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#$Date: 2020-04-20 21:36:47 +0300 (Mon, 20 Apr 2020) $
#$Revision: 250935 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517586.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_4517586
loop_
_publ_author_name
'Shah, Syed Raza'
'Shah, Zarbad'
'Khiat, Mohammed'
'Khan, Ajmal'
'Hill, Leila R.'
'Khan, Shakeel'
'Hussain, Javid'
'Csuk, René'
'Anwar, Muhammad U.'
'Al-Harrasi, Ahmed'
_publ_section_title
;
 Complexes of N- and O-Donor Ligands as Potential Urease Inhibitors
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c01089
_journal_year                    2020
_chemical_formula_moiety         'C6 H13 Co N3 O4, 2(C4 H3 N2 O3), 3(H2 O)'
_chemical_formula_sum            'C14 H25 Co N7 O13'
_chemical_formula_weight         558.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 107.954(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.564(5)
_cell_length_b                   11.051(5)
_cell_length_c                   18.100(7)
_cell_measurement_reflns_used    8850
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      3.00
_cell_volume                     2200.4(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28254
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.461
_diffrn_reflns_theta_min         3.095
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       block
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4501
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0876P)²+3.6929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3700
_reflns_number_total             4501
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c01089_si_002.cif
_cod_data_source_block           SR_114_0ma_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4517586
_shelx_shelxl_version_number     2016/6
_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.
;
loop_
_space_group_symop_operation_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_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
O23 O 0.2840(3) 0.3624(4) 0.1840(2) 0.0730(10) Uani 1 1 d D . . . .
H23A H 0.222(4) 0.399(5) 0.158(3) 0.088 Uiso 1 1 d D U . . .
H23B H 0.295(6) 0.305(4) 0.154(3) 0.088 Uiso 1 1 d D U . . .
Co1 Co 0.39518(3) 0.74462(4) 0.08567(2) 0.02650(19) Uani 1 1 d . . . . .
O22 O 0.2862(5) 0.5905(6) 0.3503(5) 0.131(2) Uani 1 1 d D . . . .
H22A H 0.246(7) 0.618(8) 0.378(5) 0.157 Uiso 1 1 d D U . . .
H22B H 0.335(7) 0.533(6) 0.358(6) 0.157 Uiso 1 1 d D U . . .
O24 O 0.4121(5) 0.2209(5) 0.1193(3) 0.0911(13) Uani 1 1 d G . . . .
H24A H 0.486255 0.200247 0.130228 0.137 Uiso 1 1 d G U . . .
H24B H 0.393636 0.247186 0.072949 0.137 Uiso 1 1 d G U . . .
O1 O 0.5302(2) 0.7537(2) 0.19459(13) 0.0341(5) Uani 1 1 d . . . . .
O3 O 0.3894(2) 0.9322(2) 0.09051(12) 0.0358(5) Uani 1 1 d . . . . .
H3A H 0.372637 0.961777 0.047546 0.054 Uiso 1 1 d R U . . .
H3B H 0.447827 0.969607 0.118256 0.054 Uiso 1 1 d R U . . .
O4 O 0.4168(3) 0.5583(2) 0.08648(14) 0.0450(6) Uani 1 1 d D . . . .
H4A H 0.381(4) 0.510(3) 0.0533(19) 0.054 Uiso 1 1 d D U . . .
H4B H 0.471(3) 0.527(4) 0.1216(18) 0.054 Uiso 1 1 d D U . . .
O5 O 0.5299(2) 0.7567(2) 0.02948(14) 0.0357(5) Uani 1 1 d . . . . .
H5A H 0.570973 0.819201 0.039157 0.054 Uiso 1 1 d R U . . .
H5B H 0.579933 0.701361 0.033917 0.054 Uiso 1 1 d R U . . .
N1 N 0.2909(2) 0.7212(3) 0.16491(15) 0.0315(6) Uani 1 1 d . . . . .
H1A H 0.237112 0.781072 0.159225 0.038 Uiso 1 1 d R U . . .
H1B H 0.250962 0.651322 0.155865 0.038 Uiso 1 1 d R U . . .
N2 N 0.3753(2) 0.7223(3) 0.24172(15) 0.0354(6) Uani 1 1 d . . . . .
H2 H 0.348992 0.705379 0.278993 0.042 Uiso 1 1 d R U . . .
