#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/86/2228615.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_2228615
loop_
_publ_author_name
'Feng, Jian-Shen'
'Zou, Li-Ke'
'Xie, Bin'
'Xiang, Yang-Guang'
'Lai, Chuan'
_publ_section_title
;
 (meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane)copper(II)
 bis[O,O'-(o-phenylene)dithiophosphate]
;
_journal_coeditor_code           XU5086
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1593
_journal_paper_doi               10.1107/S1600536810046684
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu (C16 H36 N4)] (C6 H4 O2 P S2)2'
_chemical_formula_moiety         'C16 H36 Cu N4 2+, 2(C6 H4 O2 P S2 -)'
_chemical_formula_sum            'C28 H44 Cu N4 O4 P2 S4'
_chemical_formula_weight         754.39
_chemical_name_systematic
;
(meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-
tetraazacyclotetradecane)copper(II)
bis[O,O'-(o-phenylene)dithiophosphate]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 107.136(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.3107(4)
_cell_length_b                   12.1612(3)
_cell_length_c                   12.3703(4)
_cell_measurement_reflns_used    4041
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.1616
_cell_measurement_theta_min      3.239
_cell_volume                     1769.78(10)
_computing_cell_refinement       'CrysAlis Pro CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7203
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.25
_diffrn_standards_interval_count 0
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis Pro RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            dark-violet
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             790
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0291
_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)+(0.0358P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                2662
_reflns_number_total             3621
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5086.cif
_cod_data_source_block           I
_cod_original_cell_volume        1769.78(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228615
_cod_database_fobs_code          2228615
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.60607(18) 0.32263(15) 0.63651(17) 0.0421(5) Uani d . 1 . .
H H1A 0.6460 0.2530 0.6438 0.050 Uiso calc R 1 . .
H H1B 0.5573 0.3210 0.6854 0.050 Uiso calc R 1 . .
C C6 0.5147(2) 0.85983(17) 0.5043(2) 0.0750(9) Uani d . 1 . .
H H6B 0.4588 0.8709 0.5434 0.113 Uiso calc R 1 . .
H H6A 0.4810 0.8734 0.4250 0.113 Uiso calc R 1 . .
H H6C 0.5770 0.9096 0.5336 0.113 Uiso calc R 1 . .
C C3 0.69922(17) 0.62275(15) 0.67689(17) 0.0385(5) Uani d . 1 . .
C C4 0.62020(18) 0.72195(15) 0.64523(18) 0.0448(5) Uani d . 1 . .
H H4A 0.5636 0.7154 0.6853 0.054 Uiso calc R 1 . .
H H4B 0.6647 0.7872 0.6739 0.054 Uiso calc R 1 . .
C C2 0.69001(16) 0.41537(15) 0.67066(18) 0.0417(5) Uani d . 1 . .
H H2B 0.7315 0.4094 0.7503 0.050 Uiso calc R 1 . .
H H2A 0.7441 0.4122 0.6275 0.050 Uiso calc R 1 . .
C C5 0.55801(18) 0.74158(14) 0.52163(18) 0.0412(5) Uani d . 1 . .
H H5 0.6116 0.7305 0.4777 0.049 Uiso calc R 1 . .
C C8 0.7587(2) 0.62675(19) 0.80430(19) 0.0669(7) Uani d . 1 . .
H H8A 0.7031 0.6214 0.8445 0.100 Uiso calc R 1 . .
H H8C 0.7993 0.6949 0.8231 0.100 Uiso calc R 1 . .
H H8B 0.8111 0.5665 0.8253 0.100 Uiso calc R 1 . .
C C7 0.78770(19) 0.62258(17) 0.6133(2) 0.0589(7) Uani d . 1 . .
H H7B 0.8442 0.5677 0.6449 0.088 Uiso calc R 1 . .
H H7C 0.8232 0.6936 0.6198 0.088 Uiso calc R 1 . .
H H7A 0.7516 0.6063 0.5349 0.088 Uiso calc R 1 . .
