#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102758.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_8102758
loop_
_publ_author_name
'Chen Xu'
'Ying-Fei Li'
'Hong-Mei Li'
'Zhi-Qiang Wang'
'Yu-Qing Zhang'
_publ_section_title
;
 Crystal structure of N,N'-bis(3,5-dihydroxybenzamide)-1,4-benzene,
 C20H20N2O8
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              513
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C20 H20 N2 O8'
_chemical_formula_weight         416.38
_chemical_name_systematic
;
N,N^'^-Bis(3,5-dihydroxybenzamide)-1,4-benzene, C₂₀H₂₀N₂O₈
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.067(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.6352(16)
_cell_length_b                   10.200(3)
_cell_length_c                   16.093(5)
_cell_measurement_reflns_used    914
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      2.37
_cell_volume                     915.9(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5524
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9478
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0453
_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)+(0.0596P)²+0.2527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                1163
_reflns_number_total             1689
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3053.cff
_cod_data_source_block           b
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8102758
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_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
O1 O -0.5000(3) 0.22816(17) 0.32923(10) 0.0438(5) Uani 1 1 d . . .
H1 H -0.5558 0.2061 0.3715 0.066 Uiso 1 1 calc R . .
O2 O 0.0247(3) -0.12383(17) 0.42127(10) 0.0497(5) Uani 1 1 d . . .
H2 H 0.1345 -0.1666 0.4064 0.075 Uiso 1 1 calc R . .
O3 O 0.1127(3) 0.22489(16) 0.12853(10) 0.0444(5) Uani 1 1 d . . .
O4 O 0.8325(3) 0.3129(2) 0.97541(11) 0.0601(6) Uani 1 1 d . . .
H1W H 0.9027 0.2809 1.0200 0.090 Uiso 1 1 d R . .
H2W H 0.6950 0.3375 0.9824 0.090 Uiso 1 1 d R . .
N1 N 0.2386(4) 0.0138(2) 0.13615(11) 0.0413(5) Uani 1 1 d . . .
H1A H 0.2327 -0.0583 0.1635 0.050 Uiso 1 1 calc R . .
C1 C -0.3105(4) 0.1485(2) 0.31901(14) 0.0345(5) Uani 1 1 d . . .
C2 C -0.2381(4) 0.0490(2) 0.37534(13) 0.0369(6) Uani 1 1 d . . .
H2A H -0.3197 0.0339 0.4208 0.044 Uiso 1 1 calc R . .
C3 C -0.0435(4) -0.0279(2) 0.36344(13) 0.0351(6) Uani 1 1 d . . .
C4 C 0.0769(4) -0.0082(2) 0.29517(13) 0.0359(6) Uani 1 1 d . . .
H4 H 0.2068 -0.0607 0.2873 0.043 Uiso 1 1 calc R . .
C5 C 0.0005(4) 0.0915(2) 0.23842(13) 0.0343(5) Uani 1 1 d . . .
C6 C -0.1924(4) 0.1709(2) 0.25063(13) 0.0353(5) Uani 1 1 d . . .
H6 H -0.2414 0.2382 0.2132 0.042 Uiso 1 1 calc R . .
C7 C 0.1218(4) 0.1165(2) 0.16355(13) 0.0352(6) Uani 1 1 d . . .
C8 C 0.2894(4) 0.0709(3) -0.00894(14) 0.0410(6) Uani 1 1 d . . .
H8 H 0.1473 0.1186 -0.0152 0.049 Uiso 1 1 calc R . .
C9 C 0.3711(4) 0.0109(2) 0.06695(13) 0.0359(6) Uani 1 1 d . . .
C10 C 0.5810(4) -0.0598(2) 0.07514(14) 0.0411(6) Uani 1 1 d . . .
H10 H 0.6360 -0.1005 0.1259 0.049 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'
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
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
H1W O4 H2W 109.7 . . ?
C7 N1 C9 127.4(2) . . ?
C7 N1 H1A 116.3 . . ?
C9 N1 H1A 116.3 . . ?
O1 C1 C6 117.9(2) . . ?
O1 C1 C2 121.30(19) . . ?
C6 C1 C2 120.8(2) . . ?
C3 C2 C1 119.45(19) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
O2 C3 C2 117.63(19) . . ?
O2 C3 C4 121.4(2) . . ?
C2 C3 C4 120.9(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 C7 118.1(2) . . ?
C4 C5 C7 121.4(2) . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O3 C7 N1 122.5(2) . . ?
O3 C7 C5 121.8(2) . . ?
N1 C7 C5 115.7(2) . . ?
C10 C8 C9 119.9(2) 3_655 . ?
C10 C8 H8 120.1 3_655 . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 N1 118.3(2) . . ?
C8 C9 N1 122.2(2) . . ?
C9 C10 C8 120.7(2) . 3_655 ?
C9 C10 H10 119.6 . . ?
C8 C10 H10 119.6 3_655 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.370(3) . ?
O1 H1 0.8200 . ?
O2 C3 1.368(3) . ?
O2 H2 0.8200 . ?
O3 C7 1.238(3) . ?
O4 H1W 0.8361 . ?
O4 H2W 0.8371 . ?
N1 C7 1.344(3) . ?
N1 C9 1.425(3) . ?
N1 H1A 0.8600 . ?
C1 C6 1.383(3) . ?
C1 C2 1.384(3) . ?
C2 C3 1.383(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.384(3) . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 C7 1.489(3) . ?
C6 H6 0.9300 . ?
C8 C10 1.379(3) 3_655 ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(3) . ?
C10 C8 1.378(3) 3_655 ?
C10 H10 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86 2.55 3.289(3) 144.1 2_445
O4 H2W O2 0.84 2.15 2.859(2) 142.1 2_556
O4 H1W O3 0.84 2.05 2.877(3) 171.2 1_656
O2 H2 O3 0.82 1.95 2.768(2) 177.5 2_545
O1 H1 O4 0.82 1.88 2.688(2) 169.4 4_465
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
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.0(2) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 O2 179.0(2) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
O2 C3 C4 C5 -179.7(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C7 -179.5(2) . . . . ?
O1 C1 C6 C5 -179.9(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C7 C5 C6 C1 179.1(2) . . . . ?
C9 N1 C7 O3 1.5(4) . . . . ?
C9 N1 C7 C5 -179.3(2) . . . . ?
C6 C5 C7 O3 23.6(3) . . . . ?
C4 C5 C7 O3 -156.3(2) . . . . ?
C6 C5 C7 N1 -155.6(2) . . . . ?
C4 C5 C7 N1 24.5(3) . . . . ?
C10 C8 C9 C10 -0.3(4) 3_655 . . . ?
C10 C8 C9 N1 -176.9(2) 3_655 . . . ?
C7 N1 C9 C10 140.9(2) . . . . ?
C7 N1 C9 C8 -42.4(4) . . . . ?
C8 C9 C10 C8 0.3(4) . . . 3_655 ?
N1 C9 C10 C8 177.1(2) . . . 3_655 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139207296
