Route exploration and synthesis of the reported pyridone-based PDI inhibitor STK076545.
Greve, Eric; Lindeman, Sergey V.; Scartelli, Christina; Lin, Lin; Flaumenhaft, Robert; Dockendorff, Chris; Organic & biomolecular chemistry 18 (2020) 6665–6681; doi:10.1039/d0ob01205j

data_7157662
_publ_section_title
;
 Route exploration and synthesis of the reported pyridone-based PDI
 inhibitor STK076545.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6665
_journal_page_last               6681
_journal_paper_doi               10.1039/d0ob01205j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C14 H13 N O4, 2(H2 O)'
_chemical_formula_sum            'C14 H17 N O6'
_chemical_formula_weight         295.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-14 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.672(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.1618(8)
_cell_length_b                   6.1459(2)
_cell_length_c                   20.0176(6)
_cell_measurement_reflns_used    4399
_cell_measurement_temperature    99.8(3)
_cell_measurement_theta_max      70.2010
_cell_measurement_theta_min      4.4090
_cell_volume                     2835.56(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -17.00   1.00    8.00    --  -41.71 -37.00   0.00   99
  2  \w    -83.00  38.00   1.00    8.00    --  -41.71  19.00-150.00  121
  3  \w     27.00 126.00   1.00   32.00    --  100.00 -45.00-150.00   99
  4  \w     94.00 173.00   1.00   32.00    --  100.00 125.00-150.00   79
  5  \w     17.00 110.00   1.00   32.00    --  100.00 -94.00 -30.00   93
  6  \w     72.00 176.00   1.00   32.00    --  100.00  30.00  30.00  104
  7  \w     74.00 173.00   1.00   32.00    --  100.00  45.00 -30.00   99
  8  \w     94.00 173.00   1.00   32.00    --  100.00 125.00-180.00   79
  9  \w     24.00 133.00   1.00   32.00    --  100.00 -77.00 120.00  109
 10  \w   -116.00 -17.00   1.00    8.00    --  -41.71 -37.00-180.00   99
 11  \w   -114.00 -14.00   1.00    8.00    --  -41.71 -57.00 120.00  100
 12  \w     47.00 178.00   1.00   32.00    --  100.00  15.00-180.00  131
 13  \w     71.00 172.00   1.00   32.00    --  100.00  61.00  60.00  101
 14  \w     71.00 170.00   1.00   32.00    --  100.00  61.00-150.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0021223000
_diffrn_orient_matrix_UB_12      -0.0198173000
_diffrn_orient_matrix_UB_13      -0.0769381000
_diffrn_orient_matrix_UB_21      0.0644592000
_diffrn_orient_matrix_UB_22      -0.0666768000
_diffrn_orient_matrix_UB_23      0.0065901000
_diffrn_orient_matrix_UB_31      -0.0175367000
_diffrn_orient_matrix_UB_32      -0.2407786000
_diffrn_orient_matrix_UB_33      0.0045418000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12120
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        70.721
_diffrn_reflns_theta_max         70.721
_diffrn_reflns_theta_min         3.836
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0684P)^2^+1.8284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2302
_reflns_number_total             2702
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01205j2.cif
_cod_data_source_block           dock1m
_cod_depositor_comments
'Adding full bibliography for 7157660--7157663.cif.'
_cod_original_cell_volume        2835.54(16)
_cod_database_code               7157662
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C14 H17 N O6'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
;
_olex2_date_sample_data_collection 2019-04-23
_olex2_date_sample_submission    2019-04-23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.718
_oxdiff_exptl_absorpt_empirical_full_min 0.683