Synthesis of a D-Ring Isomer of Galanthamine via a Radical-Based Smiles Rearrangement Reaction.
Lan, Ping; Jackson, Colin J.; Banwell, Martin G.; Willis, Anthony C.; The Journal of organic chemistry 79 (2014) 6759–6764; doi:10.1021/jo501255c

data_4029675
_publ_section_title
;
 Synthesis of a D-Ring Isomer of Galanthamine via a Radical-Based Smiles
 Rearrangement Reaction.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6759
_journal_page_last               6764
_journal_paper_doi               10.1021/jo501255c
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_compound_source        local
_chemical_formula_moiety         'C17 H21 N O3'
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.36
_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
_audit_creation_date             13-05-29
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-04-29 - Report on C17 H21 N O3
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2013-04-29 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2260(3)
_cell_length_b                   8.3026(3)
_cell_length_c                   28.0590(12)
_cell_measurement_reflns_used    15342
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.6
_cell_volume                     1450.43(11)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_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      200
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13312
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.558
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9506
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.0019968
_refine_ls_shift/su_mean         0.0001269
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.26P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0816
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0816
_reflns_limit_h_max              7
_reflns_limit_h_min              0
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                1178
_reflns_number_total             1529
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.84
_oxford_diffrn_Wilson_scale      5.77
_oxford_refine_ls_r_factor_ref   0.0596
_oxford_refine_ls_scale          0.4172(8)
_oxford_reflns_number_all        1529
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1335 At 14:40 on 29/ 5/13'
_cod_data_source_file            jo501255c_si_002.cif
_cod_data_source_block           ban1335
_cod_depositor_comments
'Adding full bibliography for 4029675--4029677.cif.'
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4029675
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S H(41,X'S) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,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                                                                             
;