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#$Date: 2019-10-29 03:11:48 +0200 (Tue, 29 Oct 2019) $
#$Revision: 220331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/25/1552500.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_1552500
loop_
_publ_author_name
'Mcleod, Matthew J.'
'Krismanich, Anthony P.'
'Assoud, Abdeljalil'
'Dmitrienko, Gary I.'
'Holyoak, Todd'
_publ_section_title
;
 Characterization of 3-[(Carboxymethyl)thio]picolinic Acid: A Novel
 Inhibitor of Phosphoenolpyruvate Carboxykinase.
;
_journal_issue                   37
_journal_name_full               Biochemistry
_journal_page_first              3918
_journal_page_last               3926
_journal_paper_doi               10.1021/acs.biochem.9b00583
_journal_volume                  58
_journal_year                    2019
_chemical_formula_sum            'C8 H7 N O4 S'
_chemical_formula_weight         213.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 94.6669(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8712(2)
_cell_length_b                   15.8059(5)
_cell_length_c                   9.0571(3)
_cell_measurement_reflns_used    505
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      1.5
_cell_volume                     837.71(5)
_computing_cell_refinement       'SMART, 'Bruker APEX II'
_computing_data_collection       'Bruker kappa APEX II'
_computing_data_reduction        'SAINT, 'Bruker APEX II'
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016/6)'
_computing_structure_solution    'SHELXL-2016 (Sheldrick, 2016/6)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER SMART APEX II'
_diffrn_measurement_method       'Omega and phi scan'
_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  0.0204
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14410
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.992
_diffrn_reflns_theta_min         2.577
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  1
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0290
_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)+(0.0383P)²+0.3467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1762
_reflns_number_total             2016
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bi9b00583_si_002.cif
_cod_data_source_block           GD3_0m
_cod_database_code               1552500
_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.
;
_shelx_estimated_absorpt_t_min   0.879
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.26273(6) 0.68866(2) 0.66200(4) 0.02794(11) Uani 1 1 d . .
C2 C 0.4668(2) 0.74390(8) 0.56821(14) 0.0214(3) Uani 1 1 d . .
C3 C 0.4598(2) 0.83233(8) 0.56337(14) 0.0231(3) Uani 1 1 d . .
N4 N 0.6166(2) 0.87339(7) 0.49012(13) 0.0271(3) Uani 1 1 d . .
H4 H 0.611365 0.927769 0.489163 0.032 Uiso 1 1 calc R U
C5 C 0.7790(2) 0.83632(9) 0.41907(17) 0.0310(3) Uani 1 1 d . .
H5 H 0.882426 0.868460 0.370347 0.037 Uiso 1 1 calc R U
C6 C 0.7909(2) 0.74948(9) 0.41916(16) 0.0306(3) Uani 1 1 d . .
H6 H 0.902202 0.721949 0.369639 0.037 Uiso 1 1 calc R U
C7 C 0.6365(2) 0.70360(8) 0.49327(16) 0.0277(3) Uani 1 1 d . .
H7 H 0.644932 0.644845 0.493666 0.033 Uiso 1 1 calc R U
C8 C 0.2865(2) 0.89076(8) 0.62665(17) 0.0293(3) Uani 1 1 d . .
O9 O 0.2827(2) 0.96404(7) 0.57972(17) 0.0529(4) Uani 1 1 d . .
O10 O 0.1616(2) 0.85860(7) 0.71667(14) 0.0413(3) Uani 1 1 d . .
C11 C 0.3211(2) 0.57928(8) 0.61516(17) 0.0281(3) Uani 1 1 d . .
H11A H 0.335592 0.573705 0.509677 0.034 Uiso 1 1 calc R U
H11B H 0.462038 0.560212 0.668144 0.034 Uiso 1 1 calc R U
C12 C 0.1200(2) 0.52753(8) 0.66047(15) 0.0266(3) Uani 1 1 d . .
O13 O 0.18048(19) 0.45297(6) 0.71408(13) 0.0358(3) Uani 1 1 d . .
H13 H 0.057(3) 0.4245(8) 0.736(2) 0.054 Uiso 1 1 calc R U
O14 O -0.07480(18) 0.55251(7) 0.64436(13) 0.0363(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'
S S 0.1246 0.1234 '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
C2 S1 C11 102.17(6)
C3 C2 C7 117.29(12)
C3 C2 S1 119.50(10)
C7 C2 S1 123.19(10)
N4 C3 C2 118.57(11)
N4 C3 C8 113.50(11)
C2 C3 C8 127.88(12)
C5 N4 C3 124.96(12)
C5 N4 H4 117.5
C3 N4 H4 117.5
N4 C5 C6 118.58(13)
N4 C5 H5 120.7
C6 C5 H5 120.7
C5 C6 C7 119.38(13)
C5 C6 H6 120.3
C7 C6 H6 120.3
C6 C7 C2 121.21(12)
C6 C7 H7 119.4
C2 C7 H7 119.4
O9 C8 O10 127.75(13)
O9 C8 C3 115.77(12)
O10 C8 C3 116.46(12)
C12 C11 S1 106.45(9)
C12 C11 H11A 110.4
S1 C11 H11A 110.4
C12 C11 H11B 110.4
S1 C11 H11B 110.4
H11A C11 H11B 108.6
O14 C12 O13 124.28(13)
O14 C12 C11 122.71(12)
O13 C12 C11 112.98(12)
C12 O13 H13 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.7563(13)
S1 C11 1.8194(13)
C2 C3 1.3989(17)
C2 C7 1.4037(17)
C3 N4 1.3448(16)
C3 C8 1.5202(18)
N4 C5 1.3293(18)
N4 H4 0.8600
C5 C6 1.374(2)
C5 H5 0.9300
C6 C7 1.3774(19)
C6 H6 0.9300
C7 H7 0.9300
C8 O9 1.2333(18)
C8 O10 1.2483(17)
C11 C12 1.5200(18)
C11 H11A 0.9700
C11 H11B 0.9700
C12 O14 1.2077(17)
C12 O13 1.3124(16)
O13 H13 0.89(2)
