N-Benzoyl-N',N''-diphenyl-guanidinium chloride.

In the title compound, C(20)H(18)N(3)O(+)·Cl(-), the orientation of the aromatic rings around the planar CN(3) (+) unit produces steric hindrance. As a consequence of this particular orientation of the guanidinium cation, hydrogen bonding is restricted to N-H⋯Cl and intra-molecular N-H⋯O hydrogen bonds within the discrete unit. The guanidinium and carbonyl groups are coplanar as a result of the six-membered ring formed by the N-H⋯O intra-molecular hydrogen bond. The dihedral angles between the guanidinium plane and the two phenyl rings are 62.31 (8) and 64.24 (8)°.

Related literature

For related structures, see: Said et al. (2006 ▶); Cunha et al. (2005 ▶). For related literature, see: Aldhaheri (1998 ▶); Cunha et al. (2002 ▶); Köhn et al. (2004 ▶); Moroni et al. (2001 ▶); Taniguchi et al. (1993 ▶); Yoshiizumi et al. (1998 ▶).

Experimental

Crystal data

C20H18N3O+·Cl−

M = 351.82

Triclinic,

a = 8.586 (4) Å

b = 10.254 (5) Å

c = 10.966 (6) Å

α = 70.193 (10)°

β = 88.612 (19)°

γ = 84.524 (18)°

V = 904.2 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 (2) K

0.50 × 0.40 × 0.25 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: integration (Higashi, 1999 ▶) T min = 0.653, T max = 0.803

7197 measured reflections

4050 independent reflections

3534 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.133

S = 1.13

4050 reflections

238 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.32 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, 1997 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and TEXSAN.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065166/ez2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065166/ez2109Isup2.hkl

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

C20H18N3O+·Cl–	Z = 2
Mr = 351.82	F000 = 368
Triclinic, P1	Dx = 1.292 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71070 Å
a = 8.586 (4) Å	Cell parameters from 2693 reflections
b = 10.254 (5) Å	θ = 3.2–27.5º
c = 10.966 (6) Å	µ = 0.22 mm−1
α = 70.193 (10)º	T = 296 (2) K
β = 88.612 (19)º	Block, colourless
γ = 84.524 (18)º	0.50 × 0.40 × 0.25 mm
V = 904.2 (8) Å3

