(1R,2R,E,E)-N,N'-Bis(4-chloro-benzyl-idene)cyclo-hexane-1,2-diamine.

The title Schiff base ligand, C(20)H(20)Cl(2)N(2), was prepared by condensation of commercially available p-chloro-benzalde-hyde and (R,R)-1,2-diammonium-cyclo-hexane mono-(+)-tartrate. The cyclo-hexane ring adopts a chair conformation. The dihedral angle between the two aromatic rings is 62.52 (8)°. The crystal structure is stabilized by an inter-molecular C-H⋯Cl hydrogen bond.

Related literature

For the crystal structures of some Schiff bases derived from cyclo­hexane-1,2-diamine, see: Fan et al. (2011 ▶); Glidewell et al. (2005 ▶); Saleh Salga et al. (2010 ▶). For applications of chiral Schiff base ligands, see: Da Silva et al. (2011 ▶); Przybylski et al. (2009 ▶); Gupta & Sutar (2008 ▶); Dhar & Taploo (1982 ▶); Munslow et al. (2001 ▶); Gillespie et al. (2002 ▶); Kureshy et al. (2001 ▶); Takenaka et al. (2002 ▶). For the synthesis of the title compound, see: Larrow & Jacobsen (1998 ▶); Periasamy et al. (2001 ▶).

Experimental

Crystal data

C20H20Cl2N2

M = 359.28

Orthorhombic,

a = 5.5058 (11) Å

b = 15.734 (3) Å

c = 21.302 (4) Å

V = 1845.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 120 K

0.5 × 0.23 × 0.15 mm

Data collection

Stoe IPDS 2T diffractometer

12920 measured reflections

4973 independent reflections

4065 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.113

S = 1.13

4973 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 2099 Friedel pairs

Flack parameter: −0.11 (7)

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000724/bt5777sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000724/bt5777Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000724/bt5777Isup3.cml

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

C20H20Cl2N2	F(000) = 752
Mr = 359.28	Dx = 1.293 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4973 reflections
a = 5.5058 (11) Å	θ = 2.3–29.2°
b = 15.734 (3) Å	µ = 0.36 mm−1
c = 21.302 (4) Å	T = 120 K
V = 1845.4 (6) Å3	Needle, colorless
Z = 4	0.5 × 0.23 × 0.15 mm

Stoe IPDS 2T diffractometer	4065 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.088
graphite	θmax = 29.2°, θmin = 2.3°
Detector resolution: 0.15 mm pixels mm-1	h = −7→7
rotation method scans	k = −19→21
12920 measured reflections	l = −29→29
4973 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054	w = 1/[σ2(Fo2) + (0.0326P)2 + 0.5925P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max = 0.002
S = 1.13	Δρmax = 0.29 e Å−3
4973 reflections	Δρmin = −0.34 e Å−3
218 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0059 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2099 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.11 (7)

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	−0.02567 (12)	1.06658 (5)	0.95529 (3)	0.03732 (17)
Cl2	1.02450 (16)	0.61772 (5)	1.03022 (3)	0.0446 (2)
C9	0.5215 (5)	1.08153 (16)	0.83309 (11)	0.0302 (5)
H9	0.6498	1.1182	0.8246	0.036*
N2	0.9823 (4)	0.78245 (13)	0.73687 (9)	0.0292 (5)
C3	1.0135 (5)	0.91257 (17)	0.56137 (10)	0.0316 (5)
H3A	0.9729	0.9310	0.5192	0.038*
H3B	1.1598	0.9422	0.5742	0.038*
C18	0.9686 (5)	0.65212 (16)	0.95383 (11)	0.0333 (6)
N1	0.6607 (4)	0.92267 (14)	0.71446 (9)	0.0284 (5)
C12	0.1355 (5)	0.97300 (18)	0.85723 (11)	0.0293 (5)
H12	0.0050	0.9371	0.8655	0.035*
C8	0.4930 (5)	1.00840 (15)	0.79711 (10)	0.0258 (5)
C10	0.3615 (5)	1.10062 (18)	0.88148 (12)	0.0319 (6)
H10	0.3825	1.1493	0.9057	0.038*
C7	0.6765 (5)	0.98715 (16)	0.74955 (10)	0.0256 (5)
H7	0.8102	1.0228	0.7451	0.031*
C14	0.8364 (5)	0.73657 (17)	0.76733 (12)	0.0302 (6)
H14	0.6916	0.7206	0.7482	0.036*
C11	0.1706 (5)	1.04590 (17)	0.89291 (11)	0.0279 (5)
C1	0.8652 (5)	0.90495 (16)	0.67300 (11)	0.0269 (5)
H1	1.0099	0.9347	0.6884	0.032*
C15	0.8846 (5)	0.70693 (17)	0.83196 (12)	0.0301 (6)
C2	0.8063 (5)	0.93512 (19)	0.60586 (11)	0.0301 (5)
H2A	0.6575	0.9083	0.5916	0.036*
H2B	0.7814	0.9962	0.6058	0.036*
C17	1.1362 (6)	0.70438 (18)	0.92486 (12)	0.0339 (6)
H17	1.2761	0.7210	0.9460	0.041*
C13	0.2957 (5)	0.95433 (17)	0.80948 (11)	0.0285 (6)
H13	0.2732	0.9057	0.7854	0.034*
C4	1.0598 (6)	0.81726 (19)	0.56146 (11)	0.0366 (6)
H4A	1.1963	0.8045	0.5343	0.044*
H4B	0.9183	0.7880	0.5451	0.044*
C5	1.1139 (6)	0.78524 (18)	0.62769 (12)	0.0349 (6)
H5A	1.1323	0.7239	0.6268	0.042*
H5B	1.2658	0.8096	0.6421	0.042*
C6	0.9115 (5)	0.80889 (17)	0.67350 (11)	0.0292 (6)
H6	0.7621	0.7792	0.6615	0.035*
C19	0.7602 (5)	0.6264 (2)	0.92339 (13)	0.0382 (7)
H19	0.6486	0.5912	0.9433	0.046*
C16	1.0941 (5)	0.73191 (17)	0.86384 (12)	0.0328 (6)
H16	1.2062	0.7672	0.8441	0.039*
C20	0.7205 (5)	0.65407 (19)	0.86231 (13)	0.0372 (6)
