#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/96/2239645.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239645
loop_
_publ_author_name
'Cho, Seonghwa'
'Kim, Jineun'
'Lee, Sangjin'
'Kim, Tae Ho'
_publ_section_title
;
 Vinclozolin:
 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-1,3-oxazolidine-2,4-dione
;
_journal_coeditor_code           SJ5407
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o754
_journal_paper_doi               10.1107/S1600536814012781
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H9 Cl2 N O3'
_chemical_formula_moiety         'C12 H9 Cl2 N O3'
_chemical_formula_sum            'C12 H9 Cl2 N O3'
_chemical_formula_weight         286.10
_chemical_name_common
;
Vinclozolin
;
_chemical_name_systematic
;
3-(3,5-Dichlorophenyl)-5-ethenyl-5-methyl-1,3-oxazolidine-2,4-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.916(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0727(12)
_cell_length_b                   5.2947(5)
_cell_length_c                   15.5390(12)
_cell_measurement_reflns_used    4964
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.08
_cell_measurement_theta_min      2.67
_cell_volume                     1217.66(18)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2010)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7915
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.8743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0581P)²+0.9965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                1720
_reflns_number_total             2103
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5407sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               2239645
_cod_database_fobs_code          2239645
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.01684(5) 0.22311(15) 0.42408(5) 0.0385(2) Uani d . 1 1
Cl Cl2 -0.16975(5) 0.99394(15) 0.25170(5) 0.0376(2) Uani d . 1 1
O O1 0.19649(12) 0.9720(4) 0.22124(12) 0.0290(5) Uani d . 1 1
O O2 0.06758(13) 0.2867(4) 0.06863(13) 0.0359(5) Uani d . 1 1
O O3 0.23229(11) 0.7650(3) 0.10675(11) 0.0240(4) Uani d . 1 1
N N1 0.11223(13) 0.6312(4) 0.15799(13) 0.0229(5) Uani d . 1 1
C C1 0.06127(17) 0.4411(5) 0.28171(17) 0.0255(6) Uani d . 1 1
H H1 0.1090 0.3216 0.2872 0.031 Uiso calc R 1 1
C C2 0.00147(18) 0.4404(5) 0.33904(17) 0.0259(6) Uani d . 1 1
C C3 -0.06989(17) 0.6085(6) 0.33076(17) 0.0274(6) Uani d . 1 1
H H3 -0.1110 0.6039 0.3702 0.033 Uiso calc R 1 1
C C4 -0.07979(17) 0.7832(5) 0.26364(17) 0.0271(6) Uani d . 1 1
C C5 -0.02013(17) 0.7960(5) 0.20586(17) 0.0262(6) Uani d . 1 1
H H5 -0.0268 0.9199 0.1609 0.031 Uiso calc R 1 1
C C6 0.04936(16) 0.6214(5) 0.21620(16) 0.0233(6) Uani d . 1 1
C C7 0.18216(17) 0.8082(5) 0.16778(16) 0.0224(6) Uani d . 1 1
C C8 0.11644(17) 0.4631(5) 0.09092(17) 0.0259(6) Uani d . 1 1
