#------------------------------------------------------------------------------
#$Date: 2017-08-07 04:53:34 +0300 (Mon, 07 Aug 2017) $
#$Revision: 199607 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/02/2210299.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210299
loop_
_publ_author_name
'Choi, Jong-Ha'
'Suzuki, Takayoshi'
'Kaizaki, Sumio'
_publ_section_title
;(5,16-Dimethyl-2,6,13,17-tetraazatricyclo[14,4,0^1,18^,0^7,12^]docosane-κ⁴N)dinitratocopper(II)
 trihydrate
;
_journal_coeditor_code           HY2020
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2383
_journal_page_last               m2385
_journal_paper_doi               10.1107/S1600536806034234
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu (N1 O3)2 (C20 H40 N4)], 3H2 O'
_chemical_formula_moiety         'C20 H40 Cu N4 2+, 2N O3 -, 3H2 O'
_chemical_formula_sum            'C20 H46 Cu N6 O9'
_chemical_formula_weight         578.17
_chemical_name_systematic
;
[5,16-Dimethyl-2,6,13,17-tetraazatricyclo[14,4,0^1.18^,0^7.12^]docosane-
κ⁴N]dinitratocopper(II) trihydrate
;
_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                93.06(3)
_cell_angle_beta                 106.86(2)
_cell_angle_gamma                108.43(3)
_cell_formula_units_Z            1
_cell_length_a                   7.813(5)
_cell_length_b                   8.746(7)
_cell_length_c                   10.715(7)
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     656.2(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6435
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  0.9162
_exptl_absorpt_correction_T_min  0.8419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            red--pink
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             309
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.421
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0300
_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)+(0.0752P)²+0.2496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2809
_reflns_number_total             2969
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            hy2020.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-08-07
;
_cod_database_code               2210299
_cod_database_fobs_code          2210299
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_attached_hydrogens
Cu Cu1 0.0000 0.0000 0.0000 0.01594(13) Uani d S 1 0
O O1 0.1797(3) -0.2240(2) 0.00098(18) 0.0340(4) Uani d . 1 0
O O2 0.2211(3) -0.2795(2) 0.20003(16) 0.0335(4) Uani d . 1 0
O O3 0.2222(3) -0.4498(2) 0.04641(19) 0.0341(4) Uani d . 1 0
O O4 -0.0160(4) -0.5639(3) 0.2688(2) 0.0493(6) Uani d . 1 0
O O5 -0.0376(6) -0.3449(5) 0.4723(4) 0.0422(9) Uani d P 0.50 2
N N1 0.0250(2) -0.03671(19) 0.18891(15) 0.0153(3) Uani d . 1 0
H H1N 0.0836 -0.1147 0.2005 0.018 Uiso calc R 1 0
N N2 0.2353(2) 0.20037(19) 0.08223(15) 0.0153(3) Uani d . 1 0
H H2N 0.1927 0.2873 0.0899 0.018 Uiso calc R 1 0
N N3 0.2077(2) -0.3193(2) 0.08223(18) 0.0219(4) Uani d . 1 0
C C1 0.1703(3) 0.1115(2) 0.28035(18) 0.0167(4) Uani d . 1 0
H H1A 0.1093 0.1951 0.2861 0.020 Uiso calc R 1 0
