#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/90/2019057.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_2019057
loop_
_publ_author_name
'Nath, Babul Chandra'
'Suarez, Sebastián'
'Doctorovich, Fabio'
'Roy, Tapashi G.'
'Baggio, Ricardo'
_publ_section_title
;
 Two solvatomorphic forms of a copper complex formulated as
 Cu(L¹)(ClO₄)₂·1.2H₂O and
 Cu(L¹)(ClO₄)₂, where L¹ is
 3,10-C-meso-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane
;
_journal_coeditor_code           SK3486
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              689
_journal_page_last               695
_journal_paper_doi               10.1107/S0108270113013711
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Cu (Cl O4)2 (C18 H40 N4)] , 1.2H2 O'
_chemical_formula_moiety         'C18 H40 Cl2 Cu N4 O8, 1.2(H2 O)'
_chemical_formula_sum            'C18 H42.4 Cl2 Cu N4 O9.2'
_chemical_formula_weight         596.61
_chemical_name_systematic
'(3,10-C-meso-3,5,7,7,10,12,14,14-Octamethyl-1,4,8,11-tetraazacyclotetradecane)bis(perchlorato-κO)copper(II) 1.2-hydrate'
_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           SHELXL97
_cell_angle_alpha                114.835(13)
_cell_angle_beta                 98.036(10)
_cell_angle_gamma                98.616(11)
_cell_formula_units_Z            1
_cell_length_a                   8.5783(10)
_cell_length_b                   8.7819(12)
_cell_length_c                   10.2156(13)
_cell_measurement_reflns_used    2039
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.9870
_cell_measurement_theta_min      3.6919
_cell_volume                     672.67(17)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'Oxford Gemini S Ultra CCD area-detector'
_diffrn_measurement_method       'ω scans, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0582
_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            9475
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.05
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             315.0
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.489
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0550
_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)+(0.0891P)²+0.8414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1702
_reflns_number_gt                2285
_reflns_number_total             3193
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3486.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C18 H42.40 Cl2 Cu N4 O9.20'
_cod_database_code               2019057
_cod_database_fobs_code          2019057
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.5000 0.5000 0.5000 0.0396(2) Uani d S 1 2 . .
N N1 0.4193(4) 0.4998(4) 0.3045(3) 0.0432(7) Uani d . 1 1 B .
H H1N 0.4850 0.4473 0.2459 0.052 Uiso calc R 1 1 . .
N N2 0.3720(4) 0.2576(4) 0.4358(3) 0.0399(7) Uani d . 1 1 B .
H H2N 0.4379 0.1906 0.3899 0.048 Uiso calc R 1 1 . .
C C1 0.4601(5) 0.6810(5) 0.3304(5) 0.0516(9) Uani d . 1 1 . .
H H1A 0.3821 0.7410 0.3777 0.062 Uiso calc R 1 1 B .
H H1B 0.4557 0.6853 0.2367 0.062 Uiso calc R 1 1 . .
C C2 0.2487(5) 0.4023(5) 0.2150(5) 0.0518(10) Uani d . 1 1 . .
C C3 0.2286(5) 0.2165(5) 0.1939(4) 0.0499(9) Uani d . 1 1 B .
H H3A 0.1324 0.1470 0.1163 0.060 Uiso calc R 1 1 . .
H H3B 0.3201 0.1750 0.1574 0.060 Uiso calc R 1 1 . .
C C4 0.2151(4) 0.1818(5) 0.3250(4) 0.0435(8) Uani d . 1 1 . .
H H4 0.1333 0.2381 0.3713 0.052 Uiso calc R 1 1 B .
C C5 0.3710(5) 0.2314(5) 0.5712(4) 0.0462(9) Uani d . 1 1 . .
H H5 0.3524 0.1075 0.5421 0.055 Uiso calc R 1 1 B .
C C6 0.2299(9) 0.3967(8) 0.0608(6) 0.094(2) Uani d . 1 1 B .
H H6A 0.3201 0.3615 0.0201 0.141 Uiso calc R 1 1 . .
