#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:55:18 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179312 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/09/4320919.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_4320919
loop_
_publ_author_name
'Paul V. Bernhardt'
'Philip C. Sharpe'
_publ_section_title
;
 Structurally Reinforced Tetraazamacrocyclic Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2020
_journal_page_last               2025
_journal_paper_doi               10.1021/ic9906353
_journal_volume                  39
_journal_year                    2000
_chemical_formula_sum            'C19 H36 Cl Cu N5 O5'
_chemical_formula_weight         513.52
_chemical_name_systematic
; 
 ? 
;
_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     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.070(10)
_cell_angle_beta                 96.76(2)
_cell_angle_gamma                92.990(10)
_cell_formula_units_Z            2
_cell_length_a                   10.041(2)
_cell_length_b                   10.1720(10)
_cell_length_c                   11.2020(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     1133.6(3)
_computing_cell_refinement       CAD4
_computing_data_collection       CAD4
_computing_data_reduction        'XTAL 3.2'
_computing_molecular_graphics    PLATON
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       'omega-2theta 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  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4225
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.83
_diffrn_standards_interval_count 250
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.981
_refine_diff_density_min         -2.811
_refine_diff_density_rms         0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0805
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1710P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1956
_refine_ls_wR_factor_ref         0.2091
_reflns_number_gt                3283
_reflns_number_total             3976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9906353_1.cif
_cod_data_source_block           1344ps22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1710P)^2^+0.0000P] 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^)+(0.1710P)^2^+0.0000P] 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               4320919
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_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.21285(5) 0.21109(5) 0.25548(4) 0.0278(2) Uani 1 d . . .
Cl1 Cl 0.07476(12) 0.00089(11) 0.30499(11) 0.0412(3) Uani 1 d . . .
N1 N 0.3851(4) 0.1740(4) 0.3542(3) 0.0314(8) Uani 1 d . . .
H1 H 0.4453 0.2408 0.3422 0.038 Uiso 1 d R . .
N2 N 0.2858(4) 0.1094(4) 0.1199(3) 0.0328(8) Uani 1 d . . .
H2 H 0.2348 0.0325 0.1073 0.039 Uiso 1 d R . .
N3 N 0.0554(4) 0.2745(4) 0.1474(3) 0.0325(8) Uani 1 d . . .
H3 H -0.0077 0.2063 0.1376 0.039 Uiso 1 d R . .
N4 N 0.1554(4) 0.3359(3) 0.3869(3) 0.0284(8) Uani 1 d . . .
N5 N 0.3631(4) 0.4044(4) 0.4855(3) 0.0317(8) Uani 1 d . . .
H5A H 0.4008 0.4629 0.5435 0.033(12) Uiso 1 d R . .
C1 C 0.4334(5) 0.0532(5) 0.2979(5) 0.0395(11) Uani 1 d . . .
H1A H 0.3775 -0.0235 0.3134 0.047 Uiso 1 d R . .
H1B H 0.5254 0.0399 0.3304 0.047 Uiso 1 d R . .
C2 C 0.4238(5) 0.0734(5) 0.1640(5) 0.0413(11) Uani 1 d . . .
H2A H 0.4883 0.1431 0.1485 0.050 Uiso 1 d R . .
H2B H 0.4443 -0.0068 0.1221 0.050 Uiso 1 d R . .
C3 C 0.2797(5) 0.1711(6) 0.0033(4) 0.0448(12) Uani 1 d . . .
H3A H 0.3151 0.1128 -0.0541 0.054 Uiso 1 d R . .
H3B H 0.3356 0.2524 0.0117 0.054 Uiso 1 d R . .
C4 C 0.1374(6) 0.2007(6) -0.0445(4) 0.0493(13) Uani 1 d . . .
H4A H 0.1354 0.2236 -0.1280 0.059 Uiso 1 d R . .
H4B H 0.0800 0.1214 -0.0422 0.059 Uiso 1 d R . .
C5 C 0.0805(5) 0.3112(5) 0.0244(4) 0.0419(11) Uani 1 d . . .
H5C H 0.1426 0.3882 0.0303 0.050 Uiso 1 d R . .
H5D H -0.0033 0.3346 -0.0199 0.050 Uiso 1 d R . .
