Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling.
Kim, Byoungmoo; Chinn, Alex J.; Fandrick, Daniel R.; Senanayake, Chris H.; Singer, Robert A.; Miller, Scott J.; Journal of the American Chemical Society 138 (2016) 7939–7945; doi:10.1021/jacs.6b03444

data_4125100
_publ_contact_author
;
 Prof. Scott J. Miller        
 The Department of Chemistry 
 Yale University 
 P. O. Box 208107 
 New Haven 
 Connecticut 06520 USA.
;
_publ_section_title
;
 Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional
 Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7939
_journal_page_last               7945
_journal_paper_doi               10.1021/jacs.6b03444
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C21 H18 Br2 F6 N2 O2'
_chemical_formula_sum            'C21 H18 Br2 F6 N2 O2'
_chemical_formula_weight         604.19
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.340(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3264(17)
_cell_length_b                   13.9962(19)
_cell_length_c                   13.3450(18)
_cell_measurement_reflns_used    26157
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.1
_cell_volume                     2264.9(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics
;
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 6.8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32082
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
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_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    3.650
_exptl_absorpt_correction_T_max  0.450
_exptl_absorpt_correction_T_min  0.367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0271P)^2^+3.5091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3288
_reflns_number_total             4131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03444_si_002.cif
_cod_data_source_block           mini-15006
_cod_depositor_comments
'Adding full bibliography for 4125098--4125102.cif.'
_cod_database_code               4125100
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.353
_shelx_estimated_absorpt_t_max   0.450
_shelx_res_checksum              11065
_shelx_hkl_checksum              7488