Synthesis of 2-fluoro-2-pyrrolines via tandem reaction of α-trifluoromethyl-α,β-unsaturated carbonyl compounds with N-tosylated 2-aminomalonates.
Yang, Jieru; Zhou, Xiaofan; Zeng, Yu; Huang, Chaoqian; Xiao, Yuanjing; Zhang, Junliang; Chemical communications (Cambridge, England) 52 (2016) 4922–4925; doi:10.1039/c6cc00831c

data_7118851
_publ_section_title
;
 Synthesis of 2-fluoro-2-pyrrolines via tandem reaction of
 \a-trifluoromethyl-\a,\b-unsaturated carbonyl compounds with N-tosylated
 2-aminomalonates.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4922
_journal_page_last               4925
_journal_paper_doi               10.1039/c6cc00831c
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C26 H27 Cl F N O8 S'
_chemical_formula_weight         568.00
_chemical_melting_point          125.0(10)
_chemical_name_systematic
'triethyl 3-(4-chlorophenyl)-5-fluoro-1-tosyl-1H-pyrrole-2,2,4(3H)-tricarboxylate'
_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
;
2016-01-05 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 114.440(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3397(13)
_cell_length_b                   20.295(2)
_cell_length_c                   13.4500(16)
_cell_measurement_temperature    296(2)
_cell_volume                     2818.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32666
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9615
_exptl_absorpt_correction_T_min  0.9204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hexane'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4956
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+1.4107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1664
_reflns_number_gt                3114
_reflns_number_total             4956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc00831c2.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '124-126' was changed to '125.0(10)'
- 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 7118851.cif.
;
_cod_original_cell_volume        2818.0(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7118851