6-(4-Methyl­phen­yl)-1,3,5-triazine-2,4-di­amine–benzoic acid (1/1)

Thanigaimani, K.; Khalib, N.C.; Razak, I.A.; Lavanya, P.; Balasubramani, K.

doi:10.1107/S1600536813013883

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o968-o969

doi:10.1107/S1600536813013883

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6-(4-Methylphenyl)-1,3,5-triazine-2,4-diamine–benzoic acid (1/1)

Kaliyaperumal Thanigaimani,^a Nuridayanti Che Khalib,^a Ibrahim Abdul Razak,^a ^*‡ Palanisamy Lavanya ^b and Kasthuri Balasubramani ^b

^aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu, India
^*Correspondence e-mail: arazaki@usm.my

(Received 7 May 2013; accepted 20 May 2013; online 25 May 2013)

The benzoic acid molecule of the title adduct, C₁₀H₁₁N₅·C₇H₆O₂, is approximately planar, with a dihedral angle of 7.2 (3)° between the carboxylic acid group and the benzene ring. In the triazine molecule, the plane of the triazine ring makes a dihedral angle of 28.85 (9)° with that of the adjacent benzene ring. In the crystal, the two components are linked by N—H⋯O and O—H⋯N hydrogen bonds with an R₂²(8) motif, thus generating a 1 + 1 unit of triazine and benzoic acid molecules. The acid–base units are further connected by N—H⋯N hydrogen bonds with R₂²(8) motifs, forming a supramolecular ribbon along [101]. The crystal structure also features weak π–π [centroid–centroid distances = 3.7638 (12) and 3.6008 (12) Å] and C—H⋯π interactions.

Related literature

For the biological activity of triazine derivatives, see: Bork et al. (2003 ). For related structures, see: Thanigaimani et al. (2007 , 2012a ,b ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₀H₁₁N₅·C₇H₆O₂
M_r = 323.36
Triclinic, $[P \overline 1]$
a = 7.4324 (5) Å
b = 10.9717 (3) Å
c = 11.2267 (3) Å
α = 117.202 (1)°
β = 101.645 (2)°
γ = 94.032 (2)°
V = 783.47 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.53 × 0.43 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.952, T_max = 0.980
16402 measured reflections
4578 independent reflections
3744 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.157
S = 1.11
4578 reflections
238 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯N2ⁱ	0.839 (19)	2.19 (2)	3.021 (2)	172 (2)
N4—H2N4⋯O2ⁱⁱ	0.86 (3)	2.11 (3)	2.965 (3)	172 (3)
N5—H1N5⋯N3ⁱⁱⁱ	0.85 (3)	2.14 (3)	2.984 (3)	169 (3)
O1—H1O1⋯N1^iv	0.83 (3)	1.80 (3)	2.613 (2)	167 (3)
C1—H1B⋯Cg2^v	0.98	2.75	3.661 (2)	156
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z+1; (iii) -x+2, -y+1, -z+2; (iv) x, y-1, z-1; (v) -x+2, -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/S1600536813013883/is5271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013883/is5271Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013883/is5271Isup3.cml

checkCIF report

Comment top

Triazine derivatives show antitumor activity, as well as a broad range of biological activities, such as anti-angiogenesis and antimicrobial effects (Bork et al., 2003). Related crystal structures of 2,4-diamino-6-phenyl-1,3,5-triazine- sorbic acid (1/1) (Thanigaimani et al., 2007), 6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diamine (Thanigaimani et al., 2012a) and adipic acid-2.4-diamino- 6-(4-methoxyphenyl)-1,3,5-triazine (1/2) (Thanigaimani et al., 2012b) have been reported. In the present study, hydrogen-bonding patterns in the 2,4-diamino-6-(4-methylphenyl)-1,3,5-triazine-benzoic acid (1/1) co-crystal are investigated.

The asymmetric unit (Fig. 1) contains one 2,4-diamino-6-(4-methylphenyl)-1,3,5-triazine molecule and one benzoic acid molecule. The dihedral angle between the triazine ring [N1/C10/N2/C8/N3/C9, maximum deviation = 0.006 (2) Å for atoms N2 & C10] and the plane formed by the benzoic acid molecule (O1/O2/C11–C17) is 11.16 (7)°. The triazine ring forms dihedral angle of 28.85 (9)° with the benzene ring (C2–C7). The bond lengths (Allen et al., 1987) and angles are normal.

