Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides
Lin, Yan; Wang, Qijun; Wu, Yang; Wang, Chang; Jia, Hao; Zhang, Cheng; Huang, Jiaxing; Guo, Hongchao; RSC Advances 8 (2018) 40798–; doi:10.1039/C8RA08881K

data_7231960
_publ_section_title
;
 Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with
 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine
 2,2-dioxides
;
_journal_issue                   71
_journal_name_full               'RSC Advances'
_journal_page_first              40798
_journal_paper_doi               10.1039/C8RA08881K
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C22 H17 N3 O3 S'
_chemical_formula_sum            'C22 H17 N3 O3 S'
_chemical_formula_weight         403.44
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-15 deposited with the CCDC.
2018-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.86(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6209(15)
_cell_length_b                   12.073(2)
_cell_length_c                   21.125(4)
_cell_measurement_reflns_used    5141
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4833
_cell_measurement_theta_min      1.6867
_cell_volume                     1929.7(6)
_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  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14264
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         1.942
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       Plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.225
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0732
_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^)+(0.0228P)^2^+1.8228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3917
_reflns_number_total             4390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra08881k2.cif
_cod_data_source_block           mx5919
_cod_original_cell_volume        1929.8(7)
_cod_database_code               7231960
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
;
_shelx_res_checksum              72221
_shelx_hkl_checksum              88649
_olex2_submission_special_instructions 'No special instructions were received'