2-Benzoyl-1-(2,4-dichloro­phen­yl)-3-phenyl­guanidine

Murtaza, G.; Ebihara, M.; Said, M.; Khawar Rauf, M.; Anwar, S.

doi:10.1107/S160053680903387X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2297-o2298

doi:10.1107/S160053680903387X

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2-Benzoyl-1-(2,4-dichlorophenyl)-3-phenylguanidine

Ghulam Murtaza,^a Masahiro Ebihara,^b Muhammad Said,^a M. Khawar Rauf ^a ^* and Saeed Anwar ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bDepartment of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu City 501-1193, Japan, and ^cDepartment of Chemistry, Abdul Wali Khan University, Mardan, Pakistan
^*Correspondence e-mail: khawar_rauf@hotmail.com

(Received 14 August 2009; accepted 24 August 2009; online 29 August 2009)

In the title compound, C₂₀H₁₅Cl₂N₃O, a typical polysubstituted guanidine with normal geometric parameters, the torsion angles [C—N—C—O = 3.8 (2), N—C—N—C = −6.1 (2)°] indicate that the guanidine and carbonyl groups are almost coplanar, due to the pseudo-hexagonal ring formed by intramolecular N—H⋯O hydrogen bonds. The crystal packing is stabilized by intermolecular N—H⋯O hydrogen bonds, which link the molecules into centrosymmetric dimers.

Related literature

The guanidinium group is present in diverse biologically active substances, see: Manimala & Anslyn (2002 ); Berlinck (2002 ). These compounds have received increasing interest as medicinal agents, for example having an effect on the neuromuscular junction, see: Rodrigues-Simioni et al. (1997 ). Guanidine derivatives are also useful building blocks in synthetic organic chemistry, see: Costa et al. (1998 ); Kovacevic & Maksic (2001 ), and due to their strongly basic character, guanidines can be considered as super-bases for biological systems, see: Ishikawa & Isobe (2002 ). For related structures, see: Cunha et al. (2005 ); Murtaza et al. (2007 , 2008 , 2009 ). For the preparation of N-benzoyl-N′-phenylthiourea, see: Rauf et al. (2009 ).

Experimental

Crystal data

C₂₀H₁₅Cl₂N₃O
M_r = 384.25
Monoclinic, P 2₁ /c
a = 16.461 (6) Å
b = 6.663 (2) Å
c = 19.388 (6) Å
β = 124.072 (5)°
V = 1761.0 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 123 K
0.42 × 0.40 × 0.18 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: none
13586 measured reflections
4023 independent reflections
3768 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.099
S = 1.12
4023 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.84 (2)	2.01 (2)	2.6471 (19)	132.7 (18)
N3—H3⋯O1ⁱ	0.84 (2)	2.36 (2)	3.032 (2)	138.2 (18)
Symmetry code: (i) -x, -y+1, -z.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPII (Johnson, 1976 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and TEXSAN.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903387X/hg2555sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903387X/hg2555Isup2.hkl

checkCIF report

Comment top

Polysubstituted guanidines is a field of intense investigation as guanidinium group is present in diverse biologically active substances (Manimala & Anslyn, 2002; Berlinck, 2002) These compounds have received increasing interest as medicinal agents, e.g it has effect on the neuromuscular junction (Rodrigues-Simioni et al., 1997). In addition to their biological role, guanidine derivatives are very useful building blocks in synthetic organic chemistry (Costa et al., 1998; Kovacevic & Maksic, 2001). Due to their strongly basic character, guanidines can be considered as super-bases for the biological systems (Ishikawa & Isobe, 2002). The title compound (I), (Fig.1) is a typical N,N',N"-tri-substituted guanidine with normal geometric parameters (Cunha et al., 2005; Murtaza et al., 2007, 2008, 2009). The C3—O1 bond shows expected full double bond character while the short values for C1—N1, C2—N1, C2—N2 and C2—N3 bonds indicate partial double bond character. The dihedral angles between the guanidine plane [C2/N1/N2/N3] and the mean planes of phenyl rings C3–C8, C9–C14 & C15–C20 are 22.23 (11)°, 48.06 (7)° & 83.53 (7)°, respectively. The guanidine moiety and carbonyl group are almost co-planar as reflected by the torsion angles [C1—N1—C2—O1 = 3.8 (2)° and N3—C1—N1—C2= -6.1 (2)°], due to the presence of intramolecular N—H···O hydrogen bonding (Table 1), forming a six-membered ring commonly observed in this class of compounds (Cunha et al., 2005). The crystal packing shows intermolecular N—H···O hydrogen bonds which link the molecules into centrosymmetric dimers (Fig. 2).

