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#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/95/4329576.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_4329576
loop_
_publ_author_name
'Runyu Tan'
'Zhi-Bin Wang'
'Yu Li'
'Daniel J. Kozera'
'Zheng-Hong Lu'
'Datong Song'
_publ_section_title
;
 Syntheses, Structures, and Luminescent Properties of
 Dipyridylamine-Functionalized Anthracene and Its Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7039
_journal_page_last               7049
_journal_paper_doi               10.1021/ic201757r
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C52 H32 F6 N6 O6 S2 Zn'
_chemical_formula_weight         1080.33
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 108.5820(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6487(4)
_cell_length_b                   19.4576(6)
_cell_length_c                   16.5977(6)
_cell_measurement_reflns_used    20002
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      1.93
_cell_volume                     4484.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20002
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  0.9576
_exptl_absorpt_correction_T_min  0.7951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'bruker apex 2'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_description       block
_exptl_crystal_F_000             2200
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0512
_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)+(0.0725P)²+11.6820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                3836
_reflns_number_total             5151
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic201757r_si_001_5.cif
_cod_data_source_block           2c
_cod_database_code               4329576
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.0000 0.77552(2) 0.7500 0.02189(15) Uani 1 2 d S
C1 C -0.0889(2) 0.23850(16) 0.5932(2) 0.0273(7) Uani 1 1 d .
C2 C -0.1332(2) 0.19956(18) 0.5225(2) 0.0319(7) Uani 1 1 d .
H2A H -0.1668 0.2222 0.4709 0.038 Uiso 1 1 calc R
C3 C -0.1306(3) 0.12715(18) 0.5241(2) 0.0360(8) Uani 1 1 d .
H3A H -0.1607 0.1019 0.4736 0.043 Uiso 1 1 calc R
C4 C -0.0852(3) 0.09361(18) 0.5973(2) 0.0342(8) Uani 1 1 d .
H4A H -0.0819 0.0448 0.5976 0.041 Uiso 1 1 calc R
C5 C -0.0421(2) 0.13087(16) 0.6739(2) 0.0277(7) Uani 1 1 d .
C6 C 0.0000 0.0960(2) 0.7500 0.0307(10) Uani 1 2 d S
H6A H 0.0000 0.0472 0.7500 0.037 Uiso 1 2 calc SR
C7 C 0.0000 0.2405(2) 0.7500 0.0255(9) Uani 1 2 d S
H7A H 0.0000 0.2893 0.7500 0.031 Uiso 1 2 calc SR
C8 C -0.0426(2) 0.20460(16) 0.67384(19) 0.0257(6) Uani 1 1 d .
C9 C -0.0877(2) 0.31183(17) 0.58475(19) 0.0279(7) Uani 1 1 d .
C10 C -0.0883(2) 0.37247(17) 0.5720(2) 0.0291(7) Uani 1 1 d .
C11 C -0.0893(2) 0.44625(17) 0.5699(2) 0.0290(7) Uani 1 1 d .
C12 C -0.1661(2) 0.48457(17) 0.5165(2) 0.0322(7) Uani 1 1 d .
H12A H -0.2139 0.4621 0.4717 0.039 Uiso 1 1 calc R
C13 C -0.1734(2) 0.55448(18) 0.5283(2) 0.0333(7) Uani 1 1 d .
H13A H -0.2270 0.5796 0.4932 0.040 Uiso 1 1 calc R
C14 C -0.1017(2) 0.58758(16) 0.5918(2) 0.0284(7) Uani 1 1 d .
C15 C -0.0210(2) 0.55163(18) 0.6386(2) 0.0368(8) Uani 1 1 d .
H15A H 0.0308 0.5752 0.6784 0.044 Uiso 1 1 calc R
C16 C -0.0152(3) 0.48185(19) 0.6277(2) 0.0401(9) Uani 1 1 d .
H16A H 0.0406 0.4577 0.6605 0.048 Uiso 1 1 calc R
C17 C -0.1054(2) 0.71489(16) 0.5740(2) 0.0265(6) Uani 1 1 d .
C18 C -0.0770(2) 0.83137(17) 0.5697(2) 0.0301(7) Uani 1 1 d .
