One-pot synthesis of functionalized benzo[c]coumarins and their precursors via the reaction of 2-(polyfluoroalkyl)chromones with 4-alkyl-3-cyanocoumarins
Sosnovskikh, Vyacheslav; Korotaev, Vladislav; Kutyashev, Igor; Barkov, Alexey; Safrygin, Alexander; RSC Adv.  (2016) –; doi:10.1039/C6RA12492E

data_7225504
_publ_section_title
;
 One-pot synthesis of functionalized benzo[c]coumarins and their
 precursors via the reaction of 2-(polyfluoroalkyl)chromones with
 4-alkyl-3-cyanocoumarins
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA12492E
_journal_year                    2016
_chemical_formula_moiety         'C21 H8 Br2 F3 N2 O6, C6 H16 N'
_chemical_formula_sum            'C27 H24 Br2 F3 N3 O6'
_chemical_formula_weight         703.31
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2015-08-24
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2016-03-11 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.926(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.0863(13)
_cell_length_b                   12.0796(6)
_cell_length_c                   14.2137(12)
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.1700
_cell_measurement_theta_min      2.3460
_cell_volume                     2860.0(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9439
_diffrn_measured_fraction_theta_max 0.9439
_diffrn_measurement_details
;
  1 omega  -20.00   16.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360  -99.0000 -150.0000 36

  2 omega   58.00   93.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000  150.0000 35

  3 omega   39.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360  178.0000  -30.0000 60

  4 omega   -1.00   96.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   38.0000   90.0000 97

  5 omega   -5.00   22.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000  150.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0424184000
_diffrn_orient_matrix_UB_12      0.0048443000
_diffrn_orient_matrix_UB_13      0.0209124000
_diffrn_orient_matrix_UB_21      -0.0035070000
_diffrn_orient_matrix_UB_22      0.0581354000
_diffrn_orient_matrix_UB_23      -0.0076862000
_diffrn_orient_matrix_UB_31      -0.0003350000
_diffrn_orient_matrix_UB_32      0.0069590000
_diffrn_orient_matrix_UB_33      0.0493803000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15490
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.30
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         6767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1659
_reflns_number_gt                4051
_reflns_number_total             6767
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra12492e2.cif
_cod_data_source_block           exp_614
_cod_database_code               7225504
_chemical_oxdiff_formula         'C108 H96 Br8 F12 N12 O24 '
_reflns_odcompleteness_completeness 94.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22