5-Amino-1-benzoyl-3-methylpyrazole: complex sheets built from N—H···N, C—H···O and C—H···π(arene) hydrogen bonds
Quiroga, Jairo; Portilla, Jaime; Hursthouse, Michael B.; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 66 (2010) o159–o162; doi:10.1107/S0108270110006980

data_2017610
_publ_section_title
;
 5-Amino-1-benzoyl-3-methylpyrazole: complex sheets built from
 N---H&#x00B7;&#x00B7;&#x00B7;N, C---H&#x00B7;&#x00B7;&#x00B7;O and
 C---H&#x00B7;&#x00B7;&#x00B7;\p(arene) hydrogen bonds
;
_journal_coeditor_code           GG3230
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o159
_journal_page_last               o162
_journal_paper_doi               10.1107/S0108270110006980
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C11 H11 N3 O'
_chemical_formula_sum            'C11 H11 N3 O'
_chemical_formula_weight         201.23
_chemical_name_common            5-Amino-1-benzoyl-3-methylpyrazole
_chemical_name_systematic
;
(5-amino-3-methylpyrazol-1-yl)(phenyl)methanone
;
_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                 106.119(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7443(6)
_cell_length_b                   5.7669(2)
_cell_length_c                   12.0082(3)
_cell_measurement_reflns_used    12071
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.42
_cell_volume                     980.90(6)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg <i>et al.</i>,  2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg <i>et al.</i>,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla <i>et al.</i>,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1919
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0167P)^2^+0.9259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                1673
_reflns_number_total             1919
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gg3230.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017610
_cod_database_fobs_code          2017610