In the title compound, 2C
6H
6N
3+·C
6Cl
2O
42−, the chloranilate dianion lies on an inversion centre. Ions are linked by three N—H
O hydrogen bonds into layers in the form of a (4,4)-net built up from
R86(32) and
R12(5) rings. The layers are further linked into a three-dimensional network by π–π stacking interactions.
Supporting information
CCDC reference: 620650
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.139
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio
PLAT736_ALERT_1_C H...A Calc 2.00(3), Rep 2.000(10) ...... 3.00 su-Ra
H1 -O1 1.555 1.655
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Bis(1,2,3-benzotriazolium) chloranilate
top
Crystal data top
2C6H6N3+·C6Cl2O42− | F(000) = 456 |
Mr = 447.24 | Dx = 1.633 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1151 reflections |
a = 4.4423 (13) Å | θ = 2.9–23.0° |
b = 17.401 (5) Å | µ = 0.40 mm−1 |
c = 11.851 (3) Å | T = 292 K |
β = 96.882 (5)° | Plate, red |
V = 909.5 (4) Å3 | 0.30 × 0.05 × 0.02 mm |
Z = 2 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1964 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 1338 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 27.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −5→5 |
Tmin = 0.890, Tmax = 0.992 | k = −21→21 |
4958 measured reflections | l = −15→10 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0711P)2] where P = (Fo2 + 2Fc2)/3 |
1964 reflections | (Δ/σ)max < 0.001 |
142 parameters | Δρmax = 0.32 e Å−3 |
2 restraints | Δρmin = −0.25 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.3359 (6) | 0.78863 (15) | 0.0466 (2) | 0.0337 (6) | |
C2 | 0.1749 (7) | 0.78832 (17) | −0.0618 (2) | 0.0444 (8) | |
H2 | 0.2080 | 0.7511 | −0.1153 | 0.053* | |
C3 | −0.0336 (7) | 0.84539 (18) | −0.0856 (3) | 0.0479 (8) | |
H3 | −0.1428 | 0.8477 | −0.1575 | 0.058* | |
C4 | −0.0877 (7) | 0.90084 (17) | −0.0039 (2) | 0.0444 (8) | |
H4 | −0.2350 | 0.9381 | −0.0231 | 0.053* | |
C5 | 0.0667 (6) | 0.90182 (16) | 0.1014 (3) | 0.0371 (7) | |
H5 | 0.0308 | 0.9391 | 0.1545 | 0.045* | |
C6 | 0.2831 (6) | 0.84415 (14) | 0.1267 (2) | 0.0298 (6) | |
C7 | 0.1941 (6) | 0.50676 (15) | 0.1046 (2) | 0.0326 (6) | |
C8 | 0.0042 (6) | 0.56984 (15) | 0.0650 (2) | 0.0327 (6) | |
C9 | −0.2013 (6) | 0.56121 (16) | −0.0466 (2) | 0.0335 (6) | |
Cl1 | 0.42760 (18) | 0.52033 (4) | 0.23132 (6) | 0.0446 (3) | |
N1 | 0.5606 (6) | 0.74450 (13) | 0.0993 (2) | 0.0402 (6) | |
H1 | 0.658 (6) | 0.7057 (12) | 0.079 (3) | 0.048* | |
N2 | 0.6493 (6) | 0.76797 (13) | 0.2037 (2) | 0.0428 (6) | |
N3 | 0.4812 (6) | 0.82772 (14) | 0.2205 (2) | 0.0374 (6) | |
H3A | 0.511 (7) | 0.8486 (16) | 0.2872 (14) | 0.051* | |
O1 | −0.0023 (5) | 0.63091 (11) | 0.11613 (17) | 0.0444 (5) | |
O2 | −0.3676 (5) | 0.62016 (11) | −0.07572 (16) | 0.0429 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0423 (16) | 0.0244 (14) | 0.0356 (16) | −0.0029 (12) | 0.0097 (13) | −0.0009 (12) |
C2 | 0.061 (2) | 0.0401 (18) | 0.0325 (16) | −0.0025 (15) | 0.0085 (15) | −0.0109 (13) |
C3 | 0.057 (2) | 0.0487 (19) | 0.0361 (17) | −0.0076 (16) | −0.0037 (15) | 0.0022 (14) |
C4 | 0.0451 (18) | 0.0330 (16) | 0.053 (2) | −0.0014 (14) | −0.0016 (15) | 0.0038 (14) |
