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Oxazolidin-2-ones are widely used as protective groups for 1,2-amino alcohols and chiral derivatives are employed as chiral auxiliaries. The crystal structures of four differently substituted oxazolidinecarbohydrazides, namely N′-[(E)-benzyl­idene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12N3O3, (I), N′-[(E)-2-chloro­benzyl­idene]-N-methyl-2-oxo-1,3-oxazolidine-4-car­bohydrazide, C12H12ClN3O3, (II), (4S)-N′-[(E)-4-chloro­benzyl­idene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12ClN3O3, (III), and (4S)-N′-[(E)-2,6-di­chloro­benzyl­idene]-N,3-dimethyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C13H13Cl2N3O3, (IV), show that an unexpected mild-condition racemization from the chiral starting materials has occurred in (I) and (II). In the extended structures, the centrosymmetric phases, which each crystallize with two mol­ecules (A and B) in the asymmetric unit, form A+B dimers linked by pairs of N—H...O hydrogen bonds, albeit with different O-atom acceptors. One dimer is composed of one mol­ecule with an S configuration for its stereogenic centre and the other with an R configuration, and possesses approximate local inversion symmetry. The other dimer consists of either R,R or S,S pairs and possesses approximate local twofold symmetry. In the chiral structure, N—H...O hydrogen bonds link the mol­ecules into C(5) chains, with adjacent mol­ecules related by a 21 screw axis. A wide variety of weak inter­actions, including C—H...O, C—H...Cl, C—H...π and π–π stacking inter­actions, occur in these structures, but there is little conformity between them.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615012450/uk3114sup1.cif
Contains datablocks I, II, III, IV, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012450/uk3114Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012450/uk3114IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012450/uk3114IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012450/uk3114IVsup5.hkl
Contains datablock IV

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615012450/uk3114Isup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615012450/uk3114IIsup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615012450/uk3114IIIsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615012450/uk3114IVsup9.cml
Supplementary material

CCDC references: 1409419; 1409418; 1409417; 1409416

Computing details top

For all compounds, data collection: CrystalClear (Rigaku, 2012); cell refinement: CrystalClear (Rigaku, 2012); data reduction: CrystalClear (Rigaku, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) N'-[(E)-Benzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide top
Crystal data top
C12H13N3O3F(000) = 1040
Mr = 247.26Dx = 1.427 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.8881 (9) ÅCell parameters from 10133 reflections
b = 14.0296 (17) Åθ = 3.1–27.6°
c = 20.810 (3) ŵ = 0.11 mm1
β = 91.749 (7)°T = 100 K
V = 2301.9 (5) Å3Chip, colourless
Z = 80.07 × 0.04 × 0.02 mm
Data collection top
Rugaku CCD
diffractometer
2385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.108
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω scansh = 106
21153 measured reflectionsk = 1818
5267 independent reflectionsl = 2526
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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H atoms treated by a mixture of independent and constrained refinement
S = 0.92 w = 1/[σ2(Fo2) + (0.080P)2]
where P = (Fo2 + 2Fc2)/3
5267 reflections(Δ/σ)max < 0.001
333 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.30 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
C10.9028 (4)0.6339 (2)0.42060 (16)0.0292 (8)
H10.95500.60780.38400.035*
C20.8429 (4)0.5745 (2)0.46741 (16)0.0319 (8)
H20.85460.50750.46290.038*
C30.7665 (4)0.6107 (2)0.52070 (16)0.0335 (8)
H30.72480.56890.55250.040*
C40.7506 (4)0.7085 (2)0.52782 (16)0.0320 (8)
H40.69880.73410.56470.038*
C50.8106 (4)0.7688 (2)0.48105 (15)0.0286 (8)
H50.79960.83580.48600.034*
C60.8867 (4)0.7324 (2)0.42700 (15)0.0247 (7)
C70.9506 (4)0.7979 (2)0.37904 (15)0.0269 (7)
H70.94180.86470.38570.032*
C81.0827 (5)0.93197 (19)0.29462 (16)0.0337 (8)
H8A0.96540.95470.29610.051*
H8B1.13970.96330.25910.051*
H8C1.14260.94710.33530.051*
C91.1566 (4)0.7896 (2)0.23345 (15)0.0256 (7)
C101.1489 (4)0.6811 (2)0.23093 (15)0.0267 (7)
H101.19880.65310.27150.032*
C110.9681 (4)0.6431 (2)0.21806 (15)0.0300 (8)
H11A0.93790.59590.25120.036*
H11B0.88470.69580.21840.036*
C121.1301 (5)0.5990 (2)0.13464 (16)0.0312 (8)
N11.0180 (3)0.76675 (16)0.32839 (12)0.0256 (6)
N21.0833 (3)0.82943 (16)0.28472 (12)0.0255 (6)
N31.2335 (4)0.64422 (18)0.17600 (13)0.0315 (7)
H1N1.344 (5)0.654 (2)0.1622 (16)0.038*
O11.2231 (3)0.83676 (14)0.19142 (10)0.0312 (5)
