#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:41:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179073 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/35/4303563.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_4303563
loop_
_publ_author_name
'Haiyang He'
'Jennifer E. Morley'
'Brendan Twamley'
'Ryan H. Groeneman'
'Dejan-Krešimir Bučǎr'
'Leonard R. MacGillivray'
'Paul D. Benny'
_publ_contact_author             'Benny, Paul'
_publ_contact_author_address
;Department of Chemistry
Washington State University
Pullman, WA 99164-4630 
USA
;
_publ_contact_author_email       bennyp@wsu.edu
_publ_contact_author_phone       '509 335-3858'
_publ_section_title
;
Investigation of the Coordination Interactions of
S-(Pyridin-2-ylmethyl)-l-Cysteine Ligands with M(CO)3+ (M = Re, 99mTc)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10625
_journal_page_last               10634
_journal_paper_doi               10.1021/ic901159r
_journal_volume                  48
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H12 N2 O5 Re S, C2 F3 O2'
_chemical_formula_sum            'C14 H12 F3 N2 O7 Re S'
_chemical_formula_weight         595.52
_chemical_name_common            '[C12H12N2O5ReS][C2F3O2]'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2755(3)
_cell_length_b                   10.7053(4)
_cell_length_c                   20.7099(7)
_cell_measurement_reflns_used    9287
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.65
_cell_volume                     1834.73(11)
_computing_cell_refinement       'SAINT+  v. 7.23a (Bruker, 2006)'
_computing_data_collection       'SMART v. 5.632 (Bruker, 2006)'
_computing_data_reduction        'SAINT+  v. 7.23a (Bruker, 2006)'
_computing_molecular_graphics    'XP, SHELXTL  v. 6.14 (Bruker, 2003)'
_computing_publication_material  'XCIF, SHELXTL, v. 6.14 (Bruker, 2003)'
_computing_structure_refinement  'XL, SHELXTL  v. 6.14 (Bruker, 2003)'
_computing_structure_solution    'XS, SHELXTL  v. 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker/Siemens SMART APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27139
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.97
_diffrn_source                   'normal-focus sealed tube'
_diffrn_source_type              'Bruker SMART APEX'
_exptl_absorpt_coefficient_mu    6.807
_exptl_absorpt_correction_T_max  0.439
_exptl_absorpt_correction_T_min  0.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2007/4 (Bruker, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.485
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0162
_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)+(0.0128P)²+0.6133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0365
_refine_ls_wR_factor_ref         0.0371
_reflns_number_gt                4022
_reflns_number_total             4216
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic901159r_si_002_2.cif
_cod_data_source_block           2a
_cod_database_code               4303563
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.6033(4) 0.4501(3) 0.07385(16) 0.0210(7) Uani 1 1 d . . .
C2 C 0.5711(4) 0.4937(3) 0.20100(17) 0.0219(8) Uani 1 1 d . . .
C3 C 0.7490(5) 0.3040(3) 0.15815(13) 0.0203(6) Uani 1 1 d . . .
C5 C 0.6668(4) 0.7665(3) 0.14279(16) 0.0206(7) Uani 1 1 d . . .
H5 H 0.5826 0.7383 0.1704 0.025 Uiso 1 1 calc R . .
C6 C 0.6761(4) 0.8923(3) 0.12846(16) 0.0229(7) Uani 1 1 d . . .
H6 H 0.6008 0.9495 0.1465 0.027 Uiso 1 1 calc R . .
C7 C 0.7964(4) 0.9338(3) 0.08755(16) 0.0231(7) Uani 1 1 d . . .
H7 H 0.8040 1.0197 0.0763 0.028 Uiso 1 1 calc R . .
C8 C 0.9053(4) 0.8482(3) 0.06324(16) 0.0199(7) Uani 1 1 d . . .
H8 H 0.9895 0.8749 0.0353 0.024 Uiso 1 1 calc R . .
