#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:53:44 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180321 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/35/7153519.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7153519
loop_
_publ_author_name
'van Staveren, Dave R.'
'Mundwiler, Stefan'
'Hoffmanns, Ulrich'
'Pak, Jae Kyoung'
'Spingler, Bernhard'
'Metzler-Nolte, Nils'
'Alberto, Roger'
_publ_section_title
;
 Conjugation of a novel histidine derivative to biomolecules and labelling
 with [99mTc(OH2)3(CO)3]+Electronic supplementary information (ESI)
 available: complete 1H and 13C NMR spectra of 14, 15, 16 and 19. See
 http://www.rsc.org/suppdata/ob/b4/b405575f/
;
_journal_issue                   18
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              2593
_journal_page_last               2603
_journal_paper_doi               10.1039/b405575f
_journal_volume                  2
_journal_year                    2004
_chemical_formula_sum            'C16 H16 N3 O6 Tc'
_chemical_formula_weight         444.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   9.0094(5)
_cell_length_b                   13.0282(7)
_cell_length_c                   15.5661(12)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    183(2)
_cell_volume                     1827.1(2)
_computing_cell_refinement       'IPDS (Stoe, 1999)'
_computing_data_collection       'IPDS (Stoe, 1999)'
_computing_data_reduction        'X-RED (Stoe, 1999)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       '/f oscillation scan'
_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  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28804
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.61
_diffrn_standards_interval_count 'every image'
_diffrn_standards_interval_time  5
_diffrn_standards_number         50-200
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_T_max  0.9396
_exptl_absorpt_correction_T_min  0.8631
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4425
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                3590
_reflns_number_total             4425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b405575fsup1.cif
_cod_data_source_block           ra041201
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7153519
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
Tc1 Tc 0.02099(4) 0.60922(3) -0.12908(2) 0.03676(9) Uani 1 1 d .
N1 N -0.1442(4) 0.6382(3) -0.0279(2) 0.0389(8) Uani 1 1 d .
H1A H -0.1889 0.6990 -0.0371 0.047 Uiso 1 1 calc R
H1B H -0.2140 0.5888 -0.0288 0.047 Uiso 1 1 calc R
N2 N 0.0605(4) 0.4713(2) -0.0503(2) 0.0322(7) Uani 1 1 d .
N3 N 0.1564(4) 0.3226(3) -0.0114(2) 0.0366(7) Uani 1 1 d .
O1 O -0.1845(5) 0.5020(3) -0.2569(2) 0.0637(10) Uani 1 1 d .
O2 O 0.2815(5) 0.5653(4) -0.2506(2) 0.0756(13) Uani 1 1 d .
O3 O -0.0317(6) 0.8089(3) -0.2295(3) 0.0804(13) Uani 1 1 d .
O4 O 0.1448(3) 0.6850(2) -0.02814(18) 0.0382(7) Uani 1 1 d .
O5 O 0.1532(4) 0.7156(3) 0.1122(2) 0.0533(9) Uani 1 1 d .
O10 O 0.0957(7) 0.7167(5) 0.2894(3) 0.0946(16) Uani 1 1 d D
H11 H 0.116(11) 0.782(2) 0.281(4) 0.113 Uiso 1 1 d D
H12 H 0.088(10) 0.692(5) 0.238(2) 0.113 Uiso 1 1 d D
C1 C -0.1051(6) 0.5421(4) -0.2086(3) 0.0503(12) Uani 1 1 d .
C2 C 0.1839(6) 0.5819(4) -0.2048(3) 0.0504(12) Uani 1 1 d .
C3 C -0.0126(7) 0.7354(4) -0.1909(3) 0.0574(12) Uani 1 1 d .
C4 C 0.0870(5) 0.6842(3) 0.0476(3) 0.0384(9) Uani 1 1 d .
C5 C -0.0686(5) 0.6391(3) 0.0570(3) 0.0358(9) Uani 1 1 d .
H5 H -0.1261 0.6812 0.0972 0.043 Uiso 1 1 calc R
C6 C -0.0583(5) 0.5292(3) 0.0915(3) 0.0353(9) Uani 1 1 d .
H6A H -0.0145 0.5313 0.1483 0.042 Uiso 1 1 calc R
H6B H -0.1581 0.5020 0.0973 0.042 Uiso 1 1 calc R
C7 C 0.0307(5) 0.4567(3) 0.0366(2) 0.0331(7) Uani 1 1 d .
