2,6-Bis(2-chloro­phen­yl)-4-oxo-3,5-diphenyl­heptane-1,1,7,7-tetra­carbo­nitrile

Ali, A.J.; Athimoolam, S.; Bahadur, S.A.; Raja, V.P.A.

doi:10.1107/S1600536811017284

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1407-o1408

doi:10.1107/S1600536811017284

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2,6-Bis(2-chlorophenyl)-4-oxo-3,5-diphenylheptane-1,1,7,7-tetracarbonitrile

A. Jahubar Ali,^a S. Athimoolam,^b S. Asath Bahadur ^c ^* and V. P. Alex Raja ^d

^aDepartment of Science and Humanities, National College of Engineering, Maruthakulam, Tirunelveli 627 151, India, ^bDepartment of Physics, University College of Engineering Nagercoil, Anna University of Technology Tirunelveli, Nagercoil 629 004, India, ^cDepartment of Physics, Kalasalingam University, Anand Nagar, Krishnan Koil 626 190, India, and ^dDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: s_a_bahadur@yahoo.co.in

(Received 30 April 2011; accepted 7 May 2011; online 14 May 2011)

In the title compound, C₃₅H₂₄Cl₂N₄O, the phenyl rings are oriented almost parallel to each other, making a dihedral angle of 0.6 (2)°, whereas the chlorophenyl rings are oriented at a dihedral angle of 28.3 (1)°. The crystal structure is stabilized through an extensive series of C—H⋯N, C—H⋯O and C—H⋯Cl interactions. One of the C—H⋯N interactions generates an R₂²(12) ring motif around a crystallographic inversion centre. C(5), C(10) and C(12) chain motifs are observed in the unit cell through C—H⋯N and C—H⋯Cl interactions. During the structure analysis, it was observed that the unit cell contains large accessible voids, which host disordered solvent molecules. This affects the diffraction pattern, mostly at low scattering angles and was corrected with the SQUEEZE program [Spek, A. L. (2009 ). Acta Cryst. D65, 148–155].

Related literature

For our investigations into regio/stereoselectivity in adduct reactions and weak hydrogen bonding, see: Ali et al. (2010 ). For weak hydrogen-bonding interactions, see: Desiraju & Steiner (1999 ). For ring and chain motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₃₅H₂₄Cl₂N₄O
M_r = 587.48
Monoclinic, P 2₁ /c
a = 17.7226 (6) Å
b = 10.6169 (3) Å
c = 20.8491 (7) Å
β = 113.724 (2)°
V = 3591.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.28 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
32501 measured reflections
6324 independent reflections
3647 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.211
S = 1.07
6324 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N11ⁱ	0.98	2.33	3.186 (4)	145
C23—H23⋯N11ⁱⁱ	0.93	2.65	3.409 (5)	139
C34—H34⋯N72ⁱⁱⁱ	0.93	2.52	3.443 (8)	176
C52—H52⋯N12^iv	0.93	2.64	3.489 (5)	152
C36—H36⋯N12^iv	0.93	2.96	3.805 (7)	152
C54—H54⋯N71^v	0.93	2.91	3.564 (6)	128
C53—H53⋯N71^v	0.93	2.96	3.583 (5)	126
C64—H64⋯Cl2^vi	0.93	2.97	3.663 (5)	133
C64—H64⋯O1^vi	0.93	2.88	3.673 (5)	144
C65—H65⋯Cl1^vi	0.93	2.80	3.728 (4)	174
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+2; (iii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+2, -y, -z+2; (v) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL/PC; molecular graphics: Mercury (Macrae et al., 2006 ) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017284/sj5139sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017284/sj5139Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017284/sj5139Isup3.cml

checkCIF report

Comment top

In continuation of our investigations into regio/stereoselectivity in adduct reactions and weak hydrogen bonding (Ali et al., 2010), the title compound was synthesized and crystallized and the structural features are disucussed here.

The molecular structure of the title compound is shown in Fig. 1. The two phenyl rings are oriented almost parallel to each other with the dihedral angle of 0.6 (2)°, whereas the two chlorophenyl rings are oriented with an angle of 28.3 (1)°. This large variation may be due to the strong and moderate C—H···Cl interactions observed in the lattice. Also, due to these C—H···Cl interactions in the crystal packing (Fig. 2, Table 1), the chlorine atoms in the chlorophenyl rings lie away from the benzene ring planes with the distances of 0.01 (1)Å (for Cl1 atom in C21/C26/Cl1 ring) and 0.08 (1)Å (for Cl2 atom in C61/C66/Cl2 ring).