O20.9705 (3)0.59923 (15)0.15560 (10)0.0357 (6)
O31.1654 (3)0.56158 (15)0.08375 (11)0.0419 (6)
C130.8928 (4)0.8429 (2)0.09588 (15)0.0293 (8)
H130.83250.86980.06150.035*
C140.9609 (4)0.9015 (2)0.14116 (15)0.0306 (8)
H140.94930.96870.13740.037*
C151.0457 (4)0.8637 (2)0.19184 (16)0.0316 (8)
H151.09400.90470.22270.038*
C161.0608 (4)0.7661 (2)0.19794 (16)0.0324 (8)
H161.11700.73990.23360.039*
C170.9946 (4)0.7066 (2)0.15245 (14)0.0279 (8)
H171.00580.63950.15680.033*
C180.9110 (4)0.7443 (2)0.09986 (14)0.0256 (7)
C190.8448 (4)0.6804 (2)0.05104 (14)0.0246 (7)
H190.85160.61320.05600.029*
C200.7170 (5)0.5545 (2)0.03913 (16)0.0350 (8)
H20A0.83510.53330.03690.052*
H20B0.65370.53410.00030.052*
H20C0.66560.52650.07700.052*
C210.6424 (4)0.7036 (2)0.09435 (15)0.0262 (7)
C220.6542 (4)0.8120 (2)0.09171 (15)0.0261 (7)
H220.60480.83630.05000.031*
C230.8370 (4)0.8482 (2)0.10210 (15)0.0301 (8)
H23A0.91830.79440.10240.036*
H23B0.86700.89330.06760.036*
C240.6797 (5)0.9008 (2)0.18577 (17)0.0317 (8)
N40.7782 (3)0.71670 (17)0.00197 (12)0.0260 (6)
N50.7120 (3)0.65802 (16)0.04380 (12)0.0276 (6)
N60.5719 (4)0.85637 (18)0.14523 (14)0.0314 (7)
H2N0.466 (5)0.857 (2)0.1542 (16)0.038*
O40.5786 (3)0.66074 (14)0.13891 (11)0.0325 (6)
O50.8399 (3)0.89520 (14)0.16334 (10)0.0335 (6)
O60.6516 (3)0.94059 (15)0.23570 (11)0.0417 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0306 (19)0.0274 (16)0.0297 (18)0.0008 (14)0.0017 (15)0.0016 (14)
C20.038 (2)0.0218 (15)0.036 (2)0.0033 (14)0.0052 (16)0.0005 (14)
C30.036 (2)0.0362 (18)0.0277 (18)0.0107 (16)0.0011 (16)0.0071 (15)
C40.032 (2)0.0346 (18)0.0293 (18)0.0034 (15)0.0027 (16)0.0018 (15)
C50.0292 (19)0.0264 (16)0.0300 (18)0.0002 (14)0.0021 (15)0.0031 (14)
C60.0234 (17)0.0233 (15)0.0274 (18)0.0019 (13)0.0011 (14)0.0006 (13)
C70.0314 (19)0.0219 (15)0.0273 (18)0.0009 (13)0.0009 (16)0.0028 (13)
C80.051 (2)0.0144 (14)0.0363 (19)0.0035 (15)0.0045 (17)0.0015 (13)
C90.0261 (19)0.0208 (14)0.0299 (18)0.0020 (13)0.0008 (15)0.0026 (14)
C100.0319 (19)0.0216 (15)0.0268 (18)0.0014 (13)0.0052 (15)0.0022 (13)
C110.039 (2)0.0224 (15)0.0291 (19)0.0035 (14)0.0037 (16)0.0034 (13)
C120.042 (2)0.0213 (15)0.0309 (19)0.0035 (15)0.0060 (17)0.0034 (15)
N10.0300 (16)0.0215 (12)0.0252 (15)0.0025 (11)0.0010 (13)0.0032 (11)
N20.0331 (16)0.0177 (12)0.0257 (15)0.0000 (11)0.0028 (12)0.0001 (11)
N30.0332 (17)0.0250 (14)0.0367 (17)0.0005 (13)0.0076 (14)0.0024 (12)
O10.0328 (14)0.0255 (11)0.0354 (13)0.0018 (10)0.0047 (11)0.0039 (10)
O20.0393 (16)0.0319 (12)0.0358 (13)0.0043 (11)0.0005 (12)0.0061 (10)
O30.0607 (18)0.0304 (12)0.0350 (14)0.0019 (12)0.0060 (13)0.0066 (11)
C130.0328 (19)0.0284 (16)0.0268 (18)0.0026 (15)0.0033 (15)0.0051 (14)
C140.035 (2)0.0263 (15)0.0309 (18)0.0053 (15)0.0002 (16)0.0018 (14)
C150.030 (2)0.0340 (17)0.0306 (19)0.0055 (15)0.0004 (16)0.0035 (15)
C160.036 (2)0.0321 (17)0.0292 (19)0.0022 (16)0.0035 (16)0.0021 (15)
C170.0260 (19)0.0272 (16)0.0303 (19)0.0030 (14)0.0002 (15)0.0020 (14)
C180.0249 (17)0.0241 (15)0.0277 (18)0.0030 (13)0.0011 (15)0.0038 (13)
C190.0245 (18)0.0236 (15)0.0255 (17)0.0021 (13)0.0018 (14)0.0032 (13)
C200.051 (2)0.0202 (15)0.034 (2)0.0038 (15)0.0058 (17)0.0023 (14)
C210.0229 (18)0.0264 (15)0.0293 (18)0.0011 (13)0.0024 (15)0.0027 (14)
C220.033 (2)0.0208 (14)0.0251 (17)0.0043 (14)0.0026 (15)0.0000 (13)
C230.0317 (19)0.0243 (15)0.034 (2)0.0014 (14)0.0016 (16)0.0012 (14)
C240.043 (2)0.0176 (14)0.035 (2)0.0007 (15)0.0025 (17)0.0017 (14)
N40.0259 (15)0.0250 (13)0.0273 (15)0.0053 (11)0.0028 (12)0.0026 (12)
N50.0344 (16)0.0202 (12)0.0285 (15)0.0015 (12)0.0035 (13)0.0010 (11)
N60.0332 (17)0.0295 (14)0.0319 (16)0.0019 (14)0.0054 (14)0.0054 (12)
O40.0345 (14)0.0275 (11)0.0358 (13)0.0017 (10)0.0071 (11)0.0047 (10)
O50.0361 (15)0.0259 (11)0.0386 (14)0.0058 (10)0.0012 (11)0.0072 (10)
O60.0583 (17)0.0265 (12)0.0405 (14)0.0067 (11)0.0082 (13)0.0122 (11)
Geometric parameters (Å, º) top
C1—C21.376 (4)C13—C141.373 (4)
C1—C61.395 (4)C13—C181.393 (4)
C1—H10.9500C13—H130.9500
C2—C31.376 (5)C14—C151.373 (5)
C2—H20.9500C14—H140.9500
C3—C41.386 (4)C15—C161.381 (4)
C3—H30.9500C15—H150.9500
C4—C51.383 (4)C16—C171.377 (4)
C4—H40.9500C16—H160.9500
C5—C61.388 (4)C17—C181.398 (4)
C5—H50.9500C17—H170.9500
C6—C71.458 (4)C18—C191.463 (4)
C7—N11.272 (4)C19—N41.269 (4)
C7—H70.9500C19—H190.9500
C8—N21.453 (3)C20—N51.456 (4)
C8—H8A0.9800C20—H20A0.9800
C8—H8B0.9800C20—H20B0.9800
C8—H8C0.9800C20—H20C0.9800
C9—O11.228 (4)C21—O41.226 (4)
C9—N21.350 (4)C21—N51.361 (4)
C9—C101.523 (4)C21—C221.525 (4)
C10—N31.438 (4)C22—N61.447 (4)
C10—C111.539 (4)C22—C231.538 (5)
C10—H101.0000C22—H221.0000
C11—O21.439 (4)C23—O51.434 (4)
C11—H11A0.9900C23—H23A0.9900
C11—H11B0.9900C23—H23B0.9900
C12—O31.222 (4)C24—O61.206 (4)
C12—N31.329 (4)C24—N61.334 (4)
C12—O21.345 (4)C24—O51.363 (4)
N1—N21.376 (3)N4—N51.374 (3)
N3—H1N0.93 (4)N6—H2N0.86 (4)
C2—C1—C6119.9 (3)C14—C13—C18120.7 (3)