C8 C 0.0899(5) 0.3644(3) 0.0612(2) 0.0357(9) Uani 1 1 d .
H8 H 0.0862 0.3354 0.1157 0.043 Uiso 1 1 calc R
C9 C 0.1367(4) 0.3899(3) -0.0764(2) 0.0352(7) Uani 1 1 d .
H9 H 0.1719 0.3804 -0.1320 0.042 Uiso 1 1 calc R
C10 C 0.2365(5) 0.2250(3) -0.0156(3) 0.0438(10) Uani 1 1 d .
H10A H 0.3156 0.2254 0.0267 0.053 Uiso 1 1 calc R
H10B H 0.2815 0.2180 -0.0719 0.053 Uiso 1 1 calc R
C11 C 0.1361(5) 0.1336(3) 0.0009(3) 0.0390(9) Uani 1 1 d .
C12 C 0.0402(5) 0.0980(4) -0.0618(3) 0.0498(10) Uani 1 1 d .
H12' H 0.0365 0.1311 -0.1147 0.060 Uiso 1 1 calc R
C13 C -0.0507(6) 0.0136(4) -0.0468(4) 0.0591(13) Uani 1 1 d .
H13 H -0.1151 -0.0094 -0.0894 0.071 Uiso 1 1 calc R
C14 C -0.0449(6) -0.0361(4) 0.0318(4) 0.0595(14) Uani 1 1 d .
H14 H -0.1047 -0.0930 0.0419 0.071 Uiso 1 1 calc R
C15 C 0.0496(6) -0.0013(4) 0.0951(4) 0.0562(13) Uani 1 1 d .
H15 H 0.0532 -0.0347 0.1478 0.067 Uiso 1 1 calc R
C16 C 0.1399(6) 0.0838(3) 0.0803(3) 0.0464(11) Uani 1 1 d .
H16 H 0.2028 0.1074 0.1234 0.056 Uiso 1 1 calc R
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'
Tc Tc -1.4390 0.7593 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 Tc1 C2 88.4(2)
C1 Tc1 C3 88.5(2)
C2 Tc1 C3 88.4(2)
C1 Tc1 O4 173.62(17)
C2 Tc1 O4 97.84(17)
C3 Tc1 O4 93.12(17)
C1 Tc1 N1 98.14(18)
C2 Tc1 N1 172.21(18)
C3 Tc1 N1 96.01(19)
O4 Tc1 N1 75.56(12)
C1 Tc1 N2 94.84(17)
C2 Tc1 N2 93.84(17)
C3 Tc1 N2 176.05(17)
O4 Tc1 N2 83.36(12)
N1 Tc1 N2 81.41(12)
C5 N1 Tc1 109.2(2)
C9 N2 C7 106.7(3)
C9 N2 Tc1 124.4(2)
C7 N2 Tc1 128.4(2)
C9 N3 C8 107.3(3)
C9 N3 C10 126.5(4)
C8 N3 C10 126.1(4)
C4 O4 Tc1 116.9(3)
O1 C1 Tc1 178.8(5)
O2 C2 Tc1 179.7(5)
O3 C3 Tc1 178.2(5)
O5 C4 O4 123.0(4)
O5 C4 C5 119.5(4)
O4 C4 C5 117.4(4)
N1 C5 C4 109.8(3)
N1 C5 C6 109.4(3)
C4 C5 C6 109.7(3)
C7 C6 C5 114.8(3)
C8 C7 N2 108.4(3)
C8 C7 C6 126.9(3)
N2 C7 C6 124.6(3)
C7 C8 N3 106.6(3)
N2 C9 N3 111.0(3)
N3 C10 C11 112.3(4)
C12 C11 C16 118.9(4)
C12 C11 C10 121.1(4)
C16 C11 C10 119.9(4)
C11 C12 C13 121.0(5)
C14 C13 C12 119.6(5)
C15 C14 C13 120.0(5)
C14 C15 C16 120.3(5)
C15 C16 C11 120.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Tc1 C1 1.895(6)
