Radical–Anion Coupling Through Reagent Design: Hydroxylation of Aryl Halides
Greener, Andrew John; Ubysz, Patrycja; Owens-Ward, Will; Smith, George; Ocaña, Ivan; Whitwood, Adrian Charles; Chechik, Victor; James, Michael J.; Chemical Science  (2021) –; doi:10.1039/D1SC04748E

data_1565057
_publ_section_title
;
 Radical--Anion Coupling Through Reagent Design: Hydroxylation of Aryl
 Halides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04748E
_journal_year                    2021
_chemical_formula_moiety         'C23 H31 N3 O'
_chemical_formula_sum            'C23 H31 N3 O'
_chemical_formula_weight         365.51
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-11 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.562(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5000(3)
_cell_length_b                   11.7569(3)
_cell_length_c                   18.0932(5)
_cell_measurement_reflns_used    3909
_cell_measurement_temperature    109.9(6)
_cell_measurement_theta_max      70.8510
_cell_measurement_theta_min      4.5020
_cell_volume                     1979.83(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_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    -19.00  30.00   1.00    1.00    --    0.00 -77.00 -60.00   49
  2  \w    -20.00   6.00   1.00    1.00    --    0.00 -77.00 150.00   26
  3  \w    -19.00  13.00   1.00    1.00    --    0.00 -77.00  60.00   32
  4  \w     38.00  65.00   1.00    3.00    --   54.00  57.00 -90.00   27
  5  \w     37.00 123.00   1.00    3.00    --   54.00  57.00 -60.00   86
  6  \w     43.00 118.00   1.00    3.00    --   54.00  57.00  60.00   75
  7  \w    -13.00  65.00   1.00    3.00    --   54.00 -57.00 150.00   78
  8  \w     97.00 141.00   1.00    3.00    --  108.00 -25.00 120.00   44
  9  \w     38.00  78.00   1.00    3.00    --  108.00 -25.00 120.00   40
 10  \w     38.00  89.00   1.00    3.00    --  108.00 -50.00-180.00   51
 11  \w     99.00 126.00   1.00    3.00    --  108.00 -50.00 -90.00   27
 12  \w     61.00 106.00   1.00    3.00    --  108.00 -91.00-120.00   45
 13  \w    114.00 149.00   1.00    3.00    --  108.00 111.00-150.00   35
 14  \w     42.00  84.00   1.00    3.00    --  108.00 -50.00 -90.00   42
 15  \w    115.00 177.00   1.00    3.00    --  108.00 111.00-180.00   62
 16  \w     42.00  69.00   1.00    3.00    --  108.00 -91.00-180.00   27
 17  \w     99.00 126.00   1.00    3.00    --  108.00 -50.00-180.00   27
 18  \w     36.00 176.00   1.00    3.00    --  108.00   0.00  30.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1625227000
_diffrn_orient_matrix_UB_12      0.0222189000
_diffrn_orient_matrix_UB_13      0.0240974000
_diffrn_orient_matrix_UB_21      -0.0158482000
_diffrn_orient_matrix_UB_22      0.1078357000
_diffrn_orient_matrix_UB_23      -0.0493920000
_diffrn_orient_matrix_UB_31      -0.0270161000
_diffrn_orient_matrix_UB_32      0.0711158000
_diffrn_orient_matrix_UB_33      0.0673008000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.513
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
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    1.226
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method 'Crystallisation from DMSO'
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00040(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.5760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3032
_reflns_number_total             3538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04748e2.cif
_cod_data_source_block           mjj21001
_cod_database_code               1565057
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H31 N3 O1'
_chemical_oxdiff_usercomment     'Andrew Greener AJG-02-010-3'
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.853
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              86125
_shelx_hkl_checksum              80750
_olex2_date_sample_data_collection 2021-06-14
_olex2_date_sample_submission    2021-06-11
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id AJG-020-010-3
_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.783