Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011011/ci6043sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011011/ci6043Isup2.hkl |
CCDC reference: 170893
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.037
- wR factor = 0.138
- Data-to-parameter ratio = 8.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2231 Count of symmetry unique reflns 2232 Completeness (_total/calc) 99.96% 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.
The title compound was synthesized by the slow addition of 20 ml of a solution of phthaloyl chloride (4.3 ml, 60 mmol) in tetrahydrofuran to 100 ml of a solution containing benzotriazole (7.14 g, 60 mmol) and triethylamine (8.4 ml, 60 mmol) (also in tetrahydrofuran), maintained at 273–278 K. After stirring for ca 12 h, the mixture was poured onto ice and the resulting precipitate washed with water and recrystallized from chloroform from which data-quality crystals were obtained.
The positional and isotropic displacement parameters of the H atoms were fixed in the refinement.
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); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: TEXSAN for Windows.
Fig. 1. The molecular configuration and atom-numbering scheme for (I). are shown as 30% probability ellipsoids. |
C20H12N6O2 | Dx = 1.450 Mg m−3 |
Mr = 368.36 | Melting point = 464–466 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
a = 10.744 (5) Å | Cell parameters from 25 reflections |
b = 22.193 (4) Å | θ = 8.4–14.7° |
c = 7.079 (5) Å | µ = 0.10 mm−1 |
V = 1687.9 (14) Å3 | T = 295 K |
Z = 4 | Plate, colourless |
F(000) = 760 | 0.38 × 0.25 × 0.20 mm |
Rigaku AFC-7R diffractometer | Rint = 0.000 |
Radiation source: Rigaku rotating anode | θmax = 27.5°, θmin = 2.1° |
Graphite monochromator | h = 0→13 |
ω–2θ scans | k = 0→28 |
2231 measured reflections | l = 0→9 |
2231 independent reflections | 3 standard reflections every 150 reflections |
992 reflections with I > 2σ(I)' | intensity decay: 0.0% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.0638P)2 + 0.2455P] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max < 0.001 |
2231 reflections | Δρmax = 0.18 e Å−3 |
254 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (2) |
C20H12N6O2 | V = 1687.9 (14) Å3 |
Mr = 368.36 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.744 (5) Å | µ = 0.10 mm−1 |
b = 22.193 (4) Å | T = 295 K |
c = 7.079 (5) Å | 0.38 × 0.25 × 0.20 mm |
Rigaku AFC-7R diffractometer | Rint = 0.000 |
2231 measured reflections | 3 standard reflections every 150 reflections |
2231 independent reflections | intensity decay: 0.0% |
992 reflections with I > 2σ(I)' |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.18 e Å−3 |
2231 reflections | Δρmin = −0.18 e Å−3 |
254 parameters |
