N-(2,3-Dichloro­phen­yl)benzamide

Gowda, B.T.; Sowmya, B.P.; Tokarčík, M.; Kožíšek, J.; Fuess, H.

doi:10.1107/S1600536807030243

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N-(2,3-Dichlorophenyl)benzamide

B. T. Gowda, B. P. Sowmya, M. Tokarčík, J. Kožíšek and H. Fuess

In the structure of the title compound, C₁₃H₉Cl₂NO, the conformation of the N—H bond is syn to the chloro substituents on the aniline benzene ring, similar to that observed in N-(2,3-dichlorophenyl)acetamide, but in contrast to the anti conformation observed with respect to the ortho-Cl substituent in N-(2-chlorophenyl)benzamide. The structure closely resembles the structures of 2-chloro-N-phenylbenzamide, N-(2-chlorophenyl)benzamide and N-(2,3-dichlorophenyl)acetamide. The molecules are linked into a chain through an N—H

O hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030243/bt2404sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030243/bt2404Isup2.hkl Contains datablock I

CCDC reference: 655047

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R factor = 0.036
wR factor = 0.093
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the present work, the structure of N-(2,3-dichlorophenyl)-benzamide has been determined to explore the substituent effects on the structures of N-aromatic amides (Gowda et al., 2003; Gowda, Foro, & Fuess, 2007; Gowda, Kozisek, et al., 2007; Gowda, Sowmya, et al., 2007). The conformation of the N—H bond (Fig. 1) is syn to the chloro substituents in the aniline phenyl ring, similar to that observed in N-(2,3-dichlorophenyl)-acetamide (Gowda, Foro, & Fuess, 2007), but in contrast to the anti conformation observed with respect to the ortho-Cl substituent in N-(2-chlorophenyl)-benzamide (Gowda, Sowmya, et al., 2007). The structure resembles the structure of N-(phenyl)-2-chlorobenzamide (Gowda et al., 2003), N-(2-chlorophenyl)-benzamide (Gowda, Sowmya, et al., 2007) and N-(2,3-dichlorophenyl)-acetamide (Gowda, Foro, & Fuess, 2007). The packing diagram showis the infinite chain of molecules along [0 0 1] linked by N—H···O hydrogen bonds (Fig. 2 and Table 2).

Related literature top

For related literature, see: Gowda et al. (2003); Gowda, Foro & Fuess (2007); Gowda, Kozisek et al. (2007); Gowda, Sowmya et al. (2007).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution.

Structure description top

For related literature, see: Gowda et al. (2003); Gowda, Foro & Fuess (2007); Gowda, Kozisek et al. (2007); Gowda, Sowmya et al. (2007).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of crystal structure of the title compound showing the infinite chain of molecules along [0 0 1] linked by hydrogen bonds N1—H1N···O1(i). Symmetry operation (i): x, -y + 1, z + 1/2.

N-(2,3-Dichlorophenyl)benzamide top

Crystal data top

C₁₃H₉Cl₂NO	F(000) = 1088
M_r = 266.11	D_x = 1.47 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2616 reflections
a = 24.2968 (12) Å	θ = 3.1–29.4°
b = 11.3273 (5) Å	µ = 0.52 mm⁻¹
c = 8.7396 (3) Å	T = 295 K
V = 2405.29 (18) Å³	Needle, colorless
Z = 8	0.45 × 0.09 × 0.07 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2319 independent reflections
Radiation source: Enhance (Mo) X-ray Source	981 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
Detector resolution: 10.4340 pixels mm^-1	θ_max = 25.9°, θ_min = 4.3°
φ scans, and ω scans with κ offsets	h = −29→29
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −13→13
T_min = 0.894, T_max = 0.961	l = −10→10
21027 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0374P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.093	(Δ/σ)_max = 0.002
S = 0.91	Δρ_max = 0.17 e Å⁻³
2319 reflections	Δρ_min = −0.19 e Å⁻³
154 parameters

