Synthesis and Photodimerization of 2- and 2,3-Disubstituted Anthracenes: Influence of Steric Interactions and London Dispersion on Diastereoselectivity.
Geiger, Thomas; Haupt, Anne; Maichle-Mössmer, Cäcilia; Schrenk, Claudio; Schnepf, Andreas; Bettinger, Holger F.; The Journal of organic chemistry 84 (2019) 10120–10135; doi:10.1021/acs.joc.9b01317

data_4034048
_publ_section_title
;
 Synthesis and Photodimerization of 2- and 2,3-Disubstituted Anthracenes:
 Influence of Steric Interactions and London Dispersion on
 Diastereoselectivity.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10120
_journal_page_last               10135
_journal_paper_doi               10.1021/acs.joc.9b01317
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C44 H52'
_chemical_formula_weight         580.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9017(16)
_cell_length_b                   26.689(3)
_cell_length_c                   6.9776(6)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    152(2)
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      2.864
_cell_volume                     3520.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker COSMO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-13 (Sheldrick 2008)'
_diffrn_ambient_temperature      152(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
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_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
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_diffrn_reflns_theta_max         66.890
_diffrn_reflns_theta_min         2.865
_diffrn_source                   'ImuS-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_description       column
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(12)
_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     424
_refine_ls_number_reflns         6218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0485P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4912
_reflns_number_total             6218
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01317_si_007.cif
_cod_data_source_block           38a_orthcu_tg113_0ma_a
_cod_original_cell_volume        3520.0(5)
_cod_database_code               4034048
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.863
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              62005
_shelx_hkl_checksum              11668