C2—C1—H1120.1C14—C13—H13119.6
C6—C1—H1120.1C18—C13—H13119.6
C3—C2—C1121.0 (3)C15—C14—C13120.4 (3)
C3—C2—H2119.5C15—C14—H14119.8
C1—C2—H2119.5C13—C14—H14119.8
C2—C3—C4119.7 (3)C14—C15—C16120.0 (3)
C2—C3—H3120.2C14—C15—H15120.0
C4—C3—H3120.2C16—C15—H15120.0
C5—C4—C3119.7 (3)C17—C16—C15120.1 (3)
C5—C4—H4120.2C17—C16—H16119.9
C3—C4—H4120.2C15—C16—H16119.9
C4—C5—C6120.8 (3)C16—C17—C18120.5 (3)
C4—C5—H5119.6C16—C17—H17119.8
C6—C5—H5119.6C18—C17—H17119.8
C5—C6—C1119.0 (3)C13—C18—C17118.3 (3)
C5—C6—C7119.3 (3)C13—C18—C19121.8 (3)
C1—C6—C7121.7 (3)C17—C18—C19119.9 (3)
N1—C7—C6120.8 (3)N4—C19—C18118.5 (3)
N1—C7—H7119.6N4—C19—H19120.7
C6—C7—H7119.6C18—C19—H19120.7
N2—C8—H8A109.5N5—C20—H20A109.5
N2—C8—H8B109.5N5—C20—H20B109.5
H8A—C8—H8B109.5H20A—C20—H20B109.5
N2—C8—H8C109.5N5—C20—H20C109.5
H8A—C8—H8C109.5H20A—C20—H20C109.5
H8B—C8—H8C109.5H20B—C20—H20C109.5
O1—C9—N2122.8 (3)O4—C21—N5122.6 (3)
O1—C9—C10122.1 (3)O4—C21—C22122.9 (3)
N2—C9—C10115.0 (3)N5—C21—C22114.5 (3)
N3—C10—C9111.6 (3)N6—C22—C21111.8 (3)
N3—C10—C11100.8 (2)N6—C22—C23101.0 (2)
C9—C10—C11112.8 (3)C21—C22—C23112.5 (3)
N3—C10—H10110.4N6—C22—H22110.4
C9—C10—H10110.4C21—C22—H22110.4
C11—C10—H10110.4C23—C22—H22110.4
O2—C11—C10105.5 (3)O5—C23—C22105.4 (3)
O2—C11—H11A110.6O5—C23—H23A110.7
C10—C11—H11A110.6C22—C23—H23A110.7
O2—C11—H11B110.6O5—C23—H23B110.7
C10—C11—H11B110.6C22—C23—H23B110.7
H11A—C11—H11B108.8H23A—C23—H23B108.8
O3—C12—N3127.9 (3)O6—C24—N6129.1 (4)
O3—C12—O2121.5 (3)O6—C24—O5121.3 (3)
N3—C12—O2110.6 (3)N6—C24—O5109.6 (3)
C7—N1—N2120.1 (2)C19—N4—N5119.5 (2)
C9—N2—N1115.8 (2)C21—N5—N4115.2 (2)
C9—N2—C8121.7 (3)C21—N5—C20122.2 (3)
N1—N2—C8122.4 (2)N4—N5—C20122.7 (3)
C12—N3—C10113.3 (3)C24—N6—C22113.3 (3)
C12—N3—H1N115 (2)C24—N6—H2N118 (2)
C10—N3—H1N131 (2)C22—N6—H2N129 (2)
C12—O2—C11109.4 (3)C24—O5—C23110.0 (2)
C6—C1—C2—C30.2 (5)C18—C13—C14—C151.2 (5)
C1—C2—C3—C40.6 (5)C13—C14—C15—C160.9 (5)
C2—C3—C4—C50.5 (5)C14—C15—C16—C171.6 (5)
C3—C4—C5—C60.1 (5)C15—C16—C17—C180.3 (5)
C4—C5—C6—C10.3 (5)C14—C13—C18—C172.5 (5)
C4—C5—C6—C7179.2 (3)C14—C13—C18—C19177.8 (3)
C2—C1—C6—C50.2 (5)C16—C17—C18—C131.7 (5)
C2—C1—C6—C7179.1 (3)C16—C17—C18—C19178.5 (3)
C5—C6—C7—N1178.6 (3)C13—C18—C19—N44.3 (4)
C1—C6—C7—N12.5 (5)C17—C18—C19—N4176.0 (3)
O1—C9—C10—N32.4 (4)O4—C21—C22—N63.8 (4)
N2—C9—C10—N3178.4 (3)N5—C21—C22—N6177.6 (3)
O1—C9—C10—C11110.3 (3)O4—C21—C22—C23109.0 (3)
N2—C9—C10—C1168.9 (4)N5—C21—C22—C2369.6 (3)
N3—C10—C11—O25.7 (3)N6—C22—C23—O58.1 (3)
C9—C10—C11—O2113.4 (3)C21—C22—C23—O5111.3 (3)
C6—C7—N1—N2177.6 (3)C18—C19—N4—N5178.6 (3)
O1—C9—N2—N1178.5 (3)O4—C21—N5—N4180.0 (3)
C10—C9—N2—N12.3 (4)C22—C21—N5—N41.3 (4)
O1—C9—N2—C81.9 (5)O4—C21—N5—C200.5 (5)
C10—C9—N2—C8178.9 (3)C22—C21—N5—C20178.1 (3)
C7—N1—N2—C9178.1 (3)C19—N4—N5—C21179.6 (3)
C7—N1—N2—C81.5 (4)C19—N4—N5—C201.0 (4)
O3—C12—N3—C10179.1 (3)O6—C24—N6—C22176.5 (3)
O2—C12—N3—C100.3 (4)O5—C24—N6—C222.6 (4)
C9—C10—N3—C12116.1 (3)C21—C22—N6—C24113.1 (3)
C11—C10—N3—C123.9 (3)C23—C22—N6—C246.7 (3)
O3—C12—O2—C11176.7 (3)O6—C24—O5—C23177.5 (3)
N3—C12—O2—C113.8 (3)N6—C24—O5—C233.3 (3)
C10—C11—O2—C126.0 (3)C22—C23—O5—C247.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N···O4i0.93 (4)1.93 (4)2.861 (4)174 (3)
N6—H2N···O1ii0.86 (4)2.11 (4)2.955 (4)168 (3)
C11—H11A···O6iii0.992.313.154 (4)143
C14—H14···O5iv0.952.603.296 (4)130
C19—H19···O3v0.952.523.463 (4)171
C10—H10···Cg4vi1.002.813.587 (3)135
C22—H22···Cg2vii1.002.673.512 (3)142
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+3/2, y1/2, z+1/2; (iv) x+2, y+2, z; (v) x+2, y+1, z; (vi) x1/2, y+3/2, z+1/2; (vii) x3/2, y+3/2, z1/2.
(II) N'-[(E)-2-Chlorobenzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide top
Crystal data top
C12H12ClN3O3F(000) = 1168
Mr = 281.70Dx = 1.515 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
a = 15.7925 (11) ÅCell parameters from 38129 reflections
b = 13.7715 (4) Åθ = 3.2–27.6°
c = 11.3887 (3) ŵ = 0.32 mm1
β = 94.350 (7)°T = 100 K
V = 2469.8 (2) Å3Cut needle, colourless
Z = 80.14 × 0.05 × 0.05 mm
Data collection top
Rigaku CCD
diffractometer
4918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 27.5°, θmin = 3.2°
ω scansh = 2020
53991 measured reflectionsk = 1717
5667 independent reflectionsl = 1414
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0416P)2 + 1.0893P]
where P = (Fo2 + 2Fc2)/3
5667 reflections(Δ/σ)max = 0.001
351 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.37 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
C10.08148 (9)0.15608 (10)0.75150 (12)0.0205 (3)
C20.14794 (9)0.21323 (11)0.78375 (12)0.0246 (3)
H20.17680.19740.85150.030*
C30.17192 (9)0.29331 (12)0.71665 (13)0.0268 (3)
H30.21770.33260.73810.032*
C40.12970 (10)0.31697 (11)0.61792 (13)0.0259 (3)
H40.14540.37320.57310.031*
C50.06473 (9)0.25811 (11)0.58545 (12)0.0229 (3)
H50.03650.27400.51720.028*
C60.03945 (8)0.17575 (10)0.65047 (12)0.0191 (3)
