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#$Date: 2025-08-20 22:19:29 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301836 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/98/4309854.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_4309854
loop_
_publ_author_name
'François Cuenot'
'Michel Meyer'
'Enrique Espinosa'
'Roger Guilard'
_publ_contact_author
; Pr. Roger Guilard,
  LIMSAG, CNRS UMR 5633, 
  Université de Bourgogne, Faculté des Sciences, 
  6 boulevard Gabriel, 21100 Dijon, 
  France 
;
_publ_contact_author_email       Roger.Guilard@u-bourgogne.fr
_publ_contact_author_fax         '+33 3 80 39 61 17'
_publ_contact_author_phone       '+33 3 80 39 61 11'
_publ_section_title
;
Synthesis, Characterization, and X-ray Crystal Structures of Cyclam
Derivatives. 8. Thermodynamic and Kinetic Appraisal of Lead(II) Chelation
by Octadentate Carbamoyl-Armed Macrocycles1
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7895
_journal_page_last               7910
_journal_paper_doi               10.1021/ic0508019
_journal_volume                  44
_journal_year                    2005
_chemical_formula_moiety         'C18 H38 N8 O4, 2(N O3), 2(H2 O)'
_chemical_formula_sum            'C18 H42 N10 O12'
_chemical_formula_weight         590.62
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.904(2)
_cell_angle_beta                 108.550(2)
_cell_angle_gamma                111.047(2)
_cell_formula_units_Z            1
_cell_length_a                   8.5200(3)
_cell_length_b                   8.8830(3)
_cell_length_c                   10.6060(4)
_cell_measurement_reflns_used    5365
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.13
_cell_volume                     676.60(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5365
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0447P)²+0.2490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                2728
_reflns_number_total             3446
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0508019si20050804_090712_2.cif
_cod_data_source_block           ab126
_cod_database_code               4309854
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C2 C 0.68178(18) 0.33255(17) 0.51814(15) 0.0173(3) Uani 1 1 d . . .
C3 C 0.72693(19) 0.18135(17) 0.51815(15) 0.0185(3) Uani 1 1 d . . .
C4 C 0.89527(19) 0.19783(18) 0.48937(14) 0.0177(3) Uani 1 1 d . . .
C6 C 1.03763(18) 0.19517(17) 0.31759(15) 0.0183(3) Uani 1 1 d . . .
C7 C 1.20606(18) 0.36368(17) 0.39934(15) 0.0180(3) Uani 1 1 d . . .
C11 C 0.89376(19) 0.48491(18) 0.76071(14) 0.0172(3) Uani 1 1 d . . .
C12 C 1.08071(18) 0.48105(16) 0.81158(14) 0.0162(3) Uani 1 1 d . . .
C51 C 0.69489(18) 0.05844(17) 0.23085(14) 0.0162(3) Uani 1 1 d . . .
C52 C 0.66308(18) -0.11951(17) 0.23762(14) 0.0179(3) Uani 1 1 d . . .
N1 N 0.83598(15) 0.49211(14) 0.61677(11) 0.0155(2) Uani 1 1 d . . .
N5 N 0.87151(15) 0.19482(14) 0.34174(12) 0.0151(2) Uani 1 1 d . . .
N12 N 1.10573(19) 0.38774(17) 0.89466(14) 0.0232(3) Uani 1 1 d . . .
N52 N 0.49147(17) -0.23670(16) 0.16051(14) 0.0235(3) Uani 1 1 d . . .
O12 O 1.20344(13) 0.56802(12) 0.77852(10) 0.0193(2) Uani 1 1 d . . .
O52 O 0.78640(14) -0.15149(13) 0.30524(12) 0.0289(3) Uani 1 1 d . . .
H2A H 0.648(2) 0.347(2) 0.4243(18) 0.0243(9) Uiso 1 1 d . . .
H51B H 0.593(2) 0.080(2) 0.2377(17) 0.0243(9) Uiso 1 1 d . . .
H7A H 1.249(2) 0.375(2) 0.4985(18) 0.0243(9) Uiso 1 1 d . . .
H3A H 0.617(2) 0.077(2) 0.4519(18) 0.0243(9) Uiso 1 1 d . . .
H7B H 1.301(2) 0.361(2) 0.3661(17) 0.0243(9) Uiso 1 1 d . . .
H11B H 0.914(2) 0.590(2) 0.8287(18) 0.0243(9) Uiso 1 1 d . . .
H4A H 1.002(2) 0.307(2) 0.5499(18) 0.0243(9) Uiso 1 1 d . . .
H6B H 1.003(2) 0.172(2) 0.2176(19) 0.0243(9) Uiso 1 1 d . . .
H2B H 0.570(2) 0.307(2) 0.5376(17) 0.0243(9) Uiso 1 1 d . . .
