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The title compound, C10H11N2O2+·NO3-·0.5H2O, crystallizes in a monoclinic unit cell with two benzimidazolium cations, two NO3- anions and one water mol­ecule in the asymmetric unit. Intermolecular hydrogen bonds link the cations, anions and water mol­ecules into two-dimensional layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030235/cv6421sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030235/cv6421Isup2.hkl
Contains datablock I

CCDC reference: 259618

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.078
  • wR factor = 0.249
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. 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 ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C19 .. 5.09 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N5 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N6 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C11 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

6-Methoxycarbonyl-2-methyl-1H-benzimidazol-3-ium nitrate hemihydrate top
Crystal data top
C10H11N2O2+·NO3·0.5H2ODx = 1.438 Mg m3
Mr = 262.23Melting point = 374–375 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.9107 (6) ÅCell parameters from 937 reflections
b = 21.5276 (17) Åθ = 2.4–25.0°
c = 14.2691 (11) ŵ = 0.12 mm1
β = 94.573 (2)°T = 293 K
V = 2422.3 (3) Å3Colomn, brown yellow
Z = 80.20 × 0.15 × 0.09 mm
F(000) = 1096
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
4284 independent reflections
Radiation source: fine-focus sealed tube1703 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 1.7°
ω scansh = 59
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 2525
Tmin = 0.977, Tmax = 0.989l = 1615
12579 measured reflections
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)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.249H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.1161P)2]
where P = (Fo2 + 2Fc2)/3
4284 reflections(Δ/σ)max = 0.002
334 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.32 e Å3
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
O1W0.301 (3)0.4430 (8)0.0967 (11)0.635 (17)
H1W10.21400.42350.07290.762*
H2W10.38780.42620.07600.762*
O10.0866 (6)0.10217 (18)0.2874 (3)0.1096 (14)
O20.3559 (6)0.09091 (18)0.3448 (3)0.1055 (13)
O30.2064 (6)0.2921 (2)0.0534 (4)0.1307 (18)
O40.0157 (5)0.35596 (18)0.0126 (3)0.0956 (12)
O50.7844 (5)0.4881 (2)0.4601 (4)0.1233 (16)
O60.6504 (5)0.40196 (18)0.4493 (3)0.1061 (13)
O70.5397 (5)0.48377 (16)0.3849 (3)0.0901 (12)
O80.7327 (5)0.29137 (18)0.1892 (3)0.0940 (12)
O90.7460 (6)0.38918 (19)0.2125 (3)0.1263 (16)
O100.5221 (6)0.34922 (19)0.1424 (3)0.1197 (15)
N10.3129 (6)0.38043 (19)0.3367 (3)0.0780 (12)
H1A0.39430.40520.35490.094*
