#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:04:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178767 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/21/4102175.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_4102175
loop_
_publ_author_name
'Zoë R. Turner'
'Ronan Bellabarba'
'Robert P. Tooze'
'Polly L. Arnold'
_publ_section_title
;
 Addition-Elimination Reactions across the M-C Bond of Metal
 N-Heterocyclic Carbenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4050
_journal_page_last               4051
_journal_paper_doi               10.1021/ja910673q
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C38 H58 I2 N4 O2 U'
_chemical_formula_sum            'C38 H58 I2 N4 O2 U'
_chemical_formula_weight         1094.71
_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                 90.2120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2758(2)
_cell_length_b                   12.5624(3)
_cell_length_c                   17.6005(3)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.3
_cell_volume                     2050.91(7)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'ORTEP (Farrugia, 1997)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Giacovazzo, 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20792
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.498
_exptl_absorpt_correction_T_max  0.372
_exptl_absorpt_correction_T_min  0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'ORANGE RED'
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         2.634
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         6091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0403
_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)+(0.0374P)²+2.5708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                5478
_reflns_number_total             6091
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910673q_si_002.cif
_cod_data_source_block           po8081
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4102175
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
C1 C 0.1654(4) 0.5587(3) 0.61545(19) 0.0175(6) Uani 1 1 d .
C5 C 0.3199(4) 0.6483(3) 0.7010(2) 0.0265(8) Uani 1 1 d .
H5A H 0.2930 0.6764 0.7515 0.032 Uiso 1 1 calc R
H5B H 0.4040 0.6884 0.6817 0.032 Uiso 1 1 calc R
C6 C 0.3509(5) 0.5297(4) 0.7043(3) 0.0329(10) Uani 1 1 d .
H6A H 0.4536 0.5148 0.6935 0.039 Uiso 1 1 calc R
H6B H 0.3261 0.4999 0.7547 0.039 Uiso 1 1 calc R
C7 C 0.2452(4) 0.3713(3) 0.6352(2) 0.0248(8) Uani 1 1 d .
H7A H 0.1498 0.3482 0.6541 0.030 Uiso 1 1 calc R
H7B H 0.3196 0.3366 0.6672 0.030 Uiso 1 1 calc R
C8 C 0.2624(4) 0.3323(3) 0.5531(2) 0.0237(8) Uani 1 1 d .
C9 C 0.4086(5) 0.3613(4) 0.5213(3) 0.0349(10) Uani 1 1 d .
H9A H 0.4143 0.3382 0.4682 0.052 Uiso 1 1 calc R
H9B H 0.4841 0.3258 0.5510 0.052 Uiso 1 1 calc R
H9C H 0.4220 0.4386 0.5241 0.052 Uiso 1 1 calc R
C10 C 0.2338(5) 0.2124(3) 0.5514(3) 0.0365(10) Uani 1 1 d .
H10A H 0.1377 0.1980 0.5719 0.055 Uiso 1 1 calc R
H10B H 0.3065 0.1758 0.5824 0.055 Uiso 1 1 calc R
H10C H 0.2389 0.1867 0.4989 0.055 Uiso 1 1 calc R
C21 C 0.1123(4) 0.7489(3) 0.6371(2) 0.0216(7) Uani 1 1 d .
C22 C 0.1738(4) 0.8365(3) 0.6011(2) 0.0234(7) Uani 1 1 d .
C23 C 0.0926(5) 0.9300(3) 0.5952(2) 0.0293(9) Uani 1 1 d .
H23 H 0.1325 0.9902 0.5703 0.035 Uiso 1 1 calc R
C24 C -0.0439(5) 0.9360(3) 0.6251(2) 0.0319(9) Uani 1 1 d .
H24 H -0.0972 1.0004 0.6213 0.038 Uiso 1 1 calc R
C25 C -0.1036(5) 0.8483(3) 0.6605(2) 0.0293(9) Uani 1 1 d .
H25 H -0.1981 0.8535 0.6809 0.035 Uiso 1 1 calc R
C26 C -0.0290(4) 0.7525(3) 0.6672(2) 0.0227(7) Uani 1 1 d .
C220 C 0.3256(5) 0.8355(3) 0.5685(2) 0.0284(8) Uani 1 1 d .
H220 H 0.3578 0.7597 0.5653 0.034 Uiso 1 1 calc R
C221 C 0.3344(6) 0.8834(4) 0.4890(3) 0.0380(10) Uani 1 1 d .