The packing diagram of the title compound is shown in Fig. 2. The crystal packing is stabilized through an extensive series of C—H···N, C—H···O and C—H···Cl interactions (Desiraju & Steiner, 1999). One C—H···O, two C—H···Cl and seven C—H···N interactions are observed in the lattice (Table 1). The two C—H···Cl interactions are involved in making chain motifs, viz., a zigzag C(12) chain motif [through C65—H65···Cl1 (-x + 1, y - 1/2,-z + 3/2)] and a linear C(5) chain motif [through C64—H64···Cl2 (-x + 1, y - 1/2, -z + 3/2)] (Etter et al., 1990). These chain motifs are speckled on the ab-plane of the unit cell as shown in Fig. 3. A C(10) chain motif is observed through C7—H7···N11 (x, -y + 1/2, 2–1/2) interactions which connect the molecules in a head-to-tail fashion along the c axis. Another C—H···N interaction makes a zigzag C(12) chain motif extending along c (Fig. 4). A centrosymmetric R₂²(16) ring motif is observed around a crystallographic inversion centre through C—H···N interactions (Fig. 5).

Related literature top

For our investigations into regio/stereoselectivity in adduct reactions and weak hydrogen bonding, see: Ali et al. (2010). For weak hydrogen-bonding interactions, see: Desiraju & Steiner (1999). For ring and chain motifs, see: Etter et al. (1990).

Experimental top

A mixture of 1,3-diphenylacetone 5 (1 mmol), 2-[(2-chlorophenyl)methylene]malononitrile 6 (2 mmol), and sodium ethoxide (2 mmol) was ground well in a mortar and pestle at ambient temperature for about 15–30 sec. Then water (50–70 ml) was added to the mixture and the product was filtered and washed with water, dried in vacuo and subjected to flash chromatographic purification employing flash silica gel (230–400 mesh) with petroleum ether-ethyl acetate mixture (1:2 v/v) as eluent. The products were further recrystallized from ethanol-ethyl acetate mixture (1:2 v/v).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with the atom numbering scheme. The displacement ellipsoids are shown at the 30% probability level.
	Fig. 2. Packing diagram of the title structure viewed down the a axis. (Cl is shown in green, N in blue, O in red, C in black and H as a circles)
	Fig. 3. Linear chain C(5) and zigzag chain C(12) motifs speckled along ab-plane of the crystal through C—H···Cl interactions. (Cl is shown in green, N in blue, O in red, C in black and H as a circles)
	Fig. 4. Zigzag chain C(12) motif extending along c axis of the unit cell. (Cl is shown in green, N in blue, O in red, C in black and H as a circles)
	Fig. 5. Ring R₂²(12) motif formed through C—H···N interactions. (Cl is shown in green, N in blue, O in red, C in black and H as a circles)

2,6-Bis(2-chlorophenyl)-4-oxo-3,5-diphenylheptane-1,1,7,7-tetracarbonitrile top

Crystal data top

C₃₅H₂₄Cl₂N₄O	F(000) = 1216
M_r = 587.48	D_x = 1.087 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4531 reflections
a = 17.7226 (6) Å	θ = 2.8–24.8°
b = 10.6169 (3) Å	µ = 0.21 mm⁻¹
c = 20.8491 (7) Å	T = 293 K
β = 113.724 (2)°	Bulk, colourless
V = 3591.4 (2) Å³	0.28 × 0.26 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3647 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 25.0°, θ_min = 1.3°
ω scans	h = −21→21
32501 measured reflections	k = −12→12
6324 independent reflections	l = −24→24