N3 N 0.7555(2) 0.7587(2) 0.47638(14) 0.0253(5) Uani 1 1 d . . . . .
C1 C 0.4918(3) 0.7414(2) 0.25045(17) 0.0247(6) Uani 1 1 d . . . . .
C2 C 0.5794(3) 0.7469(2) 0.33083(17) 0.0239(6) Uani 1 1 d . . . . .
C3 C 0.6993(3) 0.7750(3) 0.33814(18) 0.0343(7) Uani 1 1 d . . . . .
H3 H 0.722916 0.789923 0.294300 0.041 Uiso 1 1 calc R U . . .
C4 C 0.7833(3) 0.7805(4) 0.41138(19) 0.0388(8) Uani 1 1 d . . . . .
H4 H 0.863144 0.800514 0.415536 0.047 Uiso 1 1 calc R U . . .
C5 C 0.6394(3) 0.7304(3) 0.46842(19) 0.0376(8) Uani 1 1 d . . . . .
H5 H 0.618233 0.714035 0.512987 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5497(3) 0.7244(3) 0.39752(19) 0.0371(8) Uani 1 1 d . . . . .
H6 H 0.470190 0.705349 0.394878 0.045 Uiso 1 1 calc R U . . .
O9 O 0.8392(2) 0.4578(2) 0.45378(14) 0.0463(6) Uani 1 1 d . . . . .
O10 O 0.6071(2) 0.4738(3) 0.20336(14) 0.0473(7) Uani 1 1 d . . . . .
O11 O 0.4191(3) 0.3741(3) 0.38187(16) 0.0657(9) Uani 1 1 d . . . . .
N7 N 0.7196(2) 0.4614(3) 0.32960(15) 0.0352(6) Uani 1 1 d . . . . .
H7 H 0.783336 0.480094 0.317131 0.042 Uiso 1 1 d R U . . .
H8 H 0.452(4) 0.414(4) 0.259(2) 0.042 Uiso 1 1 d . U . . .
N8 N 0.5153(3) 0.4199(3) 0.29379(17) 0.0387(7) Uani 1 1 d . . . . .
C13 C 0.6128(3) 0.4527(3) 0.27206(18) 0.0321(7) Uani 1 1 d . . . . .
C14 C 0.7329(3) 0.4422(3) 0.40764(19) 0.0344(7) Uani 1 1 d . . . . .
C15 C 0.6309(4) 0.4091(4) 0.4267(2) 0.0461(9) Uani 1 1 d . . . . .
H15 H 0.637468 0.393480 0.478355 0.055 Uiso 1 1 calc R U . . .
C16 C 0.5179(3) 0.3987(4) 0.3702(2) 0.0428(8) Uani 1 1 d . . . . .
O12 O 0.5745(2) 0.0593(3) 0.21020(13) 0.0435(6) Uani 1 1 d . . . . .
O13 O 0.7958(2) 0.0844(2) 0.46477(14) 0.0432(6) Uani 1 1 d . . . . .
O14 O 0.3904(2) 0.0166(2) 0.40720(13) 0.0407(6) Uani 1 1 d . . . . .
N9 N 0.5926(2) 0.0511(3) 0.43467(14) 0.0325(6) Uani 1 1 d . . . . .
H9 H 0.599246 0.045627 0.483194 0.039 Uiso 1 1 d R U . . .
N10 N 0.6815(2) 0.0787(3) 0.33787(15) 0.0373(7) Uani 1 1 d . . . . .
H10 H 0.744208 0.096049 0.323994 0.045 Uiso 1 1 d R U . . .
C25 C 0.5720(3) 0.0604(3) 0.27975(18) 0.0339(7) Uani 1 1 d . . . . .
C26 C 0.4701(3) 0.0436(3) 0.30308(17) 0.0325(7) Uani 1 1 d . . . . .
H26 H 0.394417 0.036800 0.265610 0.039 Uiso 1 1 calc R U . . .
C27 C 0.4776(3) 0.0367(3) 0.38118(17) 0.0304(6) Uani 1 1 d . . . . .
C28 C 0.6956(3) 0.0723(3) 0.41516(18) 0.0318(7) 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'
Co Co 0.3494 0.9721 '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
H23A O23 H23B 105(6) . . ?
O4 Co1 O3 175.03(10) . . ?
O4 Co1 O1 89.29(9) . . ?
O3 Co1 O1 86.41(9) . . ?
