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#$Date: 2021-07-02 04:04:07 +0300 (Fri, 02 Jul 2021) $
#$Revision: 266881 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/38/1563860.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_1563860
loop_
_publ_author_name
'Wassy, Daniel'
'Hermann, Mathias'
'Wössner, Jan S.'
'Frédéric, Lucas'
'Pieters, Grégory'
'Esser, Birgit'
_publ_section_title
;
 Enantiopure nanohoops through racemic resolution of diketo[n]CPPs by
 chiral derivatization as precursors to DBP[n]CPPs
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02718B
_journal_year                    2021
_chemical_formula_moiety         'C30 H20 Br2'
_chemical_formula_sum            'C30 H20 Br2'
_chemical_formula_weight         540.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1ln9j2
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-05-11 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.211(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8475(8)
_cell_length_b                   7.3631(4)
_cell_length_c                   12.8990(8)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.375
_cell_measurement_theta_min      5.200
_cell_volume                     1103.76(12)
_computing_cell_refinement       'SAINT V8.37A'
_computing_data_collection       APEXII
_computing_data_reduction        'SAINT V8.37A'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_device_type  'Bruker SMART APEXII QUAZAR'
_diffrn_measurement_method       'Omega and Phi Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19418
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.154
_diffrn_reflns_theta_min         2.137
_diffrn_source                   'INCOATEC Mo  Microsource'
_exptl_absorpt_coefficient_mu    3.689
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.5601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       needle
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.320
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4425
_refine_ls_number_restraints     106
_refine_ls_restrained_S_all      1.306
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0344
_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)+(0.0149P)²+1.4104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0765
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4010
_reflns_number_total             4425
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02718b2.cif
_cod_data_source_block           Esser_MB256_2s1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1563860
_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   0.497
_shelx_estimated_absorpt_t_max   0.809
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Br1 Br 0.10148(2) 0.46265(3) 0.11073(2) 0.01747(5) Uani 1 1 d . . . . .
C1 C 0.82561(16) 0.5575(3) 0.42489(15) 0.0149(3) Uani 0.936(3) 1 d D U P A 1
C2 C 0.90783(18) 0.5036(3) 0.36669(18) 0.0195(4) Uani 0.936(3) 1 d D U P A 1
H2 H 0.9691 0.5840 0.3614 0.023 Uiso 0.936(3) 1 calc R U P A 1
C3 C 0.9029(2) 0.3365(3) 0.31638(17) 0.0212(4) Uani 0.936(3) 1 d D U P A 1
H3 H 0.9604 0.3035 0.2779 0.025 Uiso 0.936(3) 1 calc R U P A 1
C4 C 0.81320(18) 0.2176(3) 0.32260(16) 0.0186(4) Uani 0.936(3) 1 d D U P A 1
H4 H 0.8086 0.1033 0.2879 0.022 Uiso 0.936(3) 1 calc R U P A 1
C5 C 0.73049(17) 0.2675(3) 0.37995(15) 0.0158(4) Uani 0.936(3) 1 d D U P A 1
