2-Benzoyl-1-(2,4-dichloro-phen-yl)-3-phenyl-guanidine.

In the title compound, C(20)H(15)Cl(2)N(3)O, 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-hexa-gonal ring formed by intra-molecular N-H⋯O hydrogen bonds. The crystal packing is stabilized by inter-molecular N-H⋯O hydrogen bonds, which link the mol-ecules 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 = 384.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.099

S = 1.12

4023 reflections

241 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.27 e Å−3

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 class="Chemical">N.

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

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

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

C20H15Cl2N3O	F(000) = 792
Mr = 384.25	Dx = 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

Rigaku/MSC Mercury CCD diffractometer	3768 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 27.5°, θmin = 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 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(Fo2) + (0.0364P)2 + 1.087P] where P = (Fo2 + 2Fc2)/3
4023 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .