#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:56:45 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179907 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/03/7020334.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_7020334
loop_
_publ_author_name
'Safko, Jason P.'
'Kuperstock, Jacob E.'
'McCullough, Shannon M.'
'Noviello, Andrew M.'
'Li, Xiaobo'
'Killarney, James P.'
'Murphy, Caitlin'
'Patterson, Howard H.'
'Bayse, Craig A.'
'Pike, Robert D.'
_publ_section_title
;
 Network formation and photoluminescence in copper(I) halide complexes
 with substituted piperazine ligands.
;
_journal_issue                   38
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11663
_journal_page_last               11674
_journal_paper_doi               10.1039/c2dt31241g
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C16 H20 Cu2 I2 N4'
_chemical_formula_sum            'C16 H20 Cu2 I2 N4'
_chemical_formula_weight         649.24
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.8310(10)
_cell_angle_beta                 91.449(2)
_cell_angle_gamma                95.4470(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6487(2)
_cell_length_b                   9.9098(2)
_cell_length_c                   12.4157(3)
_cell_measurement_reflns_used    8676
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.05
_cell_measurement_theta_min      4.87
_cell_volume                     974.07(4)
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'XSHELL (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker SMART Apex II CCD'
_diffrn_measurement_method       'ω and ψ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16265
_diffrn_reflns_theta_full        66.99
_diffrn_reflns_theta_max         66.99
_diffrn_reflns_theta_min         3.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    27.613
_exptl_absorpt_correction_T_max  0.3763
_exptl_absorpt_correction_T_min  0.0626
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.874
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0492P)²+0.0555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0762
_reflns_number_gt                3096
_reflns_number_total             3360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt31241g.txt
_cod_data_source_block           p1bar
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7020334
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.83863(2) 0.33329(2) 0.753669(17) 0.01819(10) Uani 1 1 d .
I2 I 0.58999(2) 0.70588(2) 0.734809(18) 0.01988(10) Uani 1 1 d .
Cu1 Cu 0.58545(6) 0.45647(6) 0.75210(4) 0.01825(14) Uani 1 1 d .
Cu2 Cu 0.85146(6) 0.58562(6) 0.73831(5) 0.01982(14) Uani 1 1 d .
N1 N 0.4277(3) 0.2888(3) 0.6394(3) 0.0179(6) Uani 1 1 d .
N2 N 0.4226(3) 0.4425(3) 0.8831(3) 0.0172(6) Uani 1 1 d .
N3 N 1.0179(3) 0.7489(3) 0.8483(3) 0.0194(6) Uani 1 1 d .
N4 N 0.9916(3) 0.6314(3) 0.6048(3) 0.0164(6) Uani 1 1 d .
C1 C 0.3955(4) 0.5869(4) 0.9730(3) 0.0179(7) Uani 1 1 d .
H1B H 0.3046 0.5740 1.0164 0.021 Uiso 1 1 calc R
H1A H 0.3718 0.6540 0.9345 0.021 Uiso 1 1 calc R
C2 C 0.4615(4) 0.3450(4) 0.9415(3) 0.0176(7) Uani 1 1 d .
H2B H 0.4820 0.2488 0.8819 0.021 Uiso 1 1 calc R
H2A H 0.3719 0.3275 0.9844 0.021 Uiso 1 1 calc R
C3 C 0.2764(4) 0.3787(4) 0.8089(3) 0.0192(7) Uani 1 1 d .
H3A H 0.2277 0.4583 0.7962 0.023 Uiso 1 1 calc R
H3B H 0.2035 0.3362 0.8507 0.023 Uiso 1 1 calc R
C4 C 0.3009(4) 0.2603(4) 0.6913(3) 0.0182(7) Uani 1 1 d .
C5 C 0.1953(4) 0.1362(4) 0.6366(3) 0.0201(7) Uani 1 1 d .
H5 H 0.1088 0.1164 0.6760 0.024 Uiso 1 1 calc R
C6 C 0.2180(4) 0.0411(4) 0.5233(3) 0.0222(7) Uani 1 1 d .
H6 H 0.1470 -0.0447 0.4838 0.027 Uiso 1 1 calc R
C7 C 0.3460(4) 0.0732(4) 0.4685(3) 0.0217(7) Uani 1 1 d .
H7 H 0.3628 0.0115 0.3902 0.026 Uiso 1 1 calc R
C8 C 0.4479(4) 0.1968(4) 0.5305(3) 0.0194(7) Uani 1 1 d .
H8 H 0.5370 0.2174 0.4939 0.023 Uiso 1 1 calc R
C9 C 0.9018(4) 0.6041(4) 0.4944(3) 0.0183(7) Uani 1 1 d .
