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_7112603
_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_formula_moiety         'C7 H15 N2 O2, Cl'
_chemical_formula_sum            'C7 H15 Cl N2 O2'
_chemical_formula_weight         194.66
_chemical_melting_point          171
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.363(2)
_cell_length_b                   12.708(3)
_cell_length_c                   13.781(3)
_cell_measurement_temperature    298(2)
_cell_volume                     1814.9(7)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13514
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         26.21
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0511
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1559
_reflns_number_gt                1336
_reflns_number_total             1812
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc49759c.txt
_cod_data_source_block           mdeacn
_cod_original_cell_volume        1814.8(6)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7112603