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_1554759
_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         'C21 H16 Cl N3 O3'
_chemical_formula_sum            'C21 H16 Cl N3 O3'
_chemical_formula_weight         393.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-12 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                71.104(10)
_cell_angle_beta                 70.410(11)
_cell_angle_gamma                73.474(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0444(10)
_cell_length_b                   10.7234(12)
_cell_length_c                   11.5467(13)
_cell_measurement_reflns_used    4164
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.0600
_cell_measurement_theta_min      2.7150
_cell_volume                     870.38(19)
_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 0.860
_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    -88.00  21.00   1.00    2.00    --  -11.59 -77.00  60.00  109
  2  \w    -60.00  40.00   1.00    2.00    --   11.74 -57.00-180.00  100
  3  \w    -20.00  53.00   1.00    2.00    --   11.74 -99.00-180.00   73
  4  \w    -16.00  85.00   1.00    2.00    --   11.74  57.00 -30.00  101
  5  \w    -86.00 -47.00   1.00    2.00    --  -11.59 -37.00 150.00   39
  6  \w    -20.00  53.00   1.00    2.00    --   11.74 -99.00   0.00   73
;
_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      0.0845227000
_diffrn_orient_matrix_UB_12      0.0148201000
_diffrn_orient_matrix_UB_13      -0.0086707000
_diffrn_orient_matrix_UB_21      -0.0342412000
_diffrn_orient_matrix_UB_22      0.0209335000
_diffrn_orient_matrix_UB_23      0.0573191000
_diffrn_orient_matrix_UB_31      0.0282393000
_diffrn_orient_matrix_UB_32      -0.0665426000
_diffrn_orient_matrix_UB_33      0.0343716000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11524
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.586
_diffrn_reflns_theta_min         2.048
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49795
_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    1.503
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0561
_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/[\s^2^(Fo^2^)+(0.0589P)^2^+0.4737P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3235
_reflns_number_total             4192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00170k2.cif
_cod_data_source_block           54-1
_cod_original_cell_volume        870.4(2)
_cod_database_code               1554759
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.968
_reflns_odcompleteness_completeness 99.97
_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.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C12(H12), C17(H17), C4(H4), C19(H19), C2(H2A), C21(H21),
 C18(H18), C11(H11), C9(H9), C10(H10)
;
_shelx_res_checksum              87773
_shelx_hkl_checksum              58327
_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 1.645
_oxdiff_exptl_absorpt_empirical_full_min 0.653