Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.
Dong, Zhe; Lu, Gang; Wang, Jianchun; Liu, Peng; Dong, Guangbin; Journal of the American Chemical Society 140 (2018) 8551–8562; doi:10.1021/jacs.8b04153

data_4132466
_publ_section_title
;
 Modular ipso/ ortho Difunctionalization of Aryl Bromides via
 Palladium/Norbornene Cooperative Catalysis.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8551
_journal_page_last               8562
_journal_paper_doi               10.1021/jacs.8b04153
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C28 H26 Fe O3'
_chemical_formula_sum            'C28 H26 Fe O3'
_chemical_formula_weight         466.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.7420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8154(5)
_cell_length_b                   18.7822(10)
_cell_length_c                   11.4495(6)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.72
_cell_measurement_theta_min      2.18
_cell_volume                     2189.11(19)
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/1 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31677
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.311
_diffrn_reflns_theta_min         2.001
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0879 before and 0.0426 after correction. The Ratio of minimum to maximum transmission is 0.9277. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method
'obtained by the evaporation of ethyl acetate/hexanes'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+1.2610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0788
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4937
_reflns_number_total             5949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b04153_si_001.cif
_cod_data_source_block           dzdao-l-139-6
_cod_database_code               4132466
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C28(H28), C26(H26), C27(H27), C25(H25), C9(H9), C11(H11), C12(H12),
 C24(H24), C20(H20), C8(H8), C7(H7), C3(H3), C21(H21), C4(H4), C22(H22), C6(H6)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              60998
_shelx_hkl_checksum              70428
_olex2_exptl_crystal_mounting_method 'mounted with a 20um-loop base'
_olex2_submission_special_instructions 'No special instructions were received'