7-Chloro-4-[(E)-2-(3,4,5-trimeth­oxy­benzyl­idene)hydrazin-1-yl]quinoline

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

doi:10.1107/S1600536812012755

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1214-o1215

doi:10.1107/S1600536812012755

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7-Chloro-4-[(E)-2-(3,4,5-trimethoxybenzylidene)hydrazin-1-yl]quinoline

Marcelle de Lima Ferreira,^a Marcus V. N. de Souza,^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 23 March 2012; online 28 March 2012)

In the title compound, C₁₉H₁₈ClN₃O₃, the r.m.s. deviation through the 23 non-H and non-methoxy atoms is 0.088 Å, indicating a planar molecule with the exception of the methoxy groups. One methoxy group, surrounded on either side by the other methoxy groups, is almost normal to the benzene ring to which it is connected [C—O—C_ar—C_ar torsion angle = 81.64 (15)°]. In the crystal, N—H⋯O, C—H⋯O and π–π interactions [between quinoline residues; centroid–centroid distance = 3.4375 (8) Å] link molecules into a three-dimensional architecture.

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. (2012 ). For related structures, see: Howie et al. (2010 ); de Souza et al. (2010 , 2012 ).

Experimental

Crystal data

C₁₉H₁₈ClN₃O₃
M_r = 371.81
Orthorhombic, P b c a
a = 7.6338 (2) Å
b = 15.5335 (4) Å
c = 28.7960 (7) Å
V = 3414.62 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 120 K
0.45 × 0.40 × 0.30 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
22673 measured reflections
3899 independent reflections
3353 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.02
3899 reflections
241 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O3ⁱ	0.87 (1)	2.53 (2)	3.0349 (15)	118 (1)
C19—H19B⋯N1ⁱⁱ	0.98	2.48	3.3602 (18)	149
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536812012755/bt5858sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012755/bt5858Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012755/bt5858Isup3.cml

checkCIF report

Comment top

The title compound, (I), was investigated as part of on-going crystallographic investigations of arylaldehyde 7-chloroquinoline-4-hydrazone species (Howie et al., 2010; de Souza et al., 2010; de Souza et al., 2012). The structural studies complement biological studies which show these hydrazones to possess a wide range of pharmacological activities such as anti-tubercular (Candea et al., 2009) and anti-tumour (Montenegro et al., 2012) activities, which are ascribed to the presence of the quinoline nucleus (de Souza et al., 2009).

In (I), Fig. 1, with the exception of two of the methyoxy groups, the molecule is planar. The r.m.s. deviation through the 23 non-hydrogen and non-methoxy atoms is 0.0879 Å. The maximum deviations from this plane are 0.1219 (11) Å for the N2 atom and -0.1498 (11) for the C14 atom. The terminal carbon atoms, C17–C19, of the methoxy groups lie -0.0840 (17), 0.7910 (16) and -0.3504 (19) Å, respectively, out of the least-squares plane, indicating that the central methoxy group is almost orthogonal to the benzene ring to which it is connected with the C18—O2—C14—C13 torsion angle being 81.64 (15)°. The conformation about the N3═C10 bond [1.2829 (17) Å] is E.

In the crystal packing, weak N—H···O hydrogen bonds along with C—H···O interactions, Table 1, and π—π interactions between symmetry related quinolinyl residues [centroid···centroid distance = 3.4375 (8) Å for symmetry operation -1/2 + x, y, 1/2 - z] link molecules into a three-dimensional architecture. Globally, molecules stack along the c axis with alternating layers of quinolinyl and trimethoxybenzene residues, Fig. 2.

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. (2012). For related structures, see: Howie et al. (2010); de Souza et al. (2010, 2012).

Experimental top

The compound was prepared from 7-chloro-4-quinolinylhydrazone and 3,4,5-trimethoxybenzaldehyde (Montenegro et al., 2012) and was recrystallized from an EtOCH₂CH₂OH solution of the compound.

Structure description top

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 in projection down the a axis of the unit-cell contents of (I). The N—H···O, C—H···N and π···π interactions are shown as orange, blue and purple dashed lines, respectively.

