#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/26/7012676.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_7012676
loop_
_publ_author_name
'Dong, Ying'
'Farquhar, Sandra'
'Gloe, Karsten'
'Lindoy, Leonard F.'
'Rumbel, Brendan R.'
'Turner, Peter'
'Wichmann, Kathrin'
_publ_section_title
;
 Metal ion recognition. Interaction of a series of successively
 N-benzylated derivatives of 1,4,8,11-tetraazacyclotetradecane (cyclam)
 with selected transition and post-transition metal ions
;
_journal_issue                   8
_journal_name_full               'Dalton Transactions'
_journal_page_first              1558
_journal_paper_doi               10.1039/b300002h
_journal_year                    2003
_chemical_formula_sum            'C24 H38 N6 O7 Pb'
_chemical_formula_weight         729.79
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1228(13)
_cell_length_b                   9.4321(7)
_cell_length_c                   18.4865(15)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.081
_cell_measurement_theta_min      2.540
_cell_volume                     2811.3(4)
_computing_cell_refinement       'SAINT (Bruker,1995)'
_computing_data_collection       'SMART (Bruker,1995)'
_computing_data_reduction        'SAINT and XPREP (Bruker 1995)'
_computing_molecular_graphics
;
teXsan for Windows (MSC, 1997) 
xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999)
ORTEPII  (Johnson,C.K., 1976). 
WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_crystal_treatment
;
attached to a thin glass fibre
;
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27909
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0.54
_diffrn_standards_number         211
_exptl_absorpt_coefficient_mu    6.053
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.294
_exptl_crystal_size_min          0.264
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00043(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.350
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.350
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0176
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0496
_refine_ls_wR_factor_ref         0.0553
_reflns_number_gt                2361
_reflns_number_total             3412
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b300002h.txt
_cod_data_source_block           lfl62
_cod_original_sg_symbol_H-M      'P b c n    '
_cod_database_code               7012676
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
Pb1 Pb 0.5000 0.488340(13) 0.7500 0.03246(6) Uani 1 2 d S . .
N1 N 0.60441(14) 0.5809(2) 0.65508(12) 0.0400(5) Uani 1 1 d . . .
N2 N 0.42353(13) 0.6865(2) 0.69643(12) 0.0406(5) Uani 1 1 d . . .
H2N H 0.4521 0.7673 0.7065 0.049 Uiso 1 1 calc R . .
C1 C 0.56784(19) 0.6078(4) 0.58203(16) 0.0544(8) Uani 1 1 d . . .
H1A H 0.5486 0.5180 0.5627 0.065 Uiso 1 1 calc R . .
H1B H 0.6117 0.6413 0.5505 0.065 Uiso 1 1 calc R . .
C2 C 0.49645(18) 0.7132(4) 0.57815(19) 0.0561(8) Uani 1 1 d . . .
H2A H 0.5161 0.8028 0.5974 0.067 Uiso 1 1 calc R . .
H2B H 0.4835 0.7285 0.5275 0.067 Uiso 1 1 calc R . .
C3 C 0.41604(18) 0.6760(4) 0.61687(16) 0.0515(8) Uani 1 1 d . . .
H3A H 0.3726 0.7395 0.6005 0.062 Uiso 1 1 calc R . .
H3B H 0.4000 0.5802 0.6040 0.062 Uiso 1 1 calc R . .
C4 C 0.34194(17) 0.6964(3) 0.73341(17) 0.0487(8) Uani 1 1 d . . .
H4A H 0.3091 0.6128 0.7227 0.058 Uiso 1 1 calc R . .
H4B H 0.3120 0.7789 0.7161 0.058 Uiso 1 1 calc R . .
C5 C 0.35553(19) 0.7082(3) 0.81473(17) 0.0471(7) Uani 1 1 d . . .
H5A H 0.3899 0.7904 0.8247 0.057 Uiso 1 1 calc R . .
H5B H 0.3025 0.7225 0.8384 0.057 Uiso 1 1 calc R . .
C6 C 0.66340(17) 0.4582(3) 0.65068(15) 0.0418(6) Uani 1 1 d . . .
H6A H 0.6321 0.3744 0.6374 0.050 Uiso 1 1 calc R . .
H6B H 0.6861 0.4419 0.6986 0.050 Uiso 1 1 calc R . .
C7 C 0.73478(17) 0.4736(3) 0.59836(16) 0.0415(6) Uani 1 1 d . . .
C8 C 0.80882(18) 0.5404(3) 0.61836(18) 0.0485(7) Uani 1 1 d . . .
H8 H 0.8147 0.5784 0.6645 0.058 Uiso 1 1 calc R . .
C9 C 0.87368(19) 0.5494(3) 0.5687(2) 0.0606(9) Uani 1 1 d . . .
H9 H 0.9228 0.5940 0.5821 0.073 Uiso 1 1 calc R . .
