N′-(5-Chloro-2-hy­droxy­benzyl­idene)-4-meth­oxy­benzohydrazide

Tan, Y.

doi:10.1107/S1600536812010707

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1079

doi:10.1107/S1600536812010707

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N′-(5-Chloro-2-hydroxybenzylidene)-4-methoxybenzohydrazide

Yao Tan ^a ^*

^aSchool of Chemistry and Environmental Engineering, Chongqing Three Gorges University, Chongqing 404000, People's Republic of China
^*Correspondence e-mail: tanyao1984@yahoo.cn

(Received 10 March 2012; accepted 11 March 2012; online 17 March 2012)

The asymmetric unit of the title compound, C₁₅H₁₃ClN₂O₃, contains two independent hydrazone molecules. Each molecule adopts an E configuration with respect to the methylidene unit and forms an intramolecular O—H⋯N hydrogen bond. The principal difference between the two unique molecules is the relative orientation of the two benzene rings, the dihedral angles between them being 4.0 (3) and 65.9 (3)°, respectively. In the crystal, molecules are linked through N—H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For similar hydrazone derivatives, see: Li (2012 ); Zhu et al. (2012 ); Shen et al. (2012 ); Liu et al. (2011 ); Lei (2011 ).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₃
M_r = 304.72
Monoclinic, P 2₁ /c
a = 17.569 (3) Å
b = 8.367 (2) Å
c = 19.454 (3) Å
β = 93.683 (3)°
V = 2853.8 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.11 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.970, T_max = 0.981
11127 measured reflections
3752 independent reflections
2545 reflections with I > 2σ(I)
R_int = 0.031
θ_max = 22.7°

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.02
3752 reflections
389 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O2ⁱ	0.89 (1)	1.98 (1)	2.843 (3)	164 (2)
N2—H2⋯O5	0.89 (1)	2.01 (1)	2.883 (3)	166 (2)
O4—H4⋯N3	0.82	1.82	2.540 (3)	145
O1—H1⋯N1	0.82	1.80	2.526 (3)	146
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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/S1600536812010707/sj5210sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010707/sj5210Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010707/sj5210Isup3.cml

checkCIF report

Comment top

As an extension of the work on the structures of hydrazone derivatives (Li, 2012; Zhu et al., 2012; Shen et al., 2012; Liu et al., 2011; Lei, 2011), the author reports here the structure of a new benzohydrazide compound, (I). The asymmetric unit of (I) contains two independent hydrazone molecules, Fig 1. Each molecule adopts a trans configuration with respect to the methylidene unit. The dihedral angles between the C1—C6 and C9—C14 benzene rings is 4.0 (3)°. The dihedral angles between the C16—C21 and C24—C29 benzene rings is 65.9 (3)°. In the crystal, molecules are linked through N—H···O hydrogen bonds (Table 1), to form chains running along the c-axis (Fig. 2).

Related literature top

For similar hydrazone derivatives, see: Li (2012); Zhu et al. (2012); Shen et al. (2012); Liu et al. (2011); Lei (2011).

Experimental top

4-Methoxybenzohydrazide (0.1 mmol, 16.6 mg) and 5-chloro-2-hydroxybenzaldehyde (0.1 mmol, 15.6 mg) were dissolved in methanol (30 ml). The reaction mixture was heated under reflux for 30 min and cooled gradually to room temperature. Thin, colourless needle-like crystals were obtained by slow evaporation of the solution containing the compound in air.

Structure description top

For similar hydrazone derivatives, see: Li (2012); Zhu et al. (2012); Shen et al. (2012); Liu et al. (2011); Lei (2011).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 30% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The chain stucture of (I), viewed along the b axis. Hydrogen bonds are shown as dashed lines.

