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#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/29/7012983.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_7012983
loop_
_publ_author_name
'Bazzicalupi, Carla'
'Bencini, Andrea'
'Berni, Emanuela'
'Bianchi, Antonio'
'Fornasari, Patrizia'
'Giorgi, Claudia'
'Marinelli, Cristian'
'Valtancoli, Barbara'
_publ_section_title
;
 Protonated macrocyclic Zn(ii) complexes as polyfunctional receptors
 for ATPElectronic supplementary information (ESI) available:
 Protonation constants of ligands L1?L4, formation constants of the ATP
 complexes with ligands L1?L4 and the crystal packing of
 [ZnHL4Br]Br(ClO4). See http://www.rsc.org/suppdata/dt/b3/b303264g/
;
_journal_issue                   12
_journal_name_full               'Dalton Transactions'
_journal_page_first              2564
_journal_paper_doi               10.1039/b303264g
_journal_year                    2003
_chemical_formula_moiety
;
(C23 H33 N6 Zn Br 2+), (Br 1-), (Cl O4 1-)
;
_chemical_formula_sum            'C23 H33 Br2 Cl N6 O4 Zn'
_chemical_formula_weight         718.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 91.73(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.351(2)
_cell_length_b                   17.809(6)
_cell_length_c                   21.469(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      20
_cell_measurement_theta_min      10
_cell_volume                     2809.3(14)
_computing_cell_refinement       'XSCANS BRUKER'
_computing_data_collection       'XSCANS BRUKER'
_computing_data_reduction        'XSCANS BRUKER'
_computing_molecular_graphics    'ORTEP3 Ver. 1.01β (Farrugia, 1997)'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97(Altomare, 1999)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.810
_diffrn_measured_fraction_theta_max 0.810
_diffrn_measurement_device_type  'siemens P4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4778
_diffrn_reflns_theta_full        60.01
_diffrn_reflns_theta_max         60.01
_diffrn_reflns_theta_min         3.22
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.763
_exptl_absorpt_correction_T_max  0.28
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.907
_refine_diff_density_min         -1.581
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w==1/[σ²(Fo²)+(0.1091P)²+7.6138P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                3145
_reflns_number_total             3380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303264g.txt
_cod_data_source_block           '[ZnHL4Br]Br(ClO4)'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7012983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn 0.62893(13) 0.22885(4) 0.06495(3) 0.0352(3) Uani 1 1 d . . .
Br2 Br 0.67992(12) 0.40261(4) -0.08733(3) 0.0502(3) Uani 1 1 d . . .
Br1 Br 0.90044(13) 0.20616(5) 0.01267(5) 0.0683(3) Uani 1 1 d . . .
Cl1 Cl 0.9260(3) 0.60633(11) -0.24536(7) 0.0571(5) Uani 1 1 d . . .
O11 O 1.0249(9) 0.6500(3) -0.2887(3) 0.0759(18) Uani 1 1 d . . .
O12 O 0.7501(11) 0.5931(4) -0.2685(3) 0.090(2) Uani 1 1 d . . .
O13 O 0.9067(13) 0.6496(8) -0.1904(4) 0.181(6) Uani 1 1 d . . .
O14 O 1.0198(16) 0.5433(7) -0.2344(6) 0.198(7) Uani 1 1 d . . .
N1 N 0.4353(7) 0.1431(2) 0.01063(19) 0.0283(11) Uani 1 1 d . . .
C1 C 0.3832(9) 0.1361(3) -0.0490(3) 0.0329(14) Uani 1 1 d . . .
C2 C 0.2804(10) 0.0742(3) -0.0710(3) 0.0429(17) Uani 1 1 d . . .
H2A H 0.2484 0.0707 -0.1131 0.051 Uiso 1 1 calc R . .
C3 C 0.2276(10) 0.0196(3) -0.0308(3) 0.0436(17) Uani 1 1 d . . .
H3A H 0.1583 -0.0209 -0.0453 0.052 Uiso 1 1 calc R . .
C4 C 0.2790(9) 0.0251(3) 0.0325(3) 0.0376(15) Uani 1 1 d . . .
C5 C 0.3829(9) 0.0877(3) 0.0505(3) 0.0299(14) Uani 1 1 d . . .
C6 C 0.4496(10) 0.0925(3) 0.1143(3) 0.0346(15) Uani 1 1 d . . .
C7 C 0.2913(12) -0.0240(4) 0.1373(4) 0.057(2) Uani 1 1 d . . .
H7 H 0.2564 -0.0601 0.1659 0.068 Uiso 1 1 calc R . .
C8 C 0.2330(11) -0.0297(3) 0.0777(4) 0.0503(19) Uani 1 1 d . . .
H8 H 0.1609 -0.0703 0.0656 0.060 Uiso 1 1 calc R . .
N2 N 0.5635(8) 0.1498(3) 0.1297(2) 0.0370(13) Uani 1 1 d . . .
C9 C 0.4046(11) 0.0359(3) 0.1575(3) 0.0453(19) Uani 1 1 d . . .
