Silver-catalysed tandem hydroamination and cyclization of 2-trifluoromethyl-1,3-enynes with primary amines: modular entry to 4-trifluoromethyl-3-pyrrolines.
Zhou, Xiaofan; Huang, Chaoqian; Zeng, Yu; Xiong, Jiarui; Xiao, Yuanjing; Zhang, Junliang; Chemical communications (Cambridge, England) 53 (2017) 1084–1087; doi:10.1039/c6cc09595j

data_7119273
_publ_section_title
;
 Silver-catalysed tandem hydroamination and cyclization of
 2-trifluoromethyl-1,3-enynes with primary amines: modular entry to
 4-trifluoromethyl-3-pyrrolines.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1084
_journal_page_last               1087
_journal_paper_doi               10.1039/c6cc09595j
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C18 H13 F3 I N'
_chemical_formula_weight         427.19
_chemical_melting_point          336.8(9)
_chemical_name_systematic
1-benzyl-3-iodo-2-phenyl-4-(trifluoromethyl)-1H-pyrrole
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-08-12 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.793(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.015(4)
_cell_length_b                   14.627(5)
_cell_length_c                   11.621(4)
_cell_measurement_reflns_used    9745
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.36
_cell_volume                     1726.1(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18868
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    1.882
_exptl_absorpt_correction_T_max  0.6609
_exptl_absorpt_correction_T_min  0.4591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/petroleum'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0224P)^2^+2.0734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                2634
_reflns_number_total             3027
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc09595j2.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '335.9-337.6' was changed to
'336.8(9)' - the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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

 Adding full bibliography for 7119272--7119273.cif.
;
_cod_original_cell_volume        1726.1(10)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7119273