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#$Date: 2016-03-26 03:38:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180190 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/86/7108622.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_7108622
loop_
_publ_author_name
'Yu Zeng'
'Shijun Liao'
'Jingcao Dai'
'Zhiyong Fu'
_publ_section_title
;
 Fluorescent and photochromic bifunctional molecular switch based on a
 stable crystalline metal-viologen complex
;
_journal_name_full               Chem.Commun.
_journal_page_first              11641
_journal_paper_doi               10.1039/c2cc35115c
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C26 H18 N2 O9 Zn'
_chemical_formula_weight         567.79
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.56(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5601(19)
_cell_length_b                   14.382(3)
_cell_length_c                   18.401(5)
_cell_measurement_reflns_used    4240
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      3.08
_cell_volume                     2319.1(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18247
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    1.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.683
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1005P)²+0.9328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1513
_reflns_number_gt                3245
_reflns_number_total             4240
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc35115c.txt
_cod_data_source_block           3
_cod_original_cell_volume        2318.6(9)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7108622
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.37279(4) -0.54196(3) 0.13966(2) 0.04961(19) Uani 1 1 d .
O1 O 0.3489(3) -0.4204(2) 0.08732(16) 0.0701(8) Uani 1 1 d .
O2 O 0.5112(5) -0.3543(3) 0.19362(18) 0.1127(14) Uani 1 1 d .
O3 O 0.2243(4) -0.5323(2) 0.1893(2) 0.0810(10) Uani 1 1 d .
O4 O 0.2378(5) -0.6819(3) 0.2021(2) 0.1005(12) Uani 1 1 d .
O5 O -0.3822(4) -0.5775(3) 0.12199(19) 0.0972(11) Uani 1 1 d .
O6 O -0.4313(3) -0.5721(3) 0.2272(2) 0.0947(12) Uani 1 1 d .
O7 O 0.0023(4) -0.6277(3) 0.49396(17) 0.0955(11) Uani 1 1 d .
O8 O 0.2368(3) -0.6276(2) 0.49827(16) 0.0678(8) Uani 1 1 d .
O9 O 0.6494(4) -0.1693(3) -0.14900(17) 0.1192(16) Uani 1 1 d .
H3 H 0.5981 -0.1577 -0.1978 0.179 Uiso 1 1 d R
H2 H 0.6920 -0.2122 -0.1645 0.179 Uiso 1 1 d R
N2 N -0.2529(3) -0.1066(2) -0.53150(16) 0.0530(7) Uani 1 1 d .
C1 C 0.4221(4) -0.3517(3) 0.1246(2) 0.0558(9) Uani 1 1 d .
C2 C 0.3968(4) -0.2612(3) 0.07959(19) 0.0481(8) Uani 1 1 d .
C3 C 0.4526(4) -0.1787(3) 0.1198(2) 0.0570(9) Uani 1 1 d .
H3A H 0.5067 -0.1797 0.1745 0.068 Uiso 1 1 calc R
C4 C 0.4286(4) -0.0953(3) 0.0795(2) 0.0646(10) Uani 1 1 d .
H4A H 0.4664 -0.0404 0.1071 0.077 Uiso 1 1 calc R
C5 C 0.3480(4) -0.0935(3) -0.0022(2) 0.0616(10) Uani 1 1 d .
H5A H 0.3320 -0.0380 -0.0302 0.074 Uiso 1 1 calc R
C6 C 0.3151(4) -0.2597(3) -0.00192(19) 0.0496(8) Uani 1 1 d .
H6A H 0.2765 -0.3144 -0.0298 0.059 Uiso 1 1 calc R
C7 C 0.2924(4) -0.1762(3) -0.04046(19) 0.0490(8) Uani 1 1 d .
N1 N 0.1991(3) -0.1726(2) -0.12624(16) 0.0504(7) Uani 1 1 d .
C9 C 0.2640(4) -0.1791(3) -0.1784(2) 0.0579(9) Uani 1 1 d .
H9A H 0.3686 -0.1889 -0.1604 0.069 Uiso 1 1 calc R
C10 C 0.1779(4) -0.1716(3) -0.2577(2) 0.0581(10) Uani 1 1 d .
H10A H 0.2245 -0.1762 -0.2933 0.070 Uiso 1 1 calc R
C11 C 0.0474(4) -0.1610(3) -0.1516(2) 0.0621(10) Uani 1 1 d .
H11A H 0.0028 -0.1585 -0.1150 0.075 Uiso 1 1 calc R
C12 C -0.0413(4) -0.1529(3) -0.2304(2) 0.0607(10) Uani 1 1 d .
H12A H -0.1460 -0.1444 -0.2471 0.073 Uiso 1 1 calc R
C13 C 0.0216(4) -0.1572(2) -0.28597(19) 0.0476(8) Uani 1 1 d .
