#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:29:17 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222606 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/40/4034046.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4034046
loop_
_publ_author_name
'Geiger, Thomas'
'Haupt, Anne'
'Maichle-Mössmer, Cäcilia'
'Schrenk, Claudio'
'Schnepf, Andreas'
'Bettinger, Holger F.'
_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            'C44 H52'
_chemical_formula_weight         580.86
_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   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                106.8510(10)
_cell_angle_beta                 109.5060(10)
_cell_angle_gamma                105.4740(10)
_cell_formula_units_Z            1
_cell_length_a                   9.7346(2)
_cell_length_b                   10.0564(2)
_cell_length_c                   10.2632(2)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.31
_cell_volume                     829.51(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0091
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22418
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.054
_diffrn_reflns_theta_min         2.312
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0380
_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/[σ²(Fo²)+(0.0644P)²+0.2887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3339
_reflns_number_total             3631
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01317_si_009.cif
_cod_data_source_block           40a_TG030717
_cod_database_code               4034046
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.34927(14) 0.77277(13) 0.38175(12) 0.0238(2) Uani 1 1 d . .
H2 H 0.4507 0.8410 0.3948 0.036 Uiso 1 1 calc R U
H1 H 0.3698 0.7212 0.4492 0.036 Uiso 1 1 calc R U
H11 H 0.2890 0.8317 0.4070 0.036 Uiso 1 1 calc R U
C2 C 0.25327(12) 0.65529(11) 0.21724(11) 0.0165(2) Uani 1 1 d . .
H12 H 0.2337 0.7081 0.1495 0.020 Uiso 1 1 calc R U
H13 H 0.1487 0.5900 0.2034 0.020 Uiso 1 1 calc R U
C3 C 0.33780(11) 0.55580(11) 0.17114(11) 0.0141(2) Uani 1 1 d . .
H3 H 0.3473 0.4948 0.2314 0.017 Uiso 1 1 calc R U
H4 H 0.4467 0.6214 0.1947 0.017 Uiso 1 1 calc R U
C4 C 0.24898(11) 0.44956(11) 0.00222(10) 0.0127(2) Uani 1 1 d . .
H5 H 0.1342 0.4037 -0.0251 0.015 Uiso 1 1 calc R U
H6 H 0.2611 0.5111 -0.0562 0.015 Uiso 1 1 calc R U
C5 C 0.30136(11) 0.32235(10) -0.04824(11) 0.01145(19) Uani 1 1 d . .
C6 C 0.42831(11) 0.30928(10) 0.05506(10) 0.01171(19) Uani 1 1 d . .
H24 H 0.4844 0.3837 0.1573 0.014 Uiso 1 1 calc R U
C7 C 0.47459(11) 0.19082(10) 0.01253(10) 0.01124(19) Uani 1 1 d . .
C8 C 0.60540(11) -0.08162(10) 0.13745(10) 0.01139(19) Uani 1 1 d . .
C9 C 0.54820(11) 0.04398(10) 0.17751(10) 0.01160(19) Uani 1 1 d . .
H25 H 0.5899 0.0924 0.2905 0.014 Uiso 1 1 calc R U
C10 C 0.61038(11) 0.17313(10) 0.12258(10) 0.01146(19) Uani 1 1 d . .
H26 H 0.6765 0.2721 0.2141 0.014 Uiso 1 1 calc R U
C11 C 0.71178(11) 0.13858(10) 0.04430(11) 0.0125(2) Uani 1 1 d . .
C12 C 0.63220(11) 0.02908(11) -0.10651(11) 0.0125(2) Uani 1 1 d . .
C13 C 0.71940(12) -0.00674(11) -0.18431(11) 0.0155(2) Uani 1 1 d . .
H10 H 0.6659 -0.0807 -0.2866 0.019 Uiso 1 1 calc R U
C14 C 0.88507(12) 0.06577(12) -0.11235(12) 0.0179(2) Uani 1 1 d . .
H7 H 0.9443 0.0410 -0.1657 0.022 Uiso 1 1 calc R U
C15 C 0.96366(12) 0.17410(12) 0.03698(12) 0.0182(2) Uani 1 1 d . .
H8 H 1.0766 0.2231 0.0860 0.022 Uiso 1 1 calc R U
C16 C 0.87684(11) 0.21091(11) 0.11504(11) 0.0154(2) Uani 1 1 d . .
H9 H 0.9307 0.2857 0.2170 0.019 Uiso 1 1 calc R U
C17 C 0.77989(11) -0.21174(10) 0.19971(10) 0.01162(19) Uani 1 1 d . .
C18 C 0.91729(11) -0.21986(11) 0.31759(10) 0.0136(2) Uani 1 1 d . .
H22 H 0.9860 -0.1167 0.3997 0.016 Uiso 1 1 calc R U
H21 H 0.9819 -0.2540 0.2696 0.016 Uiso 1 1 calc R U
C19 C 0.86454(12) -0.32776(11) 0.38823(11) 0.0169(2) Uani 1 1 d . .