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.114P)² + 0.3187P] where P = (F_o² + 2F_c²)/3
6324 reflections	(Δ/σ)_max < 0.001
379 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₃₅H₂₄Cl₂N₄O	V = 3591.4 (2) Å³
M_r = 587.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.7226 (6) Å	µ = 0.21 mm⁻¹
b = 10.6169 (3) Å	T = 293 K
c = 20.8491 (7) Å	0.28 × 0.26 × 0.22 mm
β = 113.724 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3647 reflections with I > 2σ(I)
32501 measured reflections	R_int = 0.042
6324 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 1.07	Δρ_max = 0.31 e Å⁻³
6324 reflections	Δρ_min = −0.27 e Å⁻³
379 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
C1	0.8486 (2)	0.2323 (3)	1.03039 (17)	0.0623 (9)
H1	0.8131	0.1752	1.0428	0.075*
C2	0.80856 (18)	0.2513 (2)	0.95012 (16)	0.0511 (7)
H2	0.7513	0.2768	0.9379	0.061*
C3	0.80630 (17)	0.1253 (2)	0.91167 (15)	0.0471 (7)
H3	0.8628	0.1041	0.9185	0.057*
C4	0.75542 (17)	0.1395 (2)	0.83391 (14)	0.0432 (7)
C5	0.78235 (17)	0.0628 (2)	0.78571 (14)	0.0469 (7)
H5	0.8066	−0.0159	0.8097	0.056*
C6	0.70861 (17)	0.0294 (2)	0.71749 (15)	0.0478 (7)
H6	0.6838	0.1091	0.6953	0.057*
C7	0.73918 (19)	−0.0388 (3)	0.66625 (17)	0.0574 (8)
H7	0.7774	0.0182	0.6574	0.069*
C11	0.8527 (2)	0.3532 (4)	1.06706 (19)	0.0695 (9)
C12	0.9297 (3)	0.1773 (3)	1.05569 (18)	0.0682 (9)
C21	0.84917 (19)	0.3550 (3)	0.92648 (16)	0.0544 (8)
C22	0.9254 (2)	0.3393 (3)	0.92435 (18)	0.0649 (9)
H22	0.9522	0.2625	0.9386	0.078*
C23	0.9631 (3)	0.4317 (4)	0.9022 (2)	0.0888 (12)
H23	1.0151	0.4180	0.9025	0.107*
C24	0.9248 (4)	0.5425 (5)	0.8801 (2)	0.1061 (16)
H24	0.9499	0.6049	0.8641	0.127*
C25	0.8508 (3)	0.5635 (4)	0.8809 (3)	0.1058 (15)
H25	0.8248	0.6405	0.8654	0.127*
C26	0.8118 (2)	0.4710 (3)	0.9049 (2)	0.0785 (11)
C31	0.7717 (3)	0.0166 (3)	0.93763 (18)	0.0689 (10)
C32	0.6897 (3)	0.0163 (4)	0.9284 (2)	0.0900 (13)
H32	0.6555	0.0832	0.9059	0.108*
C33	0.6594 (5)	−0.0833 (6)	0.9528 (4)	0.148 (3)
H33	0.6047	−0.0834	0.9473	0.178*
C34	0.7084 (9)	−0.1801 (8)	0.9843 (5)	0.189 (5)
H34	0.6874	−0.2456	1.0018	0.227*
C35	0.7875 (7)	−0.1860 (6)	0.9916 (4)	0.167 (3)
H35	0.8196	−0.2565	1.0112	0.200*
C36	0.8197 (4)	−0.0850 (3)	0.9692 (2)	0.1048 (15)
H36	0.8747	−0.0861	0.9756	0.126*
C51	0.84908 (17)	0.1359 (2)	0.77357 (15)	0.0483 (7)
C52	0.9270 (2)	0.0907 (3)	0.79355 (18)	0.0672 (9)
H52	0.9402	0.0123	0.8150	0.081*
C53	0.9874 (2)	0.1595 (4)	0.7825 (2)	0.0877 (12)
H53	1.0407	0.1282	0.7971	0.105*
C54	0.9676 (3)	0.2725 (4)	0.7502 (2)	0.0889 (12)
H54	1.0074	0.3184	0.7418	0.107*
C55	0.8901 (3)	0.3199 (4)	0.7298 (2)	0.0827 (11)
H55	0.8775	0.3978	0.7076	0.099*
C56	0.8309 (2)	0.2548 (3)	0.74135 (19)	0.0692 (9)
H56	0.7784	0.2888	0.7280	0.083*
C61	0.64183 (18)	−0.0448 (2)	0.72805 (15)	0.0498 (7)
C62	0.6602 (2)	−0.1490 (3)	0.77301 (18)	0.0629 (9)
H62	0.7149	−0.1713	0.7984	0.076*
C63	0.5993 (3)	−0.2186 (3)	0.7803 (2)	0.0818 (11)
H63	0.6132	−0.2869	0.8108	0.098*
C64	0.5187 (3)	−0.1890 (5)	0.7436 (3)	0.0953 (13)
H64	0.4776	−0.2379	0.7482	0.114*
C65	0.4985 (2)	−0.0889 (4)	0.7005 (2)	0.0857 (12)
H65	0.4433	−0.0676	0.6764	0.103*
C66	0.5586 (2)	−0.0174 (3)	0.69163 (17)	0.0598 (8)
C71	0.7844 (2)	−0.1558 (4)	0.6959 (2)	0.0728 (10)
C72	0.6731 (2)	−0.0659 (3)	0.5998 (2)	0.0707 (9)
Cl1	0.71848 (7)	0.50340 (9)	0.90878 (9)	0.1247 (6)
