#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:03:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179522 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/19/4341984.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_4341984
loop_
_publ_author_name
'Boiocchi, Massimo'
'Licchelli, Maurizio'
'Milani, Michele'
'Poggi, Antonio'
'Sacchi, Donatella'
_publ_contact_author
;
  Maurizio Licchelli
  Dipartimento di Chimica Generale
  University of Pavia
  via Taramelli 12, I-27100 Pavia, ITALY
;
_publ_section_title
;
 Oxo-anion recognition by mono- and bisurea pendant-arm macrocyclic
 complexes.
;
_journal_issue                   1
_journal_name_full               'Inorganic chemistry'
_journal_page_first              47
_journal_page_last               58
_journal_paper_doi               10.1021/ic501527k
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C26 H40 Cu N12 O6, 2 (Cl O4)'
_chemical_formula_sum            'C26 H40 Cl2 Cu N12 O14'
_chemical_formula_weight         879.15
_chemical_name_common
;
(3,10-bis(2-(3-(4-nitrophenyl)urea)ethyl)-1,3,5,8,10,12-hexa-
azacyclotetradecane)-copper(ii) diperchlorate
;
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                76.59(5)
_cell_angle_beta                 75.01(5)
_cell_angle_gamma                68.05(4)
_cell_formula_units_Z            1
_cell_length_a                   8.153(4)
_cell_length_b                   9.129(6)
_cell_length_c                   13.618(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      5
_cell_volume                     897.7(9)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_molecular_graphics    'MERCURY (Macrae et al.2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0785
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3415
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             455
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3162
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0837
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+3.6059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1743
_refine_ls_wR_factor_ref         0.2039
_reflns_number_gt                2321
_reflns_number_total             3162
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic501527k_si_002.cif
_cod_data_source_block           '[3]_ClO4'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'PSI-SCAN' changed to
'psi-scan' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4341984--4341986.cif.
;
_cod_database_code               4341984
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
Cu1 Cu 0.0000 0.5000 0.5000 0.0378(3) Uani 1 2 d S
C1 C -0.2559(10) 0.5280(9) 0.6865(6) 0.0491(18) Uani 1 1 d .
H1A H -0.3590 0.6030 0.6580 0.059 Uiso 1 1 calc R
H1B H -0.2825 0.5280 0.7602 0.059 Uiso 1 1 calc R
C2 C -0.1234(10) 0.7447(8) 0.6395(6) 0.0491(18) Uani 1 1 d .
H2A H -0.2263 0.8098 0.6077 0.059 Uiso 1 1 calc R
H2B H -0.1540 0.7625 0.7104 0.059 Uiso 1 1 calc R
C3 C 0.0766(10) 0.7966(8) 0.4799(6) 0.0473(17) Uani 1 1 d .
H3A H 0.1611 0.8543 0.4516 0.057 Uiso 1 1 calc R
H3B H -0.0296 0.8535 0.4495 0.057 Uiso 1 1 calc R
C4 C 0.2164(10) 0.6363(9) 0.3361(5) 0.0489(18) Uani 1 1 d .
H4A H 0.3228 0.6678 0.3111 0.059 Uiso 1 1 calc R
H4B H 0.1207 0.7127 0.3020 0.059 Uiso 1 1 calc R
C5 C 0.1736(10) 0.7597(10) 0.6419(6) 0.057(2) Uani 1 1 d .
H5A H 0.2709 0.7907 0.5950 0.069 Uiso 1 1 calc R
H5B H 0.2188 0.6451 0.6633 0.069 Uiso 1 1 calc R
C6 C 0.1171(10) 0.8427(10) 0.7352(6) 0.056(2) Uani 1 1 d .
H6A H 0.0174 0.9409 0.7249 0.067 Uiso 1 1 calc R
H6B H 0.0756 0.7747 0.7949 0.067 Uiso 1 1 calc R
C7 C 0.3481(11) 0.8075(9) 0.8336(6) 0.0520(19) Uani 1 1 d .
C8 C 0.5843(10) 0.8263(9) 0.9102(5) 0.0497(18) Uani 1 1 d .
C9 C 0.6155(13) 0.6833(11) 0.9754(7) 0.070(2) Uani 1 1 d .
