Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity
Robert D. Giacometti; Jan Duchek; Lukas Werner; Afeef S. Husni; Christopher R. McCurdy; Stephen J. Cutler; D. Phillip Cox; Tomas Hudlicky; Journal of Organic Chemistry 78 (2013) 2914–2925; doi:10.1021/jo3026753

data_4028070
_publ_section_title
;
 Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2914
_journal_page_last               2925
_journal_paper_doi               10.1021/jo3026753
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H22 O4'
_chemical_formula_sum            'C19 H22 O4'
_chemical_formula_weight         314.37
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.0160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5814(2)
_cell_length_b                   6.9221(2)
_cell_length_c                   12.0783(3)
_cell_measurement_reflns_used    1944
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.91
_cell_measurement_theta_min      3.90
_cell_volume                     752.69(3)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'rotating anode'
_diffrn_radiation_source         'fine-focus parallel mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5218
_diffrn_reflns_theta_full        71.66
_diffrn_reflns_theta_max         71.66
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.9546
_exptl_absorpt_correction_T_min  0.7251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   twinabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       hexagon
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5218
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.1125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0854
_reflns_number_gt                5176
_reflns_number_total             5218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3026753_si_002.cif
_cod_data_source_block           twin5
_cod_database_code               4028070