C10 C 0.8663(3) 0.4939(4) 0.5008(2) 0.0666(12) Uani 1 1 d . . .
H10 H 0.9102 0.5009 0.4684 0.080 Uiso 1 1 calc R . .
C11 C 0.7937(2) 0.4274(5) 0.4803(2) 0.0694(10) Uani 1 1 d . . .
H11 H 0.7882 0.3901 0.4339 0.083 Uiso 1 1 calc R . .
C12 C 0.72906(19) 0.4170(4) 0.52971(18) 0.0571(8) Uani 1 1 d . . .
H12 H 0.6806 0.3706 0.5162 0.069 Uiso 1 1 calc R . .
O1 O 0.4651(2) 0.2594(4) 0.63629(19) 0.1217(14) Uani 1 1 d . . .
O2 O 0.35665(18) 0.3485(3) 0.67886(17) 0.0933(9) Uani 1 1 d . . .
O3 O 0.3742(2) 0.1274(3) 0.68673(19) 0.1174(12) Uani 1 1 d . . .
N3 N 0.3994(2) 0.2436(4) 0.66615(18) 0.0684(8) Uani 1 1 d . . .
O4 O 0.5000 -0.0398(5) 0.7500 0.0907(16) Uani 1 2 d SD . .
H4O H 0.467(3) 0.005(4) 0.717(3) 0.109 Uiso 1 1 d D . .
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'
Pb Pb -3.3944 10.1111 '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 Pb1 N2 80.47(11) 3_656 . ?
N2 Pb1 N1 71.86(7) 3_656 . ?
N2 Pb1 N1 78.20(7) . . ?
N2 Pb1 N1 78.20(7) 3_656 3_656 ?
N2 Pb1 N1 71.86(7) . 3_656 ?
N1 Pb1 N1 140.51(10) . 3_656 ?
N2 Pb1 O2 155.58(8) 3_656 . ?
N2 Pb1 O2 76.58(8) . . ?
N1 Pb1 O2 110.89(8) . . ?
N1 Pb1 O2 86.77(8) 3_656 . ?
N2 Pb1 O1 155.15(8) 3_656 . ?
N2 Pb1 O1 99.68(10) . . ?
N1 Pb1 O1 83.78(9) . . ?
N1 Pb1 O1 125.75(8) 3_656 . ?
O2 Pb1 O1 40.58(8) . . ?
C5 N1 C1 112.1(2) 3_656 . ?
C5 N1 C6 111.8(2) 3_656 . ?
C1 N1 C6 109.4(2) . . ?
C5 N1 Pb1 107.68(16) 3_656 . ?
C1 N1 Pb1 114.44(17) . . ?
C6 N1 Pb1 100.92(15) . . ?
C3 N2 C4 112.9(2) . . ?
C3 N2 Pb1 113.10(17) . . ?
C4 N2 Pb1 107.93(16) . . ?
C3 N2 H2N 107.5 . . ?
C4 N2 H2N 107.5 . . ?
Pb1 N2 H2N 107.5 . . ?
N1 C1 C2 116.8(3) . . ?
N1 C1 H1A 108.1 . . ?
C2 C1 H1A 108.1 . . ?
N1 C1 H1B 108.1 . . ?
C2 C1 H1B 108.1 . . ?
H1A C1 H1B 107.3 . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2A 107.8 . . ?
C1 C2 H2A 107.8 . . ?
C3 C2 H2B 107.8 . . ?
C1 C2 H2B 107.8 . . ?
H2A C2 H2B 107.1 . . ?
N2 C3 C2 112.5(2) . . ?
N2 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N2 C4 C5 109.4(2) . . ?
N2 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C4 112.1(2) 3_656 . ?
N1 C5 H5A 109.2 3_656 . ?
C4 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 3_656 . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C7 116.3(2) . . ?
N1 C6 H6A 108.2 . . ?
C7 C6 H6A 108.2 . . ?
N1 C6 H6B 108.2 . . ?
C7 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C12 C7 C8 118.3(3) . . ?
C12 C7 C6 120.1(3) . . ?
C8 C7 C6 121.6(3) . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.1(4) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C11 121.8(3) . . ?
C7 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
N3 O1 Pb1 86.2(2) . . ?
N3 O2 Pb1 90.3(2) . . ?
O1 N3 O3 122.9(4) . . ?
O1 N3 O2 118.8(4) . . ?
O3 N3 O2 118.2(4) . . ?
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
Pb1 N2 2.448(2) 3_656 ?
Pb1 N2 2.448(2) . ?
Pb1 N1 2.583(2) . ?
Pb1 N1 2.583(2) 3_656 ?
Pb1 O2 2.968(3) . ?
Pb1 O1 3.066(3) . ?
N1 C5 1.474(4) 3_656 ?
N1 C1 1.495(3) . ?
N1 C6 1.500(3) . ?
