Cocaethylene, the in vivo product of cocaine and ethanol, is a narcotic more potent than its precursors.
Maia, Angélica Faleiros da Silva; Martins, Felipe T.; Silva Neto, Leonardo da; Alves, Rosemeire Brondi; De Fátima, Ângelo; Acta crystallographica. Section C, Structural chemistry 73 (2017) 780–783; doi:10.1107/S2053229617012852

data_2311914
_publ_section_title
;
 Cocaethylene, the in vivo product of cocaine and ethanol, is a narcotic
 more potent than its precursors.
;
_journal_coeditor_code           CU3117
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              780
_journal_page_last               783
_journal_paper_doi               10.1107/S2053229617012852
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C18 H23 N O4'
_chemical_formula_moiety         'C18 H23 N O4'
_chemical_formula_sum            'C18 H23 N O4'
_chemical_formula_weight         317.37
_chemical_name_systematic
;
ethyl
(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 107.8810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4533(2)
_cell_length_b                   10.2380(3)
_cell_length_c                   10.2552(2)
_cell_measurement_reflns_used    2631
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.05
_cell_measurement_theta_min      5.955
_cell_volume                     844.66(4)
_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, 1997), Mercury (Macrae <i>et al</i>.,
2006)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al</i>.,  1993)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.94
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       CCD
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.53
_diffrn_reflns_theta_min         5.958
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.725
_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    1.248
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.166
_refine_ls_abs_structure_details
;
Flack x parameter determined using 568 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013).
;
_refine_ls_abs_structure_Flack   -0.03(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0631P)^2^+0.0701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                2026
_reflns_number_total             2133
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cu3117sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2311914
_shelx_hkl_checksum              66145
_shelx_res_checksum              21375
_shelxl_version_number           2.014