#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:57:08 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180241 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/27/7112702.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_7112702
loop_
_publ_author_name
'Ding, Yubin'
'Xie, Yongshu'
'Li, Xin'
'Hill, Jonathan P.'
'Zhang, Weibing'
'Zhu, Weihong'
_publ_section_title
;
 Selective and sensitive "turn-on" fluorescent Zn2+ sensors
 based on di- and tripyrrins with readily modulated emission wavelengths.
;
_journal_issue                   19
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5431
_journal_page_last               5433
_journal_paper_doi               10.1039/c1cc11493j
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C45 H24 F10 N4 O3 Zn'
_chemical_formula_weight         924.05
_chemical_name_systematic
;
?
;
_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                 115.894(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.864(2)
_cell_length_b                   10.2060(10)
_cell_length_c                   14.8521(13)
_cell_measurement_reflns_used    1358
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.751
_cell_measurement_theta_min      2.753
_cell_volume                     3936.0(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9831
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.9186
_exptl_absorpt_correction_T_min  0.8577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0147P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                1813
_reflns_number_total             3460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc11493j.txt
_cod_data_source_block           101222k
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7112702
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 0.5000 0.34160(6) 0.2500 0.0571(2) Uani 1 2 d S
N1 N 0.57480(10) 0.3188(3) 0.2994(2) 0.0470(7) Uani 1 1 d .
N2 N 0.50176(12) 0.4820(3) 0.1499(2) 0.0511(8) Uani 1 1 d .
F1 F 0.65290(8) 0.4597(2) 0.11032(19) 0.0868(8) Uani 1 1 d .
F2 F 0.72870(9) 0.6204(3) 0.1181(2) 0.1132(10) Uani 1 1 d .
F3 F 0.75040(9) 0.8392(3) 0.2291(2) 0.1293(11) Uani 1 1 d .
F4 F 0.70041(12) 0.8914(3) 0.3399(3) 0.1678(16) Uani 1 1 d .
F5 F 0.62686(11) 0.7293(3) 0.3359(2) 0.1357(12) Uani 1 1 d .
O1 O 0.52508(10) 0.1630(2) 0.37137(19) 0.0647(7) Uani 1 1 d .
O2 O 0.4641(3) 0.9365(7) 0.2790(7) 0.153(3) Uani 0.50 1 d P
H2 H 0.4767 1.0077 0.3026 0.229 Uiso 0.50 1 calc PR
C1 C 0.60162(15) 0.2338(4) 0.3732(3) 0.0512(10) Uani 1 1 d .
C2 C 0.65414(15) 0.2573(4) 0.4096(3) 0.0666(11) Uani 1 1 d .
H2A H 0.6806 0.2116 0.4602 0.080 Uiso 1 1 calc R
C3 C 0.65923(14) 0.3608(4) 0.3563(3) 0.0669(12) Uani 1 1 d .
H3 H 0.6900 0.3988 0.3639 0.080 Uiso 1 1 calc R
C4 C 0.60966(14) 0.3992(4) 0.2883(3) 0.0494(10) Uani 1 1 d .
C5 C 0.59459(15) 0.5054(3) 0.2194(3) 0.0522(10) Uani 1 1 d .
C6 C 0.54635(16) 0.5429(4) 0.1555(3) 0.0529(10) Uani 1 1 d .
C7 C 0.53115(17) 0.6496(4) 0.0868(3) 0.0659(11) Uani 1 1 d .
H7 H 0.5531 0.7070 0.0754 0.079 Uiso 1 1 calc R
C8 C 0.47995(17) 0.6522(4) 0.0417(3) 0.0728(12) Uani 1 1 d .
H8 H 0.4591 0.7104 -0.0074 0.087 Uiso 1 1 calc R
C9 C 0.46362(16) 0.5468(4) 0.0847(3) 0.0662(12) Uani 1 1 d .
H9 H 0.4293 0.5273 0.0673 0.079 Uiso 1 1 calc R
C10 C 0.63722(14) 0.5909(4) 0.2223(3) 0.0603(11) Uani 1 1 d .
C11 C 0.66396(16) 0.5658(4) 0.1675(3) 0.0654(12) Uani 1 1 d .
C12 C 0.70307(16) 0.6476(5) 0.1710(4) 0.0730(13) Uani 1 1 d .
C13 C 0.71332(17) 0.7577(5) 0.2279(4) 0.0898(16) Uani 1 1 d .
C14 C 0.6887(2) 0.7839(5) 0.2835(5) 0.1031(18) Uani 1 1 d .