N2 C3 1.479(4) . ?
N2 C4 1.485(3) . ?
N2 H2N 0.9100 . ?
C1 C2 1.523(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.522(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.523(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.474(4) 3_656 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.510(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C12 1.380(4) . ?
C7 C8 1.399(4) . ?
C8 C9 1.394(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
O1 N3 1.204(4) . ?
O2 N3 1.229(4) . ?
O3 N3 1.229(4) . ?
O4 H4O 0.909(19) . ?
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
N2 H2N O4 0.91 2.13 3.028(5) 167.1 1_565
O4 H4O O3 0.909(19) 1.98(3) 2.823(4) 155(6) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Pb1 N1 C5 -5.23(17) 3_656 . . 3_656 ?
N2 Pb1 N1 C5 78.47(17) . . . 3_656 ?
N1 Pb1 N1 C5 37.38(16) 3_656 . . 3_656 ?
O2 Pb1 N1 C5 148.99(17) . . . 3_656 ?
O1 Pb1 N1 C5 179.75(19) . . . 3_656 ?
N2 Pb1 N1 C1 -130.6(2) 3_656 . . . ?
N2 Pb1 N1 C1 -46.91(19) . . . . ?
N1 Pb1 N1 C1 -88.00(19) 3_656 . . . ?
O2 Pb1 N1 C1 23.6(2) . . . . ?
O1 Pb1 N1 C1 54.4(2) . . . . ?
N2 Pb1 N1 C6 112.05(17) 3_656 . . . ?
N2 Pb1 N1 C6 -164.24(17) . . . . ?
N1 Pb1 N1 C6 154.67(17) 3_656 . . . ?
O2 Pb1 N1 C6 -93.72(16) . . . . ?
O1 Pb1 N1 C6 -62.96(17) . . . . ?
N2 Pb1 N2 C3 128.1(2) 3_656 . . . ?
N1 Pb1 N2 C3 54.76(18) . . . . ?
N1 Pb1 N2 C3 -151.3(2) 3_656 . . . ?
O2 Pb1 N2 C3 -60.34(19) . . . . ?
O1 Pb1 N2 C3 -26.7(2) . . . . ?
N2 Pb1 N2 C4 -106.3(2) 3_656 . . . ?
N1 Pb1 N2 C4 -179.56(19) . . . . ?
N1 Pb1 N2 C4 -25.65(17) 3_656 . . . ?
O2 Pb1 N2 C4 65.33(19) . . . . ?
O1 Pb1 N2 C4 98.94(19) . . . . ?
C5 N1 C1 C2 -64.7(3) 3_656 . . . ?
C6 N1 C1 C2 170.7(3) . . . . ?
Pb1 N1 C1 C2 58.3(3) . . . . ?
N1 C1 C2 C3 -64.3(4) . . . . ?
C4 N2 C3 C2 161.6(3) . . . . ?
Pb1 N2 C3 C2 -75.5(3) . . . . ?
C1 C2 C3 N2 72.5(4) . . . . ?
C3 N2 C4 C5 -179.4(2) . . . . ?
Pb1 N2 C4 C5 54.8(2) . . . . ?
N2 C4 C5 N1 -63.5(3) . . . 3_656 ?
C5 N1 C6 C7 -66.3(3) 3_656 . . . ?
C1 N1 C6 C7 58.5(3) . . . . ?
Pb1 N1 C6 C7 179.5(2) . . . . ?
N1 C6 C7 C12 -96.2(3) . . . . ?
N1 C6 C7 C8 86.0(3) . . . . ?
C12 C7 C8 C9 0.8(4) . . . . ?
C6 C7 C8 C9 178.6(3) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C8 C7 C12 C11 -1.4(5) . . . . ?
C6 C7 C12 C11 -179.2(3) . . . . ?
C10 C11 C12 C7 1.2(6) . . . . ?
N2 Pb1 O1 N3 -169.3(2) 3_656 . . . ?
N2 Pb1 O1 N3 -81.1(3) . . . . ?
N1 Pb1 O1 N3 -158.0(3) . . . . ?
N1 Pb1 O1 N3 -6.5(3) 3_656 . . . ?
O2 Pb1 O1 N3 -25.2(2) . . . . ?
N2 Pb1 O2 N3 168.0(2) 3_656 . . . ?
N2 Pb1 O2 N3 147.6(3) . . . . ?
N1 Pb1 O2 N3 76.0(3) . . . . ?
N1 Pb1 O2 N3 -140.3(2) 3_656 . . . ?
O1 Pb1 O2 N3 24.6(2) . . . . ?
Pb1 O1 N3 O3 -127.7(3) . . . . ?
Pb1 O1 N3 O2 49.8(3) . . . . ?
Pb1 O2 N3 O1 -52.0(4) . . . . ?
Pb1 O2 N3 O3 125.7(3) . . . . ?
