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In the title compound, C9H10N3O2+·C10H7O3S, the asymmetric unit comprises a carbendazim cation and a napsylate anion. Three inter­molecular N—H...O hydrogen bonds stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035549/sj2109sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035549/sj2109Isup2.hkl
Contains datablock I

CCDC reference: 628396

Key indicators

  • Single-crystal X-ray study
  • T = 170 K
  • Mean [sigma](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

Computing details top

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+·C10H7O3SDx = 1.457 Mg m3
Mr = 399.42Melting point: 496 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1346 reflections
a = 7.696 (3) Åθ = 2.5–16.5°
b = 14.729 (6) ŵ = 0.22 mm1
c = 16.061 (6) ÅT = 170 K
V = 1820.6 (12) Å3Rod, colourless
Z = 40.24 × 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 tubeRint = 0.123
Graphite monochromatorθmax = 26.5°, θmin = 1.9°
thin–slice ω scansh = 99
20111 measured reflectionsk = 1818
2143 independent reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-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 reflectionsΔρmax = 0.40 e Å3
254 parametersΔρmin = 0.33 e Å3
0 restraintsAbsolute structure: Flack (1983), with 1582 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
S180.75319 (13)0.48508 (6)0.61240 (5)0.0242 (2)
O20.6678 (4)0.32441 (17)0.36567 (16)0.0377 (7)
O40.9077 (4)0.23841 (18)0.38242 (17)0.0448 (8)
O150.8175 (3)0.54212 (16)0.68012 (14)0.0319 (7)
O160.5993 (3)0.52255 (18)0.57297 (14)0.0314 (6)
O170.7346 (4)0.39053 (15)0.63646 (15)0.0404 (7)
N50.8682 (4)0.32692 (19)0.26720 (18)0.0271 (8)
H5A0.79590.36400.24180.033*
N71.0680 (4)0.34013 (19)0.15609 (17)0.0259 (8)
H7A1.00710.37810.12540.031*
N141.1421 (4)0.2512 (2)0.25806 (18)0.0299 (8)
H14A1.13860.22120.30540.036*
C10.5994 (6)0.2934 (3)0.4447 (2)0.0476 (12)
H1A0.48530.32100.45440.071*
H1B0.67890.31100.48950.071*
H1C0.58770.22710.44370.071*
C30.8214 (6)0.2917 (3)0.3440 (2)0.0308 (10)
C61.0194 (5)0.3066 (2)0.2299 (2)0.0263 (9)
C81.2307 (5)0.3052 (2)0.1356 (2)0.0265 (8)
C91.3365 (5)0.3186 (2)0.0669 (2)0.0318 (10)
H9A1.30430.35790.02260.038*
C101.4908 (6)0.2718 (2)0.0666 (3)0.0363 (11)
H10A1.56790.27920.02090.044*
C111.5377 (6)0.2135 (3)0.1314 (3)0.0434 (12)
H11A1.64510.18180.12820.052*
C121.4337 (5)0.2006 (3)0.1993 (3)0.0351 (10)
H12A1.46620.16130.24350.042*
C131.2782 (5)0.2481 (2)0.2002 (2)0.0281 (9)
C190.9186 (5)0.4850 (2)0.5356 (2)0.0204 (8)
C200.8901 (5)0.5159 (2)0.4570 (2)0.0253 (8)
H20A0.77950.53970.44230.030*
C211.0253 (4)0.5128 (2)0.3970 (2)0.0227 (8)
C221.0005 (5)0.5428 (3)0.3142 (2)0.0312 (10)
H22A0.89160.56730.29790.037*
C231.1319 (5)0.5367 (3)0.2580 (2)0.0340 (10)
H23A1.11330.55670.20250.041*
C241.2937 (5)0.5015 (2)0.2803 (2)0.0299 (10)
H24A1.38350.49730.23990.036*
