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###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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# This file may be used for bona fide research purposes within the           #
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data_global
_audit_creation_method     'from SHELXL-97'
_journal_date_recd_electronic     2010-02-22
_journal_date_accepted     2010-02-23
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o159
_journal_page_last     o162
_journal_paper_category     FO
_journal_coeditor_code     GG3230
_publ_contact_author_name     'Professor Christopher Glidewell'
_publ_contact_author_address
;
University of St Andrews
Fife KY16 9ST
Scotland
;
_publ_contact_author_email     cg@st-andrews.ac.uk
_publ_contact_author_fax     '+1334-463808'
_publ_contact_author_phone     '+1334-463839'
_publ_section_title
;
5-Amino-1-benzoyl-3-methylpyrazole: complex sheets built from N---H...N,
C---H...O and C---H...π(arene) hydrogen bonds
;
loop_
    _publ_author_name
    _publ_author_address
    'Quiroga, Jairo'
;
Departamento de Química
Universidad de Valle
AA 25360 Cali
Colombia
;
    'Portilla, Jaime'
;
Grupo de Investigación en Compuestos Bio-orgánicos
Departamento de Química
Universidad de los Andes
Cra. 1E No. 18A-10, Edificio H
AA 4976 Bogotá D.C.
Colombia
;
    'Hursthouse, Michael B.'
;
School of Chemistry
University of Southampton
Highfield
Southampton SO17 1BJ
England
;
    'Cobo, Justo'
;
Departamento de Química Inorgánica y Orgánica
Universidad de Jaén
23071 Jaén
Spain
;
    'Glidewell, Christopher'
;
School of Chemistry
University of St Andrews
St Andrews
Fife KY16 9ST
Scotland
;
data_I
_chemical_name_systematic
;
(5-amino-3-methylpyrazol-1-yl)(phenyl)methanone
;
_chemical_name_common     '5-Amino-1-benzoyl-3-methylpyrazole'
_chemical_formula_moiety     'C11 H11 N3 O'
_chemical_formula_sum     'C11 H11 N3 O'
_chemical_formula_weight     201.23
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     14.7443(6)
_cell_length_b     5.7669(2)
_cell_length_c     12.0082(3)
_cell_angle_alpha     90.00
_cell_angle_beta     106.119(2)
_cell_angle_gamma     90.00
_cell_volume     980.90(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     12071
_cell_measurement_theta_min     3.42
_cell_measurement_theta_max     27.49
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.363
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     424
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.982
_exptl_absorpt_correction_T_max     0.993
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     1919
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0385
_diffrn_reflns_theta_min     3.42
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -6
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     1919
_reflns_number_gt     1673
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0633
_refine_ls_R_factor_gt     0.0537
_refine_ls_wR_factor_gt     0.1100
_refine_ls_wR_factor_ref     0.1129
_refine_ls_goodness_of_fit_ref     1.197
_refine_ls_restrained_S_all     1.197
_refine_ls_number_reflns     1919
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0167P)²+0.9259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.221
_refine_diff_density_min     -0.202
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1999)'
_computing_cell_refinement     'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_reduction     'EVALCCD (Duisenberg et al.,  2003)'
_computing_structure_solution     'SIR2004 (Burla et al.,  2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.20857(11) 0.7648(3) 0.46776(14) 0.0169(4) Uani d . 1 . .
    N N2 0.17823(12) 0.5803(3) 0.52468(14) 0.0174(4) Uani d . 1 . .
    C C3 0.11733(14) 0.4671(4) 0.44037(17) 0.0195(5) Uani d . 1 . .
    C C4 0.10605(15) 0.5706(4) 0.33066(18) 0.0222(5) Uani d . 1 . .
    H H4 0.0665 0.5181 0.2585 0.027 Uiso calc R 1 . .
    C C5 0.16335(14) 0.7615(4) 0.34908(17) 0.0195(5) Uani d . 1 . .
    C C11 0.27686(14) 0.9182(4) 0.52861(18) 0.0179(4) Uani d . 1 . .
    O O11 0.29408(11) 1.0967(3) 0.48344(13) 0.0247(4) Uani d . 1 . .
    C C111 0.32752(14) 0.8565(4) 0.65061(17) 0.0165(4) Uani d . 1 . .
    C C112 0.37538(14) 0.6463(4) 0.67863(17) 0.0175(4) Uani d . 1 . .
    H H112 0.3715 0.5319 0.6206 0.021 Uiso calc R 1 . .
