#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:40:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179341 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/38/4323879.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_4323879
loop_
_publ_author_name
'Monica Rossignoli'
'Christine C. Allen'
'Trevor W. Hambley'
'Geoffrey A. Lawrance'
'Marcel Maeder'
_publ_contact_author
;
        Prof. Geoffrey A. Lawrance
        Department of Chemistry
        University of Newcastle
        Callaghan 2308
        Australia
;
_publ_section_title
;
 "Swollen" Macrocycles: Palladium(II)-Directed Template Syntheses of
 Pendant-Arm 14-, 16-, and 18-Membered Macrocycles
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4961
_journal_page_last               4966
_journal_paper_doi               10.1021/ic951628r
_journal_volume                  35
_journal_year                    1996
_chemical_formula_sum            'C16 H32 Cl2 N6 O14 Pd'
_chemical_formula_weight         709.78
_chemical_name_common            '[Pd(dino[18]mac)](ClO₄)₂'
_chemical_name_systematic
;(3,12-Dimethyl-3,12-dinitro-1,5,10,14-tetraazacyclooctadecane)palladium(II) 
 perchlorate 
;
_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_date             96-04-03
_audit_creation_method           SHELXL
_cell_angle_alpha                91.76(6)
_cell_angle_beta                 101.73(7)
_cell_angle_gamma                112.83(5)
_cell_formula_units_Z            2
_cell_length_a                   7.746(5)
_cell_length_b                   9.912(5)
_cell_length_c                   18.96(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     1303.9(19)
_computing_data_collection       'CAD4 (Enraf-Nonius)'
_computing_data_reduction
'Enraf-Nonius Structure Determination Package'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'CAD4 (Enraf-Nonius)'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    56.0267
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4595
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.10
_diffrn_standards_decay_%        1.03
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.83
_exptl_crystal_colour            near-colourless
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_meas      1.82
_exptl_crystal_density_method    flotation
_exptl_crystal_description       plate
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.075
_refine_diff_density_max         1.119
_refine_diff_density_min         -1.734
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.044
_refine_ls_goodness_of_fit_obs   1.110
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_restrained_S_obs      1.110
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_obs          0.0713
_refine_ls_shift/esd_max         -0.109
_refine_ls_shift/esd_mean        0.024
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1337P)²+5.5100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2149
_refine_ls_wR_factor_obs         0.2061
_reflns_number_observed          3921
_reflns_number_total             4595
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic951628r_3.cif
_cod_data_source_block           (III)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1337P)^2^+5.5100P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1337P)^2^+5.5100P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1303.9(11)
_cod_database_code               4323879
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Pd1 Pd 0.07735(7) 0.24996(6) 0.24999(3) 0.0384(2) Uani 1 d . .
N1 N 0.1965(9) 0.4772(7) 0.2542(4) 0.0446(14) Uani 1 d . .
H1 H 0.1597(9) 0.5114(7) 0.2911(4) 0.129(10) Uiso 1 calc R .
N2 N 0.0028(11) 0.2306(9) 0.1374(4) 0.056(2) Uani 1 d . .
H2 H 0.0151(11) 0.2217(9) 0.1856(4) 0.129(10) Uiso 1 calc R .
N3 N -0.0348(9) 0.0232(7) 0.2462(4) 0.0457(14) Uani 1 d . .
H3 H -0.1423(9) -0.0107(7) 0.2093(4) 0.129(10) Uiso 1 calc R .
N4 N 0.1380(10) 0.2699(9) 0.3620(4) 0.057(2) Uani 1 d . .
H4 H 0.1133(10) 0.2788(9) 0.3138(4) 0.129(10) Uiso 1 calc R .
C1 C 0.1364(13) 0.5430(9) 0.1907(5) 0.056(2) Uani 1 d . .
H1A H 0.2245(13) 0.5542(9) 0.1594(5) 0.129(10) Uiso 1 calc R .
H1B H 0.1503(13) 0.6411(9) 0.2071(5) 0.129(10) Uiso 1 calc R .
C2 C -0.0674(11) 0.4595(10) 0.1457(5) 0.051(2) Uani 1 d . .
C21 C -0.1175(16) 0.5561(12) 0.0912(6) 0.070(3) Uani 1 d . .
H21A H -0.0921(16) 0.6501(12) 0.1161(6) 0.129(10) Uiso 1 calc R .
H21B H -0.2515(16) 0.5090(12) 0.0671(6) 0.129(10) Uiso 1 calc R .
H21C H -0.0407(16) 0.5702(12) 0.0560(6) 0.129(10) Uiso 1 calc R .
