Access to cyclic gem-difluoroacyl scaffolds via electrochemical and visible light photocatalytic radical tandem cyclization of heteroaryl chlorodifluoromethyl ketones
Adouama, Chérif; Keyrouz, Robert; pilet, guillaume; Monnereau, Cyrille; Gueyrard, David; Noel, Timothy; Médebielle, Maurice; Chem. Commun.  (2017) –; doi:10.1039/C7CC02979A

data_7120056
_publ_section_title
;
 Access to cyclic gem-difluoroacyl scaffolds via electrochemical and
 visible light photocatalytic radical tandem cyclization of heteroaryl
 chlorodifluoromethyl ketones
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02979A
_journal_year                    2017
_chemical_formula_moiety         'C18 H17 F2 N1 O2'
_chemical_formula_sum            'C18 H17 F2 N O2'
_chemical_formula_weight         317.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2016-12-12 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 104.776(8)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   16.1287(11)
_cell_length_b                   11.1367(9)
_cell_length_c                   8.7194(9)
_cell_measurement_reflns_used    1292
_cell_measurement_temperature    293
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     1514.4(2)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis, (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    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7530
_diffrn_reflns_theta_full        25.264
_diffrn_reflns_theta_max         29.377
_diffrn_reflns_theta_min         3.036
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1190
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1476
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.0001721
_refine_ls_shift/su_mean         0.0000161
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 6.04 4.79 5.22 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0767
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0532
_reflns_limit_h_max              20
_reflns_limit_h_min              -21
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1902
_reflns_number_total             3512
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.85
_oxford_diffrn_Wilson_scale      0.53
_oxford_refine_ls_r_factor_ref   0.0470
_oxford_refine_ls_scale          1.060(4)
_oxford_reflns_number_all        3504
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            c7cc02979a2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_atom_sites_solution_primary' value 'Direct' changed to 'direct'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C18 H17 F2 N1 O2'
_cod_database_code               7120056
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;