#------------------------------------------------------------------------------
#$Date: 2019-11-23 00:58:26 +0200 (Sat, 23 Nov 2019) $
#$Revision: 231722 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/63/4346302.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_4346302
loop_
_publ_author_name
'Boiocchi, Massimo'
'Ciarrocchi, Carlo'
'Fabbrizzi, Luigi'
'Licchelli, Maurizio'
'Mangano, Carlo'
'Poggi, Antonio'
'Vázquez López, Miguel'
_publ_contact_author
;
  Luigi Fabbrizzi
  Dipartimento di Chimica 
  University of Pavia
  via Taramelli 12, I-27100 Pavia, ITALY
;
_publ_section_title
;
 Copper(II) Complexes of Cyclams Containing Nitrophenyl Substituents:
 Push-Pull Behavior and Scorpionate Coordination of the Nitro Group.
;
_journal_issue                   21
_journal_name_full               'Inorganic chemistry'
_journal_page_first              10197
_journal_page_last               10207
_journal_paper_doi               10.1021/acs.inorgchem.5b01273
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C16 H27 Cu N5 O2, 2 (C N O), 2 (H2 O)'
_chemical_formula_sum            'C18 H31 Cu N7 O6'
_chemical_formula_weight         505.04
_chemical_name_common
;
trans-III-(RRSS)-(1-(4-nitrophenyl)-1,4,8,11-tetra-azacyclotetradecane)
-copper(ii) dicyanate dihydrate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                93.02(3)
_cell_angle_beta                 109.01(2)
_cell_angle_gamma                106.69(3)
_cell_formula_units_Z            2
_cell_length_a                   9.094(3)
_cell_length_b                   11.082(2)
_cell_length_c                   12.948(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      7
_cell_volume                     1166.2(6)
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4317
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.895
_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            BLUE
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'PLATY PRISM'
_exptl_crystal_F_000             530
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+1.3153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                3534
_reflns_number_total             4111
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic5b01273_si_002.cif
_cod_data_source_block           TRANS_III_CuII(2)_2(NCO)_2(H2O)
_cod_original_cell_volume        1166.3(6)
_cod_database_code               4346302
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_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
Cu1 Cu 0.49205(6) 0.26936(4) 0.27085(4) 0.04487(18) Uani 1 1 d . . . . .
C1 C 0.3293(11) 0.1648(6) 0.4111(6) 0.106(3) Uani 1 1 d . . . . .
H1A H 0.3218 0.2472 0.4331 0.127 Uiso 1 1 calc R U . . .
H1B H 0.2539 0.0997 0.4334 0.127 Uiso 1 1 calc R U . . .
C2 C 0.5021(13) 0.1630(6) 0.4654(5) 0.121(3) Uani 1 1 d . . . . .
H2A H 0.5356 0.1835 0.5451 0.146 Uiso 1 1 calc R U . . .
H2B H 0.5070 0.0784 0.4478 0.146 Uiso 1 1 calc R U . . .
C3 C 0.7788(11) 0.2391(8) 0.4547(6) 0.122(3) Uani 1 1 d . . . . .
H3A H 0.7657 0.1536 0.4234 0.147 Uiso 1 1 calc R U . . .
H3B H 0.8291 0.2482 0.5345 0.147 Uiso 1 1 calc R U . . .
C4 C 0.8927(9) 0.3351(8) 0.4122(9) 0.143(4) Uani 1 1 d . . . . .
H4A H 0.8987 0.4202 0.4397 0.171 Uiso 1 1 calc R U . . .
H4B H 1.0020 0.3284 0.4433 0.171 Uiso 1 1 calc R U . . .
C5 C 0.8456(8) 0.3213(7) 0.2914(8) 0.120(3) Uani 1 1 d . . . . .
H5A H 0.9356 0.3754 0.2734 0.144 Uiso 1 1 calc R U . . .
H5B H 0.8270 0.2336 0.2621 0.144 Uiso 1 1 calc R U . . .
C6 C 0.6506(10) 0.3424(6) 0.1159(6) 0.104(2) Uani 1 1 d . . . . .
