#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:42:34 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179343 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/40/4324062.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_4324062
loop_
_publ_author_name
'Paul V. Bernhardt'
'Karl A. Byriel'
'Colin H. L. Kennard'
'Philip C. Sharpe'
_publ_contact_author
;
Dr Paul V. Bernhardt
Department of Chemistry
University of Queensland
Brisbane, 4072
Australia
;
_publ_contact_author_email       bernhard@chem.chemistry.uq.oz.au
_publ_contact_author_fax         '+61 7 3365 4273'
_publ_contact_author_phone       '+61 7 3365 4266'
_publ_section_title
;
 The Potentially Hexadentate Isomeric Macrocycles trans- and
 cis-6,13-Diethyl-1,4,8,11-tetraazacyclotetradecane-6,13-diamine and Their
 Cobalt(III) Complexes: Unexpected Conformational Behavior
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2045
_journal_page_last               2052
_journal_paper_doi               10.1021/ic951260y
_journal_volume                  35
_journal_year                    1996
_chemical_formula_sum            'C14 H34 Cl3 Co N6 O12'
_chemical_formula_weight         643.75
_chemical_name_systematic
;
trans-6,13-diethyl-1,4,8,11-tetraazacyclotetradecane-6,13-diamine 
cobalt(III) perchlorate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 111.96(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.461(6)
_cell_length_b                   11.580(2)
_cell_length_c                   15.865(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     2464.0(14)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4 microvax controlled'
_computing_data_reduction        'DIFDAT, XTAL3.2'
_computing_molecular_graphics    PLATON
_computing_publication_material  SHELXL-93
_computing_structure_refinement  SHELXL-93
_computing_structure_solution    SHELXS-86
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Enraf Nonius CAD4-circle diffractometer'
_diffrn_measurement_method       '2θ/w scan mode'
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2254
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 250
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  1.767
_exptl_absorpt_correction_T_min  1.012
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       prisms
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.102
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.046
_refine_ls_goodness_of_fit_obs   1.084
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_restrained_S_obs      1.084
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_obs          0.0586
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1276P)²+2.9964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1706
_refine_ls_wR_factor_obs         0.1543
_reflns_number_observed          1689
_reflns_number_total             2165
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic951260y_2.cif
_cod_data_source_block           891pcs2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1276P)^2^+2.9964P] 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^)+(0.1276P)^2^+2.9964P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4324062
_cod_database_fobs_code          4324062
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Co Co 0.2500 0.7500 0.0000 0.0231(3) Uani 1 d S .
N1 N 0.2034(3) 0.8873(3) -0.0752(2) 0.0360(8) Uani 1 d . .
H1 H 0.1357(3) 0.8820(3) -0.1000(2) 0.047 Uiso 1 d R .
N2 N 0.1605(3) 0.7812(3) 0.0636(3) 0.0320(8) Uani 1 d . .
H2 H 0.0973(3) 0.7865(3) 0.0215(3) 0.042 Uiso 1 d R .
N3 N 0.3372(2) 0.8586(3) 0.0883(2) 0.0299(8) Uani 1 d . .
H3A H 0.3623(2) 0.8275(3) 0.1444(2) 0.039 Uiso 1 d R .
H3B H 0.3875(2) 0.8829(3) 0.0724(2) 0.039 Uiso 1 d R .
C1 C 0.1866(4) 0.8942(5) 0.1105(4) 0.0520(14) Uani 1 d . .
H1A H 0.2128(4) 0.8821(5) 0.1757(4) 0.068 Uiso 1 d R .
H1B H 0.1276(4) 0.9424(5) 0.0947(4) 0.068 Uiso 1 d R .
C2 C 0.2655(3) 0.9532(4) 0.0833(3) 0.0345(10) Uani 1 d . .
C3 C 0.2262(5) 0.9901(4) -0.0158(3) 0.0522(14) Uani 1 d . .
H3C H 0.1665(5) 1.0365(4) -0.0291(3) 0.068 Uiso 1 d R .
H3D H 0.2759(5) 1.0366(4) -0.0274(3) 0.068 Uiso 1 d R .
C4 C 0.2363(6) 0.8819(6) -0.1531(5) 0.045(2) Uani 0.79(2) d P 1
H4A H 0.2379(6) 0.9584(6) -0.1774(5) 0.059 Uiso 0.79(2) d PR 1
H4B H 0.1901(6) 0.8344(6) -0.2007(5) 0.059 Uiso 0.79(2) d PR 1
C5 C 0.3372(7) 0.8264(9) -0.1203(6) 0.047(2) Uani 0.79(2) d P 1
H5A H 0.3558(7) 0.8063(9) -0.1712(6) 0.061 Uiso 0.79(2) d PR 1
H5B H 0.3853(7) 0.8818(9) -0.0827(6) 0.061 Uiso 0.79(2) d PR 1
C4' C 0.2927(17) 0.9063(18) -0.1124(16) 0.025(6) Uiso 0.21(2) d P 2
H4'1 H 0.2672(17) 0.9541(18) -0.1664(16) 0.033 Uiso 0.21(2) d PR 2
H4'2 H 0.3508(17) 0.9444(18) -0.0692(16) 0.033 Uiso 0.21(2) d PR 2
C5' C 0.3174(25) 0.7913(27) -0.1407(21) 0.035(8) Uiso 0.21(2) d P 2
H5'1 H 0.3757(25) 0.8004(27) -0.1564(21) 0.045 Uiso 0.21(2) d PR 2
H5'2 H 0.2635(25) 0.7606(27) -0.1932(21) 0.045 Uiso 0.21(2) d PR 2
C6 C 0.3124(4) 1.0532(4) 0.1481(3) 0.0462(12) Uani 1 d . .
