4-Chloro-N-(3,4,5-trimethoxy-benzyl-idene)aniline.

The title compound, C(16)H(16)ClNO(3), is a Schiff base displaying a trans configuration of the C=N double bond. In the crystal structure, inter-molecular C-H⋯N and bifurcated C-H⋯(O,O) hydrogen bonds are observed.

Related literature

For backgroud and related structures, see: Khalaji et al. (2008 ▶); Khalaji & Harrison (2008 ▶); Khalaji et al. (2007 ▶); Zhang (2008 ▶); Akkurt et al. (2008 ▶); Kashmiri et al. (2008 ▶); Ren & Jian (2008 ▶). For the synthesis of the title compound, see: Khalaji & Ng (2008 ▶).

Experimental

Crystal data

C16H16ClNO3

M = 305.75

Monoclinic,

a = 7.2012 (2) Å

b = 8.18700 (10) Å

c = 12.9734 (3) Å

β = 105.050 (2)°

V = 738.63 (3) Å3

Z = 2

Cu Kα radiation

μ = 2.37 mm−1

T = 120 K

0.22 × 0.20 × 0.11 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: numerical [Clark & Reid (1995 ▶) in CrysAlis RED (Oxford Diffraction, 2008 ▶)] T min = 0.680, T max = 0.809

5670 measured reflections

2225 independent reflections

2039 reflections with I > 3σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.109

S = 1.93

2225 reflections

189 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 915 Friedel pairs

Flack parameter: 0.06 (2)

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2007 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000300/bt2844sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000300/bt2844Isup2.hkl

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

C16H16ClNO3	F(000) = 320
Mr = 305.75	Dx = 1.379 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 4239 reflections
a = 7.2012 (2) Å	θ = 3.5–62.6°
b = 8.1870 (1) Å	µ = 2.37 mm−1
c = 12.9734 (3) Å	T = 120 K
β = 105.050 (2)°	Prism, colorless
V = 738.63 (3) Å3	0.22 × 0.20 × 0.11 mm
Z = 2

Oxford Diffraction Gemini diffractometer with Xcalibur goniometer, Atlas detector and Gemini ultra Cu source	2225 independent reflections
Radiation source: X-ray tube	2039 reflections with I > 3σ(I)
mirror	Rint = 0.048
Detector resolution: 20.7567 pixels mm-1	θmax = 62.7°, θmin = 3.5°
rotation method data acquisition using ω scans	h = −8→7
Absorption correction: numerical [based on the crystal shape, using the method implemented in CrysAlis RED (Oxford Diffraction, 2008) according to Clark & Reid (1995)]	k = −9→9
Tmin = 0.680, Tmax = 0.809	l = −14→14
5670 measured reflections

Refinement on F2	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
wR(F2) = 0.109	(Δ/σ)max = 0.013
S = 1.93	Δρmax = 0.28 e Å−3
2225 reflections	Δρmin = −0.21 e Å−3
189 parameters	Absolute structure: Flack (1983), 915 Friedel pairs
0 restraints	Flack parameter: 0.06 (2)
65 constraints

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
Cl1	0.00790 (13)	0.16442 (1)	0.00937 (6)	0.0366 (3)
O1	1.2823 (3)	0.6425 (3)	0.64185 (15)	0.0252 (7)
O2	1.4726 (3)	0.8288 (3)	0.53638 (16)	0.0255 (7)
O3	1.3717 (3)	0.8527 (3)	0.32476 (16)	0.0298 (8)
N1	0.7360 (4)	0.5116 (4)	0.2085 (2)	0.0261 (10)
C1	1.2081 (4)	0.6506 (4)	0.5342 (2)	0.0199 (9)
C2	1.3141 (5)	0.7435 (4)	0.4792 (2)	0.0220 (10)
C3	1.2528 (5)	0.7593 (4)	0.3685 (3)	0.0226 (11)
C4	1.0855 (4)	0.6828 (4)	0.3111 (2)	0.0239 (10)
C5	0.9789 (5)	0.5918 (4)	0.3668 (2)	0.0212 (10)
C6	1.0392 (5)	0.5747 (4)	0.4767 (2)	0.0226 (11)
C7	0.7985 (5)	0.5127 (4)	0.3104 (2)	0.0226 (10)
C8	0.5578 (5)	0.4334 (4)	0.1638 (2)	0.0240 (10)
C9	0.4039 (4)	0.4350 (4)	0.2092 (2)	0.0250 (11)
C10	0.2330 (5)	0.3568 (4)	0.1612 (2)	0.0263 (11)
C11	0.2161 (5)	0.2724 (4)	0.0662 (2)	0.0273 (11)
C12	0.3676 (5)	0.2727 (4)	0.0172 (3)	0.0324 (12)
C13	0.5356 (5)	0.3535 (5)	0.0654 (2)	0.0315 (12)
C14	1.1767 (5)	0.5531 (5)	0.7017 (3)	0.0370 (13)
C15	1.6479 (5)	0.7425 (5)	0.5441 (3)	0.0319 (12)
C16	1.3098 (5)	0.8853 (5)	0.2132 (3)	0.0366 (14)
H4	1.043968	0.692286	0.234845	0.0286*
H6	0.964788	0.510597	0.51341	0.0271*
H9	0.415976	0.491463	0.275474	0.03*
H10	0.126966	0.360818	0.193233	0.0316*
H12	0.354653	0.217079	−0.049398	0.0389*
H13	0.638975	0.355215	0.031235	0.0378*
H14a	1.230813	0.572264	0.776497	0.0444*
H14b	1.044923	0.588152	0.682085	0.0444*
H14c	1.182975	0.43867	0.686918	0.0444*
H15a	1.753739	0.805308	0.585471	0.0382*
H15b	1.643203	0.638974	0.578074	0.0382*
H15c	1.664554	0.725127	0.473844	0.0382*
H16a	1.401652	0.954863	0.192956	0.0439*
H16b	1.299241	0.784387	0.174383	0.0439*
H16c	1.186828	0.938464	0.197126	0.0439*
H7	0.723679	0.459098	0.351803	0.0271*

	U11	U22	U33	U12	U13	U23
Cl1	0.0321 (4)	0.0363 (4)	0.0337 (4)	−0.0062 (4)	−0.0049 (3)	−0.0031 (4)
O1	0.0277 (12)	0.0274 (12)	0.0184 (10)	−0.0043 (10)	0.0021 (8)	−0.0007 (9)
O2	0.0210 (12)	0.0256 (12)	0.0276 (11)	−0.0031 (9)	0.0023 (9)	−0.0061 (9)
O3	0.0298 (13)	0.0353 (12)	0.0235 (11)	−0.0092 (11)	0.0054 (10)	0.0014 (10)
N1	0.0248 (16)	0.0292 (15)	0.0227 (15)	−0.0020 (12)	0.0032 (12)	−0.0012 (11)
C1	0.0216 (16)	0.0189 (14)	0.0184 (14)	0.0012 (14)	0.0039 (11)	−0.0004 (13)
C2	0.0190 (16)	0.0203 (15)	0.0239 (17)	−0.0012 (13)	0.0007 (13)	−0.0033 (12)
C3	0.0235 (18)	0.0192 (17)	0.0280 (17)	−0.0008 (13)	0.0115 (14)	0.0002 (12)
C4	0.0229 (17)	0.0235 (17)	0.0235 (15)	0.0008 (14)	0.0030 (12)	0.0005 (13)
C5	0.0182 (18)	0.0199 (15)	0.0251 (17)	0.0011 (12)	0.0046 (14)	−0.0007 (12)
C6	0.0239 (19)	0.0209 (17)	0.0227 (17)	0.0018 (13)	0.0057 (13)	0.0015 (12)
C7	0.0211 (17)	0.0200 (16)	0.0251 (17)	−0.0003 (13)	0.0033 (13)	−0.0005 (13)
C8	0.0263 (17)	0.0220 (16)	0.0206 (16)	−0.0015 (15)	0.0007 (13)	−0.0004 (13)
C9	0.0252 (18)	0.0281 (18)	0.0201 (16)	0.0027 (15)	0.0032 (13)	0.0004 (13)
C10	0.0254 (19)	0.0296 (18)	0.0219 (17)	0.0010 (14)	0.0024 (13)	0.0003 (14)
C11	0.034 (2)	0.0230 (16)	0.0191 (16)	0.0008 (14)	−0.0037 (14)	0.0007 (12)
C12	0.032 (2)	0.0353 (19)	0.0270 (18)	0.0025 (16)	0.0020 (15)	−0.0050 (14)
C13	0.032 (2)	0.040 (2)	0.0226 (17)	−0.0018 (16)	0.0080 (14)	−0.0030 (15)
C14	0.035 (2)	0.048 (2)	0.0262 (19)	−0.0060 (18)	0.0048 (15)	0.0083 (16)
C15	0.0185 (18)	0.0334 (18)	0.040 (2)	0.0021 (15)	0.0018 (15)	0.0018 (15)
C16	0.042 (2)	0.043 (2)	0.0260 (18)	−0.0086 (17)	0.0097 (16)	0.0074 (15)

Cl1—C10	2.708 (3)	C7—H7	0.96
Cl1—C11	1.732 (3)	C8—C9	1.384 (5)
Cl1—C12	2.714 (4)	C8—C13	1.406 (5)
O1—C1	1.362 (3)	C9—C10	1.383 (4)
O1—C14	1.423 (5)	C9—H9	0.96
O2—C2	1.379 (4)	C10—C11	1.390 (5)
O2—C15	1.427 (4)	C10—H10	0.96
O3—C3	1.375 (4)	C11—C12	1.398 (6)
O3—C16	1.424 (4)	C12—C13	1.378 (5)
N1—C7	1.282 (4)	C12—H12	0.96
N1—C8	1.417 (4)	C13—H13	0.96
C1—C2	1.397 (5)	C14—H14a	0.96
C1—C6	1.397 (4)	C14—H14b	0.96
C2—C3	1.395 (4)	C14—H14c	0.96
C3—C4	1.390 (4)	C15—H15a	0.96
C4—C5	1.398 (5)	C15—H15b	0.96
C4—H4	0.96	C15—H15c	0.96
C5—C6	1.385 (4)	C16—H16a	0.96
C5—C7	1.466 (4)	C16—H16b	0.96
C6—H6	0.96	C16—H16c	0.96
C10—Cl1—C12	52.95 (11)	C8—C9—H9	119.2976
C1—O1—C14	117.5 (2)	C10—C9—H9	119.2983
C2—O2—C15	112.4 (3)	C9—C10—C11	119.5 (3)
C3—O3—C16	117.3 (2)	C9—C10—H10	120.2657
C7—N1—C8	117.6 (3)	C11—C10—H10	120.265
O1—C1—C2	115.4 (3)	C10—C11—C12	120.2 (3)
O1—C1—C6	125.5 (3)	C11—C12—C13	119.5 (3)
C2—C1—C6	119.0 (3)	C11—C12—H12	120.2721
O2—C2—C1	119.1 (3)	C13—C12—H12	120.2719
O2—C2—C3	120.3 (3)	C8—C13—C12	120.9 (4)
C1—C2—C3	120.5 (3)	C8—C13—H13	119.5347
O3—C3—C2	114.3 (3)	C12—C13—H13	119.5353
O3—C3—C4	125.1 (3)	O1—C14—H14a	109.4713
C2—C3—C4	120.5 (3)	O1—C14—H14b	109.4711
C3—C4—C5	118.6 (3)	O1—C14—H14c	109.4713
C3—C4—H4	120.6757	H14a—C14—H14b	109.4712
C5—C4—H4	120.6756	H14a—C14—H14c	109.4714
C4—C5—C6	121.2 (3)	H14b—C14—H14c	109.471
C4—C5—C7	120.8 (3)	O2—C15—H15a	109.4714
C6—C5—C7	118.0 (3)	O2—C15—H15b	109.4711
C1—C6—C5	120.1 (3)	O2—C15—H15c	109.4715
C1—C6—H6	119.9695	H15a—C15—H15b	109.4705
C5—C6—H6	119.9698	H15a—C15—H15c	109.4714
N1—C7—C5	123.1 (3)	H15b—C15—H15c	109.4714
N1—C7—H7	118.4336	O3—C16—H16a	109.4709
C5—C7—H7	118.4335	O3—C16—H16b	109.4714
N1—C8—C9	124.2 (3)	O3—C16—H16c	109.4711
N1—C8—C13	117.3 (3)	H16a—C16—H16b	109.4712
C9—C8—C13	118.4 (3)	H16a—C16—H16c	109.4712
C8—C9—C10	121.4 (3)	H16b—C16—H16c	109.4715

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.96	2.59	3.177 (4)	119
C7—H7···O2i	0.96	2.51	3.471 (4)	178
C12—H12···N1ii	0.96	2.61	3.545 (5)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.96	2.59	3.177 (4)	119
C7—H7⋯O2i	0.96	2.51	3.471 (4)	178
C12—H12⋯N1ii	0.96	2.61	3.545 (5)	164

Symmetry codes: (i) ; (ii) .