C10 C 0.4857(13) 0.0426(4) 0.2180(3) 0.058(2) Uani 1 1 d . . .
H10 H 0.4583 0.0073 0.2483 0.069 Uiso 1 1 calc R . .
C11 C 0.6013(14) 0.0989(4) 0.2327(3) 0.064(3) Uani 1 1 d . . .
H11 H 0.6544 0.1022 0.2724 0.077 Uiso 1 1 calc R . .
C12 C 0.6416(12) 0.1534(4) 0.1864(3) 0.053(2) Uani 1 1 d . . .
C13 C 0.7763(12) 0.2159(4) 0.1969(3) 0.056(2) Uani 1 1 d . . .
H13A H 0.7754 0.2316 0.2402 0.068 Uiso 1 1 calc R . .
H13B H 0.8977 0.1980 0.1883 0.068 Uiso 1 1 calc R . .
N3 N 0.7316(10) 0.2798(3) 0.1566(2) 0.0467(15) Uani 1 1 d . . .
H2 H 0.829(9) 0.310(3) 0.149(3) 0.021(15) Uiso 1 1 d . . .
C14 C 0.5816(11) 0.3246(4) 0.1805(3) 0.0448(17) Uani 1 1 d . . .
H14A H 0.6080 0.3365 0.2239 0.054 Uiso 1 1 calc R . .
H14B H 0.4713 0.2947 0.1786 0.054 Uiso 1 1 calc R . .
C15 C 0.5480(11) 0.3969(3) 0.1450(3) 0.0431(17) Uani 1 1 d . . .
H15A H 0.6287 0.4351 0.1623 0.052 Uiso 1 1 calc R . .
H15B H 0.4242 0.4130 0.1518 0.052 Uiso 1 1 calc R . .
C16 C 0.5757(10) 0.3926(3) 0.0743(3) 0.0357(15) Uani 1 1 d . . .
H16A H 0.5280 0.4380 0.0550 0.043 Uiso 1 1 calc R . .
H16B H 0.7051 0.3906 0.0669 0.043 Uiso 1 1 calc R . .
N4 N 0.4857(8) 0.3263(3) 0.0439(2) 0.0328(13) Uani 1 1 d . . .
H1 H 0.504(8) 0.333(3) 0.014(2) 0.004(14) Uiso 1 1 d . . .
C17 C 0.2880(10) 0.3208(3) 0.0514(3) 0.0368(15) Uani 1 1 d . . .
H17A H 0.2669 0.3057 0.0940 0.044 Uiso 1 1 calc R . .
H17B H 0.2423 0.2808 0.0245 0.044 Uiso 1 1 calc R . .
C18 C 0.1750(11) 0.3910(3) 0.0376(3) 0.0437(17) Uani 1 1 d . . .
H18A H 0.0481 0.3791 0.0438 0.052 Uiso 1 1 calc R . .
H18B H 0.2101 0.4293 0.0678 0.052 Uiso 1 1 calc R . .
C19 C 0.1913(11) 0.4242(3) -0.0275(3) 0.0436(17) Uani 1 1 d . . .
H19A H 0.1246 0.4711 -0.0298 0.052 Uiso 1 1 calc R . .
H19B H 0.3182 0.4350 -0.0348 0.052 Uiso 1 1 calc R . .
N5 N 0.1203(10) 0.3729(3) -0.0768(2) 0.0421(14) Uani 1 1 d . . .
H3 H -0.015(11) 0.370(3) -0.077(3) 0.031(17) Uiso 1 1 d . . .
H4 H 0.171(9) 0.328(4) -0.074(3) 0.025(15) Uiso 1 1 d . . .
C20 C 0.1547(12) 0.4006(4) -0.1418(3) 0.051(2) Uani 1 1 d . . .
H20A H 0.0612 0.4365 -0.1543 0.061 Uiso 1 1 calc R . .
H20B H 0.2714 0.4260 -0.1422 0.061 Uiso 1 1 calc R . .
C21 C 0.1541(11) 0.3367(4) -0.1871(3) 0.0505(19) Uani 1 1 d . . .
H21A H 0.1644 0.3564 -0.2290 0.061 Uiso 1 1 calc R . .
H21B H 0.0391 0.3102 -0.1852 0.061 Uiso 1 1 calc R . .
C22 C 0.3090(12) 0.2818(4) -0.1737(3) 0.050(2) Uani 1 1 d . . .
H22A H 0.3168 0.2465 -0.2079 0.060 Uiso 1 1 calc R . .
H22B H 0.4231 0.3091 -0.1703 0.060 Uiso 1 1 calc R . .
N6 N 0.2795(10) 0.2404(3) -0.1151(3) 0.0387(15) Uani 1 1 d . . .
H5 H 0.204(10) 0.222(3) -0.122(3) 0.015(19) Uiso 1 1 d . . .
C23 C 0.4391(11) 0.1952(3) -0.0952(3) 0.0412(17) Uani 1 1 d . . .
H23A H 0.5311 0.2276 -0.0761 0.049 Uiso 1 1 calc R . .
