Literature DB >> 23795125

6-(4-Methyl-phen-yl)-1,3,5-triazine-2,4-di-amine-benzoic acid (1/1).

Kaliyaperumal Thanigaimani1, Nuridayanti Che Khalib, Ibrahim Abdul Razak, Palanisamy Lavanya, Kasthuri Balasubramani.   

Abstract

The benzoic acid mol-ecule of the title adduct, C10H11N5·C7H6O2, is approximately planar, with a dihedral angle of 7.2 (3)° between the carb-oxy-lic acid group and the benzene ring. In the triazine mol-ecule, 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 R 2 (2)(8) motif, thus generating a 1 + 1 unit of triazine and benzoic acid mol-ecules. The acid-base units are further connected by N-H⋯N hydrogen bonds with R 2 (2)(8) motifs, forming a supra-molecular 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 inter-actions.

Entities:  

Year:  2013        PMID： 23795125      PMCID： PMC3685106          DOI： 10.1107/S1600536813013883

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 323.36 Triclinic, 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[F 2 > 2σ(F 2)] = 0.062 wR(F 2) = 0.157 S = 1.11 4578 reflections 238 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.38 e Å−3 Δρmin = −0.40 e Å−3 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 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013883/is5271sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013883/is5271Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813013883/is5271Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C10H11N5·C7H6O2Z = 2
Mr = 323.36F(000) = 340
Triclinic, P1Dx = 1.371 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4324 (5) ÅCell parameters from 7150 reflections
b = 10.9717 (3) Åθ = 2.9–30.0°
c = 11.2267 (3) ŵ = 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
Bruker SMART APEXII CCD area-detector diffractometer4578 independent reflections
Radiation source: fine-focus sealed tube3744 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −10→10
Tmin = 0.952, Tmax = 0.980k = −15→14
16402 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.0412P)2 + 1.1661P] where P = (Fo2 + 2Fc2)/3
4578 reflections(Δ/σ)max < 0.001
238 parametersΔρmax = 0.38 e Å−3
1 restraintΔρmin = −0.40 e Å−3
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.
xyzUiso*/Ueq
N10.7322 (2)0.67180 (16)0.85847 (15)0.0142 (3)
N20.6434 (2)0.46349 (15)0.63917 (16)0.0134 (3)
N30.8105 (2)0.45860 (16)0.84190 (15)0.0143 (3)
N40.5792 (2)0.67431 (17)0.66117 (17)0.0174 (3)
N50.8918 (3)0.66235 (18)1.05089 (17)0.0183 (3)
O10.7991 (2)−0.06107 (15)0.03289 (15)0.0225 (3)
O20.6262 (2)−0.02682 (15)−0.13338 (15)0.0238 (3)
C10.7538 (3)−0.1872 (2)0.3826 (2)0.0216 (4)
H1A0.7117−0.23880.42680.032*
H1B0.8831−0.19590.37880.032*
H1C0.6732−0.22550.28810.032*
C20.7436 (2)−0.03535 (19)0.4656 (2)0.0161 (4)
C30.7435 (3)0.02206 (19)0.6053 (2)0.0165 (4)
H3A0.7479−0.03570.64770.020*
C40.7371 (3)0.16236 (19)0.68307 (19)0.0154 (3)
H4A0.73770.19970.77800.018*
C50.7297 (2)0.24850 (18)0.62243 (18)0.0128 (3)
C60.7296 (3)0.19181 (19)0.48277 (19)0.0147 (3)
H6A0.72470.24950.44020.018*
C70.7367 (3)0.05171 (19)0.40579 (19)0.0169 (4)
H7A0.73690.01460.31100.020*
C80.7265 (2)0.39923 (18)0.70582 (18)0.0127 (3)
C90.8102 (2)0.59648 (18)0.91395 (18)0.0136 (3)
C100.6516 (2)0.60150 (18)0.72027 (18)0.0138 (3)
C110.7236 (3)0.0182 (2)−0.01503 (19)0.0173 (4)
C120.7677 (3)0.17012 (19)0.0888 (2)0.0174 (4)
C130.8950 (3)0.2206 (2)0.2173 (2)0.0192 (4)
H13A0.95520.15820.24110.023*
C140.9343 (3)0.3624 (2)0.3110 (2)0.0224 (4)
H14A1.02180.39700.39880.027*
C150.8454 (3)0.4537 (2)0.2765 (2)0.0258 (5)
H15A0.87240.55070.34090.031*
C160.7172 (3)0.4037 (2)0.1480 (2)0.0256 (5)
H16A0.65700.46630.12450.031*
C170.6776 (3)0.2617 (2)0.0543 (2)0.0211 (4)
H17A0.58930.2269−0.03320.025*
H1N40.527 (3)0.638 (2)0.576 (2)0.012 (5)*
H2N40.584 (4)0.762 (3)0.715 (3)0.021 (6)*
H1N50.965 (4)0.621 (3)1.082 (3)0.026 (7)*
H2N50.909 (4)0.746 (3)1.090 (3)0.026 (7)*
H1O10.762 (5)−0.1439 (16)−0.029 (3)0.066 (11)*
U11U22U33U12U13U23
N10.0161 (7)0.0122 (7)0.0114 (7)0.0041 (5)0.0008 (5)0.0042 (6)
N20.0143 (7)0.0117 (7)0.0125 (7)0.0032 (5)0.0009 (5)0.0053 (6)
N30.0160 (7)0.0125 (7)0.0118 (7)0.0039 (6)0.0015 (5)0.0045 (6)
N40.0241 (8)0.0127 (7)0.0109 (7)0.0057 (6)−0.0014 (6)0.0041 (6)