H6A H 0.7279 0.4095 0.0967 0.125 Uiso 1 1 calc R U . . .
H6B H 0.6516 0.2608 0.0857 0.125 Uiso 1 1 calc R U . . .
C7 C 0.4857(10) 0.3523(6) 0.0688(5) 0.095(2) Uani 1 1 d . . . . .
H7A H 0.4483 0.3373 -0.0114 0.114 Uiso 1 1 calc R U . . .
H7B H 0.4863 0.4369 0.0929 0.114 Uiso 1 1 calc R U . . .
C8 C 0.2121(8) 0.2667(6) 0.0727(5) 0.093(2) Uani 1 1 d . . . . .
H8A H 0.1693 0.2603 -0.0072 0.112 Uiso 1 1 calc R U . . .
H8B H 0.2180 0.3498 0.1048 0.112 Uiso 1 1 calc R U . . .
C9 C 0.0986(7) 0.1659(6) 0.1069(7) 0.106(3) Uani 1 1 d . . . . .
H9A H 0.1005 0.0835 0.0794 0.128 Uiso 1 1 calc R U . . .
H9B H -0.0121 0.1686 0.0720 0.128 Uiso 1 1 calc R U . . .
C10 C 0.1371(7) 0.1764(5) 0.2292(7) 0.096(2) Uani 1 1 d . . . . .
H10A H 0.0433 0.1216 0.2430 0.115 Uiso 1 1 calc R U . . .
H10B H 0.1551 0.2636 0.2594 0.115 Uiso 1 1 calc R U . . .
C11 C 0.2581(5) 0.0047(4) 0.2521(4) 0.0512(10) Uani 1 1 d . . . . .
C12 C 0.1209(6) -0.0896(5) 0.2535(5) 0.0734(15) Uani 1 1 d . . . . .
H12 H 0.0461 -0.0671 0.2787 0.088 Uiso 1 1 calc R U . . .
C13 C 0.0934(6) -0.2161(5) 0.2182(4) 0.0660(13) Uani 1 1 d . . . . .
H13 H 0.0005 -0.2790 0.2187 0.079 Uiso 1 1 calc R U . . .
C14 C 0.2055(5) -0.2475(4) 0.1825(3) 0.0518(10) Uani 1 1 d . . . . .
C15 C 0.3440(6) -0.1573(4) 0.1827(4) 0.0568(11) Uani 1 1 d . . . . .
H15 H 0.4199 -0.1807 0.1594 0.068 Uiso 1 1 calc R U . . .
C16 C 0.3698(5) -0.0299(4) 0.2184(4) 0.0555(11) Uani 1 1 d . . . . .
H16 H 0.4642 0.0324 0.2193 0.067 Uiso 1 1 calc R U . . .
N1 N 0.2858(5) 0.1396(3) 0.2876(3) 0.0569(9) Uani 1 1 d . . . . .
N2 N 0.6119(7) 0.2550(4) 0.4266(4) 0.0793(14) Uani 1 1 d D . . . .
H2N H 0.617(7) 0.330(3) 0.459(4) 0.095 Uiso 1 1 d D U . . .
N3 N 0.7000(5) 0.3545(4) 0.2386(5) 0.0791(14) Uani 1 1 d D . . . .
H3N H 0.716(7) 0.436(2) 0.264(4) 0.095 Uiso 1 1 d D U . . .
N4 N 0.3768(6) 0.2559(4) 0.1075(3) 0.0639(10) Uani 1 1 d D . . . .
H4N H 0.374(6) 0.180(2) 0.078(4) 0.077 Uiso 1 1 d D U . . .
N5 N 0.1764(6) -0.3816(4) 0.1406(3) 0.0623(10) Uani 1 1 d . . . . .
O1 O 0.0486(5) -0.4602(3) 0.1362(4) 0.0955(13) Uani 1 1 d . . . . .
O2 O 0.2800(6) -0.4071(3) 0.1120(4) 0.0882(12) Uani 1 1 d . . . . .
C17 C 0.3822(7) 0.4989(5) 0.3527(4) 0.0653(13) Uani 1 1 d D . . . .
