#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:10:05 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179442 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/39/4333973.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_4333973
loop_
_publ_author_name
'Theshini Perera'
'Pramuditha Abhayawardhana'
'Patricia A. Marzilli'
'Frank R. Fronczek'
'Luigi G. Marzilli'
_publ_section_title
;
 Formation of a Metal-to-Nitrogen Bond of Normal Length by a Neutral
 Sufonamide Group within a Tridentate Ligand. A New Approach to
 Radiopharmaceutical Bioconjugation
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2412
_journal_page_last               2421
_journal_paper_doi               10.1021/ic302180t
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C16 H15 N3 O5 Re S, P F6'
_chemical_formula_sum            'C16 H15 F6 N3 O5 P Re S'
_chemical_formula_weight         692.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 123.039(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.549(2)
_cell_length_b                   20.297(2)
_cell_length_c                   12.5771(10)
_cell_measurement_reflns_used    10085
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      35.6
_cell_measurement_theta_min      2.5
_cell_volume                     4397.5(7)
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius 1999)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution
'direct_methods (SIR, Altomare, et al., 1994)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Nonius KappaCCD (with Oxford Cryostream)'
_diffrn_measurement_method       'ω and φ 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  0.028
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            60314
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         35.6
_diffrn_reflns_theta_min         2.7
_exptl_absorpt_coefficient_mu    5.779
_exptl_absorpt_correction_T_max  0.655
_exptl_absorpt_correction_T_min  0.326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.092
_exptl_crystal_description       'needle fragment'
_exptl_crystal_F_000             2656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.58
_refine_diff_density_min         -1.36
_refine_diff_density_rms         0.161
_refine_ls_extinction_coef       0.000054(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         10038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.026
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0210P)²+0.6452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.052
_refine_ls_wR_factor_ref         0.055
_reflns_number_gt                8298
_reflns_number_total             10038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic302180t_si_002_1.cif
_cod_data_source_block           Theshini62
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               4333973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Re1 Re 0.648073(4) 0.590330(4) 0.728068(7) 0.00977(2) Uani 1 1 d .
S1 S 0.79974(3) 0.48773(3) 0.86390(4) 0.01158(8) Uani 1 1 d .
O1 O 0.65143(10) 0.54650(9) 0.96530(15) 0.0211(3) Uani 1 1 d .
O2 O 0.48545(9) 0.64742(9) 0.61783(16) 0.0220(3) Uani 1 1 d .
O3 O 0.56890(10) 0.45643(9) 0.61567(16) 0.0228(3) Uani 1 1 d .
O4 O 0.79549(9) 0.49332(8) 0.97329(14) 0.0161(3) Uani 1 1 d .
O5 O 0.75206(9) 0.44111(8) 0.76683(15) 0.0181(3) Uani 1 1 d .
N1 N 0.65352(10) 0.62360(10) 0.56882(16) 0.0148(3) Uani 1 1 d .
N2 N 0.77247(9) 0.56541(8) 0.79099(14) 0.0091(3) Uani 1 1 d .
N3 N 0.71068(10) 0.68356(9) 0.80542(16) 0.0128(3) Uani 1 1 d .
C1 C 0.65172(12) 0.56364(11) 0.8784(2) 0.0150(4) Uani 1 1 d .
C2 C 0.54672(12) 0.62482(11) 0.6617(2) 0.0160(4) Uani 1 1 d .
C3 C 0.59949(12) 0.50626(11) 0.65558(19) 0.0150(4) Uani 1 1 d .
C4 C 0.59910(14) 0.66172(14) 0.4740(2) 0.0269(6) Uani 1 1 d .
H4 H 0.5508 0.6677 0.4660 0.032 Uiso 1 1 calc R
C5 C 0.61094(16) 0.69240(15) 0.3881(3) 0.0314(6) Uani 1 1 d .
H5 H 0.5713 0.7187 0.3219 0.038 Uiso 1 1 calc R
C6 C 0.68147(15) 0.68441(13) 0.3997(2) 0.0249(5) Uani 1 1 d .
H6 H 0.6911 0.7055 0.3422 0.030 Uiso 1 1 calc R
C7 C 0.73764(13) 0.64528(11) 0.4965(2) 0.0168(4) Uani 1 1 d .
H7 H 0.7867 0.6396 0.5070 0.020 Uiso 1 1 calc R
C8 C 0.72149(11) 0.61446(10) 0.57799(18) 0.0119(3) Uani 1 1 d .
