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_7225503
_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 H11 F3 N2 O6'
_chemical_formula_sum            'C21 H11 F3 N2 O6'
_chemical_formula_weight         444.32
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-08-31
_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                 96.187(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8312(6)
_cell_length_b                   6.5653(2)
_cell_length_c                   20.2552(9)
_cell_measurement_reflns_used    1860
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.6950
_cell_measurement_theta_min      2.9430
_cell_volume                     1828.58(13)
_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 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_details
;
  1 omega   23.00   50.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360   77.0000    0.0000 27

  2 omega   54.00   93.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000 -150.0000 39

  3 omega   16.00   71.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000 -180.0000 55

  4 omega   -2.00   35.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000  -90.0000 37

  5 omega   -6.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000    0.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0243164000
_diffrn_orient_matrix_UB_12      -0.0892469000
_diffrn_orient_matrix_UB_13      -0.0126237000
_diffrn_orient_matrix_UB_21      -0.0450466000
_diffrn_orient_matrix_UB_22      0.0525337000
_diffrn_orient_matrix_UB_23      -0.0022231000
_diffrn_orient_matrix_UB_31      0.0064350000
_diffrn_orient_matrix_UB_32      0.0307932000
_diffrn_orient_matrix_UB_33      -0.0327997000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8783
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97217
_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    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0700P)^2^+0.0600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                2511
_reflns_number_total             4037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra12492e2.cif
_cod_data_source_block           exp_635
_cod_database_code               7225503
_reflns_odcompleteness_completeness 89.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22