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_7126270
_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         'C28 H34 N2 O2'
_chemical_formula_sum            'C28 H34 N2 O2'
_chemical_formula_weight         430.57
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-23
_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                 105.2865(12)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   16.29085(17)
_cell_length_b                   20.8151(2)
_cell_length_c                   23.2057(3)
_cell_measurement_reflns_used    10102
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      69.8280
_cell_measurement_theta_min      4.3720
_cell_volume                     7590.55(15)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -66.00 -39.00   1.00    6.25    --    0.00 146.00 -55.00   27
  2  \w    -51.00 -22.00   1.00    6.25    --    0.00 125.00 138.00   29
  3  \w      6.00  60.00   1.00    6.25    --    0.00  57.00 -30.00   54
  4  \w      1.00  65.00   1.00   25.00    --   54.00 -99.00  60.00   64
  5  \w     45.00 120.00   1.00   25.00    --   54.00  37.00 -60.00   75
  6  \w     33.00  96.00   1.00   25.00    --   54.00 -99.00-180.00   63
  7  \w     24.00  79.00   1.00   25.00    --   54.00-125.00 150.00   55
  8  \w     17.00  74.00   1.00   25.00    --   54.00 -57.00 -90.00   57
  9  \w     58.00 125.00   1.00   25.00    --  108.00 -37.00-120.00   67
 10  \w     88.00 176.00   1.00   25.00    --  108.00  63.00-150.00   88
 11  \w     78.00 173.00   1.00   25.00    --  108.00  77.00 -90.00   95
 12  \w     38.00 134.00   1.00   25.00    --  108.00 -77.00 150.00   96
 13  \w     80.00 113.00   1.00   25.00    --  108.00-111.00 -90.00   33
 14  \w     78.00 112.00   1.00   25.00    --  108.00  77.00-180.00   34
 15  \w     48.00 136.00   1.00   25.00    --  108.00 -77.00 -30.00   88
;
_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      0.0431064000
_diffrn_orient_matrix_UB_12      -0.0630952000
_diffrn_orient_matrix_UB_13      -0.0108294000
_diffrn_orient_matrix_UB_21      0.0266774000
_diffrn_orient_matrix_UB_22      -0.0127634000
_diffrn_orient_matrix_UB_23      0.0677487000
_diffrn_orient_matrix_UB_31      -0.0839181000
_diffrn_orient_matrix_UB_32      -0.0365114000
_diffrn_orient_matrix_UB_33      -0.0051269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29179
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.524
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.859
_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    1.130
_exptl_crystal_description       plate
_exptl_crystal_F_000             2784
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00024(3)
_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   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     926
_refine_ls_number_reflns         13536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0590P)^2^+4.8015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1379
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10818
_reflns_number_total             13536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01192d2.cif
_cod_data_source_block           mn1909
_cod_depositor_comments
'Adding full bibliography for 7126266--7126270.cif.'
_cod_original_cell_volume        7590.57(15)
_cod_database_code               7126270
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H34 N2 O2'
_chemical_oxdiff_usercomment     'Katie Lamb KL 4-T Cry'
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.031) H3(0.032) H5(0.03) H7(0.028) H9(0.042) H10(0.054)
 H11(0.062) H12(0.052) H14(0.03) H16(0.03) H18(0.045) H19(0.046) H22A(0.058)
 H22B(0.058) H22C(0.058) H23A(0.051) H23B(0.051) H23C(0.051) H24A(0.06)
 H24B(0.06) H24C(0.06) H26A(0.088) H26B(0.088) H26C(0.088) H27A(0.075)
 H27B(0.075) H27C(0.075) H28A(0.061) H28B(0.061) H28C(0.061) H30(0.038)
 H31(0.04) H33(0.034) H35(0.033) H37(0.047) H38(0.054) H39(0.054) H40(0.047)
 H42(0.034) H44(0.031) H46(0.045) H47(0.049) H50A(0.065) H50B(0.065)
 H50C(0.065) H51A(0.096) H51B(0.096) H51C(0.096) H52A(0.081) H52B(0.081)
 H52C(0.081) H54A(0.064) H54B(0.064) H54C(0.064) H55A(0.063) H55B(0.063)
 H55C(0.063) H56A(0.064) H56B(0.064) H56C(0.064) H3B(0.05) H4A(0.068)
 H58(0.034) H59(0.035) H61(0.029) H63(0.027) H65(0.039) H66(0.045) H67(0.047)
 H68(0.039) H70(0.027) H72(0.027) H74(0.034) H75(0.035) H78A(0.072) H78B(0.072)
 H78C(0.072) H79A(0.064) H79B(0.064) H79C(0.064) H80A(0.071) H80B(0.071)
 H80C(0.071) H82A(0.069) H82B(0.069) H82C(0.069) H83A(0.057) H83B(0.057)
