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_4034041
_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_formula_sum            'C34 H30 Cl6'
_chemical_formula_weight         651.28
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                83.627(7)
_cell_angle_beta                 87.534(7)
_cell_angle_gamma                87.470(6)
_cell_formula_units_Z            1
_cell_length_a                   8.3036(12)
_cell_length_b                   8.4034(12)
_cell_length_c                   11.0420(17)
_cell_measurement_reflns_used    2136
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      2.560
_cell_volume                     764.4(2)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_collection       'Apex 2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/5,SHELXS-13 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Smart APEX II '
_diffrn_measurement_method       omega/phi-scans
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
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_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            3071
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.441
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.8354
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.131
_refine_diff_density_max         1.209
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       0.027(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0880
_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^)+(0.1144P)^2^+6.0320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2958
_refine_ls_wR_factor_ref         0.3012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2622
_reflns_number_total             3071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01317_si_008.cif
_cod_data_source_block           39a_mo_tg1a_0m_tw
_cod_database_code               4034041
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.927
_shelx_res_checksum              57284
_shelx_hkl_checksum              2283