#------------------------------------------------------------------------------
#$Date: 2022-11-30 10:12:31 +0200 (Wed, 30 Nov 2022) $
#$Revision: 279638 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106298.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_8106298
loop_
_publ_author_name
'Ren, Zong-Li'
'Wei, Zhi-Li'
'Wang, Lan'
'Ma, Jian-Chun'
'Dong, Wen-Kui'
_publ_section_title
;
 Synthesis and crystal structure of
 2,2′-ethylenedioxybis(benzimide)-2,2′-bis[O-(1-propyloxyamide)]oxime-4,4′,6,6′-tetrachlorodiphenol,
 C36H34Cl4N4O8
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              795
_journal_page_last               797
_journal_paper_doi               10.1515/ncrs-2017-0419
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C36 H34 Cl4 N4 O8'
_chemical_formula_sum            'C36 H34 Cl4 N4 O8'
_chemical_formula_weight         792.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 133.30(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.048(10)
_cell_length_b                   6.4688(7)
_cell_length_c                   24.301(7)
_cell_measurement_reflns_used    3312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.01
_cell_volume                     3781(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXTL (Bruker, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8189
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         3.259
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_crystal_colour            'clear light green'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3701
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.03P)²+1.22P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2195
_reflns_number_total             3701
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0419_suppl.cif
_cod_data_source_block           D458
_cod_original_cell_volume        3781(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8106298
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.930
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.15219(11) 1.4807(4) 0.59708(13) 0.0671(7) Uani 1 1 d . . . . .
C2 C 0.16715(11) 1.6609(4) 0.58401(13) 0.0706(8) Uani 1 1 d . . . . .
C3 C 0.12762(11) 1.7811(4) 0.52123(13) 0.0700(8) Uani 1 1 d . . . . .
H3 H 0.138040 1.902154 0.513084 0.084 Uiso 1 1 calc R U . . .
C4 C 0.07230(11) 1.7207(4) 0.47035(13) 0.0686(7) Uani 1 1 d . U . . .
C5 C 0.05695(11) 1.5413(4) 0.48281(13) 0.0661(7) Uani 1 1 d . . . . .
H5 H 0.019819 1.501223 0.448730 0.079 Uiso 1 1 calc R U . . .
C6 C 0.09656(11) 1.4208(4) 0.54577(13) 0.0654(7) Uani 1 1 d . U . . .
C7 C 0.07855(11) 1.2414(4) 0.55704(13) 0.0686(7) Uani 1 1 d . U . . .
H7 H 0.041398 1.201844 0.520972 0.082 Uiso 1 1 calc R U . . .
C8 C 0.12879(11) 0.8751(4) 0.68994(14) 0.0734(8) Uani 1 1 d . . . . .
H8A H 0.142845 0.972804 0.729936 0.088 Uiso 1 1 calc R U . . .
H8B H 0.159698 0.822844 0.697226 0.088 Uiso 1 1 calc R U . . .
C9 C 0.09822(12) 0.7004(4) 0.68934(14) 0.0721(8) Uani 1 1 d . . . . .
H9A H 0.068162 0.755368 0.683525 0.086 Uiso 1 1 calc R U . . .
H9B H 0.082349 0.609006 0.647063 0.086 Uiso 1 1 calc R U . . .
C10 C 0.13741(12) 0.5838(4) 0.76117(14) 0.0795(9) Uani 1 1 d . . . . .
H10A H 0.167218 0.524009 0.767312 0.095 Uiso 1 1 calc R U . . .
H10B H 0.153318 0.672191 0.804155 0.095 Uiso 1 1 calc R U . . .
C11 C 0.11024(11) 0.1593(4) 0.81554(14) 0.0667(7) Uani 1 1 d . . . . .
H11 H 0.073114 0.138763 0.771719 0.080 Uiso 1 1 calc R U . . .
C12 C 0.13708(11) 0.0218(4) 0.87881(13) 0.0628(7) Uani 1 1 d . . . . .
C13 C 0.19006(11) 0.0630(4) 0.94719(13) 0.0701(8) Uani 1 1 d . . . . .
H13 H 0.208270 0.182056 0.952557 0.084 Uiso 1 1 calc R U . . .
C14 C 0.21584(12) -0.0674(4) 1.00646(15) 0.0823(9) Uani 1 1 d . . . . .
