A new total synthesis of the zinc matrixmetalloproteinase inhibitor ageladine A featuring a biogenetically patterned 6pi-2-azatriene electrocyclization.
Meketa, Matthew L.; Weinreb, Steven M.; Organic letters 9 (2007) 853–855; doi:10.1021/ol063038a

data_1505297
_publ_section_title
;
 A new total synthesis of the zinc matrixmetalloproteinase inhibitor
 ageladine A featuring a biogenetically patterned 6pi-2-azatriene
 electrocyclization.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              853
_journal_page_last               855
_journal_paper_doi               10.1021/ol063038a
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C13 H12 Br2 N2 O2'
_chemical_formula_sum            'C13 H12 Br2 N2 O2'
_chemical_formula_weight         388.07
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.28(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.811(3)
_cell_length_b                   20.027(10)
_cell_length_c                   12.310(5)
_cell_measurement_reflns_used    3116
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.713
_cell_volume                     1316.0(11)
_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      98(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11855
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    6.159
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.970
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.5133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                2615
_reflns_number_total             3230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol063038asi20061214_104049.cif
_cod_data_source_block           mlm5s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/C
_cod_database_code               1505297