Formal Total Synthesis of (+)-C9-Deoxyomuralide from l-Leucine Using a Double Sacrificial Chirality Transfer Approach.
Bulman Page, Philip C.; Goodyear, Ross L.; Horton, Alexandra E.; Chan, Yohan; Karim, Rehana; O'Connell, Maria A; Hamilton, Christopher; Slawin, Alexandra M. Z.; Buckley, Benjamin R.; Allin, Steven M.; The Journal of organic chemistry 82 (2017) 12209–12223; doi:10.1021/acs.joc.7b02078

data_4033171
_publ_section_title
;
 Formal Total Synthesis of (+)-C9-Deoxyomuralide from l-Leucine Using a
 Double Sacrificial Chirality Transfer Approach.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12209
_journal_page_last               12223
_journal_paper_doi               10.1021/acs.joc.7b02078
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H30 N2 O9'
_chemical_formula_sum            'C27 H30 N2 O9'
_chemical_formula_weight         526.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-03-29
_audit_creation_method           'by CrystalStructure 4.2'
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.292(12)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            16
_cell_length_a                   18.721(12)
_cell_length_b                   18.189(8)
_cell_length_c                   30.942(16)
_cell_measurement_reflns_used    10585
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.24
_cell_volume                     10398(10)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1498
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26675
_diffrn_reflns_point_group_measured_fraction_full 0.748
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_theta_full        25.202
_diffrn_reflns_theta_max         25.202
_diffrn_reflns_theta_min         2.239
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4448.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.71
_refine_diff_density_min         -0.50
_refine_ls_abs_structure_details
;
 Flack x determined using 1005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.4(10)
_refine_ls_extinction_coef       0.0004(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     1370
_refine_ls_number_reflns         14021
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2020
_refine_ls_R_factor_gt           0.1548
_refine_ls_shift/su_max          0.041
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3752
_refine_ls_wR_factor_ref         0.4401
_reflns_Friedel_coverage         0.573
_reflns_Friedel_fraction_full    0.545
_reflns_Friedel_fraction_max     0.545
_reflns_number_gt                7337
_reflns_number_total             14021
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo7b02078_si_002.cif
_cod_data_source_block           16a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value ' unk' changed to 'unk'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033169--4033173.cif.
;
_cod_database_code               4033171
_shelx_res_checksum              55499
_shelx_hkl_checksum              36448