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_1562391
_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         'C16 H8 F6 O6 S2'
_chemical_formula_sum            'C16 H8 F6 O6 S2'
_chemical_formula_weight         474.34
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-29
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2019-09-09 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                84.758(6)
_cell_angle_beta                 87.356(7)
_cell_angle_gamma                74.878(9)
_cell_formula_units_Z            2
_cell_length_a                   5.4457(5)
_cell_length_b                   9.7022(10)
_cell_length_c                   17.3622(8)
_cell_measurement_reflns_used    3814
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.9880
_cell_measurement_theta_min      4.7090
_cell_volume                     881.63(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_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 0.9821
_diffrn_measured_fraction_theta_max 0.9769
_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    -42.00  25.00   1.00   10.64    --  -38.50  37.00 -90.00   67
  2  \w    -27.00  33.00   1.00   10.64    --  -38.50  77.00 -30.00   60
  3  \w    -67.00 -29.00   1.00   10.64    --  -38.50  77.00 -30.00   38
  4  \w     18.00  50.00   1.00   10.64    --   41.95  57.00 -90.00   32
  5  \w     59.00  98.00   1.00   10.64    --   41.95  22.00  31.00   39
  6  \w     79.00 123.00   1.00   10.64    --   41.95-178.00  90.00   44
  7  \w     66.00  99.00   1.00   10.64    --   41.95  77.00   0.00   33
  8  \w     58.00 125.00   1.00   10.64    --   41.95 178.00 -90.00   67
  9  \w     68.00 105.00   1.00   10.64    --   41.95  57.00 -90.00   37
 10  \w     23.00  64.00   1.00   10.64    --   41.95  37.00 120.00   41
 11  \w      6.00  32.00   1.00   10.64    --   41.95  90.00  54.27   26
 12  \w     18.00 111.00   1.00   10.64    --   41.95  77.00-180.00   93
 13  \w     12.00  87.00   1.00   10.64    --   41.95  77.00 120.00   75
 14  \w    -23.00  61.00   1.00   10.64    --   41.95 -37.00  30.00   84
 15  \w     12.00  64.00   1.00   10.64    --   41.95  77.00 -60.00   52
 16  \w     16.00  59.00   1.00   10.64    --   41.95  77.00   0.00   43
 17  \w     13.00  57.00   1.00   10.64    --   41.95  22.00  31.00   44
 18  \w     85.00 111.00   1.00   33.00    --  111.00  61.00  30.00   26
 19  \w     42.00  85.00   1.00   33.00    --  111.00-125.00-150.00   43
 20  \w     85.00 114.00   1.00   33.00    --  111.00  59.00 -88.76   29
 21  \w     81.00 156.00   1.00   33.00    --  111.00  77.00  60.00   75
 22  \w    111.00 176.00   1.00   33.00    --  111.00  77.00  90.00   65
 23  \w     81.00 108.00   1.00   33.00    --  111.00  77.00 120.00   27
 24  \w     81.00 107.00   1.00   33.00    --  111.00  77.00  90.00   26
 25  \w     89.00 150.00   1.00   33.00    --  111.00  45.00   0.00   61
 26  \w     81.00 107.00   1.00   33.00    --  111.00  77.00 -60.00   26
 27  \w     81.00 178.00   1.00   33.00    --  111.00  77.00 -90.00   97
 28  \w     36.00  76.00   1.00   33.00    --  111.00 -94.00 -60.00   40
 29  \w     81.00 109.00   1.00   33.00    --  111.00 -94.00 -60.00   28
 30  \w     82.00 109.00   1.00   33.00    --  111.00  77.00 -30.00   27
 31  \w     82.00 109.00   1.00   33.00    --  111.00  73.00-112.18   27
 32  \w    153.00 178.00   1.00   33.00    --  111.00  52.00 177.87   25
 33  \w     81.00 162.00   1.00   33.00    --  111.00  77.00-150.00   81
 34  \w    116.00 164.00   1.00   33.00    --  111.00  61.00 -30.00   48
 35  \w     85.00 114.00   1.00   33.00    --  111.00  61.00   0.00   29
 36  \w    147.00 178.00   1.00   33.00    --  111.00  61.00 120.00   31
 37  \w     87.00 114.00   1.00   33.00    --  111.00  61.00 120.00   27
 38  \w     85.00 111.00   1.00   33.00    --  111.00  61.00  90.00   26
 39  \w     83.00 130.00   1.00   33.00    --  111.00  67.00  56.17   47
 40  \w     77.00 107.00   1.00   33.00    --  111.00 -94.00   0.00   30
 41  \w     41.00  66.00   1.00   33.00    --  111.00 -94.00   0.00   25
 42  \w     85.00 112.00   1.00   33.00    --  111.00  61.00 -30.00   27
 43  \w     83.00 112.00   1.00   33.00    --  111.00  77.00  30.00   29
 44  \w     33.00 106.00   1.00   33.00    --  111.00 -94.00-150.00   73
 45  \w     86.00 111.00   1.00   33.00    --  111.00  61.00-180.00   25
 46  \w     85.00 177.00   1.00   33.00    --  111.00  61.00 150.00   92
 47  \w     81.00 174.00   1.00   33.00    --  111.00  77.00   0.00   93
 48  \w     33.00  58.00   1.00   33.00    --  111.00 -94.00  60.00   25
 49  \w     82.00 109.00   1.00   33.00    --  111.00 -94.00  60.00   27
 50  \w     90.00 121.00   1.00   33.00    --  111.00  45.00 -90.00   31
 51  \w     31.00 109.00   1.00   33.00    --  111.00 -94.00 -90.00   78
 52  \w     89.00 115.00   1.00   33.00    --  111.00  45.00 120.00   26
 53  \w     85.00 123.00   1.00   33.00    --  111.00  61.00-150.00   38
 54  \w     46.00 108.00   1.00   33.00    --  111.00 -94.00 120.00   62
 55  \w     89.00 116.00   1.00   33.00    --  111.00  45.00-150.00   27
 56  \w     86.00 156.00   1.00   33.00    --  111.00  61.00 -60.00   70
 57  \w     85.00 173.00   1.00   33.00    --  111.00  61.00-120.00   88
 58  \w    131.00 154.00   1.00   33.00    --  111.00  61.00  30.00   23
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0864421000
_diffrn_orient_matrix_UB_12      -0.1640386000
_diffrn_orient_matrix_UB_13      0.0162232000
_diffrn_orient_matrix_UB_21      -0.2666604000
_diffrn_orient_matrix_UB_22      -0.0110048000
_diffrn_orient_matrix_UB_23      -0.0198931000
_diffrn_orient_matrix_UB_31      0.0856810000
_diffrn_orient_matrix_UB_32      -0.0144380000
_diffrn_orient_matrix_UB_33      -0.0853508000
_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  0.0650
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11552
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.331
_diffrn_reflns_theta_min         2.556
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.674
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (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    1.787
_exptl_crystal_description       plate
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0614
_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^)+(0.1110P)^2^+0.2466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1782
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2672
_reflns_number_total             3434
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02065j2.cif
_cod_data_source_block           4
_cod_original_cell_volume        881.63(14)
_cod_database_code               1562391
_chemical_oxdiff_formula         'C16 H8 F6 O6 S2'
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_date_sample_data_collection 2016-07-27
_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 1.526
_oxdiff_exptl_absorpt_empirical_full_min 0.570
_shelx_hkl_checksum              16159
_shelx_res_checksum              1351
_shelxl_version_number           2014-3