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_7710919
_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_formula_moiety         'C24 H22 O2'
_chemical_formula_sum            'C24 H22 O2'
_chemical_formula_weight         342.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-03
_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                91.128(3)
_cell_angle_beta                 106.294(3)
_cell_angle_gamma                112.674(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2137(3)
_cell_length_b                   10.7277(4)
_cell_length_c                   11.1202(3)
_cell_measurement_reflns_used    8790
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      76.4170
_cell_measurement_theta_min      4.1880
_cell_volume                     963.26(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_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    -57.00  30.00   1.00    1.00    --  -38.50  37.00  90.00   87
  2  \w    -57.00  26.00   1.00    1.00    --  -38.50  37.00-180.00   83
  3  \w    -44.00  18.00   1.00    1.00    --  -38.50  37.00 -90.00   62
  4  \w    -58.00  17.00   1.00    1.00    --  -38.50  37.00   0.00   75
  5  \w     44.00  82.00   1.00    1.00    --   42.70-125.00-120.00   38
  6  \w     22.00  55.00   1.00    1.00    --   42.70  37.00 -60.00   33
  7  \w     13.00  38.00   1.00    1.00    --   42.70  77.00-172.00   25
  8  \w     16.00 104.00   1.00    1.00    --   42.70  65.00-174.00   88
  9  \w     32.00  76.00   1.00    1.00    --   42.70 -99.00  30.00   44
 10  \w     26.00  56.00   1.00    1.00    --   42.70  57.00 150.00   30
 11  \w     18.00 103.00   1.00    1.00    --   42.70  57.00  90.00   85
 12  \w     24.00 101.00   1.00    1.00    --   42.70  37.00  30.00   77
 13  \w     27.00  92.00   1.00    1.00    --   42.70  57.00 -60.00   65
 14  \w     12.00  42.00   1.00    1.00    --   42.70  81.00  37.91   30
 15  \w     12.00  38.00   1.00    1.00    --   42.70  78.00-107.99   26
 16  \w     12.00  41.00   1.00    1.00    --   42.70  81.00 -34.51   29
 17  \w     85.00 143.00   1.00    2.00    --  111.00  61.00  30.00   58
 18  \w     78.00 107.00   1.00    2.00    --  111.00-102.00  74.04   29
 19  \w    129.00 178.00   1.00    2.00    --  111.00  70.00  95.89   49
 20  \w     85.00 174.00   1.00    2.00    --  111.00  59.00 -14.88   89
 21  \w     82.00 107.00   1.00    2.00    --  111.00 -94.00-150.00   25
 22  \w    129.00 172.00   1.00    2.00    --  111.00  45.00-150.00   43
 23  \w    146.00 177.00   1.00    2.00    --  111.00  63.00-138.56   31
 24  \w     90.00 117.00   1.00    2.00    --  111.00  45.00 150.00   27
 25  \w     90.00 115.00   1.00    2.00    --  111.00  45.00  90.00   25
 26  \w    122.00 151.00   1.00    2.00    --  111.00  45.00  90.00   29
 27  \w     43.00  69.00   1.00    2.00    --  111.00 -61.00 -30.00   26
 28  \w     88.00 137.00   1.00    2.00    --  111.00 -61.00 -30.00   49
 29  \w     47.00  74.00   1.00    2.00    --  111.00-125.00 -60.00   27
 30  \w     85.00 113.00   1.00    2.00    --  111.00  61.00 -30.00   28
 31  \w     83.00 121.00   1.00    2.00    --  111.00  70.00  95.89   38
 32  \w     91.00 116.00   1.00    2.00    --  111.00  45.00-150.00   25
 33  \w     85.00 178.00   1.00    2.00    --  111.00  61.00 120.00   93
 34  \w     84.00 129.00   1.00    2.00    --  111.00  63.00-138.56   45
 35  \w     89.00 120.00   1.00    2.00    --  111.00  45.00 -60.00   31
 36  \w    131.00 173.00   1.00    2.00    --  111.00  61.00-180.00   42
 37  \w     84.00 132.00   1.00    2.00    --  111.00  65.00-106.17   48
 38  \w     87.00 157.00   1.00    2.00    --  111.00  61.00   5.79   70
