New heteroanalogs of tricyclic ascidian alkaloids: synthesis and biological activity.
Goryaeva, Marina V.; Kushch, Svetlana O.; Burgart, Yanina V.; Ezhikova, Marina A.; Kodess, Mikhail I.; Slepukhin, Pavel A.; Triandafilova, Galina A.; Krasnykh, Olga P.; Yakovleva, Ekaterina I.; Zarubaev, Vladimir V.; Sinegubova, Ekaterina O.; Esaulkova, Iana L.; Shtro, Anna A.; Galochkina, Anastasia V.; Nikolaeva, Yulia V.; Saloutin, Victor I.; Organic & biomolecular chemistry 19 (2021) 9925–9935; doi:10.1039/d1ob01843d

data_7158387
_publ_section_title
;
 New heteroanalogs of tricyclic ascidian alkaloids: synthesis and
 biological activity.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9925
_journal_page_last               9935
_journal_paper_doi               10.1039/d1ob01843d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C12 H16 F3 N O3'
_chemical_formula_sum            'C12 H16 F3 N O3'
_chemical_formula_weight         279.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-03-09
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                77.963(4)
_cell_angle_beta                 77.679(4)
_cell_angle_gamma                76.073(4)
_cell_formula_units_Z            2
_cell_length_a                   5.6852(3)
_cell_length_b                   9.4367(4)
_cell_length_c                   12.6134(6)
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.0210
_cell_measurement_theta_min      3.0360
_cell_volume                     632.80(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.8641
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -49.00  34.00   1.00    7.50    --   17.59 -57.00 -60.00   83
  2  \w    -41.00  34.00   1.00    7.50    --   17.59 -57.00-180.00   75
  3  \w     -9.00  32.00   1.00    7.50    --   17.59  77.00  60.00   41
  4  \w     -9.00  36.00   1.00    7.50    --   17.59  77.00 -60.00   45
  5  \w      5.00  38.00   1.00    7.50    --   17.59  77.00 150.00   33
  6  \w    -16.00  10.00   1.00    7.50    --   17.59 -99.00 -90.00   26
  7  \w     14.00  85.00   1.00    7.50    --   17.59  57.00  90.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0539702000
_diffrn_orient_matrix_UB_12      -0.0538551000
_diffrn_orient_matrix_UB_13      0.0392856000
_diffrn_orient_matrix_UB_21      0.1057235000
_diffrn_orient_matrix_UB_22      -0.0199426000
_diffrn_orient_matrix_UB_23      0.0255149000
_diffrn_orient_matrix_UB_31      -0.0541849000
_diffrn_orient_matrix_UB_32      0.0535577000
_diffrn_orient_matrix_UB_33      0.0348190000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5210
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         1.68
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1374
_reflns_number_gt                1854
_reflns_number_total             2929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01843d2.cif
_cod_data_source_block           exp_1145
_cod_depositor_comments
'Adding full bibliography for 7158386--7158394.cif.'
_cod_database_code               7158387
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.077
_oxdiff_exptl_absorpt_empirical_full_min 0.900