Weak C-H...O and C-H...[pi] hydrogen bonds and [pi]-[pi] stacking inter­actions in a series of four N'-[(E)-(ar­yl)methyl­idene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazides

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...[pi] and [pi]-[pi] stacking inter­actions, occur in these structures, but there is little conformity between them.

Computing details

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

Crystal data

C12H13N3O3	F(000) = 1040
Mr = 247.26	Dx = 1.427 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.8881 (9) Å	Cell parameters from 10133 reflections
b = 14.0296 (17) Å	θ = 3.1–27.6°
c = 20.810 (3) Å	µ = 0.11 mm^−1
β = 91.749 (7)°	T = 100 K
V = 2301.9 (5) Å^3	Chip, colourless
Z = 8	0.07 × 0.04 × 0.02 mm

Data collection

Rugaku CCD diffractometer	2385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.108
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
ω scans	h = −10→6
21153 measured reflections	k = −18→18
5267 independent reflections	l = −25→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.186	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ^2(Fo^2) + (0.080P)^2] where P = (Fo^2 + 2Fc^2)/3
5267 reflections	(Δ/σ)max < 0.001
333 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9028 (4)	0.6339 (2)	0.42060 (16)	0.0292 (8)
H1	0.9550	0.6078	0.3840	0.035*
C2	0.8429 (4)	0.5745 (2)	0.46741 (16)	0.0319 (8)
H2	0.8546	0.5075	0.4629	0.038*
C3	0.7665 (4)	0.6107 (2)	0.52070 (16)	0.0335 (8)
H3	0.7248	0.5689	0.5525	0.040*
C4	0.7506 (4)	0.7085 (2)	0.52782 (16)	0.0320 (8)
H4	0.6988	0.7341	0.5647	0.038*
C5	0.8106 (4)	0.7688 (2)	0.48105 (15)	0.0286 (8)
H5	0.7996	0.8358	0.4860	0.034*
C6	0.8867 (4)	0.7324 (2)	0.42700 (15)	0.0247 (7)
C7	0.9506 (4)	0.7979 (2)	0.37904 (15)	0.0269 (7)
H7	0.9418	0.8647	0.3857	0.032*
C8	1.0827 (5)	0.93197 (19)	0.29462 (16)	0.0337 (8)
H8A	0.9654	0.9547	0.2961	0.051*
H8B	1.1397	0.9633	0.2591	0.051*
H8C	1.1426	0.9471	0.3353	0.051*
C9	1.1566 (4)	0.7896 (2)	0.23345 (15)	0.0256 (7)
C10	1.1489 (4)	0.6811 (2)	0.23093 (15)	0.0267 (7)
H10	1.1988	0.6531	0.2715	0.032*
C11	0.9681 (4)	0.6431 (2)	0.21806 (15)	0.0300 (8)
H11A	0.9379	0.5959	0.2512	0.036*
H11B	0.8847	0.6958	0.2184	0.036*
C12	1.1301 (5)	0.5990 (2)	0.13464 (16)	0.0312 (8)
N1	1.0180 (3)	0.76675 (16)	0.32839 (12)	0.0256 (6)
N2	1.0833 (3)	0.82943 (16)	0.28472 (12)	0.0255 (6)
N3	1.2335 (4)	0.64422 (18)	0.17600 (13)	0.0315 (7)
H1N	1.344 (5)	0.654 (2)	0.1622 (16)	0.038*
O1	1.2231 (3)	0.83676 (14)	0.19142 (10)	0.0312 (5)
O2	0.9705 (3)	0.59923 (15)	0.15560 (10)	0.0357 (6)
O3	1.1654 (3)	0.56158 (15)	0.08375 (11)	0.0419 (6)
C13	0.8928 (4)	0.8429 (2)	−0.09588 (15)	0.0293 (8)
H13	0.8325	0.8698	−0.0615	0.035*
C14	0.9609 (4)	0.9015 (2)	−0.14116 (15)	0.0306 (8)
H14	0.9493	0.9687	−0.1374	0.037*
C15	1.0457 (4)	0.8637 (2)	−0.19184 (16)	0.0316 (8)
H15	1.0940	0.9047	−0.2227	0.038*
C16	1.0608 (4)	0.7661 (2)	−0.19794 (16)	0.0324 (8)
H16	1.1170	0.7399	−0.2336	0.039*
C17	0.9946 (4)	0.7066 (2)	−0.15245 (14)	0.0279 (8)
H17	1.0058	0.6395	−0.1568	0.033*
C18	0.9110 (4)	0.7443 (2)	−0.09986 (14)	0.0256 (7)
C19	0.8448 (4)	0.6804 (2)	−0.05104 (14)	0.0246 (7)
H19	0.8516	0.6132	−0.0560	0.029*
C20	0.7170 (5)	0.5545 (2)	0.03913 (16)	0.0350 (8)
H20A	0.8351	0.5333	0.0369	0.052*
H20B	0.6537	0.5341	0.0003	0.052*
H20C	0.6656	0.5265	0.0770	0.052*
C21	0.6424 (4)	0.7036 (2)	0.09435 (15)	0.0262 (7)
C22	0.6542 (4)	0.8120 (2)	0.09171 (15)	0.0261 (7)
H22	0.6048	0.8363	0.0500	0.031*
C23	0.8370 (4)	0.8482 (2)	0.10210 (15)	0.0301 (8)
H23A	0.9183	0.7944	0.1024	0.036*
H23B	0.8670	0.8933	0.0676	0.036*
C24	0.6797 (5)	0.9008 (2)	0.18577 (17)	0.0317 (8)
N4	0.7782 (3)	0.71670 (17)	−0.00197 (12)	0.0260 (6)
N5	0.7120 (3)	0.65802 (16)	0.04380 (12)	0.0276 (6)
N6	0.5719 (4)	0.85637 (18)	0.14523 (14)	0.0314 (7)
H2N	0.466 (5)	0.857 (2)	0.1542 (16)	0.038*
O4	0.5786 (3)	0.66074 (14)	0.13891 (11)	0.0325 (6)
O5	0.8399 (3)	0.89520 (14)	0.16334 (10)	0.0335 (6)
O6	0.6516 (3)	0.94059 (15)	0.23570 (11)	0.0417 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0306 (19)	0.0274 (16)	0.0297 (18)	0.0008 (14)	0.0017 (15)	−0.0016 (14)
C2	0.038 (2)	0.0218 (15)	0.036 (2)	−0.0033 (14)	−0.0052 (16)	−0.0005 (14)
C3	0.036 (2)	0.0362 (18)	0.0277 (18)	−0.0107 (16)	−0.0011 (16)	0.0071 (15)
C4	0.032 (2)	0.0346 (18)	0.0293 (18)	−0.0034 (15)	0.0027 (16)	−0.0018 (15)
C5	0.0292 (19)	0.0264 (16)	0.0300 (18)	−0.0002 (14)	−0.0021 (15)	−0.0031 (14)
C6	0.0234 (17)	0.0233 (15)	0.0274 (18)	−0.0019 (13)	0.0011 (14)	0.0006 (13)
C7	0.0314 (19)	0.0219 (15)	0.0273 (18)	−0.0009 (13)	−0.0009 (16)	−0.0028 (13)
C8	0.051 (2)	0.0144 (14)	0.0363 (19)	−0.0035 (15)	0.0045 (17)	−0.0015 (13)
C9	0.0261 (19)	0.0208 (14)	0.0299 (18)	−0.0020 (13)	−0.0008 (15)	0.0026 (14)
C10	0.0319 (19)	0.0216 (15)	0.0268 (18)	0.0014 (13)	0.0052 (15)	0.0022 (13)
C11	0.039 (2)	0.0224 (15)	0.0291 (19)	−0.0035 (14)	0.0037 (16)	−0.0034 (13)
C12	0.042 (2)	0.0213 (15)	0.0309 (19)	0.0035 (15)	0.0060 (17)	0.0034 (15)
N1	0.0300 (16)	0.0215 (12)	0.0252 (15)	−0.0025 (11)	0.0010 (13)	0.0032 (11)
N2	0.0331 (16)	0.0177 (12)	0.0257 (15)	0.0000 (11)	0.0028 (12)	0.0001 (11)
N3	0.0332 (17)	0.0250 (14)	0.0367 (17)	0.0005 (13)	0.0076 (14)	−0.0024 (12)
O1	0.0328 (14)	0.0255 (11)	0.0354 (13)	−0.0018 (10)	0.0047 (11)	0.0039 (10)
O2	0.0393 (16)	0.0319 (12)	0.0358 (13)	−0.0043 (11)	0.0005 (12)	−0.0061 (10)
O3	0.0607 (18)	0.0304 (12)	0.0350 (14)	0.0019 (12)	0.0060 (13)	−0.0066 (11)
C13	0.0328 (19)	0.0284 (16)	0.0268 (18)	−0.0026 (15)	0.0033 (15)	−0.0051 (14)
C14	0.035 (2)	0.0263 (15)	0.0309 (18)	−0.0053 (15)	0.0002 (16)	0.0018 (14)
C15	0.030 (2)	0.0340 (17)	0.0306 (19)	−0.0055 (15)	0.0004 (16)	0.0035 (15)
C16	0.036 (2)	0.0321 (17)	0.0292 (19)	−0.0022 (16)	0.0035 (16)	−0.0021 (15)
C17	0.0260 (19)	0.0272 (16)	0.0303 (19)	−0.0030 (14)	0.0002 (15)	−0.0020 (14)
C18	0.0249 (17)	0.0241 (15)	0.0277 (18)	−0.0030 (13)	−0.0011 (15)	−0.0038 (13)
C19	0.0245 (18)	0.0236 (15)	0.0255 (17)	−0.0021 (13)	−0.0018 (14)	−0.0032 (13)
C20	0.051 (2)	0.0202 (15)	0.034 (2)	−0.0038 (15)	0.0058 (17)	−0.0023 (14)
C21	0.0229 (18)	0.0264 (15)	0.0293 (18)	−0.0011 (13)	0.0024 (15)	0.0027 (14)
C22	0.033 (2)	0.0208 (14)	0.0251 (17)	0.0043 (14)	0.0026 (15)	0.0000 (13)
C23	0.0317 (19)	0.0243 (15)	0.034 (2)	0.0014 (14)	−0.0016 (16)	0.0012 (14)
C24	0.043 (2)	0.0176 (14)	0.035 (2)	−0.0007 (15)	0.0025 (17)	0.0017 (14)
N4	0.0259 (15)	0.0250 (13)	0.0273 (15)	−0.0053 (11)	0.0028 (12)	0.0026 (12)
N5	0.0344 (16)	0.0202 (12)	0.0285 (15)	−0.0015 (12)	0.0035 (13)	0.0010 (11)
N6	0.0332 (17)	0.0295 (14)	0.0319 (16)	0.0019 (14)	0.0054 (14)	−0.0054 (12)
O4	0.0345 (14)	0.0275 (11)	0.0358 (13)	−0.0017 (10)	0.0071 (11)	0.0047 (10)
O5	0.0361 (15)	0.0259 (11)	0.0386 (14)	−0.0058 (10)	0.0012 (11)	−0.0072 (10)
O6	0.0583 (17)	0.0265 (12)	0.0405 (14)	−0.0067 (11)	0.0082 (13)	−0.0122 (11)

