#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:12:22 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179444 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/41/4334115.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_4334115
loop_
_publ_author_name
'Shalina C. Bottorff'
'Adam L. Moore'
'Ariana R. Wemple'
'Dejan-Krešimir Bučar'
'Leonard R. MacGillivray'
'Paul D. Benny'
_publ_contact_author_address
;
Department of Chemistry,
Washington State University, 
PO Box 644630, 
Pullman, WA 99164, USA 
;
_publ_contact_author_email       bennyp@wsu.edu
_publ_contact_author_name        'Bennny, Paul D.'
_publ_contact_author_phone       509-335-3858
_publ_section_title
;
 pH-Controlled Coordination Mode Rearrangements of "Clickable"
 Huisgen-Based Multidentate Ligands with [MI(CO)3]+ (M = Re,99mTc)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2939
_journal_page_last               2950
_journal_paper_doi               10.1021/ic302330u
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C14 H11 N2 O5 Re'
_chemical_formula_sum            'C14 H11 N2 O5 Re'
_chemical_formula_weight         473.45
_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_date             2010-04-08T00:57:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.645(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.026(4)
_cell_length_b                   6.8209(8)
_cell_length_c                   14.1322(15)
_cell_measurement_reflns_used    6614
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     2938.1(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9485
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    8.296
_exptl_absorpt_correction_T_max  0.7600
_exptl_absorpt_correction_T_min  0.2047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.141
_exptl_crystal_description       plate
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.388
_refine_diff_density_min         -1.807
_refine_diff_density_rms         0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0867P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.093
_reflns_number_gt                2452
_reflns_number_total             2584
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic302330u_si_002_2.cif
_cod_data_source_block           6
_cod_database_code               4334115
loop_
_space_group_symop_operation_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
C1 C 0.16519(14) -0.1064(6) 0.1338(3) 0.0172(9) Uani 1 1 d .
C2 C 0.18713(14) 0.2214(7) 0.0652(3) 0.0194(8) Uani 1 1 d U
C3 C 0.10796(14) 0.1899(6) 0.0721(3) 0.0174(8) Uani 1 1 d U
C4 C 0.20605(15) -0.0911(7) -0.0923(3) 0.0191(9) Uani 1 1 d .
C5 C 0.22355(15) -0.2130(6) -0.1440(3) 0.0203(9) Uani 1 1 d .
C6 C 0.20461(15) -0.3939(7) -0.1776(3) 0.0222(9) Uani 1 1 d .
C7 C 0.1676(2) -0.4457(6) -0.1593(4) 0.0258(12) Uani 1 1 d .
C8 C 0.15164(14) -0.3170(6) -0.1061(3) 0.0182(9) Uani 1 1 d .
C9 C 0.11331(16) -0.3633(6) -0.0794(4) 0.0219(10) Uani 1 1 d .
C10 C 0.06297(15) -0.1038(7) -0.1796(3) 0.0259(10) Uani 1 1 d .
C11 C 0.08120(16) 0.0829(7) -0.2080(3) 0.0205(9) Uani 1 1 d .
C12 C 0.05793(14) -0.2322(7) -0.0229(3) 0.0214(9) Uani 1 1 d .
C13 C 0.02595(15) -0.3828(7) -0.0798(4) 0.0247(10) Uani 1 1 d .
C14 C 0.0008(2) -0.5043(9) -0.1257(4) 0.0329(12) Uani 1 1 d .
H4 H 0.2192 0.0335 -0.0703 0.023 Uiso 1 1 calc R
H5 H 0.2486 -0.1733 -0.1566 0.024 Uiso 1 1 calc R
H6 H 0.2166 -0.4809 -0.2124 0.027 Uiso 1 1 calc R
H7 H 0.1534 -0.5676 -0.1829 0.031 Uiso 1 1 calc R
H9A H 0.1235 -0.4305 -0.0121 0.026 Uiso 1 1 calc R
H9B H 0.0933 -0.4533 -0.1314 0.026 Uiso 1 1 calc R
H10A H 0.0327 -0.0775 -0.1848 0.031 Uiso 1 1 calc R
H10B H 0.0613 -0.2067 -0.2305 0.031 Uiso 1 1 calc R
H12A H 0.075 -0.2802 0.0473 0.026 Uiso 1 1 calc R
H12B H 0.0421 -0.1125 -0.0173 0.026 Uiso 1 1 calc R
H14 H -0.0195 -0.6025 -0.1629 0.039 Uiso 1 1 calc R
N1 N 0.17095(11) -0.1417(5) -0.0718(2) 0.0145(7) Uani 1 1 d .