C6 C -0.0045(5) 0.3820(5) 0.2105(4) 0.0405(11) Uani 1 d . . .
H6A H -0.0996 0.3830 0.1822 0.049 Uiso 1 d R . .
H6B H 0.0382 0.4660 0.1938 0.049 Uiso 1 d R . .
C7 C 0.0146(4) 0.3617(5) 0.3449(4) 0.0366(10) Uani 1 d . . .
H7A H -0.0105 0.4396 0.3876 0.044 Uiso 1 d R . .
H7B H -0.0437 0.2878 0.3629 0.044 Uiso 1 d R . .
C8 C 0.1681(5) 0.2703(5) 0.5029(4) 0.0357(10) Uani 1 d . . .
H8A H 0.1340 0.1791 0.4930 0.043 Uiso 1 d R . .
H8B H 0.1208 0.3156 0.5613 0.043 Uiso 1 d R . .
C9 C 0.3183(5) 0.2804(4) 0.5405(4) 0.0350(10) Uani 1 d . . .
C10 C 0.3884(5) 0.1656(5) 0.4861(4) 0.0381(10) Uani 1 d . . .
H10A H 0.4810 0.1672 0.5227 0.046 Uiso 1 d R . .
H10B H 0.3442 0.0828 0.5041 0.046 Uiso 1 d R . .
C11 C 0.2463(4) 0.4573(4) 0.4203(4) 0.0298(9) Uani 1 d . . .
H11 H 0.2040 0.5141 0.4757 0.036 Uiso 1 d R . .
C12 C 0.2760(4) 0.5356(4) 0.3130(4) 0.0286(9) Uani 1 d . . .
C13 C 0.2145(5) 0.6538(4) 0.2930(4) 0.0356(10) Uani 1 d . . .
H13 H 0.1646 0.6885 0.3503 0.043 Uiso 1 d R . .
C14 C 0.2266(5) 0.7196(4) 0.1889(4) 0.0360(10) Uani 1 d . . .
H14 H 0.1849 0.7983 0.1767 0.043 Uiso 1 d R . .
C15 C 0.3003(4) 0.6701(4) 0.1026(4) 0.0310(9) Uani 1 d . . .
C16 C 0.3669(4) 0.5557(4) 0.1248(4) 0.0330(9) Uani 1 d . . .
H16 H 0.4195 0.5229 0.0688 0.040 Uiso 1 d R . .
C17 C 0.3557(4) 0.4893(4) 0.2296(4) 0.0315(9) Uani 1 d . . .
H17 H 0.4021 0.4135 0.2439 0.038 Uiso 1 d R . .
C18 C 0.3023(5) 0.7335(5) -0.0175(4) 0.0379(11) Uani 1 d . . .
C19 C 0.3534(6) 0.2833(6) 0.6768(4) 0.0507(13) Uani 1 d . . .
H19A H 0.4493 0.2897 0.6962 0.076 Uiso 1 d R . .
H19B H 0.3175 0.2040 0.7080 0.076 Uiso 1 d R . .
H19C H 0.3158 0.3581 0.7121 0.076 Uiso 1 d R . .
O1 O 0.2388(4) 0.8369(4) -0.0325(3) 0.0545(10) Uani 1 d . . .
O2 O 0.3622(5) 0.6774(4) -0.0933(3) 0.0584(10) Uani 1 d . . .
O3 O 0.3551(4) 0.6587(4) -0.3370(3) 0.0575(10) Uani 1 d . . .
H31 H 0.3511 0.6796 -0.2610 0.086 Uiso 1 d R . .
H32 H 0.2953 0.6297 -0.3601 0.086 Uiso 1 d R . .
O4 O 0.2305(4) 0.9556(5) -0.2464(4) 0.0673(12) Uani 1 d . . .
H41 H 0.2395 0.9058 -0.3020 0.101 Uiso 1 d R . .
H42 H 0.1424 0.9623 -0.2429 0.101 Uiso 1 d R . .
O5 O 0.2233(7) -0.1477(6) 0.5316(5) 0.0916(17) 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'
Cu Cu 0.3201 1.2651 '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
N1 Cu1 N3 170.72(15) . . ?
N1 Cu1 N2 85.49(15) . . ?
