Cyclopenta[b]pyrroles from triazines: synthetic and mechanistic studies.
Ye, Long; Haddadin, Makhluf J.; Lodewyk, Michael W.; Ferreira, Andrew J.; Fettinger, James C.; Tantillo, Dean J.; Kurth, Mark J.; Organic letters 12 (2010) 164–167; doi:10.1021/ol902559u

data_1503359
_publ_section_title
;
 Cyclopenta[b]pyrroles from triazines: synthetic and mechanistic studies.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              164
_journal_page_last               167
_journal_paper_doi               10.1021/ol902559u
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C25 H22 Br N3 O'
_chemical_formula_sum            'C25 H22 Br N3 O'
_chemical_formula_weight         460.37
_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                 96.3000(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4028(11)
_cell_length_b                   20.9078(19)
_cell_length_c                   8.1340(7)
_cell_measurement_reflns_used    8278
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.70
_cell_volume                     2096.5(3)
_computing_cell_refinement       'SAINT (7.60A) (Bruker, 2008)'
_computing_data_collection       'SMART (Version 5.054) (Bruker, 2002)'
_computing_data_reduction        'SAINT (7.60A) (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART1000 CCD'
_diffrn_measurement_method       '\f and \w 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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18515
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  0.7798
_exptl_absorpt_correction_T_min  0.5306
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2008/2 (Sheldrick, 2008)'
_exptl_crystal_colour            'Faint Yellow'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0391P)^2^+1.3611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0885
_reflns_number_gt                3634
_reflns_number_total             4820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902559u_si_003.cif
_cod_data_source_block           jf1836fmi_CCDC751264
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Numerical'
changed to 'numerical' 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 21/c'
_cod_database_code               1503359