In the crystal (Fig. 2), the triazine molecules are base-paired [with a graph-set (Bernstein et al., 1995) of R₂²(8)] on either side via N4—H1N4···N2ⁱ and N5—H1N5···N3ⁱⁱⁱ hydrogen bonds (symmetry codes in Table 1), forming a supramolecular ribbon. Each triazine molecule interacts with the carboxyl group of benzoic acid molecule via N4—H2N4···O2ⁱⁱ and O1—H1O1···N1^iv hydrogen bonds (symmetry codes in Table 1), generating R₂²(8) ring motifs. The crystal structure is further stabilized by π–π interactions between the benzene (Cg2; C2–C7) rings [Cg2···Cg2= 3.7638 (12) Å; 1 - x, -y, 1 - z] and that between triazine (Cg1; N1/C9/N3/C8/N2/C10) and benzene rings (Cg3; C12–C17) [Cg1···Cg3= 3.6008 (12) Å; 2 - x,1 - y, 1 - z] and C—H···π interactions (Table 1) involving the C2–C7 (centroid Cg2) ring.

Related literature top

For the biological activity of triazine derivatives, see: Bork et al. (2003). For related structures, see: Thanigaimani et al. (2007, 2012a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

Hot methanol solutions (20 ml) of 2,4-diamino-6-(4-methylphenyl)-1,3,5-triazine (50 mg, Aldrich) and benzoic acid (31 mg, Aldrich) were mixed and warmed over a heating magnetic stirrer hotplate for a few minutes. The resulting solution was allowed to cool slowly at room temperature and crystals of the title compound (I) appeared after a few days.

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 with atom labels with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

6-(4-Methylphenyl)-1,3,5-triazine-2,4-diamine–benzoic acid (1/1) top

Crystal data top

C₁₀H₁₁N₅·C₇H₆O₂	Z = 2
M_r = 323.36	F(000) = 340
Triclinic, P1	D_x = 1.371 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4324 (5) Å	Cell parameters from 7150 reflections
b = 10.9717 (3) Å	θ = 2.9–30.0°
c = 11.2267 (3) Å	µ = 0.09 mm⁻¹
α = 117.202 (1)°	T = 100 K
β = 101.645 (2)°	Block, colourless
γ = 94.032 (2)°	0.53 × 0.43 × 0.21 mm
V = 783.47 (6) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4578 independent reflections
Radiation source: fine-focus sealed tube	3744 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.952, T_max = 0.980	k = −15→14
16402 measured reflections	l = −15→15

