The title compound, C
8H
9N
2O
2+·Cl
-·H
2O, comprises C
8H
9N
2O
2+ cations, chloride anions and lattice water molecules. Individual components are linked into an
R
(8) hydrogen-bonded ring to form the crystallographic asymmetric unit. The asymmetric units are linked by hydrogen-bonding contacts to form an extended three-dimensional structure.
Supporting information
CCDC reference: 177240
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.100
- Data-to-parameter ratio = 11.9
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
DIFF_012 Alert A _diffrn_reflns_av_R_equivalents is missing
R factor for symmetry-equivalent intensities.
The following tests will not be performed
RINTA
| Author response: ...
No equivalent data were collected so there is no value for the merging R.
|
Alert Level C:
PLAT_731 Alert C Bond Calc 0.82(3), Rep 0.819(10) .... 3.00 s.u-Ratio
O211 -H211 1.555 1.555
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2001).
1
H-Benzimidazole-2-methanediol monohydrochloride monohydrate
top
Crystal data top
| C8H9N2O2+·Cl−·H2O | F(000) = 456 |
| Mr = 218.64 | Dx = 1.463 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 12.513 (4) Å | Cell parameters from 22 reflections |
| b = 4.977 (3) Å | θ = 13.3–17.4° |
| c = 16.388 (9) Å | µ = 0.37 mm−1 |
| β = 103.38 (6)° | T = 150 K |
| V = 992.9 (9) Å3 | Tablet, colourless |
| Z = 4 | 0.48 × 0.29 × 0.19 mm |
Data collection top
Stoe Stadi-4 four-circle
diffractometer | θmax = 25.0°, θmin = 2.7° |
| Radiation source: fine-focus sealed tube | h = −14→14 |
| Graphite monochromator | k = 0→5 |
| ω/θ scans | l = 0→19 |
| 1724 measured reflections | 3 standard reflections every 60 min |
| 1724 independent reflections | intensity decay: none |
| 1470 reflections with I > 2σ(I) | |
Refinement top
| Refinement on F2 | Primary atom site location: direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier synthesis |
| R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: difference Fourier synthesis |
| wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.21 | w = 1/[σ2(Fo2) + (0.038P)2 + 0.848P]
where P = (Fo2 + 2Fc2)/3 |
| 1724 reflections | (Δ/σ)max = 0.001 |
| 145 parameters | Δρmax = 0.24 e Å−3 |
| 7 restraints | Δρmin = −0.21 e Å−3 |
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 | |
| Cl1 | 0.28249 (5) | 0.80898 (12) | 0.96645 (4) | 0.02668 (19) | |
| O1 | 0.25808 (15) | 0.3143 (4) | 0.84544 (11) | 0.0294 (4) | |
| H11 | 0.258 (3) | 0.433 (4) | 0.8807 (14) | 0.044* | |
| H12 | 0.258 (3) | 0.171 (3) | 0.8707 (16) | 0.044* | |
| N1 | 0.69793 (16) | 0.7279 (4) | 0.90177 (12) | 0.0217 (4) | |
| H1 | 0.690 (2) | 0.856 (4) | 0.9365 (13) | 0.026* | |
