Δ^9^-Tetrahydrocannabinolic acid A, the precursor to Δ^9^-tetrahydrocannabinol (THC)
Skell, Jeffrey M.; Kahn, Michael; Foxman, Bruce M.; Acta Crystallographica Section C 77 (2021) 84–89; doi:10.1107/S2053229621000280

data_2022311
_publ_section_title
;
 \D^9^-Tetrahydrocannabinolic acid A, the precursor to
 \D^9^-tetrahydrocannabinol (THC)
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              84
_journal_page_last               89
_journal_paper_doi               10.1107/S2053229621000280
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H30 O4'
_chemical_formula_sum            'C22 H30 O4'
_chemical_formula_weight         358.48
_chemical_melting_point          ?
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2021-01-01
_audit_creation_method           'CRYSTALS_ver_14.61_build_7408 '
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4069(4)
_cell_length_b                   17.9819(7)
_cell_length_c                   19.1565(7)
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.37
_cell_volume                     3929.3(3)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'USER DEFINED STRUCTURE SOLUTION'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_unetI/netI     0.036
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27315
_diffrn_reflns_theta_full        28.278
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         1.553
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prism fragment'
_exptl_crystal_F_000             1551.985
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.570
_exptl_crystal_size_min          0.550
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 3595 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.02(19)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         9732
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.0006012
_refine_ls_shift/su_mean         0.0000869
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.57P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0863
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0863
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                9216
_reflns_number_total             9732
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.53
_oxford_diffrn_Wilson_scale      56.72
_oxford_refine_ls_r_factor_ref   0.0357
_oxford_refine_ls_scale          0.14092(4)
_oxford_reflns_number_all        9732
_oxford_structure_analysis_title 'thca_0m in P2(1)2(1)2(1)'
_cod_data_source_file            cu3167sup3.txt
_cod_data_source_block           THCA_unaveraged
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 2022311.cif.
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               2022311
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_hooft_y                  -0.07(17)
_oxford_bijvoet_difference       0.02(19)
_oxford_refined_flack_x          -0.3(4)