N5 N -0.2024(13) 0.4397(16) 0.1969(6) 0.096(4) Uani 1 d . .
O51 O -0.1556(18) 0.5376(20) 0.2454(8) 0.158(6) Uani 1 d . .
O52 O -0.3448(22) 0.3433(24) 0.1825(10) 0.238(11) Uani 1 d . .
C3 C -0.1068(18) 0.3147(11) 0.1068(6) 0.080(3) Uani 1 d . .
H3A H -0.2422(18) 0.2529(11) 0.1015(6) 0.129(10) Uiso 1 calc R .
H3B H -0.0870(18) 0.3309(11) 0.0583(6) 0.129(10) Uiso 1 calc R .
C4 C 0.1497(27) 0.2158(22) 0.1046(11) 0.0615(13) Uani 0.50 d P .
H4A H 0.0901(27) 0.1729(22) 0.0545(11) 0.129(10) Uiso 0.50 calc PR .
H4B H 0.2458(27) 0.3138(22) 0.1041(11) 0.129(10) Uiso 0.50 calc PR .
C4' C -0.0578(27) 0.1085(21) 0.0931(11) 0.0615(13) Uani 0.50 d P .
H4'A H -0.0939(27) 0.1286(21) 0.0437(11) 0.129(10) Uiso 0.50 calc PR .
H4'B H -0.1720(27) 0.0360(21) 0.1045(11) 0.129(10) Uiso 0.50 calc PR .
C5 C 0.2473(27) 0.1284(21) 0.1385(11) 0.0615(13) Uani 0.50 d P .
H5A H 0.3259(27) 0.1808(21) 0.1856(11) 0.129(10) Uiso 0.50 calc PR .
H5B H 0.3340(27) 0.1221(21) 0.1094(11) 0.129(10) Uiso 0.50 calc PR .
C5' C 0.1004(26) 0.0404(22) 0.0974(11) 0.0615(13) Uani 0.50 d P .
H5'A H 0.0356(26) -0.0613(22) 0.0751(11) 0.129(10) Uiso 0.50 calc PR .
H5'B H 0.1893(26) 0.0935(22) 0.0685(11) 0.129(10) Uiso 0.50 calc PR .
C6 C 0.1194(29) -0.0296(23) 0.1497(11) 0.0615(13) Uani 0.50 d P .
H6A H -0.0061(29) -0.0602(23) 0.1167(11) 0.129(10) Uiso 0.50 calc PR .
H6B H 0.1767(29) -0.0959(23) 0.1376(11) 0.129(10) Uiso 0.50 calc PR .
C6' C 0.2143(28) 0.0432(23) 0.1708(11) 0.0615(13) Uani 0.50 d P .
H6'A H 0.2871(28) 0.1452(23) 0.1919(11) 0.129(10) Uiso 0.50 calc PR .
H6'B H 0.3063(28) 0.0015(23) 0.1659(11) 0.129(10) Uiso 0.50 calc PR .
C7 C 0.0941(16) -0.0424(11) 0.2257(6) 0.065(2) Uani 1 d . .
H7A H 0.1324(16) -0.1100(11) 0.2552(6) 0.129(10) Uiso 1 calc R .
C8 C -0.0974(13) -0.0421(9) 0.3089(5) 0.054(2) Uani 1 d . .
H8A H 0.0101(13) -0.0544(9) 0.3401(5) 0.129(10) Uiso 1 calc R .
H8B H -0.1981(13) -0.1397(9) 0.2922(5) 0.129(10) Uiso 1 calc R .
C9 C -0.1721(12) 0.0409(10) 0.3545(5) 0.051(2) Uani 1 d . .
C91 C -0.2633(15) -0.0560(12) 0.4094(6) 0.071(3) Uani 1 d . .
H91A H -0.3567(15) -0.1498(12) 0.3845(6) 0.129(10) Uiso 1 calc R .
H91B H -0.3254(15) -0.0086(12) 0.4339(6) 0.129(10) Uiso 1 calc R .
H91C H -0.1651(15) -0.0705(12) 0.4442(6) 0.129(10) Uiso 1 calc R .
N6 N -0.3417(17) 0.0579(16) 0.3026(6) 0.093(3) Uani 1 d . .
O61 O -0.4387(18) -0.0374(19) 0.2545(7) 0.151(6) Uani 1 d . .
O62 O -0.3675(36) 0.1600(26) 0.3176(11) 0.254(13) Uani 1 d . .
C10 C -0.0292(17) 0.1843(11) 0.3936(6) 0.076(3) Uani 1 d . .
H10A H 0.0224(17) 0.1674(11) 0.4420(6) 0.129(10) Uiso 1 calc R .
