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_4036771
_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         'C13 H25 Br O4'
_chemical_formula_sum            'C13 H25 Br O4'
_chemical_formula_weight         325.24
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-24
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_cell_angle_alpha                66.516(9)
_cell_angle_beta                 73.360(6)
_cell_angle_gamma                87.831(6)
_cell_formula_units_Z            1
_cell_length_a                   6.0963(3)
_cell_length_b                   8.7014(8)
_cell_length_c                   8.7050(8)
_cell_measurement_reflns_used    2489
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2200
_cell_measurement_theta_min      2.5540
_cell_volume                     404.25(7)
_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 0.880
_diffrn_measurement_details
;
  1 omega  -96.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000    0.0000 -180.0000 140

  2 omega  -97.00   20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -72.0000    0.0000 117

  3 omega  -76.00   20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -72.0000 -180.0000 96

  4 omega  -41.00  -24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   72.0000  -30.0000 17

  5 omega  -23.00   -6.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   36.0000  150.0000 17

  6 omega  -31.00  -20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   72.0000  150.0000 11
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.0013379000
_diffrn_orient_matrix_UB_12      -0.0475866000
_diffrn_orient_matrix_UB_13      -0.0496381000
_diffrn_orient_matrix_UB_21      -0.1021235000
_diffrn_orient_matrix_UB_22      -0.0470550000
_diffrn_orient_matrix_UB_23      0.0636313000
_diffrn_orient_matrix_UB_31      -0.0665377000
_diffrn_orient_matrix_UB_32      0.0589950000
_diffrn_orient_matrix_UB_33      -0.0462334000
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4082
_diffrn_reflns_point_group_measured_fraction_full 0.723
_diffrn_reflns_point_group_measured_fraction_max 0.595
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.841
_diffrn_reflns_theta_min         2.562
_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    2.547
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82030
_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    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             170
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of pentane and Et2O by slow evaporation'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.003(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0753P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.353
_reflns_Friedel_fraction_full    0.448
_reflns_Friedel_fraction_max     0.310
_reflns_number_gt                2470
_reflns_number_total             3019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00489_si_002.cif
_cod_data_source_block           17a
_cod_original_cell_volume        404.26(6)
_cod_database_code               4036771
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 88.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.77
_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, All C(H,H,H,H,H) groups
2. Restrained distances
 H4-O4
 0.84 with sigma of 0.02
 H3-O3
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C9(H9A,H9B,H9C), C13(H13A,
 H13B,H13C)
;
_shelx_res_checksum              74893
_shelx_hkl_checksum              95915
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_submission    30/10/14
_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 JM7190-57f2
_olex2_submission_special_instructions 'No special instructions were received'