Photoinduced, copper-catalyzed three components cyanofluoroalkylation of alkenes with fluoroalkyl iodides as fluoroalkylation reagents
Guo, Quanping; Wang, Mengran; Wang, Yanfang; Xu, Zhaoqing; Wang, Rui; Chemical Communications  (2017) –; doi:10.1039/C7CC07128K

data_7120842
_publ_section_title
;
 Photoinduced, copper-catalyzed three components cyanofluoroalkylation of
 alkenes with fluoroalkyl iodides as fluoroalkylation reagents
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C7CC07128K
_journal_year                    2017
_chemical_formula_moiety         'C16 H9 F9 N2 O2'
_chemical_formula_sum            'C16 H9 F9 N2 O2'
_chemical_formula_weight         432.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-05-26 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                76.581(10)
_cell_angle_beta                 85.498(10)
_cell_angle_gamma                83.205(10)
_cell_formula_units_Z            2
_cell_length_a                   5.7476(7)
_cell_length_b                   11.2870(13)
_cell_length_c                   14.0380(17)
_cell_measurement_reflns_used    906
_cell_measurement_temperature    291.08(10)
_cell_measurement_theta_max      21.4180
_cell_measurement_theta_min      3.7990
_cell_volume                     878.38(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      air
_diffrn_ambient_temperature      291.08(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -9.00   25.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -150.0000 23

  2 omega   38.00   74.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  -30.0000 24

  3 omega    2.00   95.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -180.0000 62

  4 omega    2.00   29.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000   90.0000 18

  5 omega  -48.00   45.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000   60.0000 62

  6 omega  -49.00   44.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000  -30.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0555944000
_diffrn_orient_matrix_UB_12      -0.0502498000
_diffrn_orient_matrix_UB_13      0.0336241000
_diffrn_orient_matrix_UB_21      -0.0867347000
_diffrn_orient_matrix_UB_22      0.0096333000
_diffrn_orient_matrix_UB_23      0.0370220000
_diffrn_orient_matrix_UB_31      -0.0698387000
_diffrn_orient_matrix_UB_32      -0.0400096000
_diffrn_orient_matrix_UB_33      -0.0143107000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5554
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.57
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1501
_refine_ls_R_factor_gt           0.0905
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1160P)^2^+0.9947P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.2871
_reflns_number_gt                1859
_reflns_number_total             3444
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc07128k2.cif
_cod_data_source_block           guoqp_0508
_cod_original_cell_volume        878.38(18)
_cod_database_code               7120842
_chemical_oxdiff_formula         'C H O N F'
_reflns_odcompleteness_completeness 99.69
_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. Uiso/Uaniso restraints and constraints
Uanis(F6') \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F8) \\sim
Ueq, Uanis(F9) \\sim Ueq, Uanis(F5') \\sim Ueq, Uanis(F5) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F5(0.6) F6(0.6) F5'(0.4) F6'(0.4)
4.a Ternary CH refined with riding coordinates:
 C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_olex2_date_sample_data_collection 2017-05-10
_olex2_submission_special_instructions 'No special instructions were received'