In the title compound, C
9H
10N
3O
2+·C
10H
7O
3S
−, the asymmetric unit comprises a carbendazim cation and a napsylate anion. Three intermolecular N—H
O hydrogen bonds stabilize the structure.
Supporting information
CCDC reference: 628396
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.005 Å
- R factor = 0.064
- wR factor = 0.114
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level B
SHFSU01_ALERT_2_B The absolute value of parameter shift to su ratio > 0.10
Absolute value of the parameter shift to su ratio given 0.136
Additional refinement cycles may be required.
PLAT080_ALERT_2_B Maximum Shift/Error ............................ 0.14
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.123
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.13
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 26.49
From the CIF: _reflns_number_total 2143
Count of symmetry unique reflns 2166
Completeness (_total/calc) 98.94%
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 yes
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury
(Version 1.4; Macrae et al., 2006); software used to prepare material for publication: SHELXTL and local programs.
2-(methoxycarbonylamino)benzimidazolium naphthalene-1-sulfonate
top
Crystal data top
C9H10N3O2+·C10H7O3S− | Dx = 1.457 Mg m−3 |
Mr = 399.42 | Melting point: 496 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1346 reflections |
a = 7.696 (3) Å | θ = 2.5–16.5° |
b = 14.729 (6) Å | µ = 0.22 mm−1 |
c = 16.061 (6) Å | T = 170 K |
V = 1820.6 (12) Å3 | Rod, colourless |
Z = 4 | 0.24 × 0.09 × 0.08 mm |
F(000) = 832 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 1707 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.123 |
Graphite monochromator | θmax = 26.5°, θmin = 1.9° |
thin–slice ω scans | h = −9→9 |
20111 measured reflections | k = −18→18 |
2143 independent reflections | l = −20→20 |
Refinement top
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)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0336P)2 + 0.4451P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.136 |
3725 reflections | Δρmax = 0.40 e Å−3 |
254 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Absolute structure: Flack (1983), with 1582 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (13) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S18 | 0.75319 (13) | 0.48508 (6) | 0.61240 (5) | 0.0242 (2) | |
