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_1562395
_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         'C48 H44 O4, C6 H6'
_chemical_formula_sum            'C54 H50 O4'
_chemical_formula_weight         762.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-09-09 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.594(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1578(3)
_cell_length_b                   11.0555(3)
_cell_length_c                   17.2821(4)
_cell_measurement_reflns_used    18441
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.4030
_cell_measurement_theta_min      2.9980
_cell_volume                     2107.90(9)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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    -74.00 -24.00   1.00  125.00    --  -18.03 126.00-123.20   50
  2  \w    -88.00   9.00   1.00  125.00    --  -18.03 -57.00-150.00   97
  3  \w    -92.00 -38.00   1.00  125.00    --  -18.03 153.00  -9.19   54
  4  \w      9.00  77.00   1.00  125.00    --   18.42-130.00-128.79   68
  5  \w     -1.00  91.00   1.00  125.00    --   18.42  38.00 120.00   92
  6  \w      2.00  91.00   1.00  125.00    --   18.42  38.00  30.00   89
  7  \w    -13.00  58.00   1.00  125.00    --   18.42  77.00-150.00   71
  8  \w    -46.00  41.00   1.00  125.00    --   18.42 -38.00 -60.00   87
  9  \w     41.00  68.00   1.00  125.00    --   18.42 178.00 -30.00   27
 10  \w    -50.00  45.00   1.00  125.00    --   18.42 -57.00  30.00   95
 11  \w    -50.00  11.00   1.00  125.00    --   18.42 -38.00  90.00   61
;
_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      -0.0262738000
_diffrn_orient_matrix_UB_12      0.0519407000
_diffrn_orient_matrix_UB_13      0.0147679000
_diffrn_orient_matrix_UB_21      -0.0584097000
_diffrn_orient_matrix_UB_22      -0.0259421000
_diffrn_orient_matrix_UB_23      -0.0099403000
_diffrn_orient_matrix_UB_31      0.0054950000
_diffrn_orient_matrix_UB_32      -0.0273263000
_diffrn_orient_matrix_UB_33      0.0374970000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47712
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_min         2.608
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.620
_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    1.202
_exptl_crystal_description       needle
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         6166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0717P)^2^+1.0537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5319
_reflns_number_total             6166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02065j2.cif
_cod_data_source_block           Syn-6
_cod_database_code               1562395
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C54 H50 O4'
_diffrn_oxdiff_ac3_digest_frames
;
012e1fa854c22c34c6f5709ef7e64d61f900825c67f
;
_diffrn_oxdiff_ac3_digest_hkl
;
01b88c6da9b7e911185f08e7fcdfcc2cdf552d
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C25(H25), C26(H26),
 C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              91979
_shelx_hkl_checksum              41775
_olex2_date_sample_data_collection 2017-07-28
_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.802