C70.02752 (9)0.11153 (10)0.61446 (12)0.0199 (3)
H70.04960.06210.66630.024*
C80.15138 (10)0.01736 (11)0.56425 (14)0.0286 (3)
H8A0.10550.06210.58060.043*
H8B0.17460.01230.63800.043*
H8C0.19640.05310.52820.043*
C90.15298 (8)0.07315 (10)0.37916 (12)0.0199 (3)
C100.11701 (8)0.15820 (10)0.30531 (11)0.0181 (3)
H100.05460.14970.28600.022*
C110.13572 (9)0.25819 (10)0.36310 (12)0.0197 (3)
H11A0.08260.29570.36810.024*
H11B0.16360.25040.44340.024*
C120.20637 (8)0.24831 (10)0.19538 (11)0.0191 (3)
N10.05645 (7)0.12174 (8)0.51339 (10)0.0189 (2)
N20.11838 (7)0.05800 (9)0.48424 (10)0.0212 (2)
N30.16061 (8)0.16725 (9)0.19918 (10)0.0213 (2)
H1N0.1711 (11)0.1198 (13)0.1517 (16)0.026*
O10.20897 (7)0.02183 (8)0.34666 (9)0.0266 (2)
O20.19164 (6)0.30651 (7)0.28724 (8)0.0223 (2)
O30.25463 (6)0.27309 (8)0.12262 (9)0.0241 (2)
Cl10.04998 (2)0.05875 (3)0.84234 (3)0.02474 (9)
C130.56251 (10)0.14917 (10)0.42951 (13)0.0250 (3)
C140.53076 (11)0.15874 (11)0.31362 (13)0.0287 (3)
H140.56770.17410.25420.034*
C150.44561 (11)0.14600 (11)0.28483 (13)0.0292 (3)
H150.42340.15170.20520.035*
C160.39207 (11)0.12482 (11)0.37209 (13)0.0288 (3)
H160.33300.11600.35240.035*
C170.42431 (10)0.11642 (11)0.48793 (12)0.0240 (3)
H170.38680.10280.54720.029*
C180.51063 (9)0.12747 (10)0.51929 (12)0.0199 (3)
C190.54573 (9)0.11580 (10)0.64101 (12)0.0197 (3)
H190.60530.10980.65830.024*
C200.62059 (9)0.09449 (11)0.86619 (13)0.0245 (3)
H20A0.64050.03370.83300.037*
H20B0.63220.09370.95190.037*
H20C0.65030.14940.83310.037*
C210.47414 (9)0.11161 (9)0.92288 (11)0.0183 (3)
C220.38093 (8)0.11961 (10)0.87722 (11)0.0175 (3)
H220.37160.17940.82810.021*
C230.34884 (9)0.02976 (11)0.80753 (12)0.0217 (3)
H23A0.33180.04720.72480.026*
H23B0.39370.02050.80830.026*
C240.26361 (9)0.05338 (10)0.95763 (11)0.0195 (3)
N40.49557 (7)0.11382 (8)0.72380 (9)0.0177 (2)
N50.52995 (7)0.10439 (8)0.83740 (10)0.0187 (2)
N60.32536 (7)0.11978 (9)0.97243 (10)0.0190 (2)
H2N0.3167 (11)0.1701 (13)1.0160 (15)0.023*
O40.49702 (7)0.11180 (7)1.02703 (8)0.0237 (2)
O50.27691 (6)0.00512 (7)0.86555 (8)0.0210 (2)
O60.20361 (7)0.04052 (8)1.01606 (9)0.0265 (2)
Cl20.67070 (3)0.16703 (4)0.46267 (4)0.04530 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0231 (6)0.0230 (7)0.0154 (6)0.0034 (5)0.0012 (5)0.0008 (5)
C20.0236 (7)0.0340 (8)0.0170 (6)0.0031 (6)0.0061 (5)0.0045 (6)
C30.0251 (7)0.0345 (8)0.0211 (7)0.0055 (6)0.0033 (6)0.0067 (6)
C40.0282 (7)0.0290 (8)0.0204 (7)0.0076 (6)0.0014 (6)0.0001 (6)
C50.0260 (7)0.0269 (7)0.0164 (6)0.0027 (6)0.0045 (5)0.0012 (5)
C60.0197 (6)0.0230 (7)0.0147 (6)0.0012 (5)0.0018 (5)0.0012 (5)
C70.0222 (6)0.0206 (7)0.0169 (6)0.0006 (5)0.0013 (5)0.0021 (5)
C80.0307 (8)0.0293 (8)0.0261 (8)0.0121 (6)0.0041 (6)0.0088 (6)
C90.0189 (6)0.0221 (7)0.0187 (6)0.0005 (5)0.0013 (5)0.0016 (5)
C100.0197 (6)0.0219 (7)0.0132 (6)0.0007 (5)0.0040 (5)0.0010 (5)
C110.0218 (6)0.0223 (7)0.0154 (6)0.0006 (5)0.0046 (5)0.0004 (5)
C120.0209 (6)0.0227 (7)0.0135 (6)0.0000 (5)0.0002 (5)0.0007 (5)
N10.0181 (5)0.0205 (6)0.0184 (5)0.0024 (4)0.0032 (4)0.0011 (4)
N20.0213 (6)0.0225 (6)0.0203 (6)0.0059 (4)0.0051 (4)0.0037 (5)
N30.0268 (6)0.0221 (6)0.0159 (6)0.0040 (5)0.0078 (5)0.0044 (5)
O10.0249 (5)0.0291 (6)0.0267 (5)0.0071 (4)0.0066 (4)0.0015 (4)
O20.0292 (5)0.0225 (5)0.0159 (5)0.0065 (4)0.0053 (4)0.0030 (4)
O30.0270 (5)0.0279 (5)0.0182 (5)0.0059 (4)0.0063 (4)0.0006 (4)
Cl10.03303 (19)0.02462 (18)0.01709 (16)0.00449 (14)0.00523 (13)0.00336 (12)
C130.0289 (7)0.0211 (7)0.0266 (7)0.0107 (6)0.0120 (6)0.0066 (6)
C140.0466 (9)0.0211 (7)0.0206 (7)0.0134 (6)0.0165 (6)0.0050 (6)
C150.0523 (10)0.0204 (7)0.0151 (7)0.0051 (7)0.0032 (6)0.0006 (5)
C160.0377 (8)0.0262 (8)0.0218 (7)0.0027 (6)0.0020 (6)0.0013 (6)
C170.0306 (7)0.0238 (7)0.0182 (7)0.0029 (6)0.0049 (6)0.0023 (5)
C180.0277 (7)0.0161 (6)0.0166 (6)0.0048 (5)0.0064 (5)0.0023 (5)
C190.0215 (6)0.0178 (6)0.0201 (7)0.0016 (5)0.0041 (5)0.0027 (5)
C200.0202 (7)0.0304 (8)0.0224 (7)0.0012 (6)0.0013 (5)0.0031 (6)
C210.0245 (6)0.0142 (6)0.0160 (6)0.0013 (5)0.0006 (5)0.0006 (5)
C220.0216 (6)0.0185 (6)0.0126 (6)0.0020 (5)0.0035 (5)0.0009 (5)
C230.0211 (6)0.0266 (7)0.0180 (6)0.0025 (5)0.0057 (5)0.0056 (5)
C240.0252 (7)0.0195 (6)0.0140 (6)0.0029 (5)0.0030 (5)0.0014 (5)
N40.0217 (5)0.0168 (5)0.0144 (5)0.0009 (4)0.0006 (4)0.0025 (4)
N50.0194 (5)0.0215 (6)0.0148 (5)0.0001 (4)0.0004 (4)0.0030 (4)
N60.0239 (6)0.0193 (6)0.0145 (5)0.0003 (4)0.0053 (4)0.0024 (4)
O40.0289 (5)0.0280 (5)0.0139 (5)0.0018 (4)0.0012 (4)0.0000 (4)
O50.0249 (5)0.0210 (5)0.0179 (5)0.0025 (4)0.0069 (4)0.0034 (4)
O60.0312 (5)0.0274 (5)0.0227 (5)0.0044 (4)0.0127 (4)0.0032 (4)
Cl20.02391 (19)0.0669 (3)0.0474 (3)0.01720 (19)0.01757 (17)0.0329 (2)
Geometric parameters (Å, º) top
C1—C21.384 (2)C13—C141.382 (2)
C1—C61.3978 (18)C13—C181.3904 (19)
C1—Cl11.7426 (14)C13—Cl21.7390 (16)
C2—C31.378 (2)C14—C151.371 (2)
