#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/21/2202172.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_2202172
loop_
_publ_author_name
'Li, Xiao-Fang'
'Feng, Ya-Qing'
'Xu, Mian'
_publ_section_title
4-(4-Chlorophenyl)-3-(2,6-dichlorophenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-en-6-one
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o675
_journal_page_last               o676
_journal_paper_doi               10.1107/S1600536803008134
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C18 H12 Cl3 N O3'
_chemical_formula_moiety         'C18 H12 Cl3 N O3'
_chemical_formula_sum            'C18 H12 Cl3 N O3'
_chemical_formula_weight         396.64
_chemical_name_systematic
; 4-[(2-Chloro-phenyl)-hydroxyimino-methyl]
-1,5-dimethyl-2-phenyl-pyrazolidin-3-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 104.768(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.600(6)
_cell_length_b                   20.177(9)
_cell_length_c                   14.202(6)
_cell_measurement_reflns_used    699
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.33
_cell_measurement_theta_min      3.46
_cell_volume                     3491(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8872
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.870243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.084P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                1702
_reflns_number_total             3078
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6021.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2202172
_cod_database_fobs_code          2202172
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.45260(11) 0.81182(7) 0.10115(10) 0.1227(6) Uani d . 1 . . Cl
Cl2 0.29602(8) 1.06152(5) 0.03211(8) 0.0728(3) Uani d . 1 . . Cl
Cl3 0.14847(11) 0.72810(6) 0.37502(8) 0.1041(5) Uani d . 1 . . Cl
N1 0.2605(2) 0.88569(14) -0.0668(2) 0.0563(8) Uani d . 1 . . N
O1 0.14935(18) 0.86562(11) -0.10339(15) 0.0555(6) Uani d . 1 . . O
O2 0.0619(2) 1.01248(12) -0.10202(17) 0.0648(7) Uani d . 1 . . O
O3 -0.06824(18) 0.93826(12) -0.16235(16) 0.0581(6) Uani d . 1 . . O
C1 0.0289(3) 0.95672(19) -0.1037(2) 0.0462(8) Uani d . 1 . . C
C2 0.0836(2) 0.89728(15) -0.0444(2) 0.0419(8) Uani d . 1 . . C
C3 -0.0145(3) 0.85400(17) -0.0456(2) 0.0538(9) Uani d . 1 . . C
H3A -0.0481 0.8658 0.0064 0.065 Uiso calc R 1 . . H
H3B 0.0055 0.8075 -0.0399 0.065 Uiso calc R 1 . . H
C4 -0.0904(3) 0.86942(18) -0.1452(2) 0.0587(10) Uani d . 1 . . C
H4A -0.0742 0.8411 -0.1949 0.070 Uiso calc R 1 . . H
H4B -0.1667 0.8633 -0.1447 0.070 Uiso calc R 1 . . H
C5 0.1672(2) 0.91561(15) 0.0506(2) 0.0414(8) Uani d . 1 . . C
H5 0.1538 0.9610 0.0694 0.050 Uiso calc R 1 . . H
C6 0.2717(3) 0.91360(16) 0.0158(2) 0.0449(8) Uani d . 1 . . C
C7 0.1693(3) 0.86894(16) 0.1344(2) 0.0440(8) Uani d . 1 . . C
C8 0.1894(3) 0.80186(18) 0.1277(3) 0.0649(11) Uani d . 1 . . C
H8 0.2068 0.7858 0.0721 0.078 Uiso calc R 1 . . H
C9 0.1842(3) 0.75841(18) 0.2008(3) 0.0692(11) Uani d . 1 . . C
H9 0.1971 0.7134 0.1948 0.083 Uiso calc R 1 . . H
C10 0.1594(3) 0.78275(19) 0.2830(3) 0.0604(10) Uani d . 1 . . C
C11 0.1409(3) 0.84868(18) 0.2926(2) 0.0524(9) Uani d . 1 . . C
H11 0.1251 0.8645 0.3490 0.063 Uiso calc R 1 . . H
C12 0.1458(2) 0.89165(17) 0.2187(2) 0.0439(8) Uani d . 1 . . C
H12 0.1330 0.9366 0.2255 0.053 Uiso calc R 1 . . H
C13 0.3805(3) 0.9388(2) 0.0696(2) 0.0513(9) Uani d . 1 . . C
C14 0.4688(3) 0.8968(2) 0.1099(3) 0.0713(12) Uani d . 1 . . C
C15 0.5703(4) 0.9211(3) 0.1568(3) 0.0883(15) Uani d . 1 . . C
H15 0.6278 0.8921 0.1827 0.106 Uiso calc R 1 . . H
C16 0.5864(3) 0.9879(3) 0.1653(3) 0.0863(16) Uani d . 1 . . C
H16 0.6553 1.0042 0.1970 0.104 Uiso calc R 1 . . H
C17 0.5026(4) 1.0315(2) 0.1280(3) 0.0737(12) Uani d . 1 . . C
H17 0.5140 1.0770 0.1341 0.088 Uiso calc R 1 . . H
C18 0.4008(3) 1.0063(2) 0.0810(2) 0.0563(10) Uani d . 1 . . C
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
_geom_angle_publ_flag
C6 N1 O1 109.2(2) y
N1 O1 C2 108.3(2) y
C1 O3 C4 110.2(3) y
O2 C1 O3 121.9(3) y
O2 C1 C2 128.4(3) ?
