Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045680/rk2037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045680/rk2037Isup2.hkl |
CCDC reference: 667270
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.146
- Data-to-parameter ratio = 18.1
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 ............ 0.50 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT417_ALERT_2_C Short Inter D-H..H-D H21 .. H701 .. 2.11 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C12 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C22 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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
1–(2-Hydroxy–3–chloropropyl)–2-methyl–5–nitroimidazole was recrystallized from C5H5OH/H2O (1:1) to give the ornidazole hemihydrate. Diffraction quality crystal was obtained by slow evaporation of at room temperature.
The H atoms on the oxygen were located in a difference Fourier map and the other H atoms were placed in calculated posistion with C—H = 0.96–0.98 Å. All H atoms included in the final cycles of refinement as riding mode, with Uiso(H) = 1.2Ueq of the carrier atoms.
5–Nitroimidazoles are a well–established group of antiprotozoan and antibacterial agents. 1–(2–Hydroxy–3–chloropropyl)–2–methyl–5–nitroimidazole (ornidazole) is a member of the nitroimidazole group so it is used for the treatment of susceptible protozoal infections and prophylaxis of anaerobic bacterial infections. Due to its antimicrobial activity it inhibits the growth of both anaerobic bacteria and certain anaerobic protozoa such as Trichomonas vaginalis, Entamoeba histolytica and Giardia lamblia (López Nigro et al., 2003). The asymmetric unit have two independent molecules of ornidazole with the different chirality - C12 atom is R and C22 atom is S absolute configuration. The crystal structure of the title compound is formed by the system of intermolecular hydrogen bonds, which involve the water molecules.
For related literature, see: López Nigro et al. (2003).
Data collection: PROCESS-AUTO (Rigaku/MSC & Rigaku, 2004); cell refinement: PROCESS-AUTO (Rigaku/MSC & Rigaku, 2004); data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC & Rigaku, 2004).
C7H10ClN3O3·0.5H2O | F(000) = 1904.00 |
Mr = 228.64 | Dx = 1.462 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -C 2yc | Cell parameters from 14509 reflections |
a = 23.202 (8) Å | θ = 3.1–27.5° |
b = 8.289 (2) Å | µ = 0.36 mm−1 |
c = 22.270 (7) Å | T = 298 K |
β = 103.996 (14)° | Block, colourless |
V = 4156 (2) Å3 | 0.31 × 0.28 × 0.25 mm |
Z = 16 |
Rigaku R-AXIS RAPID diffractometer | 3287 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.026 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −30→30 |