Geometric parameters (Å, º)

C1—C2	1.376 (4)	C13—C14	1.373 (4)
C1—C6	1.395 (4)	C13—C18	1.393 (4)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.376 (5)	C14—C15	1.373 (5)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.386 (4)	C15—C16	1.381 (4)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.383 (4)	C16—C17	1.377 (4)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.388 (4)	C17—C18	1.398 (4)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.458 (4)	C18—C19	1.463 (4)
C7—N1	1.272 (4)	C19—N4	1.269 (4)
C7—H7	0.9500	C19—H19	0.9500
C8—N2	1.453 (3)	C20—N5	1.456 (4)
C8—H8A	0.9800	C20—H20A	0.9800
C8—H8B	0.9800	C20—H20B	0.9800
C8—H8C	0.9800	C20—H20C	0.9800
C9—O1	1.228 (4)	C21—O4	1.226 (4)
C9—N2	1.350 (4)	C21—N5	1.361 (4)
C9—C10	1.523 (4)	C21—C22	1.525 (4)
C10—N3	1.438 (4)	C22—N6	1.447 (4)
C10—C11	1.539 (4)	C22—C23	1.538 (5)
C10—H10	1.0000	C22—H22	1.0000
C11—O2	1.439 (4)	C23—O5	1.434 (4)
C11—H11A	0.9900	C23—H23A	0.9900
C11—H11B	0.9900	C23—H23B	0.9900
C12—O3	1.222 (4)	C24—O6	1.206 (4)
C12—N3	1.329 (4)	C24—N6	1.334 (4)
C12—O2	1.345 (4)	C24—O5	1.363 (4)
N1—N2	1.376 (3)	N4—N5	1.374 (3)
N3—H1N	0.93 (4)	N6—H2N	0.86 (4)
C2—C1—C6	119.9 (3)	C14—C13—C18	120.7 (3)
C2—C1—H1	120.1	C14—C13—H13	119.6
C6—C1—H1	120.1	C18—C13—H13	119.6
C3—C2—C1	121.0 (3)	C15—C14—C13	120.4 (3)
C3—C2—H2	119.5	C15—C14—H14	119.8
C1—C2—H2	119.5	C13—C14—H14	119.8
C2—C3—C4	119.7 (3)	C14—C15—C16	120.0 (3)
C2—C3—H3	120.2	C14—C15—H15	120.0
C4—C3—H3	120.2	C16—C15—H15	120.0
C5—C4—C3	119.7 (3)	C17—C16—C15	120.1 (3)
C5—C4—H4	120.2	C17—C16—H16	119.9
C3—C4—H4	120.2	C15—C16—H16	119.9
C4—C5—C6	120.8 (3)	C16—C17—C18	120.5 (3)
C4—C5—H5	119.6	C16—C17—H17	119.8
C6—C5—H5	119.6	C18—C17—H17	119.8
C5—C6—C1	119.0 (3)	C13—C18—C17	118.3 (3)
C5—C6—C7	119.3 (3)	C13—C18—C19	121.8 (3)
C1—C6—C7	121.7 (3)	C17—C18—C19	119.9 (3)
N1—C7—C6	120.8 (3)	N4—C19—C18	118.5 (3)
N1—C7—H7	119.6	N4—C19—H19	120.7
C6—C7—H7	119.6	C18—C19—H19	120.7
N2—C8—H8A	109.5	N5—C20—H20A	109.5
N2—C8—H8B	109.5	N5—C20—H20B	109.5
H8A—C8—H8B	109.5	H20A—C20—H20B	109.5
N2—C8—H8C	109.5	N5—C20—H20C	109.5
H8A—C8—H8C	109.5	H20A—C20—H20C	109.5
H8B—C8—H8C	109.5	H20B—C20—H20C	109.5
O1—C9—N2	122.8 (3)	O4—C21—N5	122.6 (3)
O1—C9—C10	122.1 (3)	O4—C21—C22	122.9 (3)
N2—C9—C10	115.0 (3)	N5—C21—C22	114.5 (3)
N3—C10—C9	111.6 (3)	N6—C22—C21	111.8 (3)
N3—C10—C11	100.8 (2)	N6—C22—C23	101.0 (2)
C9—C10—C11	112.8 (3)	C21—C22—C23	112.5 (3)
N3—C10—H10	110.4	N6—C22—H22	110.4
C9—C10—H10	110.4	C21—C22—H22	110.4
C11—C10—H10	110.4	C23—C22—H22	110.4
O2—C11—C10	105.5 (3)	O5—C23—C22	105.4 (3)
O2—C11—H11A	110.6	O5—C23—H23A	110.7
C10—C11—H11A	110.6	C22—C23—H23A	110.7
O2—C11—H11B	110.6	O5—C23—H23B	110.7
C10—C11—H11B	110.6	C22—C23—H23B	110.7
H11A—C11—H11B	108.8	H23A—C23—H23B	108.8
O3—C12—N3	127.9 (3)	O6—C24—N6	129.1 (4)
O3—C12—O2	121.5 (3)	O6—C24—O5	121.3 (3)
N3—C12—O2	110.6 (3)	N6—C24—O5	109.6 (3)
C7—N1—N2	120.1 (2)	C19—N4—N5	119.5 (2)
C9—N2—N1	115.8 (2)	C21—N5—N4	115.2 (2)
C9—N2—C8	121.7 (3)	C21—N5—C20	122.2 (3)
N1—N2—C8	122.4 (2)	N4—N5—C20	122.7 (3)
C12—N3—C10	113.3 (3)	C24—N6—C22	113.3 (3)
C12—N3—H1N	115 (2)	C24—N6—H2N	118 (2)
C10—N3—H1N	131 (2)	C22—N6—H2N	129 (2)
C12—O2—C11	109.4 (3)	C24—O5—C23	110.0 (2)
C6—C1—C2—C3	0.2 (5)	C18—C13—C14—C15	1.2 (5)
C1—C2—C3—C4	−0.6 (5)	C13—C14—C15—C16	0.9 (5)
C2—C3—C4—C5	0.5 (5)	C14—C15—C16—C17	−1.6 (5)
C3—C4—C5—C6	−0.1 (5)	C15—C16—C17—C18	0.3 (5)
C4—C5—C6—C1	−0.3 (5)	C14—C13—C18—C17	−2.5 (5)
C4—C5—C6—C7	−179.2 (3)	C14—C13—C18—C19	177.8 (3)
C2—C1—C6—C5	0.2 (5)	C16—C17—C18—C13	1.7 (5)
C2—C1—C6—C7	179.1 (3)	C16—C17—C18—C19	−178.5 (3)
C5—C6—C7—N1	−178.6 (3)	C13—C18—C19—N4	−4.3 (4)
C1—C6—C7—N1	2.5 (5)	C17—C18—C19—N4	176.0 (3)
O1—C9—C10—N3	2.4 (4)	O4—C21—C22—N6	−3.8 (4)
N2—C9—C10—N3	−178.4 (3)	N5—C21—C22—N6	177.6 (3)
O1—C9—C10—C11	−110.3 (3)	O4—C21—C22—C23	109.0 (3)
N2—C9—C10—C11	68.9 (4)	N5—C21—C22—C23	−69.6 (3)
N3—C10—C11—O2	−5.7 (3)	N6—C22—C23—O5	8.1 (3)
C9—C10—C11—O2	113.4 (3)	C21—C22—C23—O5	−111.3 (3)
C6—C7—N1—N2	−177.6 (3)	C18—C19—N4—N5	178.6 (3)
O1—C9—N2—N1	−178.5 (3)	O4—C21—N5—N4	−180.0 (3)
C10—C9—N2—N1	2.3 (4)	C22—C21—N5—N4	−1.3 (4)
O1—C9—N2—C8	−1.9 (5)	O4—C21—N5—C20	−0.5 (5)
C10—C9—N2—C8	178.9 (3)	C22—C21—N5—C20	178.1 (3)
C7—N1—N2—C9	178.1 (3)	C19—N4—N5—C21	−179.6 (3)
C7—N1—N2—C8	1.5 (4)	C19—N4—N5—C20	1.0 (4)
O3—C12—N3—C10	179.1 (3)	O6—C24—N6—C22	−176.5 (3)
O2—C12—N3—C10	−0.3 (4)	O5—C24—N6—C22	2.6 (4)
C9—C10—N3—C12	−116.1 (3)	C21—C22—N6—C24	113.1 (3)
C11—C10—N3—C12	3.9 (3)	C23—C22—N6—C24	−6.7 (3)
O3—C12—O2—C11	176.7 (3)	O6—C24—O5—C23	−177.5 (3)
N3—C12—O2—C11	−3.8 (3)	N6—C24—O5—C23	3.3 (3)
C10—C11—O2—C12	6.0 (3)	C22—C23—O5—C24	−7.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···O4^i	0.93 (4)	1.93 (4)	2.861 (4)	174 (3)
N6—H2N···O1^ii	0.86 (4)	2.11 (4)	2.955 (4)	168 (3)
C11—H11A···O6^iii	0.99	2.31	3.154 (4)	143
C14—H14···O5^iv	0.95	2.60	3.296 (4)	130
C19—H19···O3^v	0.95	2.52	3.463 (4)	171
C10—H10···Cg4^vi	1.00	2.81	3.587 (3)	135
C22—H22···Cg2^vii	1.00	2.67	3.512 (3)	142