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0412P)² + 1.1661P] where P = (F_o² + 2F_c²)/3
4578 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.38 e Å⁻³
1 restraint	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₀H₁₁N₅·C₇H₆O₂	γ = 94.032 (2)°
M_r = 323.36	V = 783.47 (6) Å³
Triclinic, P1	Z = 2
a = 7.4324 (5) Å	Mo Kα radiation
b = 10.9717 (3) Å	µ = 0.09 mm⁻¹
c = 11.2267 (3) Å	T = 100 K
α = 117.202 (1)°	0.53 × 0.43 × 0.21 mm
β = 101.645 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4578 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3744 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.980	R_int = 0.028
16402 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	1 restraint
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.38 e Å⁻³
4578 reflections	Δρ_min = −0.40 e Å⁻³
238 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 100.0 (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
N1	0.7322 (2)	0.67180 (16)	0.85847 (15)	0.0142 (3)
N2	0.6434 (2)	0.46349 (15)	0.63917 (16)	0.0134 (3)
N3	0.8105 (2)	0.45860 (16)	0.84190 (15)	0.0143 (3)
N4	0.5792 (2)	0.67431 (17)	0.66117 (17)	0.0174 (3)
N5	0.8918 (3)	0.66235 (18)	1.05089 (17)	0.0183 (3)
O1	0.7991 (2)	−0.06107 (15)	0.03289 (15)	0.0225 (3)
O2	0.6262 (2)	−0.02682 (15)	−0.13338 (15)	0.0238 (3)
C1	0.7538 (3)	−0.1872 (2)	0.3826 (2)	0.0216 (4)
H1A	0.7117	−0.2388	0.4268	0.032*
H1B	0.8831	−0.1959	0.3788	0.032*
H1C	0.6732	−0.2255	0.2881	0.032*
C2	0.7436 (2)	−0.03535 (19)	0.4656 (2)	0.0161 (4)
C3	0.7435 (3)	0.02206 (19)	0.6053 (2)	0.0165 (4)
H3A	0.7479	−0.0357	0.6477	0.020*
C4	0.7371 (3)	0.16236 (19)	0.68307 (19)	0.0154 (3)
H4A	0.7377	0.1997	0.7780	0.018*
C5	0.7297 (2)	0.24850 (18)	0.62243 (18)	0.0128 (3)
C6	0.7296 (3)	0.19181 (19)	0.48277 (19)	0.0147 (3)
H6A	0.7247	0.2495	0.4402	0.018*
C7	0.7367 (3)	0.05171 (19)	0.40579 (19)	0.0169 (4)
H7A	0.7369	0.0146	0.3110	0.020*
C8	0.7265 (2)	0.39923 (18)	0.70582 (18)	0.0127 (3)
C9	0.8102 (2)	0.59648 (18)	0.91395 (18)	0.0136 (3)
C10	0.6516 (2)	0.60150 (18)	0.72027 (18)	0.0138 (3)
C11	0.7236 (3)	0.0182 (2)	−0.01503 (19)	0.0173 (4)
C12	0.7677 (3)	0.17012 (19)	0.0888 (2)	0.0174 (4)
C13	0.8950 (3)	0.2206 (2)	0.2173 (2)	0.0192 (4)
H13A	0.9552	0.1582	0.2411	0.023*
C14	0.9343 (3)	0.3624 (2)	0.3110 (2)	0.0224 (4)
H14A	1.0218	0.3970	0.3988	0.027*
C15	0.8454 (3)	0.4537 (2)	0.2765 (2)	0.0258 (5)
H15A	0.8724	0.5507	0.3409	0.031*
C16	0.7172 (3)	0.4037 (2)	0.1480 (2)	0.0256 (5)
H16A	0.6570	0.4663	0.1245	0.031*
C17	0.6776 (3)	0.2617 (2)	0.0543 (2)	0.0211 (4)
H17A	0.5893	0.2269	−0.0332	0.025*
H1N4	0.527 (3)	0.638 (2)	0.576 (2)	0.012 (5)*
H2N4	0.584 (4)	0.762 (3)	0.715 (3)	0.021 (6)*
H1N5	0.965 (4)	0.621 (3)	1.082 (3)	0.026 (7)*
H2N5	0.909 (4)	0.746 (3)	1.090 (3)	0.026 (7)*
H1O1	0.762 (5)	−0.1439 (16)	−0.029 (3)	0.066 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0161 (7)	0.0122 (7)	0.0114 (7)	0.0041 (5)	0.0008 (5)	0.0042 (6)
N2	0.0143 (7)	0.0117 (7)	0.0125 (7)	0.0032 (5)	0.0009 (5)	0.0053 (6)
N3	0.0160 (7)	0.0125 (7)	0.0118 (7)	0.0039 (6)	0.0015 (5)	0.0045 (6)
N4	0.0241 (8)	0.0127 (7)	0.0109 (7)	0.0057 (6)	−0.0014 (6)	0.0041 (6)
N5	0.0250 (9)	0.0135 (7)	0.0120 (7)	0.0072 (6)	0.0001 (6)	0.0041 (6)
O1	0.0317 (8)	0.0136 (6)	0.0159 (7)	0.0043 (6)	−0.0003 (6)	0.0045 (5)
O2	0.0323 (8)	0.0166 (7)	0.0174 (7)	0.0055 (6)	0.0005 (6)	0.0063 (6)
C1	0.0202 (9)	0.0141 (8)	0.0263 (10)	0.0055 (7)	0.0070 (8)	0.0056 (8)
C2	0.0115 (8)	0.0136 (8)	0.0192 (9)	0.0025 (6)	0.0030 (6)	0.0050 (7)
C3	0.0159 (8)	0.0146 (8)	0.0206 (9)	0.0038 (7)	0.0043 (7)	0.0100 (7)
C4	0.0150 (8)	0.0163 (8)	0.0134 (8)	0.0029 (6)	0.0024 (6)	0.0066 (7)
C5	0.0112 (7)	0.0118 (7)	0.0132 (8)	0.0024 (6)	0.0016 (6)	0.0049 (6)
C6	0.0148 (8)	0.0159 (8)	0.0145 (8)	0.0042 (6)	0.0036 (6)	0.0081 (7)
C7	0.0185 (9)	0.0157 (8)	0.0137 (8)	0.0042 (7)	0.0046 (7)	0.0046 (7)
C8	0.0121 (8)	0.0118 (7)	0.0137 (8)	0.0022 (6)	0.0032 (6)	0.0059 (6)
C9	0.0145 (8)	0.0130 (8)	0.0123 (8)	0.0039 (6)	0.0032 (6)	0.0053 (6)
C10	0.0135 (8)	0.0132 (8)	0.0137 (8)	0.0033 (6)	0.0021 (6)	0.0061 (7)
C11	0.0201 (9)	0.0146 (8)	0.0167 (8)	0.0032 (7)	0.0058 (7)	0.0068 (7)
C12	0.0206 (9)	0.0125 (8)	0.0186 (9)	0.0032 (7)	0.0096 (7)	0.0053 (7)
C13	0.0211 (9)	0.0157 (9)	0.0200 (9)	0.0033 (7)	0.0078 (7)	0.0070 (7)
C14	0.0213 (9)	0.0176 (9)	0.0214 (9)	−0.0011 (7)	0.0085 (8)	0.0032 (8)
C15	0.0276 (11)	0.0136 (9)	0.0321 (11)	0.0003 (8)	0.0154 (9)	0.0050 (8)
C16	0.0294 (11)	0.0176 (9)	0.0370 (12)	0.0090 (8)	0.0179 (9)	0.0147 (9)
C17	0.0241 (10)	0.0190 (9)	0.0242 (10)	0.0059 (7)	0.0108 (8)	0.0117 (8)