C2—H20.9500C14—H140.9500
C3—C41.389 (2)C15—C161.384 (2)
C3—H30.9500C15—H150.9500
C4—C51.380 (2)C16—C171.382 (2)
C4—H40.9500C16—H160.9500
C5—C61.3962 (19)C17—C181.391 (2)
C5—H50.9500C17—H170.9500
C6—C71.4610 (19)C18—C191.4623 (19)
C7—N11.2779 (18)C19—N41.2770 (17)
C7—H70.9500C19—H190.9500
C8—N21.4515 (18)C20—N51.4505 (17)
C8—H8A0.9800C20—H20A0.9800
C8—H8B0.9800C20—H20B0.9800
C8—H8C0.9800C20—H20C0.9800
C9—O11.2116 (17)C21—O41.2134 (16)
C9—N21.3687 (17)C21—N51.3656 (17)
C9—C101.5262 (19)C21—C221.5275 (19)
C10—N31.4411 (17)C22—N61.4458 (16)
C10—C111.5450 (19)C22—C231.5352 (18)
C10—H101.0000C22—H221.0000
C11—O21.4439 (16)C23—O51.4393 (16)
C11—H11A0.9900C23—H23A0.9900
C11—H11B0.9900C23—H23B0.9900
C12—O31.2164 (16)C24—O61.2116 (17)
C12—N31.3324 (18)C24—N61.3381 (18)
C12—O21.3520 (16)C24—O51.3514 (16)
N1—N21.3736 (15)N4—N51.3707 (15)
N3—H1N0.873 (18)N6—H2N0.869 (18)
C2—C1—C6121.70 (13)C14—C13—C18122.10 (15)
C2—C1—Cl1117.91 (11)C14—C13—Cl2118.24 (12)
C6—C1—Cl1120.38 (11)C18—C13—Cl2119.66 (12)
C3—C2—C1119.34 (13)C15—C14—C13119.63 (14)
C3—C2—H2120.3C15—C14—H14120.2
C1—C2—H2120.3C13—C14—H14120.2
C2—C3—C4120.53 (14)C14—C15—C16119.79 (14)
C2—C3—H3119.7C14—C15—H15120.1
C4—C3—H3119.7C16—C15—H15120.1
C5—C4—C3119.45 (14)C17—C16—C15120.14 (15)
C5—C4—H4120.3C17—C16—H16119.9
C3—C4—H4120.3C15—C16—H16119.9
C4—C5—C6121.57 (13)C16—C17—C18121.24 (14)
C4—C5—H5119.2C16—C17—H17119.4
C6—C5—H5119.2C18—C17—H17119.4
C5—C6—C1117.35 (13)C13—C18—C17117.10 (13)
C5—C6—C7121.79 (12)C13—C18—C19121.23 (13)
C1—C6—C7120.86 (12)C17—C18—C19121.67 (12)
N1—C7—C6120.14 (12)N4—C19—C18119.37 (12)
N1—C7—H7119.9N4—C19—H19120.3
C6—C7—H7119.9C18—C19—H19120.3
N2—C8—H8A109.5N5—C20—H20A109.5
N2—C8—H8B109.5N5—C20—H20B109.5
H8A—C8—H8B109.5H20A—C20—H20B109.5
N2—C8—H8C109.5N5—C20—H20C109.5
H8A—C8—H8C109.5H20A—C20—H20C109.5
H8B—C8—H8C109.5H20B—C20—H20C109.5
O1—C9—N2121.81 (13)O4—C21—N5122.45 (13)
O1—C9—C10121.94 (12)O4—C21—C22122.72 (12)
N2—C9—C10116.24 (11)N5—C21—C22114.83 (11)
N3—C10—C9110.30 (11)N6—C22—C21111.65 (11)
N3—C10—C11101.08 (10)N6—C22—C23101.17 (10)
C9—C10—C11113.46 (11)C21—C22—C23112.94 (11)
N3—C10—H10110.6N6—C22—H22110.3
C9—C10—H10110.6C21—C22—H22110.3
C11—C10—H10110.6C23—C22—H22110.3
O2—C11—C10105.17 (10)O5—C23—C22105.83 (10)
O2—C11—H11A110.7O5—C23—H23A110.6
C10—C11—H11A110.7C22—C23—H23A110.6
O2—C11—H11B110.7O5—C23—H23B110.6
C10—C11—H11B110.7C22—C23—H23B110.6
H11A—C11—H11B108.8H23A—C23—H23B108.7
O3—C12—N3128.80 (13)O6—C24—N6128.58 (13)
O3—C12—O2120.95 (12)O6—C24—O5120.87 (13)
N3—C12—O2110.24 (11)N6—C24—O5110.52 (11)
C7—N1—N2117.21 (12)C19—N4—N5118.38 (11)
C9—N2—N1116.92 (11)C21—N5—N4115.79 (11)
C9—N2—C8120.65 (11)C21—N5—C20121.66 (11)
N1—N2—C8122.24 (11)N4—N5—C20122.40 (11)
C12—N3—C10113.24 (11)C24—N6—C22112.48 (11)
C12—N3—H1N118.6 (11)C24—N6—H2N118.2 (11)
C10—N3—H1N125.5 (11)C22—N6—H2N124.0 (11)
C12—O2—C11109.80 (10)C24—O5—C23109.37 (10)
C6—C1—C2—C31.9 (2)C18—C13—C14—C150.4 (2)
Cl1—C1—C2—C3177.13 (11)Cl2—C13—C14—C15179.40 (11)
C1—C2—C3—C40.3 (2)C13—C14—C15—C160.8 (2)
C2—C3—C4—C51.7 (2)C14—C15—C16—C170.1 (2)
C3—C4—C5—C60.9 (2)C15—C16—C17—C181.0 (2)
C4—C5—C6—C11.2 (2)C14—C13—C18—C170.6 (2)
C4—C5—C6—C7178.07 (14)Cl2—C13—C18—C17178.39 (11)
C2—C1—C6—C52.6 (2)C14—C13—C18—C19178.80 (13)
Cl1—C1—C6—C5176.37 (11)Cl2—C13—C18—C192.26 (19)
C2—C1—C6—C7176.66 (13)C16—C17—C18—C131.2 (2)
Cl1—C1—C6—C74.32 (18)C16—C17—C18—C19178.11 (14)
C5—C6—C7—N19.9 (2)C13—C18—C19—N4167.13 (13)
C1—C6—C7—N1169.41 (13)C17—C18—C19—N413.5 (2)
O1—C9—C10—N31.63 (18)O4—C21—C22—N64.35 (18)
N2—C9—C10—N3178.44 (11)N5—C21—C22—N6175.76 (11)
O1—C9—C10—C11114.20 (14)O4—C21—C22—C23117.57 (14)
N2—C9—C10—C1165.87 (15)N5—C21—C22—C2362.54 (15)
N3—C10—C11—O24.05 (13)N6—C22—C23—O53.89 (13)
C9—C10—C11—O2114.01 (12)C21—C22—C23—O5123.35 (12)
C6—C7—N1—N2178.98 (12)C18—C19—N4—N5178.97 (11)
O1—C9—N2—N1178.75 (13)O4—C21—N5—N4174.42 (12)
C10—C9—N2—N11.31 (18)C22—C21—N5—N45.47 (16)
O1—C9—N2—C83.7 (2)O4—C21—N5—C201.2 (2)
C10—C9—N2—C8176.39 (13)C22—C21—N5—C20178.87 (12)
C7—N1—N2—C9175.91 (12)C19—N4—N5—C21174.24 (12)
C7—N1—N2—C80.91 (19)C19—N4—N5—C201.39 (19)
O3—C12—N3—C10174.04 (14)O6—C24—N6—C22173.57 (14)
O2—C12—N3—C107.14 (16)O5—C24—N6—C228.49 (16)
C9—C10—N3—C12113.51 (13)C21—C22—N6—C24127.83 (12)
C11—C10—N3—C126.81 (15)C23—C22—N6—C247.45 (14)
O3—C12—O2—C11177.11 (12)O6—C24—O5—C23176.42 (13)
N3—C12—O2—C113.97 (15)N6—C24—O5—C235.45 (15)
C10—C11—O2—C120.36 (14)C22—C23—O5—C240.61 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N···O6i0.873 (18)1.990 (18)2.8410 (16)164.7 (16)
N6—H2N···O3ii0.869 (18)2.152 (18)2.9868 (16)161.1 (15)
C8—H8C···Cl2iii0.982.623.5168 (17)153
C11—H11B···O3iv0.992.433.4067 (17)170
C15—H15···O4i0.952.483.1405 (18)127
C16—H16···O10.952.353.214 (2)152
C20—H20B···Cg3v0.982.843.5467 (16)130
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1; (iii) x+1, y, z+1; (iv) x, y+1/2, z+1/2; (v) x+1, y, z+2.