C9 C 0.77625(12) 0.56546(11) 0.67459(18) 0.0132(4) Uani 1 1 d .
H9A H 0.8299 0.5759 0.6996 0.016 Uiso 1 1 calc R
H9B H 0.7634 0.5209 0.6364 0.016 Uiso 1 1 calc R
C10 C 0.82586(12) 0.61619(11) 0.88621(19) 0.0149(4) Uani 1 1 d .
H10A H 0.8415 0.6018 0.9722 0.018 Uiso 1 1 calc R
H10B H 0.8733 0.6195 0.8845 0.018 Uiso 1 1 calc R
C11 C 0.78848(11) 0.68259(10) 0.86010(18) 0.0119(3) Uani 1 1 d .
C12 C 0.83263(13) 0.73957(11) 0.89872(19) 0.0162(4) Uani 1 1 d .
H12 H 0.8871 0.7373 0.9365 0.019 Uiso 1 1 calc R
C13 C 0.79702(15) 0.79959(12) 0.8821(2) 0.0213(4) Uani 1 1 d .
H13 H 0.8264 0.8392 0.9077 0.026 Uiso 1 1 calc R
C14 C 0.71702(15) 0.80109(12) 0.8269(3) 0.0238(5) Uani 1 1 d .
H14 H 0.6909 0.8417 0.8146 0.029 Uiso 1 1 calc R
C15 C 0.67631(14) 0.74236(11) 0.7903(2) 0.0205(4) Uani 1 1 d .
H15 H 0.6218 0.7436 0.7529 0.025 Uiso 1 1 calc R
C16 C 0.89705(12) 0.47821(12) 0.9112(2) 0.0184(4) Uani 1 1 d .
H16A H 0.9153 0.4342 0.9476 0.028 Uiso 1 1 calc R
H16B H 0.9291 0.5116 0.9749 0.028 Uiso 1 1 calc R
H16C H 0.9010 0.4835 0.8374 0.028 Uiso 1 1 calc R
P1 P 1.0000 0.63181(4) 0.7500 0.01994(16) Uani 1 2 d S
F1 F 0.96842(10) 0.57655(8) 0.8019(2) 0.0386(4) Uani 1 1 d .
F2 F 0.91884(9) 0.63203(9) 0.61664(15) 0.0344(4) Uani 1 1 d .
F3 F 0.96818(10) 0.68763(8) 0.80088(15) 0.0316(4) Uani 1 1 d .
P2 P 0.50810(16) 0.87138(6) 0.7435(3) 0.0152(4) Uani 0.50 1 d P
F4 F 0.5510(3) 0.8073(2) 0.8241(4) 0.0337(9) Uani 0.50 1 d P
F5 F 0.58974(18) 0.90930(18) 0.8118(3) 0.0350(8) Uani 0.50 1 d P
F6 F 0.5202(2) 0.8477(2) 0.6346(3) 0.0373(9) Uani 0.50 1 d P
F7 F 0.4965(2) 0.8947(2) 0.8539(3) 0.0351(8) Uani 0.50 1 d P
F8 F 0.4658(2) 0.93553(17) 0.6625(3) 0.0448(10) Uani 0.50 1 d P
F9 F 0.4269(2) 0.8333(2) 0.6746(4) 0.0283(8) Uani 0.50 1 d P
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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'
S S 0.1246 0.1234 '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
C2 Re1 C1 88.94(9) . .
C2 Re1 C3 87.57(9) . .
C1 Re1 C3 87.05(9) . .
C2 Re1 N1 94.33(8) . .
C1 Re1 N1 175.30(8) . .
C3 Re1 N1 96.45(8) . .
C2 Re1 N3 96.55(8) . .
C1 Re1 N3 96.18(8) . .
C3 Re1 N3 174.80(7) . .
N1 Re1 N3 80.12(7) . .
C2 Re1 N2 169.58(8) . .
C1 Re1 N2 99.22(7) . .
C3 Re1 N2 99.23(7) . .
N1 Re1 N2 77.16(6) . .
N3 Re1 N2 76.25(6) . .
O5 S1 O4 120.10(10) . .
O5 S1 N2 105.88(9) . .
O4 S1 N2 105.17(9) . .
O5 S1 C16 109.86(11) . .
O4 S1 C16 109.76(10) . .
N2 S1 C16 104.82(10) . .
C4 N1 C8 118.35(19) . .
C4 N1 Re1 123.99(15) . .
C8 N1 Re1 116.69(13) . .
