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

Thanigaimani, K.; Arshad, S.; Razak, I.A.; Makeshvaran, D.; Balasubramani, K.

doi:10.1107/S1600536813013895

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o970

doi:10.1107/S1600536813013895

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

Kaliyaperumal Thanigaimani,^a Suhana Arshad,^a Ibrahim Abdul Razak,^a ^*‡ Duraisamy Makeshvaran ^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 4-methylbenzoic acid molecule of the title adduct, C₁₀H₁₁N₅·C₈H₈O₂, is approximately planar with a dihedral angle of 6.3 (2)° between the carboxylic acid group and the benzene ring. In the triazine molecule, the plane of the triazine ring makes a dihedral angle of 29.2 (2)° with that of the adjacent benzene ring. In the crystal, the acid and base molecules are linked via N—H⋯O and O—H⋯N hydrogen bonds with an R₂²(8) motif, and the acid–base pairs are further connected via N—H⋯N hydrogen bonds with R₂²(8) motifs, forming a supramolecular ribbon along [101]. Between the tapes, a weak C—H⋯π interaction is observed.

Related literature

The background to this study has been described in the preceding paper, see: Thanigaimani et al. (2013 ). 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·C₈H₈O₂
M_r = 337.38
Monoclinic, C c
a = 11.1271 (3) Å
b = 20.9492 (6) Å
c = 7.4189 (2) Å
β = 101.321 (2)°
V = 1695.73 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.965, T_max = 0.982
8715 measured reflections
1932 independent reflections
1811 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.135
S = 1.19
1932 reflections
244 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2	0.77 (6)	1.92 (6)	2.682 (4)	171 (6)
N4—H1N4⋯O1	0.97 (6)	1.98 (6)	2.936 (5)	169 (6)
N4—H2N4⋯N3ⁱ	0.84 (4)	2.26 (4)	3.099 (5)	172 (4)
N5—H1N5⋯N1ⁱⁱ	0.90 (6)	2.11 (6)	3.003 (5)	173 (5)
C10—H10C⋯Cg2ⁱⁱⁱ	0.98	2.83	3.723 (6)	152
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

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/S1600536813013895/is5272sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013895/is5272Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013895/is5272Isup3.cml

checkCIF report

Comment top

This work follows on from our previous report on 2,4-diamino-6-(4-methylphenyl)-1,3,5-triazine–benzoic acid (1/1) (Thanigaimani et al., 2013).

The asymmetric unit (Fig. 1) contains one 2,4-diamino-6-(4-methylphenyl)- 1,3,5-triazine molecule and one 4-methylbenzoic acid molecule. The dihedral angle between the triazine ring [N1/C1/N2/C2/N3/C3, maximum deviation = 0.003 (4) Å for atom N1] and the plane formed by the benzoic acid molecule (O1/O2/C11–C18) is 12.04 (19)°. The triazine ring forms a dihedral angle of 29.2 (2)° with the benzene ring (C4–C10). The bond lengths (Allen et al., 1987) and angles are normal.

In the crystal (Fig. 2), the triazine molecules are base-paired with a R₂²(8) graph-set motifs (Bernstein et al., 1995) on either side via N4—H2N4···N3ⁱⁱ and N5—H1N5···N1ⁱ hydrogen bonds (symmetry codes in Table 1) and further interact with the carboxyl group of 4-methylbenzoic acid molecules via N4—H1N4···O1 and O2—H1O2···N2 hydrogen bonds, forming an R₂²(8) motif and a supramolecular ribbon along the [101]. In addition, the crystal structure is stabilized by weak C—H···π interactions (Table 1) involving the C4–C9 (centroid Cg2) ring.

