2-Benzoyl-1,1-diethyl-3-phenyl-guanidine.

In the title tetrasubstituted guanidine, C(18)H(21)N(3)O, the guanidine and carbonyl groups are not coplanar, as reflected by the torsion angles involving the N=C atoms [17.6 (3), -141.68 (17) and 42.2 (3)°]. This is probably due to the absence of an intra-molecular N-H⋯O hydrogen bond, forming a six-membered ring, and is commonly observed in this class of compounds. In the crystal structure, centrosymmetric dimers are formed via pairs of inter-molecular N-H⋯O hydrogen bonds. The dihedral angles between the guanidine plane and the phenyl ring and benzoyl plane are38.06 (9) and 41.54 (7)°, respectively.

Related literature

For thio­urea derivatives with biological activity, see: Berlinck (2002 ▶); Heys et al. (2000 ▶); Laeckmann et al. (2002 ▶); Kelley et al. (2001 ▶); Moroni et al. (2001 ▶); Ishikawa et al. (2002 ▶). For related structures, see: Murtaza et al. (2007 ▶, 2008 ▶); Cunha et al. (2005 ▶).

Experimental

Crystal data

C18H21N3O

M = 295.38

Monoclinic,

a = 10.472 (6) Å

b = 15.010 (8) Å

c = 10.154 (6) Å

β = 102.992 (6)°

V = 1555.2 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 (2) K

0.50 × 0.40 × 0.30 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: none

12318 measured reflections

3556 independent reflections

3239 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.112

S = 1.27

3556 reflections

205 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.19 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 ▶); software used to prepare material for publication: SHELXL97 and TEXSAn class="Chemical">N.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001469/su2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001469/su2090Isup2.hkl

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

C18H21N3O	F(000) = 632
Mr = 295.38	Dx = 1.262 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 4060 reflections
a = 10.472 (6) Å	θ = 6.3–55.0°
b = 15.010 (8) Å	µ = 0.08 mm−1
c = 10.154 (6) Å	T = 113 K
β = 102.992 (6)°	Block, colourless
V = 1555.2 (15) Å3	0.50 × 0.40 × 0.30 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	3239 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 14.62 pixels mm-1	θmax = 27.5°, θmin = 3.4°
ω scans	h = −13→8
12318 measured reflections	k = −19→19
3556 independent reflections	l = −13→13

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.27	w = 1/[σ2(Fo2) + (0.0155P)2 + 1.0509P] where P = (Fo2 + 2Fc2)/3
3556 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.21836 (16)	0.49684 (12)	0.59825 (17)	0.0158 (3)
N1	0.28409 (14)	0.54983 (10)	0.53093 (14)	0.0174 (3)
N2	0.24622 (14)	0.50194 (10)	0.73344 (14)	0.0172 (3)
N3	0.12913 (15)	0.43370 (10)	0.53944 (14)	0.0171 (3)
H3	0.063 (2)	0.4210 (15)	0.580 (2)	0.035 (6)*
C2	0.22449 (17)	0.58833 (11)	0.41264 (16)	0.0162 (3)
O1	0.10437 (12)	0.59798 (9)	0.36752 (12)	0.0208 (3)
C3	0.31721 (17)	0.62748 (11)	0.33424 (17)	0.0168 (4)
C4	0.45097 (18)	0.63592 (12)	0.39163 (18)	0.0201 (4)
H4	0.4854	0.6146	0.4806	0.024*
C5	0.53391 (19)	0.67529 (13)	0.31946 (19)	0.0248 (4)
H5	0.6247	0.6810	0.3593	0.030*
C6	0.4846 (2)	0.70640 (13)	0.18924 (19)	0.0249 (4)
H6	0.5414	0.7337	0.1402	0.030*
C7	0.35200 (19)	0.69752 (12)	0.13084 (18)	0.0228 (4)
H7	0.3182	0.7184	0.0414	0.027*
C8	0.26838 (18)	0.65820 (12)	0.20278 (17)	0.0195 (4)
H8	0.1777	0.6522	0.1623	0.023*
C9	0.32896 (18)	0.57493 (13)	0.80129 (18)	0.0222 (4)
H9A	0.3065	0.5871	0.8892	0.027*
H9B	0.3097	0.6294	0.7455	0.027*
C10	0.47450 (19)	0.55474 (14)	0.82538 (19)	0.0286 (4)
H10A	0.4928	0.4974	0.8718	0.043*
H10B	0.5243	0.6018	0.8814	0.043*
H10C	0.5003	0.5521	0.7385	0.043*
C11	0.20739 (18)	0.43504 (12)	0.82325 (17)	0.0202 (4)
H11A	0.2858	0.4169	0.8922	0.024*
H11B	0.1734	0.3816	0.7694	0.024*
C12	0.10328 (19)	0.46898 (14)	0.89432 (19)	0.0262 (4)
H12A	0.1380	0.5199	0.9518	0.039*
H12B	0.0793	0.4213	0.9502	0.039*
H12C	0.0256	0.4876	0.8267	0.039*
C13	0.12031 (17)	0.39230 (11)	0.41262 (16)	0.0156 (3)
C14	0.22270 (18)	0.39048 (12)	0.34509 (17)	0.0195 (4)
H14	0.3026	0.4205	0.3821	0.023*
C15	0.20751 (19)	0.34464 (12)	0.22372 (18)	0.0225 (4)
H15	0.2771	0.3444	0.1777	0.027*
C16	0.09264 (19)	0.29929 (12)	0.16861 (18)	0.0240 (4)
H16	0.0834	0.2680	0.0857	0.029*
C17	−0.00860 (19)	0.30017 (12)	0.23605 (18)	0.0227 (4)
H17	−0.0876	0.2691	0.1993	0.027*
C18	0.00458 (17)	0.34619 (12)	0.35696 (17)	0.0190 (4)
H18	−0.0655	0.3464	0.4023	0.023*