H20	0.5809	0.6368	0.8413	0.045*

	U11	U22	U33	U12	U13	U23
Cl1	0.0353 (3)	0.0513 (4)	0.0254 (2)	0.0067 (3)	0.0022 (3)	−0.0030 (3)
Cl2	0.0633 (5)	0.0419 (4)	0.0286 (3)	0.0112 (4)	0.0068 (3)	0.0108 (3)
C9	0.0313 (13)	0.0296 (12)	0.0298 (10)	−0.0005 (12)	−0.0019 (11)	−0.0020 (10)
N2	0.0323 (11)	0.0293 (10)	0.0260 (9)	−0.0006 (10)	−0.0026 (10)	0.0040 (8)
C3	0.0306 (13)	0.0398 (14)	0.0244 (10)	0.0026 (12)	0.0017 (11)	0.0063 (10)
C18	0.0463 (15)	0.0281 (12)	0.0257 (10)	0.0069 (13)	0.0033 (12)	0.0060 (10)
N1	0.0292 (11)	0.0311 (11)	0.0248 (9)	0.0003 (10)	−0.0013 (8)	−0.0026 (9)
C12	0.0284 (13)	0.0353 (14)	0.0242 (11)	−0.0005 (12)	−0.0041 (10)	0.0025 (11)
C8	0.0280 (13)	0.0271 (12)	0.0221 (9)	0.0014 (11)	−0.0050 (10)	0.0011 (8)
C10	0.0356 (14)	0.0317 (14)	0.0283 (11)	0.0033 (12)	−0.0057 (11)	−0.0058 (10)
C7	0.0286 (12)	0.0261 (12)	0.0223 (10)	−0.0007 (10)	−0.0018 (10)	0.0039 (10)
C14	0.0313 (14)	0.0307 (14)	0.0287 (12)	−0.0028 (12)	0.0007 (11)	0.0002 (11)
C11	0.0291 (12)	0.0340 (14)	0.0206 (10)	0.0089 (11)	−0.0021 (10)	0.0017 (10)
C1	0.0267 (12)	0.0299 (13)	0.0240 (10)	−0.0016 (11)	0.0006 (10)	−0.0006 (10)
C15	0.0341 (13)	0.0268 (13)	0.0295 (12)	0.0005 (11)	0.0025 (11)	0.0038 (10)
C2	0.0307 (12)	0.0337 (14)	0.0259 (11)	0.0052 (12)	0.0000 (10)	0.0050 (11)
C17	0.0394 (15)	0.0322 (14)	0.0301 (13)	−0.0022 (13)	−0.0025 (11)	0.0001 (11)
C13	0.0346 (13)	0.0285 (13)	0.0225 (10)	−0.0002 (11)	−0.0058 (10)	0.0001 (10)
C4	0.0426 (16)	0.0417 (15)	0.0253 (11)	0.0037 (14)	0.0015 (11)	−0.0037 (11)
C5	0.0404 (16)	0.0330 (14)	0.0312 (13)	0.0088 (13)	0.0005 (12)	0.0006 (11)
C6	0.0341 (14)	0.0299 (13)	0.0235 (11)	0.0002 (12)	−0.0031 (10)	0.0020 (10)
C19	0.0355 (15)	0.0385 (16)	0.0405 (14)	−0.0014 (13)	0.0086 (12)	0.0122 (13)
C16	0.0362 (15)	0.0300 (14)	0.0323 (13)	−0.0047 (12)	0.0008 (11)	0.0062 (11)
C20	0.0313 (14)	0.0388 (16)	0.0415 (15)	−0.0053 (13)	0.0012 (12)	0.0060 (13)

