organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Li, X.-Y. (2012). Acta Cryst. E68, o709.]); Zhu et al. (2012[Zhu, Z.-F., Shao, L.-J. & Shen, X.-H. (2012). Acta Cryst. E68, o559.]); Shen et al. (2012[Shen, X.-H., Zhu, L.-X., Shao, L.-J. & Zhu, Z.-F. (2012). Acta Cryst. E68, o297.]); Liu et al. (2011[Liu, H., Cai, Y., Wu, J., Li, Z. & Li, G. (2011). Acta Cryst. E67, o2139.]); Lei (2011[Lei, Y. (2011). Acta Cryst. E67, o162.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13ClN2O3

  • Mr = 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.981

  • 11127 measured reflections

  • 3752 independent reflections

  • 2545 reflections with I > 2σ(I)

  • Rint = 0.031

  • θmax = 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

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H2 and H4B were located in a difference Fourier map and refined isotropically, with N—H distances restrained to 0.90 (1) Å. The remaining hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O1, O4, C15, and C30). Crystals were very small and weakly diffracting with no useful data observed beyond theta = 22.66°.

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
[Figure 1] Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
[Figure 2] 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
C15H13ClN2O3F(000) = 1264
Mr = 304.72Dx = 1.418 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2580 reflections
a = 17.569 (3) Åθ = 2.3–24.1°
b = 8.367 (2) ŵ = 0.28 mm1
c = 19.454 (3) ÅT = 298 K
β = 93.683 (3)°Cut from a needle, colorless
V = 2853.8 (9) Å30.11 × 0.08 × 0.07 mm
Z = 8
Data collection top
Bruker SMART CCD area detector
diffractometer
3752 independent reflections
Radiation source: fine-focus sealed tube2545 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 22.7°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1818
Tmin = 0.970, Tmax = 0.981k = 79
11127 measured reflectionsl = 2120
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0449P)2 + 0.5824P]
where P = (Fo2 + 2Fc2)/3
3752 reflections(Δ/σ)max = 0.001
389 parametersΔρmax = 0.15 e Å3
2 restraintsΔρmin = 0.23 e Å3
Crystal data top
C15H13ClN2O3V = 2853.8 (9) Å3
Mr = 304.72Z = 8
Monoclinic, P21/cMo Kα radiation
a = 17.569 (3) ŵ = 0.28 mm1
b = 8.367 (2) ÅT = 298 K
c = 19.454 (3) Å0.11 × 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)
Tmin = 0.970, Tmax = 0.981Rint = 0.031
11127 measured reflectionsθmax = 22.7°
Refinement top
R[F2 > 2σ(F2)] = 0.0382 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.15 e Å3
3752 reflectionsΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
