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The structure analyses of racemic 3-chloro-1-(4-morpholino-5-nitro­imidazol-1-yl)­propan-2-ol, C10H15ClN4O4, (II), and 3-chloro-1-(5-morpholino-4-nitro­imidazol-1-yl)­propan-2-ol, C10H15ClN4O4, (III), have been undertaken in order to determine the position of the morpholine residue in these two isomers. The morpholine residue in (II) is connected at the 4-position, while in (III), it is connected at the 5-position of the imidazole ring. The morpholine mean planes and nitro groups in the two compounds deviate from the imidazole planes to different extents. The nitro groups in (II) and (III) take part in the conjugation system of the imidazole rings. In consequence, the exocyclic C—N bonds are significantly shorter than the normal single Csp2—NO2 bond and the nitro groups in (II) and (III) show an extraordinary stability on treatment with morpholine and piperidine [Gzella, Wrzeciono & Pöppel (1999). Acta Cryst. C55, 1562–1565]. In the crystal lattice, the mol­ecules of both compounds are linked by O—H...N and C—H...O intermolecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008635/jz1415sup1.cif
Contains datablocks II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008635/jz1415IIsup2.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008635/jz1415IIIsup3.hkl
Contains datablock III

CCDC references: 150863; 150864

Computing details top

For both compounds, data collection: Kuma KM-4 Software (Kuma Diffraction, 1991); cell refinement: Kuma KM-4 Software; data reduction: Kuma KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(II) 3-Chloro-1-(4-morpholinyl-5-nitroimidazol-1-yl)propan-2-ol top
Crystal data top
C10H15ClN4O4F(000) = 304
Mr = 290.71Dx = 1.534 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 9.6840 (8) ÅCell parameters from 55 reflections
b = 5.2868 (8) Åθ = 16.8–31.8°
c = 12.8212 (7) ŵ = 2.88 mm1
β = 106.470 (6)°T = 293 K
V = 629.48 (11) Å3Needle, yellow
Z = 20.54 × 0.17 × 0.10 mm
Data collection top
Kuma Diffraction KM-4
diffractometer
2201 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 70.1°, θmin = 3.6°
ω/2θ scansh = 1111
Absorption correction: ψ-scan
(North et al., 1968)
k = 66
Tmin = 0.511, Tmax = 0.750l = 015
2286 measured reflections2 standard reflections every 100 reflections
2245 independent reflections intensity decay: 0.8%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.025 w = 1/[σ2(Fo2) + (0.0482P)2 + 0.0886P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.072(Δ/σ)max = 0.010
S = 1.04Δρmax = 0.17 e Å3
2245 reflectionsΔρmin = 0.26 e Å3