C C2 0.2534(3) 0.0784(3) 0.4198(2) 0.0242(4) Uani d . 1 0
H H2A 0.1502 0.0389 0.4588 0.029 Uiso calc R 1 0
H H2B 0.3092 -0.0080 0.4153 0.029 Uiso calc R 1 0
C C3 0.4067(4) 0.2325(3) 0.5074(2) 0.0304(5) Uani d . 1 0
H H3A 0.3483 0.3152 0.5193 0.036 Uiso calc R 1 0
H H3B 0.4631 0.2067 0.5955 0.036 Uiso calc R 1 0
C C4 0.5625(3) 0.3020(3) 0.4467(2) 0.0281(5) Uani d . 1 0
H H4A 0.6306 0.2243 0.4441 0.034 Uiso calc R 1 0
H H4B 0.6559 0.4055 0.5025 0.034 Uiso calc R 1 0
C C5 0.4804(3) 0.3339(3) 0.3063(2) 0.0243(4) Uani d . 1 0
H H5A 0.4241 0.4202 0.3096 0.029 Uiso calc R 1 0
H H5B 0.5840 0.3729 0.2675 0.029 Uiso calc R 1 0
C C6 0.3276(3) 0.1782(2) 0.21965(18) 0.0166(4) Uani d . 1 0
H H6A 0.3887 0.0944 0.2145 0.020 Uiso calc R 1 0
C C7 0.3737(3) 0.2485(3) 0.0084(2) 0.0225(4) Uani d . 1 0
H H7A 0.4343 0.1649 0.0072 0.027 Uiso calc R 1 0
H H7B 0.4753 0.3533 0.0550 0.027 Uiso calc R 1 0
C C8 0.2796(3) 0.2669(2) -0.13312(19) 0.0209(4) Uani d . 1 0
H H8A 0.3812 0.3238 -0.1695 0.025 Uiso calc R 1 0
H H8B 0.2036 0.3381 -0.1311 0.025 Uiso calc R 1 0
C C9 0.1502(3) 0.1094(2) -0.22755(19) 0.0168(4) Uani d . 1 0
H H9A 0.1084 0.1385 -0.3177 0.020 Uiso calc R 1 0
C C10 0.2519(3) -0.0120(3) -0.2355(2) 0.0253(4) Uani d . 1 0
H H10A 0.1628 -0.1109 -0.2971 0.030 Uiso calc R 1 0
H H10B 0.2983 -0.0402 -0.1477 0.030 Uiso calc R 1 0
H H10C 0.3600 0.0373 -0.2667 0.030 Uiso calc R 1 0
H H4P 0.058(5) -0.493(4) 0.250(3) 0.036(8) Uiso d . 1 0
H H4O -0.087(6) -0.614(5) 0.194(4) 0.052(10) Uiso d . 1 0
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
N2 Cu1 N1 . . 85.04(7) yes
N2 Cu1 O1 . . 97.83(9) yes
N1 Cu1 O1 . . 84.08(6) yes
N1 Cu1 N2 . 2 94.96(7) yes
N1 Cu1 O1 . 2 95.92(6) yes
N2 Cu1 O1 . 2 82.17(9) yes
N3 O1 Cu1 . . 129.37(14) ?
C1 N1 C9 . 2 114.46(15) ?
C1 N1 Cu1 . . 108.90(12) ?
C9 N1 Cu1 2 . 120.16(12) ?
C7 N2 C6 . . 112.03(16) ?
C7 N2 Cu1 . . 117.40(13) ?
C6 N2 Cu1 . . 107.32(12) ?
O3 N3 O2 . . 120.65(18) ?
O3 N3 O1 . . 120.26(19) ?
O2 N3 O1 . . 119.08(18) ?
N1 C1 C6 . . 107.45(15) ?
N1 C1 C2 . . 113.26(16) ?
C6 C1 C2 . . 110.51(17) ?
C3 C2 C1 . . 110.98(18) ?
C4 C3 C2 . . 110.93(19) ?
C3 C4 C5 . . 111.44(19) ?
C6 C5 C4 . . 110.55(17) ?
N2 C6 C1 . . 107.48(16) ?
N2 C6 C5 . . 113.92(16) ?
C1 C6 C5 . . 110.62(17) ?
N2 C7 C8 . . 112.35(17) ?
C7 C8 C9 . . 116.18(17) ?
N1 C9 C8 2 . 109.32(16) ?
N1 C9 C10 2 . 111.96(16) ?
C8 C9 C10 . . 112.68(18) ?
H4P O4 H4O . . 101(3) ?
C1 N1 H1N . . 103.7 ?
C9 N1 H1N 2 . 103.7 ?
Cu1 N1 H1N . . 103.7 ?
C7 N2 H2N . . 106.5 ?
C6 N2 H2N . . 106.5 ?
Cu1 N2 H2N . . 106.5 ?
N1 C1 H1A . . 108.5 ?
C6 C1 H1A . . 108.5 ?
C2 C1 H1A . . 108.5 ?
C3 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
C3 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.0 ?
C3 C4 H4A . . 109.3 ?
C5 C4 H4A . . 109.3 ?
C3 C4 H4B . . 109.3 ?
C5 C4 H4B . . 109.3 ?
H4A C4 H4B . . 108.0 ?
C6 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
C6 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
N2 C6 H6A . . 108.2 ?
C1 C6 H6A . . 108.2 ?
C5 C6 H6A . . 108.2 ?
N2 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
N2 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.9 ?