C14 C -0.0742(4) -0.1434(2) -0.37194(19) 0.0456(7) Uani 1 1 d .
C15 C -0.0116(4) -0.1367(4) -0.4270(2) 0.0744(13) Uani 1 1 d .
H15A H 0.0929 -0.1446 -0.4116 0.089 Uiso 1 1 calc R
C16 C -0.1026(4) -0.1185(4) -0.5046(2) 0.0731(13) Uani 1 1 d .
H16A H -0.0569 -0.1141 -0.5406 0.088 Uiso 1 1 calc R
C17 C -0.2285(4) -0.1339(4) -0.3996(2) 0.0757(14) Uani 1 1 d .
H17A H -0.2768 -0.1406 -0.3650 0.091 Uiso 1 1 calc R
C18 C -0.3135(4) -0.1145(4) -0.4780(2) 0.0742(13) Uani 1 1 d .
H18A H -0.4183 -0.1064 -0.4946 0.089 Uiso 1 1 calc R
C19 C 0.1917(4) -0.6052(3) 0.2130(2) 0.0557(9) Uani 1 1 d .
C20 C 0.0849(4) -0.5990(3) 0.25548(19) 0.0489(8) Uani 1 1 d .
C21 C 0.1366(4) -0.6101(3) 0.3372(2) 0.0522(8) Uani 1 1 d .
H21A H 0.2401 -0.6193 0.3675 0.063 Uiso 1 1 calc R
C22 C 0.0348(4) -0.6075(3) 0.37398(19) 0.0493(8) Uani 1 1 d .
C23 C -0.1194(4) -0.5957(3) 0.3287(2) 0.0527(8) Uani 1 1 d .
H23A H -0.1876 -0.5933 0.3532 0.063 Uiso 1 1 calc R
C24 C -0.1727(4) -0.5873(3) 0.2466(2) 0.0499(8) Uani 1 1 d .
C25 C -0.0695(4) -0.5873(3) 0.21129(19) 0.0513(8) Uani 1 1 d .
H25A H -0.1047 -0.5794 0.1567 0.062 Uiso 1 1 calc R
C26 C -0.3410(4) -0.5785(3) 0.1945(3) 0.0648(10) Uani 1 1 d .
C27 C 0.0878(4) -0.6210(3) 0.4619(2) 0.0559(9) Uani 1 1 d .
H1 H 0.270(6) -0.637(3) 0.550(3) 0.092(16) Uiso 1 1 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'
Zn Zn 0.2839 1.4301 '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
O1 Zn1 O6 118.86(14) . 1_655
O1 Zn1 O3 101.54(13) . .
O6 Zn1 O3 105.17(14) 1_655 .
O1 Zn1 N2 90.98(12) . 2_544
O6 Zn1 N2 131.70(16) 1_655 2_544
O3 Zn1 N2 104.53(14) . 2_544
O1 Zn1 C26 105.77(13) . 1_655
O6 Zn1 C26 27.94(13) 1_655 1_655
O3 Zn1 C26 133.11(15) . 1_655
N2 Zn1 C26 112.25(14) 2_544 1_655
C1 O1 Zn1 120.4(2) . .
C19 O3 Zn1 115.9(3) . .
C26 O6 Zn1 103.8(3) . 1_455
C27 O8 H1 114(3) . .
H3 O9 H2 86.5 . .
C16 N2 C18 116.1(3) . .
C16 N2 Zn1 120.9(2) . 2_554
C18 N2 Zn1 120.6(2) . 2_554
O2 C1 O1 123.8(4) . .
O2 C1 C2 119.5(4) . .
O1 C1 C2 116.7(3) . .
C6 C2 C3 119.6(3) . .
C6 C2 C1 120.3(3) . .
C3 C2 C1 120.1(3) . .
C4 C3 C2 120.7(3) . .
C4 C3 H3A 119.7 . .
C2 C3 H3A 119.7 . .
C3 C4 C5 119.9(4) . .
C3 C4 H4A 120.0 . .
C5 C4 H4A 120.0 . .
C7 C5 C4 118.2(4) . .
C7 C5 H5A 120.9 . .
C4 C5 H5A 120.9 . .
C7 C6 C2 118.6(3) . .
C7 C6 H6A 120.7 . .
C2 C6 H6A 120.7 . .
C6 C7 C5 123.0(3) . .
C6 C7 N1 119.3(3) . .
C5 C7 N1 117.6(3) . .
C9 N1 C11 120.4(3) . .
C9 N1 C7 120.7(3) . .
C11 N1 C7 118.9(3) . .
N1 C9 C10 120.5(3) . .
N1 C9 H9A 119.8 . .
