7-Chloro-4-[(E)-2-(2,5-dimeth­oxy­benzyl­idene)hydrazin-1-yl]quinoline

Souza, M.V.N. de; Ferreira, M. de L.; Wardell, S.M.S.V.; Tiekink, E.R.T.; Wardell, J.L.

doi:10.1107/S1600536812012871

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1244-o1245

doi:10.1107/S1600536812012871

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7-Chloro-4-[(E)-2-(2,5-dimethoxybenzylidene)hydrazin-1-yl]quinoline

Marcus V. N. de Souza,^a Marcelle de Lima Ferreira,^a Solange M. S. V. Wardell,^b Edward R. T. Tiekink ^c ^* and James L. Wardell ^d ‡

^aInstituto de Tecnologia em Fármacos–Farmanguinhos, FioCruz–Fundação Oswaldo Cruz, R. Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, ^bCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 23 March 2012; accepted 24 March 2012; online 31 March 2012)

In the nearly planar title compound (r.m.s. deviation for the 24 non-H atoms = 0.064 Å), C₁₈H₁₆ClN₃O₂, the conformation about the N=C bond is E. Supramolecular chains propagated by glide symmetry along [001] are found in the crystal packing. These are sustained by N—H⋯N hydrogen bonds with the quinoline N atom being the acceptor. The chains are connected into a three-dimensional architecture by π–π interactions involving all three aromatic rings [centroid–centroid distances = 3.5650 (9)–3.6264 (9) Å].

Related literature

For the biological activity, including anti-tubercular and anti-tumour activity, of compounds containing the quinolinyl nucleus, see: de Souza et al. (2009 ); Candea et al. (2009 ); Montenegro et al. (2011 , 2012 ). For related structures, see: Howie et al. (2010 ); de Souza et al. (2010 ); de Lima Ferreira et al. (2010 ). For the synthesis, see: Montenegro et al. (2012).

Experimental

Crystal data

C₁₈H₁₆ClN₃O₂
M_r = 341.79
Monoclinic, P 2₁ /c
a = 10.5183 (2) Å
b = 12.9132 (3) Å
c = 12.9861 (2) Å
β = 112.723 (2)°
V = 1626.93 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 120 K
0.32 × 0.20 × 0.15 mm

Data collection

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.652, T_max = 0.746
20405 measured reflections
3723 independent reflections
3067 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 1.03
3723 reflections
222 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯N1ⁱ	0.88 (1)	2.19 (1)	3.0572 (17)	167 (2)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012871/xu5494sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012871/xu5494Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012871/xu5494Isup3.cml

checkCIF report

Comment top

The quinoline nucleus is an important moiety found in various synthetic and natural products with a wide range of pharmacological activities (de Souza et al., 2009), including anti-tubercular (Candea et al., 2009) and anti-tumour (Montenegro et al., 2012) activities. Among the derivatives studied have been arylaldehyde 7-chloroquinoline-4-hydrazones (Candea et al., 2009; Montenegro et al., 2011). Some crystal structures of the these hydrazones, including related methoxy-substituted derivatives have been reported (Howie et al., 2010; de Souza et al., 2010; de Lima Ferreira et al., 2010). We now wish to report the crystal structure of the title compound, (I).

In (I), Fig. 1, the entire molecule is planar with the r.m.s. deviation of all 24 non-hydrogen atoms being 0.064 Å. The maximum deviations from the least-squares plane are 0.108 (2) for the C5 atom and -0.165 (1) Å for the Cl1 atom. The conformation about the N3═C10 bond [1.2834 (18) Å] is E.

The most prominent feature of the crystal packing is the formation of supramolecular chains via N—H···N hydrogen bonds with the quinolinyl-N atom being the acceptor, Table 1. The chains a propagated by glide symmetry along the c axis, Fig. 2. Molecules are consolidated into a three-dimensional architecture by π—π interactions whereby the dimethoxybenzene ring interacts with both components of the quinolinyl residue along with symmetry related dimethoxybenzene rings [centroid(dimethoxybenzene)···centroid(NC₅)ⁱ; (C₆)ⁱ; (dimethoxybenzene)ⁱⁱ = 3.5650 (9), 3.6264 (9) and 3.5872 (9) Å, with angles of inclination = 2.36 (7) 4.20 (7) and 0° for symmetry operations i: 1 - x, -y, 1 - z and ii: 2 - x, -y, 1 - z]. The π—π interactions between the dimethoxybenzene and quinolinyl residues lead to zigzag layers in the bc plane and the π(dimethoxybenzene)···π(dimethoxybenzene) interactions link these layers along the a axis, Fig. 3.

