.0562 (6)	0.05665 (19)	0.5918 (4)	0.0544 (17)
N4	0.1951 (6)	0.0840 (2)	0.5477 (5)	0.0597 (17)
C18	−0.1801 (7)	0.0613 (2)	0.7159 (5)	0.053 (2)
C19	−0.2382 (7)	0.0038 (2)	0.6776 (5)	0.0515 (19)
C20	−0.3885 (7)	−0.0194 (3)	0.7188 (6)	0.061 (2)
C21	−0.4786 (8)	0.0161 (3)	0.7980 (6)	0.082 (3)
C22	−0.4209 (9)	0.0736 (3)	0.8346 (7)	0.089 (3)
C23	−0.2746 (8)	0.0965 (3)	0.7968 (6)	0.075 (3)
C24	−0.0276 (7)	0.0874 (2)	0.6696 (6)	0.060 (2)
C25	0.2855 (7)	0.0518 (3)	0.4634 (6)	0.060 (2)
C26	0.4379 (7)	0.0804 (2)	0.4208 (5)	0.055 (2)
C27	0.5402 (8)	0.0456 (3)	0.3454 (6)	0.061 (2)
C28	0.6896 (8)	0.0694 (3)	0.3020 (6)	0.071 (3)
C29	0.7313 (8)	0.1279 (3)	0.3357 (7)	0.082 (3)
C30	0.6338 (9)	0.1639 (3)	0.4091 (7)	0.087 (3)
C31	0.4889 (8)	0.1399 (3)	0.4511 (6)	0.077 (3)
C32	0.7986 (9)	0.0305 (4)	0.2240 (7)	0.106 (3)
C33	−0.6007 (7)	−0.0994 (3)	0.6885 (6)	0.080 (3)
C34	−0.6145 (10)	−0.1627 (3)	0.6347 (8)	0.124 (4)
H1	0.16610	0.23080	0.57010	0.0920*
H2	0.147 (6)	0.3700 (9)	0.338 (5)	0.0800*
H4A	0.42150	0.25040	1.07830	0.1240*
H4B	−0.10510	0.22200	0.08810	0.1340*
H5A	0.49160	0.34820	1.03180	0.1520*
H6	0.40510	0.38840	0.81230	0.1180*
H7	0.27330	0.37740	0.56320	0.0810*
H12	−0.14490	0.39330	−0.24440	0.1170*
H13	−0.03800	0.45450	−0.05900	0.1120*
H14	0.04590	0.41280	0.16290	0.0980*
H15A	−0.24110	0.29850	−0.34760	0.1720*
H15B	−0.31570	0.25540	−0.24440	0.1720*
H15C	−0.12690	0.24490	−0.27580	0.1720*
H16A	0.21790	0.17580	1.10140	0.0970*
H16B	0.39800	0.14610	1.08710	0.0970*
H17A	0.06800	0.09060	1.00610	0.1510*
H17B	0.21200	0.06940	1.13140	0.1510*
H17C	0.24200	0.06160	0.97680	0.1510*
H4	0.243 (7)	0.1196 (13)	0.577 (5)	0.0800*
H5	−0.07000	−0.01560	0.57610	0.0900*
H8	0.397 (3)	−0.015 (3)	0.327 (6)	0.0800*
H21	−0.57850	0.00130	0.82670	0.0980*
H22	−0.48410	0.09740	0.88680	0.1080*
H23	−0.23710	0.13530	0.82430	0.0910*
H24	0.00870	0.12640	0.69670	0.0720*
H29	0.82990	0.14440	0.30810	0.0990*
H30	0.66600	0.20380	0.42960	0.1050*
H31	0.42330	0.16390	0.50080	0.0920*
H32A	0.73200	0.02030	0.13370	0.1580*
H32B	0.83150	−0.00580	0.27630	0.1580*
H32C	0.90200	0.05220	0.21210	0.1580*
H33A	−0.69100	−0.07450	0.63430	0.0950*
H33B	−0.61510	−0.09850	0.78580	0.0950*
H34A	−0.60150	−0.16290	0.53820	0.1870*
H34B	−0.72690	−0.17890	0.64270	0.1870*
