(E)-(2-Chloro-benzyl-idene)amino 2-amino-4-chloro-benzoate.

In the title compound, C(14)H(10)Cl(2)N(2)O(2), the configuration about the C=N double bond is E and the dihedral angle between the benzene rings is 1.75 (5)°. An intra-molecular N-H⋯O inter-action generates an S(6) ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, resulting in [101] chains.

Related literature

For background to 2-amino-4-chloro­benzoic acid derivatives, see: Jahnke et al. (2010 ▶); Lee et al. (2005 ▶). For a related structure, see: Seong et al. (2008 ▶).

Experimental

Crystal data

C14H10Cl2N2O2

M = 309.14

Monoclinic,

a = 7.4034 (5) Å

b = 23.8190 (15) Å

c = 7.6362 (5) Å

β = 96.382 (1)°

V = 1338.23 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 100 K

0.16 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.926, T max = 0.953

12076 measured reflections

3879 independent reflections

3637 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.084

S = 1.05

3879 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.53 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003844/hb6586sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003844/hb6586Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003844/hb6586Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H10Cl2N2O2	F(000) = 632
Mr = 309.14	Dx = 1.534 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.4034 (5) Å	Cell parameters from 9848 reflections
b = 23.8190 (15) Å	θ = 2.8–32.0°
c = 7.6362 (5) Å	µ = 0.49 mm−1
β = 96.382 (1)°	T = 100 K
V = 1338.23 (15) Å3	Block, colorless
Z = 4	0.16 × 0.15 × 0.10 mm

Bruker SMART APEX CCD diffractometer	3879 independent reflections
Radiation source: fine-focus sealed tube	3637 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.926, Tmax = 0.953	k = −33→32
12076 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H-atom parameters constrained
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.5103P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3879 reflections	Δρmax = 0.53 e Å−3
182 parameters	Δρmin = −0.53 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (10)

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.

