#------------------------------------------------------------------------------
#$Date: 2021-05-05 11:59:48 +0300 (Wed, 05 May 2021) $
#$Revision: 264939 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/04/7060455.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_7060455
loop_
_publ_author_name
'Zhao, Guozheng'
'Liu, Wenya'
'Yuan, Fang'
'Liu, Jinjian'
_publ_section_title
;
 Three Mn--viologen complexes containing
 1-carboxyethyl-4,4′-bipyridinium: crystal structures,
 photochromism and theoretical calculations
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6787
_journal_page_last               6795
_journal_paper_doi               10.1039/D0NJ06279K
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety
'H12 Mn O6, 2(C12 H10 N2 O2), C8 H4 O4, 2(H2 O)'
_chemical_formula_sum            'C32 H40 Mn N4 O16'
_chemical_formula_weight         791.62
_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   mixed
_audit_creation_date             2021-02-11
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2021.02.06 svn.rb'dbe4f857' for OlexSys, GUI svn.r6224)
;
_audit_update_record
;
2021-02-24 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.498(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.9837(13)
_cell_length_b                   6.9704(3)
_cell_length_c                   24.5066(13)
_cell_measurement_reflns_used    4824
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.1910
_cell_measurement_theta_min      3.8190
_cell_volume                     3482.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 16.0710
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  31.00   1.00    3.05    --   22.39 -77.00 -30.00   66
  2  ω    -25.00  64.00   1.00    3.05    --   22.39 -99.00 -60.00   89
  3  ω    -21.00  63.00   1.00    3.05    --   22.39 -99.00  60.00   84
  4  ω     60.00  86.00   1.00    3.05    --   22.39  57.00  90.00   26
  5  ω      6.00  80.00   1.00    3.05    --   22.39  77.00 120.00   74
  6  ω    -40.00  31.00   1.00    3.05    --   22.39 -57.00-180.00   71
  7  ω    -42.00   0.00   1.00    3.05    --  -22.71 -77.00-180.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16719
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.591
_diffrn_reflns_theta_min         3.749
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67484
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             1652
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.053
_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     253
_refine_ls_number_reflns         4944
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0365P)²+2.9951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3865
_reflns_number_total             4944
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj06279k2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7060454--7060456.cif.'
_cod_database_code               7060455
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O002-H00C = O002-H00D
 0.85 with sigma of 0.02
 H00C-H00D
 1.34 with sigma of 0.04
 Mn01-H00E \\sim Mn01-H00F
 with sigma of 0.02
 Mn01-H00C \\sim Mn01-H00D
 with sigma of 0.02
3.a Free rotating group:
 O003(H00E,H00F), O00A(H00S,H00T)
3.b Rotating group:
 O004(H00G,H00H)
3.c Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B)
3.d Aromatic/amide H refined with riding coordinates:
 C00C(H00I), C00G(H00M), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn01 Mn 0.500000 0.62021(5) 0.750000 0.02577(10) Uani 1 2 d DS T P . .
O002 O 0.43336(6) 0.39542(17) 0.69217(6) 0.0315(3) Uani 1 1 d D . . . .
H00C H 0.4450(9) 0.326(3) 0.6715(9) 0.047 Uiso 1 1 d D U . . .
H00D H 0.4185(9) 0.321(3) 0.7097(9) 0.047 Uiso 1 1 d D U . . .
O003 O 0.55382(7) 0.61568(19) 0.69846(6) 0.0397(3) Uani 1 1 d G . . . .
H00E H 0.540697 0.552785 0.665123 0.060 Uiso 1 1 d DG U . . .
H00F H 0.573102 0.713024 0.693440 0.060 Uiso 1 1 d DG U . . .
O004 O 0.56618(6) 0.84425(18) 0.81202(6) 0.0400(3) Uani 1 1 d . . . . .
H00G H 0.576802 0.921884 0.791287 0.060 Uiso 1 1 d R U . . .
H00H H 0.545184 0.912913 0.825688 0.060 Uiso 1 1 d R U . . .
O005 O 0.62727(7) 0.91947(19) 0.69662(7) 0.0475(4) Uani 1 1 d . . . . .
