rac-(E,E)-N,N'-Bis(2-chloro-benzyl-idene)cyclo-hexane-1,2-di-amine.

In the title racemic Schiff base ligand, C20H20Cl2N2, which was prepared by the condensation of 2-chloro-benzaldehyde and cyclo-hexane-1,2-di-amine, the cyclo-hexane ring adopts a chair conformation and the dihedral angle between the aromatic rings of the 2-chloro-phenyl substituent groups is 62.52 (8)°. In the structure, there are two short intra-molecular methine C-H⋯Cl inter-actions [C⋯Cl = 3.066 (2) and 3.076 (3) Å], and in the crystal there are also weak inter-molecular aromatic C-H⋯Cl [3.464 (3), 3.553 (3) and 3.600 (3) Å] and Cl⋯Cl [3.557 (3) and 3.891 (3) Å] contacts.

Related literature

For the crystal structures of some Schiff bases derived from cyclo­hexane-1,2-di­amine, see: Arvinnezhad et al. (2012 ▶); Fan et al. (2011 ▶); Saleh Salga et al. (2010 ▶). For applications of chiral Schiff base ligands, see: Da Silva et al. (2011 ▶); Dhar & Taploo (1982 ▶); Przybylski et al. (2009 ▶); Gupta & Sutar (2008 ▶). For the synthesis of the title compound, see: Larrow & Jacobsen (1998 ▶).

Experimental

Crystal data

C20H20Cl2N2

M = 359.28

Monoclinic,

a = 5.9029 (5) Å

b = 19.5613 (13) Å

c = 16.1662 (11) Å

β = 93.493 (7)°

V = 1863.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.30 × 0.20 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.902, T max = 0.949

7483 measured reflections

3273 independent reflections

2252 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.106

S = 1.02

3273 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014554/zs2261sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014554/zs2261Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014554/zs2261Isup3.cml

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

C20H20Cl2N2	F(000) = 752
Mr = 359.28	Dx = 1.281 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2442 reflections
a = 5.9029 (5) Å	θ = 3.1–29.1°
b = 19.5613 (13) Å	µ = 0.35 mm−1
c = 16.1662 (11) Å	T = 293 K
β = 93.493 (7)°	Block, colourless
V = 1863.2 (2) Å3	0.30 × 0.20 × 0.15 mm
Z = 4