Cl2	0.52710 (6)	0.10805 (10)	0.63456 (5)	0.0895 (4)
N11	0.8558 (2)	0.4487 (4)	1.09207 (19)	0.0953 (11)
N12	0.9931 (3)	0.1336 (4)	1.0738 (2)	0.1026 (11)
N71	0.8197 (2)	−0.2441 (4)	0.7193 (2)	0.1078 (12)
N72	0.6215 (2)	−0.0886 (4)	0.5485 (2)	0.1075 (12)
O1	0.69628 (13)	0.20891 (19)	0.81126 (12)	0.0644 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.073 (2)	0.0613 (17)	0.060 (2)	−0.0149 (17)	0.0352 (19)	−0.0043 (15)
C2	0.0488 (17)	0.0524 (15)	0.0531 (19)	−0.0042 (13)	0.0216 (15)	−0.0043 (13)
C3	0.0486 (17)	0.0468 (14)	0.0483 (18)	−0.0044 (12)	0.0220 (15)	−0.0012 (12)
C4	0.0418 (16)	0.0410 (13)	0.0476 (18)	−0.0076 (13)	0.0189 (14)	0.0009 (12)
C5	0.0474 (17)	0.0470 (14)	0.0462 (17)	0.0011 (12)	0.0189 (14)	0.0046 (12)
C6	0.0509 (17)	0.0503 (15)	0.0453 (17)	−0.0023 (13)	0.0228 (15)	0.0008 (12)
C7	0.0534 (19)	0.0652 (17)	0.064 (2)	−0.0067 (15)	0.0342 (18)	−0.0031 (15)
C11	0.065 (2)	0.087 (2)	0.067 (2)	−0.0161 (18)	0.0382 (19)	−0.0177 (19)
C12	0.079 (3)	0.073 (2)	0.049 (2)	−0.005 (2)	0.020 (2)	−0.0031 (16)
C21	0.057 (2)	0.0517 (16)	0.0488 (18)	−0.0103 (14)	0.0153 (15)	−0.0030 (13)
C22	0.065 (2)	0.0675 (19)	0.062 (2)	−0.0153 (16)	0.0255 (18)	−0.0023 (16)
C23	0.090 (3)	0.098 (3)	0.083 (3)	−0.038 (2)	0.039 (2)	−0.002 (2)
C24	0.131 (4)	0.095 (3)	0.086 (3)	−0.053 (3)	0.037 (3)	0.007 (2)
C25	0.116 (4)	0.059 (2)	0.119 (4)	−0.014 (2)	0.023 (3)	0.023 (2)
C26	0.072 (2)	0.0543 (18)	0.092 (3)	−0.0060 (17)	0.015 (2)	0.0025 (17)
C31	0.105 (3)	0.0566 (18)	0.057 (2)	−0.0177 (18)	0.045 (2)	−0.0049 (15)
C32	0.104 (3)	0.084 (2)	0.110 (3)	−0.040 (2)	0.072 (3)	−0.023 (2)
C33	0.227 (7)	0.122 (4)	0.172 (6)	−0.084 (5)	0.159 (6)	−0.050 (4)
C34	0.367 (15)	0.104 (5)	0.152 (6)	−0.095 (8)	0.163 (9)	−0.018 (4)
C35	0.291 (10)	0.073 (3)	0.151 (6)	−0.013 (5)	0.104 (7)	0.023 (3)
C36	0.169 (5)	0.054 (2)	0.096 (3)	0.003 (2)	0.058 (3)	0.017 (2)
C51	0.0420 (17)	0.0577 (16)	0.0450 (17)	−0.0033 (13)	0.0173 (14)	0.0051 (13)
C52	0.055 (2)	0.075 (2)	0.076 (2)	0.0024 (16)	0.0301 (19)	0.0075 (17)
C53	0.055 (2)	0.110 (3)	0.105 (3)	−0.007 (2)	0.039 (2)	−0.004 (3)
C54	0.071 (3)	0.114 (3)	0.090 (3)	−0.025 (2)	0.042 (2)	0.006 (2)
C55	0.083 (3)	0.088 (2)	0.076 (3)	−0.021 (2)	0.031 (2)	0.021 (2)
C56	0.057 (2)	0.0697 (19)	0.073 (2)	−0.0032 (16)	0.0188 (18)	0.0171 (17)
C61	0.0455 (17)	0.0542 (15)	0.0548 (19)	−0.0018 (13)	0.0257 (15)	−0.0092 (14)
C62	0.060 (2)	0.0599 (17)	0.072 (2)	−0.0060 (15)	0.0300 (18)	0.0092 (16)
C63	0.083 (3)	0.076 (2)	0.095 (3)	−0.016 (2)	0.044 (2)	0.001 (2)
C64	0.084 (3)	0.118 (3)	0.097 (3)	−0.034 (3)	0.050 (3)	−0.007 (3)
C65	0.046 (2)	0.129 (3)	0.085 (3)	−0.004 (2)	0.030 (2)	−0.008 (3)
C66	0.050 (2)	0.078 (2)	0.054 (2)	0.0052 (16)	0.0242 (16)	−0.0077 (15)
C71	0.066 (2)	0.088 (2)	0.075 (3)	0.006 (2)	0.040 (2)	−0.007 (2)
C72	0.068 (2)	0.092 (2)	0.056 (2)	0.005 (2)	0.029 (2)	−0.0180 (19)
Cl1	0.0854 (8)	0.0705 (6)	0.1940 (15)	0.0109 (5)	0.0308 (9)	−0.0038 (7)
Cl2	0.0723 (7)	0.1123 (8)	0.0810 (7)	0.0277 (5)	0.0279 (5)	0.0140 (5)
N11	0.100 (3)	0.107 (2)	0.104 (3)	−0.024 (2)	0.067 (2)	−0.040 (2)
N12	0.106 (3)	0.112 (3)	0.081 (3)	0.016 (2)	0.028 (2)	0.007 (2)
N71	0.100 (3)	0.104 (3)	0.128 (3)	0.034 (2)	0.055 (3)	0.010 (2)
N72	0.089 (3)	0.141 (3)	0.083 (3)	0.001 (2)	0.026 (2)	−0.041 (2)
O1	0.0532 (13)	0.0653 (12)	0.0664 (15)	0.0092 (11)	0.0154 (11)	−0.0047 (11)