Related literature top

For the biological activity, including anti-tubercular and anti-tumour activity, of compounds containing the quinolinyl nucleus, see: de Souza et al. (2009); Candea et al. (2009); Montenegro et al. (2011, 2012). For related structures, see: Howie et al. (2010); de Souza et al. (2010); de Lima Ferreira et al. (2010). For the synthesis, see: Montenegro et al. (2012).

Experimental top

The compound was prepared from 7-chloro-4-quinolinylhydrazone with 2,5-dimethoxybenzaldehyde (Montenegro et al., 2012). The crystals used in the structure determination were grown from an ethanol solution of the compound.

Structure description top

For the biological activity, including anti-tubercular and anti-tumour activity, of compounds containing the quinolinyl nucleus, see: de Souza et al. (2009); Candea et al. (2009); Montenegro et al. (2011, 2012). For related structures, see: Howie et al. (2010); de Souza et al. (2010); de Lima Ferreira et al. (2010). For the synthesis, see: Montenegro et al. (2012).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular chain along [001] in (I). The N—H···N hydrogen bonds are shown as blue dashed lines.
	Fig. 3. A view in projection down the c axis of unit-cell contents of (I). The N—H···N and π···π interactions are shown as blue and purple dashed lines, respectively.

7-Chloro-4-[(E)-2-(2,5-dimethoxybenzylidene)hydrazin-1-yl]quinoline top

Crystal data top

C₁₈H₁₆ClN₃O₂	F(000) = 712
M_r = 341.79	D_x = 1.395 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8419 reflections
a = 10.5183 (2) Å	θ = 2.9–27.5°
b = 12.9132 (3) Å	µ = 0.25 mm⁻¹
c = 12.9861 (2) Å	T = 120 K
β = 112.723 (2)°	Prism, yellow
V = 1626.93 (5) Å³	0.32 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer	3723 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	3067 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −15→16
T_min = 0.652, T_max = 0.746	l = −16→16
20405 measured reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0516P)² + 0.6611P] where P = (F_o² + 2F_c²)/3
3723 reflections	(Δ/σ)_max = 0.001
222 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₈H₁₆ClN₃O₂	V = 1626.93 (5) Å³
M_r = 341.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5183 (2) Å	µ = 0.25 mm⁻¹
b = 12.9132 (3) Å	T = 120 K
c = 12.9861 (2) Å	0.32 × 0.20 × 0.15 mm
β = 112.723 (2)°

