Phosphine-Catalyzed [3+2] Annulation of β-Sulfonamido-Substituted Enones with Sulfamate-Derived Cyclic Imines.
Shi, Wangyu; Zhou, Leijie; Mao, Biming; Wang, Qijun; Wang, Chang; Zhang, Cheng; Li, Xuefeng; Xiao, Yumei; Guo, Hongchao; The Journal of organic chemistry 84 (2019) 679–686; doi:10.1021/acs.joc.8b02515

data_4036021
_publ_section_title
;
 Phosphine-Catalyzed [3+2] Annulation of \b-Sulfonamido-Substituted Enones
 with Sulfamate-Derived Cyclic Imines.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              679
_journal_page_last               686
_journal_paper_doi               10.1021/acs.joc.8b02515
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C25 H24 N2 O7 S2, C H Cl3'
_chemical_formula_sum            'C26 H25 Cl3 N2 O7 S2'
_chemical_formula_weight         647.95
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
????
;
_cell_angle_alpha                67.89(3)
_cell_angle_beta                 69.42(3)
_cell_angle_gamma                84.54(3)
_cell_formula_units_Z            2
_cell_length_a                   9.846(2)
_cell_length_b                   12.222(2)
_cell_length_c                   13.290(3)
_cell_measurement_reflns_used    4846
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4769
_cell_measurement_theta_min      1.7603
_cell_volume                     1385.9(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, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19407
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         3.250
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.156
_refine_diff_density_max         1.548
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0670
_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^)+(0.0547P)^2^+2.2190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5749
_reflns_number_total             6326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02515_si_002.cif
_cod_data_source_block           sa5284
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1385.8(6)
_cod_database_code               4036021
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.847
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              48064
_shelx_hkl_checksum              10272
_olex2_submission_special_instructions 'No special instructions were received'