#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/77/4507787.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_4507787
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         'C17 H16 N2 O5, C12 H10 N2'
_chemical_formula_sum            'C29 H26 N4 O5'
_chemical_formula_weight         510.54
_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                 95.2820(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8373(11)
_cell_length_b                   13.6735(14)
_cell_length_c                   16.8579(17)
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.40
_cell_volume                     2487.5(4)
_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 0.976
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6863
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0566P)²+0.8110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                2253
_reflns_number_total             2805
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301878r_si_002.cif
_cod_data_source_block           1:3(a120912his1)
_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_sg_symbol_H-M      'C2/c  '
_cod_database_code               4507787
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
C14 C 0.40412(13) 0.00227(10) 0.58783(8) 0.0342(3) Uani 1 1 d .
H14 H 0.4603 0.0135 0.6336 0.041 Uiso 1 1 calc R
C7 C 0.60394(11) 0.33267(9) 0.67767(7) 0.0271(3) Uani 1 1 d .
C8 C 0.54789(11) 0.42299(9) 0.66233(7) 0.0274(3) Uani 1 1 d .
H8 H 0.4749 0.4277 0.6267 0.033 Uiso 1 1 calc R
C15 C 0.24063(12) -0.20919(9) 0.47921(8) 0.0316(3) Uani 1 1 d .
H15 H 0.1940 -0.2145 0.4288 0.038 Uiso 1 1 calc R
C3 C 0.59902(11) 0.50621(9) 0.69926(7) 0.0269(3) Uani 1 1 d .
C1 C 0.5000 0.65279(12) 0.7500 0.0288(4) Uani 1 2 d S
C6 C 0.71284(12) 0.32672(9) 0.72822(8) 0.0311(3) Uani 1 1 d .
H6 H 0.7502 0.2649 0.7398 0.037 Uiso 1 1 calc R
C12 C 0.28505(12) -0.11126(9) 0.50352(8) 0.0293(3) Uani 1 1 d .
C10 C 0.28558(13) 0.06192(10) 0.47938(8) 0.0347(3) Uani 1 1 d .
H10 H 0.2560 0.1157 0.4474 0.042 Uiso 1 1 calc R
C13 C 0.36720(12) -0.09285(10) 0.57062(8) 0.0331(3) Uani 1 1 d .
H13 H 0.3974 -0.1451 0.6041 0.040 Uiso 1 1 calc R
C4 C 0.71022(12) 0.50060(9) 0.74732(8) 0.0309(3) Uani 1 1 d .
H4 H 0.7473 0.5582 0.7702 0.037 Uiso 1 1 calc R
C5 C 0.76659(12) 0.41042(10) 0.76156(8) 0.0338(3) Uani 1 1 d .
H5 H 0.8425 0.4063 0.7944 0.041 Uiso 1 1 calc R
C11 C 0.24485(13) -0.03098(10) 0.45775(8) 0.0342(3) Uani 1 1 d .
H11 H 0.1892 -0.0399 0.4114 0.041 Uiso 1 1 calc R
C9 C 0.54792(12) 0.23987(9) 0.64413(8) 0.0289(3) Uani 1 1 d .
C2 C 0.57867(14) 0.65507(10) 0.61962(9) 0.0403(4) Uani 1 1 d .
H2A H 0.5301 0.7154 0.6127 0.061 Uiso 1 1 calc R
H2B H 0.5664 0.6157 0.5710 0.061 Uiso 1 1 calc R
H2C H 0.6667 0.6714 0.6303 0.061 Uiso 1 1 calc R
O3 O 0.59010(9) 0.16020(6) 0.66385(6) 0.0389(3) Uani 1 1 d .
O2 O 0.45054(9) 0.25251(6) 0.59215(6) 0.0380(3) Uani 1 1 d .
H2 H 0.4237 0.1978 0.5758 0.057 Uiso 1 1 calc R
O1 O 0.5000 0.74225(9) 0.7500 0.0405(4) Uani 1 2 d S
N1 N 0.53805(10) 0.59944(8) 0.68669(7) 0.0299(3) Uani 1 1 d .
N2 N 0.36501(10) 0.07926(8) 0.54347(7) 0.0322(3) 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'
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
N2 C14 C13 123.51(12) . .
N2 C14 H14 118.2 . .
C13 C14 H14 118.2 . .
C8 C7 C6 119.79(11) . .
C8 C7 C9 121.90(11) . .
C6 C7 C9 118.26(11) . .
C3 C8 C7 119.70(11) . .
C3 C8 H8 120.2 . .
C7 C8 H8 120.2 . .
C15 C15 C12 126.20(15) 7_546 .
C15 C15 H15 116.9 7_546 .
C12 C15 H15 116.9 . .
C8 C3 C4 120.32(11) . .
C8 C3 N1 120.01(11) . .
C4 C3 N1 119.66(11) . .
O1 C1 N1 121.74(7) . .
O1 C1 N1 121.75(7) . 2_656
N1 C1 N1 116.51(15) . 2_656
C5 C6 C7 120.18(12) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C11 C12 C13 116.84(12) . .
C11 C12 C15 119.19(11) . .
C13 C12 C15 123.96(12) . .
N2 C10 C11 122.77(13) . .
N2 C10 H10 118.6 . .
C11 C10 H10 118.6 . .
C14 C13 C12 119.32(12) . .
C14 C13 H13 120.3 . .
C12 C13 H13 120.3 . .
C5 C4 C3 119.60(12) . .
C5 C4 H4 120.2 . .
C3 C4 H4 120.2 . .
C6 C5 C4 120.27(11) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C10 C11 C12 120.24(12) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
O3 C9 O2 123.82(11) . .
O3 C9 C7 121.85(11) . .
O2 C9 C7 114.33(10) . .
N1 C2 H2A 109.5 . .
N1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C9 O2 H2 109.5 . .
C1 N1 C3 121.10(10) . .
C1 N1 C2 116.95(11) . .
C3 N1 C2 113.98(11) . .
C14 N2 C10 117.31(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C14 N2 1.3374(17) .
C14 C13 1.3837(18) .
C14 H14 0.9500 .
C7 C8 1.3901(17) .
C7 C6 1.3930(17) .
C7 C9 1.4950(17) .
C8 C3 1.3878(17) .
C8 H8 0.9500 .
C15 C15 1.324(3) 7_546
C15 C12 1.4685(18) .
C15 H15 0.9500 .
C3 C4 1.3909(18) .
C3 N1 1.4425(15) .
C1 O1 1.223(2) .
C1 N1 1.3864(14) .
C1 N1 1.3864(14) 2_656
C6 C5 1.3801(18) .
C6 H6 0.9500 .
C12 C11 1.3886(19) .
C12 C13 1.3965(18) .
C10 N2 1.3392(17) .
C10 C11 1.3826(18) .
C10 H10 0.9500 .
C13 H13 0.9500 .
C4 C5 1.3872(18) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C11 H11 0.9500 .
C9 O3 1.2157(15) .
C9 O2 1.3195(15) .
C2 N1 1.4637(17) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
O2 H2 0.8400 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146525