N2 N 0.08912(11) -0.1814(5) -0.0747(3) 0.0162(7) Uani 1 1 d .
O1 O 0.18088(11) -0.1954(5) 0.2089(2) 0.0293(7) Uani 1 1 d .
O2 O 0.21592(11) 0.3305(5) 0.0987(3) 0.0334(8) Uani 1 1 d .
O3 O 0.09102(11) 0.2832(5) 0.1136(2) 0.0310(8) Uani 1 1 d .
O4 O 0.11137(9) 0.1707(4) -0.1366(2) 0.0202(6) Uani 1 1 d .
O5 O 0.06312(12) 0.1408(5) -0.2968(2) 0.0323(8) Uani 1 1 d .
Re1 Re 0.140422(5) 0.03760(2) 0.009747(10) 0.01307(14) Uani 1 1 d U
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.231 '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
C1 Re1 C2 88.16(18)
C1 Re1 C3 88.52(17)
C1 Re1 N1 94.32(15)
C1 Re1 N2 96.67(15)
C1 Re1 O4 174.19(15)
C2 Re1 C3 87.83(18)
C2 Re1 N1 96.94(16)
C2 Re1 N2 171.36(14)
C2 Re1 O4 96.33(16)
C3 Re1 N1 174.51(15)
C3 Re1 N2 99.42(15)
C3 Re1 O4 95.32(15)
C4 C5 C6 119.7(4)
C4 C5 H5 120.1
C4 N1 C8 118.4(4)
C4 N1 Re1 125.7(3)
C5 C4 H4 118.9
C5 C6 C7 118.5(4)
C5 C6 H6 120.8
C6 C5 H5 120.1
C6 C7 H7 120.5
C7 C6 H6 120.8
C7 C8 C9 122.8(4)
C8 C7 C6 119.1(4)
C8 C7 H7 120.5
C8 C9 H9A 109.4
C8 C9 H9B 109.4
C8 C9 N2 111.0(3)
C8 N1 Re1 115.8(3)
C9 N2 C10 111.4(4)
C9 N2 C12 107.8(3)
C9 N2 Re1 105.8(3)
C10 N2 C12 108.6(3)
C10 N2 Re1 108.9(3)
C11 C10 H10A 108.6
C11 C10 H10B 108.6
C11 O4 Re1 119.9(3)
C12 N2 Re1 114.4(2)
C13 C12 H12A 109.2
C13 C12 H12B 109.2
C13 C12 N2 112.0(3)
C13 C14 H14 180
C14 C13 C12 179.0(5)
H9A C9 H9B 108
H10A C10 H10B 107.5
H12A C12 H12B 107.9
N1 C4 C5 122.3(4)
N1 C4 H4 118.9
N1 C8 C7 121.9(4)
N1 C8 C9 115.2(4)
N1 Re1 N2 75.61(12)
N2 C10 C11 114.8(4)
N2 C10 H10A 108.6
N2 C10 H10B 108.6
N2 C12 H12A 109.2
N2 C12 H12B 109.2
N2 C9 H9A 109.4
N2 C9 H9B 109.4
O1 C1 Re1 178.8(4)
O2 C2 Re1 178.9(4)
O3 C3 Re1 176.0(4)
O4 C11 C10 117.1(4)
O4 Re1 N1 81.49(12)
O4 Re1 N2 78.43(12)
O5 C11 C10 116.8(4)
O5 C11 O4 126.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O2 1.156(5)
C2 Re1 1.906(4)
C3 O3 1.146(5)
C4 H4 0.95
C4 N1 1.344(6)
C5 C4 1.373(6)
C5 C6 1.382(6)
C5 H5 0.95
C6 C7 1.390(7)
C6 H6 0.95
C7 H7 0.95
C8 C7 1.384(7)
C8 C9 1.487(6)
C8 N1 1.354(5)
C9 H9A 0.99
C9 H9B 0.99
C10 C11 1.527(7)
C10 H10A 0.99
C10 H10B 0.99
C11 O4 1.263(6)
C11 O5 1.229(6)
C12 H12A 0.99
C12 H12B 0.99
C13 C12 1.470(6)
C13 C14 1.176(8)
C14 H14 0.95
N2 C10 1.496(6)
N2 C12 1.516(5)
N2 C9 1.491(6)
N2 Re1 2.229(3)
O1 C1 1.158(5)
Re1 C1 1.898(4)
Re1 C3 1.932(4)
Re1 N1 2.176(3)
Re1 O4 2.120(3)