H6A H 1.061(2) 0.103(2) 0.3474(17) 0.0243(9) Uiso 1 1 d . . .
H5 H 0.868(2) 0.298(2) 0.3274(18) 0.0243(9) Uiso 1 1 d . . .
H51A H 0.702(2) 0.066(2) 0.1411(18) 0.0243(9) Uiso 1 1 d . . .
H52A H 0.467(2) -0.342(2) 0.1584(17) 0.0243(9) Uiso 1 1 d . . .
H52B H 0.401(2) -0.211(2) 0.1129(18) 0.0243(9) Uiso 1 1 d . . .
H3B H 0.754(2) 0.165(2) 0.6113(18) 0.0243(9) Uiso 1 1 d . . .
H11A H 0.796(2) 0.381(2) 0.7684(17) 0.0243(9) Uiso 1 1 d . . .
H12A H 1.013(2) 0.319(2) 0.9088(18) 0.0243(9) Uiso 1 1 d . . .
H4B H 0.927(2) 0.104(2) 0.5056(17) 0.0243(9) Uiso 1 1 d . . .
H12B H 1.205(3) 0.379(2) 0.9242(18) 0.0243(9) Uiso 1 1 d . . .
N8 N 0.22078(15) 0.99411(14) 0.09657(12) 0.0181(2) Uani 1 1 d . . .
O9 O 0.17469(14) 0.84098(12) 0.03264(10) 0.0218(2) Uani 1 1 d . . .
O10 O 0.28424(15) 1.04331(14) 0.22594(11) 0.0272(3) Uani 1 1 d . . .
O11 O 0.20373(15) 1.09236(13) 0.02636(11) 0.0277(3) Uani 1 1 d . . .
OW O 0.45077(16) 0.43138(14) 0.16276(14) 0.0319(3) Uani 1 1 d . . .
HW1 H 0.378(3) 0.328(2) 0.1329(18) 0.0243(9) Uiso 1 1 d . . .
HW2 H 0.556(3) 0.435(2) 0.1781(18) 0.0243(9) Uiso 1 1 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'
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
N1 C2 C3 112.89(11) . . ?
N1 C2 H2A 107.7(10) . . ?
C3 C2 H2A 110.6(10) . . ?
N1 C2 H2B 111.8(10) . . ?
C3 C2 H2B 108.3(10) . . ?
H2A C2 H2B 105.3(14) . . ?
C4 C3 C2 115.57(11) . . ?
C4 C3 H3A 110.8(9) . . ?
C2 C3 H3A 109.4(10) . . ?
C4 C3 H3B 105.1(10) . . ?
C2 C3 H3B 109.3(10) . . ?
H3A C3 H3B 106.2(14) . . ?
N5 C4 C3 114.11(11) . . ?
N5 C4 H4A 105.7(10) . . ?
C3 C4 H4A 110.6(10) . . ?
N5 C4 H4B 106.1(10) . . ?
C3 C4 H4B 111.0(10) . . ?
H4A C4 H4B 109.0(14) . . ?
N5 C6 C7 111.27(11) . . ?
N5 C6 H6B 106.1(10) . . ?
C7 C6 H6B 111.6(10) . . ?
N5 C6 H6A 107.6(9) . . ?
C7 C6 H6A 110.2(10) . . ?
H6B C6 H6A 109.9(14) . . ?
N1 C7 C6 111.86(11) 2_766 . ?
N1 C7 H7A 106.7(10) 2_766 . ?
C6 C7 H7A 109.8(10) . . ?
N1 C7 H7B 113.0(10) 2_766 . ?
C6 C7 H7B 106.1(10) . . ?
H7A C7 H7B 109.4(14) . . ?
N1 C11 C12 111.16(10) . . ?
N1 C11 H11B 111.9(10) . . ?
C12 C11 H11B 104.0(10) . . ?
N1 C11 H11A 110.4(9) . . ?
C12 C11 H11A 110.7(9) . . ?
H11B C11 H11A 108.6(13) . . ?
O12 C12 N12 122.96(13) . . ?
O12 C12 C11 120.10(12) . . ?
N12 C12 C11 116.89(12) . . ?
N5 C51 C52 113.96(11) . . ?
N5 C51 H51B 109.0(10) . . ?
C52 C51 H51B 109.4(10) . . ?
N5 C51 H51A 106.3(10) . . ?
C52 C51 H51A 108.0(10) . . ?
H51B C51 H51A 110.1(14) . . ?
O52 C52 N52 123.41(13) . . ?
O52 C52 C51 122.51(12) . . ?
N52 C52 C51 114.05(12) . . ?
C11 N1 C7 113.45(11) . 2_766 ?
