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_7126268
_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         '0.33(C30 H38 N2 O4)'
_chemical_formula_sum            'C10 H12.67 N0.67 O1.33'
_chemical_formula_weight         163.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-02-10 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.301(4)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   17.8343(6)
_cell_length_b                   12.4405(4)
_cell_length_c                   13.0921(5)
_cell_measurement_reflns_used    2622
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      71.1550
_cell_measurement_theta_min      7.9390
_cell_volume                     2773.29(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -14.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000  -30.0000 100

  2 omega   42.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 40

  3 omega   40.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 36

  4 omega    2.00   41.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -90.0000 39

  5 omega   27.00   54.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000    0.0000 27

  6 omega   39.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   30.0000 25

  7 omega   60.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 44

  8 omega   59.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 39

  9 omega   56.00   96.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 40

 10 omega   52.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 39

 11 omega   43.00  169.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  120.0000 126

 12 omega   81.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 89

 13 omega   17.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 50

 14 omega   -3.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000   60.0000 31

 15 omega  -12.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 82

 16 omega  -59.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000   60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356161000
_diffrn_orient_matrix_UB_12      0.1053144000
_diffrn_orient_matrix_UB_13      -0.0266910000
_diffrn_orient_matrix_UB_21      -0.0407470000
_diffrn_orient_matrix_UB_22      -0.0187870000
_diffrn_orient_matrix_UB_23      -0.1199950000
_diffrn_orient_matrix_UB_31      -0.0724565000
_diffrn_orient_matrix_UB_32      0.0624686000
_diffrn_orient_matrix_UB_33      0.0086931000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.486
_diffrn_reflns_theta_min         4.402
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.648
_exptl_absorpt_correction_T_min  0.518
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.175
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2008
_exptl_crystal_size_mid          0.1607
_exptl_crystal_size_min          0.1298
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0505P)^2^+1.3821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2332
_reflns_number_total             2640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01192d2.cif
_cod_data_source_block           mn1601
_cod_depositor_comments
'Adding full bibliography for 7126266--7126270.cif.'
_cod_original_cell_volume        2773.29(17)
_cod_database_code               7126268
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C30 H34 Cl1 Cr1 N2 O4'
_chemical_oxdiff_usercomment     'Katie KL OMe cat THF sample 1'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.047) H1(0.03) H8(0.025) H10(0.031) H12(0.025) H14(0.036)
 H11A(0.054) H11B(0.054) H11C(0.054) H15(0.043) H3A(0.068) H3B(0.068)
 H3C(0.068) H1A(0.073) H1B(0.073) H1C(0.073) H2A(0.076) H2B(0.076) H2C(0.076)
 Fixed X: H2(0.63) H1(0.5174) H8(0.4209) H10(0.6053) H12(0.4345) H14(0.528)
 H11A(0.3523) H11B(0.3599) H11C(0.3804) H15(0.5133) H3A(0.7497) H3B(0.8151)
 H3C(0.7344) H1A(0.7476) H1B(0.8231) H1C(0.7572) H2A(0.719) H2B(0.802)
 H2C(0.7307)
 Fixed Y: H2(0.333) H1(0.2593) H8(0.5408) H10(0.7225) H12(0.36) H14(0.0678)
 H11A(0.6858) H11B(0.8073) H11C(0.7175) H15(-0.0931) H3A(0.4335) H3B(0.5162)
 H3C(0.5166) H1A(0.6219) H1B(0.58) H1C(0.499) H2A(0.7115) H2B(0.7041)
 H2C(0.7509)
 Fixed Z: H2(0.7031) H1(0.5906) H8(0.6052) H10(0.6018) H12(0.6545) H14(0.5887)
 H11A(0.5146) H11B(0.5479) H11C(0.636) H15(0.6684) H3A(0.6253) H3B(0.6215)
 H3C(0.5313) H1A(0.8312) H1B(0.8059) H1C(0.8119) H2A(0.5663) H2B(0.6513)
 H2C(0.6838)
;
_shelx_res_checksum              29276
_olex2_date_sample_data_collection 2016-02-16
_olex2_date_sample_submission    2016-02-15
_olex2_submission_original_sample_id 'KL OMe cat THF'
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.837