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. The absolute configuration could not be determined because of the composition of the compound and the quantity of data collected. The lower than desirable reflection-to-parameter ratio (8.78) is considered acceptable because of the noncentrosymmetric space group (Acta recommended ratio: 8.0). |
x | y | z | Uiso*/Ueq | ||
O11 | 0.9414 (3) | 0.19130 (14) | −0.1172 (5) | 0.0514 (9) | |
O21 | 0.6808 (3) | 0.20081 (14) | 0.1940 (5) | 0.0545 (9) | |
N11 | 1.1388 (3) | 0.17183 (15) | −0.0238 (5) | 0.0382 (9) | |
N12 | 1.2205 (4) | 0.16543 (19) | 0.1263 (6) | 0.0514 (11) | |
N13 | 1.3070 (4) | 0.12837 (19) | 0.0815 (6) | 0.0546 (11) | |
N21 | 0.8174 (3) | 0.12445 (15) | 0.2230 (6) | 0.0419 (9) | |
N22 | 0.9395 (3) | 0.10449 (16) | 0.2440 (6) | 0.0485 (10) | |
N23 | 0.9395 (4) | 0.04697 (16) | 0.2481 (6) | 0.0515 (11) | |
C1 | 1.0017 (4) | 0.23523 (18) | 0.1734 (6) | 0.0402 (11) | |
C2 | 0.8883 (4) | 0.22956 (18) | 0.2698 (6) | 0.0396 (11) | |
C3 | 0.8648 (4) | 0.2658 (2) | 0.4268 (7) | 0.0473 (12) | |
C4 | 0.9521 (5) | 0.3068 (2) | 0.4859 (7) | 0.0538 (13) | |
C5 | 1.0631 (5) | 0.3131 (2) | 0.3921 (7) | 0.0520 (13) | |
C6 | 1.0878 (4) | 0.27723 (19) | 0.2374 (7) | 0.0469 (12) | |
C11 | 1.0212 (4) | 0.19918 (19) | −0.0001 (7) | 0.0404 (11) | |
C14 | 1.2838 (4) | 0.1079 (2) | −0.1022 (7) | 0.0445 (12) | |
C15 | 1.3493 (4) | 0.0662 (2) | −0.2089 (7) | 0.0561 (14) | |
C16 | 1.3064 (5) | 0.0540 (2) | −0.3865 (8) | 0.0586 (14) | |
C17 | 1.2006 (5) | 0.0832 (2) | −0.4557 (7) | 0.0552 (14) | |
C18 | 1.1344 (4) | 0.1248 (2) | −0.3524 (7) | 0.0444 (12) | |
C19 | 1.1771 (4) | 0.13560 (18) | −0.1692 (6) | 0.0372 (11) | |
C21 | 0.7875 (4) | 0.1867 (2) | 0.2197 (6) | 0.0415 (11) | |
C24 | 0.8166 (4) | 0.02648 (19) | 0.2318 (7) | 0.0425 (11) | |
C25 | 0.7708 (5) | −0.0328 (2) | 0.2411 (8) | 0.0559 (14) | |
C26 | 0.6447 (5) | −0.0393 (2) | 0.2290 (8) | 0.0607 (15) | |
C27 | 0.5663 (5) | 0.0104 (2) | 0.2119 (8) | 0.0595 (14) | |
C28 | 0.6098 (4) | 0.0683 (2) | 0.2031 (7) | 0.0498 (12) | |
C29 | 0.7382 (4) | 0.0754 (2) | 0.2171 (6) | 0.0398 (10) | |
H3 | 0.7882 | 0.2622 | 0.4927 | 0.056* | |
H4 | 0.9360 | 0.3313 | 0.5935 | 0.064* | |
H5 | 1.1227 | 0.3418 | 0.4332 | 0.061* | |
H6 | 1.1650 | 0.2814 | 0.1731 | 0.055* | |
H15 | 1.4215 | 0.0469 | −0.1601 | 0.066* | |
H16 | 1.3488 | 0.0255 | −0.4633 | 0.069* | |
H17 | 1.1735 | 0.0741 | −0.5803 | 0.065* | |
H18 | 1.0635 | 0.1448 | −0.4028 | 0.052* | |
H25 | 0.8249 | −0.0665 | 0.2547 | 0.067* | |
H26 | 0.6090 | −0.0785 | 0.2328 | 0.072* | |
H27 | 0.4788 | 0.0040 | 0.2060 | 0.070* | |
H28 | 0.5553 | 0.1018 | 0.1880 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0431 (19) | 0.063 (2) | 0.0482 (19) | 0.0048 (17) | −0.0095 (18) | −0.0097 (19) |
O21 | 0.0412 (18) | 0.056 (2) | 0.067 (2) | 0.0128 (16) | −0.0062 (19) | 0.0020 (19) |
N11 | 0.039 (2) | 0.045 (2) | 0.0304 (19) | 0.0005 (18) | −0.0027 (18) | −0.0016 (18) |
