#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:48:03 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179491 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/88/4338823.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_4338823
loop_
_publ_author_name
'Anbu, Sellamuthu'
'Ravishankaran, Rajendran'
'Guedes da Silva, M Fátima C'
'Karande, Anjali A.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Differentially selective chemosensor with fluorescence off-on responses
 on cu(2+) and zn(2+) ions in aqueous media and applications in
 pyrophosphate sensing, live cell imaging, and cytotoxicity.
;
_journal_issue                   13
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6655
_journal_page_last               6664
_journal_paper_doi               10.1021/ic500313m
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C46 H38 N8 O6 Zn2'
_chemical_formula_sum            'C46 H38 N8 O6 Zn2'
_chemical_formula_weight         929.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 122.8490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.8851(9)
_cell_length_b                   15.0765(5)
_cell_length_c                   16.2798(6)
_cell_measurement_reflns_used    6723
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.52
_cell_volume                     5131.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27209
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.470
_diffrn_reflns_theta_min         2.562
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       prism
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.090
_platon_squeeze_details
;
;
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4739
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1777
_refine_ls_wR_factor_ref         0.1968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3212
_reflns_number_total             4739
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic500313m_si_001.cif
_cod_data_source_block           R-Zn2+
_cod_depositor_comments
'Adding full bibliography for 4338822--4338823.cif.'
_cod_database_code               4338823
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.694
_shelx_estimated_absorpt_t_max   0.917
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C -0.1036(2) 0.2876(3) 0.7116(4) 0.0555(12) Uani 1 1 d . . .
C2 C -0.1599(2) 0.2272(3) 0.6620(4) 0.0604(13) Uani 1 1 d . U .
C3 C -0.1730(3) 0.1838(4) 0.5795(4) 0.0823(17) Uani 1 1 d . U .
H3 H -0.1468 0.1910 0.5556 0.099 Uiso 1 1 calc R U .
C4 C -0.2266(4) 0.1282(5) 0.5315(5) 0.104(2) Uani 1 1 d . U .
H4 H -0.2355 0.0957 0.4770 0.124 Uiso 1 1 calc R U .
C5 C -0.2658(3) 0.1225(5) 0.5665(6) 0.104(2) Uani 1 1 d . U .
H5 H -0.3022 0.0872 0.5334 0.125 Uiso 1 1 calc R U .
C6 C -0.2535(3) 0.1657(4) 0.6462(6) 0.093(2) Uani 1 1 d . U .
H6 H -0.2812 0.1604 0.6676 0.112 Uiso 1 1 calc R U .
C7 C -0.2003(3) 0.2180(4) 0.6969(5) 0.0765(16) Uani 1 1 d . U .
H7 H -0.1910 0.2471 0.7536 0.092 Uiso 1 1 calc R U .
C8 C 0.0024(2) 0.3765(3) 0.9397(4) 0.0468(11) Uani 1 1 d . . .
H8 H -0.0094 0.3441 0.9762 0.056 Uiso 1 1 calc R U .
C11 C 0.0829(3) 0.7481(3) 0.7339(4) 0.0660(15) Uani 1 1 d . . .
C12 C 0.1062(3) 0.8214(4) 0.7009(4) 0.0728(15) Uani 1 1 d . U .
C13 C 0.0804(3) 0.8331(4) 0.6038(5) 0.094(2) Uani 1 1 d . U .
H13 H 0.0480 0.7955 0.5590 0.113 Uiso 1 1 calc R U .
C14 C 0.1018(5) 0.9010(6) 0.5707(6) 0.121(3) Uani 1 1 d . U .
H14 H 0.0835 0.9085 0.5040 0.145 Uiso 1 1 calc R U .
C15 C 0.1483(4) 0.9553(6) 0.6338(6) 0.124(3) Uani 1 1 d . U .
H15 H 0.1629 1.0000 0.6113 0.148 Uiso 1 1 calc R U .
C16 C 0.1746(4) 0.9446(6) 0.7322(7) 0.131(3) Uani 1 1 d . U .
H16 H 0.2057 0.9841 0.7762 0.157 Uiso 1 1 calc R U .
C17 C 0.1555(4) 0.8769(5) 0.7662(6) 0.118(3) Uani 1 1 d . U .
H17 H 0.1756 0.8680 0.8332 0.142 Uiso 1 1 calc R U .
C18 C 0.1286(3) 0.6374(3) 0.9470(4) 0.0631(14) Uani 1 1 d . . .
H18 H 0.1662 0.6691 0.9868 0.076 Uiso 1 1 calc R U .
C21 C 0.0630(2) 0.5082(2) 0.9364(3) 0.0410(10) Uani 1 1 d . . .
C22 C 0.05227(19) 0.4421(2) 0.9893(3) 0.0425(10) Uani 1 1 d . . .
