#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:22:11 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179324 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/21/4322156.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_4322156
loop_
_publ_author_name
'Paul V. Bernhardt'
_publ_section_title
;
 A Supramolecular Synthon for H-Bonded Transition Metal Arrays
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3481
_journal_page_last               3483
_journal_paper_doi               10.1021/ic990074f
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C16 H36 Cl2 Cu N12 O14'
_chemical_formula_weight         755.01
_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
_cell_angle_alpha                97.85(3)
_cell_angle_beta                 91.82(2)
_cell_angle_gamma                111.40(2)
_cell_formula_units_Z            2
_cell_length_a                   8.436(2)
_cell_length_b                   8.439(2)
_cell_length_c                   22.997(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1504.1(8)
_computing_cell_refinement       CAD4
_computing_data_collection       CAD4
_computing_data_reduction        XTAL3.2
_computing_molecular_graphics    PLUTON
_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-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  0.1237
_diffrn_reflns_av_sigmaI/netI    0.2370
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5779
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.79
_diffrn_standards_interval_count 250
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       needles
_exptl_crystal_F_000             782
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.042
_refine_diff_density_min         -1.527
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       0.0073(32)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.032
_refine_ls_goodness_of_fit_obs   1.269
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         5257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_restrained_S_obs      1.269
_refine_ls_R_factor_all          0.2800
_refine_ls_R_factor_obs          0.1192
_refine_ls_shift/esd_max         -0.009
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2040P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.4124
_refine_ls_wR_factor_obs         0.2873
_reflns_number_observed          1821
_reflns_number_total             5263
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic990074f_2.cif
_cod_data_source_block           pb29noab
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.2040P)^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^)+(0.2040P)^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_original_cell_volume        1504.1(7)
_cod_database_code               4322156
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
Cu1 Cu 0.2824(3) 0.1905(3) 0.15040(10) 0.0413(8) Uani 1 d . .
N1 N 0.1323(18) 0.1257(17) 0.2157(6) 0.043(4) Uani 1 d . .
H1 H 0.0446(18) 0.1625(17) 0.2108(6) 0.052 Uiso 1 d R .
N2 N 0.1620(15) -0.0570(17) 0.1123(6) 0.038(3) Uani 1 d . .
H2 H 0.2324(15) -0.1130(17) 0.1199(6) 0.045 Uiso 1 d R .
N3 N 0.4412(17) 0.2556(18) 0.0851(7) 0.045(4) Uani 1 d . .
H3 H 0.5222(17) 0.2095(18) 0.0895(7) 0.055 Uiso 1 d R .
N4 N 0.4134(16) 0.4341(16) 0.1904(6) 0.039(4) Uani 1 d . .
H4 H 0.3506(16) 0.4976(16) 0.1825(6) 0.047 Uiso 1 d R .
N5 N 0.2918(20) 0.3847(16) 0.2805(7) 0.050(4) Uani 1 d . .
N6 N 0.2851(18) 0.6519(15) 0.3136(6) 0.040(3) Uani 1 d . .
N7 N 0.0364(21) 0.6612(17) 0.3498(7) 0.054(4) Uani 1 d . .
H7 H -0.0217(21) 0.7226(17) 0.3619(7) 0.065 Uiso 1 d R .
N8 N 0.0469(19) 0.3907(17) 0.3178(6) 0.046(4) Uani 1 d . .
N9 N 0.2710(19) 0.9053(17) 0.3563(7) 0.054(4) Uani 1 d . .
H9A H 0.3750(19) 0.9598(17) 0.3495(7) 0.065 Uiso 1 d R .
H9B H 0.2130(19) 0.9608(17) 0.3732(7) 0.065 Uiso 1 d R .
N10 N -0.1946(21) 0.4104(18) 0.3537(8) 0.065(5) Uani 1 d . .
H10A H -0.2395(21) 0.2997(18) 0.3478(8) 0.078 Uiso 1 d R .
H10B H -0.2529(21) 0.4695(18) 0.3677(8) 0.078 Uiso 1 d R .
N11 N 0.1537(20) 1.4060(17) 0.4626(6) 0.050(4) Uani 1 d . .
H11 H 0.0524(20) 1.3701(17) 0.4741(6) 0.060 Uiso 1 d R .
N12 N 0.3972(18) 1.6334(17) 0.4518(6) 0.047(4) Uani 1 d . .
H12 H 0.4511(18) 1.7430(17) 0.4554(6) 0.056 Uiso 1 d R .