H18A H -0.0594 0.8738 0.5988 0.036 Uiso 1 1 calc R
C19 C -0.1029(3) 0.83160(19) 0.4835(2) 0.0362(8) Uani 1 1 d .
H19A H -0.1038 0.8732 0.4533 0.043 Uiso 1 1 calc R
C20 C -0.1279(3) 0.7699(2) 0.4407(2) 0.0393(8) Uani 1 1 d .
H20A H -0.1439 0.7683 0.3806 0.047 Uiso 1 1 calc R
C21 C -0.1294(3) 0.71102(18) 0.4859(2) 0.0348(8) Uani 1 1 d .
H21A H -0.1466 0.6683 0.4574 0.042 Uiso 1 1 calc R
C22 C -0.1442(2) 0.65818(16) 0.69387(19) 0.0253(6) Uani 1 1 d .
C23 C -0.2116(2) 0.60966(17) 0.7020(2) 0.0296(7) Uani 1 1 d .
H23A H -0.2363 0.5761 0.6590 0.035 Uiso 1 1 calc R
C24 C -0.2417(2) 0.61079(18) 0.7721(2) 0.0333(7) Uani 1 1 d .
H24A H -0.2867 0.5777 0.7783 0.040 Uiso 1 1 calc R
C25 C 0.1393(2) 0.70600(17) 0.6778(2) 0.0307(7) Uani 1 1 d .
H25A H 0.1145 0.7402 0.6357 0.037 Uiso 1 1 calc R
C26 C 0.2060(3) 0.66050(18) 0.6663(2) 0.0339(8) Uani 1 1 d .
H26A H 0.2269 0.6631 0.6177 0.041 Uiso 1 1 calc R
C27 C 0.2595(3) 0.8899(2) 0.7346(2) 0.0409(9) Uani 1 1 d .
N1 N 0.10732(17) 0.70476(13) 0.74489(16) 0.0233(5) Uani 1 1 d .
N2 N -0.07487(18) 0.77399(13) 0.61624(17) 0.0267(6) Uani 1 1 d .
N3 N -0.11218(19) 0.65650(14) 0.62170(16) 0.0275(6) Uani 1 1 d .
S1 S 0.14396(6) 0.91848(5) 0.74003(6) 0.0341(2) Uani 1 1 d .
F1 F 0.25064(18) 0.84789(14) 0.67019(16) 0.0569(7) Uani 1 1 d .
F2 F 0.3092(2) 0.85796(17) 0.80453(17) 0.0736(9) Uani 1 1 d .
F3 F 0.31159(19) 0.94402(16) 0.72384(19) 0.0690(8) Uani 1 1 d .
O1 O 0.1096(2) 0.96318(15) 0.6670(2) 0.0585(8) Uani 1 1 d .
O2 O 0.1656(2) 0.95102(15) 0.82114(19) 0.0534(8) Uani 1 1 d .
O3 O 0.09181(18) 0.85496(13) 0.73116(18) 0.0413(6) Uani 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N1 Zn1 N1 98.62(14) . 2_556
N1 Zn1 O3 87.39(10) . .
N1 Zn1 O3 171.53(10) 2_556 .
N1 Zn1 O3 171.53(10) . 2_556
N1 Zn1 O3 87.39(10) 2_556 2_556
O3 Zn1 O3 87.30(14) . 2_556
N1 Zn1 N2 83.72(10) . 2_556
N1 Zn1 N2 95.23(10) 2_556 2_556
O3 Zn1 N2 91.34(10) . 2_556
O3 Zn1 N2 89.81(10) 2_556 2_556
N1 Zn1 N2 95.24(10) . .
N1 Zn1 N2 83.72(10) 2_556 .
O3 Zn1 N2 89.81(10) . .
O3 Zn1 N2 91.34(10) 2_556 .
N2 Zn1 N2 178.41(14) 2_556 .
C2 C1 C9 118.9(3) . .
C2 C1 C8 119.4(3) . .
C9 C1 C8 121.7(3) . .
C1 C2 C3 122.2(3) . .
C4 C3 C2 120.1(3) . .
C3 C4 C5 120.5(3) . .
C6 C5 C4 120.3(3) . .
C6 C5 C8 119.2(3) . .
C4 C5 C8 120.5(3) . .
C5 C6 C5 121.7(4) 2_556 .
