Switchable Ring-Contractive Extrusion Reactions of 2,5-Dihydro-1,4,5-thiadiazepine S-Oxides: Entries to Pyridazines or Pyrazoles.
Cheng, Bin; Li, Yuntong; Li, Hui; Zhang, Xinping; Wang, Taimin; Li, Yun; Zhai, Hongbin; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b03003

data_4037769
_publ_section_title
;
 Switchable Ring-Contractive Extrusion Reactions of
 2,5-Dihydro-1,4,5-thiadiazepine S-Oxides: Entries to Pyridazines or
 Pyrazoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03003
_journal_year                    2019
_chemical_formula_moiety         'C11 H16 N2 O4'
_chemical_formula_sum            'C11 H16 N2 O4'
_chemical_formula_weight         240.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
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_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                75.879(6)
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_cell_angle_gamma                65.866(6)
_cell_formula_units_Z            8
_cell_length_a                   13.8348(8)
_cell_length_b                   14.2875(8)
_cell_length_c                   15.0081(10)
_cell_measurement_reflns_used    2680
_cell_measurement_temperature    293.65(10)
_cell_measurement_theta_max      21.6240
_cell_measurement_theta_min      3.5320
_cell_volume                     2620.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.65(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -11.00   15.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000 -150.0000 26

  2 omega  -19.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  -30.0000 87

  3 omega  -44.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000    0.0000 89

  4 omega    0.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  150.0000 93

  5 omega  -46.00   -4.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000   90.0000 42

  6 omega    1.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -120.0000 90
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0080187000
_diffrn_orient_matrix_UB_12      -0.0143026000
_diffrn_orient_matrix_UB_13      -0.0402182000
_diffrn_orient_matrix_UB_21      0.0425370000
_diffrn_orient_matrix_UB_22      -0.0503678000
_diffrn_orient_matrix_UB_23      0.0157212000
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_diffrn_orient_matrix_UB_32      -0.0202748000
_diffrn_orient_matrix_UB_33      0.0227936000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19065
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.361
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         10286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1475
_refine_ls_R_factor_gt           0.0815
_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^)+(0.1093P)^2^+0.0172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1875
_refine_ls_wR_factor_ref         0.2496
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5186
_reflns_number_total             10286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03003_si_003.cif
_cod_data_source_block           liyt_1026
_cod_depositor_comments
;

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '4(C11 H16 N2 O4)'
_cod_original_formula_sum        'C44 H64 N8 O16'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     961.03
_cod_database_code               4037769
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N11(H11)
2.b Idealised Me refined as rotating group:
 C43(H43a,H43b,H43c), C50(H50a,H50b,H50c), C51(H51a,H51b,H51c), C52(H52a,H52b,
 H52c), C53(H53a,H53b,H53c), C54(H54a,H54b,H54c), C55(H55a,H55b,H55c), C56(H56a,
 H56b,H56c), C57(H57a,H57b,H57c), C58(H58a,H58b,H58c), C59(H59a,H59b,H59c),
 C60(H60a,H60b,H60c), C61(H61a,H61b,H61c), C62(H62a,H62b,H62c), C63(H63a,H63b,
 H63c), C64(H64a,H64b,H64c), C65(H65a,H65b,H65c), C66(H66a,H66b,H66c),
 C1AA(H1Aa,H1Ab,H1Ac), C0AA(H0Aa,H0Ab,H0Ac)
;
_shelx_res_checksum              64350
_shelx_hkl_checksum              66231
_olex2_date_sample_data_collection 2018-10-26
_olex2_submission_special_instructions 'No special instructions were received'