N-Benzoyl-N′,N′′-diphenyl­guanidinium chloride

Murtaza, G.; Said, M.; Khawar Rauf, M.; Masahiro, E.; Badshah, A.

doi:10.1107/S1600536807065166

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o333

https://doi.org/10.1107/S1600536807065166

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N-Benzoyl-N′,N′′-diphenylguanidinium chloride

Ghulam Murtaza,^a Muhammad Said,^a M. Khawar Rauf,^b Ebihara Masahiro ^b and Amin Badshah ^a ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Engineering, Gifu University Yanagido, Gifu 501-1193, Japan
^*Correspondence e-mail: aminbadshah@yahoo.com

(Received 29 October 2007; accepted 2 December 2007; online 21 December 2007)

In the title compound, C₂₀H₁₈N₃O⁺·Cl⁻, the orientation of the aromatic rings around the planar CN₃⁺ unit produces steric hindrance. As a consequence of this particular orientation of the guanidinium cation, hydrogen bonding is restricted to N—H⋯Cl and intramolecular 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 intramolecular 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_r = 351.82
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.133
S = 1.13
4050 reflections
238 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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)

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065166/ez2109Isup2.hkl

checkCIF report

Comment top

Guanidines are used in medicine as analgesic, antihypertensive, antibacterial, cancerostatic and cytotoxic agents (Taniguchi et al., 1993; Yoshiizumi et al., 1998; Moroni et al., 2001). They have potential applications in the fields of analytical and synthetic organic chemistry (Aldhaheri,1998; Köhn et al., 2004). The title compound (I), Fig. 1, is a typical N,N',N"-trisubstituted guanidinium halide salt with normal geometric parameters (Said et al., 2006). The C(1)—O(1) bond shows the expected full double bond character while the short values for the C(1)—N(1), C(2)—N(1), C(2)—N(2), and C(2)—N(3) bond lengths indicate partial double bond character (Table 1). The dihedral angles between the guanidinium plane (C(2)/N(1)/N(2)/N(3)) and the two phenyl ring planes formed by C(15)—C(20) & C(9)—C(14) are 62.31 (8)° & 64.24 (8)° respectively, and that between the guanidinium plane and the aroyl group is 20.17 (10)°. The guanidinium and carbonyl groups are almost coplanar, as reflected by the torsion angles O(1)—C(1)—N(1)—C(2) = -7.5 (3)°, N(2)—C(2)— N(1)—C(1) = -174.26 (17))°, N(3)—C(2)—N(1)—C(1) = 7.2 (3)° and C(3)— C(1)—N(1)—C(2) = 175.92 (16)° (Table 1), this is associated with the intramolecular N—H···O hydrogen bond (Table 2), forming the six-membered ring commonly observed in this class of compounds (Cunha et al., 2005).

Related literature top

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 top

The guanidine was synthesized by a previously reported method (Cunha et al., 2002), from N-benzoyl-N'-phenylthiourea and aniline. 0.315 g (1 mmol) of synthesized guanidine was added to a mixture of 20 ml e thanol and 1 ml of 37% v/v HCl with constant stirring at 323 K for 30 min. The reaction mixture was concentrated by evaporating 50% of the solvent under reduced pressure, and block like X-ray quality crystals were obtained by slow evaporation at room temperature.

Structure description top

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).

Computing details top

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.

Figures top

Fig. 1. Molecular structure of (I) showing atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown by dashed lines.

N-Benzoyl-N',N''-diphenylguanidinium chloride top

Crystal data top

C₂₀H₁₈N₃O⁺·Cl⁻	Z = 2
M_r = 351.82	F(000) = 368
Triclinic, P1	D_x = 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 = 3.2–27.5°
c = 10.966 (6) Å	µ = 0.22 mm⁻¹
α = 70.193 (10)°	T = 296 K
β = 88.612 (19)°	Block, colourless
γ = 84.524 (18)°	0.50 × 0.40 × 0.25 mm
V = 904.2 (8) Å³

Data collection top

Rigaku/MSC Mercury CCD diffractometer	4050 independent reflections
Radiation source: fine-focus sealed tube	3534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 14.62 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −8→11
Absorption correction: integration (Higashi, 1999)	k = −13→8
T_min = 0.653, T_max = 0.803	l = −14→14
7197 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0563P)² + 0.2415P] where P = (F_o² + 2F_c²)/3
4050 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₀H₁₈N₃O⁺·Cl⁻	γ = 84.524 (18)°
M_r = 351.82	V = 904.2 (8) Å³
Triclinic, P1	Z = 2
a = 8.586 (4) Å	Mo Kα radiation
b = 10.254 (5) Å	µ = 0.22 mm⁻¹
c = 10.966 (6) Å	T = 296 K
α = 70.193 (10)°	0.50 × 0.40 × 0.25 mm
β = 88.612 (19)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	4050 independent reflections
Absorption correction: integration (Higashi, 1999)	3534 reflections with I > 2σ(I)
T_min = 0.653, T_max = 0.803	R_int = 0.026
7197 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.20 e Å⁻³
4050 reflections	Δρ_min = −0.32 e Å⁻³
238 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₃O⁺·Cl⁻
M_r	351.82
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.586 (4), 10.254 (5), 10.966 (6)
α, β, γ (°)	70.193 (10), 88.612 (19), 84.524 (18)
V (Å³)	904.2 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.50 × 0.40 × 0.25

Data collection
Diffractometer	Rigaku/MSC Mercury CCD
Absorption correction	Integration (Higashi, 1999)
T_min, T_max	0.653, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	7197, 4050, 3534
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.133, 1.13
No. of reflections	4050
No. of parameters	238
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.32

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

Selected bond lengths (Å) top

C1—O1	1.224 (2)	C2—N2	1.321 (2)
C1—N1	1.376 (2)	C2—N3	1.326 (2)

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

The authors are grateful to the HEC Pakistan for financial support of this research project.

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