N,N'-Bis(2-chloro-phen-yl)propane-diamide.

The crystal structure of the title compound, C(15)H(12)Cl(2)N(2)O(2), contains three intramolecular hydrogen bonds; two C-H⋯O and a nonclassical N-H⋯Cl. The structure is further stabilized by intermolecular N-H⋯O hydrogen bonds and C-H⋯π interactions, resulting in a three-dimensional network. The two benzene rings make an interplanar angle of 58.0 (1)°.

Related literature

For literature on related compounds, see: Gowda et al. (2007 ▶, 2009 ▶, 2010 ▶).

Experimental

Crystal data

C15H12Cl2N2O2

M = 323.17

Monoclinic,

a = 13.8819 (9) Å

b = 15.3556 (10) Å

c = 7.0316 (5) Å

β = 104.027 (7)°

V = 1454.19 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 295 K

0.57 × 0.54 × 0.15 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.743, T max = 0.938

13088 measured reflections

2687 independent reflections

1930 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.03

2687 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044090/bt5396sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044090/bt5396Isup2.hkl

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

C15H12Cl2N2O2	F(000) = 664
Mr = 323.17	Dx = 1.476 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6793 reflections
a = 13.8819 (9) Å	θ = 3.7–29.3°
b = 15.3556 (10) Å	µ = 0.45 mm−1
c = 7.0316 (5) Å	T = 295 K
β = 104.027 (7)°	Block, colorless
V = 1454.19 (17) Å3	0.57 × 0.54 × 0.14 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	2687 independent reflections
graphite	1930 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.042
ω scans	θmax = 25.4°, θmin = 2.7°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −15→16
Tmin = 0.743, Tmax = 0.938	k = −15→18
13088 measured reflections	l = −8→8

