6-(Aryldiazenyl)pyrazolo[1,5-a]pyrimidines as Strategic Intermediates for the Synthesis of Pyrazolo[5,1-b]purines.
Castillo, Juan-Carlos; Estupiñan, Diego; Nogueras, Manuel; Cobo, Justo; Portilla, Jaime; The Journal of organic chemistry 81 (2016) 12364–12373; doi:10.1021/acs.joc.6b02431

data_4037462
_publ_section_title
;
 6-(Aryldiazenyl)pyrazolo[1,5-a]pyrimidines as Strategic Intermediates for
 the Synthesis of Pyrazolo[5,1-b]purines.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12364
_journal_page_last               12373
_journal_paper_doi               10.1021/acs.joc.6b02431
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C10 H9 N3 O'
_chemical_formula_weight         187.2
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-09-26T20:14:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.352(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8354(5)
_cell_length_b                   11.3494(10)
_cell_length_c                   12.1390(9)
_cell_measurement_reflns_used    191
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      3.60
_cell_volume                     912.33(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2014 (Giacovazzo et al, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3695
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        27.485
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.494
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS-2012/1 - Bruker AXS scaling for twinned crystals.
two twin component present,
twin fraction 0.5/0.5 related by 
Rotation angle  (degrees)         : 179.946
Rotation vector (laboratory)      :  -0.3464 -0.8574  0.3807
Rotation vector (reciprocal cell) :  -0.00   -0.00    1.00
Rotation vector (direct cell)     :  10.98   -0.01   25.00

Unit cell relationships           : a' =  -1 * a                
                                    b' =          +1 * b        
                                    c' =                  -1 * c 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       neddles
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1073P)^2^+0.4118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.175
_reflns_Friedel_coverage         0
_reflns_number_gt                3284
_reflns_number_total             3695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02431_si_001.cif
_cod_data_source_block           3'a
_cod_depositor_comments
;
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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037462
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              26104
_shelx_hkl_checksum              42081