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_7710925
_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         'C112 H196 Al4 N4 Si16, 1[C6H6], 1.5[C6H6]'
_chemical_formula_sum            'C127 H211 Al4 N4 Si16'
_chemical_formula_weight         2351.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-18
_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                 108.0983(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.0412(3)
_cell_length_b                   20.17214(13)
_cell_length_c                   25.6654(3)
_cell_measurement_reflns_used    59340
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      76.0790
_cell_measurement_theta_min      2.6470
_cell_volume                     14783.6(3)
_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      100.1(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_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    -45.00  33.00   1.00    2.00    --  -38.50  37.00 -30.00   78
  2  \w    -49.00  33.00   1.00    2.00    --  -38.50  37.00-120.00   82
  3  \w   -124.00  42.00   1.00    2.00    --  -38.50   0.00-180.00  166
  4  \w     14.00  41.00   1.00    2.00    --   42.70  82.00-117.03   27
  5  \w     13.00  40.00   1.00    2.00    --   42.70  76.00 -19.73   27
  6  \w     28.00  78.00   1.00    2.00    --   42.70-125.00  90.00   50
  7  \w     11.00  42.00   1.00    2.00    --   42.70  81.00 175.34   31
  8  \w     28.00  71.00   1.00    2.00    --   42.70-125.00-180.00   43
  9  \w     12.00  41.00   1.00    2.00    --   42.70  82.00   9.20   29
 10  \w     24.00  81.00   1.00    2.00    --   42.70 -99.00 -90.00   57
 11  \w     19.00  89.00   1.00    2.00    --   42.70  57.00  30.00   70
 12  \w     21.00  83.00   1.00    2.00    --   42.70  57.00 -60.00   62
 13  \w     22.00 108.00   1.00    2.00    --   42.70  37.00  90.00   86
 14  \w     12.00  42.00   1.00    2.00    --   42.70  80.00  74.38   30
 15  \w     17.00  42.00   1.00    2.00    --   42.70  79.00 117.23   25
 16  \w     18.00  71.00   1.00    2.00    --   42.70  57.00-120.00   53
 17  \w     22.00 113.00   1.00    2.00    --   42.70  37.00-180.00   91
 18  \w     86.00 113.00   1.00   14.00    --  111.00  55.00  27.89   27
 19  \w    118.00 178.00   1.00   14.00    --  111.00  63.00  69.81   60
 20  \w     83.00 109.00   1.00   14.00    --  111.00  70.00 -59.84   26
 21  \w     84.00 110.00   1.00   14.00    --  111.00  63.00  69.81   26
 22  \w     83.00 109.00   1.00   14.00    --  111.00  68.00  25.11   26
 23  \w     84.00 174.00   1.00   14.00    --  111.00  63.00 131.92   90
 24  \w     86.00 112.00   1.00   14.00    --  111.00  57.00 149.11   26
 25  \w     83.00 109.00   1.00   14.00    --  111.00  68.00  92.05   26
 26  \w    121.00 178.00   1.00   14.00    --  111.00  68.00  92.05   57
 27  \w     86.00 112.00   1.00   14.00    --  111.00  56.00 -32.62   26
 28  \w     84.00 110.00   1.00   14.00    --  111.00  64.00-129.94   26
 29  \w     86.00 163.00   1.00   14.00    --  111.00  60.00 -12.44   77
 30  \w     88.00 126.00   1.00   14.00    --  111.00-143.00 120.24   38
 31  \w     84.00 156.00   1.00   14.00    --  111.00  63.00-137.65   72
 32  \w     85.00 111.00   1.00   14.00    --  111.00  62.00   5.90   26
 33  \w     84.00 110.00   1.00   14.00    --  111.00  63.00 106.90   26
 34  \w     83.00 178.00   1.00   14.00    --  111.00  69.00  32.77   95
 35  \w     84.00 110.00   1.00   14.00    --  111.00  65.00 -74.58   26
 36  \w     82.00 108.00   1.00   14.00    --  111.00  71.00 -91.22   26
 37  \w     37.00 105.00   1.00   14.00    --  111.00 -94.00   0.00   68
 38  \w     87.00 113.00   1.00   14.00    --  111.00  53.00-147.44   26
 39  \w     88.00 178.00   1.00   14.00    --  111.00  48.00-177.33   90
 40  \w     85.00 121.00   1.00   14.00    --  111.00  61.00 -99.79   36
 41  \w    147.00 174.00   1.00   14.00    --  111.00  63.00 -21.84   27
 42  \w     44.00 137.00   1.00   14.00    --  111.00 -61.00  90.00   93
 43  \w     85.00 111.00   1.00   14.00    --  111.00  61.00  60.00   26
 44  \w     84.00 136.00   1.00   14.00    --  111.00  63.00 -21.84   52
 45  \w     42.00 132.00   1.00   14.00    --  111.00 -45.00 -30.00   90
 46  \w     85.00 176.00   1.00   14.00    --  111.00  61.00   0.00   91
 47  \w     85.00 113.00   1.00   14.00    --  111.00  61.00 120.00   28
 48  \w     85.00 176.00   1.00   14.00    --  111.00  61.00 -60.00   91
 49  \w     85.00 113.00   1.00   14.00    --  111.00  61.00  90.00   28
