#------------------------------------------------------------------------------
#$Date: 2015-06-07 03:21:15 +0300 (Sun, 07 Jun 2015) $
#$Revision: 138733 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/51/7035104.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7035104
loop_
_publ_author_name
'Bryant, Macguire R.'
'Burrows, Andrew D.'
'Fitchett, Christopher M.'
'Hawes, Chris S.'
'Hunter, Sally O.'
'Keenan, Luke L.'
'Kelly, David J.'
'Kruger, Paul E.'
'Mahon, Mary F.'
'Richardson, Christopher'
_publ_section_title
;
 The synthesis and characterisation of coordination and hydrogen-bonded
 networks based on 4-(3,5-dimethyl-1H-pyrazol-4-yl)benzoic acid.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9269
_journal_page_last               9280
_journal_paper_doi               10.1039/c5dt00011d
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C12 H13 N2 O2, N O3'
_chemical_formula_sum            'C12 H13 N3 O5'
_chemical_formula_weight         279.25
_chemical_name_common
'4-(3,5-dimethyl-1H,2H-pyrazolium-4-yl)benzoic acid nitrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2014-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-03-12 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                72.810(4)
_cell_angle_beta                 70.221(4)
_cell_angle_gamma                78.066(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4272(4)
_cell_length_b                   8.9566(6)
_cell_length_c                   10.4607(6)
_cell_measurement_reflns_used    1852
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      22.42
_cell_measurement_theta_min      2.79
_cell_volume                     621.14(7)
_computing_data_reduction        'SAINT v7.53A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XLMP (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0961
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14759
_diffrn_reflns_theta_full        28.43
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         2.79
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.704295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                1604
_reflns_number_total             3077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt00011d2.cif
_cod_data_source_block           csh27
_cod_depositor_comments
'Adding full bibliography for 7035103--7035111.cif.'
_cod_original_cell_volume        621.14(6)
_cod_database_code               7035104
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.03) H6(0.029) H3(0.027) H1(0.03) H2B(0.027) H5(0.03)
 H51A(0.044) H51B(0.044) H51C(0.044) H31A(0.048) H31B(0.048) H31C(0.048)
 Fixed X: H6(0.4881) H3(-0.1371) H2B(0.0293) H5(0.3244) H51A(0.2035)
 H51B(0.1021) H51C(0.0086) H31A(-0.3441) H31B(-0.131) H31C(-0.2868)
 Fixed Y: H6(0.3696) H3(0.2432) H2B(0.339) H5(0.2652) H51A(0.2847)
 H51B(0.4325) H51C(0.3806) H31A(0.0557) H31B(-0.035) H31C(-0.1045)
 Fixed Z: H6(0.6453) H3(0.8904) H2B(0.9955) H5(0.5436) H51A(0.335)
 H51B(0.4005) H51C(0.3054) H31A(0.9128) H31B(0.8964) H31C(0.8624)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.2982(2) 0.43256(19) 1.02639(14) 0.0286(4) Uani 1 d .
O3 O 0.5390(2) 0.0987(2) 0.36388(15) 0.0334(4) Uani 1 d .
N2 N -0.1679(3) 0.1634(2) 0.48789(18) 0.0252(5) Uani 1 d D
H2 H -0.204(3) 0.169(3) 0.4104(15) 0.030 Uiso 1 d DR
O2 O 0.5454(2) 0.4665(2) 0.82872(17) 0.0334(4) Uani 1 d D
N3 N 0.6431(3) 0.1569(2) 0.24158(19) 0.0300(5) Uani 1 d .
C6 C 0.3616(3) 0.3426(3) 0.6958(2) 0.0245(5) Uani 1 d .
H6 H 0.4881 0.3696 0.6453 0.029 Uiso 1 calc R
C7 C 0.3756(3) 0.4245(3) 0.9019(2) 0.0237(5) Uani 1 d .
C4 C 0.0744(3) 0.2451(2) 0.7060(2) 0.0203(5) Uani 1 d .
C1 C 0.2756(3) 0.3640(3) 0.8311(2) 0.0215(5) Uani 1 d .
C3 C -0.0096(3) 0.2678(3) 0.8405(2) 0.0228(5) Uani 1 d .
H3 H -0.1371 0.2432 0.8904 0.027 Uiso 1 calc R
N1 N -0.2525(3) 0.0705(2) 0.61421(18) 0.0248(5) Uani 1 d D
H1 H -0.347(2) 0.011(2) 0.623(2) 0.030 Uiso 1 d DR
C2 C 0.0890(3) 0.3255(3) 0.9031(2) 0.0224(5) Uani 1 d .
H2B H 0.0293 0.3390 0.9955 0.027 Uiso 1 calc R
O5 O 0.7895(2) 0.2147(2) 0.23106(16) 0.0402(5) Uani 1 d .
C5 C 0.2632(3) 0.2820(3) 0.6348(2) 0.0253(5) Uani 1 d .
H5 H 0.3244 0.2652 0.5436 0.030 Uiso 1 calc R
C4' C -0.0378(3) 0.1887(3) 0.6398(2) 0.0213(5) Uani 1 d .
C5' C -0.0343(3) 0.2372(2) 0.5011(2) 0.0166(5) Uani 1 d .
C51 C 0.0796(3) 0.3427(3) 0.3749(2) 0.0296(6) Uani 1 d .
H51A H 0.2035 0.2847 0.3350 0.044 Uiso 1 calc GR
H51B H 0.1021 0.4325 0.4005 0.044 Uiso 1 calc GR
H51C H 0.0086 0.3806 0.3054 0.044 Uiso 1 calc GR
C31 C -0.2402(3) -0.0079(3) 0.8580(2) 0.0318(6) Uani 1 d .