    C C113 0.42857(14) 0.6055(4) 0.79143(18) 0.0207(5) Uani d . 1 . .
    H H113 0.4633 0.4653 0.8102 0.025 Uiso calc R 1 . .
    C C114 0.43127(14) 0.7690(4) 0.87716(18) 0.0223(5) Uani d . 1 . .
    H H114 0.4668 0.7385 0.9548 0.027 Uiso calc R 1 . .
    C C115 0.38249(15) 0.9765(4) 0.85033(18) 0.0225(5) Uani d . 1 . .
    H H115 0.3835 1.0866 0.9095 0.027 Uiso calc R 1 . .
    C C116 0.33197(14) 1.0226(4) 0.73593(18) 0.0195(5) Uani d . 1 . .
    H H116 0.3007 1.1672 0.7163 0.023 Uiso calc R 1 . .
    C C31 0.06761(15) 0.2591(4) 0.46859(19) 0.0246(5) Uani d . 1 . .
    H H31A 0.0916 0.2244 0.5515 0.037 Uiso calc R 1 . .
    H H31B 0.0789 0.1262 0.4234 0.037 Uiso calc R 1 . .
    H H31C -0.0003 0.2903 0.4494 0.037 Uiso calc R 1 . .
    N N51 0.17776(14) 0.9329(4) 0.27829(17) 0.0252(4) Uani d . 1 . .
    H H51A 0.1690(18) 0.894(4) 0.204(2) 0.030 Uiso d . 1 . .
    H H51B 0.2260(18) 1.034(5) 0.313(2) 0.030 Uiso d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.0185(8) 0.0204(9) 0.0121(8) 0.0014(7) 0.0049(6) 0.0013(7)
    N2 0.0188(9) 0.0188(9) 0.0151(8) 0.0002(7) 0.0052(7) 0.0004(7)
    C3 0.0160(10) 0.0239(11) 0.0185(10) 0.0035(8) 0.0044(8) -0.0051(9)
    C4 0.0185(10) 0.0313(12) 0.0148(10) 0.0032(9) 0.0012(8) -0.0048(9)
    C5 0.0197(10) 0.0279(11) 0.0115(9) 0.0078(9) 0.0051(8) -0.0004(9)
    C11 0.0191(10) 0.0168(10) 0.0196(10) 0.0019(8) 0.0083(8) -0.0010(9)
    O11 0.0303(8) 0.0220(8) 0.0226(8) -0.0007(7) 0.0083(7) 0.0042(7)
    C111 0.0147(9) 0.0184(10) 0.0173(10) -0.0029(8) 0.0056(8) -0.0004(8)
    C112 0.0176(10) 0.0190(10) 0.0174(10) -0.0020(8) 0.0073(8) -0.0033(9)
    C113 0.0175(10) 0.0212(11) 0.0226(11) -0.0012(9) 0.0043(8) 0.0026(9)
    C114 0.0193(10) 0.0300(12) 0.0159(10) -0.0064(9) 0.0020(8) 0.0018(9)
    C115 0.0233(11) 0.0248(11) 0.0197(10) -0.0087(9) 0.0064(9) -0.0084(9)
    C116 0.0191(10) 0.0176(10) 0.0233(11) -0.0018(8) 0.0081(9) -0.0028(9)
    C31 0.0212(10) 0.0248(11) 0.0268(12) -0.0023(9) 0.0048(9) -0.0057(10)
    N51 0.0311(11) 0.0310(11) 0.0141(9) 0.0036(9) 0.0073(8) 0.0026(8)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C11 . 1.386(3) ?
    N1 C5 . 1.396(2) ?
    N1 N2 . 1.404(2) ?
    N2 C3 . 1.324(3) ?
    C3 C4 . 1.413(3) ?
    C3 C31 . 1.493(3) ?
    C4 C5 . 1.368(3) ?
    C4 H4 . 0.9500 ?
    C5 N51 . 1.359(3) ?
    C11 O11 . 1.223(3) ?
    C11 C111 . 1.491(3) ?
    C111 C116 . 1.391(3) ?
    C111 C112 . 1.396(3) ?
    C112 C113 . 1.384(3) ?
    C112 H112 . 0.9500 ?
    C113 C114 . 1.388(3) ?
    C113 H113 . 0.9500 ?
    C114 C115 . 1.388(3) ?
    C114 H114 . 0.9500 ?
    C115 C116 . 1.395(3) ?
    C115 H115 . 0.9500 ?
    C116 H116 . 0.9500 ?
