#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:20:49 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179323 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/20/4322080.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_4322080
loop_
_publ_author_name
'Rebecca R. Conry'
'William S. Striejewske'
'A. Alex Tipton'
_publ_contact_author_address
;   University of Nevada, Reno
    Department of Chemistry 216
    Reno, Nevada  89557   USA
;
_publ_contact_author_email       conry@chem.unr.edu
_publ_contact_author_name        'Rebecca R. Conry'
_publ_section_title
;
 Copper(I) Complexes with a NS2-Macrocyclic Ligand Bearing a Pendant
 Naphthyl Group: Structures of
 {N-[2-(1-Naphthyl)ethyl]-1-aza-4,8-dithiacyclodecane}copper(I)-Ligand,
 where Ligand = η2-Naphthalene, Acetonitrile, or Triphenylphosphine
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2833
_journal_page_last               2843
_journal_paper_doi               10.1021/ic981418p
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C21 H28 Cu F6 N2 P S2'
_chemical_formula_weight         581.08
_chemical_name_common            'Complex 1'
_chemical_name_systematic
;  [(N-(2-(1-naphthyl)ethyl)-1-aza-4,8-
 dithiacyclodecane)copper(I)(acetonitrile)]hexafluorophosphate 
;
_chemical_temperature_decomposition 426
_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 methods'
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL generated with manual editing'
_cell_angle_alpha                98.996(8)
_cell_angle_beta                 117.188(6)
_cell_angle_gamma                105.354(7)
_cell_formula_units_Z            2
_cell_length_a                   11.1901(10)
_cell_length_b                   11.2735(12)
_cell_length_c                   12.1350(10)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.50
_cell_measurement_theta_min      4.83
_cell_volume                     1242.6(2)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3801
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        5.38
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.169
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            cream
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       wedge
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.053
_refine_ls_goodness_of_fit_obs   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_restrained_S_obs      1.087
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_obs          0.0505
_refine_ls_shift/esd_max         -0.020
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0860P)²+0.6490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1418
_refine_ls_wR_factor_obs         0.1291
_reflns_number_observed          2567
_reflns_number_total             3202
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic981418p_1.cif
_cod_data_source_block           complex1.IC981418P
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+0.6490P] 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^)+(0.0860P)^2^+0.6490P] 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               4322080
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
Cu Cu 0.46418(6) 0.55138(6) 0.25573(6) 0.0606(3) Uani 1 d . 1
S1 S 0.58275(14) 0.63968(12) 0.47651(12) 0.0601(4) Uani 1 d . 1