N'-(5-Chloro-2-hydroxybenzylidene)-4-methoxybenzohydrazide top

Crystal data top

C₁₅H₁₃ClN₂O₃	F(000) = 1264
M_r = 304.72	D_x = 1.418 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2580 reflections
a = 17.569 (3) Å	θ = 2.3–24.1°
b = 8.367 (2) Å	µ = 0.28 mm⁻¹
c = 19.454 (3) Å	T = 298 K
β = 93.683 (3)°	Cut from a needle, colorless
V = 2853.8 (9) Å³	0.11 × 0.08 × 0.07 mm
Z = 8

Data collection top

Bruker SMART CCD area detector diffractometer	3752 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 22.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→18
T_min = 0.970, T_max = 0.981	k = −7→9
11127 measured reflections	l = −21→20

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0449P)² + 0.5824P] where P = (F_o² + 2F_c²)/3
3752 reflections	(Δ/σ)_max = 0.001
389 parameters	Δρ_max = 0.15 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₂O₃	V = 2853.8 (9) Å³
M_r = 304.72	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.569 (3) Å	µ = 0.28 mm⁻¹
b = 8.367 (2) Å	T = 298 K
c = 19.454 (3) Å	0.11 × 0.08 × 0.07 mm
β = 93.683 (3)°

Data collection top

Bruker SMART CCD area detector diffractometer	3752 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2545 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.981	R_int = 0.031
11127 measured reflections	θ_max = 22.7°

