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_1562396
_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_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 O2'
_chemical_formula_sum            'C24 H22 O2'
_chemical_formula_weight         342.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-22
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.74087(5)
_cell_length_b                   32.16370(14)
_cell_length_c                   9.77293(5)
_cell_measurement_reflns_used    48691
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.6820
_cell_measurement_theta_min      3.9600
_cell_volume                     3690.55(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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 0.9998
_diffrn_measured_fraction_theta_max 0.9482
_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 -16.00   1.00    3.37    --  -42.33 -57.00 -90.00   26
  2  \w    -62.00 -11.00   1.00    3.37    --  -42.33 -77.00   0.00   51
  3  \w    -41.00 -16.00   1.00    3.37    --  -42.33 -57.00  90.00   25
  4  \w    -79.00 -11.00   1.00    3.37    --  -42.33 -77.00  90.00   68
  5  \w      1.00  74.00   1.00    3.37    --   42.33 -99.00  30.00   73
  6  \w     42.00  69.00   1.00   13.47    --  111.00 -94.00 150.00   27
  7  \w     38.00 104.00   1.00   13.47    --  111.00 -94.00  60.00   66
  8  \w     60.00 120.00   1.00   13.47    --  111.00-125.00  60.00   60
  9  \w     39.00 139.00   1.00   13.47    --  111.00 -77.00  60.00  100
 10  \w     68.00 117.00   1.00   13.47    --  111.00-125.00-120.00   49
 11  \w     47.00 105.00   1.00   13.47    --  111.00 -94.00-120.00   58
 12  \w     30.00  80.00   1.00   13.47    --  111.00 -94.00   0.00   50
 13  \w     31.00 106.00   1.00   13.47    --  111.00 -94.00 -60.00   75
 14  \w     83.00 109.00   1.00   13.47    --  111.00  61.00-150.00   26
 15  \w    110.00 170.00   1.00   13.47    --  111.00  77.00-120.00   60
 16  \w    139.00 178.00   1.00   13.47    --  111.00  77.00 -60.00   39
 17  \w    114.00 172.00   1.00   13.47    --  111.00  77.00 -90.00   58
 18  \w    112.00 176.00   1.00   13.47    --  111.00  77.00  30.00   64
 19  \w    129.00 157.00   1.00   13.47    --  111.00  64.00  63.46   28
 20  \w     85.00 148.00   1.00   13.47    --  111.00  55.00 -44.48   63
 21  \w     83.00 109.00   1.00   13.47    --  111.00  61.00  30.00   26
 22  \w     83.00 109.00   1.00   13.47    --  111.00  61.00  60.00   26
 23  \w     83.00 148.00   1.00   13.47    --  111.00  61.00  90.00   65
 24  \w     83.00 109.00   1.00   13.47    --  111.00  61.00   0.00   26
 25  \w     81.00 175.00   1.00   13.47    --  111.00  77.00 -30.00   94
 26  \w     83.00 109.00   1.00   13.47    --  111.00  61.00-120.00   26
 27  \w     83.00 126.00   1.00   13.47    --  111.00  61.00 -90.00   43
 28  \w     80.00 172.00   1.00   13.47    --  111.00  77.00-150.00   92
 29  \w     80.00 106.00   1.00   13.47    --  111.00  77.00-120.00   26
 30  \w     80.00 106.00   1.00   13.47    --  111.00  77.00 -90.00   26
 31  \w     80.00 106.00   1.00   13.47    --  111.00  77.00 -60.00   26
 32  \w     83.00 109.00   1.00   13.47    --  111.00  61.00 -60.00   26
 33  \w     83.00 109.00   1.00   13.47    --  111.00  61.00 -30.00   26
 34  \w     80.00 106.00   1.00   13.47    --  111.00  77.00  30.00   26
 35  \w     80.00 176.00   1.00   13.47    --  111.00  77.00   0.00   96
 36  \w     80.00 106.00   1.00   13.47    --  111.00  77.00-180.00   26
 37  \w     83.00 169.00   1.00   13.47    --  111.00  61.00-180.00   86
 38  \w     58.00 129.00   1.00    3.37    --   42.33 178.00 -90.00   71
 39  \w     80.00 106.00   1.00   13.47    --  111.00  77.00  60.00   26
 40  \w     80.00 177.00   1.00   13.47    --  111.00  77.00  90.00   97
 41  \w     83.00 109.00   1.00   13.47    --  111.00  61.00 120.00   26
 42  \w     83.00 152.00   1.00   13.47    --  111.00  61.00 150.00   69
 43  \w     80.00 169.00   1.00   13.47    --  111.00  77.00 150.00   89
 44  \w     83.00 123.00   1.00   13.47    --  111.00  64.00  63.46   40
 45  \w     80.00 149.00   1.00   13.47    --  111.00  77.00 120.00   69
 46  \w    -25.00  66.00   1.00    3.37    --   42.33 -57.00-120.00   91
 47  \w    -27.00  65.00   1.00    3.37    --   42.33 -38.00  30.00   92
 48  \w    -42.00 -16.00   1.00    3.37    --  -42.33 -57.00-180.00   26
 49  \w    -69.00 -43.00   1.00    3.37    --  -42.33 -57.00 -90.00   26
 50  \w    -79.00 -13.00   1.00    3.37    --  -42.33 -77.00 -90.00   66
 51  \w    -70.00 -11.00   1.00    3.37    --  -42.33 -77.00-180.00   59
 52  \w   -103.00 -52.00   1.00    3.37    --  -42.33 -57.00-180.00   51
 53  \w   -116.00 -89.00   1.00    3.37    --  -42.33 -77.00-180.00   27
 54  \w   -116.00 -90.00   1.00    3.37    --  -42.33 -77.00   0.00   26
 55  \w   -115.00 -24.00   1.00    3.37    --  -42.33 -38.00   0.00   91
 56  \w   -100.00 -52.00   1.00    3.37    --  -42.33 -57.00  90.00   48
;
_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      -0.0082962000
_diffrn_orient_matrix_UB_12      -0.0466252000
_diffrn_orient_matrix_UB_13      -0.0348861000
_diffrn_orient_matrix_UB_21      0.1305604000
_diffrn_orient_matrix_UB_22      -0.0021286000
_diffrn_orient_matrix_UB_23      -0.0139390000
_diffrn_orient_matrix_UB_31      0.0100142000
_diffrn_orient_matrix_UB_32      -0.0108211000
_diffrn_orient_matrix_UB_33      0.1530526000
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            63776
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.321
_diffrn_reflns_theta_min         2.748
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 2990 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         6940
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0256
_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^)+(0.0456P)^2^+0.4750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0681
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                6850
_reflns_number_total             6940
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02065j2.cif
_cod_data_source_block           5
_cod_database_code               1562396
_chemical_oxdiff_formula         'C24 H22 O2'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.20
_olex2_date_sample_data_collection 2017-05-19
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.871
_shelx_hkl_checksum              56003
_shelx_res_checksum              64693
_shelx_shelxl_version_number     2014/7