Expanding the Boxmi Ligand Family: Synthesis and Application of New NON and NSN Ligands.
Blasius, Clemens; Ren, Bing-Tao; Bürgy, David; Liu, Yan-Kai; Li, Bin; Michalsky, Ina; Wadepohl, Hubert; Deng, Qing-Hai; Gade, Lutz H.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00751

data_4038291
_publ_section_title
;
 Expanding the Boxmi Ligand Family: Synthesis and Application of New NON
 and NSN Ligands.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00751
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H30 N2 O3'
_chemical_formula_sum            'C24 H30 N2 O3'
_chemical_formula_weight         394.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_cb17
_audit_creation_date             2019-02-14
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_audit_update_record             '14.02.2019 13:47:30 CET UTC+01:00  encif 1.90'
_cell_angle_alpha                90
_cell_angle_beta                 100.461(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.52511(16)
_cell_length_b                   16.3905(5)
_cell_length_c                   11.8602(3)
_cell_measurement_reflns_used    8267
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      69.5870
_cell_measurement_theta_min      4.6490
_cell_volume                     1056.20(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_publication_material
'encif (Wadepohl, 2009-19); encifer 1.7.x (CCDC, 2018)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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     35.00  65.00   1.00    4.00    --    0.00  57.00-120.00   30
  2  \w    -19.00  15.00   1.00    4.00    --    0.00  57.00-120.00   34
  3  \w     -8.00  18.00   1.00    4.00    --    0.00 -57.00 -90.00   26
  4  \w    -19.00  68.00   1.00    4.00    --    0.00  57.00  60.00   87
  5  \w    -69.00 -14.00   1.00    4.00    --    0.00 -57.00 -90.00   55
  6  \w    -42.00 -17.00   1.00    4.00    --   14.00 123.00 101.04   25
  7  \w    -27.00   4.00   1.00    4.00    --   22.00 115.00 176.56   31
  8  \w    -11.00  14.00   1.00   16.00    --   34.00 105.00  17.98   25
  9  \w     -1.00  25.00   1.00   16.00    --   38.00  94.00-116.47   26
 10  \w      6.00  31.00   1.00   16.00    --   42.00  88.00  24.53   25
 11  \w     13.00  38.00   1.00   16.00    --   46.00  83.00  30.59   25
 12  \w     12.00  37.00   1.00   16.00    --   46.00  84.00 103.55   25
 13  \w     13.00  38.00   1.00   16.00    --   46.00  83.00-132.39   25
 14  \w     19.00  44.00   1.00   16.00    --   50.00  78.00 149.46   25
 15  \w     19.00  44.00   1.00   16.00    --   50.00  79.00  37.16   25
 16  \w     22.00  49.00   1.00   16.00    --   50.00  76.00 -29.45   27
 17  \w     24.00  57.00   1.00   16.00    --   54.00  77.00 -90.00   33
 18  \w     28.00  69.00   1.00   16.00    --   54.00  77.00 150.00   41
 19  \w     28.00  55.00   1.00   16.00    --   54.00  77.00 -30.00   27
 20  \w     24.00  85.00   1.00   16.00    --   54.00-125.00  30.00   61
 21  \w     25.00  50.00   1.00   16.00    --   54.00  77.00 -60.00   25
 22  \w      1.00  96.00   1.00   16.00    --   54.00 -99.00 150.00   95
 23  \w     25.00  52.00   1.00   16.00    --   54.00  77.00-150.00   27
 24  \w     26.00  64.00   1.00   16.00    --   54.00  77.00  90.00   38
 25  \w     74.00 120.00   1.00   16.00    --   54.00  77.00 150.00   46
 26  \w     25.00  50.00   1.00   16.00    --   54.00  77.00 120.00   25
 27  \w     24.00  67.00   1.00   16.00    --   54.00-125.00  90.00   43
 28  \w     35.00  62.00   1.00   16.00    --   54.00  77.00   0.00   27
 29  \w     29.00  55.00   1.00   16.00    --   58.00  76.00 115.24   26
 30  \w     29.00  55.00   1.00   16.00    --   58.00  77.00  68.19   26