C15 C 0.65108(18) 0.7000(5) 0.2795(4) 0.0881(15) Uani 1 1 d .
C16 C 0.57220(16) 0.1483(3) 0.4070(3) 0.0534(10) Uani 1 1 d .
C17 C 0.59770(16) 0.0488(4) 0.4858(3) 0.0599(11) Uani 1 1 d .
C18 C 0.57779(17) 0.0220(4) 0.5534(4) 0.0775(13) Uani 1 1 d .
H18 H 0.5483 0.0654 0.5479 0.093 Uiso 1 1 calc R
C19 C 0.6012(2) -0.0682(5) 0.6286(4) 0.0969(17) Uani 1 1 d .
H19 H 0.5875 -0.0846 0.6737 0.116 Uiso 1 1 calc R
C20 C 0.6434(2) -0.1326(5) 0.6375(4) 0.1102(19) Uani 1 1 d .
H20 H 0.6593 -0.1919 0.6895 0.132 Uiso 1 1 calc R
C21 C 0.6630(2) -0.1111(5) 0.5706(5) 0.1124(19) Uani 1 1 d .
H21 H 0.6916 -0.1584 0.5757 0.135 Uiso 1 1 calc R
C22 C 0.64082(18) -0.0197(4) 0.4948(4) 0.0896(15) Uani 1 1 d .
H22 H 0.6549 -0.0044 0.4501 0.108 Uiso 1 1 calc R
C23 C 0.5000 0.8635(7) 0.2500 0.145(3) Uani 1 2 d S
H23A H 0.5107 0.9193 0.2105 0.218 Uiso 0.50 1 d PR
H23B H 0.4832 0.7873 0.2118 0.218 Uiso 0.50 1 d PR
H23C H 0.5296 0.8373 0.3095 0.218 Uiso 0.50 1 d PR
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'
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 166.41(16) 2_655 .
N1 Zn1 N2 89.02(12) 2_655 2_655
N1 Zn1 N2 100.37(12) . 2_655
N1 Zn1 N2 100.37(12) 2_655 .
N1 Zn1 N2 89.02(12) . .
N2 Zn1 N2 92.98(15) 2_655 .
N1 Zn1 O1 73.31(10) 2_655 2_655
N1 Zn1 O1 96.34(10) . 2_655
N2 Zn1 O1 161.79(10) 2_655 2_655
N2 Zn1 O1 94.51(10) . 2_655
N1 Zn1 O1 96.34(10) 2_655 .
N1 Zn1 O1 73.31(10) . .
N2 Zn1 O1 94.51(10) 2_655 .
N2 Zn1 O1 161.79(10) . .
O1 Zn1 O1 83.36(12) 2_655 .
C1 N1 C4 107.1(3) . .
C1 N1 Zn1 121.8(2) . .
C4 N1 Zn1 129.2(3) . .
C9 N2 C6 106.2(3) . .
C9 N2 Zn1 127.7(3) . .
C6 N2 Zn1 124.9(3) . .
C16 O1 Zn1 108.9(2) . .
C23 O2 H2 109.5 . .
N1 C1 C2 110.3(3) . .
N1 C1 C16 117.0(3) . .
C2 C1 C16 132.3(4) . .
C3 C2 C1 106.5(4) . .
C3 C2 H2A 126.8 . .
C1 C2 H2A 126.8 . .
C2 C3 C4 107.5(3) . .
C2 C3 H3 126.3 . .
C4 C3 H3 126.3 . .
N1 C4 C3 108.7(3) . .
N1 C4 C5 122.4(3) . .
C3 C4 C5 128.9(4) . .
C6 C5 C4 128.1(3) . .
C6 C5 C10 116.0(4) . .
C4 C5 C10 115.8(4) . .
C5 C6 N2 123.7(4) . .
C5 C6 C7 128.2(4) . .
N2 C6 C7 108.0(3) . .
C8 C7 C6 107.6(4) . .
C8 C7 H7 126.2 . .
C6 C7 H7 126.2 . .
C7 C8 C9 105.7(4) . .
C7 C8 H8 127.1 . .
C9 C8 H8 127.1 . .
N2 C9 C8 112.5(4) . .
N2 C9 H9 123.8 . .
C8 C9 H9 123.8 . .
C15 C10 C11 116.0(4) . .
C15 C10 C5 121.0(4) . .
C11 C10 C5 123.0(4) . .
F1 C11 C10 119.6(4) . .
F1 C11 C12 118.7(4) . .
