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_7710924
_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         'C92 H176 Al4 Si16, C6 H6'
_chemical_formula_sum            'C98 H182 Al4 Si16'
_chemical_formula_weight         1917.79
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-22
_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                102.967(2)
_cell_angle_beta                 103.576(2)
_cell_angle_gamma                97.456(2)
_cell_formula_units_Z            2
_cell_length_a                   15.1482(3)
_cell_length_b                   18.5350(3)
_cell_length_c                   23.3981(4)
_cell_measurement_reflns_used    47681
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      76.2690
_cell_measurement_theta_min      2.6720
_cell_volume                     6106.6(2)
_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 (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      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_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    -76.00  -6.00   1.00    2.50    --  -38.50 125.00  30.00   70
  2  \w   -116.00  -8.00   1.00    2.50    --  -38.50 -19.00  90.00  108
  3  \w    -74.00 -29.00   1.00    2.50    --  -38.50 125.00  90.00   45
  4  \w    -56.00  33.00   1.00    2.50    --  -38.50  37.00 -90.00   89
  5  \w    -56.00  28.00   1.00    2.50    --  -38.50  57.00  30.00   84
  6  \w    -37.00  31.00   1.00    2.50    --  -38.50  37.00-180.00   68
  7  \w     17.00  88.00   1.00    2.50    --   42.20  71.00-126.58   71
  8  \w     27.00  96.00   1.00    2.50    --   42.20-125.00 -30.00   69
  9  \w     11.00  36.00   1.00    2.50    --   42.20  82.00-149.74   25
 10  \w     13.00  42.00   1.00    2.50    --   42.20  78.00 107.23   29
 11  \w     11.00  40.00   1.00    2.50    --   42.20  81.00 -86.00   29
 12  \w     58.00  97.00   1.00    2.50    --   42.20  37.00-150.00   39
 13  \w     16.00  99.00   1.00    2.50    --   42.20  67.00 -27.86   83
 14  \w     17.00  50.00   1.00    2.50    --   42.20  57.00  90.00   33
 15  \w     23.00  53.00   1.00    2.50    --   42.20  37.00-150.00   30
 16  \w     55.00  82.00   1.00    2.50    --   42.20  57.00  90.00   27
 17  \w     11.00  38.00   1.00    2.50    --   42.20  80.00  31.99   27
 18  \w     13.00  42.00   1.00    2.50    --   42.20  76.00 159.39   29
 19  \w     18.00  87.00   1.00    2.50    --   42.20  57.00  30.00   69
 20  \w     13.00  38.00   1.00    2.50    --   42.20  77.00  -3.22   25
 21  \w     17.00 111.00   1.00    2.50    --   42.20  57.00 -90.00   94
 22  \w     85.00 125.00   1.00   10.00    --  111.00  62.00-112.45   40
 23  \w    153.00 178.00   1.00   10.00    --  111.00  67.00 149.05   25
 24  \w     88.00 115.00   1.00   10.00    --  111.00  47.00 149.19   27
 25  \w     85.00 117.00   1.00   10.00    --  111.00  60.00 168.22   32
 26  \w    129.00 177.00   1.00   10.00    --  111.00  57.00 144.79   48
 27  \w     83.00 112.00   1.00   10.00    --  111.00  70.00-168.30   29
 28  \w     83.00 110.00   1.00   10.00    --  111.00  69.00  88.11   27
 29  \w    147.00 178.00   1.00   10.00    --  111.00  69.00  88.11   31
 30  \w     46.00 107.00   1.00   10.00    --  111.00 -97.00  76.22   61
 31  \w     83.00 110.00   1.00   10.00    --  111.00  67.00 149.05   27
 32  \w     86.00 113.00   1.00   10.00    --  111.00  57.00 144.79   27
 33  \w     85.00 112.00   1.00   10.00    --  111.00  61.00  11.02   27
 34  \w     83.00 178.00   1.00   10.00    --  111.00  67.00 -13.95   95
 35  \w     82.00 109.00   1.00   10.00    --  111.00  71.00 177.84   27
 36  \w     86.00 139.00   1.00   10.00    --  111.00  58.00 -18.98   53
 37  \w    142.00 178.00   1.00   10.00    --  111.00  64.00 -77.58   36
 38  \w     84.00 111.00   1.00   10.00    --  111.00  64.00 -77.58   27
 39  \w     85.00 113.00   1.00   10.00    --  111.00  60.00 -66.59   28
 40  \w     87.00 114.00   1.00   10.00    --  111.00  52.00-116.48   27
 41  \w    115.00 178.00   1.00   10.00    --  111.00  61.00 120.00   63
 42  \w     85.00 112.00   1.00   10.00    --  111.00  61.00 120.00   27
 43  \w     89.00 155.00   1.00   10.00    --  111.00  45.00  60.00   66
 44  \w     31.00 107.00   1.00   10.00    --  111.00 -94.00 120.00   76
 45  \w     84.00 126.00   1.00   10.00    --  111.00  64.00 102.58   42
 46  \w     87.00 113.00   1.00   10.00    --  111.00-125.00  60.00   26
 47  \w     85.00 171.00   1.00   10.00    --  111.00  61.00  74.76   86
 48  \w     43.00 135.00   1.00   10.00    --  111.00 -61.00 120.00   92
 49  \w     85.00 168.00   1.00   10.00    --  111.00  61.00  30.00   83
 50  \w     85.00 112.00   1.00   10.00    --  111.00  61.00  60.00   27
 51  \w     86.00 113.00   1.00   10.00    --  111.00  61.00   0.00   27
 52  \w     89.00 116.00   1.00   10.00    --  111.00  45.00-120.00   27
