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_4034786
_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         'C24 H29 N O7, 0.553(H2 O)'
_chemical_formula_sum            'C24 H30.11 N O7.55'
_chemical_formula_weight         453.46
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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             16-03-17
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2016-03-18 - Report on C24 H30.10 N O7.55 
             by Anthony C. Willis
       for   Steve Pyne and Anthony Carroll

2016-03-18 - details of refinement in _refine_special_details below

2016-03-18 - passes checkcif tests with minor warnings 
 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8947(1)
_cell_length_b                   11.9409(1)
_cell_length_c                   32.5277(4)
_cell_measurement_reflns_used    15624
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      5
_cell_volume                     2289.56(5)
_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 0.998
_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  0.055
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            36015
_diffrn_reflns_theta_full        72.502
_diffrn_reflns_theta_max         72.502
_diffrn_reflns_theta_min         3.944
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.81
_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    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             966.109
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.15
_refine_ls_abs_structure_details 'Flack (1983), 1893 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4539
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.0058214
_refine_ls_shift/su_mean         0.0004725
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.33P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0730
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0730
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              0
_reflns_number_gt                4398
_reflns_number_total             4539
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.83
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0297
_oxford_refine_ls_scale          6.69(11)
_oxford_reflns_number_all        4539
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\pyn1605SN\Tony_pyn1605SN_data At 17:25 on'
_cod_data_source_file            jo8b00585_si_003.cif
_cod_data_source_block           pyn1605SN
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4034786
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, O(1,U'S) UNTIL C(18) 
CONT C(19,U'S,OCC) UNTIL C(124) 
CONT ENANTIO O(8,OCC) H(1,X'S) UNTIL H(5) 
EQUIV C(19,OCC) UNTIL C(124) 
WEIGHT -1 C(119,OCC) UNTIL C(124) 
RIDE O(8,X'S) H(8,X'S) H(9,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   (  120,X'S) H   ( 1201,X'S) 
RIDE C   (  121,X'S) H   ( 1211,X'S) 
RIDE C   (  122,X'S) H   ( 1221,X'S) 
RIDE C   (  123,X'S) H   ( 1231,X'S) 
RIDE C   (  124,X'S) H   ( 1241,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 1.51, .01 = C(18) TO C(19), C(18) TO C(119) 
DIST 1.39, .01 = C(19) TO C(20), C(119) TO C(120) 
DIST 1.39, .01 = C(20) TO C(21), C(120) TO C(121) 
DIST 1.39, .01 = C(21) TO C(22), C(121) TO C(122) 
DIST 1.39, .01 = C(22) TO C(23), C(122) TO C(123) 
DIST 1.39, .01 = C(23) TO C(24), C(123) TO C(124) 
DIST 1.39, .01 = C(24) TO C(19), C(124) TO C(119) 
PLANAR C(18) C(19) UNTIL C(24) 
PLANAR C(18) C(119) UNTIL C(124) 
ANGLE 120, 2 = C(24) TO C(19) TO C(20), C(19) TO C(20) TO C(21) 
CONT C(20) TO C(21) TO C(22), C(21) TO C(22) TO C(23) 
CONT C(22) TO C(23) TO C(24), C(23) TO C(24) TO C(19) 
ANGLE 120, 2 = C(124) TO C(119) TO C(120), C(119) TO C(120) TO C(121) 
CONT C(120) TO C(121) TO C(122), C(121) TO C(122) TO C(123) 
CONT C(122) TO C(123) TO C(124), C(123) TO C(124) TO C(119) 
REM 
U(IJ) 0.0, .01 = C(19) TO C(119) 
U(IJ) 0.0, .01 = C(20) TO C(120) 
U(IJ) 0.0, .01 = C(21) TO C(121) 
U(IJ) 0.0, .01 = C(22) TO C(122) 
U(IJ) 0.0, .01 = C(23) TO C(123) 
U(IJ) 0.0, .01 = C(24) TO C(124) 
VIBR 0.0, .01 = C(19) TO C(20) 
VIBR 0.0, .01 = C(20) TO C(21) 
VIBR 0.0, .01 = C(21) TO C(22) 
VIBR 0.0, .01 = C(22) TO C(23) 
VIBR 0.0, .01 = C(23) TO C(24) 
VIBR 0.0, .01 = C(24) TO C(19) 
VIBR 0.0, .01 = C(119) TO C(120) 
VIBR 0.0, .01 = C(120) TO C(121) 
VIBR 0.0, .01 = C(121) TO C(122) 
VIBR 0.0, .01 = C(122) TO C(123) 
VIBR 0.0, .01 = C(123) TO C(124) 
VIBR 0.0, .01 = C(124) TO C(119) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;