Related literature top

The guanidinium group is present in diverse biologically active substances, see: Manimala & Anslyn (2002); Berlinck (2002). These compounds have received increasing interest as medicinal agents, for example having an effect on the neuromuscular junction, see: Rodrigues-Simioni et al. (1997). Guanidine derivatives are also useful building blocks in synthetic organic chemistry, see: Costa et al. (1998); Kovacevic & Maksic (2001), and due to their strongly basic character, guanidines can be considered as super-bases for biological systems, see: Ishikawa & Isobe (2002). For related structures, see: Cunha et al. (2005); Murtaza et al. (2007, 2008, 2009). For the preparation of N-benzoyl-N'-phenylthiourea, see: Rauf et al. (2009).

Experimental top

N-Benzoyl-N'-phenylthiourea (0.256 g, 1 mmol) was prepared (Rauf et al., 2009) and dissolved in 10 ml of dimethylformamide and taken into two neck round bottom flask. 2,4-dichloroaniline (0.16 g, 1 mmol) and triethylamine (0.28 ml, 2 mmol) were added and the mixture was stirred well below 5°C. Mercuric chloride (0.272 g, 1 mmol) was then added and mixture was vigorously stirred for 15 h till the completion of reaction as monitored by TLC. When all the thiourea was consumed, 20 ml of chloroform was added and the suspension was filtered through sintered glass funnel to remove residual HgS formed as a byproduct during the reaction. The solvent was evaporated under reduced pressure and residue was dissolved in 20 ml of CH₂Cl₂. Other byproducts were extracted out with water (4×30 ml). The organic phase was dried over anhydrous MgSO₄ and then filtered. The solvent was evaporated and product was further purified by column chromatography. The target guanidine was recrystallized in ethanol to obtain single crystals suitable for X-ray analysis.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004).

Figures top

	Fig. 1. Molecular structure of (I) showing atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Hydrogen-bonded dimer structure of (I). Hydrogen bonds shown as dashed lines.

2-Benzoyl-1-(2,4-dichlorophenyl)-3-phenylguanidine top

Crystal data top

C₂₀H₁₅Cl₂N₃O	F(000) = 792
M_r = 384.25	D_x = 1.449 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 5226 reflections
a = 16.461 (6) Å	θ = 3.1–27.5°
b = 6.663 (2) Å	µ = 0.38 mm⁻¹
c = 19.388 (6) Å	T = 123 K
β = 124.072 (5)°	Block, colourless
V = 1761.0 (10) Å³	0.42 × 0.40 × 0.18 mm
Z = 4

