Diastereoselective Pd-Catalyzed C-H Arylation of Ferrocenylmethanamines with Arylboronic Acids or Pinacol Esters.
Plevová, Kristína; Mudráková, Brigita; Rakovský, Erik; Šebesta, Radovan; The Journal of organic chemistry 84 (2019) 7312–7319; doi:10.1021/acs.joc.9b00953

data_4034635
_publ_section_title
;
 Diastereoselective Pd-Catalyzed C-H Arylation of Ferrocenylmethanamines
 with Arylboronic Acids or Pinacol Esters.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7312
_journal_page_last               7319
_journal_paper_doi               10.1021/acs.joc.9b00953
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 Fe N, C6 H6 O'
_chemical_formula_sum            'C26 H29 Fe N O'
_chemical_formula_weight         427.35
_chemical_name_systematic
'(R,Rp)-N,N-dimethyl-1-(2-phenylferrocenyl)ethan-1-amine - phenol (1/1)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-02-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.02944(9)
_cell_length_b                   10.3803(2)
_cell_length_c                   23.2249(2)
_cell_measurement_reflns_used    135432
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.23
_cell_measurement_theta_min      3.81
_cell_volume                     2176.83(5)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)'
_computing_data_reduction
'X-Area Integrate 1.73.1.0 (STOE, 2018) X-Area LANA 1.73.2.0 (STOE, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            99750
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.604
_diffrn_reflns_theta_min         3.807
_diffrn_source                   'Genix3D Cu HF'
_exptl_absorpt_coefficient_mu    5.666
_exptl_absorpt_correction_T_max  0.1238
_exptl_absorpt_correction_T_min  0.0340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities. 
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different 
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, 
pp. 136 - 140. Afterwards a spherical absorption correction was performed within
STOE LANA.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1686 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0294P)^2^+1.3451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0713
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4102
_reflns_number_total             4236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00953_si_001.cif
_cod_data_source_block           jm1113
_cod_original_cell_volume        2176.82(4)
_cod_database_code               4034635
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.222
_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, All C(H,H,H,H) groups
2.a Ternary CH refined with riding coordinates and stretchable bonds:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates and stretchable bonds:
 C20(H20), C16(H16), C7(H7), C8(H8), C19(H19), C14(H14), C9(H9), C12(H12),
 C18(H18), C11(H11), C101(H101), C13(H13), C10(H10), C103(H103), C102(H102),
 C17(H17), C104(H104), C105(H105)
2.c Idealised Me refined as rotating group with stretchable bonds:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              37282
_shelx_hkl_checksum              59101
_olex2_submission_special_instructions 'No special instructions were received'