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+2, −y+2, −z; (v) −x+2, −y+1, −z; (vi) x−1/2, −y+3/2, z+1/2; (vii) x−3/2, −y+3/2, z−1/2.

(II) N'-[(E)-2-Chlorobenzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide

Crystal data

C12H12ClN3O3	F(000) = 1168
Mr = 281.70	Dx = 1.515 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 15.7925 (11) Å	Cell parameters from 38129 reflections
b = 13.7715 (4) Å	θ = 3.2–27.6°
c = 11.3887 (3) Å	µ = 0.32 mm^−1
β = 94.350 (7)°	T = 100 K
V = 2469.8 (2) Å^3	Cut needle, colourless
Z = 8	0.14 × 0.05 × 0.05 mm

Data collection

Rigaku CCD diffractometer	4918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
ω scans	h = −20→20
53991 measured reflections	k = −17→17
5667 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0416P)^2 + 1.0893P] where P = (Fo^2 + 2Fc^2)/3
5667 reflections	(Δ/σ)max = 0.001
351 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.08148 (9)	0.15608 (10)	0.75150 (12)	0.0205 (3)
C2	−0.14794 (9)	0.21323 (11)	0.78375 (12)	0.0246 (3)
H2	−0.1768	0.1974	0.8515	0.030*
C3	−0.17192 (9)	0.29331 (12)	0.71665 (13)	0.0268 (3)
H3	−0.2177	0.3326	0.7381	0.032*
C4	−0.12970 (10)	0.31697 (11)	0.61792 (13)	0.0259 (3)
H4	−0.1454	0.3732	0.5731	0.031*
C5	−0.06473 (9)	0.25811 (11)	0.58545 (12)	0.0229 (3)
H5	−0.0365	0.2740	0.5172	0.028*
C6	−0.03945 (8)	0.17575 (10)	0.65047 (12)	0.0191 (3)
C7	0.02752 (9)	0.11153 (10)	0.61446 (12)	0.0199 (3)
H7	0.0496	0.0621	0.6663	0.024*
C8	0.15138 (10)	−0.01736 (11)	0.56425 (14)	0.0286 (3)
H8A	0.1055	−0.0621	0.5806	0.043*
H8B	0.1746	0.0123	0.6380	0.043*
H8C	0.1964	−0.0531	0.5282	0.043*
C9	0.15298 (8)	0.07315 (10)	0.37916 (12)	0.0199 (3)
C10	0.11701 (8)	0.15820 (10)	0.30531 (11)	0.0181 (3)
H10	0.0546	0.1497	0.2860	0.022*
C11	0.13572 (9)	0.25819 (10)	0.36310 (12)	0.0197 (3)
H11A	0.0826	0.2957	0.3681	0.024*
H11B	0.1636	0.2504	0.4434	0.024*
C12	0.20637 (8)	0.24831 (10)	0.19538 (11)	0.0191 (3)
N1	0.05645 (7)	0.12174 (8)	0.51339 (10)	0.0189 (2)
N2	0.11838 (7)	0.05800 (9)	0.48424 (10)	0.0212 (2)
N3	0.16061 (8)	0.16725 (9)	0.19918 (10)	0.0213 (2)
H1N	0.1711 (11)	0.1198 (13)	0.1517 (16)	0.026*
O1	0.20897 (7)	0.02183 (8)	0.34666 (9)	0.0266 (2)
O2	0.19164 (6)	0.30651 (7)	0.28724 (8)	0.0223 (2)
O3	0.25463 (6)	0.27309 (8)	0.12262 (9)	0.0241 (2)
Cl1	−0.04998 (2)	0.05875 (3)	0.84234 (3)	0.02474 (9)
C13	0.56251 (10)	0.14917 (10)	0.42951 (13)	0.0250 (3)
C14	0.53076 (11)	0.15874 (11)	0.31362 (13)	0.0287 (3)
H14	0.5677	0.1741	0.2542	0.034*
C15	0.44561 (11)	0.14600 (11)	0.28483 (13)	0.0292 (3)
H15	0.4234	0.1517	0.2052	0.035*
C16	0.39207 (11)	0.12482 (11)	0.37209 (13)	0.0288 (3)
H16	0.3330	0.1160	0.3524	0.035*
C17	0.42431 (10)	0.11642 (11)	0.48793 (12)	0.0240 (3)
H17	0.3868	0.1028	0.5472	0.029*
C18	0.51063 (9)	0.12747 (10)	0.51929 (12)	0.0199 (3)
C19	0.54573 (9)	0.11580 (10)	0.64101 (12)	0.0197 (3)
H19	0.6053	0.1098	0.6583	0.024*
C20	0.62059 (9)	0.09449 (11)	0.86619 (13)	0.0245 (3)
H20A	0.6405	0.0337	0.8330	0.037*
H20B	0.6322	0.0937	0.9519	0.037*
H20C	0.6503	0.1494	0.8331	0.037*
C21	0.47414 (9)	0.11161 (9)	0.92288 (11)	0.0183 (3)
C22	0.38093 (8)	0.11961 (10)	0.87722 (11)	0.0175 (3)
H22	0.3716	0.1794	0.8281	0.021*
C23	0.34884 (9)	0.02976 (11)	0.80753 (12)	0.0217 (3)
H23A	0.3318	0.0472	0.7248	0.026*
H23B	0.3937	−0.0205	0.8083	0.026*
C24	0.26361 (9)	0.05338 (10)	0.95763 (11)	0.0195 (3)
N4	0.49557 (7)	0.11382 (8)	0.72380 (9)	0.0177 (2)
N5	0.52995 (7)	0.10439 (8)	0.83740 (10)	0.0187 (2)
N6	0.32536 (7)	0.11978 (9)	0.97243 (10)	0.0190 (2)
H2N	0.3167 (11)	0.1701 (13)	1.0160 (15)	0.023*
O4	0.49702 (7)	0.11180 (7)	1.02703 (8)	0.0237 (2)
O5	0.27691 (6)	−0.00512 (7)	0.86555 (8)	0.0210 (2)
O6	0.20361 (7)	0.04052 (8)	1.01606 (9)	0.0265 (2)
Cl2	0.67070 (3)	0.16703 (4)	0.46267 (4)	0.04530 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0231 (6)	0.0230 (7)	0.0154 (6)	−0.0034 (5)	0.0012 (5)	−0.0008 (5)
C2	0.0236 (7)	0.0340 (8)	0.0170 (6)	−0.0031 (6)	0.0061 (5)	−0.0045 (6)
C3	0.0251 (7)	0.0345 (8)	0.0211 (7)	0.0055 (6)	0.0033 (6)	−0.0067 (6)
C4	0.0282 (7)	0.0290 (8)	0.0204 (7)	0.0076 (6)	0.0014 (6)	−0.0001 (6)
C5	0.0260 (7)	0.0269 (7)	0.0164 (6)	0.0027 (6)	0.0045 (5)	0.0012 (5)
C6	0.0197 (6)	0.0230 (7)	0.0147 (6)	−0.0012 (5)	0.0018 (5)	−0.0012 (5)
C7	0.0222 (6)	0.0206 (7)	0.0169 (6)	−0.0006 (5)	0.0013 (5)	0.0021 (5)
C8	0.0307 (8)	0.0293 (8)	0.0261 (8)	0.0121 (6)	0.0041 (6)	0.0088 (6)
C9	0.0189 (6)	0.0221 (7)	0.0187 (6)	−0.0005 (5)	0.0013 (5)	−0.0016 (5)
C10	0.0197 (6)	0.0219 (7)	0.0132 (6)	−0.0007 (5)	0.0040 (5)	−0.0010 (5)
C11	0.0218 (6)	0.0223 (7)	0.0154 (6)	−0.0006 (5)	0.0046 (5)	−0.0004 (5)
C12	0.0209 (6)	0.0227 (7)	0.0135 (6)	0.0000 (5)	−0.0002 (5)	−0.0007 (5)
N1	0.0181 (5)	0.0205 (6)	0.0184 (5)	0.0024 (4)	0.0032 (4)	0.0011 (4)
N2	0.0213 (6)	0.0225 (6)	0.0203 (6)	0.0059 (4)	0.0051 (4)	0.0037 (5)
N3	0.0268 (6)	0.0221 (6)	0.0159 (6)	−0.0040 (5)	0.0078 (5)	−0.0044 (5)
O1	0.0249 (5)	0.0291 (6)	0.0267 (5)	0.0071 (4)	0.0066 (4)	−0.0015 (4)
O2	0.0292 (5)	0.0225 (5)	0.0159 (5)	−0.0065 (4)	0.0053 (4)	−0.0030 (4)
O3	0.0270 (5)	0.0279 (5)	0.0182 (5)	−0.0059 (4)	0.0063 (4)	−0.0006 (4)
Cl1	0.03303 (19)	0.02462 (18)	0.01709 (16)	−0.00449 (14)	0.00523 (13)	0.00336 (12)
C13	0.0289 (7)	0.0211 (7)	0.0266 (7)	0.0107 (6)	0.0120 (6)	0.0066 (6)
C14	0.0466 (9)	0.0211 (7)	0.0206 (7)	0.0134 (6)	0.0165 (6)	0.0050 (6)
C15	0.0523 (10)	0.0204 (7)	0.0151 (7)	0.0051 (7)	0.0032 (6)	0.0006 (5)
C16	0.0377 (8)	0.0262 (8)	0.0218 (7)	−0.0027 (6)	−0.0020 (6)	0.0013 (6)
C17	0.0306 (7)	0.0238 (7)	0.0182 (7)	−0.0029 (6)	0.0049 (6)	0.0023 (5)
C18	0.0277 (7)	0.0161 (6)	0.0166 (6)	0.0048 (5)	0.0064 (5)	0.0023 (5)
C19	0.0215 (6)	0.0178 (6)	0.0201 (7)	0.0016 (5)	0.0041 (5)	0.0027 (5)
C20	0.0202 (7)	0.0304 (8)	0.0224 (7)	−0.0012 (6)	−0.0013 (5)	0.0031 (6)
C21	0.0245 (6)	0.0142 (6)	0.0160 (6)	−0.0013 (5)	0.0006 (5)	0.0006 (5)
C22	0.0216 (6)	0.0185 (6)	0.0126 (6)	0.0020 (5)	0.0035 (5)	0.0009 (5)
C23	0.0211 (6)	0.0266 (7)	0.0180 (6)	−0.0025 (5)	0.0057 (5)	−0.0056 (5)
C24	0.0252 (7)	0.0195 (6)	0.0140 (6)	0.0029 (5)	0.0030 (5)	0.0014 (5)
N4	0.0217 (5)	0.0168 (5)	0.0144 (5)	0.0009 (4)	0.0006 (4)	0.0025 (4)
N5	0.0194 (5)	0.0215 (6)	0.0148 (5)	−0.0001 (4)	−0.0004 (4)	0.0030 (4)
N6	0.0239 (6)	0.0193 (6)	0.0145 (5)	0.0003 (4)	0.0053 (4)	−0.0024 (4)
O4	0.0289 (5)	0.0280 (5)	0.0139 (5)	−0.0018 (4)	−0.0012 (4)	0.0000 (4)
O5	0.0249 (5)	0.0210 (5)	0.0179 (5)	−0.0025 (4)	0.0069 (4)	−0.0034 (4)
O6	0.0312 (5)	0.0274 (5)	0.0227 (5)	−0.0044 (4)	0.0127 (4)	−0.0032 (4)
Cl2	0.02391 (19)	0.0669 (3)	0.0474 (3)	0.01720 (19)	0.01757 (17)	0.0329 (2)

Geometric parameters (Å, º)

