#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/29/1512962.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_1512962
loop_
_publ_author_name
'Neil F. Curtis'
'Jan Wikaira'
_publ_section_title
;
 meso-(5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradec-4,11-diene)
 copper(II) perchlorate; an unexpected preparation and structure
 determination
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              14
_journal_page_last               16
_journal_paper_doi               10.1016/j.ica.2012.11.027
_journal_volume                  396
_journal_year                    2013
_chemical_formula_moiety         'C16 H32 N4 Cu, 2(Cl O4)'
_chemical_formula_sum            'C16 H32 Cl2 Cu N4 O8'
_chemical_formula_weight         542.90
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 111.179(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2477(3)
_cell_length_b                   10.4920(2)
_cell_length_c                   10.9152(3)
_cell_measurement_reflns_used    2463
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      73.3308
_cell_measurement_theta_min      4.2102
_cell_volume                     1094.32(5)
_computing_data_collection
; CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'ORTEP3.2 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3474
_diffrn_reflns_theta_full        65.49
_diffrn_reflns_theta_max         65.49
_diffrn_reflns_theta_min         4.63
_exptl_absorpt_coefficient_mu    4.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
 
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             566
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0267
_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)+(0.0403P)²+0.9409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0737
_reflns_number_gt                1759
_reflns_number_total             1876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-396-14-16.cif
_cod_data_source_block           nfc4-9-4
_cod_database_code               1512962
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_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 0.0000 0.0000 0.0000 0.00913(13) Uani 1 2 d S
C5 C -0.2725(2) 0.00691(17) -0.21820(19) 0.0116(4) Uani 1 1 d .
N8 N -0.13880(16) 0.04434(15) 0.08365(14) 0.0100(3) Uani 1 1 d .
H8 H -0.1710 -0.0310 0.1031 0.012 Uiso 1 1 calc R
C9 C -0.0575(2) 0.10507(19) 0.21148(17) 0.0139(4) Uani 1 1 d .
H9A H -0.1139 0.1102 0.2661 0.017 Uiso 1 1 calc R
H5B H -0.0302 0.1907 0.1973 0.017 Uiso 1 1 calc R
C7 C -0.26532(19) 0.11727(18) -0.00119(18) 0.0113(4) Uani 1 1 d .
N4 N -0.13907(17) 0.00118(14) -0.18235(15) 0.0116(3) Uani 1 1 d .
C6 C -0.34173(19) 0.03351(19) -0.12056(19) 0.0132(4) Uani 1 1 d .
H6A H -0.3606 -0.0478 -0.0881 0.016 Uiso 1 1 calc R
H6B H -0.4315 0.0729 -0.1678 0.016 Uiso 1 1 calc R
C72 C -0.2226(2) 0.24422(18) -0.04368(19) 0.0154(4) Uani 1 1 d .
H72A H -0.1881 0.3000 0.0308 0.023 Uiso 1 1 calc R
H72B H -0.3023 0.2825 -0.1096 0.023 Uiso 1 1 calc R
H72C H -0.1505 0.2300 -0.0790 0.023 Uiso 1 1 calc R
C71 C -0.3649(2) 0.1403(2) 0.07276(19) 0.0169(4) Uani 1 1 d .
H71A H -0.3844 0.0608 0.1062 0.025 Uiso 1 1 calc R
H71B H -0.4506 0.1766 0.0140 0.025 Uiso 1 1 calc R
H71C H -0.3221 0.1978 0.1444 0.025 Uiso 1 1 calc R
C10 C 0.0711(2) 0.0243(2) 0.27814(19) 0.0159(4) Uani 1 1 d .
H10A H 0.1352 0.0690 0.3538 0.019 Uiso 1 1 calc R
H10B H 0.0447 -0.0552 0.3080 0.019 Uiso 1 1 calc R
C51 C -0.3719(2) -0.0151(2) -0.3563(2) 0.0182(4) Uani 1 1 d .
H51A H -0.3530 0.0451 -0.4141 0.027 Uiso 1 1 calc R
H51B H -0.4663 -0.0044 -0.3601 0.027 Uiso 1 1 calc R
H51C H -0.3599 -0.1001 -0.3831 0.027 Uiso 1 1 calc R
Cl1 Cl -0.24421(5) -0.32976(4) -0.15136(4) 0.01550(14) Uani 1 1 d .
O1 O -0.14069(17) -0.26259(16) -0.04507(15) 0.0278(4) Uani 1 1 d .
O2 O -0.24422(19) -0.46269(15) -0.11860(16) 0.0294(4) Uani 1 1 d .
O3 O -0.37992(16) -0.27605(16) -0.17399(17) 0.0297(4) Uani 1 1 d .
O4 O -0.21163(18) -0.31632(15) -0.26901(15) 0.0265(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
N4 Cu1 N4 180.00(6) 3 .
N4 Cu1 N8 94.86(6) 3 3
N4 Cu1 N8 85.14(6) . 3
N4 Cu1 N8 85.14(6) 3 .
N4 Cu1 N8 94.86(6) . .
N8 Cu1 N8 180.00(6) 3 .
N4 Cu1 O3 126.49(5) 3 .
N4 Cu1 O3 53.51(5) . .
N8 Cu1 O3 107.19(5) 3 .
N8 Cu1 O3 72.81(5) . .
N4 C5 C51 124.21(18) . .
N4 C5 C6 121.14(17) . .
C51 C5 C6 114.64(16) . .
C9 N8 C7 115.27(14) . .
C9 N8 Cu1 106.14(11) . .
C7 N8 Cu1 115.73(11) . .
N8 C9 C10 107.88(15) . .
N8 C7 C72 110.71(15) . .
N8 C7 C6 107.12(15) . .
C72 C7 C6 110.91(15) . .
N8 C7 C71 110.26(15) . .
C72 C7 C71 109.97(16) . .
C6 C7 C71 107.78(15) . .
C5 N4 C10 121.15(16) . 3
C5 N4 Cu1 127.38(14) . .
C10 N4 Cu1 110.96(12) 3 .
C5 C6 C7 118.81(16) . .
N4 C10 C9 108.23(15) 3 .
O3 Cl1 O2 109.61(10) . .
O3 Cl1 O1 109.37(10) . .
O2 Cl1 O1 109.86(10) . .
O3 Cl1 O4 109.20(10) . .
O2 Cl1 O4 109.62(9) . .
O1 Cl1 O4 109.16(10) . .
Cl1 O3 Cu1 63.92(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N4 1.9858(16) 3
Cu1 N4 1.9858(16) .
Cu1 N8 2.0030(15) 3
Cu1 N8 2.0030(15) .
C5 N4 1.280(3) .
C5 C51 1.502(3) .
C5 C6 1.505(3) .
N8 C9 1.486(2) .
N8 C7 1.502(2) .
C9 C10 1.513(3) .
C7 C72 1.526(3) .
C7 C6 1.532(3) .
C7 C71 1.532(3) .
N4 C10 1.475(2) 3
C10 N4 1.475(2) 3
Cl1 O3 1.4369(16) .
Cl1 O2 1.4397(16) .
Cl1 O1 1.4418(16) .
Cl1 O4 1.4458(15) .
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
N8 H8 O4 0.91 2.26 3.120(2) 157.2 4_556
