#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/76/1517648.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_1517648
loop_
_publ_author_name
'Ying-Ying Liu'
'Jie Liu'
'Jin Yang'
'Bo Liu'
'Jian-Fang Ma'
_publ_section_title
;
 Eight coordination compounds based on a reduced Schiff base
 tetraaminodiphenol macrocyclic ligand
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              85
_journal_page_last               96
_journal_volume                  403
_journal_year                    2013
_chemical_formula_sum            'C30 H48 Cu2 N4 O24'
_chemical_formula_weight         975.80
_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
_cell_angle_alpha                117.721(2)
_cell_angle_beta                 102.109(2)
_cell_angle_gamma                102.6000(10)
_cell_formula_units_Z            1
_cell_length_a                   10.0490(12)
_cell_length_b                   10.8530(11)
_cell_length_c                   11.1940(13)
_cell_measurement_temperature    293(2)
_cell_volume                     983.86(19)
_computing_cell_refinement       CrysAlis
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2006)'
_computing_data_reduction        CrysAlis
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6042
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    1.178
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis (Oxford Diffraction, 2006)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4371
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0727P)²+0.6444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1424
_reflns_number_gt                3610
_reflns_number_total             4371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-403-85-96-2.cif
_cod_data_source_block           2
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               1517648
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 0.49965(4) 0.36324(4) 0.03753(4) 0.02997(14) Uani 1 1 d .
C1 C -0.3777(4) 0.1725(5) 0.2508(4) 0.0452(9) Uani 1 1 d .
H1A H -0.3433 0.1968 0.3486 0.068 Uiso 1 1 calc R
H1B H -0.4258 0.0662 0.1863 0.068 Uiso 1 1 calc R
H1C H -0.4454 0.2205 0.2409 0.068 Uiso 1 1 calc R
C2 C -0.2500(3) 0.2261(4) 0.2140(4) 0.0313(7) Uani 1 1 d .
C3 C -0.2680(3) 0.2064(3) 0.0797(3) 0.0303(6) Uani 1 1 d .
H3 H -0.3612 0.1541 0.0090 0.036 Uiso 1 1 calc R
C4 C -0.1524(3) 0.2615(3) 0.0449(3) 0.0282(6) Uani 1 1 d .
C5 C -0.0129(3) 0.3420(3) 0.1519(3) 0.0271(6) Uani 1 1 d .
C6 C 0.0099(3) 0.3538(3) 0.2853(3) 0.0274(6) Uani 1 1 d .
C7 C -0.1075(4) 0.2976(3) 0.3153(3) 0.0307(6) Uani 1 1 d .
H7 H -0.0911 0.3076 0.4049 0.037 Uiso 1 1 calc R
C8 C 0.1639(3) 0.4159(4) 0.3885(3) 0.0305(6) Uani 1 1 d .
H8A H 0.1629 0.4337 0.4816 0.037 Uiso 1 1 calc R
H8B H 0.2167 0.5106 0.4024 0.037 Uiso 1 1 calc R
C9 C 0.1631(4) 0.1600(4) 0.3064(4) 0.0346(7) Uani 1 1 d .
H9A H 0.0618 0.1218 0.2445 0.042 Uiso 1 1 calc R
H9B H 0.1646 0.1728 0.3985 0.042 Uiso 1 1 calc R
C10 C 0.2328(3) 0.0478(4) 0.2376(3) 0.0318(7) Uani 1 1 d .
H10A H 0.2458 0.0454 0.1532 0.038 Uiso 1 1 calc R
H10B H 0.3280 0.0756 0.3058 0.038 Uiso 1 1 calc R
C11 C 0.1800(3) -0.2291(4) 0.1061(3) 0.0309(7) Uani 1 1 d .
H11A H 0.2831 -0.2040 0.1534 0.037 Uiso 1 1 calc R
H11B H 0.1258 -0.3181 0.1012 0.037 Uiso 1 1 calc R
C12 C 0.2389(3) 0.1685(3) -0.0282(3) 0.0287(6) Uani 1 1 d .