O2 | 0.6678 (4) | 0.32441 (17) | 0.36567 (16) | 0.0377 (7) | |
O4 | 0.9077 (4) | 0.23841 (18) | 0.38242 (17) | 0.0448 (8) | |
O15 | 0.8175 (3) | 0.54212 (16) | 0.68012 (14) | 0.0319 (7) | |
O16 | 0.5993 (3) | 0.52255 (18) | 0.57297 (14) | 0.0314 (6) | |
O17 | 0.7346 (4) | 0.39053 (15) | 0.63646 (15) | 0.0404 (7) | |
N5 | 0.8682 (4) | 0.32692 (19) | 0.26720 (18) | 0.0271 (8) | |
H5A | 0.7959 | 0.3640 | 0.2418 | 0.033* | |
N7 | 1.0680 (4) | 0.34013 (19) | 0.15609 (17) | 0.0259 (8) | |
H7A | 1.0071 | 0.3781 | 0.1254 | 0.031* | |
N14 | 1.1421 (4) | 0.2512 (2) | 0.25806 (18) | 0.0299 (8) | |
H14A | 1.1386 | 0.2212 | 0.3054 | 0.036* | |
C1 | 0.5994 (6) | 0.2934 (3) | 0.4447 (2) | 0.0476 (12) | |
H1A | 0.4853 | 0.3210 | 0.4544 | 0.071* | |
H1B | 0.6789 | 0.3110 | 0.4895 | 0.071* | |
H1C | 0.5877 | 0.2271 | 0.4437 | 0.071* | |
C3 | 0.8214 (6) | 0.2917 (3) | 0.3440 (2) | 0.0308 (10) | |
C6 | 1.0194 (5) | 0.3066 (2) | 0.2299 (2) | 0.0263 (9) | |
C8 | 1.2307 (5) | 0.3052 (2) | 0.1356 (2) | 0.0265 (8) | |
C9 | 1.3365 (5) | 0.3186 (2) | 0.0669 (2) | 0.0318 (10) | |
H9A | 1.3043 | 0.3579 | 0.0226 | 0.038* | |
C10 | 1.4908 (6) | 0.2718 (2) | 0.0666 (3) | 0.0363 (11) | |
H10A | 1.5679 | 0.2792 | 0.0209 | 0.044* | |
C11 | 1.5377 (6) | 0.2135 (3) | 0.1314 (3) | 0.0434 (12) | |
H11A | 1.6451 | 0.1818 | 0.1282 | 0.052* | |
C12 | 1.4337 (5) | 0.2006 (3) | 0.1993 (3) | 0.0351 (10) | |
H12A | 1.4662 | 0.1613 | 0.2435 | 0.042* | |
C13 | 1.2782 (5) | 0.2481 (2) | 0.2002 (2) | 0.0281 (9) | |
C19 | 0.9186 (5) | 0.4850 (2) | 0.5356 (2) | 0.0204 (8) | |
C20 | 0.8901 (5) | 0.5159 (2) | 0.4570 (2) | 0.0253 (8) | |
H20A | 0.7795 | 0.5397 | 0.4423 | 0.030* | |
C21 | 1.0253 (4) | 0.5128 (2) | 0.3970 (2) | 0.0227 (8) | |
C22 | 1.0005 (5) | 0.5428 (3) | 0.3142 (2) | 0.0312 (10) | |
H22A | 0.8916 | 0.5673 | 0.2979 | 0.037* | |
C23 | 1.1319 (5) | 0.5367 (3) | 0.2580 (2) | 0.0340 (10) | |
H23A | 1.1133 | 0.5567 | 0.2025 | 0.041* | |
C24 | 1.2937 (5) | 0.5015 (2) | 0.2803 (2) | 0.0299 (10) | |
H24A | 1.3835 | 0.4973 | 0.2399 | 0.036* | |
C25 | 1.3236 (5) | 0.4730 (3) | 0.3598 (2) | 0.0312 (9) | |
H25A | 1.4346 | 0.4499 | 0.3745 | 0.037* | |
C26 | 1.1900 (5) | 0.4777 (2) | 0.4208 (2) | 0.0231 (8) | |
C27 | 1.2149 (5) | 0.4474 (2) | 0.5030 (2) | 0.0288 (9) | |
H27A | 1.3255 | 0.4255 | 0.5199 | 0.035* | |
