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#$Date: 2022-06-13 12:03:28 +0300 (Mon, 13 Jun 2022) $
#$Revision: 275995 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105400.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_8105400
loop_
_publ_author_name
'Wu, Chong'
'Wu, Shou-Ting'
'Zhang, Qi-Long'
'Zou, Juan'
_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 für 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/[σ²(Fo²)+(0.0625P)²+0.1881P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0203_suppl.cif
_cod_data_source_block           a
_cod_database_code               8105400
_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_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)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.9537(2) 0.3885(2) 0.0968(2) 0.0416(5) Uani 1 1 d . . . . .
C2 C 0.9199(2) 0.3146(2) 0.1820(2) 0.0397(4) Uani 1 1 d . . . . .
C3 C 0.7715(2) 0.2072(2) 0.1142(2) 0.0423(5) Uani 1 1 d . . . . .
H3 H 0.6892 0.1775 0.0085 0.051 Uiso 1 1 calc R . . . .
C4 C 0.7439(2) 0.1438(2) 0.2007(2) 0.0440(5) Uani 1 1 d . . . . .
H4 H 0.6436 0.0726 0.1542 0.053 Uiso 1 1 calc R . . . .
C5 C 0.8681(2) 0.1875(2) 0.3590(2) 0.0399(4) Uani 1 1 d . . . . .
C6 C 1.0166(2) 0.2942(2) 0.4263(2) 0.0472(5) Uani 1 1 d . . . . .
H6 H 1.0998 0.3229 0.5311 0.057 Uiso 1 1 calc R . . . .
C7 C 1.0421(2) 0.3579(2) 0.3402(3) 0.0476(5) Uani 1 1 d . . . . .
H7 H 1.1418 0.4306 0.3878 0.057 Uiso 1 1 calc R . . . .
C8 C 0.7317(2) 0.0177(2) 0.4217(2) 0.0411(5) Uani 1 1 d . . . . .
C9 C 0.6736(2) -0.1015(2) 0.5708(2) 0.0389(4) Uani 1 1 d . . . . .
C10 C 0.5186(2) -0.2033(2) 0.4473(2) 0.0457(5) Uani 1 1 d . . . . .
H10 H 0.4685 -0.2074 0.3457 0.055 Uiso 1 1 calc R . . . .
C11 C 0.7411(2) -0.1003(2) 0.7199(2) 0.0446(5) Uani 1 1 d . . . . .
H11 H 0.8451 -0.0314 0.8038 0.053 Uiso 1 1 calc R . . . .
C12 C 0.4403(3) -0.2983(3) 0.4787(3) 0.0525(5) Uani 1 1 d . . . . .
H12 H 0.3361 -0.3681 0.3975 0.063 Uiso 1 1 calc R . . . .
C13 C 0.5152(3) -0.2905(2) 0.6288(3) 0.0499(5) Uani 1 1 d . . . . .
H13 H 0.4602 -0.3557 0.6475 0.060 Uiso 1 1 calc R . . . .
C14 C 0.8047(2) -0.2519(2) 0.0846(2) 0.0431(5) Uani 1 1 d . . . . .
C15 C 0.6331(2) -0.3584(2) -0.0187(2) 0.0414(5) Uani 1 1 d . . . . .
H15A H 0.6118 -0.4346 -0.1318 0.050 Uiso 1 1 calc R . . . .
H15B H 0.5649 -0.2946 -0.0288 0.050 Uiso 1 1 calc R . . . .
C16 C 0.5873(2) -0.4482(2) 0.0530(2) 0.0435(5) Uani 1 1 d . . . . .
H16A H 0.6533 -0.5142 0.0608 0.052 Uiso 1 1 calc R . . . .
H16B H 0.6097 -0.3725 0.1668 0.052 Uiso 1 1 calc R . . . .
N1 N 0.7691(2) 0.0014(2) 0.5581(2) 0.0487(5) Uani 1 1 d . . . . .
H1 H 0.8621 0.0619 0.6457 0.058 Uiso 1 1 calc R . . . .
N2 N 0.8551(2) 0.1330(2) 0.4592(2) 0.0500(5) Uani 1 1 d . . . . .
H2 H 0.9367 0.1787 0.5592 0.060 Uiso 1 1 calc R . . . .
N3 N 0.6643(2) -0.19289(19) 0.7491(2) 0.0460(4) Uani 1 1 d . . . . .
O1 O 0.60740(17) -0.06004(16) 0.28759(16) 0.0515(4) Uani 1 1 d . . . . .
O2 O 0.83928(17) 0.33400(17) -0.05790(17) 0.0523(4) Uani 1 1 d . . . . .
H2A H 0.8676 0.3811 -0.0962 0.078 Uiso 1 1 calc R . . . .
O3 O 1.08046(18) 0.49416(18) 0.16600(18) 0.0582(4) Uani 1 1 d . . . . .
