Asymmetric Fluorinative Dearomatization of Tryptamine Derivatives
Liang, Xiao-Wei; Liu, Chuan; Zhang, Wei; You, Shuli; Chem. Commun.  (2017) –; doi:10.1039/C7CC02419C

data_7120006
_publ_section_title
;
 Asymmetric Fluorinative Dearomatization of Tryptamine Derivatives
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02419C
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H20 F4 N2 O3'
_chemical_formula_weight         388.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-01-10 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.946(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.606(4)
_cell_length_b                   6.390(3)
_cell_length_c                   13.828(6)
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.600
_cell_measurement_theta_min      4.617
_cell_volume                     932.1(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4955
_diffrn_reflns_point_group_measured_fraction_full 0.880
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         2.308
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
; 
 Flack x determined using 742 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0888
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1190P)^2^+0.2719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2281
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    0.760
_reflns_Friedel_fraction_max     0.774
_reflns_number_gt                2456
_reflns_number_total             2965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc02419c2.cif
_cod_data_source_block           cd214591
_cod_original_cell_volume        932.0(7)
_cod_database_code               7120006
_shelxl_version_number           2013-4
_shelx_res_checksum              23552