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_7158386
_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_absolute_configuration unk
_chemical_formula_moiety         'C12 H17 F3 N2 O2'
_chemical_formula_sum            'C12 H17 F3 N2 O2'
_chemical_formula_weight         278.276
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-06-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_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            4
_cell_length_a                   5.5102(5)
_cell_length_b                   9.0870(9)
_cell_length_c                   25.588(3)
_cell_measurement_reflns_used    1442
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.9280
_cell_measurement_theta_min      3.9070
_cell_volume                     1281.2(2)
_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  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_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 0.9860
_diffrn_measured_fraction_theta_max 0.8789
_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     23.00  76.10   0.30   10.00    --   22.36-133.00  29.00  177
  2  \w    -45.00  25.20   0.30   10.00    --  -24.08  19.00-120.00  234
  3  \w     37.00  87.10   0.30   10.00    --   22.36  57.00-120.00  167
;
_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      0.0288543000
_diffrn_orient_matrix_UB_12      -0.0673595000
_diffrn_orient_matrix_UB_13      -0.0125646000
_diffrn_orient_matrix_UB_21      -0.0133080000
_diffrn_orient_matrix_UB_22      0.0345168000
_diffrn_orient_matrix_UB_23      -0.0247235000
_diffrn_orient_matrix_UB_31      0.1246161000
_diffrn_orient_matrix_UB_32      0.0192237000
_diffrn_orient_matrix_UB_33      0.0002686000
_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  0.0401
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.9860
_diffrn_reflns_Laue_measured_fraction_max 0.8789
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            5041
_diffrn_reflns_point_group_measured_fraction_full 0.9860
_diffrn_reflns_point_group_measured_fraction_max 0.8789
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         30.73
_diffrn_reflns_theta_min         3.78
_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  0.24158
_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    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             584.427
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.2770
_refine_diff_density_min         -0.3309
_refine_diff_density_rms         0.0691
_refine_ls_d_res_high            0.6955
_refine_ls_d_res_low             5.3867
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0116
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^+0.0410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1783
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              0
_reflns_number_gt                1458
_reflns_number_total             2039
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ob01843d2.cif
_cod_data_source_block           exp_767
_cod_depositor_comments
'Adding full bibliography for 7158386--7158394.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7158386
_reflns_odcompleteness_completeness 98.79
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C8(H8a,H8b), C7(H7a,H7b), C6(H6a,H6b), C11(H11a,H11b), C12(H12a,
 H12b), C3(H3a,H3b)
;
_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 2.338
_oxdiff_exptl_absorpt_empirical_full_min 0.542