Unprecedented reductive cyclisation of salophen ligands to tetrahydroquinoxalines during metal complex formation.
Lamb, Katie J.; Dowsett, Mark R.; North, Michael; Parker, Rachel R.; Whitwood, Adrian C.; Chemical communications (Cambridge, England) 56 (2020) 4844–4847; doi:10.1039/d0cc01192d

data_7126266
_publ_section_title
;
 Unprecedented reductive cyclisation of salophen ligands to
 tetrahydroquinoxalines during metal complex formation.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4844
_journal_page_last               4847
_journal_paper_doi               10.1039/d0cc01192d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H16 F6 N2 O2'
_chemical_formula_sum            'C22 H16 F6 N2 O2'
_chemical_formula_weight         454.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-10 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.1272(4)
_cell_length_b                   9.04947(13)
_cell_length_c                   14.7304(2)
_cell_measurement_reflns_used    3984
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.8870
_cell_measurement_theta_min      5.9310
_cell_volume                     3749.42(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -19.00  23.00   1.00    1.00    --    0.00 -77.00-120.00   42
  2  \w    -16.00  19.00   1.00    1.00    --    0.00 -77.00 150.00   35
  3  \w    -17.00  10.00   1.00    1.00    --    0.00 -77.00 120.00   27
  4  \w     47.00  73.00   1.00    1.50    --   54.00  61.00 -47.00   26
  5  \w     16.00  72.00   1.00    1.50    --   54.00 -57.00 -30.00   56
  6  \w    -16.00  75.00   1.00    1.50    --   54.00 -37.00-180.00   91
  7  \w     45.00  87.00   1.00    3.00    --  108.00 -91.00-120.00   42
  8  \w     45.00 126.00   1.00    3.00    --  108.00 -63.00  60.00   81
  9  \w     61.00 107.00   1.00    3.00    --  108.00 -91.00 -60.00   46
 10  \w    121.00 164.00   1.00    3.00    --  108.00 111.00  60.00   43
 11  \w     55.00 103.00   1.00    3.00    --  108.00 -91.00  30.00   48
 12  \w     37.00  64.00   1.00    3.00    --  108.00 -91.00-150.00   27
 13  \w    148.00 174.00   1.00    3.00    --  108.00  77.00 -90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0266056000
_diffrn_orient_matrix_UB_12      0.1382026000
_diffrn_orient_matrix_UB_13      0.0340186000
_diffrn_orient_matrix_UB_21      -0.0409808000
_diffrn_orient_matrix_UB_22      0.0328900000
_diffrn_orient_matrix_UB_23      0.0663833000
_diffrn_orient_matrix_UB_31      0.0247830000
_diffrn_orient_matrix_UB_32      -0.0938030000
_diffrn_orient_matrix_UB_33      0.0732666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8178
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.052
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_min         5.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.00027(6)
_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   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+2.2558P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2987
_reflns_number_total             3350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01192d2.cif
_cod_data_source_block           mn2001
_cod_depositor_comments
'Adding full bibliography for 7126266--7126270.cif.'
_cod_original_cell_volume        3749.43(9)
_cod_database_code               7126266
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H16 F6 N2 O2'
_chemical_oxdiff_usercomment     'Katie Lamb KL CF3 col NMR'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              5677
_olex2_date_sample_data_collection 2020-01-08
_olex2_date_sample_submission    2019-12-17
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id 'KL CF3 col NMR'
_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 1.110
_oxdiff_exptl_absorpt_empirical_full_min 0.838