H34C	−0.52410	−0.18680	0.68870	0.1870*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.084 (3)	0.041 (2)	0.058 (2)	−0.008 (2)	0.010 (2)	−0.0046 (18)
O2	0.089 (3)	0.061 (3)	0.060 (2)	−0.002 (2)	0.0147 (19)	0.006 (2)
O3	0.132 (4)	0.049 (3)	0.084 (3)	−0.022 (3)	0.014 (2)	0.005 (2)
O4	0.105 (3)	0.057 (3)	0.100 (3)	−0.002 (3)	0.003 (3)	−0.009 (2)
N1	0.076 (3)	0.040 (3)	0.073 (3)	−0.006 (3)	0.013 (3)	0.000 (3)
N2	0.084 (4)	0.037 (3)	0.075 (3)	−0.006 (3)	0.011 (3)	0.009 (3)
C1	0.067 (4)	0.048 (4)	0.072 (4)	0.001 (3)	0.011 (3)	−0.002 (3)
C2	0.059 (4)	0.054 (4)	0.056 (4)	−0.003 (3)	0.007 (3)	−0.003 (3)
C3	0.073 (4)	0.058 (4)	0.062 (4)	−0.001 (3)	0.010 (3)	−0.002 (3)
C4	0.141 (7)	0.085 (6)	0.075 (5)	−0.024 (5)	−0.006 (4)	−0.002 (4)
C5	0.172 (8)	0.113 (7)	0.074 (5)	−0.030 (6)	−0.030 (5)	−0.025 (5)
C6	0.126 (6)	0.058 (4)	0.104 (5)	−0.023 (4)	−0.002 (5)	−0.022 (4)
C7	0.075 (4)	0.043 (4)	0.086 (5)	−0.001 (3)	0.016 (3)	0.003 (3)
C8	0.070 (4)	0.047 (4)	0.077 (4)	−0.001 (3)	0.018 (3)	−0.002 (3)
C9	0.067 (4)	0.039 (3)	0.065 (4)	−0.001 (3)	0.010 (3)	0.009 (3)
C10	0.071 (4)	0.057 (4)	0.078 (4)	0.007 (3)	0.014 (3)	−0.001 (4)
C11	0.093 (5)	0.078 (5)	0.066 (4)	0.019 (4)	0.005 (4)	−0.003 (4)
C12	0.126 (6)	0.094 (6)	0.075 (5)	0.024 (5)	0.027 (4)	0.016 (4)
C13	0.145 (7)	0.053 (4)	0.082 (5)	0.003 (4)	0.019 (5)	0.007 (4)
C14	0.108 (5)	0.060 (4)	0.074 (4)	−0.012 (4)	0.012 (4)	0.012 (3)
C15	0.129 (6)	0.119 (6)	0.086 (5)	0.026 (5)	−0.007 (4)	−0.018 (5)
C16	0.081 (4)	0.102 (5)	0.060 (4)	0.024 (4)	0.011 (3)	0.017 (4)
C17	0.106 (6)	0.106 (6)	0.092 (5)	−0.007 (5)	0.021 (4)	0.049 (5)
O5	0.064 (3)	0.041 (2)	0.079 (3)	−0.0014 (18)	0.023 (2)	−0.010 (2)
O6	0.072 (3)	0.045 (3)	0.108 (3)	−0.011 (2)	0.028 (2)	−0.013 (2)
O7	0.066 (3)	0.062 (3)	0.101 (3)	−0.011 (2)	0.023 (2)	−0.005 (2)
O8	0.078 (3)	0.064 (3)	0.104 (3)	0.001 (3)	0.032 (3)	−0.012 (2)
N3	0.047 (3)	0.048 (3)	0.066 (3)	−0.007 (2)	0.004 (2)	0.000 (2)
N4	0.060 (3)	0.040 (3)	0.081 (3)	−0.006 (3)	0.018 (3)	0.003 (3)
C18	0.053 (4)	0.042 (3)	0.066 (4)	0.005 (3)	0.014 (3)	0.003 (3)
C19	0.056 (4)	0.045 (3)	0.056 (3)	0.012 (3)	0.017 (3)	0.001 (3)
C20	0.059 (4)	0.055 (4)	0.070 (4)	−0.001 (3)	0.013 (3)	0.005 (3)
C21	0.077 (5)	0.078 (5)	0.100 (5)	0.009 (4)	0.041 (4)	0.006 (4)
C22	0.091 (5)	0.074 (5)	0.116 (6)	0.008 (4)	0.053 (4)	−0.011 (4)
