(Z)-N-[2-(N′-Hy­droxy­carbamimido­yl)phen­yl]acetamide

Fun, H.-K.; Ooi, C.W.; Dinesha; Viveka, S.; Nagaraja, G.K.

doi:10.1107/S1600536813003371

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o370-o371

doi:10.1107/S1600536813003371

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(Z)-N-[2-(N′-Hydroxycarbamimidoyl)phenyl]acetamide

Hoong-Kun Fun,^a,^b ^*‡ Chin Wei Ooi,^a § Dinesha,^c S. Viveka ^c and G.K. Nagaraja ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^cDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 2 February 2013; accepted 2 February 2013; online 9 February 2013)

The asymmetric unit of the title compound, C₉H₁₁N₃O₂, contains two molecules (A and B), which exist in Z conformations with respect to their C=N double bond. The dihedral angles between the benzene ring and the pendant hydroxycarbamimidoyl and acetamide groups are 28.58 (7) and 1.30 (5)°, respectively, in molecule A and 25.04 (7) and 27.85 (9)°, respectively, in molecule B. An intramolecular N—H⋯N hydrogen bond generates an S(6) ring in both molecules. Molecule A also features an intramolecular C—H⋯O interaction, which closes an S(6) ring. In the crystal, the molecules are linked by N—H⋯O, N—H⋯N, O—H⋯O, O—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π interactions, generating a three-dimensional network.

Related literature

For background and applications of amidoximes, see: Clapp (1976 , 1984 ); Jochims (1996 ); Fylaktakidou et al. (2008 ); Mansuy & Boucher (2004 ); Kontogiorgis & Hadjipavlou-Litina (2002 ); Wang et al. (2002 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₉H₁₁N₃O₂
M_r = 193.21
Triclinic, $[P \overline 1]$
a = 8.7813 (12) Å
b = 9.5432 (13) Å
c = 11.9770 (15) Å
α = 80.722 (2)°
β = 78.531 (2)°
γ = 70.181 (2)°
V = 920.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.35 × 0.20 × 0.05 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.965, T_max = 0.995
12849 measured reflections
4680 independent reflections
3815 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.07
4680 reflections
287 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—H3NA⋯N1A	0.883 (19)	2.048 (19)	2.7463 (18)	135.2 (15)
N3B—H3NB⋯N1B	0.86 (2)	1.963 (19)	2.6798 (17)	139.7 (17)
N2B—H1NB⋯O2Bⁱ	0.88 (2)	2.10 (2)	2.9725 (17)	173.0 (17)
N2A—H2NA⋯O2Aⁱⁱ	0.87 (3)	2.53 (2)	3.3004 (17)	149.0 (17)
N2A—H2NA⋯N2Bⁱⁱⁱ	0.87 (3)	2.54 (2)	3.2522 (18)	139.6 (17)
N2B—H2NB⋯O2A^iv	0.903 (19)	2.12 (2)	2.8900 (17)	142.1 (16)
O1A—H1OA⋯O1B	0.933 (19)	1.844 (19)	2.7733 (15)	173.9 (18)
O1B—H1OB⋯N1A^v	0.951 (18)	1.809 (18)	2.7597 (15)	177.0 (17)
C2A—H2AA⋯O2A	0.95	2.22	2.8556 (17)	123
C5A—H5AA⋯O2B^vi	0.95	2.55	3.2773 (17)	133
C9A—H9AC⋯N1B	0.98	2.56	3.499 (2)	160
C4A—H4AA⋯Cg2ⁱⁱ	0.95	2.95	3.7524 (16)	143
C3B—H3BA⋯Cg1^vii	0.95	2.88	3.6645 (17)	141
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+1; (iv) x+1, y, z; (v) -x+2, -y, -z+1; (vi) x, y+1, z-1; (vii) x, y, z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813003371/hb7034sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003371/hb7034Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813003371/hb7034Isup3.cml

