Ligand-controlled Regiodivergent Ni-Catalyzed Reductive Carboxylation of Allyl Esters with CO2.
Moragas, Toni; Cornella, Josep; Martin, Ruben; Journal of the American Chemical Society  (2014) 141212124924001–; doi:10.1021/ja509077a

data_4123111
_publ_section_title
;
 Ligand-controlled Regiodivergent Ni-Catalyzed Reductive Carboxylation of
 Allyl Esters with CO2.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141212124924001
_journal_paper_doi               10.1021/ja509077a
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H14 N4 Ni'
_chemical_formula_weight         369.06
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 106.786(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.790(11)
_cell_length_b                   25.183(14)
_cell_length_c                   6.297(4)
_cell_measurement_reflns_used    475
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      16.55
_cell_measurement_theta_min      3.75
_cell_volume                     3005(3)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.563
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1381
_diffrn_reflns_av_unetI/netI     0.1313
_diffrn_reflns_Laue_measured_fraction_full 0.563
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6827
_diffrn_reflns_point_group_measured_fraction_full 0.552
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        20.990
_diffrn_reflns_theta_max         17.360
_diffrn_reflns_theta_min         1.345
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    1.301
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_description       BLock
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         1790
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0687P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1590
_reflns_Friedel_coverage         0.954
_reflns_Friedel_fraction_full    0.541
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                1213
_reflns_number_total             1790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509077a_si_002.cif
_cod_data_source_block           mo_JC_4Pyr_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 2935 2014-11-11 08:27:57Z andrius 
;
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               4123111
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.974
_shelxl_version_number           2014-3
_shelx_res_checksum              82642
_shelx_hkl_checksum              60595