C10 C11 C12 121.8(4) . .
F2 C12 C13 121.1(5) . .
F2 C12 C11 120.6(5) . .
C13 C12 C11 118.3(4) . .
C14 C13 F3 120.3(6) . .
C14 C13 C12 121.4(5) . .
F3 C13 C12 118.3(5) . .
C13 C14 F4 119.8(5) . .
C13 C14 C15 118.6(5) . .
F4 C14 C15 121.6(5) . .
F5 C15 C10 119.0(4) . .
F5 C15 C14 117.2(5) . .
C10 C15 C14 123.8(5) . .
O1 C16 C1 118.7(4) . .
O1 C16 C17 119.8(4) . .
C1 C16 C17 121.5(4) . .
C22 C17 C18 118.1(4) . .
C22 C17 C16 122.7(4) . .
C18 C17 C16 119.2(4) . .
C19 C18 C17 120.6(4) . .
C19 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C20 C19 C18 120.8(5) . .
C20 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
C19 C20 C21 120.0(5) . .
C19 C20 H20 120.0 . .
C21 C20 H20 120.0 . .
C20 C21 C22 120.7(5) . .
C20 C21 H21 119.7 . .
C22 C21 H21 119.7 . .
C17 C22 C21 119.8(5) . .
C17 C22 H22 120.1 . .
C21 C22 H22 120.1 . .
O2 C23 O2 119.8(7) . 2_655
O2 C23 H23A 109.4 . .
O2 C23 H23A 22.1 2_655 .
O2 C23 H23B 110.0 . .
O2 C23 H23B 118.1 2_655 .
H23A C23 H23B 109.5 . .
O2 C23 H23C 109.0 . .
O2 C23 H23C 87.4 2_655 .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 1.967(3) 2_655
Zn1 N1 1.967(3) .
Zn1 N2 2.081(3) 2_655
Zn1 N2 2.081(3) .
Zn1 O1 2.441(2) 2_655
Zn1 O1 2.441(2) .
N1 C1 1.346(4) .
N1 C4 1.363(4) .
N2 C9 1.287(4) .
N2 C6 1.399(4) .
F1 C11 1.326(4) .
F2 C12 1.322(4) .
F3 C13 1.349(4) .
F4 C14 1.332(5) .
F5 C15 1.339(4) .
O1 C16 1.234(4) .
O2 C23 1.483(7) .
O2 H2 0.8200 .
C1 C2 1.390(4) .
C1 C16 1.451(5) .
C2 C3 1.365(5) .
C2 H2A 0.9300 .
C3 C4 1.399(5) .
C3 H3 0.9300 .
C4 C5 1.423(5) .
C5 C6 1.353(5) .
C5 C10 1.494(4) .
C6 C7 1.425(5) .
C7 C8 1.330(4) .
C7 H7 0.9300 .
C8 C9 1.431(5) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 C15 1.351(5) .
C10 C11 1.368(5) .
C11 C12 1.387(5) .
C12 C13 1.358(6) .
C13 C14 1.331(6) .
C14 C15 1.362(5) .
C16 C17 1.480(5) .
C17 C22 1.382(5) .
C17 C18 1.384(5) .
C18 C19 1.375(6) .
C18 H18 0.9300 .
C19 C20 1.340(6) .
C19 H19 0.9300 .
C20 C21 1.359(6) .
C20 H20 0.9300 .
C21 C22 1.385(6) .
C21 H21 0.9300 .
C22 H22 0.9300 .
C23 O2 1.483(7) 2_655
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
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
N1 Zn1 N1 C1 -46.4(2) 2_655
N2 Zn1 N1 C1 86.7(3) 2_655
N2 Zn1 N1 C1 179.5(3) .
O1 Zn1 N1 C1 -86.0(3) 2_655
O1 Zn1 N1 C1 -4.9(2) .
N1 Zn1 N1 C4 151.5(3) 2_655
N2 Zn1 N1 C4 -75.4(3) 2_655
N2 Zn1 N1 C4 17.4(3) .
O1 Zn1 N1 C4 111.8(3) 2_655
O1 Zn1 N1 C4 -167.1(3) .
N1 Zn1 N2 C9 8.8(3) 2_655
N1 Zn1 N2 C9 178.9(3) .
N2 Zn1 N2 C9 -80.7(3) 2_655
O1 Zn1 N2 C9 82.7(3) 2_655
O1 Zn1 N2 C9 165.1(3) .
N1 Zn1 N2 C6 174.7(3) 2_655
N1 Zn1 N2 C6 -15.2(3) .
