4-Chloro-N-[4-(diethyl-amino)benzyl-idene]aniline.

The asymmetric unit of the title compound, C(17)H(19)ClN(2), contains two independent mol-ecules which differ by a 180° flip in the orientation of the 4-chloro-aniline unit with respect to the diethyl-amino-benzyl-idene unit [N=C-C-C = 10.0 (3) and -170.6 (2)°]. The dihedral angles between the two aromatic rings are 64.0 (1) and 66.5 (1)° in the two independent mol-ecules.

Related literature

For general background to Schiff base compounds in coordin­ation chemistry, see: Yu et al. (2007 ▶). For a related structure, see: You et al. (2004 ▶).

Experimental

Crystal data

C17H19ClN2

M = 286.79

Monoclinic,

a = 20.153 (2) Å

b = 8.7434 (7) Å

c = 20.1446 (19) Å

β = 118.444 (2)°

V = 3121.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.25 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.958

22416 measured reflections

5494 independent reflections

4266 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.07

5494 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000125X/ci2995sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000125X/ci2995Isup2.hkl

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

C17H19ClN2	F(000) = 1216
Mr = 286.79	Dx = 1.221 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1362 reflections
a = 20.153 (2) Å	θ = 2.4–21.4°
b = 8.7434 (7) Å	µ = 0.24 mm−1
c = 20.1446 (19) Å	T = 293 K
β = 118.444 (2)°	Block, light yellow
V = 3121.0 (5) Å3	0.25 × 0.22 × 0.18 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	5494 independent reflections
Radiation source: fine-focus sealed tube	4266 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.942, Tmax = 0.958	k = −10→10
22416 measured reflections	l = −23→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0646P)2 + 0.3803P] where P = (Fo2 + 2Fc2)/3
5494 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.34 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
Cl2	0.85148 (4)	−0.53996 (7)	0.76082 (4)	0.0984 (2)
Cl1	0.64613 (4)	1.53729 (7)	0.41511 (4)	0.1002 (2)
N2	0.59641 (9)	1.07076 (17)	0.18309 (8)	0.0637 (4)
N3	0.90381 (8)	0.57265 (16)	0.41592 (8)	0.0619 (4)
C7	0.58844 (9)	0.83306 (19)	0.07682 (9)	0.0562 (4)
H7A	0.5731	0.9299	0.0560	0.067*
C5	0.60395 (9)	0.56348 (18)	0.05880 (9)	0.0530 (4)
C23	0.91666 (10)	0.30238 (19)	0.44633 (10)	0.0581 (4)
H23A	0.9321	0.2837	0.4103	0.070*
C6	0.58355 (9)	0.71363 (19)	0.03069 (9)	0.0567 (4)
H6A	0.5664	0.7319	−0.0204	0.068*
N4	0.90566 (9)	−0.05533 (17)	0.58706 (9)	0.0659 (4)
C24	0.91207 (10)	0.18314 (19)	0.48779 (9)	0.0583 (4)
H24A	0.9252	0.0855	0.4798	0.070*
C22	0.89856 (9)	0.45309 (18)	0.45679 (9)	0.0522 (4)