(III) (4S)-N'-[(E)-4-Chlorobenzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide top
Crystal data top
C12H12ClN3O3F(000) = 292
Mr = 281.70Dx = 1.539 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54187 Å
a = 9.274 (4) ÅCell parameters from 900 reflections
b = 4.1096 (18) Åθ = 22.6–68.4°
c = 16.104 (7) ŵ = 2.88 mm1
β = 97.813 (9)°T = 100 K
V = 608.1 (5) Å3Needle, colourless
Z = 20.60 × 0.04 × 0.02 mm
Data collection top
CCD
diffractometer
1934 independent reflections
Radiation source: fine-focus sealed tube1776 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 69.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.277, Tmax = 0.945k = 44
5567 measured reflectionsl = 1919
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)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0378P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1934 reflectionsΔρmax = 0.28 e Å3
176 parametersΔρmin = 0.27 e Å3
1 restraintAbsolute structure: Flack (1983), 526 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.054 (17)
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
C10.6652 (3)0.2819 (8)0.12635 (14)0.0157 (6)
H10.58580.39910.14320.019*
C20.6531 (3)0.1512 (8)0.04637 (15)0.0174 (6)
H20.56620.17870.00830.021*
C30.7699 (3)0.0206 (7)0.02274 (15)0.0156 (6)
C40.8974 (3)0.0623 (7)0.07731 (15)0.0177 (7)
H40.97640.18100.06040.021*
C50.9081 (3)0.0713 (8)0.15672 (15)0.0177 (6)
H50.99560.04520.19430.021*
C60.7925 (3)0.2437 (7)0.18239 (14)0.0147 (7)
C70.8117 (3)0.3926 (7)0.26580 (15)0.0161 (6)
H70.90540.39630.29810.019*
C80.8710 (3)0.6957 (8)0.42061 (16)0.0221 (7)
H8A0.91210.47660.42900.033*
H8B0.86290.79480.47510.033*
H8C0.93470.82910.39070.033*
C90.6101 (2)0.8259 (9)0.39733 (13)0.0153 (6)
C100.4620 (2)0.7264 (7)0.35087 (14)0.0168 (7)
H100.45390.48380.34900.020*
C110.4249 (2)0.8679 (9)0.26145 (14)0.0183 (7)
H11A0.50461.00990.24770.022*
H11B0.40970.69080.21950.022*
C120.2491 (3)1.0320 (8)0.34004 (14)0.0168 (6)
N10.7026 (2)0.5182 (6)0.29560 (12)0.0158 (5)
N20.7272 (2)0.6757 (6)0.37152 (11)0.0145 (5)
N30.3457 (2)0.8615 (7)0.39094 (13)0.0192 (6)
H1N0.335 (3)0.791 (9)0.4426 (17)0.023*
O10.62190 (19)1.0110 (5)0.45697 (11)0.0227 (5)
O20.29284 (18)1.0528 (6)0.26243 (10)0.0207 (5)
O30.13829 (18)1.1634 (6)0.35500 (11)0.0241 (5)
Cl10.75467 (6)0.17898 (18)0.07843 (3)0.02190 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0184 (12)0.0154 (18)0.0142 (10)0.0006 (13)0.0051 (9)0.0017 (13)
C20.0183 (13)0.0187 (18)0.0146 (12)0.0006 (13)0.0001 (10)0.0024 (13)
C30.0203 (13)0.0139 (17)0.0132 (12)0.0040 (12)0.0049 (10)0.0011 (12)
C40.0202 (13)0.0177 (18)0.0160 (12)0.0035 (12)0.0052 (10)0.0012 (12)
C50.0181 (13)0.0190 (18)0.0160 (12)0.0025 (12)0.0024 (10)0.0009 (13)
C60.0177 (12)0.0121 (19)0.0149 (11)0.0024 (11)0.0043 (10)0.0031 (11)
C70.0169 (12)0.0169 (19)0.0141 (11)0.0009 (12)0.0004 (9)0.0013 (12)
C80.0187 (13)0.029 (2)0.0168 (12)0.0000 (13)0.0027 (10)0.0019 (13)
C90.0219 (12)0.0132 (15)0.0108 (10)0.0008 (14)0.0020 (9)0.0044 (14)
C100.0185 (13)0.0170 (19)0.0149 (11)0.0014 (11)0.0017 (10)0.0009 (11)
C110.0167 (12)0.026 (2)0.0117 (10)0.0007 (13)0.0003 (9)0.0002 (14)
C120.0150 (13)0.0210 (18)0.0137 (12)0.0024 (13)0.0007 (10)0.0012 (13)
N10.0192 (11)0.0169 (15)0.0112 (9)0.0020 (10)0.0017 (8)0.0008 (10)
N20.0167 (10)0.0159 (14)0.0103 (9)0.0004 (10)0.0007 (8)0.0023 (10)
N30.0192 (10)0.0260 (17)0.0133 (9)0.0051 (12)0.0052 (8)0.0045 (12)
O10.0277 (10)0.0233 (14)0.0167 (9)0.0015 (9)0.0018 (7)0.0069 (9)
O20.0172 (9)0.0322 (14)0.0129 (8)0.0046 (9)0.0022 (7)0.0076 (9)
O30.0161 (9)0.0322 (14)0.0243 (9)0.0049 (9)0.0038 (7)0.0026 (10)
Cl10.0240 (3)0.0270 (4)0.0145 (3)0.0017 (3)0.0019 (2)0.0037 (4)
Geometric parameters (Å, º) top
C1—C21.386 (3)C8—H8B0.9800
C1—C61.394 (3)C8—H8C0.9800
C1—H10.9500C9—O11.219 (3)
C2—C31.389 (4)C9—N21.362 (3)
C2—H20.9500C9—C101.528 (3)
C3—C41.385 (3)C10—N31.441 (3)
C3—Cl11.742 (3)C10—C111.548 (3)
C4—C51.383 (4)C10—H101.0000
C4—H40.9500C11—O21.444 (3)
C5—C61.394 (4)C11—H11A0.9900
C5—H50.9500C11—H11B0.9900
C6—C71.465 (3)C12—O31.213 (3)
C7—N11.285 (3)C12—N31.329 (4)
C7—H70.9500C12—O21.368 (3)
C8—N21.457 (3)N1—N21.375 (3)
C8—H8A0.9800N3—H1N0.90 (3)
C2—C1—C6120.8 (2)O1—C9—N2122.2 (2)
C2—C1—H1119.6O1—C9—C10122.1 (2)
C6—C1—H1119.6N2—C9—C10115.5 (2)
C1—C2—C3118.9 (2)N3—C10—C9110.8 (2)