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.15 e Å⁻³
3752 reflections	Δρ_min = −0.23 e Å⁻³
389 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
Cl1	0.43413 (5)	0.26184 (11)	0.43593 (6)	0.1157 (4)
Cl2	0.46637 (5)	0.46291 (14)	0.15497 (6)	0.1363 (4)
N1	0.14645 (12)	0.6342 (2)	0.52429 (10)	0.0574 (5)
N2	0.07370 (12)	0.6759 (3)	0.50355 (10)	0.0576 (6)
N3	0.15526 (12)	0.6563 (2)	0.26936 (11)	0.0604 (6)
N4	0.07935 (12)	0.6606 (3)	0.24935 (10)	0.0600 (6)
O1	0.25873 (11)	0.6596 (3)	0.61141 (10)	0.0842 (6)
H1	0.2159	0.6780	0.5939	0.126*
O2	0.06353 (10)	0.7996 (2)	0.60402 (9)	0.0713 (5)
O3	−0.26093 (11)	0.9580 (2)	0.46447 (10)	0.0847 (6)
O4	0.26641 (13)	0.7120 (3)	0.35609 (11)	0.1122 (8)
H4	0.2214	0.7009	0.3429	0.168*
O5	0.04802 (10)	0.6214 (2)	0.35756 (9)	0.0716 (5)
O6	−0.27527 (11)	0.6996 (3)	0.19814 (10)	0.0878 (6)
C1	0.26287 (14)	0.5095 (3)	0.50765 (14)	0.0598 (7)
C2	0.29662 (16)	0.5671 (3)	0.56912 (15)	0.0680 (8)
C3	0.37158 (18)	0.5317 (4)	0.58736 (17)	0.0892 (10)
H3	0.3944	0.5729	0.6280	0.107*
C4	0.41271 (18)	0.4375 (4)	0.5469 (2)	0.0911 (10)
H4A	0.4631	0.4129	0.5602	0.109*
C5	0.38012 (16)	0.3790 (4)	0.48679 (18)	0.0792 (9)
C6	0.30662 (15)	0.4144 (3)	0.46739 (15)	0.0732 (8)
H6	0.2851	0.3739	0.4261	0.088*
C7	0.18546 (14)	0.5496 (3)	0.48577 (14)	0.0610 (7)
H7	0.1643	0.5136	0.4436	0.073*
C8	0.03506 (14)	0.7664 (3)	0.54710 (14)	0.0549 (6)
C9	−0.04190 (14)	0.8190 (3)	0.52330 (12)	0.0517 (6)
C10	−0.07920 (15)	0.7694 (3)	0.46248 (13)	0.0648 (7)
H10	−0.0546	0.7010	0.4334	0.078*
C11	−0.15120 (16)	0.8190 (3)	0.44458 (14)	0.0700 (8)
H11	−0.1753	0.7849	0.4032	0.084*
C12	−0.18882 (16)	0.9187 (3)	0.48663 (14)	0.0635 (7)
C13	−0.15250 (16)	0.9716 (3)	0.54685 (13)	0.0663 (7)
H13	−0.1770	1.0408	0.5756	0.080*
C14	−0.08003 (15)	0.9212 (3)	0.56394 (13)	0.0637 (7)
H14	−0.0555	0.9576	0.6048	0.076*
C15	−0.30577 (17)	1.0475 (4)	0.50860 (17)	0.0905 (10)
H15A	−0.3096	0.9908	0.5511	0.136*
H15B	−0.3559	1.0628	0.4869	0.136*
H15C	−0.2823	1.1496	0.5177	0.136*
C16	0.28167 (14)	0.6057 (3)	0.24456 (14)	0.0608 (7)
C17	0.31081 (17)	0.6535 (4)	0.30840 (17)	0.0820 (9)
C18	0.3881 (2)	0.6417 (5)	0.3241 (2)	0.1183 (14)
H18	0.4081	0.6743	0.3672	0.142*
C19	0.4352 (2)	0.5837 (5)	0.2780 (2)	0.1143 (13)
H19	0.4873	0.5763	0.2896	0.137*
C20	0.40683 (16)	0.5361 (4)	0.21483 (19)	0.0863 (10)
C21	0.33051 (15)	0.5475 (3)	0.19787 (15)	0.0730 (8)
H21	0.3112	0.5156	0.1544	0.088*
C22	0.20133 (15)	0.6144 (3)	0.22551 (14)	0.0623 (7)
H22	0.1833	0.5891	0.1809	0.075*
C23	0.02814 (14)	0.6472 (3)	0.29745 (14)	0.0549 (6)
C24	−0.05182 (14)	0.6598 (3)	0.27157 (12)	0.0520 (6)
C25	−0.10656 (15)	0.5695 (3)	0.30053 (13)	0.0618 (7)
H25	−0.0924	0.5008	0.3367	0.074*
C26	−0.18192 (15)	0.5784 (3)	0.27714 (14)	0.0661 (7)
H26	−0.2182	0.5148	0.2968	0.079*
C27	−0.20315 (15)	0.6807 (3)	0.22506 (14)	0.0617 (7)
C28	−0.14915 (16)	0.7721 (3)	0.19611 (14)	0.0664 (7)
H28	−0.1637	0.8429	0.1608	0.080*
C29	−0.07463 (14)	0.7606 (3)	0.21823 (13)	0.0584 (7)
H29	−0.0385	0.8215	0.1972	0.070*
C30	−0.33470 (17)	0.6190 (5)	0.23012 (19)	0.1119 (12)
H30A	−0.3272	0.5057	0.2270	0.168*
H30B	−0.3829	0.6472	0.2073	0.168*
H30C	−0.3342	0.6498	0.2777	0.168*
H2	0.0577 (14)	0.658 (3)	0.4600 (7)	0.080*