N20.0684 (6)0.3481 (2)0.2819 (3)0.0840 (13)
H2A0.03550.34820.25890.101*
N30.3823 (6)0.11389 (18)0.1087 (3)0.0729 (12)
H3A0.37950.07400.11080.087*
N40.4734 (5)0.20724 (17)0.1234 (3)0.0679 (11)
H4A0.53940.23830.13630.082*
N50.6597 (6)0.4572 (2)0.4318 (3)0.0846 (14)
N60.6644 (7)0.3442 (2)0.1809 (3)0.0836 (13)
C10.0982 (8)0.4637 (3)0.2958 (5)0.118 (2)
H1B0.01730.46410.26950.177*
H1C0.16760.48660.25570.177*
H1D0.10480.48250.35700.177*
C20.1599 (8)0.3981 (3)0.3040 (4)0.0836 (16)
C30.3234 (7)0.3162 (2)0.3373 (3)0.0653 (13)
C40.4514 (7)0.2758 (3)0.3658 (3)0.0741 (15)
H4B0.55770.29010.38850.089*
C50.4166 (7)0.2131 (2)0.3595 (3)0.0738 (15)
H5A0.50000.18460.38000.089*
C60.2578 (7)0.1914 (2)0.3228 (3)0.0690 (14)
C70.1302 (7)0.2324 (2)0.2935 (3)0.0728 (14)
H7A0.02430.21850.26920.087*
C80.1663 (7)0.2952 (3)0.3016 (3)0.0688 (14)
C90.2187 (10)0.1254 (3)0.3152 (4)0.0853 (17)
C100.3336 (10)0.0230 (3)0.3402 (5)0.138 (3)
H10A0.43780.00300.36240.207*
H10B0.30330.01080.27640.207*
H10C0.24540.01090.37890.207*
C110.6800 (7)0.1249 (3)0.1796 (4)0.0945 (18)
H11A0.67740.08030.18160.142*
H11B0.70010.14080.24240.142*
H11C0.76930.13820.14250.142*
C120.5155 (7)0.1484 (2)0.1372 (4)0.0703 (14)
C130.2484 (7)0.1512 (2)0.0749 (3)0.0648 (13)
C140.0873 (7)0.1381 (2)0.0379 (4)0.0758 (15)
H14A0.04820.09750.03040.091*
C150.0126 (7)0.1879 (3)0.0126 (4)0.0781 (15)
H15A0.12320.18100.01230.094*
C160.0456 (7)0.2493 (2)0.0229 (3)0.0674 (14)
C170.2082 (7)0.2620 (2)0.0598 (3)0.0663 (13)
H17A0.24820.30250.06710.080*
C180.3077 (6)0.2117 (2)0.0851 (3)0.0586 (12)
C190.0737 (8)0.2996 (3)0.0104 (4)0.0845 (16)
C200.1264 (9)0.4074 (3)0.0174 (5)0.120 (2)
H20A0.07420.44590.00290.180*
H20B0.23290.40300.00980.180*
H20C0.14530.40720.08470.180*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1W0.67 (4)0.47 (3)0.73 (4)0.09 (2)0.20 (3)0.03 (2)
O10.107 (3)0.086 (3)0.135 (4)0.036 (3)0.006 (3)0.012 (2)
O20.128 (4)0.066 (3)0.122 (3)0.013 (2)0.004 (3)0.004 (2)
O30.079 (3)0.114 (4)0.191 (5)0.009 (3)0.045 (3)0.007 (3)
O40.096 (3)0.077 (3)0.112 (3)0.011 (2)0.004 (2)0.001 (2)
O50.073 (3)0.092 (3)0.200 (5)0.015 (2)0.016 (3)0.002 (3)
O60.103 (3)0.061 (2)0.150 (4)0.004 (2)0.013 (3)0.018 (2)
O70.076 (3)0.073 (2)0.118 (3)0.013 (2)0.013 (2)0.008 (2)
O80.089 (3)0.064 (2)0.127 (3)0.002 (2)0.006 (2)0.002 (2)
O90.115 (3)0.067 (3)0.188 (4)0.015 (2)0.045 (3)0.017 (3)
O100.078 (3)0.106 (3)0.169 (4)0.007 (3)0.032 (3)0.006 (3)
N10.076 (3)0.064 (3)0.092 (3)0.011 (2)0.010 (3)0.001 (2)
N20.068 (3)0.088 (3)0.091 (3)0.010 (3)0.023 (3)0.013 (3)
N30.072 (3)0.053 (2)0.095 (3)0.009 (3)0.010 (3)0.004 (2)
N40.067 (3)0.053 (3)0.083 (3)0.012 (2)0.004 (2)0.000 (2)
N50.067 (3)0.071 (3)0.115 (4)0.000 (3)0.002 (3)0.003 (3)
N60.075 (4)0.075 (3)0.099 (4)0.009 (3)0.004 (3)0.007 (3)
C10.123 (6)0.079 (4)0.147 (6)0.013 (4)0.020 (5)0.018 (4)
