A Combined NMR, DFT, and X-ray Investigation of Some Cinchona Alkaloid O-Ethers
Igor Busygin; Ville Nieminen; Antti Taskinen; Jari Sinkkonen; Esa Toukoniitty; Reijo Sillanpää; Dmitry Yu. Murzin; Reko Leino; Journal of Organic Chemistry 73 (2008) 6559–6569; doi:10.1021/jo8008462

data_4023631
_publ_section_title
;
 A Combined NMR, DFT, and X-ray Investigation
 of Some Cinchona Alkaloid O-Ethers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6559
_journal_page_last               6569
_journal_paper_doi               10.1021/jo8008462
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C20 H24 N2 O'
_chemical_formula_sum            'C20 H24 N2 O'
_chemical_formula_weight         308.41
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.034(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7869(3)
_cell_length_b                   11.0482(7)
_cell_length_c                   11.0367(5)
_cell_measurement_reflns_used    4742
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.733
_cell_measurement_theta_min      0.407
_cell_volume                     825.51(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3045
_diffrn_reflns_theta_full        26.76
_diffrn_reflns_theta_max         26.76
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+0.4860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                2694
_reflns_number_total             3045
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo8008462-file003.cif
_cod_data_source_block           meocd
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023631