#------------------------------------------------------------------------------
#$Date: 2019-07-15 12:31:05 +0300 (Mon, 15 Jul 2019) $
#$Revision: 217037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233127.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_7233127
loop_
_publ_author_name
'Xue-Jun Zhou'
'Cheng Chen'
'Cai-Xia Ren'
'Jian-Ke Sun'
'Jie Zhang'
_publ_section_title
;
 Tunable solid-state photoluminescence based on proton-triggered
 structural transformation of 4,4'-bipyridinium derivative
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              744
_journal_page_last               750
_journal_paper_doi               10.1039/C2TC00111J
_journal_volume                  1
_journal_year                    2013
_chemical_formula_moiety         'C18 H20 Cl2 N2 O12'
_chemical_formula_sum            'C18 H20 Cl2 N2 O12'
_chemical_formula_weight         527.26
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                96.509(7)
_cell_angle_beta                 93.700(14)
_cell_angle_gamma                93.897(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1914(4)
_cell_length_b                   7.9109(4)
_cell_length_c                   20.1775(11)
_cell_measurement_reflns_used    2226
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4934
_cell_measurement_theta_min      2.0372
_cell_volume                     1134.85(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  Saturn70
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7578
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        <1.0
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9313
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     738
_refine_ls_restrained_S_all      1.264
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0675
_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)+(0.0080P)²+1.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                3044
_reflns_number_total             4035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Chem-Mater-C-2013-1-744-1.cif
_cod_data_source_block           H2L(3)
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1134.84(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7233127
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1750(4) 0.1669(4) 0.01060(16) 0.0696(9) Uani 1 1 d . . .
O2 O 0.1235(5) 0.2652(4) -0.08725(15) 0.0708(9) Uani 1 1 d . . .
H2 H 0.0793 0.1671 -0.0984 0.085 Uiso 1 1 calc R . .
N1 N 0.3089(5) 0.7006(5) 0.21644(16) 0.0553(8) Uani 1 1 d . . .
N2 N -0.4654(6) 0.7529(7) 0.40592(19) 0.0777(12) Uani 1 1 d . . .
H2A H -0.5656 0.7577 0.4269 0.093 Uiso 1 1 calc R . .
C1 C 0.1793(5) 0.2843(5) -0.0228(2) 0.0542(10) Uani 1 1 d . . .
C2 C 0.2454(5) 0.4619(5) 0.0040(2) 0.0476(9) Uani 1 1 d . . .
C3 C 0.2387(6) 0.5961(5) -0.0345(2) 0.0542(10) Uani 1 1 d . . .
H3 H 0.1915 0.5766 -0.0789 0.065 Uiso 1 1 calc R . .
C4 C 0.3024(6) 0.7591(5) -0.0066(2) 0.0603(11) Uani 1 1 d . . .
H4 H 0.2969 0.8493 -0.0323 0.072 Uiso 1 1 calc R . .
C5 C 0.3736(6) 0.7888(5) 0.0589(2) 0.0596(11) Uani 1 1 d . . .
H5 H 0.4163 0.8989 0.0772 0.072 Uiso 1 1 calc R . .
C6 C 0.3822(5) 0.6552(5) 0.0978(2) 0.0528(10) Uani 1 1 d . . .
C7 C 0.3186(5) 0.4927(5) 0.0698(2) 0.0512(10) Uani 1 1 d . . .
H7 H 0.3249 0.4025 0.0955 0.061 Uiso 1 1 calc R . .
C8 C 0.4619(6) 0.6861(7) 0.1694(2) 0.0689(13) Uani 1 1 d . . .
H8A H 0.5360 0.5928 0.1791 0.083 Uiso 1 1 calc R . .
H8B H 0.5434 0.7904 0.1759 0.083 Uiso 1 1 calc R . .
C9 C 0.2301(7) 0.8470(6) 0.2274(2) 0.0703(13) Uani 1 1 d . . .
H9 H 0.2761 0.9413 0.2082 0.084 Uiso 1 1 calc R . .
C10 C 0.0822(7) 0.8616(6) 0.2665(2) 0.0663(12) Uani 1 1 d . . .
H10 H 0.0285 0.9653 0.2732 0.080 Uiso 1 1 calc R . .