N12 | 0.050 (2) | 0.063 (3) | 0.040 (2) | 0.008 (2) | −0.007 (2) | −0.001 (2) |
N13 | 0.046 (2) | 0.066 (3) | 0.052 (3) | 0.011 (2) | −0.009 (2) | −0.001 (2) |
N21 | 0.0317 (18) | 0.0378 (19) | 0.056 (2) | 0.0048 (19) | −0.009 (2) | 0.004 (2) |
N22 | 0.042 (2) | 0.042 (2) | 0.062 (3) | 0.0072 (18) | −0.002 (2) | 0.007 (2) |
N23 | 0.046 (2) | 0.042 (2) | 0.066 (3) | 0.0039 (19) | −0.007 (2) | 0.006 (2) |
C1 | 0.048 (3) | 0.033 (2) | 0.040 (3) | 0.002 (2) | −0.003 (2) | 0.005 (2) |
C2 | 0.042 (2) | 0.037 (2) | 0.040 (3) | 0.008 (2) | −0.003 (2) | 0.003 (2) |
C3 | 0.049 (3) | 0.048 (3) | 0.045 (3) | 0.005 (2) | 0.004 (2) | 0.001 (2) |
C4 | 0.069 (3) | 0.051 (3) | 0.042 (3) | 0.005 (3) | −0.003 (3) | −0.007 (3) |
C5 | 0.062 (3) | 0.041 (3) | 0.053 (3) | 0.000 (3) | −0.005 (3) | 0.000 (3) |
C6 | 0.050 (3) | 0.045 (3) | 0.046 (3) | −0.006 (2) | 0.002 (3) | 0.002 (3) |
C11 | 0.042 (3) | 0.039 (2) | 0.041 (3) | −0.004 (2) | 0.001 (3) | 0.004 (2) |
C14 | 0.036 (3) | 0.050 (3) | 0.047 (3) | 0.001 (2) | −0.001 (2) | −0.002 (2) |
C15 | 0.050 (3) | 0.057 (3) | 0.062 (3) | 0.010 (3) | 0.011 (3) | 0.002 (3) |
C16 | 0.058 (3) | 0.057 (3) | 0.061 (3) | 0.004 (3) | 0.018 (3) | −0.011 (3) |
C17 | 0.058 (3) | 0.058 (3) | 0.050 (3) | −0.014 (3) | 0.007 (3) | −0.013 (3) |
C18 | 0.042 (3) | 0.050 (3) | 0.041 (3) | −0.009 (2) | −0.001 (2) | −0.003 (2) |
C19 | 0.042 (3) | 0.035 (2) | 0.035 (2) | −0.003 (2) | 0.008 (2) | 0.003 (2) |
C21 | 0.046 (3) | 0.044 (3) | 0.035 (2) | 0.008 (2) | −0.001 (2) | −0.001 (2) |
C24 | 0.049 (3) | 0.039 (2) | 0.040 (3) | 0.001 (2) | −0.004 (3) | 0.004 (2) |
C25 | 0.073 (4) | 0.043 (3) | 0.052 (3) | −0.001 (3) | −0.010 (3) | 0.004 (3) |
C26 | 0.070 (4) | 0.056 (3) | 0.056 (3) | −0.017 (3) | −0.005 (3) | −0.003 (3) |
C27 | 0.049 (3) | 0.072 (4) | 0.057 (3) | −0.011 (3) | −0.007 (3) | −0.008 (3) |
C28 | 0.043 (3) | 0.057 (3) | 0.050 (3) | 0.001 (2) | −0.002 (2) | −0.015 (3) |
C29 | 0.039 (2) | 0.046 (3) | 0.035 (2) | −0.002 (2) | −0.003 (2) | −0.004 (2) |
O11—C11 | 1.205 (5) | C5—H5 | 0.95 |
O21—C21 | 1.203 (5) | C6—H6 | 0.95 |
N11—C19 | 1.370 (5) | C14—C15 | 1.386 (6) |
N11—N12 | 1.385 (5) | C14—C19 | 1.385 (6) |
N11—C11 | 1.412 (5) | C15—C16 | 1.366 (7) |
N12—N13 | 1.281 (5) | C15—H15 | 0.95 |
N13—C14 | 1.400 (6) | C16—C17 | 1.398 (7) |
N21—C29 | 1.383 (5) | C16—H16 | 0.95 |
N21—N22 | 1.393 (5) | C17—C18 | 1.375 (6) |
N21—C21 | 1.419 (5) | C17—H17 | 0.95 |
N22—N23 | 1.277 (5) | C18—C19 | 1.396 (6) |
N23—C24 | 1.401 (6) | C18—H18 | 0.95 |
C1—C6 | 1.389 (6) | C24—C29 | 1.378 (6) |
C1—C2 | 1.402 (6) | C24—C25 | 1.407 (6) |
C1—C11 | 1.480 (6) | C25—C26 | 1.365 (8) |
C2—C3 | 1.395 (6) | C25—H25 | 0.95 |
C2—C21 | 1.484 (6) | C26—C27 | 1.392 (7) |
C3—C4 | 1.372 (6) | C26—H26 | 0.95 |
C3—H3 | 0.95 | C27—C28 | 1.368 (6) |
C4—C5 | 1.372 (7) | C27—H27 | 0.95 |
C4—H4 | 0.95 | C28—C29 | 1.392 (6) |
C5—C6 | 1.380 (7) | C28—H28 | 0.95 |
