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#$Date: 2023-02-02 11:42:35 +0200 (Thu, 02 Feb 2023) $
#$Revision: 280763 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/66/8106673.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106673
loop_
_publ_author_name
'Hong, Zhi'
'Zhao, Sha-sha'
'Pan, Hong'
'Jin, Qian'
'Tang, Xiao-qin'
'Liu, Jun-li'
_publ_section_title
;
 Crystal structure of
 3-cyclohexyl-2-(cyclohexylimino)-2,3-dihydro-6,8-diiodo-4H-1,3-benzoxazin-4-one,
 C20H24I2N2O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              773
_journal_page_last               774
_journal_paper_doi               10.1515/ncrs-2017-0027
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C20 H24 I2 N2 O2'
_chemical_formula_sum            'C20 H24 I2 N2 O2'
_chemical_formula_weight         578.21
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.8990(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.5052(10)
_cell_length_b                   12.7846(7)
_cell_length_c                   9.4663(5)
_cell_measurement_reflns_used    4119
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.34
_cell_volume                     2110.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II area-detector diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18798
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    2.996
_exptl_absorpt_correction_T_max  0.5097
_exptl_absorpt_correction_T_min  0.4668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         1.588
_refine_diff_density_min         -1.491
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+2.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                4119
_reflns_number_total             4763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0027_suppl.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106673
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.607746(15) 0.08603(2) 0.04186(3) 0.04630(10) Uani 1 1 d . . .
I2 I 0.361425(15) 0.18745(3) 0.42753(4) 0.05878(12) Uani 1 1 d . . .
O1 O 0.69760(14) 0.0655(2) 0.3435(3) 0.0361(5) Uani 1 1 d . . .
O2 O 0.64463(17) 0.1270(3) 0.7404(3) 0.0567(8) Uani 1 1 d . . .
N1 N 0.73514(16) 0.0976(2) 0.5860(3) 0.0327(6) Uani 1 1 d . . .
N2 N 0.81591(16) 0.0131(2) 0.4407(3) 0.0327(6) Uani 1 1 d . . .
C1 C 0.5264(2) 0.1365(3) 0.5172(4) 0.0376(7) Uani 1 1 d . . .
H1A H 0.5111 0.1480 0.6076 0.045 Uiso 1 1 calc R . .
C2 C 0.47484(19) 0.1443(3) 0.4000(4) 0.0380(8) Uani 1 1 d . . .
C3 C 0.4963(2) 0.1273(3) 0.2643(4) 0.0383(7) Uani 1 1 d . . .
H3A H 0.4604 0.1332 0.1865 0.046 Uiso 1 1 calc R . .
C4 C 0.5717(2) 0.1016(3) 0.2451(4) 0.0350(7) Uani 1 1 d . . .
C5 C 0.62399(19) 0.0930(3) 0.3637(4) 0.0312(7) Uani 1 1 d . . .
C6 C 0.75238(18) 0.0558(2) 0.4556(3) 0.0292(6) Uani 1 1 d . . .
C7 C 0.6610(2) 0.1117(3) 0.6199(4) 0.0371(7) Uani 1 1 d . . .
C8 C 0.60234(19) 0.1110(3) 0.4978(4) 0.0336(7) Uani 1 1 d . . .
C9 C 0.8012(2) 0.1053(3) 0.6961(4) 0.0340(7) Uani 1 1 d . . .
H9A H 0.8476 0.1047 0.6449 0.041 Uiso 1 1 calc R . .
C10 C 0.8073(2) 0.0119(3) 0.7934(4) 0.0411(8) Uani 1 1 d . . .
H10A H 0.8067 -0.0519 0.7379 0.049 Uiso 1 1 calc R . .
H10B H 0.7639 0.0105 0.8505 0.049 Uiso 1 1 calc R . .
C11 C 0.8819(3) 0.0188(3) 0.8896(5) 0.0533(10) Uani 1 1 d . . .
H11A H 0.8839 -0.0383 0.9573 0.064 Uiso 1 1 calc R . .
