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_2021018
_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          '3C20 H23 N O4, C4 H8 O2'
_chemical_formula_moiety         '3(C20 H23 N O4), C4 H8 O2'
_chemical_formula_sum            'C64 H77 N3 O14'
_chemical_formula_weight         1112.29
_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 ethyl acetate 0.33-solvate'
_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   constr
_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                   13.0034(4)
_cell_length_b                   14.0829(4)
_cell_length_c                   31.4790(10)
_cell_measurement_reflns_used    2253
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      52.10
_cell_measurement_theta_min      4.213
_cell_volume                     5764.6(3)
_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 0.946
_diffrn_measured_fraction_theta_max 0.966
_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  0.0339
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            20908
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         2.807
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.793
_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    1.282
_exptl_crystal_description       prism
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.232
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2489 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.00(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     756
_refine_ls_number_reflns         9344
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0843P)^2^+0.2244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                7082
_reflns_number_total             9344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cu3125sup1.cif
_cod_data_source_block           naltrexone_AcOEt
_cod_database_code               2021018
_cod_database_fobs_code          2021018
_shelx_hkl_checksum              93355
_shelx_res_checksum              43654
_shelxl_version_number           2.014