7-Chloro-4-[(E)-2-(3,4,5-trimethoxybenzylidene)hydrazin-1-yl]quinoline top

Crystal data top

C₁₉H₁₈ClN₃O₃	F(000) = 1552
M_r = 371.81	D_x = 1.447 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 24183 reflections
a = 7.6338 (2) Å	θ = 2.9–27.5°
b = 15.5335 (4) Å	µ = 0.25 mm⁻¹
c = 28.7960 (7) Å	T = 120 K
V = 3414.62 (15) Å³	Prism, colourless
Z = 8	0.45 × 0.40 × 0.30 mm

Data collection top

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer	3899 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	3353 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
φ and ω scans	h = −7→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −19→20
T_min = 0.652, T_max = 0.746	l = −26→37
22673 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0576P)² + 1.3595P] where P = (F_o² + 2F_c²)/3
3899 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₉H₁₈ClN₃O₃	V = 3414.62 (15) Å³
M_r = 371.81	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.6338 (2) Å	µ = 0.25 mm⁻¹
b = 15.5335 (4) Å	T = 120 K
c = 28.7960 (7) Å	0.45 × 0.40 × 0.30 mm

Data collection top

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer	3899 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	3353 reflections with I > 2σ(I)
T_min = 0.652, T_max = 0.746	R_int = 0.040
22673 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
3899 reflections	Δρ_min = −0.30 e Å⁻³
241 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	0.32570 (5)	0.04598 (2)	0.339654 (12)	0.02558 (12)
O1	−0.29202 (13)	0.51292 (6)	−0.01170 (3)	0.0189 (2)
O2	−0.26948 (13)	0.42177 (6)	−0.09143 (3)	0.0185 (2)
O3	−0.08960 (13)	0.27516 (6)	−0.09550 (3)	0.0185 (2)
N1	0.03404 (15)	0.32333 (7)	0.28807 (4)	0.0185 (2)
N2	0.06914 (15)	0.25871 (7)	0.14639 (4)	0.0166 (2)
H2n	0.123 (2)	0.2115 (8)	0.1386 (5)	0.020*
N3	−0.00092 (14)	0.30964 (7)	0.11233 (4)	0.0160 (2)
C1	−0.02236 (18)	0.37484 (8)	0.25478 (5)	0.0183 (3)
H1	−0.0738	0.4278	0.2641	0.022*
C2	−0.01331 (18)	0.35863 (9)	0.20702 (5)	0.0168 (3)
H2A	−0.0579	0.3991	0.1853	0.020*
C3	0.06177 (17)	0.28249 (8)	0.19210 (4)	0.0144 (3)
C4	0.12967 (17)	0.22434 (8)	0.22641 (4)	0.0141 (3)
C5	0.21216 (17)	0.14533 (9)	0.21567 (5)	0.0167 (3)
H5	0.2271	0.1295	0.1840	0.020*
C6	0.27103 (18)	0.09103 (9)	0.24970 (5)	0.0177 (3)
H6	0.3268	0.0383	0.2419	0.021*
C7	0.24732 (18)	0.11490 (9)	0.29641 (5)	0.0174 (3)
C8	0.16982 (18)	0.19071 (9)	0.30860 (5)	0.0179 (3)
H8	0.1564	0.2052	0.3405	0.021*
C9	0.10938 (17)	0.24777 (9)	0.27378 (4)	0.0152 (3)
C10	0.01112 (17)	0.27774 (9)	0.07136 (5)	0.0157 (3)
H10	0.0656	0.2231	0.0679	0.019*
C11	−0.05455 (17)	0.32096 (9)	0.02980 (4)	0.0152 (3)
C12	−0.14098 (17)	0.40041 (8)	0.03151 (4)	0.0155 (3)