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3768 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
Detector resolution: 14.62 pixels mm^-1	h = −21→16
ω scans	k = −8→8
13586 measured reflections	l = −17→25
4023 independent 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0364P)² + 1.087P] where P = (F_o² + 2F_c²)/3
4023 reflections	(Δ/σ)_max < 0.001
241 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₀H₁₅Cl₂N₃O	V = 1761.0 (10) Å³
M_r = 384.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.461 (6) Å	µ = 0.38 mm⁻¹
b = 6.663 (2) Å	T = 123 K
c = 19.388 (6) Å	0.42 × 0.40 × 0.18 mm
β = 124.072 (5)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3768 reflections with I > 2σ(I)
13586 measured reflections	R_int = 0.031
4023 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.34 e Å⁻³
4023 reflections	Δρ_min = −0.27 e Å⁻³
241 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.16683 (11)	0.5401 (2)	0.00837 (10)	0.0159 (3)
N1	0.23055 (9)	0.3930 (2)	0.05737 (8)	0.0168 (3)
N2	0.27838 (10)	0.1383 (2)	0.15357 (9)	0.0190 (3)
H2	0.2660 (14)	0.070 (3)	0.1846 (13)	0.023*
N3	0.12213 (10)	0.2596 (2)	0.09071 (9)	0.0176 (3)
H3	0.0802 (15)	0.344 (3)	0.0586 (13)	0.021*
C2	0.20779 (11)	0.2689 (2)	0.09780 (10)	0.0159 (3)
O1	0.08319 (8)	0.57114 (18)	−0.00799 (7)	0.0198 (2)
C3	0.20711 (11)	0.6783 (2)	−0.02684 (10)	0.0169 (3)
C4	0.16230 (12)	0.8635 (3)	−0.05922 (10)	0.0197 (3)
H4	0.1064	0.9001	−0.0594	0.024*
C5	0.19875 (13)	0.9949 (3)	−0.09131 (11)	0.0244 (4)
H5	0.1687	1.1222	−0.1121	0.029*
C6	0.27903 (13)	0.9406 (3)	−0.09309 (11)	0.0270 (4)
H6	0.3033	1.0292	−0.1159	0.032*
C7	0.32341 (14)	0.7558 (3)	−0.06128 (12)	0.0294 (4)
H7	0.3782	0.7180	−0.0626	0.035*
C8	0.28878 (13)	0.6261 (3)	−0.02765 (11)	0.0233 (4)
H8	0.3206	0.5011	−0.0050	0.028*
C9	0.37728 (11)	0.1401 (2)	0.17925 (10)	0.0160 (3)
C10	0.45195 (12)	0.1401 (2)	0.26411 (10)	0.0162 (3)
C11	0.55020 (11)	0.1405 (2)	0.29205 (10)	0.0170 (3)
H11	0.6005	0.1393	0.3499	0.020*
C12	0.57271 (11)	0.1428 (2)	0.23292 (11)	0.0173 (3)
C13	0.50041 (12)	0.1377 (2)	0.14848 (10)	0.0186 (3)
H13	0.5175	0.1366	0.1091	0.022*
C14	0.40293 (12)	0.1341 (2)	0.12201 (10)	0.0184 (3)
H14	0.3530	0.1276	0.0642	0.022*
Cl1	0.42229 (3)	0.14079 (6)	0.33735 (2)	0.02082 (11)
Cl2	0.69542 (3)	0.15526 (6)	0.26631 (3)	0.02167 (11)
C15	0.10396 (11)	0.1209 (2)	0.13708 (10)	0.0160 (3)
C16	0.11539 (12)	0.1817 (3)	0.21063 (11)	0.0216 (3)
H16	0.1332	0.3162	0.2295	0.026*
C17	0.10044 (13)	0.0438 (3)	0.25644 (11)	0.0259 (4)
H17	0.1086	0.0843	0.3069	0.031*
C18	0.07378 (12)	−0.1519 (3)	0.22886 (11)	0.0237 (4)
H18	0.0639	−0.2454	0.2605	0.028*
C19	0.06150 (12)	−0.2117 (3)	0.15488 (11)	0.0224 (4)
H19	0.0423	−0.3454	0.1355	0.027*
C20	0.07740 (11)	−0.0753 (3)	0.10929 (10)	0.0191 (3)
H20	0.0701	−0.1165	0.0592	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0155 (7)	0.0168 (7)	0.0129 (7)	−0.0014 (6)	0.0065 (6)	−0.0022 (6)
N1	0.0163 (6)	0.0181 (7)	0.0157 (6)	0.0015 (5)	0.0086 (5)	0.0019 (5)
N2	0.0148 (6)	0.0207 (7)	0.0200 (7)	0.0019 (5)	0.0089 (6)	0.0060 (6)
N3	0.0143 (6)	0.0184 (7)	0.0177 (7)	0.0020 (5)	0.0074 (5)	0.0049 (6)
C2	0.0155 (7)	0.0152 (7)	0.0140 (7)	0.0002 (6)	0.0064 (6)	−0.0012 (6)
O1	0.0161 (5)	0.0210 (6)	0.0226 (6)	0.0033 (4)	0.0110 (5)	0.0056 (5)
C3	0.0158 (7)	0.0205 (8)	0.0114 (7)	−0.0024 (6)	0.0058 (6)	−0.0008 (6)
C4	0.0186 (7)	0.0226 (8)	0.0143 (7)	0.0000 (6)	0.0070 (6)	0.0013 (6)
C5	0.0273 (8)	0.0230 (9)	0.0166 (8)	−0.0022 (7)	0.0085 (7)	0.0035 (7)
C6	0.0302 (9)	0.0326 (10)	0.0199 (8)	−0.0075 (8)	0.0152 (7)	0.0026 (8)
C7	0.0284 (9)	0.0380 (11)	0.0301 (10)	0.0001 (8)	0.0215 (8)	0.0038 (8)
C8	0.0233 (8)	0.0271 (9)	0.0223 (8)	0.0037 (7)	0.0145 (7)	0.0039 (7)
C9	0.0147 (7)	0.0123 (7)	0.0183 (8)	0.0014 (6)	0.0076 (6)	0.0019 (6)
C10	0.0195 (7)	0.0139 (7)	0.0170 (7)	0.0002 (6)	0.0113 (6)	0.0008 (6)
C11	0.0160 (7)	0.0146 (7)	0.0159 (7)	0.0009 (6)	0.0062 (6)	0.0007 (6)
C12	0.0149 (7)	0.0139 (7)	0.0212 (8)	0.0011 (6)	0.0089 (6)	0.0005 (6)
C13	0.0204 (8)	0.0170 (8)	0.0199 (8)	0.0025 (6)	0.0123 (7)	0.0023 (6)
C14	0.0186 (7)	0.0174 (8)	0.0151 (7)	0.0010 (6)	0.0069 (6)	0.0007 (6)
Cl1	0.0237 (2)	0.0222 (2)	0.0199 (2)	0.00056 (15)	0.01430 (17)	0.00129 (15)
Cl2	0.01518 (19)	0.0240 (2)	0.0251 (2)	0.00091 (14)	0.01083 (16)	0.00198 (16)
C15	0.0118 (6)	0.0189 (8)	0.0151 (7)	0.0017 (6)	0.0062 (6)	0.0035 (6)
C16	0.0253 (8)	0.0186 (8)	0.0193 (8)	−0.0010 (6)	0.0114 (7)	−0.0014 (7)
C17	0.0311 (9)	0.0315 (10)	0.0180 (8)	0.0018 (8)	0.0155 (7)	0.0019 (7)
C18	0.0219 (8)	0.0255 (9)	0.0235 (9)	0.0023 (7)	0.0126 (7)	0.0087 (7)
C19	0.0199 (8)	0.0178 (8)	0.0260 (9)	−0.0009 (6)	0.0106 (7)	0.0015 (7)
C20	0.0173 (7)	0.0218 (8)	0.0162 (8)	0.0006 (6)	0.0082 (6)	0.0001 (6)