Tmin = 0.890, Tmax = 0.914 | k = −10→9 |
18814 measured reflections | l = −28→28 |
4755 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[0.002Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.146 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.59 e Å−3 |
4755 reflections | Δρmin = −0.62 e Å−3 |
263 parameters | Extinction correction: Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, pp. 291–294. Copenhagen: Munksgaard. |
0 restraints | Extinction coefficient: 94 (36) |
C7H10ClN3O3·0.5H2O | V = 4156 (2) Å3 |
Mr = 228.64 | Z = 16 |
Monoclinic, C2/c | Mo Kα radiation |
a = 23.202 (8) Å | µ = 0.36 mm−1 |
b = 8.289 (2) Å | T = 298 K |
c = 22.270 (7) Å | 0.31 × 0.28 × 0.25 mm |
β = 103.996 (14)° |
Rigaku R-AXIS RAPID diffractometer | 4755 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3287 reflections with F2 > 2σ(F2) |
Tmin = 0.890, Tmax = 0.914 | Rint = 0.026 |
18814 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.59 e Å−3 |
4755 reflections | Δρmin = −0.62 e Å−3 |
263 parameters |
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 using all reflections. The weighted R–factor (wR) and goodness of fit (S) are based on F2. R–factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R–factor (gt). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.51877 (3) | 0.54256 (8) | 0.64516 (4) | 0.0940 (2) | |
Cl2 | 0.36375 (4) | 1.26213 (8) | 0.21447 (4) | 0.0870 (2) | |
O7 | 0.12252 (6) | 0.44528 (16) | 0.43419 (6) | 0.0487 (3) | |
O11 | 0.38555 (6) | 0.74189 (13) | 0.52290 (6) | 0.0433 (3) | |
O12 | 0.43759 (6) | 0.28657 (19) | 0.48376 (8) | 0.0615 (4) | |
O13 | 0.37775 (9) | 0.1710 (2) | 0.40646 (9) | 0.0889 (6) | |
O21 | 0.43764 (6) | 0.9665 (2) | 0.18369 (6) | 0.0604 (4) | |
O22 | 0.31344 (9) | 0.6537 (2) | 0.19209 (8) | 0.0759 (5) | |
O23 | 0.25133 (9) | 0.5497 (2) | 0.23892 (10) | 0.0952 (7) | |
N11 | 0.33913 (6) | 0.42982 (16) | 0.51646 (6) | 0.0347 (3) | |
N12 | 0.24678 (6) | 0.42340 (19) | 0.45819 (8) | 0.0454 (4) | |
N13 | 0.38789 (8) | 0.2606 (2) | 0.45115 (8) | 0.0508 (4) | |
N21 | 0.38473 (6) | 0.75918 (17) | 0.30684 (6) | 0.0384 (3) | |
N22 | 0.36136 (8) | 0.7319 (2) | 0.39693 (8) | 0.0484 (4) | |
N23 | 0.29640 (8) | 0.6258 (2) | 0.23892 (9) | 0.0590 (5) | |
C11 | 0.46743 (8) | 0.6864 (2) | 0.60469 (10) | 0.0475 (5) | |
C12 | 0.42434 (8) | 0.6139 (2) | 0.54889 (8) | 0.0374 (4) | |
C13 | 0.38913 (6) | 0.4751 (2) | 0.56720 (8) | 0.0368 (4) | |
C14 | 0.33813 (8) | 0.3374 (2) | 0.46472 (8) | 0.0388 (4) | |
C15 | 0.28143 (9) | 0.3346 (2) | 0.43015 (9) | 0.0438 (4) | |
C16 | 0.28216 (8) | 0.4799 (2) | 0.51017 (8) | 0.0378 (4) | |
