#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/92/7109228.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_7109228
loop_
_publ_author_name
'Sabrina M. Huber'
'Guillaume Mata'
'Anthony Linden'
'Nathan W. Luedtke'
_publ_section_title
;
 Synthesis and structure of a hydrogenated zinc hemiporphyrazine
;
_journal_name_full               Chem.Commun.
_journal_page_first              4280
_journal_paper_doi               10.1039/c2cc37151k
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C26 H22 N8 O Zn 2+, 2(C F3 O3 S -)'
_chemical_formula_sum            'C28 H22 F6 N8 O7 S2 Zn'
_chemical_formula_weight         826.02
_chemical_name_common            HpH₄Zn(OH₂).(OTf)₂
_chemical_name_systematic
;
rac-aquatetrahydro-hemiporphyrazinezinc(II) ditriflate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             10-09-17
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.3430(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.9506(3)
_cell_length_b                   10.16731(13)
_cell_length_c                   16.0497(2)
_cell_measurement_reflns_used    12426
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      30.4039
_cell_measurement_theta_min      3.2354
_cell_volume                     3263.34(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.914
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21655
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         30.47
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85774
_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            orange
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0351
_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)+(0.0553P)²+4.6680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                4152
_reflns_number_total             4547
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c2cc37151k.txt
_cod_data_source_block           2
_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        3263.34(7)
_cod_database_code               7109228
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 0.22979(3) 0.7500 0.01816(8) Uani 1 2 d S
O4 O 0.0000 0.4228(2) 0.7500 0.0612(10) Uani 1 2 d S
H41 H 0.0279(16) 0.462(4) 0.755(3) 0.071(12) Uiso 1 1 d .
N1 N 0.07592(7) 0.16055(14) 0.83912(9) 0.0210(3) Uani 1 1 d .
N2 N 0.16344(7) 0.19355(16) 0.77728(9) 0.0225(3) Uani 1 1 d .
H2 H 0.2031(14) 0.200(3) 0.7914(18) 0.039(7) Uiso 1 1 d .
N3 N 0.06306(7) 0.20905(15) 0.65954(9) 0.0208(3) Uani 1 1 d .
N4 N 0.03379(8) 0.21068(19) 0.95955(10) 0.0299(3) Uani 1 1 d .
H4 H 0.0534(16) 0.234(3) 1.013(2) 0.048(8) Uiso 1 1 d .
C1 C 0.06817(9) 0.1164(2) 0.92219(10) 0.0266(4) Uani 1 1 d .
H1 H 0.0428 0.0317 0.9129 0.032 Uiso 1 1 calc R
C2 C 0.13898(8) 0.09141(18) 0.97820(10) 0.0245(3) Uani 1 1 d .
C3 C 0.18161(8) 0.11216(16) 0.92781(10) 0.0205(3) Uani 1 1 d .
C4 C 0.13886(8) 0.15625(16) 0.84159(10) 0.0204(3) Uani 1 1 d .
C5 C 0.16328(10) 0.0524(2) 1.06450(12) 0.0318(4) Uani 1 1 d .
H5 H 0.1341 0.0371 1.0988 0.038 Uiso 1 1 calc R
C6 C 0.23229(9) 0.0363(2) 1.09921(11) 0.0304(4) Uani 1 1 d .
H6 H 0.2505 0.0116 1.1587 0.036 Uiso 1 1 calc R
C7 C 0.27474(9) 0.05590(19) 1.04853(11) 0.0278(4) Uani 1 1 d .
H7 H 0.3214 0.0428 1.0737 0.033 Uiso 1 1 calc R
C8 C 0.25027(8) 0.09434(19) 0.96140(11) 0.0258(3) Uani 1 1 d .
H8 H 0.2793 0.1077 0.9265 0.031 Uiso 1 1 calc R
C9 C 0.12957(8) 0.23000(16) 0.69101(10) 0.0201(3) Uani 1 1 d .
C10 C 0.16744(9) 0.2832(2) 0.64195(12) 0.0275(4) Uani 1 1 d .
H10 H 0.2141 0.2977 0.6668 0.033 Uiso 1 1 calc R
C11 C 0.13542(9) 0.3146(2) 0.55566(12) 0.0324(4) Uani 1 1 d .
H11 H 0.1601 0.3520 0.5206 0.039 Uiso 1 1 calc R
C12 C 0.06800(9) 0.2919(2) 0.52040(12) 0.0314(4) Uani 1 1 d .
H12 H 0.0456 0.3128 0.4612 0.038 Uiso 1 1 calc R
C13 C 0.03341(8) 0.23708(18) 0.57440(11) 0.0234(3) Uani 1 1 d .
S1 S 0.12883(2) 0.34501(4) 0.21669(3) 0.02369(11) Uani 1 1 d .
O1 O 0.19583(7) 0.33853(16) 0.21142(9) 0.0356(3) Uani 1 1 d .