Related literature top

The background to this study has been described in the preceding paper, see: Thanigaimani et al. (2013). 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 4-methylbenzoic acid (34 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–4-methylbenzoic acid (1/1) top

Crystal data top

C₁₀H₁₁N₅·C₈H₈O₂	F(000) = 712
M_r = 337.38	D_x = 1.322 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6815 reflections
a = 11.1271 (3) Å	θ = 3.2–33.7°
b = 20.9492 (6) Å	µ = 0.09 mm⁻¹
c = 7.4189 (2) Å	T = 100 K
β = 101.321 (2)°	Plate, colourless
V = 1695.73 (8) Å³	0.40 × 0.40 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1932 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.965, T_max = 0.982	k = −27→27
8715 measured reflections	l = −9→7

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ²(F_o²) + (0.0311P)² + 4.4301P] where P = (F_o² + 2F_c²)/3
1932 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.27 e Å⁻³
3 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₀H₁₁N₅·C₈H₈O₂	V = 1695.73 (8) Å³
M_r = 337.38	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 11.1271 (3) Å	µ = 0.09 mm⁻¹
b = 20.9492 (6) Å	T = 100 K
c = 7.4189 (2) Å	0.40 × 0.40 × 0.20 mm
β = 101.321 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1932 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1811 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.982	R_int = 0.031
8715 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	3 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.27 e Å⁻³
1932 reflections	Δρ_min = −0.27 e Å⁻³
244 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	0.4994 (3)	0.25996 (17)	0.3556 (5)	0.0165 (8)
N2	0.3884 (4)	0.16295 (15)	0.2802 (6)	0.0170 (7)
N3	0.2919 (3)	0.26326 (16)	0.1933 (6)	0.0164 (7)
N4	0.5874 (3)	0.16186 (18)	0.4348 (5)	0.0200 (8)
H1N4	0.581 (5)	0.116 (3)	0.447 (8)	0.030*
H2N4	0.646 (3)	0.183 (2)	0.496 (7)	0.030*
N5	0.1876 (3)	0.16862 (19)	0.1268 (6)	0.0235 (9)
H1N5	0.126 (5)	0.188 (3)	0.049 (9)	0.035*
H2N5	0.188 (5)	0.126 (3)	0.120 (8)	0.035*
C1	0.4899 (4)	0.19523 (19)	0.3563 (6)	0.0156 (8)
C2	0.2928 (4)	0.19889 (19)	0.2015 (6)	0.0169 (8)
C3	0.3982 (4)	0.29042 (16)	0.2738 (7)	0.0150 (7)
C4	0.4034 (4)	0.36131 (17)	0.2713 (7)	0.0166 (8)
C5	0.2976 (4)	0.3973 (2)	0.2713 (6)	0.0189 (9)
H5A	0.2217	0.3762	0.2690	0.023*
C6	0.3023 (4)	0.4632 (2)	0.2746 (7)	0.0228 (10)
H6A	0.2296	0.4870	0.2744	0.027*
C7	0.4126 (4)	0.49501 (18)	0.2781 (7)	0.0216 (9)
C8	0.5170 (4)	0.4596 (2)	0.2779 (7)	0.0236 (10)
H8A	0.5926	0.4809	0.2798	0.028*
C9	0.5136 (4)	0.39311 (19)	0.2749 (6)	0.0187 (9)
H9A	0.5865	0.3695	0.2753	0.022*
C10	0.4170 (5)	0.5672 (2)	0.2789 (8)	0.0306 (11)
H10A	0.4988	0.5814	0.3396	0.046*
