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_1554758
_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         'C19 H20 N4 O3'
_chemical_formula_sum            'C19 H20 N4 O3'
_chemical_formula_weight         352.39
_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             2016-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2018-08-28 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                86.429(5)
_cell_angle_beta                 79.097(5)
_cell_angle_gamma                77.958(6)
_cell_formula_units_Z            2
_cell_length_a                   7.8860(4)
_cell_length_b                   9.5658(7)
_cell_length_c                   11.4661(7)
_cell_measurement_reflns_used    4467
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2260
_cell_measurement_theta_min      3.9110
_cell_volume                     830.42(9)
_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 0.9980
_diffrn_measured_fraction_theta_max 0.9665
_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    -53.00 -15.00   1.00    1.00    --  -40.98 125.00   0.00   38
  2  \w    -95.00  -8.00   1.00    1.00    --  -40.98 125.00 -90.00   87
  3  \w   -112.00 -17.00   1.00    1.00    --  -40.98 -37.00 120.00   95
  4  \w     60.00  94.00   1.00    1.00    --   40.98-125.00  90.00   34
  5  \w     54.00 120.00   1.00    1.00    --  106.95-125.00  30.00   66
  6  \w     54.00 113.00   1.00    1.00    --  106.95-125.00-120.00   59
  7  \w     88.00 114.00   1.00    1.00    --  106.95-125.00-180.00   26
  8  \w     54.00 140.00   1.00    1.00    --  106.95 -77.00-150.00   86
  9  \w     81.00 169.00   1.00    1.00    --  106.95  45.00 -60.00   88
 10  \w    107.00 133.00   1.00    1.00    --  106.95 125.00  90.00   26
 11  \w     55.00 129.00   1.00    1.00    --  106.95  15.00  60.00   74
 12  \w     40.00 140.00   1.00    1.00    --  106.95 -77.00  30.00  100
 13  \w     40.00  67.00   1.00    1.00    --  106.95-125.00-180.00   27
 14  \w     33.00 134.00   1.00    1.00    --  106.95 -30.00 -30.00  101
 15  \w     34.00 134.00   1.00    1.00    --  106.95 -30.00 120.00  100
 16  \w   -108.00 -30.00   1.00    1.00    --  -40.98 -37.00-150.00   78
;
_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      -0.0604800000
_diffrn_orient_matrix_UB_12      -0.0123866000
_diffrn_orient_matrix_UB_13      0.1354288000
_diffrn_orient_matrix_UB_21      0.1938274000
_diffrn_orient_matrix_UB_22      -0.0417937000
_diffrn_orient_matrix_UB_23      0.0161439000
_diffrn_orient_matrix_UB_31      0.0039824000
_diffrn_orient_matrix_UB_32      0.1588462000
_diffrn_orient_matrix_UB_33      0.0114346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5513
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         3.927
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88880
_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            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0521P)^2^+0.3785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3112
_reflns_number_total             3233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00170k2.cif
_cod_data_source_block           exp_181
_cod_database_code               1554758
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C16(H16A,H16B), C19(H19A,H19B), C2(H2A,H2B), C18(H18A,H18B), C1(H1A,H1B),
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C13(H13), C5(H5), C14(H14), C8(H8), C6(H6), C7(H7)
;
_shelx_shelxl_version_number     2014/7
_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 1.138
_oxdiff_exptl_absorpt_empirical_full_min 0.858