Enantiopure molecules form apparently racemic monolayers of chiral cyclic pentamers.
Heiner, Benjamin R.; Handy, Kaitlyn M.; Devlin, Angela M.; Soucek, Jewel L.; Pittsford, Alexander M.; Turner, David A.; Petersen, Jacob P.; Oliver, Allen G.; Corcelli, Steven A.; Kandel, S. Alex; Physical chemistry chemical physics : PCCP 26 (2024) 25430–25438; doi:10.1039/d4cp02094d

data_7249351
_publ_section_title
;
 Enantiopure molecules form apparently racemic monolayers of chiral cyclic
 pentamers.
;
_journal_issue                   39
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              25430
_journal_page_last               25438
_journal_paper_doi               10.1039/d4cp02094d
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C9 H9 N O2'
_chemical_formula_sum            'C9 H9 N O2'
_chemical_formula_weight         163.17
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-17 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.824(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3771(2)
_cell_length_b                   5.7567(2)
_cell_length_c                   12.4675(5)
_cell_measurement_reflns_used    2671
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.31
_cell_measurement_theta_min      3.67
_cell_volume                     377.73(2)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5982
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.425
_diffrn_reflns_theta_min         3.622
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8311
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 530 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1419
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0547P)^2^+0.0269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                1306
_reflns_number_total             1419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cp02094d2.cif
_cod_data_source_block           dt2001
_cod_depositor_comments          'Adding full bibliography for 7249351.cif.'
_cod_original_cell_volume        377.74(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7249351
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.907
_shelx_estimated_absorpt_t_max   0.984
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              4381