#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:45:59 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179346 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/43/4324326.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_4324326
loop_
_publ_author_name
'Garam Park'
'Hojin Yang'
'Tae Ho Kim'
'Jineun Kim'
_publ_contact_author_address
; 
Department of Chemistry(BK21)and Research Institute of Natural Science 
Jinju 660-701, Republic of Korea 
;
_publ_contact_author_email       jekim@gnu.ac.kr
_publ_contact_author_fax         +82-55-758-5532
_publ_contact_author_name        'Jineun Kim'
_publ_contact_author_phone       +82-55-751-6024
_publ_section_title
;
 Copper(I) Coordination Polymers of
 N,N'-Bis[3-(methylthio)propyl]pyromellitic Diimide: Crystal
 Transformation and Solvatochromism by Halogen-π Interactions
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              961
_journal_page_last               968
_journal_paper_doi               10.1021/ic101562p
_journal_volume                  50
_journal_year                    2011
_chemical_formula_sum            'C18 H20 Cu I N2 O4 S2'
_chemical_formula_weight         582.92
_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           SHELXTL
_cell_angle_alpha                100.062(11)
_cell_angle_beta                 99.706(10)
_cell_angle_gamma                90.402(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2384(14)
_cell_length_b                   7.7561(15)
_cell_length_c                   19.188(4)
_cell_measurement_reflns_used    9720
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.67
_cell_volume                     1044.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16887
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    2.750
_exptl_absorpt_correction_T_max  0.9221
_exptl_absorpt_correction_T_min  0.7338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         4.105
_refine_diff_density_min         -1.089
_refine_diff_density_rms         0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0888P)²+13.4223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1811
_refine_ls_wR_factor_ref         0.1876
_reflns_number_gt                3847
_reflns_number_total             4538
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic101562p_si_002_2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1044.7(4)
_cod_database_code               4324326
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
Cu1 Cu 0.96417(14) 0.96331(13) 0.42575(6) 0.0268(3) Uani 1 1 d .
I1 I 0.78410(7) 1.20401(7) 0.49976(3) 0.02472(19) Uani 1 1 d .
S1 S 0.7508(3) 0.7651(3) 0.34792(11) 0.0260(4) Uani 1 1 d .
S2 S 1.1156(3) 1.0983(3) 0.35035(11) 0.0267(4) Uani 1 1 d .
O1 O -0.0089(11) 0.8555(10) 0.1607(4) 0.0478(18) Uani 1 1 d .
O2 O 0.5005(9) 0.5573(10) 0.0992(4) 0.0425(16) Uani 1 1 d .
O3 O 0.9791(10) 1.2084(10) 0.0797(4) 0.0418(16) Uani 1 1 d .
O4 O 0.4526(10) 1.2519(10) 0.1830(4) 0.0455(17) Uani 1 1 d .
N1 N 0.2740(11) 0.7269(11) 0.1458(4) 0.0354(17) Uani 1 1 d .
N2 N 0.7439(11) 1.2553(11) 0.1473(4) 0.0344(17) Uani 1 1 d .
C1 C 0.7104(17) 0.5856(14) 0.3919(6) 0.047(3) Uani 1 1 d .
H1A H 0.6532 0.6285 0.4341 0.070 Uiso 1 1 calc R
H1B H 0.8301 0.5332 0.4069 0.070 Uiso 1 1 calc R
H1C H 0.6261 0.4973 0.3586 0.070 Uiso 1 1 calc R
C2 C 0.5191(13) 0.8508(13) 0.3404(5) 0.037(2) Uani 1 1 d .
H2A H 0.4703 0.8460 0.3852 0.044 Uiso 1 1 calc R
H2B H 0.5272 0.9753 0.3353 0.044 Uiso 1 1 calc R
C3 C 0.3804(14) 0.7502(13) 0.2763(5) 0.036(2) Uani 1 1 d .
H3A H 0.4106 0.6247 0.2681 0.044 Uiso 1 1 calc R
H3B H 0.2511 0.7592 0.2867 0.044 Uiso 1 1 calc R
C4 C 0.3934(15) 0.8263(15) 0.2101(5) 0.044(2) Uani 1 1 d .