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0805P)2] where P = (Fo2 + 2Fc2)/3
2687 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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	−0.19293 (15)	0.77176 (14)	0.5062 (3)	0.0449 (5)
C2	−0.19188 (15)	0.86196 (14)	0.4842 (3)	0.0469 (5)
C3	−0.27859 (19)	0.90983 (16)	0.4347 (3)	0.0582 (6)
H3	−0.2764	0.97	0.422	0.07*
C4	−0.36823 (18)	0.86717 (19)	0.4044 (4)	0.0666 (7)
H4	−0.4272	0.8986	0.3704	0.08*
C5	−0.37089 (17)	0.77888 (18)	0.4241 (4)	0.0635 (7)
H5	−0.4319	0.7508	0.4031	0.076*
C6	−0.28444 (16)	0.73034 (16)	0.4747 (3)	0.0543 (6)
H6	−0.2876	0.6702	0.4875	0.065*
C7	−0.08275 (16)	0.64231 (14)	0.5353 (3)	0.0444 (5)
C8	0.02513 (16)	0.61601 (14)	0.6081 (3)	0.0465 (5)
H8A	0.0515	0.6411	0.7369	0.056*
H8B	0.0292	0.5531	0.6211	0.056*
C9	0.08797 (15)	0.64552 (15)	0.4718 (3)	0.0437 (5)
C10	0.23819 (17)	0.60854 (14)	0.3636 (3)	0.0494 (5)
C11	0.33523 (18)	0.58501 (16)	0.4524 (3)	0.0567 (6)
C12	0.4116 (2)	0.60164 (18)	0.3623 (4)	0.0701 (7)
H12	0.4763	0.585	0.4224	0.084*
C13	0.3912 (2)	0.6429 (2)	0.1836 (4)	0.0764 (8)
H13	0.4422	0.6547	0.1228	0.092*
C14	0.2958 (2)	0.66657 (18)	0.0949 (4)	0.0710 (7)
H14	0.2825	0.6947	−0.0258	0.085*
C15	0.21891 (19)	0.64911 (16)	0.1830 (4)	0.0595 (6)
H15	0.1542	0.6647	0.1206	0.071*
N1	−0.10196 (12)	0.72631 (11)	0.5652 (3)	0.0479 (4)
H1N	−0.0523	0.7564	0.6287	0.057*
N2	0.16193 (13)	0.59006 (12)	0.4599 (3)	0.0514 (5)
H2N	0.1627	0.5399	0.5148	0.062*
O1	−0.14642 (13)	0.59039 (10)	0.4540 (3)	0.0607 (4)
O2	0.07446 (11)	0.71541 (10)	0.3868 (2)	0.0543 (4)
Cl1	−0.07891 (4)	0.91714 (4)	0.52012 (9)	0.0599 (2)
Cl2	0.36153 (5)	0.53220 (6)	0.67829 (10)	0.0792 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0449 (12)	0.0454 (14)	0.0446 (11)	0.0017 (9)	0.0115 (9)	−0.0026 (9)
C2	0.0521 (13)	0.0417 (14)	0.0490 (12)	0.0019 (10)	0.0164 (10)	−0.0002 (9)
C3	0.0653 (16)	0.0489 (15)	0.0625 (15)	0.0124 (12)	0.0192 (12)	0.0028 (11)
C4	0.0545 (15)	0.072 (2)	0.0730 (17)	0.0135 (13)	0.0144 (12)	0.0016 (13)
C5	0.0466 (13)	0.074 (2)	0.0698 (16)	−0.0023 (12)	0.0144 (11)	−0.0043 (13)
C6	0.0515 (13)	0.0530 (15)	0.0605 (13)	−0.0026 (11)	0.0173 (11)	−0.0016 (11)
C7	0.0541 (13)	0.0376 (13)	0.0424 (11)	−0.0014 (10)	0.0134 (10)	0.0026 (9)
C8	0.0534 (13)	0.0413 (13)	0.0449 (11)	0.0057 (10)	0.0121 (10)	0.0009 (9)
C9	0.0464 (12)	0.0392 (13)	0.0438 (11)	−0.0002 (10)	0.0075 (9)	−0.0033 (9)
C10	0.0526 (13)	0.0401 (13)	0.0584 (13)	0.0017 (10)	0.0189 (10)	−0.0028 (10)
C11	0.0546 (14)	0.0564 (16)	0.0598 (14)	−0.0020 (11)	0.0151 (11)	−0.0047 (11)
C12	0.0548 (15)	0.077 (2)	0.0827 (19)	−0.0055 (13)	0.0240 (14)	−0.0054 (15)
C13	0.0774 (19)	0.077 (2)	0.088 (2)	−0.0130 (16)	0.0453 (16)	−0.0037 (16)
C14	0.091 (2)	0.0587 (17)	0.0704 (16)	−0.0004 (14)	0.0334 (15)	0.0047 (13)
C15	0.0691 (16)	0.0501 (14)	0.0620 (14)	0.0044 (12)	0.0210 (12)	0.0043 (11)
N1	0.0429 (10)	0.0368 (11)	0.0623 (11)	−0.0002 (8)	0.0096 (8)	−0.0050 (8)
N2	0.0529 (11)	0.0420 (11)	0.0614 (11)	0.0048 (8)	0.0178 (9)	0.0070 (8)
O1	0.0604 (10)	0.0435 (10)	0.0734 (11)	−0.0032 (8)	0.0069 (8)	−0.0059 (8)
O2	0.0569 (9)	0.0424 (10)	0.0649 (9)	0.0056 (7)	0.0172 (7)	0.0097 (7)
Cl1	0.0637 (4)	0.0444 (4)	0.0747 (4)	−0.0066 (3)	0.0230 (3)	−0.0025 (3)
Cl2	0.0572 (4)	0.1069 (6)	0.0703 (5)	0.0077 (3)	0.0092 (3)	0.0168 (4)

