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_7158394
_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         'C17 H19 F3 N2 O2, C2 H3 N'
_chemical_formula_sum            'C19 H22 F3 N3 O2'
_chemical_formula_weight         381.401
_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_Int_Tables_number      14
_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                 104.837(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2653(9)
_cell_length_b                   9.7195(12)
_cell_length_c                   19.2671(17)
_cell_measurement_reflns_used    1472
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.8050
_cell_measurement_theta_min      3.9520
_cell_volume                     1858.3(3)
_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 0.9813
_diffrn_measured_fraction_theta_max 0.8399
_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    -91.00   1.00   1.00   15.00    --  -24.08 -77.00 150.00   92
  2  \w    -54.00  38.00   1.00   15.00    --  -24.08  77.00 -90.00   92
  3  \w    -93.00  -3.00   1.00   15.00    --  -24.08 -57.00  30.00   90
  4  \w    -50.00 -41.00   1.00   15.00    --  -24.08  77.00   0.00    9
;
_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      -0.0443416000
_diffrn_orient_matrix_UB_12      0.0469593000
_diffrn_orient_matrix_UB_13      0.0104572000
_diffrn_orient_matrix_UB_21      -0.0554809000
_diffrn_orient_matrix_UB_22      -0.0310337000
_diffrn_orient_matrix_UB_23      -0.0247439000
_diffrn_orient_matrix_UB_31      -0.0078195000
_diffrn_orient_matrix_UB_32      -0.0465594000
_diffrn_orient_matrix_UB_33      0.0269731000
_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  0.0537
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.9813
_diffrn_reflns_Laue_measured_fraction_max 0.8399
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11434
_diffrn_reflns_point_group_measured_fraction_full 0.9813
_diffrn_reflns_point_group_measured_fraction_max 0.8399
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         31.04
_diffrn_reflns_theta_min         3.89
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82513
_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    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             800.505
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.3708
_refine_diff_density_min         -0.4323
_refine_diff_density_rms         0.0984
_refine_ls_d_res_high            0.6892
_refine_ls_d_res_low             5.2320
_refine_ls_goodness_of_fit_ref   1.0099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0099
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0850P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.2223
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2208
_reflns_number_total             4978
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ob01843d2.cif
_cod_data_source_block           exp_769
_cod_depositor_comments
'Adding full bibliography for 7158386--7158394.cif.'
_cod_database_code               7158394
_reflns_odcompleteness_completeness 96.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b), C12(H12a,H12b), C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C3s(H3sa,H3sb,H3sc)
;
_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 1.105
_oxdiff_exptl_absorpt_empirical_full_min 0.861