#------------------------------------------------------------------------------
#$Date: 2023-05-05 04:24:27 +0300 (Fri, 05 May 2023) $
#$Revision: 283209 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/65/7246537.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246537
loop_
_publ_author_name
'Straker, Hannah E.'
'McMillan, Lynn'
'Mardiana, Lina'
'Hebberd, Glen R.'
'Watson, Elle'
'Waddell, Paul G.'
'Probert, Michael R.'
'Hall, Michael J.'
_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         'C20 H28 O2'
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42
_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                   9.7147(5)
_cell_length_b                   13.1197(7)
_cell_length_c                   13.9392(8)
_cell_measurement_reflns_used    9467
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      66.6115
_cell_measurement_theta_min      3.1705
_cell_volume                     1776.61(17)
_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      150.00
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω 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  0.0189
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10363
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.606
_diffrn_reflns_theta_max         66.606
_diffrn_reflns_theta_min         4.628
_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    0.546
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_correction_T_min  0.8259
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0871 before and 0.0359 after correction.
The Ratio of minimum to maximum transmission is 0.8473.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1281 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0284
_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/[σ²(Fo²)+(0.0471P)²+0.2393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3068
_reflns_number_total             3103
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00041a2.cif
_cod_data_source_block           4202304_face_abs
_cod_depositor_comments
'Adding full bibliography for 7246535--7246539.cif.'
_cod_database_code               7246537
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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:
 C4(H4A,H4B), C17(H17A,H17B), C3(H3A,H3B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C7(H7), C15(H15)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C9(H9A,H9B,H9C)
;
_local_gw_agreement_sow_number   'GWR-SER-00009453 dated 17th December 2019'
_local_gw_authors                'Lynn McMillan and Hannah Straker'
_local_gw_compound_number        GWP4202304
_local_gw_crystal_method         Evaporation
_local_gw_lnb_reference          4202304
_local_gw_project_name           'GWP4202304 Crystal Structure Determination'
_local_gw_quality_factor         1
_local_gw_submitting_chemist     'Lynn McMillan'
_local_gw_xrd_lnb_reference      '4202304 cbd-4'
_olex2_exptl_crystal_mounting_method 'Standard Kapton mount in Fomblin 1800 oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.71582(13) 0.42394(9) 0.44397(8) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.72670(14) 0.45587(10) 0.78493(8) 0.0310(3) Uani 1 1 d . . . . .
C16 C 0.78222(17) 0.47382(12) 0.69456(10) 0.0241(3) Uani 1 1 d . . . . .
C11 C 0.71850(16) 0.43508(11) 0.61302(10) 0.0214(3) Uani 1 1 d . . . . .
C12 C 0.77944(16) 0.46003(11) 0.52470(10) 0.0217(3) Uani 1 1 d . . . . .
C13 C 0.89926(17) 0.51717(12) 0.51995(11) 0.0246(3) Uani 1 1 d . . . . .
H13 H 0.938111 0.532960 0.459203 0.030 Uiso 1 1 calc R . . . .
C14 C 0.96333(16) 0.55169(12) 0.60318(12) 0.0249(3) Uani 1 1 d . . . . .
C7 C 0.47698(16) 0.41564(12) 0.67549(11) 0.0250(3) Uani 1 1 d . . . . .
H7 H 0.466313 0.487506 0.671697 0.030 Uiso 1 1 calc R . . . .
C6 C 0.59198(16) 0.36786(12) 0.61759(10) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.557452 0.359526 0.550458 0.027 Uiso 1 1 calc R . . . .
C15 C 0.90310(17) 0.53041(12) 0.69126(11) 0.0260(3) Uani 1 1 d . . . . .
H15 H 0.944202 0.554355 0.748845 0.031 Uiso 1 1 calc R . . . .
C2 C 0.38970(17) 0.36466(13) 0.73129(11) 0.0275(4) Uani 1 1 d . . . . .
C5 C 0.62599(17) 0.25981(12) 0.65627(11) 0.0257(4) Uani 1 1 d . . . . .
H5 H 0.665541 0.267855 0.722068 0.031 Uiso 1 1 calc R . . . .
C8 C 0.73211(19) 0.20537(13) 0.59514(13) 0.0327(4) Uani 1 1 d . . . . .
C4 C 0.49010(18) 0.20089(13) 0.66582(13) 0.0313(4) Uani 1 1 d . . . . .
H4A H 0.442860 0.199412 0.602901 0.038 Uiso 1 1 calc R . . . .
H4B H 0.509863 0.129674 0.684849 0.038 Uiso 1 1 calc R . . . .
C17 C 1.09822(16) 0.60986(13) 0.59635(13) 0.0308(4) Uani 1 1 d . . . . .
H17A H 1.168926 0.564685 0.567924 0.037 Uiso 1 1 calc R . . . .
H17B H 1.128940 0.627976 0.661886 0.037 Uiso 1 1 calc R . . . .
C3 C 0.3956(2) 0.24985(14) 0.74026(13) 0.0342(4) Uani 1 1 d . . . . .
H3A H 0.301611 0.221801 0.732783 0.041 Uiso 1 1 calc R . . . .
H3B H 0.428605 0.231778 0.805266 0.041 Uiso 1 1 calc R . . . .
C1 C 0.2762(2) 0.41692(15) 0.78573(13) 0.0385(4) Uani 1 1 d . . . . .
H1A H 0.281214 0.397724 0.853587 0.058 Uiso 1 1 calc GR . . . .