H23B H 0.4909 0.1713 -0.1312 0.049 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
N2 Zn N4 126.6(2) . . ?
N2 Zn N3 76.4(2) . . ?
N4 Zn N3 90.5(2) . . ?
N2 Zn Br1 115.20(16) . . ?
N4 Zn Br1 118.17(16) . . ?
N3 Zn Br1 102.54(19) . . ?
N2 Zn N1 74.98(17) . . ?
N4 Zn N1 97.96(19) . . ?
N3 Zn N1 149.4(2) . . ?
Br1 Zn N1 99.21(12) . . ?
O14 Cl1 O12 113.0(8) . . ?
O14 Cl1 O13 112.0(9) . . ?
O12 Cl1 O13 105.9(5) . . ?
O14 Cl1 O11 107.6(5) . . ?
O12 Cl1 O11 110.2(4) . . ?
O13 Cl1 O11 108.1(5) . . ?
C1 N1 C5 117.1(5) . . ?
C1 N1 Zn 133.2(4) . . ?
C5 N1 Zn 109.4(3) . . ?
N1 C1 C2 122.1(5) . . ?
N1 C1 C23 119.3(5) . . ?
C2 C1 C23 118.6(5) . . ?
C3 C2 C1 120.4(6) . . ?
C2 C3 C4 119.2(6) . . ?
C5 C4 C3 116.9(6) . . ?
C5 C4 C8 119.7(6) . . ?
C3 C4 C8 123.4(6) . . ?
N1 C5 C4 124.2(5) . . ?
N1 C5 C6 117.2(5) . . ?
C4 C5 C6 118.5(5) . . ?
N2 C6 C9 122.2(6) . . ?
N2 C6 C5 117.8(5) . . ?
C9 C6 C5 119.9(6) . . ?
C8 C7 C9 121.1(6) . . ?
C7 C8 C4 121.6(7) . . ?
C12 N2 C6 120.4(5) . . ?
C12 N2 Zn 119.0(5) . . ?
C6 N2 Zn 120.6(4) . . ?
C7 C9 C6 119.0(6) . . ?
C7 C9 C10 124.9(6) . . ?
C6 C9 C10 116.1(7) . . ?
C11 C10 C9 121.4(6) . . ?
C10 C11 C12 119.2(7) . . ?
N2 C12 C11 120.7(7) . . ?
N2 C12 C13 115.9(6) . . ?
C11 C12 C13 123.3(7) . . ?
N3 C13 C12 110.7(6) . . ?
C13 N3 C14 112.1(6) . . ?
C13 N3 Zn 105.3(4) . . ?
C14 N3 Zn 106.6(4) . . ?
N3 C14 C15 113.6(6) . . ?
C14 C15 C16 115.5(5) . . ?
N4 C16 C15 113.6(5) . . ?
C17 N4 C16 115.4(5) . . ?
C17 N4 Zn 114.7(4) . . ?
C16 N4 Zn 110.5(4) . . ?
N4 C17 C18 117.3(5) . . ?
C19 C18 C17 116.0(6) . . ?
N5 C19 C18 112.4(5) . . ?
C19 N5 C20 113.2(5) . . ?
C21 C20 N5 110.8(5) . . ?
C20 C21 C22 112.2(6) . . ?
N6 C22 C21 110.7(6) . . ?
C23 N6 C22 112.5(6) . . ?
N6 C23 C1 109.9(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn N2 2.047(5) . ?
Zn N4 2.072(5) . ?
Zn N3 2.276(5) . ?
Zn Br1 2.3541(14) . ?
Zn N1 2.370(5) . ?
Cl1 O14 1.334(9) . ?
Cl1 O12 1.391(8) . ?
Cl1 O13 1.421(8) . ?
Cl1 O11 1.429(6) . ?
N1 C1 1.332(7) . ?
N1 C5 1.369(7) . ?
C1 C2 1.409(9) . ?
C1 C23 1.512(8) . ?
C2 C3 1.365(9) . ?
C3 C4 1.403(9) . ?
C4 C5 1.400(8) . ?
C4 C8 1.423(9) . ?
C5 C6 1.444(8) . ?
C6 N2 1.354(8) . ?
C6 C9 1.415(8) . ?
C7 C8 1.342(11) . ?
C7 C9 1.413(11) . ?
N2 C12 1.331(8) . ?
C9 C10 1.419(10) . ?
C10 C11 1.346(12) . ?
C11 C12 1.426(10) . ?
C12 C13 1.503(11) . ?
C13 N3 1.461(9) . ?
N3 C14 1.466(10) . ?
C14 C15 1.512(9) . ?
C15 C16 1.538(8) . ?
C16 N4 1.494(7) . ?
N4 C17 1.471(9) . ?
C17 C18 1.526(9) . ?
C18 C19 1.525(9) . ?
C19 N5 1.481(8) . ?
N5 C20 1.509(8) . ?
C20 C21 1.497(10) . ?
C21 C22 1.521(11) . ?
C22 N6 1.480(8) . ?
N6 C23 1.475(10) . ?
