#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:58:55 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179272 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/92/4319201.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_4319201
loop_
_publ_author_name
'Hongyan Luo'
'Natashia Eberly'
'Robin D. Rogers'
'Martin W. Brechbiel'
_publ_section_title
;
 Syntheses and Characterizations of Metal Complexes Derived from
 cis,cis-1,3,5-Triaminocyclohexane-N,N',N''-triacetic Acid
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              493
_journal_page_last               498
_journal_paper_doi               10.1021/ic000603b
_journal_volume                  40
_journal_year                    2001
_chemical_formula_structural     'NIH8 RL-127-1'
_chemical_formula_sum            'C12 H28 Cl3 N3 O8'
_chemical_formula_weight         448.72
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 108.058(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1688(4)
_cell_length_b                   8.4708(2)
_cell_length_c                   15.9408(2)
_cell_measurement_reflns_used    3566
_cell_measurement_temperature    173(2)
_cell_volume                     1947.37(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_method       'phi and omega scans'
_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  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0737
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11880
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.095
_refine_ls_goodness_of_fit_obs   1.122
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_restrained_S_obs      1.122
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_obs          0.0558
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      '0.0328, 3.0692'
_refine_ls_wR_factor_all         0.1247
_refine_ls_wR_factor_obs         0.1010
_reflns_number_observed          3044
_reflns_number_total             4512
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic000603b_2.cif
_cod_data_source_block           nih8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4319201
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cl1 Cl 0.29376(6) 0.59365(10) 0.03083(5) 0.0229(2) Uani 1 d . .
Cl2 Cl 0.00736(6) -0.14126(10) -0.10684(5) 0.0224(2) Uani 1 d . .
Cl3 Cl 0.57693(5) 0.09643(9) 0.22070(5) 0.0167(2) Uani 1 d . .
O1 O 0.0414(2) -0.5150(3) 0.0975(2) 0.0291(6) Uani 1 d . .
H1AO H 0.0322(2) -0.6249(3) 0.0961(2) 0.035 Uiso 1 d R .
O2 O 0.1736(2) -0.5334(3) 0.2104(2) 0.0253(6) Uani 1 d . .
O3 O 0.5072(2) 0.2261(3) 0.54982(14) 0.0241(6) Uani 1 d . .
H3AO H 0.5394(2) 0.2955(3) 0.60097(14) 0.029 Uiso 1 d R .
O4 O 0.54767(15) 0.3845(3) 0.45394(14) 0.0199(5) Uani 1 d . .
O5 O 0.1865(2) 0.3666(3) -0.16162(15) 0.0234(6) Uani 1 d . .
O6 O 0.0397(2) 0.2782(3) -0.2021(2) 0.0329(7) Uani 1 d . .
H6AO H 0.0335(2) 0.3162(3) -0.2606(2) 0.039 Uiso 1 d R .
O7 O 0.2070(2) -0.2812(3) 0.3546(2) 0.0281(6) Uani 1 d . .
H7AO H 0.1468(2) -0.3041(3) 0.3647(2) 0.034 Uiso 1 d R .
H7BO H 0.2306(2) -0.2110(3) 0.4031(2) 0.034 Uiso 1 d R .
O8 O 0.3214(2) 0.0657(3) -0.08114(15) 0.0225(6) Uani 1 d . .
H8AO H 0.3704(2) 0.0083(3) -0.04139(15) 0.027 Uiso 1 d R .
H8BO H 0.2844(2) -0.0143(3) -0.11309(15) 0.027 Uiso 1 d R .
N1 N 0.2261(2) -0.2340(3) 0.1841(2) 0.0146(6) Uani 1 d . .
H1AN H 0.2396(2) -0.2699(3) 0.2440(2) 0.018 Uiso 1 d R .
H1BN H 0.2701(2) -0.2867(3) 0.1702(2) 0.018 Uiso 1 d R .
N2 N 0.4333(2) 0.2193(3) 0.3110(2) 0.0135(6) Uani 1 d . .
H2AN H 0.4434(2) 0.3217(3) 0.3104(2) 0.016 Uiso 1 d R .
H2BN H 0.4866(2) 0.1960(3) 0.2879(2) 0.016 Uiso 1 d R .
N3 N 0.2249(2) 0.2474(3) 0.0037(2) 0.0117(5) Uani 1 d . .
H3AN H 0.2454(2) 0.3541(3) 0.0090(2) 0.014 Uiso 1 d R .
H3BN H 0.2612(2) 0.1847(3) -0.0185(2) 0.014 Uiso 1 d R .
C1 C 0.2375(2) -0.0582(4) 0.1835(2) 0.0130(6) Uani 1 d . .
H1B H 0.1885(2) -0.0088(4) 0.2049(2) 0.016 Uiso 1 calc R .
C2 C 0.3324(2) -0.0129(4) 0.2472(2) 0.0151(7) Uani 1 d . .
H2B H 0.3380(2) -0.0515(4) 0.3073(2) 0.018 Uiso 1 calc R .
H2C H 0.3822(2) -0.0619(4) 0.2281(2) 0.018 Uiso 1 calc R .
