#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/95/4329571.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_4329571
loop_
_publ_author_name
'Sabrina M. Huber'
'Martin S. Seyfried'
'Anthony Linden'
'Nathan W. Luedtke'
_publ_section_title
;
 Excitonic Luminescence of Hemiporphyrazines
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7032
_journal_page_last               7038
_journal_paper_doi               10.1021/ic2017566
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C28 H24 N8 O2 Zn 2+, 2(C F3 O3 S -)'
_chemical_formula_sum            'C30 H24 F6 N8 O8 S2 Zn'
_chemical_formula_weight         868.06
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             10-08-25
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.121(3)
_cell_angle_beta                 95.376(2)
_cell_angle_gamma                106.102(5)
_cell_formula_units_Z            1
_cell_length_a                   8.2520(2)
_cell_length_b                   10.8769(4)
_cell_length_c                   11.4996(5)
_cell_measurement_reflns_used    9487
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      28.2885
_cell_measurement_theta_min      2.7920
_cell_volume                     852.89(7)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Atlas CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_measurement_method       'ω scans with κ offsets'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) x-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13290
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0044(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0267
_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)+(0.0318P)²+0.5460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0703
_reflns_number_gt                3518
_reflns_number_total             3780
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic2017566_si_003.cif
_cod_data_source_block           LK1001a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        852.88(5)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4329571
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.5000 0.0000 0.5000 0.01667(8) Uani 1 2 d S
S1 S 0.75169(5) 0.26751(4) 0.23558(4) 0.02041(10) Uani 1 1 d .
F1 F 0.5328(2) 0.38263(17) 0.35194(16) 0.0625(4) Uani 1 1 d .
F2 F 0.8010(2) 0.52508(15) 0.44278(14) 0.0690(5) Uani 1 1 d .
F3 F 0.6677(2) 0.48877(15) 0.25324(16) 0.0619(4) Uani 1 1 d .
O1 O 0.70377(16) 0.21708(13) 0.56115(12) 0.0243(3) Uani 1 1 d .
H1 H 0.729(3) 0.222(3) 0.497(3) 0.042(7) Uiso 1 1 d .
O2 O 0.61209(16) 0.17108(14) 0.11290(11) 0.0280(3) Uani 1 1 d .
O3 O 0.91699(18) 0.32809(18) 0.21608(16) 0.0446(4) Uani 1 1 d .
O4 O 0.75590(17) 0.20949(14) 0.32557(12) 0.0287(3) Uani 1 1 d .
N1 N 0.39356(16) 0.09445(14) 0.64699(12) 0.0169(3) Uani 1 1 d .
N2 N 0.18187(17) 0.14531(15) 0.53063(13) 0.0199(3) Uani 1 1 d .
N3 N 0.32710(16) 0.02669(14) 0.35897(12) 0.0163(3) Uani 1 1 d .
N4 N 0.44439(17) -0.09284(15) 0.17287(13) 0.0182(3) Uani 1 1 d .
H4 H 0.438(3) -0.114(2) 0.094(2) 0.028(5) Uiso 1 1 d .
C1 C 0.43179(19) 0.12220(16) 0.77336(14) 0.0165(3) Uani 1 1 d .
C2 C 0.3202(2) 0.19349(17) 0.85174(15) 0.0187(3) Uani 1 1 d .
C3 C 0.2101(2) 0.20621(17) 0.76242(15) 0.0191(3) Uani 1 1 d .
C4 C 0.25702(19) 0.14451(17) 0.63213(15) 0.0175(3) Uani 1 1 d .
C5 C 0.3094(2) 0.24184(18) 0.98452(16) 0.0226(3) Uani 1 1 d .
H5 H 0.3845 0.2330 1.0458 0.027 Uiso 1 1 calc R
C6 C 0.1832(2) 0.30380(19) 1.02331(17) 0.0256(4) Uani 1 1 d .
