#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:31:18 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179332 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/29/4322965.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_4322965
loop_
_publ_author_name
'Paul V. Bernhardt'
'Elizabeth J. Hayes'
_publ_section_title
;
 Aminotriazines as Locking Fragments in Macrocyclic Synthesis
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4214
_journal_page_last               4219
_journal_paper_doi               10.1021/ic980243g
_journal_volume                  37
_journal_year                    1998
_chemical_formula_sum            'C24 H54 Cl4 Cu2 N18 O20'
_chemical_formula_weight         1183.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yac'
_symmetry_space_group_name_H-M   'C 1 2/n 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                 117.82(2)
_cell_angle_gamma                90.000(9)
_cell_formula_units_Z            4
_cell_length_a                   18.624(8)
_cell_length_b                   17.160(2)
_cell_length_c                   15.998(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     4522(3)
_computing_cell_refinement       CAD4
_computing_data_collection       CAD4
_computing_data_reduction        XTAL
_computing_molecular_graphics    PLATON
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       'omega-2 theta 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  0.0893
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4087
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.71
_diffrn_standards_interval_count 250
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.272
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_description       prism
_exptl_crystal_F_000             2440
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.437
_refine_diff_density_min         -2.063
_refine_diff_density_rms         0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.138
_refine_ls_goodness_of_fit_obs   1.188
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_restrained_S_obs      1.188
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_obs          0.0898
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1885P)²+4.0423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2653
_refine_ls_wR_factor_obs         0.2344
_reflns_number_observed          2881
_reflns_number_total             3957
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic980243g_2.cif
_cod_data_source_block           1234eh7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1885P)^2^+4.0423P] 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^)+(0.1885P)^2^+4.0423P] 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        4521.8(26)
_cod_original_sg_symbol_H-M      'C 1 2/c 1'
_cod_database_code               4322965
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Cu1 Cu 0.03147(5) 0.23431(4) 0.21520(5) 0.0307(3) Uani 1 d . .
N1 N 0.1383(3) 0.2937(3) 0.2563(4) 0.0325(12) Uani 1 d . .
H1 H 0.1634(3) 0.2697(3) 0.2264(4) 0.039 Uiso 1 calc R .
N2 N -0.0154(3) 0.3134(3) 0.1114(4) 0.0369(13) Uani 1 d . .
H2 H -0.0474(3) 0.3461(3) 0.1244(4) 0.044 Uiso 1 calc R .
N3 N -0.0762(3) 0.1821(3) 0.1759(4) 0.0387(13) Uani 1 d . .
H3 H -0.1071(3) 0.2151(3) 0.1903(4) 0.046 Uiso 1 calc R .
N4 N 0.0729(3) 0.1599(3) 0.3249(4) 0.0319(12) Uani 1 d . .
H4 H 0.0936(3) 0.1185(3) 0.3077(4) 0.038 Uiso 1 calc R .
C1 C 0.1981(4) 0.2932(4) 0.3580(5) 0.0355(14) Uani 1 d . .
H1A H 0.2504(4) 0.3109(4) 0.3658(5) 0.043 Uiso 1 calc R .
H1B H 0.1806(4) 0.3288(4) 0.3921(5) 0.043 Uiso 1 calc R .
C2 C 0.1160(4) 0.3713(4) 0.2136(5) 0.042(2) Uani 1 d . .
H2A H 0.1630(4) 0.3973(4) 0.2157(5) 0.051 Uiso 1 calc R .
H2B H 0.0950(4) 0.4029(4) 0.2476(5) 0.051 Uiso 1 calc R .
C3 C 0.0516(4) 0.3600(4) 0.1122(6) 0.045(2) Uani 1 d . .
H3A H 0.0313(4) 0.4102(4) 0.0827(6) 0.054 Uiso 1 calc R .
H3B H 0.0746(4) 0.3333(4) 0.0768(6) 0.054 Uiso 1 calc R .
C4 C -0.0657(5) 0.2782(4) 0.0188(5) 0.045(2) Uani 1 d . .
H4A H -0.0339(5) 0.2401(4) 0.0056(5) 0.054 Uiso 1 calc R .
H4B H -0.0828(5) 0.3182(4) -0.0295(5) 0.054 Uiso 1 calc R .
C5 C -0.1391(5) 0.2393(5) 0.0152(6) 0.054(2) Uani 1 d . .
H5A H -0.1763(5) 0.2272(5) -0.0501(6) 0.065 Uiso 1 calc R .
H5B H -0.1662(5) 0.2760(5) 0.0374(6) 0.065 Uiso 1 calc R .
C6 C -0.1219(5) 0.1650(4) 0.0733(5) 0.048(2) Uani 1 d . .
H6A H -0.1727(5) 0.1396(4) 0.0596(5) 0.057 Uiso 1 calc R .
H6B H -0.0906(5) 0.1296(4) 0.0557(5) 0.057 Uiso 1 calc R .
