#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224133.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224133
loop_
_publ_author_name
'Chitradevi, A.'
'Athimoolam, S.'
'Sridhar, B.'
'Bahadur, S. Asath'
_publ_section_title
;
 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium
 2-hydroxybenzoate
;
_journal_coeditor_code           BT5124
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3041
_journal_page_last               o3042
_journal_paper_doi               10.1107/S1600536809045760
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H14 N3 O +, C7 H5 O3 -'
_chemical_formula_moiety         'C11 H14 N3 O +, C7 H5 O3 -'
_chemical_formula_sum            'C18 H19 N3 O4'
_chemical_formula_weight         341.36
_chemical_name_common            '4-aminoantipyrene salicylic acid'
_chemical_name_systematic
;
1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium
2-hydroxybenzoate
;
_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
_audit_creation_method           SHELXTL/PC
_cell_angle_alpha                90.00
_cell_angle_beta                 101.5170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3182(6)
_cell_length_b                   23.3006(16)
_cell_length_c                   8.8503(6)
_cell_measurement_reflns_used    3884
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9
_cell_measurement_theta_min      2.6
_cell_volume                     1680.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2006 ) and PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16025
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      1.339
_exptl_crystal_density_method
;
flotation technique using a liquid-mixture of xylene and carbon tetrachloride
;
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0515P)²+0.4777P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                2599
_reflns_number_total             2959
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5124.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224133
_cod_database_fobs_code          2224133
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'
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
C C1 0.88415(19) 0.55024(6) 0.81347(17) 0.0448(3) Uani d . 1 . .
C C11 1.0648(2) 0.54675(8) 0.8259(2) 0.0584(4) Uani d . 1 . .
H H11A 1.0898 0.5168 0.7597 0.088 Uiso calc R 1 . .
H H11C 1.1164 0.5385 0.9306 0.088 Uiso calc R 1 . .
H H11B 1.1048 0.5827 0.7955 0.088 Uiso calc R 1 . .
N N2 0.81742(15) 0.57725(6) 0.92231(15) 0.0484(3) Uani d . 1 . .
C C22 0.8940(2) 0.62350(8) 1.0208(2) 0.0625(5) Uani d . 1 . .
H H22A 1.0071 0.6143 1.0603 0.094 Uiso calc R 1 . .
H H22B 0.8383 0.6285 1.1050 0.094 Uiso calc R 1 . .
H H22C 0.8874 0.6584 0.9621 0.094 Uiso calc R 1 . .
N N3 0.64810(15) 0.57811(6) 0.86977(15) 0.0496(3) Uani d . 1 . .
C C4 0.60726(19) 0.54839(7) 0.73428(17) 0.0479(4) Uani d . 1 . .
O O4 0.46461(14) 0.53935(6) 0.66452(14) 0.0662(4) Uani d . 1 . .
C C5 0.75999(18) 0.53088(6) 0.70220(16) 0.0442(3) Uani d . 1 . .
N N5 0.77414(16) 0.50034(6) 0.56334(14) 0.0508(3) Uani d . 1 . .
H H5A 0.6744 0.4926 0.5091 0.076 Uiso calc R 1 . .
H H5B 0.8286 0.4677 0.5883 0.076 Uiso calc R 1 . .
H H5C 0.8281 0.5219 0.5071 0.076 Uiso calc R 1 . .
C C31 0.54080(18) 0.60115(7) 0.96225(17) 0.0471(4) Uani d . 1 . .
C C32 0.4479(2) 0.64820(8) 0.9101(2) 0.0619(5) Uani d . 1 . .
H H32 0.4516 0.6640 0.8144 0.074 Uiso calc R 1 . .
C C33 0.3485(2) 0.67208(9) 1.0009(3) 0.0743(6) Uani d . 1 . .
H H33 0.2847 0.7040 0.9661 0.089 Uiso calc R 1 . .
C C34 0.3436(2) 0.64892(10) 1.1417(2) 0.0697(6) Uani d . 1 . .
H H34 0.2785 0.6657 1.2037 0.084 Uiso calc R 1 . .
C C35 0.4341(2) 0.60110(10) 1.1917(2) 0.0680(5) Uani d . 1 . .
H H35 0.4285 0.5850 1.2867 0.082 Uiso calc R 1 . .
C C36 0.5338(2) 0.57665(8) 1.10183(19) 0.0588(4) Uani d . 1 . .
H H36 0.5952 0.5441 1.1354 0.071 Uiso calc R 1 . .
C C41 0.9974(3) 0.38422(8) 0.5503(2) 0.0628(5) Uani d . 1 . .
C C42 1.0840(2) 0.34016(6) 0.47447(17) 0.0493(4) Uani d . 1 . .
C C43 1.2516(2) 0.34179(8) 0.4878(2) 0.0653(5) Uani d . 1 . .