P P1 0.76165(4) 0.41284(4) 0.34491(4) 0.03621(14) Uani d . 1 . .
S S1 0.62560(5) 0.50447(5) 0.31713(5) 0.05140(17) Uani d . 1 . .
S S2 0.77079(5) 0.27519(4) 0.42553(5) 0.04891(16) Uani d . 1 . .
O O1 0.79072(12) 0.39508(11) 0.22398(12) 0.0475(4) Uani d . 1 . .
O O2 0.87362(11) 0.49007(10) 0.40083(12) 0.0452(4) Uani d . 1 . .
C C9 0.91021(16) 0.53308(17) 0.31328(19) 0.0411(5) Uani d . 1 . .
N N1 0.53721(13) 0.33932(11) 0.51843(12) 0.0309(4) Uani d . 1 . .
H H1 0.5849 0.3263 0.4759 0.037 Uiso calc R 1 . .
C C10 0.98455(17) 0.61848(17) 0.3208(2) 0.0554(6) Uani d . 1 . .
H H10 1.0162 0.6554 0.3886 0.067 Uiso calc R 1 . .
C C13 0.8889(2) 0.50583(19) 0.1159(2) 0.0611(7) Uani d . 1 . .
H H13 0.8572 0.4685 0.0483 0.073 Uiso calc R 1 . .
C C14 0.86346(18) 0.47825(17) 0.21245(19) 0.0438(5) Uani d . 1 . .
Cu Cu1 0.5000 0.5000 0.5000 0.03160(11) Uani d S 1 . .
N N2 0.62678(12) 0.52077(11) 0.64861(13) 0.0315(4) Uani d . 1 . .
H H2 0.5886 0.5211 0.7014 0.038 Uiso calc R 1 . .
C C11 1.0108(2) 0.6478(2) 0.2226(3) 0.0656(8) Uani d . 1 . .
H H11 1.0605 0.7058 0.2246 0.079 Uiso calc R 1 . .
C C12 0.9647(2) 0.5925(2) 0.1231(3) 0.0713(8) Uani d . 1 . .
H H12 0.9844 0.6133 0.0590 0.086 Uiso calc R 1 . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 C2 H2B . . 110.0 ?
C1 C2 H2A . . 110.0 ?
C1 N1 C5 . 3_666 113.81(14) ?
C1 N1 H1 . . 105.6 ?
C1 N1 Cu1 . . 107.04(11) ?
H1A C1 H1B . . 108.3 ?
C6 C5 H5 . . 108.4 ?
H6B C6 H6A . . 109.5 ?
H6B C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
C3 C4 H4A . . 107.7 ?
C3 C4 H4B . . 107.7 ?
C3 C8 H8A . . 109.5 ?
C3 C8 H8C . . 109.5 ?
C3 C8 H8B . . 109.5 ?
C3 C7 H7B . . 109.5 ?
C3 C7 H7C . . 109.5 ?
C3 C7 H7A . . 109.5 ?
C3 N2 Cu1 . . 123.54(11) ?
C3 N2 H2 . . 103.1 ?
C4 C3 C8 . . 108.33(17) ?
C4 C5 C6 . . 110.00(17) ?
C4 C5 H5 . . 108.4 ?
H4A C4 H4B . . 107.1 ?
C2 C1 H1A . . 109.9 ?
C2 C1 H1B . . 109.9 ?
C2 N2 C3 . . 115.21(15) ?
C2 N2 Cu1 . . 106.18(11) ?
C2 N2 H2 . . 103.1 ?
H2B C2 H2A . . 108.4 ?
C5 C6 H6B . . 109.5 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6C . . 109.5 ?
C5 C4 C3 . . 118.56(17) ?
C5 C4 H4A . . 107.7 ?
C5 C4 H4B . . 107.7 ?
C5 N1 H1 3_666 . 105.6 ?
C5 N1 Cu1 3_666 . 118.17(12) ?
