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The crystal structure of the novel title benzyl­ated carboxy­triazole, C14H11N3O2, having potential as a corrosion inhibitor for copper and copper-based alloys, confirms that the site of the benzyl substituent is on the triazole ring nitro­gen which is trans-related rather than cis-related to the carboxyl­ic acid group. The mol­ecules participate in asymmetric intermolecular hydrogen-bonding interactions involving the carboxyl­ic acid H atom and two of the triazole N atoms [O...N 2.683 (5) and 3.413 (5) Å], giving rise to a chain polymer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008133/tk6012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008133/tk6012Isup2.hkl
Contains datablock I

CCDC reference: 170306

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.042
  • wR factor = 0.102
  • Data-to-parameter ratio = 7.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
SYMMS_02 Alert B The unit-cell lengths a and b should not be equal for an orthorhombic cell Cell 12.2039 12.2039 8.3430 Angles 90.0000 90.0000 90.0000
Author response: This fact was recognized and a comment made in exptl_special_details that our checks for higher symmetry indicated that the cell was orthorhombic (space group P21 21 21) not tetragonal.
General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.97 From the CIF: _reflns_number_total 1277 Count of symmetry unique reflns 1277 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 1999).

1-N-benzyl-4-carboxybenzotriazole top
Crystal data top
C14H11N3O2Dx = 1.354 Mg m3
Mr = 253.26Melting point: 493–495 K K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
a = 12.2039 (8) ÅCell parameters from 25 reflections
b = 12.2039 (8) Åθ = 19.0–21.0°
c = 8.343 (1) ŵ = 0.09 mm1
V = 1242.57 (19) Å3T = 298 K
Z = 4Prism, colourless
F(000) = 5280.35 × 0.25 × 0.20 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.000
Radiation source: X-ray tubeθmax = 25.0°, θmin = 2.4°
Graphite monochromatorh = 014
ω–2θ scansk = 014
1277 measured reflectionsl = 09
1277 independent reflections3 standard reflections every 150 reflections
655 reflections with I > 2σ(I) intensity decay: 10.2%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0361P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.16 e Å3
1277 reflectionsΔρmin = 0.17 e Å3
176 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.019 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983)
Secondary atom site location: difference Fourier map
Special details top

Experimental. Although the a and b cell parameters were identical, no symmetry higher than orthorhombic could be identified. The poor data to parameter ratio (7.26) (non-centrosymmetric) arises because of the significant decomposition (ca 12%) in the crystal. Since there is no possibility of re-collection possibly at low temperature this less than desirable feature of the structure has to be accepted.

