Total Synthesis of (-)-Luminacin D.
Malassis, Julien; Bartlett, Nathan; Hands, Kane; Selby, Matthew D.; Linclau, Bruno; The Journal of organic chemistry 81 (2016) 3818–3837; doi:10.1021/acs.joc.6b00489

data_4036770
_publ_section_title
;
 Total Synthesis of (-)-Luminacin D.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3818
_journal_page_last               3837
_journal_paper_doi               10.1021/acs.joc.6b00489
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H22 O4 S'
_chemical_formula_sum            'C16 H22 O4 S'
_chemical_formula_weight         310.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.11.03 svn.r3071 for OlexSys, GUI svn.r4932)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.88884(12)
_cell_length_b                   12.3215(3)
_cell_length_c                   22.2795(5)
_cell_measurement_reflns_used    10959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.2600
_cell_measurement_theta_min      1.9970
_cell_volume                     1616.59(6)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
  1 omega  -59.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000   54.0000   30.0000 107

  2 omega -105.00   12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -36.0000 -120.0000 117

  3 omega -113.00 -102.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -18.0000 -180.0000 11

  4 omega  -84.00   53.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000   18.0000    0.0000 137

  5 omega -111.00 -100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000 -120.0000 11
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0203289000
_diffrn_orient_matrix_UB_12      -0.0554998000
_diffrn_orient_matrix_UB_13      -0.0065302000
_diffrn_orient_matrix_UB_21      -0.0553160000
_diffrn_orient_matrix_UB_22      0.0062335000
_diffrn_orient_matrix_UB_23      -0.0280696000
_diffrn_orient_matrix_UB_31      0.1050660000
_diffrn_orient_matrix_UB_32      0.0139708000
_diffrn_orient_matrix_UB_33      -0.0135128000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17203
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.306
_diffrn_reflns_theta_min         2.465
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       rod
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of pentane and ethanol by slow evaporation'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1913 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         5362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.1752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0755
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                4890
_reflns_number_total             5362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00489_si_002.cif
_cod_data_source_block           syn-9Tol
_cod_original_cell_volume        1616.58(6)
_cod_database_code               4036770
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 95.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.23
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C9(H9A,H9B,H9C), C16(H16A,
 H16B,H16C)
;
_shelx_res_checksum              65334
_shelx_hkl_checksum              21322
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id JM7196-87FL
_olex2_submission_special_instructions 'No special instructions were received'