#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:44:20 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178961 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/90/4119031.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_4119031
loop_
_publ_author_name
'Maialen Espinal de Viguri'
'Miguel A. Huertos'
'Julio Pérez'
'Lucía Riera'
'Irene Ara'
_publ_contact_author
;    LUCIA RIERA 
     Departamento de Quimica Inorganica
     ISQCH - Facultad de Ciencias
     Universidad de Zaragoza-CSIC
     C/ Pedro Cerbuna 12
     50009 Zaragoza  
     SPAIN
;
_publ_contact_author_email       riera@unizar.es
_publ_contact_author_fax         +34-976761187
_publ_contact_author_phone       +34-976761184
_publ_section_title
;
 Re-Mediated C-C Coupling of Pyridines and Imidazoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20326
_journal_page_last               20329
_journal_paper_doi               10.1021/ja310981m
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C16 H14 F3 N2 O6 Re S'
_chemical_formula_weight         605.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.269(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4146(5)
_cell_length_b                   13.4021(6)
_cell_length_c                   14.6235(7)
_cell_measurement_reflns_used    8962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.56
_cell_volume                     1938.23(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17486
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    6.442
_exptl_absorpt_correction_T_max  0.7389
_exptl_absorpt_correction_T_min  0.4658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.075
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.400
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0226
_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)+(0.0337P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0551
_refine_ls_wR_factor_ref         0.0569
_reflns_number_gt                3914
_reflns_number_total             4560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310981m_si_001_4.cif
_cod_data_source_block           ial195a-complexI
_cod_original_cell_volume        1938.23(16)
_cod_database_code               4119031
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Re Re 0.527940(12) 0.129988(9) 0.205641(9) 0.02104(5) Uani 1 1 d .
S S 0.46665(8) 0.33584(7) 0.30385(6) 0.02529(18) Uani 1 1 d .
F1 F 0.6034(2) 0.37377(15) 0.48325(16) 0.0356(5) Uani 1 1 d .
F2 F 0.5041(3) 0.50038(17) 0.40052(18) 0.0488(6) Uani 1 1 d .
F3 F 0.6862(2) 0.44076(18) 0.38060(18) 0.0458(6) Uani 1 1 d .
O1 O 0.5001(3) -0.06008(18) 0.08572(18) 0.0340(6) Uani 1 1 d .
O2 O 0.3631(2) 0.24238(19) 0.02257(18) 0.0333(6) Uani 1 1 d .
O3 O 0.2675(3) 0.0643(2) 0.2457(2) 0.0450(7) Uani 1 1 d .
O4 O 0.5657(2) 0.25461(17) 0.30589(17) 0.0268(5) Uani 1 1 d .
O5 O 0.4320(3) 0.3926(2) 0.21617(19) 0.0403(7) Uani 1 1 d .
O6 O 0.3590(3) 0.3044(2) 0.33889(19) 0.0409(7) Uani 1 1 d .
N1 N 0.7164(3) 0.1836(2) 0.18439(19) 0.0216(6) Uani 1 1 d .
N2 N 0.6598(3) 0.0550(2) 0.33482(19) 0.0212(6) Uani 1 1 d .
C1 C 0.5111(4) 0.0135(3) 0.1299(2) 0.0252(7) Uani 1 1 d .
C2 C 0.4226(3) 0.2012(3) 0.0920(2) 0.0253(7) Uani 1 1 d .
C3 C 0.3653(4) 0.0897(3) 0.2311(3) 0.0286(8) Uani 1 1 d .
C4 C 0.7364(3) 0.1771(2) 0.0977(2) 0.0231(7) Uani 1 1 d .
H4 H 0.6690 0.1455 0.0466 0.028 Uiso 1 1 calc R
C5 C 0.8491(3) 0.2140(2) 0.0795(2) 0.0244(7) Uani 1 1 d .
H5 H 0.8584 0.2068 0.0172 0.029 Uiso 1 1 calc R
C6 C 0.9494(3) 0.2615(2) 0.1519(3) 0.0248(7) Uani 1 1 d .
C7 C 0.9296(3) 0.2682(2) 0.2410(2) 0.0236(7) Uani 1 1 d .
H7 H 0.9959 0.2999 0.2928 0.028 Uiso 1 1 calc R
C8 C 0.8144(3) 0.2294(2) 0.2554(2) 0.0230(7) Uani 1 1 d .
H8 H 0.8037 0.2350 0.3174 0.028 Uiso 1 1 calc R
C9 C 1.0729(4) 0.3039(3) 0.1348(3) 0.0377(9) Uani 1 1 d .