H12	−0.1551	0.4297	0.0602	0.019*
C13	−0.20597 (17)	0.43605 (8)	−0.00934 (5)	0.0153 (3)
C14	−0.18806 (17)	0.39204 (9)	−0.05162 (4)	0.0157 (3)
C15	−0.09928 (17)	0.31355 (8)	−0.05291 (4)	0.0152 (3)
C16	−0.03088 (18)	0.27845 (8)	−0.01241 (4)	0.0160 (3)
H16	0.0318	0.2257	−0.0135	0.019*
C17	−0.31426 (19)	0.55864 (9)	0.03114 (5)	0.0219 (3)
H17A	−0.3887	0.5249	0.0521	0.033*
H17B	−0.3696	0.6144	0.0250	0.033*
H17C	−0.1997	0.5678	0.0456	0.033*
C18	−0.1751 (2)	0.48981 (9)	−0.11456 (5)	0.0225 (3)
H18A	−0.1514	0.5364	−0.0925	0.034*
H18B	−0.2456	0.5120	−0.1404	0.034*
H18C	−0.0641	0.4673	−0.1266	0.034*
C19	−0.0276 (2)	0.18760 (9)	−0.09654 (5)	0.0228 (3)
H19A	0.0954	0.1860	−0.0869	0.034*
H19B	−0.0382	0.1648	−0.1282	0.034*
H19C	−0.0979	0.1524	−0.0753	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0281 (2)	0.0275 (2)	0.02106 (19)	0.00361 (14)	−0.00295 (14)	0.00990 (14)
O1	0.0219 (5)	0.0175 (5)	0.0174 (5)	0.0038 (4)	−0.0027 (4)	0.0002 (4)
O2	0.0205 (5)	0.0199 (5)	0.0151 (5)	−0.0036 (4)	−0.0054 (4)	0.0060 (4)
O3	0.0240 (5)	0.0200 (5)	0.0115 (4)	0.0007 (4)	−0.0005 (4)	−0.0013 (4)
N1	0.0204 (6)	0.0187 (6)	0.0164 (5)	−0.0006 (5)	0.0001 (4)	−0.0014 (5)
N2	0.0216 (6)	0.0163 (5)	0.0120 (5)	0.0049 (5)	−0.0013 (4)	0.0017 (4)
N3	0.0168 (6)	0.0177 (5)	0.0135 (5)	−0.0003 (4)	−0.0015 (4)	0.0039 (4)
C1	0.0193 (7)	0.0155 (6)	0.0201 (7)	0.0008 (5)	0.0019 (5)	−0.0019 (5)
C2	0.0187 (7)	0.0154 (6)	0.0164 (6)	−0.0006 (5)	−0.0004 (5)	0.0022 (5)
C3	0.0133 (6)	0.0161 (6)	0.0139 (6)	−0.0025 (5)	0.0002 (5)	0.0008 (5)
C4	0.0133 (6)	0.0157 (6)	0.0133 (6)	−0.0033 (5)	−0.0001 (5)	0.0013 (5)
C5	0.0168 (6)	0.0185 (6)	0.0148 (6)	−0.0011 (5)	−0.0010 (5)	−0.0010 (5)
C6	0.0172 (7)	0.0151 (6)	0.0209 (7)	−0.0001 (5)	−0.0018 (5)	−0.0004 (5)
C7	0.0161 (6)	0.0191 (6)	0.0169 (6)	−0.0031 (5)	−0.0030 (5)	0.0057 (5)
C8	0.0186 (7)	0.0222 (7)	0.0128 (6)	−0.0024 (5)	0.0001 (5)	0.0005 (5)
C9	0.0139 (6)	0.0166 (6)	0.0151 (6)	−0.0028 (5)	0.0002 (5)	−0.0001 (5)
C10	0.0166 (6)	0.0154 (6)	0.0152 (6)	0.0000 (5)	−0.0006 (5)	0.0009 (5)
C11	0.0134 (6)	0.0184 (6)	0.0139 (6)	−0.0028 (5)	−0.0008 (5)	0.0019 (5)
C12	0.0162 (6)	0.0174 (6)	0.0129 (6)	−0.0025 (5)	−0.0012 (5)	−0.0005 (5)
C13	0.0137 (6)	0.0137 (6)	0.0184 (7)	−0.0018 (5)	−0.0009 (5)	0.0012 (5)
C14	0.0157 (6)	0.0182 (6)	0.0132 (6)	−0.0030 (5)	−0.0034 (5)	0.0035 (5)
C15	0.0165 (6)	0.0169 (6)	0.0123 (6)	−0.0040 (5)	0.0004 (5)	−0.0002 (5)
C16	0.0165 (6)	0.0158 (6)	0.0159 (6)	−0.0009 (5)	−0.0001 (5)	0.0019 (5)
C17	0.0241 (7)	0.0196 (7)	0.0218 (7)	0.0045 (6)	−0.0039 (6)	−0.0038 (6)
C18	0.0281 (8)	0.0202 (7)	0.0190 (7)	−0.0047 (6)	−0.0019 (6)	0.0062 (6)
C19	0.0316 (8)	0.0207 (7)	0.0162 (6)	0.0024 (6)	0.0010 (6)	−0.0032 (6)

