Copper-catalyzed intermolecular and regioselective aminofluorination of styrenes: facile access to beta-fluoro-N-protected phenethylamines
Jorge Saavedra-Olavarria; Gean C. Arteaga; Jhon J. Lopez; Edwin G. Perez; Chem.Commun. 51 (2015) 3379–; doi:10.1039/C4cc10162F

data_7116533
_publ_section_title
;
 Copper-catalyzed intermolecular and regioselective aminofluorination of
 styrenes: facile access to beta-fluoro-N-protected phenethylamines
;
_journal_name_full               Chem.Commun.
_journal_page_first              3379
_journal_paper_doi               10.1039/C4cc10162F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C15 H15 Br F N O2 S'
_chemical_formula_sum            'C15 H15 Br F N O2 S'
_chemical_formula_weight         372.24
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_audit_update_record
;
2014-12-06 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.278(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.571(2)
_cell_length_b                   5.2088(10)
_cell_length_c                   26.139(5)
_cell_measurement_temperature    297(2)
_cell_volume                     1572.8(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23482
_diffrn_reflns_theta_full        25.9988
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.56
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    2.759
_exptl_absorpt_correction_T_max  0.516
_exptl_absorpt_correction_T_min  0.337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS Bruker'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5719
_exptl_crystal_description       block
_exptl_crystal_F_000             752.0
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate'
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.2911
_refine_diff_density_min         -1.5598
_refine_diff_density_rms         0.1308
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             13.0480
_refine_ls_goodness_of_fit_ref   1.0549
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0548
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0706P)^2^+2.5502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                2329
_reflns_number_total             3100
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4cc10162f2.cif
_cod_data_source_block           EGPH_531
_cod_original_cell_volume        1572.9(5)
_cod_database_code               7116533
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_olex2_submission_original_sample_id EGPH-531
_olex2_submission_special_instructions 'No special instructions were received'