C17 | 0.26214 (9) | 0.5812 (2) | 0.55585 (10) | 0.0501 (5) | |
C21 | 0.39930 (12) | 1.0974 (2) | 0.26126 (11) | 0.0650 (7) | |
C22 | 0.39831 (9) | 0.9501 (2) | 0.22289 (9) | 0.0496 (5) | |
C23 | 0.41990 (8) | 0.8002 (2) | 0.26236 (9) | 0.0459 (5) | |
C24 | 0.33042 (8) | 0.6820 (2) | 0.29689 (9) | 0.0438 (4) | |
C25 | 0.31703 (9) | 0.6678 (2) | 0.35252 (10) | 0.0506 (5) | |
C26 | 0.40150 (8) | 0.7856 (2) | 0.36831 (8) | 0.0388 (4) | |
C27 | 0.45826 (9) | 0.8620 (2) | 0.40072 (9) | 0.0519 (5) | |
H11 | 0.3781 | 0.7312 | 0.4804 | 0.052* | |
H21 | 0.4123 | 0.9602 | 0.1424 | 0.074* | |
H111 | 0.4450 | 0.7297 | 0.6326 | 0.057* | |
H112 | 0.4892 | 0.7728 | 0.5908 | 0.057* | |
H122 | 0.4460 | 0.5762 | 0.5189 | 0.045* | |
H131 | 0.3742 | 0.5078 | 0.6024 | 0.044* | |
H132 | 0.4151 | 0.3827 | 0.5785 | 0.044* | |
H151 | 0.2684 | 0.2799 | 0.3929 | 0.053* | |
H171 | 0.2206 | 0.6048 | 0.5409 | 0.060* | |
H172 | 0.2684 | 0.5244 | 0.5945 | 0.060* | |
H173 | 0.2843 | 0.6800 | 0.5619 | 0.060* | |
H211 | 0.4402 | 1.1262 | 0.2802 | 0.078* | |
H212 | 0.3786 | 1.0757 | 0.2933 | 0.078* | |
H221 | 0.3579 | 0.9317 | 0.1978 | 0.060* | |
H231 | 0.4606 | 0.8191 | 0.2852 | 0.055* | |
H232 | 0.4187 | 0.7091 | 0.2347 | 0.055* | |
H251 | 0.2826 | 0.6213 | 0.3592 | 0.061* | |
H271 | 0.4599 | 0.8700 | 0.4441 | 0.062* | |
H272 | 0.4909 | 0.7975 | 0.3950 | 0.062* | |
H273 | 0.4608 | 0.9679 | 0.3841 | 0.062* | |
H701 | 0.1147 | 0.5476 | 0.4490 | 0.058* | |
H702 | 0.1637 | 0.4386 | 0.4380 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0725 (4) | 0.0614 (3) | 0.1148 (6) | 0.0113 (3) | −0.0424 (4) | −0.0073 (3) |
Cl2 | 0.1094 (5) | 0.0701 (4) | 0.0873 (5) | 0.0288 (3) | 0.0349 (4) | 0.0337 (3) |
O7 | 0.0426 (7) | 0.0498 (7) | 0.0506 (7) | 0.0022 (5) | 0.0053 (5) | −0.0054 (5) |
O11 | 0.0546 (7) | 0.0402 (6) | 0.0349 (6) | 0.0055 (5) | 0.0103 (5) | 0.0015 (5) |
O12 | 0.0428 (7) | 0.0742 (9) | 0.0691 (10) | 0.0090 (7) | 0.0168 (7) | −0.0120 (8) |
O13 | 0.0853 (12) | 0.1008 (13) | 0.0805 (12) | 0.0155 (10) | 0.0200 (10) | −0.0501 (11) |
O21 | 0.0479 (7) | 0.0967 (11) | 0.0396 (7) | 0.0034 (7) | 0.0165 (6) | 0.0138 (7) |
O22 | 0.0980 (13) | 0.0804 (11) | 0.0395 (8) | −0.0058 (9) | −0.0024 (8) | −0.0063 (7) |
O23 | 0.0642 (11) | 0.1136 (15) | 0.0996 (15) | −0.0259 (11) | 0.0042 (10) | −0.0344 (12) |
N11 | 0.0328 (7) | 0.0361 (6) | 0.0346 (7) | 0.0018 (5) | 0.0069 (5) | −0.0001 (5) |
N12 | 0.0355 (7) | 0.0486 (8) | 0.0483 (9) | 0.0001 (6) | 0.0025 (6) | 0.0026 (7) |
N13 | 0.0540 (10) | 0.0498 (9) | 0.0506 (9) | 0.0072 (7) | 0.0167 (8) | −0.0085 (7) |
N21 | 0.0413 (7) | 0.0424 (7) | 0.0313 (7) | 0.0063 (6) | 0.0083 (5) | 0.0046 (5) |
N22 | 0.0544 (9) | 0.0546 (9) | 0.0376 (8) | 0.0031 (7) | 0.0134 (7) | 0.0078 (7) |