 53  \w    132.00 176.00   1.00   10.00    --  111.00  71.00 -60.90   44
 54  \w     85.00 178.00   1.00   10.00    --  111.00  61.00-180.00   93
 55  \w     85.00 111.00   1.00   10.00    --  111.00  61.00 150.00   26
 56  \w     89.00 154.00   1.00   10.00    --  111.00  45.00 -90.00   65
 57  \w     31.00 107.00   1.00   10.00    --  111.00 -94.00 -60.00   76
 58  \w     85.00 112.00   1.00   10.00    --  111.00  60.00-119.85   27
 59  \w     84.00 178.00   1.00   10.00    --  111.00  65.00-150.79   94
 60  \w     85.00 113.00   1.00   10.00    --  111.00  61.00 -60.00   28
 61  \w     84.00 176.00   1.00   10.00    --  111.00  63.00 -89.12   92
 62  \w     88.00 113.00   1.00   10.00    --  111.00-125.00-120.00   25
 63  \w     85.00 113.00   1.00   10.00    --  111.00  61.00 -30.00   28
 64  \w     42.00 113.00   1.00   10.00    --  111.00-125.00 -60.00   71
 65  \w     84.00 110.00   1.00   10.00    --  111.00  64.00  15.44   26
 66  \w     85.00 112.00   1.00   10.00    --  111.00  61.00  90.00   27
 67  \w     46.00 132.00   1.00   10.00    --  111.00 -61.00 -60.00   86
 68  \w     44.00  71.00   1.00   10.00    --  111.00-125.00-120.00   27
 69  \w    130.00 158.00   1.00   10.00    --  111.00  62.00-112.45   28
 70  \w     89.00 125.00   1.00   10.00    --  111.00  44.00 -20.88   36
 71  \w     82.00 108.00   1.00   10.00    --  111.00  71.00 -60.90   26
;
_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      -0.0985738000
_diffrn_orient_matrix_UB_12      0.0108727000
_diffrn_orient_matrix_UB_13      0.0016414000
_diffrn_orient_matrix_UB_21      -0.0219829000
_diffrn_orient_matrix_UB_22      -0.0800346000
_diffrn_orient_matrix_UB_23      0.0080396000
_diffrn_orient_matrix_UB_31      0.0341688000
_diffrn_orient_matrix_UB_32      0.0321102000
_diffrn_orient_matrix_UB_33      0.0697528000
_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  0.0573
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            124476
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.015
_diffrn_reflns_theta_min         2.493
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.140
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.759
_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    1.043
_exptl_crystal_description       plate
_exptl_crystal_F_000             2092
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1142
_refine_ls_number_reflns         25339
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+5.3929P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20284
_reflns_number_total             25339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02118h2.cif
_cod_data_source_block           anti-9
_cod_database_code               7710924
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C98H182Al4Si16
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.712
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C62 \\sim C62B \\sim C63 \\sim C63B \\sim C64 \\sim C64B: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.01
3. Others
 Sof(C62B)=Sof(H62D)=Sof(H62E)=Sof(H62F)=Sof(C63B)=Sof(H63D)=Sof(H63E)=
 Sof(H63F)=Sof(C64B)=Sof(H64D)=Sof(H64E)=Sof(H64F)=1-FVAR(1)
 Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(H63C)=
 Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10), C17(H17), C24(H24), C37(H37), C44(H44), C51(H51), C58(H58),
 C65(H65), C72(H72), C79(H79), C86(H86)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C19(H19), C20(H20),
 C21(H21), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34), C35(H35), C36(H36), C93(H93), C94(H94), C95(H95),
 C96(H96), C97(H97), C98(H98)
4.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,
 H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C45(H45A,H45B,H45C), C46(H46A,
 H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C),
 C50(H50A,H50B,H50C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C59(H59A,
 H59B,H59C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C),
 C62B(H62D,H62E,H62F), C63(H63A,H63B,H63C), C63B(H63D,H63E,H63F), C64(H64A,H64B,
 H64C), C64B(H64D,H64E,H64F), C66(H66A,H66B,H66C), C67(H67A,H67B,H67C),
 C68(H68A,H68B,H68C), C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C71(H71A,H71B,
 H71C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C), C75(H75A,H75B,H75C), C76(H76A,
 H76B,H76C), C77(H77A,H77B,H77C), C78(H78A,H78B,H78C), C80(H80A,H80B,H80C),
 C81(H81A,H81B,H81C), C82(H82A,H82B,H82C), C83(H83A,H83B,H83C), C84(H84A,H84B,
 H84C), C85(H85A,H85B,H85C), C87(H87A,H87B,H87C), C88(H88A,H88B,H88C), C89(H89A,
 H89B,H89C), C90(H90A,H90B,H90C), C91(H91A,H91B,H91C), C92(H92A,H92B,H92C)
;
_shelx_res_checksum              8345
_olex2_exptl_crystal_mounting_method
;
One SiMe- group
is disordered with ratio 56:44, SIMU restraints were applied
for disordered atoms.
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.729