Polymorph prediction through observed structural isomorphism leading to a new crystalline form of cannabidiol
Straker, Hannah E.; McMillan, Lynn; Mardiana, Lina; Hebberd, Glen R.; Watson, Elle; Waddell, Paul G.; Probert, Michael R.; Hall, Michael J.; CrystEngComm 25 (2023) 2479–2484; doi:10.1039/D3CE00041A

data_7246538
_publ_section_title
;
 Polymorph prediction through observed structural isomorphism leading to a
 new crystalline form of cannabidiol
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2479
_journal_page_last               2484
_journal_paper_doi               10.1039/D3CE00041A
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H32 O2'
_chemical_formula_sum            'C22 H32 O2'
_chemical_formula_weight         328.47
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-16
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-04 deposited with the CCDC.	2023-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1727(13)
_cell_length_b                   12.5417(14)
_cell_length_c                   13.6848(16)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      66.94
_cell_measurement_theta_min      4.78
_cell_volume                     1917.6(4)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service v6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker Photon II area detector'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Hybrid area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_type       'Bruker AXS Inc. convention APEX3'
_diffrn_radiation_collimation    'focussed source'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14661
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.984
_diffrn_reflns_theta_max         66.984
_diffrn_reflns_theta_min         4.783
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type
;
'Incoatec microfocus 3.0 (cu) X-ray Source'
;
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7504
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1223 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.7504.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method 'Crystallised in freezer'
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0391P)^2^+0.2146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3348
_reflns_number_total             3394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00041a2.cif
_cod_data_source_block           cbd_6_face_abs
_cod_depositor_comments
'Adding full bibliography for 7246535--7246539.cif.'
_cod_database_code               7246538
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C4(H4A,H4B), C18(H18A,H18B), C20(H20A,H20B),
 C3(H3A,H3B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C13(H13), C7(H7)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C1(H1A,H1B,H1C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              84718
_olex2_exptl_crystal_mounting_method
'Standard Kapton mount with Fomblin 1800 oil'
_olex2_submission_special_instructions 'No special instructions were received'