H H43 1.3123 0.3703 0.5472 0.078 Uiso calc R 1 . .
C C44 1.3309(3) 0.30161(12) 0.4140(3) 0.0940(8) Uani d . 1 . .
H H44 1.4445 0.3022 0.4255 0.113 Uiso calc R 1 . .
C C45 1.2386(5) 0.26065(11) 0.3230(3) 0.1051(10) Uani d . 1 . .
H H45 1.2907 0.2340 0.2708 0.126 Uiso calc R 1 . .
C C46 1.0744(4) 0.25848(9) 0.3083(3) 0.0926(8) Uani d . 1 . .
H H46 1.0143 0.2309 0.2452 0.111 Uiso calc R 1 . .
C C47 0.9954(3) 0.29676(8) 0.3861(2) 0.0652(5) Uani d . 1 . .
O O41 1.0717(2) 0.42857(6) 0.60326(16) 0.0872(5) Uani d . 1 . .
O O42 0.8508(2) 0.37591(8) 0.5565(2) 0.0980(5) Uani d . 1 . .
O O43 0.8319(2) 0.29178(8) 0.3741(2) 0.1032(6) Uani d . 1 . .
H H43A 0.8004 0.3156 0.4299 0.155 Uiso calc R 1 . .
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'
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
C5 C1 N2 . . 108.04(13) ?
C5 C1 C11 . . 130.42(14) ?
N2 C1 C11 . . 121.52(13) ?
C1 C11 H11A . . 109.5 ?
C1 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
C1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11C C11 H11B . . 109.5 ?
C1 N2 N3 . . 107.41(12) ?
C1 N2 C22 . . 125.26(14) ?
N3 N2 C22 . . 118.91(13) ?
N2 C22 H22A . . 109.5 ?
N2 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
N2 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C4 N3 N2 . . 110.07(12) ?
C4 N3 C31 . . 128.14(13) ?
N2 N3 C31 . . 121.29(12) ?
O4 C4 N3 . . 124.58(14) ?
O4 C4 C5 . . 131.15(14) ?
N3 C4 C5 . . 104.24(13) ?
C1 C5 C4 . . 110.04(13) ?
C1 C5 N5 . . 127.06(14) ?
C4 C5 N5 . . 122.76(13) ?
C5 N5 H5A . . 109.5 ?
C5 N5 H5B . . 109.5 ?
H5A N5 H5B . . 109.5 ?
C5 N5 H5C . . 109.5 ?
H5A N5 H5C . . 109.5 ?
H5B N5 H5C . . 109.5 ?
C32 C31 C36 . . 120.94(15) ?
C32 C31 N3 . . 118.89(15) ?
C36 C31 N3 . . 120.16(15) ?
C31 C32 C33 . . 119.41(18) ?
C31 C32 H32 . . 120.3 ?
C33 C32 H32 . . 120.3 ?
C34 C33 C32 . . 120.15(19) ?
C34 C33 H33 . . 119.9 ?
C32 C33 H33 . . 119.9 ?
C33 C34 C35 . . 120.15(17) ?
C33 C34 H34 . . 119.9 ?
C35 C34 H34 . . 119.9 ?
C34 C35 C36 . . 120.29(18) ?
C34 C35 H35 . . 119.9 ?
C36 C35 H35 . . 119.9 ?
C31 C36 C35 . . 119.02(18) ?
C31 C36 H36 . . 120.5 ?
C35 C36 H36 . . 120.5 ?
O42 C41 O41 . . 121.88(19) y
O42 C41 C42 . . 118.59(19) ?
O41 C41 C42 . . 119.52(19) ?
C43 C42 C47 . . 118.73(17) ?
C43 C42 C41 . . 121.05(17) ?
C47 C42 C41 . . 120.21(18) ?
C42 C43 C44 . . 120.8(2) ?
C42 C43 H43 . . 119.6 ?
C44 C43 H43 . . 119.6 ?
C45 C44 C43 . . 118.8(2) ?
C45 C44 H44 . . 120.6 ?
C43 C44 H44 . . 120.6 ?
C46 C45 C44 . . 121.2(2) ?
C46 C45 H45 . . 119.4 ?
C44 C45 H45 . . 119.4 ?
C45 C46 C47 . . 120.4(2) ?
C45 C46 H46 . . 119.8 ?
C47 C46 H46 . . 119.8 ?
O43 C47 C46 . . 118.8(2) ?
O43 C47 C42 . . 121.22(18) ?
C46 C47 C42 . . 120.0(2) ?
C47 O43 H43A . . 109.5 ?
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
C1 C5 . 1.354(2) ?
C1 N2 . 1.3585(19) ?
C1 C11 . 1.487(2) ?
C11 H11A . 0.9600 ?
