Synthesis of bi- and tetradentate poly-Lewis acids by hydroalumination of poly-alkynyl-anthracene derivatives
Mitzel, Norbert Werner; Aders, Niklas; Lamm, Jan-Hendrik; Beckmann, Jean Louis; Neumann, Beate; Stammler, Georg; Dalton Transactions  (2022) –; doi:10.1039/D2DT02118H

data_7710923
_publ_section_title
;
 Synthesis of bi- and tetradentate poly-Lewis acids by hydroalumination of
 poly-alkynyl-anthracene derivatives
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02118H
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C36 H20'
_chemical_formula_sum            'C36 H20'
_chemical_formula_weight         452.52
_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     dual
_audit_creation_date             2020-09-15
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-04-01 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.596(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.97671(17)
_cell_length_b                   15.5959(3)
_cell_length_c                   10.1573(2)
_cell_measurement_reflns_used    12854
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9260
_cell_measurement_theta_min      5.7430
_cell_volume                     1217.08(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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    -75.00  -6.00   1.00    1.00    --  -38.50 125.00 -60.00   69
  2  \w    -86.00  -7.00   1.00    1.00    --  -38.50 125.00-150.00   79
  3  \w    -59.00  31.00   1.00    1.00    --  -38.50  38.00-150.00   90
  4  \w    -63.00  25.00   1.00    1.00    --  -38.50  57.00 120.00   88
  5  \w     14.00  40.00   1.00    1.00    --   42.70  82.00 -31.46   26
  6  \w     24.00  55.00   1.00    1.00    --   42.70  57.00  30.00   31
  7  \w     23.00 113.00   1.00    1.00    --   42.70  38.00 150.00   90
  8  \w     11.00  36.00   1.00    1.00    --   42.70  82.00-124.61   25
  9  \w     64.00 105.00   1.00    1.00    --   42.70  57.00  30.00   41
 10  \w     19.00 111.00   1.00    1.00    --   42.70  57.00-150.00   92
 11  \w     58.00  93.00   1.00    1.00    --   42.70  57.00  90.00   35
 12  \w     18.00  46.00   1.00    1.00    --   42.70  57.00  90.00   28
 13  \w     18.00  55.00   1.00    1.00    --   42.70  57.00 -90.00   37
 14  \w     16.00  42.00   1.00    1.00    --   42.70  78.00  49.78   26
 15  \w     11.00  42.00   1.00    1.00    --   42.70  81.00 114.63   31
 16  \w     22.00  65.00   1.00    1.00    --   42.70  38.00   0.00   43
 17  \w     13.00  38.00   1.00    1.00    --   42.70  76.00 -66.37   25
 18  \w     15.00  40.00   1.00    1.00    --   42.70  78.00 175.56   25
 19  \w     59.00  87.00   1.00    1.00    --   42.70  57.00 -90.00   28
 20  \w     83.00 109.00   1.00    1.00    --  111.00  68.00 144.55   26
 21  \w     83.00 115.00   1.00    1.00    --  111.00  67.00 162.39   32
 22  \w    146.00 173.00   1.00    1.00    --  111.00  56.00 -37.52   27
 23  \w     88.00 116.00   1.00    1.00    --  111.00  61.00-180.00   28
 24  \w    125.00 156.00   1.00    1.00    --  111.00  52.00-125.20   31
 25  \w     85.00 112.00   1.00    1.00    --  111.00  61.00 -30.00   27
 26  \w     85.00 175.00   1.00    1.00    --  111.00  61.00-120.00   90
 27  \w     42.00 113.00   1.00    1.00    --  111.00-125.00 -60.00   71
 28  \w     85.00 133.00   1.00    1.00    --  111.00  61.00 -90.00   48
 29  \w     88.00 118.00   1.00    1.00    --  111.00  52.00-125.20   30
 30  \w     87.00 112.00   1.00    1.00    --  111.00  56.00 -37.52   25
 31  \w    149.00 178.00   1.00    1.00    --  111.00  68.00 102.01   29
 32  \w     87.00 113.00   1.00    1.00    --  111.00-125.00-120.00   26
 33  \w     88.00 118.00   1.00    1.00    --  111.00  61.00 120.00   30
 34  \w     87.00 119.00   1.00    1.00    --  111.00  54.00-162.63   32