N6 N 0.4554(6) 0.4448(4) 0.3234(4) 0.0746(12) Uani 1 1 d D . . . .
O3 O 0.3035(6) 0.5539(5) 0.3816(4) 0.1109(16) Uani 1 1 d D . . . .
C18A C -0.3162(15) -0.0164(14) 0.1094(10) 0.063(4) Uani 0.5 1 d D . P A 1
N7A N -0.390(2) -0.031(2) 0.0165(11) 0.098(5) Uani 0.5 1 d D . P A 1
O4A O -0.2454(12) 0.0069(10) 0.2072(10) 0.118(4) Uani 0.5 1 d D . P A 1
C18B C -0.1554(17) -0.0497(17) 0.3699(14) 0.098(8) Uani 0.5 1 d D . P B 2
N7B N -0.071(2) -0.031(3) 0.4615(13) 0.175(11) Uani 0.5 1 d D . P B 2
O4B O -0.2478(16) -0.0826(19) 0.2773(14) 0.179(7) Uani 0.5 1 d D . P B 2
O1W O 0.7370(11) 0.6326(6) 0.2908(11) 0.210(4) Uani 1 1 d D . . . .
H1WA H 0.730(18) 0.627(13) 0.358(5) 0.252 Uiso 1 1 d D U . . .
H1WB H 0.721(15) 0.708(6) 0.281(11) 0.252 Uiso 1 1 d D U . . .
O2WA O -0.189(2) -0.1181(14) 0.3846(12) 0.139(6) Uani 0.5 1 d . . P C 1
O2WB O -0.325(2) -0.0359(16) 0.0582(11) 0.083(4) Uani 0.5 1 d . . P D 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'
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_3
N2 Cu1 N4 170.36(16) .
N2 Cu1 N3 94.7(2) .
N4 Cu1 N3 84.6(2) .
N2 Cu1 N1 86.0(2) .
N4 Cu1 N1 92.29(17) .
N3 Cu1 N1 165.35(15) .
N2 Cu1 N6 91.94(17) .
N4 Cu1 N6 97.69(16) .
N3 Cu1 N6 96.47(18) .
N1 Cu1 N6 98.13(16) .
C2 C1 N1 108.0(5) .
C2 C1 H1A 110.1 .
N1 C1 H1A 110.1 .
C2 C1 H1B 110.1 .
N1 C1 H1B 110.1 .
H1A C1 H1B 108.4 .
N2 C2 C1 109.6(5) .
N2 C2 H2A 109.7 .
C1 C2 H2A 109.7 .
N2 C2 H2B 109.7 .
C1 C2 H2B 109.7 .
H2A C2 H2B 108.2 .
N2 C3 C4 113.0(6) .
N2 C3 H3A 109.0 .
C4 C3 H3A 109.0 .
N2 C3 H3B 109.0 .
C4 C3 H3B 109.0 .
H3A C3 H3B 107.8 .
C5 C4 C3 115.7(6) .
C5 C4 H4A 108.4 .
C3 C4 H4A 108.4 .
C5 C4 H4B 108.4 .
C3 C4 H4B 108.4 .
H4A C4 H4B 107.4 .
N3 C5 C4 112.8(6) .
N3 C5 H5A 109.0 .
C4 C5 H5A 109.0 .
N3 C5 H5B 109.0 .
C4 C5 H5B 109.0 .
H5A C5 H5B 107.8 .
C7 C6 N3 109.4(5) .
C7 C6 H6A 109.8 .
N3 C6 H6A 109.8 .
C7 C6 H6B 109.8 .
N3 C6 H6B 109.8 .
H6A C6 H6B 108.3 .
C6 C7 N4 107.6(5) .
C6 C7 H7A 110.2 .
N4 C7 H7A 110.2 .
C6 C7 H7B 110.2 .
N4 C7 H7B 110.2 .
H7A C7 H7B 108.5 .
N4 C8 C9 111.8(4) .
N4 C8 H8A 109.3 .
C9 C8 H8A 109.3 .
N4 C8 H8B 109.3 .
C9 C8 H8B 109.3 .
H8A C8 H8B 107.9 .
C8 C9 C10 114.8(5) .