C28	0.88144 (10)	0.0793 (2)	0.58554 (9)	0.0593 (4)
H28A	0.8577	0.0992	0.6145	0.071*
N1	0.59608 (9)	0.44244 (16)	0.01260 (9)	0.0627 (4)
C11	0.62332 (9)	0.9374 (2)	0.20476 (10)	0.0568 (4)
H11A	0.6495	0.9186	0.2564	0.068*
C25	0.88817 (9)	0.20400 (19)	0.54188 (9)	0.0559 (4)
C27	0.87455 (10)	0.47377 (19)	0.51171 (10)	0.0585 (4)
H27A	0.8619	0.5712	0.5205	0.070*
C8	0.61580 (9)	0.81317 (19)	0.15426 (9)	0.0539 (4)
C10	0.63215 (10)	0.5445 (2)	0.13724 (10)	0.0612 (4)
H10A	0.6474	0.4480	0.1585	0.073*
C12	0.61080 (10)	1.18249 (19)	0.23937 (9)	0.0564 (4)
C26	0.86968 (10)	0.3532 (2)	0.55194 (10)	0.0609 (4)
H26A	0.8534	0.3708	0.5874	0.073*
C29	0.89088 (10)	−0.16858 (19)	0.62846 (9)	0.0571 (4)
C9	0.63739 (10)	0.6647 (2)	0.18232 (10)	0.0609 (4)
H9A	0.6560	0.6476	0.2337	0.073*
C15	0.63294 (11)	1.4018 (2)	0.34658 (11)	0.0645 (5)
C34	0.95037 (10)	−0.25322 (19)	0.68199 (11)	0.0628 (5)
H34A	0.9991	−0.2339	0.6903	0.075*
C32	0.86616 (10)	−0.3967 (2)	0.70916 (10)	0.0625 (4)
C17	0.68257 (10)	1.2175 (2)	0.29554 (11)	0.0669 (5)
H17A	0.7238	1.1663	0.2972	0.080*
C16	0.69412 (11)	1.3272 (2)	0.34924 (12)	0.0704 (5)
H16A	0.7427	1.3504	0.3867	0.084*
C14	0.56102 (11)	1.3704 (2)	0.29018 (12)	0.0730 (5)
H14A	0.5199	1.4220	0.2885	0.088*
C33	0.93858 (10)	−0.3652 (2)	0.72303 (11)	0.0660 (5)
H33A	0.9792	−0.4194	0.7598	0.079*
C2	0.61471 (11)	0.2868 (2)	0.04203 (12)	0.0709 (5)
H2B	0.5867	0.2156	0.0012	0.085*
H2C	0.5982	0.2725	0.0796	0.085*
C13	0.55034 (10)	1.2624 (2)	0.23647 (11)	0.0674 (5)
H13A	0.5019	1.2430	0.1977	0.081*
C30	0.81858 (10)	−0.2037 (2)	0.61520 (11)	0.0696 (5)
H30A	0.7778	−0.1496	0.5787	0.084*
C4	0.57312 (12)	0.4657 (2)	−0.06713 (11)	0.0720 (5)
H4B	0.5317	0.5382	−0.0878	0.086*
H4C	0.5546	0.3696	−0.0936	0.086*
C19	0.88835 (11)	0.72995 (19)	0.42921 (12)	0.0699 (5)
H19A	0.9164	0.7989	0.4141	0.084*
H19B	0.9068	0.7438	0.4829	0.084*
C21	0.92008 (12)	0.5464 (2)	0.35369 (12)	0.0730 (5)
H21A	0.9627	0.4772	0.3705	0.088*
H21B	0.9347	0.6427	0.3405	0.088*
C31	0.80608 (11)	−0.3174 (2)	0.65510 (12)	0.0714 (5)
H31A	0.7572	−0.3402	0.6455	0.086*
C20	0.85481 (14)	0.4803 (3)	0.28411 (12)	0.0883 (7)
H20A	0.8693	0.4669	0.2455	0.132*
H20B	0.8126	0.5488	0.2664	0.132*
H20C	0.8410	0.3832	0.2962	0.132*
C3	0.63511 (14)	0.5236 (3)	−0.08195 (13)	0.0882 (7)
H3A	0.6160	0.5365	−0.1353	0.132*
H3B	0.6758	0.4512	−0.0630	0.132*
H3C	0.6531	0.6201	−0.0570	0.132*
C18	0.80592 (12)	0.7741 (2)	0.38778 (15)	0.0933 (7)
H18A	0.8003	0.8782	0.3995	0.140*
H18B	0.7776	0.7081	0.4031	0.140*
H18C	0.7874	0.7642	0.3344	0.140*
C1	0.69744 (13)	0.2482 (3)	0.07706 (15)	0.0991 (8)
H1A	0.7053	0.1449	0.0954	0.149*
H1B	0.7257	0.3167	0.1182	0.149*
H1C	0.7141	0.2584	0.0398	0.149*

	U11	U22	U33	U12	U13	U23
Cl2	0.1067 (5)	0.0772 (4)	0.1268 (5)	−0.0034 (3)	0.0682 (4)	0.0204 (3)
Cl1	0.1127 (5)	0.0755 (4)	0.1135 (5)	−0.0022 (3)	0.0549 (4)	−0.0307 (3)
N2	0.0695 (9)	0.0627 (9)	0.0590 (9)	0.0001 (7)	0.0307 (8)	0.0018 (7)
N3	0.0668 (9)	0.0526 (8)	0.0632 (9)	−0.0015 (6)	0.0283 (8)	−0.0032 (7)
C7	0.0584 (10)	0.0542 (9)	0.0571 (10)	0.0021 (7)	0.0285 (8)	0.0076 (7)
C5	0.0499 (9)	0.0542 (9)	0.0561 (9)	−0.0034 (7)	0.0263 (8)	0.0027 (7)
C23	0.0627 (10)	0.0593 (10)	0.0541 (9)	0.0065 (8)	0.0292 (8)	−0.0027 (8)
C6	0.0590 (10)	0.0612 (10)	0.0489 (9)	−0.0001 (7)	0.0250 (8)	0.0058 (8)
N4	0.0775 (10)	0.0637 (9)	0.0628 (9)	0.0058 (7)	0.0386 (8)	−0.0002 (7)
C24	0.0643 (10)	0.0539 (9)	0.0556 (10)	0.0077 (7)	0.0279 (8)	−0.0038 (7)
C22	0.0468 (8)	0.0536 (9)	0.0462 (9)	−0.0011 (7)	0.0140 (7)	−0.0058 (7)
C28	0.0617 (10)	0.0649 (11)	0.0503 (9)	0.0030 (8)	0.0258 (8)	−0.0044 (8)
N1	0.0700 (9)	0.0542 (8)	0.0627 (9)	−0.0029 (6)	0.0306 (8)	−0.0007 (7)
C11	0.0531 (9)	0.0658 (11)	0.0538 (10)	−0.0010 (8)	0.0275 (8)	0.0034 (8)
C25	0.0561 (9)	0.0593 (10)	0.0469 (9)	0.0017 (7)	0.0202 (8)	−0.0042 (7)
C27	0.0618 (10)	0.0533 (9)	0.0547 (10)	0.0029 (7)	0.0231 (8)	−0.0117 (8)
C8	0.0506 (9)	0.0603 (10)	0.0535 (9)	−0.0019 (7)	0.0269 (8)	0.0015 (7)
C10	0.0674 (11)	0.0572 (10)	0.0583 (10)	0.0029 (8)	0.0295 (9)	0.0111 (8)
C12	0.0627 (10)	0.0536 (9)	0.0563 (10)	−0.0012 (7)	0.0311 (8)	0.0073 (7)
C26	0.0655 (10)	0.0649 (11)	0.0511 (9)	0.0028 (8)	0.0268 (8)	−0.0111 (8)
C29	0.0644 (10)	0.0549 (9)	0.0543 (9)	0.0026 (8)	0.0302 (8)	−0.0080 (7)
C9	0.0656 (10)	0.0670 (11)	0.0509 (9)	0.0011 (8)	0.0285 (8)	0.0089 (8)
C15	0.0738 (12)	0.0501 (9)	0.0743 (12)	−0.0026 (8)	0.0390 (10)	−0.0017 (8)
C34	0.0560 (10)	0.0571 (10)	0.0753 (12)	0.0021 (8)	0.0313 (9)	−0.0027 (9)
C32	0.0703 (11)	0.0512 (9)	0.0708 (11)	−0.0025 (8)	0.0376 (10)	−0.0052 (8)
C17	0.0571 (10)	0.0704 (11)	0.0779 (12)	0.0002 (8)	0.0358 (10)	−0.0042 (10)
C16	0.0578 (10)	0.0689 (12)	0.0783 (13)	−0.0053 (8)	0.0275 (10)	−0.0101 (10)
C14	0.0632 (11)	0.0575 (11)	0.0990 (15)	0.0086 (8)	0.0391 (11)	0.0011 (10)
C33	0.0603 (10)	0.0568 (10)	0.0727 (12)	0.0047 (8)	0.0250 (9)	0.0030 (9)
C2	0.0719 (12)	0.0535 (10)	0.0827 (13)	−0.0025 (8)	0.0332 (10)	0.0006 (9)
C13	0.0558 (10)	0.0578 (10)	0.0772 (12)	0.0040 (8)	0.0225 (9)	0.0035 (9)
C30	0.0580 (11)	0.0717 (12)	0.0693 (12)	0.0081 (9)	0.0223 (9)	0.0018 (9)
C4	0.0848 (13)	0.0649 (11)	0.0613 (11)	−0.0090 (9)	0.0307 (10)	−0.0107 (9)
C19	0.0666 (11)	0.0515 (10)	0.0813 (13)	−0.0012 (8)	0.0267 (10)	−0.0028 (9)
C21	0.0829 (13)	0.0669 (12)	0.0791 (13)	−0.0034 (9)	0.0465 (11)	0.0061 (10)
C31	0.0574 (10)	0.0690 (12)	0.0881 (14)	−0.0030 (9)	0.0349 (10)	−0.0062 (10)
C20	0.1086 (18)	0.0907 (15)	0.0606 (12)	0.0092 (12)	0.0362 (12)	0.0058 (11)
C3	0.1165 (19)	0.0832 (14)	0.0860 (16)	0.0070 (13)	0.0652 (15)	−0.0008 (12)
C18	0.0720 (13)	0.0778 (14)	0.1146 (18)	0.0135 (10)	0.0319 (13)	0.0052 (13)
C1	0.0780 (15)	0.0875 (16)	0.1166 (19)	0.0177 (12)	0.0342 (14)	0.0075 (14)

Cl2—C32	1.7415 (19)	C15—C16	1.373 (3)
Cl1—C15	1.7407 (19)	C15—C14	1.378 (3)
N2—C11	1.273 (2)	C34—C33	1.373 (2)
N2—C12	1.418 (2)	C34—H34A	0.93
N3—C22	1.366 (2)	C32—C31	1.370 (3)
N3—C21	1.457 (2)	C32—C33	1.377 (2)
N3—C19	1.463 (2)	C17—C16	1.380 (3)
C7—C6	1.370 (2)	C17—H17A	0.93
C7—C8	1.396 (2)	C16—H16A	0.93
C7—H7A	0.93	C14—C13	1.373 (3)
C5—N1	1.368 (2)	C14—H14A	0.93
C5—C6	1.411 (2)	C33—H33A	0.93
C5—C10	1.411 (2)	C2—C1	1.507 (3)
C23—C24	1.366 (2)	C2—H2B	0.97
C23—C22	1.410 (2)	C2—H2C	0.97
C23—H23A	0.93	C13—H13A	0.93
C6—H6A	0.93	C30—C31	1.375 (3)
N4—C28	1.269 (2)	C30—H30A	0.93
N4—C29	1.415 (2)	C4—C3	1.504 (3)
C24—C25	1.397 (2)	C4—H4B	0.97
C24—H24A	0.93	C4—H4C	0.97
C22—C27	1.414 (2)	C19—C18	1.511 (3)
C28—C25	1.447 (2)	C19—H19A	0.97
C28—H28A	0.93	C19—H19B	0.97
N1—C4	1.459 (2)	C21—C20	1.507 (3)
N1—C2	1.460 (2)	C21—H21A	0.97
C11—C8	1.446 (2)	C21—H21B	0.97
C11—H11A	0.93	C31—H31A	0.93
C25—C26	1.398 (2)	C20—H20A	0.96
C27—C26	1.361 (2)	C20—H20B	0.96
C27—H27A	0.93	C20—H20C	0.96
C8—C9	1.400 (2)	C3—H3A	0.96
C10—C9	1.360 (2)	C3—H3B	0.96
C10—H10A	0.93	C3—H3C	0.96
C12—C17	1.381 (3)	C18—H18A	0.96
C12—C13	1.381 (2)	C18—H18B	0.96
C26—H26A	0.93	C18—H18C	0.96
C29—C34	1.384 (2)	C1—H1A	0.96
C29—C30	1.385 (3)	C1—H1B	0.96
C9—H9A	0.93	C1—H1C	0.96
C11—N2—C12	117.75 (15)	C12—C17—H17A	119.5
C22—N3—C21	120.79 (14)	C15—C16—C17	119.11 (18)
C22—N3—C19	121.66 (16)	C15—C16—H16A	120.4
C21—N3—C19	117.42 (16)	C17—C16—H16A	120.4
C6—C7—C8	121.71 (15)	C13—C14—C15	119.69 (17)
C6—C7—H7A	119.1	C13—C14—H14A	120.2
C8—C7—H7A	119.1	C15—C14—H14A	120.2
N1—C5—C6	121.97 (15)	C34—C33—C32	119.40 (17)
N1—C5—C10	121.69 (15)	C34—C33—H33A	120.3
C6—C5—C10	116.33 (15)	C32—C33—H33A	120.3
C24—C23—C22	121.62 (16)	N1—C2—C1	114.34 (17)
C24—C23—H23A	119.2	N1—C2—H2B	108.7
C22—C23—H23A	119.2	C1—C2—H2B	108.7
C7—C6—C5	121.59 (15)	N1—C2—H2C	108.7
C7—C6—H6A	119.2	C1—C2—H2C	108.7
C5—C6—H6A	119.2	H2B—C2—H2C	107.6
C28—N4—C29	118.48 (15)	C14—C13—C12	120.69 (17)
C23—C24—C25	121.73 (15)	C14—C13—H13A	119.7
