Synthesis of quaternary α-perfluoroalkyl lactams via electrophilic perfluoroalkylation.
Katayev, D.; Václavík, J; Brüning, F; Commare, B.; Togni, A.; Chemical communications (Cambridge, England) 52 (2016) 4049–4052; doi:10.1039/c6cc00700g

data_7118746
_publ_section_title
;
 Synthesis of quaternary \a-perfluoroalkyl lactams via electrophilic
 perfluoroalkylation.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4049
_journal_page_last               4052
_journal_paper_doi               10.1039/c6cc00700g
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C14 H14 F5 N O'
_chemical_formula_sum            'C14 H14 F5 N O'
_chemical_formula_weight         307.26
_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
_audit_creation_date             2015-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-16 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                89.626(3)
_cell_angle_beta                 85.989(3)
_cell_angle_gamma                89.673(3)
_cell_formula_units_Z            4
_cell_length_a                   8.4914(8)
_cell_length_b                   10.2896(9)
_cell_length_c                   15.2108(13)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    103
_cell_measurement_theta_max      29.47
_cell_measurement_theta_min      2.38
_cell_volume                     1325.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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_temperature      103.0
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4852
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.385
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0792 before and 0.0708 after correction.
 The Ratio of minimum to maximum transmission is 0.91.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 49665 reflections, Rint = 0.0742
 (23362 with I > 3sig(I), Rint = 0.0482)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate, Hexane'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.245
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0371P)^2^+1.0374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3873
_reflns_number_total             4852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc00700g2.cif
_cod_data_source_block           kd-191
_cod_depositor_comments          'Adding full bibliography for 7118746.cif.'
_cod_database_code               7118746
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6342(18) 0.3658(18)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C4(H4A,H4B), C7(H7A,H7B), C17(H17A,H17B), C3(H3A,H3B),
 C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C23(H23), C12(H12), C13(H13), C11(H11), C10(H10), C9(H9), C24(H24),
 C26(H26), C25(H25)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              51566
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-05
_olex2_submission_special_instructions 'No special instructions were received'