Biomimetic Total Synthesis of the Pentacyclic Amaryllidaceae Alkaloid Derivative Gracilamine.
Gao, Nadia Yuqian; Banwell, Martin G.; Willis, Anthony C.; Organic letters 19 (2017) 162–165; doi:10.1021/acs.orglett.6b03465

data_1544938
_publ_section_title
;
 Biomimetic Total Synthesis of the Pentacyclic Amaryllidaceae Alkaloid
 Derivative Gracilamine.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              162
_journal_page_last               165
_journal_paper_doi               10.1021/acs.orglett.6b03465
_journal_volume                  19
_journal_year                    2017
_chemical_compound_source        local
_chemical_formula_moiety         'C32 H37 N3 O8 S'
_chemical_formula_sum            'C32 H37 N3 O8 S'
_chemical_formula_weight         623.73
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-04-24
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-04-24 - Report on C24 H22 N2 O7 S 
             by Anthony C. Willis
             for   Nadia Gao and Martin Banwell

2013-04-26 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90.2580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8900(2)
_cell_length_b                   31.1842(7)
_cell_length_c                   11.2873(3)
_cell_measurement_reflns_used    72232
_cell_measurement_temperature    200
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     3129.12(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.048
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37511
_diffrn_reflns_theta_full        27.480
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.613
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1320.000
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9883
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         7177
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.0297736
_refine_ls_shift/su_mean         0.0002054
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 1.59P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1334
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1334
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              40
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                4884
_reflns_number_total             7177
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.29
_oxford_diffrn_Wilson_scale      5.24
_oxford_refine_ls_r_factor_ref   0.0878
_oxford_refine_ls_scale          0.4898(8)
_oxford_reflns_number_all        7177
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1318a At 14:53 on 23/4/13'
_cod_data_source_file            ol6b03465_si_004.cif
_cod_data_source_block           ban1318a
_cod_depositor_comments
'Adding full bibliography for 1544938--1544940.cif.'
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               1544938
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, C(1,U'S) UNTIL O(29) 
CONT O(30,U'S,OCC) UNTIL C(32) 
CONT S(33,U'S) UNTIL O(44) 
CONT O(130,U'S,OCC) UNTIL C(132) H(201,X'S) 
EQUIV O(30,OCC) UNTIL C(32) O(130,OCC) UNTIL C(132) 
WEIGHT -1 O(130,OCC) UNTIL C(132) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) H   ( 263,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) H   ( 273,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   ( 131,X'S) H   ( 1311,X'S) H   ( 1312,X'S) 
RIDE C   ( 132,X'S) H   ( 1321,X'S) H   ( 1322,X'S) H   ( 1323,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 0.0, .02 = MEAN C(28) TO O(30), C(28) TO O(130) 
DIST 0.0, .02 = MEAN O(30) TO C(31), O(130) TO C(131) 
DIST 0.0, .02 = MEAN C(31) TO C(32), C(131) TO C(132) 
ANGLE 0.0, 2. = MEAN C(28) TO O(30) TO C(31), C(28) TO O(130) TO C(131) 
ANGLE 0.0, 2. = MEAN O(30) TO C(31) TO C(32), O(130) TO C(131) TO C(132) 
VIBR 0.0, .01 = C(28) TO O(30), C(28) TO O(130) 
VIBR 0.0, .01 = O(30) TO C(31), O(130) TO C(131) 
VIBR 0.0, .01 = C(31) TO C(32), C(131) TO C(132) 
DIST 0.85, .01 = N(20) TO H(201) 
LIMIT 0.001 H(201,X) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;