C10 N2 C9 111.77(16) . .
C10 N2 S1 108.22(12) . .
C9 N2 S1 109.69(13) . .
C10 N2 Re1 108.47(12) . .
C9 N2 Re1 107.70(11) . .
S1 N2 Re1 111.00(8) . .
C15 N3 C11 117.91(19) . .
C15 N3 Re1 124.47(15) . .
C11 N3 Re1 117.22(14) . .
O1 C1 Re1 177.5(2) . .
O2 C2 Re1 177.1(2) . .
O3 C3 Re1 176.71(19) . .
N1 C4 C5 122.5(2) . .
N1 C4 H4 118.8 . .
C5 C4 H4 118.8 . .
C4 C5 C6 119.1(2) . .
C4 C5 H5 120.5 . .
C6 C5 H5 120.5 . .
C7 C6 C5 118.9(2) . .
C7 C6 H6 120.5 . .
C5 C6 H6 120.5 . .
C6 C7 C8 119.2(2) . .
C6 C7 H7 120.4 . .
C8 C7 H7 120.4 . .
N1 C8 C7 121.88(19) . .
N1 C8 C9 116.45(18) . .
C7 C8 C9 121.52(18) . .
C8 C9 N2 112.01(16) . .
C8 C9 H9A 109.2 . .
N2 C9 H9A 109.2 . .
C8 C9 H9B 109.2 . .
N2 C9 H9B 109.2 . .
H9A C9 H9B 107.9 . .
C11 C10 N2 112.18(16) . .
C11 C10 H10A 109.2 . .
N2 C10 H10A 109.2 . .
C11 C10 H10B 109.2 . .
N2 C10 H10B 109.2 . .
H10A C10 H10B 107.9 . .
N3 C11 C12 122.2(2) . .
N3 C11 C10 116.59(18) . .
C12 C11 C10 121.05(19) . .
C13 C12 C11 119.6(2) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C14 118.7(2) . .
C12 C13 H13 120.7 . .
C14 C13 H13 120.7 . .
C15 C14 C13 118.8(2) . .
C15 C14 H14 120.6 . .
C13 C14 H14 120.6 . .
N3 C15 C14 122.8(2) . .
N3 C15 H15 118.6 . .
C14 C15 H15 118.6 . .
S1 C16 H16A 109.5 . .
S1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
S1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
F2 P1 F2 179.67(15) 2_756 .
F2 P1 F1 90.39(10) 2_756 2_756
F2 P1 F1 89.84(9) . 2_756
F2 P1 F1 89.84(9) 2_756 .
F2 P1 F1 90.39(10) . .
F1 P1 F1 91.14(15) 2_756 .
F2 P1 F3 89.91(9) 2_756 .
F2 P1 F3 89.86(9) . .
F1 P1 F3 179.45(10) 2_756 .
F1 P1 F3 89.33(9) . .
F2 P1 F3 89.86(9) 2_756 2_756
F2 P1 F3 89.91(9) . 2_756
F1 P1 F3 89.33(9) 2_756 2_756
F1 P1 F3 179.45(10) . 2_756
F3 P1 F3 90.21(13) . 2_756
F4 P2 F8 179.4(3) . .
F4 P2 F6 90.5(2) . .
F8 P2 F6 89.0(3) . .
F4 P2 F9 90.1(3) . .
F8 P2 F9 90.2(3) . .
F6 P2 F9 89.7(2) . .
F4 P2 F7 89.0(3) . .
F8 P2 F7 91.5(2) . .
F6 P2 F7 179.4(3) . .
F9 P2 F7 90.5(2) . .
F4 P2 F5 89.8(3) . .
F8 P2 F5 89.8(2) . .
F6 P2 F5 89.84(19) . .
F9 P2 F5 179.5(3) . .
F7 P2 F5 90.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Re1 C2 1.905(2) .
Re1 C1 1.928(2) .
Re1 C3 1.936(2) .
Re1 N1 2.1736(17) .
Re1 N3 2.1948(18) .
Re1 N2 2.2826(16) .
S1 O5 1.4288(17) .
S1 O4 1.4299(15) .
S1 N2 1.7552(17) .
S1 C16 1.759(2) .
O1 C1 1.150(3) .
O2 C2 1.159(3) .
O3 C3 1.151(3) .
N1 C4 1.348(3) .
N1 C8 1.350(3) .
N2 C10 1.506(3) .
N2 C9 1.508(2) .
N3 C15 1.346(3) .
N3 C11 1.353(3) .