H4B	0.0664 (14)	0.662 (3)	0.2044 (6)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0708 (6)	0.1124 (7)	0.1654 (10)	0.0061 (5)	0.0199 (5)	−0.0250 (6)
Cl2	0.0713 (6)	0.1579 (10)	0.1830 (11)	0.0187 (6)	0.0332 (6)	0.0071 (8)
N1	0.0566 (14)	0.0641 (14)	0.0509 (13)	−0.0031 (11)	0.0003 (11)	0.0036 (11)
N2	0.0580 (14)	0.0720 (15)	0.0426 (13)	−0.0007 (11)	0.0009 (11)	−0.0018 (12)
N3	0.0559 (14)	0.0726 (15)	0.0522 (14)	−0.0024 (11)	−0.0008 (11)	0.0058 (12)
N4	0.0553 (14)	0.0812 (16)	0.0432 (13)	0.0033 (11)	0.0002 (11)	0.0041 (12)
O1	0.0845 (14)	0.1094 (17)	0.0571 (12)	−0.0066 (13)	−0.0066 (10)	−0.0078 (12)
O2	0.0685 (12)	0.0989 (14)	0.0459 (11)	−0.0023 (10)	−0.0005 (9)	−0.0081 (10)
O3	0.0774 (14)	0.0921 (15)	0.0832 (14)	0.0190 (11)	−0.0061 (11)	−0.0025 (12)
O4	0.0952 (17)	0.176 (2)	0.0638 (14)	−0.0141 (17)	−0.0116 (13)	−0.0161 (15)
O5	0.0738 (12)	0.1003 (15)	0.0402 (11)	0.0095 (10)	0.0010 (9)	−0.0005 (10)
O6	0.0610 (13)	0.1084 (16)	0.0922 (15)	0.0039 (11)	−0.0086 (11)	0.0064 (12)
C1	0.0575 (17)	0.0615 (17)	0.0598 (18)	−0.0100 (14)	0.0004 (14)	0.0032 (14)
C2	0.069 (2)	0.076 (2)	0.0587 (19)	−0.0064 (15)	0.0001 (16)	0.0029 (16)
C3	0.073 (2)	0.113 (3)	0.078 (2)	−0.011 (2)	−0.0167 (18)	0.006 (2)
C4	0.062 (2)	0.102 (3)	0.107 (3)	−0.0021 (19)	−0.010 (2)	0.015 (2)
C5	0.0587 (19)	0.077 (2)	0.102 (3)	−0.0065 (15)	0.0061 (17)	−0.0010 (19)
C6	0.0585 (18)	0.077 (2)	0.083 (2)	−0.0081 (15)	0.0012 (16)	−0.0086 (17)
C7	0.0579 (17)	0.0694 (18)	0.0554 (17)	−0.0076 (14)	0.0006 (14)	−0.0057 (15)
C8	0.0615 (17)	0.0606 (17)	0.0430 (16)	−0.0097 (13)	0.0067 (14)	0.0054 (14)
C9	0.0626 (17)	0.0521 (15)	0.0409 (15)	−0.0071 (13)	0.0079 (13)	0.0046 (12)
C10	0.0662 (18)	0.0723 (19)	0.0554 (18)	0.0018 (14)	0.0006 (14)	−0.0087 (14)
C11	0.075 (2)	0.0770 (19)	0.0571 (18)	0.0035 (16)	−0.0060 (15)	−0.0107 (15)
C12	0.0667 (19)	0.0624 (18)	0.0609 (19)	0.0016 (14)	0.0005 (15)	0.0101 (15)
C13	0.081 (2)	0.0647 (18)	0.0543 (18)	0.0082 (15)	0.0094 (15)	0.0012 (14)
C14	0.074 (2)	0.0667 (18)	0.0499 (17)	−0.0009 (15)	0.0025 (14)	0.0029 (14)
C15	0.081 (2)	0.089 (2)	0.102 (3)	0.0167 (18)	0.0116 (19)	0.006 (2)
C16	0.0530 (17)	0.0727 (18)	0.0556 (18)	−0.0054 (13)	−0.0043 (14)	0.0155 (15)
C17	0.067 (2)	0.110 (3)	0.067 (2)	−0.0139 (18)	−0.0104 (17)	0.0100 (19)
C18	0.076 (3)	0.182 (4)	0.093 (3)	−0.019 (3)	−0.026 (2)	0.008 (3)
C19	0.058 (2)	0.153 (4)	0.128 (4)	−0.011 (2)	−0.021 (2)	0.025 (3)
C20	0.0536 (19)	0.097 (2)	0.108 (3)	0.0026 (16)	0.0074 (19)	0.026 (2)
C21	0.0596 (19)	0.084 (2)	0.075 (2)	−0.0016 (15)	−0.0003 (16)	0.0158 (17)
C22	0.0597 (17)	0.0742 (19)	0.0520 (17)	−0.0034 (14)	−0.0034 (14)	0.0081 (14)
C23	0.0652 (18)	0.0570 (16)	0.0426 (16)	0.0010 (13)	0.0037 (14)	−0.0039 (13)
C24	0.0594 (16)	0.0518 (16)	0.0451 (15)	0.0052 (13)	0.0059 (12)	−0.0032 (13)
C25	0.0703 (19)	0.0636 (18)	0.0516 (17)	0.0030 (14)	0.0035 (14)	0.0052 (14)
C26	0.0650 (19)	0.0663 (19)	0.0678 (19)	−0.0045 (14)	0.0088 (15)	−0.0001 (16)
C27	0.0582 (18)	0.0659 (18)	0.0603 (18)	0.0050 (15)	−0.0009 (14)	−0.0055 (15)
C28	0.0682 (19)	0.0692 (19)	0.0612 (18)	0.0134 (15)	−0.0009 (15)	0.0100 (15)
C29	0.0637 (18)	0.0559 (16)	0.0561 (17)	0.0043 (13)	0.0089 (13)	0.0049 (14)
C30	0.060 (2)	0.139 (3)	0.137 (3)	−0.012 (2)	0.006 (2)	0.009 (3)