N23 | 0.0562 (11) | 0.0573 (10) | 0.0544 (11) | 0.0027 (9) | −0.0046 (8) | −0.0087 (8) |
C11 | 0.0412 (9) | 0.0422 (9) | 0.0540 (11) | 0.0029 (7) | 0.0015 (8) | −0.0085 (8) |
C12 | 0.0368 (8) | 0.0372 (8) | 0.0383 (9) | 0.0032 (7) | 0.0093 (7) | −0.0038 (7) |
C13 | 0.0361 (8) | 0.0416 (8) | 0.0310 (8) | 0.0013 (7) | 0.0047 (6) | −0.0005 (6) |
C14 | 0.0429 (9) | 0.0363 (8) | 0.0372 (9) | 0.0008 (7) | 0.0097 (7) | −0.0023 (6) |
C15 | 0.0480 (10) | 0.0429 (9) | 0.0365 (9) | −0.0042 (8) | 0.0024 (7) | −0.0026 (7) |
C16 | 0.0342 (8) | 0.0371 (8) | 0.0416 (9) | 0.0024 (7) | 0.0084 (7) | 0.0046 (7) |
C17 | 0.0457 (10) | 0.0535 (10) | 0.0532 (11) | 0.0095 (8) | 0.0160 (9) | 0.0003 (8) |
C21 | 0.0857 (17) | 0.0616 (12) | 0.0488 (12) | 0.0138 (12) | 0.0181 (11) | 0.0135 (10) |
C22 | 0.0488 (10) | 0.0629 (11) | 0.0405 (10) | 0.0081 (9) | 0.0177 (8) | 0.0127 (8) |
C23 | 0.0440 (10) | 0.0590 (11) | 0.0365 (9) | 0.0114 (8) | 0.0135 (7) | 0.0057 (8) |
C24 | 0.0420 (9) | 0.0460 (9) | 0.0411 (10) | 0.0029 (7) | 0.0055 (7) | 0.0017 (7) |
C25 | 0.0481 (11) | 0.0520 (10) | 0.0519 (11) | −0.0038 (9) | 0.0124 (9) | 0.0058 (8) |
C26 | 0.0431 (9) | 0.0397 (8) | 0.0328 (8) | 0.0065 (7) | 0.0077 (7) | 0.0048 (6) |
C27 | 0.0492 (11) | 0.0606 (11) | 0.0417 (10) | 0.0022 (9) | 0.0027 (8) | −0.0016 (8) |
Cl1—C11 | 1.7702 (19) | C22—C23 | 1.534 (2) |
Cl2—C21 | 1.793 (2) | C24—C25 | 1.353 (3) |
O11—C12 | 1.421 (2) | C26—C27 | 1.482 (2) |
O12—N13 | 1.224 (2) | O7—H701 | 0.944 |
O13—N13 | 1.218 (2) | O7—H702 | 0.940 |
O21—C22 | 1.414 (2) | O11—H11 | 0.925 |
O22—N23 | 1.223 (2) | O21—H21 | 0.965 |
O23—N23 | 1.221 (2) | C11—H111 | 0.970 |
N11—C13 | 1.4593 (19) | C11—H112 | 0.970 |
N11—C14 | 1.379 (2) | C12—H122 | 0.980 |
N11—C16 | 1.360 (2) | C13—H131 | 0.970 |
N12—C15 | 1.350 (2) | C13—H132 | 0.970 |
N12—C16 | 1.332 (2) | C15—H151 | 0.930 |
N13—C14 | 1.414 (2) | C17—H171 | 0.960 |
N21—C23 | 1.468 (2) | C17—H172 | 0.960 |
N21—C24 | 1.383 (2) | C17—H173 | 0.960 |
N21—C26 | 1.347 (2) | C21—H211 | 0.970 |
N22—C25 | 1.351 (2) | C21—H212 | 0.970 |
N22—C26 | 1.326 (2) | C22—H221 | 0.980 |
N23—C24 | 1.419 (2) | C23—H231 | 0.970 |
C11—C12 | 1.518 (2) | C23—H232 | 0.970 |
C12—C13 | 1.522 (2) | C25—H251 | 0.930 |
C14—C15 | 1.354 (2) | C27—H271 | 0.960 |
C16—C17 | 1.478 (2) | C27—H272 | 0.960 |
C21—C22 | 1.488 (3) | C27—H273 | 0.960 |
C13—N11—C14 | 129.75 (14) | Cl1—C11—H112 | 108.8 |
C13—N11—C16 | 124.89 (14) | C12—C11—H111 | 108.8 |
C14—N11—C16 | 105.31 (13) | C12—C11—H112 | 108.8 |
C15—N12—C16 | 106.46 (15) | H111—C11—H112 | 109.5 |
O12—N13—O13 | 124.1 (2) | O11—C12—H122 | 109.8 |
O12—N13—C14 | 119.65 (16) | C11—C12—H122 | 109.8 |