Cl10.43413 (5)0.26184 (11)0.43593 (6)0.1157 (4)
Cl20.46637 (5)0.46291 (14)0.15497 (6)0.1363 (4)
N10.14645 (12)0.6342 (2)0.52429 (10)0.0574 (5)
N20.07370 (12)0.6759 (3)0.50355 (10)0.0576 (6)
N30.15526 (12)0.6563 (2)0.26936 (11)0.0604 (6)
N40.07935 (12)0.6606 (3)0.24935 (10)0.0600 (6)
O10.25873 (11)0.6596 (3)0.61141 (10)0.0842 (6)
H10.21590.67800.59390.126*
O20.06353 (10)0.7996 (2)0.60402 (9)0.0713 (5)
O30.26093 (11)0.9580 (2)0.46447 (10)0.0847 (6)
O40.26641 (13)0.7120 (3)0.35609 (11)0.1122 (8)
H40.22140.70090.34290.168*
O50.04802 (10)0.6214 (2)0.35756 (9)0.0716 (5)
O60.27527 (11)0.6996 (3)0.19814 (10)0.0878 (6)
C10.26287 (14)0.5095 (3)0.50765 (14)0.0598 (7)
C20.29662 (16)0.5671 (3)0.56912 (15)0.0680 (8)
C30.37158 (18)0.5317 (4)0.58736 (17)0.0892 (10)
H30.39440.57290.62800.107*
C40.41271 (18)0.4375 (4)0.5469 (2)0.0911 (10)
H4A0.46310.41290.56020.109*
C50.38012 (16)0.3790 (4)0.48679 (18)0.0792 (9)
C60.30662 (15)0.4144 (3)0.46739 (15)0.0732 (8)
H60.28510.37390.42610.088*
C70.18546 (14)0.5496 (3)0.48577 (14)0.0610 (7)
H70.16430.51360.44360.073*
C80.03506 (14)0.7664 (3)0.54710 (14)0.0549 (6)
C90.04190 (14)0.8190 (3)0.52330 (12)0.0517 (6)
C100.07920 (15)0.7694 (3)0.46248 (13)0.0648 (7)
H100.05460.70100.43340.078*
C110.15120 (16)0.8190 (3)0.44458 (14)0.0700 (8)
H110.17530.78490.40320.084*
C120.18882 (16)0.9187 (3)0.48663 (14)0.0635 (7)
C130.15250 (16)0.9716 (3)0.54685 (13)0.0663 (7)
H130.17701.04080.57560.080*
C140.08003 (15)0.9212 (3)0.56394 (13)0.0637 (7)
H140.05550.95760.60480.076*
C150.30577 (17)1.0475 (4)0.50860 (17)0.0905 (10)
H15A0.30960.99080.55110.136*
H15B0.35591.06280.48690.136*
H15C0.28231.14960.51770.136*
C160.28167 (14)0.6057 (3)0.24456 (14)0.0608 (7)
C170.31081 (17)0.6535 (4)0.30840 (17)0.0820 (9)
C180.3881 (2)0.6417 (5)0.3241 (2)0.1183 (14)
H180.40810.67430.36720.142*
C190.4352 (2)0.5837 (5)0.2780 (2)0.1143 (13)
H190.48730.57630.28960.137*
C200.40683 (16)0.5361 (4)0.21483 (19)0.0863 (10)
C210.33051 (15)0.5475 (3)0.19787 (15)0.0730 (8)
H210.31120.51560.15440.088*
C220.20133 (15)0.6144 (3)0.22551 (14)0.0623 (7)
H220.18330.58910.18090.075*
C230.02814 (14)0.6472 (3)0.29745 (14)0.0549 (6)
C240.05182 (14)0.6598 (3)0.27157 (12)0.0520 (6)
C250.10656 (15)0.5695 (3)0.30053 (13)0.0618 (7)
H250.09240.50080.33670.074*
C260.18192 (15)0.5784 (3)0.27714 (14)0.0661 (7)
H260.21820.51480.29680.079*
C270.20315 (15)0.6807 (3)0.22506 (14)0.0617 (7)
C280.14915 (16)0.7721 (3)0.19611 (14)0.0664 (7)
H280.16370.84290.16080.080*
C290.07463 (14)0.7606 (3)0.21823 (13)0.0584 (7)
H290.03850.82150.19720.070*