S2 S 0.6040(2) 0.4727(2) 0.2032(2) 0.0868(5) Uani 1 d . 1
N1 N 0.5607(4) 0.7380(4) 0.2419(4) 0.0597(11) Uani 1 d . .
N2 N 0.2557(5) 0.4674(4) 0.1570(4) 0.0650(11) Uani 1 d . 1
C1 C 0.6821(6) 0.8228(5) 0.3749(5) 0.0725(15) Uani 1 d . 1
H1A H 0.7040(6) 0.9128(5) 0.3775(5) 0.087 Uiso 1 calc R 1
H1B H 0.7679(6) 0.8042(5) 0.3929(5) 0.087 Uiso 1 calc R 1
C2 C 0.6498(7) 0.8056(5) 0.4808(5) 0.0731(15) Uani 1 d . 1
H2A H 0.5785(7) 0.8424(5) 0.4737(5) 0.088 Uiso 1 calc R 1
H2B H 0.7381(7) 0.8549(5) 0.5653(5) 0.088 Uiso 1 calc R 1
C3 C 0.7435(6) 0.5996(6) 0.5484(5) 0.0715(15) Uani 1 d . 1
H3A H 0.8141(6) 0.6669(6) 0.6321(5) 0.086 Uiso 1 calc R 1
H3B H 0.7157(6) 0.5195(6) 0.5669(5) 0.086 Uiso 1 calc R 1
C4 C 0.8217(6) 0.5826(6) 0.4776(6) 0.074(2) Uani 1 d . 1
H4A H 0.9124(6) 0.5775(6) 0.5390(6) 0.089 Uiso 1 calc R 1
H4B H 0.8467(6) 0.6610(6) 0.4558(6) 0.089 Uiso 1 calc R 1
C5 C 0.7471(7) 0.4684(6) 0.3544(7) 0.090(2) Uani 1 d . 1
H5A H 0.7059(7) 0.3916(6) 0.3717(7) 0.108 Uiso 1 calc R 1
H5B H 0.8214(7) 0.4567(6) 0.3386(7) 0.108 Uiso 1 calc R 1
C6 C 0.6935(7) 0.6194(8) 0.1790(7) 0.103(2) Uani 1 d . 1
H6A H 0.7906(7) 0.6655(8) 0.2554(7) 0.124 Uiso 1 calc R 1
H6B H 0.7031(7) 0.5933(8) 0.1044(7) 0.124 Uiso 1 calc R 1
C7 C 0.6145(7) 0.7117(8) 0.1564(6) 0.096(2) Uani 1 d . 1
H7A H 0.6800(7) 0.7937(8) 0.1653(6) 0.115 Uiso 1 calc R 1
H7B H 0.5328(7) 0.6765(8) 0.0668(6) 0.115 Uiso 1 calc R 1
C8 C 0.4497(6) 0.7995(7) 0.1925(8) 0.063(2) Uani 0.820(9) d P 1
H8A H 0.4190(6) 0.8131(7) 0.2548(8) 0.076 Uiso 0.820(9) calc PR 1
H8B H 0.3651(6) 0.7384(7) 0.1105(8) 0.076 Uiso 0.820(9) calc PR 1
C8A C 0.4392(23) 0.7343(22) 0.1197(24) 0.033(6) Uani 0.180(9) d P 2
H8AA H 0.3627(23) 0.7407(22) 0.1346(24) 0.040 Uiso 0.180(9) calc PR 2
H8AB H 0.4004(23) 0.6511(22) 0.0537(24) 0.040 Uiso 0.180(9) calc PR 2
C9 C 0.5005(8) 0.9295(8) 0.1705(9) 0.092(3) Uani 0.820(9) d P 1
H9A H 0.5321(8) 0.9168(8) 0.1088(9) 0.110 Uiso 0.820(9) calc PR 1
H9B H 0.5838(8) 0.9917(8) 0.2527(9) 0.110 Uiso 0.820(9) calc PR 1
C9A C 0.4800(24) 0.8400(22) 0.0684(24) 0.042(7) Uani 0.180(9) d P 2
H9AA H 0.5184(24) 0.8124(22) 0.0161(24) 0.050 Uiso 0.180(9) calc PR 2
H9AB H 0.5569(24) 0.9163(22) 0.1417(24) 0.050 Uiso 0.180(9) calc PR 2
C10 C 0.3828(8) 0.9878(7) 0.1181(8) 0.068(2) Uani 0.820(9) d P 1
C10A C 0.3547(23) 0.8769(19) -0.0143(23) 0.029(6) Uani 0.180(9) d P 2
C11 C 0.3864(9) 1.0794(10) 0.2062(8) 0.124(3) Uani 1 d . 1
H11A H 0.4560(9) 1.1029(10) 0.2945(8) 0.149 Uiso 1 calc R 1
C12 C 0.2826(11) 1.1421(8) 0.1646(8) 0.120(3) Uani 1 d . 1
H12A H 0.2835(11) 1.2048(8) 0.2251(8) 0.144 Uiso 1 calc R 1
C13 C 0.1851(8) 1.1061(7) 0.0356(7) 0.094(2) Uani 1 d . 1
H13A H 0.1164(8) 1.1435(7) 0.0054(7) 0.112 Uiso 1 calc R 1
C14 C 0.1873(6) 1.0107(5) -0.0546(6) 0.0688(14) Uani 1 d . 1
C15 C 0.0901(8) 0.9811(7) -0.1897(7) 0.097(2) Uani 1 d . 1
H15A H 0.0237(8) 1.0212(7) -0.2164(7) 0.116 Uiso 1 calc R 1
C16 C 0.0902(9) 0.8980(8) -0.2798(8) 0.112(2) Uani 1 d . 1
H16A H 0.0283(9) 0.8832(8) -0.3684(8) 0.135 Uiso 1 calc R 1
C17 C 0.1789(8) 0.8372(6) -0.2418(7) 0.092(2) Uani 1 d . 1
H17A H 0.1728(8) 0.7765(6) -0.3076(7) 0.110 Uiso 1 calc R 1
C18 C 0.2764(7) 0.8525(6) -0.1202(8) 0.080(2) Uani 1 d . 1
H18A H 0.3361(7) 0.8055(6) -0.1019(8) 0.096 Uiso 1 calc R 1
C19 C 0.2867(7) 0.9524(5) -0.0097(7) 0.072(2) Uani 1 d . .