O4 O 0.85402(16) -0.17033(17) 0.03139(18) 0.0519(4) Uani 1 1 d . . . . .
H4A H 0.7919 -0.1238 0.0090 0.078 Uiso 1 1 calc R . . . .
O5 O 0.89897(18) -0.2404(2) 0.21382(19) 0.0677(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'
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
O2 C1 C2 115.64(16) . .
O3 C1 C2 121.95(17) . .
O3 C1 O2 122.40(16) . .
C3 C2 C1 123.12(17) . .
C3 C2 C7 118.81(17) . .
C7 C2 C1 118.05(17) . .
C2 C3 H3 119.4 . .
C4 C3 C2 121.16(18) . .
C4 C3 H3 119.4 . .
C3 C4 H4 120.3 . .
C3 C4 C5 119.40(18) . .
C5 C4 H4 120.3 . .
C6 C5 C4 119.40(16) . .
C6 C5 N2 115.66(16) . .
N2 C5 C4 124.93(17) . .
C5 C6 H6 119.7 . .
C7 C6 C5 120.68(18) . .
C7 C6 H6 119.7 . .
C2 C7 H7 119.7 . .
C6 C7 C2 120.53(18) . .
C6 C7 H7 119.7 . .
N2 C8 N1 110.24(16) . .
O1 C8 N1 124.76(17) . .
O1 C8 N2 125.01(16) . .
C10 C9 C11 118.03(17) . .
C10 C9 N1 125.21(16) . .
C11 C9 N1 116.77(17) . .
C9 C10 H10 120.9 . .
C12 C10 C9 118.23(18) . .
C12 C10 H10 120.9 . .
C9 C11 H11 118.4 . .
N3 C11 C9 123.27(19) . .
N3 C11 H11 118.4 . .
C10 C12 H12 119.9 . .
C13 C12 C10 120.23(19) . .
C13 C12 H12 119.9 . .
C12 C13 H13 118.9 . .
N3 C13 C12 122.26(17) . .
N3 C13 H13 118.9 . .
O4 C14 C15 118.43(16) . .
O5 C14 C15 122.42(17) . .
O5 C14 O4 119.15(18) . .
C14 C15 H15A 108.6 . .
C14 C15 H15B 108.6 . .
C14 C15 C16 114.55(16) . .
H15A C15 H15B 107.6 . .
C16 C15 H15A 108.6 . .
C16 C15 H15B 108.6 . .
C15 C16 H16A 109.0 . .
C15 C16 H16B 109.0 . .
C16 C16 C15 112.95(19) 2_645 .
C16 C16 H16A 109.0 2_645 .
C16 C16 H16B 109.0 2_645 .
H16A C16 H16B 107.8 . .
C8 N1 C9 127.63(16) . .
C8 N1 H1 116.2 . .
C9 N1 H1 116.2 . .
C5 N2 H2 115.3 . .
C8 N2 C5 129.38(16) . .
C8 N2 H2 115.3 . .
C13 N3 C11 117.99(17) . .
C1 O2 H2A 109.5 . .
C14 O4 H4A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.468(2) .
C1 O2 1.314(2) .
C1 O3 1.225(2) .
C2 C3 1.387(3) .
C2 C7 1.392(3) .
C3 H3 0.9300 .
C3 C4 1.378(3) .
C4 H4 0.9300 .
C4 C5 1.398(3) .
C5 C6 1.386(3) .
C5 N2 1.392(2) .
C6 H6 0.9300 .
C6 C7 1.368(3) .
C7 H7 0.9300 .
C8 N1 1.377(2) .
C8 N2 1.366(2) .
C8 O1 1.213(2) .
C9 C10 1.382(3) .
C9 C11 1.388(3) .
C9 N1 1.396(2) .
C10 H10 0.9300 .
C10 C12 1.377(3) .
C11 H11 0.9300 .
C11 N3 1.333(2) .
C12 H12 0.9300 .
C12 C13 1.366(3) .
C13 H13 0.9300 .
C13 N3 1.331(3) .
C14 C15 1.498(3) .
C14 O4 1.307(2) .
C14 O5 1.210(2) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 C16 1.516(2) .
C16 C16 1.512(4) 2_645
C16 H16A 0.9700 .
C16 H16B 0.9700 .
N1 H1 0.8600 .
N2 H2 0.8600 .
O2 H2A 0.8200 .
O4 H4A 0.8200 .
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
C4 H4 O1 0.93 2.37 2.946(2) 119.7 .
C10 H10 O1 0.93 2.31 2.893(2) 120.4 .
C12 H12 O3 0.93 2.31 3.220(3) 165.9 1_445
N1 H1 O5 0.86 2.20 2.993(2) 154.1 2_756
N2 H2 O5 0.86 1.96 2.807(2) 167.0 2_756
O2 H2A O3 0.82 1.81 2.6207(17) 171.9 2_765
O4 H4A N3 0.82 2.14 2.612(2) 116.3 1_554
