Anodically Coupled Electrolysis for the Heterodifunctionalization of Alkenes.
Ye, Ke-Yin; Pombar, Gisselle; Fu, Niankai; Sauer, Gregory S.; Keresztes, Ivan; Lin, Song; Journal of the American Chemical Society 140 (2018) 2438–2441; doi:10.1021/jacs.7b13387

data_4131942
_publ_section_title
;
 Anodically Coupled Electrolysis for the Heterodifunctionalization of
 Alkenes.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2438
_journal_page_last               2441
_journal_paper_doi               10.1021/jacs.7b13387
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H22 Cl F3 N2 O'
_chemical_formula_sum            'C20 H22 Cl F3 N2 O'
_chemical_formula_weight         398.84
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-18
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9980(2)
_cell_length_b                   11.5663(2)
_cell_length_c                   17.6674(5)
_cell_measurement_reflns_used    3881
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.0320
_cell_measurement_theta_min      4.5710
_cell_volume                     1838.71(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     11.00  45.00   0.50    0.10    --   62.87  91.00-137.89   68
  2  \w     12.00  45.00   0.50    0.10    --   62.87  91.00-115.30   66
  3  \w    121.00 148.00   0.50    0.10    --  125.75 111.00-180.00   54
  4  \w    103.00 129.00   0.50    0.10    --  125.75 111.00 -90.00   52
  5  \w     89.00 149.00   0.50    0.10    --   62.87 128.00  46.00  120
  6  \w     90.00 168.00   0.50    0.10    --  125.75 128.00  46.00  156
  7  \w    142.00 168.00   0.50    0.10    --  125.75 111.00 -90.00   52
  8  \w     34.00 174.00   0.50    0.10    --  125.75 -80.00  39.00  280
  9  \w     98.00 178.00   0.50    0.10    --  125.75  50.00  90.00  160
 10  \w     81.00 127.00   0.50    0.10    --  125.75  77.00   0.00   92
 11  \w     82.00 168.00   0.50    0.10    --  125.75  50.00   0.00  172
 12  \w     70.00 178.00   0.50    0.10    --  125.75  41.00  -8.00  216
 13  \w    129.00 178.00   0.50    0.10    --  125.75  77.00 -90.00   98
 14  \w     81.00 124.00   0.50    0.10    --  125.75  77.00 -90.00   86
 15  \w     83.00 109.00   0.50    0.10    --  125.75 -63.00  30.00   52
 16  \w    -79.00 -20.00   0.50    0.05    --    0.00 142.00-141.00  118
 17  \w   -110.00  26.00   0.50    0.10    --  -62.87  80.00 163.00  272
 18  \w    -64.00 -17.00   0.50    0.05    --    0.00 -57.00 -30.00   94
 19  \w     36.00 115.00   0.50    0.10    --  125.75-111.00-120.00  158
 20  \w     40.00  74.00   0.50    0.10    --  125.75 -91.00 120.00   68
 21  \w    102.00 128.00   0.50    0.10    --  125.75 -91.00 120.00   52
 22  \w     44.00 129.00   0.50    0.10    --  125.75-142.00 160.00  170
 23  \w   -150.00  -9.00   0.50    0.10    --  -62.87 -41.00-161.00  282
 24  \w   -147.00 -69.00   0.50    0.10    --  -62.87-128.00 -27.00  156
 25  \w   -160.00 -59.00   0.50    0.10    -- -104.25-142.00 160.00  202
 26  \w     -3.00  57.00   0.50    0.05    --    0.00 -99.00 150.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0078278000
_diffrn_orient_matrix_UB_12      0.0221500000
_diffrn_orient_matrix_UB_13      -0.0858982000
_diffrn_orient_matrix_UB_21      -0.0887366000
_diffrn_orient_matrix_UB_22      -0.1117281000
_diffrn_orient_matrix_UB_23      -0.0144315000
_diffrn_orient_matrix_UB_31      -0.1461833000
_diffrn_orient_matrix_UB_32      0.0690616000
_diffrn_orient_matrix_UB_33      0.0041977000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11128
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.464
_diffrn_reflns_theta_min         4.569
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.218
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.261
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3662
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+1.1779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                3438
_reflns_number_total             3662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b13387_si_002.cif
_cod_data_source_block           rky2_abs
_cod_database_code               4131942
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C20H23ClF3N2O
_chemical_oxdiff_usercomment     'Crystallized from acetone/pentane'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
2. Restrained distances
 O-H
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C17(H17), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.457
_oxdiff_exptl_absorpt_empirical_full_min 0.834