N50.0250 (9)0.0135 (7)0.0120 (7)0.0072 (6)0.0001 (6)0.0041 (6)
O10.0317 (8)0.0136 (6)0.0159 (7)0.0043 (6)−0.0003 (6)0.0045 (5)
O20.0323 (8)0.0166 (7)0.0174 (7)0.0055 (6)0.0005 (6)0.0063 (6)
C10.0202 (9)0.0141 (8)0.0263 (10)0.0055 (7)0.0070 (8)0.0056 (8)
C20.0115 (8)0.0136 (8)0.0192 (9)0.0025 (6)0.0030 (6)0.0050 (7)
C30.0159 (8)0.0146 (8)0.0206 (9)0.0038 (7)0.0043 (7)0.0100 (7)
C40.0150 (8)0.0163 (8)0.0134 (8)0.0029 (6)0.0024 (6)0.0066 (7)
C50.0112 (7)0.0118 (7)0.0132 (8)0.0024 (6)0.0016 (6)0.0049 (6)
C60.0148 (8)0.0159 (8)0.0145 (8)0.0042 (6)0.0036 (6)0.0081 (7)
C70.0185 (9)0.0157 (8)0.0137 (8)0.0042 (7)0.0046 (7)0.0046 (7)
C80.0121 (8)0.0118 (7)0.0137 (8)0.0022 (6)0.0032 (6)0.0059 (6)
C90.0145 (8)0.0130 (8)0.0123 (8)0.0039 (6)0.0032 (6)0.0053 (6)
C100.0135 (8)0.0132 (8)0.0137 (8)0.0033 (6)0.0021 (6)0.0061 (7)
C110.0201 (9)0.0146 (8)0.0167 (8)0.0032 (7)0.0058 (7)0.0068 (7)
C120.0206 (9)0.0125 (8)0.0186 (9)0.0032 (7)0.0096 (7)0.0053 (7)
C130.0211 (9)0.0157 (9)0.0200 (9)0.0033 (7)0.0078 (7)0.0070 (7)
C140.0213 (9)0.0176 (9)0.0214 (9)−0.0011 (7)0.0085 (8)0.0032 (8)
C150.0276 (11)0.0136 (9)0.0321 (11)0.0003 (8)0.0154 (9)0.0050 (8)
C160.0294 (11)0.0176 (9)0.0370 (12)0.0090 (8)0.0179 (9)0.0147 (9)
C170.0241 (10)0.0190 (9)0.0242 (10)0.0059 (7)0.0108 (8)0.0117 (8)
N1—C91.341 (2)C3—C41.390 (3)
N1—C101.351 (2)C3—H3A0.9500
N2—C81.340 (2)C4—C51.393 (3)
N2—C101.353 (2)C4—H4A0.9500
N3—C81.340 (2)C5—C61.398 (2)
N3—C91.351 (2)C5—C81.487 (2)
N4—C101.330 (2)C6—C71.388 (3)
N4—H1N40.84 (2)C6—H6A0.9500
N4—H2N40.86 (3)C7—H7A0.9500
N5—C91.342 (2)C11—C121.495 (3)
N5—H1N50.85 (3)C12—C131.389 (3)
N5—H2N50.80 (3)C12—C171.398 (3)
O1—C111.318 (2)C13—C141.388 (3)
O1—H1O10.833 (10)C13—H13A0.9500
O2—C111.222 (2)C14—C151.392 (3)
C1—C21.509 (3)C14—H14A0.9500
C1—H1A0.9800C15—C161.392 (3)
C1—H1B0.9800C15—H15A0.9500
C1—H1C0.9800C16—C171.391 (3)
C2—C71.395 (3)C16—H16A0.9500
C2—C31.397 (3)C17—H17A0.9500
C9—N1—C10115.80 (15)C6—C7—H7A119.5
C8—N2—C10114.74 (15)C2—C7—H7A119.5
C8—N3—C9114.64 (15)N2—C8—N3126.06 (16)
C10—N4—H1N4122.6 (16)N2—C8—C5117.84 (15)
C10—N4—H2N4116.8 (17)N3—C8—C5116.10 (15)
H1N4—N4—H2N4121 (2)N1—C9—N5117.70 (16)
C9—N5—H1N5117.4 (18)N1—C9—N3124.60 (16)
C9—N5—H2N5117.2 (19)N5—C9—N3117.69 (17)
H1N5—N5—H2N5119 (3)N4—C10—N1117.28 (16)
C11—O1—H1O1108 (3)N4—C10—N2118.57 (16)
C2—C1—H1A109.5N1—C10—N2124.15 (16)
C2—C1—H1B109.5O2—C11—O1123.70 (18)
H1A—C1—H1B109.5O2—C11—C12122.39 (18)
C2—C1—H1C109.5O1—C11—C12113.91 (17)
H1A—C1—H1C109.5C13—C12—C17120.07 (18)
H1B—C1—H1C109.5C13—C12—C11121.28 (18)
C7—C2—C3118.31 (17)C17—C12—C11118.65 (18)
C7—C2—C1120.98 (18)C14—C13—C12119.9 (2)
C3—C2—C1120.70 (18)C14—C13—H13A120.0
C4—C3—C2121.04 (18)C12—C13—H13A120.0
C4—C3—H3A119.5C13—C14—C15120.1 (2)
C2—C3—H3A119.5C13—C14—H14A120.0
C3—C4—C5120.29 (17)C15—C14—H14A120.0
C3—C4—H4A119.9C14—C15—C16120.27 (19)
C5—C4—H4A119.9C14—C15—H15A119.9
C4—C5—C6119.00 (16)C16—C15—H15A119.9
C4—C5—C8120.53 (16)C17—C16—C15119.7 (2)
C6—C5—C8120.46 (16)C17—C16—H16A120.2
C7—C6—C5120.42 (17)C15—C16—H16A120.2
C7—C6—H6A119.8C16—C17—C12120.0 (2)
C5—C6—H6A119.8C16—C17—H17A120.0
C6—C7—C2120.94 (17)C12—C17—H17A120.0
C7—C2—C3—C4−0.1 (3)C10—N1—C9—N3−0.8 (3)
C1—C2—C3—C4179.00 (17)C8—N3—C9—N10.7 (3)
C2—C3—C4—C50.3 (3)C8—N3—C9—N5179.86 (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—N21.3 (3)
C4—C5—C6—C70.0 (3)C8—N2—C10—N4177.28 (17)
C8—C5—C6—C7178.61 (17)C8—N2—C10—N1−1.5 (3)
C5—C6—C7—C20.1 (3)O2—C11—C12—C13−172.78 (19)
C3—C2—C7—C6−0.1 (3)O1—C11—C12—C137.2 (3)
C1—C2—C7—C6−179.21 (17)O2—C11—C12—C177.3 (3)
C10—N2—C8—N31.4 (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—C14179.43 (18)
C9—N3—C8—C5178.05 (16)C12—C13—C14—C150.3 (3)
C4—C5—C8—N2−152.42 (17)C13—C14—C15—C16−0.1 (3)
C6—C5—C8—N229.0 (2)C14—C15—C16—C170.2 (3)
C4—C5—C8—N328.5 (2)C15—C16—C17—C12−0.6 (3)
C6—C5—C8—N3−150.08 (17)C13—C12—C17—C160.8 (3)
C10—N1—C9—N5179.96 (17)C11—C12—C17—C16−179.30 (18)
D—H···AD—HH···AD···AD—H···A
N4—H1N4···N2i0.839 (19)2.19 (2)3.021 (2)172 (2)
N4—H2N4···O2ii0.86 (3)2.11 (3)2.965 (3)172 (3)
N5—H1N5···N3iii0.85 (3)2.14 (3)2.984 (3)169 (3)
O1—H1O1···N1iv0.83 (3)1.80 (3)2.613 (2)167 (3)
C1—H1B···Cg2v0.982.753.661 (2)156
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 ring.