H6A H 0.2600(4) 1.1082(4) 0.1431(3) 0.060 Uiso 1 d R .
H6B H 0.3373(4) 1.0237(4) 0.2098(3) 0.060 Uiso 1 d R .
C7 C 0.3946(6) 1.1183(6) 0.1319(5) 0.078(2) Uani 1 d . .
H7A H 0.4177(6) 1.1791(6) 0.1760(5) 0.102 Uiso 1 d R .
H7B H 0.3709(6) 1.1506(6) 0.0719(5) 0.102 Uiso 1 d R .
H7C H 0.4484(6) 1.0659(6) 0.1389(5) 0.102 Uiso 1 d R .
Cl1 Cl 0.08710(8) 0.30186(11) 0.11984(8) 0.0414(4) Uani 1 d . .
O11 O 0.0362(4) 0.3985(6) 0.0634(4) 0.059(2) Uani 0.920(12) d P 3
O12 O 0.1910(3) 0.3105(5) 0.1426(5) 0.073(2) Uani 0.920(12) d P 3
O13 O 0.0663(5) 0.3072(5) 0.2014(3) 0.079(2) Uani 0.920(12) d P 3
O14 O 0.0493(5) 0.1963(5) 0.0750(4) 0.077(2) Uani 0.920(12) d P 3
O11' O 0.1327(53) 0.3057(52) 0.2100(39) 0.065(18) Uiso 0.080(12) d P 4
O12' O 0.1701(29) 0.2723(32) 0.0875(29) 0.025(11) Uiso 0.080(12) d P 4
O13' O 0.0183(43) 0.3558(52) 0.0425(39) 0.039(15) Uiso 0.080(12) d P 4
O14' O 0.0163(33) 0.2110(38) 0.1035(29) 0.029(11) Uiso 0.080(12) d P 4
Cl2 Cl 0.0000 -0.0605(2) 0.2500 0.0547(5) Uani 1 d S .
O21 O -0.1011(11) -0.1053(17) 0.2175(9) 0.079(5) Uani 0.50 d P .
O22 O 0.0634(16) -0.1289(17) 0.2349(17) 0.145(10) Uani 0.50 d P .
O23 O 0.0198(9) -0.0604(20) 0.3484(8) 0.134(6) Uani 0.50 d P .
O24 O -0.0062(15) 0.0486(11) 0.2158(12) 0.151(12) Uani 0.50 d P .
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'
Cl Cl 0.1484 0.1585 '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'
Co Co 0.3494 0.9721 '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
_geom_angle_publ_flag
N2 Co N2 180.0 . 7_565 ?
N2 Co N1 91.2(2) . . yes
N2 Co N1 88.8(2) 7_565 . ?
N2 Co N1 88.8(2) . 7_565 ?
N2 Co N1 91.2(2) 7_565 7_565 ?
N1 Co N1 180.0 . 7_565 ?
N2 Co N3 83.37(15) . . yes
N2 Co N3 96.63(15) 7_565 . ?
N1 Co N3 84.1(2) . . yes
N1 Co N3 95.9(2) 7_565 . ?
N2 Co N3 96.63(15) . 7_565 ?
N2 Co N3 83.37(15) 7_565 7_565 ?
N1 Co N3 95.9(2) . 7_565 ?
N1 Co N3 84.1(2) 7_565 7_565 ?
N3 Co N3 180.0 . 7_565 ?
C3 N1 C4 120.1(5) . . yes
C3 N1 C4' 96.0(9) . . yes
C3 N1 Co 108.8(3) . . yes
C4 N1 Co 109.3(3) . . yes
C4' N1 Co 101.1(7) . . yes
C5' N2 C1 99.0(13) 7_565 . ?
C1 N2 C5 118.6(5) . 7_565 ?
C5' N2 Co 111.0(13) 7_565 . ?
C1 N2 Co 109.3(3) . . yes
C5 N2 Co 106.3(4) 7_565 . ?
C2 N3 Co 100.7(2) . . yes
N2 C1 C2 109.3(3) . . yes
N3 C2 C3 104.2(3) . . yes
N3 C2 C1 103.6(4) . . yes
C3 C2 C1 112.9(4) . . yes
N3 C2 C6 113.3(4) . . yes
C3 C2 C6 112.6(4) . . yes
C1 C2 C6 109.9(4) . . yes
N1 C3 C2 110.0(4) . . yes
N1 C4 C5 107.7(6) . . yes
C4 C5 N2 111.0(6) . 7_565 ?