H10B	0.3558	0.5838	0.3455	0.046*
H10C	0.3991	0.5830	0.1521	0.046*
O1	0.5390 (3)	0.02412 (14)	0.4355 (5)	0.0245 (7)
O2	0.3551 (3)	0.03627 (15)	0.2514 (5)	0.0248 (7)
C11	0.3135 (5)	−0.1599 (2)	0.1798 (7)	0.0298 (12)
H11A	0.2450	−0.1770	0.0970	0.036*
C12	0.3269 (4)	−0.0939 (2)	0.1967 (7)	0.0253 (10)
H12A	0.2683	−0.0662	0.1258	0.030*
C13	0.4271 (4)	−0.0689 (2)	0.3187 (6)	0.0201 (10)
C14	0.5126 (5)	−0.1101 (2)	0.4226 (7)	0.0268 (10)
H14A	0.5807	−0.0934	0.5069	0.032*
C15	0.4970 (5)	−0.1754 (2)	0.4014 (7)	0.0305 (12)
H15A	0.5557	−0.2033	0.4711	0.037*
C16	0.3977 (6)	−0.20104 (19)	0.2808 (10)	0.0338 (12)
C17	0.3816 (7)	−0.2731 (2)	0.2623 (12)	0.0459 (16)
H17A	0.3450	−0.2838	0.1348	0.069*
H17B	0.3278	−0.2879	0.3437	0.069*
H17C	0.4617	−0.2939	0.2967	0.069*
C18	0.4468 (4)	0.0016 (2)	0.3420 (6)	0.0202 (9)
H1O2	0.370 (6)	0.072 (3)	0.253 (9)	0.038 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0140 (17)	0.0145 (17)	0.0190 (18)	−0.0002 (14)	−0.0018 (15)	−0.0001 (15)
N2	0.0159 (16)	0.0136 (14)	0.0195 (15)	0.0007 (15)	−0.0012 (13)	−0.0001 (17)
N3	0.0125 (15)	0.0127 (17)	0.0224 (18)	0.0006 (14)	−0.0002 (14)	0.0021 (15)
N4	0.0155 (17)	0.0140 (17)	0.027 (2)	−0.0007 (14)	−0.0055 (15)	−0.0017 (15)
N5	0.0146 (18)	0.0144 (19)	0.037 (2)	−0.0030 (14)	−0.0063 (17)	0.0027 (16)
C1	0.0154 (18)	0.0128 (18)	0.0183 (19)	0.0004 (16)	0.0024 (16)	0.0000 (17)
C2	0.0151 (18)	0.017 (2)	0.018 (2)	−0.0021 (17)	0.0015 (16)	0.0000 (18)
C3	0.0138 (17)	0.0147 (16)	0.0168 (17)	0.0002 (17)	0.0041 (14)	−0.0008 (19)
C4	0.0211 (19)	0.0130 (16)	0.0141 (18)	0.0003 (18)	−0.0009 (15)	−0.0020 (19)
C5	0.0129 (19)	0.020 (2)	0.021 (2)	−0.0008 (16)	−0.0049 (16)	−0.0015 (17)
C6	0.022 (2)	0.019 (2)	0.024 (2)	0.0083 (18)	−0.0040 (18)	−0.0040 (18)
C7	0.032 (2)	0.0132 (17)	0.0169 (18)	−0.0022 (19)	−0.0026 (18)	0.000 (2)
C8	0.025 (2)	0.017 (2)	0.027 (2)	−0.0084 (17)	0.0001 (19)	0.0010 (18)
C9	0.018 (2)	0.0148 (19)	0.021 (2)	−0.0005 (16)	−0.0018 (17)	−0.0002 (17)
C10	0.047 (3)	0.0130 (18)	0.030 (2)	0.002 (2)	0.003 (2)	0.001 (2)
O1	0.0219 (16)	0.0158 (13)	0.0323 (18)	−0.0005 (13)	−0.0035 (13)	0.0004 (14)
O2	0.0205 (15)	0.0135 (14)	0.037 (2)	−0.0021 (12)	−0.0022 (14)	0.0019 (14)
C11	0.031 (3)	0.024 (2)	0.039 (3)	−0.013 (2)	0.019 (2)	−0.015 (2)
C12	0.025 (2)	0.020 (2)	0.034 (3)	0.0007 (18)	0.014 (2)	−0.007 (2)
C13	0.019 (2)	0.0170 (19)	0.028 (3)	−0.0016 (16)	0.0145 (19)	−0.0006 (17)
C14	0.032 (3)	0.019 (2)	0.033 (3)	0.0043 (19)	0.015 (2)	0.003 (2)
C15	0.041 (3)	0.020 (2)	0.036 (3)	0.008 (2)	0.020 (2)	0.009 (2)
C16	0.052 (3)	0.0146 (19)	0.045 (3)	−0.001 (2)	0.034 (2)	−0.005 (3)
C17	0.074 (4)	0.017 (2)	0.058 (4)	−0.008 (3)	0.041 (3)	−0.005 (3)
C18	0.019 (2)	0.0158 (19)	0.026 (2)	0.0017 (17)	0.0062 (18)	−0.002 (2)