O13—N13—C14 | 116.28 (17) | C13—C12—H122 | 109.8 |
C23—N21—C24 | 129.28 (15) | N11—C13—H131 | 109.0 |
C23—N21—C26 | 125.24 (15) | N11—C13—H132 | 109.0 |
C24—N21—C26 | 105.43 (16) | C12—C13—H131 | 109.0 |
C25—N22—C26 | 106.19 (17) | C12—C13—H132 | 109.0 |
O22—N23—O23 | 123.43 (19) | H131—C13—H132 | 109.5 |
O22—N23—C24 | 119.36 (18) | N12—C15—H151 | 125.3 |
O23—N23—C24 | 117.2 (2) | C14—C15—H151 | 125.3 |
Cl1—C11—C12 | 112.27 (13) | C16—C17—H171 | 109.5 |
O11—C12—C11 | 105.34 (13) | C16—C17—H172 | 109.5 |
O11—C12—C13 | 110.20 (14) | C16—C17—H173 | 109.5 |
C11—C12—C13 | 111.70 (15) | H171—C17—H172 | 109.5 |
N11—C13—C12 | 111.38 (13) | H171—C17—H173 | 109.5 |
N11—C14—N13 | 125.40 (14) | H172—C17—H173 | 109.5 |
N11—C14—C15 | 107.59 (16) | Cl2—C21—H211 | 109.2 |
N13—C14—C15 | 127.01 (16) | Cl2—C21—H212 | 109.2 |
N12—C15—C14 | 109.45 (16) | C22—C21—H211 | 109.2 |
N11—C16—N12 | 111.18 (16) | C22—C21—H212 | 109.2 |
N11—C16—C17 | 124.20 (14) | H211—C21—H212 | 109.5 |
N12—C16—C17 | 124.61 (16) | O21—C22—H221 | 109.6 |
Cl2—C21—C22 | 110.50 (15) | C21—C22—H221 | 109.6 |
O21—C22—C21 | 110.69 (18) | C23—C22—H221 | 109.6 |
O21—C22—C23 | 105.16 (16) | N21—C23—H231 | 108.2 |
C21—C22—C23 | 112.22 (16) | N21—C23—H232 | 108.2 |
N21—C23—C22 | 114.63 (16) | C22—C23—H231 | 108.2 |
N21—C24—N23 | 125.63 (18) | C22—C23—H232 | 108.2 |
N21—C24—C25 | 107.19 (15) | H231—C23—H232 | 109.5 |
N23—C24—C25 | 127.17 (18) | N22—C25—H251 | 125.3 |
N22—C25—C24 | 109.48 (18) | C24—C25—H251 | 125.3 |
N21—C26—N22 | 111.71 (15) | C26—C27—H271 | 109.5 |
N21—C26—C27 | 124.64 (18) | C26—C27—H272 | 109.5 |
N22—C26—C27 | 123.64 (16) | C26—C27—H273 | 109.5 |
H701—O7—H702 | 107.3 | H271—C27—H272 | 109.5 |
C12—O11—H11 | 106.7 | H271—C27—H273 | 109.5 |
C22—O21—H21 | 104.3 | H272—C27—H273 | 109.5 |
Cl1—C11—H111 | 108.8 | ||
C13—N11—C14—N13 | 2.1 (2) | C24—N21—C26—N22 | −0.6 (2) |
C13—N11—C14—C15 | −177.86 (16) | C24—N21—C26—C27 | 178.17 (17) |
C14—N11—C13—C12 | 79.1 (2) | C26—N21—C24—N23 | −178.00 (17) |
C13—N11—C16—N12 | 177.80 (15) | C26—N21—C24—C25 | 0.8 (2) |
C13—N11—C16—C17 | −3.4 (2) | C25—N22—C26—N21 | 0.2 (2) |
C16—N11—C13—C12 | −97.8 (2) | C25—N22—C26—C27 | −178.59 (17) |
C14—N11—C16—N12 | 0.24 (19) | C26—N22—C25—C24 | 0.3 (2) |
C14—N11—C16—C17 | 179.06 (17) | O22—N23—C24—N21 | −4.4 (2) |
C16—N11—C14—N13 | 179.52 (17) | O22—N23—C24—C25 | 177.1 (2) |
C16—N11—C14—C15 | −0.46 (19) | O23—N23—C24—N21 | 174.86 (19) |
C15—N12—C16—N11 | 0.07 (19) | O23—N23—C24—C25 | −3.6 (3) |
C15—N12—C16—C17 | −178.74 (18) | Cl1—C11—C12—O11 | 178.33 (13) |
C16—N12—C15—C14 | −0.4 (2) | Cl1—C11—C12—C13 | 58.69 (19) |
O12—N13—C14—N11 | −7.1 (2) | O11—C12—C13—N11 | 50.51 (19) |