O3 C1 C2 109.6(3) ?
O1 C2 C3 108.8(3) ?
O1 C2 C1 105.6(2) ?
C3 C2 C1 101.2(3) ?
O1 C2 C5 104.3(2) y
C3 C2 C5 121.8(3) ?
C1 C2 C5 114.2(3) ?
C2 C3 C4 102.2(3) ?
C2 C3 H3A 111.3 ?
C4 C3 H3A 111.3 ?
C2 C3 H3B 111.3 ?
C4 C3 H3B 111.3 ?
H3A C3 H3B 109.2 ?
O3 C4 C3 104.4(3) ?
O3 C4 H4A 110.9 ?
C3 C4 H4A 110.9 ?
O3 C4 H4B 110.9 ?
C3 C4 H4B 110.9 ?
H4A C4 H4B 108.9 ?
C7 C5 C6 113.4(3) ?
C7 C5 C2 114.4(3) ?
C6 C5 C2 99.5(2) ?
C7 C5 H5 109.7 ?
C6 C5 H5 109.7 ?
C2 C5 H5 109.7 ?
N1 C6 C13 119.8(3) ?
N1 C6 C5 114.2(3) ?
C13 C6 C5 126.0(3) ?
C12 C7 C8 117.8(3) ?
C12 C7 C5 120.7(3) ?
C8 C7 C5 121.4(3) ?
C9 C8 C7 121.8(3) ?
C9 C8 H8 119.1 ?
C7 C8 H8 119.1 ?
C8 C9 C10 118.6(3) ?
C8 C9 H9 120.7 ?
C10 C9 H9 120.7 ?
C11 C10 C9 121.0(3) ?
C11 C10 Cl3 119.7(3) ?
C9 C10 Cl3 119.3(3) ?
C10 C11 C12 119.9(3) ?
C10 C11 H11 120.1 ?
C12 C11 H11 120.1 ?
C11 C12 C7 120.9(3) ?
C11 C12 H12 119.6 ?
C7 C12 H12 119.6 ?
C18 C13 C14 116.3(3) ?
C18 C13 C6 121.0(3) ?
C14 C13 C6 122.6(4) ?
C15 C14 C13 121.9(4) ?
C15 C14 Cl1 117.9(4) ?
C13 C14 Cl1 120.3(3) ?
C16 C15 C14 119.6(4) ?
C16 C15 H15 120.2 ?
C14 C15 H15 120.2 ?
C15 C16 C17 121.1(4) ?
C15 C16 H16 119.5 ?
C17 C16 H16 119.5 ?
C16 C17 C18 118.6(4) ?
C16 C17 H17 120.7 ?
C18 C17 H17 120.7 ?
C17 C18 C13 122.5(4) ?
C17 C18 Cl2 118.4(3) ?
C13 C18 Cl2 119.1(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C14 . 1.728(5) ?
Cl2 C18 . 1.731(4) ?
Cl3 C10 . 1.742(4) y
N1 C6 . 1.276(4) y
N1 O1 . 1.423(3) y
O1 C2 . 1.466(3) y
O2 C1 . 1.197(4) y
O3 C1 . 1.345(4) y
O3 C4 . 1.450(4) ?
