Asymmetric total synthesis of ent-cyclooroidin.
Mukherjee, Sabuj; Sivappa, Rasapalli; Yousufuddin, Muhammed; Lovely, Carl J.; Organic letters 12 (2010) 4940–4943; doi:10.1021/ol1020916

data_1503265
_publ_section_title
;
 Asymmetric total synthesis of ent-cyclooroidin.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4940
_journal_page_last               4943
_journal_paper_doi               10.1021/ol1020916
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C14 H17 Br2 Cl2 N5 O3 S'
_chemical_formula_weight         566.11
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.185(2)
_cell_angle_beta                 82.371(2)
_cell_angle_gamma                74.790(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1542(10)
_cell_length_b                   10.4880(14)
_cell_length_c                   15.104(2)
_cell_measurement_reflns_used    3014
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1033.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6844
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    4.306
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4765
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0929P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                3683
_reflns_number_total             4765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1020916_si_002.cif
_cod_data_source_block           sabuj7m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1503265