C5' C4' N1 107.6(19) . . yes
N2 C5' C4' 105.7(21) 7_565 . ?
C7 C6 C2 116.4(4) . . yes
O11' Cl1 O13' 145.8(38) . . ?
O12 Cl1 O14 111.3(3) . . ?
O11' Cl1 O14' 104.7(31) . . ?
O13' Cl1 O14' 86.7(29) . . ?
O12 Cl1 O13 109.2(4) . . ?
O14 Cl1 O13 108.5(4) . . ?
O12 Cl1 O11 110.4(3) . . ?
O14 Cl1 O11 110.2(4) . . ?
O13 Cl1 O11 107.1(4) . . ?
O11' Cl1 O12' 103.6(32) . . ?
O13' Cl1 O12' 101.4(28) . . ?
O14' Cl1 O12' 112.3(23) . . ?
O22 Cl2 O22 104.9(17) . 2 ?
O22 Cl2 O24 133.7(14) . 2 ?
O22 Cl2 O24 115.9(14) 2 2 ?
O22 Cl2 O24 115.9(14) . . ?
O22 Cl2 O24 133.7(14) 2 . ?
O24 Cl2 O24 44.4(18) 2 . ?
O22 Cl2 O21 113.8(11) . . ?
O22 Cl2 O21 33.1(12) 2 . ?
O24 Cl2 O21 112.3(12) 2 . ?
O24 Cl2 O21 106.4(10) . . ?
O22 Cl2 O21 33.1(12) . 2 ?
O22 Cl2 O21 113.8(11) 2 2 ?
O24 Cl2 O21 106.4(10) 2 2 ?
O24 Cl2 O21 112.3(12) . 2 ?
O21 Cl2 O21 138.2(16) . 2 ?
O22 Cl2 O23 108.9(14) . . ?
O22 Cl2 O23 71.2(12) 2 . ?
O24 Cl2 O23 67.7(10) 2 . ?
O24 Cl2 O23 112.1(15) . . ?
O21 Cl2 O23 98.5(8) . . ?
O21 Cl2 O23 81.6(8) 2 . ?
O22 Cl2 O23 71.2(12) . 2 ?
O22 Cl2 O23 108.9(14) 2 2 ?
O24 Cl2 O23 112.1(15) 2 2 ?
O24 Cl2 O23 67.7(10) . 2 ?
O21 Cl2 O23 81.6(8) . 2 ?
O21 Cl2 O23 98.5(8) 2 2 ?
O23 Cl2 O23 179.8(18) . 2 ?
O22 O21 Cl2 62.9(20) 2 . ?
O21 O22 Cl2 84.0(25) 2 . ?
O21 O22 O23 129.8(32) 2 2 ?
Cl2 O22 O23 59.5(10) . 2 ?
Cl2 O23 O24 52.7(7) . 2 ?
Cl2 O23 O22 49.3(7) . 2 ?
O24 O23 O22 89.4(11) 2 2 ?
O24 O24 Cl2 67.8(9) 2 . ?
O24 O24 O23 127.3(8) 2 2 ?
Cl2 O24 O23 59.5(7) . 2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co N2 1.949(3) . yes
Co N2 1.949(3) 7_565 ?
Co N1 1.951(4) . yes
Co N1 1.951(4) 7_565 ?
Co N3 1.953(3) . yes
Co N3 1.953(3) 7_565 ?
N1 C3 1.476(6) . yes
N1 C4 1.483(7) . yes
N1 C4' 1.62(2) . yes
N2 C5' 1.42(3) 7_565 ?
N2 C1 1.482(6) . yes
N2 C5 1.531(9) 7_565 ?
N3 C2 1.490(5) . yes
C1 C2 1.524(6) . yes
C2 C3 1.520(7) . yes
C2 C6 1.528(6) . yes
C4 C5 1.498(11) . yes
C5 N2 1.531(9) 7_565 ?
C4' C5' 1.49(4) . yes
C5' N2 1.42(3) 7_565 ?
C6 C7 1.508(8) . yes
Cl1 O11' 1.33(6) . ?
Cl1 O13' 1.40(6) . ?
Cl1 O12 1.411(4) . ?
Cl1 O14 1.417(5) . ?
Cl1 O14' 1.42(4) . ?
Cl1 O13 1.435(5) . ?
Cl1 O11 1.450(5) . ?
Cl1 O12' 1.51(4) . ?
Cl2 O22 1.30(2) . ?
Cl2 O22 1.30(2) 2 ?
Cl2 O24 1.365(11) 2 ?
Cl2 O24 1.365(11) . ?
Cl2 O21 1.45(2) . ?
Cl2 O21 1.45(2) 2 ?
Cl2 O23 1.479(11) . ?
Cl2 O23 1.479(11) 2 ?
O21 O22 0.80(3) 2 ?
O22 O21 0.80(3) 2 ?
O22 O23 1.62(2) 2 ?
O23 O24 1.59(2) 2 ?
O23 O22 1.62(2) 2 ?
O24 O24 1.03(4) 2 ?
O24 O23 1.59(2) 2 ?
