#------------------------------------------------------------------------------
#$Date: 2019-11-08 02:22:57 +0200 (Fri, 08 Nov 2019) $
#$Revision: 224744 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/86/7058629.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_7058629
loop_
_publ_author_name
'Liu, Jinjian'
'Li, Jing'
'Lu, Wenbo'
_publ_section_title
;
 Effect of counter cations on the photochromic behaviors of three
 Zn--viologen complexes
;
_journal_issue                   32
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12678
_journal_paper_doi               10.1039/C9NJ03022K
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C9 H13 O11 Zn, C8 H11 N, H2 O'
_chemical_formula_sum            'C17 H26 N O12 Zn'
_chemical_formula_weight         501.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-22 deposited with the CCDC.    2019-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.4294(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9320(2)
_cell_length_b                   11.7094(3)
_cell_length_c                   15.8407(3)
_cell_measurement_reflns_used    3368
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      71.8560
_cell_measurement_theta_min      3.7810
_cell_volume                     2027.09(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      273(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0710
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  64.00   1.00    1.00    --    0.00  77.00  30.00   67
  2  ω     -3.00  36.00   1.00    1.00    --    0.00 -99.00-120.00   39
  3  ω     79.00 114.00   1.00    5.00    --   54.94  57.00-180.00   35
  4  ω      4.00  76.00   1.00    5.00    --   54.94 -57.00 120.00   72
  5  ω     49.00 115.00   1.00    5.00    --   54.94  57.00-120.00   66
  6  ω    -17.00  78.00   1.00    5.00    --   54.94 -38.00   0.00   95
  7  ω     38.00 106.00   1.00    2.50    --  109.89-111.00  30.00   68
  8  ω     52.00  78.00   1.00    2.50    --  109.89-111.00 150.00   26
  9  ω    114.00 178.00   1.00    2.50    --  109.89 111.00  30.00   64
 10  ω     45.00  89.00   1.00    2.50    --  109.89-111.00-120.00   44
 11  ω     44.00 103.00   1.00    2.50    --  109.89-111.00 120.00   59
 12  ω     85.00 110.00   1.00    2.50    --  109.89-111.00 150.00   25
 13  ω     84.00 177.00   1.00    2.50    --  109.89  25.00-120.00   93
 14  ω     89.00 178.00   1.00    2.50    --  109.89  50.00 120.00   89
 15  ω     69.00 106.00   1.00    2.50    --  109.89 -25.00  60.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0161749000
_diffrn_orient_matrix_UB_12      -0.1219044000
_diffrn_orient_matrix_UB_13      -0.0345468000
_diffrn_orient_matrix_UB_21      0.1243780000
_diffrn_orient_matrix_UB_22      -0.0093215000
_diffrn_orient_matrix_UB_23      0.0474645000
_diffrn_orient_matrix_UB_31      -0.0644266000
_diffrn_orient_matrix_UB_32      -0.0486429000
_diffrn_orient_matrix_UB_33      0.0775283000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.033
_diffrn_reflns_theta_min         4.697
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.300
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0608P)²+2.0480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3505
_reflns_number_total             3911
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj03022k2.cif
_cod_data_source_block           liujj20190412c
_cod_depositor_comments
'Adding full bibliography for 7058629--7058631.cif.'
_cod_database_code               7058629
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N Br Zn'
_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.
;
_shelx_estimated_absorpt_t_max   0.656
_shelx_estimated_absorpt_t_min   0.545
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O12(H12A,H12B)
2.b Rotating group:
 O10(H10A,H10B), O7(H7A,H7B), O9(H9A,H9B), O11(H11A,H11B), O8(H8A,H8B)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C4(H4), C6(H6), C5(H5), C11(H11), C7(H7)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.095
_oxdiff_exptl_absorpt_empirical_full_min 0.759
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Zn1 Zn 0.56063(3) 0.45386(3) 0.15614(2) 0.02165(13) Uani 1 1 d .
O6 O 0.45603(18) 0.46157(14) 0.26612(11) 0.0279(4) Uani 1 1 d .
O5 O 0.38646(18) 0.64007(16) 0.25382(11) 0.0307(4) Uani 1 1 d .
O10 O 0.64370(18) 0.31179(16) 0.20762(11) 0.0302(4) Uani 1 1 d .