Geometric parameters (Å, º) top

Cl1—C7	1.7478 (13)	C6—H6	0.9500
O1—C13	1.3646 (16)	C7—C8	1.364 (2)
O1—C17	1.4335 (17)	C8—C9	1.4156 (18)
O2—C14	1.3836 (15)	C8—H8	0.9500
O2—C18	1.4422 (16)	C10—C11	1.4609 (18)
O3—C15	1.3659 (15)	C10—H10	0.9500
O3—C19	1.4403 (17)	C11—C16	1.3949 (18)
N1—C1	1.3208 (18)	C11—C12	1.4003 (18)
N1—C9	1.3704 (17)	C12—C13	1.3915 (18)
N2—C3	1.3684 (16)	C12—H12	0.9500
N2—N3	1.3687 (15)	C13—C14	1.4030 (18)
N2—H2n	0.871 (9)	C14—C15	1.3954 (19)
N3—C10	1.2829 (17)	C15—C16	1.3893 (18)
C1—C2	1.4001 (19)	C16—H16	0.9500
C1—H1	0.9500	C17—H17A	0.9800
C2—C3	1.3826 (19)	C17—H17B	0.9800
C2—H2A	0.9500	C17—H17C	0.9800
C3—C4	1.4355 (18)	C18—H18A	0.9800
C4—C5	1.4136 (19)	C18—H18B	0.9800
C4—C9	1.4202 (17)	C18—H18C	0.9800
C5—C6	1.3689 (19)	C19—H19A	0.9800
C5—H5	0.9500	C19—H19B	0.9800
C6—C7	1.4068 (19)	C19—H19C	0.9800

C13—O1—C17	116.59 (10)	C11—C10—H10	118.3
C14—O2—C18	113.76 (10)	C16—C11—C12	120.60 (12)
C15—O3—C19	116.66 (10)	C16—C11—C10	116.86 (12)
C1—N1—C9	115.96 (12)	C12—C11—C10	122.53 (12)
C3—N2—N3	121.14 (11)	C13—C12—C11	119.26 (12)
C3—N2—H2n	119.7 (11)	C13—C12—H12	120.4
N3—N2—H2n	119.1 (11)	C11—C12—H12	120.4
C10—N3—N2	114.06 (11)	O1—C13—C12	124.19 (12)
N1—C1—C2	126.01 (13)	O1—C13—C14	115.47 (11)
N1—C1—H1	117.0	C12—C13—C14	120.33 (12)
C2—C1—H1	117.0	O2—C14—C15	119.20 (12)
C3—C2—C1	118.65 (12)	O2—C14—C13	120.84 (12)
C3—C2—H2A	120.7	C15—C14—C13	119.75 (12)
C1—C2—H2A	120.7	O3—C15—C16	124.20 (12)
N2—C3—C2	123.15 (12)	O3—C15—C14	115.58 (11)
N2—C3—C4	118.51 (12)	C16—C15—C14	120.21 (12)
C2—C3—C4	118.30 (12)	C15—C16—C11	119.79 (12)
C5—C4—C9	118.76 (12)	C15—C16—H16	120.1
C5—C4—C3	123.82 (12)	C11—C16—H16	120.1
C9—C4—C3	117.41 (12)	O1—C17—H17A	109.5
C6—C5—C4	121.64 (12)	O1—C17—H17B	109.5
C6—C5—H5	119.2	H17A—C17—H17B	109.5
C4—C5—H5	119.2	O1—C17—H17C	109.5
C5—C6—C7	118.67 (12)	H17A—C17—H17C	109.5
C5—C6—H6	120.7	H17B—C17—H17C	109.5
C7—C6—H6	120.7	O2—C18—H18A	109.5
C8—C7—C6	121.97 (12)	O2—C18—H18B	109.5
C8—C7—Cl1	119.60 (10)	H18A—C18—H18B	109.5
C6—C7—Cl1	118.40 (11)	O2—C18—H18C	109.5
C7—C8—C9	119.98 (12)	H18A—C18—H18C	109.5
C7—C8—H8	120.0	H18B—C18—H18C	109.5
C9—C8—H8	120.0	O3—C19—H19A	109.5
N1—C9—C8	117.41 (12)	O3—C19—H19B	109.5
N1—C9—C4	123.62 (12)	H19A—C19—H19B	109.5
C8—C9—C4	118.97 (12)	O3—C19—H19C	109.5
N3—C10—C11	123.46 (12)	H19A—C19—H19C	109.5
N3—C10—H10	118.3	H19B—C19—H19C	109.5