O006 O 0.62130(8) 1.10404(19) 0.76792(7) 0.0473(4) Uani 1 1 d . . . . .
O007 O 0.45807(8) 0.1474(2) 0.62177(7) 0.0480(4) Uani 1 1 d . . . . .
O008 O 0.50618(8) 0.3903(2) 0.59949(7) 0.0551(4) Uani 1 1 d . . . . .
N009 N 0.69828(7) 1.1816(2) 0.67039(7) 0.0314(3) Uani 1 1 d . . . . .
O00A O 0.68520(10) 0.6328(3) 0.65890(8) 0.0656(5) Uani 1 1 d G . . . .
H00S H 0.665359 0.738169 0.655845 0.098 Uiso 1 1 d G U . . .
H00T H 0.688103 0.624493 0.625622 0.098 Uiso 1 1 d G U . . .
N00B N 0.79404(10) 0.9303(3) 0.44438(9) 0.0513(5) Uani 1 1 d . . . . .
C00C C 0.50655(9) -0.1973(2) 0.50581(8) 0.0329(4) Uani 1 1 d . . . . .
H00I H 0.510995 -0.329824 0.509905 0.040 Uiso 1 1 calc R U . . .
C00D C 0.63807(9) 1.0686(2) 0.72750(9) 0.0327(4) Uani 1 1 d . . . . .
C00E C 0.73631(8) 1.0773(2) 0.58237(8) 0.0299(3) Uani 1 1 d . . . . .
C00F C 0.49044(8) 0.1070(2) 0.54355(8) 0.0288(3) Uani 1 1 d . . . . .
C00G C 0.49696(8) -0.0910(2) 0.54899(8) 0.0329(4) Uani 1 1 d . . . . .
H00M H 0.494910 -0.152835 0.581683 0.039 Uiso 1 1 calc R U . . .
C00H C 0.75623(8) 1.0273(2) 0.53466(8) 0.0311(3) Uani 1 1 d . . . . .
C00I C 0.48441(8) 0.2243(3) 0.59247(8) 0.0339(4) Uani 1 1 d . . . . .
C00J C 0.76132(9) 1.1455(3) 0.68696(9) 0.0381(4) Uani 1 1 d . . . . .
H00J H 0.792109 1.154582 0.728175 0.046 Uiso 1 1 calc R U . . .
C00K C 0.78132(9) 1.0953(3) 0.64424(9) 0.0386(4) Uani 1 1 d . . . . .
H00K H 0.825568 1.072849 0.656730 0.046 Uiso 1 1 calc R U . . .
C00L C 0.71020(9) 0.9793(3) 0.47486(9) 0.0389(4) Uani 1 1 d . . . . .
H00L H 0.665691 0.978483 0.463906 0.047 Uiso 1 1 calc R U . . .
C00M C 0.67642(9) 1.2306(3) 0.71666(9) 0.0373(4) Uani 1 1 d . . . . .
H00A H 0.648987 1.344117 0.703185 0.045 Uiso 1 1 calc R U . . .
H00B H 0.714501 1.261021 0.755240 0.045 Uiso 1 1 calc R U . . .
C00N C 0.82189(9) 1.0263(3) 0.54753(9) 0.0402(4) Uani 1 1 d . . . . .
H00N H 0.854546 1.058138 0.586572 0.048 Uiso 1 1 calc R U . . .
C00O C 0.65410(9) 1.1699(3) 0.61152(10) 0.0476(5) Uani 1 1 d . . . . .
H00O H 0.610513 1.198942 0.600188 0.057 Uiso 1 1 calc R U . . .
C00P C 0.67126(9) 1.1163(3) 0.56730(9) 0.0450(5) Uani 1 1 d . . . . .
H00P H 0.639086 1.105600 0.526639 0.054 Uiso 1 1 calc R U . . .
C00Q C 0.83778(11) 0.9774(3) 0.50148(10) 0.0497(5) Uani 1 1 d . . . . .
H00Q H 0.881882 0.977347 0.510891 0.060 Uiso 1 1 calc R U . . .
C00R C 0.73133(12) 0.9329(3) 0.43196(10) 0.0481(5) Uani 1 1 d . . . . .