O2 O 0.07742(8) 0.3105(2) 0.13896(10) 0.0452(4) Uani 1 1 d .
O3 O 0.11575(7) 0.45988(15) 0.26175(10) 0.0377(3) Uani 1 1 d .
C14 C 0.12765(14) 0.2120(2) 0.29365(17) 0.0462(6) Uani 1 1 d .
F1 F 0.06856(11) 0.2031(3) 0.30688(14) 0.0882(7) Uani 1 1 d .
F2 F 0.17228(9) 0.23145(19) 0.36989(10) 0.0602(5) Uani 1 1 d .
F3 F 0.14329(17) 0.09899(17) 0.26297(15) 0.1049(9) 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 112 0.0033 0.0016
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 88 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
F F 24 0.0171 0.0103
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 32 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 28 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
S S 8 0.1246 0.1234
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
Zn Zn 4 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 137.15(9) 2_556 .
N1 Zn1 O4 111.42(4) . .
N1 Zn1 N3 90.02(5) . 2_556
O4 Zn1 N3 95.39(4) . 2_556
N1 Zn1 N3 86.05(5) . .
O4 Zn1 N3 95.39(4) . .
N3 Zn1 N3 169.22(8) 2_556 .
Zn1 O4 H41 125(3) . .
C4 N1 C1 110.32(13) . .
C4 N1 Zn1 129.51(12) . .
C1 N1 Zn1 119.85(11) . .
C4 N2 C9 129.61(14) . .
C4 N2 H2 114.3(19) . .
C9 N2 H2 116.0(19) . .
C9 N3 C13 117.19(14) . .
C9 N3 Zn1 118.94(11) . .
C13 N3 Zn1 116.88(11) . .
C13 N4 C1 123.18(15) 2_556 .
C13 N4 H4 118(2) 2_556 .
C1 N4 H4 117(2) . .
N4 C1 N1 112.52(16) . .
N4 C1 C2 113.01(15) . .
N1 C1 C2 103.79(14) . .
N4 C1 H1 109.1 . .
N1 C1 H1 109.1 . .
C2 C1 H1 109.1 . .
C5 C2 C3 121.21(16) . .
C5 C2 C1 130.35(16) . .
C3 C2 C1 108.44(14) . .
C2 C3 C8 121.72(15) . .
C2 C3 C4 106.04(14) . .
C8 C3 C4 132.22(15) . .
N1 C4 N2 125.68(14) . .
N1 C4 C3 111.29(14) . .
N2 C4 C3 122.92(14) . .
C2 C5 C6 117.47(17) . .
C2 C5 H5 121.3 . .
C6 C5 H5 121.3 . .
C7 C6 C5 121.23(16) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C6 C7 C8 121.34(16) . .
C6 C7 H7 119.3 . .
C8 C7 H7 119.3 . .
C3 C8 C7 117.02(16) . .
C3 C8 H8 121.5 . .
C7 C8 H8 121.5 . .
N3 C9 C10 123.49(15) . .
N3 C9 N2 119.28(15) . .
C10 C9 N2 117.21(15) . .
C9 C10 C11 118.07(16) . .
C9 C10 H10 121.0 . .
C11 C10 H10 121.0 . .
C12 C11 C10 120.32(17) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C11 C12 C13 118.00(16) . .
C11 C12 H12 121.0 . .
C13 C12 H12 121.0 . .
N3 C13 N4 117.81(15) . 2_556
N3 C13 C12 122.87(16) . .
N4 C13 C12 119.32(16) 2_556 .
O2 S1 O1 115.74(9) . .
O2 S1 O3 115.50(9) . .
O1 S1 O3 113.75(9) . .
O2 S1 C14 104.40(12) . .
O1 S1 C14 102.46(11) . .
O3 S1 C14 102.49(11) . .
F2 C14 F1 107.5(2) . .
F2 C14 F3 106.8(3) . .
F1 C14 F3 110.3(3) . .
F2 C14 S1 111.53(18) . .
F1 C14 S1 111.1(2) . .
F3 C14 S1 109.47(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 1.9274(13) .
Zn1 O4 1.962(2) .
Zn1 N3 2.2453(14) .
O4 H41 0.69(3) .
N1 C4 1.308(2) .
N1 C1 1.461(2) .
N2 C4 1.338(2) .
N2 C9 1.404(2) .
N2 H2 0.80(3) .
N3 C9 1.350(2) .
N3 C13 1.352(2) .
N4 C13 1.376(2) 2_556
N4 C1 1.433(2) .
N4 H4 0.86(3) .
C1 C2 1.510(2) .
C1 H1 1.0000 .
C2 C5 1.384(2) .
C2 C3 1.388(2) .
C3 C8 1.389(2) .
C3 C4 1.476(2) .
C5 C6 1.395(3) .
C5 H5 0.9500 .
C6 C7 1.387(3) .
C6 H6 0.9500 .
C7 C8 1.394(2) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C10 1.384(2) .