C11 C 0.0120(5) 0.7245(5) 0.29596(18) 0.0483(9) Uani 1 1 d . . .
C12 C 0.0999(7) 0.5754(6) 0.2844(2) 0.0713(13) Uani 1 1 d . . .
H12 H 0.0587 0.4798 0.3039 0.086 Uiso 1 1 calc R . .
C13 C 0.2465(7) 0.5663(6) 0.2448(3) 0.0731(13) Uani 1 1 d . . .
H13 H 0.3036 0.4645 0.2376 0.088 Uiso 1 1 calc R . .
C14 C -0.1532(6) 0.7355(5) 0.33672(18) 0.0505(9) Uani 1 1 d . . .
C15 C -0.2328(7) 0.8874(6) 0.3513(3) 0.0766(14) Uani 1 1 d . . .
H15 H -0.1795 0.9868 0.3375 0.092 Uiso 1 1 calc R . .
C16 C -0.3904(8) 0.8925(8) 0.3860(3) 0.0870(16) Uani 1 1 d . . .
H16 H -0.4442 0.9953 0.3955 0.104 Uiso 1 1 calc R . .
C17 C -0.3912(8) 0.6059(8) 0.3946(3) 0.0916(17) Uani 1 1 d . . .
H17 H -0.4459 0.5095 0.4101 0.110 Uiso 1 1 calc R . .
C18 C -0.2340(7) 0.5938(6) 0.3600(3) 0.0786(15) Uani 1 1 d . . .
H18 H -0.1819 0.4895 0.3524 0.094 Uiso 1 1 calc R . .
Cl1 Cl 0.64270(17) 0.21363(15) 0.21947(6) 0.0668(3) Uani 1 1 d D . .
Cl2 Cl 0.18658(19) 0.24405(18) 0.42654(7) 0.0778(4) Uani 1 1 d D . .
O3 O 0.7660(10) 0.3357(10) 0.2025(3) 0.159(4) Uani 0.754(8) 1 d PDU A 1
O4 O 0.6077(13) 0.2391(9) 0.2861(3) 0.156(4) Uani 0.754(8) 1 d PDU A 1
O5 O 0.4710(8) 0.2107(8) 0.1813(4) 0.143(3) Uani 0.754(8) 1 d PDU A 1
O6 O 0.7032(10) 0.0505(7) 0.2068(4) 0.146(3) Uani 0.754(8) 1 d PDU A 1
O3B O 0.525(3) 0.166(3) 0.2661(9) 0.183(11) Uani 0.246(8) 1 d PDU A 2
O4B O 0.634(3) 0.3857(11) 0.2140(11) 0.161(10) Uani 0.246(8) 1 d PDU A 2
O5B O 0.604(3) 0.118(2) 0.1592(6) 0.151(9) Uani 0.246(8) 1 d PDU A 2
O6B O 0.8267(15) 0.193(2) 0.2431(11) 0.148(9) Uani 0.246(8) 1 d PDU A 2
O7 O 0.3819(7) 0.2651(13) 0.4384(4) 0.131(4) Uani 0.661(12) 1 d PDU B 1
O8 O 0.1486(16) 0.2289(12) 0.3585(3) 0.146(4) Uani 0.661(12) 1 d PDU B 1
O9 O 0.1361(17) 0.0862(13) 0.4484(6) 0.205(6) Uani 0.661(12) 1 d PDU B 1
O10 O 0.1043(19) 0.3707(16) 0.4600(5) 0.227(6) Uani 0.661(12) 1 d PDU B 1
O7B O 0.327(3) 0.169(2) 0.3979(11) 0.234(11) Uani 0.339(12) 1 d PDU B 2
O8B O 0.034(2) 0.250(2) 0.3813(9) 0.161(9) Uani 0.339(12) 1 d PDU B 2
O9B O 0.124(2) 0.1653(15) 0.4798(6) 0.099(5) Uani 0.339(12) 1 d PDU B 2
O10B O 0.244(3) 0.4156(12) 0.4516(6) 0.133(7) Uani 0.339(12) 1 d PDU B 2
O1W O 0.0374(5) 0.0484(4) 0.12376(18) 0.0783(10) Uani 1 1 d D . .