H00R H 0.699925 0.901922 0.392286 0.058 Uiso 1 1 calc R U . . .
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'
Mn Mn 0.3368 0.7283 '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'
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
_geom_angle_publ_flag
O002 Mn01 O002 88.74(7) . 2_656 y
O002 Mn01 O004 90.40(5) . 2_656 y
O002 Mn01 O004 177.28(5) 2_656 2_656 y
O002 Mn01 O004 177.29(5) . . y
O002 Mn01 O004 90.40(5) 2_656 . y
O003 Mn01 O002 87.09(5) . 2_656 y
O003 Mn01 O002 87.09(5) 2_656 . y
O003 Mn01 O002 91.70(5) 2_656 2_656 y
O003 Mn01 O002 91.70(5) . . y
O003 Mn01 O003 178.31(7) . 2_656 y
O003 Mn01 O004 90.36(5) 2_656 . y
O003 Mn01 O004 90.36(5) . 2_656 y
O003 Mn01 O004 90.83(5) . . y
O003 Mn01 O004 90.83(5) 2_656 2_656 y
O004 Mn01 O004 90.58(7) . 2_656 y
Mn01 O002 H00C 119.2(13) . . ?
Mn01 O002 H00D 116.1(13) . . ?
H00C O002 H00D 106(2) . . ?
Mn01 O003 H00E 122.0 . . ?
Mn01 O003 H00F 123.8 . . ?
H00E O003 H00F 104.5 . . ?
Mn01 O004 H00G 109.5 . . ?
Mn01 O004 H00H 109.4 . . ?
H00G O004 H00H 104.4 . . ?
C00J N009 C00M 121.06(16) . . ?
C00O N009 C00J 119.75(16) . . ?
C00O N009 C00M 119.18(15) . . ?
H00S O00A H00T 104.5 . . ?
C00R N00B C00Q 116.72(18) . . ?
C00F C00C H00I 119.7 5_656 . ?
C00G C00C H00I 119.7 . . ?
C00G C00C C00F 120.61(16) . 5_656 ?
O005 C00D O006 127.17(16) . . ?
O005 C00D C00M 118.77(15) . . ?
O006 C00D C00M 114.05(15) . . ?
C00K C00E C00H 122.43(15) . . ?
C00P C00E C00H 121.51(16) . . ?
C00P C00E C00K 116.02(17) . . ?
C00C C00F C00I 120.30(16) 5_656 . ?
C00G C00F C00C 119.08(15) . 5_656 ?
C00G C00F C00I 120.51(16) . . ?
C00C C00G H00M 119.8 . . ?
C00F C00G C00C 120.31(16) . . ?
C00F C00G H00M 119.8 . . ?
C00L C00H C00E 121.65(16) . . ?
C00N C00H C00E 121.35(16) . . ?
C00N C00H C00L 116.99(17) . . ?
O007 C00I C00F 117.97(16) . . ?
O008 C00I O007 126.17(17) . . ?
O008 C00I C00F 115.86(16) . . ?
N009 C00J H00J 119.5 . . ?
N009 C00J C00K 121.05(17) . . ?
C00K C00J H00J 119.5 . . ?
C00E C00K H00K 119.6 . . ?
C00J C00K C00E 120.87(16) . . ?
C00J C00K H00K 119.6 . . ?
C00H C00L H00L 120.3 . . ?
C00R C00L C00H 119.45(19) . . ?
C00R C00L H00L 120.3 . . ?
N009 C00M C00D 112.99(14) . . ?
N009 C00M H00A 109.0 . . ?
N009 C00M H00B 109.0 . . ?
C00D C00M H00A 109.0 . . ?
C00D C00M H00B 109.0 . . ?
H00A C00M H00B 107.8 . . ?
C00H C00N H00N 120.5 . . ?
C00Q C00N C00H 118.98(19) . . ?
C00Q C00N H00N 120.5 . . ?
N009 C00O H00O 119.2 . . ?
N009 C00O C00P 121.50(17) . . ?
C00P C00O H00O 119.2 . . ?
C00E C00P H00P 119.6 . . ?
C00O C00P C00E 120.77(18) . . ?
C00O C00P H00P 119.6 . . ?