Geometric parameters (Å, º) top

N1—C3	1.333 (5)	C9—H9A	0.9500
N1—C1	1.360 (5)	C10—H10A	0.9800
N2—C2	1.340 (5)	C10—H10B	0.9800
N2—C1	1.342 (6)	C10—H10C	0.9800
N3—C3	1.342 (5)	O1—C18	1.215 (5)
N3—C2	1.350 (5)	O2—C18	1.324 (5)
N4—C1	1.326 (5)	O2—H1O2	0.77 (6)
N4—H1N4	0.97 (6)	C11—C16	1.380 (8)
N4—H2N4	0.849 (11)	C11—C12	1.395 (6)
N5—C2	1.351 (5)	C11—H11A	0.9500
N5—H1N5	0.90 (6)	C12—C13	1.393 (6)
N5—H2N5	0.89 (6)	C12—H12A	0.9500
C3—C4	1.487 (5)	C13—C14	1.398 (6)
C4—C9	1.390 (6)	C13—C18	1.498 (6)
C4—C5	1.398 (6)	C14—C15	1.384 (6)
C5—C6	1.382 (6)	C14—H14A	0.9500
C5—H5A	0.9500	C15—C16	1.386 (8)
C6—C7	1.392 (7)	C15—H15A	0.9500
C6—H6A	0.9500	C16—C17	1.523 (6)
C7—C8	1.378 (6)	C17—H17A	0.9800
C7—C10	1.512 (5)	C17—H17B	0.9800
C8—C9	1.394 (6)	C17—H17C	0.9800
C8—H8A	0.9500

C3—N1—C1	114.8 (3)	C8—C9—H9A	120.0
C2—N2—C1	115.5 (3)	C7—C10—H10A	109.5
C3—N3—C2	113.9 (3)	C7—C10—H10B	109.5
C1—N4—H1N4	120 (3)	H10A—C10—H10B	109.5
C1—N4—H2N4	116 (4)	C7—C10—H10C	109.5
H1N4—N4—H2N4	122 (5)	H10A—C10—H10C	109.5
C2—N5—H1N5	123 (4)	H10B—C10—H10C	109.5
C2—N5—H2N5	119 (4)	C18—O2—H1O2	113 (5)
H1N5—N5—H2N5	115 (5)	C16—C11—C12	121.4 (5)
N4—C1—N2	117.9 (4)	C16—C11—H11A	119.3
N4—C1—N1	118.0 (4)	C12—C11—H11A	119.3
N2—C1—N1	124.1 (4)	C13—C12—C11	119.2 (5)
N2—C2—N3	125.4 (4)	C13—C12—H12A	120.4
N2—C2—N5	117.7 (4)	C11—C12—H12A	120.4
N3—C2—N5	116.9 (4)	C12—C13—C14	119.9 (4)
N1—C3—N3	126.3 (3)	C12—C13—C18	121.7 (4)
N1—C3—C4	116.9 (4)	C14—C13—C18	118.5 (4)
N3—C3—C4	116.8 (3)	C15—C14—C13	119.4 (5)
C9—C4—C5	118.8 (3)	C15—C14—H14A	120.3
C9—C4—C3	121.0 (4)	C13—C14—H14A	120.3
C5—C4—C3	120.2 (4)	C14—C15—C16	121.5 (5)
C6—C5—C4	120.6 (4)	C14—C15—H15A	119.2
C6—C5—H5A	119.7	C16—C15—H15A	119.2
C4—C5—H5A	119.7	C11—C16—C15	118.6 (4)
C5—C6—C7	120.6 (4)	C11—C16—C17	121.0 (6)
C5—C6—H6A	119.7	C15—C16—C17	120.5 (6)
C7—C6—H6A	119.7	C16—C17—H17A	109.5
C8—C7—C6	118.9 (4)	C16—C17—H17B	109.5
C8—C7—C10	120.7 (4)	H17A—C17—H17B	109.5
C6—C7—C10	120.4 (4)	C16—C17—H17C	109.5
C7—C8—C9	121.2 (4)	H17A—C17—H17C	109.5
C7—C8—H8A	119.4	H17B—C17—H17C	109.5
C9—C8—H8A	119.4	O1—C18—O2	123.8 (4)
C4—C9—C8	120.0 (4)	O1—C18—C13	122.5 (4)
C4—C9—H9A	120.0	O2—C18—C13	113.7 (4)

