Visible-light promoted intermolecular halofunctionalization of alkenes with N-halogen saccharins
Song, Lu; Luo, Sanzhong; Cheng, Jin-Pei; Organic Chemistry Frontiers 3 (2016) 447–; doi:10.1039/C5QO00432B

data_1553237
_publ_section_title
;
 Visible-light promoted intermolecular halofunctionalization of alkenes
 with N-halogen saccharins
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              447
_journal_paper_doi               10.1039/C5QO00432B
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C16 H14 Br N O3 S'
_chemical_formula_sum            'C16 H14 Br N O3 S'
_chemical_formula_weight         380.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2015-12-16 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.905(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.825(4)
_cell_length_b                   8.982(3)
_cell_length_c                   11.426(6)
_cell_measurement_reflns_used    4283
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4811
_cell_measurement_theta_min      2.6488
_cell_volume                     1527.1(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0885
_diffrn_orient_matrix_UB_12      -0.0209
_diffrn_orient_matrix_UB_13      -0.0197
_diffrn_orient_matrix_UB_21      0.0342
_diffrn_orient_matrix_UB_22      -0.0692
_diffrn_orient_matrix_UB_23      -0.0802
_diffrn_orient_matrix_UB_31      -0.0199
_diffrn_orient_matrix_UB_32      -0.0526
_diffrn_orient_matrix_UB_33      0.0369
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10011
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         1.369
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.840
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0378P)^2^+6.1349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3090
_reflns_number_total             3465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00432b2.cif
_cod_data_source_block           a
_cod_original_cell_volume        1527.2(10)
_cod_database_code               1553237
_shelxl_version_number           2013-4
_diffrn_number_total             3694
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              44616
_shelx_hkl_checksum              97722