Crystal structure of 3-(9H-carbazol-9-yl)-N'-[(E)-4-chloro-benzyl-idene]propano-hydrazide.

In the title compound, C22H18ClN3O, the carbazole ring system is essentially planar (r.m.s deviation = 0.003 Å), and makes a dihedral angle of 9.01 (8)° with the plane of the chloro-phenyl ring. In the crystal, neighbouring mol-ecules are linked into centrosymmetric R 2 (2)(8) dimers by pairs of N-H⋯O inter-actions and into a three-dimensional network by C-H⋯π inter-actions. The dimers are arranged into layers parallel to (010).

Related literature

For synthesis and pharmacuetical studies of carbazole containing compounds, see: Hewlins et al. (1984 ▸); Kansal & Potier (1986 ▸); Haider et al. (1998 ▸); Hirata et al. (1999 ▸); Chowdhury et al. (1978 ▸); Sakano et al. (1980 ▸); Pindur (1990 ▸); Knölker & Reddy (2002 ▸); Martin & Prasad (2006 ▸); Saturnino et al. (2003 ▸).

Experimental

Crystal data

C22H18ClN3O

M = 375.84

Monoclinic,

a = 16.0126 (7) Å

b = 7.4316 (3) Å

c = 16.1654 (9) Å

β = 94.607 (4)°

V = 1917.46 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.42 × 0.36 × 0.08 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.847, T max = 1.000

12277 measured reflections

6312 independent reflections

3066 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.167

S = 1.02

6312 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015020770/qm2112sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020770/qm2112Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020770/qm2112Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020770/qm2112fig1.tif

View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015020770/qm2112fig2.tif

View of the dimers formed by N—H⋯O hydrogen bonds down the b axis.

CCDC reference: 1434700

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H18ClN3O	F(000) = 784
Mr = 375.84	Dx = 1.302 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2141 reflections
a = 16.0126 (7) Å	θ = 3.7–30.7°
b = 7.4316 (3) Å	µ = 0.22 mm−1
c = 16.1654 (9) Å	T = 293 K
β = 94.607 (4)°	Plate, orange
V = 1917.46 (16) Å3	0.42 × 0.36 × 0.08 mm
Z = 4

Agilent Xcalibur Eos Gemini diffractometer	6312 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3066 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.0416 pixels mm-1	θmax = 32.8°, θmin = 3.0°
ω scans	h = −21→24
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −5→10
Tmin = 0.847, Tmax = 1.000	l = −23→19
12277 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.350P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
6312 reflections	Δρmax = 0.20 e Å−3
244 parameters	Δρmin = −0.24 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.99666 (4)	−0.31996 (9)	0.20792 (5)	0.0942 (3)
O1	0.50960 (9)	−0.32276 (16)	0.57559 (9)	0.0624 (5)
N1	0.66300 (10)	0.17932 (18)	0.56956 (10)	0.0547 (5)
N2	0.60196 (9)	−0.39049 (19)	0.48394 (9)	0.0535 (5)
N3	0.67596 (9)	−0.35405 (19)	0.44990 (10)	0.0511 (5)
C1	0.64514 (12)	0.2806 (2)	0.63777 (12)	0.0539 (6)
C2	0.57672 (16)	0.2737 (3)	0.68399 (17)	0.0803 (9)
C3	0.5780 (2)	0.3896 (4)	0.75265 (19)	0.1108 (14)
C4	0.6440 (3)	0.5071 (4)	0.77117 (19)	0.1203 (16)
C5	0.7099 (2)	0.5122 (3)	0.72554 (17)	0.0944 (12)
C6	0.71287 (14)	0.3976 (2)	0.65793 (12)	0.0609 (7)
C7	0.77393 (13)	0.3604 (3)	0.60061 (13)	0.0649 (7)
C8	0.85479 (19)	0.4244 (4)	0.5889 (2)	0.1049 (13)
C9	0.8972 (2)	0.3490 (6)	0.5267 (3)	0.1362 (18)
C10	0.8626 (3)	0.2141 (6)	0.4766 (3)	0.1306 (17)
C11	0.78534 (18)	0.1509 (4)	0.48540 (17)	0.0887 (10)
C12	0.74149 (13)	0.2233 (2)	0.54750 (13)	0.0578 (6)
C13	0.61339 (13)	0.0290 (2)	0.53681 (13)	0.0646 (7)
C14	0.63465 (11)	−0.1461 (2)	0.58248 (12)	0.0522 (6)
C15	0.57783 (12)	−0.2941 (2)	0.54829 (12)	0.0502 (6)
C16	0.69414 (11)	−0.4544 (2)	0.39006 (12)	0.0546 (6)
C17	0.76989 (11)	−0.4242 (2)	0.34818 (11)	0.0507 (6)
C18	0.83316 (12)	−0.3082 (2)	0.37949 (12)	0.0567 (6)
C19	0.90254 (12)	−0.2777 (3)	0.33665 (14)	0.0625 (7)
C20	0.90972 (13)	−0.3622 (3)	0.26225 (14)	0.0626 (7)
C21	0.84950 (14)	−0.4801 (3)	0.23015 (14)	0.0701 (8)
C22	0.78026 (13)	−0.5105 (3)	0.27385 (13)	0.0647 (7)
H2	0.53200	0.19640	0.67050	0.0960*
H2N	0.57290	−0.47400	0.46610	0.0640*
H3	0.53370	0.38750	0.78640	0.1330*
H4	0.64240	0.58410	0.81640	0.1450*
H5	0.75350	0.59220	0.73900	0.1130*
H8	0.87900	0.51530	0.62240	0.1260*
H9	0.95070	0.39030	0.51840	0.1640*
H10	0.89350	0.16560	0.43560	0.1570*
H11	0.76210	0.06110	0.45070	0.1060*
H13A	0.62230	0.01380	0.47860	0.0780*
H13B	0.55450	0.05590	0.54060	0.0780*
H14A	0.69250	−0.17810	0.57610	0.0630*
H14B	0.62810	−0.13070	0.64120	0.0630*
H16	0.65840	−0.54830	0.37290	0.0660*
H18	0.82840	−0.25080	0.43000	0.0680*
H19	0.94440	−0.20000	0.35810	0.0750*
H21	0.85520	−0.53820	0.18000	0.0840*
H22	0.73950	−0.59110	0.25280	0.0780*

