#------------------------------------------------------------------------------
#$Date: 2020-09-06 13:22:10 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256178 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157662.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_7157662
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 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    8.00    --  -41.71 -37.00   0.00   99
  2  ω    -83.00  38.00   1.00    8.00    --  -41.71  19.00-150.00  121
  3  ω     27.00 126.00   1.00   32.00    --  100.00 -45.00-150.00   99
  4  ω     94.00 173.00   1.00   32.00    --  100.00 125.00-150.00   79
  5  ω     17.00 110.00   1.00   32.00    --  100.00 -94.00 -30.00   93
  6  ω     72.00 176.00   1.00   32.00    --  100.00  30.00  30.00  104
  7  ω     74.00 173.00   1.00   32.00    --  100.00  45.00 -30.00   99
  8  ω     94.00 173.00   1.00   32.00    --  100.00 125.00-180.00   79
  9  ω     24.00 133.00   1.00   32.00    --  100.00 -77.00 120.00  109
 10  ω   -116.00 -17.00   1.00    8.00    --  -41.71 -37.00-180.00   99
 11  ω   -114.00 -14.00   1.00    8.00    --  -41.71 -57.00 120.00  100
 12  ω     47.00 178.00   1.00   32.00    --  100.00  15.00-180.00  131
 13  ω     71.00 172.00   1.00   32.00    --  100.00  61.00  60.00  101
 14  ω     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       'ω 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/[σ²(Fo²)+(0.0684P)²+1.8284P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_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 99.75
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.43420(5) 0.55094(19) 0.27445(5) 0.0265(3) Uani 1 1 d . . . . .
O2 O 0.43379(5) 0.84264(18) 0.20708(6) 0.0274(3) Uani 1 1 d . . . . .
H2 H 0.4371(11) 0.923(4) 0.2459(13) 0.047(6) Uiso 1 1 d . . . . .
O3 O 0.44990(5) 0.71211(18) 0.00951(5) 0.0260(3) Uani 1 1 d . . . . .
O4 O 0.41390(5) 0.28485(18) 0.16705(6) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.4338(12) 0.214(5) 0.1380(14) 0.058(7) Uiso 1 1 d . . . . .
N1 N 0.37786(5) 0.4864(2) 0.03892(6) 0.0210(3) Uani 1 1 d . . . . .
C1 C 0.43089(6) 0.6337(3) 0.21911(8) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.42468(7) 0.5050(2) 0.15395(8) 0.0218(3) Uani 1 1 d . . . . .
H2A H 0.462485 0.513551 0.133896 0.026 Uiso 1 1 calc R . . . .
C3 C 0.37760(6) 0.6063(2) 0.10331(7) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.390414 0.758213 0.094711 0.025 Uiso 1 1 calc R . . . .
C4 C 0.31725(6) 0.6228(2) 0.12587(7) 0.0218(3) Uani 1 1 d . . . . .
C5 C 0.28094(7) 0.7826(3) 0.09579(9) 0.0289(4) Uani 1 1 d . . . . .
H5 H 0.294472 0.872369 0.061975 0.035 Uiso 1 1 calc R . . . .
C6 C 0.22551(8) 0.8135(3) 0.11420(10) 0.0350(4) Uani 1 1 d . . . . .
H6 H 0.201445 0.924107 0.093259 0.042 Uiso 1 1 calc R . . . .
C7 C 0.20512(7) 0.6833(3) 0.16306(9) 0.0323(4) Uani 1 1 d . . . . .
H7 H 0.167091 0.704064 0.175850 0.039 Uiso 1 1 calc R . . . .
C8 C 0.24049(8) 0.5225(3) 0.19320(9) 0.0335(4) Uani 1 1 d . . . . .
H8 H 0.226542 0.432241 0.226626 0.040 Uiso 1 1 calc R . . . .
C9 C 0.29647(7) 0.4920(3) 0.17486(8) 0.0288(4) Uani 1 1 d . . . . .
H9 H 0.320485 0.381407 0.195923 0.035 Uiso 1 1 calc R . . . .
C10 C 0.41710(6) 0.5528(3) -0.00524(7) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.41695(7) 0.4302(3) -0.06591(8) 0.0247(3) Uani 1 1 d . . . . .
H11 H 0.441737 0.473603 -0.098583 0.030 Uiso 1 1 calc R . . . .
C12 C 0.38236(7) 0.2534(3) -0.07815(8) 0.0265(4) Uani 1 1 d . . . . .
H12 H 0.383714 0.172988 -0.118497 0.032 Uiso 1 1 calc R . . . .
C13 C 0.34431(8) 0.1893(3) -0.03071(8) 0.0283(4) Uani 1 1 d . . . . .
