#------------------------------------------------------------------------------
#$Date: 2021-07-13 12:17:51 +0300 (Tue, 13 Jul 2021) $
#$Revision: 267494 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/41/1564121.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_1564121
loop_
_publ_author_name
'Li, Jing'
'Liu, Jinjian'
'Lu, Wenbo'
_publ_section_title
;
 Photochromism and hydrochromism of three complexes based on a new
 viologen 1-(4-carboxybutyl)-4,4′-bipyridinium ligand
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119921
_journal_paper_doi               10.1016/j.ica.2020.119921
_journal_volume                  512
_journal_year                    2020
_chemical_formula_moiety         'C15 H27 N2 Ni O7, C9 H3 O6, 5.5(H2 O)'
_chemical_formula_sum            'C24 H41 N2 Ni O18.5'
_chemical_formula_weight         712.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 117.905(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.1546(15)
_cell_length_b                   13.9895(9)
_cell_length_c                   22.906(2)
_cell_measurement_reflns_used    9749
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.28
_cell_volume                     6273.8(8)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            44439
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.30
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
? was used for absorption correction.
wR2(int) was 0.1271 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.8541.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3000
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         2.875
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         7807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1185P)²+19.7148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.1941
_reflns_number_gt                6863
_reflns_number_total             7807
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2020-512-119921.cif
_cod_data_source_block           Ni
_cod_original_cell_volume        6273.7(8)
_cod_original_formula_sum        'C24 H41 N2 Ni O18.50'
_cod_database_code               1564121
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H3A,H3B} of C3, H18 of C18, {H2A,H2B} of C2, {H4A,H4B} of C4, H13 of C13,
  H9 of C9, H14 of C14, H12 of C12, H7 of C7, H8 of C8, H6 of C6, {H5A,H5B} of
  C5, H24 of C24, H21 of C21, H15 of C15
 At 1.5 times of:
  {H4C,H4D} of O4, {H18A,H18B} of O18, {H6A,H6B} of O6, {H16A,H16B} of O16,
  {H14A,H14B} of O14, {H19A,H19B} of O19, {H5C,H5D} of O5, {H1A,H1B} of O1, H2
  of O2, {H17A,H17B} of O17, {H15A,H15B} of O15, {H13A,H13B} of O13
2. Others
 Fixed Sof: H19A(0.5) H19B(0.5)
3.a Free rotating group:
 O13(H13A,H13B), O15(H15A,H15B), O17(H17A,H17B), O6(H6A,H6B), O1(H1A,H1B),
 O5(H5C,H5D), O19(H19A,H19B), O4(H4C,H4D), O18(H18A,H18B)
3.b Rotating group:
 O14(H14A,H14B), O16(H16A,H16B)
3.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B)
3.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C13(H13), C9(H9), C14(H14), C12(H12), C7(H7), C8(H8), C6(H6),
 C24(H24), C21(H21), C18(H18)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -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_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
Ni1 Ni 0.465072(16) 0.30999(3) 0.101384(15) 0.02477(13) Uani 1 1 d . . .
O13 O 0.48679(11) 0.42091(18) 0.16697(11) 0.0372(5) Uani 1 1 d G . .
H13A H 0.5239 0.4318 0.2019 0.056 Uiso 1 1 d G . .
H13B H 0.4532 0.4375 0.1731 0.056 Uiso 1 1 d G . .
O15 O 0.36581(10) 0.35762(16) 0.05448(9) 0.0314(4) Uani 1 1 d G . .
H15A H 0.3490 0.3839 0.0166 0.047 Uiso 1 1 d G . .
H15B H 0.3504 0.3851 0.0779 0.047 Uiso 1 1 d G . .
O17 O 0.43216(11) 0.22429(17) 0.15531(11) 0.0354(5) Uani 1 1 d G . .
H17A H 0.3898 0.2106 0.1365 0.053 Uiso 1 1 d G . .
H17B H 0.4546 0.1788 0.1809 0.053 Uiso 1 1 d G . .
N2 N 0.56695(12) 0.26497(18) 0.15157(11) 0.0290(5) Uani 1 1 d . . .
C15 C 0.59827(15) 0.2535(2) 0.21724(14) 0.0323(6) Uani 1 1 d . . .