C10 C9 H9A 119.8 . .
C9 C10 C13 120.8(3) . .
C9 C10 H10A 119.6 . .
C13 C10 H10A 119.6 . .
N1 C11 C12 120.4(3) . .
N1 C11 H11A 119.8 . .
C12 C11 H11A 119.8 . .
C11 C12 C13 121.0(3) . .
C11 C12 H12A 119.5 . .
C13 C12 H12A 119.5 . .
C12 C13 C10 116.9(3) . .
C12 C13 C14 121.0(3) . .
C10 C13 C14 122.1(3) . .
C17 C14 C15 116.4(3) . .
C17 C14 C13 121.6(3) . .
C15 C14 C13 122.0(3) . .
C16 C15 C14 120.1(3) . .
C16 C15 H15A 119.9 . .
C14 C15 H15A 119.9 . .
N2 C16 C15 123.7(3) . .
N2 C16 H16A 118.2 . .
C15 C16 H16A 118.2 . .
C14 C17 C18 120.8(3) . .
C14 C17 H17A 119.6 . .
C18 C17 H17A 119.6 . .
N2 C18 C17 123.0(3) . .
N2 C18 H18A 118.5 . .
C17 C18 H18A 118.5 . .
O3 C19 O4 123.4(4) . .
O3 C19 C20 116.9(4) . .
O4 C19 C20 119.7(4) . .
C25 C20 C21 119.0(3) . .
C25 C20 C19 119.0(3) . .
C21 C20 C19 121.9(3) . .
C20 C21 C22 120.5(3) . .
C20 C21 H21A 119.8 . .
C22 C21 H21A 119.8 . .
C23 C22 C21 119.7(3) . .
C23 C22 C27 118.9(3) . .
C21 C22 C27 121.4(3) . .
C22 C23 C24 120.2(3) . .
C22 C23 H23A 119.9 . .
C24 C23 H23A 119.9 . .
C25 C24 C23 119.3(3) . .
C25 C24 C26 118.6(3) . .
C23 C24 C26 122.1(3) . .
C24 C25 C20 121.3(3) . .
C24 C25 H25A 119.4 . .
C20 C25 H25A 119.4 . .
O5 C26 O6 122.9(4) . .
O5 C26 C24 119.1(4) . .
O6 C26 C24 118.0(4) . .
O5 C26 Zn1 75.1(2) . 1_455
O6 C26 Zn1 48.22(19) . 1_455
C24 C26 Zn1 164.4(3) . 1_455
O7 C27 O8 124.3(3) . .
O7 C27 C22 122.8(3) . .
O8 C27 C22 112.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.965(3) .
Zn1 O6 1.969(3) 1_655
Zn1 O3 1.976(3) .
Zn1 N2 2.077(3) 2_544
Zn1 C26 2.564(4) 1_655
O1 C1 1.246(5) .
O2 C1 1.215(4) .
O3 C19 1.222(5) .
O4 C19 1.234(5) .
O5 C26 1.231(5) .
O6 C26 1.237(5) .
O6 Zn1 1.969(3) 1_455
O7 C27 1.188(4) .
O8 C27 1.312(4) .
O8 H1 0.88(5) .
O9 H3 0.8500 .
O9 H2 0.8501 .
N2 C16 1.330(5) .
N2 C18 1.332(5) .
N2 Zn1 2.077(3) 2_554
C1 C2 1.509(5) .
C2 C6 1.387(4) .
C2 C3 1.387(5) .
C3 C4 1.381(6) .
C3 H3A 0.9300 .
C4 C5 1.388(5) .
C4 H4A 0.9300 .
C5 C7 1.376(6) .
C5 H5A 0.9300 .
C6 C7 1.367(5) .
C6 H6A 0.9300 .
C7 N1 1.471(4) .
N1 C9 1.338(4) .
N1 C11 1.344(5) .
C9 C10 1.363(5) .
C9 H9A 0.9300 .
C10 C13 1.387(5) .
C10 H10A 0.9300 .
C11 C12 1.362(5) .
C11 H11A 0.9300 .
C12 C13 1.379(5) .
C12 H12A 0.9300 .
C13 C14 1.491(5) .
C14 C17 1.362(5) .
C14 C15 1.371(5) .
C15 C16 1.368(5) .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
C17 C18 1.372(5) .
C17 H17A 0.9300 .
C18 H18A 0.9300 .
C19 C20 1.517(5) .
C20 C25 1.382(5) .
C20 C21 1.392(5) .
C21 C22 1.390(5) .
C21 H21A 0.9300 .
C22 C23 1.384(5) .
C22 C27 1.502(5) .
C23 C24 1.392(5) .
C23 H23A 0.9300 .
C24 C25 1.382(5) .
C24 C26 1.513(5) .
