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_1562397
_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         'C104 H76 B4 N4'
_chemical_formula_sum            'C104 H76 B4 N4'
_chemical_formula_weight         1424.92
_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             2018-07-09
_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                90
_cell_angle_beta                 91.677(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0002(4)
_cell_length_b                   40.8950(12)
_cell_length_c                   17.3331(6)
_cell_measurement_reflns_used    11562
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      71.9380
_cell_measurement_theta_min      3.2810
_cell_volume                     9919.6(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_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 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    -64.00  30.00   1.00   32.00    --  -38.50  57.00 -30.00   94
  2  \w   -107.00 -15.00   1.00   32.00    --  -38.50 -57.00-180.00   92
  3  \w    -79.00  -8.00   1.00   32.00    --  -38.50 125.00 -30.00   71
  4  \w    -57.00  33.00   1.00   32.00    --  -38.50  38.00 120.00   90
  5  \w     33.00  86.00   1.00   32.00    --   43.45-125.00-180.00   53
  6  \w     37.00 124.00   1.00  120.00    --  109.35 -30.00 -90.00   87
  7  \w     52.00 123.00   1.00  120.00    --  109.35 -30.00-180.00   71
  8  \w     44.00 117.00   1.00  120.00    --  109.35-125.00-180.00   73
  9  \w    139.00 171.00   1.00  120.00    --  109.35 125.00 -60.00   32
 10  \w     55.00 113.00   1.00  120.00    --  109.35 -30.00  90.00   58
 11  \w     50.00  77.00   1.00  120.00    --  109.35 -94.00 -60.00   27
 12  \w    100.00 176.00   1.00  120.00    --  109.35  30.00-120.00   76
 13  \w     89.00 117.00   1.00  120.00    --  109.35-125.00  30.00   28
 14  \w     32.00 107.00   1.00  120.00    --  109.35 -94.00-120.00   75
 15  \w     96.00 124.00   1.00  120.00    --  109.35 125.00 -60.00   28
 16  \w    118.00 169.00   1.00  120.00    --  109.35  30.00 -60.00   51
 17  \w     47.00 123.00   1.00  120.00    --  109.35 -45.00   0.00   76
 18  \w     43.00 131.00   1.00  120.00    --  109.35 -77.00 -30.00   88
;
_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      -0.1073987000
_diffrn_orient_matrix_UB_12      -0.0029894000
_diffrn_orient_matrix_UB_13      -0.0206932000
_diffrn_orient_matrix_UB_21      0.0210568000
_diffrn_orient_matrix_UB_22      -0.0287885000
_diffrn_orient_matrix_UB_23      -0.0543226000
_diffrn_orient_matrix_UB_31      -0.0117347000
_diffrn_orient_matrix_UB_32      -0.0241039000
_diffrn_orient_matrix_UB_33      0.0673180000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            66655
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.750
_diffrn_reflns_theta_min         2.770
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.15e (Rigaku Oxford Diffraction, 2015)
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    0.954
_exptl_crystal_description       plate
_exptl_crystal_F_000             2992
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1113
_refine_ls_number_reflns         17595
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0871
_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^)+(0.1445P)^2^+1.4548P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2509
_refine_ls_wR_factor_ref         0.2793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10611
_reflns_number_total             17595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02065j2.cif
_cod_data_source_block           9
_cod_database_code               1562397
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c110 h82 B4 N4'
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.65
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C42-B2 \\sim C42B-B2 \\sim C69-B3 \\sim C69B-B3 \\sim C75-B3 \\sim C75B-B3
 with sigma of 0.02
3. Others
 Sof(C74B)=Sof(H74B)=Sof(C73B)=Sof(H73B)=Sof(C72B)=Sof(H72B)=Sof(C71B)=
 Sof(H71B)=Sof(C70B)=Sof(H70B)=Sof(C69B)=Sof(C75B)=Sof(C76B)=Sof(H76B)=
 Sof(C77B)=Sof(H77B)=Sof(C78B)=Sof(H78B)=Sof(C79B)=Sof(H79B)=Sof(C80B)=
 Sof(H80B)=1-FVAR(1)
 Sof(C69)=Sof(C70)=Sof(H70)=Sof(C71)=Sof(H71)=Sof(C72)=Sof(H72)=Sof(C73)=
 Sof(H73)=Sof(C74)=Sof(H74)=Sof(C76)=Sof(H76)=Sof(C77)=Sof(H77)=Sof(C78)=
 Sof(H78)=Sof(C79)=Sof(H79)=Sof(C80)=Sof(H80)=Sof(C75)=FVAR(1)
 Sof(C42B)=Sof(C47B)=Sof(H47B)=Sof(C46B)=Sof(H46B)=Sof(C45B)=Sof(H45B)=
 Sof(C44B)=Sof(H44B)=Sof(C43B)=Sof(H43B)=1-FVAR(2)
 Sof(C42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=Sof(C46)=
 Sof(H46)=Sof(C47)=Sof(H47)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10), C55(H55), C62(H62)
4.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),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C37(H37), C38(H38),
 C39(H39), C40(H40), C41(H41), C47B(H47B), C46B(H46B), C45B(H45B), C44B(H44B),
 C43B(H43B), C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48),
 C49(H49), C50(H50), C51(H51), C52(H52), C58(H58), C59(H59), C60(H60), C64(H64),
  C65(H65), C66(H66), C70(H70), C71(H71), C72(H72), C73(H73), C74(H74),
 C74B(H74B), C73B(H73B), C72B(H72B), C71B(H71B), C70B(H70B), C76B(H76B),
 C77B(H77B), C78B(H78B), C79B(H79B), C80B(H80B), C76(H76), C77(H77), C78(H78),
 C79(H79), C80(H80), C81(H81), C82(H82), C83(H83), C84(H84), C85(H85), C89(H89),
  C90(H90), C91(H91), C92(H92), C93(H93), C95(H95), C96(H96), C97(H97),
 C98(H98), C99(H99), C100(H100), C101(H101), C102(H102), C103(H103), C104(H104)
4.c Fitted hexagon refined as free rotating group:
 C42B(C47B,C46B,C45B,C44B,C43B), C69(C70,C71,C72,C73,C74), C74B(C73B,C72B,C71B,
 C70B,C69B), C75B(C76B,C77B,C78B,C79B,C80B), C76(C77,C78,C79,C80,C75)
;
_shelx_res_checksum              48752
_shelx_hkl_checksum              42240
_shelx_fab_checksum              74324
_olex2_date_sample_data_collection 2018-06-08
_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 2.159
_oxdiff_exptl_absorpt_empirical_full_min 0.516