#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/31/7223135.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_7223135
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                 112.33(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.911(2)
_cell_length_b                   23.760(8)
_cell_length_c                   7.502(3)
_cell_measurement_temperature    290
_cell_volume                     1304.4(8)
_computing_cell_refinement       unknown
_computing_data_collection       unknown
_computing_data_reduction        unknown
_computing_molecular_graphics    unknown
_computing_structure_solution    unknown
_diffrn_ambient_temperature      290
_diffrn_measured_fraction_theta_full 0.92
_diffrn_measured_fraction_theta_max 0
_diffrn_radiation_probe          neutron
_diffrn_radiation_wavelength     -1
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4056
_diffrn_reflns_theta_full        10.09
_diffrn_reflns_theta_max         68.84
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0
_exptl_crystal_density_diffrn    1.5329
_exptl_crystal_F_000             616
_refine_ls_extinction_coef       53.4(15)
_refine_ls_extinction_method
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_goodness_of_fit_gt    3.01
_refine_ls_goodness_of_fit_ref   2.87
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_constraints    0
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.0468
_refine_ls_shift/su_mean         0.0049
_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          0.1510
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                3638
_reflns_number_total             4056
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            c5ra06733b1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1304.4(7)
_cod_original_sg_symbol_Hall     '-P 2ycb'
_cod_database_code               7223135
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 0.5477(6) 0.63725(16) 0.3798(7) Uani 0.050(2) 4 1 d
O2 O 0.8318(8) 0.87889(19) 0.6468(10) Uani 0.074(3) 4 1 d
O3 O 0.5664(7) 0.89802(19) 0.4388(9) Uani 0.066(3) 4 1 d
N2 N 0.6842(4) 0.86406(10) 0.5263(5) Uani 0.0490(14) 4 1 d
Cl1 Cl 0.2448(3) 0.70952(11) 0.1518(5) Uani 0.0536(12) 4 1 d
Cl2 Cl 0.9130(4) 0.66207(10) 0.6837(5) Uani 0.0592(14) 4 1 d
C1 C 0.5811(4) 0.68923(13) 0.4160(5) Uani 0.0360(14) 4 1 d
C2 C 0.4517(4) 0.73127(13) 0.3207(5) Uani 0.0360(14) 4 1 d
C3 C 0.4834(5) 0.78810(14) 0.3514(6) Uani 0.0366(15) 4 1 d
C4 C 0.6496(5) 0.80540(13) 0.4907(6) Uani 0.0380(16) 4 1 d
C5 C 0.7824(5) 0.76641(14) 0.5932(6) Uani 0.0381(16) 4 1 d
C6 C 0.7492(4) 0.71018(13) 0.5557(5) Uani 0.0375(15) 4 1 d
H2 H 0.3810(11) 0.8191(3) 0.2786(13) Uani 0.065(4) 4 1 d
H3 H 0.9117(11) 0.7811(3) 0.7007(13) Uani 0.063(4) 4 1 d
N1 N 0.7010(4) 0.54265(11) 0.4846(5) Uani 0.0473(13) 4 1 d
C7 C 0.7259(5) 0.52335(15) 0.6619(6) Uani 0.0451(17) 4 1 d
C8 C 0.7745(5) 0.46826(14) 0.7127(6) Uani 0.0416(16) 4 1 d
C9 C 0.8002(5) 0.43348(15) 0.5762(6) Uani 0.0451(17) 4 1 d
C10 C 0.7755(5) 0.45407(15) 0.3975(6) Uani 0.0471(18) 4 1 d
C11 C 0.7261(6) 0.50963(15) 0.3540(7) Uani 0.0496(19) 4 1 d
C12 C 0.8015(8) 0.4475(3) 0.9105(8) Uani 0.059(3) 4 1 d
H1 H 0.6497(11) 0.5888(3) 0.4465(14) Uani 0.070(4) 4 1 d
H4 H 0.6993(13) 0.5536(3) 0.7564(14) Uani 0.081(5) 4 1 d
H5 H 0.8371(13) 0.3899(3) 0.6121(14) Uani 0.078(5) 4 1 d
H6 H 0.7930(15) 0.4268(4) 0.2881(16) Uani 0.096(6) 4 1 d
H7 H 0.7058(14) 0.5292(4) 0.2177(15) Uani 0.085(5) 4 1 d
H8 H 0.911(2) 0.4258(8) 0.971(2) Uani 0.135(9) 4 1 d
H9 H 0.799(3) 0.4789(7) 1.000(2) Uani 0.163(12) 4 1 d
H10 H 0.697(2) 0.4192(6) 0.904(2) Uani 0.153(9) 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
