#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/51/4315120.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_4315120
loop_
_publ_author_name
'Radu F. Semeniuc'
'Thomas J. Reamer'
'Jonathan P. Blitz'
'Kraig A. Wheeler'
'Mark D. Smith'
_publ_contact_author_address
;
Department of Chemistry
Eatern Illinois University
Charleston, Illinois 61920
USA
;
_publ_contact_author_email       rsemeniuc@eiu.edu
_publ_contact_author_name        'Radu F. Semeniuc'
_publ_contact_author_phone       '1 217 581 5422'
_publ_section_title
;
 Functionalized O-Alkyldithiocarbonates: A New Class of Ligands Designed
 for Luminescent Heterometallic Materials
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2624
_journal_page_last               2629
_journal_paper_doi               10.1021/ic901551t
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         'C20 H14 N3 O4 Re S2, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C20.5 H15 Cl N3 O4 Re S2'
_chemical_formula_weight         653.13
_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                112.213(2)
_cell_angle_beta                 99.322(2)
_cell_angle_gamma                90.503(2)
_cell_formula_units_Z            2
_cell_length_a                   6.4657(5)
_cell_length_b                   13.0464(11)
_cell_length_c                   14.5100(12)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.343
_cell_measurement_theta_min      2.691
_cell_volume                     1114.89(16)
_computing_cell_refinement       'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_data_collection       'SMART Version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_molecular_graphics    various
_computing_publication_material  'SHELXTL Version 6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega 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  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11493
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    5.790
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS Version 2.05 (Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.946
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.247
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                3425
_reflns_number_total             3939
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901551t_si_003_2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_formula_sum        'C20.50 H15 Cl N3 O4 Re S2'
_cod_database_code               4315120
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.40497(4) 0.11258(2) 0.32843(2) 0.02170(11) Uani 1 1 d . . .
S1 S 0.1653(3) 0.16359(14) 0.20253(13) 0.0253(4) Uani 1 1 d . . .
S2 S -0.0525(3) 0.35231(18) 0.17789(16) 0.0420(5) Uani 1 1 d . . .
C1 C 0.1110(10) 0.3004(6) 0.2465(5) 0.0277(16) Uani 1 1 d . . .
C2 C 0.1804(12) 0.4768(6) 0.3861(6) 0.0351(18) Uani 1 1 d . . .
H2A H 0.2219 0.5024 0.4605 0.042 Uiso 1 1 calc R . .
H2B H 0.0289 0.4870 0.3710 0.042 Uiso 1 1 calc R . .
C3 C 0.3021(11) 0.5471(6) 0.3497(5) 0.0295(16) Uani 1 1 d . . .
C4 C 0.4774(12) 0.5116(6) 0.3045(6) 0.040(2) Uani 1 1 d . . .
H4 H 0.5237 0.4400 0.2950 0.049 Uiso 1 1 calc R . .
C5 C 0.5824(12) 0.5823(7) 0.2738(7) 0.042(2) Uani 1 1 d . . .
H5 H 0.7000 0.5565 0.2422 0.051 Uiso 1 1 calc R . .
C6 C 0.3660(12) 0.7191(6) 0.3312(5) 0.0326(17) Uani 1 1 d . . .
H6 H 0.3275 0.7923 0.3422 0.039 Uiso 1 1 calc R . .
C7 C 0.2487(12) 0.6543(6) 0.3634(5) 0.0332(17) Uani 1 1 d . . .
H7 H 0.1322 0.6829 0.3948 0.040 Uiso 1 1 calc R . .
C8 C 0.0339(10) -0.0488(6) 0.3178(5) 0.0258(15) Uani 1 1 d . . .
H8 H 0.0190 0.0086 0.3800 0.031 Uiso 1 1 calc R . .
C9 C -0.1063(11) -0.1427(6) 0.2795(6) 0.0312(17) Uani 1 1 d . . .
H9 H -0.2120 -0.1508 0.3152 0.037 Uiso 1 1 calc R . .
C10 C -0.0863(11) -0.2235(6) 0.1877(6) 0.0354(18) Uani 1 1 d . . .
