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_7246536
_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 rmad
_chemical_formula_moiety         'C21 H30 O2'
_chemical_formula_sum            'C21 H30 O2'
_chemical_formula_weight         314.45
_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
_audit_creation_date             2020-01-23
_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                 95.4518(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.43482(16)
_cell_length_b                   10.88547(17)
_cell_length_c                   16.7749(3)
_cell_measurement_reflns_used    8070
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.5880
_cell_measurement_theta_min      4.2150
_cell_volume                     1896.81(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -108.00 -28.00   1.00    1.00    --  -41.59 140.00-151.00   80
  2  \w    -32.00  71.00   1.00    1.00    --   41.59 -57.00 -60.00  103
  3  \w      8.00 120.00   1.00    1.00    --   41.59  77.00  60.00  112
  4  \w     15.00 117.00   1.00    1.00    --   41.59  38.00   0.00  102
  5  \w      9.00 133.00   1.00    3.50    --   93.50 -93.00-137.91  124
  6  \w      9.00 133.00   1.00    3.50    --   93.50 -93.00 152.68  124
  7  \w     19.00 124.00   1.00    3.50    --   93.50 -61.00 -60.00  105
  8  \w      9.00 133.00   1.00    3.50    --   93.50 -93.00 -97.36  124
  9  \w     66.00 168.00   1.00    3.50    --   93.50  45.00  30.00  102
 10  \w     73.00 168.00   1.00    3.50    --   93.50 125.00 -90.00   95
 11  \w     16.00 124.00   1.00    3.50    --   93.50 -30.00 -30.00  108
 12  \w      9.00  83.00   1.00    3.50    --   93.50 -94.00-120.00   74
 13  \w      8.00 131.00   1.00    3.50    --   93.50 -88.00   5.53  123
 14  \w     32.00 177.00   1.00    3.50    --   93.50  15.00 -30.00  145
 15  \w     19.00  96.00   1.00    3.50    --   93.50-125.00 120.00   77
 16  \w     19.00  96.00   1.00    3.50    --   93.50-125.00 150.00   77
 17  \w     63.00 135.00   1.00    3.50    --   93.50  61.00-180.00   72
 18  \w     19.00  72.00   1.00    3.50    --   93.50-125.00-150.00   53
 19  \w     72.00  98.00   1.00    3.50    --   93.50-130.00 -36.00   26
 20  \w     10.00  48.00   1.00    3.50    --   93.50 -94.00 150.00   38
 21  \w     32.00  82.00   1.00    3.50    --   93.50 -45.00-120.00   50
 22  \w     53.00 139.00   1.00    3.50    --   93.50  15.00-180.00   86
 23  \w     99.00 126.00   1.00    3.50    --   93.50 -93.00 -58.00   27
 24  \w     10.00  38.00   1.00    3.50    --   93.50 -94.00   0.00   28
 25  \w     50.00  96.00   1.00    3.50    --   93.50-125.00-180.00   46
 26  \w     55.00  81.00   1.00    3.50    --   93.50 -93.00 -58.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0055098000
_diffrn_orient_matrix_UB_12      0.1414129000
_diffrn_orient_matrix_UB_13      -0.0013187000
_diffrn_orient_matrix_UB_21      -0.0066729000
_diffrn_orient_matrix_UB_22      -0.0018118000
_diffrn_orient_matrix_UB_23      -0.0921757000
_diffrn_orient_matrix_UB_31      -0.1479916000
_diffrn_orient_matrix_UB_32      -0.0051586000
_diffrn_orient_matrix_UB_33      -0.0045952000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26857
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.975
_diffrn_reflns_theta_max         66.975
_diffrn_reflns_theta_min         4.256
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 2563 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6671
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0344
_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^+0.2105P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5989
_reflns_number_total             6671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00041a2.cif
_cod_data_source_block           mjh200017_fa
_cod_depositor_comments
'Adding full bibliography for 7246535--7246539.cif.'
_cod_original_cell_volume        1896.80(5)
_cod_database_code               7246536
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C21 H30 O2'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C28(H28), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B), C30(H30A,H30B), C31(H31A,H31B), C38(H38A,H38B), C39(H39A,H39B),
  C40(H40A,H40B), C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C12(H12), C24(H24), C26(H26), C33(H33)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B), C35(H35A,H35B)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              35760
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.111
_oxdiff_exptl_absorpt_empirical_full_min 0.920