178 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0246 (15)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.344 (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
N10.25344 (13)0.2996 (3)0.44535 (10)0.0324 (3)
C20.35945 (16)0.1446 (4)0.49604 (12)0.0364 (3)
H2A0.40130.02880.45960.044*
N30.39995 (14)0.1702 (3)0.60289 (11)0.0360 (3)
C40.31146 (15)0.3495 (3)0.62562 (12)0.0316 (3)
C50.22027 (15)0.4378 (3)0.52711 (12)0.0315 (3)
C60.17975 (16)0.2867 (3)0.32829 (12)0.0346 (3)
H6A0.08450.36060.31420.042*
H6B0.16850.11110.30550.042*
C70.26426 (16)0.4268 (3)0.26313 (12)0.0341 (3)
H7A0.27710.60240.28850.041*
C80.1863 (2)0.4274 (4)0.14286 (13)0.0437 (4)
H8A0.24320.52020.10450.052*
H8B0.09500.51460.13130.052*
Cl90.15358 (5)0.11495 (11)0.08745 (3)0.05587 (16)
O100.40081 (13)0.3153 (3)0.28177 (10)0.0419 (3)
H10A0.462 (3)0.395 (5)0.3097 (19)0.049 (7)*
N110.32214 (13)0.4247 (3)0.72854 (10)0.0363 (3)
C120.45195 (17)0.3614 (3)0.81480 (12)0.0362 (3)
H12A0.53540.36950.78730.043*
H12B0.44460.19100.84080.043*
C130.46770 (18)0.5472 (4)0.90583 (13)0.0403 (4)
H13A0.55190.50350.96480.048*
H13B0.48280.71480.88030.048*
O140.34471 (13)0.5516 (3)0.94579 (10)0.0488 (3)
C150.21984 (19)0.6160 (5)0.86044 (15)0.0494 (4)
H15A0.23130.78430.83400.059*
H15B0.13670.61800.88840.059*
C160.19449 (17)0.4310 (4)0.76809 (13)0.0417 (4)
H16A0.17630.26400.79270.050*
H16B0.11100.48180.70990.050*
N170.14224 (13)0.6623 (3)0.50655 (11)0.0351 (3)
O180.11854 (15)0.7774 (3)0.58335 (11)0.0509 (3)
O190.10343 (15)0.7434 (3)0.41192 (11)0.0492 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0317 (6)0.0353 (7)0.0286 (6)0.0005 (5)0.0060 (5)0.0009 (5)
C20.0366 (7)0.0351 (8)0.0369 (8)0.0061 (7)0.0092 (6)0.0013 (7)
N30.0350 (6)0.0350 (8)0.0356 (6)0.0068 (6)0.0063 (5)0.0009 (6)
C40.0295 (6)0.0318 (8)0.0319 (7)0.0004 (6)0.0062 (5)0.0002 (6)
C50.0300 (6)0.0327 (8)0.0309 (7)0.0022 (6)0.0073 (5)0.0011 (6)
C60.0325 (7)0.0407 (9)0.0283 (7)0.0067 (7)0.0049 (5)0.0012 (6)
C70.0362 (7)0.0340 (8)0.0324 (7)0.0055 (6)0.0103 (6)0.0020 (6)
C80.0492 (9)0.0483 (10)0.0333 (8)0.0023 (8)0.0109 (6)0.0045 (7)
Cl90.0524 (3)0.0688 (3)0.0433 (2)0.0123 (2)0.00850 (17)0.0192 (2)
O100.0322 (6)0.0464 (8)0.0471 (7)0.0075 (5)0.0110 (5)0.0112 (6)
N110.0309 (6)0.0478 (8)0.0290 (6)0.0055 (6)0.0064 (5)0.0010 (6)
C120.0354 (7)0.0393 (9)0.0309 (7)0.0051 (6)0.0046 (6)0.0025 (6)
C130.0405 (8)0.0488 (10)0.0316 (7)0.0037 (7)0.0102 (6)0.0026 (7)
O140.0475 (7)0.0691 (9)0.0329 (6)0.0036 (6)0.0164 (5)0.0027 (6)
C150.0435 (9)0.0637 (12)0.0450 (9)0.0055 (9)0.0190 (7)0.0047 (9)
C160.0338 (7)0.0534 (10)0.0389 (8)0.0010 (7)0.0121 (6)0.0008 (8)
N170.0314 (6)0.0319 (7)0.0411 (7)0.0037 (6)0.0088 (5)0.0047 (6)