	x	y	z	Uiso*/Ueq
C1	0.45478 (14)	0.08217 (4)	0.17648 (13)	0.01523 (18)
C2	0.36816 (14)	0.09752 (5)	0.01219 (13)	0.01805 (19)
H2	0.3133	0.0698	−0.0659	0.022*
C3	0.36279 (15)	0.15379 (5)	−0.03640 (14)	0.0197 (2)
H3	0.3043	0.1646	−0.1483	0.024*
C4	0.44295 (15)	0.19433 (5)	0.07849 (14)	0.0190 (2)
H4	0.4383	0.2328	0.0453	0.023*
C5	0.52956 (14)	0.17850 (4)	0.24135 (13)	0.01681 (19)
H5	0.5854	0.2063	0.3184	0.020*
C6	0.53611 (13)	0.12204 (4)	0.29440 (13)	0.01445 (18)
C7	0.62742 (13)	0.10574 (4)	0.46828 (13)	0.01528 (18)
H7	0.6660	0.0682	0.4918	0.018*
C9	0.80555 (13)	0.16068 (4)	0.86039 (13)	0.01431 (18)
C10	0.89159 (13)	0.13801 (4)	1.02756 (13)	0.01340 (17)
C11	0.97488 (13)	0.17569 (4)	1.15683 (13)	0.01466 (18)
C12	1.05960 (14)	0.15271 (4)	1.31596 (13)	0.01651 (19)
H12	1.1176	0.1767	1.4044	0.020*
C13	1.05789 (14)	0.09568 (4)	1.34250 (13)	0.01679 (19)
C14	0.97615 (14)	0.05787 (4)	1.21752 (14)	0.01768 (19)
H14	0.9772	0.0186	1.2394	0.021*
C15	0.89387 (13)	0.07991 (4)	1.06104 (13)	0.01523 (18)
H15	0.8374	0.0552	0.9739	0.018*
Cl1	0.45712 (4)	0.011502 (10)	0.23325 (3)	0.01985 (8)
Cl2	1.16302 (4)	0.069412 (12)	1.54105 (3)	0.02424 (8)
N1	0.65290 (13)	0.14358 (4)	0.58580 (12)	0.01819 (18)
N2	0.97461 (13)	0.23234 (4)	1.13648 (13)	0.02025 (19)
H2A	1.0264	0.2539	1.2213	0.024*
H2B	0.9226	0.2475	1.0385	0.024*
O1	0.74622 (10)	0.11954 (3)	0.74289 (10)	0.01663 (15)
O2	0.78875 (12)	0.21027 (3)	0.82487 (11)	0.02169 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0162 (4)	0.0151 (4)	0.0144 (4)	0.0010 (3)	0.0017 (3)	−0.0007 (3)
C2	0.0188 (4)	0.0214 (5)	0.0136 (4)	0.0015 (4)	−0.0002 (3)	−0.0026 (3)
C3	0.0209 (5)	0.0236 (5)	0.0145 (4)	0.0046 (4)	0.0011 (4)	0.0016 (4)
C4	0.0220 (5)	0.0179 (4)	0.0173 (4)	0.0025 (4)	0.0034 (4)	0.0030 (4)
C5	0.0192 (4)	0.0158 (4)	0.0156 (4)	−0.0005 (3)	0.0027 (3)	−0.0001 (3)
C6	0.0147 (4)	0.0159 (4)	0.0127 (4)	0.0010 (3)	0.0018 (3)	0.0001 (3)
C7	0.0158 (4)	0.0157 (4)	0.0140 (4)	−0.0002 (3)	0.0002 (3)	0.0006 (3)
C9	0.0131 (4)	0.0141 (4)	0.0151 (4)	−0.0011 (3)	−0.0016 (3)	0.0003 (3)
C10	0.0129 (4)	0.0133 (4)	0.0134 (4)	−0.0004 (3)	−0.0014 (3)	0.0004 (3)
C11	0.0134 (4)	0.0142 (4)	0.0160 (4)	−0.0009 (3)	−0.0001 (3)	−0.0010 (3)
C12	0.0155 (4)	0.0195 (5)	0.0139 (4)	−0.0010 (3)	−0.0008 (3)	−0.0010 (3)
C13	0.0150 (4)	0.0217 (5)	0.0133 (4)	0.0003 (3)	−0.0002 (3)	0.0041 (3)
C14	0.0181 (4)	0.0157 (4)	0.0187 (5)	−0.0008 (3)	−0.0003 (4)	0.0040 (3)
C15	0.0152 (4)	0.0134 (4)	0.0166 (4)	−0.0012 (3)	−0.0005 (3)	0.0009 (3)
Cl1	0.02618 (14)	0.01429 (12)	0.01833 (13)	−0.00055 (8)	−0.00089 (9)	−0.00137 (8)
Cl2	0.02529 (14)	0.03026 (15)	0.01581 (13)	−0.00042 (10)	−0.00378 (10)	0.00817 (9)
N1	0.0215 (4)	0.0180 (4)	0.0137 (4)	0.0028 (3)	−0.0036 (3)	0.0012 (3)
N2	0.0244 (4)	0.0134 (4)	0.0210 (4)	−0.0021 (3)	−0.0062 (3)	−0.0016 (3)
O1	0.0210 (4)	0.0146 (3)	0.0130 (3)	0.0009 (3)	−0.0041 (3)	−0.0002 (2)
O2	0.0264 (4)	0.0138 (3)	0.0223 (4)	−0.0026 (3)	−0.0090 (3)	0.0035 (3)

