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_4038290
_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         'C30 H26 N2 O3'
_chemical_formula_sum            'C30 H26 N2 O3'
_chemical_formula_weight         462.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_cb15
_audit_creation_date             2018-11-26
_audit_creation_method
;
encif (version 1.112)

encifer (version_id = 270009.64)

Olex2 1.3
(compiled 2019.11.22 svn.r41b7951 for OlexSys, GUI svn.r6003)
;
_audit_update_record
'19.02.2020 10:22:42 CET UTC+01:00  encif 1.112'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.68389(6)
_cell_length_b                   12.24377(14)
_cell_length_c                   33.9789(3)
_cell_measurement_reflns_used    30545
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      69.3310
_cell_measurement_theta_min      3.8100
_cell_volume                     2364.67(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_publication_material
'encif (Wadepohl, 2009-19); encifer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2014 (Giacovazzo et al., 2014)'
_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 0.999
_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    -22.00  69.00   1.00    2.50    --    0.00  57.00 150.00   91
  2  \w    -22.00  69.00   1.00    2.50    --    0.00  57.00-120.00   91
  3  \w    -34.00  17.00   1.00    2.50    --   12.00 103.00 -16.35   51
  4  \w    -30.00  17.00   1.00    2.50    --   16.00 103.00-170.89   47
  5  \w    -31.00  14.00   1.00    2.50    --   16.00 106.00 101.56   45
  6  \w    -26.00  17.00   1.00    2.50    --   20.00 104.00 -88.06   43
  7  \w     -4.00  28.00   1.00    7.50    --   36.00  92.00-163.78   32
  8  \w      5.00  32.00   1.00    7.50    --   44.00  90.00  -9.58   27
  9  \w      5.00  32.00   1.00    7.50    --   44.00  90.00 116.24   27
 10  \w      6.00  33.00   1.00    7.50    --   44.00  89.00 -73.46   27
 11  \w     13.00  40.00   1.00    7.50    --   48.00  83.00 170.35   27
 12  \w     14.00  45.00   1.00    7.50    --   48.00  81.00 -67.24   31
 13  \w     13.00  40.00   1.00    7.50    --   48.00  83.00  91.18   27
 14  \w     15.00  45.00   1.00    7.50    --   48.00  79.00  73.93   30
 15  \w     19.00  45.00   1.00    7.50    --   52.00  80.00  -6.90   26
 16  \w     18.00  45.00   1.00    7.50    --   52.00  82.00-103.73   27
 17  \w     19.00  45.00   1.00    7.50    --   52.00  80.00-167.44   26
 18  \w    -15.00  76.00   1.00    7.50    --   54.00 -57.00 150.00   91
 19  \w     22.00 125.00   1.00    7.50    --   54.00  77.00  90.00  103
 20  \w     -1.00  96.00   1.00    7.50    --   54.00 -97.00 -64.00   97
 21  \w     23.00 112.00   1.00    7.50    --   54.00-125.00 120.00   89
 22  \w    -19.00  81.00   1.00    7.50    --   54.00 -38.00 -60.00  100
 23  \w     25.00 127.00   1.00    7.50    --   56.00  75.00-118.24  102
 24  \w     25.00 127.00   1.00    7.50    --   56.00  76.00  28.28  102
 25  \w     25.00 127.00   1.00    7.50    --   56.00  75.00 -55.29  102
 26  \w     29.00 126.00   1.00    7.50    --   56.00  69.00 154.14   97
 27  \w     24.00 127.00   1.00    7.50    --   56.00  77.00-174.85  103
 28  \w     29.00 131.00   1.00    7.50    --   60.00  75.00-173.51  102
 29  \w     29.00 131.00   1.00    7.50    --   60.00  75.00  60.55  102
 30  \w     29.00 131.00   1.00    7.50    --   60.00  76.00 -57.57  102
 31  \w     29.00 131.00   1.00    7.50    --   60.00  75.00-142.59  102
 32  \w     30.00 130.00   1.00    7.50    --   60.00  74.00  48.04  100
 33  \w     28.00 131.00   1.00    7.50    --   60.00  77.00 112.15  103
 34  \w     29.00 131.00   1.00    7.50    --   60.00  75.00 -20.27  102
 35  \w     31.00 130.00   1.00    7.50    --   60.00  73.00  97.09   99
 36  \w     36.00 134.00   1.00    7.50    --   64.00  70.00 -77.57   98