Geometric parameters (Å, º) top

C1—C12	1.441 (5)	C31—C32	1.387 (5)
C1—C11	1.481 (5)	C32—C33	1.373 (6)
C1—C2	1.546 (4)	C32—H32	0.9300
C1—H1	0.9800	C33—C34	1.335 (12)
C2—C21	1.503 (4)	C33—H33	0.9300
C2—C3	1.551 (4)	C34—C35	1.348 (12)
C2—H2	0.9800	C34—H34	0.9300
C3—C31	1.506 (4)	C35—C36	1.381 (8)
C3—C4	1.513 (4)	C35—H35	0.9300
C3—H3	0.9800	C36—H36	0.9300
C4—O1	1.211 (3)	C51—C52	1.359 (4)
C4—C5	1.512 (4)	C51—C56	1.405 (4)
C5—C51	1.518 (4)	C52—C53	1.389 (5)
C5—C6	1.537 (4)	C52—H52	0.9300
C5—H5	0.9800	C53—C54	1.351 (6)
C6—C61	1.510 (4)	C53—H53	0.9300
C6—C7	1.557 (4)	C54—C55	1.361 (5)
C6—H6	0.9800	C54—H54	0.9300
C7—C72	1.438 (5)	C55—C56	1.356 (5)
C7—C71	1.473 (5)	C55—H55	0.9300
C7—H7	0.9800	C56—H56	0.9300
C11—N11	1.132 (4)	C61—C66	1.391 (4)
C12—N12	1.132 (5)	C61—C62	1.401 (4)
C21—C22	1.379 (4)	C62—C63	1.365 (5)
C21—C26	1.385 (4)	C62—H62	0.9300
C22—C23	1.368 (5)	C63—C64	1.359 (6)
C22—H22	0.9300	C63—H63	0.9300
C23—C24	1.343 (7)	C64—C65	1.343 (6)
C23—H23	0.9300	C64—H64	0.9300
C24—C25	1.338 (7)	C65—C66	1.380 (5)
C24—H24	0.9300	C65—H65	0.9300
C25—C26	1.403 (6)	C66—Cl2	1.723 (3)
C25—H25	0.9300	C71—N71	1.123 (4)
C26—Cl1	1.723 (4)	C72—N72	1.119 (4)
C31—C36	1.366 (5)