O180.0546 (7)0.0446 (8)0.0558 (8)0.0154 (6)0.0193 (6)0.0037 (6)
O190.0543 (7)0.0433 (7)0.0473 (7)0.0109 (6)0.0098 (5)0.0170 (6)
Geometric parameters (Å, º) top
N1—C21.330 (2)C8—Cl91.791 (2)
N1—C51.388 (2)O10—H10A0.73 (3)
N1—C61.4693 (18)N11—C121.4585 (19)
C2—N31.321 (2)N11—C161.4634 (19)
N3—C41.364 (2)C12—C131.500 (2)
C4—N111.354 (2)C13—O141.424 (2)
C4—C51.400 (2)O14—C151.423 (2)
C5—N171.391 (2)C15—C161.501 (3)
C6—C71.518 (2)N17—O181.2331 (18)
C7—O101.405 (2)N17—O191.2403 (18)
C7—C81.512 (2)
C2—N1—C5105.48 (12)C8—C7—C6111.77 (13)
C2—N1—C6123.67 (14)C7—C8—Cl9112.55 (13)
C5—N1—C6130.28 (13)C7—O10—H10A116 (2)
N3—C2—N1113.89 (14)C4—N11—C12118.88 (13)
C2—N3—C4105.83 (13)C4—N11—C16120.38 (13)
N11—C4—N3122.24 (14)C12—N11—C16111.94 (12)
N11—C4—C5129.48 (15)N11—C12—C13108.38 (14)
N3—C4—C5108.23 (13)O14—C13—C12112.32 (14)
N1—C5—N17122.36 (13)C15—O14—C13110.02 (12)
N1—C5—C4106.50 (13)O14—C15—C16111.35 (17)
N17—C5—C4128.68 (14)N11—C16—C15108.82 (14)
N1—C6—C7110.98 (12)O18—N17—O19122.50 (15)
O10—C7—C8110.39 (13)O18—N17—C5118.92 (13)
O10—C7—C6109.28 (14)O19—N17—C5118.54 (13)
C5—N1—C2—N30.76 (19)C6—C7—C8—Cl959.45 (17)
C6—N1—C2—N3172.93 (14)N3—C4—N11—C1215.4 (2)
N1—C2—N3—C42.1 (2)C5—C4—N11—C12161.53 (16)
C2—N3—C4—N11179.97 (16)N3—C4—N11—C16129.44 (18)
C2—N3—C4—C52.49 (18)C5—C4—N11—C1653.6 (3)
C2—N1—C5—N17162.78 (15)C4—N11—C12—C13156.38 (15)
C6—N1—C5—N1725.8 (2)C16—N11—C12—C1355.97 (19)
C2—N1—C5—C40.84 (17)N11—C12—C13—O1456.87 (18)
C6—N1—C5—C4170.61 (15)C12—C13—O14—C1558.9 (2)
N11—C4—C5—N1179.38 (16)C13—O14—C15—C1658.9 (2)
N3—C4—C5—N12.08 (17)C4—N11—C16—C15156.19 (17)
N11—C4—C5—N1717.1 (3)C12—N11—C16—C1556.7 (2)
N3—C4—C5—N17160.15 (15)O14—C15—C16—N1157.5 (2)
C2—N1—C6—C783.3 (2)N1—C5—N17—O18178.89 (14)
C5—N1—C6—C7106.64 (17)C4—C5—N17—O1819.1 (2)
N1—C6—C7—O1060.52 (17)N1—C5—N17—O191.3 (2)
N1—C6—C7—C8176.99 (15)C4—C5—N17—O19158.41 (16)
O10—C7—C8—Cl962.41 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H10A···N3i0.73 (3)2.08 (3)2.7948 (19)167 (3)
C6—H6B···O19ii0.972.553.224 (2)126
C8—H8A···O14iii0.972.503.372 (2)149
C16—H16B···O180.972.272.918 (2)124
C16—H16B···O19iv0.972.553.295 (2)134
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y1, z; (iii) x, y, z1; (iv) x, y1/2, z+1.
(III) 3-Chloro-1-(5-morpholinyl-4-nitroimidazol-1-yl)propan-2-ol top
Crystal data top
C10H15ClN4O4Z = 2
Mr = 290.71F(000) = 304
Triclinic, P1Dx = 1.521 Mg m3
a = 6.5036 (8) ÅCu Kα radiation, λ = 1.54178 Å
b = 7.8493 (9) ÅCell parameters from 43 reflections
c = 12.9757 (14) Åθ = 11.3–30.0°
α = 91.101 (9)°µ = 2.85 mm1
β = 101.026 (10)°T = 293 K
γ = 101.94 (1)°Plate, yellow
V = 634.91 (13) Å30.38 × 0.27 × 0.05 mm
