Mechanism of Acylative Oxidation-Reduction-Condensation Reactions Using Benzoisothiazolones as Oxidant and Triethylphosphite as Stoichiometric Reductant.
Gangireddy, Pavankumar; Patro, Vidyavathi; Lam, Leighann; Morimoto, Mariko; Liebeskind, Lanny S.; The Journal of organic chemistry 82 (2017) 3513–3529; doi:10.1021/acs.joc.7b00020

data_4032469
_publ_section_title
;
 Mechanism of Acylative Oxidation-Reduction-Condensation Reactions Using
 Benzoisothiazolones as Oxidant and Triethylphosphite as Stoichiometric
 Reductant.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3513
_journal_page_last               3529
_journal_paper_doi               10.1021/acs.joc.7b00020
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C24 H16 N4 S2'
_chemical_formula_sum            'C24 H16 N4 S2'
_chemical_formula_weight         424.53
_chemical_name_systematic
; 
 N,N'-di(pyridin-2-yl)-6H,12H-dibenzo[b,f][1,5]dithiocine-6,12-diamine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-04-14
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.03.31 svn.r3164 for OlexSys, GUI svn.r5023)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.308(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9977(14)
_cell_length_b                   12.1880(14)
_cell_length_c                   13.648(2)
_cell_measurement_reflns_used    2237
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.964
_cell_measurement_theta_min      2.383
_cell_volume                     1992.4(4)
_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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0444
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15453
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.993
_diffrn_reflns_theta_min         2.762
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1114 before and 0.0448 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1164 before and 0.0520 after correction.
 The Ratio of minimum to maximum transmission is 0.58.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 15220 reflections, Rint = 0.0466
 (8419 with I > 3sig(I), Rint = 0.0411)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_recrystallization_method
'The material was recrystallised from toluene by slow evaporation'
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.196
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0759P)^2^+4.3354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2541
_reflns_number_total             3036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00020_si_003.cif
_cod_data_source_block           twin4
_cod_database_code               4032469
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12)
;
_shelx_res_checksum              54942
_shelx_hkl_checksum              26310
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id LSL-PA-137-1
_olex2_submission_special_instructions 'No special instructions were received'