#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/77/4507790.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_4507790
loop_
_publ_author_name
'Hisamatsu, Shugo'
'Masu, Hyuma'
'Takahashi, Masahiro'
'Kishikawa, Keiki'
'Kohmoto, Shigeo'
_publ_section_title
;
 Conformation-Directed Hydrogen-Bonding inmeta-Substituted Aromatic
 Ureadicarboxylic Acid: A Conformationally Flexible U-Shaped Building
 Block
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2327
_journal_paper_doi               10.1021/cg301878r
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C24 H16 N2, C17 H16 N2 O5'
_chemical_formula_sum            'C41 H32 N4 O5'
_chemical_formula_weight         660.71
_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'
_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                 93.8750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3667(7)
_cell_length_b                   12.4342(12)
_cell_length_c                   35.712(3)
_cell_measurement_reflns_used    2893
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.29
_cell_volume                     3263.7(5)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            8814
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.79
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0559
_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)+(0.0967P)²+2.6942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1803
_reflns_number_gt                2801
_reflns_number_total             3712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301878r_si_002.cif
_cod_data_source_block           1:5(a120627his2)
_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 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3263.8(5)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               4507790
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_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
C19 C 0.8717(3) 0.97236(16) 0.02599(5) 0.0330(4) Uani 1 1 d .
O2 O 0.8543(2) 0.83209(14) 0.14943(5) 0.0469(4) Uani 1 1 d .
H2 H 0.9436 0.8266 0.1361 0.070 Uiso 1 1 calc R
C7 C 0.5532(3) 0.83734(17) 0.18981(5) 0.0314(4) Uani 1 1 d .
H7 H 0.6381 0.8949 0.1917 0.038 Uiso 1 1 calc R
O1 O 0.7755(2) 0.67626(14) 0.12194(5) 0.0555(5) Uani 1 1 d .
C2 C 0.5825(3) 0.75084(16) 0.16623(5) 0.0318(4) Uani 1 1 d .
C18 C 0.8474(3) 0.93789(16) -0.01238(5) 0.0330(4) Uani 1 1 d .
N1 N 0.3612(2) 0.93340(15) 0.23224(5) 0.0401(4) Uani 1 1 d .
N2 N 0.1453(2) 0.83489(15) 0.11102(5) 0.0377(4) Uani 1 1 d .
C20 C 0.7361(3) 0.94539(17) 0.05166(6) 0.0355(5) Uani 1 1 d .
H20 H 0.7524 0.9677 0.0771 0.043 Uiso 1 1 calc R
C14 C 0.4384(3) 0.86755(17) 0.06590(6) 0.0341(5) Uani 1 1 d .
C1 C 0.7467(3) 0.74862(17) 0.14360(5) 0.0354(5) Uani 1 1 d .
C16 C 0.5631(3) 0.85240(18) 0.00183(6) 0.0375(5) Uani 1 1 d .
H16 H 0.4587 0.8115 -0.0062 0.045 Uiso 1 1 calc R
C21 C 1.0235(3) 1.03370(17) 0.03737(5) 0.0346(5) Uani 1 1 d .
H21 H 1.0394 1.0567 0.0627 0.042 Uiso 1 1 calc R
C13 C 0.4036(3) 0.93771(18) 0.09501(6) 0.0358(5) Uani 1 1 d .
H13 H 0.4798 0.9983 0.1001 0.043 Uiso 1 1 calc R
C3 C 0.4559(3) 0.66712(18) 0.16300(6) 0.0388(5) Uani 1 1 d .
H3 H 0.4729 0.6089 0.1463 0.047 Uiso 1 1 calc R
C5 C 0.2775(3) 0.7548(2) 0.20808(6) 0.0427(5) Uani 1 1 d .
H5 H 0.1744 0.7550 0.2227 0.051 Uiso 1 1 calc R
C15 C 0.5846(3) 0.88830(17) 0.03996(6) 0.0347(5) Uani 1 1 d .
C17 C 0.6895(3) 0.87583(18) -0.02315(6) 0.0381(5) Uani 1 1 d .
H17 H 0.6720 0.8503 -0.0482 0.046 Uiso 1 1 calc R
C6 C 0.3995(3) 0.84003(17) 0.21067(5) 0.0331(4) Uani 1 1 d .
C12 C 0.2567(3) 0.91825(18) 0.11649(6) 0.0376(5) Uani 1 1 d .
H12 H 0.2347 0.9671 0.1361 0.045 Uiso 1 1 calc R
O3 O 0.5000 1.0911(2) 0.2500 0.0682(8) Uani 1 2 d S
C11 C 0.1813(3) 0.76612(19) 0.08395(6) 0.0425(5) Uani 1 1 d .
H11 H 0.1052 0.7049 0.0801 0.051 Uiso 1 1 calc R
C4 C 0.3056(3) 0.6695(2) 0.18422(7) 0.0444(5) Uani 1 1 d .