C1—C6	1.390 (3)	C8—H8B	0.97
C1—C2	1.394 (3)	C9—O2	1.221 (3)
C1—N1	1.414 (3)	C9—N2	1.352 (3)
C2—C3	1.381 (3)	C10—C15	1.381 (3)
C2—Cl1	1.746 (2)	C10—C11	1.388 (3)
C3—C4	1.376 (3)	C10—N2	1.417 (3)
C3—H3	0.93	C11—C12	1.385 (3)
C4—C5	1.364 (4)	C11—Cl2	1.742 (2)
C4—H4	0.93	C12—C13	1.374 (4)
C5—C6	1.384 (3)	C12—H12	0.93
C5—H5	0.93	C13—C14	1.370 (4)
C6—H6	0.93	C13—H13	0.93
C7—O1	1.224 (2)	C14—C15	1.384 (3)
C7—N1	1.344 (3)	C14—H14	0.93
C7—C8	1.515 (3)	C15—H15	0.93
C8—C9	1.514 (3)	N1—H1N	0.86
C8—H8A	0.97	N2—H2N	0.86
C6—C1—C2	118.09 (19)	O2—C9—N2	123.54 (19)
C6—C1—N1	122.5 (2)	O2—C9—C8	121.98 (18)
C2—C1—N1	119.36 (18)	N2—C9—C8	114.42 (19)
C3—C2—C1	121.7 (2)	C15—C10—C11	118.8 (2)
C3—C2—Cl1	118.39 (18)	C15—C10—N2	121.9 (2)
C1—C2—Cl1	119.95 (16)	C11—C10—N2	119.3 (2)
C4—C3—C2	119.1 (2)	C12—C11—C10	120.9 (2)
C4—C3—H3	120.5	C12—C11—Cl2	119.2 (2)
C2—C3—H3	120.5	C10—C11—Cl2	119.83 (18)
C5—C4—C3	120.2 (2)	C13—C12—C11	119.5 (3)
C5—C4—H4	119.9	C13—C12—H12	120.3
C3—C4—H4	119.9	C11—C12—H12	120.3
C4—C5—C6	121.2 (2)	C14—C13—C12	120.1 (3)
C4—C5—H5	119.4	C14—C13—H13	119.9
C6—C5—H5	119.4	C12—C13—H13	119.9
C5—C6—C1	119.8 (2)	C13—C14—C15	120.7 (3)
C5—C6—H6	120.1	C13—C14—H14	119.7
C1—C6—H6	120.1	C15—C14—H14	119.7
O1—C7—N1	123.4 (2)	C10—C15—C14	120.0 (2)
O1—C7—C8	121.79 (19)	C10—C15—H15	120
N1—C7—C8	114.84 (19)	C14—C15—H15	120
C9—C8—C7	112.33 (17)	C7—N1—C1	128.66 (18)
C9—C8—H8A	109.1	C7—N1—H1N	115.7
C7—C8—H8A	109.1	C1—N1—H1N	115.7
C9—C8—H8B	109.1	C9—N2—C10	124.75 (19)
C7—C8—H8B	109.1	C9—N2—H2N	117.6
H8A—C8—H8B	107.9	C10—N2—H2N	117.6
C6—C1—C2—C3	0.7 (3)	C15—C10—C11—Cl2	−178.97 (18)
N1—C1—C2—C3	−177.32 (19)	N2—C10—C11—Cl2	0.8 (3)
C6—C1—C2—Cl1	−179.48 (15)	C10—C11—C12—C13	0.7 (4)
N1—C1—C2—Cl1	2.5 (3)	Cl2—C11—C12—C13	179.7 (2)
C1—C2—C3—C4	−0.7 (3)	C11—C12—C13—C14	−0.5 (4)
Cl1—C2—C3—C4	179.50 (18)	C12—C13—C14—C15	−0.3 (4)
C2—C3—C4—C5	0.3 (4)	C11—C10—C15—C14	−0.8 (4)
C3—C4—C5—C6	0.0 (4)	N2—C10—C15—C14	179.5 (2)
C4—C5—C6—C1	0.0 (4)	C13—C14—C15—C10	1.0 (4)
C2—C1—C6—C5	−0.4 (3)	O1—C7—N1—C1	−2.9 (3)
N1—C1—C6—C5	177.61 (19)	C8—C7—N1—C1	176.46 (18)
O1—C7—C8—C9	101.8 (2)	C6—C1—N1—C7	26.0 (3)
N1—C7—C8—C9	−77.5 (2)	C2—C1—N1—C7	−156.1 (2)
C7—C8—C9—O2	37.4 (3)	O2—C9—N2—C10	6.1 (3)
C7—C8—C9—N2	−145.36 (18)	C8—C9—N2—C10	−171.12 (19)
C15—C10—C11—C12	0.0 (4)	C15—C10—N2—C9	−43.0 (3)
N2—C10—C11—C12	179.7 (2)	C11—C10—N2—C9	137.2 (2)

Cg2 is the centroid of the C10/C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.24	3.038 (2)	154
N2—H2N···O1ii	0.86	2.03	2.856 (2)	160
C8—H8A···O2i	0.97	2.43	3.219 (3)	138
C15—H15···O2iii	0.93	2.54	3.265 (3)	135
C3—H3···Cg2iv	0.93	2.74	3.608 (2)	155
C6—H6···O1	0.93	2.37	2.906 (3)	116
C15—H15···O2	0.93	2.52	2.916 (3)	106
N1—H1N···Cl1	0.86	2.58	2.9730 (18)	109

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10/C15 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.24	3.038 (2)	154
N2—H2N⋯O1ii	0.86	2.03	2.856 (2)	160
C8—H8A⋯O2i	0.97	2.43	3.219 (3)	138
C3—H3⋯Cg2iv	0.93	2.74	3.608 (2)	155
C15—H15⋯O2	0.93	2.52	2.916 (3)	106
N1—H1N⋯Cl1	0.86	2.58	2.9730 (18)	109

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .