(Z)-N-(2,6-Diiso-propyl-phen-yl)-4-nitro-benzimidoyl chloride.

In the title compound, C19H21ClN2O2, the aromatic rings are approximately perpendicular to each other, subtending a dihedral angle of 87.7 (1)°. In the crystal, the 4-nitro-phenyl groups of pairs of neighbouring mol-ecules are parallel and oriented head-to-tail with a ring centroid-centroid distance of 3.9247 (12) Å, leading to a π-π inter-action between the pair. The faces of each phenyl ring of the 2,6-diiso-propyl-phenyl group inter-act with two different groups, viz. a chloro group of an adjacent mol-ecule on one side and the edge of the 4-nitro-phenyl ring of a second mol-ecule on the other side.

Related literature

For the synthesis and applications of imidoyl chlorides, see: Pelter et al. (1975 ▶); Manley & Bilodeau (2002 ▶); Cunico & Pandey (2005 ▶); Raussukana et al. (2006 ▶); Zheng & Alper (2008 ▶); Kuszpit et al. (2011 ▶). For a related structure of an imidoyl chloride, see: Seidelmann et al. (1998 ▶).

Experimental

Crystal data

C19H21ClN2O2

M = 344.83

Triclinic,

a = 8.2988 (4) Å

b = 10.4667 (3) Å

c = 10.9665 (3) Å

α = 75.568 (2)°

β = 85.411 (2)°

γ = 74.145 (2)°

V = 887.33 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 150 K

0.35 × 0.20 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.924, T max = 0.967

6021 measured reflections

4232 independent reflections

3108 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.173

S = 1.06

4232 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.41 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP99 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813020862/is5293sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020862/is5293Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020862/is5293Isup3.cml

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

C19H21ClN2O2	Z = 2
Mr = 344.83	F(000) = 364
Triclinic, P1	Dx = 1.291 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2988 (4) Å	Cell parameters from 3108 reflections
b = 10.4667 (3) Å	θ = 2.8–28.3°
c = 10.9665 (3) Å	µ = 0.23 mm−1
α = 75.568 (2)°	T = 150 K
β = 85.411 (2)°	Block, yellow
γ = 74.145 (2)°	0.35 × 0.20 × 0.15 mm
V = 887.33 (6) Å3

Nonius KappaCCD diffractometer	4232 independent reflections
Radiation source: fine-focus sealed tube	3108 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scans	θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −11→10
Tmin = 0.924, Tmax = 0.967	k = −13→13
6021 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)] = 0.062	H-atom parameters constrained
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.0765P)2 + 0.589P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.005
4232 reflections	Δρmax = 0.32 e Å−3
222 parameters	Δρmin = −0.41 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.094 (10)

Experimental. 1H (400 MHz; CDCl3) δ: 8.25 (2 H, d, J = 8.4 Hz), 8.17 (2 H, d, J = 8.4 Hz), 7.05–7.12 (2 H, m), 6.97–7.04 (1 H, m), 2.66 (2 H, app. sept, J = 6.9 Hz), 1.11 (6 H, d, J = 6.6 Hz), 1.05 (6 H, d, J = 6.6 Hz) – the two 6 H doublets coalesced at 50 °C; 13C (125 MHz; CDCl3) δ: 149.9 (s), 143.4 (s), 141.8 (s), 140.1 (s), 136.3 (s), 130.3 (d), 125.5 (d), 123.7 (d), 123.3 (d), 28.8 (d), 23.3 (q), 22.8 (q); vmax (thin film/cm-1): 3017, 2966, 2929, 2871, 1662, 1605, 1529, 1349, 1216, 1168, 1461.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.2830 (3)	0.0882 (2)	1.0555 (2)	0.0319 (5)
C2	0.2874 (3)	0.0814 (2)	0.9309 (2)	0.0343 (5)
H2	0.2496	0.0132	0.9075	0.041*
C3	0.3483 (3)	0.1763 (2)	0.8410 (2)	0.0299 (5)
H3	0.3551	0.1720	0.7552	0.036*
C4	0.3996 (2)	0.27816 (19)	0.87595 (19)	0.0234 (4)
C5	0.3944 (3)	0.2816 (2)	1.0028 (2)	0.0277 (5)
H5	0.4310	0.3500	1.0269	0.033*
C6	0.3360 (3)	0.1857 (2)	1.0938 (2)	0.0320 (5)
H6	0.3326	0.1873	1.1803	0.038*
C7	0.4587 (3)	0.3856 (2)	0.78235 (18)	0.0237 (4)
C8	0.5521 (3)	0.5859 (2)	0.72503 (18)	0.0239 (4)
C9	0.7254 (3)	0.5618 (2)	0.70425 (19)	0.0259 (4)
C10	0.7851 (3)	0.6667 (2)	0.6259 (2)	0.0306 (5)
H10	0.9022	0.6527	0.6104	0.037*
C11	0.6771 (3)	0.7907 (2)	0.5702 (2)	0.0317 (5)
H11	0.7201	0.8614	0.5180	0.038*
C12	0.5055 (3)	0.8114 (2)	0.5911 (2)	0.0306 (5)
H12	0.4321	0.8961	0.5513	0.037*
C13	0.4386 (3)	0.7111 (2)	0.6689 (2)	0.0267 (5)
C14	0.8468 (3)	0.4269 (2)	0.7645 (2)	0.0307 (5)
H14	0.7792	0.3633	0.8100	0.037*
C15	0.9545 (3)	0.3613 (3)	0.6651 (3)	0.0427 (6)
H15A	0.8819	0.3544	0.6022	0.064*
H15B	1.0214	0.2697	0.7057	0.064*
H15C	1.0293	0.4178	0.6239	0.064*
C16	0.9550 (3)	0.4460 (3)	0.8613 (2)	0.0406 (6)
H16A	1.0282	0.5032	0.8185	0.061*
H16B	1.0235	0.3566	0.9054	0.061*
H16C	0.8827	0.4905	0.9222	0.061*
C17	0.2510 (3)	0.7304 (2)	0.6917 (2)	0.0308 (5)
H17	0.2250	0.6450	0.6838	0.037*
C18	0.2005 (3)	0.7468 (3)	0.8252 (3)	0.0446 (6)
H18A	0.2680	0.6693	0.8861	0.067*
H18B	0.0816	0.7497	0.8397	0.067*
H18C	0.2195	0.8320	0.8353	0.067*
C19	0.1440 (3)	0.8492 (3)	0.5950 (3)	0.0438 (6)
H19A	0.1614	0.9356	0.6032	0.066*
H19B	0.0255	0.8510	0.6101	0.066*
H19C	0.1766	0.8370	0.5099	0.066*
N1	0.2200 (3)	−0.0141 (2)	1.1512 (2)	0.0457 (6)
N2	0.4892 (2)	0.48451 (17)	0.81255 (16)	0.0246 (4)
O1	0.1607 (3)	−0.0925 (2)	1.1148 (2)	0.0716 (7)
O2	0.2325 (3)	−0.0162 (2)	1.2616 (2)	0.0651 (6)
Cl1	0.48157 (10)	0.36574 (7)	0.62743 (5)	0.0461 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0304 (11)	0.0202 (10)	0.0391 (12)	−0.0059 (8)	0.0081 (9)	0.0008 (9)
C2	0.0350 (12)	0.0224 (10)	0.0473 (14)	−0.0115 (9)	0.0001 (10)	−0.0074 (9)
C3	0.0334 (11)	0.0270 (11)	0.0312 (11)	−0.0100 (9)	0.0017 (9)	−0.0085 (9)
C4	0.0235 (10)	0.0192 (9)	0.0265 (10)	−0.0061 (7)	0.0001 (8)	−0.0031 (8)
C5	0.0318 (11)	0.0257 (10)	0.0269 (10)	−0.0105 (8)	0.0008 (9)	−0.0056 (8)
C6	0.0360 (12)	0.0272 (11)	0.0284 (11)	−0.0063 (9)	0.0046 (9)	−0.0023 (9)
C7	0.0267 (10)	0.0229 (9)	0.0205 (9)	−0.0056 (8)	−0.0003 (8)	−0.0043 (7)
C8	0.0308 (11)	0.0219 (9)	0.0210 (9)	−0.0102 (8)	0.0014 (8)	−0.0056 (7)
C9	0.0302 (11)	0.0233 (10)	0.0249 (10)	−0.0092 (8)	0.0009 (8)	−0.0050 (8)
C10	0.0328 (11)	0.0293 (11)	0.0304 (11)	−0.0125 (9)	0.0025 (9)	−0.0045 (9)
C11	0.0396 (12)	0.0267 (11)	0.0296 (11)	−0.0154 (9)	0.0027 (9)	−0.0017 (8)
C12	0.0359 (12)	0.0241 (10)	0.0296 (11)	−0.0086 (9)	−0.0027 (9)	−0.0010 (8)
C13	0.0312 (11)	0.0247 (10)	0.0260 (10)	−0.0095 (8)	0.0000 (8)	−0.0070 (8)
C14	0.0301 (11)	0.0264 (11)	0.0326 (11)	−0.0076 (9)	0.0018 (9)	−0.0018 (9)
C15	0.0432 (14)	0.0384 (13)	0.0435 (14)	−0.0016 (11)	−0.0010 (11)	−0.0143 (11)
C16	0.0391 (13)	0.0400 (13)	0.0367 (13)	−0.0010 (10)	−0.0049 (11)	−0.0070 (10)
C17	0.0302 (11)	0.0239 (10)	0.0377 (12)	−0.0081 (8)	−0.0002 (9)	−0.0051 (9)
C18	0.0389 (14)	0.0480 (15)	0.0462 (15)	−0.0086 (11)	0.0087 (11)	−0.0156 (12)
C19	0.0318 (12)	0.0367 (13)	0.0554 (16)	−0.0076 (10)	−0.0063 (11)	0.0028 (11)
N1	0.0472 (13)	0.0264 (10)	0.0566 (15)	−0.0112 (9)	0.0153 (11)	−0.0006 (10)
N2	0.0272 (9)	0.0228 (8)	0.0239 (8)	−0.0092 (7)	0.0009 (7)	−0.0035 (7)
O1	0.0921 (18)	0.0478 (12)	0.0828 (17)	−0.0473 (12)	0.0134 (14)	−0.0024 (11)
O2	0.0942 (17)	0.0485 (12)	0.0469 (12)	−0.0290 (12)	0.0254 (12)	0.0019 (9)
Cl1	0.0793 (5)	0.0479 (4)	0.0234 (3)	−0.0365 (3)	0.0067 (3)	−0.0110 (2)