H11B H 0.9251 0.0116 0.8327 0.064 Uiso 1 1 calc R . .
C12 C 0.8879(3) 0.1215(4) 0.9682(5) 0.0582(12) Uani 1 1 d . . .
H12A H 0.9375 0.1255 1.0223 0.070 Uiso 1 1 calc R . .
H12B H 0.8487 0.1243 1.0346 0.070 Uiso 1 1 calc R . .
C13 C 0.8788(3) 0.2146(3) 0.8697(5) 0.0495(10) Uani 1 1 d . . .
H13A H 0.9208 0.2161 0.8093 0.059 Uiso 1 1 calc R . .
H13B H 0.8806 0.2785 0.9250 0.059 Uiso 1 1 calc R . .
C14 C 0.8028(3) 0.2088(3) 0.7779(5) 0.0461(9) Uani 1 1 d . . .
H14A H 0.7984 0.2672 0.7123 0.055 Uiso 1 1 calc R . .
H14B H 0.7602 0.2118 0.8371 0.055 Uiso 1 1 calc R . .
C15 C 0.83213(19) -0.0297(3) 0.3025(4) 0.0356(7) Uani 1 1 d . . .
H15A H 0.8120 0.0174 0.2266 0.043 Uiso 1 1 calc R . .
C16 C 0.7953(2) -0.1374(3) 0.2820(5) 0.0477(10) Uani 1 1 d . . .
H16A H 0.7405 -0.1312 0.2884 0.057 Uiso 1 1 calc R . .
H16B H 0.8033 -0.1631 0.1880 0.057 Uiso 1 1 calc R . .
C17 C 0.8279(3) -0.2153(3) 0.3914(6) 0.0597(12) Uani 1 1 d . . .
H17A H 0.8047 -0.2833 0.3722 0.072 Uiso 1 1 calc R . .
H17B H 0.8158 -0.1933 0.4849 0.072 Uiso 1 1 calc R . .
C18 C 0.9145(3) -0.2237(4) 0.3881(7) 0.0674(14) Uani 1 1 d . . .
H18A H 0.9348 -0.2710 0.4621 0.081 Uiso 1 1 calc R . .
H18B H 0.9264 -0.2523 0.2976 0.081 Uiso 1 1 calc R . .
C19 C 0.9520(2) -0.1175(4) 0.4096(5) 0.0518(10) Uani 1 1 d . . .
H19A H 0.9445 -0.0922 0.5041 0.062 Uiso 1 1 calc R . .
H19B H 1.0067 -0.1241 0.4022 0.062 Uiso 1 1 calc R . .
C20 C 0.9188(2) -0.0392(3) 0.3011(4) 0.0425(8) Uani 1 1 d . . .
H20A H 0.9312 -0.0607 0.2074 0.051 Uiso 1 1 calc R . .
H20B H 0.9421 0.0287 0.3208 0.051 Uiso 1 1 calc R . .
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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 O1 C6 121.3(3) . .
C7 N1 C6 122.3(3) . .
C7 N1 C9 121.2(3) . .
C6 N1 C9 115.3(3) . .
C6 N2 C15 120.2(3) . .
C2 C1 C8 118.6(3) . .
C2 C1 H1A 120.7 . .
C8 C1 H1A 120.7 . .
C1 C2 C3 121.7(3) . .
C1 C2 I2 118.8(3) . .
C3 C2 I2 119.4(3) . .
C2 C3 C4 119.7(3) . .
C2 C3 H3A 120.1 . .
C4 C3 H3A 120.1 . .
C3 C4 C5 118.7(3) . .
C3 C4 I1 120.7(3) . .
C5 C4 I1 120.5(3) . .
O1 C5 C8 120.7(3) . .
O1 C5 C4 118.1(3) . .
C8 C5 C4 121.2(3) . .
N2 C6 O1 121.2(3) . .
N2 C6 N1 121.6(3) . .
O1 C6 N1 117.2(3) . .
O2 C7 N1 122.9(3) . .
O2 C7 C8 122.0(3) . .
N1 C7 C8 115.0(3) . .
