Benzoisothiazolone Organo/Copper-Cocatalyzed Redox Dehydrative Construction of Amides and Peptides from Carboxylic Acids using (EtO)3P as the Reductant and O2 in Air as the Terminal Oxidant.
Liebeskind, Lanny S.; Gangireddy, Pavankumar; Lindale, Matthew G.; Journal of the American Chemical Society 138 (2016) 6715–6718; doi:10.1021/jacs.6b03168

data_4130414
_publ_section_title
;
 Benzoisothiazolone Organo/Copper-Cocatalyzed Redox Dehydrative
 Construction of Amides and Peptides from Carboxylic Acids using (EtO)3P
 as the Reductant and O2 in Air as the Terminal Oxidant.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6715
_journal_page_last               6718
_journal_paper_doi               10.1021/jacs.6b03168
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C16 H24 Cu I2 N8'
_chemical_formula_sum            'C16 H0.5 Cu I2 N8'
_chemical_formula_weight         622.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-11-19
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.602(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8238(12)
_cell_length_b                   9.7820(15)
_cell_length_c                   14.414(2)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.590
_cell_measurement_theta_min      2.517
_cell_volume                     1102.7(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'APEX2 Mo source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14602
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.590
_diffrn_reflns_theta_min         2.517
_diffrn_source                   'sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.805
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1841 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.7431.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_description       plate
_exptl_crystal_F_000             575
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.188
_refine_diff_density_max         2.067
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0269
_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^)+(0.0370P)^2^+0.9560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3029
_reflns_number_total             3346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03168_si_002.cif
_cod_data_source_block           lsl-pa-167
_cod_original_formula_sum        'C16 H0.50 Cu I2 N8'
_cod_database_code               4130414
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3-H3 \\sim C2-H2 \\sim C1-H1
 with sigma of 0.004
 C7-H7 \\sim C6-H6 \\sim C5-H5
 with sigma of 0.004
3. Uiso/Uaniso restraints and constraints
Uiso(H2) = Uiso(H3) = Uiso(H1)
Uiso(H7) = Uiso(H6) = Uiso(H5)
4.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              90290
_shelx_hkl_checksum              20387
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'