 37  \w     34.00 134.00   1.00    7.50    --   64.00  74.00 -55.44  100
 38  \w     40.00 138.00   1.00    7.50    --   68.00  71.00-132.04   98
 39  \w     36.00 139.00   1.00    7.50    --   68.00  77.00  29.09  103
 40  \w     37.00 139.00   1.00    7.50    --   68.00  76.00 -33.57  102
 41  \w     37.00 139.00   1.00    7.50    --   68.00  76.00 132.11  102
 42  \w     39.00 138.00   1.00    7.50    --   68.00  72.00-175.36   99
 43  \w     37.00 139.00   1.00    7.50    --   68.00  76.00 161.02  102
 44  \w     46.00 141.00   1.00    7.50    --   72.00  67.00-176.64   95
 45  \w     42.00 142.00   1.00    7.50    --   72.00  74.00-111.42  100
 46  \w     44.00 142.00   1.00    7.50    --   72.00  70.00-110.99   98
 47  \w     41.00 143.00   1.00    7.50    --   72.00  75.00  89.29  102
 48  \w     43.00 142.00   1.00    7.50    --   72.00  73.00  75.74   99
 49  \w     46.00 141.00   1.00    7.50    --   72.00  66.00 179.41   95
 50  \w     43.00 142.00   1.00    7.50    --   72.00  73.00  66.04   99
 51  \w     54.00 146.00   1.00    7.50    --   76.00  55.00 124.29   92
 52  \w     49.00 151.00   1.00    7.50    --   80.00  76.00-152.81  102
 53  \w     56.00 148.00   1.00    7.50    --   80.00  62.00 -35.10   92
 54  \w     54.00 149.00   1.00    7.50    --   80.00  66.00 -14.79   95
 55  \w     52.00 150.00   1.00    7.50    --   80.00  71.00   7.34   98
 56  \w     52.00 155.00   1.00   15.00    --   84.00  77.00  35.01  103
 57  \w     55.00 154.00   1.00   15.00    --   84.00  73.00  50.85   99
 58  \w     53.00 155.00   1.00   15.00    --   84.00  75.00-145.38  102
 59  \w     60.00 156.00   1.00   15.00    --   84.00  45.00-157.67   96
 60  \w     58.00 158.00   1.00   15.00    --   88.00  74.00-162.79  100
 61  \w     64.00 156.00   1.00   15.00    --   88.00  62.00  -3.89   92
 62  \w     67.00 160.00   1.00   15.00    --   92.00  64.00  93.91   93
 63  \w     64.00 162.00   1.00   15.00    --   92.00  70.00 117.64   98
 64  \w     65.00 167.00   1.00   15.00    --   96.00  76.00 -95.05  102
 65  \w     68.00 166.00   1.00   15.00    --   96.00  70.00  10.56   98
 66  \w     65.00 167.00   1.00   15.00    --   96.00  76.00-127.15  102
 67  \w     37.00 131.00   1.00   15.00    --  108.00 -50.00  90.00   94
 68  \w     83.00 176.00   1.00   15.00    --  108.00  64.00  30.00   93
 69  \w     76.00 178.00   1.00   15.00    --  108.00  77.00 150.00  102
 70  \w     81.00 178.00   1.00   15.00    --  108.00  38.00 -30.00   97
 71  \w     35.00 109.00   1.00   15.00    --  108.00 -92.00 -90.00   74
 72  \w     35.00 109.00   1.00   15.00    --  108.00 -92.00   0.00   74
 73  \w     35.00 109.00   1.00   15.00    --  108.00 -92.00 120.00   74
 74  \w     35.00 109.00   1.00   15.00    --  108.00 -92.00-180.00   74
 75  \w     83.00 176.00   1.00   15.00    --  108.00  64.00 -30.00   93
 76  \w     80.00 178.00   1.00   15.00    --  108.00  71.00  76.88   98
 77  \w     76.00 178.00   1.00   15.00    --  108.00  77.00-150.00  102
 78  \w     76.00 178.00   1.00   15.00    --  108.00  77.00-120.00  102
 79  \w     83.00 176.00   1.00   15.00    --  108.00  64.00-180.00   93
 80  \w     40.00 133.00   1.00   15.00    --  108.00 -64.00 -90.00   93
 81  \w     83.00 176.00   1.00   15.00    --  108.00  64.00 150.00   93
 82  \w     76.00 178.00   1.00   15.00    --  108.00  77.00  60.00  102
 83  \w     35.00 112.00   1.00   15.00    --  108.00-111.00 -90.00   77
 84  \w     76.00 178.00   1.00   15.00    --  108.00  77.00 -60.00  102
 85  \w     83.00 176.00   1.00   15.00    --  108.00  64.00-150.00   93
 86  \w     76.00 178.00   1.00   15.00    --  108.00  77.00  90.00  102
 87  \w     76.00 178.00   1.00   15.00    --  108.00  77.00  30.00  102
 88  \w     76.00 178.00   1.00   15.00    --  108.00  77.00 -30.00  102
