#------------------------------------------------------------------------------
#$Date: 2020-09-06 13:22:10 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256178 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157661.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_7157661
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         'C14 H11 N O3'
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.24
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-08-28
_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                 98.0678(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1412(2)
_cell_length_b                   8.63104(12)
_cell_length_c                   12.6120(2)
_cell_measurement_reflns_used    6113
_cell_measurement_temperature    100.00(14)
_cell_measurement_theta_max      70.4640
_cell_measurement_theta_min      4.9400
_cell_volume                     1200.77(3)
_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(14)
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -14.00   1.00    1.00    --  -42.58 -57.00 -30.00  101
  2  ω    -34.00  75.00   1.00    1.00    --   42.58 -77.00-180.00  109
  3  ω     27.00 126.00   1.00    4.00    --  100.00 -45.00  90.00   99
  4  ω     72.00 176.00   1.00    4.00    --  100.00  30.00 -90.00  104
  5  ω     17.00 110.00   1.00    4.00    --  100.00 -94.00  60.00   93
  6  ω     94.00 173.00   1.00    4.00    --  100.00 125.00 -90.00   79
  7  ω     17.00 110.00   1.00    4.00    --  100.00 -94.00 -30.00   93
  8  ω     94.00 173.00   1.00    4.00    --  100.00 125.00  30.00   79
  9  ω   -115.00 -14.00   1.00    1.00    --  -42.58 -57.00 150.00  101
 10  ω   -125.00 -79.00   1.00    1.00    --  -42.58 -88.00-111.00   46
 11  ω     47.00 178.00   1.00    4.00    --  100.00  15.00 120.00  131
 12  ω     74.00 173.00   1.00    4.00    --  100.00  45.00   0.00   99
 13  ω     71.00 172.00   1.00    4.00    --  100.00  61.00-150.00  101
 14  ω     67.00 176.00   1.00    4.00    --  100.00  77.00 150.00  109
 15  ω   -119.00 -44.00   1.00    1.00    --  -42.58 -77.00  90.00   75
 16  ω   -115.00 -14.00   1.00    1.00    --  -42.58 -57.00-120.00  101
;
_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      0.0328752000
_diffrn_orient_matrix_UB_12      0.1395957000
_diffrn_orient_matrix_UB_13      -0.0663672000
_diffrn_orient_matrix_UB_21      -0.0276207000
_diffrn_orient_matrix_UB_22      0.1106018000
_diffrn_orient_matrix_UB_23      0.0893807000
_diffrn_orient_matrix_UB_31      0.1328925000
_diffrn_orient_matrix_UB_32      -0.0115851000
_diffrn_orient_matrix_UB_33      0.0531971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11444
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        70.502
_diffrn_reflns_theta_max         70.502
_diffrn_reflns_theta_min         4.008
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87413
_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    1.334
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0300
_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)+(0.0356P)²+0.4238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2100
_reflns_number_total             2276
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01205j2.cif
_cod_data_source_block           dock1n
_cod_depositor_comments
'Adding full bibliography for 7157660--7157663.cif.'
_cod_original_cell_volume        1200.77(4)
_cod_database_code               7157661
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C14 H11 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 99.96
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_olex2_date_sample_data_collection 2019-08-27
_olex2_date_sample_submission    2019-08-15
_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 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.849
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 0.06953(7) -0.09244(9) 0.68031(6) 0.02243(19) Uani 1 1 d . . . . .
H1 H -0.0038(16) -0.1224(19) 0.6964(13) 0.042(4) Uiso 1 1 d . . . . .
O2 O -0.03755(7) 0.10665(9) 0.60096(6) 0.0226(2) Uani 1 1 d . . . . .
O3 O 0.12921(7) 0.32161(9) 0.75351(6) 0.02057(19) Uani 1 1 d . . . . .
N1 N 0.16722(8) 0.27379(10) 0.58496(7) 0.0173(2) Uani 1 1 d . . . . .
C1 C 0.05828(10) 0.04310(12) 0.63027(8) 0.0182(2) Uani 1 1 d . . . . .
C2 C 0.17718(10) 0.11322(12) 0.61516(8) 0.0181(2) Uani 1 1 d . . . . .
C3 C 0.28263(10) 0.03729(13) 0.63173(8) 0.0214(2) Uani 1 1 d . . . . .
H3 H 0.275724 -0.069386 0.648420 0.026 Uiso 1 1 calc R . . . .
C4 C 0.40736(10) 0.09013(14) 0.62861(9) 0.0243(3) Uani 1 1 d . . . . .
C5 C 0.44350(11) 0.24443(15) 0.61875(10) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.384350 0.324427 0.612116 0.035 Uiso 1 1 calc R . . . .
C6 C 0.56475(11) 0.28176(19) 0.61858(10) 0.0367(3) Uani 1 1 d . . . . .
H6 H 0.587603 0.386754 0.610860 0.044 Uiso 1 1 calc R . . . .
C7 C 0.65238(11) 0.1674(2) 0.62956(10) 0.0395(4) Uani 1 1 d . . . . .
H7 H 0.735194 0.193472 0.629368 0.047 Uiso 1 1 calc R . . . .
C8 C 0.61883(12) 0.0149(2) 0.64079(10) 0.0388(3) Uani 1 1 d . . . . .