C12—C1—C11	109.1 (3)	C25—C26—Cl1	119.8 (3)
C12—C1—C2	113.9 (3)	C36—C31—C32	118.6 (4)
C11—C1—C2	110.6 (3)	C36—C31—C3	120.9 (4)
C12—C1—H1	107.7	C32—C31—C3	120.5 (3)
C11—C1—H1	107.7	C33—C32—C31	119.7 (5)
C2—C1—H1	107.7	C33—C32—H32	120.2
C21—C2—C1	112.3 (2)	C31—C32—H32	120.2
C21—C2—C3	112.2 (2)	C34—C33—C32	120.1 (7)
C1—C2—C3	110.6 (2)	C34—C33—H33	120.0
C21—C2—H2	107.1	C32—C33—H33	120.0
C1—C2—H2	107.1	C33—C34—C35	122.1 (7)
C3—C2—H2	107.1	C33—C34—H34	118.9
C31—C3—C4	107.9 (2)	C35—C34—H34	118.9
C31—C3—C2	113.9 (2)	C34—C35—C36	118.5 (8)
C4—C3—C2	110.4 (2)	C34—C35—H35	120.7
C31—C3—H3	108.2	C36—C35—H35	120.7
C4—C3—H3	108.2	C31—C36—C35	120.9 (6)
C2—C3—H3	108.2	C31—C36—H36	119.5
O1—C4—C5	121.6 (3)	C35—C36—H36	119.5
O1—C4—C3	121.8 (2)	C52—C51—C56	118.2 (3)
C5—C4—C3	116.6 (2)	C52—C51—C5	122.1 (3)
C4—C5—C51	108.1 (2)	C56—C51—C5	119.7 (3)
C4—C5—C6	111.2 (2)	C51—C52—C53	121.3 (3)
C51—C5—C6	113.2 (2)	C51—C52—H52	119.4
C4—C5—H5	108.1	C53—C52—H52	119.4
C51—C5—H5	108.1	C54—C53—C52	119.2 (4)
C6—C5—H5	108.1	C54—C53—H53	120.4
C61—C6—C5	114.2 (2)	C52—C53—H53	120.4
C61—C6—C7	111.5 (2)	C53—C54—C55	120.7 (4)
C5—C6—C7	110.0 (2)	C53—C54—H54	119.7
C61—C6—H6	106.9	C55—C54—H54	119.7
C5—C6—H6	106.9	C56—C55—C54	120.8 (3)
C7—C6—H6	106.9	C56—C55—H55	119.6
C72—C7—C71	109.3 (3)	C54—C55—H55	119.6
C72—C7—C6	112.3 (3)	C55—C56—C51	119.9 (3)
C71—C7—C6	112.6 (3)	C55—C56—H56	120.1
C72—C7—H7	107.4	C51—C56—H56	120.1
C71—C7—H7	107.4	C66—C61—C62	116.1 (3)
C6—C7—H7	107.4	C66—C61—C6	122.2 (3)
N11—C11—C1	176.4 (4)	C62—C61—C6	121.7 (3)
N12—C12—C1	178.2 (4)	C63—C62—C61	121.4 (3)
C22—C21—C26	116.4 (3)	C63—C62—H62	119.3
C22—C21—C2	121.7 (3)	C61—C62—H62	119.3
C26—C21—C2	121.9 (3)	C64—C63—C62	120.7 (4)
C23—C22—C21	122.8 (4)	C64—C63—H63	119.6
C23—C22—H22	118.6	C62—C63—H63	119.6
C21—C22—H22	118.6	C65—C64—C63	119.8 (4)
C24—C23—C22	119.8 (4)	C65—C64—H64	120.1
C24—C23—H23	120.1	C63—C64—H64	120.1
C22—C23—H23	120.1	C64—C65—C66	120.8 (4)
C25—C24—C23	120.2 (4)	C64—C65—H65	119.6
C25—C24—H24	119.9	C66—C65—H65	119.6
C23—C24—H24	119.9	C65—C66—C61	121.2 (3)
C24—C25—C26	120.9 (4)	C65—C66—Cl2	117.7 (3)
C24—C25—H25	119.5	C61—C66—Cl2	121.1 (2)
C26—C25—H25	119.5	N71—C71—C7	179.0 (5)
C21—C26—C25	119.9 (4)	N72—C72—C7	179.0 (5)
C21—C26—Cl1	120.3 (3)

