Late-Stage C-H Functionalization of Nicotinamides for the Expedient Discovery of Novel Antifungal Leads.
Wang, Guotong; Cui, Pengcheng; Bai, Hongjin; Wei, Sanyue; Li, Shengkun; Journal of agricultural and food chemistry 67 (2019) 11901–11910; doi:10.1021/acs.jafc.9b05349

data_1552486
_publ_section_title
;
 Late-Stage C-H Functionalization of Nicotinamides for the Expedient
 Discovery of Novel Antifungal Leads.
;
_journal_issue                   43
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              11901
_journal_page_last               11910
_journal_paper_doi               10.1021/acs.jafc.9b05349
_journal_volume                  67
_journal_year                    2019
_chemical_formula_moiety         'C21 H15 Cl2 N3 O3'
_chemical_formula_sum            'C21 H15 Cl2 N3 O3'
_chemical_formula_weight         428.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                72.442(5)
_cell_angle_beta                 88.586(5)
_cell_angle_gamma                80.117(6)
_cell_formula_units_Z            2
_cell_length_a                   7.2225(5)
_cell_length_b                   9.7431(7)
_cell_length_c                   13.8099(7)
_cell_measurement_reflns_used    3663
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.6460
_cell_measurement_theta_min      2.8760
_cell_volume                     912.39(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -60.00  40.00   1.00    1.50    --   11.74 -57.00-150.00  100
  2  \w    -21.00  88.00   1.00    1.50    --   11.74  77.00 120.00  109
  3  \w    -16.00  85.00   1.00    1.50    --   11.74  57.00   0.00  101
  4  \w     35.00  76.00   1.00    1.50    --   11.74 178.00-150.00   41
;
_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      -0.0759271000
_diffrn_orient_matrix_UB_12      0.0500629000
_diffrn_orient_matrix_UB_13      0.0100413000
_diffrn_orient_matrix_UB_21      -0.0024204000
_diffrn_orient_matrix_UB_22      0.0437493000
_diffrn_orient_matrix_UB_23      -0.0515089000
_diffrn_orient_matrix_UB_31      -0.0646139000
_diffrn_orient_matrix_UB_32      -0.0398565000
_diffrn_orient_matrix_UB_33      -0.0122706000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7428
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.226
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43293
_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    1.559
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0486P)^2^+0.2223P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2673
_reflns_number_total             3215
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf9b05349_si_002.cif
_cod_data_source_block           61-3
_cod_depositor_comments
'Adding full bibliography for 1552483--1552486.cif.'
_cod_database_code               1552486
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.92
_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:
 C15(H15A,H15B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C11(H11), C17(H17), C2(H2A), C19(H19), C8(H8), C18(H18),
 C9(H9), C3(H3), C10(H10)
;
_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 2.048
_oxdiff_exptl_absorpt_empirical_full_min 0.407