Data collection top
Kuma Diffraction KM-4
diffractometer
2036 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 70.0°, θmin = 3.5°
ω/2θ scansh = 77
Absorption correction: ψ-scan
(North et al., 1968)
k = 99
Tmin = 0.440, Tmax = 0.867l = 015
2386 measured reflections2 standard reflections every 100 reflections
2281 independent reflections intensity decay: 3.8%
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0695P)2 + 0.2622P]
where P = (Fo2 + 2Fc2)/3
2281 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.28 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
N10.8161 (2)0.51309 (19)0.14522 (12)0.0354 (3)
C20.7643 (3)0.5726 (2)0.04814 (15)0.0379 (4)
H2A0.74880.68630.03680.046*
N30.7385 (2)0.4537 (2)0.02739 (12)0.0396 (4)
C40.7703 (3)0.3077 (2)0.02411 (14)0.0364 (4)
C50.8218 (3)0.3398 (2)0.13179 (14)0.0338 (4)
C60.8466 (3)0.6089 (2)0.24612 (15)0.0386 (4)
H6A0.94240.72130.24560.046*
H6B0.91320.54480.30140.046*
C70.6325 (3)0.6369 (2)0.26959 (14)0.0387 (4)
H7A0.59640.73920.23440.046*
C80.6605 (4)0.6696 (3)0.38694 (16)0.0502 (5)
H8A0.78630.76160.41190.060*
H8B0.68340.56470.42160.060*
Cl90.43074 (12)0.73111 (11)0.42040 (5)0.0762 (3)
O100.4646 (2)0.49088 (19)0.23518 (12)0.0462 (4)
H10A0.389 (5)0.512 (4)0.175 (2)0.071 (9)*
N110.7442 (3)0.1472 (2)0.03436 (13)0.0439 (4)
O120.7421 (3)0.0135 (2)0.01360 (14)0.0599 (4)
O130.7223 (3)0.1494 (2)0.13030 (12)0.0661 (5)
N140.8900 (3)0.2497 (2)0.21725 (12)0.0368 (4)
C150.7373 (3)0.1714 (3)0.28089 (16)0.0436 (5)
H15A0.65530.05940.24830.052*
H15B0.63840.24650.28670.052*
C160.8614 (4)0.1479 (3)0.38845 (19)0.0571 (6)
H16A0.93320.26130.42260.068*
H16B0.76290.09110.43100.068*
O171.0168 (3)0.0456 (2)0.38198 (13)0.0600 (5)
C181.1640 (4)0.1254 (3)0.32027 (18)0.0507 (5)
H18A1.26890.05470.31760.061*
H18B1.23960.23910.35280.061*
C191.0502 (3)0.1458 (3)0.21028 (16)0.0439 (5)
H19A1.15200.20390.16980.053*
H19B0.98090.03220.17560.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0401 (8)0.0308 (8)0.0360 (8)0.0085 (7)0.0082 (6)0.0034 (6)
C20.0368 (9)0.0372 (10)0.0414 (10)0.0095 (8)0.0093 (7)0.0093 (7)
N30.0356 (8)0.0477 (9)0.0373 (8)0.0128 (7)0.0074 (6)0.0066 (7)
C40.0336 (9)0.0397 (10)0.0367 (9)0.0095 (8)0.0070 (7)0.0001 (7)
C50.0334 (9)0.0326 (9)0.0367 (9)0.0074 (7)0.0095 (7)0.0025 (7)
C60.0424 (10)0.0322 (9)0.0390 (9)0.0069 (8)0.0041 (7)0.0013 (7)
C70.0452 (11)0.0330 (9)0.0373 (9)0.0101 (8)0.0052 (8)0.0014 (7)
C80.0545 (12)0.0578 (13)0.0404 (11)0.0191 (10)0.0073 (9)0.0023 (9)
Cl90.0755 (5)0.1039 (6)0.0603 (4)0.0367 (4)0.0231 (3)0.0085 (3)
O100.0460 (8)0.0439 (8)0.0457 (8)0.0068 (6)0.0050 (6)0.0047 (6)
N110.0394 (9)0.0478 (10)0.0444 (9)0.0134 (7)0.0044 (7)0.0064 (7)