 35  \w     85.00 112.00   1.00    1.00    --  111.00  61.00  60.00   27
 36  \w     46.00 137.00   1.00    1.00    --  111.00 -61.00   0.00   91
 37  \w     83.00 109.00   1.00    1.00    --  111.00  70.00  -4.31   26
 38  \w    121.00 177.00   1.00    1.00    --  111.00  58.00  -3.58   56
 39  \w     82.00 109.00   1.00    1.00    --  111.00  73.00-122.02   27
 40  \w     32.00 107.00   1.00    1.00    --  111.00 -94.00 -60.00   75
 41  \w     85.00 177.00   1.00    1.00    --  111.00  61.00 -60.00   92
 42  \w     61.00 136.00   1.00    1.00    --  111.00 -61.00 120.00   75
 43  \w     85.00 112.00   1.00    1.00    --  111.00  61.00  30.00   27
 44  \w     44.00  69.00   1.00    1.00    --  111.00-125.00 120.00   25
 45  \w     86.00 113.00   1.00    1.00    --  111.00-125.00 120.00   27
 46  \w     85.00 178.00   1.00    1.00    --  111.00  61.00  90.00   93
 47  \w     84.00 111.00   1.00    1.00    --  111.00  64.00  78.77   27
 48  \w     89.00 172.00   1.00    1.00    --  111.00  45.00  60.00   83
 49  \w     86.00 123.00   1.00    1.00    --  111.00  57.00 -13.79   37
 50  \w     91.00 163.00   1.00    1.00    --  111.00  45.00  30.00   72
 51  \w     42.00 107.00   1.00    1.00    --  111.00-125.00-180.00   65
 52  \w    127.00 175.00   1.00    1.00    --  111.00  61.00-180.00   48
 53  \w     87.00 114.00   1.00    1.00    --  111.00  50.00-142.24   27
 54  \w     91.00 118.00   1.00    1.00    --  111.00  45.00  90.00   27
 55  \w     44.00 101.00   1.00    1.00    --  111.00 -94.00   0.00   57
 56  \w    125.00 178.00   1.00    1.00    --  111.00  68.00 144.55   53
 57  \w     83.00 134.00   1.00    1.00    --  111.00  68.00 -81.48   51
 58  \w     86.00 119.00   1.00    1.00    --  111.00  58.00  -3.58   33
 59  \w     83.00 109.00   1.00    1.00    --  111.00  68.00 102.01   26
 60  \w     85.00 138.00   1.00    1.00    --  111.00  59.00 139.19   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0287734000
_diffrn_orient_matrix_UB_12      -0.0506755000
_diffrn_orient_matrix_UB_13      0.1344449000
_diffrn_orient_matrix_UB_21      0.1751176000
_diffrn_orient_matrix_UB_22      -0.0332240000
_diffrn_orient_matrix_UB_23      -0.0164239000
_diffrn_orient_matrix_UB_31      0.0932982000
_diffrn_orient_matrix_UB_32      0.0779998000
_diffrn_orient_matrix_UB_33      0.0803815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21149
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.562
_diffrn_reflns_theta_min         5.759
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
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    1.235
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_coef       0.0036(8)
_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   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4977
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0483P)^2^+0.1842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4805
_reflns_number_total             4977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02118h2.cif
_cod_data_source_block           anti-5
_cod_original_cell_volume        1217.08(5)
_cod_database_code               7710923
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C36 H20'
_diffrn_oxdiff_digest_frames
;
013dcb5d03c194dbc51931b7ba8db3d95102765dce2
;
_diffrn_oxdiff_digest_hkl
;
0139e3fbc2513c943d6986169a48b401f1b430
;
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10), C21(H21), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C23(H23), C24(H24),
 C25(H25), C30(H30), C31(H31), C32(H32)
2.c :
 C16(H16), C18(H18), C34(H34), C36(H36)
;
_shelx_res_checksum              39678
_olex2_date_sample_data_collection 2020-09-14
_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 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.828