C20.074 (4)0.081 (4)0.091 (4)0.008 (3)0.020 (3)0.012 (3)
C30.061 (4)0.073 (3)0.062 (3)0.010 (3)0.003 (3)0.002 (3)
C40.059 (3)0.081 (4)0.081 (4)0.012 (3)0.001 (3)0.015 (3)
C50.074 (4)0.069 (4)0.078 (4)0.004 (3)0.001 (3)0.005 (3)
C60.074 (4)0.067 (3)0.066 (3)0.013 (3)0.005 (3)0.006 (3)
C70.069 (4)0.084 (4)0.065 (3)0.017 (3)0.001 (3)0.003 (3)
C80.065 (4)0.078 (4)0.062 (3)0.007 (3)0.001 (3)0.000 (3)
C90.098 (5)0.076 (4)0.083 (4)0.006 (4)0.010 (4)0.002 (3)
C100.169 (7)0.069 (4)0.177 (7)0.009 (4)0.025 (6)0.001 (4)
C110.071 (4)0.092 (4)0.119 (5)0.003 (3)0.002 (4)0.006 (3)
C120.069 (4)0.060 (3)0.083 (4)0.007 (3)0.010 (3)0.000 (3)
C130.067 (4)0.059 (3)0.070 (3)0.016 (3)0.013 (3)0.003 (3)
C140.072 (4)0.063 (3)0.092 (4)0.015 (3)0.006 (3)0.004 (3)
C150.062 (3)0.079 (4)0.093 (4)0.017 (3)0.001 (3)0.007 (3)
C160.061 (3)0.073 (3)0.069 (3)0.004 (3)0.005 (3)0.001 (3)
C170.065 (4)0.069 (3)0.064 (3)0.006 (3)0.003 (3)0.005 (2)
C180.050 (3)0.060 (3)0.066 (3)0.006 (3)0.006 (3)0.002 (2)
C190.073 (4)0.087 (4)0.093 (4)0.005 (4)0.006 (4)0.010 (3)
C200.130 (6)0.097 (5)0.134 (5)0.047 (4)0.012 (5)0.005 (4)
Geometric parameters (Å, º) top
O1W—H1W10.8539C3—C41.372 (7)
O1W—H2W10.8485C3—C81.381 (7)
O1—C91.197 (7)C4—C51.379 (7)
O2—C91.354 (7)C4—H4B0.9300
O2—C101.474 (6)C5—C61.401 (7)
O3—C191.184 (6)C5—H5A0.9300
O4—C191.329 (6)C6—C71.381 (7)
O4—C201.455 (6)C6—C91.458 (8)
O5—N51.230 (5)C7—C81.384 (7)
O6—N51.219 (5)C7—H7A0.9300
O7—N51.255 (5)C10—H10A0.9600
O8—N61.260 (5)C10—H10B0.9600
O9—N61.230 (5)C10—H10C0.9600
O10—N61.218 (5)C11—C121.480 (7)
N1—C21.318 (6)C11—H11A0.9600
N1—C31.385 (6)C11—H11B0.9600
N1—H1A0.8600C11—H11C0.9600
N2—C21.321 (6)C13—C141.370 (7)
N2—C81.393 (6)C13—C181.387 (6)
N2—H2A0.8600C14—C151.364 (7)
N3—C121.327 (6)C14—H14A0.9300
N3—C131.384 (6)C15—C161.402 (7)
N3—H3A0.8600C15—H15A0.9300
N4—C121.321 (5)C16—C171.378 (6)
N4—C181.383 (6)C16—C191.490 (8)
N4—H4A0.8600C17—C181.370 (6)
C1—C21.497 (8)C17—H17A0.9300
C1—H1B0.9600C20—H20A0.9600
C1—H1C0.9600C20—H20B0.9600
C1—H1D0.9600C20—H20C0.9600
H1W1—O1W—H2W1107.5C7—C8—N2132.3 (5)
C9—O2—C10116.1 (5)O1—C9—O2122.1 (6)
C19—O4—C20115.7 (5)O1—C9—C6127.3 (7)
C2—N1—C3110.1 (5)O2—C9—C6110.6 (6)
C2—N1—H1A125.0O2—C10—H10A109.5
C3—N1—H1A125.0O2—C10—H10B109.5
C2—N2—C8109.4 (5)H10A—C10—H10B109.5
C2—N2—H2A125.3O2—C10—H10C109.5
C8—N2—H2A125.3H10A—C10—H10C109.5
C12—N3—C13110.4 (4)H10B—C10—H10C109.5
C12—N3—H3A124.8C12—C11—H11A109.5
C13—N3—H3A124.8C12—C11—H11B109.5
C12—N4—C18110.2 (4)H11A—C11—H11B109.5
C12—N4—H4A124.9C12—C11—H11C109.5
C18—N4—H4A124.9H11A—C11—H11C109.5
O6—N5—O5121.3 (5)H11B—C11—H11C109.5
O6—N5—O7119.9 (5)N4—C12—N3107.8 (5)
O5—N5—O7118.9 (5)N4—C12—C11126.3 (5)
O10—N6—O9122.3 (5)N3—C12—C11125.8 (5)
O10—N6—O8119.8 (5)C14—C13—N3132.6 (5)
O9—N6—O8117.9 (5)C14—C13—C18122.0 (5)