H9B H 0.9627 0.6495 0.4482 0.022 Uiso 1 1 calc R
H9A H 0.8039 0.6503 0.5120 0.022 Uiso 1 1 calc R
C10 C 1.1357(4) 0.5590(4) 0.5765(3) 0.0190(7) Uani 1 1 d .
H10B H 1.1963 0.5749 0.6499 0.023 Uiso 1 1 calc R
H10A H 1.2003 0.6037 0.5316 0.023 Uiso 1 1 calc R
C11 C 1.0326(4) 0.7914(4) 0.6696(3) 0.0216(7) Uani 1 1 d .
H11A H 0.9400 0.8426 0.6691 0.026 Uiso 1 1 calc R
H11B H 1.1144 0.8272 0.6295 0.026 Uiso 1 1 calc R
C12 C 1.0902(4) 0.8285(4) 0.7939(3) 0.0203(7) Uani 1 1 d .
C13 C 1.2082(5) 0.9418(4) 0.8523(4) 0.0263(8) Uani 1 1 d .
H13 H 1.2610 0.9946 0.8120 0.032 Uiso 1 1 calc R
C14 C 1.2477(5) 0.9766(5) 0.9693(4) 0.0297(9) Uani 1 1 d .
H14 H 1.3261 1.0552 1.0108 0.036 Uiso 1 1 calc R
C15 C 1.1717(5) 0.8954(5) 1.0253(3) 0.0281(8) Uani 1 1 d .
H15 H 1.1965 0.9172 1.1057 0.034 Uiso 1 1 calc R
C16 C 1.0584(4) 0.7812(4) 0.9608(3) 0.0232(8) Uani 1 1 d .
H16 H 1.0076 0.7237 0.9983 0.028 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
Cu2 I1 Cu1 59.386(17) . .
Cu1 I2 Cu2 58.873(16) . .
N1 Cu1 N2 82.22(12) . .
N1 Cu1 I2 116.29(9) . .
N2 Cu1 I2 110.62(8) . .
N1 Cu1 Cu2 136.50(9) . .
N2 Cu1 Cu2 140.92(8) . .
I2 Cu1 Cu2 62.549(18) . .
N1 Cu1 I1 104.78(9) . .
N2 Cu1 I1 113.86(8) . .
I2 Cu1 I1 122.145(19) . .
Cu2 Cu1 I1 59.599(17) . .
N3 Cu2 N4 80.25(12) . .
N3 Cu2 Cu1 138.33(9) . .
N4 Cu2 Cu1 139.42(8) . .
N3 Cu2 I1 116.54(9) . .
N4 Cu2 I1 120.79(8) . .
Cu1 Cu2 I1 61.015(18) . .
N3 Cu2 I2 108.23(9) . .
N4 Cu2 I2 104.46(8) . .
Cu1 Cu2 I2 58.578(17) . .
I1 Cu2 I2 119.590(19) . .
C8 N1 C4 118.5(3) . .
C8 N1 Cu1 127.4(2) . .
C4 N1 Cu1 113.4(2) . .
C2 N2 C3 109.2(3) . .
C2 N2 C1 109.0(3) . .
C3 N2 C1 107.7(3) . .
C2 N2 Cu1 115.0(2) . .
C3 N2 Cu1 101.3(2) . .
C1 N2 Cu1 114.2(2) . .
C16 N3 C12 119.2(3) . .
C16 N3 Cu2 128.5(3) . .
C12 N3 Cu2 112.3(2) . .
C9 N4 C11 109.5(3) . .
C9 N4 C10 108.6(3) . .
C11 N4 C10 109.4(3) . .
C9 N4 Cu2 114.1(2) . .
C11 N4 Cu2 98.51(19) . .
C10 N4 Cu2 116.2(2) . .
N2 C1 C2 110.7(3) . 2_667
N2 C1 H1B 109.5 . .
C2 C1 H1B 109.5 2_667 .
N2 C1 H1A 109.5 . .
C2 C1 H1A 109.5 2_667 .
H1B C1 H1A 108.1 . .
N2 C2 C1 110.9(3) . 2_667
N2 C2 H2B 109.5 . .
C1 C2 H2B 109.5 2_667 .
N2 C2 H2A 109.5 . .
C1 C2 H2A 109.5 2_667 .
H2B C2 H2A 108.0 . .
N2 C3 C4 112.9(3) . .
N2 C3 H3A 109.0 . .
C4 C3 H3A 109.0 . .
N2 C3 H3B 109.0 . .
C4 C3 H3B 109.0 . .
H3A C3 H3B 107.8 . .
N1 C4 C5 122.0(3) . .
N1 C4 C3 115.2(3) . .
C5 C4 C3 122.6(3) . .
C4 C5 C6 118.9(3) . .
C4 C5 H5 120.6 . .
C6 C5 H5 120.6 . .
C5 C6 C7 119.0(3) . .
C5 C6 H6 120.5 . .
C7 C6 H6 120.5 . .