C20 C 0.1361(6) 0.4179(5) 0.1145(5) 0.0604(13) Uani 1 d . 1
C21 C -0.0192(6) 0.3539(6) 0.0612(6) 0.088(2) Uani 1 d . 1
H21A H -0.0372(8) 0.2766(25) 0.0848(40) 0.133 Uiso 1 calc R 1
H21B H -0.0707(7) 0.3314(42) -0.0325(7) 0.133 Uiso 1 calc R 1
H21C H -0.0520(12) 0.4117(18) 0.0961(36) 0.133 Uiso 1 calc R 1
P P 0.1538(2) 0.75919(14) 0.36271(15) 0.0677(4) Uani 1 d . .
F1 F 0.2707(17) 0.7917(29) 0.5018(15) 0.211(12) Uani 0.58(2) d P 1
F1A F 0.1421(62) 0.6986(51) 0.4586(45) 0.268(22) Uani 0.42(2) d P 2
F2 F 0.0614(16) 0.6366(17) 0.3715(26) 0.152(9) Uani 0.58(2) d P 1
F2A F 0.0300(26) 0.6406(31) 0.2530(42) 0.219(19) Uani 0.42(2) d P 2
F3 F 0.0277(18) 0.7234(21) 0.2189(10) 0.145(6) Uani 0.58(2) d P 1
F3A F 0.1742(38) 0.8236(43) 0.2668(29) 0.212(14) Uani 0.42(2) d P 2
F4 F 0.2381(22) 0.8843(11) 0.3581(26) 0.162(8) Uani 0.58(2) d P 1
F4A F 0.2799(24) 0.8735(27) 0.4726(34) 0.226(19) Uani 0.42(2) d P 2
F5 F 0.2197(23) 0.6896(21) 0.3044(28) 0.188(11) Uani 0.58(2) d P 1
F5A F 0.2657(25) 0.6955(18) 0.3709(32) 0.131(10) Uani 0.42(2) d P 2
F6 F 0.0616(21) 0.8194(19) 0.4029(17) 0.137(7) Uani 0.58(2) d P 1
F6A F 0.0619(34) 0.8327(28) 0.3589(33) 0.179(13) Uani 0.42(2) d P 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
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 Cu N1 118.0(2) . . ?
N2 Cu S2 121.73(14) . . ?
N1 Cu S2 90.76(12) . . ?
N2 Cu S1 119.32(14) . . ?
N1 Cu S1 90.26(11) . . ?
S2 Cu S1 109.04(6) . . ?
C2 S1 C3 104.9(3) . . ?
C2 S1 Cu 95.6(2) . . ?
C3 S1 Cu 108.1(2) . . ?
C5 S2 C6 103.9(3) . . ?
C5 S2 Cu 106.7(2) . . ?
C6 S2 Cu 96.4(2) . . ?
C7 N1 C1 110.7(4) . . ?
C7 N1 C8 113.7(5) . . ?
C1 N1 C8 108.9(5) . . ?
C7 N1 Cu 105.6(4) . . ?
C1 N1 Cu 107.8(3) . . ?
C8 N1 Cu 110.1(3) . . ?
C20 N2 Cu 171.0(4) . . ?
N1 C1 C2 113.3(4) . . ?
C1 C2 S1 115.1(4) . . ?
C4 C3 S1 121.4(4) . . ?
C3 C4 C5 119.2(5) . . ?
C4 C5 S2 119.0(4) . . ?
C7 C6 S2 114.5(4) . . ?
N1 C7 C6 116.5(5) . . ?
N1 C8 C9 115.9(5) . . ?
N1 C8A C9A 113.8(17) . . ?
