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_1562390
_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 H10 F6 O6 S2'
_chemical_formula_sum            'C16 H10 F6 O6 S2'
_chemical_formula_weight         476.36
_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             2016-07-19
_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                87.983(3)
_cell_angle_beta                 78.962(3)
_cell_angle_gamma                69.485(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5762(4)
_cell_length_b                   10.0978(5)
_cell_length_c                   10.1439(3)
_cell_measurement_reflns_used    10422
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.3640
_cell_measurement_theta_min      4.3980
_cell_volume                     901.15(7)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9899
_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    -29.00  65.00   1.00    1.00    --   42.33 -37.00   0.00   94
  2  \w      2.00  78.00   1.00    1.00    --   42.33 -99.00 -30.00   76
  3  \w     56.00  98.00   1.00    1.00    --   42.33-178.00 -30.00   42
  4  \w     39.00 119.00   1.00    2.10    --  109.86-125.00  30.00   80
  5  \w     30.00 104.00   1.00    2.10    --  109.86 -94.00  60.00   74
  6  \w     31.00 106.00   1.00    2.10    --  109.86 -94.00 150.00   75
  7  \w    117.00 160.00   1.00    2.10    --  109.86  43.00  90.09   43
  8  \w    136.00 163.00   1.00    2.10    --  109.86  77.00  60.00   27
  9  \w    125.00 176.00   1.00    2.10    --  109.86  61.00  30.00   51
 10  \w    120.00 177.00   1.00    2.10    --  109.86  71.00-117.40   57
 11  \w    141.00 168.00   1.00    2.10    --  109.86  61.00-167.11   27
 12  \w    118.00 145.00   1.00    2.10    --  109.86  61.00-150.00   27
 13  \w     86.00 117.00   1.00    2.10    --  109.86  45.00 -60.00   31
 14  \w     82.00 112.00   1.00    2.10    --  109.86  61.00 -30.00   30
 15  \w     84.00 156.00   1.00    2.10    --  109.86  53.00  -8.41   72
 16  \w     87.00 112.00   1.00    2.10    --  109.86  43.00  90.09   25
 17  \w     87.00 115.00   1.00    2.10    --  109.86  45.00  60.00   28
 18  \w     82.00 108.00   1.00    2.10    --  109.86  61.00  30.00   26
 19  \w     86.00 178.00   1.00    2.10    --  109.86  61.00   0.00   92
 20  \w     86.00 118.00   1.00    2.10    --  109.86  45.00 150.00   32
 21  \w     83.00 177.00   1.00    2.10    --  109.86  61.00 150.00   94
 22  \w     78.00 105.00   1.00    2.10    --  109.86  77.00  60.00   27
 23  \w     82.00 115.00   1.00    2.10    --  109.86  61.00  90.00   33
 24  \w     83.00 109.00   1.00    2.10    --  109.86  61.00 120.00   26
 25  \w     84.00 112.00   1.00    2.10    --  109.86  59.00 164.34   28
 26  \w     78.00 166.00   1.00    2.10    --  109.86  77.00  90.00   88
 27  \w     82.00 178.00   1.00    2.10    --  109.86  61.00 -60.00   96
 28  \w     82.00 109.00   1.00    2.10    --  109.86  61.00-180.00   27
 29  \w     82.00 108.00   1.00    2.10    --  109.86  61.00-167.11   26
 30  \w     83.00 109.00   1.00    2.10    --  109.86  61.00-120.00   26
 31  \w     83.00 116.00   1.00    2.10    --  109.86  61.00-150.00   33
 32  \w     82.00 108.00   1.00    2.10    --  109.86  61.00 -90.00   26
 33  \w     78.00 171.00   1.00    2.10    --  109.86  77.00-150.00   93
 34  \w     79.00 106.00   1.00    2.10    --  109.86  77.00 -90.00   27
 35  \w     78.00 104.00   1.00    2.10    --  109.86  77.00 -60.00   26
 36  \w     80.00 107.00   1.00    2.10    --  109.86  71.00-117.40   27
 37  \w     78.00 105.00   1.00    2.10    --  109.86  77.00   0.00   27
 38  \w     82.00 109.00   1.00    2.10    --  109.86  63.00  52.41   27
 39  \w     82.00 109.00   1.00    2.10    --  109.86  61.00  60.00   27
 40  \w     57.00 120.00   1.00    1.00    --   42.33 178.00-120.00   63
 41  \w    -53.00 -24.00   1.00    1.00    --  -42.33 -37.00  60.00   29
 42  \w    -41.00 -11.00   1.00    1.00    --  -42.33 -77.00 120.00   30
 43  \w    -72.00 -11.00   1.00    1.00    --  -42.33 -77.00  60.00   61
 44  \w    -62.00 -21.00   1.00    1.00    --  -42.33 -37.00 -30.00   41
 45  \w     36.00 139.00   1.00    2.10    --  109.86 -77.00-180.00  103
 46  \w    -62.00 -11.00   1.00    1.00    --  -42.33 -77.00 -30.00   51
 47  \w    -69.00 -18.00   1.00    1.00    --  -42.33 -57.00-120.00   51
 48  \w    -85.00 -11.00   1.00    1.00    --  -42.33 -77.00-150.00   74
 49  \w   -116.00 -89.00   1.00    1.00    --  -42.33 -77.00  60.00   27
 50  \w   -113.00 -88.00   1.00    1.00    --  -42.33 -37.00  60.00   25
 51  \w   -112.00 -81.00   1.00    1.00    --  -42.33 -77.00 120.00   31
 52  \w   -110.00 -63.00   1.00    1.00    --  -42.33 -37.00 150.00   47
 53  \w   -113.00 -68.00   1.00    1.00    --  -42.33 -37.00 -30.00   45
 54  \w   -112.00 -85.00   1.00    1.00    --  -42.33 -77.00 -30.00   27
;
_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      0.0321146000
_diffrn_orient_matrix_UB_12      -0.0140970000
_diffrn_orient_matrix_UB_13      -0.1545595000
_diffrn_orient_matrix_UB_21      0.1625379000
_diffrn_orient_matrix_UB_22      -0.0024171000
_diffrn_orient_matrix_UB_23      -0.0041683000
_diffrn_orient_matrix_UB_31      0.0563512000
_diffrn_orient_matrix_UB_32      -0.1623640000
_diffrn_orient_matrix_UB_33      0.0080875000
_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  0.0191
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13616
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.349
_diffrn_reflns_theta_min         4.444
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.595
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.824
_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_description       fragment
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0449P)^2^+0.5195P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3333
_reflns_number_total             3536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02065j2.cif
_cod_data_source_block           4a
_cod_original_cell_volume        901.16(7)
_cod_database_code               1562390
_chemical_oxdiff_formula         'C16 H10 F6 O6 S2'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_date_sample_data_collection 2016-07-19
_olex2_date_sample_submission    1468792800
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14)
;
_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 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.913
_shelx_hkl_checksum              12087
_shelx_res_checksum              91957
_shelxl_version_number           2013-2