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_1565056
_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         'C6 H8 N2 O'
_chemical_formula_sum            'C6 H8 N2 O'
_chemical_formula_weight         124.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-08-11 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.1149(5)
_cell_length_b                   7.9429(2)
_cell_length_c                   18.0218(5)
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    111(3)
_cell_measurement_theta_max      31.8620
_cell_measurement_theta_min      4.0920
_cell_volume                     2593.06(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      111(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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    -47.00  81.00   1.00  100.00    --   25.64   0.00-180.00  128
  2  \w      8.00  77.00   1.00  100.00    --   25.64  57.00  30.00   69
  3  \w    -88.00 -59.00   1.00  100.00    --  -25.95 178.00-180.00   29
  4  \w   -102.00 -59.00   1.00  100.00    --  -25.95 178.00 -30.00   43
;
_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      -0.0149270000
_diffrn_orient_matrix_UB_12      -0.0201425000
_diffrn_orient_matrix_UB_13      0.0352803000
_diffrn_orient_matrix_UB_21      0.0262712000
_diffrn_orient_matrix_UB_22      0.0535371000
_diffrn_orient_matrix_UB_23      0.0172193000
_diffrn_orient_matrix_UB_31      -0.0248567000
_diffrn_orient_matrix_UB_32      0.0686043000
_diffrn_orient_matrix_UB_33      -0.0030637000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15188
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.078
_diffrn_reflns_theta_min         3.189
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.786
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.272
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_recrystallization_method
'Crystallisationfrom dichloromethane and hexane'
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0486P)^2^+1.2103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2957
_reflns_number_total             3802
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04748e2.cif
_cod_data_source_block           mjj2001
_cod_original_cell_volume        2593.05(12)
_cod_database_code               1565056
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C6 H8 N2 O'
_chemical_oxdiff_usercomment     'Michael James WOW-01-001-4'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_refinement_description
;
;
_shelx_res_checksum              3722
_shelx_hkl_checksum              69176
_olex2_date_sample_data_collection 2020-10-12
_olex2_date_sample_submission    2020-10-12
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id WOW-01-001-4
_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 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.912