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_4034787
_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         'C30 H35 N O5'
_chemical_formula_sum            'C30 H35 N O5'
_chemical_formula_weight         489.61
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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             17-05-22
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2017-05-24 - Report on C30 H35 N O5 
             by Anthony C. Willis
       for   Steve Pyne and ???

2017-05-24 - details of refinement in _refine_special_details below

2017-05-24 - passes checkcif tests with no warnings 

;
_cell_angle_alpha                90
_cell_angle_beta                 97.7303(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.3461(2)
_cell_length_b                   5.1418(1)
_cell_length_c                   19.3686(2)
_cell_measurement_reflns_used    13283
_cell_measurement_temperature    150
_cell_measurement_theta_max      74
_cell_measurement_theta_min      2
_cell_volume                     1317.05(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20574
_diffrn_reflns_theta_full        73.853
_diffrn_reflns_theta_max         73.853
_diffrn_reflns_theta_min         2.302
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 1663 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.06(15)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         4647
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.0008173
_refine_ls_shift/su_mean         0.0000564
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.24P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1038
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1038
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              6
_reflns_limit_k_min              -5
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                4524
_reflns_number_total             4647
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.38
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0389
_oxford_refine_ls_scale          11.0(4)
_oxford_reflns_number_all        4647
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\pyn1705SNQ\Tony_pyn1705SNQ_da At 14:38 on'
_cod_data_source_file            jo8b00585_si_005.cif
_cod_data_source_block           pyn1705SNQ
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4034787
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S H(1,X'S) H(2,X'S) 
CONT ENANTIO 
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   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) H   (  83,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,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) H   ( 162,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,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) H   ( 232,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  124,X'S) H   ( 1241,X'S) H   ( 1242,X'S) 
RIDE C   (  126,X'S) H   ( 1261,X'S) 
RIDE C   (  127,X'S) H   ( 1271,X'S) 
RIDE C   (  128,X'S) H   ( 1281,X'S) 
RIDE C   (  129,X'S) H   ( 1291,X'S) 
RIDE C   (  130,X'S) H   ( 1301,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
DIST 1.39, .02 = C(25) TO C(26), C(25) TO C(126) 
DIST 1.39, .02 = C(25) TO C(30), C(25) TO C(130) 
DIST 1.39, .02 = C(26) TO C(27), C(126) TO C(127) 
DIST 1.39, .02 = C(27) TO C(28), C(127) TO C(128) 
DIST 1.39, .02 = C(28) TO C(29), C(128) TO C(129) 
DIST 1.39, .02 = C(29) TO C(30), C(129) TO C(130) 
REM 
ANGLE 120, 2 = C(30) TO C(25) TO C(26), C(130) TO C(25) TO C(126) 
ANGLE 120, 2 = C(25) TO C(26) TO C(27), C(25) TO C(126) TO C(127) 
ANGLE 120, 2 = C(26) TO C(27) TO C(28), C(126) TO C(127) TO C(128) 
ANGLE 120, 2 = C(27) TO C(28) TO C(29), C(127) TO C(128) TO C(129) 
ANGLE 120, 2 = C(28) TO C(29) TO C(30), C(128) TO C(129) TO C(130) 
ANGLE 120, 2 = C(29) TO C(30) TO C(25), C(129) TO C(130) TO C(25) 
REM 
PLANAR C(25) C(26) UNTIL C(30) 
PLANAR C(25) C(126) UNTIL C(130) 
REM 
U(IJ) 0.0, .02 = C(26) TO C(126) 
U(IJ) 0.0, .02 = C(27) TO C(127) 
U(IJ) 0.0, .02 = C(28) TO C(128) 
U(IJ) 0.0, .02 = C(29) TO C(129) 
U(IJ) 0.0, .02 = C(30) TO C(130) 
REM 
U(IJ) 0.0, .02 = C(24) TO C(124) 
DIST 0.0, .02 = MEAN C(25) TO C(24), C(25) TO C(124) 
DIST 0.0, .02 = MEAN O(5) TO C(24), O(5) TO C(124) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;