Contrasting reactivity of fluorinated 2,6-heptanediones towards amines and ammonia, leading to cyclohexanediones or 2-oxa-6-azabicyclo[2.2.2]octanes and evaluation of their cytotoxicity
Pikun, Nadiia V.; Kolesnyk, Natalya P.; Rusanov, Eduard B.; Plotniece, Aiva; Sobolev, Arkadij; Domracheva, Ilona; Shermolovich, Yuriy G.; New Journal of Chemistry 43 (2019) 10537–; doi:10.1039/C9NJ01446B

data_7058444
_publ_section_title
;
 Contrasting reactivity of fluorinated 2,6-heptanediones towards amines
 and ammonia, leading to cyclohexanediones or
 2-oxa-6-azabicyclo[2.2.2]octanes and evaluation of their cytotoxicity
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10537
_journal_paper_doi               10.1039/C9NJ01446B
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C17 H15 F2 O5, C3 H10 N'
_chemical_formula_sum            'C20 H25 F2 N O5'
_chemical_formula_weight         397.41
_chemical_melting_point          434.0(10)
_chemical_name_systematic
'propan-1-aminium 3-acetyl-5-(ethoxycarbonyl)-3,5-difluoro-2,6-dioxo-4-phenylcyclohexan-1-ide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2018-04-27 deposited with the CCDC.    2019-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.081(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.196(3)
_cell_length_b                   16.494(4)
_cell_length_c                   9.256(2)
_cell_measurement_reflns_used    1134
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      23.23
_cell_measurement_theta_min      2.47
_cell_volume                     1954.1(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19718
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.185
_diffrn_reflns_theta_min         2.014
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0459P)^2^+0.5151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2992
_reflns_number_total             4326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj01446b2.cif
_cod_data_source_block           n561
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '433-435' was changed to '434.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7058444.cif.
;
_cod_database_code               7058444
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              30829