	U11	U22	U33	U12	U13	U23
C1	0.0136 (8)	0.0170 (8)	0.0167 (8)	0.0015 (7)	0.0033 (6)	0.0001 (6)
N1	0.0168 (7)	0.0203 (8)	0.0156 (7)	−0.0023 (6)	0.0049 (5)	0.0008 (6)
N2	0.0190 (7)	0.0188 (7)	0.0145 (7)	−0.0030 (6)	0.0049 (6)	0.0001 (6)
N3	0.0158 (7)	0.0209 (8)	0.0153 (7)	−0.0029 (6)	0.0053 (6)	0.0002 (6)
C2	0.0181 (9)	0.0161 (8)	0.0156 (8)	−0.0008 (7)	0.0062 (7)	−0.0028 (6)
O1	0.0167 (6)	0.0247 (7)	0.0217 (6)	0.0005 (5)	0.0058 (5)	0.0048 (5)
C3	0.0200 (9)	0.0151 (8)	0.0175 (8)	0.0000 (7)	0.0086 (7)	−0.0019 (6)
C4	0.0210 (9)	0.0198 (9)	0.0201 (9)	−0.0001 (7)	0.0059 (7)	0.0017 (7)
C5	0.0213 (9)	0.0243 (10)	0.0308 (10)	−0.0031 (8)	0.0098 (8)	0.0006 (8)
C6	0.0304 (10)	0.0207 (9)	0.0291 (10)	−0.0032 (8)	0.0180 (8)	0.0001 (8)
C7	0.0332 (11)	0.0197 (9)	0.0177 (8)	0.0006 (8)	0.0101 (8)	0.0015 (7)
C8	0.0221 (9)	0.0189 (9)	0.0181 (8)	0.0001 (7)	0.0060 (7)	−0.0009 (7)
C9	0.0272 (10)	0.0227 (9)	0.0168 (8)	−0.0064 (8)	0.0053 (7)	−0.0036 (7)
C10	0.0258 (10)	0.0346 (11)	0.0234 (9)	−0.0083 (9)	0.0011 (8)	−0.0010 (8)
C11	0.0228 (9)	0.0232 (9)	0.0146 (8)	−0.0021 (7)	0.0041 (7)	0.0041 (7)
C12	0.0269 (10)	0.0337 (11)	0.0205 (9)	−0.0046 (8)	0.0105 (8)	0.0014 (8)
C13	0.0176 (8)	0.0139 (8)	0.0145 (8)	0.0016 (7)	0.0022 (6)	0.0020 (6)
C14	0.0167 (9)	0.0217 (9)	0.0202 (9)	−0.0014 (7)	0.0044 (7)	−0.0008 (7)
C15	0.0231 (9)	0.0224 (9)	0.0242 (9)	0.0018 (7)	0.0102 (7)	−0.0009 (7)
C16	0.0339 (11)	0.0197 (9)	0.0183 (9)	−0.0010 (8)	0.0056 (8)	−0.0035 (7)
C17	0.0248 (10)	0.0193 (9)	0.0225 (9)	−0.0042 (7)	0.0023 (7)	−0.0011 (7)
C18	0.0172 (9)	0.0200 (9)	0.0201 (8)	−0.0007 (7)	0.0049 (7)	0.0022 (7)

