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_4038292
_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         'C28 H22 N2 O2 S'
_chemical_formula_sum            'C28 H22 N2 O2 S'
_chemical_formula_weight         450.53
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_db3
_audit_creation_date             2019-09-24
_audit_creation_method
;
encif (version 1.102)

encifer (version_id = 257312.64)

Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_audit_update_record
'24.09.2019 13:43:07 CEST UTC+02:00  encif 1.102'
_cell_angle_alpha                90
_cell_angle_beta                 100.951(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.68294(15)
_cell_length_b                   34.9964(6)
_cell_length_c                   11.1399(3)
_cell_measurement_reflns_used    10094
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      28.3320
_cell_measurement_theta_min      2.5470
_cell_volume                     2175.19(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_publication_material
'encif (Wadepohl, 2009-19); encifer 1.7.x (CCDC, 2019)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      N~2~
_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 0.999
_diffrn_measured_fraction_theta_max 0.967
_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    -45.00  41.00   0.50   15.00    --  -25.00  57.00 150.00  172
  2  \w     -5.00  20.00   0.50   15.00    --   28.00  82.00 -95.38   50
  3  \w     -5.00  20.00   0.50   15.00    --   28.00  82.00 -33.27   50
  4  \w    -37.00  56.00   0.50   15.00    --   31.15 -38.00 -60.00  186
  5  \w    -15.00  73.00   0.50   15.00    --   31.15 -99.00 -90.00  176
  6  \w     11.00  38.00   0.50   15.00    --   31.15  57.00   0.00   54
  7  \w     67.00  97.00   0.50   15.00    --   31.15  66.00-106.28   60
  8  \w    -36.00  49.00   0.50   15.00    --   31.15 -57.00 150.00  170
  9  \w      6.00 101.00   0.50   15.00    --   31.15  38.00-120.00  190
 10  \w     72.00  98.00   0.50   15.00    --   31.15  72.00  30.46   52
 11  \w    -34.00  -8.00   0.50   15.00    --   31.15 -77.00 -60.00   52
 12  \w    -34.00  15.00   0.50   15.00    --   31.15 -77.00 120.00   98
 13  \w     35.00  61.00   0.50   15.00    --   31.15 -77.00 120.00   52
 14  \w      6.00 101.00   0.50   15.00    --   31.15  38.00  30.00  190
 15  \w      3.00  86.00   0.50   15.00    --   31.15  73.00  95.67  166
 16  \w      4.00  54.00   0.50   15.00    --   31.15  71.00 169.86  100
 17  \w      7.00  41.00   0.50   15.00    --   31.15  73.00 -54.98   68
 18  \w     49.00  75.00   0.50   15.00    --   31.15  73.00 -54.98   52
 19  \w     43.00  71.00   0.50   15.00    --   31.15 -99.00 -30.00   56
 20  \w     11.00  44.00   0.50   15.00    --   31.15  72.00  30.46   66
 21  \w    -14.00  72.00   0.50   15.00    --   31.15 -99.00  90.00  172
 22  \w      8.00  47.00   0.50   15.00    --   31.15  66.00-106.28   78
 23  \w     70.00  96.00   0.50   15.00    --   31.15  69.00  52.49   52
;
_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      0.0517607000
_diffrn_orient_matrix_UB_12      -0.0018326000
_diffrn_orient_matrix_UB_13      -0.0528579000
_diffrn_orient_matrix_UB_21      0.0504829000
_diffrn_orient_matrix_UB_22      0.0185173000
_diffrn_orient_matrix_UB_23      0.0104442000
_diffrn_orient_matrix_UB_31      0.1045585000
_diffrn_orient_matrix_UB_32      -0.0080358000
_diffrn_orient_matrix_UB_33      0.0360908000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.1063
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            70077
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.155
_diffrn_reflns_theta_min         2.196
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (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            bronze
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       irregular
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 3773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         17031
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0625
_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^)+(0.0384P)^2^+0.0258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                11110
_reflns_number_total             17031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00751_si_002.cif
_cod_data_source_block           ga_db3
_cod_original_cell_volume        2175.18(9)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038292
_audit_block_refno               3424
_audit_block_usercomment         'DB050K2, irregular, bronze'
_chemical_oxdiff_formula         'C28 H22 N2 O2 S'
_chemical_oxdiff_usercomment     'DB050K2, irregular, bronze'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.50
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C16(H16), C51(H51), C66(H66)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C15(H15A,H15B), C52(H52A,H52B), C65(H65A,H65B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C54(H54), C57(H57), C58(H58), C59(H59), C60(H60), C63(H63), C68(H68),
 C69(H69), C70(H70), C71(H71), C72(H72), C74(H74), C75(H75), C76(H76), C77(H77),
  C78(H78)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.838
_shelx_res_checksum              51673
_cell_oxdiff_length_a            5.68297(16)
_cell_oxdiff_length_b            34.9948(5)
_cell_oxdiff_length_c            11.1400(3)
_cell_oxdiff_angle_alpha         90.0119(16)
_cell_oxdiff_angle_beta          100.943(2)
_cell_oxdiff_angle_gamma         89.9920(17)
_cell_oxdiff_volume              2175.18(9)
_cell_oxdiff_measurement_reflns_used 10094