 31  \w     29.00  56.00   1.00   16.00    --   58.00  77.00 -20.44   27
 32  \w     32.00  59.00   1.00   16.00    --   58.00  77.00-122.97   27
 33  \w     29.00  54.00   1.00   16.00    --   58.00  77.00  30.19   25
 34  \w     75.00 102.00   1.00   16.00    --   58.00  77.00  30.19   27
 35  \w     40.00  66.00   1.00   16.00    --   62.00  68.00 -35.79   26
 36  \w     42.00  67.00   1.00   16.00    --   62.00  74.00-110.28   25
 37  \w     35.00  63.00   1.00   16.00    --   62.00  73.00-156.82   28
 38  \w     34.00  67.00   1.00   16.00    --   62.00  75.00 153.14   33
 39  \w     40.00  67.00   1.00   16.00    --   66.00  77.00  11.99   27
 40  \w     55.00 134.00   1.00   16.00    --   66.00  66.00-167.61   79
 41  \w     86.00 114.00   1.00   16.00    --   66.00  51.00 -62.82   28
 42  \w     81.00 132.00   1.00   16.00    --   66.00  48.00 123.28   51
 43  \w     45.00  82.00   1.00   16.00    --   66.00  51.00 -62.82   37
 44  \w     44.00  76.00   1.00   16.00    --   66.00  48.00 123.28   32
 45  \w    111.00 136.00   1.00   16.00    --   66.00  77.00  11.99   25
 46  \w     40.00  66.00   1.00   16.00    --   70.00  77.00 103.07   26
 47  \w    107.00 134.00   1.00   16.00    --   74.00  68.00 -49.46   27
 48  \w     51.00 104.00   1.00   16.00    --   74.00  68.00 -49.46   53
 49  \w     55.00  81.00   1.00   16.00    --   74.00  54.00 -11.91   26
 50  \w     57.00  86.00   1.00   16.00    --   78.00  56.00  46.75   29
 51  \w     52.00  89.00   1.00   16.00    --   78.00  72.00   2.25   37
 52  \w     49.00  90.00   1.00   16.00    --   78.00  77.00 150.65   41
 53  \w     57.00 147.00   1.00   16.00    --   78.00  55.00-125.24   90
 54  \w     53.00 151.00   1.00   24.00    --   82.00  75.00  48.64   98
 55  \w     60.00  90.00   1.00   24.00    --   82.00  47.00   8.08   30
 56  \w     75.00 102.00   1.00   24.00    --   82.00  53.00  91.62   27
 57  \w     57.00  83.00   1.00   24.00    --   82.00  69.00 -62.93   26
 58  \w     64.00  94.00   1.00   24.00    --   86.00  61.00 -13.88   30
 59  \w     65.00  92.00   1.00   24.00    --   86.00  67.00  98.88   27
 60  \w    100.00 153.00   1.00   24.00    --   86.00  61.00 -13.88   53
 61  \w     61.00 145.00   1.00   24.00    --   90.00  76.00 111.83   84
 62  \w     66.00 101.00   1.00   24.00    --   94.00  75.00 156.01   35
 63  \w     78.00 124.00   1.00   24.00    --   98.00  53.00 165.01   46
 64  \w    123.00 175.00   1.00   24.00    --  108.00  64.00 -60.00   52
 65  \w     85.00 118.00   1.00   24.00    --  108.00  64.00 -60.00   33
 66  \w     86.00 171.00   1.00   24.00    --  108.00  64.00  90.00   85
 67  \w     78.00 105.00   1.00   24.00    --  108.00  77.00 -30.00   27
 68  \w     37.00  93.00   1.00   24.00    --  108.00 -92.00-150.00   56
 69  \w     70.00 112.00   1.00   24.00    --  108.00-111.00  30.00   42
 70  \w    150.00 175.00   1.00   24.00    --  108.00  64.00-180.00   25
 71  \w     86.00 111.00   1.00   24.00    --  108.00  64.00-180.00   25
 72  \w     79.00 177.00   1.00   24.00    --  108.00  77.00 -90.00   98
 73  \w     80.00 111.00   1.00   24.00    --  108.00-111.00 150.00   31
 74  \w    127.00 178.00   1.00   24.00    --  108.00  77.00  60.00   51
 75  \w     79.00 104.00   1.00   24.00    --  108.00  77.00  60.00   25
 76  \w     86.00 113.00   1.00   24.00    --  108.00  64.00  30.00   27
 77  \w     85.00 174.00   1.00   24.00    --  108.00  64.00-150.00   89
 78  \w     98.00 128.00   1.00   24.00    --  108.00 -64.00 -60.00   30
 79  \w     78.00 105.00   1.00   24.00    --  108.00  77.00 -60.00   27
 80  \w     41.00  88.00   1.00   24.00    --  108.00 -64.00 -60.00   47
 81  \w     39.00 137.00   1.00   24.00    --  108.00 -77.00  60.00   98