H14 H 0.7835 -0.4269 0.3054 0.020 Uiso 1 1 calc R U
H15 H 0.9574 -0.3450 0.4456 0.020 Uiso 1 1 calc R U
C20 C 0.79559(13) -0.26839(12) 0.49444(12) 0.0207(2) Uani 1 1 d . .
H16 H 0.7140 -0.2357 0.4426 0.025 Uiso 1 1 calc R U
H17 H 0.8814 -0.1784 0.5861 0.025 Uiso 1 1 calc R U
C21 C 0.72044(13) -0.38663(14) 0.54318(13) 0.0262(3) Uani 1 1 d . .
H19 H 0.6292 -0.4721 0.4539 0.039 Uiso 1 1 calc R U
H20 H 0.6846 -0.3408 0.6165 0.039 Uiso 1 1 calc R U
H18 H 0.7992 -0.4229 0.5904 0.039 Uiso 1 1 calc R U
C22 C 0.73155(11) -0.09331(10) 0.24143(10) 0.0119(2) Uani 1 1 d . .
H23 H 0.7864 -0.0189 0.3436 0.014 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 H2 109.5 . .
C2 C1 H1 109.5 . .
H2 C1 H1 109.5 . .
C2 C1 H11 109.5 . .
H2 C1 H11 109.5 . .
H1 C1 H11 109.5 . .
C1 C2 C3 112.43(8) . .
C1 C2 H12 109.1 . .
C3 C2 H12 109.1 . .
C1 C2 H13 109.1 . .
C3 C2 H13 109.1 . .
H12 C2 H13 107.9 . .
C2 C3 C4 112.00(8) . .
C2 C3 H3 109.2 . .
C4 C3 H3 109.2 . .
C2 C3 H4 109.2 . .
C4 C3 H4 109.2 . .
H3 C3 H4 107.9 . .
C5 C4 C3 116.03(8) . .
C5 C4 H5 108.3 . .
C3 C4 H5 108.3 . .
C5 C4 H6 108.3 . .
C3 C4 H6 108.3 . .
H5 C4 H6 107.4 . .
C6 C5 C17 118.32(8) . 2_655
C6 C5 C4 121.01(8) . .
C17 C5 C4 120.64(8) 2_655 .
C7 C6 C5 121.95(9) . .
C7 C6 H24 119.0 . .
C5 C6 H24 119.0 . .
C6 C7 C8 119.76(8) . 2_655
C6 C7 C10 122.97(8) . .
C8 C7 C10 117.27(8) 2_655 .
C7 C8 C22 118.93(8) 2_655 .
C7 C8 C9 117.34(8) 2_655 .
C22 C8 C9 123.72(8) . .
C12 C9 C8 107.52(7) 2_655 .
C12 C9 C10 111.78(7) 2_655 .
C8 C9 C10 112.18(7) . .
C12 C9 H25 108.4 2_655 .
C8 C9 H25 108.4 . .
C10 C9 H25 108.4 . .
C11 C10 C7 107.32(7) . .
C11 C10 C9 111.80(7) . .
C7 C10 C9 112.35(7) . .
C11 C10 H26 108.4 . .
C7 C10 H26 108.4 . .
C9 C10 H26 108.4 . .
C16 C11 C12 119.91(9) . .
C16 C11 C10 122.89(9) . .
C12 C11 C10 117.20(8) . .
C13 C12 C11 119.67(9) . .
C13 C12 C9 123.14(9) . 2_655
C11 C12 C9 117.18(8) . 2_655
C12 C13 C14 120.10(9) . .
C12 C13 H10 119.9 . .
C14 C13 H10 119.9 . .
C15 C14 C13 120.15(9) . .
C15 C14 H7 119.9 . .
C13 C14 H7 119.9 . .
C14 C15 C16 119.95(9) . .
C14 C15 H8 120.0 . .
C16 C15 H8 120.0 . .
C11 C16 C15 120.21(9) . .
C11 C16 H9 119.9 . .
C15 C16 H9 119.9 . .
C22 C17 C5 119.20(8) . 2_655
C22 C17 C18 119.75(8) . .
C5 C17 C18 121.05(8) 2_655 .
C17 C18 C19 113.66(8) . .
C17 C18 H22 108.8 . .
C19 C18 H22 108.8 . .
C17 C18 H21 108.8 . .
C19 C18 H21 108.8 . .
H22 C18 H21 107.7 . .
C20 C19 C18 113.65(8) . .
C20 C19 H14 108.8 . .
C18 C19 H14 108.8 . .
C20 C19 H15 108.8 . .
C18 C19 H15 108.8 . .
H14 C19 H15 107.7 . .
C19 C20 C21 112.74(9) . .
C19 C20 H16 109.0 . .
C21 C20 H16 109.0 . .