H9 H 0.5558 0.6140 0.9758 0.084 Uiso 1 1 calc R
C10 C 0.7358(14) 0.6429(12) 1.0403(7) 0.078(3) Uani 1 1 d .
H10 H 0.7556 0.5469 1.0852 0.093 Uiso 1 1 calc R
C11 C 0.8266(11) 0.7441(12) 1.0388(6) 0.064(2) Uani 1 1 d .
C12 C 0.7985(11) 0.8871(11) 0.9741(6) 0.063(2) Uani 1 1 d .
H12 H 0.8582 0.9561 0.9745 0.075 Uiso 1 1 calc R
C13 C 0.6795(11) 0.9267(10) 0.9083(6) 0.058(2) Uani 1 1 d .
H13 H 0.6627 1.0214 0.8621 0.070 Uiso 1 1 calc R
N1 N -0.0920(8) 0.5738(7) 0.6381(4) 0.0415(13) Uani 1 1 d D
H1N H 0.003(6) 0.514(7) 0.675(5) 0.050 Uiso 1 1 d D
N2 N 0.0261(8) 0.7978(7) 0.5880(5) 0.0474(15) Uani 1 1 d .
N3 N 0.1605(7) 0.6330(7) 0.4492(4) 0.0387(13) Uani 1 1 d D
H3N H 0.272(5) 0.585(7) 0.473(5) 0.046 Uiso 1 1 d D
N4 N 0.2631(11) 0.8793(9) 0.7545(6) 0.073(2) Uani 1 1 d D
H4N H 0.277(12) 0.976(6) 0.714(6) 0.088 Uiso 1 1 d D
N5 N 0.4681(10) 0.8773(8) 0.8403(5) 0.0579(17) Uani 1 1 d D
H5N H 0.444(11) 0.983(4) 0.803(5) 0.070 Uiso 1 1 d D
N6 N 0.9534(12) 0.6975(13) 1.1079(6) 0.085(3) Uani 1 1 d .
O1 O 0.3251(11) 0.6927(9) 0.8886(6) 0.101(3) Uani 1 1 d .
O2 O 0.9906(12) 0.5606(11) 1.1559(6) 0.114(3) Uani 1 1 d .
O3 O 1.0108(11) 0.7980(12) 1.1175(6) 0.112(3) Uani 1 1 d .
Cl1 Cl 0.3970(2) 0.2374(2) 0.61291(16) 0.0565(5) Uani 1 1 d .
O4 O 0.5165(13) 0.0987(11) 0.6017(16) 0.256(10) Uani 1 1 d .
O5 O 0.391(3) 0.232(3) 0.7115(9) 0.287(12) Uani 1 1 d .
O6 O 0.2320(10) 0.2504(9) 0.6005(8) 0.129(3) Uani 1 1 d .
O7 O 0.4555(9) 0.3622(8) 0.5554(6) 0.094(2) Uani 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
N3 Cu1 N3 180.000(1) 2_566 .
N3 Cu1 N1 94.0(2) 2_566 2_566
N3 Cu1 N1 86.0(2) . 2_566
N3 Cu1 N1 86.0(2) 2_566 .
N3 Cu1 N1 94.0(2) . .
N1 Cu1 N1 180.000(1) 2_566 .
N1 C1 C4 107.0(6) . 2_566
N1 C1 H1A 110.3 . .
C4 C1 H1A 110.3 2_566 .
N1 C1 H1B 110.3 . .
C4 C1 H1B 110.3 2_566 .
H1A C1 H1B 108.6 . .
N2 C2 N1 114.9(6) . .
N2 C2 H2A 108.5 . .
N1 C2 H2A 108.5 . .
N2 C2 H2B 108.5 . .
N1 C2 H2B 108.5 . .
H2A C2 H2B 107.5 . .
N2 C3 N3 114.5(6) . .
N2 C3 H3A 108.6 . .
N3 C3 H3A 108.6 . .
N2 C3 H3B 108.6 . .
N3 C3 H3B 108.6 . .
H3A C3 H3B 107.6 . .
N3 C4 C1 108.1(6) . 2_566
N3 C4 H4A 110.1 . .
C1 C4 H4A 110.1 2_566 .