C8 C7 C6 118.3(3) . .
C8 C7 H7 120.8 . .
C6 C7 H7 120.8 . .
N1 C8 C7 123.2(3) . .
N1 C8 H8 118.4 . .
C7 C8 H8 118.4 . .
N4 C9 C10 110.8(3) . 2_766
N4 C9 H9B 109.5 . .
C10 C9 H9B 109.5 2_766 .
N4 C9 H9A 109.5 . .
C10 C9 H9A 109.5 2_766 .
H9B C9 H9A 108.1 . .
N4 C10 C9 110.9(3) . 2_766
N4 C10 H10B 109.5 . .
C9 C10 H10B 109.5 2_766 .
N4 C10 H10A 109.5 . .
C9 C10 H10A 109.5 2_766 .
H10B C10 H10A 108.1 . .
N4 C11 C12 111.9(3) . .
N4 C11 H11A 109.2 . .
C12 C11 H11A 109.2 . .
N4 C11 H11B 109.2 . .
C12 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
N3 C12 C13 121.1(3) . .
N3 C12 C11 116.2(3) . .
C13 C12 C11 122.6(3) . .
C14 C13 C12 119.4(4) . .
C14 C13 H13 120.3 . .
C12 C13 H13 120.3 . .
C13 C14 C15 119.2(4) . .
C13 C14 H14 120.4 . .
C15 C14 H14 120.4 . .
C14 C15 C16 118.3(4) . .
C14 C15 H15 120.8 . .
C16 C15 H15 120.8 . .
N3 C16 C15 122.7(3) . .
N3 C16 H16 118.7 . .
C15 C16 H16 118.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Cu2 2.5729(6) .
I1 Cu1 2.6094(5) .
I2 Cu1 2.5593(6) .
I2 Cu2 2.6614(6) .
Cu1 N1 2.061(3) .
Cu1 N2 2.214(3) .
Cu1 Cu2 2.5673(7) .
Cu2 N3 2.073(3) .
Cu2 N4 2.237(3) .
N1 C8 1.333(5) .
N1 C4 1.347(5) .
N2 C2 1.472(5) .
N2 C3 1.478(4) .
N2 C1 1.478(5) .
N3 C16 1.335(5) .
N3 C12 1.346(5) .
N4 C9 1.475(5) .
N4 C11 1.474(5) .
N4 C10 1.479(5) .
C1 C2 1.528(5) 2_667
C1 H1B 0.9900 .
C1 H1A 0.9900 .
C2 C1 1.528(5) 2_667
C2 H2B 0.9900 .
C2 H2A 0.9900 .
C3 C4 1.512(5) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.384(5) .
C5 C6 1.388(6) .
C5 H5 0.9500 .
C6 C7 1.389(6) .
C6 H6 0.9500 .
C7 C8 1.378(6) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C10 1.507(5) 2_766
C9 H9B 0.9900 .
C9 H9A 0.9900 .
C10 C9 1.507(5) 2_766
C10 H10B 0.9900 .
C10 H10A 0.9900 .
C11 C12 1.501(5) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.393(6) .
C13 C14 1.382(6) .
C13 H13 0.9500 .
C14 C15 1.386(7) .
C14 H14 0.9500 .
C15 C16 1.389(6) .
C15 H15 0.9500 .
C16 H16 0.9500 .
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_4
Cu2 I2 Cu1 N1 -130.93(10) .
Cu2 I2 Cu1 N2 137.67(9) .
Cu2 I2 Cu1 I1 -0.652(18) .
Cu2 I1 Cu1 N1 135.64(9) .
Cu2 I1 Cu1 N2 -136.44(9) .
Cu2 I1 Cu1 I2 0.671(18) .
N1 Cu1 Cu2 N3 -177.52(17) .
N2 Cu1 Cu2 N3 -7.2(2) .
I2 Cu1 Cu2 N3 82.25(14) .
I1 Cu1 Cu2 N3 -98.39(14) .
N1 Cu1 Cu2 N4 25.51(18) .
N2 Cu1 Cu2 N4 -164.14(17) .
I2 Cu1 Cu2 N4 -74.72(12) .
I1 Cu1 Cu2 N4 104.64(12) .
N1 Cu1 Cu2 I1 -79.13(13) .
N2 Cu1 Cu2 I1 91.23(14) .
I2 Cu1 Cu2 I1 -179.360(17) .
N1 Cu1 Cu2 I2 100.23(13) .
N2 Cu1 Cu2 I2 -89.41(14) .
I1 Cu1 Cu2 I2 179.360(17) .
Cu1 I1 Cu2 N3 132.68(10) .
Cu1 I1 Cu2 N4 -132.89(10) .
Cu1 I1 Cu2 I2 -0.628(17) .
Cu1 I2 Cu2 N3 -136.09(9) .