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. Absolute configuration could not be determined with any certainty (Flack, 1983). A 10% intensity loss during the data collection period indicated significant crystal decay and was allowed for by a linear correction.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O400.2233 (3)0.4828 (3)0.0420 (5)0.0838 (15)
O410.3489 (2)0.5638 (3)0.1892 (5)0.0650 (11)
N10.4301 (3)0.1840 (3)0.2118 (5)0.0459 (10)
N20.3396 (3)0.2311 (3)0.2740 (5)0.0546 (12)
N30.3145 (3)0.3163 (3)0.1863 (5)0.0459 (11)
C40.3989 (4)0.4014 (3)0.0608 (6)0.0406 (12)
C50.4878 (4)0.3900 (4)0.1578 (6)0.0544 (15)
C60.5647 (4)0.3056 (5)0.1386 (6)0.0674 (16)
C70.5544 (4)0.2277 (4)0.0208 (7)0.0554 (15)
C80.4643 (4)0.2399 (3)0.0791 (6)0.0403 (12)
C90.3888 (4)0.3245 (3)0.0626 (6)0.0367 (11)
C100.4714 (4)0.0825 (4)0.2818 (6)0.0576 (15)
C110.4051 (4)0.0147 (4)0.2357 (6)0.0510 (14)
C120.4401 (5)0.0872 (5)0.1215 (7)0.0642 (16)
C130.3794 (7)0.1784 (5)0.0795 (7)0.087 (2)
C140.2807 (7)0.1967 (6)0.1505 (11)0.097 (3)
C150.2418 (5)0.1251 (5)0.2628 (10)0.095 (2)
C160.3041 (5)0.0345 (4)0.3065 (8)0.0747 (19)
C410.3141 (4)0.4855 (4)0.0942 (6)0.0449 (13)
H410.285 (5)0.606 (5)0.223 (9)0.101*
H50.4980.4420.2420.065*
H60.6260.3020.2100.081*
H70.6060.1700.0080.066*
H120.5080.0750.0690.077*
H130.4070.2280.0010.104*
H140.2390.2590.1220.117*
H150.1720.1370.3110.114*
H160.2770.0140.3860.090*
H1010.5450.0720.2460.069*
H1020.4700.0890.3950.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O400.049 (3)0.076 (3)0.127 (4)0.023 (2)0.022 (3)0.045 (3)
O410.0377 (19)0.063 (2)0.094 (3)0.0063 (19)0.001 (2)0.034 (2)
N10.044 (2)0.039 (2)0.054 (3)0.008 (2)0.005 (2)0.006 (2)
N20.050 (2)0.051 (2)0.064 (3)0.003 (2)0.008 (3)0.006 (2)
N30.046 (3)0.034 (2)0.058 (3)0.007 (2)0.006 (3)0.002 (2)
C40.035 (3)0.038 (3)0.049 (3)0.003 (2)0.004 (3)0.001 (3)
C50.053 (3)0.054 (3)0.056 (4)0.009 (3)0.002 (3)0.015 (3)
C60.057 (3)0.091 (4)0.054 (3)0.035 (4)0.016 (3)0.013 (4)
C70.047 (3)0.063 (3)0.056 (3)0.023 (3)0.001 (3)0.004 (3)
C80.042 (3)0.039 (3)0.040 (3)0.007 (2)0.009 (3)0.002 (2)
C90.035 (3)0.034 (2)0.042 (3)0.002 (2)0.001 (3)0.004 (2)
C100.062 (4)0.043 (3)0.068 (4)0.009 (3)0.012 (3)0.009 (3)
C110.061 (4)0.036 (3)0.055 (4)0.006 (3)0.005 (3)0.008 (3)
C120.078 (4)0.057 (3)0.058 (4)0.010 (4)0.002 (3)0.017 (3)
C130.143 (7)0.059 (4)0.059 (4)0.011 (5)0.033 (5)0.002 (4)
C140.128 (7)0.063 (4)0.100 (7)0.024 (5)0.045 (6)0.021 (4)
C150.083 (5)0.086 (5)0.116 (7)0.027 (4)0.005 (5)0.034 (5)
C160.074 (4)0.059 (4)0.091 (5)0.001 (3)0.011 (4)0.012 (4)
C410.037 (3)0.035 (3)0.063 (4)0.002 (3)0.001 (3)0.007 (3)
Geometric parameters (Å, º) top
O40—C411.191 (5)C7—H70.95
O41—C411.312 (5)C8—C91.392 (6)
O41—H410.98 (6)C10—C111.486 (6)
N1—N21.348 (5)C10—H1010.95
N1—C81.365 (5)C10—H1020.95
N1—C101.460 (5)C11—C121.369 (7)
N2—N31.307 (5)C11—C161.388 (7)
N3—C91.377 (5)C12—C131.382 (8)
C4—C51.361 (6)C12—H120.95
C4—C91.398 (5)C13—C141.361 (9)
C4—C411.484 (6)C13—H130.95
C5—C61.402 (6)C14—C151.366 (9)
C5—H50.95C14—H140.95
C6—C71.374 (6)C15—C161.391 (8)
C6—H60.95C15—H150.95
C7—C81.387 (6)C16—H160.95
C41—O41—H41107 (4)C11—C10—H101109
N2—N1—C8110.5 (3)N1—C10—H102109
N2—N1—C10119.4 (4)C11—C10—H102109
C8—N1—C10130.0 (4)H101—C10—H102109
N3—N2—N1108.4 (4)C12—C11—C16117.5 (5)
N2—N3—C9108.9 (4)C12—C11—C10121.8 (5)
C5—C4—C9116.1 (4)C16—C11—C10120.8 (5)
C5—C4—C41121.0 (4)C11—C12—C13122.0 (6)
C9—C4—C41122.7 (4)C11—C12—H12119
C4—C5—C6122.7 (5)C13—C12—H12119
C4—C5—H5119C14—C13—C12119.8 (7)
C6—C5—H5119C14—C13—H13120
C7—C6—C5121.9 (5)C12—C13—H13120
C7—C6—H6119C13—C14—C15120.1 (7)
C5—C6—H6119C13—C14—H14120
C6—C7—C8115.4 (5)C15—C14—H14120
C6—C7—H7122C14—C15—C16119.9 (7)
C8—C7—H7122C14—C15—H15120
N1—C8—C7132.5 (4)C16—C15—H15120
N1—C8—C9104.4 (4)C11—C16—C15120.8 (6)
C7—C8—C9123.0 (5)C11—C16—H16120
N3—C9—C8107.9 (4)C15—C16—H16120
N3—C9—C4131.2 (4)O40—C41—O41122.8 (5)
C8—C9—C4120.8 (4)O40—C41—C4124.1 (5)
N1—C10—C11112.7 (4)O41—C41—C4113.0 (4)
N1—C10—H101109
C8—N1—N2—N30.4 (5)C41—C4—C9—N39.6 (7)
C10—N1—N2—N3176.1 (4)C5—C4—C9—C82.2 (6)
N1—N2—N3—C90.9 (5)C41—C4—C9—C8173.1 (4)
C9—C4—C5—C61.0 (7)N2—N1—C10—C1175.9 (5)
C41—C4—C5—C6174.3 (5)C8—N1—C10—C1198.7 (5)
C4—C5—C6—C70.7 (9)N1—C10—C11—C12102.9 (5)
C5—C6—C7—C81.2 (8)N1—C10—C11—C1676.4 (6)
N2—N1—C8—C7176.3 (5)C16—C11—C12—C131.4 (7)
C10—N1—C8—C78.6 (8)C10—C11—C12—C13179.3 (5)
N2—N1—C8—C90.3 (4)C11—C12—C13—C141.3 (9)
C10—N1—C8—C9174.8 (4)C12—C13—C14—C150.1 (10)
C6—C7—C8—N1176.0 (5)C13—C14—C15—C161.1 (10)
C6—C7—C8—C90.1 (7)C12—C11—C16—C150.3 (8)
N2—N3—C9—C81.1 (5)C10—C11—C16—C15179.6 (5)
N2—N3—C9—C4178.7 (4)C14—C15—C16—C110.9 (10)
N1—C8—C9—N30.8 (5)C5—C4—C41—O40160.2 (5)
C7—C8—C9—N3176.2 (4)C9—C4—C41—O4014.8 (8)
N1—C8—C9—C4178.7 (4)C5—C4—C41—O4119.2 (7)
C7—C8—C9—C41.7 (7)C9—C4—C41—O41165.8 (4)
C5—C4—C9—N3175.2 (5)
 

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