C28 | 1.0813 (5) | 0.4495 (2) | 0.5582 (2) | 0.0265 (9) | |
H28A | 1.0982 | 0.4267 | 0.6130 | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S18 | 0.0225 (5) | 0.0270 (5) | 0.0230 (4) | 0.0009 (5) | 0.0043 (5) | −0.0008 (4) |
O2 | 0.0422 (17) | 0.0368 (17) | 0.0341 (16) | 0.0135 (14) | 0.0126 (14) | 0.0065 (13) |
O4 | 0.050 (2) | 0.0483 (18) | 0.0365 (18) | 0.0198 (16) | 0.0095 (16) | 0.0159 (16) |
O15 | 0.0308 (15) | 0.0414 (17) | 0.0236 (14) | 0.0034 (12) | 0.0005 (12) | −0.0095 (12) |
O16 | 0.0231 (14) | 0.0436 (16) | 0.0275 (14) | 0.0036 (13) | 0.0007 (12) | −0.0087 (13) |
O17 | 0.0506 (18) | 0.0289 (14) | 0.0417 (16) | −0.0022 (15) | 0.0165 (17) | 0.0092 (11) |
N5 | 0.0251 (19) | 0.0295 (18) | 0.0267 (17) | 0.0060 (15) | 0.0015 (15) | 0.0072 (14) |
N7 | 0.0312 (19) | 0.0232 (17) | 0.0232 (18) | 0.0054 (15) | −0.0037 (15) | 0.0082 (14) |
N14 | 0.037 (2) | 0.0273 (17) | 0.0256 (18) | 0.0060 (16) | −0.0004 (16) | 0.0055 (15) |
C1 | 0.065 (3) | 0.042 (3) | 0.036 (3) | 0.014 (2) | 0.014 (3) | 0.003 (2) |
C3 | 0.037 (2) | 0.025 (2) | 0.031 (2) | 0.0004 (19) | −0.002 (2) | −0.0057 (19) |
C6 | 0.029 (2) | 0.022 (2) | 0.027 (2) | −0.0013 (18) | −0.0031 (19) | 0.0006 (17) |
C8 | 0.026 (2) | 0.0216 (19) | 0.032 (2) | 0.0007 (18) | −0.002 (2) | −0.0039 (15) |
C9 | 0.041 (3) | 0.026 (2) | 0.028 (2) | −0.002 (2) | 0.0050 (19) | 0.0021 (18) |
C10 | 0.037 (3) | 0.028 (2) | 0.044 (3) | −0.002 (2) | 0.010 (2) | 0.004 (2) |
C11 | 0.037 (3) | 0.037 (2) | 0.057 (3) | 0.012 (2) | 0.011 (2) | 0.002 (2) |
C12 | 0.034 (2) | 0.030 (2) | 0.042 (3) | 0.0104 (19) | 0.002 (2) | 0.009 (2) |
C13 | 0.036 (3) | 0.0230 (18) | 0.025 (2) | 0.0036 (18) | −0.0012 (19) | −0.0021 (16) |
C19 | 0.024 (2) | 0.0164 (17) | 0.0204 (18) | 0.0004 (17) | 0.0026 (16) | −0.0043 (16) |
C20 | 0.023 (2) | 0.0246 (19) | 0.028 (2) | −0.0020 (18) | −0.0017 (16) | −0.0020 (17) |
C21 | 0.025 (2) | 0.0193 (18) | 0.0234 (19) | −0.0044 (16) | 0.0006 (16) | −0.0037 (17) |
C22 | 0.026 (2) | 0.037 (2) | 0.031 (2) | 0.0016 (18) | −0.0061 (19) | −0.0020 (18) |
C23 | 0.035 (3) | 0.039 (2) | 0.028 (2) | −0.003 (2) | 0.001 (2) | 0.0031 (18) |
C24 | 0.029 (2) | 0.031 (2) | 0.030 (2) | −0.0053 (17) | 0.0091 (17) | −0.0014 (17) |
C25 | 0.027 (2) | 0.032 (2) | 0.035 (2) | −0.0002 (18) | 0.0025 (19) | 0.0001 (19) |
C26 | 0.028 (2) | 0.0187 (18) | 0.0221 (18) | 0.0017 (17) | −0.0010 (17) | −0.0013 (16) |