C1—C2	1.384 (2)	C13—C14	1.382 (2)
C1—C6	1.3978 (18)	C13—C18	1.3904 (19)
C1—Cl1	1.7426 (14)	C13—Cl2	1.7390 (16)
C2—C3	1.378 (2)	C14—C15	1.371 (2)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.389 (2)	C15—C16	1.384 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.380 (2)	C16—C17	1.382 (2)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.3962 (19)	C17—C18	1.391 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.4610 (19)	C18—C19	1.4623 (19)
C7—N1	1.2779 (18)	C19—N4	1.2770 (17)
C7—H7	0.9500	C19—H19	0.9500
C8—N2	1.4515 (18)	C20—N5	1.4505 (17)
C8—H8A	0.9800	C20—H20A	0.9800
C8—H8B	0.9800	C20—H20B	0.9800
C8—H8C	0.9800	C20—H20C	0.9800
C9—O1	1.2116 (17)	C21—O4	1.2134 (16)
C9—N2	1.3687 (17)	C21—N5	1.3656 (17)
C9—C10	1.5262 (19)	C21—C22	1.5275 (19)
C10—N3	1.4411 (17)	C22—N6	1.4458 (16)
C10—C11	1.5450 (19)	C22—C23	1.5352 (18)
C10—H10	1.0000	C22—H22	1.0000
C11—O2	1.4439 (16)	C23—O5	1.4393 (16)
C11—H11A	0.9900	C23—H23A	0.9900
C11—H11B	0.9900	C23—H23B	0.9900
C12—O3	1.2164 (16)	C24—O6	1.2116 (17)
C12—N3	1.3324 (18)	C24—N6	1.3381 (18)
C12—O2	1.3520 (16)	C24—O5	1.3514 (16)
N1—N2	1.3736 (15)	N4—N5	1.3707 (15)
N3—H1N	0.873 (18)	N6—H2N	0.869 (18)
C2—C1—C6	121.70 (13)	C14—C13—C18	122.10 (15)
C2—C1—Cl1	117.91 (11)	C14—C13—Cl2	118.24 (12)
C6—C1—Cl1	120.38 (11)	C18—C13—Cl2	119.66 (12)
C3—C2—C1	119.34 (13)	C15—C14—C13	119.63 (14)
C3—C2—H2	120.3	C15—C14—H14	120.2
C1—C2—H2	120.3	C13—C14—H14	120.2
C2—C3—C4	120.53 (14)	C14—C15—C16	119.79 (14)
C2—C3—H3	119.7	C14—C15—H15	120.1
C4—C3—H3	119.7	C16—C15—H15	120.1
C5—C4—C3	119.45 (14)	C17—C16—C15	120.14 (15)
C5—C4—H4	120.3	C17—C16—H16	119.9
C3—C4—H4	120.3	C15—C16—H16	119.9
C4—C5—C6	121.57 (13)	C16—C17—C18	121.24 (14)
C4—C5—H5	119.2	C16—C17—H17	119.4
C6—C5—H5	119.2	C18—C17—H17	119.4
C5—C6—C1	117.35 (13)	C13—C18—C17	117.10 (13)
C5—C6—C7	121.79 (12)	C13—C18—C19	121.23 (13)
C1—C6—C7	120.86 (12)	C17—C18—C19	121.67 (12)
N1—C7—C6	120.14 (12)	N4—C19—C18	119.37 (12)
N1—C7—H7	119.9	N4—C19—H19	120.3
C6—C7—H7	119.9	C18—C19—H19	120.3
N2—C8—H8A	109.5	N5—C20—H20A	109.5
N2—C8—H8B	109.5	N5—C20—H20B	109.5
H8A—C8—H8B	109.5	H20A—C20—H20B	109.5
N2—C8—H8C	109.5	N5—C20—H20C	109.5
H8A—C8—H8C	109.5	H20A—C20—H20C	109.5
H8B—C8—H8C	109.5	H20B—C20—H20C	109.5
O1—C9—N2	121.81 (13)	O4—C21—N5	122.45 (13)
O1—C9—C10	121.94 (12)	O4—C21—C22	122.72 (12)
N2—C9—C10	116.24 (11)	N5—C21—C22	114.83 (11)
N3—C10—C9	110.30 (11)	N6—C22—C21	111.65 (11)
N3—C10—C11	101.08 (10)	N6—C22—C23	101.17 (10)
C9—C10—C11	113.46 (11)	C21—C22—C23	112.94 (11)
N3—C10—H10	110.6	N6—C22—H22	110.3
C9—C10—H10	110.6	C21—C22—H22	110.3
C11—C10—H10	110.6	C23—C22—H22	110.3
O2—C11—C10	105.17 (10)	O5—C23—C22	105.83 (10)
O2—C11—H11A	110.7	O5—C23—H23A	110.6
C10—C11—H11A	110.7	C22—C23—H23A	110.6
O2—C11—H11B	110.7	O5—C23—H23B	110.6
C10—C11—H11B	110.7	C22—C23—H23B	110.6
H11A—C11—H11B	108.8	H23A—C23—H23B	108.7
O3—C12—N3	128.80 (13)	O6—C24—N6	128.58 (13)
O3—C12—O2	120.95 (12)	O6—C24—O5	120.87 (13)
N3—C12—O2	110.24 (11)	N6—C24—O5	110.52 (11)
C7—N1—N2	117.21 (12)	C19—N4—N5	118.38 (11)
C9—N2—N1	116.92 (11)	C21—N5—N4	115.79 (11)
C9—N2—C8	120.65 (11)	C21—N5—C20	121.66 (11)
N1—N2—C8	122.24 (11)	N4—N5—C20	122.40 (11)
C12—N3—C10	113.24 (11)	C24—N6—C22	112.48 (11)
C12—N3—H1N	118.6 (11)	C24—N6—H2N	118.2 (11)
C10—N3—H1N	125.5 (11)	C22—N6—H2N	124.0 (11)
C12—O2—C11	109.80 (10)	C24—O5—C23	109.37 (10)
C6—C1—C2—C3	−1.9 (2)	C18—C13—C14—C15	−0.4 (2)
Cl1—C1—C2—C3	177.13 (11)	Cl2—C13—C14—C15	−179.40 (11)
C1—C2—C3—C4	−0.3 (2)	C13—C14—C15—C16	0.8 (2)
C2—C3—C4—C5	1.7 (2)	C14—C15—C16—C17	−0.1 (2)
C3—C4—C5—C6	−0.9 (2)	C15—C16—C17—C18	−1.0 (2)
C4—C5—C6—C1	−1.2 (2)	C14—C13—C18—C17	−0.6 (2)
C4—C5—C6—C7	178.07 (14)	Cl2—C13—C18—C17	178.39 (11)
C2—C1—C6—C5	2.6 (2)	C14—C13—C18—C19	178.80 (13)
Cl1—C1—C6—C5	−176.37 (11)	Cl2—C13—C18—C19	−2.26 (19)
C2—C1—C6—C7	−176.66 (13)	C16—C17—C18—C13	1.2 (2)
Cl1—C1—C6—C7	4.32 (18)	C16—C17—C18—C19	−178.11 (14)
C5—C6—C7—N1	−9.9 (2)	C13—C18—C19—N4	167.13 (13)
C1—C6—C7—N1	169.41 (13)	C17—C18—C19—N4	−13.5 (2)
O1—C9—C10—N3	−1.63 (18)	O4—C21—C22—N6	−4.35 (18)
N2—C9—C10—N3	178.44 (11)	N5—C21—C22—N6	175.76 (11)
O1—C9—C10—C11	−114.20 (14)	O4—C21—C22—C23	−117.57 (14)
N2—C9—C10—C11	65.87 (15)	N5—C21—C22—C23	62.54 (15)
N3—C10—C11—O2	−4.05 (13)	N6—C22—C23—O5	3.89 (13)
C9—C10—C11—O2	114.01 (12)	C21—C22—C23—O5	123.35 (12)
C6—C7—N1—N2	−178.98 (12)	C18—C19—N4—N5	−178.97 (11)
O1—C9—N2—N1	178.75 (13)	O4—C21—N5—N4	−174.42 (12)
C10—C9—N2—N1	−1.31 (18)	C22—C21—N5—N4	5.47 (16)
O1—C9—N2—C8	3.7 (2)	O4—C21—N5—C20	1.2 (2)
C10—C9—N2—C8	−176.39 (13)	C22—C21—N5—C20	−178.87 (12)
C7—N1—N2—C9	−175.91 (12)	C19—N4—N5—C21	174.24 (12)
C7—N1—N2—C8	−0.91 (19)	C19—N4—N5—C20	−1.39 (19)
O3—C12—N3—C10	174.04 (14)	O6—C24—N6—C22	−173.57 (14)
O2—C12—N3—C10	−7.14 (16)	O5—C24—N6—C22	8.49 (16)
C9—C10—N3—C12	−113.51 (13)	C21—C22—N6—C24	−127.83 (12)
C11—C10—N3—C12	6.81 (15)	C23—C22—N6—C24	−7.45 (14)
O3—C12—O2—C11	−177.11 (12)	O6—C24—O5—C23	176.42 (13)
N3—C12—O2—C11	3.97 (15)	N6—C24—O5—C23	−5.45 (15)
C10—C11—O2—C12	0.36 (14)	C22—C23—O5—C24	0.61 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···O6^i	0.873 (18)	1.990 (18)	2.8410 (16)	164.7 (16)
N6—H2N···O3^ii	0.869 (18)	2.152 (18)	2.9868 (16)	161.1 (15)
C8—H8C···Cl2^iii	0.98	2.62	3.5168 (17)	153
C11—H11B···O3^iv	0.99	2.43	3.4067 (17)	170
C15—H15···O4^i	0.95	2.48	3.1405 (18)	127
C16—H16···O1	0.95	2.35	3.214 (2)	152
C20—H20B···Cg3^v	0.98	2.84	3.5467 (16)	130