Agilent Xcalibur Eos diffractometer	3273 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2252 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 16.0534 pixels mm-1	θmax = 25.0°, θmin = 3.3°
ω scans	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −23→18
Tmin = 0.902, Tmax = 0.949	l = −19→17
7483 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0349P)2 + 0.4202P] where P = (Fo2 + 2Fc2)/3
3273 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.20 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
Cl1	0.73684 (13)	0.05324 (3)	0.02770 (4)	0.0762 (2)
Cl2	1.12436 (13)	0.46542 (4)	0.17646 (5)	0.0914 (3)
N1	0.7836 (3)	0.26396 (10)	−0.03727 (11)	0.0555 (5)
C8	0.9564 (4)	0.17516 (12)	0.04725 (12)	0.0489 (6)
C1	0.5739 (4)	0.29405 (11)	−0.07382 (12)	0.0520 (6)
H1B	0.4442	0.2674	−0.0567	0.062*
C6	0.5559 (4)	0.36693 (12)	−0.04157 (13)	0.0583 (7)
H6A	0.6885	0.3932	−0.0568	0.070*
N2	0.5510 (4)	0.36480 (10)	0.04896 (11)	0.0613 (6)
C14	0.7170 (5)	0.39062 (12)	0.09007 (14)	0.0586 (6)
H14A	0.8318	0.4110	0.0617	0.070*
C7	0.7660 (4)	0.20790 (12)	−0.00033 (12)	0.0492 (6)
H7A	0.6258	0.1861	−0.0032	0.059*
C13	1.1395 (4)	0.21396 (13)	0.07903 (13)	0.0587 (6)
H13A	1.1465	0.2602	0.0661	0.070*
C15	0.7373 (4)	0.38992 (12)	0.18143 (14)	0.0550 (6)
C10	1.1237 (5)	0.07662 (14)	0.11857 (14)	0.0673 (8)
H10A	1.1179	0.0304	0.1317	0.081*
C9	0.9546 (4)	0.10611 (12)	0.06799 (12)	0.0540 (6)
C16	0.9153 (4)	0.42153 (12)	0.22641 (15)	0.0615 (7)
C20	0.5769 (5)	0.35715 (13)	0.22604 (15)	0.0669 (7)
H20A	0.4546	0.3359	0.1976	0.080*
C11	1.3010 (5)	0.11644 (17)	0.14930 (15)	0.0777 (9)
H11A	1.4156	0.0972	0.1838	0.093*
C17	0.9323 (5)	0.42009 (15)	0.31214 (17)	0.0756 (8)
H17A	1.0535	0.4415	0.3411	0.091*
C2	0.5740 (4)	0.29389 (13)	−0.16818 (13)	0.0634 (7)
H2B	0.7073	0.3178	−0.1853	0.076*
H2C	0.5804	0.2472	−0.1880	0.076*
C3	0.3615 (5)	0.32848 (13)	−0.20597 (14)	0.0679 (7)
H3A	0.3679	0.3298	−0.2658	0.081*
H3B	0.2292	0.3020	−0.1931	0.081*
C5	0.3413 (5)	0.40078 (14)	−0.07892 (15)	0.0783 (9)
H5A	0.3340	0.4476	−0.0594	0.094*
H5B	0.2093	0.3766	−0.0610	0.094*
C12	1.3100 (4)	0.18501 (17)	0.12915 (15)	0.0725 (8)
H12A	1.4315	0.2116	0.1495	0.087*