C2—N2—C1—N4	−179.5 (4)	C5—C6—C7—C10	179.1 (5)
C2—N2—C1—N1	−0.5 (7)	C6—C7—C8—C9	−0.2 (8)
C3—N1—C1—N4	179.7 (4)	C10—C7—C8—C9	−179.2 (4)
C3—N1—C1—N2	0.7 (7)	C5—C4—C9—C8	−0.2 (7)
C1—N2—C2—N3	0.3 (7)	C3—C4—C9—C8	−178.1 (4)
C1—N2—C2—N5	−178.5 (4)	C7—C8—C9—C4	0.3 (7)
C3—N3—C2—N2	−0.3 (7)	C16—C11—C12—C13	−0.2 (7)
C3—N3—C2—N5	178.5 (4)	C11—C12—C13—C14	−0.1 (7)
C1—N1—C3—N3	−0.7 (8)	C11—C12—C13—C18	179.6 (4)
C1—N1—C3—C4	179.3 (4)	C12—C13—C14—C15	0.6 (7)
C2—N3—C3—N1	0.5 (8)	C18—C13—C14—C15	−179.2 (5)
C2—N3—C3—C4	−179.5 (4)	C13—C14—C15—C16	−0.7 (8)
N1—C3—C4—C9	28.0 (7)	C12—C11—C16—C15	0.2 (8)
N3—C3—C4—C9	−152.0 (5)	C12—C11—C16—C17	179.5 (5)
N1—C3—C4—C5	−149.9 (5)	C14—C15—C16—C11	0.3 (9)
N3—C3—C4—C5	30.1 (7)	C14—C15—C16—C17	−179.0 (6)
C9—C4—C5—C6	0.1 (7)	C12—C13—C18—O1	−173.4 (4)
C3—C4—C5—C6	178.0 (4)	C14—C13—C18—O1	6.4 (7)
C4—C5—C6—C7	−0.1 (7)	C12—C13—C18—O2	6.4 (6)
C5—C6—C7—C8	0.1 (8)	C14—C13—C18—O2	−173.8 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.77 (6)	1.92 (6)	2.682 (4)	171 (6)
N4—H1N4···O1	0.97 (6)	1.98 (6)	2.936 (5)	169 (6)
N4—H2N4···N3ⁱ	0.84 (4)	2.26 (4)	3.099 (5)	172 (4)
N5—H1N5···N1ⁱⁱ	0.90 (6)	2.11 (6)	3.003 (5)	173 (5)
C10—H10C···Cg2ⁱⁱⁱ	0.98	2.83	3.723 (6)	152

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁N₅·C₈H₈O₂
M_r	337.38
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	11.1271 (3), 20.9492 (6), 7.4189 (2)
β (°)	101.321 (2)
V (Å³)	1695.73 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.965, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	8715, 1932, 1811
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.135, 1.19
No. of reflections	1932
No. of parameters	244
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.27

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 C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.77 (6)	1.92 (6)	2.682 (4)	171 (6)
N4—H1N4···O1	0.97 (6)	1.98 (6)	2.936 (5)	169 (6)
N4—H2N4···N3ⁱ	0.84 (4)	2.26 (4)	3.099 (5)	172 (4)
N5—H1N5···N1ⁱⁱ	0.90 (6)	2.11 (6)	3.003 (5)	173 (5)
C10—H10C···Cg2ⁱⁱⁱ	0.98	2.83	3.723 (6)	152

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

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

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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