N00B C00Q C00N 124.3(2) . . ?
N00B C00Q H00Q 117.9 . . ?
C00N C00Q H00Q 117.9 . . ?
N00B C00R C00L 123.6(2) . . ?
N00B C00R H00R 118.2 . . ?
C00L C00R H00R 118.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn01 O002 2.1920(12) 2_656 ?
Mn01 O002 2.1920(12) . ?
Mn01 O003 2.1378(12) 2_656 ?
Mn01 O003 2.1377(12) . ?
Mn01 O004 2.2198(13) . ?
Mn01 O004 2.2198(12) 2_656 ?
O002 H00C 0.831(14) . ?
O002 H00D 0.841(14) . ?
O003 H00E 0.8502 . ?
O003 H00F 0.8498 . ?
O004 H00G 0.8515 . ?
O004 H00H 0.8505 . ?
O005 C00D 1.241(2) . ?
O006 C00D 1.242(2) . ?
O007 C00I 1.253(2) . ?
O008 C00I 1.241(2) . ?
N009 C00J 1.336(2) . ?
N009 C00M 1.477(2) . ?
N009 C00O 1.329(2) . ?
O00A H00S 0.8496 . ?
O00A H00T 0.8503 . ?
N00B C00Q 1.333(3) . ?
N00B C00R 1.329(3) . ?
C00C H00I 0.9300 . ?
C00C C00F 1.393(2) 5_656 ?
C00C C00G 1.390(2) . ?
C00D C00M 1.529(2) . ?
C00E C00H 1.481(2) . ?
C00E C00K 1.392(3) . ?
C00E C00P 1.391(2) . ?
C00F C00G 1.388(2) . ?
C00F C00I 1.510(2) . ?
C00G H00M 0.9300 . ?
C00H C00L 1.395(3) . ?
C00H C00N 1.392(2) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.369(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00R 1.385(3) . ?
C00M H00A 0.9700 . ?
C00M H00B 0.9700 . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.380(3) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.365(3) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O005 C00D C00M N009 -2.2(3) . . . . ?
O006 C00D C00M N009 177.47(16) . . . . ?
N009 C00J C00K C00E -1.1(3) . . . . ?
N009 C00O C00P C00E -1.9(3) . . . . ?
C00C C00F C00G C00C 0.2(3) 5_656 . . . ?
C00C C00F C00I O007 153.88(17) 5_656 . . . ?
C00C C00F C00I O008 -25.8(2) 5_656 . . . ?
C00E C00H C00L C00R -179.77(16) . . . . ?
C00E C00H C00N C00Q 179.60(17) . . . . ?
C00F C00C C00G C00F -0.2(3) 5_656 . . . ?
C00G C00F C00I O007 -30.0(2) . . . . ?
C00G C00F C00I O008 150.35(18) . . . . ?
C00H C00E C00K C00J 178.69(17) . . . . ?
C00H C00E C00P C00O -177.27(19) . . . . ?
C00H C00L C00R N00B 0.3(3) . . . . ?
C00H C00N C00Q N00B 0.1(3) . . . . ?
C00I C00F C00G C00C -176.03(15) . . . . ?
C00J N009 C00M C00D -107.55(19) . . . . ?
C00J N009 C00O C00P 1.9(3) . . . . ?
C00K C00E C00H C00L 169.39(17) . . . . ?
C00K C00E C00H C00N -10.7(3) . . . . ?
C00K C00E C00P C00O 0.4(3) . . . . ?
C00L C00H C00N C00Q -0.5(3) . . . . ?
C00M N009 C00J C00K 178.30(17) . . . . ?
C00M N009 C00O C00P -176.83(19) . . . . ?
C00N C00H C00L C00R 0.3(3) . . . . ?
C00O N009 C00J C00K -0.4(3) . . . . ?
C00O N009 C00M C00D 71.1(2) . . . . ?
C00P C00E C00H C00L -13.0(3) . . . . ?
C00P C00E C00H C00N 166.87(18) . . . . ?
C00P C00E C00K C00J 1.0(3) . . . . ?
C00Q N00B C00R C00L -0.7(3) . . . . ?
C00R N00B C00Q C00N 0.5(3) . . . . ?