C27 | 0.024 (2) | 0.030 (2) | 0.032 (2) | 0.0048 (17) | −0.0046 (19) | 0.0023 (17) |
C28 | 0.031 (2) | 0.027 (2) | 0.022 (2) | 0.0002 (18) | −0.0039 (19) | −0.0012 (16) |
Geometric parameters (Å, º) top
S18—O16 | 1.452 (3) | C10—H10A | 0.9500 |
S18—O17 | 1.452 (2) | C11—C12 | 1.365 (5) |
S18—O15 | 1.461 (2) | C11—H11A | 0.9500 |
S18—C19 | 1.773 (4) | C12—C13 | 1.386 (5) |
O2—C3 | 1.323 (5) | C12—H12A | 0.9500 |
O2—C1 | 1.448 (4) | C19—C20 | 1.359 (5) |
O4—C3 | 1.199 (4) | C19—C28 | 1.405 (5) |
N5—C6 | 1.342 (5) | C20—C21 | 1.419 (5) |
N5—C3 | 1.386 (5) | C20—H20A | 0.9500 |
N5—H5A | 0.8800 | C21—C22 | 1.414 (5) |
N7—C6 | 1.338 (4) | C21—C26 | 1.421 (5) |
N7—C8 | 1.392 (5) | C22—C23 | 1.359 (5) |
N7—H7A | 0.8800 | C22—H22A | 0.9500 |
N14—C6 | 1.328 (5) | C23—C24 | 1.395 (5) |
N14—C13 | 1.401 (5) | C23—H23A | 0.9500 |
N14—H14A | 0.8800 | C24—C25 | 1.363 (5) |
C1—H1A | 0.9800 | C24—H24A | 0.9500 |
C1—H1B | 0.9800 | C25—C26 | 1.423 (5) |
C1—H1C | 0.9800 | C25—H25A | 0.9500 |
C8—C13 | 1.385 (5) | C26—C27 | 1.405 (5) |
C8—C9 | 1.385 (5) | C27—C28 | 1.359 (5) |
C9—C10 | 1.374 (5) | C27—H27A | 0.9500 |
C9—H9A | 0.9500 | C28—H28A | 0.9500 |
C10—C11 | 1.398 (6) | | |
| | | |
O16—S18—O17 | 113.59 (18) | C12—C11—H11A | 119.0 |
O16—S18—O15 | 112.49 (15) | C10—C11—H11A | 119.0 |
O17—S18—O15 | 112.74 (15) | C11—C12—C13 | 116.4 (4) |
O16—S18—C19 | 106.41 (15) | C11—C12—H12A | 121.8 |
O17—S18—C19 | 104.76 (16) | C13—C12—H12A | 121.8 |
O15—S18—C19 | 106.01 (16) | C8—C13—C12 | 121.8 (4) |
C3—O2—C1 | 116.1 (3) | C8—C13—N14 | 106.2 (3) |
C6—N5—C3 | 122.6 (3) | C12—C13—N14 | 132.0 (3) |
C6—N5—H5A | 118.7 | C20—C19—C28 | 120.6 (3) |
C3—N5—H5A | 118.7 | C20—C19—S18 | 122.0 (3) |
C6—N7—C8 | 109.0 (3) | C28—C19—S18 | 117.4 (3) |
C6—N7—H7A | 125.5 | C19—C20—C21 | 120.1 (3) |
C8—N7—H7A | 125.5 | C19—C20—H20A | 120.0 |
C6—N14—C13 | 109.0 (3) | C21—C20—H20A | 120.0 |
C6—N14—H14A | 125.5 | C22—C21—C20 | 122.0 (3) |
C13—N14—H14A | 125.5 | C22—C21—C26 | 119.2 (3) |
O2—C1—H1A | 109.5 | C20—C21—C26 | 118.9 (3) |
O2—C1—H1B | 109.5 | C23—C22—C21 | 120.3 (4) |
H1A—C1—H1B | 109.5 | C23—C22—H22A | 119.9 |
O2—C1—H1C | 109.5 | C21—C22—H22A | 119.9 |
H1A—C1—H1C | 109.5 | C22—C23—C24 | 121.2 (3) |
H1B—C1—H1C | 109.5 | C22—C23—H23A | 119.4 |
O4—C3—O2 | 126.7 (4) | C24—C23—H23A | 119.4 |
O4—C3—N5 | 124.0 (4) | C25—C24—C23 | 120.3 (3) |
