#------------------------------------------------------------------------------
#$Date: 2019-11-24 09:54:53 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/84/4088402.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_4088402
loop_
_publ_author_name
'Hoover, Andrew J.'
'Lazari, Mark'
'Ren, Hong'
'Narayanam, Maruthi Kumar'
'Murphy, Jennifer M.'
'van Dam, R. Michael'
'Hooker, Jacob M.'
'Ritter, Tobias'
_publ_section_title
;
 A Transmetalation Reaction Enables the Synthesis of
 [¹⁸F]5-Fluorouracil from [¹⁸F]Fluoride for Human
 PET Imaging.
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1008
_journal_page_last               1014
_journal_paper_doi               10.1021/acs.organomet.6b00059
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C35 H26 Cl2 N8 Ni O8 S2'
_chemical_formula_weight         880.37
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                103.787(5)
_cell_angle_beta                 98.329(5)
_cell_angle_gamma                112.385(5)
_cell_formula_units_Z            1
_cell_length_a                   9.134(2)
_cell_length_b                   9.293(2)
_cell_length_c                   12.052(3)
_cell_measurement_reflns_used    2497
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      25.335
_cell_measurement_theta_min      2.499
_cell_volume                     886.5(4)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10289
_diffrn_reflns_theta_full        25.71
_diffrn_reflns_theta_max         25.71
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  0.9169
_exptl_absorpt_correction_T_min  0.7191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0448
_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)+(0.0818P)²+0.1490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1385
_reflns_number_gt                2686
_reflns_number_total             3355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om6b00059_si_003.cif
_cod_data_source_block           mgc_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4088402
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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
H00D H 0.6236 0.3476 0.5506 0.017 Uiso 1 1 calc R . .
H00F H 0.4586 0.2809 1.0239 0.021 Uiso 1 1 calc R . .
H00G H 0.6771 0.5254 1.0358 0.022 Uiso 1 1 calc R . .
H00H H 0.1910 0.2404 0.7228 0.016 Uiso 1 1 calc R . .
H00I H -0.0033 -0.0083 0.6147 0.019 Uiso 1 1 calc R . .
H00J H 0.2263 -0.3763 0.6275 0.017 Uiso 1 1 calc R . .
H00L H 0.5789 0.5651 0.6529 0.020 Uiso 1 1 calc R . .
H00M H 0.4242 0.0307 0.8969 0.017 Uiso 1 1 calc R . .
H00O H 0.3617 0.5126 0.7436 0.019 Uiso 1 1 calc R . .
H00P H -0.0489 -0.4535 0.6268 0.023 Uiso 1 1 calc R . .
H00Q H -0.1655 -0.2712 0.6150 0.024 Uiso 1 1 calc R . .
H00R H 0.8646 0.5196 0.9237 0.021 Uiso 1 1 calc R . .
C00B C 0.2776(4) -0.1459(4) 0.6221(3) 0.0112(7) Uani 1 1 d . . .
C00C C 0.2093(4) -0.0336(4) 0.6192(3) 0.0118(7) Uani 1 1 d . . .
C00D C 0.5351(4) 0.3257(4) 0.5866(3) 0.0139(7) Uani 1 1 d . . .
C00E C 0.3124(4) 0.1362(4) 0.6262(3) 0.0111(7) Uani 1 1 d . . .
C00F C 0.5332(4) 0.2785(4) 0.9770(3) 0.0177(8) Uani 1 1 d . . .
C00G C 0.6636(4) 0.4237(4) 0.9844(3) 0.0180(8) Uani 1 1 d . . .
C00H C 0.2812(4) 0.2641(4) 0.6884(3) 0.0133(7) Uani 1 1 d . . .
C00I C 0.0439(4) -0.0831(4) 0.6170(3) 0.0157(7) Uani 1 1 d . . .
C00J C 0.1802(4) -0.3008(4) 0.6249(3) 0.0140(7) Uani 1 1 d . . .
C00K C 0.7484(4) 0.2713(4) 0.8406(3) 0.0148(7) Uani 1 1 d . . .
C00L C 0.5094(4) 0.4558(4) 0.6474(3) 0.0164(7) Uani 1 1 d . . .
C00M C 0.5123(4) 0.1299(4) 0.9009(3) 0.0144(7) Uani 1 1 d . . .
C00N C 0.6189(4) 0.1252(4) 0.8307(3) 0.0119(7) Uani 1 1 d . . .
C00O C 0.3810(4) 0.4249(4) 0.7001(3) 0.0155(7) Uani 1 1 d . . .
C00P C 0.0160(4) -0.3475(4) 0.6237(3) 0.0190(8) Uani 1 1 d . . .
C00Q C -0.0526(4) -0.2388(4) 0.6181(3) 0.0199(8) Uani 1 1 d . . .
C00R C 0.7737(4) 0.4211(4) 0.9174(3) 0.0178(8) Uani 1 1 d . . .
N007 N 0.4395(3) 0.1678(3) 0.5761(2) 0.0111(6) Uani 1 1 d . . .
N008 N 0.4426(3) -0.1008(3) 0.6164(2) 0.0113(6) Uani 1 1 d . . .
