Crystal structure of 4-(3-(pyridin-3-yl)ureido)benzoic acid — adipic acid (2/1), C16H16N3O5
Wu, Chong; Wu, Shou-Ting; Zhang, Qi-Long; Zou, Juan; Zeitschrift für Kristallographie - New Crystal Structures 235 (2020) 1135–1136; doi:10.1515/ncrs-2020-0203

data_8105400
_publ_section_title
;
 Crystal structure of 4-(3-(pyridin-3-yl)ureido)benzoic acid --- adipic
 acid (2/1), C16H16N3O5
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1135
_journal_page_last               1136
_journal_paper_doi               10.1515/ncrs-2020-0203
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C13 H11 N3 O3, C3 H5 O2'
_chemical_formula_sum            'C16 H16 N3 O5'
_chemical_formula_weight         330.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                116.680(2)
_cell_angle_beta                 113.268(2)
_cell_angle_gamma                95.809(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6481(6)
_cell_length_b                   10.0123(6)
_cell_length_c                   10.1667(6)
_cell_measurement_reflns_used    1650
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.68
_cell_volume                     758.31(8)
_computing_cell_refinement       'SAINT (Brucker, 2012)[2]'
_computing_data_collection       'APEX2 (Brucker, 2012)[2]'
_computing_data_reduction        'SAINT (Brucker, 2012)[2]'
_computing_molecular_graphics    'Diamond 4.0[4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[1]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[3]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4933
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.961
_diffrn_reflns_theta_max         24.961
_diffrn_reflns_theta_min         2.416
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+0.1881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2131
_reflns_number_total             2663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2020-0203_suppl.cif
_cod_data_source_block           a
_cod_database_code               8105400
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 N1(H1), N2(H2)
2.c Tetrahedral OH refined with riding coordinates:
 O2(H2A), O4(H4A)
;