C7 C8 H8A . . 108.2 ?
C9 C8 H8A . . 108.2 ?
C7 C8 H8B . . 108.2 ?
C9 C8 H8B . . 108.2 ?
H8A C8 H8B . . 107.4 ?
N1 C9 H9A 2 . 107.5 ?
C8 C9 H9A . . 107.5 ?
C10 C9 H9A . . 107.5 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
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
Cu1 N2 . 2.021(2) yes
Cu1 N1 . 2.029(2) yes
Cu1 O1 . 2.746(2) yes
O1 N3 . 1.258(2) ?
O2 N3 . 1.256(3) ?
O3 N3 . 1.234(3) ?
N1 C1 . 1.489(3) ?
N1 C9 2 1.501(2) ?
N2 C7 . 1.489(3) ?
N2 C6 . 1.493(3) ?
C1 C6 . 1.524(3) ?
C1 C2 . 1.529(3) ?
C2 C3 . 1.525(3) ?
C3 C4 . 1.520(3) ?
C4 C5 . 1.533(3) ?
C5 C6 . 1.528(3) ?
C7 C8 . 1.523(3) ?
C8 C9 . 1.524(3) ?
C9 C10 . 1.526(3) ?
O4 H4P . 0.79(4) ?
O4 H4O . 0.84(4) ?
N1 H1N . 0.9300 ?
N2 H2N . 0.9300 ?
C1 H1A . 1.0000 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 1.0000 ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 1.0000 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
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
_geom_hbond_publ_flag
N1 H1N O2 . 0.93 2.05 2.975(3) 171.3 yes
N2 H2N O3 1_565 0.93 2.32 3.133(3) 145.4 yes
O4 H4P O2 . 0.79(4) 2.10(3) 2.870(3) 169(4) yes
O4 H4O O1 2_545 0.84(4) 2.25(4) 3.036(2) 158(4) yes
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_4
_geom_torsion
N2 Cu1 O1 N3 . . 97.99(19)
N2 Cu1 O1 N3 2 . -82.01(19)
N1 Cu1 O1 N3 . . 13.85(18)
N1 Cu1 O1 N3 2 . -166.15(18)
N2 Cu1 N1 C1 . . 10.43(12)
N2 Cu1 N1 C1 2 . -169.57(12)
O1 Cu1 N1 C1 . . 108.85(13)
N2 Cu1 N1 C9 . 2 145.27(14)
N2 Cu1 N1 C9 2 2 -34.73(14)
O1 Cu1 N1 C9 . 2 -116.31(14)
N1 Cu1 N2 C7 . . 145.82(14)
N1 Cu1 N2 C7 2 . -34.18(14)
O1 Cu1 N2 C7 . . 62.50(14)
N1 Cu1 N2 C6 . . 18.65(12)
N1 Cu1 N2 C6 2 . -161.35(12)
O1 Cu1 N2 C6 . . -64.67(12)
Cu1 O1 N3 O3 . . 152.16(16)
Cu1 O1 N3 O2 . . -28.0(3)
C9 N1 C1 C6 2 . -174.50(14)
Cu1 N1 C1 C6 . . -36.83(16)
C9 N1 C1 C2 2 . 63.2(2)
Cu1 N1 C1 C2 . . -159.17(14)
N1 C1 C2 C3 . . 177.75(17)
C6 C1 C2 C3 . . 57.1(2)
C1 C2 C3 C4 . . -56.0(3)
C2 C3 C4 C5 . . 55.5(3)
C3 C4 C5 C6 . . -55.9(3)
C7 N2 C6 C1 . . -173.90(15)
Cu1 N2 C6 C1 . . -43.64(16)
C7 N2 C6 C5 . . 63.2(2)
Cu1 N2 C6 C5 . . -166.58(14)
N1 C1 C6 N2 . . 53.49(19)
C2 C1 C6 N2 . . 177.52(15)
N1 C1 C6 C5 . . 178.44(15)
C2 C1 C6 C5 . . -57.5(2)
C4 C5 C6 N2 . . 177.97(18)
C4 C5 C6 C1 . . 56.8(2)
C6 N2 C7 C8 . . 178.46(15)
Cu1 N2 C7 C8 . . 53.6(2)
N2 C7 C8 C9 . . -71.5(2)
C7 C8 C9 N1 . 2 68.7(2)
C7 C8 C9 C10 . . -56.5(2)