C1—C2—H2120.5N3—C10—C11100.77 (19)
C3—C2—H2120.5C9—C10—C11115.2 (2)
C4—C3—C2121.3 (2)N3—C10—H10109.9
C4—C3—Cl1120.0 (2)C9—C10—H10109.9
C2—C3—Cl1118.63 (19)C11—C10—H10109.9
C5—C4—C3119.0 (2)O2—C11—C10105.60 (18)
C5—C4—H4120.5O2—C11—H11A110.6
C3—C4—H4120.5C10—C11—H11A110.6
C4—C5—C6121.0 (2)O2—C11—H11B110.6
C4—C5—H5119.5C10—C11—H11B110.6
C6—C5—H5119.5H11A—C11—H11B108.8
C1—C6—C5118.9 (2)O3—C12—N3129.1 (2)
C1—C6—C7122.2 (2)O3—C12—O2121.2 (2)
C5—C6—C7118.8 (2)N3—C12—O2109.7 (2)
N1—C7—C6120.4 (2)C7—N1—N2118.53 (19)
N1—C7—H7119.8C9—N2—N1116.24 (18)
C6—C7—H7119.8C9—N2—C8121.2 (2)
N2—C8—H8A109.5N1—N2—C8122.5 (2)
N2—C8—H8B109.5C12—N3—C10114.2 (2)
H8A—C8—H8B109.5C12—N3—H1N126.4 (19)
N2—C8—H8C109.5C10—N3—H1N118 (2)
H8A—C8—H8C109.5C12—O2—C11109.56 (19)
H8B—C8—H8C109.5
C6—C1—C2—C30.3 (4)N3—C10—C11—O21.6 (3)
C1—C2—C3—C40.2 (4)C9—C10—C11—O2120.9 (2)
C1—C2—C3—Cl1179.1 (2)C6—C7—N1—N2175.5 (2)
C2—C3—C4—C50.2 (4)O1—C9—N2—N1169.3 (3)
Cl1—C3—C4—C5178.7 (2)C10—C9—N2—N115.3 (4)
C3—C4—C5—C60.5 (4)O1—C9—N2—C88.1 (4)
C2—C1—C6—C50.0 (4)C10—C9—N2—C8167.3 (3)
C2—C1—C6—C7176.8 (3)C7—N1—N2—C9175.2 (3)
C4—C5—C6—C10.4 (4)C7—N1—N2—C82.2 (4)
C4—C5—C6—C7177.3 (3)O3—C12—N3—C10177.2 (3)
C1—C6—C7—N111.8 (4)O2—C12—N3—C104.3 (4)
C5—C6—C7—N1171.4 (3)C9—C10—N3—C12126.0 (3)
O1—C9—C10—N34.0 (4)C11—C10—N3—C123.6 (3)
N2—C9—C10—N3171.4 (2)O3—C12—O2—C11178.4 (3)
O1—C9—C10—C11109.6 (3)N3—C12—O2—C113.0 (3)
N2—C9—C10—C1175.0 (4)C10—C11—O2—C120.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N···O1i0.90 (3)1.98 (3)2.822 (3)155 (3)
C7—H7···O3ii0.952.433.308 (3)154
C8—H8C···O3iii0.982.463.416 (4)164
C10—H10···O2iv1.002.603.398 (4)137
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+1, y1, z; (iii) x+1, y, z; (iv) x, y1, z.
(IV) (4S)-N'-[(E)-2,6-Dichlorobenzylidene]-N,3-dimethyl-2-oxo-1,3-oxazolidine-4-carbohydrazide top
Crystal data top
C13H13Cl2N3O3Dx = 1.543 Mg m3
Mr = 330.16Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212Cell parameters from 10413 reflections
a = 19.7273 (13) Åθ = 3.0–29.1°
b = 7.6749 (3) ŵ = 0.47 mm1
c = 9.3882 (3) ÅT = 100 K
V = 1421.42 (12) Å3Block, colourless
Z = 40.11 × 0.10 × 0.08 mm
F(000) = 680
Data collection top
Rigaku CCD
diffractometer
3655 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 29.1°, θmin = 3.0°
ω scansh = 2622
10592 measured reflectionsk = 810
3782 independent reflectionsl = 812
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)] = 0.023H-atom parameters constrained
wR(F2) = 0.058 w = 1/[σ2(Fo2) + (0.0304P)2 + 0.292P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
3782 reflectionsΔρmax = 0.29 e Å3
192 parametersΔρmin = 0.19 e Å3
0 restraintsAbsolute structure: Flack (1983), 1508 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (4)
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
C10.56269 (6)0.28819 (15)0.65767 (12)0.0142 (2)
C20.62682 (6)0.35432 (16)0.68474 (14)0.0179 (2)
H20.65810.36980.60880.021*
C30.64534 (6)0.39789 (17)0.82297 (15)0.0198 (3)
H30.68860.44790.84100.024*
C40.60086 (6)0.36852 (16)0.93442 (14)0.0181 (2)
H40.61340.39711.02930.022*
C50.53767 (6)0.29675 (15)0.90573 (12)0.0144 (2)
C60.51481 (5)0.25771 (17)0.76648 (11)0.01290 (19)
C70.44566 (6)0.19006 (16)0.74812 (12)0.0135 (2)
H70.42100.15440.83000.016*
C80.31324 (7)0.07201 (19)0.74848 (13)0.0190 (3)
H8A0.31060.17530.80960.029*
H8B0.33550.02290.80040.029*
H8C0.26740.03590.72100.029*
C90.32512 (6)0.09370 (16)0.48747 (13)0.0155 (2)
C100.36982 (7)0.15833 (17)0.36505 (13)0.0144 (2)
H100.41570.10320.36920.017*
C110.37560 (8)0.35994 (17)0.36365 (14)0.0202 (3)
H11A0.35260.41080.44760.024*
H11B0.42370.39650.36440.024*
C120.32291 (6)0.27228 (17)0.15739 (12)0.0155 (2)
C130.33253 (7)0.04779 (18)0.16878 (15)0.0225 (3)
H13A0.30920.12460.23630.034*
H13B0.37800.09350.14960.034*
H13C0.30680.04250.07960.034*
N10.41737 (5)0.17742 (14)0.62559 (11)0.01343 (19)
N20.35225 (5)0.11327 (14)0.62124 (11)0.0146 (2)
N30.33788 (6)0.12566 (15)0.22913 (11)0.0177 (2)
O10.26869 (5)0.03326 (14)0.46844 (10)0.0225 (2)
O20.34298 (5)0.41440 (12)0.23429 (10)0.01758 (19)
O30.29591 (5)0.28803 (14)0.04279 (9)0.0235 (2)
Cl10.545810 (13)0.23992 (4)0.47978 (3)0.01687 (6)
Cl20.485825 (14)0.25546 (5)1.05296 (3)0.01923 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0141 (5)0.0118 (5)0.0168 (5)0.0013 (4)0.0007 (4)0.0008 (4)