C19 C20 H17 109.0 . .
C21 C20 H17 109.0 . .
H16 C20 H17 107.8 . .
C20 C21 H19 109.5 . .
C20 C21 H20 109.5 . .
H19 C21 H20 109.5 . .
C20 C21 H18 109.5 . .
H19 C21 H18 109.5 . .
H20 C21 H18 109.5 . .
C8 C22 C17 121.83(8) . .
C8 C22 H23 119.1 . .
C17 C22 H23 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.5233(14) .
C1 H2 0.9800 .
C1 H1 0.9800 .
C1 H11 0.9800 .
C2 C3 1.5254(13) .
C2 H12 0.9900 .
C2 H13 0.9900 .
C3 C4 1.5254(13) .
C3 H3 0.9900 .
C3 H4 0.9900 .
C4 C5 1.5184(12) .
C4 H5 0.9900 .
C4 H6 0.9900 .
C5 C6 1.4003(13) .
C5 C17 1.4094(13) 2_655
C6 C7 1.3889(13) .
C6 H24 0.9500 .
C7 C8 1.3946(13) 2_655
C7 C10 1.5164(12) .
C8 C7 1.3946(13) 2_655
C8 C22 1.3911(12) .
C8 C9 1.5171(12) .
C9 C12 1.5170(12) 2_655
C9 C10 1.6138(13) .
C9 H25 1.0000 .
C10 C11 1.5136(12) .
C10 H26 1.0000 .
C11 C16 1.3889(13) .
C11 C12 1.4015(13) .
C12 C13 1.3918(13) .
C12 C9 1.5170(12) 2_655
C13 C14 1.3939(14) .
C13 H10 0.9500 .
C14 C15 1.3875(15) .
C14 H7 0.9500 .
C15 C16 1.3930(14) .
C15 H8 0.9500 .
C16 H9 0.9500 .
C17 C22 1.4004(13) .
C17 C5 1.4094(13) 2_655
C17 C18 1.5147(12) .
C18 C19 1.5408(13) .
C18 H22 0.9900 .
C18 H21 0.9900 .
C19 C20 1.5233(14) .
C19 H14 0.9900 .
C19 H15 0.9900 .
C20 C21 1.5246(15) .
C20 H16 0.9900 .
C20 H17 0.9900 .
C21 H19 0.9800 .
C21 H20 0.9800 .
C21 H18 0.9800 .
C22 H23 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 C2 C3 C4 -174.19(8) . .
C2 C3 C4 C5 -166.73(8) . .
C3 C4 C5 C6 -2.50(13) . .
C3 C4 C5 C17 175.66(8) . 2_655
C17 C5 C6 C7 -0.48(14) 2_655 .
C4 C5 C6 C7 177.71(8) . .
C5 C6 C7 C8 0.71(14) . 2_655
C5 C6 C7 C10 -179.29(8) . .
C7 C8 C9 C12 44.89(11) 2_655 2_655
C22 C8 C9 C12 -134.95(9) . 2_655
C7 C8 C9 C10 -78.40(10) 2_655 .
C22 C8 C9 C10 101.76(10) . .
C6 C7 C10 C11 -133.90(9) . .
C8 C7 C10 C11 46.10(11) 2_655 .
C6 C7 C10 C9 102.81(10) . .
C8 C7 C10 C9 -77.19(10) 2_655 .
C12 C9 C10 C11 -121.04(8) 2_655 .
C8 C9 C10 C11 -0.18(10) . .
C12 C9 C10 C7 -0.30(10) 2_655 .
C8 C9 C10 C7 120.56(8) . .
C7 C10 C11 C16 133.71(9) . .
C9 C10 C11 C16 -102.66(10) . .
C7 C10 C11 C12 -45.82(10) . .
C9 C10 C11 C12 77.81(10) . .
C16 C11 C12 C13 0.16(14) . .
C10 C11 C12 C13 179.71(8) . .
C16 C11 C12 C9 -179.21(8) . 2_655
C10 C11 C12 C9 0.33(12) . 2_655
C11 C12 C13 C14 0.15(14) . .
C9 C12 C13 C14 179.49(8) 2_655 .
C12 C13 C14 C15 -0.12(14) . .
C13 C14 C15 C16 -0.23(14) . .
C12 C11 C16 C15 -0.51(14) . .
C10 C11 C16 C15 179.97(8) . .
C14 C15 C16 C11 0.54(14) . .
C22 C17 C18 C19 97.10(10) . .
C5 C17 C18 C19 -82.45(11) 2_655 .
C17 C18 C19 C20 -71.14(11) . .
C18 C19 C20 C21 170.93(8) . .
C7 C8 C22 C17 -0.20(14) 2_655 .
C9 C8 C22 C17 179.64(8) . .
C5 C17 C22 C8 -0.02(14) 2_655 .
C18 C17 C22 C8 -179.58(8) . .