C251.3236 (5)0.4730 (3)0.3598 (2)0.0312 (9)
H25A1.43460.44990.37450.037*
C261.1900 (5)0.4777 (2)0.4208 (2)0.0231 (8)
C271.2149 (5)0.4474 (2)0.5030 (2)0.0288 (9)
H27A1.32550.42550.51990.035*
C281.0813 (5)0.4495 (2)0.5582 (2)0.0265 (9)
H28A1.09820.42670.61300.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S180.0225 (5)0.0270 (5)0.0230 (4)0.0009 (5)0.0043 (5)0.0008 (4)
O20.0422 (17)0.0368 (17)0.0341 (16)0.0135 (14)0.0126 (14)0.0065 (13)
O40.050 (2)0.0483 (18)0.0365 (18)0.0198 (16)0.0095 (16)0.0159 (16)
O150.0308 (15)0.0414 (17)0.0236 (14)0.0034 (12)0.0005 (12)0.0095 (12)
O160.0231 (14)0.0436 (16)0.0275 (14)0.0036 (13)0.0007 (12)0.0087 (13)
O170.0506 (18)0.0289 (14)0.0417 (16)0.0022 (15)0.0165 (17)0.0092 (11)
N50.0251 (19)0.0295 (18)0.0267 (17)0.0060 (15)0.0015 (15)0.0072 (14)
N70.0312 (19)0.0232 (17)0.0232 (18)0.0054 (15)0.0037 (15)0.0082 (14)
N140.037 (2)0.0273 (17)0.0256 (18)0.0060 (16)0.0004 (16)0.0055 (15)
C10.065 (3)0.042 (3)0.036 (3)0.014 (2)0.014 (3)0.003 (2)
C30.037 (2)0.025 (2)0.031 (2)0.0004 (19)0.002 (2)0.0057 (19)
C60.029 (2)0.022 (2)0.027 (2)0.0013 (18)0.0031 (19)0.0006 (17)
C80.026 (2)0.0216 (19)0.032 (2)0.0007 (18)0.002 (2)0.0039 (15)
C90.041 (3)0.026 (2)0.028 (2)0.002 (2)0.0050 (19)0.0021 (18)
C100.037 (3)0.028 (2)0.044 (3)0.002 (2)0.010 (2)0.004 (2)
C110.037 (3)0.037 (2)0.057 (3)0.012 (2)0.011 (2)0.002 (2)
C120.034 (2)0.030 (2)0.042 (3)0.0104 (19)0.002 (2)0.009 (2)
C130.036 (3)0.0230 (18)0.025 (2)0.0036 (18)0.0012 (19)0.0021 (16)
C190.024 (2)0.0164 (17)0.0204 (18)0.0004 (17)0.0026 (16)0.0043 (16)
C200.023 (2)0.0246 (19)0.028 (2)0.0020 (18)0.0017 (16)0.0020 (17)
C210.025 (2)0.0193 (18)0.0234 (19)0.0044 (16)0.0006 (16)0.0037 (17)
C220.026 (2)0.037 (2)0.031 (2)0.0016 (18)0.0061 (19)0.0020 (18)
C230.035 (3)0.039 (2)0.028 (2)0.003 (2)0.001 (2)0.0031 (18)
C240.029 (2)0.031 (2)0.030 (2)0.0053 (17)0.0091 (17)0.0014 (17)
C250.027 (2)0.032 (2)0.035 (2)0.0002 (18)0.0025 (19)0.0001 (19)
C260.028 (2)0.0187 (18)0.0221 (18)0.0017 (17)0.0010 (17)0.0013 (16)
C270.024 (2)0.030 (2)0.032 (2)0.0048 (17)0.0046 (19)0.0023 (17)
C280.031 (2)0.027 (2)0.022 (2)0.0002 (18)0.0039 (19)0.0012 (16)
Geometric parameters (Å, º) top
S18—O161.452 (3)C10—H10A0.9500
S18—O171.452 (2)C11—C121.365 (5)
S18—O151.461 (2)C11—H11A0.9500
S18—C191.773 (4)C12—C131.386 (5)
O2—C31.323 (5)C12—H12A0.9500
O2—C11.448 (4)C19—C201.359 (5)
O4—C31.199 (4)C19—C281.405 (5)
N5—C61.342 (5)C20—C211.419 (5)
N5—C31.386 (5)C20—H20A0.9500
N5—H5A0.8800C21—C221.414 (5)
N7—C61.338 (4)C21—C261.421 (5)
N7—C81.392 (5)C22—C231.359 (5)
N7—H7A0.8800C22—H22A0.9500
N14—C61.328 (5)C23—C241.395 (5)
N14—C131.401 (5)C23—H23A0.9500
N14—H14A0.8800C24—C251.363 (5)
C1—H1A0.9800C24—H24A0.9500
C1—H1B0.9800C25—C261.423 (5)
C1—H1C0.9800C25—H25A0.9500
C8—C131.385 (5)C26—C271.405 (5)
C8—C91.385 (5)C27—C281.359 (5)
C9—C101.374 (5)C27—H27A0.9500