O120.0669 (11)0.0411 (9)0.0676 (10)0.0133 (8)0.0025 (8)0.0075 (7)
O130.0807 (12)0.0767 (12)0.0430 (9)0.0301 (10)0.0046 (8)0.0142 (8)
N140.0394 (8)0.0371 (8)0.0384 (8)0.0139 (7)0.0118 (6)0.0088 (6)
C150.0424 (11)0.0421 (11)0.0521 (11)0.0132 (9)0.0179 (9)0.0140 (8)
C160.0650 (14)0.0686 (15)0.0511 (12)0.0303 (12)0.0255 (11)0.0227 (11)
O170.0653 (10)0.0716 (11)0.0591 (9)0.0355 (9)0.0257 (8)0.0334 (8)
C180.0454 (11)0.0594 (13)0.0528 (12)0.0207 (10)0.0115 (9)0.0172 (10)
C190.0461 (11)0.0478 (11)0.0459 (10)0.0213 (9)0.0161 (8)0.0111 (8)
Geometric parameters (Å, º) top
N1—C21.358 (2)C8—Cl91.787 (2)
N1—C51.377 (2)O10—H10A0.88 (3)
N1—C61.456 (2)N11—O131.227 (2)
C2—N31.303 (3)N11—O121.229 (2)
N3—C41.370 (2)N14—C151.458 (2)
C4—C51.379 (3)N14—C191.463 (2)
C4—N111.421 (2)C15—C161.508 (3)
C5—N141.378 (2)C16—O171.427 (3)
C6—C71.538 (3)O17—C181.419 (3)
C7—O101.407 (2)C18—C191.505 (3)
C7—C81.509 (3)
C2—N1—C5107.45 (15)C8—C7—C6108.05 (16)
C2—N1—C6127.10 (15)C7—C8—Cl9111.27 (15)
C5—N1—C6125.33 (15)C7—O10—H10A108.8 (19)
N3—C2—N1112.92 (16)O13—N11—O12123.55 (18)
C2—N3—C4103.95 (15)O13—N11—C4118.07 (18)
N3—C4—C5112.18 (16)O12—N11—C4118.38 (17)
N3—C4—N11119.78 (16)C5—N14—C15119.37 (15)
C5—C4—N11128.02 (17)C5—N14—C19118.71 (15)
N1—C5—N14120.03 (16)C15—N14—C19112.40 (14)
N1—C5—C4103.47 (15)N14—C15—C16108.18 (17)
N14—C5—C4136.16 (17)O17—C16—C15111.35 (18)
N1—C6—C7111.54 (15)C18—O17—C16110.78 (16)
O10—C7—C8109.33 (17)O17—C18—C19111.02 (18)
O10—C7—C6111.85 (15)N14—C19—C18108.05 (16)
C5—N1—C2—N30.9 (2)C6—C7—C8—Cl9172.58 (14)
C6—N1—C2—N3177.08 (17)N3—C4—N11—O139.8 (3)
N1—C2—N3—C41.6 (2)C5—C4—N11—O13171.78 (19)
C2—N3—C4—C51.7 (2)N3—C4—N11—O12169.34 (17)
C2—N3—C4—N11176.94 (17)C5—C4—N11—O129.1 (3)
C2—N1—C5—N14174.00 (16)N1—C5—N14—C1585.0 (2)
C6—N1—C5—N149.7 (3)C4—C5—N14—C15103.1 (3)
C2—N1—C5—C40.3 (2)N1—C5—N14—C19131.23 (19)
C6—N1—C5—C4176.04 (16)C4—C5—N14—C1940.7 (3)
N3—C4—C5—N11.3 (2)C5—N14—C15—C16157.27 (18)
N11—C4—C5—N1177.31 (18)C19—N14—C15—C1656.8 (2)
N3—C4—C5—N14171.6 (2)N14—C15—C16—O1756.5 (2)
N11—C4—C5—N149.9 (4)C15—C16—O17—C1859.1 (3)
C2—N1—C6—C771.6 (2)C16—O17—C18—C1959.8 (3)
C5—N1—C6—C7103.9 (2)C5—N14—C19—C18156.31 (18)
N1—C6—C7—O1037.7 (2)C15—N14—C19—C1857.5 (2)
N1—C6—C7—C8158.05 (16)O17—C18—C19—N1457.9 (2)
O10—C7—C8—Cl965.47 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H10A···N3i0.88 (3)1.98 (3)2.850 (2)169 (3)
C7—H7A···O13i0.982.573.396 (2)142
C8—H8A···O17ii0.972.503.364 (3)149
C15—H15B···O100.972.463.359 (2)154
C19—H19B···O120.972.342.947 (3)120
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z.
 

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