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_1562393
_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         'C36 H20'
_chemical_formula_sum            'C36 H20'
_chemical_formula_weight         452.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-17
_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                 111.7520(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.03642(5)
_cell_length_b                   20.42255(9)
_cell_length_c                   12.53918(8)
_cell_measurement_reflns_used    52436
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.2910
_cell_measurement_theta_min      3.7850
_cell_volume                     2387.14(2)
_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      air
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6228
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9998
_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   -115.00 -20.00   1.00    1.58    --  -42.58 -38.00 150.00   95
  2  \w    -69.00  28.00   1.00    1.58    --  -42.58  57.00 -90.00   97
  3  \w   -116.00 -11.00   1.00    1.58    --  -42.58 -77.00  90.00  105
  4  \w   -116.00 -11.00   1.00    1.58    --  -42.58 -77.00-120.00  105
  5  \w   -116.00 -11.00   1.00    1.58    --  -42.58 -77.00 150.00  105
  6  \w   -113.00 -16.00   1.00    1.58    --  -42.58 -57.00 -30.00   97
  7  \w   -116.00 -11.00   1.00    1.58    --  -42.58 -77.00 -60.00  105
  8  \w   -113.00 -16.00   1.00    1.58    --  -42.58 -57.00 120.00   97
  9  \w   -116.00 -11.00   1.00    1.58    --  -42.58 -77.00  30.00  105
 10  \w    -28.00  69.00   1.00    1.58    --   42.58 -57.00  90.00   97
 11  \w      1.00  82.00   1.00    1.58    --   42.58 -99.00   0.00   81
 12  \w     80.00 178.00   1.00    6.30    --  111.00  77.00 -90.00   98
 13  \w     81.00 178.00   1.00    6.30    --  111.00  70.00  51.16   97
 14  \w     37.00 142.00   1.00    6.30    --  111.00 -77.00 -30.00  105
 15  \w     80.00 178.00   1.00    6.30    --  111.00  77.00  30.00   98
 16  \w     80.00 178.00   1.00    6.30    --  111.00  77.00   0.00   98
 17  \w     81.00 178.00   1.00    6.30    --  111.00  70.00 134.26   97
 18  \w     39.00 121.00   1.00    6.30    --  111.00-125.00 -90.00   82
 19  \w     83.00 178.00   1.00    6.30    --  111.00  61.00 120.00   95
 20  \w     81.00 178.00   1.00    6.30    --  111.00  70.00 -96.91   97
 21  \w     80.00 178.00   1.00    6.30    --  111.00  77.00 -30.00   98
 22  \w     83.00 178.00   1.00    6.30    --  111.00  61.00-150.00   95
 23  \w     80.00 178.00   1.00    6.30    --  111.00  77.00  60.00   98
 24  \w     39.00 121.00   1.00    6.30    --  111.00-125.00  90.00   82
 25  \w     81.00 178.00   1.00    6.30    --  111.00  71.00 -39.00   97
 26  \w     30.00 109.00   1.00    6.30    --  111.00 -94.00 -60.00   79
 27  \w     80.00 178.00   1.00    6.30    --  111.00  75.00 -54.29   98
 28  \w     37.00 142.00   1.00    6.30    --  111.00 -77.00 150.00  105
 29  \w     83.00 178.00   1.00    6.30    --  111.00  61.00   0.00   95
 30  \w     30.00 109.00   1.00    6.30    --  111.00 -94.00 120.00   79
 31  \w     83.00 178.00   1.00    6.30    --  111.00  61.00-180.00   95
 32  \w     80.00 178.00   1.00    6.30    --  111.00  77.00-150.00   98
 33  \w     80.00 178.00   1.00    6.30    --  111.00  77.00 150.00   98
 34  \w     83.00 178.00   1.00    6.30    --  111.00  61.00  90.00   95
 35  \w     82.00 178.00   1.00    6.30    --  111.00  66.00  94.04   96
 36  \w     83.00 178.00   1.00    6.30    --  111.00  61.00 -60.00   95