H4A H 0.3549 0.9495 0.2175 0.053 Uiso 1 1 calc R
H4B H 0.5253 0.8259 0.2024 0.053 Uiso 1 1 calc R
C5 C 0.0815(14) 0.7512(13) 0.1285(5) 0.036(2) Uani 1 1 d .
C6 C 0.0183(13) 0.6226(12) 0.0598(5) 0.0315(19) Uani 1 1 d .
C7 C 0.1700(13) 0.5337(13) 0.0408(5) 0.0334(19) Uani 1 1 d .
C8 C 0.3373(13) 0.6027(13) 0.0966(5) 0.0335(19) Uani 1 1 d .
C9 C -0.1585(13) 0.5904(13) 0.0202(5) 0.0334(19) Uani 1 1 d .
H9 H -0.2647 0.6496 0.0340 0.040 Uiso 1 1 calc R
C10 C 1.2292(16) 1.2922(15) 0.4073(6) 0.048(3) Uani 1 1 d .
H10A H 1.2849 1.3633 0.3781 0.072 Uiso 1 1 calc R
H10B H 1.3278 1.2586 0.4435 0.072 Uiso 1 1 calc R
H10C H 1.1368 1.3603 0.4311 0.072 Uiso 1 1 calc R
C11 C 0.9307(13) 1.1892(13) 0.2953(5) 0.0339(19) Uani 1 1 d .
H11A H 0.8564 1.0925 0.2615 0.041 Uiso 1 1 calc R
H11B H 0.8465 1.2506 0.3263 0.041 Uiso 1 1 calc R
C12 C 0.9996(14) 1.3168(14) 0.2526(5) 0.038(2) Uani 1 1 d .
H12A H 1.0695 1.4161 0.2865 0.045 Uiso 1 1 calc R
H12B H 1.0877 1.2569 0.2230 0.045 Uiso 1 1 calc R
C13 C 0.8444(15) 1.3863(13) 0.2048(5) 0.038(2) Uani 1 1 d .
H13A H 0.7540 1.4418 0.2344 0.046 Uiso 1 1 calc R
H13B H 0.8972 1.4786 0.1834 0.046 Uiso 1 1 calc R
C14 C 0.8186(13) 1.1834(12) 0.0880(5) 0.0324(19) Uani 1 1 d .
C15 C 0.6662(13) 1.0787(12) 0.0365(5) 0.0335(19) Uani 1 1 d .
C16 C 0.5048(13) 1.0972(12) 0.0670(5) 0.0331(19) Uani 1 1 d .
C17 C 0.5518(13) 1.2095(13) 0.1387(5) 0.034(2) Uani 1 1 d .
C18 C 0.6653(14) 0.9847(14) -0.0320(5) 0.039(2) Uani 1 1 d .
H18 H 0.7743 0.9768 -0.0537 0.047 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 0.0033 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'
S S 0.1246 0.1234 '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'
I I -0.4742 1.8119 '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
S1 Cu1 S2 104.31(9) . .
S1 Cu1 I1 109.99(7) . 2_776
S2 Cu1 I1 107.57(6) . 2_776
S1 Cu1 I1 109.75(6) . .
S2 Cu1 I1 108.04(6) . .
I1 Cu1 I1 116.45(4) 2_776 .
S1 Cu1 Cu1 130.19(8) . 2_776
S2 Cu1 Cu1 125.50(8) . 2_776
I1 Cu1 Cu1 58.50(4) 2_776 2_776
I1 Cu1 Cu1 57.95(4) . 2_776
Cu1 I1 Cu1 63.55(4) 2_776 .
C1 S1 C2 98.4(5) . .
C1 S1 Cu1 108.5(4) . .
C2 S1 Cu1 110.3(3) . .
C11 S2 C10 101.6(5) . .
C11 S2 Cu1 104.5(3) . .
C10 S2 Cu1 104.6(4) . .
C8 N1 C5 112.7(8) . .
C8 N1 C4 124.3(8) . .
C5 N1 C4 123.0(9) . .
C14 N2 C17 111.4(8) . .
C14 N2 C13 122.8(8) . .
C17 N2 C13 124.8(8) . .
S1 C1 H1A 109.5 . .
S1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
S1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 S1 113.1(7) . .
C3 C2 H2A 109.0 . .
S1 C2 H2A 109.0 . .
C3 C2 H2B 109.0 . .
S1 C2 H2B 108.9 . .
