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_1562400
_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 H72 B4 N8, H4 N2 [+ solvent]'
_chemical_formula_sum            'C84 H76 B4 N10'
_chemical_formula_weight         1268.78
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-06
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2019-09-09 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   26.4901(4)
_cell_length_b                   26.4901(4)
_cell_length_c                   44.9400(11)
_cell_measurement_reflns_used    12065
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.6320
_cell_measurement_theta_min      3.0590
_cell_volume                     31535.5(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.51a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.51a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.51a (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      100.00(10)
_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 1.000
_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    -43.00  25.00   1.00   50.00    --  -38.50  37.00  30.00   68
  2  \w   -110.00 -18.00   1.00   50.00    --  -38.50 -37.00  60.00   92
  3  \w    -42.00  28.00   1.00   50.00    --  -38.50  37.00-120.00   70
  4  \w      1.00  81.00   1.00   50.00    --   42.70 -99.00 -60.00   80
  5  \w     60.00  92.00   1.00   50.00    --   42.70 175.00 -85.00   32
  6  \w     42.00  85.00   1.00   50.00    --   42.70-125.00 150.00   43
  7  \w     32.00 150.00   1.00  100.00    --  111.00 -15.00 -90.00  118
  8  \w     73.00 113.00   1.00  100.00    --  111.00-114.00  44.00   40
  9  \w     92.00 145.00   1.00  100.00    --  111.00  77.00  60.00   53
 10  \w     39.00 132.00   1.00  100.00    --  111.00 -30.00 120.00   93
 11  \w     44.00 127.00   1.00  100.00    --  111.00 -61.00   0.00   83
 12  \w     43.00  72.00   1.00  100.00    --  111.00 -94.00 -90.00   29
 13  \w     36.00  84.00   1.00  100.00    --  111.00 -94.00 150.00   48
 14  \w     41.00  66.00   1.00  100.00    --  111.00-125.00 150.00   25
 15  \w     53.00 103.00   1.00  100.00    --  111.00 -94.00-180.00   50
 16  \w     44.00 107.00   1.00  100.00    --  111.00 -45.00 -90.00   63
 17  \w     87.00 118.00   1.00  100.00    --  111.00-125.00 150.00   31
 18  \w     97.00 151.00   1.00  100.00    --  111.00  30.00 -60.00   54
 19  \w     51.00 108.00   1.00  100.00    --  111.00 -94.00-120.00   57
 20  \w     55.00 107.00   1.00  100.00    --  111.00 -94.00 -60.00   52
 21  \w     93.00 118.00   1.00  100.00    --  111.00-125.00-150.00   25
 22  \w    152.00 177.00   1.00  100.00    --  111.00  77.00  60.00   25
 23  \w    109.00 134.00   1.00  100.00    --  111.00 -15.00  60.00   25
 24  \w     32.00  59.00   1.00  100.00    --  111.00 -15.00  60.00   27
;
_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      -0.0581255000
_diffrn_orient_matrix_UB_12      -0.0024044000
_diffrn_orient_matrix_UB_13      0.0007338000
_diffrn_orient_matrix_UB_21      0.0007345000
_diffrn_orient_matrix_UB_22      0.0102614000
_diffrn_orient_matrix_UB_23      0.0337244000
_diffrn_orient_matrix_UB_31      -0.0025509000
_diffrn_orient_matrix_UB_32      0.0571854000
_diffrn_orient_matrix_UB_33      -0.0060309000
_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  0.1541
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            114503
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         3.071
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.51a (Rigaku Oxford Diffraction, 2019)
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    1.069
_exptl_crystal_description       block
_exptl_crystal_F_000             10720
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     963
_refine_ls_number_reflns         13948
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0750
_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^)+(0.0585P)^2^+90.9461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9399
_reflns_number_total             13948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02065j2.cif
_cod_data_source_block           12
_cod_original_cell_volume        31535.6(12)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               1562400
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C86 H89 B4 N8'
_diffrn_oxdiff_digest_frames
;
0122d8d0df13698e6d144b3590e063728b013352cb7
;
_diffrn_oxdiff_digest_hkl
;
019af1e93a5250ff1d853159ba1f2feba8435b
;
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N5-H5A \\sim N5-H5B \\sim N6-H6A \\sim N6-H6B \\sim N4-H4A \\sim N4-H4B \\sim
N3-H3A \\sim N3-H3B \\sim N2-
 H2B \\sim N2-H2A \\sim N1-H1B \\sim N1-H1A \\sim N10-H10A \\sim N10-H10B \\sim
N9-H9A \\sim N9-H9B \\sim N8-
 H8B \\sim N7-H7A \\sim N7-H7B \\sim N8-H8A
 with sigma of 0.02
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)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              53954
_shelx_hkl_checksum              98095
_shelx_fab_checksum              72292
_olex2_date_sample_data_collection 2019-05-03
_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 2.483
_oxdiff_exptl_absorpt_empirical_full_min 0.444