H1B H 0.186930 0.396148 0.759454 0.058 Uiso 1 1 calc GR . . . .
H1C H 0.286469 0.490946 0.779636 0.058 Uiso 1 1 calc GR . . . .
C18 C 1.08870(18) 0.70737(14) 0.53620(13) 0.0336(4) Uani 1 1 d . . . . .
H18A H 1.182399 0.735644 0.527724 0.040 Uiso 1 1 calc R . . . .
H18B H 1.052720 0.689790 0.471843 0.040 Uiso 1 1 calc R . . . .
C19 C 0.99745(19) 0.78858(14) 0.58002(14) 0.0385(4) Uani 1 1 d . . . . .
H19A H 1.039971 0.813484 0.640156 0.046 Uiso 1 1 calc R . . . .
H19B H 0.907095 0.758306 0.596347 0.046 Uiso 1 1 calc R . . . .
C20 C 0.9758(2) 0.87780(16) 0.51236(17) 0.0486(5) Uani 1 1 d . . . . .
H20A H 0.924967 0.854771 0.455638 0.073 Uiso 1 1 calc GR . . . .
H20B H 1.065325 0.905103 0.492623 0.073 Uiso 1 1 calc GR . . . .
H20C H 0.923127 0.931142 0.545150 0.073 Uiso 1 1 calc GR . . . .
C10 C 0.8597(2) 0.19338(18) 0.62666(16) 0.0472(5) Uani 1 1 d . . . . .
H10A H 0.926306 0.160552 0.587444 0.057 Uiso 1 1 calc R . . . .
H10B H 0.884700 0.217607 0.688488 0.057 Uiso 1 1 calc R . . . .
C9 C 0.6876(2) 0.16832(17) 0.49779(16) 0.0482(6) Uani 1 1 d . . . . .
H9A H 0.611553 0.119864 0.505028 0.072 Uiso 1 1 calc GR . . . .
H9B H 0.765174 0.134588 0.465960 0.072 Uiso 1 1 calc GR . . . .
H9C H 0.657154 0.226384 0.458992 0.072 Uiso 1 1 calc GR . . . .
H1 H 0.743(2) 0.4585(17) 0.3971(16) 0.040(6) Uiso 1 1 d . . . . .
H2 H 0.644(2) 0.4322(17) 0.7801(15) 0.039(6) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 H1 108.3(15) . . ?
C16 O2 H2 110.5(14) . . ?
O2 C16 C11 120.39(15) . . y
C15 C16 O2 116.63(13) . . y
C15 C16 C11 122.97(14) . . y
C16 C11 C12 116.34(14) . . y
C16 C11 C6 122.68(14) . . y
C12 C11 C6 120.98(13) . . y
O1 C12 C11 116.73(13) . . y
O1 C12 C13 121.81(13) . . y
C13 C12 C11 121.45(14) . . y
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.77(14) . . y
C14 C13 H13 119.6 . . ?
C13 C14 C17 119.79(15) . . y
C15 C14 C13 118.88(14) . . y
C15 C14 C17 121.32(14) . . y
C6 C7 H7 117.5 . . ?
C2 C7 H7 117.5 . . ?
C2 C7 C6 125.00(14) . . y
C11 C6 H6 107.3 . . ?
C11 C6 C5 111.95(13) . . y
C7 C6 C11 112.35(12) . . y
C7 C6 H6 107.3 . . ?
C7 C6 C5 110.49(12) . . y
C5 C6 H6 107.3 . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.52(14) . . y
C14 C15 H15 120.2 . . ?
C7 C2 C3 121.64(15) . . y
C7 C2 C1 122.20(16) . . y
C1 C2 C3 116.11(15) . . y
C6 C5 H5 107.7 . . ?
C8 C5 C6 112.32(13) . . y
C8 C5 H5 107.7 . . ?
C8 C5 C4 113.34(13) . . y
C4 C5 C6 107.87(13) . . y
C4 C5 H5 107.7 . . ?
C10 C8 C5 120.39(18) . . y
C10 C8 C9 121.98(18) . . y
C9 C8 C5 117.62(16) . . y
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 C5 111.34(14) . . y
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C14 C17 H17A 108.8 . . ?
C14 C17 H17B 108.8 . . ?
C14 C17 C18 113.68(14) . . y
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C2 C3 C4 112.68(14) . . y
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.70(15) . . y
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C18 C19 C20 111.91(17) . . y
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 C10 H10A 120.0 . . ?
C8 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.3685(18) . y
O1 H1 0.84(2) . ?
O2 C16 1.3904(18) . y
O2 H2 0.86(2) . ?
C16 C11 1.391(2) . y
C16 C15 1.390(2) . y
C11 C12 1.405(2) . y
C11 C6 1.514(2) . y
C12 C13 1.386(2) . y
C13 H13 0.9500 . ?
C13 C14 1.392(2) . y
C14 C15 1.388(2) . y
C14 C17 1.519(2) . y
C7 H7 0.9500 . ?
C7 C6 1.514(2) . y
C7 C2 1.331(2) . y
C6 H6 1.0000 . ?
C6 C5 1.552(2) . y
C15 H15 0.9500 . ?
C2 C3 1.512(2) . y
C2 C1 1.504(2) . y
C5 H5 1.0000 . ?
C5 C8 1.516(2) . y
C5 C4 1.536(2) . y
C8 C10 1.325(3) . y
C8 C9 1.505(3) . y
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.527(2) . y
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.532(3) . y
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.515(3) . y
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.518(3) . y
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