checkCIF report

Comment top

Amidoximes are bi-functional molecules exhibiting a rich and diverse chemistry and provides the shortest way to reach certain heterocycles, such as 1,2,4-oxadiazoles (Clapp, 1976, 1984; Jochims, 1996). They are also considered interesting molecules in view of their biological applications (Fylaktakidou et al., 2008). Their ability to release NO or nitrites in vitro and in vivo experiments has recently attracted attention (Mansuy et al., 2004; Kontogiorgis et al., 2002). The discovery that nitric oxide (NO) acts as an important mediator of smooth muscle relaxation has led us to the preparation and testing of a wide variety of compounds with the aim of finding suitable new NO-donors. In the process, the title compound, (Z)-N-(2-(N'-hydroxycarbamimidoyl) phenyl)acetamide (Wang et al., 2002) was prepared.

The title compound consist of two crystallographically independent molecules (A and B) as shown in Fig. 1. The molecules exist in Z configuration with respect to the C7A ═N1A and C7B ═N1B double bonds. The intramolecular N3—H3···N1 hydrogen bonds (Table 1) form S(6) ring motifs (Bernstein et al., 1995) in both molecules. Molecule A is stabilized by an additional intramolecular C2A—H2AA···O2A hydrogen bond (Table 1) which also generates an S(6) ring motif (Bernstein et al., 1995). The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal structure (Fig. 2), the molecules are linked via N2B—H1NB···O2B, N2A—H2NA···O2A, N2A—H2NA···N2B, N2B—H2NB···O2A, O1A—H1OA···O1B, O1B—H1OB···N1A, C5A—H5AA···O2B and C9A—H9AC···N1B hydrogen bonds (Table 1) into a three dimensional network The crystal is further consolidated by C4A—H4A···Cg2 and C3B—H3BA···Cg1 interactions (Table 1), where Cg1 and Cg2 are the centroids of benzene rings (C1A–C6A and C1B–C6B), respectively.

Related literature top

For background and applications of amidoximes, see: Clapp (1976, 1984); Jochims (1996); Fylaktakidou et al. (2008); Mansuy & Boucher (2004); Kontogiorgis & Hadjipavlou-Litina (2002); Wang et al. (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

Equimolar amount of N-(2-cyanophenyl)acetamide (10 mmol) and NH₂OH.HCl (10 mmol) were dissolved in a minimum amount of methanol(10 ml)-water (5 ml) and followed by the addition of Na₂CO₃ (5 mmol). The solution was refluxed for 2 h. The solid product formed was collected through filtration and then evaporated to dryness. The product was redissolved in MeOH for recrystalliziation as colourless plates. M. P.: 145°C.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. Dashed lines indicate the intramolecular hydrogen bonds.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

(Z)-N-[2-(N'-Hydroxycarbamimidoyl)phenyl]acetamide top

Crystal data top

C₉H₁₁N₃O₂	Z = 4
M_r = 193.21	F(000) = 408
Triclinic, P1	D_x = 1.394 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7813 (12) Å	Cell parameters from 3493 reflections
b = 9.5432 (13) Å	θ = 2.3–28.5°
c = 11.9770 (15) Å	µ = 0.10 mm⁻¹
α = 80.722 (2)°	T = 100 K
β = 78.531 (2)°	Plate, colourless
γ = 70.181 (2)°	0.35 × 0.20 × 0.05 mm
V = 920.6 (2) Å³

Data collection top

Bruker APEX DUO CCD diffractometer	4680 independent reflections
Radiation source: fine-focus sealed tube	3815 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 28.6°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→7
T_min = 0.965, T_max = 0.995	k = −12→12
12849 measured reflections	l = −16→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0538P)² + 0.261P] where P = (F_o² + 2F_c²)/3
4680 reflections	(Δ/σ)_max < 0.001
287 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₉H₁₁N₃O₂	γ = 70.181 (2)°
M_r = 193.21	V = 920.6 (2) Å³
Triclinic, P1	Z = 4
a = 8.7813 (12) Å	Mo Kα radiation
b = 9.5432 (13) Å	µ = 0.10 mm⁻¹
c = 11.9770 (15) Å	T = 100 K
α = 80.722 (2)°	0.35 × 0.20 × 0.05 mm
β = 78.531 (2)°

Data collection top

Bruker APEX DUO CCD diffractometer	4680 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3815 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.995	R_int = 0.031
12849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.34 e Å⁻³
4680 reflections	Δρ_min = −0.26 e Å⁻³
287 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100 (1) K.