C300.33470 (17)0.6190 (5)0.23012 (19)0.1119 (12)
H30A0.32720.50570.22700.168*
H30B0.38290.64720.20730.168*
H30C0.33420.64980.27770.168*
H20.0577 (14)0.658 (3)0.4600 (7)0.080*
H4B0.0664 (14)0.662 (3)0.2044 (6)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0708 (6)0.1124 (7)0.1654 (10)0.0061 (5)0.0199 (5)0.0250 (6)
Cl20.0713 (6)0.1579 (10)0.1830 (11)0.0187 (6)0.0332 (6)0.0071 (8)
N10.0566 (14)0.0641 (14)0.0509 (13)0.0031 (11)0.0003 (11)0.0036 (11)
N20.0580 (14)0.0720 (15)0.0426 (13)0.0007 (11)0.0009 (11)0.0018 (12)
N30.0559 (14)0.0726 (15)0.0522 (14)0.0024 (11)0.0008 (11)0.0058 (12)
N40.0553 (14)0.0812 (16)0.0432 (13)0.0033 (11)0.0002 (11)0.0041 (12)
O10.0845 (14)0.1094 (17)0.0571 (12)0.0066 (13)0.0066 (10)0.0078 (12)
O20.0685 (12)0.0989 (14)0.0459 (11)0.0023 (10)0.0005 (9)0.0081 (10)
O30.0774 (14)0.0921 (15)0.0832 (14)0.0190 (11)0.0061 (11)0.0025 (12)
O40.0952 (17)0.176 (2)0.0638 (14)0.0141 (17)0.0116 (13)0.0161 (15)
O50.0738 (12)0.1003 (15)0.0402 (11)0.0095 (10)0.0010 (9)0.0005 (10)
O60.0610 (13)0.1084 (16)0.0922 (15)0.0039 (11)0.0086 (11)0.0064 (12)
C10.0575 (17)0.0615 (17)0.0598 (18)0.0100 (14)0.0004 (14)0.0032 (14)
C20.069 (2)0.076 (2)0.0587 (19)0.0064 (15)0.0001 (16)0.0029 (16)
C30.073 (2)0.113 (3)0.078 (2)0.011 (2)0.0167 (18)0.006 (2)
C40.062 (2)0.102 (3)0.107 (3)0.0021 (19)0.010 (2)0.015 (2)
C50.0587 (19)0.077 (2)0.102 (3)0.0065 (15)0.0061 (17)0.0010 (19)
C60.0585 (18)0.077 (2)0.083 (2)0.0081 (15)0.0012 (16)0.0086 (17)
C70.0579 (17)0.0694 (18)0.0554 (17)0.0076 (14)0.0006 (14)0.0057 (15)
C80.0615 (17)0.0606 (17)0.0430 (16)0.0097 (13)0.0067 (14)0.0054 (14)
C90.0626 (17)0.0521 (15)0.0409 (15)0.0071 (13)0.0079 (13)0.0046 (12)
C100.0662 (18)0.0723 (19)0.0554 (18)0.0018 (14)0.0006 (14)0.0087 (14)
C110.075 (2)0.0770 (19)0.0571 (18)0.0035 (16)0.0060 (15)0.0107 (15)
C120.0667 (19)0.0624 (18)0.0609 (19)0.0016 (14)0.0005 (15)0.0101 (15)
C130.081 (2)0.0647 (18)0.0543 (18)0.0082 (15)0.0094 (15)0.0012 (14)
C140.074 (2)0.0667 (18)0.0499 (17)0.0009 (15)0.0025 (14)0.0029 (14)
C150.081 (2)0.089 (2)0.102 (3)0.0167 (18)0.0116 (19)0.006 (2)
C160.0530 (17)0.0727 (18)0.0556 (18)0.0054 (13)0.0043 (14)0.0155 (15)
C170.067 (2)0.110 (3)0.067 (2)0.0139 (18)0.0104 (17)0.0100 (19)
C180.076 (3)0.182 (4)0.093 (3)0.019 (3)0.026 (2)0.008 (3)
C190.058 (2)0.153 (4)0.128 (4)0.011 (2)0.021 (2)0.025 (3)
C200.0536 (19)0.097 (2)0.108 (3)0.0026 (16)0.0074 (19)0.026 (2)
C210.0596 (19)0.084 (2)0.075 (2)0.0016 (15)0.0003 (16)0.0158 (17)
C220.0597 (17)0.0742 (19)0.0520 (17)0.0034 (14)0.0034 (14)0.0081 (14)
C230.0652 (18)0.0570 (16)0.0426 (16)0.0010 (13)0.0037 (14)0.0039 (13)
