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_1563862
_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         'C76 H56, C5 H12'
_chemical_formula_sum            'C81 H68'
_chemical_formula_weight         1041.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
FinalCif V82 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2021-01-13 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.025(2)
_cell_length_b                   26.772(7)
_cell_length_c                   27.166(7)
_cell_measurement_reflns_used    7972
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.5055
_cell_measurement_theta_min      2.6425
_cell_volume                     5836(3)
_computing_cell_refinement       'SAINT V8.40A'
_computing_data_collection
'Bruker BIS 2018.9.0.3/05-Dec-2018 && APEX3_2019.1-0'
_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                 CCD
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            53755
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.275
_diffrn_reflns_theta_max         24.275
_diffrn_reflns_theta_min         1.068
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.7181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             2216
_exptl_crystal_recrystallization_method
'solvent layering of a CDCl3 solution with n-pentane'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     738
_refine_ls_number_reflns         9430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0484P)^2^+3.1437P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7541
_reflns_number_total             9430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02718b2.cif
_cod_data_source_block           Esser_JW_602_0m_a
_cod_original_cell_volume        5837(3)
_cod_database_code               1563862
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.995
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              89052
_shelx_hkl_checksum              32527