 39  \w     85.00 111.00   1.00    2.00    --  111.00  61.00-180.00   26
 40  \w     66.00 107.00   1.00    2.00    --  111.00-125.00   0.00   41
 41  \w     85.00 113.00   1.00    2.00    --  111.00  61.00  60.00   28
 42  \w     56.00 113.00   1.00    2.00    --  111.00-125.00 150.00   57
 43  \w    146.00 176.00   1.00    2.00    --  111.00  61.00-120.00   30
 44  \w     86.00 114.00   1.00    2.00    --  111.00  61.00 -90.00   28
 45  \w    124.00 168.00   1.00    2.00    --  111.00  61.00 -90.00   44
 46  \w     32.00  79.00   1.00    2.00    --  111.00 -94.00-150.00   47
 47  \w     90.00 178.00   1.00    2.00    --  111.00  45.00  60.00   88
 48  \w     85.00 157.00   1.00    2.00    --  111.00  61.00 150.00   72
 49  \w     85.00 113.00   1.00    2.00    --  111.00  61.00-150.00   28
 50  \w    142.00 174.00   1.00    2.00    --  111.00  61.00-150.00   32
 51  \w     85.00 120.00   1.00    2.00    --  111.00  61.00 -60.00   35
 52  \w    125.00 162.00   1.00    2.00    --  111.00  61.00 -60.00   37
 53  \w     85.00 124.00   1.00    2.00    --  111.00  61.00   0.00   39
 54  \w    152.00 177.00   1.00    2.00    --  111.00  61.00   0.00   25
 55  \w     85.00 116.00   1.00    2.00    --  111.00  61.00  90.00   31
 56  \w     92.00 127.00   1.00    2.00    --  111.00  45.00  30.00   35
 57  \w     88.00 169.00   1.00    2.00    --  111.00  46.00 -28.94   81
 58  \w     85.00 128.00   1.00    2.00    --  111.00  61.00-120.00   43
 59  \w     43.00  97.00   1.00    2.00    --  111.00-125.00-180.00   54
 60  \w     77.00 113.00   1.00    2.00    --  111.00-125.00 -60.00   36
 61  \w     71.00 108.00   1.00    2.00    --  111.00-107.00  44.00   37
 62  \w    114.00 169.00   1.00    2.00    --  111.00 125.00   0.00   55
 63  \w     36.00  64.00   1.00    2.00    --  111.00-107.00  44.00   28
 64  \w     97.00 124.00   1.00    2.00    --  111.00 -77.00 -90.00   27
 65  \w     71.00 106.00   1.00    2.00    --  111.00 -94.00-180.00   35
 66  \w    122.00 176.00   1.00    2.00    --  111.00 125.00  60.00   54
 67  \w     33.00  60.00   1.00    2.00    --  111.00 -94.00-180.00   27
 68  \w     88.00 113.00   1.00    2.00    --  111.00-125.00  30.00   25
 69  \w     82.00 111.00   1.00    2.00    --  111.00-125.00-150.00   29
 70  \w     45.00  78.00   1.00    2.00    --  111.00 -45.00   0.00   33
 71  \w     85.00 175.00   1.00    2.00    --  111.00  60.00 166.32   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17949
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.395
_diffrn_reflns_theta_min         4.186
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0657P)^2^+0.0887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3196
_reflns_number_total             3951
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 5.0864\% 
around [0.40 -0.91 -0.06] (reciprocal) or [0.16 -0.99 -0.04] (direct)
;
_cod_data_source_file            d2dt02118h2.cif
_cod_data_source_block           3
_cod_database_code               7710919
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H22 O2'
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.882
_olex2_refinement_description
;
1. Others
 Fixed Sof: O2(0.5) H2(0.5) O3(0.5) H3(0.5) C13(0.5) C14(0.5) H14(0.5)
 C15(0.5) H15(0.5) C16(0.5) H16(0.5) C17(0.5) C18(0.5) H18(0.5) C19(0.5)
 C20(0.5) C21(0.5) H21(0.5) C22(0.5) H22(0.5) C23(0.5) H23(0.5) C24(0.5)
 C25(0.5) H25(0.5) C26(0.5) C27(0.5) C28(0.5) C29(0.5) C30(0.5) H30A(0.5)
 H30B(0.5) H30C(0.5) C31(0.5) H31A(0.5) H31B(0.5) H31C(0.5) C32(0.5) C33(0.5)
 C34(0.5) C35(0.5) H35A(0.5) H35B(0.5) H35C(0.5) C36(0.5) H36A(0.5) H36B(0.5)
 H36C(0.5)
;
_shelx_res_checksum              44172
_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
;