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
O1A	1.06478 (11)	0.25713 (11)	0.46170 (9)	0.0183 (2)
O2A	0.37005 (11)	0.17841 (12)	0.55131 (8)	0.0200 (2)
N1A	0.91075 (13)	0.26562 (12)	0.43516 (9)	0.0136 (2)
N2A	0.91118 (15)	0.50889 (14)	0.36926 (11)	0.0188 (3)
N3A	0.59696 (13)	0.25477 (13)	0.50343 (9)	0.0132 (2)
C1A	0.55777 (15)	0.36511 (14)	0.41114 (11)	0.0125 (2)
C2A	0.40471 (16)	0.41035 (15)	0.37477 (11)	0.0149 (3)
H2AA	0.3247	0.3646	0.4118	0.018*
C3A	0.36921 (16)	0.52204 (15)	0.28463 (12)	0.0168 (3)
H3AA	0.2645	0.5525	0.2613	0.020*
C4A	0.48421 (17)	0.58940 (15)	0.22839 (11)	0.0167 (3)
H4AA	0.4596	0.6644	0.1661	0.020*
C5A	0.63585 (16)	0.54578 (15)	0.26423 (11)	0.0146 (3)
H5AA	0.7146	0.5924	0.2261	0.018*
C6A	0.67591 (15)	0.43462 (14)	0.35539 (11)	0.0121 (2)
C7A	0.83924 (15)	0.39970 (14)	0.39030 (11)	0.0125 (2)
C8A	0.50778 (15)	0.16825 (14)	0.56596 (11)	0.0134 (3)
C9A	0.59175 (17)	0.05670 (16)	0.65623 (12)	0.0185 (3)
H9AA	0.6019	−0.0446	0.6420	0.028*
H9AB	0.5271	0.0779	0.7318	0.028*
H9AC	0.7010	0.0641	0.6537	0.028*
O1B	1.10383 (11)	0.00132 (11)	0.61515 (8)	0.0152 (2)
O2B	0.71673 (13)	−0.21124 (12)	1.05408 (8)	0.0231 (2)
N1B	0.97720 (13)	0.02967 (12)	0.71262 (9)	0.0141 (2)
N2B	1.14247 (14)	0.15404 (13)	0.75828 (11)	0.0161 (2)
N3B	0.79291 (14)	−0.06646 (13)	0.89487 (10)	0.0159 (2)
C1B	0.78846 (16)	0.06046 (15)	0.94314 (11)	0.0149 (3)
C2B	0.68093 (17)	0.10631 (16)	1.04286 (12)	0.0197 (3)
H2BA	0.6093	0.0513	1.0793	0.024*
C3B	0.67802 (19)	0.23181 (17)	1.08911 (13)	0.0234 (3)
H3BA	0.6063	0.2608	1.1580	0.028*
C4B	0.77935 (18)	0.31493 (17)	1.03513 (13)	0.0223 (3)
H4BA	0.7768	0.4011	1.0665	0.027*
C5B	0.88416 (17)	0.27147 (15)	0.93527 (12)	0.0180 (3)
H5BA	0.9524	0.3295	0.8983	0.022*
C6B	0.89229 (15)	0.14440 (14)	0.88740 (11)	0.0139 (3)
C7B	1.01102 (15)	0.10389 (14)	0.78082 (11)	0.0126 (2)
C8B	0.76306 (17)	−0.19266 (16)	0.95037 (12)	0.0179 (3)
C9B	0.7947 (2)	−0.31289 (18)	0.87350 (13)	0.0274 (3)
H9BA	0.7122	−0.3641	0.8981	0.041*
H9BB	0.9041	−0.3853	0.8780	0.041*
H9BC	0.7886	−0.2676	0.7944	0.041*
H3NA	0.696 (2)	0.235 (2)	0.5204 (15)	0.030 (5)*
H3NB	0.840 (2)	−0.069 (2)	0.8244 (17)	0.028 (5)*
H1NA	0.998 (2)	0.488 (2)	0.3996 (15)	0.024 (5)*
H1NB	1.181 (2)	0.165 (2)	0.8176 (18)	0.036 (5)*