Rigaku/MSC Mercury CCD diffractometer	4050 independent reflections
Radiation source: fine-focus sealed tube	3534 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 14.62 pixels mm-1	θmax = 27.5º
T = 296(2) K	θmin = 3.2º
ω scans	h = −8→11
Absorption correction: integration(Higashi, 1999)	k = −13→8
Tmin = 0.653, Tmax = 0.803	l = −14→14
7197 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.2415P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
4050 reflections	Δρmax = 0.20 e Å−3
238 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.46455 (19)	0.16051 (18)	0.64865 (17)	0.0414 (4)
O1	0.56362 (16)	0.06102 (15)	0.68532 (14)	0.0638 (4)
C2	0.57534 (18)	0.26054 (17)	0.43234 (16)	0.0373 (3)
N1	0.46189 (16)	0.25511 (16)	0.52470 (14)	0.0393 (3)
H1	0.396 (3)	0.328 (3)	0.505 (2)	0.061 (6)*
C3	0.33471 (18)	0.18014 (18)	0.73498 (16)	0.0395 (4)
C4	0.1942 (2)	0.2597 (2)	0.69126 (18)	0.0467 (4)
H4	0.1799	0.3114	0.6038	0.056*
C5	0.0754 (2)	0.2616 (2)	0.7787 (2)	0.0584 (5)
H5	−0.0194	0.3137	0.7493	0.070*
C6	0.0966 (3)	0.1873 (3)	0.9083 (2)	0.0649 (6)
H6	0.0164	0.1895	0.9663	0.078*
C7	0.2365 (3)	0.1096 (3)	0.9525 (2)	0.0705 (7)
H7	0.2516	0.0606	1.0404	0.085*
C8	0.3544 (2)	0.1046 (2)	0.86592 (19)	0.0581 (5)
H8	0.4477	0.0501	0.8956	0.070*
N2	0.55540 (18)	0.36772 (16)	0.32355 (14)	0.0440 (4)
H2	0.487 (3)	0.434 (3)	0.327 (2)	0.058 (6)*
C9	0.62383 (19)	0.37844 (19)	0.20058 (16)	0.0409 (4)
C10	0.6906 (3)	0.4978 (2)	0.1331 (2)	0.0624 (6)
H10	0.6949	0.5679	0.1685	0.075*
C11	0.7517 (4)	0.5130 (3)	0.0115 (2)	0.0777 (7)
H11	0.7984	0.5934	−0.0344	0.093*
C12	0.7439 (3)	0.4111 (3)	−0.0417 (2)	0.0725 (7)
H12	0.7847	0.4221	−0.1235	0.087*
C13	0.6759 (3)	0.2927 (3)	0.0261 (2)	0.0696 (6)
H13	0.6708	0.2233	−0.0101	0.084*
C14	0.6142 (2)	0.2750 (2)	0.1486 (2)	0.0557 (5)
H14	0.5675	0.1947	0.1943	0.067*
N3	0.69145 (16)	0.16005 (16)	0.45603 (16)	0.0432 (3)
H3	0.683 (3)	0.100 (3)	0.530 (2)	0.065 (7)*
C15	0.84141 (18)	0.17037 (17)	0.39319 (15)	0.0362 (3)
C16	0.9279 (2)	0.27925 (19)	0.38423 (18)	0.0447 (4)
H16	0.8881	0.3502	0.4143	0.054*
C17	1.0751 (2)	0.2818 (2)	0.3298 (2)	0.0543 (5)
H17	1.1341	0.3557	0.3221	0.065*
C18	1.1351 (2)	0.1753 (2)	0.28699 (19)	0.0545 (5)
H18	1.2342	0.1776	0.2506	0.065*
C19	1.0488 (2)	0.0662 (2)	0.2980 (2)	0.0538 (5)
H19	1.0896	−0.0057	0.2695	0.065*
C20	0.9007 (2)	0.0627 (2)	0.35154 (19)	0.0472 (4)
H20	0.8418	−0.0112	0.3593	0.057*
Cl1	0.28841 (5)	0.55341 (5)	0.39536 (5)	0.05030 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0359 (8)	0.0424 (9)	0.0417 (9)	0.0028 (7)	0.0055 (7)	−0.0107 (7)
O1	0.0547 (8)	0.0564 (8)	0.0563 (8)	0.0208 (6)	0.0188 (6)	0.0039 (7)
C2	0.0352 (8)	0.0393 (8)	0.0386 (8)	0.0002 (6)	0.0047 (6)	−0.0161 (7)
N1	0.0340 (7)	0.0416 (8)	0.0395 (7)	0.0050 (6)	0.0055 (5)	−0.0125 (6)
C3	0.0341 (8)	0.0440 (9)	0.0396 (9)	0.0005 (6)	0.0047 (6)	−0.0144 (7)
C4	0.0396 (9)	0.0544 (11)	0.0423 (9)	0.0060 (7)	0.0012 (7)	−0.0144 (8)
C5	0.0384 (9)	0.0706 (14)	0.0621 (13)	0.0097 (9)	0.0065 (8)	−0.0213 (11)
C6	0.0529 (11)	0.0769 (15)	0.0576 (12)	0.0057 (10)	0.0225 (10)	−0.0179 (11)
C7	0.0669 (13)	0.0857 (17)	0.0422 (11)	0.0154 (12)	0.0141 (9)	−0.0065 (11)
C8	0.0480 (10)	0.0712 (13)	0.0422 (10)	0.0151 (9)	0.0035 (8)	−0.0078 (9)
N2	0.0470 (8)	0.0434 (8)	0.0373 (8)	0.0104 (6)	0.0062 (6)	−0.0124 (6)
C9	0.0390 (8)	0.0474 (9)	0.0326 (8)	0.0079 (7)	0.0002 (6)	−0.0119 (7)
C10	0.0884 (16)	0.0496 (11)	0.0458 (11)	−0.0048 (10)	0.0140 (10)	−0.0131 (9)
C11	0.1051 (19)	0.0655 (15)	0.0467 (12)	−0.0023 (13)	0.0217 (12)	−0.0014 (11)
C12	0.0776 (15)	0.0892 (18)	0.0357 (10)	0.0264 (13)	0.0086 (10)	−0.0114 (11)
C13	0.0798 (15)	0.0849 (17)	0.0535 (13)	0.0119 (13)	−0.0008 (11)	−0.0407 (13)
C14	0.0594 (12)	0.0614 (12)	0.0509 (11)	−0.0040 (9)	0.0045 (9)	−0.0257 (10)
N3	0.0373 (7)	0.0417 (8)	0.0443 (8)	0.0049 (6)	0.0100 (6)	−0.0092 (7)
C15	0.0327 (7)	0.0409 (8)	0.0334 (8)	0.0041 (6)	0.0033 (6)	−0.0128 (6)
C16	0.0467 (9)	0.0414 (9)	0.0474 (10)	0.0012 (7)	0.0027 (7)	−0.0184 (8)
C17	0.0442 (10)	0.0547 (11)	0.0598 (12)	−0.0093 (8)	0.0040 (8)	−0.0129 (9)
C18	0.0374 (9)	0.0683 (13)	0.0482 (11)	0.0048 (8)	0.0098 (8)	−0.0103 (9)
C19	0.0481 (10)	0.0619 (12)	0.0534 (11)	0.0141 (9)	0.0065 (8)	−0.0275 (10)
C20	0.0436 (9)	0.0475 (10)	0.0559 (11)	0.0013 (7)	0.0023 (8)	−0.0262 (9)
Cl1	0.0488 (3)	0.0513 (3)	0.0533 (3)	0.01300 (19)	−0.00668 (19)	−0.0253 (2)

