Intramolecular Oxidative C-H Coupling for Medium-Ring Synthesis
Didier G. Pintori; Michael F. Greaney; Journal of the American Chemical Society 133 (2011) 1209–1211; doi:10.1021/ja1090854

data_4105588
_publ_contact_author_email       S.Parsons@ed.ac.uk
_publ_contact_author_name        'Simon Parsons'
_publ_section_title
;
 Intramolecular Oxidative C-H Coupling for Medium-Ring Synthesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1209
_journal_page_last               1211
_journal_paper_doi               10.1021/ja1090854
_journal_volume                  133
_journal_year                    2011
_chemical_compound_source        'Didier Pintori - reaction DP803B'
_chemical_formula_moiety         'C18 H14 F1 N1 O1'
_chemical_formula_sum            'C18 H14 F N O'
_chemical_formula_weight         279.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_date             10-06-21
_audit_creation_method           CRYSTALS_ver_14.09
_cell_angle_alpha                90
_cell_angle_beta                 92.315(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8879(3)
_cell_length_b                   9.0693(3)
_cell_length_c                   12.4154(3)
_cell_measurement_reflns_used    7036
_cell_measurement_temperature    100
_cell_measurement_theta_max      73
_cell_measurement_theta_min      4
_cell_volume                     1337.47(6)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis CCD, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10234
_diffrn_reflns_theta_full        68.880
_diffrn_reflns_theta_max         73.277
_diffrn_reflns_theta_min         5.050
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9536
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.0002882
_refine_ls_shift/su_mean         0.0000364
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.43P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1024
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1024
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2191
_reflns_number_total             2619
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.12
_oxford_diffrn_Wilson_scale      3.28
_oxford_refine_ls_r_factor_ref   0.0429
_oxford_refine_ls_scale          0.5459(14)
_oxford_reflns_number_all        2617
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'mg0007 in P2(1)/n'
_cod_data_source_file            ja1090854_si_003.cif
_cod_data_source_block           mg0007
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C18 H14 F1 N1 O1'
_cod_database_code               4105588