H2A C2 H2B 107.8 . .
C4 C3 C2 109.4(8) . .
C4 C3 H3A 109.8 . .
C2 C3 H3A 109.8 . .
C4 C3 H3B 109.8 . .
C2 C3 H3B 109.8 . .
H3A C3 H3B 108.2 . .
N1 C4 C3 111.8(8) . .
N1 C4 H4A 109.3 . .
C3 C4 H4A 109.3 . .
N1 C4 H4B 109.3 . .
C3 C4 H4B 109.3 . .
H4A C4 H4B 107.9 . .
O1 C5 N1 126.7(9) . .
O1 C5 C6 128.7(9) . .
N1 C5 C6 104.6(8) . .
C7 C6 C9 122.5(9) . .
C7 C6 C5 108.8(8) . .
C9 C6 C5 128.8(9) . .
C6 C7 C9 122.8(9) . 2_565
C6 C7 C8 107.3(8) . .
C9 C7 C8 129.9(9) 2_565 .
O2 C8 N1 125.5(9) . .
O2 C8 C7 127.8(9) . .
N1 C8 C7 106.7(8) . .
C7 C9 C6 114.7(9) 2_565 .
C7 C9 H9 122.6 2_565 .
C6 C9 H9 122.6 . .
S2 C10 H10A 109.5 . .
S2 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
S2 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C12 C11 S2 113.6(7) . .
C12 C11 H11A 108.8 . .
S2 C11 H11A 108.8 . .
C12 C11 H11B 108.8 . .
S2 C11 H11B 108.8 . .
H11A C11 H11B 107.7 . .
C13 C12 C11 113.0(8) . .
C13 C12 H12A 109.0 . .
C11 C12 H12A 109.0 . .
C13 C12 H12B 109.0 . .
C11 C12 H12B 109.0 . .
H12A C12 H12B 107.8 . .
N2 C13 C12 114.4(8) . .
N2 C13 H13A 108.7 . .
C12 C13 H13A 108.7 . .
N2 C13 H13B 108.7 . .
C12 C13 H13B 108.7 . .
H13A C13 H13B 107.6 . .
O3 C14 N2 125.2(9) . .
O3 C14 C15 127.5(9) . .
N2 C14 C15 107.2(8) . .
C18 C15 C16 122.1(9) . .
C18 C15 C14 130.6(9) . .
C16 C15 C14 107.2(8) . .
C15 C16 C18 121.9(9) . 2_675
C15 C16 C17 108.5(9) . .
C18 C16 C17 129.5(8) 2_675 .
O4 C17 N2 125.4(9) . .
O4 C17 C16 129.0(9) . .
N2 C17 C16 105.6(8) . .
C15 C18 C16 115.9(9) . 2_675
C15 C18 H18 122.1 . .
C16 C18 H18 122.1 2_675 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 S1 2.317(2) .
Cu1 S2 2.332(2) .
Cu1 I1 2.6174(12) 2_776
Cu1 I1 2.6330(12) .
Cu1 Cu1 2.765(2) 2_776
I1 Cu1 2.6174(12) 2_776
S1 C1 1.795(10) .
S1 C2 1.800(10) .
S2 C11 1.788(10) .
S2 C10 1.799(11) .
O1 C5 1.198(12) .
O2 C8 1.230(12) .
O3 C14 1.218(11) .
O4 C17 1.208(11) .
N1 C8 1.365(13) .
N1 C5 1.399(12) .
N1 C4 1.470(12) .
N2 C14 1.374(12) .
N2 C17 1.408(12) .
N2 C13 1.451(12) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.539(13) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.508(14) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.508(13) .
C6 C7 1.368(13) .
C6 C9 1.370(13) .
C7 C9 1.369(13) 2_565
C7 C8 1.501(13) .
C9 C7 1.369(13) 2_565
C9 H9 0.9500 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.521(13) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.493(14) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.481(14) .
C15 C18 1.386(14) .
C15 C16 1.390(12) .
C16 C18 1.390(15) 2_675
C16 C17 1.478(14) .
C18 C16 1.390(15) 2_675
C18 H18 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_1
_geom_torsion_site_symmetry_4
S1 Cu1 I1 Cu1 125.75(9) . 2_776
S2 Cu1 I1 Cu1 -121.11(8) . 2_776
I1 Cu1 I1 Cu1 0.0 2_776 2_776
S2 Cu1 S1 C1 151.8(4) . .