H5 H 0.6691 0.1865 0.3841 0.019 Uiso 0.936(3) 1 calc R U P A 1
C6 C 0.73590(16) 0.4356(3) 0.43184(15) 0.0127(3) Uani 0.936(3) 1 d D U P A 1
C15 C 0.83017(19) 0.7449(3) 0.47073(18) 0.0213(4) Uani 0.936(3) 1 d D U P A 1
H15A H 0.7519 0.7928 0.4635 0.032 Uiso 0.936(3) 1 calc R U P A 1
H15B H 0.8750 0.8241 0.4329 0.032 Uiso 0.936(3) 1 calc R U P A 1
H15C H 0.8666 0.7403 0.5457 0.032 Uiso 0.936(3) 1 calc R U P A 1
C1A C 0.766(2) 0.356(3) 0.3739(19) 0.0149(3) Uani 0.064(3) 1 d D U P A 2
C2A C 0.857(2) 0.377(3) 0.3197(19) 0.018(4) Uani 0.064(3) 1 d D U P A 2
H2A H 0.8726 0.2834 0.2737 0.022 Uiso 0.064(3) 1 calc R U P A 2
C3A C 0.923(2) 0.532(4) 0.333(3) 0.0212(4) Uani 0.064(3) 1 d D U P A 2
H3A H 0.9847 0.5438 0.2959 0.025 Uiso 0.064(3) 1 calc R U P A 2
C4A C 0.902(2) 0.673(3) 0.3986(19) 0.017(4) Uani 0.064(3) 1 d D U P A 2
H4A H 0.9465 0.7812 0.4048 0.020 Uiso 0.064(3) 1 calc R U P A 2
C5A C 0.8156(19) 0.651(3) 0.4545(18) 0.012(4) Uani 0.064(3) 1 d D U P A 2
H5A H 0.8019 0.7430 0.5022 0.014 Uiso 0.064(3) 1 calc R U P A 2
C6A C 0.748(2) 0.496(3) 0.442(2) 0.0127(3) Uani 0.064(3) 1 d D U P A 2
C15A C 0.700(2) 0.182(3) 0.365(2) 0.017(4) Uani 0.064(3) 1 d D U P A 2
H15D H 0.6258 0.1986 0.3159 0.025 Uiso 0.064(3) 1 calc R U P A 2
H15E H 0.6859 0.1464 0.4342 0.025 Uiso 0.064(3) 1 calc R U P A 2
H15F H 0.7439 0.0870 0.3373 0.025 Uiso 0.064(3) 1 calc R U P A 2
C7 C 0.64553(14) 0.4806(2) 0.49212(13) 0.0120(3) Uani 1 1 d D . . . .
C8 C 0.52971(14) 0.4825(2) 0.45659(12) 0.0116(3) Uani 1 1 d . . . . .
C9 C 0.44227(14) 0.4628(2) 0.36054(12) 0.0122(3) Uani 1 1 d . . . . .
C10 C 0.33488(14) 0.4874(2) 0.39215(13) 0.0119(3) Uani 1 1 d . . . . .
C11 C 0.23313(15) 0.4868(2) 0.31841(13) 0.0137(3) Uani 1 1 d . . . . .
H11 H 0.1611 0.5037 0.3389 0.016 Uiso 1 1 calc R U . . .
C12 C 0.24019(15) 0.4605(3) 0.21278(13) 0.0136(3) Uani 1 1 d . . . . .
C13 C 0.34379(16) 0.4327(2) 0.18018(13) 0.0144(3) Uani 1 1 d . . . . .
H13 H 0.3450 0.4126 0.1077 0.017 Uiso 1 1 calc R U . . .
C14 C 0.44650(15) 0.4346(2) 0.25537(13) 0.0132(3) Uani 1 1 d . . . . .
H14 H 0.5182 0.4167 0.2344 0.016 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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C2 C1 C6 117.84(19) . . ?
C2 C1 C15 119.87(18) . . ?
C6 C1 C15 122.14(17) . . ?
C3 C2 C1 122.2(2) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.12(19) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.82(17) . . ?
C5 C6 C7 118.59(17) . . ?
C1 C6 C7 121.59(17) . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6A C1A C2A 117.1(16) . . ?
C6A C1A C15A 123.1(17) . . ?
C2A C1A C15A 119.6(18) . . ?
C3A C2A C1A 120.3(19) . . ?
C3A C2A H2A 119.9 . . ?
C1A C2A H2A 119.9 . . ?
C2A C3A C4A 121.8(19) . . ?
C2A C3A H3A 119.1 . . ?
C4A C3A H3A 119.1 . . ?
C5A C4A C3A 118.3(19) . . ?
C5A C4A H4A 120.9 . . ?
C3A C4A H4A 120.9 . . ?
C4A C5A C6A 120.7(18) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C5A C6A C1A 121.9(15) . . ?
C5A C6A C7 121.1(15) . . ?
C1A C6A C7 116.7(14) . . ?
C1A C15A H15D 109.5 . . ?
C1A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C1A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C8 C7 C6 127.72(15) . . ?
C8 C7 C10 106.71(14) . 3_666 ?
C6 C7 C10 125.24(15) . 3_666 ?
C8 C7 C6A 135.1(12) . . ?
C10 C7 C6A 116.4(11) 3_666 . ?
C7 C8 C8 110.47(18) . 3_666 ?
C7 C8 C9 142.03(16) . . ?
C8 C8 C9 107.50(17) 3_666 . ?
C14 C9 C10 120.39(15) . . ?
C14 C9 C8 133.83(16) . . ?
C10 C9 C8 105.72(14) . . ?
C11 C10 C9 120.76(15) . . ?
C11 C10 C7 129.59(16) . 3_666 ?
C9 C10 C7 109.59(14) . 3_666 ?
C10 C11 C12 117.56(16) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C13 C12 C11 122.76(15) . . ?
C13 C12 Br1 119.29(12) . . ?
C11 C12 Br1 117.95(13) . . ?
C12 C13 C14 119.28(15) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 119.24(16) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.8954(16) . ?
C1 C2 1.398(3) . ?
C1 C6 1.407(3) . ?
C1 C15 1.498(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.478(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1A C6A 1.398(16) . ?
C1A C2A 1.404(17) . ?
C1A C15A 1.492(17) . ?
C2A C3A 1.382(18) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.391(18) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.372(17) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.384(17) . ?
C5A H5A 0.9500 . ?
C6A C7 1.486(15) . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C7 C8 1.360(2) . ?
C7 C10 1.484(2) 3_666 ?
C8 C8 1.457(3) 3_666 ?
C8 C9 1.460(2) . ?
C9 C14 1.383(2) . ?
C9 C10 1.421(2) . ?
C10 C11 1.383(2) . ?
C10 C7 1.484(2) 3_666 ?
C11 C12 1.395(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(2) . ?
C13 C14 1.401(2) . ?
C13 H13 0.9500 . ?
C14 H14 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(3) . . . . ?
C15 C1 C2 C3 -175.4(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -179.70(18) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C15 C1 C6 C5 174.62(18) . . . . ?
C2 C1 C6 C7 179.68(18) . . . . ?
C15 C1 C6 C7 -4.8(3) . . . . ?
C6A C1A C2A C3A -1(4) . . . . ?
C15A C1A C2A C3A -176(3) . . . . ?
C1A C2A C3A C4A 0(5) . . . . ?
C2A C3A C4A C5A 2(5) . . . . ?
C3A C4A C5A C6A -3(4) . . . . ?
C4A C5A C6A C1A 1(5) . . . . ?
C4A C5A C6A C7 -173(2) . . . . ?
C2A C1A C6A C5A 1(4) . . . . ?
C15A C1A C6A C5A 176(3) . . . . ?
C2A C1A C6A C7 175(2) . . . . ?
C15A C1A C6A C7 -11(4) . . . . ?
C5 C6 C7 C8 -55.4(3) . . . . ?
C1 C6 C7 C8 124.0(2) . . . . ?
C5 C6 C7 C10 117.2(2) . . . 3_666 ?
C1 C6 C7 C10 -63.4(3) . . . 3_666 ?
C5A C6A C7 C8 108(2) . . . . ?
C1A C6A C7 C8 -66(3) . . . . ?
C5A C6A C7 C10 -54(3) . . . 3_666 ?
C1A C6A C7 C10 132(2) . . . 3_666 ?
C6 C7 C8 C8 174.65(19) . . . 3_666 ?
C10 C7 C8 C8 1.0(2) 3_666 . . 3_666 ?
C6A C7 C8 C8 -162.4(13) . . . 3_666 ?
C6 C7 C8 C9 -5.9(4) . . . . ?
C10 C7 C8 C9 -179.6(2) 3_666 . . . ?
C6A C7 C8 C9 17.0(13) . . . . ?
C7 C8 C9 C14 -1.9(4) . . . . ?
C8 C8 C9 C14 177.6(2) 3_666 . . . ?
C7 C8 C9 C10 -179.0(2) . . . . ?
C8 C8 C9 C10 0.4(2) 3_666 . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C8 C9 C10 C11 176.54(16) . . . . ?
C14 C9 C10 C7 -178.61(16) . . . 3_666 ?
C8 C9 C10 C7 -0.98(19) . . . 3_666 ?
C9 C10 C11 C12 0.2(3) . . . . ?
C7 C10 C11 C12 177.22(17) 3_666 . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C10 C11 C12 Br1 -179.15(13) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
Br1 C12 C13 C14 178.77(13) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C8 C9 C14 C13 -176.13(19) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