H H6B 0.2265 0.5092 0.0694 0.141 Uiso calc R 1 1 . .
H H6C 0.1313 0.3159 -0.0031 0.141 Uiso calc R 1 1 . .
C C7 0.1256(5) 0.4880(6) 0.2930(7) 0.0729(15) Uani d . 1 1 B .
H H7A 0.0217 0.4085 0.2532 0.109 Uiso calc R 1 1 . .
H H7B 0.1192 0.5881 0.2783 0.109 Uiso calc R 1 1 . .
H H7C 0.1579 0.5218 0.3969 0.109 Uiso calc R 1 1 . .
C C8 0.1590(5) -0.0120(5) 0.2735(5) 0.0593(11) Uani d . 1 1 B .
H H8A 0.0548 -0.0546 0.2064 0.089 Uiso calc R 1 1 . .
H H8B 0.1516 -0.0330 0.3576 0.089 Uiso calc R 1 1 . .
H H8C 0.2354 -0.0700 0.2240 0.089 Uiso calc R 1 1 . .
C C9 0.2394(6) 0.2996(6) 0.6470(5) 0.0617(11) Uani d . 1 1 B .
H H9A 0.2454 0.4158 0.6614 0.093 Uiso calc R 1 1 . .
H H9B 0.2539 0.2979 0.7413 0.093 Uiso calc R 1 1 . .
H H9C 0.1355 0.2284 0.5865 0.093 Uiso calc R 1 1 . .
O O1W 0.5853(11) 0.2881(8) 0.0354(8) 0.094(3) Uani d PD 0.60(2) 1 A 1
H H1WB 0.519(13) 0.197(9) -0.031(10) 0.141 Uiso d PD 0.60(2) 1 A 1
H H1WA 0.618(16) 0.263(14) 0.105(9) 0.141 Uiso d PD 0.60(2) 1 A 1
Cl Cl1 0.72465(13) 0.12868(15) 0.28330(15) 0.0532(4) Uani d PD 0.922(3) 1 B 1
O O3 0.8372(4) 0.1240(5) 0.3979(4) 0.0814(12) Uani d PD 0.922(3) 1 B 1
O O1 0.6966(7) 0.2981(5) 0.3343(6) 0.0854(12) Uani d PD 0.922(3) 1 B 1
O O2 0.7911(5) 0.0887(6) 0.1564(4) 0.0908(14) Uani d PD 0.922(3) 1 B 1
O O4 0.5759(4) 0.0117(5) 0.2537(5) 0.0791(13) Uani d PD 0.922(3) 1 B 1
Cl Cl1' 0.7019(16) 0.1550(18) 0.2246(19) 0.0532(4) Uani d PD 0.078(3) 1 B 2
O O3' 0.699(4) 0.191(5) 0.101(3) 0.0814(12) Uani d PD 0.078(3) 1 B 2
O O1' 0.684(6) 0.302(4) 0.348(4) 0.0854(12) Uani d PD 0.078(3) 1 B 2
O O2' 0.852(3) 0.115(6) 0.261(4) 0.0908(14) Uani d PD 0.078(3) 1 B 2
O O4' 0.572(4) 0.012(5) 0.189(5) 0.0791(13) Uani d PD 0.078(3) 1 B 2
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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 N2 2_666 2_666 94.25(12)
N1 Cu1 N2 . 2_666 85.75(12)
N1 Cu1 N2 2_666 . 85.75(12)
N1 Cu1 N2 . . 94.25(12)
N1 Cu1 O1 2_666 2_666 81.43(14)
N1 Cu1 O1 . 2_666 98.57(14)
N2 Cu1 O1 2_666 2_666 78.20(13)
N2 Cu1 O1 . 2_666 101.80(13)
N1 Cu1 O1 2_666 . 98.57(14)
N1 Cu1 O1 . . 81.43(14)
N2 Cu1 O1 2_666 . 101.80(13)
N2 Cu1 O1 . . 78.20(13)
C1 N1 C2 . . 114.2(3)
C1 N1 Cu1 . . 106.5(2)
C2 N1 Cu1 . . 120.1(2)
C1 N1 H1N . . 104.9
C2 N1 H1N . . 104.9
Cu1 N1 H1N . . 104.9
C4 N2 C5 . . 114.2(3)
C4 N2 Cu1 . . 122.3(2)
C5 N2 Cu1 . . 108.0(2)
