β,γ-Vicinal Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Directed Nucleopalladation.
Liu, Zhen; Zeng, Tian; Yang, Kin S.; Engle, Keary M.; Journal of the American Chemical Society 138 (2016) 15122–15125; doi:10.1021/jacs.6b09170

data_4131078
_publ_section_title
;
 \b,\g-Vicinal Dicarbofunctionalization of Alkenyl Carbonyl Compounds via
 Directed Nucleopalladation.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15122
_journal_page_last               15125
_journal_paper_doi               10.1021/jacs.6b09170
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C37 H33 N3 O, 0.5(C1 H2 Cl2)'
_chemical_formula_sum            'C37.5 H34 Cl N3 O'
_chemical_formula_weight         578.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-08-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_cell_angle_alpha                90
_cell_angle_beta                 116.124(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1383(4)
_cell_length_b                   25.3721(9)
_cell_length_c                   12.0025(4)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.183
_cell_measurement_theta_min      3.484
_cell_volume                     3045.42(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            52791
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.317
_diffrn_reflns_theta_min         3.484
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  0.3175
_exptl_absorpt_correction_T_min  0.2248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0883 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.7080.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       Block
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.30(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     797
_refine_ls_number_reflns         10910
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0612
_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^)+(0.1251P)^2^+0.1348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1724
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                9611
_reflns_number_total             10910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09170_si_003.cif
_cod_data_source_block           Engle20
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C37.50 H34 Cl N3 O'
_cod_database_code               4131078
_shelx_estimated_absorpt_t_max   0.815
_shelx_estimated_absorpt_t_min   0.758
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.70(3) 0.30(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=1-FVAR(1)
 Sof(Cl1S)=Sof(Cl2S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C11'(H11'), C12'(H12')
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C22(H22A,H22B), C10'(H10C,H10D), C22'(H22C,H22D), C1S(H1SA,
 H1SB), C1B(H1BA,H1BB)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), C14(H14), C15(H15), C17(H17),
  C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C35(H35), C36(H36), C37(H37),
  N2'(H2'), C2'(H2'A), C3'(H3'), C4'(H4'), C5'(H5'), C8'(H8'), C14'(H14'),
 C15'(H15'), C17'(H17'), C18'(H18'), C19'(H19'), C20'(H20'), C21'(H21'),
 C24'(H24'), C25'(H25'), C26'(H26'), C27'(H27'), C28'(H28'), C30'(H30'),
 C31'(H31'), C32'(H32'), C35'(H35'), C36'(H36'), C37'(H37')
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9'(H9'A,H9'B,H9'C)
;
_shelx_res_checksum              46690
_shelx_hkl_checksum              78805
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'