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_4038297
_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 Cl2 Co N2 O3, 0.5(C7 H8)'
_chemical_formula_sum            'C27.5 H34 Cl2 Co N2 O3'
_chemical_formula_weight         570.39
_chemical_properties_physical    'air-sensitive, moisture-sensitive'
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_cb19
_audit_creation_date             2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_audit_update_record
'27.02.2019 11:54:12 CET UTC+01:00  encif 1.90'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.53710(20)
_cell_length_b                   14.1319(2)
_cell_length_c                   28.1192(5)
_cell_measurement_reflns_used    28536
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      69.1720
_cell_measurement_theta_min      3.4890
_cell_volume                     5379.34(15)
_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    '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 0.990
_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    -30.00  70.00   1.00    5.00    --    0.00  77.00-180.00  100
  2  \w    -69.00  21.00   1.00    5.00    --    0.00 -57.00 150.00   90
  3  \w    -70.00  30.00   1.00    5.00    --    0.00 -77.00  60.00  100
  4  \w    -49.00  -3.00   1.00    5.00    --   10.00 127.00 -74.12   46
  5  \w    -25.00  12.00   1.00    5.00    --   22.00 108.00-168.19   37
  6  \w     -9.00  18.00   1.00   20.00    --   34.00 101.00 -69.92   27
  7  \w      5.00  32.00   1.00   20.00    --   42.00  90.00  94.00   27
  8  \w      5.00  33.00   1.00   20.00    --   42.00  89.00  -0.31   28
  9  \w      5.00  33.00   1.00   20.00    --   42.00  89.00-146.98   28
 10  \w     13.00  40.00   1.00   20.00    --   46.00  83.00 -92.92   27
 11  \w     17.00  45.00   1.00   20.00    --   50.00  82.00-119.10   28
 12  \w     18.00  45.00   1.00   20.00    --   50.00  81.00-149.35   27
 13  \w     18.00  45.00   1.00   20.00    --   50.00  81.00 118.02   27
 14  \w     17.00  45.00   1.00   20.00    --   50.00  82.00  71.34   28
 15  \w     18.00  45.00   1.00   20.00    --   50.00  81.00 -38.76   27
 16  \w     18.00  45.00   1.00   20.00    --   50.00  80.00   5.70   27
 17  \w     18.00  45.00   1.00   20.00    --   50.00  80.00 -78.28   27
 18  \w     18.00  45.00   1.00   20.00    --   50.00  80.00 167.65   27
 19  \w     24.00 124.00   1.00   20.00    --   54.00  77.00-180.00  100
 20  \w      1.00  96.00   1.00   20.00    --   54.00 -99.00-180.00   95
 21  \w     23.00 111.00   1.00   20.00    --   54.00-125.00   0.00   88
 22  \w      1.00  96.00   1.00   20.00    --   54.00 -99.00  60.00   95
 23  \w     29.00 128.00   1.00   20.00    --   58.00  75.00 -78.55   99
 24  \w     28.00 128.00   1.00   20.00    --   58.00  77.00  41.17  100
 25  \w     28.00 128.00   1.00   20.00    --   58.00  77.00 -36.72  100
 26  \w     32.00 132.00   1.00   20.00    --   62.00  77.00  60.49  100
 27  \w     33.00 132.00   1.00   20.00    --   62.00  76.00-143.26   99
 28  \w     32.00 132.00   1.00   20.00    --   62.00  77.00 130.91  100
 29  \w     32.00 132.00   1.00   20.00    --   62.00  77.00  -6.16  100
 30  \w     36.00 136.00   1.00   20.00    --   66.00  77.00  76.33  100
 31  \w     39.00 135.00   1.00   20.00    --   66.00  72.00 169.43   96
 32  \w     40.00 135.00   1.00   20.00    --   66.00  70.00-112.18   95
 33  \w     37.00 136.00   1.00   20.00    --   66.00  76.00 -76.70   99
 34  \w     38.00 136.00   1.00   20.00    --   66.00  74.00  38.17   98
 35  \w     36.00 136.00   1.00   20.00    --   66.00  77.00-167.60  100
 36  \w     42.00 139.00   1.00   20.00    --   70.00  73.00 176.97   97
 37  \w     47.00 143.00   1.00   20.00    --   74.00  72.00  61.29   96
 38  \w     45.00 144.00   1.00   20.00    --   74.00  75.00  96.43   99
 39  \w     50.00 148.00   1.00   20.00    --   78.00  74.00  31.46   98
 40  \w     49.00 148.00   1.00   20.00    --   78.00  76.00 129.41   99
 41  \w     49.00 148.00   1.00   20.00    --   78.00  76.00  -7.33   99
 42  \w     54.00 146.00   1.00   20.00    --   78.00  67.00 -52.01   92
 43  \w     55.00 146.00   1.00   20.00    --   78.00  65.00 162.38   91
 44  \w     56.00 100.00   1.00   20.00    --   78.00  50.00-134.47   44
 45  \w     54.00 111.00   1.00   30.00    --   82.00  74.00 -42.24   57
 46  \w     58.00  84.00   1.00   30.00    --   82.00  68.00  67.13   26
 47  \w     53.00 145.00   1.00   30.00    --   82.00  76.00-119.83   92
 48  \w     60.00 149.00   1.00   30.00    --   82.00  66.00 -91.57   89
 49  \w     56.00  81.00   1.00   30.00    --   86.00  77.00  85.26   25
 50  \w     67.00  92.00   1.00   30.00    --   90.00  64.00 169.74   25
 51  \w     63.00  94.00   1.00   30.00    --   90.00  73.00 116.51   31
 52  \w     62.00  88.00   1.00   30.00    --   90.00  74.00-152.73   26
 53  \w     71.00 101.00   1.00   30.00    --   94.00  65.00 -53.87   30
 54  \w     65.00  93.00   1.00   30.00    --   94.00  76.00-142.12   28
 55  \w     66.00  91.00   1.00   30.00    --   94.00  74.00  99.62   25