C5 C8 C1 120.1(3) . .
C5 C8 C7 119.7(3) . .
C1 C8 C7 120.1(3) . .
N1 C9 C10 112.6(3) . .
N1 C9 C14 112.9(3) . .
C10 C9 C14 112.2(3) . .
N1 C9 H9A 106.1 . .
C10 C9 H9A 106.1 . .
C14 C9 H9A 106.1 . .
C9 C10 C11 109.3(3) . .
C9 C10 H10A 109.8 . .
C11 C10 H10A 109.8 . .
C9 C10 H10B 109.8 . .
C11 C10 H10B 109.8 . .
H10A C10 H10B 108.3 . .
C12 C11 C10 111.3(4) . .
C12 C11 H11A 109.4 . .
C10 C11 H11A 109.4 . .
C12 C11 H11B 109.4 . .
C10 C11 H11B 109.4 . .
H11A C11 H11B 108.0 . .
C11 C12 C13 112.4(4) . .
C11 C12 H12A 109.1 . .
C13 C12 H12A 109.1 . .
C11 C12 H12B 109.1 . .
C13 C12 H12B 109.1 . .
H12A C12 H12B 107.9 . .
C12 C13 C14 110.8(4) . .
C12 C13 H13A 109.5 . .
C14 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
C14 C13 H13B 109.5 . .
H13A C13 H13B 108.1 . .
C13 C14 C9 107.8(3) . .
C13 C14 H14A 110.1 . .
C9 C14 H14A 110.1 . .
C13 C14 H14B 110.1 . .
C9 C14 H14B 110.1 . .
H14A C14 H14B 108.5 . .
N2 C15 C20 107.8(3) . .
N2 C15 C16 109.7(3) . .
C20 C15 C16 109.7(3) . .
N2 C15 H15A 109.8 . .
C20 C15 H15A 109.8 . .
C16 C15 H15A 109.8 . .
C17 C16 C15 112.1(3) . .
C17 C16 H16A 109.2 . .
C15 C16 H16A 109.2 . .
C17 C16 H16B 109.2 . .
C15 C16 H16B 109.2 . .
H16A C16 H16B 107.9 . .
C16 C17 C18 110.5(4) . .
C16 C17 H17A 109.5 . .
C18 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
C18 C17 H17B 109.5 . .
H17A C17 H17B 108.1 . .
C19 C18 C17 110.8(4) . .
C19 C18 H18A 109.5 . .
C17 C18 H18A 109.5 . .
C19 C18 H18B 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 108.1 . .
C20 C19 C18 111.4(4) . .
C20 C19 H19A 109.3 . .
C18 C19 H19A 109.3 . .
C20 C19 H19B 109.3 . .
C18 C19 H19B 109.3 . .
H19A C19 H19B 108.0 . .
C19 C20 C15 111.8(3) . .
C19 C20 H20A 109.3 . .
C15 C20 H20A 109.3 . .
C19 C20 H20B 109.3 . .
C15 C20 H20B 109.3 . .
H20A C20 H20B 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C4 2.084(4) .
I2 C2 2.098(3) .
O1 C5 1.365(4) .
O1 C6 1.374(4) .
O2 C7 1.215(5) .
N1 C7 1.375(4) .
N1 C6 1.401(4) .
N1 C9 1.493(4) .
N2 C6 1.258(4) .
N2 C15 1.468(4) .
C1 C2 1.373(5) .
C1 C8 1.396(5) .
C1 H1A 0.9300 .
C2 C3 1.386(5) .
C3 C4 1.387(5) .
C3 H3A 0.9300 .
C4 C5 1.391(5) .
C5 C8 1.375(5) .
C7 C8 1.479(5) .
C9 C10 1.506(5) .
C9 C14 1.532(5) .
C9 H9A 0.9800 .
C10 C11 1.529(5) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.509(6) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.511(6) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.527(6) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C20 1.524(5) .
C15 C16 1.526(5) .
C15 H15A 0.9800 .
C16 C17 1.513(7) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.522(7) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.514(7) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.515(6) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