H8A C8 H8C . . 109.5 ?
H8A C8 H8B . . 109.5 ?
H8C C8 H8B . . 109.5 ?
C7 C3 C4 . . 111.59(18) ?
C7 C3 C8 . . 109.55(19) ?
H7B C7 H7C . . 109.5 ?
H7B C7 H7A . . 109.5 ?
H7C C7 H7A . . 109.5 ?
S2 P1 S1 . . 120.01(4) ?
O1 P1 S1 . . 108.55(6) ?
O1 P1 S2 . . 111.01(6) ?
O2 P1 S1 . . 108.48(5) ?
O2 P1 S2 . . 111.31(6) ?
O2 P1 O1 . . 94.43(7) ?
C9 O2 P1 . . 108.12(12) ?
C9 C10 H10 . . 121.4 ?
C9 C10 C11 . . 117.2(2) ?
C9 C14 O1 . . 111.67(19) ?
N1 C1 H1A . . 109.9 ?
N1 C1 H1B . . 109.9 ?
N1 C1 C2 . . 108.83(15) ?
N1 C5 C6 3_666 . 111.41(17) ?
N1 C5 C4 3_666 . 110.13(15) ?
N1 C5 H5 3_666 . 108.4 ?
N1 Cu1 N1 . 3_666 180.0 ?
N1 Cu1 N2 3_666 3_666 85.98(6) ?
N1 Cu1 N2 . 3_666 94.02(6) ?
N1 Cu1 N2 . . 85.98(6) ?
N1 Cu1 N2 3_666 . 94.02(6) ?
C10 C9 O2 . . 126.6(2) ?
C10 C9 C14 . . 121.3(2) ?
C10 C11 H11 . . 119.4 ?
C13 C14 O1 . . 126.3(2) ?
C13 C14 C9 . . 122.0(2) ?
C13 C12 H12 . . 119.3 ?
C14 O1 P1 . . 108.47(12) ?
C14 C9 O2 . . 112.15(18) ?
C14 C13 H13 . . 121.5 ?
C14 C13 C12 . . 116.9(2) ?
Cu1 N1 H1 . . 105.6 ?
Cu1 N2 H2 . . 103.1 ?
N2 C3 C4 . . 107.57(15) ?
N2 C3 C8 . . 109.63(16) ?
N2 C3 C7 . . 110.12(16) ?
N2 C2 C1 . . 108.46(15) ?
N2 C2 H2B . . 110.0 ?
N2 C2 H2A . . 110.0 ?
N2 Cu1 N2 . 3_666 180.0 ?
C11 C10 H10 . . 121.4 ?
C11 C12 C13 . . 121.4(3) ?
C11 C12 H12 . . 119.3 ?
C12 C13 H13 . . 121.5 ?
C12 C11 C10 . . 121.1(2) ?
C12 C11 H11 . . 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C1 C2 . 1.504(3) ?
C1 N1 . 1.471(2) ?
C6 H6B . 0.9600 ?
C6 H6A . 0.9600 ?
C6 H6C . 0.9600 ?
C6 C5 . 1.527(3) ?
C3 C4 . 1.527(3) ?
C3 C8 . 1.531(3) ?
C3 C7 . 1.520(3) ?
C3 N2 . 1.507(2) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C4 C5 . 1.514(3) ?
C2 H2B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 N2 . 1.483(2) ?
C5 H5 . 0.9800 ?
C5 N1 3_666 1.498(2) ?
C8 H8A . 0.9600 ?
C8 H8C . 0.9600 ?
C8 H8B . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C7 H7A . 0.9600 ?
P1 S1 . 1.9560(7) ?
P1 S2 . 1.9348(8) ?
P1 O1 . 1.6517(14) ?
P1 O2 . 1.6429(14) ?
O1 C14 . 1.386(2) ?
O2 C9 . 1.392(2) ?
C9 C10 . 1.369(3) ?
C9 C14 . 1.382(3) ?
