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_4034043
_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_moiety         'C36 H36'
_chemical_formula_sum            'C36 H36'
_chemical_formula_weight         468.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.3580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.8935(15)
_cell_length_b                   7.9659(9)
_cell_length_c                   11.9709(13)
_cell_measurement_reflns_used    5104
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.858
_cell_measurement_theta_min      3.304
_cell_volume                     1322.6(3)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART Apex'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.79942
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6924
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        28.663
_diffrn_reflns_theta_max         29.895
_diffrn_reflns_theta_min         3.304
_diffrn_source                   synchrotron
_diffrn_source_type              synchrotron
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0749 before and 0.0301 after correction.
The Ratio of minimum to maximum transmission is 0.9564.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0401P)^2^+0.4300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2421
_reflns_number_total             2569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01317_si_005.cif
_cod_data_source_block           37a_93
_cod_database_code               4034043
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C6(H6), C1(H1), C3(H3), C13(H13), C2(H2)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              42943
_shelx_hkl_checksum              71972
_olex2_submission_special_instructions 'No special instructions were received'