Symmetry codes: (i) x, y, z−1; (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

Crystal data

C12H12ClN3O3	F(000) = 292
Mr = 281.70	Dx = 1.539 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54187 Å
a = 9.274 (4) Å	Cell parameters from 900 reflections
b = 4.1096 (18) Å	θ = 22.6–68.4°
c = 16.104 (7) Å	µ = 2.88 mm^−1
β = 97.813 (9)°	T = 100 K
V = 608.1 (5) Å^3	Needle, colourless
Z = 2	0.60 × 0.04 × 0.02 mm

Data collection

CCD diffractometer	1934 independent reflections
Radiation source: fine-focus sealed tube	1776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 69.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.277, Tmax = 0.945	k = −4→4
5567 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0378P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1934 reflections	Δρmax = 0.28 e Å^−3
176 parameters	Δρmin = −0.27 e Å^−3
1 restraint	Absolute structure: Flack (1983), 526 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.054 (17)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6652 (3)	0.2819 (8)	0.12635 (14)	0.0157 (6)
H1	0.5858	0.3991	0.1432	0.019*
C2	0.6531 (3)	0.1512 (8)	0.04637 (15)	0.0174 (6)
H2	0.5662	0.1787	0.0083	0.021*
C3	0.7699 (3)	−0.0206 (7)	0.02274 (15)	0.0156 (6)
C4	0.8974 (3)	−0.0623 (7)	0.07731 (15)	0.0177 (7)
H4	0.9764	−0.1810	0.0604	0.021*
C5	0.9081 (3)	0.0713 (8)	0.15672 (15)	0.0177 (6)
H5	0.9956	0.0452	0.1943	0.021*
C6	0.7925 (3)	0.2437 (7)	0.18239 (14)	0.0147 (7)
C7	0.8117 (3)	0.3926 (7)	0.26580 (15)	0.0161 (6)
H7	0.9054	0.3963	0.2981	0.019*
C8	0.8710 (3)	0.6957 (8)	0.42061 (16)	0.0221 (7)
H8A	0.9121	0.4766	0.4290	0.033*
H8B	0.8629	0.7948	0.4751	0.033*
H8C	0.9347	0.8291	0.3907	0.033*
C9	0.6101 (2)	0.8259 (9)	0.39733 (13)	0.0153 (6)
C10	0.4620 (2)	0.7264 (7)	0.35087 (14)	0.0168 (7)
H10	0.4539	0.4838	0.3490	0.020*
C11	0.4249 (2)	0.8679 (9)	0.26145 (14)	0.0183 (7)
H11A	0.5046	1.0099	0.2477	0.022*
H11B	0.4097	0.6908	0.2195	0.022*
C12	0.2491 (3)	1.0320 (8)	0.34004 (14)	0.0168 (6)
N1	0.7026 (2)	0.5182 (6)	0.29560 (12)	0.0158 (5)
N2	0.7272 (2)	0.6757 (6)	0.37152 (11)	0.0145 (5)
N3	0.3457 (2)	0.8615 (7)	0.39094 (13)	0.0192 (6)
H1N	0.335 (3)	0.791 (9)	0.4426 (17)	0.023*
O1	0.62190 (19)	1.0110 (5)	0.45697 (11)	0.0227 (5)
O2	0.29284 (18)	1.0528 (6)	0.26243 (10)	0.0207 (5)
O3	0.13829 (18)	1.1634 (6)	0.35500 (11)	0.0241 (5)
Cl1	0.75467 (6)	−0.17898 (18)	−0.07843 (3)	0.02190 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0184 (12)	0.0154 (18)	0.0142 (10)	0.0006 (13)	0.0051 (9)	0.0017 (13)
C2	0.0183 (13)	0.0187 (18)	0.0146 (12)	0.0006 (13)	−0.0001 (10)	0.0024 (13)
C3	0.0203 (13)	0.0139 (17)	0.0132 (12)	−0.0040 (12)	0.0049 (10)	0.0011 (12)
C4	0.0202 (13)	0.0177 (18)	0.0160 (12)	0.0035 (12)	0.0052 (10)	0.0012 (12)
C5	0.0181 (13)	0.0190 (18)	0.0160 (12)	0.0025 (12)	0.0024 (10)	0.0009 (13)
C6	0.0177 (12)	0.0121 (19)	0.0149 (11)	−0.0024 (11)	0.0043 (10)	0.0031 (11)
C7	0.0169 (12)	0.0169 (19)	0.0141 (11)	0.0009 (12)	0.0004 (9)	0.0013 (12)
C8	0.0187 (13)	0.029 (2)	0.0168 (12)	0.0000 (13)	−0.0027 (10)	−0.0019 (13)
C9	0.0219 (12)	0.0132 (15)	0.0108 (10)	0.0008 (14)	0.0020 (9)	0.0044 (14)
C10	0.0185 (13)	0.0170 (19)	0.0149 (11)	0.0014 (11)	0.0017 (10)	−0.0009 (11)
C11	0.0167 (12)	0.026 (2)	0.0117 (10)	0.0007 (13)	0.0003 (9)	−0.0002 (14)
C12	0.0150 (13)	0.0210 (18)	0.0137 (12)	−0.0024 (13)	−0.0007 (10)	0.0012 (13)
N1	0.0192 (11)	0.0169 (15)	0.0112 (9)	−0.0020 (10)	0.0017 (8)	−0.0008 (10)
N2	0.0167 (10)	0.0159 (14)	0.0103 (9)	0.0004 (10)	−0.0007 (8)	−0.0023 (10)
N3	0.0192 (10)	0.0260 (17)	0.0133 (9)	0.0051 (12)	0.0052 (8)	0.0045 (12)
O1	0.0277 (10)	0.0233 (14)	0.0167 (9)	−0.0015 (9)	0.0018 (7)	−0.0069 (9)
O2	0.0172 (9)	0.0322 (14)	0.0129 (8)	0.0046 (9)	0.0022 (7)	0.0076 (9)
O3	0.0161 (9)	0.0322 (14)	0.0243 (9)	0.0049 (9)	0.0038 (7)	0.0026 (10)
Cl1	0.0240 (3)	0.0270 (4)	0.0145 (3)	0.0017 (3)	0.0019 (2)	−0.0037 (4)

Geometric parameters (Å, º)