H10 H -0.1808 -0.2882 0.1582 0.042 Uiso 1 1 calc R . .
C11 C 0.0703(11) -0.2101(6) 0.1393(5) 0.0299(16) Uani 1 1 d . . .
H11 H 0.0840 -0.2658 0.0760 0.036 Uiso 1 1 calc R . .
C12 C 0.2088(10) -0.1165(6) 0.1816(5) 0.0240(15) Uani 1 1 d . . .
C13 C 0.3867(10) -0.0954(6) 0.1367(5) 0.0246(15) Uani 1 1 d . . .
C14 C 0.4323(11) -0.1700(6) 0.0471(5) 0.0322(17) Uani 1 1 d . . .
H14 H 0.3498 -0.2384 0.0116 0.039 Uiso 1 1 calc R . .
C15 C 0.5992(12) -0.1438(7) 0.0098(5) 0.0354(18) Uani 1 1 d . . .
H15 H 0.6311 -0.1934 -0.0527 0.042 Uiso 1 1 calc R . .
C16 C 0.7189(11) -0.0459(6) 0.0635(5) 0.0294(16) Uani 1 1 d . . .
H16 H 0.8355 -0.0267 0.0394 0.035 Uiso 1 1 calc R . .
C17 C 0.6662(10) 0.0242(6) 0.1533(5) 0.0268(16) Uani 1 1 d . . .
H17 H 0.7498 0.0920 0.1905 0.032 Uiso 1 1 calc R . .
C18 C 0.5894(10) 0.0638(6) 0.4194(5) 0.0274(16) Uani 1 1 d . . .
C19 C 0.6025(11) 0.2363(6) 0.3635(5) 0.0273(16) Uani 1 1 d . . .
C20 C 0.2684(11) 0.1992(6) 0.4378(5) 0.0292(16) Uani 1 1 d . . .
N1 N 0.5286(10) 0.6848(6) 0.2858(5) 0.0429(17) Uani 1 1 d . . .
N2 N 0.1877(8) -0.0353(5) 0.2718(4) 0.0247(13) Uani 1 1 d . . .
N3 N 0.5034(8) 0.0017(4) 0.1909(4) 0.0216(12) Uani 1 1 d . . .
O1 O 0.2119(8) 0.3608(4) 0.3411(3) 0.0299(11) Uani 1 1 d . . .
O2 O 0.7039(8) 0.0365(4) 0.4736(4) 0.0358(12) Uani 1 1 d . . .
O3 O 0.7268(8) 0.3104(5) 0.3842(4) 0.0381(13) Uani 1 1 d . . .
O4 O 0.1789(8) 0.2491(5) 0.5009(4) 0.0439(14) Uani 1 1 d . . .
C21 C -0.2332(14) 0.4980(17) -0.0682(14) 0.059(5) Uani 0.50 1 d PD A 1
H21A H -0.2552 0.4279 -0.1289 0.071 Uiso 0.50 1 calc PR A 1
H21B H -0.2291 0.5597 -0.0920 0.071 Uiso 0.50 1 calc PR A 1
Cl1 Cl 0.0000 0.5000 0.0000 0.0945(15) Uani 1 2 d SD . 1
Cl2 Cl -0.4432(13) 0.5085(9) -0.0112(7) 0.122(3) Uani 0.50 1 d PD . 1
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'
Re Re -1.0185 7.2310 '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
C19 Re1 C20 89.0(3) . . ?
C19 Re1 C18 88.4(3) . . ?
C20 Re1 C18 89.9(3) . . ?
C19 Re1 N3 99.4(2) . . ?
C20 Re1 N3 169.8(2) . . ?
C18 Re1 N3 96.1(2) . . ?
C19 Re1 N2 173.7(2) . . ?
C20 Re1 N2 96.8(2) . . ?
C18 Re1 N2 94.0(3) . . ?
N3 Re1 N2 74.6(2) . . ?
C19 Re1 S1 94.0(2) . . ?
C20 Re1 S1 92.9(2) . . ?
C18 Re1 S1 176.4(2) . . ?
N3 Re1 S1 80.84(14) . . ?
