Catalyst-free, direct electrochemical synthesis of annulated medium-sized lactams through C–C bond cleavage
Xu, Zhongnan; Huang, Zhixing; Li, Yueheng; Kuniyil, Rositha; Zhang, Chao; Ackermann, Lutz; Ruan, Zhixiong; Green Chemistry 22 (2020) 1099–1104; doi:10.1039/C9GC03901E

data_7239715
_publ_section_title
;
 Catalyst-free, direct electrochemical synthesis of annulated medium-sized
 lactams through C--C bond cleavage
;
_journal_issue                   4
_journal_name_full               'Green Chemistry'
_journal_page_first              1099
_journal_page_last               1104
_journal_paper_doi               10.1039/C9GC03901E
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C19 H16 F3 N O2'
_chemical_formula_sum            'C19 H16 F3 N O2'
_chemical_formula_weight         347.33
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-22 deposited with the CCDC.	2019-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3156(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4973(3)
_cell_length_b                   10.5001(2)
_cell_length_c                   9.92584(18)
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3460
_cell_measurement_theta_min      2.8270
_cell_volume                     1615.14(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_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 -13.00   1.00    1.00    --  -40.98 -57.00 -90.00  100
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00 -30.00   99
  3  \w      5.00  81.00   1.00    1.00    --   40.98 -99.00 120.00   76
  4  \w     29.00 101.00   1.00    1.00    --  106.95 -95.00 -60.00   72
  5  \w     92.00 157.00   1.00    1.00    --  106.95  45.00  30.00   65
  6  \w    101.00 176.00   1.00    1.00    --  106.95 125.00-120.00   75
  7  \w     85.00 175.00   1.00    1.00    --  106.95  30.00 -60.00   90
  8  \w     37.00 118.00   1.00    1.00    --  106.95 -45.00 -60.00   81
  9  \w     58.00  91.00   1.00    1.00    --  106.95  15.00 -30.00   33
 10  \w    153.00 178.00   1.00    1.00    --  106.95  15.00 -30.00   25
 11  \w     52.00  77.00   1.00    1.00    --  106.95 -30.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0507385000
_diffrn_orient_matrix_UB_12      0.0448916000
_diffrn_orient_matrix_UB_13      0.1252804000
_diffrn_orient_matrix_UB_21      0.0853914000
_diffrn_orient_matrix_UB_22      -0.0208195000
_diffrn_orient_matrix_UB_23      -0.0755232000
_diffrn_orient_matrix_UB_31      -0.0036909000
_diffrn_orient_matrix_UB_32      0.1381784000
_diffrn_orient_matrix_UB_33      -0.0517691000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6721
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.513
_diffrn_reflns_theta_min         2.851
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0612P)^2^+0.5201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2916
_reflns_number_total             3139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03901e2.cif
_cod_data_source_block           3-62
_cod_depositor_comments
;Adding full bibliography for 7239715.cif.

 Adding full bibliography for 7239715.cif.
;
_cod_original_cell_volume        1615.15(5)
_cod_database_code               7239715
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C16(H16), C2(H2), C15(H15), C5(H5), C3(H3), C4(H4)
;
_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.649