Insights into hydrate formation and stability of morphinanes from a combination of experimental and computational approaches.
Braun, Doris E.; Gelbrich, Thomas; Kahlenberg, Volker; Griesser, Ulrich J.; Molecular pharmaceutics 11 (2014) 3145–3163; doi:10.1021/mp500334z

data_1517279
_publ_section_title
;
 Insights into hydrate formation and stability of morphinanes from a
 combination of experimental and computational approaches.
;
_journal_issue                   9
_journal_name_full               'Molecular pharmaceutics'
_journal_page_first              3145
_journal_page_last               3163
_journal_paper_doi               10.1021/mp500334z
_journal_volume                  11
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H22 N O3, Cl'
_chemical_formula_sum            'C18 H22 Cl N O3'
_chemical_formula_weight         335.82
_chemical_name_common            'Codeine Hydrochloride Anhydrate I'
_chemical_name_systematic
;
 (5a,6a)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol hydrochloride
;
_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
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.14435(17)
_cell_length_b                   13.2304(3)
_cell_length_c                   16.5408(4)
_cell_measurement_reflns_used    7047
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.5939
_cell_measurement_theta_min      3.0732
_cell_volume                     1563.48(6)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12628
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         3.079
_exptl_absorpt_coefficient_mu    0.26
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.96688
_exptl_absorpt_correction_type   multi-scan
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;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'fragment of a prism'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1172 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.11(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.4614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0739
_reflns_number_gt                2897
_reflns_number_total             3062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            mp500334z_si_002.cif
_cod_data_source_block           CCl-I
_cod_depositor_comments
'Adding full bibliography for 1517277--1517281.cif.'
_cod_database_code               1517279