Data collection top

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer	3723 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	3067 reflections with I > 2σ(I)
T_min = 0.652, T_max = 0.746	R_int = 0.049
20405 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.33 e Å⁻³
3723 reflections	Δρ_min = −0.33 e Å⁻³
222 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.07757 (4)	0.46710 (3)	0.65860 (3)	0.02240 (13)
O1	0.67832 (11)	0.06456 (8)	0.25193 (8)	0.0200 (2)
O2	0.98754 (12)	−0.18234 (9)	0.60966 (10)	0.0273 (3)
N1	0.45113 (13)	0.19900 (10)	0.83352 (10)	0.0169 (3)
N2	0.53424 (13)	0.16602 (10)	0.54269 (10)	0.0169 (3)
H2N	0.4970 (16)	0.2057 (11)	0.4831 (10)	0.020*
N3	0.63038 (13)	0.09359 (10)	0.54186 (10)	0.0174 (3)
C1	0.54351 (15)	0.13277 (12)	0.82563 (12)	0.0173 (3)
H1	0.5927	0.0921	0.8897	0.021*
C2	0.57480 (15)	0.11751 (12)	0.73189 (12)	0.0172 (3)
H2	0.6407	0.0669	0.7327	0.021*
C3	0.50855 (15)	0.17718 (11)	0.63725 (12)	0.0143 (3)
C4	0.40798 (14)	0.25126 (11)	0.64014 (11)	0.0135 (3)
C5	0.33252 (15)	0.31670 (11)	0.54965 (12)	0.0157 (3)
H5	0.3502	0.3143	0.4833	0.019*
C6	0.23425 (15)	0.38355 (11)	0.55596 (12)	0.0168 (3)
H6	0.1850	0.4277	0.4950	0.020*
C7	0.20770 (15)	0.38559 (11)	0.65392 (12)	0.0155 (3)
C8	0.27876 (15)	0.32511 (11)	0.74402 (12)	0.0158 (3)
H8	0.2589	0.3287	0.8094	0.019*
C9	0.38202 (14)	0.25713 (11)	0.73985 (12)	0.0142 (3)
C10	0.64283 (15)	0.08142 (11)	0.44812 (12)	0.0157 (3)
H10	0.5869	0.1209	0.3851	0.019*
C11	0.74242 (15)	0.00736 (11)	0.43720 (12)	0.0145 (3)
C12	0.75975 (15)	−0.00070 (11)	0.33516 (12)	0.0156 (3)
C13	0.85456 (16)	−0.07004 (12)	0.32490 (13)	0.0194 (3)
H13	0.8663	−0.0752	0.2561	0.023*
C14	0.93308 (16)	−0.13246 (12)	0.41476 (13)	0.0203 (3)
H14	0.9977	−0.1800	0.4070	0.024*
C15	0.91658 (15)	−0.12495 (12)	0.51558 (13)	0.0195 (3)
C16	0.82194 (15)	−0.05485 (11)	0.52614 (13)	0.0172 (3)
H16	0.8114	−0.0494	0.5954	0.021*
C17	0.7013 (2)	0.06604 (15)	0.15086 (14)	0.0303 (4)
H17A	0.7981	0.0827	0.1674	0.045*
H17B	0.6421	0.1185	0.1005	0.045*
H17C	0.6796	−0.0021	0.1151	0.045*
C18	1.09064 (17)	−0.25167 (13)	0.60485 (16)	0.0306 (4)
H18A	1.0479	−0.3035	0.5466	0.046*
H18B	1.1349	−0.2864	0.6771	0.046*
H18C	1.1599	−0.2127	0.5876	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0225 (2)	0.0242 (2)	0.0220 (2)	0.00878 (15)	0.01015 (16)	0.00116 (15)
O1	0.0247 (6)	0.0234 (6)	0.0150 (5)	0.0069 (5)	0.0111 (5)	0.0024 (4)
O2	0.0263 (6)	0.0217 (6)	0.0280 (6)	0.0076 (5)	0.0040 (5)	0.0068 (5)
N1	0.0197 (6)	0.0178 (6)	0.0140 (6)	0.0014 (5)	0.0073 (5)	0.0000 (5)
N2	0.0197 (7)	0.0191 (7)	0.0141 (6)	0.0052 (5)	0.0091 (5)	0.0022 (5)
N3	0.0185 (6)	0.0176 (6)	0.0188 (6)	0.0031 (5)	0.0100 (5)	−0.0005 (5)
C1	0.0189 (8)	0.0183 (7)	0.0143 (7)	0.0015 (6)	0.0057 (6)	0.0024 (6)
C2	0.0175 (7)	0.0184 (7)	0.0161 (7)	0.0028 (6)	0.0067 (6)	0.0002 (6)
C3	0.0148 (7)	0.0152 (7)	0.0139 (7)	−0.0041 (5)	0.0068 (6)	−0.0031 (5)
C4	0.0141 (7)	0.0143 (7)	0.0127 (7)	−0.0026 (5)	0.0057 (6)	−0.0017 (5)
C5	0.0183 (7)	0.0174 (7)	0.0128 (7)	−0.0011 (6)	0.0076 (6)	0.0005 (6)
C6	0.0188 (7)	0.0155 (7)	0.0157 (7)	0.0000 (6)	0.0063 (6)	0.0024 (6)
C7	0.0149 (7)	0.0127 (7)	0.0190 (7)	0.0007 (5)	0.0067 (6)	−0.0029 (6)
C8	0.0184 (7)	0.0171 (7)	0.0141 (7)	−0.0010 (6)	0.0085 (6)	−0.0019 (6)
C9	0.0157 (7)	0.0139 (7)	0.0125 (7)	−0.0025 (6)	0.0048 (5)	−0.0021 (5)
C10	0.0163 (7)	0.0164 (7)	0.0150 (7)	−0.0008 (6)	0.0067 (6)	0.0006 (6)
C11	0.0144 (7)	0.0139 (7)	0.0162 (7)	−0.0024 (5)	0.0072 (6)	−0.0017 (5)
C12	0.0166 (7)	0.0152 (7)	0.0154 (7)	−0.0007 (6)	0.0065 (6)	−0.0002 (5)
C13	0.0207 (8)	0.0188 (8)	0.0218 (8)	−0.0006 (6)	0.0113 (6)	−0.0039 (6)
C14	0.0171 (7)	0.0152 (7)	0.0296 (8)	0.0008 (6)	0.0101 (7)	−0.0029 (6)
C15	0.0165 (7)	0.0142 (7)	0.0237 (8)	−0.0015 (6)	0.0031 (6)	0.0012 (6)
C16	0.0179 (7)	0.0162 (7)	0.0176 (7)	−0.0029 (6)	0.0071 (6)	−0.0014 (6)
C17	0.0427 (11)	0.0363 (10)	0.0193 (8)	0.0131 (8)	0.0202 (8)	0.0059 (7)
C18	0.0236 (9)	0.0184 (8)	0.0431 (11)	0.0048 (7)	0.0053 (8)	0.0037 (7)