H14 H 0.251862 -0.039185 1.051751 0.099 Uiso 1 1 calc R U . . .
C15 C 0.18842(12) -0.2452(4) 0.99986(15) 0.0772(8) Uani 1 1 d . . . . .
H15 H 0.205713 -0.333207 1.040948 0.093 Uiso 1 1 calc R U . . .
C16 C 0.13548(11) -0.2879(4) 0.93168(14) 0.0703(7) Uani 1 1 d . . . . .
H16 H 0.117310 -0.406612 0.926704 0.084 Uiso 1 1 calc R U . . .
C17 C 0.10915(11) -0.1557(4) 0.87061(13) 0.0638(7) Uani 1 1 d . . . . .
C18 C 0.02580(10) -0.3597(3) 0.78907(13) 0.0684(7) Uani 1 1 d . . . . .
H18A H 0.046015 -0.486772 0.801013 0.082 Uiso 1 1 calc R U . . .
H18B H 0.018632 -0.349508 0.821579 0.082 Uiso 1 1 calc R U . . .
Cl1 Cl 0.02396(3) 1.86723(10) 0.39303(4) 0.0821(3) Uani 1 1 d . U . . .
Cl2 Cl 0.23595(3) 1.73453(10) 0.64494(3) 0.0831(3) Uani 1 1 d . . . . .
N1 N 0.11391(10) 1.1325(3) 0.61766(11) 0.0703(6) Uani 1 1 d . . . . .
N2 N 0.13647(9) 0.3057(3) 0.81918(11) 0.0692(6) Uani 1 1 d . . . . .
O1 O 0.19343(8) 1.3770(3) 0.66015(9) 0.0780(6) Uani 1 1 d . . . . .
H1B H 0.184842 1.256410 0.671146 0.094 Uiso 1 1 d R U . . .
O2 O 0.08888(8) 0.9685(3) 0.61861(9) 0.0751(5) Uani 1 1 d . . . . .
O3 O 0.10232(8) 0.4216(2) 0.75305(9) 0.0739(5) Uani 1 1 d . . . . .
O4 O 0.05793(7) -0.1844(2) 0.80077(9) 0.0692(5) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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
O1 C1 C2 116.2(2) . .
O1 C1 C6 124.6(2) . .
C2 C1 C6 119.2(2) . .
C3 C2 C1 120.7(2) . .
C3 C2 Cl2 119.0(2) . .
C1 C2 Cl2 120.2(2) . .
C4 C3 C2 119.8(3) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C3 C4 C5 119.9(2) . .
C3 C4 Cl1 119.7(2) . .
C5 C4 Cl1 120.4(2) . .
C6 C5 C4 120.3(3) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C1 120.0(2) . .
C5 C6 C7 118.1(3) . .
C1 C6 C7 121.8(2) . .
N1 C7 C6 119.8(2) . .
N1 C7 H7 120.1 . .
C6 C7 H7 120.1 . .
O2 C8 C9 104.7(2) . .
O2 C8 H8A 110.8 . .
C9 C8 H8A 110.8 . .
O2 C8 H8B 110.8 . .
C9 C8 H8B 110.8 . .
H8A C8 H8B 108.9 . .
C10 C9 C8 109.4(2) . .
C10 C9 H9A 109.8 . .
C8 C9 H9A 109.8 . .
C10 C9 H9B 109.8 . .
C8 C9 H9B 109.8 . .
H9A C9 H9B 108.3 . .
O3 C10 C9 103.5(2) . .
O3 C10 H10A 111.1 . .
C9 C10 H10A 111.1 . .
O3 C10 H10B 111.1 . .
C9 C10 H10B 111.1 . .
H10A C10 H10B 109.0 . .
N2 C11 C12 120.3(2) . .
N2 C11 H11 119.8 . .
C12 C11 H11 119.8 . .
C13 C12 C17 119.8(2) . .
C13 C12 C11 120.7(2) . .
C17 C12 C11 119.5(2) . .
C14 C13 C12 120.9(3) . .
C14 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C13 C14 C15 120.2(3) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C16 C15 C14 119.2(3) . .
C16 C15 H15 120.4 . .
C14 C15 H15 120.4 . .
C17 C16 C15 120.7(3) . .
C17 C16 H16 119.7 . .
C15 C16 H16 119.7 . .
O4 C17 C16 125.7(2) . .