C240.0594 (16)0.0518 (16)0.0451 (15)0.0052 (13)0.0059 (12)0.0032 (13)
C250.0703 (19)0.0636 (18)0.0516 (17)0.0030 (14)0.0035 (14)0.0052 (14)
C260.0650 (19)0.0663 (19)0.0678 (19)0.0045 (14)0.0088 (15)0.0001 (16)
C270.0582 (18)0.0659 (18)0.0603 (18)0.0050 (15)0.0009 (14)0.0055 (15)
C280.0682 (19)0.0692 (19)0.0612 (18)0.0134 (15)0.0009 (15)0.0100 (15)
C290.0637 (18)0.0559 (16)0.0561 (17)0.0043 (13)0.0089 (13)0.0049 (14)
C300.060 (2)0.139 (3)0.137 (3)0.012 (2)0.006 (2)0.009 (3)
Geometric parameters (Å, º) top
Cl1—C51.721 (3)C10—H100.9300
Cl2—C201.727 (3)C11—C121.368 (4)
N1—C71.264 (3)C11—H110.9300
N1—N21.361 (3)C12—C131.371 (4)
N2—C81.351 (3)C13—C141.362 (3)
N2—H20.888 (10)C13—H130.9300
N3—C221.263 (3)C14—H140.9300
N3—N41.366 (3)C15—H15A0.9600
N4—C231.344 (3)C15—H15B0.9600
N4—H4B0.889 (10)C15—H15C0.9600
O1—C21.338 (3)C16—C171.372 (4)
O1—H10.8200C16—C211.378 (4)
O2—C81.217 (3)C16—C221.438 (3)
O3—C121.352 (3)C17—C181.375 (4)
O3—C151.416 (3)C18—C191.350 (5)
O4—C171.343 (4)C18—H180.9300
O4—H40.8200C19—C201.356 (5)
O5—C231.218 (3)C19—H190.9300
O6—C271.349 (3)C20—C211.364 (4)
O6—C301.420 (3)C21—H210.9300
C1—C61.383 (4)C22—H220.9300
C1—C21.387 (4)C23—C241.465 (3)
C1—C71.438 (3)C24—C251.372 (3)
C2—C31.374 (4)C24—C291.377 (3)
C3—C41.355 (4)C25—C261.374 (3)
C3—H30.9300C25—H250.9300
C4—C51.359 (4)C26—C271.360 (4)
C4—H4A0.9300C26—H260.9300
C5—C61.355 (4)C27—C281.368 (4)
C6—H60.9300C28—C291.355 (3)
C7—H70.9300C28—H280.9300
C8—C91.469 (3)C29—H290.9300
C9—C141.368 (3)C30—H30A0.9600
C9—C101.379 (3)C30—H30B0.9600
C10—C111.356 (3)C30—H30C0.9600
C7—N1—N2120.2 (2)O3—C15—H15A109.5
C8—N2—N1117.2 (2)O3—C15—H15B109.5
C8—N2—H2123.6 (17)H15A—C15—H15B109.5
N1—N2—H2118.2 (17)O3—C15—H15C109.5
C22—N3—N4118.1 (2)H15A—C15—H15C109.5
C23—N4—N3119.0 (2)H15B—C15—H15C109.5
C23—N4—H4B123.0 (17)C17—C16—C21119.2 (3)
N3—N4—H4B117.7 (17)C17—C16—C22121.4 (3)
C2—O1—H1109.5C21—C16—C22119.4 (3)
C12—O3—C15118.8 (2)O4—C17—C16122.2 (3)
C17—O4—H4109.5O4—C17—C18118.8 (3)
C27—O6—C30118.2 (2)C16—C17—C18119.0 (3)
C6—C1—C2117.8 (3)C19—C18—C17121.2 (4)
C6—C1—C7121.1 (3)C19—C18—H18119.4
C2—C1—C7121.2 (3)C17—C18—H18119.4
O1—C2—C3118.2 (3)C18—C19—C20120.1 (3)
O1—C2—C1122.0 (3)C18—C19—H19119.9
C3—C2—C1119.8 (3)C20—C19—H19119.9
C4—C3—C2120.9 (3)C19—C20—C21119.9 (3)
C4—C3—H3119.6C19—C20—Cl2120.8 (3)
C2—C3—H3119.6C21—C20—Cl2119.4 (3)
C3—C4—C5119.9 (3)C20—C21—C16120.6 (3)
C3—C4—H4A120.1C20—C21—H21119.7
C5—C4—H4A120.1C16—C21—H21119.7
C6—C5—C4120.1 (3)N3—C22—C16120.1 (2)
C6—C5—Cl1121.0 (3)N3—C22—H22120.0
C4—C5—Cl1118.8 (3)C16—C22—H22120.0
C5—C6—C1121.5 (3)O5—C23—N4121.3 (2)
C5—C6—H6119.3O5—C23—C24123.5 (2)