H22A H 0.2653 0.8474 0.4555 0.057 Uiso 1 1 calc R
H22B H 0.4322 0.8740 0.4691 0.057 Uiso 1 1 calc R
H22C H 0.3115 0.9595 0.4914 0.057 Uiso 1 1 calc R
C222 C 0.4300(5) 0.8945(4) 0.6221(3) 0.0401(11) Uani 1 1 d .
H22D H 0.4047 0.9702 0.6236 0.060 Uiso 1 1 calc R
H22E H 0.5289 0.8865 0.6035 0.060 Uiso 1 1 calc R
H22F H 0.4229 0.8644 0.6734 0.060 Uiso 1 1 calc R
C260 C -0.0966(4) 0.6578(3) 0.7071(2) 0.0263(8) Uani 1 1 d .
H260 H -0.0627 0.5919 0.6808 0.032 Uiso 1 1 calc R
C261 C -0.2614(5) 0.6581(4) 0.7042(3) 0.0403(11) Uani 1 1 d .
H26A H -0.2982 0.7163 0.7357 0.061 Uiso 1 1 calc R
H26B H -0.2980 0.5901 0.7235 0.061 Uiso 1 1 calc R
H26C H -0.2936 0.6680 0.6516 0.061 Uiso 1 1 calc R
C262 C -0.0458(5) 0.6517(4) 0.7900(2) 0.0361(10) Uani 1 1 d .
H26D H 0.0595 0.6463 0.7915 0.054 Uiso 1 1 calc R
H26E H -0.0882 0.5890 0.8143 0.054 Uiso 1 1 calc R
H26F H -0.0763 0.7160 0.8170 0.054 Uiso 1 1 calc R
N1 N 0.2571(4) 0.4862(2) 0.64468(19) 0.0227(7) Uani 1 1 d .
N2 N 0.1963(3) 0.6534(2) 0.64685(17) 0.0192(6) Uani 1 1 d .
O1 O 0.1539(3) 0.3832(2) 0.50833(15) 0.0242(5) Uani 1 1 d .
I1 I 0.18350(3) 0.62466(2) 0.385430(17) 0.03798(9) Uani 1 1 d .
U1 U 0.0000 0.5000 0.5000 0.01955(6) Uani 1 2 d S
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
U U -9.6767 9.6646 '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
N2 C1 N1 108.0(3) . .
N2 C1 U1 133.3(2) . .
N1 C1 U1 117.9(2) . .
N2 C5 C6 102.3(3) . .
N1 C6 C5 103.1(3) . .
N1 C7 C8 114.5(3) . .
O1 C8 C9 108.7(3) . .
O1 C8 C10 108.0(3) . .
C9 C8 C10 112.7(4) . .
O1 C8 C7 107.5(3) . .
C9 C8 C7 111.6(3) . .
C10 C8 C7 108.2(3) . .
C22 C21 C26 121.7(4) . .
C22 C21 N2 119.3(3) . .
C26 C21 N2 118.9(3) . .
C21 C22 C23 118.4(4) . .
C21 C22 C220 123.1(3) . .
C23 C22 C220 118.5(4) . .
C24 C23 C22 121.0(4) . .
C23 C24 C25 119.9(4) . .
C24 C25 C26 121.7(4) . .
C25 C26 C21 117.2(4) . .
C25 C26 C260 120.6(4) . .
C21 C26 C260 122.2(3) . .
C22 C220 C221 113.3(4) . .
C22 C220 C222 110.3(3) . .
C221 C220 C222 109.6(4) . .
C26 C260 C261 113.4(4) . .
C26 C260 C262 110.7(3) . .
C261 C260 C262 109.7(3) . .
C1 N1 C7 125.3(3) . .
C1 N1 C6 113.2(3) . .
C7 N1 C6 119.7(3) . .
C1 N2 C21 125.0(3) . .
C1 N2 C5 112.8(3) . .
C21 N2 C5 121.8(3) . .
C8 O1 U1 148.1(2) . .
O1 U1 O1 180.000(1) . 3_566
O1 U1 C1 75.12(10) . .
O1 U1 C1 104.88(10) 3_566 .
O1 U1 C1 104.88(10) . 3_566
O1 U1 C1 75.12(10) 3_566 3_566
C1 U1 C1 180.0 . 3_566
O1 U1 I1 91.40(8) . .
O1 U1 I1 88.60(8) 3_566 .
C1 U1 I1 92.34(8) . .
C1 U1 I1 87.66(8) 3_566 .
