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_1553236
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-10-08 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                87.089(10)
_cell_angle_beta                 73.797(9)
_cell_angle_gamma                70.74(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3045(15)
_cell_length_b                   9.415(2)
_cell_length_c                   11.190(2)
_cell_measurement_reflns_used    2724
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4815
_cell_measurement_theta_min      2.2938
_cell_volume                     792.3(4)
_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  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'

;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.0801
	          2theta: -20.0701
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0801
	          2theta: -20.0701
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.0801
	          2theta: -20.0701
;
_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      -0.0331
_diffrn_orient_matrix_UB_12      -0.0552
_diffrn_orient_matrix_UB_13      0.1162
_diffrn_orient_matrix_UB_21      -0.0342
_diffrn_orient_matrix_UB_22      -0.0669
_diffrn_orient_matrix_UB_23      -0.0839
_diffrn_orient_matrix_UB_31      0.0868
_diffrn_orient_matrix_UB_32      -0.0284
_diffrn_orient_matrix_UB_33      -0.0184
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10014
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.705
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.737
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0357P)^2^+0.4345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3405
_reflns_number_total             3615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00432b2.cif
_cod_data_source_block           sa3947
_cod_original_cell_volume        792.4(4)
_cod_database_code               1553236
_diffrn_number_total             3617
_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. Restrained distances
 C16-C15
 1.54 with sigma of 0.01
 C16A-C15
 1.54 with sigma of 0.01
 C16A-Br1A
 2.8 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Br1A \\sim C16 \\sim C16A \\sim Br1: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04
Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C16A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(H15A)=Sof(Br1A)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(Br1)=Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
5.a Riding coordinates:
 C16A(H16D,H16E,H16F)
5.b Ternary CH refined with riding coordinates:
 C8(H8), C15(H15), C15(H15A)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              15163
_shelx_hkl_checksum              75552
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'