C1—C2	1.386 (3)	C8—H8B	0.9800
C1—C6	1.394 (3)	C8—H8C	0.9800
C1—H1	0.9500	C9—O1	1.219 (3)
C2—C3	1.389 (4)	C9—N2	1.362 (3)
C2—H2	0.9500	C9—C10	1.528 (3)
C3—C4	1.385 (3)	C10—N3	1.441 (3)
C3—Cl1	1.742 (3)	C10—C11	1.548 (3)
C4—C5	1.383 (4)	C10—H10	1.0000
C4—H4	0.9500	C11—O2	1.444 (3)
C5—C6	1.394 (4)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.465 (3)	C12—O3	1.213 (3)
C7—N1	1.285 (3)	C12—N3	1.329 (4)
C7—H7	0.9500	C12—O2	1.368 (3)
C8—N2	1.457 (3)	N1—N2	1.375 (3)
C8—H8A	0.9800	N3—H1N	0.90 (3)
C2—C1—C6	120.8 (2)	O1—C9—N2	122.2 (2)
C2—C1—H1	119.6	O1—C9—C10	122.1 (2)
C6—C1—H1	119.6	N2—C9—C10	115.5 (2)
C1—C2—C3	118.9 (2)	N3—C10—C9	110.8 (2)
C1—C2—H2	120.5	N3—C10—C11	100.77 (19)
C3—C2—H2	120.5	C9—C10—C11	115.2 (2)
C4—C3—C2	121.3 (2)	N3—C10—H10	109.9
C4—C3—Cl1	120.0 (2)	C9—C10—H10	109.9
C2—C3—Cl1	118.63 (19)	C11—C10—H10	109.9
C5—C4—C3	119.0 (2)	O2—C11—C10	105.60 (18)
C5—C4—H4	120.5	O2—C11—H11A	110.6
C3—C4—H4	120.5	C10—C11—H11A	110.6
C4—C5—C6	121.0 (2)	O2—C11—H11B	110.6
C4—C5—H5	119.5	C10—C11—H11B	110.6
C6—C5—H5	119.5	H11A—C11—H11B	108.8
C1—C6—C5	118.9 (2)	O3—C12—N3	129.1 (2)
C1—C6—C7	122.2 (2)	O3—C12—O2	121.2 (2)
C5—C6—C7	118.8 (2)	N3—C12—O2	109.7 (2)
N1—C7—C6	120.4 (2)	C7—N1—N2	118.53 (19)
N1—C7—H7	119.8	C9—N2—N1	116.24 (18)
C6—C7—H7	119.8	C9—N2—C8	121.2 (2)
N2—C8—H8A	109.5	N1—N2—C8	122.5 (2)
N2—C8—H8B	109.5	C12—N3—C10	114.2 (2)
H8A—C8—H8B	109.5	C12—N3—H1N	126.4 (19)
N2—C8—H8C	109.5	C10—N3—H1N	118 (2)
H8A—C8—H8C	109.5	C12—O2—C11	109.56 (19)
H8B—C8—H8C	109.5
C6—C1—C2—C3	0.3 (4)	N3—C10—C11—O2	−1.6 (3)
C1—C2—C3—C4	−0.2 (4)	C9—C10—C11—O2	−120.9 (2)
C1—C2—C3—Cl1	−179.1 (2)	C6—C7—N1—N2	−175.5 (2)
C2—C3—C4—C5	−0.2 (4)	O1—C9—N2—N1	−169.3 (3)
Cl1—C3—C4—C5	178.7 (2)	C10—C9—N2—N1	15.3 (4)
C3—C4—C5—C6	0.5 (4)	O1—C9—N2—C8	8.1 (4)
C2—C1—C6—C5	0.0 (4)	C10—C9—N2—C8	−167.3 (3)
C2—C1—C6—C7	176.8 (3)	C7—N1—N2—C9	175.2 (3)
C4—C5—C6—C1	−0.4 (4)	C7—N1—N2—C8	−2.2 (4)
C4—C5—C6—C7	−177.3 (3)	O3—C12—N3—C10	177.2 (3)
C1—C6—C7—N1	11.8 (4)	O2—C12—N3—C10	−4.3 (4)
C5—C6—C7—N1	−171.4 (3)	C9—C10—N3—C12	126.0 (3)
O1—C9—C10—N3	−4.0 (4)	C11—C10—N3—C12	3.6 (3)
N2—C9—C10—N3	171.4 (2)	O3—C12—O2—C11	−178.4 (3)
O1—C9—C10—C11	109.6 (3)	N3—C12—O2—C11	3.0 (3)
N2—C9—C10—C11	−75.0 (4)	C10—C11—O2—C12	−0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···O1^i	0.90 (3)	1.98 (3)	2.822 (3)	155 (3)
C7—H7···O3^ii	0.95	2.43	3.308 (3)	154
C8—H8C···O3^iii	0.98	2.46	3.416 (4)	164
C10—H10···O2^iv	1.00	2.60	3.398 (4)	137

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x+1, y−1, z; (iii) x+1, y, z; (iv) x, y−1, z.

(IV) (4S)-N'-[(E)-2,6-Dichlorobenzylidene]-N,3-dimethyl-2-oxo-1,3-oxazolidine-4-carbohydrazide

Crystal data

C13H13Cl2N3O3	Dx = 1.543 Mg m^−3
Mr = 330.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 10413 reflections
a = 19.7273 (13) Å	θ = 3.0–29.1°
b = 7.6749 (3) Å	µ = 0.47 mm^−1
c = 9.3882 (3) Å	T = 100 K
V = 1421.42 (12) Å^3	Block, colourless
Z = 4	0.11 × 0.10 × 0.08 mm
F(000) = 680

Data collection

Rigaku CCD diffractometer	3655 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 29.1°, θmin = 3.0°
ω scans	h = −26→22
10592 measured reflections	k = −8→10
3782 independent reflections	l = −8→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.058	w = 1/[σ^2(Fo^2) + (0.0304P)^2 + 0.292P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