C7 C -0.0617(5) 0.1115(5) 0.2346(6) 0.051(2) Uani 1 d . .
H7A H -0.0436(5) 0.0691(5) 0.2089(6) 0.061 Uiso 1 calc R .
H7B H -0.1116(5) 0.0956(5) 0.2349(6) 0.061 Uiso 1 calc R .
C8 C 0.0020(5) 0.1298(5) 0.3333(6) 0.047(2) Uani 1 d . .
H8A H -0.0177(5) 0.1687(5) 0.3616(6) 0.056 Uiso 1 calc R .
H8B H 0.0166(5) 0.0832(5) 0.3722(6) 0.056 Uiso 1 calc R .
C9 C 0.1392(4) 0.1900(4) 0.4125(5) 0.0368(15) Uani 1 d . .
H9A H 0.1198(4) 0.2330(4) 0.4357(5) 0.044 Uiso 1 calc R .
H9B H 0.1583(4) 0.1494(4) 0.4602(5) 0.044 Uiso 1 calc R .
C10 C 0.2548(4) 0.1621(4) 0.3868(4) 0.0294(13) Uani 1 d . .
C11 C 0.3658(4) 0.1317(4) 0.3675(5) 0.0350(14) Uani 1 d . .
C12 C 0.2804(4) 0.0346(4) 0.3826(5) 0.039(2) Uani 1 d . .
N5 N 0.2060(3) 0.2163(3) 0.3960(4) 0.0325(12) Uani 1 d . .
N6 N 0.3161(3) 0.1870(3) 0.3717(4) 0.0322(12) Uani 1 d . .
N7 N 0.2338(3) 0.0882(3) 0.3909(4) 0.0359(13) Uani 1 d . .
N8 N 0.3462(4) 0.0532(3) 0.3727(4) 0.0419(14) Uani 1 d . .
H8 H 0.3766(4) 0.0168(3) 0.3694(4) 0.050 Uiso 1 calc R .
N9 N 0.2629(5) -0.0400(4) 0.3823(6) 0.061(2) Uani 1 d . .
H9C H 0.2208(5) -0.0537(4) 0.3875(6) 0.073 Uiso 1 calc R .
H9D H 0.2936(5) -0.0749(4) 0.3768(6) 0.073 Uiso 1 calc R .
O1 O 0.4271(3) 0.1451(3) 0.3597(4) 0.0470(13) Uani 1 d . .
Cl1 Cl 0.17094(12) -0.02720(11) 0.56121(14) 0.0487(5) Uani 1 d . .
O11 O 0.1396(8) -0.0457(8) 0.4659(7) 0.158(6) Uani 1 d . .
O12 O 0.2020(9) 0.0451(6) 0.5838(8) 0.148(5) Uani 1 d . .
O13 O 0.1166(7) -0.0424(5) 0.5984(8) 0.124(4) Uani 1 d . .
O14 O 0.2282(8) -0.0853(9) 0.6033(12) 0.189(7) Uani 1 d . .
Cl2 Cl -0.0170(6) 0.3997(5) 0.3489(5) 0.049(2) Uani 0.45(2) d P 1
Cl2' Cl -0.0555(12) 0.3811(6) 0.3167(12) 0.086(4) Uani 0.55(2) d P 2
O21 O -0.0773(9) 0.4002(8) 0.3820(9) 0.181(7) Uani 1 d . .
O22 O 0.0007(10) 0.3263(6) 0.3391(11) 0.166(6) Uani 1 d . .
O23 O -0.0513(7) 0.4416(8) 0.2652(9) 0.149(5) Uani 1 d . .
O24 O 0.0603(22) 0.4236(18) 0.4048(23) 0.166(14) Uiso 0.45(2) d P 1
O24' O -0.1262(20) 0.3350(17) 0.2226(22) 0.197(14) Uiso 0.55(2) d P 2
OW1 O 0.2735(12) -0.1818(9) 0.7398(17) 0.107(6) 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'
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'
Cu Cu 0.3201 1.2651 '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
N2 Cu1 N4 174.7(2) . . ?
N2 Cu1 N3 93.3(2) . . ?
N4 Cu1 N3 84.8(2) . . ?
N2 Cu1 N1 84.9(2) . . ?
N4 Cu1 N1 96.7(2) . . ?
N3 Cu1 N1 176.5(2) . . ?
N2 Cu1 O1 98.2(2) . 2 ?
N4 Cu1 O1 86.9(2) . 2 ?
N3 Cu1 O1 93.9(2) . 2 ?
N1 Cu1 O1 89.3(2) . 2 ?
N2 Cu1 O22 92.9(3) . . ?
N4 Cu1 O22 82.1(3) . . ?
N3 Cu1 O22 88.2(4) . . ?
N1 Cu1 O22 88.9(4) . . ?
O1 Cu1 O22 168.5(3) 2 . ?