H1B H 0.077(7) 0.089(6) 0.0908(19) 0.118 Uiso 1 1 d D . .
H1C H -0.039(7) 0.105(6) 0.143(2) 0.118 Uiso 1 1 d D . .
O2W O 0.2164(9) 0.7639(12) 0.4657(4) 0.180(3) Uani 1 1 d D . .
H2C H 0.154(15) 0.840(10) 0.481(6) 0.270 Uiso 1 1 d D . .
H2D H 0.204(19) 0.673(8) 0.481(7) 0.270 Uiso 1 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O2 H2 109.5 . .
C9 N1 C13 119.8(4) . .
C9 N1 C8 119.5(4) . .
C13 N1 C8 120.6(4) . .
C16 N2 C17 121.6(5) . .
C16 N2 H2A 119.2 . .
C17 N2 H2A 119.2 . .
O1 C1 O2 122.5(4) . .
O1 C1 C2 123.7(4) . .
O2 C1 C2 113.8(4) . .
C7 C2 C3 119.4(4) . .
C7 C2 C1 118.1(4) . .
C3 C2 C1 122.5(4) . .
C4 C3 C2 119.8(4) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C5 C4 C3 120.4(4) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 120.3(4) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C7 C6 C5 119.2(4) . .
C7 C6 C8 120.2(4) . .
C5 C6 C8 120.7(4) . .
C6 C7 C2 120.9(4) . .
C6 C7 H7 119.5 . .
C2 C7 H7 119.5 . .
N1 C8 C6 110.9(3) . .
N1 C8 H8A 109.5 . .
C6 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
N1 C9 C10 121.1(4) . .
N1 C9 H9 119.4 . .
C10 C9 H9 119.4 . .
C9 C10 C11 120.7(4) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C10 C11 C12 116.5(4) . .
C10 C11 C14 121.7(4) . .
C12 C11 C14 121.8(4) . .
C13 C12 C11 120.8(4) . .
C13 C12 H12 119.6 . .
C11 C12 H12 119.6 . .
N1 C13 C12 121.1(4) . .
N1 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C18 C14 C15 117.5(4) . .
C18 C14 C11 121.2(4) . .
C15 C14 C11 121.3(4) . .
C16 C15 C14 120.1(5) . .
C16 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
N2 C16 C15 120.2(5) . .
N2 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
N2 C17 C18 120.5(5) . .
N2 C17 H17 119.7 . .
C18 C17 H17 119.7 . .
C17 C18 C14 120.0(5) . .
C17 C18 H18 120.0 . .
C14 C18 H18 120.0 . .
O3 Cl1 O5B 100.4(9) . .
O3 Cl1 O3B 146.3(10) . .
O5B Cl1 O3B 111.9(7) . .
O3 Cl1 O4 112.2(4) . .
O5B Cl1 O4 147.4(8) . .
O3B Cl1 O4 35.8(9) . .
O3 Cl1 O4B 46.6(8) . .
O5B Cl1 O4B 111.2(7) . .
O3B Cl1 O4B 109.6(7) . .
O4 Cl1 O4B 91.1(10) . .
O3 Cl1 O6 112.5(4) . .
O5B Cl1 O6 58.5(9) . .
O3B Cl1 O6 93.0(11) . .
O4 Cl1 O6 107.6(4) . .
O4B Cl1 O6 157.4(10) . .
O3 Cl1 O6B 67.8(8) . .
O5B Cl1 O6B 109.4(7) . .
O3B Cl1 O6B 108.1(7) . .
O4 Cl1 O6B 85.2(10) . .
O4B Cl1 O6B 106.4(7) . .
O6 Cl1 O6B 63.9(7) . .
O3 Cl1 O5 110.6(4) . .
O5B Cl1 O5 56.5(9) . .
O3B Cl1 O5 81.2(10) . .
O4 Cl1 O5 107.9(4) . .
O4B Cl1 O5 79.6(8) . .
O6 Cl1 O5 105.7(4) . .
O6B Cl1 O5 165.8(8) . .
O7B Cl2 O10 155.9(9) . .
O7B Cl2 O8 72.1(9) . .
O10 Cl2 O8 114.0(5) . .
O7B Cl2 O9B 113.4(7) . .
O10 Cl2 O9B 78.8(7) . .
