Palladium-Catalyzed Intramolecular Cross-Dehydrogenative Coupling: Synthesis of Fused Imidazo[1,2-<i>a</i>]pyrimidines and Pyrazolo[1,5-<i>a</i>]pyrimidines.
Reddy Kotla, Siva K.; Vandavasi, Jaya Kishore; Wang, Jeh-Jeng; Parang, Keykavous; Tiwari, Rakesh K.; ACS omega 2 (2017) 11–19; doi:10.1021/acsomega.6b00417

data_4516832
_publ_section_title
;
 Palladium-Catalyzed Intramolecular Cross-Dehydrogenative Coupling:
 Synthesis of Fused Imidazo[1,2-<i>a</i>]pyrimidines and
 Pyrazolo[1,5-<i>a</i>]pyrimidines.
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_journal_issue                   1
_journal_name_full               'ACS omega'
_journal_page_first              11
_journal_page_last               19
_journal_paper_doi               10.1021/acsomega.6b00417
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         'C19 H13 N3 O'
_chemical_formula_sum            'C19 H13 N3 O'
_chemical_formula_weight         299.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 94.43(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8882(7)
_cell_length_b                   9.1020(5)
_cell_length_c                   13.5891(7)
_cell_measurement_reflns_used    190
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      48.5374
_cell_measurement_theta_min      8.0902
_cell_volume                     1466.03(15)
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection
'Bruker Instrument Service v6.2.0 (Bruker AXS Inc. 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS)'
_computing_structure_refinement  'XL v2014/7 (Shedrick, 2015)'
_computing_structure_solution    'XT, VERSION 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33036
_diffrn_reflns_theta_full        55.58
_diffrn_reflns_theta_max         55.58
_diffrn_reflns_theta_min         4.14
_diffrn_source                   'liquid metaljet'
_diffrn_source_type              'Excillium D2'
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  0.2006
_exptl_absorpt_correction_T_min  0.1094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. (2015). J. Appl.
Cryst. 48, 3-10.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+1.8249P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1734
_reflns_number_gt                2374
_reflns_number_total             2784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao6b00417_si_001.cif
_cod_data_source_block           skr53
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_database_code               4516832
_shelx_res_checksum              32937
_shelx_hkl_checksum              56549