Dual Roles of β-Oxodithioesters in the Copper-Catalyzed Synthesis of Benzo[e]pyrazolo[1,5-c][1,3]thiazine Derivatives.
Wen, Li-Rong; Yuan, Wen-Kui; Li, Ming; The Journal of organic chemistry 80 (2015) 4942–4949; doi:10.1021/acs.joc.5b00288

data_4036160
_publ_section_title
;
 Dual Roles of \b-Oxodithioesters in the Copper-Catalyzed Synthesis of
 Benzo[e]pyrazolo[1,5-c][1,3]thiazine Derivatives.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4942
_journal_page_last               4949
_journal_paper_doi               10.1021/acs.joc.5b00288
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C26 H21 N3 O S, 0.5(C4 H8 O)'
_chemical_formula_sum            'C28 H25 N3 O1.5 S'
_chemical_formula_weight         459.57
_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   geom
_audit_creation_date             2014-07-18
_audit_creation_method
;

Olex2 1.2

(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)

;
_cell_angle_alpha                90
_cell_angle_beta                 106.285(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.916(2)
_cell_length_b                   11.755(3)
_cell_length_c                   25.654(5)
_cell_measurement_reflns_used    13129
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4811
_cell_measurement_theta_min      0.8269
_cell_volume                     4607.1(16)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;

'SHELXS (Sheldrick, 2013)'

;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
;

Saturn724+ (2x2 bin mode)

;
_diffrn_measurement_device_details
;

AFC10: Fixed Chi 2 circle

;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0120
_diffrn_orient_matrix_UB_12      -0.0350
_diffrn_orient_matrix_UB_13      -0.0540
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_diffrn_orient_matrix_UB_22      -0.0719
_diffrn_orient_matrix_UB_23      0.0442
_diffrn_orient_matrix_UB_31      -0.0401
_diffrn_orient_matrix_UB_32      -0.0065
_diffrn_orient_matrix_UB_33      -0.0007
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            33057
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.755
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
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_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         10529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0805
_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^)+(0.0379P)^2^+4.2211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9010
_reflns_number_total             10529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00288_si_001.cif
_cod_data_source_block           mx3212
_cod_depositor_comments
;

2020-06-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4607.0(16)
_cod_original_formula_moiety     '2(C26 H21 N3 O S), C4 H8 O'
_cod_original_formula_sum        'C56 H50 N6 O3 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     919.14
_cod_database_code               4036160
_shelxl_version_number           2013-4
_diffrn_number_total             11054
_olex2_refinement_description
;

1. Fixed Uiso

 At 1.2 times of:

  All C(H) groups, All C(H,H) groups, All N(H) groups

 At 1.5 times of:

  All C(H,H,H) groups

2.a Secondary CH2 refined with riding coordinates:

 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)

2.b Aromatic/amide H refined with riding coordinates:

 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8), C11(H11), C14(H14), C15(H15),

  C17(H17), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), N3A(H3AA),

 C2A(H2A), C3A(H3AB), C4A(H4A), C5A(H5A), C8A(H8A), C11A(H11A), C14A(H14A),

 C15A(H15A), C17A(H17A), C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A),

 C26A(H26A)

2.c Idealised Me refined as rotating group:

 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C19A(H19D,H19E,H19F), C20A(H20D,

 H20E,H20F)

;
_shelx_res_checksum              65501
_shelx_hkl_checksum              54666