C8 C9 H9A 108.6 .
C10 C9 H9A 108.6 .
C8 C9 H9B 108.6 .
C10 C9 H9B 108.6 .
H9A C9 H9B 107.5 .
C9 C10 N1 112.7(4) .
C9 C10 H10A 109.1 .
N1 C10 H10A 109.1 .
C9 C10 H10B 109.1 .
N1 C10 H10B 109.1 .
H10A C10 H10B 107.8 .
C16 C11 C12 118.9(4) .
C16 C11 N1 119.9(4) .
C12 C11 N1 121.1(4) .
C13 C12 C11 121.1(4) .
C13 C12 H12 119.5 .
C11 C12 H12 119.5 .
C14 C13 C12 118.6(4) .
C14 C13 H13 120.7 .
C12 C13 H13 120.7 .
C15 C14 C13 121.8(4) .
C15 C14 N5 118.4(4) .
C13 C14 N5 119.8(4) .
C14 C15 C16 118.9(4) .
C14 C15 H15 120.6 .
C16 C15 H15 120.6 .
C11 C16 C15 120.6(4) .
C11 C16 H16 119.7 .
C15 C16 H16 119.7 .
C11 N1 C10 111.0(4) .
C11 N1 C1 109.5(4) .
C10 N1 C1 110.5(5) .
C11 N1 Cu1 115.7(2) .
C10 N1 Cu1 109.0(3) .
C1 N1 Cu1 100.7(3) .
C2 N2 C3 113.4(6) .
C2 N2 Cu1 109.3(4) .
C3 N2 Cu1 118.6(4) .
C2 N2 H2N 104(4) .
C3 N2 H2N 112(4) .
Cu1 N2 H2N 98(4) .
C5 N3 C6 113.8(6) .
C5 N3 Cu1 119.1(5) .
C6 N3 Cu1 106.7(4) .
C5 N3 H3N 110(4) .
C6 N3 H3N 107(4) .
Cu1 N3 H3N 98(4) .
C8 N4 C7 111.3(5) .
C8 N4 Cu1 116.4(4) .
C7 N4 Cu1 106.9(4) .
C8 N4 H4N 110(3) .
C7 N4 H4N 107(3) .
Cu1 N4 H4N 105(3) .
O2 N5 O1 124.0(4) .
O2 N5 C14 118.4(4) .
O1 N5 C14 117.6(5) .
N6 C17 O3 178.8(6) .
C17 N6 Cu1 151.9(5) .
N7A C18A O4A 174.1(17) .
N7B C18B O4B 173(3) .
C18B N7B N7B 149(3) 2_556
H1WA O1W H1WB 100(10) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.995(4) .
Cu1 N4 2.007(4) .
Cu1 N3 2.042(4) .
Cu1 N1 2.093(4) .
Cu1 N6 2.176(4) .
C1 C2 1.505(10) .
C1 N1 1.507(7) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 N2 1.444(9) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 N2 1.506(9) .
C3 C4 1.519(12) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.468(12) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 N3 1.440(8) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.462(10) .
C6 N3 1.492(8) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 N4 1.464(7) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 N4 1.459(7) .
C8 C9 1.482(9) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.496(10) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 N1 1.500(7) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C16 1.366(6) .
C11 C12 1.384(6) .
C11 N1 1.466(5) .
C12 C13 1.376(7) .
C12 H12 0.9300 .
C13 C14 1.367(6) .
C13 H13 0.9300 .
C14 C15 1.363(6) .
C14 N5 1.473(6) .
C15 C16 1.391(6) .
C15 H15 0.9300 .
C16 H16 0.9300 .
N2 H2N 0.894(10) .
N3 H3N 0.896(10) .
N4 H4N 0.898(10) .
N5 O2 1.214(5) .
N5 O1 1.217(5) .
C17 N6 1.148(6) .
C17 O3 1.194(6) .
C18A N7A 1.146(10) .
C18A O4A 1.194(9) .
C18B N7B 1.154(10) .
C18B O4B 1.182(10) .
N7B N7B 1.30(4) 2_556
O1W H1WA 0.900(10) .
O1W H1WB 0.900(10) .
