Hydrogen-bonded chains in isostructural 5-methyl-2-(4-methylphenyl)-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine, 2-(4-chlorophenyl)-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine and 2-(4-bromophenyl)-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine, and sheets of π-stacked hydrogen-bonded chains in 2-(4-methoxyphenyl)-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine
Portilla, Jaime; Quiroga, Jairo; Cobo, Justo; Low, John N.; Glidewell, Christopher; Acta Crystallographica Section C 61 (2005) o452–o456; doi:10.1107/S0108270105016720

data_2015052
_publ_section_title
;Hydrogen-bonded chains in isostructural
 5-methyl-2-(4-methylphenyl)-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine,
 2-(4-chlorophenyl)-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine
 and
 2-(4-bromophenyl)-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine,
 and sheets of \p-stacked hydrogen-bonded chains in
 2-(4-methoxyphenyl)-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o452
_journal_page_last               o456
_journal_paper_doi               10.1107/S0108270105016720
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H14 Cl N3'
_chemical_formula_moiety         'C16 H14 Cl N3'
_chemical_formula_sum            'C16 H14 Cl N3'
_chemical_formula_weight         283.75
_chemical_name_systematic
;
2-(4-chlorophenyl)-5-methyl-7,8-dihydro-6H-
cyclopenta[g]pyrazolo[1,5-a]pyrimidine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 106.980(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6800(11)
_cell_length_b                   6.6669(6)
_cell_length_c                   15.2010(16)
_cell_measurement_reflns_used    3040
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      3.36
_cell_volume                     1325.9(2)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement
'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'WinGX (Farrugia, 1999) and SIR92 (Altomare <i>et al.</i>, 1993)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR91 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14750
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         3.36
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.494
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0726P)^2^+0.3419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                2060
_reflns_number_total             3040
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1849.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015052