 37  \w     80.00 178.00   1.00    6.30    --  111.00  77.00-180.00   98
 38  \w     80.00 178.00   1.00    6.30    --  111.00  77.00  90.00   98
 39  \w     87.00 178.00   1.00    6.30    --  111.00  45.00 -90.00   91
 40  \w     83.00 178.00   1.00    6.30    --  111.00  61.00  30.00   95
 41  \w     87.00 178.00   1.00    6.30    --  111.00  45.00 150.00   91
 42  \w     83.00 178.00   1.00    6.30    --  111.00  61.00-120.00   95
 43  \w     83.00 178.00   1.00    6.30    --  111.00  61.00 150.00   95
 44  \w     80.00 178.00   1.00    6.30    --  111.00  77.00-120.00   98
 45  \w     80.00 178.00   1.00    6.30    --  111.00  75.00 175.34   98
 46  \w     86.00 178.00   1.00    6.30    --  111.00  51.00 173.98   92
 47  \w     83.00 178.00   1.00    6.30    --  111.00  64.00 -58.82   95
 48  \w   -116.00 -11.00   1.00    1.58    --  -42.58 -77.00-180.00  105
 49  \w   -113.00 -16.00   1.00    1.58    --  -42.58 -57.00 -90.00   97
 50  \w   -113.00 -16.00   1.00    1.58    --  -42.58 -57.00-150.00   97
 51  \w   -115.00 -20.00   1.00    1.58    --  -42.58 -38.00-120.00   95
 52  \w   -113.00 -16.00   1.00    1.58    --  -42.58 -57.00  60.00   97
 53  \w   -113.00 -16.00   1.00    1.58    --  -42.58 -57.00 150.00   97
 54  \w   -115.00 -20.00   1.00    1.58    --  -42.58 -38.00  30.00   95
 55  \w   -115.00 -20.00   1.00    1.58    --  -42.58 -38.00-150.00   95
 56  \w   -115.00 -20.00   1.00    1.58    --  -42.58 -38.00 -90.00   95
 57  \w   -115.00 -20.00   1.00    1.58    --  -42.58 -38.00  60.00   95
 58  \w     57.00 129.00   1.00    1.58    --   42.58 178.00-120.00   72
 59  \w      6.00 121.00   1.00    1.58    --   42.58  19.00  90.00  115
 60  \w     13.00  56.00   1.00    1.58    --   42.58  71.00 -39.00   43
;
_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      -0.1430728000
_diffrn_orient_matrix_UB_12      0.0151758000
_diffrn_orient_matrix_UB_13      0.0138725000
_diffrn_orient_matrix_UB_21      0.0707751000
_diffrn_orient_matrix_UB_22      0.0582162000
_diffrn_orient_matrix_UB_23      0.0787524000
_diffrn_orient_matrix_UB_31      -0.0428130000
_diffrn_orient_matrix_UB_32      0.0455036000
_diffrn_orient_matrix_UB_33      -0.1053745000
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0066
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            81574
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.323
_diffrn_reflns_theta_min         4.330
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.903
_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    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             944.0
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0547P)^2^+0.7788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4582
_reflns_number_total             4718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02065j2.cif
_cod_data_source_block           Syn-2
_cod_database_code               1562393
_chemical_oxdiff_formula         'C36 H20'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_date_sample_data_collection 2016-11-16
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10), C21(H21), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C24(H24), C25(H25),
 C26(H26), C30(H30), C31(H31), C32(H32)
2.c :
 C16(H16), C18(H18), C34(H34), C36(H36)
;
_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 2.435
_oxdiff_exptl_absorpt_empirical_full_min 0.769
_shelx_hkl_checksum              12853
_shelx_res_checksum              77308
_shelx_shelxl_version_number     2016/4