Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones.
Goryaeva, Marina V.; Kushch, Svetlana O.; Khudina, Olga G.; Burgart, Yanina V.; Kudyakova, Yulia S.; Ezhikova, Marina A.; Kodess, Mikhail I.; Slepukhin, Pavel A.; Sadretdinova, Lilya Sh; Evstigneeva, Natalya P.; Gerasimova, Natalya A.; Saloutin, Victor I.; Organic & biomolecular chemistry 17 (2019) 4273–4280; doi:10.1039/c9ob00293f

data_7156746
_publ_section_title
;
 Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo
 esters, methyl ketones and alkyl amines: a novel approach to
 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4273
_journal_page_last               4280
_journal_paper_doi               10.1039/c9ob00293f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C11 H17 F3 N2 O2'
_chemical_formula_sum            'C11 H17 F3 N2 O2'
_chemical_formula_weight         266.27
_chemical_melting_point          460.0(10)
_chemical_name_systematic
3-{[2-(Dimethylamino)ethyl]amino}-5-hydroxy-5-(trifluoromethyl)cyclohex-2-en-1-one
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_audit_update_record
;
2018-12-25 deposited with the CCDC.    2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                87.424(6)
_cell_angle_beta                 82.903(6)
_cell_angle_gamma                75.668(7)
_cell_formula_units_Z            2
_cell_length_a                   7.0958(6)
_cell_length_b                   8.4262(7)
_cell_length_c                   11.3160(8)
_cell_measurement_reflns_used    1200
_cell_measurement_temperature    145(2)
_cell_measurement_theta_max      30.0160
_cell_measurement_theta_min      3.6450
_cell_volume                     650.44(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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      145(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega 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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0908
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5313
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         30.80
_diffrn_reflns_theta_min         3.63
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0646
_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^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.2089
_reflns_number_gt                2016
_reflns_number_total             3488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00293f2.cif
_cod_data_source_block           exp_281
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '459-461' was changed to '460.0(10)'
- the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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

 Adding full bibliography for 7156746--7156747.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7156746