Simple access toward 3-halo- and 3-nitro-pyrazolo[1,5-a]pyrimidines through a one-pot sequence
Castillo, Juan-Carlos; Rosero, Hernán-Alejandro; Portilla, Jaime; RSC Adv. 7 (2017) 28483–; doi:10.1039/C7RA04336H

data_7228349
_publ_section_title
;
 Simple access toward 3-halo- and 3-nitro-pyrazolo[1,5-a]pyrimidines
 through a one-pot sequence
;
_journal_issue                   45
_journal_name_full               'RSC Adv.'
_journal_page_first              28483
_journal_paper_doi               10.1039/C7RA04336H
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C13 H9 Cl I N3'
_chemical_formula_sum            'C13 H9 Cl I N3'
_chemical_formula_weight         369.58
_chemical_melting_point          430
_chemical_name_systematic
7-(4-Chlorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-04-06 deposited with the CCDC.
2017-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                105.748(5)
_cell_angle_beta                 105.605(6)
_cell_angle_gamma                99.832(6)
_cell_formula_units_Z            4
_cell_length_a                   8.1315(6)
_cell_length_b                   12.4851(8)
_cell_length_c                   14.5014(7)
_cell_measurement_reflns_used    18407
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.390
_cell_measurement_theta_min      3.302
_cell_volume                     1316.70(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3072
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            58640
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.484
_diffrn_reflns_theta_min         3.005
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         7387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0361P)^2^+0.8410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5196
_reflns_number_total             7387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra04336h2.cif
_cod_data_source_block           shelxs
_cod_original_cell_volume        1316.71(15)
_cod_database_code               7228349
_shelx_estimated_absorpt_t_min   0.546
_shelx_estimated_absorpt_t_max   0.810
_shelxl_version_number           2014-3
_shelx_res_checksum              10653