H6 H 0.1719 0.3381 1.1132 0.031 Uiso 1 1 calc R
C7 C 0.0734(2) 0.31658(19) 0.93355(18) 0.0262(4) Uani 1 1 d .
H7 H -0.0111 0.3596 0.9636 0.031 Uiso 1 1 calc R
C8 C 0.0842(2) 0.26763(19) 0.80040(17) 0.0237(3) Uani 1 1 d .
H8 H 0.0091 0.2760 0.7388 0.028 Uiso 1 1 calc R
C9 C 0.2124(2) 0.09654(17) 0.40265(15) 0.0178(3) Uani 1 1 d .
C10 C 0.1115(2) 0.12570(18) 0.32125(16) 0.0218(3) Uani 1 1 d .
H10 H 0.0342 0.1756 0.3556 0.026 Uiso 1 1 calc R
C11 C 0.1244(2) 0.08185(19) 0.19062(16) 0.0237(3) Uani 1 1 d .
H11 H 0.0570 0.1015 0.1341 0.028 Uiso 1 1 calc R
C12 C 0.2368(2) 0.00914(18) 0.14381(15) 0.0213(3) Uani 1 1 d .
H12 H 0.2477 -0.0235 0.0539 0.026 Uiso 1 1 calc R
C13 C 0.33474(19) -0.01584(16) 0.23079(15) 0.0168(3) Uani 1 1 d .
C14 C 0.7035(3) 0.3589(2) 0.6537(2) 0.0449(5) Uani 1 1 d .
H14A H 0.6005 0.3725 0.6194 0.067 Uiso 1 1 calc R
H14B H 0.8093 0.4357 0.6639 0.067 Uiso 1 1 calc R
H14C H 0.7006 0.3664 0.7416 0.067 Uiso 1 1 calc R
C15 C 0.6856(3) 0.4251(2) 0.3262(2) 0.0377(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 30 0.0033 0.0016
; International Tables for Crystallography (1992). 
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 24 0.0000 0.0000
; International Tables for Crystallography (1992). 
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
F F 6 0.0171 0.0103
; International Tables for Crystallography (1992). 
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 8 0.0061 0.0033
; International Tables for Crystallography (1992). 
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 8 0.0106 0.0060
; International Tables for Crystallography (1992). 
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
S S 2 0.1246 0.1234
; International Tables for Crystallography (1992). 
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
Zn Zn 1 0.2839 1.4301
; International Tables for Crystallography (1992). 
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 180.0 2_656 .
N1 Zn1 O1 91.62(5) . .
N1 Zn1 O1 88.38(5) . 2_656
O1 Zn1 O1 180.0 . 2_656
N1 Zn1 N3 91.10(5) . .
O1 Zn1 N3 90.61(5) . .
N1 Zn1 N3 88.90(5) . 2_656
O1 Zn1 N3 89.39(5) . 2_656
N3 Zn1 N3 180.0 . 2_656
O3 S1 O4 115.20(9) . .
O3 S1 O2 114.79(8) . .
O4 S1 O2 113.32(8) . .
O3 S1 C15 105.14(10) . .
O4 S1 C15 103.10(9) . .
O2 S1 C15 103.37(8) . .
C14 O1 Zn1 126.05(12) . .
C14 O1 H1 106.4(17) . .
Zn1 O1 H1 112.1(17) . .
C1 N1 C4 107.79(12) . .
C1 N1 Zn1 128.53(10) . .
C4 N1 Zn1 123.68(10) . .
C4 N2 C9 129.54(14) . .
C13 N3 C9 115.99(13) . .
C13 N3 Zn1 123.29(10) . .
C9 N3 Zn1 120.62(10) . .
C1 N4 C13 131.69(13) 2_656 .
C1 N4 H4 115.0(15) 2_656 .
C13 N4 H4 112.8(15) . .
N1 C1 N4 125.89(14) . 2_656
N1 C1 C2 111.68(13) . .