O2—C3—N5 | 109.3 (4) | C25—C24—H24A | 119.8 |
N14—C6—N7 | 109.2 (3) | C23—C24—H24A | 119.8 |
N14—C6—N5 | 127.0 (4) | C24—C25—C26 | 120.6 (3) |
N7—C6—N5 | 123.8 (3) | C24—C25—H25A | 119.7 |
C13—C8—C9 | 121.8 (3) | C26—C25—H25A | 119.7 |
C13—C8—N7 | 106.6 (3) | C27—C26—C21 | 119.3 (3) |
C9—C8—N7 | 131.6 (3) | C27—C26—C25 | 122.2 (3) |
C10—C9—C8 | 116.1 (4) | C21—C26—C25 | 118.4 (3) |
C10—C9—H9A | 122.0 | C28—C27—C26 | 120.2 (3) |
C8—C9—H9A | 122.0 | C28—C27—H27A | 119.9 |
C9—C10—C11 | 122.0 (4) | C26—C27—H27A | 119.9 |
C9—C10—H10A | 119.0 | C27—C28—C19 | 120.9 (3) |
C11—C10—H10A | 119.0 | C27—C28—H28A | 119.5 |
C12—C11—C10 | 121.9 (4) | C19—C28—H28A | 119.5 |
| | | |
C1—O2—C3—O4 | 1.2 (6) | O17—S18—C19—C20 | 120.6 (3) |
C1—O2—C3—N5 | 179.5 (3) | O15—S18—C19—C20 | −119.9 (3) |
C6—N5—C3—O4 | −2.5 (6) | O16—S18—C19—C28 | −178.6 (3) |
C6—N5—C3—O2 | 179.1 (3) | O17—S18—C19—C28 | −58.0 (3) |
C13—N14—C6—N7 | 0.1 (4) | O15—S18—C19—C28 | 61.4 (3) |
C13—N14—C6—N5 | 179.4 (3) | C28—C19—C20—C21 | −0.1 (5) |
C8—N7—C6—N14 | −0.4 (4) | S18—C19—C20—C21 | −178.7 (3) |
C8—N7—C6—N5 | −179.8 (3) | C19—C20—C21—C22 | 178.9 (3) |
C3—N5—C6—N14 | 1.2 (6) | C19—C20—C21—C26 | −0.6 (5) |
C3—N5—C6—N7 | −179.6 (3) | C20—C21—C22—C23 | −178.4 (3) |
C6—N7—C8—C13 | 0.6 (4) | C26—C21—C22—C23 | 1.1 (5) |
C6—N7—C8—C9 | −179.9 (4) | C21—C22—C23—C24 | −0.4 (6) |
C13—C8—C9—C10 | 0.2 (5) | C22—C23—C24—C25 | −0.6 (6) |
N7—C8—C9—C10 | −179.3 (4) | C23—C24—C25—C26 | 0.9 (6) |
C8—C9—C10—C11 | 0.4 (6) | C22—C21—C26—C27 | −179.8 (3) |
C9—C10—C11—C12 | −0.8 (6) | C20—C21—C26—C27 | −0.3 (5) |
C10—C11—C12—C13 | 0.5 (6) | C22—C21—C26—C25 | −0.8 (5) |
C9—C8—C13—C12 | −0.5 (6) | C20—C21—C26—C25 | 178.7 (3) |
N7—C8—C13—C12 | 179.1 (3) | C24—C25—C26—C27 | 178.8 (3) |
C9—C8—C13—N14 | 179.9 (3) | C24—C25—C26—C21 | −0.2 (5) |
N7—C8—C13—N14 | −0.5 (4) | C21—C26—C27—C28 | 1.8 (5) |
C11—C12—C13—C8 | 0.2 (6) | C25—C26—C27—C28 | −177.1 (3) |
C11—C12—C13—N14 | 179.6 (4) | C26—C27—C28—C19 | −2.5 (5) |
C6—N14—C13—C8 | 0.2 (4) | C20—C19—C28—C27 | 1.6 (5) |
C6—N14—C13—C12 | −179.3 (4) | S18—C19—C28—C27 | −179.7 (3) |
O16—S18—C19—C20 | 0.0 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···O15i | 0.88 | 1.91 | 2.778 (4) | 168 |
N7—H7A···O16i | 0.88 | 1.88 | 2.744 (4) | 168 |
N14—H14A···O17ii | 0.88 | 2.03 | 2.781 (4) | 142 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) x+1/2, −y+1/2, −z+1. |