Efficient Medium Ring Size Bromolactonization Using a Sulfur-Based Zwitterionic Organocatalyst
Yi An Cheng; Tao Chen; Chong Kiat Tan; Jun Jie Heng; Ying-Yeung Yeung; Journal of the American Chemical Society 134 (2012) 16492–16495; doi:10.1021/ja307210n

data_4118737
_publ_section_title
;
 Efficient Medium Ring Size Bromolactonization Using a Sulfur-Based
 Zwitterionic Organocatalyst
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16492
_journal_page_last               16495
_journal_paper_doi               10.1021/ja307210n
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C19.5 H18 F6 N4 S'
_chemical_formula_weight         454.44
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.0247(18)
_cell_length_b                   14.497(3)
_cell_length_c                   28.512(5)
_cell_measurement_reflns_used    2058
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.47
_cell_volume                     4143.6(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18567
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.8853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         8158
_refine_ls_number_restraints     157
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0794
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.6803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.1748
_reflns_number_gt                6212
_reflns_number_total             8158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja307210n_si_001.cif
_cod_data_source_block           a187
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        4143.6(14)
_cod_original_formula_sum        'C19.50 H18 F6 N4 S'
_cod_database_code               4118737