H15 H 0.5716 0.2530 0.2388 0.039 Uiso 1 1 calc R . .
C11 C 0.70970(14) 0.2444(2) 0.22404(14) 0.0283(5) Uani 1 1 d . . .
C13 C 0.66807(15) 0.2423(2) 0.25466(14) 0.0318(6) Uani 1 1 d . . .
H13 H 0.6872 0.2335 0.3001 0.038 Uiso 1 1 calc R . .
C10 C 0.78519(15) 0.2407(2) 0.26310(15) 0.0312(6) Uani 1 1 d . . .
C9 C 0.81833(16) 0.2523(3) 0.33122(16) 0.0398(7) Uani 1 1 d . . .
H9 H 0.7926 0.2596 0.3534 0.048 Uiso 1 1 calc R . .
C14 C 0.60668(16) 0.2632(3) 0.12202(14) 0.0381(7) Uani 1 1 d . . .
H14 H 0.5858 0.2683 0.0762 0.046 Uiso 1 1 calc R . .
C12 C 0.67723(16) 0.2542(3) 0.15570(15) 0.0383(7) Uani 1 1 d . . .
H12 H 0.7025 0.2547 0.1328 0.046 Uiso 1 1 calc R . .
N1 N 0.92655(17) 0.2476(3) 0.33604(18) 0.0616(10) Uani 1 1 d . . .
C7 C 0.88794(19) 0.2532(4) 0.36633(19) 0.0548(10) Uani 1 1 d . . .
H7 H 0.9087 0.2578 0.4121 0.066 Uiso 1 1 calc R . .
C8 C 0.82618(19) 0.2278(4) 0.23249(19) 0.0549(10) Uani 1 1 d . . .
H8 H 0.8066 0.2174 0.1872 0.066 Uiso 1 1 calc R . .
C6 C 0.8962(2) 0.2308(6) 0.2703(2) 0.0852(19) Uani 1 1 d . . .
H6 H 0.9235 0.2209 0.2500 0.102 Uiso 1 1 calc R . .
C5 C 1.0046(2) 0.2533(5) 0.3750(3) 0.089(2) Uani 1 1 d . . .
H5A H 1.0235 0.2613 0.3447 0.106 Uiso 1 1 calc R . .
H5B H 1.0178 0.3081 0.4043 0.106 Uiso 1 1 calc R . .
O12 O 0.30966(11) 0.4304(2) 0.12994(11) 0.0429(6) Uani 1 1 d . . .
O11 O 0.40509(11) 0.47797(19) 0.21565(11) 0.0400(5) Uani 1 1 d . . .
O9 O 0.31408(11) 0.5682(2) 0.43177(10) 0.0444(6) Uani 1 1 d . . .
O10 O 0.40903(12) 0.5232(2) 0.43111(12) 0.0525(7) Uani 1 1 d . . .
C17 C 0.30430(13) 0.47880(19) 0.22669(13) 0.0248(5) Uani 1 1 d . . .
C24 C 0.23316(13) 0.4780(2) 0.19613(13) 0.0262(5) Uani 1 1 d . . .
H24 H 0.2087 0.4684 0.1507 0.031 Uiso 1 1 calc R . .
C16 C 0.34191(14) 0.4607(2) 0.18744(13) 0.0285(5) Uani 1 1 d . . .
C21 C 0.23530(14) 0.5078(2) 0.30038(13) 0.0271(5) Uani 1 1 d . . .
H21 H 0.2123 0.5166 0.3250 0.032 Uiso 1 1 calc R . .
C22 C 0.19840(13) 0.4913(2) 0.23256(13) 0.0263(5) Uani 1 1 d . . .
O8 O 0.09363(12) 0.4787(2) 0.23579(13) 0.0486(6) Uani 1 1 d . . .
O7 O 0.09033(12) 0.4964(3) 0.13778(12) 0.0567(8) Uani 1 1 d . . .
C19 C 0.30621(13) 0.5110(2) 0.33132(12) 0.0258(5) Uani 1 1 d . . .
C20 C 0.34581(14) 0.5354(2) 0.40368(13) 0.0302(6) Uani 1 1 d . . .
C18 C 0.34034(13) 0.4957(2) 0.29453(13) 0.0263(5) Uani 1 1 d . . .
H18 H 0.3878 0.4967 0.3153 0.032 Uiso 1 1 calc R . .
