Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α-Bromoenones with Amino Alcohols.
Rulev, Alexander Yu; Romanov, Alexey R.; Kondrashov, Evgeniy V.; Ushakov, Igor A.; Vashchenko, Alexander V.; Muzalevskiy, Vasiliy M.; Nenajdenko, Valentine G.; The Journal of organic chemistry 81 (2016) 10029–10034; doi:10.1021/acs.joc.6b01927

data_4037291
_publ_section_title
;
 Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction
 of Fluorinated \a-Bromoenones with Amino Alcohols.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10029
_journal_page_last               10034
_journal_paper_doi               10.1021/acs.joc.6b01927
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C14 H15 F3 N2 O4'
_chemical_formula_sum            'C14 H15 F3 N2 O4'
_chemical_formula_weight         332.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                83.266(3)
_cell_angle_beta                 74.936(4)
_cell_angle_gamma                80.647(4)
_cell_formula_units_Z            2
_cell_length_a                   7.3624(8)
_cell_length_b                   7.3704(7)
_cell_length_c                   14.0312(15)
_cell_measurement_temperature    0(2)
_cell_volume                     723.20(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      0.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34419
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.211
_diffrn_reflns_theta_min         2.810
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1629 before and 0.0806 after correction.
The Ratio of minimum to maximum transmission is 0.8724.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.1046
_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^)+(0.0410P)^2^+9.8984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2894
_refine_ls_wR_factor_ref         0.2935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2449
_reflns_number_total             2866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01927_si_002.cif
_cod_data_source_block           a
_cod_database_code               4037291
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.944
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), N4(H4), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              58615
_shelx_hkl_checksum              20981
_olex2_submission_special_instructions 'No special instructions were received'