#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/91/2219140.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_2219140
loop_
_publ_author_name
'Starosta, Wojciech'
'Leciejewicz, Janusz'
_publ_section_title
;
 4-Carboxypyridazin-1-ium chloride
;
_journal_coeditor_code           RK2101
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1553
_journal_paper_doi               10.1107/S1600536808022319
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C5 H5 N2 O2 +, Cl -'
_chemical_formula_moiety         'C5 H5 N2 O2 +, Cl -'
_chemical_formula_sum            'C5 H5 Cl N2 O2'
_chemical_formula_weight         160.56
_chemical_name_systematic
;
4-Carboxypyridazin-1-ium chloride
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8505(14)
_cell_length_b                   6.5905(13)
_cell_length_c                   14.561(3)
_cell_measurement_reflns_used    6
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      6
_cell_volume                     651.6(2)
_computing_cell_refinement       'KM-4 Software (Kuma, 1996)'
_computing_data_collection       'KM-4 Software (Kuma, 1996)'
_computing_data_reduction        'DATAPROC (Kuma, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kuma KM-4 four-circle'
_diffrn_measurement_method       'Profile data from ω/2θ'
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2062
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         2.82
_diffrn_standards_decay_%        1.15
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  0.95225
_exptl_absorpt_correction_T_min  0.94161
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.1527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                1318
_reflns_number_total             1917
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2101.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_hydrogens' value 'Geom' changed to
'geom' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_secondary' value 'Difmap' changed to
'difmap' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Analytical' changed
to 'analytical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_refine_ls_matrix_type'
value 'Full' changed to 'full' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_weighting_scheme' value 'Calc' changed to 'calc'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_hydrogens' value 'Geom' changed to
'geom' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_atom_sites_solution_secondary' value 'Difmap' changed
to 'difmap' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Analytical'
changed to 'analytical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_matrix_type' value 'Full' changed to 'full'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_weighting_scheme' value 'Calc' changed to
'calc' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2219140
_cod_database_fobs_code          2219140
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl Cl1 0.61082(6) 0.18289(6) 0.39362(3) 0.03696(13) Uani d . 1
O O1 0.8041(2) 0.6663(2) 0.46266(8) 0.0485(3) Uani d . 1
C C3 0.8870(3) 0.9337(3) 0.61752(11) 0.0382(4) Uani d . 1
H H3 0.8395 0.9943 0.5613 0.046 Uiso calc R 1
C C4 0.8811(2) 0.7225(2) 0.62339(10) 0.0296(3) Uani d . 1
O O2 0.7273(2) 0.4276(2) 0.56133(8) 0.0414(3) Uani d . 1
C C7 0.7988(2) 0.6028(3) 0.53974(10) 0.0330(3) Uani d . 1
C C5 0.9550(2) 0.6321(2) 0.70515(11) 0.0337(3) Uani d . 1
H H5 0.9548 0.4918 0.7120 0.040 Uiso calc R 1
N N2 0.9559(2) 1.0516(2) 0.68707(10) 0.0414(3) Uani d . 1
C C6 1.0306(3) 0.7589(3) 0.77771(11) 0.0376(4) Uani d . 1
H H6 1.0841 0.7045 0.8345 0.045 Uiso calc R 1
N N1 1.0257(2) 0.9555(2) 0.76522(10) 0.0368(3) Uani d . 1
H H1 1.063(3) 1.042(4) 0.8143(17) 0.063(7) Uiso d . 1
H H2 0.675(4) 0.358(4) 0.5097(19) 0.069(8) 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
Cl1 0.0472(2) 0.02641(19) 0.0353(2) 0.00189(16) -0.00212(15) -0.00355(14)
O1 0.0698(9) 0.0472(8) 0.0264(6) 0.0011(7) -0.0010(5) 0.0038(5)
C3 0.0507(10) 0.0319(8) 0.0309(7) 0.0058(7) 0.0017(7) 0.0058(6)
C4 0.0313(7) 0.0310(7) 0.0259(6) 0.0027(6) 0.0021(5) 0.0015(5)
O2 0.0567(8) 0.0354(6) 0.0303(6) -0.0046(6) -0.0010(5) -0.0028(5)
C7 0.0371(8) 0.0336(8) 0.0267(7) 0.0064(6) -0.0017(6) 0.0005(6)
C5 0.0406(8) 0.0291(7) 0.0295(7) 0.0003(6) -0.0025(6) 0.0030(5)
N2 0.0554(9) 0.0296(7) 0.0386(7) 0.0022(7) 0.0041(6) 0.0022(5)
C6 0.0463(9) 0.0349(8) 0.0288(7) -0.0010(7) -0.0045(6) 0.0028(6)
N1 0.0443(8) 0.0340(7) 0.0315(6) -0.0034(6) 0.0023(5) -0.0034(5)
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'
Cl Cl 0.1484 0.1585 '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
N2 C3 C4 123.60(15)
N2 C3 H3 118.2
C4 C3 H3 118.2
C5 C4 C3 118.55(15)
C5 C4 C7 122.31(15)
C3 C4 C7 119.12(14)
C7 O2 H2 111.4(17)
O1 C7 O2 126.14(16)
O1 C7 C4 121.39(16)
O2 C7 C4 112.47(13)
C4 C5 C6 117.17(16)
C4 C5 H5 121.4
C6 C5 H5 121.4
C3 N2 N1 115.32(14)
N1 C6 C5 119.27(15)
N1 C6 H6 120.4
C5 C6 H6 120.4
C6 N1 N2 126.06(15)
C6 N1 H1 120.2(16)
N2 N1 H1 113.5(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.203(2)
C3 N2 1.313(2)
C3 C4 1.395(2)
C3 H3 0.9300
C4 C5 1.367(2)
C4 C7 1.497(2)
O2 C7 1.309(2)
O2 H2 0.91(3)
C5 C6 1.392(2)
C5 H5 0.9300
N2 N1 1.334(2)
C6 N1 1.308(2)
C6 H6 0.9300
N1 H1 0.92(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
O2 H2 Cl1 . 0.91(3) 2.05(3) 2.9464(14) 169(2)
N1 H1 Cl1 4_676 0.92(3) 2.15(3) 3.0373(15) 160(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655585