O4 Co1 O5 87.76(11) . . ?
O3 Co1 O5 89.75(9) . . ?
O1 Co1 O5 90.21(10) . . ?
O4 Co1 N3 92.56(9) . 4_575 ?
O3 Co1 N3 91.79(9) . 4_575 ?
O1 Co1 N3 177.91(9) . 4_575 ?
O5 Co1 N3 90.83(10) . 4_575 ?
O4 Co1 N1 88.10(12) . . ?
O3 Co1 N1 93.43(10) . . ?
O1 Co1 N1 77.80(10) . . ?
O5 Co1 N1 167.36(10) . . ?
N3 Co1 N1 101.29(10) 4_575 . ?
H22A O22 H22B 131(9) . . ?
H24A O24 H24B 104.5 . . ?
C1 O1 Co1 114.3(2) . . ?
Co1 O3 H3A 111.3 . . ?
Co1 O3 H3B 119.9 . . ?
H3A O3 H3B 107.0 . . ?
Co1 O4 H4A 128(3) . . ?
Co1 O4 H4B 119(3) . . ?
H4A O4 H4B 113(4) . . ?
Co1 O5 H5A 114.4 . . ?
Co1 O5 H5B 120.3 . . ?
H5A O5 H5B 104.9 . . ?
N2 N1 Co1 106.93(18) . . ?
N2 N1 H1A 110.4 . . ?
Co1 N1 H1A 110.3 . . ?
N2 N1 H1B 110.3 . . ?
Co1 N1 H1B 110.3 . . ?
H1A N1 H1B 108.7 . . ?
C1 N2 N1 118.8(3) . . ?
C1 N2 H2 123.0 . . ?
N1 N2 H2 118.0 . . ?
C4 N3 C5 116.9(3) . . ?
C4 N3 Co1 120.1(2) . 4_676 ?
C5 N3 Co1 122.8(2) . 4_676 ?
O1 C1 N2 122.1(3) . . ?
O1 C1 C2 119.1(3) . . ?
N2 C1 C2 118.8(3) . . ?
C6 C2 C3 118.0(3) . . ?
C6 C2 C1 124.7(3) . . ?
C3 C2 C1 117.3(3) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
N3 C4 C3 123.3(3) . . ?
N3 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
N3 C5 C6 123.4(3) . . ?
N3 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C2 C6 C5 119.2(3) . . ?
C2 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C13 N7 C14 124.1(3) . . ?
C13 N7 H7 117.9 . . ?
C14 N7 H7 118.0 . . ?
C13 N8 C16 124.6(3) . . ?
C13 N8 H8 115(3) . . ?
C16 N8 H8 120(3) . . ?
O10 C13 N7 120.6(3) . . ?
O10 C13 N8 123.2(3) . . ?
N7 C13 N8 116.2(3) . . ?
O9 C14 C15 127.1(3) . . ?
O9 C14 N7 115.5(3) . . ?
C15 C14 N7 117.5(3) . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
O11 C16 N8 117.5(3) . . ?
O11 C16 C15 126.2(3) . . ?
N8 C16 C15 116.3(3) . . ?
C28 N9 C27 124.3(3) . . ?
C28 N9 H9 117.9 . . ?
C27 N9 H9 117.9 . . ?
C28 N10 C25 124.3(3) . . ?
C28 N10 H10 117.9 . . ?
C25 N10 H10 117.8 . . ?
O12 C25 C26 125.8(3) . . ?
O12 C25 N10 117.3(3) . . ?
C26 C25 N10 116.9(3) . . ?
C25 C26 C27 121.7(3) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
O14 C27 C26 125.7(3) . . ?
O14 C27 N9 117.7(3) . . ?
C26 C27 N9 116.6(3) . . ?
O13 C28 N10 122.0(3) . . ?
O13 C28 N9 122.0(3) . . ?
N10 C28 N9 116.0(3) . . ?
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
O23 H23A 0.83(2) . ?
O23 H23B 0.87(2) . ?
Co1 O4 2.074(3) . ?
Co1 O3 2.077(3) . ?
Co1 O1 2.107(2) . ?
Co1 O5 2.110(2) . ?
Co1 N3 2.134(3) 4_575 ?
Co1 N1 2.156(3) . ?
O22 H22A 0.834(10) . ?
O22 H22B 0.832(10) . ?
O24 H24A 0.8500 . ?
O24 H24B 0.8499 . ?