C2—C1—H1B109.5N3—C13—C18105.4 (4)
C2—C1—H1C109.5C15—C14—C13116.2 (5)
H1B—C1—H1C109.5C15—C14—H14A121.9
C2—C1—H1D109.5C13—C14—H14A121.9
H1B—C1—H1D109.5C14—C15—C16122.3 (5)
H1C—C1—H1D109.5C14—C15—H15A118.8
N1—C2—N2108.7 (5)C16—C15—H15A118.8
N1—C2—C1125.7 (5)C17—C16—C15121.0 (5)
N2—C2—C1125.6 (6)C17—C16—C19121.7 (5)
C4—C3—C8121.5 (5)C15—C16—C19117.2 (5)
C4—C3—N1132.7 (5)C18—C17—C16116.3 (5)
C8—C3—N1105.8 (5)C18—C17—H17A121.9
C3—C4—C5117.6 (5)C16—C17—H17A121.9
C3—C4—H4B121.2C17—C18—N4131.7 (4)
C5—C4—H4B121.2C17—C18—C13122.2 (5)
C4—C5—C6121.2 (5)N4—C18—C13106.2 (4)
C4—C5—H5A119.4O3—C19—O4121.8 (6)
C6—C5—H5A119.4O3—C19—C16125.4 (6)
C7—C6—C5120.9 (5)O4—C19—C16112.8 (5)
C7—C6—C9117.1 (5)O4—C20—H20A109.5
C5—C6—C9122.0 (6)O4—C20—H20B109.5
C6—C7—C8117.2 (5)H20A—C20—H20B109.5
C6—C7—H7A121.4O4—C20—H20C109.5
C8—C7—H7A121.4H20A—C20—H20C109.5
C3—C8—C7121.6 (5)H20B—C20—H20C109.5
C3—C8—N2106.1 (5)
C3—N1—C2—N20.7 (6)C18—N4—C12—N30.3 (5)
C3—N1—C2—C1177.8 (5)C18—N4—C12—C11178.1 (5)
C8—N2—C2—N10.4 (6)C13—N3—C12—N40.0 (5)
C8—N2—C2—C1178.1 (5)C13—N3—C12—C11178.4 (5)
C2—N1—C3—C4178.6 (5)C12—N3—C13—C14179.7 (5)
C2—N1—C3—C80.8 (6)C12—N3—C13—C180.3 (5)
C8—C3—C4—C51.5 (7)N3—C13—C14—C15179.2 (5)
N1—C3—C4—C5177.8 (5)C18—C13—C14—C150.8 (7)
C3—C4—C5—C61.8 (7)C13—C14—C15—C160.5 (8)
C4—C5—C6—C71.2 (7)C14—C15—C16—C170.2 (8)
C4—C5—C6—C9179.7 (5)C14—C15—C16—C19177.9 (5)
C5—C6—C7—C80.2 (7)C15—C16—C17—C180.2 (7)
C9—C6—C7—C8179.3 (4)C19—C16—C17—C18177.9 (4)
C4—C3—C8—C70.5 (8)C16—C17—C18—N4179.9 (5)
N1—C3—C8—C7178.9 (4)C16—C17—C18—C130.5 (7)
C4—C3—C8—N2178.9 (4)C12—N4—C18—C17179.1 (5)
N1—C3—C8—N20.5 (5)C12—N4—C18—C130.5 (5)
C6—C7—C8—C30.1 (7)C14—C13—C18—C170.8 (7)
C6—C7—C8—N2177.8 (5)N3—C13—C18—C17179.2 (4)
C2—N2—C8—C30.1 (6)C14—C13—C18—N4179.5 (4)
C2—N2—C8—C7178.3 (5)N3—C13—C18—N40.5 (5)
C10—O2—C9—O10.3 (8)C20—O4—C19—O30.8 (8)
C10—O2—C9—C6179.7 (4)C20—O4—C19—C16179.7 (4)
C7—C6—C9—O11.1 (9)C17—C16—C19—O3169.9 (6)
C5—C6—C9—O1178.0 (6)C15—C16—C19—O38.2 (9)
C7—C6—C9—O2178.9 (4)C17—C16—C19—O49.6 (7)
C5—C6—C9—O22.0 (7)C15—C16—C19—O4172.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O60.862.343.040 (6)138
N1—H1A···O70.862.072.906 (6)163
N2—H2A···O8i0.862.363.120 (6)148
N2—H2A···O9i0.862.002.804 (7)154
N3—H3A···O5ii0.862.433.135 (6)139
N3—H3A···O7ii0.862.042.868 (5)160
N4—H4A···O80.862.012.839 (6)163
N4—H4A···O100.862.403.090 (6)138
O1W—H1W1···O40.852.433.28 (2)173
O1W—H2W1···O100.852.152.72 (2)124
C1—H1B···O9i0.962.553.350 (8)140
C5—H5A···O20.932.352.679 (6)100
C5—H5A···O3iii0.932.493.140 (7)127
C10—H10A···O1Wii0.962.473.42 (2)173
C15—H15A···O6iv0.932.563.359 (7)145
C17—H17A···O100.932.553.258 (7)133
Symmetry codes: (i) x1, y, z; (ii) x+1, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x1, y+1/2, z1/2.
 

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