O4 C17 C12 115.2(2) . .
C16 C17 C12 119.1(2) . .
C18 C18 O4 107.82(19) 2_556 .
C18 C18 H18A 110.1 2_556 .
O4 C18 H18A 110.1 . .
C18 C18 H18B 110.1 2_556 .
O4 C18 H18B 110.1 . .
H18A C18 H18B 108.5 . .
C7 N1 O2 111.1(2) . .
C11 N2 O3 110.8(2) . .
C1 O1 H1B 118.5 . .
N1 O2 C8 106.87(19) . .
N2 O3 C10 106.81(19) . .
C17 O4 C18 118.20(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.338(3) .
C1 C2 1.385(4) .
C1 C6 1.393(4) .
C2 C3 1.380(3) .
C2 Cl2 1.724(3) .
C3 C4 1.387(4) .
C3 H3 0.9300 .
C4 C5 1.381(3) .
C4 Cl1 1.692(3) .
C5 C6 1.384(3) .
C5 H5 0.9300 .
C6 C7 1.415(4) .
C7 N1 1.292(3) .
C7 H7 0.9300 .
C8 O2 1.405(3) .
C8 C9 1.509(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.481(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 O3 1.473(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 N2 1.245(3) .
C11 C12 1.439(3) .
C11 H11 0.9300 .
C12 C13 1.381(4) .
C12 C17 1.399(4) .
C13 C14 1.352(4) .
C13 H13 0.9300 .
C14 C15 1.404(4) .
C14 H14 0.9300 .
C15 C16 1.381(4) .
C15 H15 0.9300 .
C16 C17 1.386(3) .
C16 H16 0.9300 .
C17 O4 1.356(3) .
C18 C18 1.440(5) 2_556
C18 O4 1.442(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
N1 O2 1.355(3) .
N2 O3 1.390(3) .
O1 H1B 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -178.9(2) . . . .
C6 C1 C2 C3 0.3(4) . . . .
O1 C1 C2 Cl2 2.8(4) . . . .
C6 C1 C2 Cl2 -178.0(2) . . . .
C1 C2 C3 C4 -0.3(4) . . . .
Cl2 C2 C3 C4 178.0(2) . . . .
C2 C3 C4 C5 0.3(4) . . . .
C2 C3 C4 Cl1 -179.5(2) . . . .
C3 C4 C5 C6 -0.2(4) . . . .
Cl1 C4 C5 C6 179.5(2) . . . .
C4 C5 C6 C1 0.2(4) . . . .
C4 C5 C6 C7 178.4(2) . . . .
O1 C1 C6 C5 178.9(2) . . . .
C2 C1 C6 C5 -0.3(4) . . . .
O1 C1 C6 C7 0.8(4) . . . .
C2 C1 C6 C7 -178.4(3) . . . .
C5 C6 C7 N1 -175.6(2) . . . .
C1 C6 C7 N1 2.5(4) . . . .
O2 C8 C9 C10 177.3(2) . . . .
C8 C9 C10 O3 179.6(2) . . . .
N2 C11 C12 C13 7.4(4) . . . .
N2 C11 C12 C17 -172.3(3) . . . .
C17 C12 C13 C14 0.8(4) . . . .
C11 C12 C13 C14 -178.9(3) . . . .
C12 C13 C14 C15 -1.6(5) . . . .
C13 C14 C15 C16 1.6(5) . . . .
C14 C15 C16 C17 -1.0(4) . . . .
C15 C16 C17 O4 178.4(3) . . . .
C15 C16 C17 C12 0.3(4) . . . .
C13 C12 C17 O4 -178.5(2) . . . .
C11 C12 C17 O4 1.2(4) . . . .
C13 C12 C17 C16 -0.2(4) . . . .
C11 C12 C17 C16 179.6(2) . . . .
C6 C7 N1 O2 179.5(2) . . . .
C12 C11 N2 O3 -178.3(2) . . . .
C7 N1 O2 C8 -173.0(2) . . . .
C9 C8 O2 N1 177.5(2) . . . .
C11 N2 O3 C10 -177.4(2) . . . .
C9 C10 O3 N2 -179.6(2) . . . .
C16 C17 O4 C18 4.4(4) . . . .
C12 C17 O4 C18 -177.5(2) . . . .
C18 C18 O4 C17 -178.6(2) 2_556 . . .