Geometric parameters (Å, º) top

Cl1—C7	1.7462 (15)	C6—H6	0.9500
O1—C12	1.3773 (18)	C7—C8	1.365 (2)
O1—C17	1.4235 (18)	C8—C9	1.414 (2)
O2—C15	1.3764 (18)	C8—H8	0.9500
O2—C18	1.426 (2)	C10—C11	1.465 (2)
N1—C1	1.3277 (19)	C10—H10	0.9500
N1—C9	1.3742 (18)	C11—C16	1.390 (2)
N2—C3	1.3631 (18)	C11—C12	1.409 (2)
N2—N3	1.3805 (17)	C12—C13	1.384 (2)
N2—H2N	0.884 (9)	C13—C14	1.396 (2)
N3—C10	1.2834 (18)	C13—H13	0.9500
C1—C2	1.392 (2)	C14—C15	1.389 (2)
C1—H1	0.9500	C14—H14	0.9500
C2—C3	1.389 (2)	C15—C16	1.391 (2)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.437 (2)	C17—H17A	0.9800
C4—C5	1.416 (2)	C17—H17B	0.9800
C4—C9	1.4248 (19)	C17—H17C	0.9800
C5—C6	1.373 (2)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.404 (2)	C18—H18C	0.9800

C12—O1—C17	117.14 (12)	N3—C10—C11	120.69 (13)
C15—O2—C18	117.38 (13)	N3—C10—H10	119.7
C1—N1—C9	115.86 (12)	C11—C10—H10	119.7
C3—N2—N3	118.64 (12)	C16—C11—C12	118.92 (13)
C3—N2—H2N	123.5 (11)	C16—C11—C10	121.33 (13)
N3—N2—H2N	117.7 (11)	C12—C11—C10	119.74 (13)
C10—N3—N2	115.71 (12)	O1—C12—C13	124.95 (13)
N1—C1—C2	125.86 (13)	O1—C12—C11	115.19 (13)
N1—C1—H1	117.1	C13—C12—C11	119.85 (14)
C2—C1—H1	117.1	C12—C13—C14	120.57 (14)
C3—C2—C1	119.21 (13)	C12—C13—H13	119.7
C3—C2—H2	120.4	C14—C13—H13	119.7
C1—C2—H2	120.4	C15—C14—C13	119.91 (14)
N2—C3—C2	122.16 (13)	C15—C14—H14	120.0
N2—C3—C4	119.86 (13)	C13—C14—H14	120.0
C2—C3—C4	117.96 (13)	O2—C15—C14	125.22 (14)
C5—C4—C9	118.67 (13)	O2—C15—C16	115.23 (14)
C5—C4—C3	123.90 (13)	C14—C15—C16	119.55 (14)
C9—C4—C3	117.42 (12)	C11—C16—C15	121.20 (14)
C6—C5—C4	121.28 (13)	C11—C16—H16	119.4
C6—C5—H5	119.4	C15—C16—H16	119.4
C4—C5—H5	119.4	O1—C17—H17A	109.5
C5—C6—C7	118.92 (13)	O1—C17—H17B	109.5
C5—C6—H6	120.5	H17A—C17—H17B	109.5
C7—C6—H6	120.5	O1—C17—H17C	109.5
C8—C7—C6	122.10 (13)	H17A—C17—H17C	109.5
C8—C7—Cl1	119.49 (11)	H17B—C17—H17C	109.5
C6—C7—Cl1	118.41 (11)	O2—C18—H18A	109.5
C7—C8—C9	119.80 (13)	O2—C18—H18B	109.5
C7—C8—H8	120.1	H18A—C18—H18B	109.5
C9—C8—H8	120.1	O2—C18—H18C	109.5
N1—C9—C8	117.18 (12)	H18A—C18—H18C	109.5
N1—C9—C4	123.63 (13)	H18B—C18—H18C	109.5
C8—C9—C4	119.18 (13)