C12—C1—C2—C21	−71.0 (3)	C4—C3—C31—C36	121.2 (3)
C11—C1—C2—C21	52.3 (3)	C2—C3—C31—C36	−115.9 (4)
C12—C1—C2—C3	55.2 (3)	C4—C3—C31—C32	−57.2 (4)
C11—C1—C2—C3	178.5 (2)	C2—C3—C31—C32	65.7 (4)
C21—C2—C3—C31	175.7 (3)	C36—C31—C32—C33	1.9 (6)
C1—C2—C3—C31	49.5 (3)	C3—C31—C32—C33	−179.7 (4)
C21—C2—C3—C4	−62.7 (3)	C31—C32—C33—C34	−0.9 (8)
C1—C2—C3—C4	171.1 (2)	C32—C33—C34—C35	−2.0 (12)
C31—C3—C4—O1	92.2 (3)	C33—C34—C35—C36	3.8 (13)
C2—C3—C4—O1	−32.9 (3)	C32—C31—C36—C35	−0.1 (6)
C31—C3—C4—C5	−88.1 (3)	C3—C31—C36—C35	−178.5 (5)
C2—C3—C4—C5	146.9 (2)	C34—C35—C36—C31	−2.7 (10)
O1—C4—C5—C51	95.0 (3)	C4—C5—C51—C52	117.7 (3)
C3—C4—C5—C51	−84.7 (3)	C6—C5—C51—C52	−118.7 (3)
O1—C4—C5—C6	−29.7 (3)	C4—C5—C51—C56	−61.6 (3)
C3—C4—C5—C6	150.5 (2)	C6—C5—C51—C56	62.0 (3)
C4—C5—C6—C61	−58.8 (3)	C56—C51—C52—C53	−0.1 (5)
C51—C5—C6—C61	179.2 (2)	C5—C51—C52—C53	−179.4 (3)
C4—C5—C6—C7	174.9 (2)	C51—C52—C53—C54	−1.1 (6)
C51—C5—C6—C7	53.0 (3)	C52—C53—C54—C55	1.2 (7)
C61—C6—C7—C72	55.6 (3)	C53—C54—C55—C56	−0.1 (7)
C5—C6—C7—C72	−176.6 (3)	C54—C55—C56—C51	−1.2 (6)
C61—C6—C7—C71	−68.4 (3)	C52—C51—C56—C55	1.3 (5)
C5—C6—C7—C71	59.4 (3)	C5—C51—C56—C55	−179.4 (3)
C12—C1—C11—N11	102 (6)	C5—C6—C61—C66	136.4 (3)
C2—C1—C11—N11	−24 (7)	C7—C6—C61—C66	−98.2 (3)
C11—C1—C12—N12	−131 (13)	C5—C6—C61—C62	−46.5 (4)
C2—C1—C12—N12	−7 (13)	C7—C6—C61—C62	78.9 (3)
C1—C2—C21—C22	74.6 (4)	C66—C61—C62—C63	−0.2 (5)
C3—C2—C21—C22	−50.7 (4)	C6—C61—C62—C63	−177.5 (3)
C1—C2—C21—C26	−106.2 (3)	C61—C62—C63—C64	0.5 (6)
C3—C2—C21—C26	128.5 (3)	C62—C63—C64—C65	−1.2 (6)
C26—C21—C22—C23	−0.1 (5)	C63—C64—C65—C66	1.8 (7)
C2—C21—C22—C23	179.2 (3)	C64—C65—C66—C61	−1.5 (6)
C21—C22—C23—C24	−1.4 (6)	C64—C65—C66—Cl2	179.2 (3)
C22—C23—C24—C25	1.3 (7)	C62—C61—C66—C65	0.7 (4)
C23—C24—C25—C26	0.1 (7)	C6—C61—C66—C65	178.0 (3)
C22—C21—C26—C25	1.5 (5)	C62—C61—C66—Cl2	180.0 (2)
C2—C21—C26—C25	−177.8 (3)	C6—C61—C66—Cl2	−2.7 (4)
C22—C21—C26—Cl1	−177.3 (3)	C72—C7—C71—N71	174 (100)
C2—C21—C26—Cl1	3.4 (5)	C6—C7—C71—N71	−60 (27)
C24—C25—C26—C21	−1.5 (7)	C71—C7—C72—N72	31 (24)
C24—C25—C26—Cl1	177.2 (4)	C6—C7—C72—N72	−94 (24)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N11ⁱ	0.98	2.33	3.186 (4)	145
C23—H23···N11ⁱⁱ	0.93	2.65	3.409 (5)	139
C34—H34···N72ⁱⁱⁱ	0.93	2.52	3.443 (8)	176
C52—H52···N12^iv	0.93	2.64	3.489 (5)	152
C36—H36···N12^iv	0.93	2.96	3.805 (7)	152
C54—H54···N71^v	0.93	2.91	3.564 (6)	128
C53—H53···N71^v	0.93	2.96	3.583 (5)	126
C64—H64···Cl2^vi	0.93	2.97	3.663 (5)	133
C64—H64···O1^vi	0.93	2.88	3.673 (5)	144
C65—H65···Cl1^vi	0.93	2.80	3.728 (4)	174