C13 C 0.2550(4) 0.1339(3) -0.1744(3) 0.0305(6) Uani 1 1 d .
C14 C 0.7512(4) 0.5787(4) 0.2500(3) 0.0318(7) Uani 1 1 d .
C15 C 0.7642(3) 0.5555(3) 0.1061(3) 0.0272(6) Uani 1 1 d .
O2 O 0.1234(3) 0.1077(3) -0.0243(3) 0.0371(5) Uani 1 1 d .
O3 O 0.3540(2) 0.2634(3) 0.0834(2) 0.0341(5) Uani 1 1 d .
O4 O 0.3787(3) 0.2138(3) -0.1612(2) 0.0376(5) Uani 1 1 d .
O5 O 0.1539(3) 0.0389(3) -0.2869(3) 0.0462(6) Uani 1 1 d .
O6 O 0.6278(3) 0.4988(3) 0.2355(2) 0.0357(5) Uani 1 1 d .
O7 O 0.8536(3) 0.6676(3) 0.3639(3) 0.0512(7) Uani 1 1 d .
O8 O 0.6493(2) 0.4637(2) -0.0063(2) 0.0324(5) Uani 1 1 d .
O9 O 0.8798(3) 0.6258(3) 0.1085(2) 0.0386(6) Uani 1 1 d .
N1 N 0.2404(3) 0.3075(3) 0.3301(3) 0.0291(5) Uani 1 1 d D
H1N H 0.237(4) 0.297(4) 0.247(2) 0.044 Uiso 1 1 d D
H3N H 0.326(2) 0.348(4) 0.397(3) 0.044 Uiso 1 1 d D
N2 N 0.1349(3) -0.1018(3) 0.1949(3) 0.0294(5) Uani 1 1 d D
H2N H 0.126(4) -0.108(4) 0.268(3) 0.044 Uiso 1 1 d D
H4N H 0.0462(19) -0.120(4) 0.144(4) 0.044 Uiso 1 1 d D
O1 O 0.1079(3) 0.4109(3) 0.1389(2) 0.0354(5) Uani 1 1 d .
H1 H 0.094(5) 0.399(5) 0.063(5) 0.053 Uiso 1 1 d .
O1W O 0.1220(3) -0.1337(4) 0.4222(3) 0.0559(8) Uani 1 1 d D
H1D H 0.037(3) -0.204(4) 0.387(4) 0.084 Uiso 1 1 d D
H1E H 0.131(5) -0.068(4) 0.509(2) 0.084 Uiso 1 1 d D
O2W O 0.5040(3) 0.6049(4) 0.4436(3) 0.0608(8) Uani 1 1 d D
H2D H 0.492(6) 0.679(4) 0.436(6) 0.091 Uiso 1 1 d D
H2E H 0.547(6) 0.567(5) 0.382(5) 0.091 Uiso 1 1 d D
O3W O 0.4523(10) 0.1218(12) 0.5784(9) 0.104(3) Uani 0.50 1 d P
O4W O 0.3028(11) 0.7155(11) 0.3669(11) 0.110(3) Uiso 0.50 1 d P
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'
Cu Cu 0.3201 1.2651 '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
O6 Cu1 O4 174.66(10) . .
O6 Cu1 O3 94.03(9) . .
O4 Cu1 O3 85.33(9) . .
O6 Cu1 O8 85.22(9) . .
O4 Cu1 O8 95.35(9) . .
O3 Cu1 O8 178.92(9) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C7 117.2(3) . .
C3 C2 C1 121.9(3) . .
C7 C2 C1 120.9(3) . .
C2 C3 C4 123.1(3) . .
C2 C3 H3 118.5 . .
C4 C3 H3 118.5 . .
C5 C4 C3 118.4(3) . .