H10B H -0.0973(17) 0.2465(11) 0.3991(6) 0.129(10) Uiso 1 calc R .
C11 C 0.3277(26) 0.2841(22) 0.3967(11) 0.0615(13) Uani 0.50 d P .
H11A H 0.3267(26) 0.1862(22) 0.3990(11) 0.129(10) Uiso 0.50 calc PR .
H11B H 0.3595(26) 0.3302(22) 0.4461(11) 0.129(10) Uiso 0.50 calc PR .
C11' C 0.2430(26) 0.3937(21) 0.4084(11) 0.0615(13) Uani 0.50 d P .
H11C H 0.2366(26) 0.3721(21) 0.4576(11) 0.129(10) Uiso 0.50 calc PR .
H11D H 0.1894(26) 0.4665(21) 0.3976(11) 0.129(10) Uiso 0.50 calc PR .
C12 C 0.4815(26) 0.3709(21) 0.3606(11) 0.0615(13) Uani 0.50 d P .
H12A H 0.4573(26) 0.3192(21) 0.3130(11) 0.129(10) Uiso 0.50 calc PR .
H12B H 0.6038(26) 0.3754(21) 0.3885(11) 0.129(10) Uiso 0.50 calc PR .
C12' C 0.4637(26) 0.4600(22) 0.4027(11) 0.0615(13) Uani 0.50 d P .
H12C H 0.5234(26) 0.5616(22) 0.4252(11) 0.129(10) Uiso 0.50 calc PR .
H12D H 0.5280(26) 0.4062(22) 0.4313(11) 0.129(10) Uiso 0.50 calc PR .
C13 C 0.4993(27) 0.5317(23) 0.3515(11) 0.0615(13) Uani 0.50 d P .
H13A H 0.4343(27) 0.5601(23) 0.3841(11) 0.129(10) Uiso 0.50 calc PR .
H13B H 0.6341(27) 0.5990(23) 0.3644(11) 0.129(10) Uiso 0.50 calc PR .
C13' C 0.5024(27) 0.4580(24) 0.3306(11) 0.0615(13) Uani 0.50 d P .
H13C H 0.4547(27) 0.3560(24) 0.3098(11) 0.129(10) Uiso 0.50 calc PR .
H13D H 0.6409(27) 0.5007(24) 0.3360(11) 0.129(10) Uiso 0.50 calc PR .
C14 C 0.4114(12) 0.5426(11) 0.2744(6) 0.067(3) Uani 1 d . .
H14A H 0.4874(12) 0.6100(11) 0.2447(6) 0.129(10) Uiso 1 calc R .
Cl1 Cl 0.5306(4) 0.7879(6) 0.0795(2) 0.1052(13) Uani 1 d . .
O11 O 0.6209(19) 0.7530(14) 0.1407(6) 0.121(4) Uani 1 d . .
O12 O 0.5858(18) 0.7628(15) 0.0196(6) 0.129(4) Uani 1 d . .
O13 O 0.3459(13) 0.7702(15) 0.0715(6) 0.121(4) Uani 1 d . .
O14 O 0.6349(21) 0.9542(14) 0.0973(13) 0.235(11) Uani 1 d . .
Cl2 Cl 0.1633(6) 0.7124(6) 0.4205(2) 0.1066(13) Uani 1 d . .
O21 O 0.2264(16) 0.7470(14) 0.3593(6) 0.119(4) Uani 1 d . .
O22 O 0.3040(16) 0.7361(15) 0.4807(6) 0.128(4) Uani 1 d . .
O23 O 0.0051(16) 0.7308(15) 0.4284(6) 0.120(4) Uani 1 d . .
O24 O 0.0765(29) 0.5432(14) 0.4017(12) 0.216(10) Uani 1 d . .
O1 O 0.2951(48) 0.9724(75) 0.4205(14) 0.578(47) Uani 1 d . .
O2 O 0.3978(48) 0.5159(76) 0.0792(14) 0.581(46) Uani 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 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 '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
N3 Pd1 N4 90.0(3) . .
N3 Pd1 N1 178.6(2) . .
N4 Pd1 N1 89.9(3) . .
N3 Pd1 N2 90.2(3) . .
N4 Pd1 N2 177.0(3) . .
N1 Pd1 N2 90.0(3) . .
C1 N1 C14 107.5(6) . .
C1 N1 Pd1 118.2(5) . .
C14 N1 Pd1 113.2(5) . .
C4' N2 C4 65.8(12) . .
C4' N2 C3 107.3(11) . .
C4 N2 C3 121.3(11) . .
C4' N2 Pd1 126.0(10) . .
