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In the title compound, 2C6H6N3+·C6Cl2O42−, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033976/bh2041sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033976/bh2041Isup2.hkl
Contains datablock I

CCDC reference: 620650

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](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

Computing details top

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+·C6Cl2O42F(000) = 456
Mr = 447.24Dx = 1.633 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1151 reflections
a = 4.4423 (13) Åθ = 2.9–23.0°
b = 17.401 (5) ŵ = 0.40 mm1
c = 11.851 (3) ÅT = 292 K
β = 96.882 (5)°Plate, red
V = 909.5 (4) Å30.30 × 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 tube1338 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 55
Tmin = 0.890, Tmax = 0.992k = 2121
4958 measured reflectionsl = 1510
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H 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 parametersΔρmax = 0.32 e Å3
2 restraintsΔρmin = 0.25 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3359 (6)0.78863 (15)0.0466 (2)0.0337 (6)
C20.1749 (7)0.78832 (17)0.0618 (2)0.0444 (8)
H20.20800.75110.11530.053*
C30.0336 (7)0.84539 (18)0.0856 (3)0.0479 (8)
H30.14280.84770.15750.058*
C40.0877 (7)0.90084 (17)0.0039 (2)0.0444 (8)
H40.23500.93810.02310.053*
C50.0667 (6)0.90182 (16)0.1014 (3)0.0371 (7)
H50.03080.93910.15450.045*
C60.2831 (6)0.84415 (14)0.1267 (2)0.0298 (6)
C70.1941 (6)0.50676 (15)0.1046 (2)0.0326 (6)
C80.0042 (6)0.56984 (15)0.0650 (2)0.0327 (6)
C90.2013 (6)0.56121 (16)0.0466 (2)0.0335 (6)
Cl10.42760 (18)0.52033 (4)0.23132 (6)0.0446 (3)
N10.5606 (6)0.74450 (13)0.0993 (2)0.0402 (6)
H10.658 (6)0.7057 (12)0.079 (3)0.048*
N20.6493 (6)0.76797 (13)0.2037 (2)0.0428 (6)
N30.4812 (6)0.82772 (14)0.2205 (2)0.0374 (6)
H3A0.511 (7)0.8486 (16)0.2872 (14)0.051*
O10.0023 (5)0.63091 (11)0.11613 (17)0.0444 (5)
O20.3676 (5)0.62016 (11)0.07572 (16)0.0429 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0423 (16)0.0244 (14)0.0356 (16)0.0029 (12)0.0097 (13)0.0009 (12)
C20.061 (2)0.0401 (18)0.0325 (16)0.0025 (15)0.0085 (15)0.0109 (13)
C30.057 (2)0.0487 (19)0.0361 (17)0.0076 (16)0.0037 (15)0.0022 (14)
C40.0451 (18)0.0330 (16)0.053 (2)0.0014 (14)0.0016 (15)0.0038 (14)
C50.0424 (17)0.0253 (14)0.0444 (17)0.0008 (12)0.0080 (13)0.0059 (12)
C60.0376 (15)0.0242 (14)0.0278 (14)0.0063 (11)0.0047 (12)0.0034 (11)
C70.0391 (16)0.0297 (15)0.0290 (14)0.0008 (12)0.0034 (12)0.0028 (11)
C80.0428 (16)0.0234 (14)0.0334 (15)0.0001 (12)0.0111 (12)0.0019 (11)
C90.0422 (16)0.0288 (15)0.0309 (14)0.0029 (12)0.0098 (12)0.0052 (12)
Cl10.0555 (5)0.0380 (5)0.0376 (4)0.0011 (3)0.0058 (3)0.0002 (3)
N10.0493 (16)0.0258 (13)0.0465 (16)0.0018 (11)0.0098 (12)0.0031 (11)
N20.0515 (16)0.0302 (13)0.0462 (16)0.0024 (12)0.0040 (12)0.0042 (11)
N30.0486 (15)0.0328 (13)0.0307 (13)0.0051 (11)0.0044 (12)0.0032 (10)
O10.0613 (14)0.0285 (11)0.0426 (12)0.0082 (10)0.0023 (10)0.0039 (9)
O20.0627 (14)0.0308 (11)0.0337 (11)0.0170 (10)0.0006 (10)0.0017 (8)
Geometric parameters (Å, º) top
C1—N11.352 (4)C7—C9i1.370 (4)
C1—C21.394 (4)C7—C81.429 (4)
C1—C61.394 (4)C7—Cl11.736 (3)
C2—C31.364 (4)C8—O11.225 (3)
C2—H20.9300C8—C91.522 (4)
C3—C41.408 (4)C9—O21.287 (3)
C3—H30.9300C9—C7i1.370 (4)
C4—C51.351 (4)N1—N21.317 (3)
C4—H40.9300N1—H10.853 (10)
C5—C61.397 (4)N2—N31.309 (3)
C5—H50.9300N3—H3A0.866 (10)
C6—N31.363 (3)
N1—C1—C2133.9 (3)C1—C6—C5121.3 (3)
N1—C1—C6104.7 (2)C9i—C7—C8123.2 (2)
C2—C1—C6121.4 (3)C9i—C7—Cl1120.2 (2)
C3—C2—C1116.6 (3)C8—C7—Cl1116.6 (2)
C3—C2—H2121.7O1—C8—C7123.5 (3)
C1—C2—H2121.7O1—C8—C9117.9 (2)
C2—C3—C4121.7 (3)C7—C8—C9118.6 (2)
C2—C3—H3119.2O2—C9—C7i127.0 (3)
C4—C3—H3119.2O2—C9—C8114.8 (2)
C5—C4—C3122.3 (3)C7i—C9—C8118.2 (2)
C5—C4—H4118.9N2—N1—C1112.3 (2)
C3—C4—H4118.9N2—N1—H1114 (2)
C4—C5—C6116.7 (3)C1—N1—H1133 (2)
C4—C5—H5121.6N3—N2—N1106.1 (2)
C6—C5—H5121.6N2—N3—C6111.5 (2)
N3—C6—C1105.4 (2)N2—N3—H3A117 (2)
N3—C6—C5133.3 (3)C6—N3—H3A132 (2)
N1—C1—C2—C3177.6 (3)C9i—C7—C8—C90.3 (4)
C6—C1—C2—C30.6 (4)Cl1—C7—C8—C9179.1 (2)
C1—C2—C3—C41.3 (5)O1—C8—C9—O20.9 (4)
C2—C3—C4—C51.4 (5)C7—C8—C9—O2179.2 (2)
C3—C4—C5—C60.7 (4)O1—C8—C9—C7i179.7 (3)
N1—C1—C6—N30.3 (3)C7—C8—C9—C7i0.3 (4)
C2—C1—C6—N3179.0 (2)C2—C1—N1—N2178.4 (3)
N1—C1—C6—C5178.6 (2)C6—C1—N1—N20.0 (3)
C2—C1—C6—C50.1 (4)C1—N1—N2—N30.4 (3)
C4—C5—C6—N3178.7 (3)N1—N2—N3—C60.5 (3)
C4—C5—C6—C10.1 (4)C1—C6—N3—N20.5 (3)
C9i—C7—C8—O1179.6 (3)C5—C6—N3—N2178.2 (3)
Cl1—C7—C8—O10.8 (4)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.86 (1)2.00 (1)2.761 (3)148 (3)
N1—H1···O2ii0.86 (1)2.35 (2)3.041 (3)138 (3)
N3—H3A···O2iii0.86 (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.
 

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