N4 C1 C2 122.43(13) 2_656 .
C3 C2 C5 121.48(14) . .
C3 C2 C1 105.39(13) . .
C5 C2 C1 133.13(15) . .
C8 C3 C2 121.98(14) . .
C8 C3 C4 130.97(15) . .
C2 C3 C4 107.05(13) . .
N2 C4 N1 130.12(14) . .
N2 C4 C3 121.76(14) . .
N1 C4 C3 108.10(13) . .
C2 C5 C6 116.79(15) . .
C2 C5 H5 121.6 . .
C6 C5 H5 121.6 . .
C7 C6 C5 121.54(15) . .
C7 C6 H6 119.2 . .
C5 C6 H6 119.2 . .
C6 C7 C8 121.51(15) . .
C6 C7 H7 119.2 . .
C8 C7 H7 119.2 . .
C3 C8 C7 116.69(15) . .
C3 C8 H8 121.7 . .
C7 C8 H8 121.7 . .
N3 C9 C10 122.59(14) . .
N3 C9 N2 124.73(13) . .
C10 C9 N2 112.68(13) . .
C11 C10 C9 119.75(14) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C12 C11 C10 118.64(15) . .
C12 C11 H11 120.7 . .
C10 C11 H11 120.7 . .
C11 C12 C13 118.71(14) . .
C11 C12 H12 120.6 . .
C13 C12 H12 120.6 . .
N3 C13 C12 124.30(14) . .
N3 C13 N4 121.27(13) . .
C12 C13 N4 114.42(13) . .
O1 C14 H14A 109.5 . .
O1 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O1 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
F2 C15 F1 107.79(19) . .
F2 C15 F3 108.77(17) . .
F1 C15 F3 107.29(18) . .
F2 C15 S1 111.06(15) . .
F1 C15 S1 110.83(14) . .
F3 C15 S1 110.97(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 1.9696(12) .
Zn1 O1 2.2270(12) .
Zn1 N3 2.2306(12) .
S1 O3 1.4277(14) .
S1 O4 1.4392(13) .
S1 O2 1.4469(12) .
S1 C15 1.822(2) .
F1 C15 1.328(3) .
F2 C15 1.321(2) .
F3 C15 1.329(2) .
O1 C14 1.420(2) .
O1 H1 0.80(3) .
N1 C1 1.3281(19) .
N1 C4 1.4086(19) .
N2 C4 1.274(2) .
N2 C9 1.3938(19) .
N3 C13 1.3426(19) .
N3 C9 1.3657(19) .
N4 C1 1.331(2) 2_656
N4 C13 1.4101(19) .
N4 H4 0.82(2) .
C1 N4 1.331(2) 2_656
C1 C2 1.475(2) .
C2 C3 1.387(2) .
C2 C5 1.391(2) .
C3 C8 1.385(2) .
C3 C4 1.477(2) .
C5 C6 1.393(2) .
C5 H5 0.9500 .
C6 C7 1.390(3) .
C6 H6 0.9500 .
C7 C8 1.395(2) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C10 1.393(2) .
C10 C11 1.378(2) .
C10 H10 0.9500 .
C11 C12 1.374(2) .
C11 H11 0.9500 .
C12 C13 1.395(2) .
C12 H12 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.80(3) 1.95(3) 2.7505(18) 171(2) . yes
N4 H4 O2 0.82(2) 2.13(2) 2.9469(18) 173(2) 2_655 yes
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
N1 Zn1 O1 C14 167.69(17) 2_656 .
N1 Zn1 O1 C14 -12.31(17) . .
N3 Zn1 O1 C14 78.81(16) . .
N3 Zn1 O1 C14 -101.19(16) 2_656 .
O1 Zn1 N1 C1 -88.54(13) . .
O1 Zn1 N1 C1 91.46(13) 2_656 .
N3 Zn1 N1 C1 -179.18(13) . .