C8 C9 C10 114.2(5) . . ?
C8A C9A C10A 113.8(18) . . ?
C19 C10 C11 121.9(7) . . ?
C19 C10 C9 121.0(7) . . ?
C11 C10 C9 117.1(8) . . ?
C19 C10A C9A 143.7(22) . . ?
C10 C11 C12 120.6(6) . . ?
C13 C12 C11 117.6(7) . . ?
C12 C13 C14 119.8(7) . . ?
C19 C14 C15 121.2(6) . . ?
C19 C14 C13 120.2(6) . . ?
C15 C14 C13 118.6(6) . . ?
C16 C15 C14 122.2(8) . . ?
C17 C16 C15 118.7(8) . . ?
C16 C17 C18 127.2(8) . . ?
C17 C18 C19 116.9(6) . . ?
C10 C19 C14 119.8(6) . . ?
C10 C19 C18 126.4(6) . . ?
C14 C19 C18 113.7(6) . . ?
N2 C20 C21 179.1(6) . . ?
F6A P F1A 96.7(17) . . ?
F6A P F4A 87.7(16) . . ?
F1A P F4A 89.4(24) . . ?
F1 P F4 89.7(10) . . ?
F6A P F2A 94.5(18) . . ?
F1A P F2A 89.9(20) . . ?
F4A P F2A 177.8(18) . . ?
F1 P F5 95.5(12) . . ?
F4 P F5 89.5(11) . . ?
F6A P F3A 85.3(17) . . ?
F1A P F3A 177.1(22) . . ?
F4A P F3A 88.7(18) . . ?
F2A P F3A 92.0(19) . . ?
F1 P F2 90.2(10) . . ?
F4 P F2 175.3(10) . . ?
F5 P F2 95.2(12) . . ?
F1 P F3 177.9(10) . . ?
F4 P F3 91.9(9) . . ?
F5 P F3 85.9(12) . . ?
F2 P F3 88.1(8) . . ?
F6A P F5A 173.6(15) . . ?
F1A P F5A 86.9(18) . . ?
F4A P F5A 87.1(12) . . ?
F2A P F5A 90.8(14) . . ?
F3A P F5A 90.9(15) . . ?
F1 P F6 92.8(12) . . ?
F4 P F6 94.0(9) . . ?
F5 P F6 171.0(12) . . ?
F2 P F6 81.4(10) . . ?
F3 P F6 85.7(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
Cu N2 1.923(4) . ?
Cu N1 2.167(4) . ?
Cu S2 2.260(2) . ?
Cu S1 2.2687(14) . ?
S1 C2 1.804(5) . ?
S1 C3 1.822(5) . ?
S2 C5 1.821(6) . ?
S2 C6 1.834(8) . ?
N1 C7 1.447(8) . ?
N1 C8A 1.47(2) . ?
N1 C1 1.480(7) . ?
N1 C8 1.513(8) . ?
N2 C20 1.119(6) . ?
C1 C2 1.512(8) . ?
C3 C4 1.505(8) . ?
C4 C5 1.509(8) . ?
C6 C7 1.515(10) . ?
C8 C9 1.537(9) . ?
C8A C9A 1.49(3) . ?
C9 C10 1.547(10) . ?
C9A C10A 1.52(3) . ?
C10 C19 1.332(10) . ?
C10 C11 1.343(11) . ?
C10A C19 1.29(2) . ?
C11 C12 1.454(13) . ?
C12 C13 1.347(10) . ?
C13 C14 1.423(8) . ?
C14 C19 1.383(8) . ?
C14 C15 1.411(9) . ?
C15 C16 1.324(10) . ?
C16 C17 1.308(11) . ?
C17 C18 1.322(10) . ?
C18 C19 1.548(9) . ?
C20 C21 1.457(8) . ?
P F6A 1.47(2) . ?
P F1A 1.48(2) . ?
P F4A 1.49(2) . ?
P F1 1.493(12) . ?
P F4 1.500(10) . ?
P F2A 1.50(2) . ?
P F5 1.51(2) . ?
P F3A 1.53(2) . ?
P F2 1.543(11) . ?
P F3 1.558(11) . ?
P F5A 1.57(2) . ?
P F6 1.579(14) . ?
