#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/31/7223131.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_7223131
loop_
_publ_author_name
'Majerz, Irena'
'Gutmann, Matthias'
_publ_section_title
;
 Intermolecular OHN hydrogen bond with proton moving in 3-methylpyridinium
 2,6-dichloro-4-nitrophenolate
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA06733B
_journal_year                    2015
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_name_systematic        ' ?'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_update_record
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.88(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.827(2)
_cell_length_b                   23.619(7)
_cell_length_c                   7.447(2)
_cell_measurement_temperature    170
_cell_volume                     1277.5(6)
_computing_cell_refinement       unknown
_computing_data_collection       unknown
_computing_data_reduction        unknown
_computing_molecular_graphics    unknown
_computing_structure_solution    unknown
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.9
_diffrn_measured_fraction_theta_max 0
_diffrn_radiation_probe          neutron
_diffrn_radiation_wavelength     -1
_diffrn_reflns_av_sigmaI/netI    0.087
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       58
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5943
_diffrn_reflns_theta_full        13.38
_diffrn_reflns_theta_max         73.36
_diffrn_reflns_theta_min         2.8
_exptl_absorpt_coefficient_mu    0
_exptl_crystal_density_diffrn    1.5651
_exptl_crystal_F_000             616
_refine_ls_extinction_coef       45.0(10)
_refine_ls_extinction_method
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_goodness_of_fit_gt    2.90
_refine_ls_goodness_of_fit_ref   2.74
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_constraints    0
_refine_ls_number_parameters     268
_refine_ls_number_reflns         5943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0771
_refine_ls_shift/su_max          0.0078
_refine_ls_shift/su_mean         0.0007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                5219
_reflns_number_total             5943
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            c5ra06733b1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1277.6(7)
_cod_original_sg_symbol_Hall     '-P 2ycb'
_cod_database_code               7223131
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
O1 O 0.5415(4) 0.63642(12) 0.3765(5) Uani 0.0265(12) 4 1 d
O2 O 0.8300(5) 0.87929(13) 0.6489(7) Uani 0.0395(16) 4 1 d
O3 O 0.5617(5) 0.89943(13) 0.4376(6) Uani 0.0356(16) 4 1 d
N2 N 0.6807(3) 0.86475(7) 0.5271(3) Uani 0.0252(8) 4 1 d
Cl1 Cl 0.2374(3) 0.70969(8) 0.1472(3) Uani 0.0283(8) 4 1 d
Cl2 Cl 0.9082(3) 0.66094(8) 0.6829(4) Uani 0.0318(8) 4 1 d
C1 C 0.5764(3) 0.68880(10) 0.4135(4) Uani 0.0194(9) 4 1 d
C2 C 0.4463(4) 0.73141(10) 0.3175(4) Uani 0.0199(10) 4 1 d
C3 C 0.4779(4) 0.78857(10) 0.3495(4) Uani 0.0200(10) 4 1 d
C4 C 0.6452(4) 0.80570(10) 0.4904(4) Uani 0.0197(10) 4 1 d
C5 C 0.7790(4) 0.76638(10) 0.5937(4) Uani 0.0207(10) 4 1 d
C6 C 0.7436(3) 0.70993(10) 0.5551(4) Uani 0.0202(10) 4 1 d
H2 H 0.3745(9) 0.8198(2) 0.2730(10) Uani 0.041(3) 4 1 d
H3 H 0.9084(8) 0.7813(2) 0.7036(10) Uani 0.041(3) 4 1 d
N1 N 0.6983(3) 0.54175(7) 0.4820(3) Uani 0.0258(8) 4 1 d
C7 C 0.7254(4) 0.52267(10) 0.6607(5) Uani 0.0238(11) 4 1 d
C8 C 0.7793(4) 0.46721(10) 0.7135(4) Uani 0.0226(10) 4 1 d
C9 C 0.8043(4) 0.43199(10) 0.5760(4) Uani 0.0234(10) 4 1 d
C10 C 0.7761(4) 0.45276(11) 0.3930(4) Uani 0.0257(11) 4 1 d
C11 C 0.7219(4) 0.50839(11) 0.3486(5) Uani 0.0253(11) 4 1 d
C12 C 0.8057(5) 0.44668(15) 0.9131(5) Uani 0.0331(13) 4 1 d
H1 H 0.6455(9) 0.5870(2) 0.4440(11) Uani 0.043(3) 4 1 d
H4 H 0.7014(10) 0.5534(3) 0.7591(11) Uani 0.051(3) 4 1 d
H5 H 0.8427(10) 0.3884(2) 0.6123(10) Uani 0.046(3) 4 1 d
H6 H 0.7910(10) 0.4253(3) 0.2822(11) Uani 0.052(3) 4 1 d
H7 H 0.6984(10) 0.5279(3) 0.2085(11) Uani 0.051(3) 4 1 d
H8 H 0.9289(15) 0.4229(5) 0.9734(14) Uani 0.088(5) 4 1 d
H9 H 0.8133(16) 0.4808(4) 1.0052(14) Uani 0.088(5) 4 1 d
H10 H 0.6991(13) 0.4195(4) 0.9109(14) Uani 0.088(5) 4 1 d
loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C