| C2 | 0.61967 (18) | 0.5670 (5) | 0.86111 (14) | 0.0206 (5) | |
| C21 | 0.50278 (18) | 0.5737 (5) | 0.87029 (15) | 0.0228 (5) | |
| H21 | 0.4951 | 0.4582 | 0.9170 | 0.027* | |
| O211 | 0.48246 (14) | 0.8408 (4) | 0.88820 (12) | 0.0339 (5) | |
| H211 | 0.4298 (18) | 0.828 (7) | 0.9098 (19) | 0.051* | |
| O212 | 0.43511 (13) | 0.4791 (3) | 0.79537 (10) | 0.0235 (4) | |
| H212 | 0.3827 (16) | 0.405 (6) | 0.8075 (18) | 0.035* | |
| N3 | 0.66070 (15) | 0.3899 (4) | 0.81622 (12) | 0.0207 (4) | |
| H3 | 0.6232 (18) | 0.267 (4) | 0.7831 (14) | 0.025* | |
| C4 | 0.77345 (18) | 0.4340 (5) | 0.82920 (14) | 0.0213 (5) | |
| C5 | 0.85463 (19) | 0.3080 (5) | 0.79801 (15) | 0.0264 (5) | |
| H5 | 0.8388 | 0.1666 | 0.7600 | 0.032* | |
| C6 | 0.9600 (2) | 0.4041 (6) | 0.82642 (16) | 0.0310 (6) | |
| H6 | 1.0169 | 0.3239 | 0.8075 | 0.037* | |
| C7 | 0.9840 (2) | 0.6184 (6) | 0.88284 (17) | 0.0326 (6) | |
| H7 | 1.0564 | 0.6762 | 0.9004 | 0.039* | |
| C8 | 0.9032 (2) | 0.7463 (5) | 0.91312 (16) | 0.0287 (6) | |
| H8 | 0.9190 | 0.8893 | 0.9505 | 0.034* | |
| C9 | 0.79728 (18) | 0.6493 (5) | 0.88453 (14) | 0.0208 (5) | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Cl1 | 0.0323 (3) | 0.0220 (3) | 0.0277 (3) | −0.0022 (2) | 0.0110 (2) | −0.0041 (2) |
| O1 | 0.0351 (10) | 0.0228 (10) | 0.0319 (10) | −0.0030 (8) | 0.0108 (8) | −0.0017 (8) |
| N1 | 0.0235 (10) | 0.0196 (10) | 0.0221 (10) | 0.0008 (8) | 0.0057 (8) | −0.0031 (8) |
| C2 | 0.0229 (11) | 0.0195 (12) | 0.0188 (11) | 0.0017 (10) | 0.0033 (9) | 0.0030 (10) |
| C21 | 0.0219 (12) | 0.0233 (13) | 0.0235 (12) | 0.0020 (10) | 0.0057 (9) | −0.0004 (10) |
| O211 | 0.0270 (9) | 0.0285 (10) | 0.0498 (12) | 0.0024 (8) | 0.0164 (8) | −0.0109 (9) |
| O212 | 0.0204 (8) | 0.0254 (9) | 0.0242 (8) | −0.0030 (7) | 0.0042 (7) | 0.0020 (7) |
| N3 | 0.0190 (10) | 0.0199 (10) | 0.0219 (10) | −0.0004 (8) | 0.0022 (8) | −0.0032 (8) |
| C4 | 0.0206 (11) | 0.0221 (12) | 0.0211 (11) | 0.0011 (10) | 0.0043 (9) | 0.0035 (10) |
| C5 | 0.0288 (12) | 0.0255 (13) | 0.0261 (12) | 0.0034 (11) | 0.0089 (10) | 0.0000 (11) |
| C6 | 0.0241 (12) | 0.0364 (15) | 0.0349 (14) | 0.0042 (11) | 0.0118 (10) | 0.0039 (12) |
| C7 | 0.0214 (12) | 0.0370 (15) | 0.0386 (15) | −0.0051 (11) | 0.0053 (10) | 0.0029 (12) |
| C8 | 0.0272 (12) | 0.0274 (14) | 0.0299 (13) | −0.0060 (11) | 0.0032 (10) | −0.0011 (11) |
| C9 | 0.0217 (11) | 0.0188 (12) | 0.0219 (11) | 0.0016 (10) | 0.0052 (9) | 0.0038 (9) |
Geometric parameters (Å, º) top
| N1—C2 | 1.320 (3) | C8—C9 | 1.387 (3) |
| N1—C9 | 1.393 (3) | O1—H11 | 0.827 (10) |
| C2—N3 | 1.325 (3) | O1—H12 | 0.826 (10) |
| C2—C21 | 1.505 (3) | N1—H1 | 0.876 (10) |
| C21—O211 | 1.398 (3) | C21—H21 | 0.9800 |
