Domino Reaction of Arylglyoxals with Pyrazol-5-amines: Selective Access to Pyrazolo-Fused 1,7-Naphthyridines, 1,3-Diazocanes, and Pyrroles.
Jiang, Bo; Fan, Wei; Sun, Mu-Yan; Ye, Qin; Wang, Shu-Liang; Tu, Shu-Jiang; Li, Guigen; The Journal of organic chemistry 79 (2014) 5258–5268; doi:10.1021/jo500823z

data_4029475
_publ_section_title
;
 Domino Reaction of Arylglyoxals with Pyrazol-5-amines: Selective Access
 to Pyrazolo-Fused 1,7-Naphthyridines, 1,3-Diazocanes, and Pyrroles.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5258
_journal_page_last               5268
_journal_paper_doi               10.1021/jo500823z
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C28 H22 Br2 N4 O'
_chemical_formula_weight         590.32
_chemical_name_systematic
; 
 ? 
;
_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                 105.394(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.4011(16)
_cell_length_b                   6.1969(5)
_cell_length_c                   23.223(2)
_cell_measurement_reflns_used    1146
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.637
_cell_measurement_theta_min      3.433
_cell_volume                     2553.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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
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_diffrn_reflns_av_R_equivalents  0.3029
_diffrn_reflns_av_sigmaI/netI    0.2884
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12254
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    3.203
_exptl_absorpt_correction_T_max  0.8310
_exptl_absorpt_correction_T_min  0.4784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.026
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.2586
_refine_ls_R_factor_gt           0.1119
_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^)+(0.0362P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2151
_refine_ls_wR_factor_ref         0.2560
_reflns_number_gt                1317
_reflns_number_total             4511
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500823z_si_005.cif
_cod_data_source_block           130621a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 

 Adding full bibliography for 4029474--4029477.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4029475