C9—H9A0.9500C28—H28A0.9500
C10—C111.398 (6)
O16—S18—O17113.59 (18)C12—C11—H11A119.0
O16—S18—O15112.49 (15)C10—C11—H11A119.0
O17—S18—O15112.74 (15)C11—C12—C13116.4 (4)
O16—S18—C19106.41 (15)C11—C12—H12A121.8
O17—S18—C19104.76 (16)C13—C12—H12A121.8
O15—S18—C19106.01 (16)C8—C13—C12121.8 (4)
C3—O2—C1116.1 (3)C8—C13—N14106.2 (3)
C6—N5—C3122.6 (3)C12—C13—N14132.0 (3)
C6—N5—H5A118.7C20—C19—C28120.6 (3)
C3—N5—H5A118.7C20—C19—S18122.0 (3)
C6—N7—C8109.0 (3)C28—C19—S18117.4 (3)
C6—N7—H7A125.5C19—C20—C21120.1 (3)
C8—N7—H7A125.5C19—C20—H20A120.0
C6—N14—C13109.0 (3)C21—C20—H20A120.0
C6—N14—H14A125.5C22—C21—C20122.0 (3)
C13—N14—H14A125.5C22—C21—C26119.2 (3)
O2—C1—H1A109.5C20—C21—C26118.9 (3)
O2—C1—H1B109.5C23—C22—C21120.3 (4)
H1A—C1—H1B109.5C23—C22—H22A119.9
O2—C1—H1C109.5C21—C22—H22A119.9
H1A—C1—H1C109.5C22—C23—C24121.2 (3)
H1B—C1—H1C109.5C22—C23—H23A119.4
O4—C3—O2126.7 (4)C24—C23—H23A119.4
O4—C3—N5124.0 (4)C25—C24—C23120.3 (3)
O2—C3—N5109.3 (4)C25—C24—H24A119.8
N14—C6—N7109.2 (3)C23—C24—H24A119.8
N14—C6—N5127.0 (4)C24—C25—C26120.6 (3)
N7—C6—N5123.8 (3)C24—C25—H25A119.7
C13—C8—C9121.8 (3)C26—C25—H25A119.7
C13—C8—N7106.6 (3)C27—C26—C21119.3 (3)
C9—C8—N7131.6 (3)C27—C26—C25122.2 (3)
C10—C9—C8116.1 (4)C21—C26—C25118.4 (3)
C10—C9—H9A122.0C28—C27—C26120.2 (3)
C8—C9—H9A122.0C28—C27—H27A119.9
C9—C10—C11122.0 (4)C26—C27—H27A119.9
C9—C10—H10A119.0C27—C28—C19120.9 (3)
C11—C10—H10A119.0C27—C28—H28A119.5
C12—C11—C10121.9 (4)C19—C28—H28A119.5
C1—O2—C3—O41.2 (6)O17—S18—C19—C20120.6 (3)
C1—O2—C3—N5179.5 (3)O15—S18—C19—C20119.9 (3)
C6—N5—C3—O42.5 (6)O16—S18—C19—C28178.6 (3)
C6—N5—C3—O2179.1 (3)O17—S18—C19—C2858.0 (3)
C13—N14—C6—N70.1 (4)O15—S18—C19—C2861.4 (3)
C13—N14—C6—N5179.4 (3)C28—C19—C20—C210.1 (5)
C8—N7—C6—N140.4 (4)S18—C19—C20—C21178.7 (3)
C8—N7—C6—N5179.8 (3)C19—C20—C21—C22178.9 (3)
C3—N5—C6—N141.2 (6)C19—C20—C21—C260.6 (5)
C3—N5—C6—N7179.6 (3)C20—C21—C22—C23178.4 (3)
C6—N7—C8—C130.6 (4)C26—C21—C22—C231.1 (5)
C6—N7—C8—C9179.9 (4)C21—C22—C23—C240.4 (6)
C13—C8—C9—C100.2 (5)C22—C23—C24—C250.6 (6)
N7—C8—C9—C10179.3 (4)C23—C24—C25—C260.9 (6)
C8—C9—C10—C110.4 (6)C22—C21—C26—C27179.8 (3)
C9—C10—C11—C120.8 (6)C20—C21—C26—C270.3 (5)
C10—C11—C12—C130.5 (6)C22—C21—C26—C250.8 (5)
C9—C8—C13—C120.5 (6)C20—C21—C26—C25178.7 (3)
N7—C8—C13—C12179.1 (3)C24—C25—C26—C27178.8 (3)
C9—C8—C13—N14179.9 (3)C24—C25—C26—C210.2 (5)
N7—C8—C13—N140.5 (4)C21—C26—C27—C281.8 (5)
C11—C12—C13—C80.2 (6)C25—C26—C27—C28177.1 (3)
C11—C12—C13—N14179.6 (4)C26—C27—C28—C192.5 (5)
C6—N14—C13—C80.2 (4)C20—C19—C28—C271.6 (5)
C6—N14—C13—C12179.3 (4)S18—C19—C28—C27179.7 (3)
O16—S18—C19—C200.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O15i0.881.912.778 (4)168
N7—H7A···O16i0.881.882.744 (4)168
N14—H14A···O17ii0.882.032.781 (4)142
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1/2, y+1/2, z+1.
 

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