Pyridine-NHC: Effective Ligand in Pd-Catalyzed Cyclopropanation of Esters with Substituted Allyl Carbonates.
Huang, Jian-Qiang; Ding, Chang-Hua; Hou, Xue-Long; The Journal of organic chemistry 79 (2014) 12010–12017; doi:10.1021/jo5018712

data_4030065
_publ_section_title
;
 Pyridine-NHC: Effective Ligand in Pd-Catalyzed Cyclopropanation of Esters
 with Substituted Allyl Carbonates.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12010
_journal_page_last               12017
_journal_paper_doi               10.1021/jo5018712
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H21.5 F6 N3.5 P Pd'
_chemical_formula_weight         598.31
_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                   11.993(3)
_cell_length_b                   17.981(4)
_cell_length_c                   22.586(5)
_cell_measurement_reflns_used    5668
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.566
_cell_measurement_theta_min      4.463
_cell_volume                     4871(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0784
_diffrn_reflns_av_sigmaI/netI    0.0782
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27301
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10757
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2392
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.145
_refine_diff_density_max         1.618
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.152
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         9072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0885P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1691
_reflns_number_gt                6130
_reflns_number_total             9072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5018712_si_003.cif
_cod_data_source_block           cd212616
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/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 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030065--4030066.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_original_formula_sum        'C23 H21.50 F6 N3.50 P Pd'
_cod_database_code               4030065