Geometric parameters (Å, º) top

Cl1—C5	1.721 (3)	C10—H10	0.9300
Cl2—C20	1.727 (3)	C11—C12	1.368 (4)
N1—C7	1.264 (3)	C11—H11	0.9300
N1—N2	1.361 (3)	C12—C13	1.371 (4)
N2—C8	1.351 (3)	C13—C14	1.362 (3)
N2—H2	0.888 (10)	C13—H13	0.9300
N3—C22	1.263 (3)	C14—H14	0.9300
N3—N4	1.366 (3)	C15—H15A	0.9600
N4—C23	1.344 (3)	C15—H15B	0.9600
N4—H4B	0.889 (10)	C15—H15C	0.9600
O1—C2	1.338 (3)	C16—C17	1.372 (4)
O1—H1	0.8200	C16—C21	1.378 (4)
O2—C8	1.217 (3)	C16—C22	1.438 (3)
O3—C12	1.352 (3)	C17—C18	1.375 (4)
O3—C15	1.416 (3)	C18—C19	1.350 (5)
O4—C17	1.343 (4)	C18—H18	0.9300
O4—H4	0.8200	C19—C20	1.356 (5)
O5—C23	1.218 (3)	C19—H19	0.9300
O6—C27	1.349 (3)	C20—C21	1.364 (4)
O6—C30	1.420 (3)	C21—H21	0.9300
C1—C6	1.383 (4)	C22—H22	0.9300
C1—C2	1.387 (4)	C23—C24	1.465 (3)
C1—C7	1.438 (3)	C24—C25	1.372 (3)
C2—C3	1.374 (4)	C24—C29	1.377 (3)
C3—C4	1.355 (4)	C25—C26	1.374 (3)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.359 (4)	C26—C27	1.360 (4)
C4—H4A	0.9300	C26—H26	0.9300
C5—C6	1.355 (4)	C27—C28	1.368 (4)
C6—H6	0.9300	C28—C29	1.355 (3)
C7—H7	0.9300	C28—H28	0.9300
C8—C9	1.469 (3)	C29—H29	0.9300
C9—C14	1.368 (3)	C30—H30A	0.9600
C9—C10	1.379 (3)	C30—H30B	0.9600
C10—C11	1.356 (3)	C30—H30C	0.9600