Geometric parameters (Å, º) top

N1—C9	1.341 (2)	C3—C4	1.390 (3)
N1—C10	1.351 (2)	C3—H3A	0.9500
N2—C8	1.340 (2)	C4—C5	1.393 (3)
N2—C10	1.353 (2)	C4—H4A	0.9500
N3—C8	1.340 (2)	C5—C6	1.398 (2)
N3—C9	1.351 (2)	C5—C8	1.487 (2)
N4—C10	1.330 (2)	C6—C7	1.388 (3)
N4—H1N4	0.84 (2)	C6—H6A	0.9500
N4—H2N4	0.86 (3)	C7—H7A	0.9500
N5—C9	1.342 (2)	C11—C12	1.495 (3)
N5—H1N5	0.85 (3)	C12—C13	1.389 (3)
N5—H2N5	0.80 (3)	C12—C17	1.398 (3)
O1—C11	1.318 (2)	C13—C14	1.388 (3)
O1—H1O1	0.833 (10)	C13—H13A	0.9500
O2—C11	1.222 (2)	C14—C15	1.392 (3)
C1—C2	1.509 (3)	C14—H14A	0.9500
C1—H1A	0.9800	C15—C16	1.392 (3)
C1—H1B	0.9800	C15—H15A	0.9500
C1—H1C	0.9800	C16—C17	1.391 (3)
C2—C7	1.395 (3)	C16—H16A	0.9500
C2—C3	1.397 (3)	C17—H17A	0.9500

C9—N1—C10	115.80 (15)	C6—C7—H7A	119.5
C8—N2—C10	114.74 (15)	C2—C7—H7A	119.5
C8—N3—C9	114.64 (15)	N2—C8—N3	126.06 (16)
C10—N4—H1N4	122.6 (16)	N2—C8—C5	117.84 (15)
C10—N4—H2N4	116.8 (17)	N3—C8—C5	116.10 (15)
H1N4—N4—H2N4	121 (2)	N1—C9—N5	117.70 (16)
C9—N5—H1N5	117.4 (18)	N1—C9—N3	124.60 (16)
C9—N5—H2N5	117.2 (19)	N5—C9—N3	117.69 (17)
H1N5—N5—H2N5	119 (3)	N4—C10—N1	117.28 (16)
C11—O1—H1O1	108 (3)	N4—C10—N2	118.57 (16)
C2—C1—H1A	109.5	N1—C10—N2	124.15 (16)
C2—C1—H1B	109.5	O2—C11—O1	123.70 (18)
H1A—C1—H1B	109.5	O2—C11—C12	122.39 (18)
C2—C1—H1C	109.5	O1—C11—C12	113.91 (17)
H1A—C1—H1C	109.5	C13—C12—C17	120.07 (18)
H1B—C1—H1C	109.5	C13—C12—C11	121.28 (18)
C7—C2—C3	118.31 (17)	C17—C12—C11	118.65 (18)
C7—C2—C1	120.98 (18)	C14—C13—C12	119.9 (2)
C3—C2—C1	120.70 (18)	C14—C13—H13A	120.0
C4—C3—C2	121.04 (18)	C12—C13—H13A	120.0
C4—C3—H3A	119.5	C13—C14—C15	120.1 (2)
C2—C3—H3A	119.5	C13—C14—H14A	120.0
C3—C4—C5	120.29 (17)	C15—C14—H14A	120.0
C3—C4—H4A	119.9	C14—C15—C16	120.27 (19)
C5—C4—H4A	119.9	C14—C15—H15A	119.9
C4—C5—C6	119.00 (16)	C16—C15—H15A	119.9
C4—C5—C8	120.53 (16)	C17—C16—C15	119.7 (2)
C6—C5—C8	120.46 (16)	C17—C16—H16A	120.2
C7—C6—C5	120.42 (17)	C15—C16—H16A	120.2
C7—C6—H6A	119.8	C16—C17—C12	120.0 (2)
C5—C6—H6A	119.8	C16—C17—H17A	120.0
C6—C7—C2	120.94 (17)	C12—C17—H17A	120.0