C5 C4 C11 121.9(3) . 2
C3 C4 C11 119.8(3) . 2
O1 C5 C4 125.6(3) . .
O1 C5 C6 114.9(3) . .
C4 C5 C6 119.5(3) . .
C7 C6 C5 120.1(3) . .
C7 C6 C8 120.9(3) . .
C5 C6 C8 118.7(3) . .
C6 C7 C2 121.5(3) . .
C6 C7 H7 119.3 . .
C2 C7 H7 119.3 . .
C6 C8 N1 110.3(2) . .
C6 C8 H8A 109.6 . .
N1 C8 H8A 109.6 . .
C6 C8 H8B 109.6 . .
N1 C8 H8B 109.6 . .
H8A C8 H8B 108.1 . .
N1 C9 C10 111.8(3) . .
N1 C9 H9A 109.2 . .
C10 C9 H9A 109.2 . .
N1 C9 H9B 109.2 . .
C10 C9 H9B 109.2 . .
H9A C9 H9B 107.9 . .
N2 C10 C9 108.1(2) . .
N2 C10 H10A 110.1 . .
C9 C10 H10A 110.1 . .
N2 C10 H10B 110.1 . .
C9 C10 H10B 110.1 . .
H10A C10 H10B 108.4 . .
C4 C11 N2 111.8(2) 2 .
C4 C11 H11A 109.3 2 .
N2 C11 H11A 109.3 . .
C4 C11 H11B 109.3 2 .
N2 C11 H11B 109.3 . .
H11A C11 H11B 107.9 . .
O2 C12 O3 124.4(3) . .
O2 C12 C13 120.9(3) . .
O3 C12 C13 114.7(3) . .
O5 C13 O4 126.6(3) . .
O5 C13 C12 119.4(3) . .
O4 C13 C12 114.0(3) . .
O7 C14 O6 125.8(3) . .
O7 C14 C15 120.1(3) . .
O6 C14 C15 114.2(3) . .
O9 C15 O8 125.8(3) . .
O9 C15 C14 119.1(3) . .
O8 C15 C14 115.2(3) . .
C12 O3 Cu1 111.92(19) . .
C13 O4 Cu1 112.6(2) . .
C14 O6 Cu1 113.22(19) . .
C15 O8 Cu1 111.64(18) . .
C9 N1 C8 111.7(2) . .
C9 N1 H1N 109(3) . .
C8 N1 H1N 104(3) . .
C9 N1 H3N 109(3) . .
C8 N1 H3N 105(3) . .
H1N N1 H3N 117(4) . .
C10 N2 C11 114.1(2) . .
C10 N2 H2N 114(3) . .
C11 N2 H2N 107(3) . .
C10 N2 H4N 109(3) . .
C11 N2 H4N 108(3) . .
H2N N2 H4N 104(4) . .
C5 O1 H1 113(3) . .
H1D O1W H1E 105(4) . .
H2D O2W H2E 103(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O6 1.917(2) .
Cu1 O4 1.925(2) .
Cu1 O3 1.929(2) .
Cu1 O8 1.945(2) .
C1 C2 1.508(5) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.382(5) .
C2 C7 1.399(4) .
C3 C4 1.400(4) .
C3 H3 0.9300 .
C4 C5 1.396(4) .
C4 C11 1.506(4) 2
C5 O1 1.354(4) .
C5 C6 1.402(4) .
C6 C7 1.385(4) .
C6 C8 1.502(4) .
C7 H7 0.9300 .
C8 N1 1.514(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 N1 1.487(4) .
C9 C10 1.515(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 N2 1.488(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C4 1.506(4) 2
C11 N2 1.512(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 O2 1.225(4) .
C12 O3 1.279(4) .
C12 C13 1.553(4) .
C13 O5 1.216(4) .
C13 O4 1.285(4) .
C14 O7 1.220(4) .
C14 O6 1.277(4) .
C14 C15 1.549(4) .
C15 O9 1.230(4) .
