Total syntheses of oroidin, hymenidin and clathrodin.
Rasapalli, Sivappa; Kumbam, Venkatreddy; Dhawane, Abasaheb N.; Golen, James A.; Lovely, Carl J.; Rheingold, Arnold L.; Organic & biomolecular chemistry 11 (2013) 4133–4137; doi:10.1039/c3ob40668g

data_7153758
_publ_section_title
;
 Total syntheses of oroidin, hymenidin and clathrodin.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4133
_journal_page_last               4137
_journal_paper_doi               10.1039/c3ob40668g
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         ?C15
_chemical_formula_sum            'C15 H12 Br2 Cl3 N5 O2'
_chemical_formula_weight         560.47
_chemical_name_common            ?acyl
_chemical_name_systematic
; 4,5-dibromo-N-(3-(imidazo[1,2-a]pyrimidin-3-yl)-3-oxopropyl)-1H-pyrrole-2-carboxamide
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.916(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.979(4)
_cell_length_b                   10.814(4)
_cell_length_c                   16.912(6)
_cell_measurement_reflns_used    7374
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.42
_cell_volume                     1977.9(12)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.972
_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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13769
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    4.526
_exptl_absorpt_correction_T_max  0.6603
_exptl_absorpt_correction_T_min  0.3975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4002
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0225P)^2^+3.0013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                3066
_reflns_number_total             4002
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40668g.cif
_cod_data_source_block           rasp15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1977.8(12)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7153758