Geometric parameters (Å, º) top

C1—O1	1.2447 (19)	C9—C10	1.397 (2)
C1—N1	1.359 (2)	C10—C11	1.388 (2)
C1—C3	1.504 (2)	C10—Cl1	1.7412 (17)
N1—C2	1.329 (2)	C11—C12	1.388 (2)
N2—C2	1.367 (2)	C11—H11	0.9500
N2—C9	1.411 (2)	C12—C13	1.384 (2)
N2—H2	0.86 (2)	C12—Cl2	1.7439 (17)
N3—C2	1.339 (2)	C13—C14	1.384 (2)
N3—C15	1.433 (2)	C13—H13	0.9500
N3—H3	0.84 (2)	C14—H14	0.9500
C3—C4	1.393 (2)	C15—C20	1.388 (2)
C3—C8	1.397 (2)	C15—C16	1.390 (2)
C4—C5	1.390 (2)	C16—C17	1.392 (3)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.389 (3)	C17—C18	1.384 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.388 (3)	C18—C19	1.390 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.383 (3)	C19—C20	1.391 (2)
C7—H7	0.9500	C19—H19	0.9500
C8—H8	0.9500	C20—H20	0.9500
C9—C14	1.392 (2)

O1—C1—N1	127.45 (15)	C11—C10—C9	121.57 (15)
O1—C1—C3	119.26 (14)	C11—C10—Cl1	118.64 (13)
N1—C1—C3	113.27 (13)	C9—C10—Cl1	119.79 (13)
C2—N1—C1	119.92 (13)	C10—C11—C12	117.98 (15)
C2—N2—C9	125.14 (14)	C10—C11—H11	121.0
C2—N2—H2	117.2 (13)	C12—C11—H11	121.0
C9—N2—H2	115.8 (13)	C13—C12—C11	121.75 (15)
C2—N3—C15	122.90 (14)	C13—C12—Cl2	119.34 (13)
C2—N3—H3	115.4 (14)	C11—C12—Cl2	118.91 (12)
C15—N3—H3	121.7 (14)	C12—C13—C14	119.28 (16)
N1—C2—N3	126.61 (14)	C12—C13—H13	120.4
N1—C2—N2	117.82 (14)	C14—C13—H13	120.4
N3—C2—N2	115.56 (14)	C13—C14—C9	120.69 (15)
C4—C3—C8	119.04 (15)	C13—C14—H14	119.7
C4—C3—C1	119.33 (14)	C9—C14—H14	119.7
C8—C3—C1	121.63 (15)	C20—C15—C16	120.33 (15)
C5—C4—C3	120.48 (16)	C20—C15—N3	119.68 (15)
C5—C4—H4	119.8	C16—C15—N3	119.97 (15)
C3—C4—H4	119.8	C15—C16—C17	119.43 (16)
C6—C5—C4	120.14 (17)	C15—C16—H16	120.3
C6—C5—H5	119.9	C17—C16—H16	120.3
C4—C5—H5	119.9	C18—C17—C16	120.42 (17)
C7—C6—C5	119.44 (17)	C18—C17—H17	119.8
C7—C6—H6	120.3	C16—C17—H17	119.8
C5—C6—H6	120.3	C17—C18—C19	119.99 (16)
C8—C7—C6	120.71 (17)	C17—C18—H18	120.0
C8—C7—H7	119.6	C19—C18—H18	120.0
C6—C7—H7	119.6	C18—C19—C20	119.90 (16)
C7—C8—C3	120.18 (17)	C18—C19—H19	120.1
C7—C8—H8	119.9	C20—C19—H19	120.1
C3—C8—H8	119.9	C15—C20—C19	119.93 (16)
C14—C9—C10	118.64 (15)	C15—C20—H20	120.0
C14—C9—N2	121.60 (14)	C19—C20—H20	120.0
C10—C9—N2	119.71 (15)