N3 Cu1 N2 93.94(15) . . ?
N1 Cu1 N4 93.20(14) . . ?
N3 Cu1 N4 86.08(15) . . ?
N2 Cu1 N4 172.07(14) . . ?
N1 Cu1 Cl1 97.20(11) . . ?
N3 Cu1 Cl1 92.06(11) . . ?
N2 Cu1 Cl1 90.35(11) . . ?
N4 Cu1 Cl1 97.57(10) . . ?
C10 N1 C1 111.9(4) . . ?
C10 N1 Cu1 119.3(3) . . ?
C1 N1 Cu1 106.2(3) . . ?
C3 N2 C2 112.1(4) . . ?
C3 N2 Cu1 116.9(3) . . ?
C2 N2 Cu1 108.0(3) . . ?
C6 N3 C5 111.2(4) . . ?
C6 N3 Cu1 109.4(3) . . ?
C5 N3 Cu1 116.9(3) . . ?
C7 N4 C8 112.0(3) . . ?
C7 N4 C11 114.8(3) . . ?
C8 N4 C11 100.2(3) . . ?
C7 N4 Cu1 104.8(3) . . ?
C8 N4 Cu1 109.2(3) . . ?
C11 N4 Cu1 115.9(2) . . ?
C11 N5 C9 107.9(3) . . ?
N1 C1 C2 106.8(4) . . ?
N2 C2 C1 109.3(4) . . ?
N2 C3 C4 111.8(4) . . ?
C5 C4 C3 114.3(4) . . ?
N3 C5 C4 112.5(4) . . ?
N3 C6 C7 109.4(4) . . ?
N4 C7 C6 111.1(3) . . ?
N4 C8 C9 102.6(3) . . ?
N5 C9 C8 103.2(4) . . ?
N5 C9 C19 113.1(4) . . ?
C8 C9 C19 112.4(4) . . ?
N5 C9 C10 108.1(4) . . ?
C8 C9 C10 111.8(4) . . ?
C19 C9 C10 108.1(4) . . ?
N1 C10 C9 111.4(4) . . ?
N5 C11 N4 102.6(3) . . ?
N5 C11 C12 114.3(4) . . ?
N4 C11 C12 113.4(3) . . ?
C17 C12 C13 118.7(4) . . ?
C17 C12 C11 122.0(4) . . ?
C13 C12 C11 119.2(4) . . ?
C14 C13 C12 120.6(4) . . ?
C13 C14 C15 120.8(4) . . ?
C14 C15 C16 118.7(4) . . ?
C14 C15 C18 121.2(4) . . ?
C16 C15 C18 120.0(4) . . ?
C15 C16 C17 120.8(4) . . ?
C12 C17 C16 120.3(4) . . ?
O2 C18 O1 125.9(4) . . ?
O2 C18 C15 117.2(4) . . ?
O1 C18 C15 116.9(4) . . ?
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
Cu1 N1 2.001(4) . ?
Cu1 N3 2.023(4) . ?
Cu1 N2 2.035(3) . ?
Cu1 N4 2.062(3) . ?
Cu1 Cl1 2.5998(13) . ?
N1 C10 1.480(6) . ?
N1 C1 1.490(6) . ?
N2 C3 1.465(6) . ?
N2 C2 1.484(6) . ?
N3 C6 1.473(6) . ?
N3 C5 1.487(6) . ?
N4 C7 1.477(6) . ?
N4 C8 1.478(5) . ?
N4 C11 1.505(5) . ?
N5 C11 1.446(6) . ?
N5 C9 1.494(5) . ?
C1 C2 1.514(7) . ?
C3 C4 1.515(8) . ?
C4 C5 1.514(8) . ?
C6 C7 1.519(7) . ?
C8 C9 1.514(7) . ?
C9 C19 1.526(6) . ?
C9 C10 1.539(7) . ?
C11 C12 1.515(5) . ?
C12 C17 1.386(6) . ?
C12 C13 1.393(6) . ?
C13 C14 1.380(7) . ?
C14 C15 1.381(6) . ?
C15 C16 1.388(6) . ?
C15 C18 1.514(6) . ?
C16 C17 1.388(6) . ?
C18 O2 1.237(6) . ?
C18 O1 1.264(6) . ?
