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_4032676
_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_compound_source        local
_chemical_formula_moiety         'C23 H31 N O7'
_chemical_formula_sum            'C23 H31 N O7'
_chemical_formula_weight         433.50
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_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             16-07-18
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2016-07-18 - C23 H31 N1 O7
            by Brett Schwartz
            for Josh Buckner and Martin Banwell

2016-07-18 - Tony Willis tidies up 
2016-07-18 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 106.8796(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.14845(9)
_cell_length_b                   10.61199(7)
_cell_length_c                   10.80864(10)
_cell_measurement_reflns_used    12487
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     1113.889(17)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17464
_diffrn_reflns_theta_full        72.352
_diffrn_reflns_theta_max         72.352
_diffrn_reflns_theta_min         4.275
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.13
_refine_ls_abs_structure_details 'Flack (1983), 1570 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_coef       21(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0262
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.0003895
_refine_ls_shift/su_mean         0.0000355
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.14P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0669
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0669
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3843
_reflns_number_total             3907
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.99
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0263
_oxford_refine_ls_scale          9.0(2)
_oxford_reflns_number_all        3907
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'xcalibur in C:\Users\brettoid\D At 13: 1 on '
_cod_data_source_file            jo7b01062_si_003.cif
_cod_data_source_block           ban1509SN_Brett
_cod_depositor_comments          'Adding full bibliography for 4032676.cif.'
_cod_original_cell_volume        1113.889(16)
_cod_original_sg_symbol_Hall     'p 2yb '
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4032676
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 183,X'S) H   ( 182,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 203,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) H   ( 233,X'S) 
RIDE C   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) H   ( 303,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) H   ( 313,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;