C9 C 0.8917(3) 0.7240(3) 0.07962(14) 0.0149(6) Uani 1 1 d . . .
C10 C 1.0116(4) 0.6338(3) 0.05039(14) 0.0166(6) Uani 1 1 d . . .
H10A H 1.1217 0.6673 0.0573 0.020 Uiso 1 1 calc R . .
H10B H 0.9929 0.6306 0.0032 0.020 Uiso 1 1 calc R . .
C11 C 1.1484(4) 0.4815(3) 0.14815(14) 0.0178(6) Uani 1 1 d . . .
H11A H 1.1708 0.3949 0.1625 0.021 Uiso 1 1 calc R . .
H11B H 1.2511 0.5172 0.1321 0.021 Uiso 1 1 calc R . .
C12 C 1.0931(3) 0.5571(3) 0.20613(15) 0.0149(6) Uani 1 1 d . . .
H12 H 1.1619 0.5304 0.2434 0.018 Uiso 1 1 calc R . .
C14 C 1.1106(4) 0.6984(3) 0.20063(14) 0.0162(6) Uani 1 1 d . . .
C15 C 0.2702(4) 0.0004(2) 0.10279(14) 0.0192(7) Uani 1 1 d . . .
C16 C 0.2602(6) 0.1446(3) 0.09858(15) 0.0288(7) Uani 1 1 d . . .
F1 F 0.1081(3) 0.1813(2) 0.11113(13) 0.0469(7) Uani 1 1 d . . .
F2 F 0.3536(3) 0.2004(2) 0.14256(14) 0.0450(6) Uani 1 1 d . . .
F3 F 0.2963(3) 0.1892(2) 0.04135(12) 0.0549(8) Uani 1 1 d . . .
N4 N 0.7737(3) 0.6811(2) 0.11892(11) 0.0157(6) Uani 1 1 d . . .
N13 N 0.9240(3) 0.5240(3) 0.22313(14) 0.0167(6) Uani 1 1 d . . .
O1 O 0.5077(3) 0.4311(2) 0.03478(11) 0.0272(5) Uani 1 1 d . . .
O2 O 0.4626(3) 0.4988(3) 0.23532(12) 0.0336(6) Uani 1 1 d . . .
O3 O 0.7417(4) 0.19705(18) 0.16449(10) 0.0266(5) Uani 1 1 d . . .
O4 O 1.2424(3) 0.73083(17) 0.17010(9) 0.0201(4) Uani 1 1 d . . .
H4 H 1.2478 0.8091 0.1681 0.030 Uiso 1 1 calc R . .
O5 O 1.0137(3) 0.76850(19) 0.22560(10) 0.0178(5) Uani 1 1 d . . .
O6 O 0.2803(3) -0.0581(2) 0.05249(10) 0.0259(6) Uani 1 1 d . . .
O7 O 0.2617(3) -0.03887(18) 0.16033(9) 0.0229(4) Uani 1 1 d . . .
Re1 Re 0.752359(17) 0.480807(9) 0.143345(4) 0.01426(4) Uani 1 1 d . . .
S1 S 1.00489(9) 0.47591(7) 0.08150(4) 0.01738(15) Uani 1 1 d . . .
H13A H 0.917(4) 0.464(3) 0.2497(17) 0.021 Uiso 1 1 d . . .
H13B H 0.878(4) 0.582(3) 0.2454(17) 0.021 Uiso 1 1 d . . .
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'
F F 0.0171 0.0103 '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
O1 C1 Re1 176.3(3) . . ?
O2 C2 Re1 178.6(3) . . ?
O3 C3 Re1 176.5(3) . . ?
N4 C5 C6 122.6(3) . . ?
N4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 118.7(3) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
N4 C9 C8 122.4(3) . . ?
N4 C9 C10 119.9(3) . . ?
C8 C9 C10 117.7(3) . . ?
C9 C10 S1 115.7(2) . . ?
C9 C10 H10A 108.3 . . ?