C23 C 0.0871(2) 0.4431(3) 1.0899(3) 0.0475(10) Uani 1 1 d . . .
H23 H 0.0783 0.4004 1.1222 0.057 Uiso 1 1 calc R U .
C24 C 0.1350(2) 0.5049(3) 1.1455(4) 0.0504(11) Uani 1 1 d . . .
C25 C 0.1463(3) 0.5664(3) 1.0943(4) 0.0583(12) Uani 1 1 d . . .
H25 H 0.1787 0.6078 1.1293 0.070 Uiso 1 1 calc R U .
C26 C 0.1117(2) 0.5699(3) 0.9930(3) 0.0494(11) Uani 1 1 d . . .
C27 C 0.1703(3) 0.5045(3) 1.2555(4) 0.0679(14) Uani 1 1 d . . .
H27A H 0.1550 0.4565 1.2762 0.102 Uiso 1 1 calc R U .
H27B H 0.1631 0.5597 1.2775 0.102 Uiso 1 1 calc R U .
H27C H 0.2152 0.4970 1.2829 0.102 Uiso 1 1 calc R U .
N3 N 0.1198(3) 0.7213(3) 0.8255(3) 0.0733(13) Uani 1 1 d . . .
HN3 H 0.1572 0.7435 0.8642 0.088 Uiso 1 1 calc R U .
N1 N -0.07560(17) 0.2995(2) 0.8068(3) 0.0548(10) Uani 1 1 d . . .
H1 H -0.0872 0.2712 0.8406 0.066 Uiso 1 1 calc R U .
N2 N -0.02656(16) 0.3606(2) 0.8478(3) 0.0469(9) Uani 1 1 d . . .
N4 N 0.0957(2) 0.6562(2) 0.8565(3) 0.0556(10) Uani 1 1 d . . .
O1 O -0.08402(15) 0.3245(2) 0.6647(3) 0.0598(8) Uani 1 1 d . . .
O2 O 0.02822(14) 0.51141(15) 0.8411(2) 0.0421(7) Uani 1 1 d . . .
O3 O 0.02875(18) 0.7140(2) 0.6790(2) 0.0647(9) Uani 1 1 d . . .
Zn1 Zn 0.0000 0.40323(4) 0.7500 0.0436(3) Uani 1 2 d S T P
Zn2 Zn 0.0000 0.62050(4) 0.7500 0.0482(3) Uani 1 2 d S T P
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 C1 N1 122.0(4) . .
O1 C1 C2 120.7(5) . .
N1 C1 C2 117.4(4) . .
C3 C2 C7 120.6(5) . .
C3 C2 C1 118.6(5) . .
C7 C2 C1 120.7(5) . .
C2 C3 C4 118.9(6) . .
C2 C3 H3 120.5 . .
C4 C3 H3 120.5 . .
C3 C4 C5 118.7(7) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
C6 C5 C4 122.3(6) . .
C6 C5 H5 118.8 . .
C4 C5 H5 118.8 . .
C5 C6 C7 120.4(7) . .
C5 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
C6 C7 C2 118.9(6) . .
C6 C7 H7 120.6 . .
C2 C7 H7 120.6 . .
N2 C8 C22 123.3(4) . .
N2 C8 H8 118.4 . .
C22 C8 H8 118.4 . .
O3 C11 N3 119.9(4) . .
O3 C11 C12 121.9(5) . .
N3 C11 C12 118.1(5) . .
C13 C12 C17 118.6(5) . .
C13 C12 C11 119.3(5) . .
C17 C12 C11 122.0(5) . .
C12 C13 C14 120.5(7) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
C15 C14 C13 120.6(8) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C14 C15 C16 119.4(7) . .
C14 C15 H15 120.3 . .
C16 C15 H15 120.3 . .
C17 C16 C15 120.8(8) . .
C17 C16 H16 119.6 . .
C15 C16 H16 119.6 . .
C16 C17 C12 119.9(7) . .
C16 C17 H17 120.1 . .
C12 C17 H17 120.1 . .
N4 C18 C26 124.7(5) . .
N4 C18 H18 117.6 . .
C26 C18 H18 117.6 . .
O2 C21 C26 122.3(4) . .
O2 C21 C22 121.4(4) . .
C26 C21 C22 116.2(4) . .
C23 C22 C21 120.3(4) . .
C23 C22 C8 118.0(4) . .
C21 C22 C8 121.6(4) . .
C22 C23 C24 123.1(4) . .
C22 C23 H23 118.4 . .
C24 C23 H23 118.4 . .
C25 C24 C23 116.2(4) . .
C25 C24 C27 122.9(4) . .
C23 C24 C27 120.8(4) . .
C24 C25 C26 123.1(4) . .
C24 C25 H25 118.4 . .
C26 C25 H25 118.4 . .
