Magnesiation employing Grignard reagents and catalytic amine. Application to the functionalization of N-phenylsulfonylpyrrole.
Dinsmore, Andrew; Billing, David G.; Mandy, Karen; Michael, Joseph P.; Mogano, Daniel; Patil, Shivaputra; Organic letters 6 (2004) 293–296; doi:10.1021/ol036288p

data_1506892
_publ_section_title
;
 Magnesiation employing Grignard reagents and catalytic amine. Application
 to the functionalization of N-phenylsulfonylpyrrole.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              293
_journal_page_last               296
_journal_paper_doi               10.1021/ol036288p
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C21 H21 Cl N2 O7 S'
_chemical_formula_weight         480.91
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2003-11-11T16:20:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                101.849(9)
_cell_angle_beta                 94.878(10)
_cell_angle_gamma                108.820(9)
_cell_formula_units_Z            2
_cell_length_a                   7.728(4)
_cell_length_b                   10.467(5)
_cell_length_c                   15.821(8)
_cell_measurement_temperature    298(2)
_cell_volume                     1169.6(10)
_computing_cell_refinement       'Bruker SAINT+ (Bruker, 1999)'
_computing_data_collection       'Bruker SMART-NT (Bruker, 1998)'
_computing_data_reduction        'Bruker XPREP (Bruker, 1999)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8087
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS:Sheldrick, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut needle'
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.162
_refine_ls_R_factor_gt           0.0707
_refine_ls_shift/su_max          0.085
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1236P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1929
_refine_ls_wR_factor_ref         0.2365
_reflns_number_gt                2484
_reflns_number_total             5592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol036288psi20031215_053016.cif
_cod_data_source_block           3dad1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506892