C C9 0.19567(18) 0.5543(5) 0.04975(17) 0.0258(6) Uani d . 1 1
C C10 0.1611(2) 0.6600(7) -0.04096(18) 0.0392(8) Uani d . 1 1
H H10A 0.1145 0.7872 -0.0380 0.059 Uiso calc R 1 1
H H10B 0.1352 0.5231 -0.0803 0.059 Uiso calc R 1 1
H H10C 0.2111 0.7381 -0.0633 0.059 Uiso calc R 1 1
C C11 0.26703(18) 0.3557(6) 0.05662(18) 0.0297(7) Uani d . 1 1
H H11 0.2954 0.3018 0.1135 0.036 Uiso calc R 1 1
C C12 0.2928(3) 0.2518(8) -0.0106(2) 0.0583(10) Uani d . 1 1
H H12A 0.2657 0.3016 -0.0683 0.070 Uiso calc R 1 1
H H12B 0.3386 0.1262 -0.0019 0.070 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O3 C9 111.06(18)
C8 N1 C7 111.9(2)
C8 N1 C6 125.8(2)
C7 N1 C6 122.2(2)
C2 C1 C6 117.9(2)
C2 C1 H1 121.1
C6 C1 H1 121.1
C1 C2 C3 121.9(2)
C1 C2 Cl1 118.9(2)
C3 C2 Cl1 119.2(2)
C4 C3 C2 118.2(2)
C4 C3 H3 120.9
C2 C3 H3 120.9
C3 C4 C5 122.1(3)
C3 C4 Cl2 118.8(2)
C5 C4 Cl2 119.2(2)
C6 C5 C4 117.5(3)
C6 C5 H5 121.3
C4 C5 H5 121.3
C1 C6 C5 122.5(2)
C1 C6 N1 118.8(2)
C5 C6 N1 118.7(2)
O1 C7 O3 124.4(2)
O1 C7 N1 126.7(2)
O3 C7 N1 108.9(2)
O2 C8 N1 127.3(2)
O2 C8 C9 127.4(2)
N1 C8 C9 105.2(2)
O3 C9 C11 108.0(2)
O3 C9 C10 107.8(2)
C11 C9 C10 116.3(2)
O3 C9 C8 102.78(19)
C11 C9 C8 110.8(2)
C10 C9 C8 110.2(2)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C9 124.0(3)
C12 C11 H11 118.0
C9 C11 H11 118.0
C11 C12 H12A 120.0
C11 C12 H12B 120.0
H12A C12 H12B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.734(3)
Cl2 C4 1.739(3)
O1 C7 1.192(3)
O2 C8 1.199(3)
O3 C7 1.340(3)
O3 C9 1.466(3)
N1 C8 1.381(3)
N1 C7 1.397(3)
N1 C6 1.430(3)
C1 C2 1.382(4)
C1 C6 1.382(4)
C1 H1 0.9500
C2 C3 1.383(4)
C3 C4 1.381(4)
C3 H3 0.9500
C4 C5 1.388(4)
C5 C6 1.383(4)
C5 H5 0.9500
C8 C9 1.536(4)
C9 C11 1.494(4)
C9 C10 1.515(4)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.303(4)
C11 H11 0.9500
C12 H12A 0.9500
C12 H12B 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1 O1 1_545 0.95 2.59 3.454(3) 151
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.8(4)
C6 C1 C2 Cl1 -177.9(2)
C1 C2 C3 C4 -1.0(4)
Cl1 C2 C3 C4 178.7(2)
C2 C3 C4 C5 -0.8(4)
C2 C3 C4 Cl2 179.4(2)
C3 C4 C5 C6 1.7(4)
Cl2 C4 C5 C6 -178.5(2)
C2 C1 C6 C5 -0.8(4)
C2 C1 C6 N1 177.9(2)
C4 C5 C6 C1 -0.8(4)
C4 C5 C6 N1 -179.6(2)
C8 N1 C6 C1 74.6(3)
C7 N1 C6 C1 -100.6(3)
C8 N1 C6 C5 -106.7(3)
C7 N1 C6 C5 78.2(3)
C9 O3 C7 O1 -178.6(2)
C9 O3 C7 N1 1.6(3)
C8 N1 C7 O1 -178.4(3)
C6 N1 C7 O1 -2.6(4)
C8 N1 C7 O3 1.4(3)
C6 N1 C7 O3 177.2(2)
C7 N1 C8 O2 177.7(3)
C6 N1 C8 O2 2.1(4)
C7 N1 C8 C9 -3.6(3)
C6 N1 C8 C9 -179.2(2)
C7 O3 C9 C11 -120.7(2)
C7 O3 C9 C10 112.9(2)
C7 O3 C9 C8 -3.6(3)
O2 C8 C9 O3 -177.1(3)
N1 C8 C9 O3 4.2(3)
O2 C8 C9 C11 -61.9(4)
N1 C8 C9 C11 119.3(2)
O2 C8 C9 C10 68.3(4)
N1 C8 C9 C10 -110.5(3)
O3 C9 C11 C12 -129.1(3)
C10 C9 C11 C12 -7.9(4)
C8 C9 C11 C12 119.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 780355