	U11	U22	U33	U12	U13	U23
Cl1	0.0802 (4)	0.0860 (4)	0.1213 (6)	0.0009 (3)	0.0377 (4)	−0.0096 (4)
O1	0.0627 (8)	0.0490 (7)	0.0762 (9)	−0.0175 (6)	0.0092 (7)	−0.0065 (6)
N1	0.0572 (9)	0.0354 (7)	0.0690 (10)	−0.0128 (6)	−0.0100 (7)	−0.0014 (7)
N2	0.0576 (9)	0.0383 (7)	0.0638 (10)	−0.0184 (7)	0.0009 (7)	−0.0023 (7)
N3	0.0525 (8)	0.0393 (7)	0.0605 (9)	−0.0101 (6)	−0.0020 (7)	0.0047 (7)
C1	0.0650 (12)	0.0325 (8)	0.0620 (11)	−0.0028 (8)	−0.0089 (9)	0.0074 (8)
C2	0.0819 (16)	0.0551 (12)	0.1050 (19)	0.0077 (11)	0.0151 (14)	0.0141 (13)
C3	0.157 (3)	0.0816 (19)	0.101 (2)	0.041 (2)	0.055 (2)	0.0206 (17)
C4	0.221 (4)	0.0656 (17)	0.074 (2)	0.013 (2)	0.010 (2)	−0.0023 (15)
C5	0.160 (3)	0.0472 (12)	0.0692 (16)	−0.0157 (15)	−0.0327 (17)	0.0001 (11)
C6	0.0858 (14)	0.0358 (9)	0.0567 (11)	−0.0128 (9)	−0.0216 (10)	0.0100 (8)
C7	0.0677 (12)	0.0478 (10)	0.0745 (14)	−0.0214 (9)	−0.0224 (11)	0.0250 (10)
C8	0.0827 (18)	0.093 (2)	0.133 (3)	−0.0414 (16)	−0.0290 (17)	0.0530 (19)
C9	0.0716 (19)	0.149 (3)	0.191 (4)	−0.016 (2)	0.029 (2)	0.094 (3)
C10	0.115 (3)	0.137 (3)	0.147 (3)	0.019 (2)	0.055 (2)	0.062 (3)
C11	0.101 (2)	0.0791 (16)	0.0881 (18)	0.0100 (15)	0.0215 (15)	0.0222 (14)
C12	0.0640 (12)	0.0444 (9)	0.0637 (12)	−0.0037 (9)	−0.0031 (9)	0.0148 (9)
C13	0.0723 (13)	0.0375 (9)	0.0786 (13)	−0.0143 (9)	−0.0275 (10)	0.0013 (9)
C14	0.0569 (10)	0.0389 (8)	0.0584 (11)	−0.0108 (8)	−0.0099 (8)	−0.0005 (8)
C15	0.0580 (11)	0.0334 (8)	0.0575 (11)	−0.0100 (8)	−0.0050 (8)	0.0058 (8)
C16	0.0560 (11)	0.0377 (9)	0.0682 (12)	−0.0101 (8)	−0.0073 (9)	−0.0006 (8)
C17	0.0524 (10)	0.0370 (8)	0.0609 (11)	−0.0019 (7)	−0.0073 (8)	−0.0011 (8)
C18	0.0584 (11)	0.0493 (10)	0.0611 (11)	−0.0056 (9)	−0.0033 (9)	−0.0079 (9)
C19	0.0538 (11)	0.0509 (10)	0.0811 (14)	−0.0078 (9)	−0.0043 (10)	−0.0045 (10)
C20	0.0579 (11)	0.0515 (10)	0.0783 (14)	0.0090 (9)	0.0054 (10)	−0.0043 (10)
C21	0.0703 (13)	0.0644 (13)	0.0750 (14)	0.0045 (11)	0.0019 (11)	−0.0212 (11)
C22	0.0606 (12)	0.0534 (11)	0.0781 (14)	−0.0052 (9)	−0.0060 (10)	−0.0178 (10)

