Unusual rearrangement of imidazo[1,5-a]imidazoles and imidazo[1,2-b]pyrazoles into imidazo[1,5-a]pyrimidines and pyrazolo[1,5-a]pyrimidines
Gambouz, Khadija; Driowya, Mohsine; Loubidi, Mohammed; Tber, Zahira; Allouchi, Hassan; El Kazzouli, Saïd; Akssira, Mohamed; Guillaumet, Gérald; RSC Advances 9 (2019) 29051–; doi:10.1039/C9RA04609G

data_7233879
_publ_section_title
;
 Unusual rearrangement of imidazo[1,5-a]imidazoles and
 imidazo[1,2-b]pyrazoles into imidazo[1,5-a]pyrimidines and
 pyrazolo[1,5-a]pyrimidines
;
_journal_issue                   50
_journal_name_full               'RSC Advances'
_journal_page_first              29051
_journal_paper_doi               10.1039/C9RA04609G
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C18 H17 N5 O'
_chemical_formula_weight         319.36
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-02-27 deposited with the CCDC.    2019-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.246(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7895(4)
_cell_length_b                   14.8634(7)
_cell_length_c                   10.0794(5)
_cell_measurement_reflns_used    2845
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      24.6740
_cell_measurement_theta_min      3.8540
_cell_volume                     1615.18(13)
_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_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -25.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5424  -99.0000 -180.0000 49

  2 omega -106.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5424  -57.0000 -120.0000 115

  3 omega   35.00  112.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2612  178.0000  120.0000 77

  4 omega  -43.00   31.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5424   57.0000 -150.0000 74

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0407142000
_diffrn_orient_matrix_UB_12      -0.0276662000
_diffrn_orient_matrix_UB_13      0.0390293000
_diffrn_orient_matrix_UB_21      0.0054447000
_diffrn_orient_matrix_UB_22      0.0343665000
_diffrn_orient_matrix_UB_23      0.0486979000
_diffrn_orient_matrix_UB_31      -0.0513766000
_diffrn_orient_matrix_UB_32      -0.0182106000
_diffrn_orient_matrix_UB_33      0.0326302000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9923
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.407
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: m\'ethanol / chloroforme'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0434P)^2^+0.3059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2235
_reflns_number_total             3302
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {4a4e51ad-31c7-4edb-a666-22580edb7464}
_cod_data_source_file            c9ra04609g2.cif
_cod_data_source_block           lou1-b_170k
_cod_database_code               7233879
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              22399
_publcif_funding_html
;
;