3782 reflections	Δρmax = 0.29 e Å^−3
192 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1508 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.56269 (6)	0.28819 (15)	0.65767 (12)	0.0142 (2)
C2	0.62682 (6)	0.35432 (16)	0.68474 (14)	0.0179 (2)
H2	0.6581	0.3698	0.6088	0.021*
C3	0.64534 (6)	0.39789 (17)	0.82297 (15)	0.0198 (3)
H3	0.6886	0.4479	0.8410	0.024*
C4	0.60086 (6)	0.36852 (16)	0.93442 (14)	0.0181 (2)
H4	0.6134	0.3971	1.0293	0.022*
C5	0.53767 (6)	0.29675 (15)	0.90573 (12)	0.0144 (2)
C6	0.51481 (5)	0.25771 (17)	0.76648 (11)	0.01290 (19)
C7	0.44566 (6)	0.19006 (16)	0.74812 (12)	0.0135 (2)
H7	0.4210	0.1544	0.8300	0.016*
C8	0.31324 (7)	0.07201 (19)	0.74848 (13)	0.0190 (3)
H8A	0.3106	0.1753	0.8096	0.029*
H8B	0.3355	−0.0229	0.8004	0.029*
H8C	0.2674	0.0359	0.7210	0.029*
C9	0.32512 (6)	0.09370 (16)	0.48747 (13)	0.0155 (2)
C10	0.36982 (7)	0.15833 (17)	0.36505 (13)	0.0144 (2)
H10	0.4157	0.1032	0.3692	0.017*
C11	0.37560 (8)	0.35994 (17)	0.36365 (14)	0.0202 (3)
H11A	0.3526	0.4108	0.4476	0.024*
H11B	0.4237	0.3965	0.3644	0.024*
C12	0.32291 (6)	0.27228 (17)	0.15739 (12)	0.0155 (2)
C13	0.33253 (7)	−0.04779 (18)	0.16878 (15)	0.0225 (3)
H13A	0.3092	−0.1246	0.2363	0.034*
H13B	0.3780	−0.0935	0.1496	0.034*
H13C	0.3068	−0.0425	0.0796	0.034*
N1	0.41737 (5)	0.17742 (14)	0.62559 (11)	0.01343 (19)
N2	0.35225 (5)	0.11327 (14)	0.62124 (11)	0.0146 (2)
N3	0.33788 (6)	0.12566 (15)	0.22913 (11)	0.0177 (2)
O1	0.26869 (5)	0.03326 (14)	0.46844 (10)	0.0225 (2)
O2	0.34298 (5)	0.41440 (12)	0.23429 (10)	0.01758 (19)
O3	0.29591 (5)	0.28803 (14)	0.04279 (9)	0.0235 (2)
Cl1	0.545810 (13)	0.23992 (4)	0.47978 (3)	0.01687 (6)
Cl2	0.485825 (14)	0.25546 (5)	1.05296 (3)	0.01923 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0141 (5)	0.0118 (5)	0.0168 (5)	0.0013 (4)	−0.0007 (4)	0.0008 (4)
C2	0.0133 (5)	0.0157 (6)	0.0246 (6)	0.0003 (5)	0.0012 (5)	0.0045 (5)
C3	0.0126 (5)	0.0149 (6)	0.0320 (7)	−0.0008 (5)	−0.0060 (5)	0.0010 (5)
C4	0.0176 (6)	0.0155 (6)	0.0212 (6)	0.0019 (5)	−0.0067 (5)	−0.0014 (4)
C5	0.0142 (5)	0.0136 (5)	0.0154 (5)	0.0017 (4)	−0.0004 (4)	−0.0006 (4)
C6	0.0121 (5)	0.0115 (5)	0.0151 (4)	0.0012 (5)	−0.0014 (4)	0.0000 (4)
C7	0.0121 (5)	0.0139 (5)	0.0146 (5)	0.0000 (4)	0.0001 (4)	0.0004 (4)
C8	0.0154 (6)	0.0259 (7)	0.0158 (5)	−0.0056 (5)	0.0027 (5)	−0.0017 (5)
C9	0.0127 (5)	0.0186 (6)	0.0153 (5)	0.0017 (4)	−0.0014 (4)	−0.0003 (4)
C10	0.0146 (5)	0.0158 (5)	0.0127 (5)	0.0012 (5)	−0.0023 (4)	−0.0004 (4)
C11	0.0272 (7)	0.0158 (6)	0.0175 (6)	0.0010 (5)	−0.0067 (5)	−0.0006 (5)
C12	0.0107 (4)	0.0212 (6)	0.0144 (4)	0.0024 (5)	0.0022 (4)	0.0011 (5)
C13	0.0240 (6)	0.0198 (6)	0.0238 (6)	0.0006 (6)	−0.0019 (5)	−0.0084 (5)
N1	0.0104 (4)	0.0142 (4)	0.0157 (4)	−0.0009 (4)	−0.0008 (4)	0.0008 (4)
N2	0.0103 (4)	0.0193 (5)	0.0141 (4)	−0.0023 (4)	−0.0001 (4)	0.0002 (4)
N3	0.0233 (6)	0.0164 (5)	0.0133 (5)	0.0004 (4)	−0.0046 (4)	−0.0025 (4)
O1	0.0133 (4)	0.0346 (6)	0.0197 (4)	−0.0047 (4)	−0.0023 (3)	−0.0018 (4)
O2	0.0206 (5)	0.0167 (4)	0.0154 (4)	0.0027 (4)	−0.0011 (4)	0.0013 (3)
O3	0.0229 (4)	0.0336 (6)	0.0138 (4)	0.0045 (4)	−0.0032 (3)	0.0032 (4)
Cl1	0.01605 (12)	0.01956 (13)	0.01500 (11)	−0.00092 (12)	0.00214 (9)	0.00018 (11)
Cl2	0.01828 (12)	0.02584 (15)	0.01357 (11)	0.00114 (14)	−0.00100 (9)	−0.00086 (12)