C20.0133 (5)0.0157 (6)0.0246 (6)0.0003 (5)0.0012 (5)0.0045 (5)
C30.0126 (5)0.0149 (6)0.0320 (7)0.0008 (5)0.0060 (5)0.0010 (5)
C40.0176 (6)0.0155 (6)0.0212 (6)0.0019 (5)0.0067 (5)0.0014 (4)
C50.0142 (5)0.0136 (5)0.0154 (5)0.0017 (4)0.0004 (4)0.0006 (4)
C60.0121 (5)0.0115 (5)0.0151 (4)0.0012 (5)0.0014 (4)0.0000 (4)
C70.0121 (5)0.0139 (5)0.0146 (5)0.0000 (4)0.0001 (4)0.0004 (4)
C80.0154 (6)0.0259 (7)0.0158 (5)0.0056 (5)0.0027 (5)0.0017 (5)
C90.0127 (5)0.0186 (6)0.0153 (5)0.0017 (4)0.0014 (4)0.0003 (4)
C100.0146 (5)0.0158 (5)0.0127 (5)0.0012 (5)0.0023 (4)0.0004 (4)
C110.0272 (7)0.0158 (6)0.0175 (6)0.0010 (5)0.0067 (5)0.0006 (5)
C120.0107 (4)0.0212 (6)0.0144 (4)0.0024 (5)0.0022 (4)0.0011 (5)
C130.0240 (6)0.0198 (6)0.0238 (6)0.0006 (6)0.0019 (5)0.0084 (5)
N10.0104 (4)0.0142 (4)0.0157 (4)0.0009 (4)0.0008 (4)0.0008 (4)
N20.0103 (4)0.0193 (5)0.0141 (4)0.0023 (4)0.0001 (4)0.0002 (4)
N30.0233 (6)0.0164 (5)0.0133 (5)0.0004 (4)0.0046 (4)0.0025 (4)
O10.0133 (4)0.0346 (6)0.0197 (4)0.0047 (4)0.0023 (3)0.0018 (4)
O20.0206 (5)0.0167 (4)0.0154 (4)0.0027 (4)0.0011 (4)0.0013 (3)
O30.0229 (4)0.0336 (6)0.0138 (4)0.0045 (4)0.0032 (3)0.0032 (4)
Cl10.01605 (12)0.01956 (13)0.01500 (11)0.00092 (12)0.00214 (9)0.00018 (11)
Cl20.01828 (12)0.02584 (15)0.01357 (11)0.00114 (14)0.00100 (9)0.00086 (12)
Geometric parameters (Å, º) top
C1—C21.3866 (17)C9—O11.2192 (15)
C1—C61.4109 (15)C9—N21.3734 (15)
C1—Cl11.7427 (12)C9—C101.5312 (17)
C2—C31.3890 (19)C10—N31.4450 (16)
C2—H20.9500C10—C111.5516 (17)
C3—C41.3840 (19)C10—H101.0000
C3—H30.9500C11—O21.4366 (15)
C4—C51.3891 (17)C11—H11A0.9900
C4—H40.9500C11—H11B0.9900
C5—C61.4150 (15)C12—O31.2066 (14)
C5—Cl21.7485 (12)C12—N31.3444 (16)
C6—C71.4696 (15)C12—O21.3666 (15)
C7—N11.2822 (15)C13—N31.4506 (17)
C7—H70.9500C13—H13A0.9800
C8—N21.4558 (15)C13—H13B0.9800
C8—H8A0.9800C13—H13C0.9800
C8—H8B0.9800N1—N21.3763 (14)
C8—H8C0.9800
C2—C1—C6122.60 (11)N3—C10—C9110.82 (11)
C2—C1—Cl1115.33 (9)N3—C10—C11101.40 (11)
C6—C1—Cl1122.05 (9)C9—C10—C11111.82 (11)
C1—C2—C3119.96 (12)N3—C10—H10110.8
C1—C2—H2120.0C9—C10—H10110.8
C3—C2—H2120.0C11—C10—H10110.8
C4—C3—C2120.02 (12)O2—C11—C10105.33 (11)
C4—C3—H3120.0O2—C11—H11A110.7
C2—C3—H3120.0C10—C11—H11A110.7
C3—C4—C5119.14 (12)O2—C11—H11B110.7
C3—C4—H4120.4C10—C11—H11B110.7
C5—C4—H4120.4H11A—C11—H11B108.8
C4—C5—C6123.31 (11)O3—C12—N3128.87 (13)
C4—C5—Cl2116.33 (9)O3—C12—O2121.27 (12)
C6—C5—Cl2120.36 (9)N3—C12—O2109.86 (9)
C1—C6—C5114.86 (10)N3—C13—H13A109.5
C1—C6—C7126.51 (10)N3—C13—H13B109.5
C5—C6—C7118.62 (10)H13A—C13—H13B109.5
N1—C7—C6122.41 (10)N3—C13—H13C109.5
N1—C7—H7118.8H13A—C13—H13C109.5
C6—C7—H7118.8H13B—C13—H13C109.5
N2—C8—H8A109.5C7—N1—N2117.38 (10)
N2—C8—H8B109.5C9—N2—N1115.47 (10)
H8A—C8—H8B109.5C9—N2—C8121.36 (10)
N2—C8—H8C109.5N1—N2—C8123.15 (10)
H8A—C8—H8C109.5C12—N3—C10113.14 (10)
H8B—C8—H8C109.5C12—N3—C13123.81 (11)
O1—C9—N2122.11 (11)C10—N3—C13122.41 (11)
O1—C9—C10122.62 (11)C12—O2—C11110.13 (9)
N2—C9—C10115.25 (10)
C6—C1—C2—C31.83 (19)N3—C10—C11—O23.53 (15)
Cl1—C1—C2—C3179.70 (10)C9—C10—C11—O2114.60 (11)
C1—C2—C3—C42.70 (19)C6—C7—N1—N2179.59 (11)
C2—C3—C4—C50.56 (19)O1—C9—N2—N1177.75 (12)
C3—C4—C5—C62.61 (19)C10—C9—N2—N14.09 (15)
C3—C4—C5—Cl2177.46 (10)O1—C9—N2—C83.64 (19)
C2—C1—C6—C51.12 (17)C10—C9—N2—C8174.52 (11)
Cl1—C1—C6—C5177.26 (9)C7—N1—N2—C9176.87 (11)
C2—C1—C6—C7179.28 (12)C7—N1—N2—C84.55 (17)
Cl1—C1—C6—C72.34 (18)O3—C12—N3—C10179.38 (12)
C4—C5—C6—C13.36 (18)O2—C12—N3—C100.46 (14)
Cl2—C5—C6—C1176.71 (9)O3—C12—N3—C139.6 (2)
C4—C5—C6—C7177.00 (11)O2—C12—N3—C13170.52 (12)
Cl2—C5—C6—C72.93 (16)C9—C10—N3—C12116.32 (12)
C1—C6—C7—N111.65 (19)C11—C10—N3—C122.53 (15)
C5—C6—C7—N1168.76 (12)C9—C10—N3—C1372.56 (15)
O1—C9—C10—N34.09 (17)C11—C10—N3—C13168.60 (13)
N2—C9—C10—N3177.76 (11)O3—C12—O2—C11178.05 (11)
O1—C9—C10—C11108.25 (15)N3—C12—O2—C112.10 (13)
N2—C9—C10—C1169.90 (15)C10—C11—O2—C123.56 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.423.2627 (16)148
C4—H4···O2ii0.952.563.4538 (16)158
C8—H8A···O3iii0.982.373.2404 (16)147
C8—H8C···O2iv0.982.413.3147 (17)154
C8—H8B···Cg2v0.982.853.7289 (15)149
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1, y+1, z+1; (iii) x, y, z+1; (iv) x+1/2, y1/2, z+1; (v) x+1, y, z.
 

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