C19	0.5930 (5)	0.35511 (14)	0.31149 (17)	0.0783 (8)
H19A	0.4841	0.3322	0.3401	0.094*
C4	0.3382 (5)	0.40022 (14)	−0.17353 (16)	0.0825 (9)
H4A	0.1970	0.4199	−0.1962	0.099*
H4B	0.4620	0.4281	−0.1915	0.099*
C18	0.7716 (6)	0.38728 (15)	0.35396 (17)	0.0819 (9)
H18A	0.7825	0.3866	0.4116	0.098*

	U11	U22	U33	U12	U13	U23
Cl1	0.0871 (5)	0.0566 (4)	0.0835 (5)	0.0021 (4)	−0.0058 (4)	0.0000 (3)
Cl2	0.0686 (5)	0.1026 (6)	0.1027 (6)	−0.0136 (4)	0.0018 (4)	−0.0098 (4)
N1	0.0581 (13)	0.0600 (13)	0.0482 (11)	0.0065 (10)	0.0025 (10)	0.0112 (9)
C8	0.0547 (15)	0.0576 (15)	0.0350 (11)	0.0102 (12)	0.0076 (10)	−0.0003 (10)
C1	0.0560 (15)	0.0538 (14)	0.0457 (12)	0.0028 (12)	0.0003 (11)	0.0077 (10)
C6	0.0690 (17)	0.0549 (15)	0.0499 (13)	0.0001 (13)	−0.0050 (12)	0.0039 (11)
N2	0.0686 (14)	0.0649 (13)	0.0497 (11)	0.0024 (11)	−0.0019 (10)	−0.0047 (9)
C14	0.0677 (17)	0.0493 (14)	0.0583 (15)	0.0044 (13)	0.0002 (13)	−0.0018 (11)
C7	0.0542 (14)	0.0543 (14)	0.0393 (11)	0.0055 (12)	0.0034 (10)	−0.0002 (11)
C13	0.0649 (17)	0.0636 (16)	0.0478 (13)	0.0032 (13)	0.0052 (12)	−0.0007 (11)
C15	0.0638 (16)	0.0454 (14)	0.0547 (14)	0.0065 (12)	−0.0065 (13)	−0.0056 (11)
C10	0.087 (2)	0.0641 (17)	0.0496 (14)	0.0270 (16)	−0.0021 (14)	−0.0012 (12)
C9	0.0653 (16)	0.0589 (15)	0.0376 (12)	0.0145 (13)	0.0024 (11)	−0.0025 (10)
C16	0.0647 (17)	0.0533 (15)	0.0656 (16)	0.0062 (13)	−0.0041 (13)	−0.0067 (12)
C20	0.0782 (19)	0.0636 (17)	0.0576 (16)	−0.0079 (15)	−0.0060 (14)	−0.0053 (12)
C11	0.081 (2)	0.097 (2)	0.0536 (15)	0.0358 (18)	−0.0137 (15)	−0.0084 (15)
C17	0.081 (2)	0.076 (2)	0.0680 (18)	0.0003 (17)	−0.0157 (16)	−0.0181 (15)
C2	0.0752 (18)	0.0686 (17)	0.0461 (13)	0.0056 (14)	0.0021 (13)	0.0066 (12)
C3	0.0817 (19)	0.0721 (18)	0.0481 (14)	0.0024 (15)	−0.0103 (13)	0.0079 (12)
C5	0.096 (2)	0.0648 (17)	0.0712 (18)	0.0260 (16)	−0.0146 (16)	−0.0042 (14)
C12	0.0621 (17)	0.098 (2)	0.0570 (16)	0.0101 (17)	−0.0040 (14)	−0.0143 (15)
C19	0.095 (2)	0.0727 (19)	0.0674 (18)	−0.0071 (17)	0.0074 (16)	0.0016 (14)
C4	0.100 (2)	0.0716 (19)	0.0717 (18)	0.0166 (17)	−0.0243 (17)	0.0146 (14)
C18	0.111 (3)	0.077 (2)	0.0552 (16)	0.0005 (19)	−0.0075 (18)	−0.0097 (14)

