The eco-friendly electrosynthesis of trifluoromethylated spirocyclic indolines and their anticancer activity.
Lan, Jianyong; Li, Shaoyun; Lin, Kejun; Zhou, Peng; Chen, Weili; Gao, Liqian; Zhu, Tingshun; Organic & biomolecular chemistry 20 (2022) 3475–3479; doi:10.1039/d2ob00459c

data_7158594
_publ_section_title
;
 The eco-friendly electrosynthesis of trifluoromethylated spirocyclic
 indolines and their anticancer activity.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3475
_journal_page_last               3479
_journal_paper_doi               10.1039/d2ob00459c
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C16 H14 F3 N3 O'
_chemical_formula_sum            'C16 H14 F3 N3 O'
_chemical_formula_weight         321.30
_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     dual
_audit_creation_date             2019-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-02 deposited with the CCDC.	2022-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                111.379(5)
_cell_angle_beta                 101.712(4)
_cell_angle_gamma                94.591(3)
_cell_formula_units_Z            4
_cell_length_a                   8.1282(3)
_cell_length_b                   13.2665(6)
_cell_length_c                   14.8538(8)
_cell_measurement_reflns_used    4253
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.1990
_cell_measurement_theta_min      3.8250
_cell_volume                     1439.47(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.945
_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   -113.00 -15.00   1.00    1.00    --  -41.33 -57.00-180.00   98
  2  \w    -90.00  -3.00   1.00    1.00    --  -41.33 125.00  30.00   87
  3  \w   -114.00  -9.00   1.00    1.00    --  -41.33 -77.00 -60.00  105
  4  \w     95.00 157.00   1.00    5.00    --  106.22 125.00   0.00   62
  5  \w     26.00 108.00   1.00    5.00    --  106.22 -94.00  30.00   82
  6  \w     34.00 121.00   1.00    5.00    --  106.22 -61.00  60.00   87
  7  \w     77.00 175.00   1.00    5.00    --  106.22  61.00  60.00   98
  8  \w     37.00 114.00   1.00    5.00    --  106.22-125.00-120.00   77
  9  \w     57.00 109.00   1.00    5.00    --  106.22 -45.00-120.00   52
 10  \w     43.00 108.00   1.00    5.00    --  106.22 -94.00 -90.00   65
 11  \w     57.00 178.00   1.00    5.00    --  106.22  15.00-180.00  121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0488961000
_diffrn_orient_matrix_UB_12      0.1260711000
_diffrn_orient_matrix_UB_13      0.0442912000
_diffrn_orient_matrix_UB_21      0.0629476000
_diffrn_orient_matrix_UB_22      -0.0008604000
_diffrn_orient_matrix_UB_23      0.1047449000
_diffrn_orient_matrix_UB_31      0.1794824000
_diffrn_orient_matrix_UB_32      -0.0106553000
_diffrn_orient_matrix_UB_33      -0.0173193000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8363
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.523
_diffrn_reflns_theta_min         3.630
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       irregular
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0629P)^2^+0.7591P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1493
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4441
_reflns_number_total             5483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00459c2.cif
_cod_data_source_block           a19110705a0334
_cod_depositor_comments          'Adding full bibliography for 7158594.cif.'
_cod_original_cell_volume        1439.46(12)
_cod_database_code               7158594
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     YU
_shelx_estimated_absorpt_t_max   0.834
_shelx_estimated_absorpt_t_min   0.818
_reflns_odcompleteness_completeness 98.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00M(H00M), C00O(H00O)
2.b Secondary CH2 refined with riding coordinates:
 C010(H01G,H01H), C013(H01A,H01B), C017(H01I,H01J), C018(H01K,H01L), C019(H01C,
 H01D), C01A(H01E,H01F)
2.c Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Z(H00Z), C011(H011), C012(H012),
 C015(H015), C016(H016)
;
_shelx_res_checksum              81450
_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 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.666