C5 | 0.0424 (17) | 0.0253 (14) | 0.0444 (17) | −0.0008 (12) | 0.0080 (13) | −0.0059 (12) |
C6 | 0.0376 (15) | 0.0242 (14) | 0.0278 (14) | −0.0063 (11) | 0.0047 (12) | −0.0034 (11) |
C7 | 0.0391 (16) | 0.0297 (15) | 0.0290 (14) | 0.0008 (12) | 0.0034 (12) | 0.0028 (11) |
C8 | 0.0428 (16) | 0.0234 (14) | 0.0334 (15) | −0.0001 (12) | 0.0111 (12) | 0.0019 (11) |
C9 | 0.0422 (16) | 0.0288 (15) | 0.0309 (14) | 0.0029 (12) | 0.0098 (12) | 0.0052 (12) |
Cl1 | 0.0555 (5) | 0.0380 (5) | 0.0376 (4) | 0.0011 (3) | −0.0058 (3) | −0.0002 (3) |
N1 | 0.0493 (16) | 0.0258 (13) | 0.0465 (16) | 0.0018 (11) | 0.0098 (12) | −0.0031 (11) |
N2 | 0.0515 (16) | 0.0302 (13) | 0.0462 (16) | 0.0024 (12) | 0.0040 (12) | 0.0042 (11) |
N3 | 0.0486 (15) | 0.0328 (13) | 0.0307 (13) | −0.0051 (11) | 0.0044 (12) | −0.0032 (10) |
O1 | 0.0613 (14) | 0.0285 (11) | 0.0426 (12) | 0.0082 (10) | 0.0023 (10) | −0.0039 (9) |
O2 | 0.0627 (14) | 0.0308 (11) | 0.0337 (11) | 0.0170 (10) | 0.0006 (10) | 0.0017 (8) |
Geometric parameters (Å, º) top
C1—N1 | 1.352 (4) | C7—C9i | 1.370 (4) |
C1—C2 | 1.394 (4) | C7—C8 | 1.429 (4) |
C1—C6 | 1.394 (4) | C7—Cl1 | 1.736 (3) |
C2—C3 | 1.364 (4) | C8—O1 | 1.225 (3) |
C2—H2 | 0.9300 | C8—C9 | 1.522 (4) |
C3—C4 | 1.408 (4) | C9—O2 | 1.287 (3) |
C3—H3 | 0.9300 | C9—C7i | 1.370 (4) |
C4—C5 | 1.351 (4) | N1—N2 | 1.317 (3) |
C4—H4 | 0.9300 | N1—H1 | 0.853 (10) |
C5—C6 | 1.397 (4) | N2—N3 | 1.309 (3) |
C5—H5 | 0.9300 | N3—H3A | 0.866 (10) |
C6—N3 | 1.363 (3) | | |
| | | |
N1—C1—C2 | 133.9 (3) | C1—C6—C5 | 121.3 (3) |
N1—C1—C6 | 104.7 (2) | C9i—C7—C8 | 123.2 (2) |
C2—C1—C6 | 121.4 (3) | C9i—C7—Cl1 | 120.2 (2) |
C3—C2—C1 | 116.6 (3) | C8—C7—Cl1 | 116.6 (2) |
C3—C2—H2 | 121.7 | O1—C8—C7 | 123.5 (3) |
C1—C2—H2 | 121.7 | O1—C8—C9 | 117.9 (2) |
C2—C3—C4 | 121.7 (3) | C7—C8—C9 | 118.6 (2) |
C2—C3—H3 | 119.2 | O2—C9—C7i | 127.0 (3) |
C4—C3—H3 | 119.2 | O2—C9—C8 | 114.8 (2) |
C5—C4—C3 | 122.3 (3) | C7i—C9—C8 | 118.2 (2) |
C5—C4—H4 | 118.9 | N2—N1—C1 | 112.3 (2) |
C3—C4—H4 | 118.9 | N2—N1—H1 | 114 (2) |
C4—C5—C6 | 116.7 (3) | C1—N1—H1 | 133 (2) |
C4—C5—H5 | 121.6 | N3—N2—N1 | 106.1 (2) |
C6—C5—H5 | 121.6 | N2—N3—C6 | 111.5 (2) |
N3—C6—C1 | 105.4 (2) | N2—N3—H3A | 117 (2) |
N3—C6—C5 | 133.3 (3) | C6—N3—H3A | 132 (2) |
| | | |
N1—C1—C2—C3 | −177.6 (3) | C9i—C7—C8—C9 | 0.3 (4) |
C6—C1—C2—C3 | 0.6 (4) | Cl1—C7—C8—C9 | 179.1 (2) |
C1—C2—C3—C4 | −1.3 (5) | O1—C8—C9—O2 | −0.9 (4) |
C2—C3—C4—C5 | 1.4 (5) | C7—C8—C9—O2 | 179.2 (2) |
C3—C4—C5—C6 | −0.7 (4) | O1—C8—C9—C7i | 179.7 (3) |
N1—C1—C6—N3 | −0.3 (3) | C7—C8—C9—C7i | −0.3 (4) |
C2—C1—C6—N3 | −179.0 (2) | C2—C1—N1—N2 | 178.4 (3) |
N1—C1—C6—C5 | 178.6 (2) | C6—C1—N1—N2 | 0.0 (3) |
C2—C1—C6—C5 | −0.1 (4) | C1—N1—N2—N3 | 0.4 (3) |
C4—C5—C6—N3 | 178.7 (3) | N1—N2—N3—C6 | −0.5 (3) |
C4—C5—C6—C1 | 0.1 (4) | C1—C6—N3—N2 | 0.5 (3) |
C9i—C7—C8—O1 | −179.6 (3) | C5—C6—N3—N2 | −178.2 (3) |
Cl1—C7—C8—O1 | −0.8 (4) | | |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.86 (1) | 2.00 (1) | 2.761 (3) | 148 (3) |
N1—H1···O2ii | 0.86 (1) | 2.35 (2) | 3.041 (3) | 138 (3) |
N3—H3A···O2iii | 0.86 (1) | 1.74 (1) | 2.592 (3) | 169 (3) |
Symmetry codes: (ii) x+1, y, z; (iii) x+1, −y+3/2, z+1/2. |