C3—N2—N3—C10	175.16 (13)	C3—C4—C9—N1	2.5 (2)
C9—N1—C1—C2	−0.3 (2)	C5—C4—C9—C8	2.2 (2)
N1—C1—C2—C3	1.8 (2)	C3—C4—C9—C8	−176.72 (13)
N3—N2—C3—C2	−0.6 (2)	N2—N3—C10—C11	179.47 (12)
N3—N2—C3—C4	−179.38 (12)	N3—C10—C11—C16	2.7 (2)
C1—C2—C3—N2	−179.88 (14)	N3—C10—C11—C12	−176.54 (14)
C1—C2—C3—C4	−1.1 (2)	C17—O1—C12—C13	−5.0 (2)
N2—C3—C4—C5	−1.0 (2)	C17—O1—C12—C11	174.34 (14)
C2—C3—C4—C5	−179.75 (14)	C16—C11—C12—O1	−179.20 (13)
N2—C3—C4—C9	177.93 (13)	C10—C11—C12—O1	0.1 (2)
C2—C3—C4—C9	−0.9 (2)	C16—C11—C12—C13	0.2 (2)
C9—C4—C5—C6	−1.1 (2)	C10—C11—C12—C13	179.50 (13)
C3—C4—C5—C6	177.74 (13)	O1—C12—C13—C14	179.53 (14)
C4—C5—C6—C7	−0.8 (2)	C11—C12—C13—C14	0.2 (2)
C5—C6—C7—C8	1.6 (2)	C12—C13—C14—C15	−0.2 (2)
C5—C6—C7—Cl1	−177.40 (11)	C18—O2—C15—C14	3.0 (2)
C6—C7—C8—C9	−0.5 (2)	C18—O2—C15—C16	−176.98 (13)
Cl1—C7—C8—C9	178.51 (11)	C13—C14—C15—O2	179.83 (14)
C1—N1—C9—C8	177.32 (13)	C13—C14—C15—C16	−0.2 (2)
C1—N1—C9—C4	−1.9 (2)	C12—C11—C16—C15	−0.6 (2)
C7—C8—C9—N1	179.30 (13)	C10—C11—C16—C15	−179.88 (13)
C7—C8—C9—C4	−1.4 (2)	O2—C15—C16—C11	−179.42 (13)
C5—C4—C9—N1	−178.56 (13)	C14—C15—C16—C11	0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···N1ⁱ	0.88 (1)	2.19 (1)	3.0572 (17)	167 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆ClN₃O₂
M_r	341.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	10.5183 (2), 12.9132 (3), 12.9861 (2)
β (°)	112.723 (2)
V (Å³)	1626.93 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.32 × 0.20 × 0.15

Data collection
Diffractometer	Bruker–Nonius Roper CCD camera on a κ-goniostat
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.652, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	20405, 3723, 3067
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 1.03
No. of reflections	3723
No. of parameters	222
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.33

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···N1ⁱ	0.884 (13)	2.190 (13)	3.0572 (17)	166.9 (16)

Symmetry code: (i) x, −y+1/2, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR/MOHE/SC/12) is gratefully acknowledged.

References

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