H8 H 0.678941 -0.063882 0.649118 0.047 Uiso 1 1 calc R . . . .
C9 C 0.49756(11) -0.02397(16) 0.64001(9) 0.0302(3) Uani 1 1 d . . . . .
H9 H 0.475638 -0.129399 0.647300 0.036 Uiso 1 1 calc R . . . .
C10 C 0.14179(9) 0.37608(12) 0.66332(8) 0.0179(2) Uani 1 1 d . . . . .
C11 C 0.13417(10) 0.53518(13) 0.63333(9) 0.0224(2) Uani 1 1 d . . . . .
H11 H 0.119143 0.610864 0.684559 0.027 Uiso 1 1 calc R . . . .
C12 C 0.14810(10) 0.58059(13) 0.53233(10) 0.0255(3) Uani 1 1 d . . . . .
H12 H 0.142888 0.687393 0.514058 0.031 Uiso 1 1 calc R . . . .
C13 C 0.17020(10) 0.47053(14) 0.45454(9) 0.0250(3) Uani 1 1 d . . . . .
H13 H 0.178986 0.502167 0.383890 0.030 Uiso 1 1 calc R . . . .
C14 C 0.17866(10) 0.31878(13) 0.48255(9) 0.0216(2) Uani 1 1 d . . . . .
H14 H 0.192593 0.243168 0.430909 0.026 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 O1 H1 109.2(10) . . ?
C10 N1 C2 116.22(8) . . ?
C14 N1 C2 120.56(9) . . ?
C14 N1 C10 123.18(9) . . ?
O1 C1 C2 113.07(9) . . ?
O2 C1 O1 124.39(10) . . ?
O2 C1 C2 122.52(10) . . ?
N1 C2 C1 112.82(9) . . ?
C3 C2 N1 123.23(10) . . ?
C3 C2 C1 123.91(10) . . ?
C2 C3 H3 114.4 . . ?
C2 C3 C4 131.17(11) . . ?
C4 C3 H3 114.4 . . ?
C5 C4 C3 125.60(11) . . ?
C9 C4 C3 116.56(11) . . ?
C9 C4 C5 117.80(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.79(12) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.52(14) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.57(12) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.40(13) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.90(13) . . ?
C8 C9 H9 119.6 . . ?
O3 C10 N1 117.89(9) . . ?
O3 C10 C11 126.24(10) . . ?
N1 C10 C11 115.86(9) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.03(10) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.67(10) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.76(10) . . ?
C14 C13 H13 120.6 . . ?
N1 C14 H14 119.8 . . ?
C13 C14 N1 120.42(10) . . ?
C13 C14 H14 119.8 . . ?
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 H1 0.907(18) . ?
O1 C1 1.3268(13) . ?
O2 C1 1.2111(13) . ?
O3 C10 1.2567(13) . ?
N1 C2 1.4375(13) . ?
N1 C10 1.3838(14) . ?
N1 C14 1.3717(14) . ?
C1 C2 1.4927(15) . ?
C2 C3 1.3358(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.4684(16) . ?
C4 C5 1.4018(18) . ?
C4 C9 1.3999(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3891(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.3909(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.4237(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3623(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.4119(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3564(16) . ?
C14 H14 0.9500 . ?
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
_geom_hbond_publ_flag
O1 H1 O3 0.907(18) 1.683(18) 2.5822(11) 170.9(16) 2_546 yes
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
O1 C1 C2 N1 -165.99(8) . . . . ?
O1 C1 C2 C3 11.62(15) . . . . ?
O2 C1 C2 N1 12.77(14) . . . . ?
O2 C1 C2 C3 -169.62(10) . . . . ?
O3 C10 C11 C12 -179.24(11) . . . . ?
N1 C2 C3 C4 2.46(18) . . . . ?
N1 C10 C11 C12 1.72(16) . . . . ?
C1 C2 C3 C4 -174.91(10) . . . . ?
C2 N1 C10 O3 -0.18(14) . . . . ?
C2 N1 C10 C11 178.94(9) . . . . ?
C2 N1 C14 C13 -179.46(10) . . . . ?
C2 C3 C4 C5 8.13(19) . . . . ?
C2 C3 C4 C9 -174.06(11) . . . . ?
C3 C4 C5 C6 178.83(11) . . . . ?
C3 C4 C9 C8 -178.39(10) . . . . ?
C4 C5 C6 C7 -0.85(19) . . . . ?
C5 C4 C9 C8 -0.40(17) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C9 0.66(19) . . . . ?
C7 C8 C9 C4 -0.45(19) . . . . ?
C9 C4 C5 C6 1.05(17) . . . . ?
C10 N1 C2 C1 70.35(11) . . . . ?
C10 N1 C2 C3 -107.28(12) . . . . ?
C10 N1 C14 C13 2.81(16) . . . . ?
C10 C11 C12 C13 0.17(17) . . . . ?
C11 C12 C13 C14 -0.72(17) . . . . ?
C12 C13 C14 N1 -0.71(16) . . . . ?
C14 N1 C2 C1 -107.53(10) . . . . ?
C14 N1 C2 C3 74.84(14) . . . . ?
C14 N1 C10 O3 177.64(9) . . . . ?
C14 N1 C10 C11 -3.23(15) . . . . ?
