Environmentally Friendly Protocol for the Oxidative Iodofunctionalization of Olefins in a Green Solvent
Yi, Wei; Wang, Peng-Fei; Lu, Meng; Liu, Qian-Qian; Bai, Xue; Chen, Kai-Die; Zhang, Jing-Wen; Liu, Gong-Qing; ACS Sustainable Chemistry & Engineering 7 (2019) 16777–; doi:10.1021/acssuschemeng.9b04298

data_4515221
_publ_section_title
;
 Environmentally Friendly Protocol for the Oxidative Iodofunctionalization
 of Olefins in a Green Solvent
;
_journal_issue                   19
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              16777
_journal_paper_doi               10.1021/acssuschemeng.9b04298
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C8 H8 Cl I O'
_chemical_formula_sum            'C8 H8 Cl I O'
_chemical_formula_weight         282.49
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.661(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0502(7)
_cell_length_b                   4.5002(2)
_cell_length_c                   15.3524(8)
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.2950
_cell_measurement_theta_min      2.6980
_cell_volume                     888.84(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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    -76.00  13.00   1.00    1.00    --  -11.59 -57.00 -30.00   89
  2  \w    -38.00  62.00   1.00    1.00    --  -11.59  57.00 120.00  100
  3  \w    -11.00  79.00   1.00    1.00    --   11.74  77.00-120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0513727000
_diffrn_orient_matrix_UB_12      -0.0541198000
_diffrn_orient_matrix_UB_13      -0.0018894000
_diffrn_orient_matrix_UB_21      0.0016854000
_diffrn_orient_matrix_UB_22      0.0402030000
_diffrn_orient_matrix_UB_23      0.0448589000
_diffrn_orient_matrix_UB_31      -0.0199567000
_diffrn_orient_matrix_UB_32      0.1425934000
_diffrn_orient_matrix_UB_33      -0.0133675000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5115
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.972
_diffrn_reflns_theta_max         24.972
_diffrn_reflns_theta_min         2.243
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.111
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0189
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.2136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0455
_refine_ls_wR_factor_ref         0.0461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1505
_reflns_number_total             1565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc9b04298_si_002.cif
_cod_data_source_block           nt1225
_cod_database_code               4515221
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C3(H3), C5(H5)
;
_olex2_date_sample_data_collection 2018-12-25
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.729