#------------------------------------------------------------------------------
#$Date: 2017-05-05 11:54:48 +0300 (Fri, 05 May 2017) $
#$Revision: 196244 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/29/7042907.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_7042907
loop_
_publ_author_name
'Reddy, Andrew'
'Sangenito, Leandro Stefano'
'Guedes, Arthur de Azevedo'
'Branquinha, Marta Helena'
'Kavanagh, Kevin'
'McGinley, John'
'Dos Santos, André Luis Souza'
'Velasco-Torrijos, Trinidad'
_publ_section_title
;
 Glycosylated metal chelators as anti-parasitic agents with tunable
 selectivity.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5297
_journal_page_last               5307
_journal_paper_doi               10.1039/c6dt04615k
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C12 H16 N4 Zn, 2(Cl O4)'
_chemical_formula_sum            'C12 H16 Cl2 N4 O8 Zn'
_chemical_formula_weight         480.56
_chemical_name_systematic        'Bis(2-picolylamino)zinc perchlorate '
_chemical_temperature_decomposition 518
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-11-23 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.9255(7)
_cell_length_b                   14.9255(7)
_cell_length_c                   15.3140(7)
_cell_measurement_reflns_used    5191
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.73
_cell_volume                     3411.5(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX 3 (Bruker, 2015) '
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'XP (Bruker, 2008-2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'DUO Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX DUO KAPPA'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21050
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.289
_diffrn_reflns_theta_min         1.905
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.806
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0514 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.9000.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_description       needle
_exptl_crystal_F_000             1952
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.280
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0500
_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)+24.8580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1832
_reflns_number_total             2120
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt04615k2.cif
_cod_data_source_block           tcd542
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been '518
(Decomposition) '. The value '518 (Decomposition) ' was changed to
'518'.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        3411.5(4)
_cod_database_code               7042907
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Others
 Sof(O2A)=Sof(O1A)=Sof(O4A)=Sof(O3A)=1-FVAR(1)
 Sof(O1)=Sof(O3)=Sof(O2)=Sof(O4)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6), C7(H7)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Mitegen holder in oil'
_olex2_submission_original_sample_id L211-Zn(ClO4)-THF
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5000 0.7500 0.40603(4) 0.02716(18) Uani 1 2 d S T P . .
Cl1 Cl 0.29428(6) 0.81765(6) 0.55200(5) 0.02059(19) Uani 1 1 d . . . . .
N4 N 0.40279(19) 0.7106(2) 0.31963(19) 0.0198(6) Uani 1 1 d . . . . .
N1 N 0.4776(2) 0.6301(2) 0.4615(2) 0.0261(7) Uani 1 1 d . . . . .
H1A H 0.5216 0.5910 0.4460 0.031 Uiso 1 1 calc R . . . .
H1B H 0.4777 0.6355 0.5207 0.031 Uiso 1 1 calc R . . . .
C3 C 0.3658(2) 0.6322(2) 0.3430(2) 0.0190(7) Uani 1 1 d . . . . .
C8 C 0.3067(2) 0.5876(3) 0.2869(2) 0.0243(8) Uani 1 1 d . . . . .
H8 H 0.2797 0.5328 0.3041 0.029 Uiso 1 1 calc R . . . .
C2 C 0.3895(2) 0.5962(3) 0.4315(2) 0.0237(8) Uani 1 1 d . . . . .
H2A H 0.3427 0.6140 0.4739 0.028 Uiso 1 1 calc R . . . .
H2B H 0.3911 0.5299 0.4292 0.028 Uiso 1 1 calc R . . . .
C5 C 0.3846(2) 0.7459(3) 0.2408(2) 0.0245(8) Uani 1 1 d . . . . .
H5 H 0.4112 0.8014 0.2251 0.029 Uiso 1 1 calc R . . . .
C6 C 0.3286(3) 0.7041(3) 0.1822(2) 0.0281(9) Uani 1 1 d . . . . .
H6 H 0.3178 0.7294 0.1263 0.034 Uiso 1 1 calc R . . . .
O1 O 0.3721(4) 0.7630(3) 0.5665(4) 0.0410(14) Uani 0.687(8) 1 d . . . A 1
C7 C 0.2884(3) 0.6243(3) 0.2065(3) 0.0294(9) Uani 1 1 d . . . . .
H7 H 0.2483 0.5950 0.1677 0.035 Uiso 1 1 calc R . . . .
O3 O 0.2210(5) 0.7660(5) 0.5224(4) 0.0473(19) Uani 0.687(8) 1 d . . . A 1
O2 O 0.3180(3) 0.8861(3) 0.4876(3) 0.0322(13) Uani 0.687(8) 1 d . . . A 1
O4 O 0.2721(4) 0.8611(4) 0.6328(3) 0.0384(14) Uani 0.687(8) 1 d . . . A 1
O2A O 0.3297(6) 0.8167(9) 0.4666(6) 0.038(4) Uani 0.313(8) 1 d . . . A 2
O1A O 0.3310(9) 0.7405(7) 0.6002(7) 0.033(3) Uani 0.313(8) 1 d . . . A 2
O4A O 0.1957(8) 0.8036(9) 0.5447(9) 0.032(3) Uani 0.313(8) 1 d . . . A 2
O3A O 0.3085(8) 0.8969(6) 0.5974(9) 0.043(3) Uani 0.313(8) 1 d . . . A 2
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'
Cl Cl 0.1484 0.1585 '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
N4 Zn1 N4 99.60(17) . 6_564
N1 Zn1 N4 84.22(12) 6_564 6_564
N1 Zn1 N4 84.22(12) . .
