Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functionalizations: oxidative annulations of cyclopropyl-substituted alkynes.
Deponti, Monica; Kozhushkov, Sergei I.; Yufit, Dmitry S.; Ackermann, Lutz; Organic & biomolecular chemistry 11 (2013) 142–148; doi:10.1039/c2ob26250a

data_7152761
_publ_section_title
;
 Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functionalizations:
 oxidative annulations of cyclopropyl-substituted alkynes.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              142
_journal_page_last               148
_journal_paper_doi               10.1039/c2ob26250a
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C19 H13 F3 O2'
_chemical_formula_sum            'C19 H13 F3 O2'
_chemical_formula_weight         330.29
_chemical_name_common
4-cyclopropyl-3-(3-trifluoromethylphenyl)-1H-isochromen-1-one
_chemical_name_systematic
;
4-cyclopropyl-3-(3-trifluoromethylphenyl)-1H-isochromen-1-one
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-04-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2012.03.20 svn.r2253, GUI svn.r4124)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.502(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3582(7)
_cell_length_b                   14.6219(8)
_cell_length_c                   7.6852(4)
_cell_measurement_reflns_used    7488
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      2.79
_cell_volume                     1501.03(14)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22487
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.79
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_type              'sealed X-ray tube'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0455 before and 0.0249 after correction.
The Ratio of minimum to maximum transmission is 0.6522.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.990
_refine_diff_density_min         -1.062
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.221
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0754
_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^)+(0.1000P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2099
_reflns_number_gt                3002
_reflns_number_total             3608
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26250a.txt
_cod_data_source_block           6ae_dk80
_cod_database_code               7152761