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_1562398
_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, 5.62(C2 H3 N)'
_chemical_formula_sum            'C95.25 H84.87 B4 N9.62'
_chemical_formula_weight         1407.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-18
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
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            8
_cell_length_a                   19.2454(7)
_cell_length_b                   28.1544(12)
_cell_length_c                   29.7705(10)
_cell_measurement_reflns_used    4594
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      71.8200
_cell_measurement_theta_min      3.1000
_cell_volume                     16130.9(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (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 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      5.00  32.00   1.00   20.00    --  -38.50  38.00-150.00   27
  2  \w    -59.00  33.00   1.00   20.00    --  -38.50  38.00-180.00   92
  3  \w   -104.00 -64.00   1.00   20.00    --  -38.50-148.00 154.00   40
  4  \w     43.00  78.00   1.00   20.00    --   42.89 -99.00 150.00   35
  5  \w     95.00 121.00   1.00   80.00    --  106.24 -30.00-150.00   26
  6  \w     44.00 125.00   1.00   80.00    --  106.24 -45.00  60.00   81
  7  \w     39.00 111.00   1.00   80.00    --  106.24-125.00 -60.00   72
  8  \w     94.00 143.00   1.00   80.00    --  106.24 125.00-150.00   49
  9  \w     88.00 114.00   1.00   80.00    --  106.24-125.00  90.00   26
 10  \w     95.00 174.00   1.00   80.00    --  106.24 125.00 120.00   79
 11  \w     61.00 121.00   1.00   80.00    --  106.24 -77.00 120.00   60
;
_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      0.0037914000
_diffrn_orient_matrix_UB_12      -0.0035416000
_diffrn_orient_matrix_UB_13      0.0516179000
_diffrn_orient_matrix_UB_21      -0.0549323000
_diffrn_orient_matrix_UB_22      -0.0397855000
_diffrn_orient_matrix_UB_23      -0.0007842000
_diffrn_orient_matrix_UB_31      0.0580244000
_diffrn_orient_matrix_UB_32      -0.0374094000
_diffrn_orient_matrix_UB_33      -0.0039861000
_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  0.1485
_diffrn_reflns_av_unetI/netI     0.1206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            54697
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.139
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (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    1.159
_exptl_crystal_description       plate
_exptl_crystal_F_000             5950
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.00016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1081
_refine_ls_number_reflns         14388
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0687
_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^)+(0.0894P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.2177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8076
_reflns_number_total             14388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02065j2.cif
_cod_data_source_block           10b
_cod_database_code               1562398
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C95H84.5B4N9.5
_diffrn_oxdiff_digest_frames
;
0105d0afcf403cd35decececa777ce7085005916eb1
;
_diffrn_oxdiff_digest_hkl
;
01012b5f159d32d95cab87ea9cc4a075b1a4d8
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 N11-C97 \\sim N7B-C89B \\sim N13-C99 \\sim N10-C95 \\sim N6-C87A \\sim N6-C87B
\\sim N5-C85 \\sim N8-C91
 \\sim N9-C93 \\sim N7-C89
 with sigma of 0.02
 C97-C98 \\sim C89B-C90B \\sim C90-C89 \\sim C100-C99 \\sim C95-C96 \\sim
C87A-C88A \\sim C87B-C88B ~
 C86-C85 \\sim C92-C91 \\sim C94-C93
 with sigma of 0.02
3. Others
 Sof(C87B)=Sof(C88B)=Sof(H88D)=Sof(H88E)=Sof(H88F)=Sof(N10)=Sof(C95)=Sof(C96)=
 Sof(H96A)=Sof(H96B)=Sof(H96C)=1-FVAR(1)
 Sof(C87A)=Sof(C88A)=Sof(H88A)=Sof(H88B)=Sof(H88C)=FVAR(1)
 Sof(N7B)=Sof(C89B)=Sof(C90B)=Sof(H90D)=Sof(H90E)=Sof(H90F)=Sof(N11)=Sof(C97)=
 Sof(C98)=Sof(H98A)=Sof(H98B)=Sof(H98C)=Sof(N13)=Sof(C99)=Sof(C100)=Sof(H10A)=
 Sof(H10B)=Sof(H10C)=1-FVAR(2)
 Sof(N7)=Sof(C89)=Sof(C90)=Sof(H90A)=Sof(H90B)=Sof(H90C)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10), C45(H45), C52(H52)
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),
  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)
4.c Idealised Me refined as rotating group:
 C86(H86A,H86B,H86C), C88A(H88A,H88B,H88C), C88B(H88D,H88E,H88F), C90(H90A,
 H90B,H90C), C90B(H90D,H90E,H90F), C92(H92A,H92B,H92C), C94(H94A,H94B,H94C),
 C96(H96A,H96B,H96C), C98(H98A,H98B,H98C), C100(H10A,H10B,H10C)
;
_shelx_res_checksum              73331
_shelx_hkl_checksum              49797
_olex2_date_sample_data_collection 2019-06-16
_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 2.033
_oxdiff_exptl_absorpt_empirical_full_min 0.388