C25 H25A 0.9300 .
C26 Zn1 2.564(4) 1_455
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_4
O6 Zn1 O1 C1 -28.9(3) 1_655 .
O3 Zn1 O1 C1 85.8(3) . .
N2 Zn1 O1 C1 -169.1(3) 2_544 .
C26 Zn1 O1 C1 -55.7(3) 1_655 .
O1 Zn1 O3 C19 165.8(3) . .
O6 Zn1 O3 C19 -69.8(3) 1_655 .
N2 Zn1 O3 C19 71.7(3) 2_544 .
C26 Zn1 O3 C19 -69.4(4) 1_655 .
Zn1 O1 C1 O2 0.2(6) . .
Zn1 O1 C1 C2 179.9(2) . .
O2 C1 C2 C6 169.7(4) . .
O1 C1 C2 C6 -10.0(5) . .
O2 C1 C2 C3 -11.6(5) . .
O1 C1 C2 C3 168.7(3) . .
C6 C2 C3 C4 -0.5(5) . .
C1 C2 C3 C4 -179.2(3) . .
C2 C3 C4 C5 -0.1(6) . .
C3 C4 C5 C7 0.8(6) . .
C3 C2 C6 C7 0.3(5) . .
C1 C2 C6 C7 179.0(3) . .
C2 C6 C7 C5 0.5(5) . .
C2 C6 C7 N1 -176.7(3) . .
C4 C5 C7 C6 -1.1(6) . .
C4 C5 C7 N1 176.2(3) . .
C6 C7 N1 C9 -92.8(4) . .
C5 C7 N1 C9 89.8(4) . .
C6 C7 N1 C11 88.3(4) . .
C5 C7 N1 C11 -89.1(4) . .
C11 N1 C9 C10 1.8(6) . .
C7 N1 C9 C10 -177.1(4) . .
N1 C9 C10 C13 -0.1(6) . .
C9 N1 C11 C12 -2.0(6) . .
C7 N1 C11 C12 176.9(4) . .
N1 C11 C12 C13 0.5(7) . .
C11 C12 C13 C10 1.1(6) . .
C11 C12 C13 C14 -176.8(4) . .
C9 C10 C13 C12 -1.3(6) . .
C9 C10 C13 C14 176.5(4) . .
C12 C13 C14 C17 -5.6(6) . .
C10 C13 C14 C17 176.7(4) . .
C12 C13 C14 C15 172.3(4) . .
C10 C13 C14 C15 -5.3(6) . .
C17 C14 C15 C16 2.0(7) . .
C13 C14 C15 C16 -176.0(4) . .
C18 N2 C16 C15 -0.6(7) . .
Zn1 N2 C16 C15 161.8(4) 2_554 .
C14 C15 C16 N2 -0.3(8) . .
C15 C14 C17 C18 -2.8(7) . .
C13 C14 C17 C18 175.2(4) . .
C16 N2 C18 C17 -0.2(7) . .
Zn1 N2 C18 C17 -162.7(4) 2_554 .
C14 C17 C18 N2 2.1(8) . .
Zn1 O3 C19 O4 -5.4(6) . .
Zn1 O3 C19 C20 176.6(2) . .
O3 C19 C20 C25 77.5(5) . .
O4 C19 C20 C25 -100.6(5) . .
O3 C19 C20 C21 -106.4(4) . .
O4 C19 C20 C21 75.6(5) . .
C25 C20 C21 C22 -1.4(6) . .
C19 C20 C21 C22 -177.5(4) . .
C20 C21 C22 C23 1.3(6) . .
C20 C21 C22 C27 178.9(4) . .
C21 C22 C23 C24 0.6(6) . .
C27 C22 C23 C24 -177.0(4) . .
C22 C23 C24 C25 -2.5(6) . .
C22 C23 C24 C26 177.3(4) . .
C23 C24 C25 C20 2.5(6) . .
C26 C24 C25 C20 -177.4(4) . .
C21 C20 C25 C24 -0.5(6) . .
C19 C20 C25 C24 175.7(4) . .
Zn1 O6 C26 O5 -8.5(6) 1_455 .
Zn1 O6 C26 C24 171.2(3) 1_455 .
C25 C24 C26 O5 4.6(6) . .
C23 C24 C26 O5 -175.2(4) . .
C25 C24 C26 O6 -175.1(4) . .
C23 C24 C26 O6 5.1(6) . .
C25 C24 C26 Zn1 -149.9(9) . 1_455
C23 C24 C26 Zn1 30.3(12) . 1_455
C23 C22 C27 O7 4.7(6) . .
C21 C22 C27 O7 -172.9(4) . .
C23 C22 C27 O8 -177.4(4) . .
C21 C22 C27 O8 5.0(5) . .