N009 N 0.8718(4) 0.2789(4) 0.7728(3) 0.0214(7) Uani 1 1 d . . .
O00A O 1.0067(3) 0.3065(4) 0.8281(3) 0.0485(10) Uani 1 1 d . . .
O004 O 0.7258(3) -0.0557(3) 0.6970(2) 0.0168(5) Uani 1 1 d . . .
O005 O 0.5115(3) -0.1850(3) 0.7911(2) 0.0188(6) Uani 1 1 d . . .
O006 O 0.8328(4) 0.2597(3) 0.6667(2) 0.0298(7) Uani 1 1 d . . .
S002 S 0.57761(10) -0.06982(10) 0.73046(7) 0.0116(2) Uani 1 1 d . . .
Ni01 Ni 0.5000 0.0000 0.5000 0.00876(19) Uani 1 2 d S . .
H1SA H 0.1504 0.1455 0.1206 0.111 Uiso 0.50 1 calc PR A -1
H1SB H 0.0092 -0.0202 0.1226 0.111 Uiso 0.50 1 calc PR A -1
C1S C 0.042(2) 0.054(2) 0.0748(11) 0.092(6) Uani 0.50 1 d PD A -1
Cl1 Cl -0.0989(3) 0.1342(4) 0.0565(3) 0.0477(7) Uani 0.50 1 d PD A -1
Cl2 Cl 0.0658(6) -0.0527(8) -0.0537(4) 0.1114(19) Uani 0.50 1 d PD A -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'
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'
Ni Ni 0.3393 1.1124 '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'
Cl Cl 0.1484 0.1585 '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'
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
C00C C00B N008 119.3(3) . .
C00J C00B C00C 119.4(3) . .
C00J C00B N008 121.3(3) . .
C00B C00C C00E 120.8(3) . .
C00I C00C C00B 118.8(3) . .
C00I C00C C00E 120.3(3) . .
N007 C00D C00L 122.8(3) . .
C00H C00E C00C 119.5(3) . .
N007 C00E C00C 119.9(3) . .
N007 C00E C00H 120.6(3) . .
C00M C00F C00G 119.9(3) . .
C00R C00G C00F 120.4(3) . .
C00O C00H C00E 120.2(3) . .
C00Q C00I C00C 121.2(3) . .
C00B C00J C00P 121.0(3) . .
C00N C00K C00R 122.2(3) . .
C00N C00K N009 122.6(3) . .
C00R C00K N009 115.2(3) . .
C00D C00L C00O 118.9(3) . .
C00N C00M C00F 120.5(3) . .
C00K C00N S002 124.0(3) . .
C00M C00N C00K 118.4(3) . .
C00M C00N S002 117.6(3) . .
C00L C00O C00H 118.8(3) . .
C00Q C00P C00J 119.8(3) . .
C00I C00Q C00P 119.7(3) . .
C00G C00R C00K 118.5(3) . .
C00D N007 Ni01 118.4(2) . .
C00E N007 C00D 118.7(3) . .
C00E N007 Ni01 122.8(2) . .
C00B N008 S002 119.2(2) . .
C00B N008 Ni01 114.7(2) . .
S002 N008 Ni01 121.41(16) . .
O00A N009 C00K 116.5(3) . .
O00A N009 O006 124.8(3) . .
O006 N009 C00K 118.7(3) . .
N008 S002 C00N 106.06(14) . .
O004 S002 C00N 107.50(15) . .
O004 S002 N008 108.62(14) . .
O005 S002 C00N 104.83(15) . .
O005 S002 N008 110.76(15) . .
O005 S002 O004 118.30(14) . .
N007 Ni01 N007 180.0 . 2_656
N008 Ni01 N007 88.50(11) . .
N008 Ni01 N007 91.50(11) 2_656 .
N008 Ni01 N007 88.50(11) 2_656 2_656
N008 Ni01 N007 91.50(11) . 2_656
N008 Ni01 N008 179.999(1) 2_656 .
Cl2 C1S Cl1 115.5(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C00B C00C 1.409(4) .
C00B C00J 1.386(5) .
C00C C00E 1.471(5) .
C00C C00I 1.396(5) .
C00D C00L 1.377(5) .
C00E C00H 1.397(4) .
C00F C00G 1.391(5) .
C00F C00M 1.389(5) .
C00G C00R 1.381(5) .
C00H C00O 1.382(5) .
C00I C00Q 1.383(5) .
C00J C00P 1.390(5) .
C00K C00N 1.385(5) .
C00K C00R 1.388(5) .
C00L C00O 1.381(5) .
C00M C00N 1.384(5) .
C00P C00Q 1.385(5) .
N007 C00D 1.355(4) .
N007 C00E 1.352(4) .
N008 C00B 1.419(4) .
N009 C00K 1.474(4) .
N009 O00A 1.211(4) .
O006 N009 1.227(4) .
S002 C00N 1.786(3) .
S002 N008 1.594(3) .
S002 O004 1.435(2) .
S002 O005 1.433(2) .
Ni01 N007 1.923(3) .
Ni01 N007 1.923(3) 2_656
Ni01 N008 1.894(3) .
Ni01 N008 1.894(3) 2_656
C1S Cl2 1.718(10) .
Cl1 C1S 1.732(10) .