C23 C 0.12142(14) 0.4892(2) 0.19971(15) 0.0343(6) Uani 1 1 d . . .
C2 C 1.1494(2) 0.1621(4) 0.4219(2) 0.0632(11) Uani 1 1 d . . .
H2A H 1.1460 0.2237 0.4012 0.076 Uiso 1 1 calc R . .
H2B H 1.1276 0.1154 0.3869 0.076 Uiso 1 1 calc R . .
C4 C 1.0315(3) 0.1675(6) 0.4131(4) 0.102(2) Uani 1 1 d . . .
H4A H 1.0200 0.1139 0.3829 0.122 Uiso 1 1 calc R . .
H4B H 1.0089 0.1574 0.4400 0.122 Uiso 1 1 calc R . .
C3 C 1.1113(3) 0.1667(5) 0.4599(3) 0.0812(17) Uani 1 1 d . . .
H3A H 1.1243 0.2240 0.4868 0.097 Uiso 1 1 calc R . .
H3B H 1.1232 0.1120 0.4892 0.097 Uiso 1 1 calc R . .
O2 O 1.25485(18) 0.1380(3) 0.42468(19) 0.0744(10) Uani 1 1 d . . .
H2 H 1.2957 0.1264 0.4470 0.112 Uiso 1 1 calc R . .
C1 C 1.2254(2) 0.1360(3) 0.4620(2) 0.0578(10) Uani 1 1 d . . .
O3 O 1.2520(2) 0.1178(4) 0.5192(2) 0.1046(16) Uani 1 1 d . . .
O6 O -0.04418(13) 0.5192(2) 0.07959(14) 0.0503(6) Uani 1 1 d G . .
H6A H -0.0012 0.5111 0.0994 0.075 Uiso 1 1 d G . .
H6B H -0.0623 0.4853 0.0979 0.075 Uiso 1 1 d G . .
O1 O 1.38150(18) 0.0776(3) 0.46234(16) 0.0696(9) Uani 1 1 d G . .
H1A H 1.3811 0.0610 0.4264 0.104 Uiso 1 1 d G . .
H1B H 1.4122 0.0463 0.4942 0.104 Uiso 1 1 d G . .
O5 O -0.1192(2) 0.4225(4) 0.1354(2) 0.0922(14) Uani 1 1 d G . .
H5C H -0.1515 0.4481 0.1016 0.138 Uiso 1 1 d G . .
H5D H -0.1130 0.4530 0.1698 0.138 Uiso 1 1 d G . .
O19 O 0.5000 0.0888(2) 0.2500 0.0347(6) Uani 1 2 d SG . .
H19A H 0.5266 0.0510 0.2439 0.052 Uiso 0.50 1 d PG . .
H19B H 0.4859 0.0620 0.2747 0.052 Uiso 0.50 1 d PG . .
O14 O 0.49036(11) 0.39421(17) 0.04339(10) 0.0361(5) Uani 1 1 d . . .
H14A H 0.4542 0.4193 0.0125 0.054 Uiso 1 1 d R . .
H14B H 0.5102 0.3606 0.0260 0.054 Uiso 1 1 d R . .
O16 O 0.43703(12) 0.20192(16) 0.03049(11) 0.0384(5) Uani 1 1 d . . .
H16A H 0.4542 0.2129 0.0040 0.058 Uiso 1 1 d R . .
H16B H 0.3929 0.1990 0.0072 0.058 Uiso 1 1 d R . .
O4 O 0.79590(15) 0.3271(3) 0.45998(15) 0.0596(8) Uani 1 1 d G . .
H4C H 0.7690 0.2794 0.4484 0.089 Uiso 1 1 d G . .
H4D H 0.7762 0.3741 0.4346 0.089 Uiso 1 1 d G . .
O18 O 0.29671(15) 0.1677(3) 0.08234(14) 0.0611(8) Uani 1 1 d G . .
H18A H 0.2914 0.1643 0.0432 0.092 Uiso 1 1 d G . .
H18B H 0.2694 0.1291 0.0867 0.092 Uiso 1 1 d G . .
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'
Ni Ni 0.3393 1.1124 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O13 Ni1 O15 87.97(9) . .
O13 Ni1 O17 91.62(10) . .
