Absolute configuration of the antimalarial erythro-mefloquine – Vibrational Circular Dichroism and X-ray diffraction studies of mefloquine and its thiourea derivative
Kohout, Michal; Vandenbussche, Jelle; Roller, Alexander; T°uma, Jiří; Bogaerts, Jonathan; Bultinck, Patrick; Herrebout, Wouter; Lindner, Wolfgang; RSC Adv.  (2016) –; doi:10.1039/C6RA19367F

data_7226321
_publ_section_title
;
 Absolute configuration of the antimalarial erythro-mefloquine --
 Vibrational Circular Dichroism and X-ray diffraction studies of
 mefloquine and its thiourea derivative
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA19367F
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 F6 N3 O S, C2 H3 N'
_chemical_formula_sum            'C23 H24 F6 N4 O S'
_chemical_formula_weight         518.52
_chemical_name_systematic
;
(-)-erythro-N-(N-allylthiocarbamoyl) mefloquine, (11S, 12R)
;
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.76580(10)
_cell_length_b                   15.8201(4)
_cell_length_c                   26.2887(6)
_cell_measurement_reflns_used    6516
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.245
_cell_measurement_theta_min      3.260
_cell_volume                     2397.94(9)
_computing_cell_refinement       'APEX2 V2013.6-2'
_computing_data_collection       'APEX2 V2013.6-2'
_computing_data_reduction        'APEX2 V2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14932
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         3.260
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.841
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8947
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0732 before and 0.0602 after correction. 
The Ratio of minimum to maximum transmission is 0.8947. 
The \l/2 correction factor is 0.0000.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       stick
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.099
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1570 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.015(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+1.1012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3972
_reflns_number_total             4356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra19367f2.cif
_cod_data_source_block           miko810_vienna_p212121
_cod_database_code               7226321
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.839
_shelx_res_checksum              91313