C11 N1 C2 111.97(11) . . ?
C7 N1 C2 110.76(10) 2_766 . ?
C51 N5 C4 114.96(10) . . ?
C51 N5 C6 112.16(10) . . ?
C4 N5 C6 110.93(10) . . ?
C51 N5 H5 104.1(10) . . ?
C4 N5 H5 109.5(10) . . ?
C6 N5 H5 104.4(10) . . ?
C12 N12 H12A 120.7(11) . . ?
C12 N12 H12B 120.9(12) . . ?
H12A N12 H12B 117.6(16) . . ?
C52 N52 H52A 117.6(11) . . ?
C52 N52 H52B 122.5(11) . . ?
H52A N52 H52B 119.9(15) . . ?
O10 N8 O11 121.48(12) . . ?
O10 N8 O9 119.91(11) . . ?
O11 N8 O9 118.60(11) . . ?
HW1 OW HW2 105.1(16) . . ?
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
C2 N1 1.4692(17) . ?
C2 C3 1.5242(19) . ?
C2 H2A 0.987(17) . ?
C2 H2B 0.993(17) . ?
C3 C4 1.5209(19) . ?
C3 H3A 0.993(18) . ?
C3 H3B 0.987(17) . ?
C4 N5 1.5082(17) . ?
C4 H4A 0.989(18) . ?
C4 H4B 0.987(17) . ?
C6 N5 1.5154(16) . ?
C6 C7 1.5216(19) . ?
C6 H6B 0.972(18) . ?
C6 H6A 0.983(17) . ?
C7 N1 1.4687(17) 2_766 ?
C7 H7A 0.973(17) . ?
C7 H7B 0.985(17) . ?
C11 N1 1.4668(17) . ?
C11 C12 1.5257(18) . ?
C11 H11B 1.012(17) . ?
C11 H11A 1.031(17) . ?
C12 O12 1.2450(16) . ?
C12 N12 1.3200(18) . ?
C51 N5 1.4962(17) . ?
C51 C52 1.5222(18) . ?
C51 H51B 0.977(17) . ?
C51 H51A 0.983(17) . ?
C52 O52 1.2235(17) . ?
C52 N52 1.3315(19) . ?
N1 C7 1.4687(17) 2_766 ?
N5 H5 0.963(17) . ?
N12 H12A 0.878(19) . ?
N12 H12B 0.837(18) . ?
N52 H52A 0.881(18) . ?
N52 H52B 0.901(19) . ?
N8 O10 1.2404(15) . ?
N8 O11 1.2493(15) . ?
N8 O9 1.2750(15) . ?
OW HW1 0.842(19) . ?
OW HW2 0.850(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
N5 H5 O12 0.963(17) 1.882(18) 2.7844(15) 154.9(15) 2_766
N5 H5 N1 0.963(17) 2.348(17) 2.8432(15) 111.3(12) 2_766
N52 H52A OW 0.881(18) 1.973(19) 2.8472(17) 171.6(16) 1_545
N52 H52B O9 0.901(19) 2.093(19) 2.9830(16) 169.1(15) 1_545
N12 H12A O9 0.878(19) 2.061(19) 2.9327(17) 171.6(16) 2_666
N12 H12B OW 0.837(18) 2.564(18) 3.2248(18) 136.7(15) 1_656
OW HW1 O11 0.842(19) 1.955(19) 2.7845(16) 168.4(16) 1_545
OW HW1 N8 0.842(19) 2.681(19) 3.4977(16) 163.9(16) 1_545
OW HW2 O12 0.850(19) 1.960(19) 2.8085(15) 176.0(16) 2_766
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
N1 C2 C3 C4 -55.87(16) . . . . ?
C2 C3 C4 N5 -69.10(15) . . . . ?
N5 C6 C7 N1 -47.03(15) . . . 2_766 ?
N1 C11 C12 O12 38.56(17) . . . . ?
N1 C11 C12 N12 -143.92(12) . . . . ?
N5 C51 C52 O52 -15.85(19) . . . . ?
N5 C51 C52 N52 166.04(12) . . . . ?
C12 C11 N1 C7 -124.36(12) . . . 2_766 ?
C12 C11 N1 C2 109.36(12) . . . . ?
C3 C2 N1 C11 -59.22(14) . . . . ?
C3 C2 N1 C7 173.05(11) . . . 2_766 ?
C52 C51 N5 C4 -56.88(14) . . . . ?
C52 C51 N5 C6 71.08(14) . . . . ?
C3 C4 N5 C51 -46.09(15) . . . . ?
C3 C4 N5 C6 -174.67(11) . . . . ?
C7 C6 N5 C51 161.25(11) . . . . ?
C7 C6 N5 C4 -68.68(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139129818