| C21—O212 | 1.402 (3) | O211—H211 | 0.819 (10) |
| N3—C4 | 1.395 (3) | O212—H212 | 0.817 (10) |
| C4—C5 | 1.388 (3) | N3—H3 | 0.879 (10) |
| C4—C9 | 1.391 (3) | C5—H5 | 0.9300 |
| C5—C6 | 1.378 (4) | C6—H6 | 0.9300 |
| C6—C7 | 1.398 (4) | C7—H7 | 0.9300 |
| C7—C8 | 1.380 (4) | C8—H8 | 0.9300 |
| | | |
| C2—N1—C9 | 108.7 (2) | H11—O1—H12 | 105 (2) |
| N1—C2—N3 | 110.3 (2) | C2—N1—H1 | 125.9 (17) |
| N1—C2—C21 | 124.1 (2) | C9—N1—H1 | 125.3 (17) |
| N3—C2—C21 | 125.5 (2) | O211—C21—H21 | 109.8 |
| O211—C21—O212 | 113.7 (2) | O212—C21—H21 | 109.8 |
| O211—C21—C2 | 105.68 (19) | C2—C21—H21 | 109.8 |
| O212—C21—C2 | 108.00 (19) | C21—O211—H211 | 103 (3) |
| C2—N3—C4 | 108.57 (19) | C21—O212—H212 | 107 (2) |
| C5—C4—C9 | 121.6 (2) | C2—N3—H3 | 125.9 (17) |
| C5—C4—N3 | 132.3 (2) | C4—N3—H3 | 125.5 (17) |
| C9—C4—N3 | 106.1 (2) | C6—C5—H5 | 121.8 |
| C6—C5—C4 | 116.3 (2) | C4—C5—H5 | 121.8 |
| C5—C6—C7 | 122.1 (2) | C5—C6—H6 | 119.0 |
| C8—C7—C6 | 121.8 (2) | C7—C6—H6 | 119.0 |
| C7—C8—C9 | 116.1 (2) | C8—C7—H7 | 119.1 |
| C8—C9—C4 | 122.2 (2) | C6—C7—H7 | 119.1 |
| C8—C9—N1 | 131.5 (2) | C7—C8—H8 | 121.9 |
| C4—C9—N1 | 106.4 (2) | C9—C8—H8 | 121.9 |
| | | |
| C9—N1—C2—N3 | −1.5 (3) | C4—C5—C6—C7 | −0.7 (4) |
| C9—N1—C2—C21 | 174.3 (2) | C5—C6—C7—C8 | −0.2 (4) |
| N1—C2—C21—O211 | 30.8 (3) | C6—C7—C8—C9 | 0.2 (4) |
| N3—C2—C21—O211 | −154.1 (2) | C7—C8—C9—C4 | 0.6 (4) |
| N1—C2—C21—O212 | 152.7 (2) | C7—C8—C9—N1 | 179.8 (2) |
| N3—C2—C21—O212 | −32.1 (3) | C5—C4—C9—C8 | −1.5 (4) |
| N1—C2—N3—C4 | 1.0 (3) | N3—C4—C9—C8 | 178.7 (2) |
| C21—C2—N3—C4 | −174.7 (2) | C5—C4—C9—N1 | 179.2 (2) |
| C2—N3—C4—C5 | −180.0 (2) | N3—C4—C9—N1 | −0.7 (2) |
| C2—N3—C4—C9 | −0.2 (2) | C2—N1—C9—C8 | −177.9 (2) |
| C9—C4—C5—C6 | 1.5 (3) | C2—N1—C9—C4 | 1.3 (3) |
| N3—C4—C5—C6 | −178.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H11···Cl1 | 0.83 (2) | 2.32 (2) | 3.132 (2) | 169 (3) |
| O211—H211···Cl1 | 0.82 (2) | 2.25 (2) | 3.069 (2) | 178 (3) |
| O212—H212···O1 | 0.82 (2) | 1.86 (2) | 2.664 (3) | 167 (3) |
| O1—H12···Cl1i | 0.83 (2) | 2.36 (2) | 3.173 (2) | 168 (3) |
| N1—H1···Cl1ii | 0.88 (2) | 2.27 (2) | 3.129 (2) | 165 (2) |
| N3—H3···O212iii | 0.88 (2) | 1.95 (2) | 2.819 (3) | 170 (2) |
| Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+2, −z+2; (iii) −x+1, y−1/2, −z+3/2. |
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organic compounds
(8) hydrogen-bonded ring to form the crystallographic asymmetric unit. The asymmetric units are linked by hydrogen-bonding contacts to form an extended three-dimensional structure.
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.004 Å
Alert Level A:
Alert Level C:
