Enantiopure nanohoops through racemic resolution of diketo[n]CPPs by chiral derivatization as precursors to DBP[n]CPPs
Wassy, Daniel; Hermann, Mathias; Wössner, Jan S.; Frédéric, Lucas; Pieters, Grégory; Esser, Birgit; Chemical Science  (2021) –; doi:10.1039/D1SC02718B

data_1563865
_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_absolute_configuration ad
_chemical_formula_moiety         'C52 H32 O2, C6 H5 Cl'
_chemical_formula_sum            'C58 H37 Cl O2'
_chemical_formula_weight         801.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
FinalCif V84 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2021-01-19 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.657(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.086(3)
_cell_length_b                   13.495(3)
_cell_length_c                   22.525(5)
_cell_measurement_reflns_used    9668
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.0895
_cell_measurement_theta_min      3.276
_cell_volume                     4102.1(16)
_computing_cell_refinement       'SAINT V8.40A'
_computing_data_collection       'Bruker BIS V6.2.14 Patch 4/2020-11-09'
_computing_data_reduction        'SAINT V8.40A'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            111002
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.326
_diffrn_reflns_theta_min         2.047
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.179
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             1672
_exptl_crystal_recrystallization_method
'vapor diffusion of MeOH into a PhCl solution at rt'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 4491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1099
_refine_ls_number_reflns         13955
_refine_ls_number_restraints     1669
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0614P)^2^+1.6653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.873
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                11600
_reflns_number_total             13955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02718b2.cif
_cod_data_source_block           cu_Esser_MH_838_0m_a
_cod_original_cell_volume        4102.0(14)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1563865
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.757
_shelx_estimated_absorpt_t_max   0.933
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              40867
_shelx_hkl_checksum              55086