N,N'-Bis(4-chloro-benzyl-idene)-2,2-dimethyl-propane-1,3-diamine.

The title compound, C(19)H(20)Cl(2)N(2), is a potential bidentate Schiff base ligand. Intra-molecular C-H⋯N hydrogen bonds form five-membered rings, generating S(5) ring motifs. Each imino functional group is coplanar with its adjacent benzene ring; the two benzene rings form a dihedral angle of 51.30 (4)°. An inter-esting feature of the crystal structure is weak inter-molecular Cl⋯Cl [3.4752 (4) Å] and Cl⋯N [3.2927 (9) Å] inter-actions. Inter-molecular Cl⋯N inter-actions link mol-ecules into dimers with R(2) (2)(22) ring motifs. The crystal structure is further stabilized by weak π-π [centroid-centroid distances = 3.6970 (6)-3.8560 (6) Å] inter-actions.

Related literature

For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For related structures see, for example: Li et al. (2005 ▶); Bomfim et al. (2005 ▶); Glidewell et al. (2005 ▶, 2006 ▶); Sun et al. (2004 ▶); Fun et al. (2008 ▶).

Experimental

Crystal data

C19H20Cl2N2

M = 347.27

Monoclinic,

a = 19.6392 (3) Å

b = 9.3275 (2) Å

c = 9.7841 (2) Å

β = 92.213 (1)°

V = 1790.96 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 100 (1) K

0.51 × 0.35 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.836, T max = 0.966

21670 measured reflections

6419 independent reflections

5273 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.095

S = 1.03

6419 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2 and SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035307/tk2319sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035307/tk2319Isup2.hkl

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

C19H20Cl2N2	F000 = 728
Mr = 347.27	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8119 reflections
a = 19.6392 (3) Å	θ = 3.0–38.9º
b = 9.3275 (2) Å	µ = 0.36 mm−1
c = 9.7841 (2) Å	T = 100 (1) K
β = 92.213 (1)º	Plate, colourless
V = 1790.96 (6) Å3	0.51 × 0.35 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6419 independent reflections
Radiation source: fine-focus sealed tube	5273 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 100.0(1) K	θmax = 32.5º
φ and ω scans	θmin = 1.0º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −29→29
Tmin = 0.836, Tmax = 0.966	k = −14→12
21670 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.5329P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6419 reflections	Δρmax = 0.38 e Å−3
208 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.497643 (14)	0.49166 (3)	0.17717 (3)	0.02553 (7)
Cl2	−0.166144 (13)	0.43828 (3)	0.54241 (3)	0.02640 (7)
N1	0.28500 (4)	0.54904 (10)	0.70403 (9)	0.01950 (17)
N2	0.14528 (4)	0.37002 (10)	0.85655 (9)	0.01864 (17)
C1	0.35398 (5)	0.47808 (13)	0.45572 (11)	0.0216 (2)
H1A	0.3155	0.4238	0.4731	0.026*
C2	0.39180 (6)	0.44677 (13)	0.34258 (11)	0.0226 (2)
H2A	0.3791	0.3720	0.2842	0.027*
C3	0.44914 (5)	0.52935 (12)	0.31802 (11)	0.01962 (19)
C4	0.46927 (5)	0.64046 (12)	0.40359 (11)	0.0208 (2)
H4A	0.5080	0.6939	0.3863	0.025*
C5	0.43069 (5)	0.67111 (12)	0.51594 (11)	0.01929 (19)
H5A	0.4434	0.7466	0.5735	0.023*
C6	0.37302 (5)	0.59009 (11)	0.54371 (10)	0.01710 (18)
C7	0.33470 (5)	0.62450 (12)	0.66609 (11)	0.01815 (19)
H7A	0.3474	0.7046	0.7176	0.022*
C8	0.25179 (5)	0.59532 (12)	0.82751 (11)	0.0202 (2)
H8A	0.2046	0.6187	0.8048	0.024*
H8B	0.2740	0.6813	0.8628	0.024*
C9	0.25474 (5)	0.47832 (12)	0.93875 (11)	0.01860 (19)
C10	0.21738 (5)	0.34242 (12)	0.88813 (11)	0.01881 (19)
H10A	0.2386	0.3070	0.8068	0.023*
H10B	0.2216	0.2688	0.9579	0.023*
C11	0.12219 (5)	0.33583 (11)	0.73837 (11)	0.01765 (18)
H11A	0.1515	0.2936	0.6777	0.021*
C12	0.05057 (5)	0.36042 (11)	0.69311 (10)	0.01656 (18)
C13	0.00695 (5)	0.44318 (12)	0.77071 (11)	0.01855 (19)
H13A	0.0230	0.4832	0.8529	0.022*
C14	−0.06007 (5)	0.46587 (12)	0.72583 (11)	0.01985 (19)
H14A	−0.0891	0.5207	0.7774	0.024*
C15	−0.08314 (5)	0.40546 (12)	0.60260 (11)	0.01940 (19)
C16	−0.04087 (5)	0.32318 (12)	0.52386 (11)	0.0204 (2)
H16A	−0.0571	0.2832	0.4418	0.024*
C17	0.02632 (5)	0.30141 (12)	0.56973 (11)	0.01898 (19)
H17A	0.0553	0.2470	0.5175	0.023*
C18	0.32900 (5)	0.43799 (14)	0.97383 (12)	0.0249 (2)
H18A	0.3534	0.5214	1.0058	0.037*
H18B	0.3497	0.4014	0.8937	0.037*
H18C	0.3304	0.3660	1.0440	0.037*
C19	0.22142 (6)	0.53832 (14)	1.06574 (12)	0.0261 (2)
H19A	0.2452	0.6231	1.0960	0.039*
H19B	0.2235	0.4678	1.1372	0.039*
H19C	0.1747	0.5616	1.0435	0.039*