Cl1—C20	1.733 (2)	C16—C17	1.453 (3)
O1—C15	1.229 (2)	C17—C22	1.384 (3)
N1—C1	1.384 (2)	C17—C18	1.394 (2)
N1—C12	1.373 (3)	C18—C19	1.374 (3)
N1—C13	1.446 (2)	C19—C20	1.370 (3)
N2—N3	1.373 (2)	C20—C21	1.374 (3)
N2—C15	1.345 (2)	C21—C22	1.380 (3)
N3—C16	1.274 (2)	C2—H2	0.9300
C1—C2	1.376 (3)	C3—H3	0.9300
C1—C6	1.408 (3)	C4—H4	0.9300
C2—C3	1.404 (4)	C5—H5	0.9300
N2—H2N	0.8100	C8—H8	0.9300
C3—C4	1.385 (5)	C9—H9	0.9300
C4—C5	1.336 (5)	C10—H10	0.9300
C5—C6	1.389 (3)	C11—H11	0.9300
C6—C7	1.427 (3)	C13—H13A	0.9700
C7—C12	1.405 (3)	C13—H13B	0.9700
C7—C8	1.406 (4)	C14—H14A	0.9700
C8—C9	1.377 (5)	C14—H14B	0.9700
C9—C10	1.377 (6)	C16—H16	0.9300
C10—C11	1.342 (6)	C18—H18	0.9300
C11—C12	1.380 (3)	C19—H19	0.9300
C13—C14	1.521 (2)	C21—H21	0.9300
C14—C15	1.504 (2)	C22—H22	0.9300
C1—N1—C12	109.24 (15)	C19—C20—C21	121.2 (2)
C1—N1—C13	124.70 (16)	C20—C21—C22	118.7 (2)
C12—N1—C13	125.17 (16)	C17—C22—C21	121.73 (19)
N3—N2—C15	121.05 (14)	C1—C2—H2	122.00
N2—N3—C16	116.50 (14)	C3—C2—H2	122.00
N1—C1—C2	129.57 (18)	C2—C3—H3	119.00
N1—C1—C6	108.41 (16)	C4—C3—H3	119.00
C2—C1—C6	121.98 (18)	C3—C4—H4	119.00
C1—C2—C3	116.4 (2)	C5—C4—H4	119.00
N3—N2—H2N	120.00	C4—C5—H5	120.00
C15—N2—H2N	119.00	C6—C5—H5	120.00
C2—C3—C4	121.4 (3)	C7—C8—H8	121.00
C3—C4—C5	121.4 (3)	C9—C8—H8	121.00
C4—C5—C6	119.7 (3)	C8—C9—H9	119.00
C5—C6—C7	134.3 (2)	C10—C9—H9	119.00
C1—C6—C7	106.58 (16)	C9—C10—H10	119.00
C1—C6—C5	119.1 (2)	C11—C10—H10	119.00
C6—C7—C8	135.1 (2)	C10—C11—H11	121.00
C6—C7—C12	107.36 (18)	C12—C11—H11	121.00
C8—C7—C12	117.5 (2)	N1—C13—H13A	109.00
C7—C8—C9	118.3 (3)	N1—C13—H13B	109.00
C8—C9—C10	121.8 (3)	C14—C13—H13A	109.00
C9—C10—C11	121.6 (4)	C14—C13—H13B	109.00
C10—C11—C12	117.9 (3)	H13A—C13—H13B	108.00
N1—C12—C7	108.37 (17)	C13—C14—H14A	110.00
N1—C12—C11	128.76 (19)	C13—C14—H14B	110.00
C7—C12—C11	122.9 (2)	C15—C14—H14A	110.00
N1—C13—C14	112.84 (16)	C15—C14—H14B	110.00
C13—C14—C15	110.00 (15)	H14A—C14—H14B	108.00
N2—C15—C14	118.09 (16)	N3—C16—H16	120.00
O1—C15—C14	121.57 (16)	C17—C16—H16	120.00
O1—C15—N2	120.28 (16)	C17—C18—H18	120.00
N3—C16—C17	120.91 (15)	C19—C18—H18	120.00
C18—C17—C22	117.87 (17)	C18—C19—H19	120.00
C16—C17—C18	122.40 (16)	C20—C19—H19	120.00
