Innate pharmacophore assisted selective C–H functionalization to therapeutically important nicotinamides
Song, Zehua; Wang, Guotong; Li, Wei; Li, Shengkun; Organic Chemistry Frontiers 6 (2019) 1613–; doi:10.1039/C9QO00170K

data_1554763
_publ_section_title
;
 Innate pharmacophore assisted selective C--H functionalization to
 therapeutically important nicotinamides
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1613
_journal_paper_doi               10.1039/C9QO00170K
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C29 H19 F6 N3 O4'
_chemical_formula_sum            'C29 H19 F6 N3 O4'
_chemical_formula_weight         587.47
_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     dual
_audit_creation_date             2018-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-28 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.908(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9357(8)
_cell_length_b                   13.7866(8)
_cell_length_c                   11.8725(7)
_cell_measurement_reflns_used    4301
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.3870
_cell_measurement_theta_min      2.5420
_cell_volume                     2602.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.843
_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     35.00  96.00   1.00    2.80    --   11.74 178.00 -90.00   61
  2  \w     -2.00  40.00   1.00    2.80    --   11.74  37.00-180.00   42
  3  \w    -15.00  84.00   1.00    2.80    --   11.74  57.00  30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0234493000
_diffrn_orient_matrix_UB_12      -0.0412804000
_diffrn_orient_matrix_UB_13      -0.0146981000
_diffrn_orient_matrix_UB_21      -0.0379281000
_diffrn_orient_matrix_UB_22      -0.0261831000
_diffrn_orient_matrix_UB_23      -0.0112117000
_diffrn_orient_matrix_UB_31      -0.0017053000
_diffrn_orient_matrix_UB_32      0.0159266000
_diffrn_orient_matrix_UB_33      -0.0569800000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.586
_diffrn_reflns_theta_min         2.267
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6166
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0643
_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^)+(0.0634P)^2^+1.7607P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1664
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4413
_reflns_number_total             6166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00170k2.cif
_cod_data_source_block           x_48
_cod_database_code               1554763
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 C28, F6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C28 \\sim F6: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
4.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C27(H27), C9(H9), C26(H26), C14(H14), C2(H2A), C3(H3),
 C23(H23), C24(H24), C6(H6), C15(H15), C5(H5), C17(H17), C16(H16)
;
_shelx_res_checksum              37104
_shelx_hkl_checksum              96185
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.193
_oxdiff_exptl_absorpt_empirical_full_min 0.879