#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/76/2017626.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_2017626
loop_
_publ_author_name
'Hazra, Dipak K.'
'Chatterjee, Rajarshi'
'Ali, Mahammad'
'Mukherjee, Monika'
_publ_section_title
;
 4-(3,5-Dimethyl-1H-pyrazol-4-ylmethyl)-3,5-dimethyl-1H-pyrazol-2-ium
 dihydrogen phosphate: a combined X-ray and DFT study
;
_journal_coeditor_code           SK3363
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o190
_journal_page_last               o193
_journal_paper_doi               10.1107/S0108270110007134
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H17 N4 + , H2 O4 P -'
_chemical_formula_moiety         'C11 H17 N4 + , H2 O4 P -'
_chemical_formula_sum            'C11 H19 N4 O4 P'
_chemical_formula_weight         302.27
_chemical_name_systematic
;
4-(3,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,5-dimethyl-1H-
pyrazol-2-ium dihydrogen phosphate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                117.624(3)
_cell_angle_beta                 104.576(4)
_cell_angle_gamma                94.663(4)
_cell_formula_units_Z            2
_cell_length_a                   7.649(4)
_cell_length_b                   10.504(2)
_cell_length_c                   10.538(2)
_cell_measurement_reflns_used    1408
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.18
_cell_measurement_theta_min      2.28
_cell_volume                     706.4(4)
_computing_cell_refinement
;
APEX2 (Bruker, 2007) and SAINT (Bruker, 2007)
;
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction
;
SAINT (Bruker, 2007) and XPREP (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII Kappa CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4686
_diffrn_reflns_theta_full        24.18
_diffrn_reflns_theta_max         24.18
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flake
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.380
_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     189
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0706P)²+0.0452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                1536
_reflns_number_total             2239
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3363.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (10
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        706.4(5)
_cod_database_code               2017626
_cod_database_fobs_code          2017626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
P P1 0.39358(13) 0.05811(10) -0.31027(10) 0.0380(3) Uani d . 1 . .
O O1 0.3604(3) -0.0879(2) -0.4499(3) 0.0489(7) Uani d . 1 . .
O O2 0.4609(3) 0.0548(3) -0.1632(2) 0.0494(7) Uani d . 1 . .
O O3 0.5414(4) 0.1740(3) -0.3051(3) 0.0508(7) Uani d . 1 . .
H H3A 0.5581 0.1402 -0.3874 0.076 Uiso calc R 1 . .
O O4 0.2154(4) 0.1154(3) -0.3088(4) 0.0644(8) Uani d . 1 . .
H H4 0.2244 0.1867 -0.3215 0.097 Uiso calc R 1 . .
N N1 0.0607(4) 0.6786(3) 0.3971(3) 0.0440(8) Uani d . 1 . .
H H1 0.1403 0.7620 0.4517 0.053 Uiso calc R 1 . .
N N2 0.2495(4) 0.1435(3) 0.0302(3) 0.0435(8) Uani d . 1 . .
H H2 0.3054 0.1305 -0.0347 0.052 Uiso calc R 1 . .
N N3 0.2854(4) 0.0944(3) 0.1294(3) 0.0403(7) Uani d . 1 . .
H H3 0.3682 0.0459 0.1390 0.048 Uiso calc R 1 . .
N N4 -0.1193(4) 0.6618(3) 0.3240(3) 0.0415(7) Uani d . 1 . .
C C1 0.1130(5) 0.2159(4) 0.0482(4) 0.0415(9) Uani d . 1 . .
C C2 0.0441(7) 0.2893(5) -0.0399(5) 0.0702(13) Uani d . 1 . .
H H2A 0.1072 0.3917 0.0169 0.123(6) Uiso calc R 1 . .
H H2B -0.0869 0.2810 -0.0587 0.123(6) Uiso calc R 1 . .
H H2C 0.0677 0.2425 -0.1347 0.123(6) Uiso calc R 1 . .