H13 H 0.319897 0.065971 -0.038750 0.034 Uiso 1 1 calc R . . . .
C14 C 0.34327(7) 0.3069(3) 0.02643(8) 0.0263(3) Uani 1 1 d . . . . .
H14 H 0.317966 0.264039 0.058609 0.032 Uiso 1 1 calc R . . . .
O2W O 0.48488(5) 0.0931(2) 0.08097(6) 0.0261(3) Uani 1 1 d . . . . .
H2WA H 0.4724(11) -0.031(5) 0.0639(13) 0.051(7) Uiso 1 1 d . . . . .
H2WB H 0.5044(12) 0.157(4) 0.0498(13) 0.054(7) Uiso 1 1 d . . . . .
O1W O 0.43598(5) 0.10115(19) 0.30547(6) 0.0263(3) Uani 1 1 d . . . . .
H1WA H 0.4389(10) 0.233(4) 0.2870(12) 0.043(6) Uiso 1 1 d . . . . .
H1WB H 0.4631(12) 0.096(4) 0.3403(14) 0.055(7) Uiso 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 0.0181 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 0 -11 0.0134
7 0 11 0.0104
2 -4 0 0.1719
-2 4 0 0.1719
15 0 -3 0.0883
-15 0 3 0.0883
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
C10 N1 C3 117.72(12) . . ?
C14 N1 C3 120.31(12) . . ?
C14 N1 C10 121.80(13) . . ?
O1 C1 O2 125.36(14) . . ?
O1 C1 C2 123.84(14) . . ?
O2 C1 C2 110.77(13) . . ?
O4 C2 C1 110.14(12) . . ?
O4 C2 C3 112.56(12) . . ?
C1 C2 C3 110.74(12) . . ?
N1 C3 C2 107.86(12) . . ?
N1 C3 C4 112.03(12) . . ?
C4 C3 C2 116.35(12) . . ?
C5 C4 C3 117.04(14) . . ?
C9 C4 C3 124.45(14) . . ?
C9 C4 C5 118.50(15) . . ?
C6 C5 C4 121.25(16) . . ?
C7 C6 C5 120.00(17) . . ?
C6 C7 C8 119.55(16) . . ?
C7 C8 C9 120.47(16) . . ?
C4 C9 C8 120.23(16) . . ?
O3 C10 N1 119.83(14) . . ?
O3 C10 C11 124.13(14) . . ?
N1 C10 C11 116.04(14) . . ?
C12 C11 C10 121.80(14) . . ?
C11 C12 C13 119.84(15) . . ?
C14 C13 C12 118.86(15) . . ?
C13 C14 N1 121.59(15) . . ?
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 1.2144(19) . ?
O2 C1 1.310(2) . ?
O3 C10 1.257(2) . ?
O4 C2 1.4050(18) . ?
N1 C3 1.4851(19) . ?
N1 C10 1.3901(19) . ?
N1 C14 1.372(2) . ?
C1 C2 1.520(2) . ?
C2 C3 1.545(2) . ?
C3 C4 1.514(2) . ?
C4 C5 1.391(2) . ?
C4 C9 1.390(2) . ?
C5 C6 1.383(2) . ?
C6 C7 1.382(3) . ?
C7 C8 1.383(3) . ?
C8 C9 1.395(2) . ?
C10 C11 1.429(2) . ?
C11 C12 1.358(2) . ?
C12 C13 1.414(2) . ?
C13 C14 1.355(2) . ?
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
O2 H2 O1W 0.92(3) 1.62(3) 2.5272(16) 169(2) 1_565 yes
O4 H4 O2W 0.89(3) 1.88(3) 2.7606(16) 171(3) . yes
O2W H2WA O3 0.87(3) 1.96(3) 2.8204(17) 169(2) 1_545 yes
O2W H2WB O3 0.90(3) 1.85(3) 2.7454(16) 175(2) 5_665 yes
O1W H1WA O1 0.89(3) 1.97(3) 2.8327(17) 161(2) . yes
O1W H1WA O4 0.89(3) 2.44(2) 2.9889(16) 120.4(19) . yes
O1W H1WB O2W 0.89(3) 1.89(3) 2.7761(17) 175(2) 2_655 yes
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.9949 -0.0006 -11.0010 0.8613 -0.5233 0.0728
6.9949 0.0006 11.0010 -0.8613 0.5233 -0.0728
1.9942 -4.0020 0.0113 0.0742 0.3955 0.9287
-1.9942 4.0020 -0.0113 -0.0742 -0.3955 -0.9287
15.0007 -0.0005 -2.9898 0.1982 0.9473 -0.2765
-15.0007 0.0005 2.9898 -0.1982 -0.9473 0.2765