H2NA	0.851 (2)	0.602 (3)	0.3617 (17)	0.038 (5)*
H2NB	1.218 (2)	0.116 (2)	0.6985 (17)	0.030 (5)*
H1OA	1.085 (2)	0.168 (2)	0.5101 (17)	0.038 (5)*
H1OB	1.095 (2)	−0.089 (2)	0.5974 (17)	0.037 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0131 (5)	0.0187 (5)	0.0250 (5)	−0.0069 (4)	−0.0079 (4)	0.0030 (4)
O2A	0.0145 (5)	0.0259 (5)	0.0208 (5)	−0.0105 (4)	−0.0049 (4)	0.0061 (4)
N1A	0.0104 (5)	0.0155 (5)	0.0161 (5)	−0.0054 (4)	−0.0037 (4)	−0.0003 (4)
N2A	0.0166 (6)	0.0137 (6)	0.0280 (7)	−0.0070 (5)	−0.0077 (5)	0.0023 (5)
N3A	0.0103 (5)	0.0165 (5)	0.0125 (5)	−0.0049 (4)	−0.0020 (4)	0.0010 (4)
C1A	0.0138 (6)	0.0125 (6)	0.0101 (6)	−0.0029 (5)	−0.0008 (5)	−0.0017 (5)
C2A	0.0137 (6)	0.0172 (6)	0.0133 (6)	−0.0044 (5)	−0.0015 (5)	−0.0019 (5)
C3A	0.0141 (6)	0.0188 (7)	0.0164 (7)	−0.0019 (5)	−0.0056 (5)	−0.0023 (5)
C4A	0.0204 (7)	0.0149 (6)	0.0127 (6)	−0.0030 (5)	−0.0047 (5)	0.0011 (5)
C5A	0.0171 (6)	0.0141 (6)	0.0121 (6)	−0.0054 (5)	−0.0004 (5)	−0.0011 (5)
C6A	0.0128 (6)	0.0105 (6)	0.0123 (6)	−0.0020 (5)	−0.0015 (5)	−0.0031 (5)
C7A	0.0135 (6)	0.0137 (6)	0.0104 (6)	−0.0051 (5)	0.0007 (5)	−0.0033 (5)
C8A	0.0125 (6)	0.0145 (6)	0.0123 (6)	−0.0043 (5)	−0.0002 (5)	−0.0013 (5)
C9A	0.0165 (6)	0.0201 (7)	0.0183 (7)	−0.0079 (5)	−0.0039 (5)	0.0057 (5)
O1B	0.0169 (5)	0.0158 (5)	0.0129 (5)	−0.0068 (4)	0.0026 (4)	−0.0036 (4)
O2B	0.0321 (6)	0.0288 (6)	0.0148 (5)	−0.0197 (5)	−0.0053 (4)	0.0044 (4)
N1B	0.0142 (5)	0.0161 (5)	0.0112 (5)	−0.0051 (4)	0.0010 (4)	−0.0019 (4)
N2B	0.0182 (6)	0.0189 (6)	0.0138 (6)	−0.0093 (5)	−0.0020 (5)	−0.0020 (5)
N3B	0.0194 (6)	0.0171 (6)	0.0122 (6)	−0.0087 (5)	−0.0010 (4)	0.0008 (4)
C1B	0.0162 (6)	0.0146 (6)	0.0126 (6)	−0.0029 (5)	−0.0047 (5)	0.0015 (5)
C2B	0.0181 (7)	0.0214 (7)	0.0164 (7)	−0.0045 (5)	−0.0007 (5)	0.0013 (5)
C3B	0.0248 (7)	0.0228 (7)	0.0157 (7)	−0.0004 (6)	0.0016 (6)	−0.0039 (6)
C4B	0.0268 (7)	0.0184 (7)	0.0193 (7)	−0.0031 (6)	−0.0018 (6)	−0.0067 (6)
C5B	0.0199 (7)	0.0160 (6)	0.0175 (7)	−0.0047 (5)	−0.0034 (5)	−0.0012 (5)
C6B	0.0142 (6)	0.0139 (6)	0.0121 (6)	−0.0019 (5)	−0.0043 (5)	0.0001 (5)
C7B	0.0139 (6)	0.0102 (6)	0.0124 (6)	−0.0032 (5)	−0.0028 (5)	0.0020 (4)
C8B	0.0188 (6)	0.0210 (7)	0.0172 (7)	−0.0110 (5)	−0.0055 (5)	0.0030 (5)
C9B	0.0428 (9)	0.0228 (8)	0.0219 (8)	−0.0187 (7)	−0.0041 (7)	−0.0002 (6)