C2 N1 C1 114.9(5) . . ?
C2 N1 Cu1 106.3(4) . . ?
C1 N1 Cu1 118.0(4) . . ?
C4 N2 C3 111.9(5) . . ?
C4 N2 Cu1 112.6(4) . . ?
C3 N2 Cu1 108.7(4) . . ?
C7 N3 C6 112.4(6) . . ?
C7 N3 Cu1 107.9(4) . . ?
C6 N3 Cu1 114.0(4) . . ?
C9 N4 C8 115.2(5) . . ?
C9 N4 Cu1 114.9(4) . . ?
C8 N4 Cu1 107.8(4) . . ?
N5 C1 N1 110.2(5) . . ?
N1 C2 C3 107.1(6) . . ?
N2 C3 C2 108.8(6) . . ?
N2 C4 C5 111.4(6) . . ?
C4 C5 C6 114.9(7) . . ?
N3 C6 C5 111.0(6) . . ?
N3 C7 C8 108.5(6) . . ?
N4 C8 C7 106.1(5) . . ?
N5 C9 N4 110.2(5) . . ?
N7 C10 N6 127.1(6) . . ?
N7 C10 N5 114.7(5) . . ?
N6 C10 N5 118.1(6) . . ?
O1 C11 N6 124.4(6) . . ?
O1 C11 N8 117.6(6) . . ?
N6 C11 N8 118.0(5) . . ?
N7 C12 N9 120.4(6) . . ?
N7 C12 N8 121.8(6) . . ?
N9 C12 N8 117.8(6) . . ?
C10 N5 C1 121.8(5) . . ?
C10 N5 C9 118.6(5) . . ?
C1 N5 C9 115.9(5) . . ?
C10 N6 C11 116.4(5) . . ?
C12 N7 C10 115.9(5) . . ?
C12 N8 C11 120.6(5) . . ?
C11 O1 Cu1 137.3(4) . 2 ?
O12 Cl1 O14 113.4(10) . . ?
O12 Cl1 O11 114.4(6) . . ?
O14 Cl1 O11 101.6(10) . . ?
O12 Cl1 O13 111.0(6) . . ?
O14 Cl1 O13 101.7(9) . . ?
O11 Cl1 O13 113.7(6) . . ?
O22 Cl2 O24 96.8(16) . . ?
O22 Cl2 O23 113.9(10) . . ?
O24 Cl2 O23 110.5(16) . . ?
O22 Cl2 O21 109.0(10) . . ?
O24 Cl2 O21 121.5(16) . . ?
O23 Cl2 O21 105.3(8) . . ?
O22 Cl2' O21 117.2(11) . . ?
O22 Cl2' O23 116.6(10) . . ?
O21 Cl2' O23 114.6(11) . . ?
O22 Cl2' O24' 95.7(15) . . ?
O21 Cl2' O24' 115.2(18) . . ?
O23 Cl2' O24' 93.4(15) . . ?
Cl2' O22 Cu1 127.4(11) . . ?
Cl2 O22 Cu1 139.7(8) . . ?
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 N2 2.003(5) . ?
Cu1 N4 2.010(5) . ?
Cu1 N3 2.011(6) . ?
Cu1 N1 2.051(5) . ?
Cu1 O1 2.288(5) 2 ?
Cu1 O22 2.794(10) . ?
N1 C2 1.466(8) . ?
N1 C1 1.482(8) . ?
N2 C4 1.464(10) . ?
N2 C3 1.476(8) . ?
N3 C7 1.479(10) . ?
N3 C6 1.484(10) . ?
N4 C9 1.464(9) . ?
N4 C8 1.481(8) . ?
C1 N5 1.432(8) . ?
C2 C3 1.514(11) . ?
C4 C5 1.497(11) . ?
C5 C6 1.522(11) . ?
C7 C8 1.500(12) . ?
C9 N5 1.458(8) . ?
C10 N7 1.338(8) . ?
C10 N6 1.343(8) . ?
C10 N5 1.356(8) . ?
C11 O1 1.228(8) . ?
C11 N6 1.348(8) . ?
C11 N8 1.408(9) . ?
C12 N7 1.314(9) . ?
C12 N9 1.320(9) . ?
C12 N8 1.345(9) . ?
O1 Cu1 2.288(5) 2 ?
Cl1 O12 1.344(8) . ?
Cl1 O14 1.384(12) . ?
Cl1 O11 1.391(8) . ?
Cl1 O13 1.417(7) . ?
Cl2 O22 1.331(11) . ?
Cl2 O24 1.36(4) . ?
Cl2 O23 1.385(12) . ?
Cl2 O21 1.449(13) . ?
Cl2' O22 1.325(12) . ?
Cl2' O21 1.328(12) . ?
Cl2' O23 1.351(12) . ?
Cl2' O24' 1.67(4) . ?
OW1 OW1 1.07(3) 2_556 ?