C4 C5 1.378(3) .
C4 H4 0.9500 .
C5 C6 1.385(4) .
C5 H5 0.9500 .
C6 C7 1.383(3) .
C6 H6 0.9500 .
C7 C8 1.387(3) .
C7 H7 0.9500 .
C8 C9 1.497(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.496(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.384(3) .
C12 C13 1.377(3) .
C12 H12 0.9500 .
C13 C14 1.393(4) .
C13 H13 0.9500 .
C14 C15 1.383(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
P1 F2 1.5951(15) 2_756
P1 F2 1.5951(15) .
P1 F1 1.6022(18) 2_756
P1 F1 1.6022(18) .
P1 F3 1.6053(16) .
P1 F3 1.6053(16) 2_756
P2 P2 0.443(3) 2_656
P2 F4 1.588(4) .
P2 F8 1.589(4) .
P2 F6 1.594(4) .
P2 F9 1.598(4) .
P2 F7 1.602(4) .
P2 F5 1.604(4) .
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
C2 Re1 N1 C4 6.2(2)
C3 Re1 N1 C4 94.2(2)
N3 Re1 N1 C4 -89.7(2)
N2 Re1 N1 C4 -167.8(2)
C2 Re1 N1 C8 174.68(17)
C3 Re1 N1 C8 -97.28(17)
N3 Re1 N1 C8 78.77(16)
N2 Re1 N1 C8 0.76(15)
O5 S1 N2 C10 -175.01(13)
O4 S1 N2 C10 56.86(14)
C16 S1 N2 C10 -58.87(15)
O5 S1 N2 C9 -52.83(15)
O4 S1 N2 C9 179.04(13)
C16 S1 N2 C9 63.31(15)
O5 S1 N2 Re1 66.07(10)
O4 S1 N2 Re1 -62.06(10)
C16 S1 N2 Re1 -177.79(10)
C1 Re1 N2 C10 -73.86(14)
C3 Re1 N2 C10 -162.34(13)
N1 Re1 N2 C10 103.09(13)
N3 Re1 N2 C10 20.30(12)
C1 Re1 N2 C9 165.00(13)
C3 Re1 N2 C9 76.52(14)
N1 Re1 N2 C9 -18.05(13)
N3 Re1 N2 C9 -100.84(13)
C1 Re1 N2 S1 44.91(10)
C3 Re1 N2 S1 -43.57(10)
N1 Re1 N2 S1 -138.14(10)
N3 Re1 N2 S1 139.07(9)
C2 Re1 N3 C15 -4.81(19)
C1 Re1 N3 C15 -94.45(18)
N1 Re1 N3 C15 88.46(18)
N2 Re1 N3 C15 167.53(18)
C2 Re1 N3 C11 -177.46(15)
C1 Re1 N3 C11 92.91(15)
N1 Re1 N3 C11 -84.18(15)
N2 Re1 N3 C11 -5.11(14)
C8 N1 C4 C5 -1.2(4)
Re1 N1 C4 C5 167.1(2)
N1 C4 C5 C6 -0.5(5)
C4 C5 C6 C7 0.7(4)
C5 C6 C7 C8 0.9(4)
C4 N1 C8 C7 2.8(3)
Re1 N1 C8 C7 -166.38(16)
C4 N1 C8 C9 -172.8(2)
Re1 N1 C8 C9 18.0(2)
C6 C7 C8 N1 -2.7(3)
C6 C7 C8 C9 172.8(2)
N1 C8 C9 N2 -34.7(3)
C7 C8 C9 N2 149.63(19)
C10 N2 C9 C8 -86.8(2)
S1 N2 C9 C8 153.21(15)
Re1 N2 C9 C8 32.29(19)
C9 N2 C10 C11 85.9(2)
S1 N2 C10 C11 -153.22(14)
Re1 N2 C10 C11 -32.71(19)
C15 N3 C11 C12 -0.8(3)
Re1 N3 C11 C12 172.34(15)
C15 N3 C11 C10 174.65(19)
Re1 N3 C11 C10 -12.2(2)
N2 C10 C11 N3 31.0(2)
N2 C10 C11 C12 -153.53(18)
N3 C11 C12 C13 0.3(3)
C10 C11 C12 C13 -175.0(2)
C11 C12 C13 C14 0.3(3)
C12 C13 C14 C15 -0.3(4)
C11 N3 C15 C14 0.7(3)
Re1 N3 C15 C14 -171.86(18)
C13 C14 C15 N3 -0.2(4)