C1—C6—H6119.3N4—C23—C24115.1 (2)
N1—C7—C1119.6 (2)C25—C24—C29118.0 (2)
N1—C7—H7120.2C25—C24—C23120.1 (2)
C1—C7—H7120.2C29—C24—C23121.9 (2)
O2—C8—N2120.3 (2)C24—C25—C26121.3 (2)
O2—C8—C9122.3 (2)C24—C25—H25119.3
N2—C8—C9117.4 (2)C26—C25—H25119.3
C14—C9—C10117.4 (2)C27—C26—C25119.5 (3)
C14—C9—C8118.7 (2)C27—C26—H26120.2
C10—C9—C8123.9 (2)C25—C26—H26120.2
C11—C10—C9120.8 (3)O6—C27—C26124.7 (3)
C11—C10—H10119.6O6—C27—C28115.7 (3)
C9—C10—H10119.6C26—C27—C28119.6 (2)
C10—C11—C12120.8 (3)C29—C28—C27120.8 (3)
C10—C11—H11119.6C29—C28—H28119.6
C12—C11—H11119.6C27—C28—H28119.6
O3—C12—C11115.9 (3)C28—C29—C24120.8 (2)
O3—C12—C13124.7 (3)C28—C29—H29119.6
C11—C12—C13119.4 (3)C24—C29—H29119.6
C14—C13—C12119.0 (3)O6—C30—H30A109.5
C14—C13—H13120.5O6—C30—H30B109.5
C12—C13—H13120.5H30A—C30—H30B109.5
C13—C14—C9122.5 (3)O6—C30—H30C109.5
C13—C14—H14118.8H30A—C30—H30C109.5
C9—C14—H14118.8H30B—C30—H30C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4B···O2i0.89 (1)1.98 (1)2.843 (3)164 (2)
N2—H2···O50.89 (1)2.01 (1)2.883 (3)166 (2)
O4—H4···N30.821.822.540 (3)145
O1—H1···N10.821.802.526 (3)146
Symmetry code: (i) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC15H13ClN2O3
Mr304.72
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)17.569 (3), 8.367 (2), 19.454 (3)
β (°) 93.683 (3)
V3)2853.8 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.11 × 0.08 × 0.07
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.970, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
11127, 3752, 2545
Rint0.031
θmax (°)22.7
(sin θ/λ)max1)0.542
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.105, 1.02
No. of reflections3752
No. of parameters389
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N4—H4B···O2i0.889 (10)1.977 (12)2.843 (3)164 (2)
N2—H2···O50.888 (10)2.012 (12)2.883 (3)166 (2)
O4—H4···N30.821.822.540 (3)145.2
O1—H1···N10.821.802.526 (3)146.4
Symmetry code: (i) x, y+3/2, z1/2.
 

References

First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationLei, Y. (2011). Acta Cryst. E67, o162.  Web of Science CrossRef IUCr Journals
First citationLi, X.-Y. (2012). Acta Cryst. E68, o709.  CSD CrossRef IUCr Journals
First citationLiu, H., Cai, Y., Wu, J., Li, Z. & Li, G. (2011). Acta Cryst. E67, o2139.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShen, X.-H., Zhu, L.-X., Shao, L.-J. & Zhu, Z.-F. (2012). Acta Cryst. E68, o297.  Web of Science CSD CrossRef IUCr Journals
First citationZhu, Z.-F., Shao, L.-J. & Shen, X.-H. (2012). Acta Cryst. E68, o559.  CSD CrossRef IUCr Journals

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