H31A H -0.3441 0.0557 0.9128 0.048 Uiso 1 calc GR
H31B H -0.1310 -0.0350 0.8964 0.048 Uiso 1 calc GR
H31C H -0.2868 -0.1045 0.8624 0.048 Uiso 1 calc GR
O4 O 0.6008(3) 0.1575(3) 0.13800(17) 0.0561(6) Uani 1 d .
C3' C -0.1772(3) 0.0840(3) 0.7088(2) 0.0225(5) Uani 1 d .
H2A H 0.586(4) 0.506(3) 0.877(3) 0.071(11) Uiso 1 d D
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
N1 N2 H2 120.3(14)
N1 N2 C5' 109.25(17)
C5' N2 H2 130.5(14)
C7 O2 H2A 108.7(19)
O5 N3 O3 117.62(18)
O4 N3 O3 120.85(18)
O4 N3 O5 121.53(18)
C1 C6 H6 119.9
C5 C6 H6 119.9
C5 C6 C1 120.23(19)
O1 C7 O2 123.1(2)
O1 C7 C1 120.37(18)
O2 C7 C1 116.56(18)
C3 C4 C5 118.1(2)
C3 C4 C4' 119.98(17)
C5 C4 C4' 121.86(18)
C6 C1 C7 122.38(18)
C2 C1 C6 119.1(2)
C2 C1 C7 118.48(18)
C4 C3 H3 119.3
C2 C3 C4 121.33(18)
C2 C3 H3 119.3
N2 N1 H1 120.3(13)
C3' N1 N2 108.95(17)
C3' N1 H1 130.8(13)
C1 C2 H2B 119.9
C3 C2 C1 120.25(19)
C3 C2 H2B 119.9
C6 C5 C4 120.9(2)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5' C4' C4 126.48(18)
C5' C4' C3' 107.19(19)
C3' C4' C4 126.20(19)
N2 C5' C4' 106.88(17)
N2 C5' C51 118.65(18)
C4' C5' C51 134.5(2)
C5' C51 H51A 109.5
C5' C51 H51B 109.5
C5' C51 H51C 109.5
H51A C51 H51B 109.5
H51A C51 H51C 109.5
H51B C51 H51C 109.5
H31A C31 H31B 109.5
H31A C31 H31C 109.5
H31B C31 H31C 109.5
C3' C31 H31A 109.5
C3' C31 H31B 109.5
C3' C31 H31C 109.5
N1 C3' C4' 107.74(18)
N1 C3' C31 121.09(19)
C4' C3' C31 131.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.250(2)
O3 N3 1.269(2)
N2 H2 0.924(9)
N2 N1 1.356(2)
N2 C5' 1.364(3)
O2 C7 1.300(2)
O2 H2A 0.849(10)
N3 O5 1.257(2)
N3 O4 1.224(2)
C6 H6 0.9500
C6 C1 1.395(3)
C6 C5 1.385(3)
C7 C1 1.472(3)
C4 C3 1.391(3)
C4 C5 1.404(3)
C4 C4' 1.484(3)
C1 C2 1.395(3)
C3 H3 0.9500
C3 C2 1.383(3)
N1 H1 0.934(9)
N1 C3' 1.334(3)
C2 H2B 0.9500
C5 H5 0.9500
C4' C5' 1.378(3)
C4' C3' 1.403(3)
C5' C51 1.479(3)
C51 H51A 0.9800
C51 H51B 0.9800
C51 H51C 0.9800
C31 H31A 0.9800
C31 H31B 0.9800
C31 H31C 0.9800
C31 C3' 1.496(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O5 0.924(9) 1.812(11) 2.705(2) 162(2) 1_455
N1 H1 O3 0.934(9) 1.837(10) 2.770(2) 177(2) 2_556
O2 H2A O1 0.849(10) 1.784(11) 2.627(2) 171(3) 2_667
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
O1 C7 C1 C6 -175.4(2)
O1 C7 C1 C2 3.9(3)
N2 N1 C3' C4' -0.5(2)
N2 N1 C3' C31 -178.8(2)
O2 C7 C1 C6 4.1(3)
O2 C7 C1 C2 -176.6(2)
C6 C1 C2 C3 -0.4(3)
C7 C1 C2 C3 -179.8(2)
C4 C3 C2 C1 0.7(3)
C4 C4' C5' N2 -176.0(2)
C4 C4' C5' C51 5.2(4)
C4 C4' C3' N1 176.4(2)
C4 C4' C3' C31 -5.6(4)
C1 C6 C5 C4 1.7(3)
C3 C4 C5 C6 -1.4(3)
C3 C4 C4' C5' 141.3(2)
C3 C4 C4' C3' -33.9(3)
N1 N2 C5' C4' -0.3(2)
N1 N2 C5' C51 178.69(19)
C5 C6 C1 C7 178.5(2)
C5 C6 C1 C2 -0.8(3)
C5 C4 C3 C2 0.2(3)
C5 C4 C4' C5' -36.5(3)
C5 C4 C4' C3' 148.3(2)
C4' C4 C3 C2 -177.7(2)
C4' C4 C5 C6 176.5(2)
C5' N2 N1 C3' 0.5(2)
C5' C4' C3' N1 0.4(2)
C5' C4' C3' C31 178.4(2)
C3' C4' C5' N2 -0.1(2)
C3' C4' C5' C51 -178.8(2)
