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_7158393
_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 H17 F3 N2 O2'
_chemical_formula_sum            'C12 H17 F3 N2 O2'
_chemical_formula_weight         278.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8729(14)
_cell_length_b                   12.6636(14)
_cell_length_c                   15.6817(15)
_cell_measurement_reflns_used    1358
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.0710
_cell_measurement_theta_min      4.4360
_cell_volume                     2556.4(5)
_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    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.851
_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    -90.00 -59.00   1.00   30.00    --  -24.08 -73.00  84.00   31
  2  \w    -35.00  17.00   1.00   30.00    --  -24.08  49.00  28.00   52
  3  \w     36.00  61.00   1.00   30.00    --   22.36 178.00   0.00   25
  4  \w     35.00  93.00   1.00   30.00    --   22.36 178.00 -90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319862000
_diffrn_orient_matrix_UB_12      0.0389387000
_diffrn_orient_matrix_UB_13      0.0191236000
_diffrn_orient_matrix_UB_21      0.0443752000
_diffrn_orient_matrix_UB_22      -0.0229554000
_diffrn_orient_matrix_UB_23      -0.0193801000
_diffrn_orient_matrix_UB_31      -0.0068150000
_diffrn_orient_matrix_UB_32      0.0330089000
_diffrn_orient_matrix_UB_33      -0.0361338000
_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  0.0454
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8484
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.999
_diffrn_reflns_theta_min         3.470
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74621
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0023(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0584
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.2194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1684
_reflns_number_total             3475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01843d2.cif
_cod_data_source_block           exp_816
_cod_depositor_comments
'Adding full bibliography for 7158386--7158394.cif.'
_cod_database_code               7158393
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.940
_reflns_odcompleteness_completeness 98.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H6AA(0.6) H6AB(0.6) H6BC(0.4) H6BD(0.4) H8AA(0.6) H8AB(0.6)
 H8BC(0.4) H8BD(0.4) C7(0.6) H7A(0.6) H7B(0.6) C7A(0.4) H7AA(0.4) H7AB(0.4)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C2(H2A,H2B), C6(H6AA,H6AB), C6(H6BC,H6BD), C4(H4A,H4B),
 C8(H8AA,H8AB), C8(H8BC,H8BD), C3(H3A,H3B), C7(H7A,H7B), C7A(H7AA,H7AB)
;
_shelx_res_checksum              80601
_shelx_hkl_checksum              70535
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.202
_oxdiff_exptl_absorpt_empirical_full_min 0.881