Geometric parameters (Å, º) top

O1A—N1A	1.4232 (13)	O1B—N1B	1.4333 (14)
O1A—H1OA	0.93 (2)	O1B—H1OB	0.95 (2)
O2A—C8A	1.2257 (16)	O2B—C8B	1.2315 (17)
N1A—C7A	1.2992 (17)	N1B—C7B	1.2972 (17)
N2A—C7A	1.3590 (16)	N2B—C7B	1.3577 (16)
N2A—H1NA	0.857 (19)	N2B—H1NB	0.88 (2)
N2A—H2NA	0.87 (2)	N2B—H2NB	0.90 (2)
N3A—C8A	1.3644 (16)	N3B—C8B	1.3593 (17)
N3A—C1A	1.4069 (16)	N3B—C1B	1.4098 (17)
N3A—H3NA	0.885 (19)	N3B—H3NB	0.863 (19)
C1A—C2A	1.4005 (18)	C1B—C2B	1.3962 (19)
C1A—C6A	1.4179 (17)	C1B—C6B	1.4140 (18)
C2A—C3A	1.3915 (18)	C2B—C3B	1.389 (2)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.3845 (19)	C3B—C4B	1.387 (2)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.3873 (19)	C4B—C5B	1.383 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.4027 (17)	C5B—C6B	1.3977 (19)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C7A	1.4874 (17)	C6B—C7B	1.4907 (18)
C8A—C9A	1.5031 (18)	C8B—C9B	1.505 (2)
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C9A—H9AB	0.9800	C9B—H9BB	0.9800
C9A—H9AC	0.9800	C9B—H9BC	0.9800