H10A H 0.6652 0.3246 0.2595 0.045 Uiso 1 1 d GR
H10B H 0.7080 0.2946 0.1798 0.045 Uiso 1 1 d GR
O4 O 0.26288(19) 0.84403(16) 0.51448(11) 0.0313(4) Uani 1 1 d .
O1 O 0.2945(2) 0.24234(17) 0.51301(13) 0.0466(6) Uani 1 1 d .
O7 O 0.46849(17) 0.59200(16) 0.09899(11) 0.0277(4) Uani 1 1 d .
H7A H 0.4161 0.6228 0.1335 0.042 Uiso 1 1 d GR
H7B H 0.4276 0.5701 0.0535 0.042 Uiso 1 1 d GR
O9 O 0.67381(17) 0.44637(14) 0.04883(11) 0.0244(4) Uani 1 1 d .
H9A H 0.7249 0.3893 0.0530 0.037 Uiso 1 1 d GR
H9B H 0.7162 0.5090 0.0443 0.037 Uiso 1 1 d GR
O2 O 0.3060(2) 0.32781(16) 0.63752(11) 0.0357(5) Uani 1 1 d .
O3 O 0.2885(2) 0.75776(18) 0.63775(11) 0.0466(6) Uani 1 1 d .
N1 N -0.0311(2) 0.4415(2) 0.28343(18) 0.0388(6) Uani 1 1 d .
C10 C 0.3702(2) 0.5470(2) 0.38681(15) 0.0220(5) Uani 1 1 d .
C15 C 0.3167(2) 0.6476(2) 0.51404(15) 0.0224(5) Uani 1 1 d .
O12 O 0.3443(3) 0.2433(2) 0.23570(18) 0.0595(7) Uani 1 1 d .
H12A H 0.2702 0.2245 0.2430 0.089 Uiso 1 1 d G
H12B H 0.3588 0.3069 0.2597 0.089 Uiso 1 1 d G
C17 C 0.3443(2) 0.6482(2) 0.42877(15) 0.0231(5) Uani 1 1 d .
H17 H 0.3455 0.7171 0.3995 0.028 Uiso 1 1 calc R
C9 C 0.4069(2) 0.5505(2) 0.29517(15) 0.0216(5) Uani 1 1 d .
C12 C 0.3306(2) 0.4414(2) 0.51443(16) 0.0221(5) Uani 1 1 d .
C14 C 0.3121(2) 0.5435(2) 0.55658(15) 0.0225(5) Uani 1 1 d .
H14 H 0.2965 0.5426 0.6140 0.027 Uiso 1 1 calc R
C13 C 0.3107(2) 0.3277(2) 0.55791(16) 0.0257(5) Uani 1 1 d .
C16 C 0.2880(2) 0.7583(2) 0.55846(15) 0.0250(5) Uani 1 1 d .
C8 C -0.0053(3) 0.4876(2) 0.4539(2) 0.0355(6) Uani 1 1 d .
C4 C -0.0371(3) 0.5497(3) 0.3109(2) 0.0444(8) Uani 1 1 d .
H4 H -0.0497 0.6087 0.2724 0.053 Uiso 1 1 calc R
C2 C 0.0211(6) 0.4870(5) 0.1341(3) 0.0881(16) Uani 1 1 d .
H2A H 0.0089 0.4564 0.0777 0.106 Uiso 1 1 calc R
H2B H -0.0147 0.5628 0.1342 0.106 Uiso 1 1 calc R
C6 C 0.0011(4) 0.3764(3) 0.4227(2) 0.0518(9) Uani 1 1 d .
H6 H 0.0148 0.3158 0.4597 0.062 Uiso 1 1 calc R
C5 C -0.0125(4) 0.3560(3) 0.3385(2) 0.0504(8) Uani 1 1 d .
H5 H -0.0089 0.2813 0.3188 0.061 Uiso 1 1 calc R
C1 C 0.1493(5) 0.4994(6) 0.1488(4) 0.108(2) Uani 1 1 d .
H1A H 0.1814 0.5526 0.1089 0.129 Uiso 1 1 calc GR
H1B H 0.1886 0.4267 0.1424 0.129 Uiso 1 1 calc GR
H1C H 0.1645 0.5274 0.2051 0.129 Uiso 1 1 calc GR
O11 O 0.43751(18) 0.33510(16) 0.09665(12) 0.0322(4) Uani 1 1 d .