C C3 0.1765(6) 0.1002(5) 0.3339(4) 0.0576(11) Uani d . 1 . .
H H3B 0.2521 0.0304 0.3280 0.123(6) Uiso calc R 1 . .
H H3C 0.0531 0.0590 0.3226 0.123(6) Uiso calc R 1 . .
H H3D 0.2286 0.1893 0.4304 0.123(6) Uiso calc R 1 . .
C C4 0.1696(5) 0.1342(4) 0.2109(4) 0.0372(8) Uani d . 1 . .
C C5 0.0586(5) 0.2114(3) 0.1613(4) 0.0355(8) Uani d . 1 . .
C C6 -0.0901(5) 0.2780(4) 0.2208(4) 0.0439(9) Uani d . 1 . .
H H6A -0.0971 0.2583 0.3009 0.053 Uiso calc R 1 . .
H H6B -0.2085 0.2293 0.1398 0.053 Uiso calc R 1 . .
C C7 -0.0611(4) 0.4416(3) 0.2815(4) 0.0339(8) Uani d . 1 . .
C C8 -0.1938(5) 0.5165(4) 0.2529(4) 0.0370(8) Uani d . 1 . .
C C9 -0.3950(5) 0.4581(4) 0.1581(4) 0.0592(11) Uani d . 1 . .
H H9A -0.4536 0.5391 0.1735 0.123(6) Uiso calc R 1 . .
H H9B -0.4545 0.3966 0.1870 0.123(6) Uiso calc R 1 . .
H H9C -0.4059 0.4011 0.0530 0.123(6) Uiso calc R 1 . .
C C10 0.1002(5) 0.5482(4) 0.3742(4) 0.0366(8) Uani d . 1 . .
C C11 0.2918(5) 0.5410(4) 0.4450(4) 0.0567(11) Uani d . 1 . .
H H11A 0.3556 0.5111 0.3717 0.123(6) Uiso calc R 1 . .
H H11B 0.2849 0.4708 0.4788 0.123(6) Uiso calc R 1 . .
H H11C 0.3582 0.6366 0.5299 0.123(6) 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'
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'
P P 0.1023 0.0942 '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'
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
O1 P1 O2 . . 114.01(15) ?
O1 P1 O4 . . 111.46(17) ?
O2 P1 O4 . . 105.64(15) ?
O1 P1 O3 . . 109.37(13) ?
O2 P1 O3 . . 108.22(15) ?
O4 P1 O3 . . 107.89(16) ?
P1 O3 H3A . . 109.5 ?
P1 O4 H4 . . 109.5 ?
N4 N1 C10 . . 111.6(3) ?
N4 N1 H1 . . 124.2 ?
C10 N1 H1 . . 124.2 ?
C1 N2 N3 . . 109.5(3) ?
C1 N2 H2 . . 125.2 ?
N3 N2 H2 . . 125.2 ?
C4 N3 N2 . . 108.3(3) ?
C4 N3 H3 . . 125.8 ?
N2 N3 H3 . . 125.8 ?
C8 N4 N1 . . 105.2(3) ?
N2 C1 C5 . . 107.7(3) ?
N2 C1 C2 . . 123.4(3) ?
C5 C1 C2 . . 128.9(3) ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C4 C3 H3D . . 109.5 ?
H3B C3 H3D . . 109.5 ?
H3C C3 H3D . . 109.5 ?
N3 C4 C5 . . 107.9(3) ?
N3 C4 C3 . . 122.0(3) ?
C5 C4 C3 . . 130.1(3) ?
C1 C5 C4 . . 106.5(3) ?
C1 C5 C6 . . 126.8(3) ?
C4 C5 C6 . . 126.6(3) ?
C5 C6 C7 . . 114.5(3) ?
C5 C6 H6A . . 108.6 ?
C7 C6 H6A . . 108.6 ?
C5 C6 H6B . . 108.6 ?
C7 C6 H6B . . 108.6 ?
