Visible light-induced selective aerobic oxidative transposition of vinyl halides using a tetrahalogenoferrate(iii) complex catalyst
Li, Sanliang; Zhu, Bo; Lee, Richmond; Qiao, Baokun; Jiang, Zhiyong; Organic Chemistry Frontiers 5 (2018) 380–; doi:10.1039/C7QO00798A

data_1553902
_publ_section_title
;
 Visible light-induced selective aerobic oxidative transposition of vinyl
 halides using a tetrahalogenoferrate(iii) complex catalyst
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              380
_journal_paper_doi               10.1039/C7QO00798A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'Br Cl3 Fe, C16 H36 N'
_chemical_formula_sum            'C16 H36 Br Cl3 Fe N'
_chemical_formula_weight         484.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_Hall           '-P 2a 2bc'
_space_group_name_H-M_alt        'P n n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-01-03 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4928(16)
_cell_length_b                   11.5835(8)
_cell_length_c                   11.4759(8)
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.1710
_cell_measurement_theta_min      3.7920
_cell_volume                     2458.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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     -8.00  22.00   1.00    7.50    --  -33.50  37.00  60.00   30
  2  \w    -36.00   9.00   1.00    7.50    --  -33.50  37.00 -60.00   45
  3  \w    -47.00 -21.00   1.00    7.50    --  -33.50  37.00  60.00   26
  4  \w     58.00 100.00   1.00    7.50    --   36.47 178.00 -90.00   42
  5  \w     71.00  97.00   1.00    7.50    --   36.47 178.00 150.00   26
  6  \w     18.00 104.00   1.00    7.50    --   36.47  57.00 -30.00   86
  7  \w    101.00 177.00   1.00   30.00    --  108.00 111.00-180.00   76
  8  \w     43.00  85.00   1.00   30.00    --  108.00 -30.00  90.00   42
  9  \w     37.00  70.00   1.00   30.00    --  108.00 -30.00 150.00   33
 10  \w     54.00  96.00   1.00   30.00    --  108.00 -45.00-180.00   42
 11  \w     50.00  76.00   1.00   30.00    --  108.00 -77.00-120.00   26
 12  \w    100.00 137.00   1.00   30.00    --  108.00 -77.00-120.00   37
 13  \w     84.00 127.00   1.00   30.00    --  108.00 -61.00  30.00   43
 14  \w    107.00 154.00   1.00   30.00    --  108.00 111.00  90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0715012000
_diffrn_orient_matrix_UB_12      0.0510151000
_diffrn_orient_matrix_UB_13      0.0455782000
_diffrn_orient_matrix_UB_21      0.0385552000
_diffrn_orient_matrix_UB_22      0.0395631000
_diffrn_orient_matrix_UB_23      0.1120152000
_diffrn_orient_matrix_UB_31      0.0184053000
_diffrn_orient_matrix_UB_32      0.1162240000
_diffrn_orient_matrix_UB_33      -0.0584398000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5751
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.535
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       prism
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00165(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0611P)^2^+0.2098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1349
_reflns_number_total             2188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00798a2.cif
_cod_data_source_block           jzhyb
_cod_database_code               1553902
_chemical_oxdiff_formula         C1H1O1N1Fe1Cl1Br1
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Br1(0.25) Br1A(0.25) Cl1(0.75) Cl2(0.75)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              87184
_shelx_hkl_checksum              94480
_shelx_shelxl_version_number     2014/7
_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 1.734
_oxdiff_exptl_absorpt_empirical_full_min 0.659