C16—C17—C22	119.72 (16)	C20—C21—H21	121.00
C17—C18—C19	120.82 (18)	C22—C21—H21	121.00
C18—C19—C20	119.68 (19)	C17—C22—H22	119.00
Cl1—C20—C21	119.48 (17)	C21—C22—H22	119.00
Cl1—C20—C19	119.30 (16)
C1—N1—C12—C7	−2.1 (2)	C5—C6—C7—C8	−0.5 (4)
C12—N1—C1—C2	−175.4 (2)	C6—C7—C12—N1	1.2 (2)
C13—N1—C1—C2	−5.7 (3)	C6—C7—C12—C11	−178.4 (2)
C12—N1—C1—C6	2.3 (2)	C6—C7—C8—C9	177.5 (3)
C13—N1—C1—C6	171.93 (16)	C12—C7—C8—C9	−0.2 (4)
C12—N1—C13—C14	84.8 (2)	C8—C7—C12—N1	179.5 (2)
C1—N1—C13—C14	−83.2 (2)	C8—C7—C12—C11	−0.1 (3)
C13—N1—C12—C7	−171.72 (17)	C7—C8—C9—C10	−0.1 (6)
C1—N1—C12—C11	177.4 (2)	C8—C9—C10—C11	0.8 (7)
C13—N1—C12—C11	7.8 (3)	C9—C10—C11—C12	−1.1 (6)
C15—N2—N3—C16	178.89 (16)	C10—C11—C12—C7	0.7 (4)
N3—N2—C15—C14	−0.5 (2)	C10—C11—C12—N1	−178.7 (3)
N3—N2—C15—O1	176.58 (16)	N1—C13—C14—C15	177.03 (16)
N2—N3—C16—C17	178.32 (15)	C13—C14—C15—O1	−88.0 (2)
N1—C1—C6—C5	−179.18 (18)	C13—C14—C15—N2	89.05 (19)
N1—C1—C6—C7	−1.5 (2)	N3—C16—C17—C18	11.7 (3)
C6—C1—C2—C3	−0.1 (3)	N3—C16—C17—C22	−167.34 (18)
N1—C1—C2—C3	177.3 (2)	C16—C17—C18—C19	−177.55 (17)
C2—C1—C6—C7	176.36 (19)	C22—C17—C18—C19	1.5 (3)
C2—C1—C6—C5	−1.3 (3)	C16—C17—C22—C21	177.23 (19)
C1—C2—C3—C4	1.5 (4)	C18—C17—C22—C21	−1.9 (3)
C2—C3—C4—C5	−1.5 (5)	C17—C18—C19—C20	0.0 (3)
C3—C4—C5—C6	0.0 (5)	C18—C19—C20—Cl1	178.96 (16)
C4—C5—C6—C7	−175.5 (3)	C18—C19—C20—C21	−1.3 (3)
C4—C5—C6—C1	1.4 (4)	Cl1—C20—C21—C22	−179.29 (17)
C5—C6—C7—C12	177.4 (2)	C19—C20—C21—C22	1.0 (3)
C1—C6—C7—C12	0.2 (2)	C20—C21—C22—C17	0.7 (3)
C1—C6—C7—C8	−177.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1i	0.81	2.08	2.8952 (19)	175
C14—H14A···N3	0.97	2.42	2.765 (2)	100
C5—H5···Cg4ii	0.93	2.81	3.696 (3)	160
C21—H21···Cg3iii	0.93	2.97	3.858 (3)	160
C22—H22···Cg2iii	0.93	2.79	3.699 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the two benzene rings (C1–C6 and C7–C12) of the carbazole ring system and the chloro­phenyl ring (C17–C22), respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1i	0.81	2.08	2.8952 (19)	175
C5—H5⋯Cg4ii	0.93	2.81	3.696 (3)	160
C21—H21⋯Cg3iii	0.93	2.97	3.858 (3)	160
C22—H22⋯Cg2iii	0.93	2.79	3.699 (2)	166

Symmetry codes: (i) ; (ii) ; (iii) .