O13 Ni1 N2 90.13(9) . .
O13 Ni1 O16 176.20(9) . .
O15 Ni1 O17 84.88(9) . .
O15 Ni1 N2 178.09(9) . .
O15 Ni1 O16 88.40(9) . .
O17 Ni1 N2 95.04(9) . .
O17 Ni1 O16 89.15(9) . .
O14 Ni1 O13 89.90(10) . .
O14 Ni1 O15 91.44(8) . .
O14 Ni1 O17 175.96(8) . .
O14 Ni1 N2 88.70(9) . .
O14 Ni1 O16 89.10(10) . .
O16 Ni1 N2 93.50(9) . .
C15 N2 Ni1 120.76(19) . .
C14 N2 Ni1 121.54(19) . .
C14 N2 C15 116.6(2) . .
N2 C15 C13 123.5(3) . .
C13 C11 C10 121.3(3) . .
C12 C11 C13 116.9(3) . .
C12 C11 C10 121.7(3) . .
C15 C13 C11 119.8(3) . .
C9 C10 C11 121.9(3) . .
C9 C10 C8 117.0(3) . .
C8 C10 C11 121.1(3) . .
C7 C9 C10 121.4(3) . .
N2 C14 C12 123.8(3) . .
C14 C12 C11 119.3(3) . .
C7 N1 C6 119.0(3) . .
C7 N1 C5 121.2(4) . .
C6 N1 C5 119.7(4) . .
N1 C7 C9 121.1(3) . .
C6 C8 C10 119.1(4) . .
N1 C6 C8 122.2(4) . .
C4 C5 N1 110.1(5) . .
C24 C17 C16 120.7(2) . .
C24 C17 C18 119.0(2) . .
C18 C17 C16 120.3(2) . .
C22 C24 C17 120.8(2) . .
O12 C16 O11 124.0(3) . .
O12 C16 C17 119.1(2) . .
O11 C16 C17 117.0(2) . .
C19 C21 C22 120.5(2) . .
C24 C22 C21 119.4(2) . .
C24 C22 C23 120.9(2) . .
C21 C22 C23 119.7(2) . .
C21 C19 C20 120.4(2) . .
C18 C19 C21 119.5(2) . .
C18 C19 C20 120.0(2) . .
O9 C20 O10 124.3(3) . .
O9 C20 C19 118.3(2) . .
O10 C20 C19 117.4(2) . .
C19 C18 C17 120.8(2) . .
O8 C23 C22 117.7(3) . .
O8 C23 O7 125.2(3) . .
O7 C23 C22 117.1(3) . .
C3 C2 C1 115.5(4) . .
C5 C4 C3 115.5(6) . .
C2 C3 C4 111.7(5) . .
O2 C1 C2 110.5(4) . .
O3 C1 C2 123.3(4) . .
O3 C1 O2 126.2(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O13 2.054(2) .
Ni1 O15 2.055(2) .
Ni1 O17 2.083(2) .
Ni1 N2 2.094(2) .
Ni1 O14 2.040(2) .
Ni1 O16 2.089(2) .
N2 C15 1.339(4) .
N2 C14 1.338(4) .
C15 C13 1.382(4) .
C11 C13 1.396(4) .
C11 C10 1.483(4) .
C11 C12 1.390(4) .
C10 C9 1.388(4) .
C10 C8 1.395(4) .
C9 C7 1.365(5) .
C14 C12 1.387(4) .
N1 C7 1.332(5) .
N1 C6 1.351(6) .
N1 C5 1.533(5) .
C8 C6 1.379(6) .
C5 C4 1.439(9) .
O12 C16 1.243(3) .
O11 C16 1.260(3) .
O9 C20 1.242(3) .
O10 C20 1.250(4) .
C17 C24 1.393(4) .
C17 C16 1.506(3) .
C17 C18 1.395(3) .
C24 C22 1.388(4) .
C21 C22 1.395(4) .
C21 C19 1.389(4) .
C22 C23 1.508(4) .
O8 C23 1.249(4) .
O7 C23 1.258(4) .
C19 C20 1.508(3) .
C19 C18 1.387(3) .
C2 C3 1.469(7) .
C2 C1 1.538(6) .
C4 C3 1.581(7) .
O2 C1 1.295(5) .
C1 O3 1.186(6) .
