Metal-free and site-selective α-C–H functionalization of tetrahydrofuran enabled by the photocatalytic generation of bromine radicals
Zhu, Can-Ming; Liang, Rong-Bin; Xiao, Yonghong; Zhou, Wei; Tong, Qing-Xiao; Zhong, Jian-Ji; Green Chemistry 25 (2023) 960–965; doi:10.1039/D2GC03347J

data_7245794
_publ_section_title
;
 Metal-free and site-selective \a-C--H functionalization of
 tetrahydrofuran enabled by the photocatalytic generation of bromine
 radicals
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              960
_journal_page_last               965
_journal_paper_doi               10.1039/D2GC03347J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C16 H16 O S'
_chemical_formula_sum            'C16 H16 O S'
_chemical_formula_weight         256.35
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2bk2cc
_audit_creation_date             2022-03-08
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.02.24 svn.r684696ac for OlexSys, GUI svn.r6476)
;
_audit_update_record
;
2022-03-23 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.536(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0752(3)
_cell_length_b                   9.8777(5)
_cell_length_c                   22.1887(13)
_cell_measurement_reflns_used    2423
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0540
_cell_measurement_theta_min      4.9060
_cell_volume                     1331.04(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.964
_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     43.00  80.00   0.50    1.50    --    0.00  57.00  60.00   74
  2  \w    -78.00 -24.00   0.50    1.50    --    0.00 -57.00  30.00  108
  3  \w    -21.00  18.00   0.50    1.50    --    0.00  57.00  60.00   78
  4  \w     58.00 108.00   0.50    6.00    --   89.30  82.00-180.00  100
  5  \w     62.00 135.00   0.50    6.00    --   89.30  82.00-150.00  146
  6  \w     57.00 164.00   0.50    6.00    --   89.30  82.00   0.00  214
  7  \w     80.00 111.00   0.50    6.00    --   89.30 -61.00  60.00   62
  8  \w      6.00  56.00   0.50    6.00    --   89.30 -61.00  60.00  100
  9  \w    130.00 179.00   0.50    6.00    --   89.30  82.00-180.00   98
 10  \w     65.00 127.00   0.50    6.00    --   89.30  61.00   0.00  124
 11  \w     50.00 122.00   0.50    6.00    --   89.30 -82.00  90.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0083343000
_diffrn_orient_matrix_UB_12      0.1437446000
_diffrn_orient_matrix_UB_13      -0.0269173000
_diffrn_orient_matrix_UB_21      -0.1900532000
_diffrn_orient_matrix_UB_22      -0.0431812000
_diffrn_orient_matrix_UB_23      -0.0430664000
_diffrn_orient_matrix_UB_31      -0.1678405000
_diffrn_orient_matrix_UB_32      0.0421372000
_diffrn_orient_matrix_UB_33      0.0474149000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5767
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.816
_diffrn_reflns_theta_min         3.986
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       irregular
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0594P)^2^+0.7043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2075
_reflns_number_total             2471
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03347j2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7245794.cif.'
_cod_database_code               7245794
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S'
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.906
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C3(H3), C12(H12), C5(H5), C11(H11), C2(H2), C1(H1), C6(H6)
;
_shelx_res_checksum              61712
_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 1.369
_oxdiff_exptl_absorpt_empirical_full_min 0.774