C1—C2	1.3928 (14)	C9—C10	1.4649 (13)
C1—C6	1.3980 (14)	C10—C15	1.4071 (13)
C1—Cl1	1.7378 (10)	C10—C11	1.4230 (13)
C2—C3	1.3902 (15)	C11—N2	1.3581 (13)
C2—H2	0.9500	C11—C12	1.4143 (14)
C3—C4	1.3923 (15)	C12—C13	1.3736 (14)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.3866 (14)	C13—C14	1.3999 (15)
C4—H4	0.9500	C13—Cl2	1.7417 (10)
C5—C6	1.4039 (14)	C14—C15	1.3829 (14)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.4735 (14)	C15—H15	0.9500
C7—N1	1.2712 (13)	N1—O1	1.4352 (11)
C7—H7	0.9500	N2—H2A	0.8800
C9—O2	1.2151 (12)	N2—H2B	0.8800
C9—O1	1.3677 (12)
C2—C1—C6	121.62 (9)	C15—C10—C11	119.92 (9)
C2—C1—Cl1	118.01 (8)	C15—C10—C9	121.07 (9)
C6—C1—Cl1	120.37 (8)	C11—C10—C9	119.01 (9)
C3—C2—C1	119.34 (10)	N2—C11—C12	118.53 (9)
C3—C2—H2	120.3	N2—C11—C10	123.52 (9)
C1—C2—H2	120.3	C12—C11—C10	117.94 (9)
C2—C3—C4	120.20 (10)	C13—C12—C11	119.94 (9)
C2—C3—H3	119.9	C13—C12—H12	120.0
C4—C3—H3	119.9	C11—C12—H12	120.0
C5—C4—C3	119.92 (10)	C12—C13—C14	123.09 (9)
C5—C4—H4	120.0	C12—C13—Cl2	118.24 (8)
C3—C4—H4	120.0	C14—C13—Cl2	118.67 (8)
C4—C5—C6	121.13 (10)	C15—C14—C13	117.41 (9)
C4—C5—H5	119.4	C15—C14—H14	121.3
C6—C5—H5	119.4	C13—C14—H14	121.3
C1—C6—C5	117.79 (9)	C14—C15—C10	121.70 (9)
C1—C6—C7	121.54 (9)	C14—C15—H15	119.1
C5—C6—C7	120.67 (9)	C10—C15—H15	119.1
N1—C7—C6	117.81 (9)	C7—N1—O1	109.09 (8)
N1—C7—H7	121.1	C11—N2—H2A	120.0
C6—C7—H7	121.1	C11—N2—H2B	120.0
O2—C9—O1	122.17 (9)	H2A—N2—H2B	120.0
O2—C9—C10	125.21 (9)	C9—O1—N1	110.62 (7)
O1—C9—C10	112.61 (8)
C6—C1—C2—C3	0.25 (16)	C15—C10—C11—N2	−178.31 (10)
Cl1—C1—C2—C3	179.50 (8)	C9—C10—C11—N2	2.12 (15)
C1—C2—C3—C4	−0.16 (16)	C15—C10—C11—C12	0.59 (14)
C2—C3—C4—C5	0.48 (16)	C9—C10—C11—C12	−178.99 (9)
C3—C4—C5—C6	−0.89 (16)	N2—C11—C12—C13	178.24 (10)
C2—C1—C6—C5	−0.63 (15)	C10—C11—C12—C13	−0.71 (15)
Cl1—C1—C6—C5	−179.86 (8)	C11—C12—C13—C14	0.47 (16)
C2—C1—C6—C7	179.90 (9)	C11—C12—C13—Cl2	−179.67 (8)
Cl1—C1—C6—C7	0.66 (14)	C12—C13—C14—C15	−0.08 (16)
C4—C5—C6—C1	0.95 (15)	Cl2—C13—C14—C15	−179.94 (8)
C4—C5—C6—C7	−179.57 (9)	C13—C14—C15—C10	−0.04 (15)
C1—C6—C7—N1	−160.77 (10)	C11—C10—C15—C14	−0.22 (15)
C5—C6—C7—N1	19.77 (14)	C9—C10—C15—C14	179.35 (9)
O2—C9—C10—C15	175.68 (10)	C6—C7—N1—O1	−178.86 (8)
O1—C9—C10—C15	−5.26 (14)	O2—C9—O1—N1	−4.58 (14)
O2—C9—C10—C11	−4.74 (16)	C10—C9—O1—N1	176.34 (8)
O1—C9—C10—C11	174.31 (9)	C7—N1—O1—C9	168.81 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2	0.88	2.02	2.6653 (12)	130
N2—H2A···O2i	0.88	2.19	2.9332 (12)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2	0.88	2.02	2.6653 (12)	130
N2—H2A⋯O2i	0.88	2.19	2.9332 (12)	142

Symmetry code: (i) .