I1 Cu1 S1 C1 36.7(5) 2_776 .
I1 Cu1 S1 C1 -92.7(4) . .
Cu1 Cu1 S1 C1 -28.4(5) 2_776 .
S2 Cu1 S1 C2 -101.4(4) . .
I1 Cu1 S1 C2 143.5(4) 2_776 .
I1 Cu1 S1 C2 14.2(4) . .
Cu1 Cu1 S1 C2 78.4(4) 2_776 .
S1 Cu1 S2 C11 57.3(3) . .
I1 Cu1 S2 C11 174.1(3) 2_776 .
I1 Cu1 S2 C11 -59.4(3) . .
Cu1 Cu1 S2 C11 -122.4(3) 2_776 .
S1 Cu1 S2 C10 163.7(4) . .
I1 Cu1 S2 C10 -79.5(4) 2_776 .
I1 Cu1 S2 C10 47.0(4) . .
Cu1 Cu1 S2 C10 -16.1(4) 2_776 .
C1 S1 C2 C3 -81.1(8) . .
Cu1 S1 C2 C3 165.4(6) . .
S1 C2 C3 C4 -87.0(10) . .
C8 N1 C4 C3 -98.7(11) . .
C5 N1 C4 C3 81.8(12) . .
C2 C3 C4 N1 175.8(8) . .
C8 N1 C5 O1 -177.2(10) . .
C4 N1 C5 O1 2.4(16) . .
C8 N1 C5 C6 0.8(10) . .
C4 N1 C5 C6 -179.6(8) . .
O1 C5 C6 C7 177.7(10) . .
N1 C5 C6 C7 -0.3(10) . .
O1 C5 C6 C9 -3.1(17) . .
N1 C5 C6 C9 178.9(9) . .
C9 C6 C7 C9 2.0(17) . 2_565
C5 C6 C7 C9 -178.7(9) . 2_565
C9 C6 C7 C8 -179.6(9) . .
C5 C6 C7 C8 -0.3(10) . .
C5 N1 C8 O2 179.7(9) . .
C4 N1 C8 O2 0.1(15) . .
C5 N1 C8 C7 -1.0(10) . .
C4 N1 C8 C7 179.4(9) . .
C6 C7 C8 O2 -180.0(9) . .
C9 C7 C8 O2 -1.7(17) 2_565 .
C6 C7 C8 N1 0.8(10) . .
C9 C7 C8 N1 179.1(10) 2_565 .
C7 C6 C9 C7 -1.8(15) . 2_565
C5 C6 C9 C7 179.0(9) . 2_565
C10 S2 C11 C12 59.1(8) . .
Cu1 S2 C11 C12 167.7(6) . .
S2 C11 C12 C13 177.8(7) . .
C14 N2 C13 C12 -73.6(11) . .
C17 N2 C13 C12 118.2(10) . .
C11 C12 C13 N2 -65.2(11) . .
C17 N2 C14 O3 176.3(9) . .
C13 N2 C14 O3 6.7(14) . .
C17 N2 C14 C15 -1.3(10) . .
C13 N2 C14 C15 -170.9(8) . .
O3 C14 C15 C18 0.2(17) . .
N2 C14 C15 C18 177.8(10) . .
O3 C14 C15 C16 -175.9(9) . .
N2 C14 C15 C16 1.6(10) . .
C18 C15 C16 C18 3.2(16) . 2_675
C14 C15 C16 C18 179.8(8) . 2_675
C18 C15 C16 C17 -177.9(9) . .
C14 C15 C16 C17 -1.3(10) . .
C14 N2 C17 O4 178.4(9) . .
C13 N2 C17 O4 -12.2(15) . .
C14 N2 C17 C16 0.5(10) . .
C13 N2 C17 C16 169.9(8) . .
C15 C16 C17 O4 -177.3(10) . .
C18 C16 C17 O4 1.5(18) 2_675 .
C15 C16 C17 N2 0.6(10) . .
C18 C16 C17 N2 179.4(9) 2_675 .
C16 C15 C18 C16 -3.1(15) . 2_675
C14 C15 C18 C16 -178.7(9) . 2_675