O1 U1 I1 88.60(8) . 3_566
O1 U1 I1 91.40(8) 3_566 3_566
C1 U1 I1 87.66(8) . 3_566
C1 U1 I1 92.34(8) 3_566 3_566
I1 U1 I1 180.000(10) . 3_566
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.343(5) .
C1 N1 1.346(5) .
C1 U1 2.647(3) .
C5 N2 1.489(5) .
C5 C6 1.518(6) .
C6 N1 1.466(5) .
C7 N1 1.457(5) .
C7 C8 1.536(6) .
C8 O1 1.426(4) .
C8 C9 1.513(6) .
C8 C10 1.530(5) .
C21 C22 1.393(5) .
C21 C26 1.416(5) .
C21 N2 1.440(5) .
C22 C23 1.399(5) .
C22 C220 1.521(6) .
C23 C24 1.375(6) .
C24 C25 1.383(6) .
C25 C26 1.393(5) .
C26 C260 1.519(6) .
C220 C221 1.526(6) .
C220 C222 1.540(6) .
C260 C261 1.529(6) .
C260 C262 1.532(6) .
O1 U1 2.053(3) .
I1 U1 3.0727(3) .
U1 O1 2.053(3) 3_566
U1 C1 2.647(3) 3_566
U1 I1 3.0727(3) 3_566
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
_geom_torsion_site_symmetry_4
N2 C5 C6 N1 7.8(4) .
N1 C7 C8 O1 -58.6(4) .
N1 C7 C8 C9 60.5(4) .
N1 C7 C8 C10 -175.0(3) .
C26 C21 C22 C23 0.3(5) .
N2 C21 C22 C23 -177.1(3) .
C26 C21 C22 C220 179.6(3) .
N2 C21 C22 C220 2.2(5) .
C21 C22 C23 C24 0.7(6) .
C220 C22 C23 C24 -178.6(4) .
C22 C23 C24 C25 -0.9(6) .
C23 C24 C25 C26 0.0(6) .
C24 C25 C26 C21 1.0(6) .
C24 C25 C26 C260 179.4(4) .
C22 C21 C26 C25 -1.1(5) .
N2 C21 C26 C25 176.3(3) .
C22 C21 C26 C260 -179.5(3) .
N2 C21 C26 C260 -2.1(5) .
C21 C22 C220 C221 134.2(4) .
C23 C22 C220 C221 -46.5(5) .
C21 C22 C220 C222 -102.5(4) .
C23 C22 C220 C222 76.8(5) .
C25 C26 C260 C261 27.0(5) .
C21 C26 C260 C261 -154.7(4) .
C25 C26 C260 C262 -96.7(4) .
C21 C26 C260 C262 81.6(4) .
N2 C1 N1 C7 169.4(4) .
U1 C1 N1 C7 -19.8(5) .
N2 C1 N1 C6 4.7(5) .
U1 C1 N1 C6 175.6(3) .
C8 C7 N1 C1 64.8(5) .
C8 C7 N1 C6 -131.5(4) .
C5 C6 N1 C1 -8.2(5) .
C5 C6 N1 C7 -173.8(4) .
N1 C1 N2 C21 -172.5(3) .
U1 C1 N2 C21 18.6(5) .
N1 C1 N2 C5 1.1(4) .
U1 C1 N2 C5 -167.8(3) .
C22 C21 N2 C1 -116.5(4) .
C26 C21 N2 C1 66.0(5) .
C22 C21 N2 C5 70.4(5) .
C26 C21 N2 C5 -107.1(4) .
C6 C5 N2 C1 -5.9(4) .
C6 C5 N2 C21 167.9(4) .
C9 C8 O1 U1 -107.9(5) .
C10 C8 O1 U1 129.6(4) .
C7 C8 O1 U1 13.0(6) .
C8 O1 U1 C1 17.6(5) .
C8 O1 U1 C1 -162.4(5) 3_566
C8 O1 U1 I1 109.7(5) .
C8 O1 U1 I1 -70.3(5) 3_566
N2 C1 U1 O1 154.1(4) .
N1 C1 U1 O1 -14.0(3) .
N2 C1 U1 O1 -25.9(4) 3_566
N1 C1 U1 O1 166.0(3) 3_566
N2 C1 U1 I1 63.2(3) .
N1 C1 U1 I1 -104.8(3) .
N2 C1 U1 I1 -116.8(3) 3_566
N1 C1 U1 I1 75.2(3) 3_566