C23	0.091 (5)	0.053 (4)	0.085 (4)	−0.002 (4)	0.025 (4)	−0.019 (3)
C24	0.065 (4)	0.038 (3)	0.074 (4)	0.005 (3)	0.004 (3)	−0.002 (3)
C25	0.055 (4)	0.057 (4)	0.065 (4)	0.003 (3)	0.007 (3)	0.008 (3)
C26	0.060 (4)	0.045 (4)	0.059 (3)	0.000 (3)	0.009 (3)	0.006 (3)
C27	0.060 (4)	0.061 (4)	0.058 (4)	−0.004 (3)	0.001 (3)	0.007 (3)
C28	0.078 (5)	0.074 (5)	0.060 (4)	0.004 (4)	0.012 (3)	0.020 (3)
C29	0.064 (5)	0.091 (6)	0.095 (5)	−0.008 (4)	0.023 (4)	0.023 (4)
C30	0.085 (5)	0.061 (4)	0.117 (5)	−0.018 (4)	0.021 (4)	0.007 (4)
C31	0.073 (4)	0.051 (4)	0.108 (5)	−0.009 (4)	0.019 (4)	0.005 (3)
C32	0.083 (5)	0.136 (7)	0.106 (5)	0.007 (5)	0.040 (4)	0.002 (5)
C33	0.065 (4)	0.086 (5)	0.090 (4)	−0.008 (4)	0.021 (3)	0.024 (4)
C34	0.123 (7)	0.105 (7)	0.154 (7)	−0.064 (5)	0.049 (5)	−0.040 (5)

Geometric parameters (Å, º) top

O1—C2	1.369 (6)	C12—H12	0.9300
O2—C3	1.356 (7)	C13—H13	0.9300
O2—C16	1.449 (7)	C14—H14	0.9300
O3—C8	1.224 (8)	C15—H15C	0.9600
O4—C10	1.350 (8)	C15—H15A	0.9600
O1—H1	0.8200	C15—H15B	0.9600
O4—H4B	0.8200	C16—H16A	0.9700
O5—C19	1.378 (6)	C16—H16B	0.9700
O6—C25	1.239 (7)	C17—H17B	0.9600
O7—C20	1.367 (8)	C17—H17A	0.9600
O7—C33	1.433 (7)	C17—H17C	0.9600
O8—C27	1.348 (8)	C18—C19	1.380 (6)
O5—H5	0.8200	C18—C24	1.460 (8)
O8—H8	0.85 (3)	C18—C23	1.404 (8)
N1—N2	1.391 (7)	C19—C20	1.398 (8)
N1—C7	1.284 (8)	C20—C21	1.375 (9)
N2—C8	1.357 (8)	C21—C22	1.375 (9)
N2—H2	0.90 (2)	C22—C23	1.354 (9)
N3—N4	1.371 (7)	C25—C26	1.466 (8)
N3—C24	1.278 (7)	C26—C27	1.403 (8)
N4—C25	1.370 (8)	C26—C31	1.392 (8)
N4—H4	0.90 (4)	C27—C28	1.406 (9)
C1—C2	1.392 (8)	C28—C32	1.504 (10)
C1—C6	1.406 (9)	C28—C29	1.361 (9)
C1—C7	1.448 (8)	C29—C30	1.382 (9)
C2—C3	1.402 (8)	C30—C31	1.371 (9)
C3—C4	1.365 (10)	C33—C34	1.493 (9)
C4—C5	1.382 (12)	C21—H21	0.9300
C5—C6	1.368 (11)	C22—H22	0.9300
C8—C9	1.482 (8)	C23—H23	0.9300
C9—C14	1.403 (8)	C24—H24	0.9300
C9—C10	1.400 (8)	C29—H29	0.9300
C10—C11	1.392 (9)	C30—H30	0.9300
C11—C12	1.359 (11)	C31—H31	0.9300
C11—C15	1.523 (9)	C32—H32A	0.9600
C12—C13	1.370 (10)	C32—H32B	0.9600
C13—C14	1.387 (9)	C32—H32C	0.9600
C16—C17	1.509 (9)	C33—H33A	0.9700
C4—H4A	0.9300	C33—H33B	0.9700
C5—H5A	0.9300	C34—H34A	0.9600
C6—H6	0.9300	C34—H34B	0.9600
C7—H7	0.9300	C34—H34C	0.9600

C3—O2—C16	117.4 (4)	H16A—C16—H16B	109.00
C2—O1—H1	110.00	H17B—C17—H17C	109.00
C10—O4—H4B	109.00	H17A—C17—H17C	109.00
