#------------------------------------------------------------------------------
#$Date: 2020-09-06 13:22:10 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256178 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157660.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_7157660
loop_
_publ_author_name
'Greve, Eric'
'Lindeman, Sergey V.'
'Scartelli, Christina'
'Lin, Lin'
'Flaumenhaft, Robert'
'Dockendorff, Chris'
_publ_section_title
;
 Route exploration and synthesis of the reported pyridone-based PDI
 inhibitor STK076545.
;
_journal_issue                   34
_journal_name_full               'Organic & 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         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-04-16
_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                 93.573(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.04830(16)
_cell_length_b                   9.6420(2)
_cell_length_c                   17.8160(4)
_cell_measurement_reflns_used    8470
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3010
_cell_measurement_theta_min      3.7760
_cell_volume                     1208.42(5)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  35.00   1.00    6.00    --   10.69 -37.00 -60.00   99
  2  ω    -77.00  99.00   1.00    6.00    --   10.69   0.00 150.00  176
  3  ω    -64.00  35.00   1.00    6.00    --   10.69 -37.00  60.00   99
  4  ω    -20.00  22.00   1.00    6.00    --  -10.77 -99.00 150.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0730657000
_diffrn_orient_matrix_UB_12      0.0503433000
_diffrn_orient_matrix_UB_13      0.0014998000
_diffrn_orient_matrix_UB_21      -0.0359802000
_diffrn_orient_matrix_UB_22      -0.0198910000
_diffrn_orient_matrix_UB_23      -0.0364828000
_diffrn_orient_matrix_UB_31      -0.0594069000
_diffrn_orient_matrix_UB_32      -0.0498378000
_diffrn_orient_matrix_UB_33      0.0160590000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13941
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.550
_diffrn_reflns_theta_min         3.579
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0377
_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)+(0.0415P)²+0.5156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2745
_reflns_number_total             3100
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01205j2.cif
_cod_data_source_block           dock1l
_cod_depositor_comments
'Adding full bibliography for 7157660--7157663.cif.'
_cod_original_cell_volume        1208.42(4)
_cod_database_code               7157660
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C15 H13 N O3'
_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.
;
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_date_sample_submission    2019-04-15
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.844
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30098(13) 0.73124(8) 0.40963(5) 0.0233(2) Uani 1 1 d . . . . .
O2 O 0.30905(11) 0.51305(8) 0.36447(4) 0.01848(18) Uani 1 1 d . . . . .
O3 O -0.05182(11) 0.77598(8) 0.55617(4) 0.01786(18) Uani 1 1 d . . . . .
N1 N 0.26831(13) 0.73805(9) 0.56572(5) 0.01415(19) Uani 1 1 d . . . . .
C1 C 0.28654(15) 0.60790(11) 0.41886(6) 0.0161(2) Uani 1 1 d . . . . .
C2 C 0.24362(15) 0.53313(11) 0.48844(6) 0.0160(2) Uani 1 1 d . . . . .
H2 H 0.221455 0.436128 0.484585 0.019 Uiso 1 1 calc R . . . .
C3 C 0.23358(14) 0.59119(11) 0.55622(6) 0.0141(2) Uani 1 1 d . . . . .
C4 C 0.19821(14) 0.51468(11) 0.62594(6) 0.0144(2) Uani 1 1 d . . . . .
C5 C 0.20733(16) 0.58411(11) 0.69498(6) 0.0176(2) Uani 1 1 d . . . . .
H5 H 0.227970 0.681475 0.696190 0.021 Uiso 1 1 calc R . . . .
C6 C 0.18673(16) 0.51317(12) 0.76174(6) 0.0191(2) Uani 1 1 d . . . . .
H6 H 0.193260 0.562100 0.808114 0.023 Uiso 1 1 calc R . . . .
C7 C 0.15660(15) 0.37084(12) 0.76096(6) 0.0183(2) Uani 1 1 d . . . . .
H7 H 0.145158 0.321638 0.806658 0.022 Uiso 1 1 calc R . . . .