 50  \w     85.00 112.00   1.00   14.00    --  111.00  61.00 150.00   27
 51  \w     85.00 158.00   1.00   14.00    --  111.00  61.00-120.00   73
 52  \w     85.00 172.00   1.00   14.00    --  111.00  61.00 -90.00   87
 53  \w     84.00 110.00   1.00   14.00    --  111.00  63.00-108.57   26
 54  \w     42.00 113.00   1.00   14.00    --  111.00-125.00 150.00   71
 55  \w     85.00 111.00   1.00   14.00    --  111.00  61.00-180.00   26
 56  \w     51.00 107.00   1.00   14.00    --  111.00 -94.00-180.00   56
 57  \w     85.00 112.00   1.00   14.00    --  111.00  61.00 -30.00   27
 58  \w     85.00 113.00   1.00   14.00    --  111.00  60.00  81.52   28
 59  \w     42.00 108.00   1.00   14.00    --  111.00-103.00-101.33   66
 60  \w     41.00 108.00   1.00   14.00    --  111.00-103.00 -47.08   67
 61  \w     83.00 109.00   1.00   14.00    --  111.00  69.00-176.31   26
 62  \w    153.00 178.00   1.00   14.00    --  111.00  70.00 -59.84   25
 63  \w     84.00 124.00   1.00   14.00    --  111.00  64.00-147.55   40
 64  \w     88.00 114.00   1.00   14.00    --  111.00  48.00 175.75   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      -0.0139608000
_diffrn_orient_matrix_UB_12      -0.0737398000
_diffrn_orient_matrix_UB_13      -0.0035970000
_diffrn_orient_matrix_UB_21      0.0521237000
_diffrn_orient_matrix_UB_22      -0.0197243000
_diffrn_orient_matrix_UB_23      0.0198354000
_diffrn_orient_matrix_UB_31      -0.0003682000
_diffrn_orient_matrix_UB_32      0.0021011000
_diffrn_orient_matrix_UB_33      0.0598611000
_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  0.0841
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            294394
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.594
_diffrn_reflns_theta_min         2.682
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.857
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.697
_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    1.056
_exptl_crystal_description       block
_exptl_crystal_F_000             5108
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.995
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1273
_refine_ls_number_reflns         30812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0885P)^2^+8.6004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1653
_reflns_Friedel_coverage         0.000
_reflns_number_gt                23393
_reflns_number_total             30812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02118h2.cif
_cod_data_source_block           anti-9xPy4
_cod_database_code               7710925
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C130 H204 Al4 N4 Si16'
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.652
_reflns_odcompleteness_completeness 99.87
_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.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10), C17(H17), C24(H24), C36(H36), C43(H43), C57(H57), C64(H64),
 C78(H78), C85(H85), C99(H99), C106(H106)
2.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), C50(H50), C51(H51), C52(H52), C53(H53),
 C54(H54), C55(H55), C56(H56), C71(H71), C72(H72), C73(H73), C74(H74), C75(H75),
  C76(H76), C77(H77), C92(H92), C93(H93), C94(H94), C95(H95), C96(H96),
 C97(H97), C98(H98)
2.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,
 H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C44(H44A,H44B,H44C), C45(H45A,
 H45B,H45C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C),
 C49(H49A,H49B,H49C), C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,
 H60C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C65(H65A,
 H65B,H65C), C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C68(H68A,H68B,H68C),
 C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C79(H79A,H79B,H79C), C80(H80A,H80B,
 H80C), C81(H81A,H81B,H81C), C82(H82A,H82B,H82C), C83(H83A,H83B,H83C), C84(H84A,
 H84B,H84C), C86(H86A,H86B,H86C), C87(H87A,H87B,H87C), C88(H88A,H88B,H88C),
 C89(H89A,H89B,H89C), C90(H90A,H90B,H90C), C91(H91A,H91B,H91C), C100(H10A,H10B,
 H10C), C101(H10D,H10E,H10F), C102(H10G,H10H,H10I), C103(H10J,H10K,H10L),
 C104(H10M,H10N,H10O), C105(H10P,H10Q,H10R), C107(H10S,H10T,H10U), C108(H10V,
 H10W,H10X), C109(H10Y,H,HA), C110(H11A,H11B,H11C), C111(H11D,H11E,H11F),
 C112(H11G,H11H,H11I)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              68226
_shelx_fab_checksum              52418
_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 1.450
_oxdiff_exptl_absorpt_empirical_full_min 0.716