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_7710916
_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         'C48 H44 O4, (C3 H7 N1 O1)'
_chemical_formula_sum            'C51 H51 N O5'
_chemical_formula_weight         757.92
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-27
_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                92.036(5)
_cell_angle_beta                 102.618(5)
_cell_angle_gamma                114.109(6)
_cell_formula_units_Z            1
_cell_length_a                   9.8534(6)
_cell_length_b                   10.8417(7)
_cell_length_c                   11.1079(6)
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9760
_cell_measurement_theta_min      4.1150
_cell_volume                     1046.54(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (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      100.00(10)
_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 0.971
_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   -110.00 -18.00   1.00   33.00    --  -38.50 -37.00   0.00   92
  2  \w     -6.00  32.00   1.00   33.00    --  -38.50  37.00-180.00   38
  3  \w    -23.00  43.00   1.00   33.00    --   41.95 -57.00-150.00   66
  4  \w    -19.00 106.00   1.00   33.00    --   41.95   0.00   0.00  125
  5  \w     29.00  82.00   1.00   33.00    --   41.95-125.00-180.00   53
  6  \w     29.00  91.00   1.00   33.00    --   41.95-125.00   0.00   62
  7  \w     90.00 134.00   1.00   54.00    --  111.00 -61.00-120.00   44
  8  \w     42.00 126.00   1.00   54.00    --  111.00 -45.00  30.00   84
  9  \w    105.00 133.00   1.00   54.00    --  111.00 -77.00 150.00   28
 10  \w     41.00  74.00   1.00   54.00    --  111.00-125.00   0.00   33
 11  \w     84.00 112.00   1.00   54.00    --  111.00-125.00   0.00   28
 12  \w     63.00 107.00   1.00   54.00    --  111.00 -94.00  90.00   44
 13  \w     66.00 113.00   1.00   54.00    --  111.00-125.00-150.00   47
 14  \w    109.00 161.00   1.00   54.00    --  111.00  77.00  60.00   52
 15  \w    101.00 129.00   1.00   54.00    --  111.00  30.00-150.00   28
 16  \w     55.00 112.00   1.00   54.00    --  111.00-125.00  60.00   57
 17  \w     41.00 112.00   1.00   54.00    --  111.00 -30.00 150.00   71
 18  \w     35.00 100.00   1.00   54.00    --  111.00 -94.00-150.00   65
 19  \w    112.00 176.00   1.00   54.00    --  111.00  77.00 -60.00   64
 20  \w    127.00 178.00   1.00   54.00    --  111.00  77.00-180.00   51
 21  \w     42.00 113.00   1.00   54.00    --  111.00-125.00 -30.00   71
 22  \w     98.00 159.00   1.00   54.00    --  111.00  45.00 120.00   61
 23  \w     55.00 106.00   1.00   54.00    --  111.00 -15.00 -90.00   51
 24  \w    122.00 150.00   1.00   54.00    --  111.00 -15.00 -90.00   28
 25  \w     71.00 112.00   1.00   54.00    --  111.00-125.00  90.00   41
;
_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      0.0446079000
_diffrn_orient_matrix_UB_12      -0.0052716000
_diffrn_orient_matrix_UB_13      0.1409309000
_diffrn_orient_matrix_UB_21      -0.1709124000
_diffrn_orient_matrix_UB_22      -0.0593007000
_diffrn_orient_matrix_UB_23      0.0009595000
_diffrn_orient_matrix_UB_31      -0.0136672000
_diffrn_orient_matrix_UB_32      -0.1455181000
_diffrn_orient_matrix_UB_33      -0.0272188000
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12900
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.474
_diffrn_reflns_theta_min         4.119
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (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    1.203
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         8016
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0552
_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^)+(0.1098P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5607
_reflns_number_total             8016
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 2.4698\% 
around [0.39 0.77 -0.50] (reciprocal) or [0.63 0.76 -0.18] (direct)
;
_cod_data_source_file            d2dt02118h2.cif
_cod_data_source_block           syn-6
_cod_database_code               7710916
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C51 H51  N O5'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6396(14)
 0.3604(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Shared sites
{N1A, N1B}
4. Restrained distances
 N1A-C26A \\sim N1B-C27B \\sim N1A-C27A \\sim N1B-C26B
 with sigma of 0.02
 N1B-C25B \\sim N1A-C25A
 with sigma of 0.02
5. Uiso/Uaniso restraints and constraints
Uanis(N1A) = Uanis(N1B)
Uanis(C26B) = Uanis(C26A)
6. Others
 Sof(N1B)=Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=
 Sof(C27B)=Sof(H27D)=Sof(H27E)=Sof(H27F)=0.5*(1-FVAR(2))
 Sof(N1A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C27A)=Sof(H27A)=Sof(H27B)=Sof(H27C)=0.5*FVAR(2)
 Fixed Sof: O3(0.5)
7.a Me refined with riding coordinates:
 C26A(H26A,H26B,H26C), C27A(H27A,H27B,H27C), C26B(H26D,H26E,H26F), C27B(H27D,
 H27E,H27F)
7.b Aromatic/amide H refined with riding coordinates:
 C25A(H25A), C25B(H25B)
7.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              10310
_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 2.690
_oxdiff_exptl_absorpt_empirical_full_min 0.441
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2