N1A—O1A—H1OA	99.4 (12)	N1B—O1B—H1OB	99.3 (12)
C7A—N1A—O1A	109.97 (10)	C7B—N1B—O1B	109.89 (10)
C7A—N2A—H1NA	114.6 (12)	C7B—N2B—H1NB	116.8 (13)
C7A—N2A—H2NA	119.9 (13)	C7B—N2B—H2NB	114.9 (12)
H1NA—N2A—H2NA	117.3 (18)	H1NB—N2B—H2NB	115.9 (17)
C8A—N3A—C1A	129.30 (11)	C8B—N3B—C1B	127.77 (12)
C8A—N3A—H3NA	115.5 (12)	C8B—N3B—H3NB	117.8 (12)
C1A—N3A—H3NA	115.1 (12)	C1B—N3B—H3NB	113.0 (12)
C2A—C1A—N3A	121.95 (11)	C2B—C1B—N3B	121.21 (12)
C2A—C1A—C6A	119.31 (12)	C2B—C1B—C6B	119.76 (12)
N3A—C1A—C6A	118.72 (11)	N3B—C1B—C6B	119.01 (12)
C3A—C2A—C1A	120.31 (12)	C3B—C2B—C1B	120.43 (13)
C3A—C2A—H2AA	119.8	C3B—C2B—H2BA	119.8
C1A—C2A—H2AA	119.8	C1B—C2B—H2BA	119.8
C4A—C3A—C2A	120.99 (12)	C4B—C3B—C2B	120.26 (13)
C4A—C3A—H3AA	119.5	C4B—C3B—H3BA	119.9
C2A—C3A—H3AA	119.5	C2B—C3B—H3BA	119.9
C3A—C4A—C5A	119.06 (12)	C5B—C4B—C3B	119.55 (13)
C3A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.2
C5A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.2
C4A—C5A—C6A	121.70 (12)	C4B—C5B—C6B	121.71 (13)
C4A—C5A—H5AA	119.1	C4B—C5B—H5BA	119.1
C6A—C5A—H5AA	119.1	C6B—C5B—H5BA	119.1
C5A—C6A—C1A	118.61 (11)	C5B—C6B—C1B	118.27 (12)
C5A—C6A—C7A	117.69 (11)	C5B—C6B—C7B	118.22 (12)
C1A—C6A—C7A	123.68 (11)	C1B—C6B—C7B	123.51 (12)
N1A—C7A—N2A	122.40 (12)	N1B—C7B—N2B	124.22 (12)
N1A—C7A—C6A	119.40 (11)	N1B—C7B—C6B	117.67 (11)
N2A—C7A—C6A	118.14 (12)	N2B—C7B—C6B	118.01 (11)
O2A—C8A—N3A	123.82 (12)	O2B—C8B—N3B	124.54 (13)
O2A—C8A—C9A	121.50 (11)	O2B—C8B—C9B	121.64 (13)
N3A—C8A—C9A	114.68 (11)	N3B—C8B—C9B	113.82 (12)
C8A—C9A—H9AA	109.5	C8B—C9B—H9BA	109.5
C8A—C9A—H9AB	109.5	C8B—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
C8A—C9A—H9AC	109.5	C8B—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5

C8A—N3A—C1A—C2A	5.0 (2)	C8B—N3B—C1B—C2B	−31.7 (2)
C8A—N3A—C1A—C6A	−176.47 (12)	C8B—N3B—C1B—C6B	149.88 (14)
N3A—C1A—C2A—C3A	178.69 (12)	N3B—C1B—C2B—C3B	−179.89 (13)
C6A—C1A—C2A—C3A	0.20 (19)	C6B—C1B—C2B—C3B	−1.5 (2)
C1A—C2A—C3A—C4A	0.7 (2)	C1B—C2B—C3B—C4B	1.5 (2)
C2A—C3A—C4A—C5A	−1.0 (2)	C2B—C3B—C4B—C5B	−0.4 (2)
C3A—C4A—C5A—C6A	0.4 (2)	C3B—C4B—C5B—C6B	−0.7 (2)
C4A—C5A—C6A—C1A	0.45 (19)	C4B—C5B—C6B—C1B	0.7 (2)
C4A—C5A—C6A—C7A	−177.74 (12)	C4B—C5B—C6B—C7B	−178.83 (12)
C2A—C1A—C6A—C5A	−0.76 (18)	C2B—C1B—C6B—C5B	0.42 (19)
N3A—C1A—C6A—C5A	−179.30 (12)	N3B—C1B—C6B—C5B	178.85 (12)
C2A—C1A—C6A—C7A	177.32 (12)	C2B—C1B—C6B—C7B	179.89 (12)
N3A—C1A—C6A—C7A	−1.22 (18)	N3B—C1B—C6B—C7B	−1.69 (19)
O1A—N1A—C7A—N2A	2.73 (17)	O1B—N1B—C7B—N2B	3.63 (17)
O1A—N1A—C7A—C6A	179.87 (10)	O1B—N1B—C7B—C6B	179.80 (10)
C5A—C6A—C7A—N1A	−150.83 (12)	C5B—C6B—C7B—N1B	−152.96 (12)
C1A—C6A—C7A—N1A	31.08 (18)	C1B—C6B—C7B—N1B	27.57 (18)
C5A—C6A—C7A—N2A	26.43 (17)	C5B—C6B—C7B—N2B	23.45 (18)
C1A—C6A—C7A—N2A	−151.66 (13)	C1B—C6B—C7B—N2B	−156.02 (12)
C1A—N3A—C8A—O2A	−2.2 (2)	C1B—N3B—C8B—O2B	4.6 (2)
C1A—N3A—C8A—C9A	177.71 (13)	C1B—N3B—C8B—C9B	−174.30 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3NA···N1A	0.883 (19)	2.048 (19)	2.7463 (18)	135.2 (15)
N3B—H3NB···N1B	0.86 (2)	1.963 (19)	2.6798 (17)	139.7 (17)
N2B—H1NB···O2Bⁱ	0.88 (2)	2.10 (2)	2.9725 (17)	173.0 (17)
N2A—H2NA···O2Aⁱⁱ	0.87 (3)	2.53 (2)	3.3004 (17)	149.0 (17)
N2A—H2NA···N2Bⁱⁱⁱ	0.87 (3)	2.54 (2)	3.2522 (18)	139.6 (17)
N2B—H2NB···O2A^iv	0.903 (19)	2.12 (2)	2.8900 (17)	142.1 (16)
O1A—H1OA···O1B	0.933 (19)	1.844 (19)	2.7733 (15)	173.9 (18)
O1B—H1OB···N1A^v	0.951 (18)	1.809 (18)	2.7597 (15)	177.0 (17)
C2A—H2AA···O2A	0.95	2.22	2.8556 (17)	123
C5A—H5AA···O2B^vi	0.95	2.55	3.2773 (17)	133
C9A—H9AC···N1B	0.98	2.56	3.499 (2)	160
C4A—H4AA···Cg2ⁱⁱ	0.95	2.95	3.7524 (16)	143
C3B—H3BA···Cg1^vii	0.95	2.88	3.6645 (17)	141