N3 C4 H4B 110.1 . .
C1 C4 H4B 110.1 2_566 .
H4A C4 H4B 108.4 . .
N2 C5 C6 112.7(6) . .
N2 C5 H5A 109.1 . .
C6 C5 H5A 109.1 . .
N2 C5 H5B 109.1 . .
C6 C5 H5B 109.1 . .
H5A C5 H5B 107.8 . .
N4 C6 C5 112.1(7) . .
N4 C6 H6A 109.2 . .
C5 C6 H6A 109.2 . .
N4 C6 H6B 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
O1 C7 N4 122.3(8) . .
O1 C7 N5 124.8(8) . .
N4 C7 N5 112.9(7) . .
C9 C8 N5 124.4(7) . .
C9 C8 C13 119.3(8) . .
N5 C8 C13 116.2(7) . .
C8 C9 C10 119.8(9) . .
C8 C9 H9 120.1 . .
C10 C9 H9 120.1 . .
C11 C10 C9 120.3(9) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C12 C11 C10 121.1(8) . .
C12 C11 N6 120.0(9) . .
C10 C11 N6 118.9(9) . .
C11 C12 C13 118.6(8) . .
C11 C12 H12 120.7 . .
C13 C12 H12 120.7 . .
C12 C13 C8 120.9(8) . .
C12 C13 H13 119.6 . .
C8 C13 H13 119.6 . .
C2 N1 C1 112.5(6) . .
C2 N1 Cu1 116.5(5) . .
C1 N1 Cu1 107.1(4) . .
C2 N1 H1N 106(4) . .
C1 N1 H1N 110(4) . .
Cu1 N1 H1N 104(4) . .
C3 N2 C2 116.0(6) . .
C3 N2 C5 115.7(6) . .
C2 N2 C5 118.4(6) . .
C4 N3 C3 113.0(6) . .
C4 N3 Cu1 107.2(4) . .
C3 N3 Cu1 113.4(4) . .
C4 N3 H3N 104(4) . .
C3 N3 H3N 107(4) . .
Cu1 N3 H3N 113(4) . .
C7 N4 C6 124.8(7) . .
C7 N4 H4N 121(6) . .
C6 N4 H4N 113(6) . .
C7 N5 C8 127.2(7) . .
C7 N5 H5N 112(5) . .
C8 N5 H5N 119(5) . .
O3 N6 O2 124.1(9) . .
O3 N6 C11 118.0(10) . .
O2 N6 C11 117.9(10) . .
O4 Cl1 O5 98.1(12) . .
O4 Cl1 O6 113.6(8) . .
O5 Cl1 O6 108.7(9) . .
O4 Cl1 O7 112.8(6) . .
O5 Cl1 O7 109.5(8) . .
O6 Cl1 O7 113.1(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N3 1.999(5) 2_566
Cu1 N3 1.999(5) .
Cu1 N1 2.009(6) 2_566
Cu1 N1 2.009(6) .
C1 N1 1.494(9) .
C1 C4 1.499(10) 2_566
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 N2 1.433(9) .
C2 N1 1.487(8) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 N2 1.424(9) .
C3 N3 1.500(9) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 N3 1.486(8) .
C4 C1 1.499(10) 2_566
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 N2 1.460(9) .
C5 C6 1.510(10) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 N4 1.449(10) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 O1 1.185(9) .
C7 N4 1.337(10) .
C7 N5 1.383(9) .
C8 C9 1.374(11) .
C8 N5 1.397(9) .
C8 C13 1.398(10) .
C9 C10 1.380(12) .
C9 H9 0.9300 .
C10 C11 1.377(12) .
C10 H10 0.9300 .
C11 C12 1.371(12) .
C11 N6 1.458(11) .
C12 C13 1.383(11) .
C12 H12 0.9300 .
C13 H13 0.9300 .
N1 H1N 0.959(10) .
N3 H3N 0.956(10) .
N4 H4N 0.958(10) .
N5 H5N 0.956(10) .
N6 O3 1.219(11) .
N6 O2 1.234(11) .
Cl1 O4 1.291(9) .
Cl1 O5 1.322(12) .
Cl1 O6 1.357(7) .
Cl1 O7 1.392(6) .