C1—N1	1.336 (2)	C9—H9A	0.9900
C1—N2	1.340 (2)	C9—H9B	0.9900
C1—N3	1.370 (2)	C10—H10A	0.9800
N1—C2	1.352 (2)	C10—H10B	0.9800
N2—C9	1.469 (2)	C10—H10C	0.9800
N2—C11	1.474 (2)	C11—C12	1.524 (3)
N3—C13	1.414 (2)	C11—H11A	0.9900
N3—H3	0.90 (2)	C11—H11B	0.9900
C2—O1	1.247 (2)	C12—H12A	0.9800
C2—C3	1.506 (2)	C12—H12B	0.9800
C3—C8	1.396 (2)	C12—H12C	0.9800
C3—C4	1.397 (3)	C13—C14	1.397 (3)
C4—C5	1.388 (3)	C13—C18	1.400 (2)
C4—H4	0.9500	C14—C15	1.389 (3)
C5—C6	1.388 (3)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.386 (3)
C6—C7	1.388 (3)	C15—H15	0.9500
C6—H6	0.9500	C16—C17	1.385 (3)
C7—C8	1.392 (3)	C16—H16	0.9500
C7—H7	0.9500	C17—C18	1.388 (3)
C8—H8	0.9500	C17—H17	0.9500
C9—C10	1.519 (3)	C18—H18	0.9500
N1—C1—N2	118.14 (15)	C9—C10—H10A	109.5
N1—C1—N3	124.62 (15)	C9—C10—H10B	109.5
N2—C1—N3	117.14 (15)	H10A—C10—H10B	109.5
C1—N1—C2	121.38 (15)	C9—C10—H10C	109.5
C1—N2—C9	119.52 (14)	H10A—C10—H10C	109.5
C1—N2—C11	124.62 (15)	H10B—C10—H10C	109.5
C9—N2—C11	115.71 (14)	N2—C11—C12	113.04 (15)
C1—N3—C13	126.83 (15)	N2—C11—H11A	109.0
C1—N3—H3	117.8 (15)	C12—C11—H11A	109.0
C13—N3—H3	114.9 (14)	N2—C11—H11B	109.0
O1—C2—N1	127.02 (16)	C12—C11—H11B	109.0
O1—C2—C3	118.52 (16)	H11A—C11—H11B	107.8
N1—C2—C3	114.36 (15)	C11—C12—H12A	109.5
C8—C3—C4	119.10 (16)	C11—C12—H12B	109.5
C8—C3—C2	119.54 (16)	H12A—C12—H12B	109.5
C4—C3—C2	121.33 (16)	C11—C12—H12C	109.5
C5—C4—C3	120.41 (17)	H12A—C12—H12C	109.5
C5—C4—H4	119.8	H12B—C12—H12C	109.5
C3—C4—H4	119.8	C14—C13—C18	118.86 (16)
C6—C5—C4	120.22 (18)	C14—C13—N3	123.74 (16)
C6—C5—H5	119.9	C18—C13—N3	117.28 (16)
C4—C5—H5	119.9	C15—C14—C13	119.85 (17)
C5—C6—C7	119.79 (17)	C15—C14—H14	120.1
C5—C6—H6	120.1	C13—C14—H14	120.1
C7—C6—H6	120.1	C16—C15—C14	121.16 (18)
C6—C7—C8	120.23 (17)	C16—C15—H15	119.4
C6—C7—H7	119.9	C14—C15—H15	119.4
C8—C7—H7	119.9	C17—C16—C15	119.13 (17)
C7—C8—C3	120.24 (17)	C17—C16—H16	120.4
C7—C8—H8	119.9	C15—C16—H16	120.4
C3—C8—H8	119.9	C16—C17—C18	120.46 (17)
N2—C9—C10	113.05 (16)	C16—C17—H17	119.8
N2—C9—H9A	109.0	C18—C17—H17	119.8
C10—C9—H9A	109.0	C17—C18—C13	120.53 (17)
N2—C9—H9B	109.0	C17—C18—H18	119.7
C10—C9—H9B	109.0	C13—C18—H18	119.7
H9A—C9—H9B	107.8
N2—C1—N1—C2	−141.68 (17)	C5—C6—C7—C8	0.5 (3)
N3—C1—N1—C2	42.2 (3)	C6—C7—C8—C3	0.1 (3)
N1—C1—N2—C9	10.7 (2)	C4—C3—C8—C7	−0.7 (3)
N3—C1—N2—C9	−172.82 (15)	C2—C3—C8—C7	177.63 (16)
N1—C1—N2—C11	−164.64 (16)	C1—N2—C9—C10	−85.7 (2)
N3—C1—N2—C11	11.8 (2)	C11—N2—C9—C10	90.06 (19)
N1—C1—N3—C13	22.4 (3)	C1—N2—C11—C12	−110.70 (19)
N2—C1—N3—C13	−153.84 (16)	C9—N2—C11—C12	73.8 (2)
C1—N1—C2—O1	17.6 (3)	C1—N3—C13—C14	19.1 (3)
C1—N1—C2—C3	−166.17 (15)	C1—N3—C13—C18	−164.97 (16)
O1—C2—C3—C8	−12.0 (2)	C18—C13—C14—C15	1.1 (3)
N1—C2—C3—C8	171.40 (16)	N3—C13—C14—C15	176.97 (16)
O1—C2—C3—C4	166.25 (16)	C13—C14—C15—C16	−0.9 (3)
N1—C2—C3—C4	−10.3 (2)	C14—C15—C16—C17	0.2 (3)
C8—C3—C4—C5	0.8 (3)	C15—C16—C17—C18	0.3 (3)
C2—C3—C4—C5	−177.53 (16)	C16—C17—C18—C13	−0.1 (3)
C3—C4—C5—C6	−0.2 (3)	C14—C13—C18—C17	−0.6 (3)
C4—C5—C6—C7	−0.4 (3)	N3—C13—C18—C17	−176.78 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.90 (2)	1.97 (2)	2.852 (2)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.90 (2)	1.97 (2)	2.852 (2)	168 (2)

Symmetry code: (i) .