2-Benzoyl-1,1-diethyl-3-phenyl­guanidine

Murtaza, G.; Hanif-Ur-Rehman; Khawar Rauf, M.; Ebihara, M.; Badshah, A.

doi:10.1107/S1600536809001469

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o343

doi:10.1107/S1600536809001469

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2-Benzoyl-1,1-diethyl-3-phenylguanidine

Ghulam Murtaza,^a Hanif-Ur-Rehman,^b M. Khawar Rauf,^a Masahiro Ebihara ^c and Amin Badshah ^a ^*

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

(Received 9 January 2009; accepted 12 January 2009; online 17 January 2009)

In the title tetrasubstituted guanidine, C₁₈H₂₁N₃O, 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 intramolecular 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 intermolecular 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_r = 295.38
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.068
wR(F²) = 0.112
S = 1.27
3556 reflections
205 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) -x, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

Guanidines are important compounds that have many biological, chemical and medicinal applications (Berlinck et al., 2002; Heys et al., 2000). They have received increasing interest as medicinal agents with antitumour, anti-hypertensive, anti-glaucoma and cardiotonic activities (Laeckmann et al., 2002; Kelley et al., 2001; Moroni et al., 2001). Due to their strongly basic character, they can be considered as super-bases that readily undergo protonation to generate resonance-stabilized guanidinium cations (Ishikawa et al., 2002).

The molecular structure of the title compound, (I), is illustrated in Fig. 1. It is a typical N',N,N,N''-Tetrasubstituted guanidine with normal geometrical parameters (Murtaza et al., 2007, 2008; Cunha et al., 2005). The carbonyl bond (C2═O1) shows the expected full double bond character, while the shorter values for bonds C2—N1, N1-C1, C1—N2, and C1—N3 indicate partial double bond character. The dihedral angles between the guanidine mean plane (C1/N1/N2/N3), and the phenyl ring (C13–C18), the benzoyl ring (C3-C8,C2,O1) and the N2/C9/C11 plane, are 38.06 (9)°, 41.54 (7)°, and 11.97 (13)°, respectively. The guanidine moiety and the carbonyl group are not co-planar, as reflected by the torsion angles C1—N1—C2—O1 = 17.6 (3)°, N2—C1—N1—C2 = -141.68 (17)°, and N3—C1—N1—C2 = 42.2 (3)°. This is probably due to the absence of an intramolecular N—H···O hydrogen bond, forming a six-membered ring, and commonly observed in this class of compounds (Cunha et al., 2005).

The crystal packing shows intermolecular N—H···O hydrogen bonds which result in the formation of centrosymmetric dimers (Fig. 2).

Related literature top

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 top

N-Benzoyl-N'-phenylthiourea (0.512 g, 2 mmol), triethyl amine (0.56 ml, 4 mmol) and diethyl amine (0.11 mL, 2 mmol) dissolved in 20 ml dimethylformamide, were mixed with vigourous stirring at 5°C. Mercuric chloride (0.544 g, 2 mmol) was then added and the mixture vigorously stirred for 12 h. The progress of the reaction was monitored by TLC. When all the thiourea had been consumed, 20 mL of chloroform were added and the suspension was filtered through a cintered glass funnel to remove any residue (HgS) formed as a byproduct during the reaction. The solvent was evaporated under reduced pressure and the 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. After filtration the solvent was evaporated and compound (I) was recrystallized in ethanol. Full spectroscopic and physical characterization will be reported elsewhere.

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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004).

Figures top

	Fig. 1. Molecular structure of compound (I), showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the centrosymmetric hydrogen-bonded dimer structure of compound (I) [Hydrogen bonds shown as dashed lines; symmetry code: (i) -x, 1 - y, 1 - z].

2-Benzoyl-1,1-diethyl-3-phenylguanidine top

Crystal data top

C₁₈H₂₁N₃O	F(000) = 632
M_r = 295.38	D_x = 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

Data collection top

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

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)] = 0.068	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(F_o²) + (0.0155P)² + 1.0509P] where P = (F_o² + 2F_c²)/3
3556 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₂₁N₃O	V = 1555.2 (15) Å³
M_r = 295.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.472 (6) Å	µ = 0.08 mm⁻¹
b = 15.010 (8) Å	T = 113 K
c = 10.154 (6) Å	0.50 × 0.40 × 0.30 mm
β = 102.992 (6)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3239 reflections with I > 2σ(I)
12318 measured reflections	R_int = 0.042
3556 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.27	Δρ_max = 0.26 e Å⁻³
3556 reflections	Δρ_min = −0.19 e Å⁻³
205 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	0.21836 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₃O
M_r	295.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	10.472 (6), 15.010 (8), 10.154 (6)
β (°)	102.992 (6)
V (Å³)	1555.2 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.40 × 0.30

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12318, 3556, 3239
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.112, 1.27
No. of reflections	3556
No. of parameters	205
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.19

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2001), SIR97 (Altomare et al., 1999), ORTEPII (Johnson, 1976), 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···O1ⁱ	0.90 (2)	1.97 (2)	2.852 (2)	168 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

MKR is grateful to the HEC-Pakistan for financial support for the Ph D program under scholarship No. [ILC–0363104].

References

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