 H83C(0.057) H84A(0.072) H84B(0.072) H84C(0.072)
 Fixed X: H2(0.445905) H3(0.549986) H5(0.461246) H7(0.346619) H9(0.295623)
 H10(0.192143) H11(0.086005) H12(0.080776) H14(0.219931) H16(0.25322)
 H18(0.303971) H19(0.289968) H22A(0.675806) H22B(0.691654) H22C(0.617921)
 H23A(0.602024) H23B(0.682259) H23C(0.666052) H24A(0.511804) H24B(0.588616)
 H24C(0.50969) H26A(0.165982) H26B(0.226804) H26C(0.232759) H27A(0.313761)
 H27B(0.279753) H27C(0.216582) H28A(0.388342) H28B(0.382146) H28C(0.418383)
 H30(1.061158) H31(1.116175) H33(1.100093) H35(1.048133) H37(1.077057)
 H38(1.002881) H39(0.880952) H40(0.835642) H42(0.901521) H44(0.861578)
 H46(0.850586) H47(0.897644) H50A(1.266274) H50B(1.278472) H50C(1.232618)
 H51A(1.117698) H51B(1.209828) H51C(1.194038) H52A(1.121439) H52B(1.08856)
 H52C(1.04253) H54A(0.889762) H54B(0.863173) H54C(0.937546) H55A(0.787819)
 H55B(0.770227) H55C(0.86357) H56A(0.736763) H56B(0.691967) H56C(0.712291)
 H3B(1.009121) H4A(0.935426) H58(0.203193) H59(0.162697) H61(0.298521)
 H63(0.370918) H65(0.325305) H66(0.426063) H67(0.568704) H68(0.609856)
 H70(0.455905) H72(0.464533) H74(0.539217) H75(0.551554) H78A(0.087477)
 H78B(0.121809) H78C(0.16807) H79A(0.178451) H79B(0.124388) H79C(0.09504)
 H80A(0.305261) H80B(0.2534) H80C(0.306781) H82A(0.361691) H82B(0.393475)
 H82C(0.384558) H83A(0.534694) H83B(0.542309) H83C(0.607603) H84A(0.572385)
 H84B(0.505687) H84C(0.478063)
 Fixed Y: H2(0.531408) H3(0.501604) H5(0.32204) H7(0.289706) H9(0.269063)
 H10(0.195759) H11(0.167564) H12(0.214162) H14(0.388588) H16(0.449627)
 H18(0.367083) H19(0.267396) H22A(0.455088) H22B(0.422232) H22C(0.472353)
 H23A(0.295902) H23B(0.31566) H23C(0.346784) H24A(0.391726) H24B(0.344793)
 H24C(0.322702) H26A(0.48525) H26B(0.531449) H26C(0.457005) H27A(0.538455)
 H27B(0.5813) H27C(0.538295) H28A(0.459015) H28B(0.533688) H28C(0.49099)
 H30(0.399473) H31(0.498484) H33(0.555969) H35(0.489783) H37(0.299419)
 H38(0.263948) H39(0.318127) H40(0.407081) H42(0.426152) H44(0.481033)
 H46(0.671758) H47(0.678895) H50A(0.651448) H50B(0.576826) H50C(0.607074)
 H51A(0.607882) H51B(0.580129) H51C(0.654234) H52A(0.698824) H52B(0.653299)
 H52C(0.654386) H54A(0.650873) H54B(0.606265) H54C(0.58576) H55A(0.504113)
 H55B(0.481387) H55C(0.482561) H56A(0.649638) H56B(0.583661) H56C(0.604582)
 H3B(0.355203) H4A(0.555701) H58(0.82769) H59(0.760789) H61(0.866078)
 H63(0.960639) H65(1.134203) H66(1.214876) H67(1.190866) H68(1.086709)
 H70(0.925267) H72(0.812312) H74(0.717582) H75(0.813255) H78A(0.726232)
 H78B(0.684237) H78C(0.682945) H79A(0.841665) H79B(0.781665) H79C(0.824594)
 H80A(0.711822) H80B(0.710404) H80C(0.771365) H82A(0.682182) H82B(0.6452)
 H82C(0.720195) H83A(0.727567) H83B(0.652532) H83C(0.695588) H84A(0.634801)
 H84B(0.593859) H84C(0.630562)
 Fixed Z: H2(0.232916) H3(0.316895) H5(0.299526) H7(0.222908) H9(0.041878)
 H10(-0.004529) H11(0.040521) H12(0.129018) H14(0.202666) H16(0.292388)
 H18(0.453371) H19(0.409715) H22A(0.370632) H22B(0.433399) H22C(0.412714)
 H23A(0.33622) H23B(0.38709) H23C(0.323561) H24A(0.430623) H24B(0.454106)
 H24C(0.403242) H26A(0.419667) H26B(0.464837) H26C(0.47535) H27A(0.340611)
 H27B(0.384878) H27C(0.337891) H28A(0.47931) H28B(0.470428) H28C(0.427187)
 H30(0.098406) H31(0.08321) H33(0.243747) H35(0.30814) H37(0.381622)
 H38(0.447943) H39(0.454559) H40(0.39608) H42(0.234968) H44(0.144758)
 H46(0.134687) H47(0.236845) H50A(0.198344) H50B(0.196689) H50C(0.241713)
 H51A(0.063969) H51B(0.088207) H51C(0.090852) H52A(0.16274) H52B(0.20565)
 H52C(0.137204) H54A(0.044942) H54B(-0.011346) H54C(0.043516) H55A(-0.007041)
 H55B(0.052998) H55C(0.046459) H56A(0.051672) H56B(0.055267) H56C(-0.004392)
 H3B(0.221793) H4A(0.330044) H58(0.225657) H59(0.292206) H61(0.428037)
 H63(0.41372) H65(0.316402) H66(0.329581) H67(0.369203) H68(0.39605)
 H70(0.324346) H72(0.32935) H74(0.484281) H75(0.535293) H78A(0.356378)
 H78B(0.413764) H78C(0.362485) H79A(0.465821) H79B(0.473895) H79C(0.416636)
 H80A(0.438972) H80B(0.487069) H80C(0.480608) H82A(0.352508) H82B(0.303618)
 H82C(0.300514) H83A(0.295575) H83B(0.299662) H83C(0.345171) H84A(0.42757)
 H84B(0.380946) H84C(0.43178)
;
_shelx_res_checksum              2886
_shelx_fab_checksum              31620
_olex2_date_sample_data_collection 2019-09-12
_olex2_date_sample_submission    2019-08-21
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id 'KL 4-T Cry'
_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 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.807