H6A C6 H6B . . 107.6 ?
C10 C7 C8 . . 105.4(3) ?
C10 C7 C6 . . 127.9(3) ?
C8 C7 C6 . . 126.6(3) ?
N4 C8 C7 . . 110.7(3) ?
N4 C8 C9 . . 119.5(3) ?
C7 C8 C9 . . 129.8(3) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N1 C10 C7 . . 107.0(3) ?
N1 C10 C11 . . 120.7(3) ?
C7 C10 C11 . . 132.3(3) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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
P1 O1 . 1.496(2) y
P1 O2 . 1.523(2) y
P1 O3 . 1.565(2) y
P1 O4 . 1.535(3) y
O3 H3A . 0.8200 ?
O4 H4 . 0.8200 ?
N1 N4 . 1.349(4) y
N1 C10 . 1.350(4) y
N1 H1 . 0.8600 ?
N2 C1 . 1.341(4) y
N2 N3 . 1.346(4) y
N2 H2 . 0.8600 ?
N3 C4 . 1.344(4) y
N3 H3 . 0.8600 ?
N4 C8 . 1.341(4) y
C1 C5 . 1.377(5) ?
C1 C2 . 1.489(5) ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C3 C4 . 1.485(5) ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C3 H3D . 0.9600 ?
C4 C5 . 1.390(5) ?
C5 C6 . 1.502(5) ?
C6 C7 . 1.503(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C10 . 1.373(4) ?
C7 C8 . 1.392(5) ?
C8 C9 . 1.500(5) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.493(5) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
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
N1 H1 O1 1_566 0.86 1.89 2.726(4) 164.0
N2 H2 O2 . 0.86 1.96 2.789(4) 161.3
N3 H3 O2 2_655 0.86 1.79 2.649(4) 178.4
O3 H3A O1 2_654 0.82 1.83 2.639(3) 169.0
O4 H4 N4 2_565 0.82 1.85 2.571(4) 146.3
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
C1 N2 N3 C4 . . . . 0.7(4) ?
C10 N1 N4 C8 . . . . -0.3(4) ?
N3 N2 C1 C5 . . . . -0.7(4) ?
N3 N2 C1 C2 . . . . 177.6(3) ?
N2 N3 C4 C5 . . . . -0.3(4) ?
N2 N3 C4 C3 . . . . -178.3(3) ?
N2 C1 C5 C4 . . . . 0.5(4) ?
C2 C1 C5 C4 . . . . -177.7(4) ?
N2 C1 C5 C6 . . . . 179.9(3) ?
C2 C1 C5 C6 . . . . 1.7(6) ?
N3 C4 C5 C1 . . . . -0.1(4) ?
C3 C4 C5 C1 . . . . 177.7(4) ?
N3 C4 C5 C6 . . . . -179.5(3) ?
C3 C4 C5 C6 . . . . -1.8(6) ?
C1 C5 C6 C7 . . . . -57.8(5) y
C4 C5 C6 C7 . . . . 121.5(4) ?
C5 C6 C7 C10 . . . . -44.3(5) y
C5 C6 C7 C8 . . . . 134.6(4) ?
N1 N4 C8 C7 . . . . 0.2(4) ?
N1 N4 C8 C9 . . . . -179.4(3) ?
C10 C7 C8 N4 . . . . -0.1(4) ?
C6 C7 C8 N4 . . . . -179.2(3) ?
C10 C7 C8 C9 . . . . 179.5(3) ?
C6 C7 C8 C9 . . . . 0.4(6) ?
N4 N1 C10 C7 . . . . 0.2(4) ?
N4 N1 C10 C11 . . . . -179.9(3) ?
C8 C7 C10 N1 . . . . 0.0(4) ?
C6 C7 C10 N1 . . . . 179.1(3) ?
C8 C7 C10 C11 . . . . -180.0(4) ?
C6 C7 C10 C11 . . . . -0.9(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654233