N1 Zn1 N4 130.27(13) 6_564 .
N1 Zn1 N4 130.27(13) . 6_564
N1 Zn1 N1 129.99(19) . 6_564
O1 Cl1 O2 107.8(3) . .
O3 Cl1 O1 111.4(4) . .
O3 Cl1 O2 110.6(3) . .
O3 Cl1 O4 110.2(4) . .
O4 Cl1 O1 108.0(3) . .
O4 Cl1 O2 108.7(3) . .
O2A Cl1 O1A 108.5(6) . .
O2A Cl1 O4A 107.4(7) . .
O1A Cl1 O4A 107.1(7) . .
O3A Cl1 O2A 114.6(7) . .
O3A Cl1 O1A 110.9(6) . .
O3A Cl1 O4A 108.0(7) . .
C3 N4 Zn1 111.7(2) . .
C3 N4 C5 119.8(3) . .
C5 N4 Zn1 127.6(3) . .
Zn1 N1 H1A 110.0 . .
Zn1 N1 H1B 110.0 . .
H1A N1 H1B 108.3 . .
C2 N1 Zn1 108.7(2) . .
C2 N1 H1A 110.0 . .
C2 N1 H1B 110.0 . .
N4 C3 C8 120.7(3) . .
N4 C3 C2 117.1(3) . .
C8 C3 C2 122.2(3) . .
C3 C8 H8 120.5 . .
C7 C8 C3 119.0(4) . .
C7 C8 H8 120.5 . .
N1 C2 C3 111.5(3) . .
N1 C2 H2A 109.3 . .
N1 C2 H2B 109.3 . .
C3 C2 H2A 109.3 . .
C3 C2 H2B 109.3 . .
H2A C2 H2B 108.0 . .
N4 C5 H5 119.0 . .
N4 C5 C6 122.0(4) . .
C6 C5 H5 119.0 . .
C5 C6 H6 120.7 . .
C5 C6 C7 118.6(4) . .
C7 C6 H6 120.7 . .
C8 C7 C6 119.8(4) . .
C8 C7 H7 120.1 . .
C6 C7 H7 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N4 2.050(3) 6_564
Zn1 N4 2.050(3) .
Zn1 N1 2.010(3) 6_564
Zn1 N1 2.010(3) .
Cl1 O1 1.437(5) .
Cl1 O3 1.413(5) .
Cl1 O2 1.464(4) .
Cl1 O4 1.436(4) .
Cl1 O2A 1.410(8) .
Cl1 O1A 1.474(10) .
Cl1 O4A 1.491(13) .
Cl1 O3A 1.388(9) .
N4 C3 1.342(5) .
N4 C5 1.345(5) .
N1 H1A 0.9100 .
N1 H1B 0.9100 .
N1 C2 1.481(5) .
C3 C8 1.399(5) .
C3 C2 1.501(5) .
C8 H8 0.9500 .
C8 C7 1.376(6) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C5 H5 0.9500 .
C5 C6 1.376(5) .
C6 H6 0.9500 .
C6 C7 1.385(6) .
C7 H7 0.9500 .
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
N1 H1A O2 0.91 2.50 3.086(6) 123 6_564
N1 H1A O4 0.91 2.36 3.253(7) 167 4_454
N1 H1A O4A 0.91 2.43 3.014(14) 122 4_454
N1 H1B O1 0.91 2.50 3.404(7) 170 12_767
N1 H1B O4 0.91 2.61 3.168(6) 120 12_767
N1 H1B O1A 0.91 2.19 3.012(10) 150 12_767
C8 H8 O3A 0.95 2.56 3.353(10) 141 14_546
C2 H2B O1A 0.99 2.53 3.290(15) 133 4_454
C2 H2B O3A 0.99 2.37 3.242(11) 146 14_546
C5 H5 O4A 0.95 2.46 3.229(13) 138 7_554
C6 H6 O3 0.95 2.35 3.251(7) 158 13_565
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
Zn1 N4 C3 C8 -171.4(3)
Zn1 N4 C3 C2 9.6(4)
Zn1 N4 C5 C6 168.2(3)
Zn1 N1 C2 C3 27.8(4)
N4 C3 C8 C7 1.4(5)
N4 C3 C2 N1 -25.6(5)
N4 C5 C6 C7 1.6(6)
C3 N4 C5 C6 0.0(5)
C3 C8 C7 C6 0.2(5)
C8 C3 C2 N1 155.5(3)
C2 C3 C8 C7 -179.7(3)
C5 N4 C3 C8 -1.5(5)
C5 N4 C3 C2 179.5(3)
C5 C6 C7 C8 -1.6(6)