C20—O7—C33	118.1 (4)	C16—C17—H17B	110.00
C19—O5—H5	109.00	C16—C17—H17A	109.00
C27—O8—H8	101 (4)	H17A—C17—H17B	109.00
N2—N1—C7	116.8 (5)	C16—C17—H17C	110.00
N1—N2—C8	117.1 (5)	C19—C18—C24	121.8 (5)
N1—N2—H2	120 (3)	C23—C18—C24	119.2 (5)
C8—N2—H2	123 (3)	C19—C18—C23	119.0 (5)
N4—N3—C24	117.5 (4)	O5—C19—C20	116.6 (4)
N3—N4—C25	118.2 (4)	C18—C19—C20	120.8 (5)
N3—N4—H4	127 (3)	O5—C19—C18	122.6 (5)
C25—N4—H4	115 (3)	O7—C20—C19	115.2 (5)
C6—C1—C7	119.3 (6)	O7—C20—C21	125.9 (5)
C2—C1—C6	118.2 (5)	C19—C20—C21	119.0 (6)
C2—C1—C7	122.5 (5)	C20—C21—C22	119.9 (6)
O1—C2—C1	121.4 (4)	C21—C22—C23	121.8 (6)
O1—C2—C3	117.1 (4)	C18—C23—C22	119.5 (6)
C1—C2—C3	121.5 (5)	N3—C24—C18	119.9 (4)
O2—C3—C2	116.4 (5)	O6—C25—N4	119.0 (5)
C2—C3—C4	118.2 (6)	O6—C25—C26	123.0 (5)
O2—C3—C4	125.4 (6)	N4—C25—C26	118.0 (5)
C3—C4—C5	121.4 (7)	C27—C26—C31	117.6 (5)
C4—C5—C6	120.5 (7)	C25—C26—C27	118.1 (5)
C1—C6—C5	120.0 (7)	C25—C26—C31	124.3 (5)
N1—C7—C1	118.9 (6)	O8—C27—C28	116.3 (5)
N2—C8—C9	116.1 (5)	C26—C27—C28	121.7 (6)
O3—C8—N2	120.5 (5)	O8—C27—C26	122.1 (5)
O3—C8—C9	123.3 (5)	C27—C28—C29	117.3 (6)
C8—C9—C10	118.2 (5)	C27—C28—C32	120.4 (6)
C8—C9—C14	123.1 (5)	C29—C28—C32	122.4 (6)
C10—C9—C14	118.7 (5)	C28—C29—C30	123.0 (6)
C9—C10—C11	120.9 (6)	C29—C30—C31	119.0 (6)
O4—C10—C9	121.5 (5)	C26—C31—C30	121.5 (6)
O4—C10—C11	117.5 (5)	O7—C33—C34	107.6 (5)
C12—C11—C15	123.1 (6)	C20—C21—H21	120.00
C10—C11—C15	118.6 (6)	C22—C21—H21	120.00
C10—C11—C12	118.3 (6)	C21—C22—H22	119.00
C11—C12—C13	122.9 (7)	C23—C22—H22	119.00
C12—C13—C14	119.3 (6)	C18—C23—H23	120.00
C9—C14—C13	119.8 (6)	C22—C23—H23	120.00
O2—C16—C17	107.5 (5)	N3—C24—H24	120.00
C3—C4—H4A	119.00	C18—C24—H24	120.00
C5—C4—H4A	119.00	C28—C29—H29	119.00
C4—C5—H5A	120.00	C30—C29—H29	119.00
C6—C5—H5A	120.00	C29—C30—H30	120.00
C1—C6—H6	120.00	C31—C30—H30	121.00
C5—C6—H6	120.00	C26—C31—H31	119.00
N1—C7—H7	121.00	C30—C31—H31	119.00
C1—C7—H7	121.00	C28—C32—H32A	110.00
C11—C12—H12	119.00	C28—C32—H32B	110.00
C13—C12—H12	119.00	C28—C32—H32C	109.00
C14—C13—H13	120.00	H32A—C32—H32B	109.00
C12—C13—H13	120.00	H32A—C32—H32C	109.00
C13—C14—H14	120.00	H32B—C32—H32C	109.00
C9—C14—H14	120.00	O7—C33—H33A	110.00
C11—C15—H15B	110.00	O7—C33—H33B	110.00
H15A—C15—H15B	110.00	C34—C33—H33A	110.00
C11—C15—H15A	110.00	C34—C33—H33B	110.00