O1 Zn1 N1 C4 91.88(12) . .
O1 Zn1 N1 C4 -88.12(12) 2_656 .
N3 Zn1 N1 C4 1.24(12) . .
N3 Zn1 N1 C4 -178.76(12) 2_656 .
N1 Zn1 N3 C13 -1.40(12) 2_656 .
N1 Zn1 N3 C13 178.60(12) . .
O1 Zn1 N3 C13 86.97(12) . .
O1 Zn1 N3 C13 -93.03(12) 2_656 .
N1 Zn1 N3 C9 -177.57(12) 2_656 .
N1 Zn1 N3 C9 2.43(12) . .
O1 Zn1 N3 C9 -89.20(11) . .
O1 Zn1 N3 C9 90.80(11) 2_656 .
C4 N1 C1 N4 -179.04(14) . 2_656
Zn1 N1 C1 N4 1.3(2) . 2_656
C4 N1 C1 C2 0.19(17) . .
Zn1 N1 C1 C2 -179.44(10) . .
N1 C1 C2 C3 0.29(18) . .
N4 C1 C2 C3 179.56(14) 2_656 .
N1 C1 C2 C5 179.47(17) . .
N4 C1 C2 C5 -1.3(3) 2_656 .
C5 C2 C3 C8 0.1(3) . .
C1 C2 C3 C8 179.39(15) . .
C5 C2 C3 C4 -179.92(15) . .
C1 C2 C3 C4 -0.62(16) . .
C9 N2 C4 N1 0.0(3) . .
C9 N2 C4 C3 177.92(15) . .
C1 N1 C4 N2 177.58(16) . .
Zn1 N1 C4 N2 -2.8(2) . .
C1 N1 C4 C3 -0.58(17) . .
Zn1 N1 C4 C3 179.08(10) . .
C8 C3 C4 N2 2.4(3) . .
C2 C3 C4 N2 -177.58(15) . .
C8 C3 C4 N1 -179.26(17) . .
C2 C3 C4 N1 0.76(17) . .
C3 C2 C5 C6 -0.1(2) . .
C1 C2 C5 C6 -179.21(16) . .
C2 C5 C6 C7 0.0(3) . .
C5 C6 C7 C8 0.1(3) . .
C2 C3 C8 C7 0.1(2) . .
C4 C3 C8 C7 -179.91(16) . .
C6 C7 C8 C3 -0.2(3) . .
C13 N3 C9 C10 -1.4(2) . .
Zn1 N3 C9 C10 175.00(12) . .
C13 N3 C9 N2 178.14(14) . .
Zn1 N3 C9 N2 -5.4(2) . .
C4 N2 C9 N3 4.8(3) . .
C4 N2 C9 C10 -175.62(16) . .
N3 C9 C10 C11 0.8(2) . .
N2 C9 C10 C11 -178.87(15) . .
C9 C10 C11 C12 0.4(3) . .
C10 C11 C12 C13 -0.7(2) . .
C9 N3 C13 C12 1.1(2) . .
Zn1 N3 C13 C12 -175.24(12) . .
C9 N3 C13 N4 -178.12(13) . .
Zn1 N3 C13 N4 5.6(2) . .
C11 C12 C13 N3 0.0(2) . .
C11 C12 C13 N4 179.22(15) . .
C1 N4 C13 N3 -9.1(3) 2_656 .
C1 N4 C13 C12 171.63(16) 2_656 .
O3 S1 C15 F2 -59.46(18) . .
O4 S1 C15 F2 61.59(18) . .
O2 S1 C15 F2 179.82(15) . .
O3 S1 C15 F1 -179.25(14) . .
O4 S1 C15 F1 -58.19(16) . .
O2 S1 C15 F1 60.04(16) . .
O3 S1 C15 F3 61.65(17) . .
O4 S1 C15 F3 -177.29(15) . .
O2 S1 C15 F3 -59.06(17) . .