C1 C2 . 1.526(4) ?
C2 C3 . 1.511(4) ?
C2 C5 . 1.531(4) ?
C3 C4 . 1.524(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C7 . 1.513(4) ?
C5 C6 . 1.520(4) ?
C5 H5 . 0.9800 ?
C6 C13 . 1.479(4) ?
C7 C12 . 1.383(4) ?
C7 C8 . 1.384(4) ?
C8 C9 . 1.373(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.374(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.363(5) ?
C11 C12 . 1.374(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C18 . 1.389(5) ?
C13 C14 . 1.399(5) ?
C14 C15 . 1.373(5) ?
C15 C16 . 1.365(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.373(6) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.383(5) ?
C17 H17 . 0.9300 ?
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
_geom_torsion_publ_flag
C6 N1 O1 C2 12.6(3) y
C4 O3 C1 O2 -176.5(3) ?
C4 O3 C1 C2 3.2(3) ?
N1 O1 C2 C3 -152.1(2) ?
N1 O1 C2 C1 99.9(3) ?
N1 O1 C2 C5 -20.7(3) ?
O2 C1 C2 O1 -90.8(4) ?
O3 C1 C2 O1 89.5(3) y
O2 C1 C2 C3 155.9(3) ?
O3 C1 C2 C3 -23.8(3) ?
O2 C1 C2 C5 23.2(5) ?
O3 C1 C2 C5 -156.5(2) ?
O1 C2 C3 C4 -77.7(3) ?
C1 C2 C3 C4 33.2(3) ?
C5 C2 C3 C4 161.1(3) ?
C1 O3 C4 C3 18.8(3) ?
C2 C3 C4 O3 -32.7(3) ?
O1 C2 C5 C7 -101.6(3) ?
C3 C2 C5 C7 21.7(4) ?
C1 C2 C5 C7 143.7(3) ?
O1 C2 C5 C6 19.6(3) ?
C3 C2 C5 C6 142.9(3) ?
C1 C2 C5 C6 -95.1(3) ?
O1 N1 C6 C13 179.7(3) ?
O1 N1 C6 C5 1.4(4) ?
C7 C5 C6 N1 108.2(3) ?
C2 C5 C6 N1 -13.7(4) ?
C7 C5 C6 C13 -70.0(4) ?
C2 C5 C6 C13 168.1(3) ?
C6 C5 C7 C12 127.7(3) ?
C2 C5 C7 C12 -119.1(3) ?
C6 C5 C7 C8 -55.5(4) ?
C2 C5 C7 C8 57.6(4) ?
C12 C7 C8 C9 1.3(5) ?
C5 C7 C8 C9 -175.5(3) ?
C7 C8 C9 C10 -0.7(6) ?
C8 C9 C10 C11 -0.4(6) ?
C8 C9 C10 Cl3 178.1(3) ?
C9 C10 C11 C12 0.8(6) ?
Cl3 C10 C11 C12 -177.8(2) ?
C10 C11 C12 C7 -0.1(5) ?
C8 C7 C12 C11 -0.9(5) ?
C5 C7 C12 C11 175.9(3) ?
N1 C6 C13 C18 110.3(4) ?
C5 C6 C13 C18 -71.6(4) ?
N1 C6 C13 C14 -68.3(4) ?
C5 C6 C13 C14 109.8(4) ?
C18 C13 C14 C15 -0.9(5) ?
C6 C13 C14 C15 177.8(3) ?
C18 C13 C14 Cl1 179.3(3) ?
C6 C13 C14 Cl1 -2.0(5) ?
C13 C14 C15 C16 0.3(6) ?
Cl1 C14 C15 C16 -179.9(3) ?
C14 C15 C16 C17 0.2(6) ?
C15 C16 C17 C18 -0.1(6) ?
C16 C17 C18 C13 -0.5(5) ?
C16 C17 C18 Cl2 -178.9(3) ?
C14 C13 C18 C17 1.0(5) ?
C6 C13 C18 C17 -177.7(3) ?
C14 C13 C18 Cl2 179.3(2) ?
C6 C13 C18 Cl2 0.6(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139065880