O8 Cl2 O9B 137.2(7) . .
O7B Cl2 O8B 112.1(7) . .
O10 Cl2 O8B 81.5(10) . .
O8 Cl2 O8B 41.8(9) . .
O9B Cl2 O8B 107.7(7) . .
O7B Cl2 O9 87.0(9) . .
O10 Cl2 O9 111.4(5) . .
O8 Cl2 O9 108.0(5) . .
O9B Cl2 O9 35.6(6) . .
O8B Cl2 O9 98.3(9) . .
O7B Cl2 O7 46.6(9) . .
O10 Cl2 O7 111.3(5) . .
O8 Cl2 O7 106.9(5) . .
O9B Cl2 O7 105.1(7) . .
O8B Cl2 O7 146.6(9) . .
O9 Cl2 O7 104.7(5) . .
O7B Cl2 O10B 110.2(7) . .
O10 Cl2 O10B 45.7(6) . .
O8 Cl2 O10B 110.4(8) . .
O9B Cl2 O10B 106.9(6) . .
O8B Cl2 O10B 106.2(6) . .
O9 Cl2 O10B 141.2(7) . .
O7 Cl2 O10B 69.6(7) . .
H1B O1W H1C 114(2) . .
H2C O2W H2D 116(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.207(5) .
O2 C1 1.325(5) .
O2 H2 0.8200 .
N1 C9 1.326(5) .
N1 C13 1.328(5) .
N1 C8 1.501(5) .
N2 C16 1.311(6) .
N2 C17 1.315(7) .
N2 H2A 0.8600 .
C1 C2 1.482(6) .
C2 C7 1.385(5) .
C2 C3 1.386(5) .
C3 C4 1.382(6) .
C3 H3 0.9300 .
C4 C5 1.374(6) .
C4 H4 0.9300 .
C5 C6 1.388(6) .
C5 H5 0.9300 .
C6 C7 1.379(5) .
C6 C8 1.507(6) .
C7 H7 0.9300 .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.367(6) .
C9 H9 0.9300 .
C10 C11 1.377(5) .
C10 H10 0.9300 .
C11 C12 1.380(6) .
C11 C14 1.490(5) .
C12 C13 1.364(6) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 C18 1.371(6) .
C14 C15 1.376(6) .
C15 C16 1.371(7) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 C18 1.369(7) .
C17 H17 0.9300 .
C18 H18 0.9300 .
Cl1 O3 1.353(4) .
Cl1 O5B 1.359(7) .
Cl1 O3B 1.370(8) .
Cl1 O4 1.379(5) .
Cl1 O4B 1.384(7) .
Cl1 O6 1.391(4) .
Cl1 O6B 1.404(7) .
Cl1 O5 1.410(4) .
Cl2 O7B 1.334(7) .
Cl2 O10 1.338(6) .
Cl2 O8 1.372(5) .
Cl2 O9B 1.385(7) .
Cl2 O8B 1.388(7) .
Cl2 O9 1.403(6) .
Cl2 O7 1.405(5) .
Cl2 O10B 1.417(7) .
O1W H1B 0.828(13) .
O1W H1C 0.823(13) .
O2W H2C 0.817(13) .
O2W H2D 0.818(13) .
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
O2 H2 O1W 0.82 1.85 2.669(5) 175.8 2
N2 H2A O2W 0.86 1.80 2.656(6) 176.3 1_455
O1W H1B O1 0.828(13) 1.952(13) 2.779(5) 175(5) .
O1W H1C O6 0.823(13) 2.37(4) 3.018(8) 136(5) 1_455
O1W H1C O6B 0.823(13) 2.35(4) 3.08(2) 148(5) 1_455
O1W H1C O3 0.823(13) 2.61(2) 3.419(10) 169(5) 1_455
O2W H2C O9B 0.817(13) 2.20(9) 2.814(14) 132(11) 2_566
O2W H2C O9 0.817(13) 2.66(7) 3.369(16) 146(11) 2_566
O2W H2D O10 0.818(13) 2.60(11) 3.029(16) 114(10) 2_566
O2W H2D O10B 0.818(13) 2.10(8) 2.760(15) 137(12) .
O2W H2D O10 0.818(13) 2.43(8) 3.147(17) 146(14) .