Tc1 C2 1.916(5)
Tc1 C3 1.929(5)
Tc1 O4 2.165(3)
Tc1 N1 2.200(3)
Tc1 N2 2.204(3)
N1 C5 1.486(5)
N2 C9 1.328(5)
N2 C7 1.392(5)
N3 C9 1.350(5)
N3 C8 1.389(5)
N3 C10 1.464(5)
O1 C1 1.161(6)
O2 C2 1.153(6)
O3 C3 1.143(6)
O4 C4 1.290(5)
O5 C4 1.237(5)
C4 C5 1.527(6)
C5 C6 1.532(6)
C6 C7 1.505(5)
C7 C8 1.370(5)
C10 C11 1.518(6)
C11 C12 1.382(6)
C11 C16 1.397(6)
C12 C13 1.391(7)
C13 C14 1.386(8)
C14 C15 1.378(8)
C15 C16 1.394(7)
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
C1 Tc1 N1 C5 150.4(3)
C2 Tc1 N1 C5 3.9(15)
C3 Tc1 N1 C5 -120.3(3)
O4 Tc1 N1 C5 -28.6(3)
N2 Tc1 N1 C5 56.7(3)
C1 Tc1 N2 C9 68.1(4)
C2 Tc1 N2 C9 -20.6(4)
C3 Tc1 N2 C9 -145(3)
O4 Tc1 N2 C9 -118.0(3)
N1 Tc1 N2 C9 165.6(3)
C1 Tc1 N2 C7 -121.1(4)
C2 Tc1 N2 C7 150.2(4)
C3 Tc1 N2 C7 26(3)
O4 Tc1 N2 C7 52.7(3)
N1 Tc1 N2 C7 -23.6(3)
C1 Tc1 O4 C4 10.6(17)
C2 Tc1 O4 C4 -156.3(3)
C3 Tc1 O4 C4 114.9(3)
N1 Tc1 O4 C4 19.5(3)
N2 Tc1 O4 C4 -63.3(3)
C2 Tc1 C1 O1 -151(22)
C3 Tc1 C1 O1 -62(22)
O4 Tc1 C1 O1 42(23)
N1 Tc1 C1 O1 34(22)
N2 Tc1 C1 O1 116(22)
C1 Tc1 C2 O2 14(99)
C3 Tc1 C2 O2 -75(99)
O4 Tc1 C2 O2 -168(100)
N1 Tc1 C2 O2 161(100)
N2 Tc1 C2 O2 108(99)
C1 Tc1 C3 O3 -49(17)
C2 Tc1 C3 O3 40(17)
O4 Tc1 C3 O3 137(17)
N1 Tc1 C3 O3 -147(17)
N2 Tc1 C3 O3 164(15)
Tc1 O4 C4 O5 172.5(3)
Tc1 O4 C4 C5 -5.6(5)
Tc1 N1 C5 C4 34.2(4)
Tc1 N1 C5 C6 -86.2(3)
O5 C4 C5 N1 161.8(4)
O4 C4 C5 N1 -20.0(5)
O5 C4 C5 C6 -78.0(5)
O4 C4 C5 C6 100.2(4)
N1 C5 C6 C7 61.8(4)
C4 C5 C6 C7 -58.7(4)
C9 N2 C7 C8 -0.5(5)
Tc1 N2 C7 C8 -172.5(3)
C9 N2 C7 C6 -177.8(4)
Tc1 N2 C7 C6 10.2(6)
C5 C6 C7 C8 161.8(4)
C5 C6 C7 N2 -21.4(6)
N2 C7 C8 N3 0.1(5)
C6 C7 C8 N3 177.3(4)
C9 N3 C8 C7 0.4(5)
C10 N3 C8 C7 178.8(4)
C7 N2 C9 N3 0.8(5)
Tc1 N2 C9 N3 173.2(3)
C8 N3 C9 N2 -0.7(5)
C10 N3 C9 N2 -179.1(4)
C9 N3 C10 C11 -116.5(5)
C8 N3 C10 C11 65.4(6)
N3 C10 C11 C12 76.7(5)
N3 C10 C11 C16 -103.5(5)
C16 C11 C12 C13 -0.4(7)
C10 C11 C12 C13 179.4(4)
C11 C12 C13 C14 -0.3(7)
C12 C13 C14 C15 0.6(8)
C13 C14 C15 C16 -0.2(8)
C14 C15 C16 C11 -0.6(7)
C12 C11 C16 C15 0.9(7)
C10 C11 C16 C15 -178.9(4)