C11 H11C . 0.9600 ?
C11 H11B . 0.9600 ?
N2 N3 . 1.3924(18) ?
N2 C22 . 1.451(2) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
N3 C4 . 1.3675(19) ?
N3 C31 . 1.4306(19) ?
C4 O4 . 1.2414(19) ?
C4 C5 . 1.416(2) y
C5 N5 . 1.4450(18) ?
N5 H5A . 0.8900 ?
N5 H5B . 0.8900 ?
N5 H5C . 0.8900 ?
C31 C32 . 1.367(2) ?
C31 C36 . 1.373(2) ?
C32 C33 . 1.380(3) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.366(3) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.368(3) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.381(3) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C41 O42 . 1.246(2) y
C41 O41 . 1.247(2) y
C41 C42 . 1.489(2) ?
C42 C43 . 1.376(3) ?
C42 C47 . 1.395(2) ?
C43 C44 . 1.382(3) ?
C43 H43 . 0.9300 ?
C44 C45 . 1.379(4) ?
C44 H44 . 0.9300 ?
C45 C46 . 1.347(4) ?
C45 H45 . 0.9300 ?
C46 C47 . 1.372(3) ?
C46 H46 . 0.9300 ?
C47 O43 . 1.348(3) ?
O43 H43A . 0.8200 ?
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
N5 H5A O4 3_666 0.89 1.88 2.696(2) 151.1
N5 H5B O41 . 0.89 2.20 2.949(2) 141.8
N5 H5B O42 . 0.89 2.17 2.972(2) 149.6
N5 H5C O41 3_766 0.89 1.82 2.705(2) 174.9
O43 H43A O42 . 0.82 1.79 2.524(3) 147.5
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
C5 C1 N2 N3 . . . . -4.57(17) ?
C11 C1 N2 N3 . . . . 174.07(14) ?
C5 C1 N2 C22 . . . . -151.94(16) ?
C11 C1 N2 C22 . . . . 26.7(2) ?
C1 N2 N3 C4 . . . . 4.24(17) ?
C22 N2 N3 C4 . . . . 154.04(15) ?
C1 N2 N3 C31 . . . . 176.75(14) ?
C22 N2 N3 C31 . . . . -33.5(2) ?
N2 N3 C4 O4 . . . . 176.11(16) ?
C31 N3 C4 O4 . . . . 4.2(3) ?
N2 N3 C4 C5 . . . . -2.15(17) ?
C31 N3 C4 C5 . . . . -174.00(15) ?
N2 C1 C5 C4 . . . . 3.34(18) ?
C11 C1 C5 C4 . . . . -175.14(16) ?
N2 C1 C5 N5 . . . . 179.12(14) ?
C11 C1 C5 N5 . . . . 0.6(3) ?
O4 C4 C5 C1 . . . . -178.80(18) ?
N3 C4 C5 C1 . . . . -0.71(18) ?
O4 C4 C5 N5 . . . . 5.2(3) ?
N3 C4 C5 N5 . . . . -176.71(14) ?
C4 N3 C31 C32 . . . . -72.0(2) ?
N2 N3 C31 C32 . . . . 116.97(17) ?
C4 N3 C31 C36 . . . . 108.9(2) ?
N2 N3 C31 C36 . . . . -62.1(2) y
C36 C31 C32 C33 . . . . 1.5(3) ?
N3 C31 C32 C33 . . . . -177.62(17) ?
C31 C32 C33 C34 . . . . 0.2(3) ?
C32 C33 C34 C35 . . . . -1.6(3) ?
C33 C34 C35 C36 . . . . 1.4(3) ?
C32 C31 C36 C35 . . . . -1.7(3) ?
N3 C31 C36 C35 . . . . 177.43(15) ?
C34 C35 C36 C31 . . . . 0.2(3) ?
O42 C41 C42 C43 . . . . -168.40(17) ?
O41 C41 C42 C43 . . . . 12.8(2) y
O42 C41 C42 C47 . . . . 12.6(2) ?
O41 C41 C42 C47 . . . . -166.22(16) ?
C47 C42 C43 C44 . . . . 0.6(3) ?
C41 C42 C43 C44 . . . . -178.37(17) ?
C42 C43 C44 C45 . . . . 1.8(3) ?
C43 C44 C45 C46 . . . . -1.6(4) ?
C44 C45 C46 C47 . . . . -1.0(4) ?
C45 C46 C47 O43 . . . . -177.1(2) ?
C45 C46 C47 C42 . . . . 3.4(3) ?
C43 C42 C47 O43 . . . . 177.36(17) ?
C41 C42 C47 O43 . . . . -3.6(2) ?
C43 C42 C47 C46 . . . . -3.2(3) ?
C41 C42 C47 C46 . . . . 175.77(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655939
