#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/03/2240382.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_2240382
loop_
_publ_author_name
'Kim, Dae-Woong'
'Shin, Jong Won'
'Moon, Dohyun'
_publ_section_title
;
 Crystal structure of
 trans-(1,8-dibutyl-1,3,6,8,10,13-hexaazacyclotetradecane-κ⁴N³,N⁶,N¹⁰,N¹³)bis(perchlorato-κO)copper(II)
 from synchrotron data
;
_journal_coeditor_code           SJ5435
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              136
_journal_page_last               138
_journal_paper_doi               10.1107/S2056989014028047
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Cu (Cl O4)2 (C16 H38 N6)]'
_chemical_formula_moiety         'C16 H38 Cl2 Cu N6 O8'
_chemical_formula_sum            'C16 H38 Cl2 Cu N6 O8'
_chemical_formula_weight         576.96
_chemical_name_systematic
trans-(1,8-Dibutyl-1,3,6,8,10,13-hexaazacyclotetradecane-κ⁴N³,N⁶,N¹⁰,N¹³)bis(perchlorato-κO)copper(II)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                92.87(3)
_cell_angle_beta                 96.12(3)
_cell_angle_gamma                116.60(3)
_cell_formula_units_Z            1
_cell_length_a                   8.2230(16)
_cell_length_b                   8.3600(17)
_cell_length_c                   10.039(2)
_cell_measurement_reflns_used    16838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.547
_cell_measurement_theta_min      0.361
_cell_volume                     609.8(3)
_computing_cell_refinement
;
HKL3000sm (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
PAL ADSC Quantum-210 ADX (Arvai & Nielsen, 1983)
;
_computing_data_reduction
;
HKL3000sm (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'ADSC Q210 CCD area-detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.62998
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            6292
_diffrn_reflns_theta_full        22.209
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.819
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
(HKL3000sm SCALEPACK; Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             303
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.861
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0574P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                2536
_reflns_number_total             3195
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5435sup1.cf
_cod_data_source_block           I
_cod_database_code               2240382
_cod_database_fobs_code          2240382
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.975
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
Cu Cu1 0.5000 0.5000 0.5000 0.01063(10) Uani d 1
N N1 0.7678(2) 0.6261(2) 0.57656(16) 0.0119(3) Uani d 1
H H1 0.8221 0.5443 0.5535 0.014 Uiso calc 1
N N2 0.4291(2) 0.3507(2) 0.65492(16) 0.0123(3) Uani d 1
H H2 0.4599 0.2490 0.6389 0.015 Uiso calc 1
N N3 0.7247(2) 0.5222(2) 0.80108(16) 0.0152(3) Uani d 1
C C1 0.8525(2) 0.7860(2) 0.5034(2) 0.0155(4) Uani d 1
H H1A 0.9876 0.8328 0.5156 0.019 Uiso calc 1
H H1B 0.8242 0.8821 0.5385 0.019 Uiso calc 1
C C2 0.8084(3) 0.6731(3) 0.7267(2) 0.0164(4) Uani d 1
H H2A 0.9432 0.7303 0.7541 0.020 Uiso calc 1
H H2B 0.7654 0.7626 0.7508 0.020 Uiso calc 1
C C3 0.5278(3) 0.4466(3) 0.7910(2) 0.0158(4) Uani d 1
H H3A 0.4948 0.5445 0.8119 0.019 Uiso calc 1
H H3B 0.4855 0.3612 0.8594 0.019 Uiso calc 1
C C4 0.2256(2) 0.2705(3) 0.6448(2) 0.0156(4) Uani d 1
H H4A 0.1894 0.3598 0.6819 0.019 Uiso calc 1
H H4B 0.1786 0.1649 0.6964 0.019 Uiso calc 1
C C5 0.8000(3) 0.3919(3) 0.7910(2) 0.0169(4) Uani d 1
H H5A 0.9359 0.4586 0.8041 0.020 Uiso calc 1
H H5B 0.7593 0.3265 0.6992 0.020 Uiso calc 1
C C6 0.7409(3) 0.2567(3) 0.8931(2) 0.0177(4) Uani d 1
H H6A 0.6067 0.1782 0.8721 0.021 Uiso calc 1
H H6B 0.7662 0.3217 0.9840 0.021 Uiso calc 1
C C7 0.8401(3) 0.1406(3) 0.8937(2) 0.0221(4) Uani d 1
H H7A 0.9723 0.2171 0.9266 0.026 Uiso calc 1
