Total Synthesis of Natural Hyacinthacine C<sub>5</sub> and Six Related Hyacinthacine C<sub>5</sub> Epimers.
Carroll, Anthony W.; Savaspun, Kongdech; Willis, Anthony C.; Hoshino, Masako; Kato, Atsushi; Pyne, Stephen G.; The Journal of organic chemistry 83 (2018) 5558–5576; doi:10.1021/acs.joc.8b00585

data_4034785
_publ_section_title
;
 Total Synthesis of Natural Hyacinthacine C<sub>5</sub> and Six Related
 Hyacinthacine C<sub>5</sub> Epimers.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5558
_journal_page_last               5576
_journal_paper_doi               10.1021/acs.joc.8b00585
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_moiety         'C27 H33 N O7, C2 H6 O'
_chemical_formula_sum            'C29 H39 N O8'
_chemical_formula_weight         529.63
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             16-04-20
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2016-03-20 - Report on C27 H33 N O7, C2 H5 O 
             by Anthony C. Willis
       for   Steve Pyne and Anthony Carroll

2016-03-20 - details of refinement in _refine_special_details below

2016-03-20 - passes checkcif tests with minor warnings 
 
;
_cell_angle_alpha                98.711(6)
_cell_angle_beta                 101.123(4)
_cell_angle_gamma                92.413(4)
_cell_formula_units_Z            2
_cell_length_a                   10.6785(4)
_cell_length_b                   10.7888(7)
_cell_length_c                   12.4332(8)
_cell_measurement_reflns_used    3928
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     1385.53(14)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.061
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16238
_diffrn_reflns_theta_full        71.318
_diffrn_reflns_theta_max         72.410
_diffrn_reflns_theta_min         3.672
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.31
_refine_ls_abs_structure_details 'Flack (1983), 1601 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         7063
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.0009516
_refine_ls_shift/su_mean         0.0001675
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.51P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1340
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1340
_reflns_limit_h_max              8
_reflns_limit_h_min              -13
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              -15
_reflns_number_gt                6118
_reflns_number_total             7065
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.53
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0637
_oxford_refine_ls_scale          7.45(18)
_oxford_reflns_number_all        7063
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\pyn1607SN\Tony_pyn1607SN_data At 9:18 on '
_cod_data_source_file            jo8b00585_si_004.cif
_cod_data_source_block           pyn1607SN
_cod_original_sg_symbol_Hall     'P 1 '
_cod_original_sg_symbol_H-M      'P 1 '
_cod_original_formula_sum        'C29 H39 N1 O8'
_cod_database_code               4034785
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE O   (   5,X'S) H   (   1,X'S) 
RIDE O   (   8,X'S) H   (   3,X'S) 
RIDE O   (  55,X'S) H   (   2,X'S) 
RIDE O   (  58,X'S) H   (   4,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   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  13,X'S) H   ( 131,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   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,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   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) H   ( 293,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) H   ( 572,X'S) H   ( 573,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) H   ( 602,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) H   ( 612,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) 
RIDE C   (  67,X'S) H   ( 671,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) H   ( 682,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) 
RIDE C   (  73,X'S) H   ( 731,X'S) 
RIDE C   (  74,X'S) H   ( 741,X'S) 
RIDE C   (  76,X'S) H   ( 761,X'S) H   ( 762,X'S) H   ( 763,X'S) 
RIDE C   (  77,X'S) H   ( 771,X'S) H   ( 772,X'S) H   ( 773,X'S) 
RIDE C   (  78,X'S) H   ( 781,X'S) H   ( 782,X'S) 
RIDE C   (  79,X'S) H   ( 791,X'S) H   ( 792,X'S) H   ( 793,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                                                                             
;