C1 C 0.0544(23) -0.0677(19) 0.2090(9) 0.050(5) Uani 1 d . .
H1A H -0.0465(23) -0.1066(19) 0.2304(9) 0.060 Uiso 1 d R .
H1B H 0.1376(23) -0.1103(19) 0.2238(9) 0.060 Uiso 1 d R .
C2 C 0.0100(23) -0.1326(21) 0.1426(8) 0.047(5) Uani 1 d . .
H2A H -0.0326(23) -0.2576(21) 0.1349(8) 0.057 Uiso 1 d R .
H2B H -0.0788(23) -0.0957(21) 0.1287(8) 0.057 Uiso 1 d R .
C3 C 0.1243(24) -0.0893(23) 0.0486(9) 0.057(5) Uani 1 d . .
H3A H 0.0407(24) -0.0403(23) 0.0394(9) 0.069 Uiso 1 d R .
H3B H 0.0747(24) -0.2125(23) 0.0347(9) 0.069 Uiso 1 d R .
C4 C 0.2825(29) -0.0124(29) 0.0165(8) 0.070(7) Uani 1 d . .
H4A H 0.3707(29) -0.0506(29) 0.0299(8) 0.084 Uiso 1 d R .
H4B H 0.2569(29) -0.0525(29) -0.0256(8) 0.084 Uiso 1 d R .
C5 C 0.3652(28) 0.1791(29) 0.0254(9) 0.070(6) Uani 1 d . .
H5A H 0.4471(28) 0.2245(29) -0.0026(9) 0.084 Uiso 1 d R .
H5B H 0.2717(28) 0.2184(29) 0.0203(9) 0.084 Uiso 1 d R .
C6 C 0.5251(23) 0.4427(20) 0.0945(9) 0.053(5) Uani 1 d . .
H6A H 0.6277(23) 0.4775(20) 0.0737(9) 0.063 Uiso 1 d R .
H6B H 0.4498(23) 0.4959(20) 0.0806(9) 0.063 Uiso 1 d R .
C7 C 0.5697(23) 0.4986(23) 0.1590(9) 0.053(5) Uani 1 d . .
H7A H 0.6497(23) 0.4500(23) 0.1723(9) 0.063 Uiso 1 d R .
H7B H 0.6233(23) 0.6232(23) 0.1679(9) 0.063 Uiso 1 d R .
C8 C 0.4544(23) 0.4660(24) 0.2554(9) 0.055(5) Uani 1 d . .
H8A H 0.5358(23) 0.4152(24) 0.2655(9) 0.066 Uiso 1 d R .
H8B H 0.5019(23) 0.5880(24) 0.2713(9) 0.066 Uiso 1 d R .
C9 C 0.2179(24) 0.1991(21) 0.2750(8) 0.050(5) Uani 1 d . .
H9C H 0.1366(24) 0.1673(21) 0.3043(8) 0.060 Uiso 1 d R .
H9D H 0.3056(24) 0.1534(21) 0.2822(8) 0.060 Uiso 1 d R .
C10 C 0.2013(22) 0.4789(20) 0.3052(7) 0.039(4) Uani 1 d . .
C11 C 0.1979(25) 0.7415(21) 0.3404(7) 0.043(4) Uani 1 d . .
C12 C -0.0354(26) 0.4906(23) 0.3405(8) 0.053(5) Uani 1 d . .
C13 C 0.3848(22) 1.3512(20) 0.4210(8) 0.047(5) Uani 1 d . .
H13 H 0.4339(22) 1.2739(20) 0.4056(8) 0.056 Uiso 1 d R .
C14 C 0.2267(23) 1.2859(20) 0.4389(8) 0.047(5) Uani 1 d . .
C15 C 0.2409(24) 1.5739(21) 0.4700(7) 0.043(4) Uani 1 d . .
C16 C 0.4834(24) 1.5258(21) 0.4261(8) 0.044(4) Uani 1 d . .
O1 O 0.1333(16) 1.1290(16) 0.4375(7) 0.066(4) Uani 1 d . .
O2 O 0.1788(16) 1.6785(13) 0.4956(6) 0.065(4) Uani 1 d . .
O3 O 0.6278(18) 1.5993(16) 0.4112(6) 0.067(4) Uani 1 d . .
O4 O -0.1462(19) 0.8717(18) 0.3775(7) 0.080(5) Uani 1 d . .
