New solvates of the drug naltrexone: protonation, conformation and interplay of synthons
Gonçalves, Karolina de Oliveira; Ribeiro, Leandro; de Oliveira, Cecilia Maria Alves; Carvalho, Jesiel Freitas; Martins, Felipe T.; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618001791

data_2021019
_publ_section_title
;
 New solvates of the drug naltrexone: protonation, conformation and
 interplay of synthons
;
_journal_coeditor_code           CU3125
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618001791
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          '2C20 H23 N O4, C4 H10 O'
_chemical_formula_moiety         '2(C20 H23 N O4), C4 H10 O'
_chemical_formula_sum            'C44 H56 N2 O9'
_chemical_formula_weight         756.91
_chemical_name_systematic
'(4<i>R</i>,4a<i>S</i>,7a<i>R</i>,12b<i>S</i>)-3-Cyclopropylmethyl-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1<i>H</i>-4,12-methanobenzofuro[3,2-<i>e</i>]isoquinolin-7-one diethyl ether hemisolvate'
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5992(2)
_cell_length_b                   13.1093(3)
_cell_length_c                   26.6586(6)
_cell_measurement_reflns_used    2455
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      50.05
_cell_measurement_theta_min      3.757
_cell_volume                     4403.11(16)
_computing_cell_refinement
;
SAINT (Bruker, 2003)
;
_computing_data_collection
;
APEX2 (Bruker, 2003)
;
_computing_data_reduction
;
SAINT (Bruker, 2003)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and
Mercury (Macrae <i>et al</i>., 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al</i>.,  1993)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.523
_diffrn_reflns_theta_min         3.316
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_description       needle
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.265
_refine_ls_abs_structure_details
;
Flack x determined using 1854 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.12(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7390
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1130P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1927
_reflns_number_gt                5222
_reflns_number_total             7390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cu3125sup1.cif
_cod_data_source_block           naltrexone_Et2O
_cod_database_code               2021019
_shelx_hkl_checksum              96223
_shelx_res_checksum              67900
_shelxl_version_number           2.014
_cod_database_fobs_code 2021019