N1 C5 3_666 1.499(2) ?
N1 H1 . 0.9100 ?
N1 Cu1 . 2.0047(13) ?
C10 H10 . 0.9300 ?
C10 C11 . 1.391(3) ?
C13 H13 . 0.9300 ?
C13 C14 . 1.363(3) ?
C13 C12 . 1.393(3) ?
Cu1 N1 3_666 2.0047(13) ?
Cu1 N2 . 2.0466(15) ?
Cu1 N2 3_666 2.0466(15) ?
N2 H2 . 0.9100 ?
C11 H11 . 0.9300 ?
C11 C12 . 1.370(4) ?
C12 H12 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 S2 . 0.91 2.62 3.4849(16) 159.5
N2 H2 S1 3_666 0.91 2.60 3.2715(16) 131.5
C1 H1A O1 4_566 0.97 2.52 3.449(2) 160
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 N2 C3 . . . . -179.14(16) ?
C1 C2 N2 Cu1 . . . . -38.57(18) ?
C1 N1 Cu1 N2 . . . . 15.68(13) ?
C1 N1 Cu1 N2 . . . 3_666 -164.32(13) ?
C3 C4 C5 C6 . . . . -162.4(2) ?
C3 C4 C5 N1 . . . 3_666 74.4(2) ?
C4 C3 N2 C2 . . . . 178.22(16) ?
C4 C3 N2 Cu1 . . . . 45.3(2) ?
C2 C1 N1 C5 . . . 3_666 -173.86(16) ?
C2 C1 N1 Cu1 . . . . -41.42(18) ?
C5 N1 Cu1 N2 3_666 . . . 145.70(14) ?
C5 N1 Cu1 N2 3_666 . . 3_666 -34.30(14) ?
C8 C3 C4 C5 . . . . 175.34(19) ?
C8 C3 N2 C2 . . . . -64.2(2) ?
C8 C3 N2 Cu1 . . . . 162.85(14) ?
C7 C3 C4 C5 . . . . 54.7(2) ?
C7 C3 N2 C2 . . . . 56.4(2) ?
C7 C3 N2 Cu1 . . . . -76.55(19) ?
P1 O1 C14 C9 . . . . 14.3(2) ?
P1 O1 C14 C13 . . . . -165.8(2) ?
P1 O2 C9 C10 . . . . 165.19(17) ?
P1 O2 C9 C14 . . . . -15.6(2) ?
S1 P1 O1 C14 . . . . 90.71(13) ?
S1 P1 O2 C9 . . . . -90.46(12) ?
S2 P1 O1 C14 . . . . -135.33(12) ?
S2 P1 O2 C9 . . . . 135.39(11) ?
O1 P1 O2 C9 . . . . 20.78(13) ?
O2 P1 O1 C14 . . . . -20.48(14) ?
O2 C9 C10 C11 . . . . 179.29(18) ?
O2 C9 C14 O1 . . . . 0.8(3) ?
O2 C9 C14 C13 . . . . -179.1(2) ?
C9 C10 C11 C12 . . . . -0.6(3) ?
N1 C1 C2 N2 . . . . 54.5(2) ?
N1 Cu1 N2 C3 . . . . 149.25(14) ?
N1 Cu1 N2 C3 3_666 . . . -30.75(14) ?
N1 Cu1 N2 C2 3_666 . . . -167.17(12) ?
N1 Cu1 N2 C2 . . . . 12.83(12) ?
C10 C9 C14 O1 . . . . -179.94(17) ?
C10 C9 C14 C13 . . . . 0.2(3) ?
C10 C11 C12 C13 . . . . 0.7(4) ?
C14 C9 C10 C11 . . . . 0.1(3) ?
C14 C13 C12 C11 . . . . -0.4(4) ?
N2 C3 C4 C5 . . . . -66.2(2) ?
C12 C13 C14 O1 . . . . -179.9(2) ?
C12 C13 C14 C9 . . . . -0.1(3) ?
