Copper-Catalyzed Remote C–H Functionalizations of Naphthylamides through a Coordinating Activation Strategy and Single-Electron-Transfer (SET) Mechanism
Li, Jun-Ming; Wang, Yong-Heng; Yu, Yang; Wu, Rui-Bo; Weng, Jiang; Lu, Gui; ACS Catalysis  (2017) 2661–; doi:10.1021/acscatal.6b03671

data_4514068
_publ_section_title
;
 Copper-Catalyzed Remote C--H Functionalizations of Naphthylamides through
 a Coordinating Activation Strategy and Single-Electron-Transfer (SET)
 Mechanism
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2661
_journal_paper_doi               10.1021/acscatal.6b03671
_journal_year                    2017
_chemical_formula_moiety         'C23 H18 N2 O3 S'
_chemical_formula_sum            'C23 H18 N2 O3 S'
_chemical_formula_weight         402.48
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                104.796(4)
_cell_angle_beta                 102.654(4)
_cell_angle_gamma                103.208(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1462(3)
_cell_length_b                   9.4252(4)
_cell_length_c                   13.2617(6)
_cell_measurement_reflns_used    5802
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      72.4840
_cell_measurement_theta_min      3.5890
_cell_volume                     915.85(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9921
_diffrn_measured_fraction_theta_max 0.9575
_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     15.00 115.00   1.00    1.00    --   43.90  77.00 120.00  100
  2  \w     74.00 172.00   1.00    1.50    --  100.00 125.00  60.00   98
  3  \w     98.00 149.00   1.00    1.50    --  100.00  34.00 167.00   51
  4  \w     66.00 106.00   1.00    1.50    --  100.00 -94.00 120.00   40
  5  \w     35.00 123.00   1.00    1.50    --  100.00 -61.00  30.00   88
  6  \w     81.00 119.00   1.00    1.50    --  100.00-125.00 -60.00   38
  7  \w     86.00 113.00   1.00    1.50    --  100.00 -45.00 -90.00   27
  8  \w     78.00 140.00   1.00    1.50    --  100.00  45.00 -90.00   62
  9  \w    102.00 160.00   1.00    1.50    --  100.00  77.00-180.00   58
 10  \w     42.00  68.00   1.00    1.50    --  100.00 -45.00 -90.00   26
 11  \w     18.00 109.00   1.00    1.50    --  100.00 -94.00   0.00   91
 12  \w     31.00 118.00   1.00    1.50    --  100.00 -61.00 150.00   87
 13  \w      4.00  95.00   1.00    1.00    --   43.90-125.00  30.00   91
 14  \w    -51.00 -21.00   1.00    1.50    --  -90.00 125.00  90.00   30
 15  \w   -161.00 -83.00   1.00    1.50    --  -90.00 -77.00  90.00   78
 16  \w   -107.00 -82.00   1.00    1.00    --  -43.90 -99.00   0.00   25
 17  \w   -113.00 -82.00   1.00    1.00    --  -43.90 -99.00 -60.00   31
 18  \w   -117.00 -92.00   1.00    1.00    --  -43.90 -99.00 -30.00   25
 19  \w   -123.00 -79.00   1.00    1.00    --  -43.90 -99.00  90.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1913312000
_diffrn_orient_matrix_UB_12      -0.0067270000
_diffrn_orient_matrix_UB_13      -0.0016119000
_diffrn_orient_matrix_UB_21      -0.0588988000
_diffrn_orient_matrix_UB_22      -0.1758179000
_diffrn_orient_matrix_UB_23      -0.0548316000
_diffrn_orient_matrix_UB_31      0.0353144000
_diffrn_orient_matrix_UB_32      -0.0219422000
_diffrn_orient_matrix_UB_33      0.1131389000
_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  0.0215
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6976
_diffrn_reflns_theta_full        67.0646
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         3.61
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.4594
_exptl_crystal_description       block
_exptl_crystal_F_000             421.9386
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2931
_refine_diff_density_min         -0.4233
_refine_diff_density_rms         0.0487
_refine_ls_d_res_high            0.8371
_refine_ls_d_res_low             12.2524
_refine_ls_goodness_of_fit_ref   1.0605
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0605
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.4182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3109
_reflns_number_total             3250
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            cs6b03671_si_002.cif
_cod_data_source_block           ljm_160323
_cod_original_cell_volume        915.85(7)
_cod_database_code               4514068
_reflns_odcompleteness_completeness 99.21
_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 Aromatic/amide H refined with riding coordinates:
 C20(H20), C16(H16)
;
_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 5.107
_oxdiff_exptl_absorpt_empirical_full_min 0.479