Ru/Cu Photoredox or Cu/Ag Catalyzed C4-H Sulfonylation of 1-Naphthylamides at Room Temperature.
Bai, Peirong; Sun, Suyan; Li, Zexian; Qiao, Huijie; Su, Xiaoxue; Yang, Fan; Wu, Yusheng; Wu, Yangjie; The Journal of organic chemistry 82 (2017) 12119–12127; doi:10.1021/acs.joc.7b01917

data_4033043
_publ_section_title
;
 Ru/Cu Photoredox or Cu/Ag Catalyzed C4-H Sulfonylation of
 1-Naphthylamides at Room Temperature.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12119
_journal_page_last               12127
_journal_paper_doi               10.1021/acs.joc.7b01917
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C22 H16 N2 O3 S'
_chemical_formula_sum            'C22 H16 N2 O3 S'
_chemical_formula_weight         388.43
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0352(3)
_cell_length_b                   10.3936(3)
_cell_length_c                   19.7212(6)
_cell_measurement_reflns_used    2846
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5680
_cell_measurement_theta_min      4.5560
_cell_volume                     1820.02(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
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_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_details
;
  1 omega -100.00  -61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -90.0000 39

  2 omega -101.00  -26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   90.0000 75

  3 omega   16.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -60.0000 26

  4 omega   58.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 35

  5 omega   15.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -150.0000 49

  6 omega   61.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -60.0000 48

  7 omega  -29.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -60.0000 85

  8 omega   58.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 26

  9 omega   88.00  128.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 40

 10 omega   40.00   69.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 29

 11 omega   84.00  160.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 76

 12 omega   86.00  176.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 90

 13 omega   50.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 49

 14 omega   45.00   71.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 26

 15 omega   68.00   95.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 27

 16 omega   64.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 27

 17 omega   40.00   66.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 26

 18 omega   54.00   97.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 43

 19 omega   64.00  149.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0811743000
_diffrn_orient_matrix_UB_12      -0.1161747000
_diffrn_orient_matrix_UB_13      -0.0251088000
_diffrn_orient_matrix_UB_21      -0.0743975000
_diffrn_orient_matrix_UB_22      0.0301404000
_diffrn_orient_matrix_UB_23      -0.0750666000
_diffrn_orient_matrix_UB_31      0.1340016000
_diffrn_orient_matrix_UB_32      0.0870222000
_diffrn_orient_matrix_UB_33      -0.0074361000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6738
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.563
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.418
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0579P)^2^+0.3527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1127
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2762
_reflns_number_total             3245
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01917_si_002.cif
_cod_data_source_block           201612194
_cod_depositor_comments          'Adding full bibliography for 4033043.cif.'
_cod_original_cell_volume        1820.01(10)
_cod_database_code               4033043
_chemical_oxdiff_formula         C30H30O2N2S1
_reflns_odcompleteness_completeness 99.68
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), N1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'