C10 C11 1.384(3) .
C10 H10 0.9500 .
C11 C12 1.376(2) .
C11 H11 0.9500 .
C12 C13 1.400(2) .
C12 H12 0.9500 .
S1 O2 1.4278(14) .
S1 O1 1.4326(14) .
S1 O3 1.4423(14) .
S1 C14 1.836(3) .
C14 F2 1.315(3) .
C14 F1 1.320(3) .
C14 F3 1.329(3) .
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
N2 H2 O1 0.80(3) 2.17(3) 2.9178(19) 157(3) 7_556 yes
N4 H4 O2 0.86(3) 2.09(3) 2.931(2) 166(3) 1_556 yes
O4 H41 O3 0.69(3) 1.98(3) 2.6583(18) 168(4) 6_566 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 N1 C4 106.08(16) 2_556 .
O4 Zn1 N1 C4 -73.92(16) . .
N3 Zn1 N1 C4 -169.72(16) 2_556 .
N3 Zn1 N1 C4 20.33(15) . .
N1 Zn1 N1 C1 -81.08(13) 2_556 .
O4 Zn1 N1 C1 98.92(13) . .
N3 Zn1 N1 C1 3.13(14) 2_556 .
N3 Zn1 N1 C1 -166.83(14) . .
N1 Zn1 N3 C9 -171.96(13) 2_556 .
N1 Zn1 N3 C9 -34.66(13) . .
O4 Zn1 N3 C9 76.51(12) . .
N3 Zn1 N3 C9 -103.49(12) 2_556 .
N1 Zn1 N3 C13 38.09(13) 2_556 .
N1 Zn1 N3 C13 175.39(14) . .
O4 Zn1 N3 C13 -73.43(13) . .
N3 Zn1 N3 C13 106.57(13) 2_556 .
C13 N4 C1 N1 71.0(2) 2_556 .
C13 N4 C1 C2 -171.86(17) 2_556 .
C4 N1 C1 N4 125.62(16) . .
Zn1 N1 C1 N4 -48.50(19) . .
C4 N1 C1 C2 3.1(2) . .
Zn1 N1 C1 C2 -171.01(11) . .
N4 C1 C2 C5 55.3(3) . .
N1 C1 C2 C5 177.5(2) . .
N4 C1 C2 C3 -125.69(17) . .
N1 C1 C2 C3 -3.5(2) . .
C5 C2 C3 C8 0.3(3) . .
C1 C2 C3 C8 -178.87(17) . .
C5 C2 C3 C4 -178.25(18) . .
C1 C2 C3 C4 2.6(2) . .
C1 N1 C4 N2 -177.97(17) . .
Zn1 N1 C4 N2 -4.6(3) . .
C1 N1 C4 C3 -1.6(2) . .
Zn1 N1 C4 C3 171.75(12) . .
C9 N2 C4 N1 -8.3(3) . .
C9 N2 C4 C3 175.76(16) . .
C2 C3 C4 N1 -0.7(2) . .
C8 C3 C4 N1 -178.97(18) . .
C2 C3 C4 N2 175.76(17) . .
C8 C3 C4 N2 -2.5(3) . .
C3 C2 C5 C6 0.8(3) . .
C1 C2 C5 C6 179.69(19) . .
C2 C5 C6 C7 -1.4(3) . .
C5 C6 C7 C8 1.0(3) . .
C2 C3 C8 C7 -0.7(3) . .
C4 C3 C8 C7 177.38(18) . .
C6 C7 C8 C3 0.0(3) . .
C13 N3 C9 C10 2.8(3) . .
Zn1 N3 C9 C10 -147.00(15) . .
C13 N3 C9 N2 -175.46(16) . .
Zn1 N3 C9 N2 34.7(2) . .
C4 N2 C9 N3 -11.0(3) . .
C4 N2 C9 C10 170.56(18) . .
N3 C9 C10 C11 -1.0(3) . .
N2 C9 C10 C11 177.34(18) . .
C9 C10 C11 C12 -0.6(3) . .
C10 C11 C12 C13 0.2(3) . .
C9 N3 C13 N4 177.15(16) . 2_556
Zn1 N3 C13 N4 -32.4(2) . 2_556
C9 N3 C13 C12 -3.2(3) . .
Zn1 N3 C13 C12 147.25(16) . .
C11 C12 C13 N3 1.8(3) . .
C11 C12 C13 N4 -178.6(2) . 2_556
O2 S1 C14 F2 -178.98(17) . .
O1 S1 C14 F2 60.0(2) . .
O3 S1 C14 F2 -58.2(2) . .
O2 S1 C14 F1 -59.0(2) . .
O1 S1 C14 F1 179.94(19) . .
O3 S1 C14 F1 61.8(2) . .
O2 S1 C14 F3 63.0(2) . .
O1 S1 C14 F3 -58.0(2) . .
O3 S1 C14 F3 -176.2(2) . .
