#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:27:16 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222601 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/40/4034041.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_4034041
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            '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
_diffrn_reflns_limit_k_min       -10
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.1144P)²+6.0320P] where P=(Fo²+2Fc²)/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 > 2σ(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_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.
;
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.927
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C01 C -0.2777(8) 0.9921(9) 0.9793(6) 0.0203(14) Uani 1 1 d . . . . .
H01A H -0.3401 0.9014 1.0158 0.030 Uiso 1 1 calc R U . . .
H01B H -0.3511 1.0842 0.9570 0.030 Uiso 1 1 calc R U . . .
H01C H -0.2018 1.0203 1.0382 0.030 Uiso 1 1 calc R U . . .
C1 C -0.1855(7) 0.9464(7) 0.8665(6) 0.0143(12) Uani 1 1 d . . . . .
C2 C -0.2231(7) 1.0242(7) 0.7516(6) 0.0131(12) Uani 1 1 d . . . . .
H2 H -0.3036 1.1084 0.7457 0.016 Uiso 1 1 calc R U . . .
C3 C -0.1436(7) 0.9795(7) 0.6457(5) 0.0124(12) Uani 1 1 d . . . . .
C4 C -0.0249(7) 0.8575(7) 0.6544(5) 0.0117(12) Uani 1 1 d . . . . .
C5 C 0.0131(7) 0.7809(7) 0.7682(6) 0.0133(12) Uani 1 1 d . . . . .
H5 H 0.0958 0.6989 0.7738 0.016 Uiso 1 1 calc R U . . .
C6 C -0.0682(8) 0.8221(8) 0.8749(6) 0.0158(13) Uani 1 1 d . . . . .
C06 C -0.0313(9) 0.7284(8) 0.9957(6) 0.0208(14) Uani 1 1 d . . . . .
H06A H -0.0022 0.8022 1.0533 0.031 Uiso 1 1 calc R U . . .
H06B H 0.0589 0.6516 0.9844 0.031 Uiso 1 1 calc R U . . .
H06C H -0.1266 0.6706 1.0280 0.031 Uiso 1 1 calc R U . . .
C7 C -0.1854(7) 1.0577(7) 0.5186(5) 0.0123(12) Uani 1 1 d . . . . .
H7 H -0.289(10) 1.116(9) 0.524(6) 0.015 Uiso 1 1 d . U . . .
C8 C -0.1991(7) 0.9228(7) 0.4394(5) 0.0111(12) Uani 1 1 d . . . . .
C9 C -0.0778(7) 0.8008(7) 0.4480(5) 0.0109(12) Uani 1 1 d . . . . .
C10 C -0.3270(7) 0.9140(8) 0.3628(6) 0.0151(12) Uani 1 1 d . . . . .
H10 H -0.4097 0.9959 0.3572 0.018 Uiso 1 1 calc R U . . .
C11 C -0.3332(7) 0.7849(8) 0.2946(6) 0.0145(12) Uani 1 1 d . . . . .
H11 H -0.4194 0.7797 0.2416 0.017 Uiso 1 1 calc R U . . .
C12 C -0.2149(8) 0.6648(7) 0.3037(6) 0.0146(12) Uani 1 1 d . . . . .
H12 H -0.2208 0.5761 0.2579 0.017 Uiso 1 1 calc R U . . .
C13 C -0.0859(7) 0.6724(7) 0.3799(6) 0.0140(12) Uani 1 1 d . . . . .
H13 H -0.0038 0.5898 0.3851 0.017 Uiso 1 1 calc R U . . .
C14 C 0.0568(7) 0.8142(7) 0.5356(5) 0.0106(12) Uani 1 1 d . . . . .
H14 H 0.106(10) 0.724(10) 0.551(6) 0.013 Uiso 1 1 d . U . . .
C20 C 0.6151(8) 0.6312(8) 0.7543(6) 0.0169(13) Uani 1 1 d . . . . .
H20A H 0.6915 0.7203 0.7517 0.020 Uiso 0.515(14) 1 calc R U P A 1
H20B H 0.6968 0.7160 0.7480 0.020 Uiso 0.485(14) 1 calc R U P A 2
Cl1 Cl 0.5282(7) 0.6369(7) 0.6102(4) 0.0226(5) Uani 0.515(14) 1 d . . P A 1
Cl2 Cl 0.7204(7) 0.4486(6) 0.7931(6) 0.0226(5) Uani 0.515(14) 1 d . . P A 1
Cl3 Cl 0.4590(6) 0.6591(8) 0.8675(6) 0.0226(5) Uani 0.515(14) 1 d . . P A 1
Cl1A Cl 0.5608(8) 0.6069(8) 0.6047(5) 0.0226(5) Uani 0.485(14) 1 d . . P A 2
Cl2A Cl 0.7088(7) 0.4502(7) 0.8220(6) 0.0226(5) Uani 0.485(14) 1 d . . P A 2
Cl3A Cl 0.4521(6) 0.6951(8) 0.8427(6) 0.0226(5) Uani 0.485(14) 1 d . . P A 2
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'
Cl Cl 0.1484 0.1585 '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_3
C6 C1 C2 119.5(6) .
C6 C1 C01 120.6(6) .
C2 C1 C01 119.9(6) .
C3 C2 C1 120.8(6) .
C4 C3 C2 119.6(6) .
C4 C3 C7 118.1(5) .
C2 C3 C7 122.2(5) .
C3 C4 C5 119.7(6) .
C3 C4 C14 117.0(5) .
C5 C4 C14 123.3(5) .
C4 C5 C6 121.3(6) .
C1 C6 C5 119.1(6) .
C1 C6 C06 121.2(6) .
C5 C6 C06 119.6(6) .
C8 C7 C3 106.7(5) .
C8 C7 C14 112.9(5) 2_576
C3 C7 C14 112.2(5) 2_576
C10 C8 C9 119.8(6) .
C10 C8 C7 123.1(6) .
C9 C8 C7 117.1(5) .
C13 C9 C8 119.7(5) .
C13 C9 C14 122.6(5) .
C8 C9 C14 117.6(5) .
C11 C10 C8 119.9(6) .
C12 C11 C10 120.3(6) .
C11 C12 C13 120.4(6) .
C9 C13 C12 119.9(6) .
C4 C14 C9 106.4(5) .
C4 C14 C7 112.2(5) 2_576
C9 C14 C7 112.1(5) 2_576
Cl3A C20 Cl1A 112.1(4) .
Cl2 C20 Cl1 111.5(4) .
Cl3A C20 Cl2A 112.1(4) .
Cl1A C20 Cl2A 109.7(4) .
Cl2 C20 Cl3 109.4(4) .
Cl1 C20 Cl3 109.2(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C01 C1 1.511(9) .
C1 C6 1.394(9) .
C1 C2 1.403(9) .
C2 C3 1.398(8) .
C3 C4 1.388(9) .
C3 C7 1.529(8) .
C4 C5 1.389(9) .
C4 C14 1.524(8) .
C5 C6 1.402(9) .
C6 C06 1.508(9) .
C7 C8 1.517(8) .
C7 C14 1.600(8) 2_576
C8 C10 1.396(8) .
C8 C9 1.403(8) .
C9 C13 1.387(9) .
C9 C14 1.525(8) .
C10 C11 1.391(9) .
C11 C12 1.376(9) .
C12 C13 1.399(9) .
C14 C7 1.600(8) 2_576
C20 Cl3A 1.735(8) .
C20 Cl2 1.752(8) .
C20 Cl1A 1.766(8) .
C20 Cl1 1.770(8) .
C20 Cl2A 1.781(8) .
C20 Cl3 1.788(8) .
