Competing amination and C-H arylation pathways in Pd/xantphos-catalyzed transformations of binaphthyl triflates: switchable routes to chiral amines and helicene derivatives.
Ruch, Aaron A.; Handa, Sachin; Kong, Fanji; Nesterov, Vladimir N.; Pahls, Dale R.; Cundari, Thomas R.; Slaughter, LeGrande M; Organic & biomolecular chemistry 14 (2016) 8123–8140; doi:10.1039/c6ob01102k

data_7155243
_publ_section_title
;
 Competing amination and C-H arylation pathways in Pd/xantphos-catalyzed
 transformations of binaphthyl triflates: switchable routes to chiral
 amines and helicene derivatives.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8123
_journal_page_last               8140
_journal_paper_doi               10.1039/c6ob01102k
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C28 H14 F6'
_chemical_formula_sum            'C28 H14 F6'
_chemical_formula_weight         464.39
_chemical_melting_point          450.5(5)
_chemical_name_systematic        1,3-bis(trifluoromethyl)naphtho[1,2-g]chrysene
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-05-13 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.9067(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.81380(10)
_cell_length_b                   22.8364(3)
_cell_length_c                   9.09370(10)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.29
_cell_volume                     2007.62(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      115(2)
_diffrn_detector_area_resol_mean 0.75
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            38424
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.338
_diffrn_reflns_theta_min         1.783
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        N/A
_diffrn_standards_interval_count N/A
_diffrn_standards_interval_time  N/A
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method 'slow diff of n-hexane into THF soln'
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0331P)^2^+0.9508P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3187
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01102k2.cif
_cod_data_source_block           cmpd4a_lms210
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '450-451' was changed to '450.5(5)' -
the average value was taken and precision was estimated.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155241--7155243.cif.
;
_cod_database_code               7155243
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.995
_shelxl_version_number           2013-4
_shelx_res_checksum              22709