C19—N11—N12 | 109.0 (3) | C16—C15—H15 | 121 |
C19—N11—C11 | 127.6 (4) | C14—C15—H15 | 121 |
N12—N11—C11 | 121.3 (4) | C15—C16—C17 | 120.3 (5) |
N13—N12—N11 | 109.6 (4) | C15—C16—H16 | 120 |
N12—N13—C14 | 108.1 (4) | C17—C16—H16 | 120 |
C29—N21—N22 | 109.4 (3) | C18—C17—C16 | 123.1 (5) |
C29—N21—C21 | 128.9 (3) | C18—C17—H17 | 119 |
N22—N21—C21 | 121.6 (3) | C16—C17—H17 | 118 |
N23—N22—N21 | 108.7 (4) | C17—C18—C19 | 116.1 (4) |
N22—N23—C24 | 108.8 (4) | C17—C18—H18 | 122 |
C6—C1—C2 | 118.7 (4) | C19—C18—H18 | 122 |
C6—C1—C11 | 122.6 (4) | N11—C19—C14 | 104.6 (4) |
C2—C1—C11 | 118.6 (4) | N11—C19—C18 | 134.4 (4) |
C3—C2—C1 | 119.6 (4) | C14—C19—C18 | 120.9 (4) |
C3—C2—C21 | 115.3 (4) | O21—C21—N21 | 118.1 (4) |
C1—C2—C21 | 125.1 (4) | O21—C21—C2 | 124.4 (4) |
C4—C3—C2 | 120.1 (4) | N21—C21—C2 | 117.1 (4) |
C4—C3—H3 | 120 | C29—C24—N23 | 109.1 (4) |
C2—C3—H3 | 120 | C29—C24—C25 | 121.7 (5) |
C5—C4—C3 | 120.9 (5) | N23—C24—C25 | 129.0 (4) |
C5—C4—H4 | 119 | C26—C25—C24 | 116.2 (5) |
C3—C4—H4 | 120 | C26—C25—H25 | 122 |
C4—C5—C6 | 119.5 (5) | C24—C25—H25 | 122 |
C4—C5—H5 | 120 | C25—C26—C27 | 121.5 (5) |
C6—C5—H5 | 120 | C25—C26—H26 | 120 |
C5—C6—C1 | 121.2 (5) | C27—C26—H26 | 119 |
C5—C6—H6 | 120 | C28—C27—C26 | 122.8 (5) |
C1—C6—H6 | 119 | C28—C27—H27 | 119 |
O11—C11—N11 | 119.5 (4) | C26—C27—H27 | 119 |
O11—C11—C1 | 123.3 (4) | C27—C28—C29 | 116.2 (5) |
N11—C11—C1 | 117.2 (4) | C27—C28—H28 | 122 |
C15—C14—C19 | 122.0 (5) | C29—C28—H28 | 122 |
C15—C14—N13 | 129.3 (5) | C24—C29—N21 | 104.0 (3) |
C19—C14—N13 | 108.7 (4) | C24—C29—C28 | 121.5 (4) |
C16—C15—C14 | 117.5 (5) | N21—C29—C28 | 134.5 (4) |
C19—N11—N12—N13 | 0.8 (5) | N12—N11—C19—C18 | −178.1 (4) |
C11—N11—N12—N13 | 165.9 (4) | C11—N11—C19—C18 | 18.1 (8) |
N11—N12—N13—C14 | −1.0 (5) | C15—C14—C19—N11 | 178.6 (4) |
C29—N21—N22—N23 | 1.0 (6) | N13—C14—C19—N11 | −0.2 (5) |
C21—N21—N22—N23 | 178.0 (4) | C15—C14—C19—C18 | −3.3 (7) |
N21—N22—N23—C24 | −0.5 (6) | N13—C14—C19—C18 | 177.9 (4) |
C6—C1—C2—C3 | −0.1 (6) | C17—C18—C19—N11 | −179.3 (5) |
C11—C1—C2—C3 | −176.0 (4) | C17—C18—C19—C14 | 3.2 (6) |
C6—C1—C2—C21 | −179.7 (4) | C29—N21—C21—O21 | −6.3 (7) |
C11—C1—C2—C21 | 4.4 (6) | N22—N21—C21—O21 | 177.2 (4) |
C1—C2—C3—C4 | 0.2 (6) | C29—N21—C21—C2 | 166.9 (4) |
C21—C2—C3—C4 | 179.7 (4) | N22—N21—C21—C2 | −9.5 (6) |
C2—C3—C4—C5 | 0.2 (7) | C3—C2—C21—O21 | 53.4 (6) |
C3—C4—C5—C6 | −0.6 (7) | C1—C2—C21—O21 | −127.0 (5) |
C4—C5—C6—C1 | 0.6 (7) | C3—C2—C21—N21 | −119.4 (4) |
C2—C1—C6—C5 | −0.3 (7) | C1—C2—C21—N21 | 60.2 (6) |
C11—C1—C6—C5 | 175.5 (4) | N22—N23—C24—C29 | −0.1 (6) |
C19—N11—C11—O11 | 0.0 (7) | N22—N23—C24—C25 | −175.7 (5) |
N12—N11—C11—O11 | −162.0 (4) | C29—C24—C25—C26 | 1.9 (8) |
C19—N11—C11—C1 | 178.4 (4) | N23—C24—C25—C26 | 177.0 (6) |
N12—N11—C11—C1 | 16.3 (6) | C24—C25—C26—C27 | −1.1 (9) |
C6—C1—C11—O11 | −135.2 (5) | C25—C26—C27—C28 | 1.0 (9) |