	U11	U22	U33	U12	U13	U23
Cl1	0.02940 (13)	0.02639 (15)	0.02128 (12)	0.00830 (10)	0.00692 (10)	0.00370 (10)
Cl2	0.01662 (11)	0.02663 (15)	0.03566 (15)	0.00011 (9)	−0.00260 (9)	0.00411 (11)
N1	0.0189 (4)	0.0204 (4)	0.0192 (4)	−0.0005 (3)	0.0014 (3)	0.0005 (3)
N2	0.0146 (3)	0.0200 (4)	0.0215 (4)	−0.0014 (3)	0.0025 (3)	0.0000 (3)
C1	0.0202 (4)	0.0231 (5)	0.0214 (5)	−0.0044 (4)	0.0001 (4)	−0.0006 (4)
C2	0.0251 (5)	0.0231 (5)	0.0197 (5)	−0.0028 (4)	−0.0007 (4)	−0.0026 (4)
C3	0.0221 (4)	0.0194 (5)	0.0175 (4)	0.0048 (4)	0.0024 (4)	0.0038 (4)
C4	0.0199 (4)	0.0176 (5)	0.0250 (5)	−0.0003 (4)	0.0039 (4)	0.0043 (4)
C5	0.0195 (4)	0.0154 (5)	0.0230 (5)	−0.0013 (3)	0.0012 (4)	0.0006 (4)
C6	0.0169 (4)	0.0167 (5)	0.0177 (4)	0.0001 (3)	−0.0004 (3)	0.0023 (4)
C7	0.0178 (4)	0.0174 (5)	0.0191 (4)	0.0002 (3)	−0.0002 (3)	0.0007 (4)
C8	0.0185 (4)	0.0197 (5)	0.0226 (5)	−0.0003 (4)	0.0044 (4)	−0.0008 (4)
C9	0.0162 (4)	0.0215 (5)	0.0182 (4)	−0.0019 (3)	0.0019 (3)	−0.0015 (4)
C10	0.0158 (4)	0.0191 (5)	0.0216 (5)	0.0002 (3)	0.0018 (3)	0.0000 (4)
C11	0.0165 (4)	0.0160 (5)	0.0207 (5)	0.0005 (3)	0.0049 (3)	0.0005 (4)
C12	0.0161 (4)	0.0153 (4)	0.0184 (4)	−0.0005 (3)	0.0028 (3)	0.0019 (3)
C13	0.0190 (4)	0.0185 (5)	0.0183 (5)	0.0007 (3)	0.0033 (3)	−0.0006 (4)
C14	0.0180 (4)	0.0189 (5)	0.0230 (5)	0.0017 (4)	0.0046 (4)	0.0015 (4)
C15	0.0156 (4)	0.0177 (5)	0.0249 (5)	−0.0010 (3)	0.0005 (3)	0.0049 (4)
C16	0.0215 (4)	0.0195 (5)	0.0202 (5)	−0.0020 (4)	−0.0003 (4)	−0.0008 (4)
C17	0.0194 (4)	0.0180 (5)	0.0197 (5)	0.0007 (3)	0.0029 (3)	−0.0006 (4)
C18	0.0186 (4)	0.0303 (6)	0.0255 (5)	−0.0024 (4)	−0.0025 (4)	0.0008 (4)
C19	0.0272 (5)	0.0292 (6)	0.0222 (5)	−0.0042 (4)	0.0065 (4)	−0.0055 (4)

