Metal-free fluoroalkylfluoroalkylselenolation of unactivated alkenes: incorporation of two photoinduced processes
Lei, Yingjie; Yang, Ju; Wang, Yawen; Wang, Hongying; Zhan, Yue; Jiang, Xianxing; Xu, Zhaoqing; Green Chemistry 22 (2020) 4878–4883; doi:10.1039/C9GC03936H

data_7240863
_publ_section_title
;
 Metal-free fluoroalkylfluoroalkylselenolation of unactivated alkenes:
 incorporation of two photoinduced processes
;
_journal_issue                   15
_journal_name_full               'Green Chemistry'
_journal_page_first              4878
_journal_page_last               4883
_journal_paper_doi               10.1039/C9GC03936H
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C13 H9 F6 N O2 Se'
_chemical_formula_sum            'C13 H9 F6 N O2 Se'
_chemical_formula_weight         404.17
_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     direct
_audit_creation_date             2019-12-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-25 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.581(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.4389(2)
_cell_length_b                   21.5791(4)
_cell_length_c                   14.6690(3)
_cell_measurement_reflns_used    4385
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8110
_cell_measurement_theta_min      5.1750
_cell_volume                     3113.27(11)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -24.00  12.00   1.00    1.00    --    0.00  38.00  30.00   36
  2  \w     19.00  69.00   1.00    1.00    --    0.00  38.00  30.00   50
  3  \w     95.00 121.00   1.00    1.00    --   54.00  57.00   0.00   26
  4  \w    105.00 140.00   1.00    1.00    --  108.00 111.00  90.00   35
  5  \w    151.00 177.00   1.00    1.00    --  108.00  50.00 -30.00   26
  6  \w    100.00 127.00   1.00    1.00    --  108.00 111.00-120.00   27
  7  \w     96.00 163.00   1.00    1.00    --  108.00  63.00-150.00   67
  8  \w     87.00 174.00   1.00    1.00    --  108.00  63.00-120.00   87
  9  \w     76.00 127.00   1.00    1.00    --  108.00 -63.00  60.00   51
 10  \w     39.00 112.00   1.00    1.00    --  108.00-111.00  90.00   73
 11  \w      2.00  81.00   1.00    1.00    --   54.00 -99.00 -60.00   79
 12  \w     23.00  66.00   1.00    1.00    --   54.00-125.00-180.00   43
 13  \w     40.00 108.00   1.00    1.00    --  108.00 -63.00-180.00   68
 14  \w     61.00 109.00   1.00    1.00    --   54.00  57.00-180.00   48
 15  \w     79.00 177.00   1.00    1.00    --  108.00  77.00 -90.00   98
 16  \w    -11.00  75.00   1.00    1.00    --   54.00 -57.00 -30.00   86
 17  \w    -15.00  11.00   1.00    1.00    --    0.00  57.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0134733000
_diffrn_orient_matrix_UB_12      -0.0384168000
_diffrn_orient_matrix_UB_13      0.0848658000
_diffrn_orient_matrix_UB_21      -0.0925580000
_diffrn_orient_matrix_UB_22      0.0503511000
_diffrn_orient_matrix_UB_23      0.0190670000
_diffrn_orient_matrix_UB_31      -0.1256660000
_diffrn_orient_matrix_UB_32      -0.0329462000
_diffrn_orient_matrix_UB_33      -0.0696843000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11769
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.573
_diffrn_reflns_theta_max         66.573
_diffrn_reflns_theta_min         3.798
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01470
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.055
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5495
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0852P)^2^+3.6994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4530
_reflns_number_total             5495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03936h2.cif
_cod_data_source_block           zengyj_1223
_cod_depositor_comments
;
 Adding full bibliography for 7240863.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        3113.26(11)
_cod_original_formula_moiety     '2(C13 H9 F6 N O2 Se)'
_cod_original_formula_sum        'C26 H18 F12 N2 O4 Se2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     808.34
_cod_database_code               7240863
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.647
_shelx_estimated_absorpt_t_min   0.535
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C24-C25
 1.49 with sigma of 0.01
3. Rigid bond restraints
 C24, C25
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4.a Ternary CH refined with riding coordinates:
 C10(H10), C23(H23)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C22(H22A,H22B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18), C19(H19)
;
_shelx_res_checksum              92511
_shelx_hkl_checksum              85741
_olex2_date_sample_data_collection 2019-12-23
_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 41.488
_oxdiff_exptl_absorpt_empirical_full_min 0.395