C8 C7 C8 120.3(4) 2_556 .
C7 C8 C5 119.7(3) . .
C7 C8 C1 123.2(3) . .
C5 C8 C1 117.1(3) . .
C10 C9 C1 175.6(3) . .
C9 C10 C11 171.1(3) . .
C16 C11 C12 117.7(3) . .
C16 C11 C10 118.9(3) . .
C12 C11 C10 123.1(3) . .
C13 C12 C11 121.0(3) . .
C12 C13 C14 119.3(3) . .
C15 C14 C13 119.8(3) . .
C15 C14 N3 116.1(3) . .
C13 C14 N3 123.4(3) . .
C16 C15 C14 120.3(3) . .
C15 C16 C11 121.2(3) . .
N2 C17 C21 121.6(3) . .
N2 C17 N3 117.9(3) . .
C21 C17 N3 120.5(3) . .
N2 C18 C19 123.5(3) . .
C18 C19 C20 118.6(3) . .
C21 C20 C19 119.4(3) . .
C20 C21 C17 119.0(3) . .
N1 C22 C23 120.5(3) 2_556 .
N1 C22 N3 119.6(3) 2_556 .
C23 C22 N3 119.8(3) . .
C24 C23 C22 119.9(3) . .
C23 C24 C26 119.4(3) . 2_556
N1 C25 C26 123.8(3) . .
C25 C26 C24 117.7(3) . 2_556
F2 C27 F1 107.9(4) . .
F2 C27 F3 108.0(3) . .
F1 C27 F3 106.9(3) . .
F2 C27 S1 111.4(3) . .
F1 C27 S1 112.2(3) . .
F3 C27 S1 110.1(3) . .
C25 N1 C22 118.7(3) . 2_556
C25 N1 Zn1 118.9(2) . .
C22 N1 Zn1 122.4(2) 2_556 .
C17 N2 C18 117.6(3) . .
C17 N2 Zn1 121.8(2) . .
C18 N2 Zn1 119.5(2) . .
C17 N3 C22 123.9(3) . .
C17 N3 C14 121.2(3) . .
C22 N3 C14 114.1(3) . .
O2 S1 O3 115.39(18) . .
O2 S1 O1 115.90(19) . .
O3 S1 O1 113.59(18) . .
O2 S1 C27 104.66(19) . .
O3 S1 C27 101.86(17) . .
O1 S1 C27 102.97(19) . .
S1 O3 Zn1 161.29(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 2.112(2) .
Zn1 N1 2.112(2) 2_556
Zn1 O3 2.136(2) .
Zn1 O3 2.136(2) 2_556
Zn1 N2 2.140(3) 2_556
Zn1 N2 2.140(3) .
C1 C2 1.373(5) .
C1 C9 1.434(5) .
C1 C8 1.452(4) .
C2 C3 1.409(5) .
C3 C4 1.353(5) .
C4 C5 1.424(5) .
C5 C6 1.393(4) .
C5 C8 1.435(4) .
C6 C5 1.393(4) 2_556
C7 C8 1.404(4) 2_556
C7 C8 1.405(4) .
C9 C10 1.198(5) .
C10 C11 1.436(5) .
C11 C16 1.384(5) .
C11 C12 1.404(5) .
C12 C13 1.383(5) .
C13 C14 1.387(5) .
C14 C15 1.380(5) .
C14 N3 1.455(4) .
C15 C16 1.376(5) .
C17 N2 1.347(4) .
C17 C21 1.393(5) .
C17 N3 1.406(4) .
C18 N2 1.353(4) .
C18 C19 1.358(5) .
C19 C20 1.383(5) .
C20 C21 1.374(5) .
C22 N1 1.340(4) 2_556
C22 C23 1.403(4) .
C22 N3 1.419(4) .
C23 C24 1.369(5) .
C24 C26 1.384(5) 2_556
C25 N1 1.339(4) .
C25 C26 1.376(5) .
C26 C24 1.384(5) 2_556
C27 F2 1.313(4) .
C27 F1 1.318(5) .
C27 F3 1.346(5) .
C27 S1 1.811(4) .
N1 C22 1.340(4) 2_556
S1 O2 1.429(3) .
S1 O3 1.436(2) .
S1 O1 1.446(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139137432
