Biomimetically inspired short access to the 2-aminoimidazole-fused tetracyclic core of (+/-)-dibromoagelaspongin.
Picon, Sylvain; Tran, Huu Dau Elise; Martin, Marie-Thérèse; Retailleau, Pascal; Zaparucha, Anne; Al-Mourabit, Ali; Organic letters 11 (2009) 2523–2526; doi:10.1021/ol900745c

data_1503944
_publ_section_title
;
 Biomimetically inspired short access to the 2-aminoimidazole-fused
 tetracyclic core of (+/-)-dibromoagelaspongin.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2523
_journal_page_last               2526
_journal_paper_doi               10.1021/ol900745c
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C14 H10 D3 Br2 N5 O3, D2 O'
_chemical_formula_sum            'C14 H10 Br2 D5 N5 O4'
_chemical_formula_weight         482.12
_chemical_name_systematic
; 
 2,3-dibromo-6,6-deuterated dihydroxy-4a-(pyrimidin-2-yl deuterated amino)
-5,6,7,8-tetrahydro-4aH, 10Hpyrrolo[1',2':3,4]imidazo[1,2-a]pyridin-10-one
deuterated hydrate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.03(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.905(4)
_cell_length_b                   13.448(5)
_cell_length_c                   12.532(5)
_cell_measurement_reflns_used    4894
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.78
_cell_measurement_theta_min      0.41
_cell_volume                     1771.0(12)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_sigmaI/netI    0.1190
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6127
_diffrn_reflns_theta_full        19.60
_diffrn_reflns_theta_max         19.60
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.607
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         1529
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+1.9885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                955
_reflns_number_total             1529
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900745c_si_002.cif
_cod_data_source_block           compound_32_CCDC_694748
_cod_original_cell_volume        1771.0(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C14 H10 D5 Br2 N5 O4'
_cod_database_code               1503944