Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family.
Dethe, Dattatraya H.; Erande, Rohan D.; Mahapatra, Samarpita; Das, Saikat; B, Vijay Kumar; Chemical communications (Cambridge, England) 51 (2015) 2871–; doi:10.1039/c4cc08562k

data_7116307
_publ_section_title
;
 Protecting group free enantiospecific total syntheses of structurally
 diverse natural products of the tetrahydrocannabinoid family.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2871
_journal_paper_doi               10.1039/c4cc08562k
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_compound_source        --
_chemical_formula_moiety         'C24 H23 O4 '
_chemical_formula_sum            'C24 H24 O4'
_chemical_formula_weight         376.43
_chemical_melting_point          477.15
_chemical_name_common            30julb
_chemical_name_systematic        30julb
_space_group_IT_number           19
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc134zbk
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-07 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.814(2)
_cell_length_b                   9.199(3)
_cell_length_c                   24.640(7)
_cell_measurement_reflns_used    4508
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.52
_cell_measurement_theta_min      2.36
_cell_volume                     1997.8(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14292
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.9776
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH/CDCl3'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.1165P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                2450
_reflns_number_total             3712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc08562k2.cif
_cod_data_source_block           c:\docume~1\admini~1\desktop\rohan\30julb
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '204 C' was changed to '477.15' - it
was converted from degrees Celsius(C) to
Kelvins(K).

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 7116307.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7116307