H4 H 0.2207 0.6119 0.1824 0.053 Uiso 1 1 calc R
C10 C 0.3238(3) 0.77939(18) 0.06111(6) 0.0412(5) Uani 1 1 d .
H10 H 0.3433 0.7280 0.0421 0.049 Uiso 1 1 calc R
C9 C 0.5000 0.9925(3) 0.2500 0.0430(8) Uani 1 2 d S
C8 C 0.2024(4) 0.9961(3) 0.21922(9) 0.0787(11) Uani 1 1 d .
H8A H 0.1704 1.0457 0.2391 0.118 Uiso 1 1 calc R
H8B H 0.1000 0.9476 0.2130 0.118 Uiso 1 1 calc R
H8C H 0.2299 1.0372 0.1969 0.118 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
C21 C19 C18 119.25(17) . .
C21 C19 C20 121.32(18) . .
C18 C19 C20 119.41(19) . .
C1 O2 H2 109.5 . .
C2 C7 C6 120.38(19) . .
C2 C7 H7 119.8 . .
C6 C7 H7 119.8 . .
C7 C2 C3 119.71(18) . .
C7 C2 C1 120.27(18) . .
C3 C2 C1 120.00(19) . .
C21 C18 C17 122.96(19) 5_775 .
C21 C18 C19 119.28(19) 5_775 .
C17 C18 C19 117.76(18) . .
C9 N1 C6 120.82(17) . .
C9 N1 C8 114.6(2) . .
C6 N1 C8 116.5(2) . .
C12 N2 C11 117.20(17) . .
C15 C20 C19 120.94(19) . .
C15 C20 H20 119.5 . .
C19 C20 H20 119.5 . .
C10 C14 C13 116.44(18) . .
C10 C14 C15 121.32(19) . .
C13 C14 C15 122.2(2) . .
O1 C1 O2 123.81(19) . .
O1 C1 C2 122.6(2) . .
O2 C1 C2 113.58(17) . .
C17 C16 C15 121.2(2) . .
C17 C16 H16 119.4 . .
C15 C16 H16 119.4 . .
C19 C21 C18 121.47(18) . 5_775
C19 C21 H21 119.3 . .
C18 C21 H21 119.3 5_775 .
C12 C13 C14 119.5(2) . .
C12 C13 H13 120.3 . .
C14 C13 H13 120.3 . .
C4 C3 C2 119.6(2) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C4 C5 C6 120.15(19) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C20 C15 C16 119.32(18) . .
C20 C15 C14 120.68(19) . .
C16 C15 C14 119.94(19) . .
C16 C17 C18 121.3(2) . .
C16 C17 H17 119.4 . .
C18 C17 H17 119.4 . .
C5 C6 C7 119.4(2) . .
C5 C6 N1 120.28(17) . .
C7 C6 N1 120.18(19) . .
N2 C12 C13 123.45(19) . .
N2 C12 H12 118.3 . .
C13 C12 H12 118.3 . .
N2 C11 C10 123.3(2) . .
N2 C11 H11 118.4 . .
C10 C11 H11 118.4 . .
C3 C4 C5 120.8(2) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
C11 C10 C14 120.1(2) . .
C11 C10 H10 119.9 . .
C14 C10 H10 119.9 . .
O3 C9 N1 122.19(14) . .
O3 C9 N1 122.19(14) . 2_655
N1 C9 N1 115.6(3) . 2_655
N1 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C19 C21 1.391(3) .
C19 C18 1.435(3) .
C19 C20 1.440(3) .
O2 C1 1.314(3) .
O2 H2 0.8400 .
C7 C2 1.392(3) .
C7 C6 1.397(3) .
C7 H7 0.9500 .
O1 C1 1.215(3) .
C2 C3 1.397(3) .
C2 C1 1.499(3) .
C18 C21 1.393(3) 5_775
C18 C17 1.427(3) .
N1 C9 1.378(3) .
N1 C6 1.432(3) .
N1 C8 1.455(3) .
N2 C12 1.328(3) .
N2 C11 1.331(3) .
C20 C15 1.364(3) .
C20 H20 0.9500 .
C14 C10 1.387(3) .
C14 C13 1.394(3) .
C14 C15 1.490(3) .
C16 C17 1.364(3) .
C16 C15 1.432(3) .
C16 H16 0.9500 .
C21 C18 1.393(3) 5_775
C21 H21 0.9500 .
C13 C12 1.390(3) .
C13 H13 0.9500 .
C3 C4 1.384(3) .
C3 H3 0.9500 .
C5 C4 1.385(3) .
C5 C6 1.389(3) .
C5 H5 0.9500 .
C17 H17 0.9500 .
C12 H12 0.9500 .
O3 C9 1.227(4) .
C11 C10 1.382(3) .
C11 H11 0.9500 .
C4 H4 0.9500 .
C10 H10 0.9500 .
C9 N1 1.378(3) 2_655
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146528