H9A H 1.0686 0.2920 0.0678 0.056 Uiso 1 1 calc R
H9B H 1.1536 0.2715 0.1780 0.056 Uiso 1 1 calc R
H9C H 1.0773 0.3758 0.1475 0.056 Uiso 1 1 calc R
C10 C 0.7621(3) -0.0052(2) 0.3314(2) 0.0247(7) Uani 1 1 d .
H10 H 0.7810 -0.0109 0.2722 0.030 Uiso 1 1 calc R
C11 C 0.8405(3) -0.0587(2) 0.4092(3) 0.0251(7) Uani 1 1 d .
H11 H 0.9119 -0.0994 0.4030 0.030 Uiso 1 1 calc R
C12 C 0.8154(3) -0.0534(2) 0.4969(2) 0.0240(7) Uani 1 1 d .
C13 C 0.7124(4) 0.0110(3) 0.5014(2) 0.0301(8) Uani 1 1 d .
H13 H 0.6934 0.0191 0.5604 0.036 Uiso 1 1 calc R
C14 C 0.6381(4) 0.0627(3) 0.4211(3) 0.0286(8) Uani 1 1 d .
H14 H 0.5684 0.1058 0.4263 0.034 Uiso 1 1 calc R
C15 C 0.8941(4) -0.1134(3) 0.5827(3) 0.0310(8) Uani 1 1 d .
H15A H 0.8608 -0.0991 0.6370 0.047 Uiso 1 1 calc R
H15B H 0.9901 -0.0957 0.6001 0.047 Uiso 1 1 calc R
H15C H 0.8829 -0.1847 0.5671 0.047 Uiso 1 1 calc R
C16 C 0.5703(4) 0.4170(3) 0.3968(3) 0.0314(8) Uani 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 Re C3 87.46(15)
C1 Re C2 88.87(14)
C3 Re C2 90.45(15)
C1 Re O4 173.21(12)
C3 Re O4 93.99(13)
C2 Re O4 97.75(12)
C1 Re N2 92.53(12)
C3 Re N2 93.24(13)
C2 Re N2 176.10(12)
O4 Re N2 80.77(9)
C1 Re N1 96.32(12)
C3 Re N1 176.13(13)
C2 Re N1 90.47(12)
O4 Re N1 82.16(9)
N2 Re N1 85.76(10)
O6 S O5 117.94(18)
O6 S O4 113.04(16)
O5 S O4 112.50(15)
O6 S C16 104.90(16)
O5 S C16 106.03(18)
O4 S C16 100.19(16)
S O4 Re 124.62(14)
C4 N1 C8 116.6(3)
C4 N1 Re 121.2(2)
C8 N1 Re 122.1(2)
C10 N2 C14 116.3(3)
C10 N2 Re 121.9(2)
C14 N2 Re 121.6(2)
O1 C1 Re 177.8(3)
O2 C2 Re 177.5(3)
O3 C3 Re 179.1(4)
N1 C4 C5 123.5(3)
C4 C5 C6 120.0(3)
C7 C6 C5 116.8(3)
C7 C6 C9 121.4(3)
C5 C6 C9 121.8(3)
C8 C7 C6 120.7(3)
N1 C8 C7 122.4(3)
N2 C10 C11 123.5(3)
C10 C11 C12 120.2(3)
C11 C12 C13 116.5(3)
C11 C12 C15 122.2(3)
C13 C12 C15 121.3(3)
C14 C13 C12 120.4(3)
N2 C14 C13 123.0(3)
F2 C16 F1 108.1(3)
F2 C16 F3 108.4(3)
F1 C16 F3 107.0(3)
F2 C16 S 110.0(3)
F1 C16 S 111.5(2)
F3 C16 S 111.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Re C1 1.890(3)
Re C3 1.922(3)
Re C2 1.932(4)
Re O4 2.175(2)
Re N2 2.199(3)
Re N1 2.202(3)
S O6 1.434(3)
S O5 1.436(3)
S O4 1.494(2)
S C16 1.810(4)
F1 C16 1.334(4)
F2 C16 1.324(4)
F3 C16 1.339(4)
O1 C1 1.165(4)
O2 C2 1.151(4)
O3 C3 1.156(4)
N1 C4 1.350(4)
N1 C8 1.354(4)
N2 C10 1.350(4)
N2 C14 1.353(4)
C4 C5 1.375(5)
C5 C6 1.388(5)
C6 C7 1.384(5)
C6 C9 1.497(5)
C7 C8 1.383(4)
C10 C11 1.376(5)
C11 C12 1.388(5)
C12 C13 1.394(5)
C12 C15 1.500(5)
C13 C14 1.374(5)