H11A H 0.3852 0.3697 0.0618 0.048 Uiso 1 1 d GR
H11B H 0.3891 0.3036 0.1338 0.048 Uiso 1 1 d GR
C11 C 0.3621(2) 0.4433(2) 0.42972(16) 0.0237(5) Uani 1 1 d .
H11 H 0.3777 0.3753 0.4017 0.028 Uiso 1 1 calc R
C7 C -0.0247(3) 0.5737(3) 0.3953(2) 0.0424(7) Uani 1 1 d .
H7 H -0.0295 0.6490 0.4135 0.051 Uiso 1 1 calc R
C3 C -0.0498(3) 0.4156(3) 0.1919(2) 0.0492(8) Uani 1 1 d .
H3A H -0.0285 0.3362 0.1825 0.059 Uiso 1 1 calc R
H3B H -0.1361 0.4243 0.1775 0.059 Uiso 1 1 calc R
O8 O 0.68599(19) 0.56460(16) 0.21279(12) 0.0317(4) Uani 1 1 d .
H8A H 0.6584 0.5911 0.2601 0.048 Uiso 1 1 d GR
H8B H 0.6943 0.6258 0.1822 0.048 Uiso 1 1 d GR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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_3
O6 Zn1 O9 177.30(7) .
O6 Zn1 O11 92.50(8) .
O10 Zn1 O6 87.15(7) .
O10 Zn1 O7 176.34(8) .
O10 Zn1 O9 91.35(7) .
O10 Zn1 O11 85.15(8) .
O10 Zn1 O8 93.08(8) .
O7 Zn1 O6 93.38(7) .
O7 Zn1 O9 88.25(7) .
O7 Zn1 O11 91.21(8) .
O9 Zn1 O11 89.61(7) .
O8 Zn1 O6 88.96(8) .
O8 Zn1 O7 90.55(8) .
O8 Zn1 O9 88.87(7) .
O8 Zn1 O11 177.64(8) .
C9 O6 Zn1 125.47(15) .
C4 N1 C3 120.1(3) .
C5 N1 C4 120.2(3) .
C5 N1 C3 119.7(3) .
C17 C10 C9 119.8(2) .
C17 C10 C11 119.5(2) .
C11 C10 C9 120.8(2) .
C17 C15 C14 119.0(2) .
C17 C15 C16 120.0(2) .
C14 C15 C16 121.0(2) .
C10 C17 C15 120.7(2) .
O6 C9 C10 116.9(2) .
O5 C9 O6 124.8(2) .
O5 C9 C10 118.3(2) .
C14 C12 C13 120.9(2) .
C14 C12 C11 119.4(2) .
C11 C12 C13 119.6(2) .
C12 C14 C15 120.9(2) .
O1 C13 O2 124.4(2) .
O1 C13 C12 117.9(2) .
O2 C13 C12 117.6(2) .
O4 C16 O3 123.9(2) .
O4 C16 C15 118.4(2) .
O3 C16 C15 117.7(2) .
C6 C8 C8 121.7(4) 3_566
C7 C8 C8 121.5(3) 3_566
C7 C8 C6 116.7(3) .
N1 C4 C7 120.4(3) .
C1 C2 C3 119.2(6) .
C5 C6 C8 120.4(3) .
N1 C5 C6 121.3(3) .
C12 C11 C10 120.3(2) .
C4 C7 C8 121.1(3) .
C2 C3 N1 115.3(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O6 2.1095(17) .
Zn1 O10 2.0542(18) .
Zn1 O7 2.0988(18) .
Zn1 O9 2.1291(17) .
Zn1 O11 2.1378(19) .
Zn1 O8 2.0745(19) .
O6 C9 1.263(3) .
O5 C9 1.254(3) .
O4 C16 1.249(3) .
O1 C13 1.237(3) .
O2 C13 1.263(3) .
O3 C16 1.256(3) .
N1 C4 1.341(4) .
N1 C5 1.340(4) .
N1 C3 1.490(4) .
C10 C17 1.391(3) .
C10 C9 1.516(3) .
C10 C11 1.395(3) .
C15 C17 1.392(3) .
C15 C14 1.394(3) .
C15 C16 1.511(3) .
C12 C14 1.387(3) .
C12 C13 1.516(3) .
C12 C11 1.394(3) .
C8 C8 1.490(6) 3_566
C8 C6 1.396(4) .
C8 C7 1.383(4) .
C4 C7 1.370(5) .
C2 C1 1.423(8) .
C2 C3 1.474(6) .
C6 C5 1.359(5) .