C1—C6	1.379 (3)	C12—C13	1.391 (3)
C1—C2	1.382 (3)	C12—H12	0.9500
C1—N1	1.477 (3)	C13—C17	1.522 (3)
C2—C3	1.386 (3)	C14—C16	1.526 (3)
C2—H2	0.9500	C14—C15	1.529 (3)
C3—C4	1.393 (3)	C14—H14	1.0000
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.397 (3)	C15—H15B	0.9800
C4—C7	1.485 (3)	C15—H15C	0.9800
C5—C6	1.388 (3)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
C7—N2	1.254 (3)	C17—C18	1.529 (4)
C7—Cl1	1.752 (2)	C17—C19	1.533 (3)
C8—C9	1.400 (3)	C17—H17	1.0000
C8—C13	1.414 (3)	C18—H18A	0.9800
C8—N2	1.427 (3)	C18—H18B	0.9800
C9—C10	1.396 (3)	C18—H18C	0.9800
C9—C14	1.520 (3)	C19—H19A	0.9800
C10—C11	1.385 (3)	C19—H19B	0.9800
C10—H10	0.9500	C19—H19C	0.9800
C11—C12	1.390 (3)	N1—O2	1.218 (3)
C11—H11	0.9500	N1—O1	1.221 (3)
C6—C1—C2	122.8 (2)	C9—C14—C15	111.36 (19)
C6—C1—N1	118.8 (2)	C16—C14—C15	111.3 (2)
C2—C1—N1	118.4 (2)	C9—C14—H14	107.7
C1—C2—C3	118.5 (2)	C16—C14—H14	107.7
C1—C2—H2	120.7	C15—C14—H14	107.7
C3—C2—H2	120.7	C14—C15—H15A	109.5
C2—C3—C4	120.3 (2)	C14—C15—H15B	109.5
C2—C3—H3	119.9	H15A—C15—H15B	109.5
C4—C3—H3	119.9	C14—C15—H15C	109.5
C3—C4—C5	119.64 (19)	H15A—C15—H15C	109.5
C3—C4—C7	122.22 (19)	H15B—C15—H15C	109.5
C5—C4—C7	118.14 (18)	C14—C16—H16A	109.5
C6—C5—C4	120.5 (2)	C14—C16—H16B	109.5
C6—C5—H5	119.7	H16A—C16—H16B	109.5
C4—C5—H5	119.7	C14—C16—H16C	109.5
C1—C6—C5	118.2 (2)	H16A—C16—H16C	109.5
C1—C6—H6	120.9	H16B—C16—H16C	109.5
C5—C6—H6	120.9	C13—C17—C18	111.42 (19)
N2—C7—C4	121.94 (18)	C13—C17—C19	113.50 (19)
N2—C7—Cl1	122.36 (16)	C18—C17—C19	110.2 (2)
C4—C7—Cl1	115.70 (15)	C13—C17—H17	107.1
C9—C8—C13	122.16 (19)	C18—C17—H17	107.1
C9—C8—N2	118.85 (17)	C19—C17—H17	107.1
C13—C8—N2	118.84 (18)	C17—C18—H18A	109.5
C10—C9—C8	117.86 (19)	C17—C18—H18B	109.5
C10—C9—C14	120.20 (19)	H18A—C18—H18B	109.5
C8—C9—C14	121.94 (18)	C17—C18—H18C	109.5
C11—C10—C9	121.3 (2)	H18A—C18—H18C	109.5
C11—C10—H10	119.3	H18B—C18—H18C	109.5
C9—C10—H10	119.3	C17—C19—H19A	109.5
C10—C11—C12	119.7 (2)	C17—C19—H19B	109.5
C10—C11—H11	120.2	H19A—C19—H19B	109.5
C12—C11—H11	120.2	C17—C19—H19C	109.5
C11—C12—C13	121.6 (2)	H19A—C19—H19C	109.5
C11—C12—H12	119.2	H19B—C19—H19C	109.5
C13—C12—H12	119.2	O2—N1—O1	124.1 (2)
C12—C13—C8	117.3 (2)	O2—N1—C1	118.0 (2)
C12—C13—C17	122.60 (19)	O1—N1—C1	117.9 (2)
C8—C13—C17	120.03 (18)	C7—N2—C8	122.75 (18)
C9—C14—C16	110.82 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg2i	0.95	2.67	3.511 (2)	147
C16—H16B···Cg1ii	0.98	2.79	3.663 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg2i	0.95	2.67	3.511 (2)	147
C16—H16B⋯Cg1ii	0.98	2.79	3.663 (3)	149

Symmetry codes: (i) ; (ii) .