The Synthesis of Certain Derivatives and Analogues of (-)- and (+)-Galanthamine and an Assessment of their Capacities to Inhibit Acetylcholine Esterase.
Buckler, Joshua N.; Taher, Ehab S.; Fraser, Nicolas J.; Willis, Anthony C.; Carr, Paul D.; Jackson, Colin J.; Banwell, Martin G.; The Journal of organic chemistry 82 (2017) 7869–7886; doi:10.1021/acs.joc.7b01062

data_4032825
_publ_section_title
;
 The Synthesis of Certain Derivatives and Analogues of (-)- and
 (+)-Galanthamine and an Assessment of their Capacities to Inhibit
 Acetylcholine Esterase.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7869
_journal_page_last               7886
_journal_paper_doi               10.1021/acs.joc.7b01062
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H23 O7.50'
_chemical_formula_sum            'C18 H23 O7.5'
_chemical_formula_weight         359.38
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-07
_audit_creation_method           CRYSTALS_ver_14.43
_audit_update_record
;
2016-10-07 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 94.8743(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.31530(10)
_cell_length_b                   31.4358(3)
_cell_length_c                   7.82450(10)
_cell_measurement_reflns_used    24081
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      6
_cell_volume                     1792.83(4)
_computing_cell_refinement
; 
 CrysAlisPro, Agilent Technologies, (2013), Yarnton, England 
;
_computing_data_collection       'SuperNova, (Agilent Technologies)'
_computing_data_reduction
; 
 CrysAlisPro, Agilent Technologies, (2013), Yarnton, England 
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_source         'microsource sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            33753
_diffrn_reflns_theta_full        72.495
_diffrn_reflns_theta_max         72.495
_diffrn_reflns_theta_min         2.811
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro, Agilent Technologies, (2013), Yarnton, England 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details 'Flack (1983), 3409 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         6989
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.0005912
_refine_ls_shift/su_mean         0.0000332
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.68P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0788
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0788
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              38
_reflns_limit_k_min              -38
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                6919
_reflns_number_total             7018
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.03
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0309
_oxford_refine_ls_scale          6.18(8)
_oxford_reflns_number_all        6989
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 'C:\Users\PaulCarr\Desktop\ban15_ At 14:19 on'
_publcif_datablock.id            {21ba5762-5392-45f0-a25d-be995292959c}
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE O(1, X'S) H(12,X'S) 
RIDE O(5, X'S) H(52,X'S) 
RIDE O(51, X'S) H(511,X'S) 
RIDE O(55, X'S) H(551,X'S) 
RIDE O   (  99,X'S) H   ( 991,X'S) H   ( 992,X'S) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) H   (  83,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) H   (  93,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 271,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
RIDE C   (  51,X'S) H   ( 512,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  55,X'S) H   ( 552,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) H   ( 582,X'S) H   ( 583,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) H   ( 592,X'S) H   ( 593,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) H   ( 602,X'S) H   ( 603,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) 
RIDE C   (  67,X'S) H   ( 671,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) H   ( 682,X'S) H   ( 683,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            jo7b01062_si_005.cif
_cod_data_source_block           ban15_pc03sn
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C18 H23 O7.50'
_cod_database_code               4032825