Catalyst-free 1 : 2 annulation of quinolines with trifluoroacetylacetylenes: an access to functionalized oxazinoquinolines.
Belyaeva, K. V.; Nikitina, L. P.; Afonin, A. V.; Vashchenko, A. V.; Muzalevskiy, V. M.; Nenajdenko, V. G.; Trofimov, B. A.; Organic & biomolecular chemistry 16 (2018) 8038–8041; doi:10.1039/c8ob02379d

data_7156513
_publ_section_title
;
 Catalyst-free 1&#x2009;:&#x2009;2 annulation of quinolines with
 trifluoroacetylacetylenes: an access to functionalized oxazinoquinolines.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8038
_journal_page_last               8041
_journal_paper_doi               10.1039/c8ob02379d
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C29 H17 F6 N O2'
_chemical_formula_sum            'C29 H17 F6 N O2'
_chemical_formula_weight         525.43
_chemical_name_systematic
2,2,2-trifluoro-1-[1-phenyl-3-(2-phenylethynyl)-3-(trifluoromethyl)-3H,4aH-[1,3]oxazino[3,2-<i>a</i>]quinolin-2-yl]-1-ethanone
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-19
_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.
2018-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.0770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2784(4)
_cell_length_b                   14.1722(6)
_cell_length_c                   9.8379(4)
_cell_measurement_reflns_used    781
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      2.4
_cell_volume                     1181.09(9)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.926
_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  0.0358
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            38293
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.907
_diffrn_reflns_theta_min         2.267
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.7159.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       'pale, cyllinder-like'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(16)
_refine_ls_extinction_coef       0.022(2)
_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   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         6736
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0347P)^2^+0.2245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0746
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                5807
_reflns_number_total             6736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02379d2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7156513.cif.'
_cod_database_code               7156513
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.940
_olex2_refinement_description
;
;
_shelx_res_checksum              46977
_olex2_submission_special_instructions 'No special instructions were received'