Atropisomerism about aryl-C(sp<sup>3</sup>) bonds: chemically driven rotational pathway in cannabidiol derivatives.
Denhez, Clément; Lameiras, Pedro; Berber, Hatice; Organic & biomolecular chemistry 21 (2023) 9572–9582; doi:10.1039/d3ob01617j

data_7159688
_publ_section_title
;
 Atropisomerism about aryl-C(sp<sup>3</sup>) bonds: chemically driven
 rotational pathway in cannabidiol derivatives.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9572
_journal_page_last               9582
_journal_paper_doi               10.1039/d3ob01617j
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H28 N2 O6'
_chemical_formula_weight         476.51
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2dr32c
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2022-12-15 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.345(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6688(4)
_cell_length_b                   7.6572(2)
_cell_length_c                   13.4891(4)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      72.11
_cell_measurement_theta_min      3.34
_cell_volume                     1181.71(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38819
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.198
_diffrn_reflns_theta_min         3.342
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6326
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             504
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1809 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0367P)^2^+0.4035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4265
_reflns_number_total             4648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01617j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7159688.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159688
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              13673