 56  \w     70.00  97.00   1.00   30.00    --   98.00  74.00 160.42   27
 57  \w    126.00 164.00   1.00   30.00    --  102.00  77.00  15.05   38
 58  \w     72.00  97.00   1.00   30.00    --  102.00  77.00  15.05   25
 59  \w    107.00 178.00   1.00   30.00    --  108.00  77.00-120.00   71
 60  \w     78.00 104.00   1.00   30.00    --  108.00  77.00-120.00   26
 61  \w     51.00 112.00   1.00   30.00    --  108.00-111.00 -90.00   61
 62  \w     78.00 178.00   1.00   30.00    --  108.00  77.00 -60.00  100
 63  \w     69.00 124.00   1.00   30.00    --  108.00 -50.00 -90.00   55
 64  \w     79.00 144.00   1.00   30.00    --  108.00  77.00 -30.00   65
 65  \w     85.00 111.00   1.00   30.00    --  108.00  64.00 -90.00   26
 66  \w     44.00  78.00   1.00   30.00    --  108.00-111.00  90.00   34
 67  \w    111.00 169.00   1.00   30.00    --  108.00 111.00 -30.00   58
 68  \w     36.00 108.00   1.00   30.00    --  108.00 -92.00 -60.00   72
 69  \w     36.00 103.00   1.00   30.00    --  108.00 -92.00 150.00   67
 70  \w     85.00 162.00   1.00   30.00    --  108.00  64.00 150.00   77
 71  \w     54.00 113.00   1.00   30.00    --  108.00-111.00 120.00   59
 72  \w     79.00 163.00   1.00   30.00    --  108.00  77.00-180.00   84
 73  \w     86.00 112.00   1.00   30.00    --  108.00  64.00 -30.00   26
 74  \w     80.00 177.00   1.00   30.00    --  108.00  77.00  90.00   97
 75  \w     78.00 177.00   1.00   30.00    --  108.00  77.00 120.00   99
 76  \w     78.00 157.00   1.00   30.00    --  108.00  77.00  60.00   79
 77  \w     78.00 174.00   1.00   30.00    --  108.00  77.00  30.00   96
 78  \w     78.00 154.00   1.00   30.00    --  108.00  77.00 -90.00   76
 79  \w     78.00 174.00   1.00   30.00    --  108.00  77.00-150.00   96
 80  \w     85.00 156.00   1.00   30.00    --  108.00  64.00   0.00   71
 81  \w     72.00 105.00   1.00   30.00    --  108.00 -92.00   0.00   33
;
_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      -0.0232842000
_diffrn_orient_matrix_UB_12      0.0822898000
_diffrn_orient_matrix_UB_13      0.0341412000
_diffrn_orient_matrix_UB_21      -0.1108416000
_diffrn_orient_matrix_UB_22      -0.0242132000
_diffrn_orient_matrix_UB_23      -0.0027631000
_diffrn_orient_matrix_UB_31      0.0114951000
_diffrn_orient_matrix_UB_32      -0.0672690000
_diffrn_orient_matrix_UB_33      0.0427377000
_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  0.0704
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            131940
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.463
_diffrn_reflns_theta_min         3.143
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.084
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.690
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 3491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0315(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         10346
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0442P)^2^+3.1052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                9007
_reflns_number_total             10346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00751_si_002.cif
_cod_data_source_block           ga_cb19
_cod_original_cell_volume        5379.33(15)
_cod_original_formula_sum        'C27.50 H34 Cl2 Co N2 O3'
_cod_database_code               4038297
_audit_block_refno               3285
_audit_block_usercomment         'CBIM24, irregular, green'
_shelx_estimated_absorpt_t_max   0.538
_shelx_estimated_absorpt_t_min   0.538
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelxl_version_number           2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C81, C82, C83, C84, C85, C86, C87
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Same fragment restrains
{C81, C82, C83, C84, C85, C86, C87} sigma for 1-2: 0.02, 1-3: 0.04
{C81, C86, C85, C84, C83, C82, C87} sigma for 1-2: 0.02, 1-3: 0.04
as
{C81, C82, C83, C84, C85, C86, C87}
4.a Ternary CH refined with riding coordinates:
 C1(H1), C16(H16), C17(H17), C20(H20), C51(H51), C66(H66), C68(H68), C70(H70)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C15(H15A,H15B), C52(H52A,H52B), C65(H65A,H65B)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C13(H13), C54(H54), C58(H58), C59(H59), C63(H63),
 C82(H82), C83(H83), C84(H84), C85(H85), C86(H86)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C67(H67A,H67B,H67C), C69(H69A,
 H69B,H69C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C), C73(H73A,H73B,H73C),
 C74(H74A,H74B,H74C), C87(H87A,H87B,H87C)
;
_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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.801
_shelx_res_checksum              52817
_cell_oxdiff_length_a            13.5323(3)
_cell_oxdiff_length_b            14.1324(3)
_cell_oxdiff_length_c            28.1281(6)
_cell_oxdiff_angle_alpha         90.0134(19)
_cell_oxdiff_angle_beta          90.0240(17)
_cell_oxdiff_angle_gamma         89.9744(17)
_cell_oxdiff_volume              5379.3(2)
_cell_oxdiff_measurement_reflns_used 28537