D—H⋯A D—HH⋯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⋯N1iv 0.83 (3)1.80 (3)2.613 (2)167 (3)
C1—H1B⋯Cg2v 0.982.753.661 (2)156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

  5 in total

1.  Novel orthogonal strategy toward solid-phase synthesis of 1,3,5-substituted triazines.

Authors:  Jacqueline T Bork; Jae Wook Lee; Sonya M Khersonsky; Ho-Sang Moon; Young-Tae Chang
Journal:  Org Lett       Date:  2003-01-23       Impact factor: 6.005

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Adipic acid-2,4-diamino-6-(4-meth-oxy-phen-yl)-1,3,5-triazine (1/2).

Authors:  Kaliyaperumal Thanigaimani; Ibrahim Abdul Razak; Suhana Arshad; Rathinavel Jagatheesan; Kulandaisamy Joseph Santhanaraj
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-15

4.  6-(4-Meth-oxy-phen-yl)-1,3,5-triazine-2,4-diamine.

Authors:  Kaliyaperumal Thanigaimani; Ibrahim Abdul Razak; Suhana Arshad; Rathinavel Jagatheesan; K Joseph Santhanaraj
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-08

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  5 in total
  1 in total

1.  6-(4-Methyl-phen-yl)-1,3,5-triazine-2,4-di-amine-4-methyl-benzoic acid (1/1).

Authors:  Kaliyaperumal Thanigaimani; Suhana Arshad; Ibrahim Abdul Razak; Duraisamy Makeshvaran; Kasthuri Balasubramani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-05-25
  1 in total

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