C3—N2—N3—C10	−177.97 (12)	N2—N3—C10—C11	−179.92 (12)
C9—N1—C1—C2	0.7 (2)	N3—C10—C11—C16	179.59 (12)
N1—C1—C2—C3	−0.4 (2)	N3—C10—C11—C12	−1.8 (2)
N3—N2—C3—C2	−0.9 (2)	C16—C11—C12—C13	1.09 (19)
N3—N2—C3—C4	176.90 (11)	C10—C11—C12—C13	−177.49 (12)
C1—C2—C3—N2	176.69 (12)	C17—O1—C13—C12	0.29 (18)
C1—C2—C3—C4	−1.07 (19)	C17—O1—C13—C14	179.15 (12)
N2—C3—C4—C5	3.29 (19)	C11—C12—C13—O1	−179.96 (12)
C2—C3—C4—C5	−178.84 (12)	C11—C12—C13—C14	1.23 (19)
N2—C3—C4—C9	−175.68 (11)	C18—O2—C14—C15	−103.67 (14)
C2—C3—C4—C9	2.19 (18)	C18—O2—C14—C13	81.64 (15)
C9—C4—C5—C6	0.58 (19)	O1—C13—C14—O2	−6.46 (18)
C3—C4—C5—C6	−178.38 (13)	C12—C13—C14—O2	172.44 (12)
C4—C5—C6—C7	0.3 (2)	O1—C13—C14—C15	178.87 (11)
C5—C6—C7—C8	−0.9 (2)	C12—C13—C14—C15	−2.22 (19)
C5—C6—C7—Cl1	−179.08 (10)	C19—O3—C15—C16	9.53 (19)
C6—C7—C8—C9	0.4 (2)	C19—O3—C15—C14	−169.05 (12)
Cl1—C7—C8—C9	178.63 (10)	O2—C14—C15—O3	4.77 (18)
C1—N1—C9—C8	−179.44 (12)	C13—C14—C15—O3	179.53 (11)
C1—N1—C9—C4	0.65 (19)	O2—C14—C15—C16	−173.87 (12)
C7—C8—C9—N1	−179.42 (12)	C13—C14—C15—C16	0.88 (19)
C7—C8—C9—C4	0.50 (19)	O3—C15—C16—C11	−177.10 (12)
C5—C4—C9—N1	178.92 (12)	C14—C15—C16—C11	1.4 (2)
C3—C4—C9—N1	−2.05 (19)	C12—C11—C16—C15	−2.4 (2)
C5—C4—C9—C8	−0.99 (18)	C10—C11—C16—C15	176.23 (12)
C3—C4—C9—C8	178.03 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O3ⁱ	0.87 (1)	2.53 (2)	3.0349 (15)	118 (1)
C19—H19B···N1ⁱⁱ	0.98	2.48	3.3602 (18)	149

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈ClN₃O₃
M_r	371.81
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	7.6338 (2), 15.5335 (4), 28.7960 (7)
V (Å³)	3414.62 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.45 × 0.40 × 0.30

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	22673, 3899, 3353
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.02
No. of reflections	3899
No. of parameters	241
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)	0.30, −0.30

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···O3ⁱ	0.870 (13)	2.529 (15)	3.0349 (15)	117.9 (11)
C19—H19B···N1ⁱⁱ	0.98	2.48	3.3602 (18)	149

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) 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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