Cl1—C9	1.745 (2)	C10—H10A	0.9300
Cl2—C16	1.742 (3)	C16—C17	1.384 (3)
N1—C7	1.256 (3)	C20—C19	1.379 (3)
N1—C1	1.462 (3)	C20—H20A	0.9300
C8—C9	1.392 (3)	C11—C12	1.382 (4)
C8—C13	1.393 (3)	C11—H11A	0.9300
C8—C7	1.469 (3)	C17—C18	1.359 (4)
C1—C6	1.524 (3)	C17—H17A	0.9300
C1—C2	1.525 (3)	C2—C3	1.520 (3)
C1—H1B	0.9800	C2—H2B	0.9700
C6—N2	1.466 (3)	C2—H2C	0.9700
C6—C5	1.522 (3)	C3—C4	1.507 (4)
C6—H6A	0.9800	C3—H3A	0.9700
N2—C14	1.256 (3)	C3—H3B	0.9700
C14—C15	1.475 (3)	C5—C4	1.529 (3)
C14—H14A	0.9300	C5—H5A	0.9700
C7—H7A	0.9300	C5—H5B	0.9700
C13—C12	1.375 (3)	C12—H12A	0.9300
C13—H13A	0.9300	C19—C18	1.375 (4)
C15—C20	1.383 (3)	C19—H19A	0.9300
C15—C16	1.386 (3)	C4—H4A	0.9700
C10—C11	1.373 (4)	C4—H4B	0.9700
C10—C9	1.378 (3)	C18—H18A	0.9300
C7—N1—C1	116.8 (2)	C15—C20—H20A	119.1
C9—C8—C13	117.2 (2)	C10—C11—C12	120.3 (2)
C9—C8—C7	122.2 (2)	C10—C11—H11A	119.9
C13—C8—C7	120.5 (2)	C12—C11—H11A	119.9
N1—C1—C6	108.26 (18)	C18—C17—C16	119.8 (3)
N1—C1—C2	110.58 (19)	C18—C17—H17A	120.1
C6—C1—C2	110.38 (18)	C16—C17—H17A	120.1
N1—C1—H1B	109.2	C3—C2—C1	110.5 (2)
C6—C1—H1B	109.2	C3—C2—H2B	109.5
C2—C1—H1B	109.2	C1—C2—H2B	109.5
N2—C6—C5	110.0 (2)	C3—C2—H2C	109.5
N2—C6—C1	108.72 (18)	C1—C2—H2C	109.5
C5—C6—C1	110.19 (19)	H2B—C2—H2C	108.1
N2—C6—H6A	109.3	C4—C3—C2	111.4 (2)
C5—C6—H6A	109.3	C4—C3—H3A	109.3
C1—C6—H6A	109.3	C2—C3—H3A	109.3
C14—N2—C6	117.0 (2)	C4—C3—H3B	109.3
N2—C14—C15	122.6 (3)	C2—C3—H3B	109.3
N2—C14—H14A	118.7	H3A—C3—H3B	108.0
C15—C14—H14A	118.7	C6—C5—C4	110.7 (2)
N1—C7—C8	123.1 (2)	C6—C5—H5A	109.5
N1—C7—H7A	118.4	C4—C5—H5A	109.5
C8—C7—H7A	118.4	C6—C5—H5B	109.5
C12—C13—C8	121.1 (3)	C4—C5—H5B	109.5
C12—C13—H13A	119.5	H5A—C5—H5B	108.1
C8—C13—H13A	119.5	C13—C12—C11	120.1 (3)
C20—C15—C16	117.0 (2)	C13—C12—H12A	119.9
C20—C15—C14	120.7 (2)	C11—C12—H12A	119.9
C16—C15—C14	122.3 (3)	C18—C19—C20	119.4 (3)
C11—C10—C9	119.1 (3)	C18—C19—H19A	120.3
C11—C10—H10A	120.5	C20—C19—H19A	120.3
C9—C10—H10A	120.5	C3—C4—C5	111.0 (2)
C10—C9—C8	122.2 (2)	C3—C4—H4A	109.4
C10—C9—Cl1	117.6 (2)	C5—C4—H4A	109.4
C8—C9—Cl1	120.09 (17)	C3—C4—H4B	109.4
C17—C16—C15	121.5 (3)	C5—C4—H4B	109.4
C17—C16—Cl2	117.6 (2)	H4A—C4—H4B	108.0
C15—C16—Cl2	120.8 (2)	C17—C18—C19	120.3 (3)
C19—C20—C15	121.9 (2)	C17—C18—H18A	119.8
C19—C20—H20A	119.1	C19—C18—H18A	119.8
C7—N1—C1—C6	126.4 (2)	C20—C15—C16—C17	0.3 (4)
C7—N1—C1—C2	−112.5 (2)	C14—C15—C16—C17	−179.7 (2)
N1—C1—C6—N2	−60.1 (3)	C20—C15—C16—Cl2	−178.99 (19)
C2—C1—C6—N2	178.69 (19)	C14—C15—C16—Cl2	1.0 (3)
N1—C1—C6—C5	179.2 (2)	C16—C15—C20—C19	−0.7 (4)
C2—C1—C6—C5	58.1 (3)	C14—C15—C20—C19	179.3 (2)
C5—C6—N2—C14	−125.3 (2)	C9—C10—C11—C12	−0.5 (4)
C1—C6—N2—C14	114.0 (2)	C15—C16—C17—C18	−0.2 (4)
C6—N2—C14—C15	−178.0 (2)	Cl2—C16—C17—C18	179.1 (2)
C1—N1—C7—C8	−173.03 (19)	N1—C1—C2—C3	−177.1 (2)
C9—C8—C7—N1	−161.7 (2)	C6—C1—C2—C3	−57.3 (3)
C13—C8—C7—N1	23.4 (3)	C1—C2—C3—C4	56.3 (3)
C9—C8—C13—C12	−0.4 (3)	N2—C6—C5—C4	−177.2 (2)
C7—C8—C13—C12	174.8 (2)	C1—C6—C5—C4	−57.3 (3)
N2—C14—C15—C20	3.3 (4)	C8—C13—C12—C11	−0.4 (4)
N2—C14—C15—C16	−176.7 (2)	C10—C11—C12—C13	0.9 (4)
C11—C10—C9—C8	−0.4 (4)	C15—C20—C19—C18	0.9 (4)
C11—C10—C9—Cl1	178.1 (2)	C2—C3—C4—C5	−55.8 (3)
C13—C8—C9—C10	0.8 (3)	C6—C5—C4—C3	56.3 (3)
C7—C8—C9—C10	−174.3 (2)	C16—C17—C18—C19	0.5 (4)
C13—C8—C9—Cl1	−177.66 (17)	C20—C19—C18—C17	−0.8 (4)
C7—C8—C9—Cl1	7.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cl1	0.93	2.72	3.066 (2)	103
C14—H14A···Cl2	0.93	2.68	3.076 (3)	107