C23—C24—H24A	119.1	C12—C13—H13A	119.7
C25—C24—H24A	119.1	C31—C30—C29	121.10 (17)
N3—C22—C23	121.71 (16)	C31—C30—H30A	119.4
N3—C22—C27	121.83 (15)	C29—C30—H30A	119.5
C23—C22—C27	116.47 (16)	N1—C4—C3	114.07 (18)
N4—C28—C25	124.55 (17)	N1—C4—H4B	108.7
N4—C28—H28A	117.7	C3—C4—H4B	108.7
C25—C28—H28A	117.7	N1—C4—H4C	108.7
C5—N1—C4	120.95 (14)	C3—C4—H4C	108.7
C5—N1—C2	121.38 (15)	H4B—C4—H4C	107.6
C4—N1—C2	117.57 (15)	N3—C19—C18	114.41 (16)
N2—C11—C8	124.21 (16)	N3—C19—H19A	108.7
N2—C11—H11A	117.9	C18—C19—H19A	108.7
C8—C11—H11A	117.9	N3—C19—H19B	108.7
C24—C25—C26	116.71 (16)	C18—C19—H19B	108.7
C24—C25—C28	122.85 (15)	H19A—C19—H19B	107.6
C26—C25—C28	120.43 (16)	N3—C21—C20	113.96 (18)
C26—C27—C22	121.02 (15)	N3—C21—H21A	108.8
C26—C27—H27A	119.5	C20—C21—H21A	108.8
C22—C27—H27A	119.5	N3—C21—H21B	108.8
C7—C8—C9	116.62 (16)	C20—C21—H21B	108.8
C7—C8—C11	123.10 (15)	H21A—C21—H21B	107.7
C9—C8—C11	120.27 (15)	C32—C31—C30	119.47 (18)
C9—C10—C5	121.25 (16)	C32—C31—H31A	120.3
C9—C10—H10A	119.4	C30—C31—H31A	120.3
C5—C10—H10A	119.4	C21—C20—H20A	109.5
C17—C12—C13	118.74 (17)	C21—C20—H20B	109.5
C17—C12—N2	122.91 (16)	H20A—C20—H20B	109.5
C13—C12—N2	118.32 (16)	C21—C20—H20C	109.5
C27—C26—C25	122.45 (17)	H20A—C20—H20C	109.5
C27—C26—H26A	118.8	H20B—C20—H20C	109.5
C25—C26—H26A	118.8	C4—C3—H3A	109.5
C34—C29—C30	118.21 (17)	C4—C3—H3B	109.5
C34—C29—N4	119.08 (16)	H3A—C3—H3B	109.5
C30—C29—N4	122.63 (16)	C4—C3—H3C	109.5
C10—C9—C8	122.46 (16)	H3A—C3—H3C	109.5
C10—C9—H9A	118.8	H3B—C3—H3C	109.5
C8—C9—H9A	118.8	C19—C18—H18A	109.5
C16—C15—C14	120.64 (18)	C19—C18—H18B	109.5
C16—C15—Cl1	119.81 (15)	H18A—C18—H18B	109.5
C14—C15—Cl1	119.54 (15)	C19—C18—H18C	109.5
C33—C34—C29	121.09 (17)	H18A—C18—H18C	109.5
C33—C34—H34A	119.5	H18B—C18—H18C	109.5
C29—C34—H34A	119.5	C2—C1—H1A	109.5
C31—C32—C33	120.69 (18)	C2—C1—H1B	109.5
C31—C32—Cl2	120.11 (15)	H1A—C1—H1B	109.5
C33—C32—Cl2	119.20 (14)	C2—C1—H1C	109.5
C16—C17—C12	121.07 (17)	H1A—C1—H1C	109.5
C16—C17—H17A	119.5	H1B—C1—H1C	109.5