C15 O8 1.277(4) .
N1 H1N 0.869(10) .
N1 H3N 0.870(10) .
N2 H2N 0.875(10) .
N2 H4N 0.876(10) .
O1 H1 0.77(5) .
O1W H1D 0.871(10) .
O1W H1E 0.869(10) .
O2W H2D 0.880(10) .
O2W H2E 0.875(10) .
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
N1 H1N O3 0.869(10) 2.32(2) 3.080(3) 147(3) .
N1 H1N O1 0.869(10) 2.48(3) 3.050(4) 124(3) .
N2 H2N O1W 0.875(10) 1.878(12) 2.748(4) 173(4) .
O2W H2E O6 0.875(10) 1.896(14) 2.766(4) 172(5) .
O1 H1 O9 0.77(5) 1.90(5) 2.642(3) 163(5) 2_665
O1W H1D O7 0.871(10) 1.937(17) 2.786(4) 164(4) 1_445
O1W H1E O5 0.869(10) 1.950(18) 2.799(4) 165(5) 1_556
O2W H2D O4W 0.880(10) 2.09(4) 2.749(10) 131(5) .
O2W H2D O3W 0.880(10) 2.20(3) 3.035(11) 158(5) 2_666
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_4
C7 C2 C3 C4 -3.6(5) . .
C1 C2 C3 C4 176.7(3) . .
C2 C3 C4 C5 -1.0(5) . .
C2 C3 C4 C11 177.2(3) . 2
C3 C4 C5 O1 -175.3(3) . .
C11 C4 C5 O1 6.5(5) 2 .
C3 C4 C5 C6 5.7(4) . .
C11 C4 C5 C6 -172.4(3) 2 .
O1 C5 C6 C7 175.1(3) . .
C4 C5 C6 C7 -5.8(4) . .
O1 C5 C6 C8 -10.1(4) . .
C4 C5 C6 C8 169.0(3) . .
C5 C6 C7 C2 1.1(5) . .
C8 C6 C7 C2 -173.6(3) . .
C3 C2 C7 C6 3.5(5) . .
C1 C2 C7 C6 -176.8(3) . .
C7 C6 C8 N1 105.6(3) . .
C5 C6 C8 N1 -69.2(4) . .
N1 C9 C10 N2 -170.4(3) . .
O2 C12 C13 O5 -4.2(5) . .
O3 C12 C13 O5 175.9(3) . .
O2 C12 C13 O4 175.2(3) . .
O3 C12 C13 O4 -4.7(4) . .
O7 C14 C15 O9 1.3(5) . .
O6 C14 C15 O9 -178.9(3) . .
O7 C14 C15 O8 -177.8(3) . .
O6 C14 C15 O8 2.0(4) . .
O2 C12 O3 Cu1 -168.4(3) . .
C13 C12 O3 Cu1 11.5(3) . .
O6 Cu1 O3 C12 173.9(2) . .
O4 Cu1 O3 C12 -11.4(2) . .
O5 C13 O4 Cu1 174.6(3) . .
C12 C13 O4 Cu1 -4.8(3) . .
O3 Cu1 O4 C13 8.7(2) . .
O8 Cu1 O4 C13 -172.1(2) . .
O7 C14 O6 Cu1 -176.2(3) . .
C15 C14 O6 Cu1 4.0(3) . .
O3 Cu1 O6 C14 173.1(2) . .
O8 Cu1 O6 C14 -6.2(2) . .
O9 C15 O8 Cu1 174.2(3) . .
C14 C15 O8 Cu1 -6.8(3) . .
O6 Cu1 O8 C15 7.2(2) . .
O4 Cu1 O8 C15 -167.4(2) . .
C10 C9 N1 C8 175.8(2) . .
C6 C8 N1 C9 -59.1(3) . .
C9 C10 N2 C11 172.0(2) . .
C4 C11 N2 C10 -71.8(3) 2 .