H15B—C15—H15C	109.00	H33A—C33—H33B	108.00
H15A—C15—H15C	109.00	C33—C34—H34A	109.00
C11—C15—H15C	109.00	C33—C34—H34B	109.00
C17—C16—H16B	110.00	C33—C34—H34C	109.00
C17—C16—H16A	110.00	H34A—C34—H34B	110.00
O2—C16—H16A	110.00	H34A—C34—H34C	110.00
O2—C16—H16B	110.00	H34B—C34—H34C	110.00

C16—O2—C3—C2	−172.1 (5)	O4—C10—C11—C15	−0.9 (8)
C16—O2—C3—C4	8.5 (8)	C9—C10—C11—C12	−1.7 (9)
C3—O2—C16—C17	172.9 (5)	C9—C10—C11—C15	179.5 (6)
C33—O7—C20—C19	−167.2 (5)	C10—C11—C12—C13	0.4 (10)
C33—O7—C20—C21	13.5 (8)	C15—C11—C12—C13	179.1 (7)
C20—O7—C33—C34	179.8 (5)	C11—C12—C13—C14	1.1 (11)
C7—N1—N2—C8	178.4 (5)	C12—C13—C14—C9	−1.2 (10)
N2—N1—C7—C1	179.0 (5)	C23—C18—C19—O5	−179.8 (5)
N1—N2—C8—C9	178.1 (5)	C23—C18—C19—C20	−0.2 (8)
N1—N2—C8—O3	0.3 (8)	C24—C18—C19—O5	2.9 (8)
N4—N3—C24—C18	178.0 (4)	C24—C18—C19—C20	−177.5 (5)
C24—N3—N4—C25	−179.5 (5)	C19—C18—C23—C22	−0.5 (8)
N3—N4—C25—O6	1.6 (8)	C24—C18—C23—C22	176.9 (6)
N3—N4—C25—C26	−177.8 (4)	C19—C18—C24—N3	−0.2 (8)
C6—C1—C2—O1	−179.9 (5)	C23—C18—C24—N3	−177.6 (5)
C6—C1—C2—C3	2.5 (8)	O5—C19—C20—O7	0.5 (7)
C7—C1—C2—O1	1.8 (8)	O5—C19—C20—C21	179.8 (5)
C2—C1—C6—C5	1.4 (10)	C18—C19—C20—O7	−179.1 (5)
C7—C1—C6—C5	179.8 (6)	C18—C19—C20—C21	0.2 (8)
C7—C1—C2—C3	−175.9 (5)	O7—C20—C21—C22	179.6 (6)
C6—C1—C7—N1	−177.7 (6)	C19—C20—C21—C22	0.4 (9)
C2—C1—C7—N1	0.6 (8)	C20—C21—C22—C23	−1.1 (10)
C1—C2—C3—C4	−4.2 (8)	C21—C22—C23—C18	1.2 (10)
C1—C2—C3—O2	176.3 (5)	O6—C25—C26—C27	−5.2 (8)
O1—C2—C3—O2	−1.5 (7)	O6—C25—C26—C31	175.3 (5)
O1—C2—C3—C4	178.0 (5)	N4—C25—C26—C27	174.2 (5)
O2—C3—C4—C5	−178.4 (6)	N4—C25—C26—C31	−5.3 (8)
C2—C3—C4—C5	2.2 (10)	C25—C26—C27—O8	0.7 (8)
C3—C4—C5—C6	1.6 (12)	C25—C26—C27—C28	−179.3 (5)
C4—C5—C6—C1	−3.4 (11)	C31—C26—C27—O8	−179.8 (5)
O3—C8—C9—C10	−8.2 (9)	C31—C26—C27—C28	0.3 (8)
O3—C8—C9—C14	174.3 (6)	C25—C26—C31—C30	179.5 (6)
N2—C8—C9—C10	174.1 (5)	C27—C26—C31—C30	0.0 (8)
N2—C8—C9—C14	−3.4 (9)	O8—C27—C28—C29	179.9 (5)
C10—C9—C14—C13	−0.1 (9)	O8—C27—C28—C32	−1.3 (8)
C8—C9—C10—O4	4.4 (8)	C26—C27—C28—C29	−0.2 (9)
C8—C9—C10—C11	−176.0 (5)	C26—C27—C28—C32	178.7 (5)
C14—C9—C10—O4	−178.0 (5)	C27—C28—C29—C30	−0.2 (10)
C14—C9—C10—C11	1.6 (9)	C32—C28—C29—C30	−179.0 (6)
C8—C9—C14—C13	177.4 (6)	C28—C29—C30—C31	0.4 (10)
O4—C10—C11—C12	177.9 (6)	C29—C30—C31—C26	−0.3 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.558 (5)	145