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x+1, y, z; (v) −x+2, −y, −z+1; (vi) x, y+1, z−1; (vii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₁N₃O₂
M_r	193.21
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.7813 (12), 9.5432 (13), 11.9770 (15)
α, β, γ (°)	80.722 (2), 78.531 (2), 70.181 (2)
V (Å³)	920.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.20 × 0.05

Data collection
Diffractometer	Bruker APEX DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.965, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	12849, 4680, 3815
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.674

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 1.07
No. of reflections	4680
No. of parameters	287
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3NA···N1A	0.883 (19)	2.048 (19)	2.7463 (18)	135.2 (15)
N3B—H3NB···N1B	0.86 (2)	1.963 (19)	2.6798 (17)	139.7 (17)
N2B—H1NB···O2Bⁱ	0.88 (2)	2.10 (2)	2.9725 (17)	173.0 (17)
N2A—H2NA···O2Aⁱⁱ	0.87 (3)	2.53 (2)	3.3004 (17)	149.0 (17)
N2A—H2NA···N2Bⁱⁱⁱ	0.87 (3)	2.54 (2)	3.2522 (18)	139.6 (17)
N2B—H2NB···O2A^iv	0.903 (19)	2.12 (2)	2.8900 (17)	142.1 (16)
O1A—H1OA···O1B	0.933 (19)	1.844 (19)	2.7733 (15)	173.9 (18)
O1B—H1OB···N1A^v	0.951 (18)	1.809 (18)	2.7597 (15)	177.0 (17)
C2A—H2AA···O2A	0.95	2.22	2.8556 (17)	123
C5A—H5AA···O2B^vi	0.95	2.55	3.2773 (17)	133
C9A—H9AC···N1B	0.98	2.56	3.499 (2)	160
C4A—H4AA···Cg2ⁱⁱ	0.95	2.95	3.7524 (16)	143
C3B—H3BA···Cg1^vii	0.95	2.88	3.6645 (17)	141

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x+1, y, z; (v) −x+2, −y, −z+1; (vi) x, y+1, z−1; (vii) x, y, z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: F-8809-2012.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/CIPPM813040). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160.

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Volume 69| Part 3| March 2013| Pages o370-o371

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