 89  \w     76.00 178.00   1.00   15.00    --  108.00  77.00 -90.00  102
 90  \w     76.00 178.00   1.00   15.00    --  108.00  77.00-180.00  102
 91  \w     83.00 176.00   1.00   15.00    --  108.00  64.00  60.00   93
 92  \w     76.00 178.00   1.00   15.00    --  108.00  77.00   0.00  102
 93  \w     83.00 176.00   1.00   15.00    --  108.00  64.00   0.00   93
 94  \w     83.00 176.00   1.00   15.00    --  108.00  64.00 120.00   93
 95  \w     35.00 112.00   1.00   15.00    --  108.00-111.00  90.00   77
 96  \w     83.00 176.00   1.00   15.00    --  108.00  64.00 -60.00   93
 97  \w     76.00 178.00   1.00   15.00    --  108.00  77.00 120.00  102
 98  \f      0.00 120.00   1.00    2.50   2.02   0.00 -40.00    --   120
 99  \f      0.00 120.00   1.00    2.50  47.94   0.00  40.00    --   120
100  \f      0.00 120.00   1.00    2.50 -47.94   0.00 -40.00    --   120
101  \f      0.00 120.00   1.00    2.50 -45.87   0.00 -60.00    --   120
102  \f      0.00 120.00   1.00    2.50   0.09   0.00 -60.00    --   120
103  \f      0.00 120.00   1.00    2.50  -2.02   0.00  40.00    --   120
104  \f      0.00 120.00   1.00    7.50   6.06  54.00 -40.00    --   120
105  \f      0.00  25.00   1.00    7.50 101.94  54.00  40.00    --    25
106  \f      0.00 120.00   1.00    7.50  51.98  54.00  40.00    --   120
107  \f      0.00 120.00   1.00    7.50  56.02  54.00 -40.00    --   120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0080582000
_diffrn_orient_matrix_UB_12      -0.0489908000
_diffrn_orient_matrix_UB_13      -0.0417394000
_diffrn_orient_matrix_UB_21      0.2325817000
_diffrn_orient_matrix_UB_22      -0.0607268000
_diffrn_orient_matrix_UB_23      0.0079859000
_diffrn_orient_matrix_UB_31      -0.1390568000
_diffrn_orient_matrix_UB_32      -0.0986888000
_diffrn_orient_matrix_UB_33      0.0157891000
_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  0.0509
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            95208
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.361
_diffrn_reflns_theta_min         2.601
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       irregular
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         4494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0336P)^2^+0.5758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4148
_reflns_number_total             4494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00751_si_002.cif
_cod_data_source_block           ga_cb15
_cod_database_code               4038290
_audit_block_refno               3208
_audit_block_usercomment         'cbdb22, irregular, yellow'
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.936
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     44.91
_shelxl_version_number           2018/3
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim N1 \\sim N2 \\sim O1
\\sim O2 \\sim O3: within 1A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 1A
2. Others
 Uiso(H1)=Uiso(H16)=FVAR(1)
 Uiso(H2A)=Uiso(H2B)=Uiso(H15A)=Uiso(H15B)=FVAR(2)
 Uiso(H4)=Uiso(H8)=Uiso(H9)=Uiso(H13)=Uiso(H18)=Uiso(H19)=Uiso(H20)=Uiso(H21)=
 Uiso(H22)=Uiso(H24)=Uiso(H25)=Uiso(H26)=Uiso(H27)=Uiso(H28)=FVAR(3)
 Uiso(H29A)=Uiso(H29B)=Uiso(H29C)=Uiso(H30A)=Uiso(H30B)=Uiso(H30C)=FVAR(4)
3.a Idealised Me refined as rotating group with stretchable bonds:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.857
_shelx_res_checksum              7233
_cell_oxdiff_length_a            5.68261(11)
_cell_oxdiff_length_b            12.2455(3)
_cell_oxdiff_length_c            33.9818(5)
_cell_oxdiff_angle_alpha         90.0169(15)
_cell_oxdiff_angle_beta          89.9913(14)
_cell_oxdiff_angle_gamma         89.9902(17)
_cell_oxdiff_volume              2364.67(8)
_cell_oxdiff_measurement_reflns_used 30545