Crystal data top

C₁₃H₉Cl₂NO	V = 2405.29 (18) Å³
M_r = 266.11	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 24.2968 (12) Å	µ = 0.52 mm⁻¹
b = 11.3273 (5) Å	T = 295 K
c = 8.7396 (3) Å	0.45 × 0.09 × 0.07 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2319 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	981 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.961	R_int = 0.097
21027 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 0.91	Δρ_max = 0.17 e Å⁻³
2319 reflections	Δρ_min = −0.19 e Å⁻³
154 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.37448 (11)	0.4513 (3)	0.2398 (3)	0.0476 (7)
C2	0.33837 (11)	0.3829 (3)	0.3452 (3)	0.0444 (7)
C3	0.34131 (12)	0.2616 (3)	0.3412 (3)	0.0555 (8)
H3	0.3652	0.2249	0.2730	0.067*
C4	0.30922 (14)	0.1938 (3)	0.4369 (4)	0.0676 (9)
H4	0.3122	0.1120	0.4358	0.081*
C5	0.27301 (13)	0.2478 (4)	0.5336 (4)	0.0709 (10)
H5	0.2513	0.2023	0.5986	0.085*
C6	0.26823 (13)	0.3682 (4)	0.5359 (4)	0.0712 (10)
H6	0.2429	0.4040	0.6009	0.085*
C7	0.30086 (12)	0.4365 (3)	0.4420 (3)	0.0562 (8)
H7	0.2977	0.5183	0.4437	0.067*
C8	0.41571 (11)	0.6480 (3)	0.1992 (3)	0.0422 (7)
C9	0.45461 (12)	0.6195 (3)	0.0898 (3)	0.0559 (8)
H9	0.4629	0.5408	0.0700	0.067*
C10	0.48119 (12)	0.7080 (3)	0.0099 (3)	0.0632 (9)
H10	0.5071	0.6881	−0.0641	0.076*
C11	0.47010 (12)	0.8235 (3)	0.0375 (4)	0.0646 (9)
H11	0.4883	0.8820	−0.0174	0.078*
C12	0.43170 (13)	0.8539 (3)	0.1474 (3)	0.0560 (8)
C13	0.40443 (11)	0.7666 (3)	0.2283 (3)	0.0477 (8)
N1	0.38766 (9)	0.5620 (2)	0.2842 (2)	0.0491 (6)
H1N	0.3777	0.5821	0.3750	0.059*
O1	0.39099 (8)	0.40812 (18)	0.1197 (2)	0.0641 (6)
Cl1	0.35585 (4)	0.80396 (7)	0.36269 (8)	0.0689 (3)
Cl2	0.41772 (4)	1.00012 (8)	0.18131 (11)	0.0968 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0566 (19)	0.043 (2)	0.0428 (17)	0.0072 (16)	−0.0068 (15)	−0.0002 (16)
C2	0.0485 (19)	0.045 (2)	0.0400 (15)	−0.0013 (15)	−0.0039 (14)	−0.0011 (16)
C3	0.060 (2)	0.055 (2)	0.0521 (17)	0.0006 (16)	−0.0035 (17)	−0.0026 (17)
C4	0.071 (2)	0.054 (2)	0.077 (2)	−0.014 (2)	−0.012 (2)	0.012 (2)
C5	0.056 (2)	0.090 (3)	0.066 (2)	−0.022 (2)	−0.0032 (19)	0.018 (2)
C6	0.058 (2)	0.083 (3)	0.072 (2)	−0.011 (2)	0.0035 (18)	−0.004 (2)
C7	0.057 (2)	0.054 (2)	0.0570 (18)	−0.0028 (18)	−0.0022 (17)	−0.0011 (18)
C8	0.0471 (18)	0.044 (2)	0.0357 (15)	0.0009 (15)	−0.0022 (13)	0.0061 (14)
C9	0.0564 (19)	0.059 (2)	0.0526 (17)	0.0070 (17)	0.0064 (16)	0.0028 (17)
C10	0.050 (2)	0.077 (3)	0.0624 (19)	0.0063 (19)	0.0122 (16)	0.003 (2)
C11	0.055 (2)	0.063 (3)	0.075 (2)	−0.0085 (19)	0.0081 (18)	0.0079 (19)
C12	0.060 (2)	0.051 (2)	0.0569 (18)	−0.0016 (16)	−0.0002 (17)	0.0035 (17)
C13	0.0522 (19)	0.051 (2)	0.0402 (15)	−0.0011 (16)	−0.0025 (14)	0.0012 (15)
N1	0.0679 (16)	0.0411 (16)	0.0383 (12)	0.0027 (14)	0.0059 (11)	−0.0020 (13)
O1	0.0942 (16)	0.0539 (14)	0.0442 (11)	0.0014 (12)	0.0097 (11)	−0.0086 (10)
Cl1	0.0925 (6)	0.0530 (5)	0.0613 (5)	0.0056 (5)	0.0242 (4)	−0.0040 (4)
Cl2	0.1238 (8)	0.0477 (6)	0.1188 (8)	−0.0073 (5)	0.0328 (6)	0.0059 (5)