N2 Re1 S1 83.37(14) . . ?
C1 S1 Re1 113.8(2) . . ?
O1 C1 S2 123.5(5) . . ?
O1 C1 S1 114.0(5) . . ?
S2 C1 S1 122.4(4) . . ?
O1 C2 C3 113.4(6) . . ?
O1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
O1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C7 C3 C4 116.8(7) . . ?
C7 C3 C2 120.5(7) . . ?
C4 C3 C2 122.6(7) . . ?
C5 C4 C3 118.9(7) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 124.0(7) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
N1 C6 C7 123.7(7) . . ?
N1 C6 H6 118.1 . . ?
C7 C6 H6 118.1 . . ?
C6 C7 C3 119.7(7) . . ?
C6 C7 H7 120.1 . . ?
C3 C7 H7 120.1 . . ?
N2 C8 C9 123.2(7) . . ?
N2 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C10 C9 C8 117.5(6) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C11 C10 C9 119.7(7) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.6(7) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N2 C12 C11 120.0(6) . . ?
N2 C12 C13 115.2(6) . . ?
C11 C12 C13 124.8(6) . . ?
N3 C13 C14 122.3(6) . . ?
N3 C13 C12 115.2(6) . . ?
C14 C13 C12 122.5(6) . . ?
C13 C14 C15 119.0(7) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 119.5(7) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 118.5(7) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
N3 C17 C16 123.4(7) . . ?
N3 C17 H17 118.3 . . ?
C16 C17 H17 118.3 . . ?
O2 C18 Re1 178.1(6) . . ?
O3 C19 Re1 178.5(6) . . ?
O4 C20 Re1 177.2(6) . . ?
C6 N1 C5 116.7(7) . . ?
C8 N2 C12 118.9(6) . . ?
C8 N2 Re1 124.0(5) . . ?
C12 N2 Re1 117.0(4) . . ?
C17 N3 C13 117.3(6) . . ?
C17 N3 Re1 124.9(5) . . ?
C13 N3 Re1 117.8(4) . . ?
C1 O1 C2 119.3(6) . . ?
Cl1 C21 Cl2 117.1(11) . . ?
Cl1 C21 H21A 108.0 . . ?
Cl2 C21 H21A 108.0 . . ?
Cl1 C21 H21B 108.0 . . ?
Cl2 C21 H21B 108.0 . . ?
H21A C21 H21B 107.3 . . ?
C21 Cl1 C21 179.997(1) 2_565 . ?
Cl2 Cl2 C21 162.6(19) 2_465 . ?
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
Re1 C19 1.905(8) . ?
Re1 C20 1.920(8) . ?
Re1 C18 1.925(8) . ?
Re1 N3 2.173(5) . ?
Re1 N2 2.180(6) . ?
Re1 S1 2.4905(17) . ?
S1 C1 1.714(7) . ?
S2 C1 1.657(7) . ?
C1 O1 1.348(8) . ?
C2 O1 1.435(8) . ?
C2 C3 1.493(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C7 1.390(10) . ?
C3 C4 1.396(10) . ?
C4 C5 1.381(11) . ?
C4 H4 0.9500 . ?
C5 N1 1.339(10) . ?
C5 H5 0.9500 . ?
C6 N1 1.323(9) . ?
C6 C7 1.382(10) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N2 1.329(8) . ?
C8 C9 1.391(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(10) . ?
C11 H11 0.9500 . ?
C12 N2 1.366(9) . ?
C12 C13 1.482(9) . ?
C13 N3 1.353(8) . ?
C13 C14 1.377(10) . ?
C14 C15 1.378(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(10) . ?
C16 H16 0.9500 . ?
C17 N3 1.339(8) . ?
C17 H17 0.9500 . ?
C18 O2 1.150(8) . ?
C19 O3 1.166(9) . ?
C20 O4 1.151(8) . ?
C21 Cl1 1.659(12) . ?
C21 Cl2 1.682(12) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
Cl1 C21 1.658(12) 2_565 ?
Cl2 Cl2 0.907(12) 2_465 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 Re1 S1 C1 -47.9(3) . . . . ?