C1—O1	1.224 (2)	C10—C11	1.385 (3)
C1—N1	1.376 (2)	C10—H10	0.9300
C1—C3	1.488 (2)	C11—C12	1.365 (4)
C2—N2	1.321 (2)	C11—H11	0.9300
C2—N3	1.326 (2)	C12—C13	1.367 (4)
C2—N1	1.379 (2)	C12—H12	0.9300
N1—H1	0.86 (2)	C13—C14	1.392 (3)
C3—C8	1.387 (3)	C13—H13	0.9300
C3—C4	1.387 (2)	C14—H14	0.9300
C4—C5	1.386 (3)	N3—C15	1.441 (2)
C4—H4	0.9300	N3—H3	0.84 (3)
C5—C6	1.373 (3)	C15—C16	1.374 (3)
C5—H5	0.9300	C15—C20	1.381 (2)
C6—C7	1.377 (3)	C16—C17	1.383 (3)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.380 (3)	C17—C18	1.381 (3)
C7—H7	0.9300	C17—H17	0.9300
C8—H8	0.9300	C18—C19	1.371 (3)
N2—C9	1.432 (2)	C18—H18	0.9300
N2—H2	0.86 (2)	C19—C20	1.386 (3)
C9—C10	1.369 (3)	C19—H19	0.9300
C9—C14	1.374 (3)	C20—H20	0.9300
O1—C1—N1	122.33 (15)	C11—C10—H10	120.3
O1—C1—C3	121.03 (16)	C12—C11—C10	120.6 (2)
N1—C1—C3	116.55 (14)	C12—C11—H11	119.7
N2—C2—N3	125.14 (15)	C10—C11—H11	119.7
N2—C2—N1	115.35 (14)	C11—C12—C13	119.7 (2)
N3—C2—N1	119.49 (15)	C11—C12—H12	120.2
C1—N1—C2	125.74 (14)	C13—C12—H12	120.2
C1—N1—H1	119.5 (15)	C12—C13—C14	120.7 (2)
C2—N1—H1	113.5 (15)	C12—C13—H13	119.6
C8—C3—C4	119.34 (16)	C14—C13—H13	119.6
C8—C3—C1	116.33 (15)	C9—C14—C13	118.7 (2)
C4—C3—C1	124.15 (16)	C9—C14—H14	120.7
C5—C4—C3	119.63 (18)	C13—C14—H14	120.7
C5—C4—H4	120.2	C2—N3—C15	125.89 (15)
C3—C4—H4	120.2	C2—N3—H3	111.2 (17)
C6—C5—C4	120.55 (18)	C15—N3—H3	119.3 (17)
C6—C5—H5	119.7	C16—C15—C20	121.04 (16)
C4—C5—H5	119.7	C16—C15—N3	120.56 (15)
C5—C6—C7	120.06 (18)	C20—C15—N3	118.21 (16)
C5—C6—H6	120.0	C15—C16—C17	119.03 (17)
C7—C6—H6	120.0	C15—C16—H16	120.5
C6—C7—C8	119.8 (2)	C17—C16—H16	120.5
C6—C7—H7	120.1	C18—C17—C16	120.43 (19)
C8—C7—H7	120.1	C18—C17—H17	119.8
C7—C8—C3	120.55 (19)	C16—C17—H17	119.8
C7—C8—H8	119.7	C19—C18—C17	120.10 (17)
C3—C8—H8	119.7	C19—C18—H18	120.0
C2—N2—C9	126.71 (15)	C17—C18—H18	120.0
C2—N2—H2	115.2 (15)	C18—C19—C20	120.09 (18)
C9—N2—H2	117.8 (15)	C18—C19—H19	120.0
C10—C9—C14	120.97 (18)	C20—C19—H19	120.0
C10—C9—N2	118.28 (17)	C15—C20—C19	119.30 (18)
C14—C9—N2	120.63 (17)	C15—C20—H20	120.3
C9—C10—C11	119.3 (2)	C19—C20—H20	120.3
C9—C10—H10	120.3
O1—C1—N1—C2	−7.5 (3)	C14—C9—C10—C11	−1.1 (3)
C3—C1—N1—C2	175.92 (16)	N2—C9—C10—C11	−177.3 (2)
N2—C2—N1—C1	−174.26 (17)	C9—C10—C11—C12	0.8 (4)
N3—C2—N1—C1	7.2 (3)	C10—C11—C12—C13	−0.3 (4)
O1—C1—C3—C8	16.6 (3)	C11—C12—C13—C14	0.1 (4)
N1—C1—C3—C8	−166.76 (18)	C10—C9—C14—C13	0.9 (3)
O1—C1—C3—C4	−158.4 (2)	N2—C9—C14—C13	176.99 (18)
N1—C1—C3—C4	18.2 (3)	C12—C13—C14—C9	−0.4 (3)
C8—C3—C4—C5	−0.5 (3)	N2—C2—N3—C15	23.2 (3)
C1—C3—C4—C5	174.43 (19)	N1—C2—N3—C15	−158.45 (16)
C3—C4—C5—C6	1.0 (3)	C2—N3—C15—C16	50.4 (3)
C4—C5—C6—C7	−0.2 (4)	C2—N3—C15—C20	−134.56 (19)
C5—C6—C7—C8	−1.2 (4)	C20—C15—C16—C17	1.5 (3)
C6—C7—C8—C3	1.7 (4)	N3—C15—C16—C17	176.39 (17)
C4—C3—C8—C7	−0.9 (3)	C15—C16—C17—C18	−1.0 (3)
C1—C3—C8—C7	−176.2 (2)	C16—C17—C18—C19	0.1 (3)
N3—C2—N2—C9	18.6 (3)	C17—C18—C19—C20	0.4 (3)
N1—C2—N2—C9	−159.87 (16)	C16—C15—C20—C19	−1.0 (3)
C2—N2—C9—C10	−133.2 (2)	N3—C15—C20—C19	−176.09 (17)
C2—N2—C9—C14	50.6 (3)	C18—C19—C20—C15	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.86 (2)	2.32 (3)	3.143 (2)	159 (2)
N2—H2···Cl1	0.86 (2)	2.27 (2)	3.0977 (18)	162 (2)
N3—H3···O1	0.84 (3)	1.91 (3)	2.628 (2)	143 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.86 (2)	2.32 (3)	3.143 (2)	159 (2)
N2—H2⋯Cl1	0.86 (2)	2.27 (2)	3.0977 (18)	162 (2)
N3—H3⋯O1	0.84 (3)	1.91 (3)	2.628 (2)	143 (2)