Cl1—C3	1.7411 (11)	C9—C19	1.5323 (15)
Cl2—C15	1.7390 (10)	C9—C10	1.5370 (15)
N1—C7	1.2703 (13)	C10—H10A	0.9700
N1—C8	1.4602 (14)	C10—H10B	0.9700
N2—C11	1.2664 (14)	C11—C12	1.4761 (14)
N2—C10	1.4603 (13)	C11—H11A	0.9300
C1—C2	1.3876 (15)	C12—C17	1.3939 (15)
C1—C6	1.3956 (15)	C12—C13	1.3987 (14)
C1—H1A	0.9300	C13—C14	1.3876 (14)
C2—C3	1.3929 (15)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.3908 (16)
C3—C4	1.3805 (16)	C14—H14A	0.9300
C4—C5	1.3886 (14)	C15—C16	1.3860 (15)
C4—H4A	0.9300	C16—C17	1.3921 (14)
C5—C6	1.3970 (14)	C16—H16A	0.9300
C5—H5A	0.9300	C17—H17A	0.9300
C6—C7	1.4741 (14)	C18—H18A	0.9600
C7—H7A	0.9300	C18—H18B	0.9600
C8—C9	1.5408 (16)	C18—H18C	0.9600
C8—H8A	0.9700	C19—H19A	0.9600
C8—H8B	0.9700	C19—H19B	0.9600
C9—C18	1.5322 (15)	C19—H19C	0.9600
C7—N1—C8	116.79 (9)	C9—C10—H10A	109.3
C11—N2—C10	117.31 (9)	N2—C10—H10B	109.3
C2—C1—C6	120.72 (10)	C9—C10—H10B	109.3
C2—C1—H1A	119.6	H10A—C10—H10B	107.9
C6—C1—H1A	119.6	N2—C11—C12	122.56 (9)
C1—C2—C3	118.84 (10)	N2—C11—H11A	118.7
C1—C2—H2A	120.6	C12—C11—H11A	118.7
C3—C2—H2A	120.6	C17—C12—C13	119.48 (9)
C4—C3—C2	121.67 (10)	C17—C12—C11	119.22 (9)
C4—C3—Cl1	118.62 (8)	C13—C12—C11	121.30 (9)
C2—C3—Cl1	119.71 (9)	C14—C13—C12	120.38 (10)
C3—C4—C5	118.84 (10)	C14—C13—H13A	119.8
C3—C4—H4A	120.6	C12—C13—H13A	119.8
C5—C4—H4A	120.6	C13—C14—C15	119.07 (10)
C4—C5—C6	120.92 (10)	C13—C14—H14A	120.5
C4—C5—H5A	119.5	C15—C14—H14A	120.5
C6—C5—H5A	119.5	C16—C15—C14	121.61 (9)
C1—C6—C5	119.00 (9)	C16—C15—Cl2	118.88 (9)
C1—C6—C7	122.08 (9)	C14—C15—Cl2	119.47 (8)
C5—C6—C7	118.91 (9)	C15—C16—C17	118.83 (10)
N1—C7—C6	122.61 (10)	C15—C16—H16A	120.6
N1—C7—H7A	118.7	C17—C16—H16A	120.6