Cl1—C11	1.743 (3)	C14—C15	1.478 (4)
Cl2—C18	1.742 (2)	C14—H14	0.9300
C9—C10	1.389 (4)	C1—C6	1.533 (4)
C9—C8	1.391 (3)	C1—C2	1.541 (3)
C9—H9	0.9300	C1—H1	0.9800
N2—C14	1.260 (3)	C15—C20	1.388 (4)
N2—C6	1.466 (3)	C15—C16	1.395 (4)
C3—C4	1.521 (4)	C2—H2A	0.9700
C3—C2	1.525 (3)	C2—H2B	0.9700
C3—H3A	0.9700	C17—C16	1.390 (3)
C3—H3B	0.9700	C17—H17	0.9300
C18—C19	1.379 (4)	C13—H13	0.9300
C18—C17	1.382 (4)	C4—C5	1.527 (4)
N1—C7	1.263 (3)	C4—H4A	0.9700
N1—C1	1.458 (3)	C4—H4B	0.9700
C12—C13	1.378 (4)	C5—C6	1.527 (4)
C12—C11	1.389 (4)	C5—H5A	0.9700
C12—H12	0.9300	C5—H5B	0.9700
C8—C13	1.404 (4)	C6—H6	0.9800
C8—C7	1.469 (3)	C19—C20	1.390 (4)
C10—C11	1.380 (4)	C19—H19	0.9300
C10—H10	0.9300	C16—H16	0.9300
C7—H7	0.9300	C20—H20	0.9300
C10—C9—C8	121.1 (3)	C16—C15—C14	120.9 (2)
C10—C9—H9	119.5	C3—C2—C1	110.3 (2)
C8—C9—H9	119.5	C3—C2—H2A	109.6
C14—N2—C6	117.9 (2)	C1—C2—H2A	109.6
C4—C3—C2	110.7 (2)	C3—C2—H2B	109.6
C4—C3—H3A	109.5	C1—C2—H2B	109.6
C2—C3—H3A	109.5	H2A—C2—H2B	108.1
C4—C3—H3B	109.5	C18—C17—C16	119.5 (3)
C2—C3—H3B	109.5	C18—C17—H17	120.3
H3A—C3—H3B	108.1	C16—C17—H17	120.3
C19—C18—C17	121.4 (2)	C12—C13—C8	120.3 (2)
C19—C18—Cl2	119.7 (2)	C12—C13—H13	119.9
C17—C18—Cl2	119.0 (2)	C8—C13—H13	119.9
C7—N1—C1	117.3 (2)	C3—C4—C5	111.0 (2)
C13—C12—C11	119.4 (3)	C3—C4—H4A	109.4
C13—C12—H12	120.3	C5—C4—H4A	109.4
C11—C12—H12	120.3	C3—C4—H4B	109.4
C9—C8—C13	119.0 (2)	C5—C4—H4B	109.4
C9—C8—C7	119.4 (2)	H4A—C4—H4B	108.0
C13—C8—C7	121.5 (2)	C6—C5—C4	111.6 (2)
C11—C10—C9	118.6 (2)	C6—C5—H5A	109.3
C11—C10—H10	120.7	C4—C5—H5A	109.3
C9—C10—H10	120.7	C6—C5—H5B	109.3
N1—C7—C8	122.9 (2)	C4—C5—H5B	109.3
N1—C7—H7	118.5	H5A—C5—H5B	108.0
C8—C7—H7	118.5	N2—C6—C5	109.0 (2)
N2—C14—C15	123.1 (3)	N2—C6—C1	109.3 (2)
N2—C14—H14	118.4	C5—C6—C1	110.9 (2)
C15—C14—H14	118.4	N2—C6—H6	109.2
C10—C11—C12	121.6 (2)	C5—C6—H6	109.2
C10—C11—Cl1	119.3 (2)	C1—C6—H6	109.2
C12—C11—Cl1	119.0 (2)	C18—C19—C20	118.6 (3)
N1—C1—C6	108.2 (2)	C18—C19—H19	120.7
N1—C1—C2	109.9 (2)	C20—C19—H19	120.7
C6—C1—C2	110.2 (2)	C17—C16—C15	120.4 (3)
N1—C1—H1	109.5	C17—C16—H16	119.8
C6—C1—H1	109.5	C15—C16—H16	119.8
C2—C1—H1	109.5	C15—C20—C19	121.5 (3)
C20—C15—C16	118.7 (2)	C15—C20—H20	119.3
C20—C15—C14	120.4 (3)	C19—C20—H20	119.3
C10—C9—C8—C13	1.3 (4)	C9—C8—C13—C12	−1.0 (4)
C10—C9—C8—C7	−175.4 (2)	C7—C8—C13—C12	175.6 (2)
C8—C9—C10—C11	−0.7 (4)	C2—C3—C4—C5	−56.8 (3)
C1—N1—C7—C8	−174.9 (2)	C3—C4—C5—C6	55.3 (3)
C9—C8—C7—N1	−178.8 (2)	C14—N2—C6—C5	−127.0 (3)
C13—C8—C7—N1	4.6 (4)	C14—N2—C6—C1	111.7 (3)
C6—N2—C14—C15	−178.9 (2)	C4—C5—C6—N2	−175.6 (2)
C9—C10—C11—C12	−0.2 (4)	C4—C5—C6—C1	−55.2 (3)
C9—C10—C11—Cl1	177.6 (2)	N1—C1—C6—N2	−63.4 (3)
C13—C12—C11—C10	0.5 (4)	C2—C1—C6—N2	176.4 (2)
C13—C12—C11—Cl1	−177.32 (19)	N1—C1—C6—C5	176.4 (2)
C7—N1—C1—C6	138.6 (2)	C2—C1—C6—C5	56.2 (3)
C7—N1—C1—C2	−101.0 (3)	C17—C18—C19—C20	0.0 (4)
N2—C14—C15—C20	−177.8 (3)	Cl2—C18—C19—C20	−179.5 (2)
N2—C14—C15—C16	2.7 (4)	C18—C17—C16—C15	−0.1 (4)
C4—C3—C2—C1	58.1 (3)	C20—C15—C16—C17	−0.2 (4)
N1—C1—C2—C3	−176.9 (2)	C14—C15—C16—C17	179.3 (3)
C6—C1—C2—C3	−57.8 (3)	C16—C15—C20—C19	0.4 (4)
C19—C18—C17—C16	0.2 (4)	C14—C15—C20—C19	−179.1 (3)
Cl2—C18—C17—C16	179.7 (2)	C18—C19—C20—C15	−0.3 (4)
C11—C12—C13—C8	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cl1i	0.97	2.81	3.525 (3)	131.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cl1i	0.97	2.81	3.525 (3)	131

Symmetry code: (i) .