S1 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
S1 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 S1 114.8(2) . . ?
C12 C11 H11A 108.6 . . ?
S1 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
S1 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
N13 C12 C11 110.1(3) . . ?
N13 C12 C14 110.1(2) . . ?
C11 C12 C14 116.2(3) . . ?
N13 C12 H12 106.6 . . ?
C11 C12 H12 106.6 . . ?
C14 C12 H12 106.6 . . ?
O5 C14 O4 126.3(3) . . ?
O5 C14 C12 121.3(3) . . ?
O4 C14 C12 112.3(3) . . ?
O6 C15 O7 129.7(3) . . ?
O6 C15 C16 117.9(3) . . ?
O7 C15 C16 112.4(2) . . ?
F3 C16 F2 108.7(3) . . ?
F3 C16 F1 106.3(3) . . ?
F2 C16 F1 106.2(3) . . ?
F3 C16 C15 113.7(3) . . ?
F2 C16 C15 112.1(3) . . ?
F1 C16 C15 109.3(3) . . ?
C9 N4 C5 117.3(3) . . ?
C9 N4 Re1 121.7(2) . . ?
C5 N4 Re1 121.0(2) . . ?
C12 N13 Re1 118.3(2) . . ?
C12 N13 H13A 113(2) . . ?
Re1 N13 H13A 106(2) . . ?
C12 N13 H13B 112(2) . . ?
Re1 N13 H13B 105(2) . . ?
H13A N13 H13B 100(3) . . ?
C14 O4 H4 109.5 . . ?
C3 Re1 C2 87.74(16) . . ?
C3 Re1 C1 86.66(14) . . ?
C2 Re1 C1 88.65(14) . . ?
C3 Re1 N4 174.46(13) . . ?
C2 Re1 N4 97.74(13) . . ?
C1 Re1 N4 92.62(11) . . ?
C3 Re1 N13 95.48(13) . . ?
C2 Re1 N13 91.26(13) . . ?
C1 Re1 N13 177.85(12) . . ?
N4 Re1 N13 85.26(10) . . ?
C3 Re1 S1 94.28(13) . . ?
C2 Re1 S1 172.42(10) . . ?
C1 Re1 S1 98.75(10) . . ?
N4 Re1 S1 80.39(7) . . ?
N13 Re1 S1 81.29(7) . . ?
C10 S1 C11 102.67(14) . . ?
C10 S1 Re1 101.08(10) . . ?
C11 S1 Re1 99.15(10) . . ?
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
C1 O1 1.150(4) . ?
C1 Re1 1.924(3) . ?
C2 O2 1.146(4) . ?
C2 Re1 1.922(3) . ?
C3 O3 1.154(3) . ?
C3 Re1 1.918(3) . ?
C5 N4 1.365(4) . ?
C5 C6 1.381(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
C9 N4 1.352(4) . ?
C9 C10 1.511(4) . ?
C10 S1 1.809(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.519(4) . ?
C11 S1 1.822(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N13 1.486(4) . ?
C12 C14 1.524(4) . ?
C12 H12 1.0000 . ?
C14 O5 1.214(4) . ?
C14 O4 1.308(4) . ?
C15 O6 1.218(3) . ?
C15 O7 1.265(3) . ?
C15 C16 1.549(4) . ?
C16 F3 1.312(4) . ?
C16 F2 1.336(4) . ?
C16 F1 1.344(5) . ?
N4 Re1 2.210(2) . ?
N13 Re1 2.227(3) . ?
N13 H13A 0.85(4) . ?
N13 H13B 0.86(4) . ?
O4 H4 0.8400 . ?
Re1 S1 2.4516(8) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O7 0.84 1.64 2.479(3) 177 1_665
N13 H13A O5 0.85(4) 2.23(4) 2.979(4) 148(3) 3_745
N13 H13A O7 0.85(4) 2.38(3) 2.939(3) 124(3) 3_655
