A novel example of double 6-exo-trig heterocyclization: nitrile conversion to new anticancer active (HeLa cells) primary amine ionic liquids
Denis Prodius; Hamid Saeed Shah; Jamshed Iqbal; Anastasia Macaeva; Anatoli Dimoglo; George E. Kostakis; Nicolas Zill; Fliur Macaev; Annie K. Powell; Chem.Commun. 50 (2014) 4888–; doi:10.1039/C3CC49759C

data_7112606
_publ_section_title
;
 A novel example of double 6-exo-trig heterocyclization: nitrile
 conversion to new anticancer active (HeLa cells) primary amine ionic
 liquids
;
_journal_name_full               Chem.Commun.
_journal_page_first              4888
_journal_paper_doi               10.1039/C3CC49759C
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_sum            'C7 H15 F6 N2 O2 P'
_chemical_formula_weight         304.18
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3381(13)
_cell_length_b                   8.1858(16)
_cell_length_c                   11.115(2)
_cell_measurement_reflns_used    6271
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.48
_cell_volume                     567.1(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2908
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_correction_T_min  0.9384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1745
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0754P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1559
_reflns_number_total             1745
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc49759c.txt
_cod_data_source_block           mdpf6
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7112606