H41 H -0.0513(19) 0.9557(18) 0.3972(7) 0.096 Uiso 1 d R .
H42 H -0.1719(19) 0.8038(18) 0.4103(7) 0.096 Uiso 1 d R .
O5 O -0.3670(18) 0.0458(16) 0.3444(7) 0.073(4) Uani 1 d . .
H51 H -0.2555(18) 0.0811(16) 0.3661(7) 0.088 Uiso 1 d R .
H52 H -0.3907(18) -0.0028(16) 0.3132(7) 0.088 Uiso 1 d R .
O6 O 0.3266(21) 1.0324(17) 0.5210(8) 0.098(6) Uani 1 d . .
H61 H 0.4065(21) 1.1551(17) 0.5093(8) 0.118 Uiso 1 d R .
H62 H 0.3104(21) 0.9964(17) 0.4875(8) 0.118 Uiso 1 d R .
Cl1 Cl 0.5762(7) -0.0164(7) 0.1828(2) 0.0582(15) Uani 1 d . .
O11 O 0.5160(22) 0.1152(21) 0.2039(7) 0.094(5) Uani 1 d . .
O12A O 0.6141(42) -0.0145(42) 0.1264(9) 0.151(14) Uani 0.87(3) d P 1
O13A O 0.7112(33) -0.0164(37) 0.2191(9) 0.108(10) Uani 0.87(3) d P 1
O14A O 0.4371(33) -0.1696(28) 0.1876(17) 0.150(13) Uani 0.87(3) d P 1
O12B O 0.7155(101) 0.0636(91) 0.1810(34) 0.022(27) Uiso 0.13(3) d P 2
O13B O 0.4910(133) -0.1433(129) 0.1438(45) 0.040(29) Uiso 0.13(3) d P 2
O14B O 0.5985(136) -0.1127(109) 0.2249(38) 0.031(26) Uiso 0.13(3) d P 2
Cl2 Cl 0.0246(7) 0.4111(7) 0.1129(3) 0.069(2) Uani 1 d . .
O21 O 0.0578(18) 0.2548(16) 0.0995(7) 0.075(4) Uani 1 d . .
O22 O -0.1303(21) 0.3910(21) 0.0858(8) 0.099(6) Uani 1 d . .
O23 O 0.0285(44) 0.4475(37) 0.1725(9) 0.200(15) Uani 1 d . .
O24 O 0.1567(25) 0.5426(26) 0.0936(16) 0.188(14) 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 N4 94.8(5) . . ?
N1 Cu1 N2 85.4(5) . . ?
N4 Cu1 N2 176.7(5) . . ?
N1 Cu1 N3 178.3(6) . . ?
N4 Cu1 N3 84.9(6) . . ?
N2 Cu1 N3 94.8(6) . . ?
N1 Cu1 O21 89.3(5) . . ?
N4 Cu1 O21 95.8(5) . . ?
N2 Cu1 O21 87.5(5) . . ?
N3 Cu1 O21 92.4(5) . . ?
N1 Cu1 O11 90.3(5) . . ?
N4 Cu1 O11 85.4(5) . . ?
N2 Cu1 O11 91.3(5) . . ?
N3 Cu1 O11 88.1(5) . . ?
O21 Cu1 O11 178.7(5) . . ?
C9 N1 C1 110.4(13) . . ?
C9 N1 Cu1 114.7(11) . . ?
C1 N1 Cu1 108.6(10) . . ?
C2 N2 C3 112.0(13) . . ?
C2 N2 Cu1 108.3(9) . . ?
C3 N2 Cu1 116.9(11) . . ?
C5 N3 C6 114.6(16) . . ?
C5 N3 Cu1 115.8(12) . . ?
C6 N3 Cu1 107.8(10) . . ?
C7 N4 C8 111.7(14) . . ?
C7 N4 Cu1 106.0(10) . . ?
C8 N4 Cu1 118.4(10) . . ?
C10 N5 C9 118.7(14) . . ?
C10 N5 C8 121.9(13) . . ?
C9 N5 C8 119.2(13) . . ?
C11 N6 C10 114.4(15) . . ?
C11 N7 C12 121.2(14) . . ?
C10 N8 C12 113.1(15) . . ?
C15 N11 C14 121.5(15) . . ?
C15 N12 C16 124.3(14) . . ?
N1 C1 C2 106.0(13) . . ?
N2 C2 C1 108.6(14) . . ?
N2 C3 C4 112.5(16) . . ?
C5 C4 C3 117.1(15) . . ?
N3 C5 C4 113.8(18) . . ?
N3 C6 C7 106.7(15) . . ?
N4 C7 C6 109.6(15) . . ?
N5 C8 N4 106.0(14) . . ?
N5 C9 N1 109.4(14) . . ?
N8 C10 N6 128.5(14) . . ?
N8 C10 N5 116.3(14) . . ?
N6 C10 N5 115.2(15) . . ?
N9 C11 N7 120.1(15) . . ?
N9 C11 N6 120.0(17) . . ?
N7 C11 N6 119.9(15) . . ?
N7 C12 N10 120.9(15) . . ?
N7 C12 N8 122.3(18) . . ?
N10 C12 N8 116.8(16) . . ?
C14 C13 C16 124.8(15) . . ?
O1 C14 C13 127.9(14) . . ?
O1 C14 N11 115.1(14) . . ?
C13 C14 N11 117.0(15) . . ?
O2 C15 N11 120.5(16) . . ?
O2 C15 N12 119.9(15) . . ?
N11 C15 N12 119.5(15) . . ?
O3 C16 C13 130.3(15) . . ?
O3 C16 N12 117.0(15) . . ?
C13 C16 N12 112.7(16) . . ?
O12B Cl1 O13B 123.3(60) . . ?
O12A Cl1 O13A 111.6(15) . . ?
O12B Cl1 O14B 97.2(58) . . ?
O13B Cl1 O14B 96.6(58) . . ?
O12B Cl1 O11 100.0(36) . . ?
O13B Cl1 O11 122.5(42) . . ?
O12A Cl1 O11 112.5(12) . . ?
O13A Cl1 O11 112.9(12) . . ?
O14B Cl1 O11 115.0(36) . . ?
O12A Cl1 O14A 110.2(20) . . ?
O13A Cl1 O14A 105.7(17) . . ?
O11 Cl1 O14A 103.3(13) . . ?
Cl1 O11 Cu1 126.3(9) . . ?
O23 Cl2 O22 111.5(15) . . ?
O23 Cl2 O24 108.6(21) . . ?
O22 Cl2 O24 111.0(14) . . ?
O23 Cl2 O21 107.4(11) . . ?
O22 Cl2 O21 110.4(10) . . ?
O24 Cl2 O21 107.8(11) . . ?
Cl2 O21 Cu1 125.4(9) . . ?
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 1.998(13) . ?
Cu1 N4 2.014(13) . ?
Cu1 N2 2.014(13) . ?
Cu1 N3 2.042(13) . ?
Cu1 O21 2.457(14) . ?
Cu1 O11 2.603(14) . ?
N1 C9 1.47(2) . ?
N1 C1 1.50(2) . ?
N2 C2 1.46(2) . ?
N2 C3 1.46(2) . ?
N3 C5 1.45(2) . ?
N3 C6 1.46(2) . ?
N4 C7 1.48(2) . ?
N4 C8 1.49(2) . ?
N5 C10 1.37(2) . ?
N5 C9 1.45(2) . ?
N5 C8 1.47(2) . ?
N6 C11 1.34(2) . ?
N6 C10 1.35(2) . ?
N7 C11 1.32(2) . ?
N7 C12 1.32(2) . ?
N8 C10 1.31(2) . ?
N8 C12 1.34(2) . ?
N9 C11 1.28(2) . ?
N10 C12 1.33(2) . ?
N11 C15 1.32(2) . ?
N11 C14 1.42(2) . ?
N12 C15 1.33(2) . ?
N12 C16 1.44(2) . ?
C1 C2 1.53(2) . ?
C3 C4 1.52(3) . ?
C4 C5 1.49(3) . ?
C6 C7 1.49(3) . ?
C13 C14 1.35(2) . ?
C13 C16 1.39(2) . ?
C14 O1 1.26(2) . ?
C15 O2 1.27(2) . ?
C16 O3 1.23(2) . ?
Cl1 O12B 1.13(8) . ?
Cl1 O13B 1.27(10) . ?
Cl1 O12A 1.35(2) . ?
Cl1 O13A 1.39(2) . ?
Cl1 O14B 1.40(9) . ?
Cl1 O11 1.416(12) . ?
Cl1 O14A 1.41(2) . ?
Cl2 O23 1.36(2) . ?
Cl2 O22 1.371(15) . ?
Cl2 O24 1.39(2) . ?
Cl2 O21 1.441(11) . ?