O1—C1—N1—C2	−3.8 (3)	N2—C9—C10—C11	179.58 (14)
C3—C1—N1—C2	174.94 (14)	C14—C9—C10—Cl1	−178.31 (12)
C1—N1—C2—N3	6.2 (2)	N2—C9—C10—Cl1	−0.7 (2)
C1—N1—C2—N2	−172.70 (14)	C9—C10—C11—C12	0.6 (2)
C15—N3—C2—N1	−179.82 (15)	Cl1—C10—C11—C12	−179.13 (12)
C15—N3—C2—N2	−0.9 (2)	C10—C11—C12—C13	−2.3 (2)
C9—N2—C2—N1	8.0 (2)	C10—C11—C12—Cl2	177.02 (12)
C9—N2—C2—N3	−171.02 (15)	C11—C12—C13—C14	1.3 (2)
O1—C1—C3—C4	15.7 (2)	Cl2—C12—C13—C14	−177.99 (12)
N1—C1—C3—C4	−163.16 (14)	C12—C13—C14—C9	1.4 (2)
O1—C1—C3—C8	−164.54 (16)	C10—C9—C14—C13	−3.0 (2)
N1—C1—C3—C8	16.6 (2)	N2—C9—C14—C13	179.45 (15)
C8—C3—C4—C5	−0.5 (2)	C2—N3—C15—C20	−82.0 (2)
C1—C3—C4—C5	179.28 (15)	C2—N3—C15—C16	96.34 (19)
C3—C4—C5—C6	1.5 (3)	C20—C15—C16—C17	0.3 (2)
C4—C5—C6—C7	−1.1 (3)	N3—C15—C16—C17	−178.04 (15)
C5—C6—C7—C8	−0.3 (3)	C15—C16—C17—C18	−0.4 (3)
C6—C7—C8—C3	1.3 (3)	C16—C17—C18—C19	−0.2 (3)
C4—C3—C8—C7	−0.9 (3)	C17—C18—C19—C20	0.9 (3)
C1—C3—C8—C7	179.35 (16)	C16—C15—C20—C19	0.4 (2)
C2—N2—C9—C14	−53.8 (2)	N3—C15—C20—C19	178.77 (14)
C2—N2—C9—C10	128.62 (17)	C18—C19—C20—C15	−1.0 (2)
C14—C9—C10—C11	2.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.84 (2)	2.01 (2)	2.6471 (19)	132.7 (18)
N3—H3···O1ⁱ	0.84 (2)	2.36 (2)	3.032 (2)	138.2 (18)

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅Cl₂N₃O
M_r	384.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	16.461 (6), 6.663 (2), 19.388 (6)
β (°)	124.072 (5)
V (Å³)	1761.0 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.42 × 0.40 × 0.18

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13586, 4023, 3768
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.099, 1.12
No. of reflections	4023
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.27

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2001), SIR97 (Altomare et al., 1999), ORTEPII (Johnson, 1976) and ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.84 (2)	2.01 (2)	2.6471 (19)	132.7 (18)
N3—H3···O1ⁱ	0.84 (2)	2.36 (2)	3.032 (2)	138.2 (18)

Symmetry code: (i) −x, −y+1, −z.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support of this research project.

References

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