C6—C7—H7A	118.7	C16—C17—C12	120.63 (9)
N1—C8—C9	111.67 (9)	C16—C17—H17A	119.7
N1—C8—H8A	109.3	C12—C17—H17A	119.7
C9—C8—H8A	109.3	C9—C18—H18A	109.5
N1—C8—H8B	109.3	C9—C18—H18B	109.5
C9—C8—H8B	109.3	H18A—C18—H18B	109.5
H8A—C8—H8B	107.9	C9—C18—H18C	109.5
C18—C9—C19	109.91 (9)	H18A—C18—H18C	109.5
C18—C9—C10	107.95 (9)	H18B—C18—H18C	109.5
C19—C9—C10	110.43 (8)	C9—C19—H19A	109.5
C18—C9—C8	109.97 (8)	C9—C19—H19B	109.5
C19—C9—C8	107.97 (9)	H19A—C19—H19B	109.5
C10—C9—C8	110.61 (9)	C9—C19—H19C	109.5
N2—C10—C9	111.70 (9)	H19A—C19—H19C	109.5
N2—C10—H10A	109.3	H19B—C19—H19C	109.5
C6—C1—C2—C3	−0.13 (17)	C11—N2—C10—C9	125.72 (10)
C1—C2—C3—C4	0.35 (17)	C18—C9—C10—N2	178.07 (9)
C1—C2—C3—Cl1	179.70 (9)	C19—C9—C10—N2	57.90 (12)
C2—C3—C4—C5	−0.74 (17)	C8—C9—C10—N2	−61.57 (11)
Cl1—C3—C4—C5	179.89 (8)	C10—N2—C11—C12	−178.94 (9)
C3—C4—C5—C6	0.93 (16)	N2—C11—C12—C17	−170.66 (10)
C2—C1—C6—C5	0.31 (17)	N2—C11—C12—C13	10.16 (16)
C2—C1—C6—C7	−178.88 (10)	C17—C12—C13—C14	0.35 (16)
C4—C5—C6—C1	−0.72 (16)	C11—C12—C13—C14	179.52 (10)
C4—C5—C6—C7	178.50 (10)	C12—C13—C14—C15	−0.14 (16)
C8—N1—C7—C6	179.80 (9)	C13—C14—C15—C16	0.08 (16)
C1—C6—C7—N1	4.79 (16)	C13—C14—C15—Cl2	−177.78 (8)
C5—C6—C7—N1	−174.40 (10)	C14—C15—C16—C17	−0.23 (16)
C7—N1—C8—C9	−120.74 (10)	Cl2—C15—C16—C17	177.64 (8)
N1—C8—C9—C18	57.83 (12)	C15—C16—C17—C12	0.44 (16)
N1—C8—C9—C19	177.75 (8)	C13—C12—C17—C16	−0.51 (16)
N1—C8—C9—C10	−61.31 (11)	C11—C12—C17—C16	−179.70 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···N1	0.96	2.60	2.9346 (15)	101
C19—H19C···N2	0.96	2.61	2.9416 (15)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯N1	0.96	2.60	2.9346 (15)	101
C19—H19C⋯N2	0.96	2.61	2.9416 (15)	101