C4 N2 H2N . . 103.3
C5 N2 H2N . . 103.3
Cu1 N2 H2N . . 103.3
N1 C1 C5 . 2_666 109.6(3)
N1 C1 H1A . . 109.8
C5 C1 H1A 2_666 . 109.8
N1 C1 H1B . . 109.8
C5 C1 H1B 2_666 . 109.8
H1A C1 H1B . . 108.2
C7 C2 N1 . . 110.6(3)
C7 C2 C3 . . 111.7(4)
N1 C2 C3 . . 107.4(3)
C7 C2 C6 . . 110.4(5)
N1 C2 C6 . . 108.9(4)
C3 C2 C6 . . 107.7(4)
C4 C3 C2 . . 118.7(3)
C4 C3 H3A . . 107.6
C2 C3 H3A . . 107.6
C4 C3 H3B . . 107.6
C2 C3 H3B . . 107.6
H3A C3 H3B . . 107.1
N2 C4 C3 . . 110.0(3)
N2 C4 C8 . . 112.1(3)
C3 C4 C8 . . 110.0(3)
N2 C4 H4 . . 108.2
C3 C4 H4 . . 108.2
C8 C4 H4 . . 108.2
N2 C5 C9 . . 112.1(3)
N2 C5 C1 . 2_666 105.9(3)
C9 C5 C1 . 2_666 113.0(4)
N2 C5 H5 . . 108.6
C9 C5 H5 . . 108.6
C1 C5 H5 2_666 . 108.6
C2 C6 H6A . . 109.5
C2 C6 H6B . . 109.5
H6A C6 H6B . . 109.5
C2 C6 H6C . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
C2 C7 H7A . . 109.5
C2 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C2 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C4 C8 H8A . . 109.5
C4 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C4 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C5 C9 H9A . . 109.5
C5 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C5 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
H1WB O1W H1WA . . 105.1(17)
O2 Cl1 O3 . . 109.2(2)
O2 Cl1 O4 . . 112.4(3)
O3 Cl1 O4 . . 108.8(2)
O2 Cl1 O1 . . 109.4(3)
O3 Cl1 O1 . . 108.7(3)
O4 Cl1 O1 . . 108.3(2)
Cl1 O1 Cu1 . . 140.1(3)
O3' Cl1' O4' . . 109.4(5)
O3' Cl1' O2' . . 109.6(5)
O4' Cl1' O2' . . 109.5(5)
O3' Cl1' O1' . . 109.5(5)
O4' Cl1' O1' . . 109.3(5)
O2' Cl1' O1' . . 109.5(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 N1 2_666 2.020(3) ?
Cu1 N1 . 2.020(3) y
Cu1 N2 2_666 2.023(3) ?
Cu1 N2 . 2.023(3) y
Cu1 O1 2_666 2.833(4) ?
Cu1 O1 . 2.833(4) y
N1 C1 . 1.476(5) ?
N1 C2 . 1.518(5) ?
N1 H1N . 0.9100 ?
N2 C4 . 1.486(5) ?
N2 C5 . 1.496(5) ?
N2 H2N . 0.9100 ?
C1 C5 2_666 1.520(6) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C7 . 1.511(7) ?
C2 C3 . 1.532(6) ?
C2 C6 . 1.539(6) ?
C3 C4 . 1.509(5) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C8 . 1.528(5) ?
C4 H4 . 0.9800 ?
C5 C9 . 1.513(6) ?
C5 C1 2_666 1.520(6) ?
C5 H5 . 0.9800 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
O1W H1WB . 0.850(10) ?
O1W H1WA . 0.851(10) ?
Cl1 O2 . 1.418(3) ?
Cl1 O3 . 1.428(3) ?
Cl1 O4 . 1.419(3) ?
Cl1 O1 . 1.427(3) ?
