Reaction of Chlorosulfonyl Isocyanate with Fluorosubstituted Alkenes: Evidence of a Concerted Pathway
Dale F. Shellhamer; Kevyn J. Davenport; Danielle M. Hassler; Kelli R. Hickle; Jacob J. Thorpe; David J. Vandenbroek; Victor L. Heasley; Jerry A. Boatz; Arnold L. Reingold; Curtis E. Moore; Journal of Organic Chemistry 75 (2010) 7913–7916; doi:10.1021/jo101240s

data_4025790
_publ_section_title
;
 Reaction of Chlorosulfonyl Isocyanate with Fluorosubstituted Alkenes:
 Evidence of a Concerted Pathway
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7913
_journal_page_last               7916
_journal_paper_doi               10.1021/jo101240s
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C9 H7 Cl F N O3 S'
_chemical_formula_weight         263.67
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.008(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4185(5)
_cell_length_b                   5.6716(3)
_cell_length_c                   13.7167(6)
_cell_measurement_reflns_used    4138
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      65.11
_cell_measurement_theta_min      4.97
_cell_volume                     1033.72(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5633
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.54
_diffrn_reflns_theta_min         4.97
_exptl_absorpt_coefficient_mu    5.265
_exptl_absorpt_correction_T_max  0.5951
_exptl_absorpt_correction_T_min  0.3528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.5560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0748
_reflns_number_gt                1560
_reflns_number_total             1710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101240s_si_002.cif
_cod_data_source_block           plnu05
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025790