C7—N1—N2	120.2 (2)	O3—C15—H15A	109.5
C8—N2—N1	117.2 (2)	O3—C15—H15B	109.5
C8—N2—H2	123.6 (17)	H15A—C15—H15B	109.5
N1—N2—H2	118.2 (17)	O3—C15—H15C	109.5
C22—N3—N4	118.1 (2)	H15A—C15—H15C	109.5
C23—N4—N3	119.0 (2)	H15B—C15—H15C	109.5
C23—N4—H4B	123.0 (17)	C17—C16—C21	119.2 (3)
N3—N4—H4B	117.7 (17)	C17—C16—C22	121.4 (3)
C2—O1—H1	109.5	C21—C16—C22	119.4 (3)
C12—O3—C15	118.8 (2)	O4—C17—C16	122.2 (3)
C17—O4—H4	109.5	O4—C17—C18	118.8 (3)
C27—O6—C30	118.2 (2)	C16—C17—C18	119.0 (3)
C6—C1—C2	117.8 (3)	C19—C18—C17	121.2 (4)
C6—C1—C7	121.1 (3)	C19—C18—H18	119.4
C2—C1—C7	121.2 (3)	C17—C18—H18	119.4
O1—C2—C3	118.2 (3)	C18—C19—C20	120.1 (3)
O1—C2—C1	122.0 (3)	C18—C19—H19	119.9
C3—C2—C1	119.8 (3)	C20—C19—H19	119.9
C4—C3—C2	120.9 (3)	C19—C20—C21	119.9 (3)
C4—C3—H3	119.6	C19—C20—Cl2	120.8 (3)
C2—C3—H3	119.6	C21—C20—Cl2	119.4 (3)
C3—C4—C5	119.9 (3)	C20—C21—C16	120.6 (3)
C3—C4—H4A	120.1	C20—C21—H21	119.7
C5—C4—H4A	120.1	C16—C21—H21	119.7
C6—C5—C4	120.1 (3)	N3—C22—C16	120.1 (2)
C6—C5—Cl1	121.0 (3)	N3—C22—H22	120.0
C4—C5—Cl1	118.8 (3)	C16—C22—H22	120.0
C5—C6—C1	121.5 (3)	O5—C23—N4	121.3 (2)
C5—C6—H6	119.3	O5—C23—C24	123.5 (2)
C1—C6—H6	119.3	N4—C23—C24	115.1 (2)
N1—C7—C1	119.6 (2)	C25—C24—C29	118.0 (2)
N1—C7—H7	120.2	C25—C24—C23	120.1 (2)
C1—C7—H7	120.2	C29—C24—C23	121.9 (2)
O2—C8—N2	120.3 (2)	C24—C25—C26	121.3 (2)
O2—C8—C9	122.3 (2)	C24—C25—H25	119.3
N2—C8—C9	117.4 (2)	C26—C25—H25	119.3
C14—C9—C10	117.4 (2)	C27—C26—C25	119.5 (3)
C14—C9—C8	118.7 (2)	C27—C26—H26	120.2
C10—C9—C8	123.9 (2)	C25—C26—H26	120.2
C11—C10—C9	120.8 (3)	O6—C27—C26	124.7 (3)
C11—C10—H10	119.6	O6—C27—C28	115.7 (3)
C9—C10—H10	119.6	C26—C27—C28	119.6 (2)
C10—C11—C12	120.8 (3)	C29—C28—C27	120.8 (3)
C10—C11—H11	119.6	C29—C28—H28	119.6
C12—C11—H11	119.6	C27—C28—H28	119.6
O3—C12—C11	115.9 (3)	C28—C29—C24	120.8 (2)
O3—C12—C13	124.7 (3)	C28—C29—H29	119.6
C11—C12—C13	119.4 (3)	C24—C29—H29	119.6
C14—C13—C12	119.0 (3)	O6—C30—H30A	109.5
C14—C13—H13	120.5	O6—C30—H30B	109.5
C12—C13—H13	120.5	H30A—C30—H30B	109.5
C13—C14—C9	122.5 (3)	O6—C30—H30C	109.5
C13—C14—H14	118.8	H30A—C30—H30C	109.5
C9—C14—H14	118.8	H30B—C30—H30C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O2ⁱ	0.89 (1)	1.98 (1)	2.843 (3)	164 (2)
N2—H2···O5	0.89 (1)	2.01 (1)	2.883 (3)	166 (2)
O4—H4···N3	0.82	1.82	2.540 (3)	145
O1—H1···N1	0.82	1.80	2.526 (3)	146

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O₃
M_r	304.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	17.569 (3), 8.367 (2), 19.454 (3)
β (°)	93.683 (3)
V (Å³)	2853.8 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.11 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.970, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	11127, 3752, 2545
R_int	0.031
θ_max (°)	22.7
(sin θ/λ)_max (Å⁻¹)	0.542

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.02
No. of reflections	3752
No. of parameters	389
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)	0.15, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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
N4—H4B···O2ⁱ	0.889 (10)	1.977 (12)	2.843 (3)	164 (2)
N2—H2···O5	0.888 (10)	2.012 (12)	2.883 (3)	166 (2)
O4—H4···N3	0.82	1.82	2.540 (3)	145.2
O1—H1···N1	0.82	1.80	2.526 (3)	146.4

Symmetry code: (i) x, −y+3/2, z−1/2.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lei, Y. (2011). Acta Cryst. E67, o162. Web of Science CrossRef IUCr Journals Google Scholar
Li, X.-Y. (2012). Acta Cryst. E68, o709. CSD CrossRef IUCr Journals Google Scholar
Liu, H., Cai, Y., Wu, J., Li, Z. & Li, G. (2011). Acta Cryst. E67, o2139. 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
Zhu, Z.-F., Shao, L.-J. & Shen, X.-H. (2012). Acta Cryst. E68, o559. CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Page o1079

doi:10.1107/S1600536812010707

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