    C31 H31A . 0.9800 ?
    C31 H31B . 0.9800 ?
    C31 H31C . 0.9800 ?
    N51 H51A . 0.89(3) ?
    N51 H51B . 0.92(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C11 N1 C5 . . 128.18(18) ?
    C11 N1 N2 . . 120.68(16) ?
    C5 N1 N2 . . 111.12(16) ?
    C3 N2 N1 . . 103.98(16) ?
    N2 C3 C4 . . 112.58(19) ?
    N2 C3 C31 . . 119.60(19) ?
    C4 C3 C31 . . 127.79(19) ?
    C5 C4 C3 . . 106.36(18) ?
    C5 C4 H4 . . 126.8 ?
    C3 C4 H4 . . 126.8 ?
    N51 C5 C4 . . 133.0(2) ?
    N51 C5 N1 . . 121.0(2) ?
    C4 C5 N1 . . 105.95(18) ?
    O11 C11 N1 . . 120.88(18) ?
    O11 C11 C111 . . 121.85(19) ?
    N1 C11 C111 . . 117.27(17) ?
    C116 C111 C112 . . 120.22(18) ?
    C116 C111 C11 . . 117.89(18) ?
    C112 C111 C11 . . 121.72(18) ?
    C113 C112 C111 . . 119.66(19) ?
    C113 C112 H112 . . 120.2 ?
    C111 C112 H112 . . 120.2 ?
    C112 C113 C114 . . 120.1(2) ?
    C112 C113 H113 . . 119.9 ?
    C114 C113 H113 . . 119.9 ?
    C115 C114 C113 . . 120.49(19) ?
    C115 C114 H114 . . 119.8 ?
    C113 C114 H114 . . 119.8 ?
    C114 C115 C116 . . 119.6(2) ?
    C114 C115 H115 . . 120.2 ?
    C116 C115 H115 . . 120.2 ?
    C111 C116 C115 . . 119.8(2) ?
    C111 C116 H116 . . 120.1 ?
    C115 C116 H116 . . 120.1 ?
    C3 C31 H31A . . 109.5 ?
    C3 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C3 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    C5 N51 H51A . . 116.0(17) ?
    C5 N51 H51B . . 114.0(16) ?
    H51A N51 H51B . . 119(2) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C11 N1 N2 C3 . . . . -177.29(17) ?
    C5 N1 N2 C3 . . . . 1.1(2) ?
    N1 N2 C3 C4 . . . . -0.4(2) ?
    N1 N2 C3 C31 . . . . -178.53(17) ?
    N2 C3 C4 C5 . . . . -0.5(2) ?
    C31 C3 C4 C5 . . . . 177.4(2) ?
    C3 C4 C5 N51 . . . . -175.7(2) ?
    C3 C4 C5 N1 . . . . 1.2(2) ?
    C11 N1 C5 N51 . . . . -5.9(3) ?
    N2 N1 C5 N51 . . . . 175.85(18) ?
    C11 N1 C5 C4 . . . . 176.79(19) ?
    N2 N1 C5 C4 . . . . -1.5(2) ?
    C5 N1 C11 O11 . . . . 12.2(3) ?
    N2 N1 C11 O11 . . . . -169.68(18) y
    C5 N1 C11 C111 . . . . -168.10(18) ?
    N2 N1 C11 C111 . . . . 10.0(3) y
    O11 C11 C111 C116 . . . . 50.9(3) ?
    N1 C11 C111 C116 . . . . -128.8(2) ?
    O11 C11 C111 C112 . . . . -124.3(2) ?
    N1 C11 C111 C112 . . . . 56.0(3) y
    C116 C111 C112 C113 . . . . -1.0(3) ?
    C11 C111 C112 C113 . . . . 174.09(19) ?
    C111 C112 C113 C114 . . . . 2.5(3) ?
    C112 C113 C114 C115 . . . . -1.4(3) ?
    C113 C114 C115 C116 . . . . -1.3(3) ?
    C112 C111 C116 C115 . . . . -1.6(3) ?
    C11 C111 C116 C115 . . . . -176.92(18) ?
    C114 C115 C116 C111 . . . . 2.8(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N51 H51A N2 4_575 0.89(2) 2.20(2) 3.048(2) 158(2) y
    N51 H51B O11 . 0.92(3) 2.05(2) 2.749(3) 132(2) y
    C115 H115 O11 4_586 0.95 2.55 3.387(3) 147 y
    C113 H113 Cg 2_646 0.95 2.84 3.514(2) 128 y