 82  \w     83.00 110.00   1.00   24.00    --  108.00  77.00-150.00   27
 83  \w     58.00 112.00   1.00   24.00    --  108.00-111.00 -60.00   54
 84  \w    126.00 157.00   1.00   24.00    --  108.00  38.00-150.00   31
 85  \w     82.00 123.00   1.00   24.00    --  108.00  38.00-150.00   41
 86  \w     85.00 122.00   1.00   24.00    --  108.00  64.00  60.00   37
 87  \w     85.00 116.00   1.00   24.00    --  108.00  64.00   0.00   31
 88  \w     85.00 111.00   1.00   24.00    --  108.00  64.00 -90.00   26
 89  \w     80.00 107.00   1.00   24.00    --  108.00  77.00  90.00   27
 90  \w     85.00 166.00   1.00   24.00    --  108.00  64.00 -30.00   81
 91  \w     78.00 177.00   1.00   24.00    --  108.00  77.00 150.00   99
 92  \w     87.00 170.00   1.00   24.00    --  108.00  64.00 120.00   83
 93  \w     84.00 171.00   1.00   24.00    --  108.00  77.00-120.00   87
 94  \w    115.00 168.00   1.00   24.00    --  108.00  77.00   0.00   53
 95  \w     78.00 104.00   1.00   24.00    --  108.00  77.00   0.00   26
 96  \w     79.00 106.00   1.00   24.00    --  108.00  77.00-180.00   27
 97  \w     79.00 106.00   1.00   24.00    --  108.00  77.00 120.00   27
 98  \w    142.00 177.00   1.00   24.00    --  108.00  77.00  30.00   35
 99  \w     79.00 116.00   1.00   24.00    --  108.00  77.00  30.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0386620000
_diffrn_orient_matrix_UB_12      0.0000696000
_diffrn_orient_matrix_UB_13      -0.1319610000
_diffrn_orient_matrix_UB_21      0.2546739000
_diffrn_orient_matrix_UB_22      -0.0396075000
_diffrn_orient_matrix_UB_23      0.0054527000
_diffrn_orient_matrix_UB_31      -0.1186454000
_diffrn_orient_matrix_UB_32      -0.0852089000
_diffrn_orient_matrix_UB_33      -0.0026342000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19211
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.825
_diffrn_reflns_theta_min         3.790
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model (Busing & Levy, 1957).
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    1.240
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.16(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0340P)^2^+0.0984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0672
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                3694
_reflns_number_total             3958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00751_si_002.cif
_cod_data_source_block           ga_cb17
_cod_original_cell_volume        1056.19(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038291
_audit_block_refno               3276
_audit_block_usercomment         'CBIM19, needle, colourless'
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.938
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelxl_version_number           2018/3
_olex2_refinement_description
;
1. Others
 Uiso(H1)=Uiso(H16)=Uiso(H17)=Uiso(H20)=FVAR(1)
 Uiso(H2A)=Uiso(H2B)=Uiso(H15A)=Uiso(H15B)=FVAR(2)
 Uiso(H4)=Uiso(H8)=Uiso(H9)=Uiso(H13)=FVAR(3)
 Uiso(H18A)=Uiso(H18B)=Uiso(H18C)=Uiso(H19A)=Uiso(H19B)=Uiso(H19C)=Uiso(H21A)=
 Uiso(H21B)=Uiso(H21C)=Uiso(H22A)=Uiso(H22B)=Uiso(H22C)=Uiso(H23A)=Uiso(H23B)=
 Uiso(H23C)=Uiso(H24A)=Uiso(H24B)=Uiso(H24C)=FVAR(4)
2.a Idealised Me refined as rotating group with stretchable bonds:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.778
_shelx_res_checksum              81913
_cell_oxdiff_length_a            5.52396(18)
_cell_oxdiff_length_b            16.3952(5)
_cell_oxdiff_length_c            11.8593(3)
_cell_oxdiff_angle_alpha         89.989(2)
_cell_oxdiff_angle_beta          100.462(2)
_cell_oxdiff_angle_gamma         90.044(3)
_cell_oxdiff_volume              1056.19(6)
_cell_oxdiff_measurement_reflns_used 8267