C8 C 0.14337(15) 0.30113(12) 0.69242(6) 0.0178(2) Uani 1 1 d . . . . .
H8 H 0.120218 0.204062 0.691469 0.021 Uiso 1 1 calc R . . . .
C9 C 0.16356(15) 0.37158(11) 0.62543(6) 0.0158(2) Uani 1 1 d . . . . .
H9 H 0.153858 0.322593 0.579079 0.019 Uiso 1 1 calc R . . . .
C10 C 0.11009(15) 0.82543(11) 0.56523(6) 0.0143(2) Uani 1 1 d . . . . .
C11 C 0.15586(16) 0.96994(11) 0.57618(6) 0.0169(2) Uani 1 1 d . . . . .
H11 H 0.055640 1.035505 0.577999 0.020 Uiso 1 1 calc R . . . .
C12 C 0.33904(17) 1.01486(11) 0.58400(6) 0.0184(2) Uani 1 1 d . . . . .
H12 H 0.364338 1.111077 0.590263 0.022 Uiso 1 1 calc R . . . .
C13 C 0.49226(16) 0.92040(12) 0.58293(6) 0.0184(2) Uani 1 1 d . . . . .
H13 H 0.620004 0.952109 0.588303 0.022 Uiso 1 1 calc R . . . .
C14 C 0.45287(15) 0.78387(11) 0.57409(6) 0.0170(2) Uani 1 1 d . . . . .
H14 H 0.554113 0.718885 0.573670 0.020 Uiso 1 1 calc R . . . .
C15 C 0.34572(17) 0.56821(13) 0.29157(6) 0.0221(2) Uani 1 1 d . . . . .
H15A H 0.372916 0.491887 0.257537 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.455295 0.630855 0.296367 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.233876 0.619382 0.271244 0.033 Uiso 1 1 calc GR . . . .
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
_geom_angle_publ_flag
C1 O2 C15 115.65(9) . . ?
C10 N1 C3 117.44(9) . . ?
C14 N1 C3 118.71(9) . . ?
C14 N1 C10 123.85(9) . . ?
O1 C1 O2 123.78(10) . . ?
O1 C1 C2 128.13(10) . . ?
O2 C1 C2 108.09(9) . . ?
C3 C2 C1 125.24(10) . . ?
N1 C3 C4 115.25(9) . . ?
C2 C3 N1 119.86(9) . . ?
C2 C3 C4 124.80(10) . . ?
C5 C4 C3 119.93(10) . . ?
C5 C4 C9 118.40(10) . . ?
C9 C4 C3 121.61(9) . . ?
C6 C5 C4 121.10(10) . . ?
C5 C6 C7 120.18(10) . . ?
C6 C7 C8 119.20(10) . . ?
C9 C8 C7 120.87(10) . . ?
C8 C9 C4 120.22(10) . . ?
O3 C10 N1 119.83(9) . . ?
O3 C10 C11 125.94(10) . . ?
N1 C10 C11 114.23(9) . . ?
C12 C11 C10 121.65(10) . . ?
C11 C12 C13 120.95(10) . . ?
C14 C13 C12 118.50(10) . . ?
C13 C14 N1 120.80(10) . . ?
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
O1 C1 1.2057(14) . ?
O2 C1 1.3489(13) . ?
O2 C15 1.4417(13) . ?
O3 C10 1.2380(13) . ?
N1 C3 1.4451(13) . ?
N1 C10 1.3972(13) . ?
N1 C14 1.3731(14) . ?
C1 C2 1.4814(14) . ?
C2 C3 1.3370(15) . ?
C3 C4 1.4791(14) . ?
C4 C5 1.3984(15) . ?
C4 C9 1.4012(15) . ?
C5 C6 1.3876(15) . ?
C6 C7 1.3886(16) . ?
C7 C8 1.3920(16) . ?
C8 C9 1.3883(15) . ?
C10 C11 1.4408(15) . ?
C11 C12 1.3607(16) . ?
C12 C13 1.4137(16) . ?
C13 C14 1.3526(15) . ?