C2—C1—C11—O11 | 40.6 (6) | C26—C27—C28—C29 | −1.5 (8) |
C6—C1—C11—N11 | 46.5 (6) | N23—C24—C29—N21 | 0.6 (5) |
C2—C1—C11—N11 | −137.7 (4) | C25—C24—C29—N21 | 176.6 (5) |
N12—N13—C14—C15 | −178.0 (5) | N23—C24—C29—C28 | −178.6 (5) |
N12—N13—C14—C19 | 0.8 (5) | C25—C24—C29—C28 | −2.6 (8) |
C19—C14—C15—C16 | 1.4 (7) | N22—N21—C29—C24 | −1.0 (5) |
N13—C14—C15—C16 | 179.9 (5) | C21—N21—C29—C24 | −177.7 (4) |
C14—C15—C16—C17 | 0.3 (7) | N22—N21—C29—C28 | 178.1 (5) |
C15—C16—C17—C18 | −0.2 (8) | C21—N21—C29—C28 | 1.3 (9) |
C16—C17—C18—C19 | −1.6 (7) | C27—C28—C29—C24 | 2.3 (8) |
N12—N11—C19—C14 | −0.3 (5) | C27—C28—C29—N21 | −176.6 (5) |
C11—N11—C19—C14 | −164.2 (4) |
Experimental details
Crystal data | |
Chemical formula | C20H12N6O2 |
Mr | 368.36 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 295 |
a, b, c (Å) | 10.744 (5), 22.193 (4), 7.079 (5) |
V (Å3) | 1687.9 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.38 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)'] reflections | 2231, 2231, 992 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.138, 0.89 |
No. of reflections | 2231 |
No. of parameters | 254 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.18 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a), MSC/AFC Diffractometer Control Software, TEXSAN for Windows (Molecular Structure Corporation, 1999b), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON for Windows (Spek, 1999), TEXSAN for Windows.
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Benzotriazole (BTAH) has long been used and remains one of the most effective inhibitors of copper corrosion in neutral and alkaline conditions. (Cotton, 1963; Cotton & Scholes, 1967; Poling, 1970; Mansfeld et al., 1971). Since the mechanism of its inhibition effect is largely attributed to the formation of a polymeric BTA-Cu-BTA-Cu film (Rubim et al., 1993; Ashour et al., 1995), the BTAH derivatives, therefore, may offer higher inhibition efficiencies than the parent molecule, with the extended molecule giving better interaction with the metal surface. With this goal in mind and in an attempt to further understand the mechanism of corrosion inhibition of the carboxybenzotriazoles, a new dicarboxamide, 1,1'-(phthaloyl)bis(benzotriazole), (I), was synthesized (Reid, 1996) and its structure determined using single-crystal X-ray methods.
The analysis shows (Fig. 1) that the ortho-substituted carboxybenzotriazole side chains adopt a syn-syn conformation to one another [torsion angles: C1–C2–C21–O21 = -127.0 (5)° and C6–C1–C11–O11 = -135.2 (5)°]. These chains are slightly distorted from planarity [torsion angles: C1–C11–N11–N12 = 16.3 (6)° and C2–C21–N21–N22 = -9.5 (6)°]. There are no intramolecular associations between the chains and in addition the packing in the unit cell shows no significant intermolecular interactions.