H H7B 0.8289 0.0888 0.8003 0.026 Uiso calc 1
C C8 0.7636(3) -0.0116(3) 0.9822(2) 0.0215(4) Uani d 1
H H8A 0.7749 0.0390 1.0749 0.032 Uiso calc 1
H H8B 0.8328 -0.0812 0.9806 0.032 Uiso calc 1
H H8C 0.6338 -0.0904 0.9481 0.032 Uiso calc 1
Cl Cl1 0.32457(6) 0.78356(6) 0.65025(4) 0.01406(11) Uani d 1
O O1 0.1610(2) 0.6610(2) 0.56090(18) 0.0282(4) Uani d 1
O O2 0.48300(19) 0.77847(19) 0.60352(16) 0.0221(3) Uani d 1
O O3 0.3102(3) 0.7249(2) 0.78200(16) 0.0319(4) Uani d 1
O O4 0.3413(2) 0.96148(19) 0.65392(18) 0.0285(4) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0050 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0090 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1230 0.1260 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3550 1.0370 '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
N1 Cu1 N1 . 2_666 180.00(9)
N1 Cu1 N2 . 2_666 86.45(7)
N1 Cu1 N2 2_666 2_666 93.55(7)
N1 Cu1 N2 . . 93.55(7)
N1 Cu1 N2 2_666 . 86.45(7)
N2 Cu1 N2 2_666 . 180.0
C1 N1 C2 . . 112.37(15)
C1 N1 Cu1 . . 106.33(11)
C2 N1 Cu1 . . 115.28(12)
C1 N1 H1 . . 107.5
C2 N1 H1 . . 107.5
Cu1 N1 H1 . . 107.5
C4 N2 C3 . . 113.49(15)
C4 N2 Cu1 . . 106.73(11)
C3 N2 Cu1 . . 115.29(12)
C4 N2 H2 . . 107.0
C3 N2 H2 . . 107.0
Cu1 N2 H2 . . 107.0
C2 N3 C3 . . 114.81(15)
C2 N3 C5 . . 114.08(15)
C3 N3 C5 . . 116.15(16)
N1 C1 C4 . 2_666 107.87(15)
N1 C1 H1A . . 110.1
C4 C1 H1A 2_666 . 110.1
N1 C1 H1B . . 110.1
C4 C1 H1B 2_666 . 110.1
H1A C1 H1B . . 108.4
N3 C2 N1 . . 114.03(15)
N3 C2 H2A . . 108.7
N1 C2 H2A . . 108.7
N3 C2 H2B . . 108.7
N1 C2 H2B . . 108.7
H2A C2 H2B . . 107.6
N3 C3 N2 . . 113.39(15)
N3 C3 H3A . . 108.9
N2 C3 H3A . . 108.9
N3 C3 H3B . . 108.9
N2 C3 H3B . . 108.9
H3A C3 H3B . . 107.7
N2 C4 C1 . 2_666 107.28(15)
N2 C4 H4A . . 110.3
C1 C4 H4A 2_666 . 110.3
N2 C4 H4B . . 110.3
C1 C4 H4B 2_666 . 110.3
H4A C4 H4B . . 108.5
N3 C5 C6 . . 113.14(15)
N3 C5 H5A . . 109.0
C6 C5 H5A . . 109.0
N3 C5 H5B . . 109.0
C6 C5 H5B . . 109.0
H5A C5 H5B . . 107.8
C5 C6 C7 . . 112.19(16)
C5 C6 H6A . . 109.2
C7 C6 H6A . . 109.2
C5 C6 H6B . . 109.2
C7 C6 H6B . . 109.2
H6A C6 H6B . . 107.9
C6 C7 C8 . . 112.45(16)
C6 C7 H7A . . 109.1
C8 C7 H7A . . 109.1
C6 C7 H7B . . 109.1
C8 C7 H7B . . 109.1
H7A C7 H7B . . 107.8
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
O4 Cl1 O3 . . 110.11(11)
O4 Cl1 O1 . . 109.74(10)
O3 Cl1 O1 . . 108.36(11)
O4 Cl1 O2 . . 110.65(10)
O3 Cl1 O2 . . 108.82(10)
O1 Cl1 O2 . . 109.12(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N1 . 2.0073(17)
Cu1 N1 2_666 2.0073(17)
Cu1 N2 2_666 2.0131(17)
Cu1 N2 . 2.0131(17)
N1 C1 . 1.478(2)
N1 C2 . 1.501(3)
N1 H1 . 1.0000
N2 C4 . 1.487(2)
N2 C3 . 1.496(3)
N2 H2 . 1.0000
N3 C2 . 1.432(2)
N3 C3 . 1.440(2)
N3 C5 . 1.478(2)
C1 C4 2_666 1.518(3)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 H3A . 0.9900
C3 H3B . 0.9900
C4 C1 2_666 1.518(3)
C4 H4A . 0.9900
C4 H4B . 0.9900
C5 C6 . 1.515(3)
C5 H5A . 0.9900
C5 H5B . 0.9900
C6 C7 . 1.522(3)
C6 H6A . 0.9900
C6 H6B . 0.9900
C7 C8 . 1.523(3)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
Cl1 O4 . 1.4293(15)
Cl1 O3 . 1.4318(17)
Cl1 O1 . 1.4420(17)
Cl1 O2 . 1.4481(14)
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 O1 1_655 1.00 2.50 3.136(2) 121.3
N2 H2 O4 1_545 1.00 2.17 3.000(2) 139.0
C1 H1A O1 1_655 0.99 2.46 3.160(2) 127.1
N1 H1 O1 2_666 1.00 2.08 3.018(2) 154.9
C6 H6B O3 2_667 0.99 2.50 3.338(3) 142.1
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_4
_geom_torsion
C2 N1 C1 C4 2_666 -169.53(14)
Cu1 N1 C1 C4 2_666 -42.53(15)
C3 N3 C2 N1 . -69.8(2)
C5 N3 C2 N1 . 67.8(2)
C1 N1 C2 N3 . 178.48(14)
Cu1 N1 C2 N3 . 56.43(18)
C2 N3 C3 N2 . 70.2(2)
C5 N3 C3 N2 . -66.5(2)
C4 N2 C3 N3 . 179.24(14)
Cu1 N2 C3 N3 . -57.23(18)
C3 N2 C4 C1 2_666 168.24(15)
Cu1 N2 C4 C1 2_666 40.14(16)
C2 N3 C5 C6 . 167.34(16)
C3 N3 C5 C6 . -55.6(2)
N3 C5 C6 C7 . -172.24(17)
C5 C6 C7 C8 . -172.38(18)