C20 Re1 S1 C1 41.3(3) . . . . ?
N3 Re1 S1 C1 -146.8(3) . . . . ?
N2 Re1 S1 C1 137.8(3) . . . . ?
Re1 S1 C1 O1 2.3(6) . . . . ?
Re1 S1 C1 S2 -177.4(3) . . . . ?
O1 C2 C3 C7 162.6(6) . . . . ?
O1 C2 C3 C4 -20.0(10) . . . . ?
C7 C3 C4 C5 -1.9(11) . . . . ?
C2 C3 C4 C5 -179.4(8) . . . . ?
C3 C4 C5 N1 1.0(14) . . . . ?
N1 C6 C7 C3 0.8(12) . . . . ?
C4 C3 C7 C6 1.0(11) . . . . ?
C2 C3 C7 C6 178.6(7) . . . . ?
N2 C8 C9 C10 -1.9(10) . . . . ?
C8 C9 C10 C11 1.3(10) . . . . ?
C9 C10 C11 C12 0.1(11) . . . . ?
C10 C11 C12 N2 -1.1(10) . . . . ?
C10 C11 C12 C13 178.4(7) . . . . ?
N2 C12 C13 N3 -0.4(8) . . . . ?
C11 C12 C13 N3 -179.9(6) . . . . ?
N2 C12 C13 C14 178.7(6) . . . . ?
C11 C12 C13 C14 -0.9(10) . . . . ?
N3 C13 C14 C15 -1.7(10) . . . . ?
C12 C13 C14 C15 179.4(6) . . . . ?
C13 C14 C15 C16 1.5(11) . . . . ?
C14 C15 C16 C17 -0.6(11) . . . . ?
C15 C16 C17 N3 -0.2(10) . . . . ?
C7 C6 N1 C5 -1.8(12) . . . . ?
C4 C5 N1 C6 0.8(13) . . . . ?
C9 C8 N2 C12 1.0(10) . . . . ?
C9 C8 N2 Re1 178.5(5) . . . . ?
C11 C12 N2 C8 0.6(9) . . . . ?
C13 C12 N2 C8 -179.0(6) . . . . ?
C11 C12 N2 Re1 -177.1(5) . . . . ?
C13 C12 N2 Re1 3.3(7) . . . . ?
C20 Re1 N2 C8 -6.8(5) . . . . ?
C18 Re1 N2 C8 83.6(5) . . . . ?
N3 Re1 N2 C8 178.8(5) . . . . ?
S1 Re1 N2 C8 -98.9(5) . . . . ?
C20 Re1 N2 C12 170.8(5) . . . . ?
C18 Re1 N2 C12 -98.8(5) . . . . ?
N3 Re1 N2 C12 -3.6(4) . . . . ?
S1 Re1 N2 C12 78.7(4) . . . . ?
C16 C17 N3 C13 0.1(9) . . . . ?
C16 C17 N3 Re1 -177.0(5) . . . . ?
C14 C13 N3 C17 0.9(9) . . . . ?
C12 C13 N3 C17 179.9(5) . . . . ?
C14 C13 N3 Re1 178.1(5) . . . . ?
C12 C13 N3 Re1 -2.8(7) . . . . ?
C19 Re1 N3 C17 2.4(5) . . . . ?
C20 Re1 N3 C17 147.3(13) . . . . ?
C18 Re1 N3 C17 -87.0(5) . . . . ?
N2 Re1 N3 C17 -179.5(5) . . . . ?
S1 Re1 N3 C17 94.9(5) . . . . ?
C19 Re1 N3 C13 -174.7(5) . . . . ?
C20 Re1 N3 C13 -29.7(16) . . . . ?
C18 Re1 N3 C13 95.9(5) . . . . ?
N2 Re1 N3 C13 3.4(4) . . . . ?
S1 Re1 N3 C13 -82.1(4) . . . . ?
S2 C1 O1 C2 -0.7(9) . . . . ?
S1 C1 O1 C2 179.6(5) . . . . ?
C3 C2 O1 C1 -78.2(8) . . . . ?
