Asymmetric total synthesis of the antimalarial drug (+)-mefloquine hydrochloride via chiral N-amino cyclic carbamate hydrazones.
Knight, John D.; Sauer, Scott J.; Coltart, Don M.; Organic letters 13 (2011) 3118–3121; doi:10.1021/ol2010193

data_1502223
_publ_section_title
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 Asymmetric total synthesis of the antimalarial drug (+)-mefloquine
 hydrochloride via chiral N-amino cyclic carbamate hydrazones.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3118
_journal_page_last               3121
_journal_paper_doi               10.1021/ol2010193
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         C30H25N3O3F6
_chemical_formula_sum            'C30 H25 F6 N3 O3'
_chemical_formula_weight         589.53
_chemical_name_systematic
; 
 ? 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2964(3)
_cell_length_b                   13.4415(6)
_cell_length_c                   27.0296(12)
_cell_measurement_reflns_used    7900
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.076
_cell_measurement_theta_min      2.2605
_cell_volume                     2650.9(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD detector Smart6000'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            29459
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular platelet'
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         6396
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+1.0739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                6051
_reflns_number_total             6396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2010193_si_002.cif
_cod_data_source_block           C30H25N3O3F6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1502223