Geometric parameters (Å, º) top

C1—O1	1.226 (3)	C8—C9	1.383 (4)
C1—N1	1.351 (3)	C8—C13	1.395 (4)
C1—C2	1.490 (4)	C8—N1	1.401 (3)
C2—C3	1.377 (4)	C9—C10	1.382 (4)
C2—C7	1.384 (4)	C9—H9	0.9300
C3—C4	1.377 (4)	C10—C11	1.357 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.364 (4)	C11—C12	1.383 (4)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.369 (5)	C12—C13	1.384 (4)
C5—H5	0.9300	C12—Cl2	1.716 (3)
C6—C7	1.378 (4)	C13—Cl1	1.718 (3)
C6—H6	0.9300	N1—H1N	0.8600
C7—H7	0.9300

O1—C1—N1	122.6 (3)	C9—C8—C13	119.0 (3)
O1—C1—C2	120.9 (3)	C9—C8—N1	122.5 (3)
N1—C1—C2	116.4 (2)	C13—C8—N1	118.5 (2)
C3—C2—C7	119.2 (3)	C10—C9—C8	120.0 (3)
C3—C2—C1	118.3 (3)	C10—C9—H9	120.0
C7—C2—C1	122.5 (3)	C8—C9—H9	120.0
C2—C3—C4	120.7 (3)	C11—C10—C9	121.1 (3)
C2—C3—H3	119.6	C11—C10—H10	119.4
C4—C3—H3	119.6	C9—C10—H10	119.4
C5—C4—C3	119.4 (3)	C10—C11—C12	119.9 (3)
C5—C4—H4	120.3	C10—C11—H11	120.1
C3—C4—H4	120.3	C12—C11—H11	120.1
C4—C5—C6	120.7 (3)	C11—C12—C13	119.9 (3)
C4—C5—H5	119.7	C11—C12—Cl2	119.6 (3)
C6—C5—H5	119.7	C13—C12—Cl2	120.4 (2)
C5—C6—C7	120.1 (3)	C12—C13—C8	120.1 (2)
C5—C6—H6	120.0	C12—C13—Cl1	120.1 (2)
C7—C6—H6	120.0	C8—C13—Cl1	119.8 (2)
C6—C7—C2	119.8 (3)	C1—N1—C8	127.4 (2)
C6—C7—H7	120.1	C1—N1—H1N	116.3
C2—C7—H7	120.1	C8—N1—H1N	116.3

O1—C1—C2—C3	25.7 (4)	C9—C10—C11—C12	0.1 (5)
N1—C1—C2—C3	−154.3 (2)	C10—C11—C12—C13	−0.4 (4)
O1—C1—C2—C7	−151.9 (3)	C10—C11—C12—Cl2	−179.8 (2)
N1—C1—C2—C7	28.1 (4)	C11—C12—C13—C8	0.1 (4)
C7—C2—C3—C4	−2.9 (4)	Cl2—C12—C13—C8	179.5 (2)
C1—C2—C3—C4	179.4 (2)	C11—C12—C13—Cl1	−178.9 (2)
C2—C3—C4—C5	1.9 (4)	Cl2—C12—C13—Cl1	0.5 (3)
C3—C4—C5—C6	0.2 (5)	C9—C8—C13—C12	0.4 (4)
C4—C5—C6—C7	−1.2 (5)	N1—C8—C13—C12	179.5 (2)
C5—C6—C7—C2	0.1 (4)	C9—C8—C13—Cl1	179.48 (19)
C3—C2—C7—C6	1.9 (4)	N1—C8—C13—Cl1	−1.5 (3)
C1—C2—C7—C6	179.4 (3)	O1—C1—N1—C8	7.4 (4)
C13—C8—C9—C10	−0.7 (4)	C2—C1—N1—C8	−172.6 (2)
N1—C8—C9—C10	−179.7 (3)	C9—C8—N1—C1	−30.1 (4)
C8—C9—C10—C11	0.5 (4)	C13—C8—N1—C1	150.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.17	2.952 (3)	152
N1—H1N···Cl1	0.86	2.57	2.929 (3)	106
C9—H9···O1	0.93	2.34	2.861 (4)	115

Symmetry code: (i) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉Cl₂NO
M_r	266.11
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	295
a, b, c (Å)	24.2968 (12), 11.3273 (5), 8.7396 (3)
V (Å³)	2405.29 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.45 × 0.09 × 0.07

Data collection
Diffractometer	Oxford Diffraction Xcalibur
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.894, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	21027, 2319, 981
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.093, 0.91
No. of reflections	2319
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.17	2.952 (3)	151.9
N1—H1N···Cl1	0.86	2.57	2.929 (3)	106.1
C9—H9···O1	0.93	2.34	2.861 (4)	114.8

Symmetry code: (i) x, −y+1, z+1/2.

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