C7—C2—C3—C4	−0.1 (3)	C10—N1—C9—N3	−0.8 (3)
C1—C2—C3—C4	179.00 (17)	C8—N3—C9—N1	0.7 (3)
C2—C3—C4—C5	0.3 (3)	C8—N3—C9—N5	179.86 (17)
C3—C4—C5—C6	−0.2 (3)	C9—N1—C10—N4	−177.53 (17)
C3—C4—C5—C8	−178.82 (17)	C9—N1—C10—N2	1.3 (3)
C4—C5—C6—C7	0.0 (3)	C8—N2—C10—N4	177.28 (17)
C8—C5—C6—C7	178.61 (17)	C8—N2—C10—N1	−1.5 (3)
C5—C6—C7—C2	0.1 (3)	O2—C11—C12—C13	−172.78 (19)
C3—C2—C7—C6	−0.1 (3)	O1—C11—C12—C13	7.2 (3)
C1—C2—C7—C6	−179.21 (17)	O2—C11—C12—C17	7.3 (3)
C10—N2—C8—N3	1.4 (3)	O1—C11—C12—C17	−172.72 (18)
C10—N2—C8—C5	−177.62 (16)	C17—C12—C13—C14	−0.7 (3)
C9—N3—C8—N2	−1.0 (3)	C11—C12—C13—C14	179.43 (18)
C9—N3—C8—C5	178.05 (16)	C12—C13—C14—C15	0.3 (3)
C4—C5—C8—N2	−152.42 (17)	C13—C14—C15—C16	−0.1 (3)
C6—C5—C8—N2	29.0 (2)	C14—C15—C16—C17	0.2 (3)
C4—C5—C8—N3	28.5 (2)	C15—C16—C17—C12	−0.6 (3)
C6—C5—C8—N3	−150.08 (17)	C13—C12—C17—C16	0.8 (3)
C10—N1—C9—N5	179.96 (17)	C11—C12—C17—C16	−179.30 (18)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···N2ⁱ	0.839 (19)	2.19 (2)	3.021 (2)	172 (2)
N4—H2N4···O2ⁱⁱ	0.86 (3)	2.11 (3)	2.965 (3)	172 (3)
N5—H1N5···N3ⁱⁱⁱ	0.85 (3)	2.14 (3)	2.984 (3)	169 (3)
O1—H1O1···N1^iv	0.83 (3)	1.80 (3)	2.613 (2)	167 (3)
C1—H1B···Cg2^v	0.98	2.75	3.661 (2)	156

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁N₅·C₇H₆O₂
M_r	323.36
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.4324 (5), 10.9717 (3), 11.2267 (3)
α, β, γ (°)	117.202 (1), 101.645 (2), 94.032 (2)
V (Å³)	783.47 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.53 × 0.43 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.952, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	16402, 4578, 3744
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.157, 1.11
No. of reflections	4578
No. of parameters	238
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.40

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···N2ⁱ	0.839 (19)	2.19 (2)	3.021 (2)	172 (2)
N4—H2N4···O2ⁱⁱ	0.86 (3)	2.11 (3)	2.965 (3)	172 (3)
N5—H1N5···N3ⁱⁱⁱ	0.85 (3)	2.14 (3)	2.984 (3)	169 (3)
O1—H1O1···N1^iv	0.83 (3)	1.80 (3)	2.613 (2)	167 (3)
C1—H1B···Cg2^v	0.98	2.75	3.661 (2)	156

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant (No. 304/PFIZIK/6312078) to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS–USM fellowship.

References

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Volume 69| Part 6| June 2013| Pages o968-o969

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