C3 C 0.3419(2) 0.1665(4) 0.2481(2) 0.0125(6) Uani 1 d . .
H3B H 0.2911(2) 0.2128(4) 0.2680(2) 0.015 Uiso 1 calc R .
C4 C 0.3322(2) 0.2301(4) 0.1557(2) 0.0142(7) Uani 1 d . .
H4A H 0.3378(2) 0.3465(4) 0.1574(2) 0.017 Uiso 1 calc R .
H4B H 0.3817(2) 0.1861(4) 0.1343(2) 0.017 Uiso 1 calc R .
C5 C 0.2370(2) 0.1812(4) 0.0941(2) 0.0111(6) Uani 1 d . .
H5A H 0.1883(2) 0.2279(4) 0.1169(2) 0.013 Uiso 1 calc R .
C6 C 0.2251(2) 0.0017(4) 0.0902(2) 0.0155(7) Uani 1 d . .
H6A H 0.1626(2) -0.0264(4) 0.0508(2) 0.019 Uiso 1 calc R .
H6B H 0.2718(2) -0.0473(4) 0.0668(2) 0.019 Uiso 1 calc R .
C7 C 0.1332(2) -0.2896(4) 0.1304(2) 0.0174(7) Uani 1 d . .
H7A H 0.1269(2) -0.2799(4) 0.0669(2) 0.021 Uiso 1 calc R .
H7B H 0.0848(2) -0.2236(4) 0.1427(2) 0.021 Uiso 1 calc R .
C8 C 0.1204(2) -0.4594(4) 0.1522(2) 0.0166(7) Uani 1 d . .
C9 C 0.4509(2) 0.1570(4) 0.4027(2) 0.0166(7) Uani 1 d . .
H9A H 0.4835(2) 0.0544(4) 0.4084(2) 0.020 Uiso 1 calc R .
H9B H 0.3910(2) 0.1391(4) 0.4138(2) 0.020 Uiso 1 calc R .
C10 C 0.5086(2) 0.2708(4) 0.4702(2) 0.0170(7) Uani 1 d . .
C11 C 0.1274(2) 0.2417(4) -0.0556(2) 0.0188(7) Uani 1 d . .
H11A H 0.0875(2) 0.3064(4) -0.0304(2) 0.023 Uiso 1 calc R .
H11B H 0.1045(2) 0.1316(4) -0.0608(2) 0.023 Uiso 1 calc R .
C12 C 0.1227(2) 0.3039(4) -0.1454(2) 0.0195(7) 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'
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
C7 N1 C1 113.8(2) . . ?
C9 N2 C3 113.2(2) . . ?
C11 N3 C5 113.5(2) . . ?
N1 C1 C6 110.9(2) . . ?
N1 C1 C2 109.3(2) . . ?
C6 C1 C2 111.7(2) . . ?
C3 C2 C1 108.8(2) . . ?
N2 C3 C2 111.5(2) . . ?
N2 C3 C4 109.3(2) . . ?
C2 C3 C4 111.2(3) . . ?
C5 C4 C3 108.2(2) . . ?
N3 C5 C4 108.9(2) . . ?
N3 C5 C6 110.7(2) . . ?
C4 C5 C6 111.8(3) . . ?
C1 C6 C5 108.3(3) . . ?
N1 C7 C8 109.8(3) . . ?
O2 C8 O1 125.1(3) . . ?
O2 C8 C7 125.0(3) . . ?
O1 C8 C7 109.9(3) . . ?
N2 C9 C10 111.1(3) . . ?
O4 C10 O3 126.1(3) . . ?
O4 C10 C9 125.1(3) . . ?
O3 C10 C9 108.8(3) . . ?
N3 C11 C12 109.8(3) . . ?
O5 C12 O6 125.9(3) . . ?
O5 C12 C11 123.7(3) . . ?
O6 C12 C11 110.4(3) . . ?
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
O1 C8 1.331(4) . ?
O2 C8 1.199(4) . ?
O3 C10 1.331(4) . ?
O4 C10 1.200(4) . ?
O5 C12 1.200(4) . ?
O6 C12 1.319(4) . ?
N1 C7 1.481(4) . ?
N1 C1 1.499(4) . ?
N2 C9 1.498(4) . ?
N2 C3 1.505(4) . ?
N3 C11 1.489(4) . ?
N3 C5 1.504(4) . ?
C1 C6 1.526(4) . ?
C1 C2 1.532(4) . ?
C2 C3 1.526(4) . ?
C3 C4 1.532(4) . ?
C4 C5 1.530(4) . ?
C5 C6 1.530(4) . ?
C7 C8 1.506(5) . ?
C9 C10 1.507(4) . ?
C11 C12 1.506(4) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -58.8(3) . . . . ?
C2 C3 C4 C5 59.1(3) . . . . ?
C3 C4 C5 C6 -59.2(3) . . . . ?
C4 C5 C6 C1 58.7(3) . . . . ?
C5 C6 C1 C2 -58.1(3) . . . . ?
C6 C1 C2 C3 58.6(3) . . . . ?