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+2; (iii) x, −y−1/2, z+1/2; (iv) −x+2, −y, −z+2; (v) −x+2, y+1/2, −z+3/2; (vi) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₃₅H₂₄Cl₂N₄O
M_r	587.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.7226 (6), 10.6169 (3), 20.8491 (7)
β (°)	113.724 (2)
V (Å³)	3591.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.28 × 0.26 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	32501, 6324, 3647
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.211, 1.07
No. of reflections	6324
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.27

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL/PC (Sheldrick, 2008), Mercury (Macrae et al., 2006) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N11ⁱ	0.98	2.33	3.186 (4)	145
C23—H23···N11ⁱⁱ	0.93	2.65	3.409 (5)	139
C34—H34···N72ⁱⁱⁱ	0.93	2.52	3.443 (8)	176
C52—H52···N12^iv	0.93	2.64	3.489 (5)	152
C36—H36···N12^iv	0.93	2.96	3.805 (7)	152
C54—H54···N71^v	0.93	2.91	3.564 (6)	128
C53—H53···N71^v	0.93	2.96	3.583 (5)	126
C64—H64···Cl2^vi	0.93	2.97	3.663 (5)	133
C64—H64···O1^vi	0.93	2.88	3.673 (5)	144
C65—H65···Cl1^vi	0.93	2.80	3.728 (4)	174

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+2; (iii) x, −y−1/2, z+1/2; (iv) −x+2, −y, −z+2; (v) −x+2, y+1/2, −z+3/2; (vi) −x+1, y−1/2, −z+3/2.

Acknowledgements

AJA and SAB sincerely thank the Vice Chancellor and Management of the Kalasalingam University, Anand Nagar, Krishnan Koil, for their support and encouragement. AJA also thanks the Principal and the Management of the National College of Engineering for their support.

References

Ali, A. J., Athimoolam, S., Bahadur, S. A. & Raja, V. P. A. (2010). Acta Cryst. E66, o2593. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 246–253. IUCr Monographs on Crystallography. Oxford University Press. Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 6| June 2011| Pages o1407-o1408

doi:10.1107/S1600536811017284

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

2,6-Bis(2-chloro­phen­yl)-4-oxo-3,5-di­phenyl­heptane-1,1,7,7-tetra­carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,6-Bis(2-chlorophenyl)-4-oxo-3,5-diphenylheptane-1,1,7,7-tetracarbonitrile