Enantioselective Synthesis of (−)-LL-C10037α from Benzoquinone
Murphy, Sean T.; Bencsik, Josef R.; Johnson, Carl R.; Organic Letters 1 (1999) 1483–; doi:10.1021/ol991038n

data_1507557
_publ_section_title
;
 Enantioselective Synthesis of (&#x2212;)-LL-C10037\a from Benzoquinone
;
_journal_issue                   9
_journal_name_full               'Organic Letters'
_journal_page_first              1483
_journal_paper_doi               10.1021/ol991038n
_journal_volume                  1
_journal_year                    1999
_chemical_formula_sum            'C6 H8 Br N3 O2'
_chemical_formula_weight         234.05
_chemical_melting_point          97.5(5)
_chemical_name_systematic
;rel-(1S,2R,3S,6R)-6-Azido-2-bromo-4-cyclohexene-1,3-diol 
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.718(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.6335(11)
_cell_length_b                   11.7727(8)
_cell_length_c                   8.5975(5)
_cell_measurement_reflns_used    4382
_cell_measurement_temperature    295(2)
_cell_volume                     1753.65(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Bruker P4/CCD'
_diffrn_measurement_method       'SMART CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.096
_diffrn_reflns_av_sigmaI/netI    0.1313
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            99388
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         1.18
_exptl_absorpt_coefficient_mu    4.652
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.608
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       0.0004(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.906
_refine_ls_goodness_of_fit_obs   1.149
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_restrained_S_obs      1.149
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_obs          0.0553
_refine_ls_shift/esd_max         0.007
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1252
_refine_ls_wR_factor_obs         0.1155
_reflns_number_observed          2120
_reflns_number_total             3718
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ol991038n.cif
_cod_data_source_block           brnn
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '97 - 98' was changed to '97.5(5)' -
the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1753.7(2)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507557