C25 C26 C21 120.9(4) . .
C25 C26 C18 118.2(4) . .
C21 C26 C18 120.9(4) . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C11 N3 N4 117.2(4) . .
C11 N3 HN3 121.4 . .
N4 N3 HN3 121.4 . .
C1 N1 N2 115.0(4) . .
C1 N1 H1 122.5 . .
N2 N1 H1 122.5 . .
C8 N2 N1 118.6(4) . .
C8 N2 Zn1 127.7(3) . .
N1 N2 Zn1 113.1(3) . .
C18 N4 N3 116.7(4) . .
C18 N4 Zn2 128.6(3) . .
N3 N4 Zn2 113.5(3) . .
C1 O1 Zn1 115.0(3) . .
C21 O2 Zn1 125.1(2) . .
C21 O2 Zn2 129.2(2) . .
Zn1 O2 Zn2 105.29(14) . .
C11 O3 Zn2 115.0(3) . .
O2 Zn1 O2 74.94(15) . 2_556
O2 Zn1 N2 79.79(12) . .
O2 Zn1 N2 131.04(12) 2_556 .
O2 Zn1 N2 131.03(12) . 2_556
O2 Zn1 N2 79.79(12) 2_556 2_556
N2 Zn1 N2 144.85(18) . 2_556
O2 Zn1 O1 137.84(12) . .
O2 Zn1 O1 98.09(12) 2_556 .
N2 Zn1 O1 74.15(14) . .
N2 Zn1 O1 86.42(13) 2_556 .
O2 Zn1 O1 98.09(12) . 2_556
O2 Zn1 O1 137.84(12) 2_556 2_556
N2 Zn1 O1 86.42(13) . 2_556
N2 Zn1 O1 74.15(14) 2_556 2_556
O1 Zn1 O1 112.48(18) . 2_556
O2 Zn2 O2 74.47(16) 2_556 .
O2 Zn2 N4 79.70(13) 2_556 2_556
O2 Zn2 N4 125.69(13) . 2_556
O2 Zn2 N4 125.69(13) 2_556 .
O2 Zn2 N4 79.70(13) . .
N4 Zn2 N4 150.6(2) 2_556 .
O2 Zn2 O3 102.49(11) 2_556 .
O2 Zn2 O3 144.65(13) . .
N4 Zn2 O3 87.02(14) 2_556 .
N4 Zn2 O3 73.89(14) . .
O2 Zn2 O3 144.65(13) 2_556 2_556
O2 Zn2 O3 102.49(11) . 2_556
N4 Zn2 O3 73.89(14) 2_556 2_556
N4 Zn2 O3 87.03(14) . 2_556
O3 Zn2 O3 99.22(17) . 2_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.237(6) .
C1 N1 1.323(6) .
C1 C2 1.489(6) .
C2 C3 1.364(8) .
C2 C7 1.405(7) .
C3 C4 1.401(8) .
C3 H3 0.9300 .
C4 C5 1.374(11) .
C4 H4 0.9300 .
C5 C6 1.330(10) .
C5 H5 0.9300 .
C6 C7 1.368(8) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 N2 1.282(6) .
C8 C22 1.445(6) .
C8 H8 0.9300 .
C11 O3 1.254(6) .
C11 N3 1.320(7) .
C11 C12 1.478(6) .
C12 C13 1.356(8) .
C12 C17 1.386(9) .
C13 C14 1.390(9) .
C13 H13 0.9300 .
C14 C15 1.333(11) .
C14 H14 0.9300 .
C15 C16 1.373(10) .
C15 H15 0.9300 .
C16 C17 1.363(9) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 N4 1.270(6) .
C18 C26 1.455(6) .
C18 H18 0.9300 .
C21 O2 1.305(5) .
C21 C26 1.405(6) .
C21 C22 1.432(5) .
C22 C23 1.376(6) .
C23 C24 1.391(6) .
C23 H23 0.9300 .
C24 C25 1.374(6) .
C24 C27 1.508(7) .
C25 C26 1.387(7) .
C25 H25 0.9300 .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
N3 N4 1.380(5) .
N3 HN3 0.8600 .
N1 N2 1.378(5) .
N1 H1 0.8600 .
N2 Zn1 2.128(4) .
N4 Zn2 2.119(4) .
O1 Zn1 2.135(3) .
O2 Zn1 2.055(3) .
O2 Zn2 2.066(3) .
O3 Zn2 2.175(3) .
Zn1 O2 2.055(3) 2_556
Zn1 N2 2.128(4) 2_556
Zn1 O1 2.135(3) 2_556
Zn2 O2 2.066(3) 2_556
Zn2 N4 2.119(4) 2_556
Zn2 O3 2.175(3) 2_556
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 1.000 0.000 0.205 667 169 ' '
2 0.500 0.500 -0.058 667 169 ' '