O4—H4B···O3	0.82	1.83	2.549 (5)	145
O5—H5···N3	0.82	1.87	2.585 (6)	145
O8—H8···O6	0.85 (3)	1.75 (4)	2.536 (6)	152 (5)
N2—H2···O5ⁱ	0.90 (2)	2.22 (2)	3.035 (6)	150 (4)
N2—H2···O7ⁱ	0.90 (2)	2.52 (4)	3.218 (6)	134 (3)
N4—H4···O1	0.90 (4)	2.26 (3)	3.027 (5)	144 (5)
C7—H7···O5ⁱ	0.93	2.59	3.353 (7)	140
C14—H14···O5ⁱ	0.93	2.60	3.516 (7)	169
C24—H24···O1	0.93	2.45	3.261 (6)	145
C33—H33A···O6ⁱⁱ	0.97	2.58	3.420 (7)	145

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₄
M_r	314.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	7.7661 (17), 22.148 (3), 9.7002 (16)
β (°)	100.382 (2)
V (Å³)	1641.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.982, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8061, 3436, 1592
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.113, 0.97
No. of reflections	3436
No. of parameters	431
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.15

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS (Sheldrick, 2008), SHELXL (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	1.84	2.558 (5)	145
O4—H4B···O3	0.82	1.83	2.549 (5)	145
O5—H5···N3	0.82	1.87	2.585 (6)	145
O8—H8···O6	0.85 (3)	1.75 (4)	2.536 (6)	152 (5)
N2—H2···O5ⁱ	0.90 (2)	2.22 (2)	3.035 (6)	150 (4)
N2—H2···O7ⁱ	0.90 (2)	2.52 (4)	3.218 (6)	134 (3)
N4—H4···O1	0.90 (4)	2.26 (3)	3.027 (5)	144 (5)
C7—H7···O5ⁱ	0.93	2.59	3.353 (7)	140
C14—H14···O5ⁱ	0.93	2.60	3.516 (7)	169
C24—H24···O1	0.93	2.45	3.261 (6)	145
C33—H33A···O6ⁱⁱ	0.97	2.58	3.420 (7)	145

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) x−1, y, z.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Horkaew, J. & Chantrapromma, S. (2011). Acta Cryst. E67, o2644–o2645. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o2985. Web of Science CSD CrossRef IUCr Journals Google Scholar
Huang, H.-T. & Wu, H.-Y. (2010). Acta Cryst. E66, o2729–o2730. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, X.-H., Zhu, L.-X., Shao, L.-J. & Zhu, Z.-F. (2012). Acta Cryst. E68, o297. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhi, F., Wang, R., Zhang, Y., Wang, Q. & Yang, Y.-L. (2011). Acta Cryst. E67, o2825. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 2| February 2012| Page o500

doi:10.1107/S1600536812002127

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