N2 Zn1 N2 C6 85.1(3) 2_655
O1 Zn1 N2 C6 -111.5(3) 2_655
O1 Zn1 N2 C6 -29.1(5) .
N1 Zn1 O1 C16 173.3(2) 2_655
N1 Zn1 O1 C16 2.3(2) .
N2 Zn1 O1 C16 -97.2(2) 2_655
N2 Zn1 O1 C16 16.8(4) .
O1 Zn1 O1 C16 101.0(2) 2_655
C4 N1 C1 C2 -0.8(4) .
Zn1 N1 C1 C2 -166.4(2) .
C4 N1 C1 C16 172.6(3) .
Zn1 N1 C1 C16 7.0(4) .
N1 C1 C2 C3 0.4(4) .
C16 C1 C2 C3 -171.6(4) .
C1 C2 C3 C4 0.1(4) .
C1 N1 C4 C3 0.9(4) .
Zn1 N1 C4 C3 165.0(2) .
C1 N1 C4 C5 -177.1(3) .
Zn1 N1 C4 C5 -12.9(5) .
C2 C3 C4 N1 -0.6(4) .
C2 C3 C4 C5 177.2(4) .
N1 C4 C5 C6 -0.9(6) .
C3 C4 C5 C6 -178.4(4) .
N1 C4 C5 C10 175.0(3) .
C3 C4 C5 C10 -2.5(5) .
C4 C5 C6 N2 2.2(6) .
C10 C5 C6 N2 -173.7(3) .
C4 C5 C6 C7 179.7(4) .
C10 C5 C6 C7 3.8(6) .
C9 N2 C6 C5 177.4(3) .
Zn1 N2 C6 C5 9.0(5) .
C9 N2 C6 C7 -0.5(4) .
Zn1 N2 C6 C7 -168.9(2) .
C5 C6 C7 C8 -178.1(4) .
N2 C6 C7 C8 -0.3(4) .
C6 C7 C8 C9 0.8(4) .
C6 N2 C9 C8 1.0(4) .
Zn1 N2 C9 C8 169.0(2) .
C7 C8 C9 N2 -1.2(5) .
C6 C5 C10 C15 83.6(5) .
C4 C5 C10 C15 -92.8(5) .
C6 C5 C10 C11 -95.6(4) .
C4 C5 C10 C11 88.0(5) .
C15 C10 C11 F1 179.3(4) .
C5 C10 C11 F1 -1.5(6) .
C15 C10 C11 C12 0.2(6) .
C5 C10 C11 C12 179.4(4) .
F1 C11 C12 F2 0.2(6) .
C10 C11 C12 F2 179.3(4) .
F1 C11 C12 C13 178.5(4) .
C10 C11 C12 C13 -2.4(7) .
F2 C12 C13 C14 -178.1(5) .
C11 C12 C13 C14 3.6(8) .
F2 C12 C13 F3 0.1(7) .
C11 C12 C13 F3 -178.2(4) .
F3 C13 C14 F4 0.5(8) .
C12 C13 C14 F4 178.7(4) .
F3 C13 C14 C15 179.3(4) .
C12 C13 C14 C15 -2.5(9) .
C11 C10 C15 F5 -179.1(4) .
C5 C10 C15 F5 1.7(7) .
C11 C10 C15 C14 1.0(7) .
C5 C10 C15 C14 -178.2(5) .
C13 C14 C15 F5 -179.8(5) .
F4 C14 C15 F5 -0.9(8) .
C13 C14 C15 C10 0.1(9) .
F4 C14 C15 C10 179.0(5) .
Zn1 O1 C16 C1 0.3(4) .
Zn1 O1 C16 C17 177.8(3) .
N1 C1 C16 O1 -4.3(5) .
C2 C1 C16 O1 167.3(4) .
N1 C1 C16 C17 178.3(3) .
C2 C1 C16 C17 -10.1(6) .
O1 C16 C17 C22 146.9(4) .
C1 C16 C17 C22 -35.8(5) .
O1 C16 C17 C18 -32.9(5) .
C1 C16 C17 C18 144.4(4) .
C22 C17 C18 C19 1.4(6) .
C16 C17 C18 C19 -178.8(4) .
C17 C18 C19 C20 -0.5(7) .
C18 C19 C20 C21 -1.4(8) .
C19 C20 C21 C22 2.3(9) .
C18 C17 C22 C21 -0.6(6) .
C16 C17 C22 C21 179.6(4) .
C20 C21 C22 C17 -1.3(8) .