Cu1 I2 Cu2 N4 139.61(8) .
Cu1 I2 Cu2 I1 0.644(17) .
N2 Cu1 N1 C8 -164.3(3) .
I2 Cu1 N1 C8 86.5(3) .
Cu2 Cu1 N1 C8 9.6(4) .
I1 Cu1 N1 C8 -51.5(3) .
N2 Cu1 N1 C4 5.7(2) .
I2 Cu1 N1 C4 -103.5(2) .
Cu2 Cu1 N1 C4 179.55(19) .
I1 Cu1 N1 C4 118.4(2) .
N1 Cu1 N2 C2 92.8(2) .
I2 Cu1 N2 C2 -152.0(2) .
Cu2 Cu1 N2 C2 -80.5(3) .
I1 Cu1 N2 C2 -10.0(3) .
N1 Cu1 N2 C3 -24.7(2) .
I2 Cu1 N2 C3 90.5(2) .
Cu2 Cu1 N2 C3 161.98(17) .
I1 Cu1 N2 C3 -127.5(2) .
N1 Cu1 N2 C1 -140.1(2) .
I2 Cu1 N2 C1 -24.9(2) .
Cu2 Cu1 N2 C1 46.6(3) .
I1 Cu1 N2 C1 117.1(2) .
N4 Cu2 N3 C16 -161.1(3) .
Cu1 Cu2 N3 C16 33.8(4) .
I1 Cu2 N3 C16 -41.5(3) .
I2 Cu2 N3 C16 96.8(3) .
N4 Cu2 N3 C12 18.8(2) .
Cu1 Cu2 N3 C12 -146.2(2) .
I1 Cu2 N3 C12 138.5(2) .
I2 Cu2 N3 C12 -83.3(2) .
N3 Cu2 N4 C9 -151.0(3) .
Cu1 Cu2 N4 C9 13.7(3) .
I1 Cu2 N4 C9 93.9(2) .
I2 Cu2 N4 C9 -44.5(2) .
N3 Cu2 N4 C11 -35.1(2) .
Cu1 Cu2 N4 C11 129.64(19) .
I1 Cu2 N4 C11 -150.23(18) .
I2 Cu2 N4 C11 71.4(2) .
N3 Cu2 N4 C10 81.5(3) .
Cu1 Cu2 N4 C10 -113.8(2) .
I1 Cu2 N4 C10 -33.7(3) .
I2 Cu2 N4 C10 -172.0(2) .
C2 N2 C1 C2 57.8(4) 2_667
C3 N2 C1 C2 176.1(3) 2_667
Cu1 N2 C1 C2 -72.3(3) 2_667
C3 N2 C2 C1 -175.2(3) 2_667
C1 N2 C2 C1 -57.9(4) 2_667
Cu1 N2 C2 C1 71.8(3) 2_667
C2 N2 C3 C4 -81.7(4) .
C1 N2 C3 C4 160.1(3) .
Cu1 N2 C3 C4 39.9(3) .
C8 N1 C4 C5 2.4(5) .
Cu1 N1 C4 C5 -168.5(3) .
C8 N1 C4 C3 -173.2(3) .
Cu1 N1 C4 C3 15.9(4) .
N2 C3 C4 N1 -40.8(4) .
N2 C3 C4 C5 143.6(3) .
N1 C4 C5 C6 -2.3(6) .
C3 C4 C5 C6 173.0(3) .
C4 C5 C6 C7 0.2(6) .
C5 C6 C7 C8 1.7(6) .
C4 N1 C8 C7 -0.4(5) .
Cu1 N1 C8 C7 169.1(3) .
C6 C7 C8 N1 -1.7(6) .
C11 N4 C9 C10 177.4(3) 2_766
C10 N4 C9 C10 58.0(4) 2_766
Cu2 N4 C9 C10 -73.3(3) 2_766
C9 N4 C10 C9 -58.1(4) 2_766
C11 N4 C10 C9 -177.5(3) 2_766
Cu2 N4 C10 C9 72.1(3) 2_766
C9 N4 C11 C12 166.5(3) .
C10 N4 C11 C12 -74.7(3) .
Cu2 N4 C11 C12 47.0(3) .
C16 N3 C12 C13 1.3(5) .
Cu2 N3 C12 C13 -178.7(3) .
C16 N3 C12 C11 -176.8(3) .
Cu2 N3 C12 C11 3.3(4) .
N4 C11 C12 N3 -38.1(4) .
N4 C11 C12 C13 143.9(4) .
N3 C12 C13 C14 -2.4(6) .
C11 C12 C13 C14 175.5(4) .
C12 C13 C14 C15 1.7(6) .
C13 C14 C15 C16 0.2(6) .
C12 N3 C16 C15 0.7(6) .
Cu2 N3 C16 C15 -179.3(3) .
C14 C15 C16 N3 -1.4(6) .