Geometric parameters (Å, º)

C1—C2	1.3866 (17)	C9—O1	1.2192 (15)
C1—C6	1.4109 (15)	C9—N2	1.3734 (15)
C1—Cl1	1.7427 (12)	C9—C10	1.5312 (17)
C2—C3	1.3890 (19)	C10—N3	1.4450 (16)
C2—H2	0.9500	C10—C11	1.5516 (17)
C3—C4	1.3840 (19)	C10—H10	1.0000
C3—H3	0.9500	C11—O2	1.4366 (15)
C4—C5	1.3891 (17)	C11—H11A	0.9900
C4—H4	0.9500	C11—H11B	0.9900
C5—C6	1.4150 (15)	C12—O3	1.2066 (14)
C5—Cl2	1.7485 (12)	C12—N3	1.3444 (16)
C6—C7	1.4696 (15)	C12—O2	1.3666 (15)
C7—N1	1.2822 (15)	C13—N3	1.4506 (17)
C7—H7	0.9500	C13—H13A	0.9800
C8—N2	1.4558 (15)	C13—H13B	0.9800
C8—H8A	0.9800	C13—H13C	0.9800
C8—H8B	0.9800	N1—N2	1.3763 (14)
C8—H8C	0.9800
C2—C1—C6	122.60 (11)	N3—C10—C9	110.82 (11)
C2—C1—Cl1	115.33 (9)	N3—C10—C11	101.40 (11)
C6—C1—Cl1	122.05 (9)	C9—C10—C11	111.82 (11)
C1—C2—C3	119.96 (12)	N3—C10—H10	110.8
C1—C2—H2	120.0	C9—C10—H10	110.8
C3—C2—H2	120.0	C11—C10—H10	110.8
C4—C3—C2	120.02 (12)	O2—C11—C10	105.33 (11)
C4—C3—H3	120.0	O2—C11—H11A	110.7
C2—C3—H3	120.0	C10—C11—H11A	110.7
C3—C4—C5	119.14 (12)	O2—C11—H11B	110.7
C3—C4—H4	120.4	C10—C11—H11B	110.7
C5—C4—H4	120.4	H11A—C11—H11B	108.8
C4—C5—C6	123.31 (11)	O3—C12—N3	128.87 (13)
C4—C5—Cl2	116.33 (9)	O3—C12—O2	121.27 (12)
C6—C5—Cl2	120.36 (9)	N3—C12—O2	109.86 (9)
C1—C6—C5	114.86 (10)	N3—C13—H13A	109.5
C1—C6—C7	126.51 (10)	N3—C13—H13B	109.5
C5—C6—C7	118.62 (10)	H13A—C13—H13B	109.5
N1—C7—C6	122.41 (10)	N3—C13—H13C	109.5
N1—C7—H7	118.8	H13A—C13—H13C	109.5
C6—C7—H7	118.8	H13B—C13—H13C	109.5
N2—C8—H8A	109.5	C7—N1—N2	117.38 (10)
N2—C8—H8B	109.5	C9—N2—N1	115.47 (10)
H8A—C8—H8B	109.5	C9—N2—C8	121.36 (10)
N2—C8—H8C	109.5	N1—N2—C8	123.15 (10)
H8A—C8—H8C	109.5	C12—N3—C10	113.14 (10)
H8B—C8—H8C	109.5	C12—N3—C13	123.81 (11)
O1—C9—N2	122.11 (11)	C10—N3—C13	122.41 (11)
O1—C9—C10	122.62 (11)	C12—O2—C11	110.13 (9)
N2—C9—C10	115.25 (10)
C6—C1—C2—C3	−1.83 (19)	N3—C10—C11—O2	3.53 (15)
Cl1—C1—C2—C3	179.70 (10)	C9—C10—C11—O2	−114.60 (11)
C1—C2—C3—C4	2.70 (19)	C6—C7—N1—N2	−179.59 (11)
C2—C3—C4—C5	−0.56 (19)	O1—C9—N2—N1	177.75 (12)
C3—C4—C5—C6	−2.61 (19)	C10—C9—N2—N1	−4.09 (15)
C3—C4—C5—Cl2	177.46 (10)	O1—C9—N2—C8	−3.64 (19)
C2—C1—C6—C5	−1.12 (17)	C10—C9—N2—C8	174.52 (11)
Cl1—C1—C6—C5	177.26 (9)	C7—N1—N2—C9	−176.87 (11)
C2—C1—C6—C7	179.28 (12)	C7—N1—N2—C8	4.55 (17)
Cl1—C1—C6—C7	−2.34 (18)	O3—C12—N3—C10	−179.38 (12)
C4—C5—C6—C1	3.36 (18)	O2—C12—N3—C10	0.46 (14)
Cl2—C5—C6—C1	−176.71 (9)	O3—C12—N3—C13	9.6 (2)
C4—C5—C6—C7	−177.00 (11)	O2—C12—N3—C13	−170.52 (12)
Cl2—C5—C6—C7	2.93 (16)	C9—C10—N3—C12	116.32 (12)
C1—C6—C7—N1	−11.65 (19)	C11—C10—N3—C12	−2.53 (15)
C5—C6—C7—N1	168.76 (12)	C9—C10—N3—C13	−72.56 (15)
O1—C9—C10—N3	−4.09 (17)	C11—C10—N3—C13	168.60 (13)
N2—C9—C10—N3	177.76 (11)	O3—C12—O2—C11	−178.05 (11)
O1—C9—C10—C11	108.25 (15)	N3—C12—O2—C11	2.10 (13)
N2—C9—C10—C11	−69.90 (15)	C10—C11—O2—C12	−3.56 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.95	2.42	3.2627 (16)	148
C4—H4···O2^ii	0.95	2.56	3.4538 (16)	158
C8—H8A···O3^iii	0.98	2.37	3.2404 (16)	147
C8—H8C···O2^iv	0.98	2.41	3.3147 (17)	154
C8—H8B···Cg2^v	0.98	2.85	3.7289 (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, y−1/2, −z+1; (v) −x+1, −y, z.