Metal-free stereoselective annulation of quinolines with trifluoroacetylacetylenes and water: an access to fluorinated oxazinoquinolines.
Trofimov, B. A.; Belyaeva, K. V.; Nikitina, L. P.; Afonin, A. V.; Vashchenko, A. V.; Muzalevskiy, V. M.; Nenajdenko, V. G.; Chemical communications (Cambridge, England) 54 (2018) 2268–2271; doi:10.1039/c7cc09725e

data_7121198
_publ_section_title
;
 Metal-free stereoselective annulation of quinolines with
 trifluoroacetylacetylenes and water: an access to fluorinated
 oxazinoquinolines.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2268
_journal_page_last               2271
_journal_paper_doi               10.1039/c7cc09725e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C9 H6 Br N, C19 H13 Br F3 N O2'
_chemical_formula_sum            'C28 H19 Br2 F3 N2 O2'
_chemical_formula_weight         632.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-20 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.46(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.054(5)
_cell_length_b                   15.229(9)
_cell_length_c                   17.101(10)
_cell_measurement_reflns_used    632
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      2.26
_cell_measurement_theta_min      23.5
_cell_volume                     2606(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  No
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            52763
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.734
_diffrn_reflns_theta_min         2.260
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    3.160
_exptl_absorpt_correction_T_max  0.5330
_exptl_absorpt_correction_T_min  0.2940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.513
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.228
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00181(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+2.6633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3696
_reflns_number_total             5518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09725e2.cif
_cod_data_source_block           a_a
_cod_depositor_comments
'Adding full bibliography for 7121197--7121198.cif.'
_cod_original_cell_volume        2607(3)
_cod_database_code               7121198
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.533
_shelx_estimated_absorpt_t_min   0.294
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C24(H24), C25(H25), C26(H26), C28(H28)
;
_shelx_res_checksum              18589
_olex2_submission_special_instructions 'No special instructions were received'