O12—N13—C14—C15 | 172.92 (19) | C11—C12—C13—N11 | 167.24 (14) |
O13—N13—C14—N11 | 173.08 (18) | N11—C14—C15—N12 | 0.5 (2) |
O13—N13—C14—C15 | −6.9 (2) | N13—C14—C15—N12 | −179.46 (17) |
C23—N21—C24—N23 | −0.5 (3) | Cl2—C21—C22—O21 | 71.3 (2) |
C23—N21—C24—C25 | 178.28 (17) | Cl2—C21—C22—C23 | −171.55 (15) |
C24—N21—C23—C22 | 78.6 (2) | O21—C22—C23—N21 | −179.62 (14) |
C23—N21—C26—N22 | −178.24 (16) | C21—C22—C23—N21 | 60.0 (2) |
C23—N21—C26—C27 | 0.5 (2) | N21—C24—C25—N22 | −0.7 (2) |
C26—N21—C23—C22 | −104.36 (19) | N23—C24—C25—N22 | 178.05 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H701···O11i | 0.94 | 1.85 | 2.7854 (17) | 169 |
O7—H702···N12 | 0.94 | 1.87 | 2.808 (2) | 172 |
O11—H11···N22 | 0.93 | 1.80 | 2.726 (2) | 174 |
O21—H21···O7ii | 0.97 | 1.71 | 2.6643 (18) | 171 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C7H10ClN3O3·0.5H2O |
Mr | 228.64 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 23.202 (8), 8.289 (2), 22.270 (7) |
β (°) | 103.996 (14) |
V (Å3) | 4156 (2) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.31 × 0.28 × 0.25 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.890, 0.914 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 18814, 4755, 3287 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.146, 1.01 |
No. of reflections | 4755 |
No. of parameters | 263 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.62 |
Computer programs: PROCESS-AUTO (Rigaku/MSC & Rigaku, 2004), CrystalStructure (Rigaku/MSC & Rigaku, 2004), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H701···O11i | 0.944 | 1.854 | 2.7854 (17) | 168.7 |
O7—H702···N12 | 0.940 | 1.874 | 2.808 (2) | 171.6 |
O11—H11···N22 | 0.925 | 1.804 | 2.726 (2) | 174.1 |
O21—H21···O7ii | 0.965 | 1.707 | 2.6643 (18) | 171.1 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1/2, y+1/2, −z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
5–Nitroimidazoles are a well–established group of antiprotozoan and antibacterial agents. 1–(2–Hydroxy–3–chloropropyl)–2–methyl–5–nitroimidazole (ornidazole) is a member of the nitroimidazole group so it is used for the treatment of susceptible protozoal infections and prophylaxis of anaerobic bacterial infections. Due to its antimicrobial activity it inhibits the growth of both anaerobic bacteria and certain anaerobic protozoa such as Trichomonas vaginalis, Entamoeba histolytica and Giardia lamblia (López Nigro et al., 2003). The asymmetric unit have two independent molecules of ornidazole with the different chirality - C12 atom is R and C22 atom is S absolute configuration. The crystal structure of the title compound is formed by the system of intermolecular hydrogen bonds, which involve the water molecules.