Cl1' O3' . 1.422(4) ?
Cl1' O4' . 1.423(4) ?
Cl1' O2' . 1.422(4) ?
Cl1' O1' . 1.423(4) ?
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 H1N O1W . 0.91 2.38 3.261(9) 163
N2 H2N O4 . 0.91 2.23 3.138(6) 173
C7 H7C O1 2_666 0.96 2.52 3.437(7) 159
C9 H9A O1 2_666 0.96 2.47 3.412(7) 168
O1W H1WA O2 . 0.851(10) 2.44(9) 3.137(9) 139(12)
O1W H1WA O1 . 0.851(10) 2.22(4) 3.029(9) 159(11)
O1W H1WB O4 2_655 0.850(10) 2.17(6) 2.967(8) 155(12)
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 N1 C1 2_666 . -14.7(3)
N2 Cu1 N1 C1 . . 165.3(3)
O1 Cu1 N1 C1 2_666 . 62.7(3)
O1 Cu1 N1 C1 . . -117.3(3)
N2 Cu1 N1 C2 2_666 . -146.4(3)
N2 Cu1 N1 C2 . . 33.6(3)
O1 Cu1 N1 C2 2_666 . -69.0(3)
O1 Cu1 N1 C2 . . 111.0(3)
N1 Cu1 N2 C4 2_666 . 150.3(3)
N1 Cu1 N2 C4 . . -29.7(3)
O1 Cu1 N2 C4 2_666 . 70.0(3)
O1 Cu1 N2 C4 . . -110.0(3)
N1 Cu1 N2 C5 2_666 . 14.6(2)
N1 Cu1 N2 C5 . . -165.4(2)
O1 Cu1 N2 C5 2_666 . -65.7(3)
O1 Cu1 N2 C5 . . 114.3(3)
C2 N1 C1 C5 . 2_666 176.4(3)
Cu1 N1 C1 C5 . 2_666 41.5(4)
C1 N1 C2 C7 . . -59.9(5)
Cu1 N1 C2 C7 . . 68.5(4)
C1 N1 C2 C3 . . 178.1(3)
Cu1 N1 C2 C3 . . -53.6(4)
C1 N1 C2 C6 . . 61.6(5)
Cu1 N1 C2 C6 . . -170.0(3)
C7 C2 C3 C4 . . -49.0(5)
N1 C2 C3 C4 . . 72.3(4)
C6 C2 C3 C4 . . -170.4(4)
C5 N2 C4 C3 . . 179.5(3)
Cu1 N2 C4 C3 . . 46.2(4)
C5 N2 C4 C8 . . -57.7(4)
Cu1 N2 C4 C8 . . 169.0(3)
C2 C3 C4 N2 . . -68.5(4)
C2 C3 C4 C8 . . 167.5(4)
C4 N2 C5 C9 . . -55.8(4)
Cu1 N2 C5 C9 . . 83.9(3)
C4 N2 C5 C1 . 2_666 -179.4(3)
Cu1 N2 C5 C1 . 2_666 -39.8(3)
O2 Cl1 O1 Cu1 . . 155.8(4)
O3 Cl1 O1 Cu1 . . -85.0(5)
O4 Cl1 O1 Cu1 . . 33.1(6)
N1 Cu1 O1 Cl1 2_666 . 62.7(5)
N1 Cu1 O1 Cl1 . . -117.3(5)
N2 Cu1 O1 Cl1 2_666 . 158.9(5)
N2 Cu1 O1 Cl1 . . -21.1(5)
O4' Cl1' O3' O1' . . 119.8(7)
O2' Cl1' O3' O1' . . -120.1(7)
O3' Cl1' O1' O4' . . 119.8(7)
O2' Cl1' O1' O4' . . -120.0(7)
O3' Cl1' O2' O1' . . 120.1(7)
O4' Cl1' O2' O1' . . -119.9(7)
O4' O1' O2' Cl1' . . 35.3(4)
O3' Cl1' O4' O1' . . -119.9(7)
O2' Cl1' O4' O1' . . 119.9(7)
