Palladium-catalyzed N-(2-pyridyl)sulfonyl-directed C(sp3)–H γ-arylation of amino acid derivatives
Rodríguez, Nuria; Romero-Revilla, Jose A.; Fernández-Ibáñez, M. Ángeles; Carretero, Juan C.; Chemical Science 4 (2013) 175–; doi:10.1039/c2sc21162a

data_1514850
_publ_section_title
;
 Palladium-catalyzed N-(2-pyridyl)sulfonyl-directed C(sp3)--H \g-arylation
 of amino acid derivatives
;
_journal_issue                   1
_journal_name_full               'Chemical Science'
_journal_page_first              175
_journal_paper_doi               10.1039/c2sc21162a
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H24 N2 O6 S'
_chemical_formula_sum            'C19 H24 N2 O6 S'
_chemical_formula_weight         408.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   9.8306(5)
_cell_length_b                   17.0929(8)
_cell_length_c                   24.3215(12)
_cell_measurement_reflns_used    5052
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      3.63
_cell_volume                     4086.8(3)
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19517
_diffrn_reflns_theta_full        66.56
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_min         3.63
_exptl_absorpt_coefficient_mu    1.735
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         6646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0816P)^2^+0.6006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1548
_reflns_number_gt                5052
_reflns_number_total             6646
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc21162a.txt
_cod_data_source_block           19fin
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_Hall     P2ac2ab
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1514850