Hydrogen-Bond-Induced Selectivity of a Head-to-Head Photo- Dimerization of Dialkynylanthracene – Access to Tetra Lewis Acids
Niermeier, Philipp; Maibom, Kristina; Lamm, Jan-Hendrik; Neumann, Beate; Stammler, Georg; Mitzel, Norbert Werner; Chemical Science  (2021) –; doi:10.1039/D1SC02065J

data_1562394
_publ_section_title
;
 Hydrogen-Bond-Induced Selectivity of a Head-to-Head Photo- Dimerization
 of Dialkynylanthracene -- Access to Tetra Lewis Acids
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02065J
_journal_year                    2021
_chemical_formula_moiety         'C84 H68 B4 N4, 3.5(C6 H6)'
_chemical_formula_sum            'C105 H89 B4 N4'
_chemical_formula_weight         1450.04
_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             2019-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-09 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                100.327(3)
_cell_angle_beta                 98.165(4)
_cell_angle_gamma                99.886(4)
_cell_formula_units_Z            2
_cell_length_a                   14.4537(8)
_cell_length_b                   14.7536(6)
_cell_length_c                   20.5177(7)
_cell_measurement_reflns_used    6708
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.2750
_cell_measurement_theta_min      3.1050
_cell_volume                     4172.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.49a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.49a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.49a (Rigaku OD, 2019)'
_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 0.999
_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 -23.00   1.00    9.50    --  -38.50 -37.00 -60.00   87
  2  \w   -110.00 -18.00   1.00    9.50    --  -38.50 -37.00-150.00   92
  3  \w    -80.00  -4.00   1.00    9.50    --  -38.50 125.00   0.00   76
  4  \w    -49.00 -14.00   1.00    9.50    --  -38.50 125.00  90.00   35
  5  \w     45.00  89.00   1.00    9.50    --   42.89-125.00 -90.00   44
  6  \w     76.00 105.00   1.00   38.00    --  106.24 -94.00  30.00   29
  7  \w     45.00  71.00   1.00   38.00    --  106.24 -94.00  30.00   26
  8  \w    132.00 178.00   1.00   38.00    --  106.24  77.00-150.00   46
  9  \w     49.00 129.00   1.00   38.00    --  106.24 -77.00  90.00   80
 10  \w     84.00 175.00   1.00   38.00    --  106.24  45.00-180.00   91
 11  \w     33.00 125.00   1.00   38.00    --  106.24 -30.00-120.00   92
 12  \w     43.00 130.00   1.00   38.00    --  106.24 -61.00 -60.00   87
 13  \w     71.00 178.00   1.00   38.00    --  106.24  15.00 -60.00  107
 14  \w     31.00 100.00   1.00   38.00    --  106.24 -94.00 -90.00   69
 15  \w     88.00 117.00   1.00   38.00    --  106.24-125.00   0.00   29
 16  \w     92.00 117.00   1.00   38.00    --  106.24-125.00-180.00   25
 17  \w     85.00 110.00   1.00   38.00    --  106.24 -94.00-180.00   25
 18  \w     37.00  88.00   1.00   38.00    --  106.24 -36.00  57.00   51
 19  \w     76.00 115.00   1.00   38.00    --  106.24  77.00-150.00   39
;
_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      0.0567453000
_diffrn_orient_matrix_UB_12      -0.0697984000
_diffrn_orient_matrix_UB_13      0.0257126000
_diffrn_orient_matrix_UB_21      0.0882766000
_diffrn_orient_matrix_UB_22      0.0467316000
_diffrn_orient_matrix_UB_23      -0.0248877000
_diffrn_orient_matrix_UB_31      0.0328208000
_diffrn_orient_matrix_UB_32      0.0684925000
_diffrn_orient_matrix_UB_33      0.0688156000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_unetI/netI     0.1398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28058
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.109
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.49a (Rigaku Oxford Diffraction, 2019)
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    1.154
_exptl_crystal_description       needle
_exptl_crystal_F_000             1534
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1097
_refine_ls_number_reflns         14901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0285P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1475
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9295
_reflns_number_total             14901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02065j2.cif
_cod_data_source_block           10
_cod_database_code               1562394
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C105H77B4N4
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.800
_diffrn_oxdiff_digest_frames
;
01d2c4b88346423e6e12db857fb812e69a01134b99a
;
_diffrn_oxdiff_digest_hkl
;
01ad57ced4edd85ec017f6d19d5e468342ee69
;
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(C95A)=Sof(H95A)=Sof(C94A)=Sof(H94A)=Sof(C93A)=Sof(H93A)=Sof(C92A)=
 Sof(H92A)=Sof(C91A)=Sof(H91A)=Sof(C96A)=Sof(H96A)=1-FVAR(1)
 Sof(C95B)=Sof(H95B)=Sof(C94B)=Sof(H94B)=Sof(C93B)=Sof(H93B)=Sof(C92B)=
 Sof(H92B)=Sof(C91B)=Sof(H91B)=Sof(C96B)=Sof(H96B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10), C45(H45), C52(H52)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C38(H38), C39(H39),
 C40(H40), C41(H41), C42(H42), C48(H48), C49(H49), C50(H50), C54(H54), C55(H55),
  C56(H56), C60(H60), C61(H61), C62(H62), C63(H63), C64(H64), C66(H66),
 C67(H67), C68(H68), C69(H69), C70(H70), C74(H74), C75(H75), C76(H76), C77(H77),
  C78(H78), C80(H80), C81(H81), C82(H82), C83(H83), C84(H84), C85(H85),
 C86(H86), C87(H87), C88(H88), C89(H89), C90(H90), C95A(H95A), C94A(H94A),
 C93A(H93A), C92A(H92A), C91A(H91A), C96A(H96A), C95B(H95B), C94B(H94B),
 C93B(H93B), C92B(H92B), C91B(H91B), C96B(H96B), C97(H97), C98(H98), C99(H99),
 C100(H100), C101(H101), C102(H102), C103(H103), C104(H104), C105(H105)
3.c Fitted hexagon refined as free rotating group:
 C95A(C94A,C93A,C92A,C91A,C96A), C95B(C94B,C93B,C92B,C91B,C96B)
;
_shelx_res_checksum              28763
_shelx_hkl_checksum              40388
_olex2_date_sample_data_collection 2019-04-17
_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 2.459
_oxdiff_exptl_absorpt_empirical_full_min 0.452