C4 N2 Pd1 112.6(9) . .
C3 N2 Pd1 115.6(6) . .
C8 N3 C7 107.9(6) . .
C8 N3 Pd1 118.6(5) . .
C7 N3 Pd1 112.8(5) . .
C11' N4 C11 65.4(12) . .
C11' N4 C10 105.8(10) . .
C11 N4 C10 119.8(11) . .
C11' N4 Pd1 127.3(10) . .
C11 N4 Pd1 115.3(9) . .
C10 N4 Pd1 114.9(6) . .
N1 C1 C2 116.5(7) . .
C3 C2 C1 115.7(8) . .
C3 C2 C21 109.2(8) . .
C1 C2 C21 109.3(7) . .
C3 C2 N5 110.1(10) . .
C1 C2 N5 107.0(8) . .
C21 C2 N5 105.0(8) . .
O52 N5 O51 124.7(15) . .
O52 N5 C2 117.6(14) . .
O51 N5 C2 117.3(11) . .
N2 C3 C2 119.1(8) . .
C5 C4 N2 116.8(17) . .
N2 C4' C5' 113.1(14) . .
C4 C5 C6 116.8(16) . .
C6' C5' C4' 116.6(16) . .
C7 C6 C5 112.9(16) . .
C5' C6' C7 115.7(15) . .
N3 C7 C6 115.4(10) . .
N3 C7 C6' 114.2(10) . .
C6 C7 C6' 30.7(9) . .
N3 C8 C9 117.1(7) . .
C10 C9 C8 115.9(8) . .
C10 C9 C91 108.7(8) . .
C8 C9 C91 109.5(7) . .
C10 C9 N6 111.5(9) . .
C8 C9 N6 106.0(7) . .
C91 C9 N6 104.7(8) . .
O62 N6 O61 126.2(15) . .
O62 N6 C9 115.1(14) . .
O61 N6 C9 118.5(11) . .
C9 C10 N4 118.7(8) . .
N4 C11 C12 115.0(16) . .
N4 C11' C12' 111.2(14) . .
C11 C12 C13 114.7(16) . .
C13' C12' C11' 117.8(16) . .
C14 C13 C12 110.7(15) . .
C12' C13' C14 116.3(16) . .
N1 C14 C13 114.9(10) . .
N1 C14 C13' 114.2(9) . .
C13 C14 C13' 30.9(9) . .
O12 Cl1 O13 117.3(8) . .
O12 Cl1 O11 114.4(8) . .
O13 Cl1 O11 119.4(8) . .
O12 Cl1 O14 102.1(12) . .
O13 Cl1 O14 101.1(10) . .
O11 Cl1 O14 96.9(10) . .
O23 Cl2 O22 117.6(8) . .
O23 Cl2 O21 119.1(7) . .
O22 Cl2 O21 114.6(8) . .
O23 Cl2 O24 99.5(9) . .
O22 Cl2 O24 103.0(11) . .
O21 Cl2 O24 97.2(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N3 2.065(6) .
Pd1 N4 2.066(7) .
Pd1 N1 2.068(6) .
Pd1 N2 2.077(7) .
N1 C1 1.465(11) .
N1 C14 1.492(10) .
N2 C4' 1.31(2) .
N2 C4 1.45(2) .
N2 C3 1.460(12) .
N3 C8 1.451(11) .
N3 C7 1.489(10) .
N4 C11' 1.35(2) .
N4 C11 1.43(2) .
N4 C10 1.500(12) .
C1 C2 1.517(12) .
C2 C3 1.483(13) .
C2 C21 1.524(12) .
C2 N5 1.530(14) .
N5 O52 1.12(2) .
N5 O51 1.21(2) .
C4 C5 1.44(3) .
C4' C5' 1.60(3) .
C5 C6 1.54(3) .
C5' C6' 1.48(3) .
C6 C7 1.50(2) .
C6' C7 1.58(2) .
C8 C9 1.511(11) .
C9 C10 1.475(13) .
C9 C91 1.530(12) .
C9 N6 1.542(13) .
N6 O62 1.14(2) .
N6 O61 1.19(2) .
C11 C12 1.48(3) .
C11' C12' 1.60(3) .
C12 C13 1.56(3) .
C12' C13' 1.46(3) .
C13 C14 1.51(2) .
C13' C14 1.60(2) .
Cl1 O12 1.341(10) .
Cl1 O13 1.347(9) .
Cl1 O11 1.356(11) .
Cl1 O14 1.519(13) .
Cl2 O23 1.344(9) .
Cl2 O22 1.351(10) .
Cl2 O21 1.352(11) .
Cl2 O24 1.543(13) .