O1 C1 1.231(4) . ?
O3 H3A 0.8101 . ?
O3 H3B 0.8191 . ?
O4 H4A 0.817(10) . ?
O4 H4B 0.819(10) . ?
O5 H5A 0.8264 . ?
O5 H5B 0.8287 . ?
N1 N2 1.432(4) . ?
N1 H1A 0.8918 . ?
N1 H1B 0.8884 . ?
N2 C1 1.325(4) . ?
N2 H2 0.8420 . ?
N3 C4 1.333(4) . ?
N3 C5 1.343(4) . ?
C1 C2 1.496(4) . ?
C2 C6 1.376(4) . ?
C2 C3 1.387(5) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
O9 C14 1.267(4) . ?
O10 C13 1.247(4) . ?
O11 C16 1.254(4) . ?
N7 C13 1.352(4) . ?
N7 C14 1.389(4) . ?
N7 H7 0.8594 . ?
N8 C13 1.353(4) . ?
N8 C16 1.394(4) . ?
N8 H8 0.81(4) . ?
C14 C15 1.377(5) . ?
C15 C16 1.394(5) . ?
C15 H15 0.9300 . ?
O12 C25 1.268(4) . ?
O13 C28 1.235(4) . ?
O14 C27 1.257(4) . ?
N9 C28 1.362(4) . ?
N9 C27 1.392(4) . ?
N9 H9 0.8601 . ?
N10 C28 1.359(4) . ?
N10 C25 1.389(4) . ?
N10 H10 0.8595 . ?
C25 C26 1.381(5) . ?
C26 C27 1.391(4) . ?
C26 H26 0.9300 . ?
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
Co1 N1 N2 C1 2.8(3) . . . . ?
Co1 O1 C1 N2 1.0(4) . . . . ?
Co1 O1 C1 C2 -179.67(19) . . . . ?
N1 N2 C1 O1 -2.8(5) . . . . ?
N1 N2 C1 C2 177.9(3) . . . . ?
O1 C1 C2 C6 -174.2(3) . . . . ?
N2 C1 C2 C6 5.2(4) . . . . ?
O1 C1 C2 C3 4.8(4) . . . . ?
N2 C1 C2 C3 -175.8(3) . . . . ?
C6 C2 C3 C4 -0.7(5) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C5 N3 C4 C3 -0.2(5) . . . . ?
Co1 N3 C4 C3 174.9(3) 4_676 . . . ?
C2 C3 C4 N3 0.8(6) . . . . ?
C4 N3 C5 C6 -0.6(5) . . . . ?
Co1 N3 C5 C6 -175.6(3) 4_676 . . . ?
C3 C2 C6 C5 -0.1(5) . . . . ?
C1 C2 C6 C5 178.9(3) . . . . ?
N3 C5 C6 C2 0.8(6) . . . . ?
C14 N7 C13 O10 178.4(3) . . . . ?
C14 N7 C13 N8 -1.8(5) . . . . ?
C16 N8 C13 O10 -178.3(4) . . . . ?
C16 N8 C13 N7 2.0(5) . . . . ?
C13 N7 C14 O9 -178.0(3) . . . . ?
C13 N7 C14 C15 1.8(5) . . . . ?
O9 C14 C15 C16 177.9(4) . . . . ?
N7 C14 C15 C16 -1.8(6) . . . . ?
C13 N8 C16 O11 176.9(4) . . . . ?
C13 N8 C16 C15 -2.0(6) . . . . ?
C14 C15 C16 O11 -176.9(4) . . . . ?
C14 C15 C16 N8 1.9(6) . . . . ?
C28 N10 C25 O12 -174.3(3) . . . . ?
C28 N10 C25 C26 5.1(5) . . . . ?
O12 C25 C26 C27 174.8(3) . . . . ?
N10 C25 C26 C27 -4.5(5) . . . . ?
C25 C26 C27 O14 -176.9(3) . . . . ?
C25 C26 C27 N9 1.9(5) . . . . ?
C28 N9 C27 O14 179.5(3) . . . . ?
C28 N9 C27 C26 0.6(5) . . . . ?
C25 N10 C28 O13 177.0(3) . . . . ?
C25 N10 C28 N9 -2.7(5) . . . . ?
C27 N9 C28 O13 -179.9(3) . . . . ?
C27 N9 C28 N10 -0.2(5) . . . . ?
