#------------------------------------------------------------------------------
#$Date: 2018-08-15 18:14:56 +0300 (Wed, 15 Aug 2018) $
#$Revision: 209728 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/36/7103628.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_7103628
loop_
_publ_author_name
'Nakai, Hidetaka'
'Tang, Yongjun'
'Gantzel, Peter'
'Meyer, Karsten'
_publ_section_title
;
 A new entry to N-heterocyclic carbene chemistry: synthesis and
 characterisation of a triscarbene complex of thallium(I)
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   1
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              24
_journal_page_last               25
_journal_paper_doi               10.1039/b209071f
_journal_year                    2003
_chemical_formula_sum            'C33 H49.25 N6'
_chemical_formula_weight         530.03
_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                 100.5090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0758(7)
_cell_length_b                   11.1310(6)
_cell_length_c                   23.7831(14)
_cell_measurement_temperature    100(2)
_cell_volume                     3143.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17623
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9545
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1157
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.192
_refine_ls_shift/su_mean         0.032
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0641P)²+1.6483P] where 
P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                3791
_reflns_number_total             4100
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b209071f.txt
_cod_data_source_block           carbene
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'Monocinic' was replaced with
'monoclinic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7103628
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.34799(11) 0.62105(13) 0.04113(6) 0.0290(4) Uani 1 1 d . . .
N2A N 0.34600(12) 0.81139(13) 0.05034(6) 0.0321(4) Uani 1 1 d . . .
N1B N -0.05077(11) 0.28706(12) 0.09374(6) 0.0266(3) Uani 1 1 d . . .
N2B N -0.11068(12) 0.22327(12) 0.16705(6) 0.0285(4) Uani 1 1 d . A .
N1C N 0.09911(12) 0.24699(13) -0.15096(6) 0.0287(4) Uani 1 1 d . . .
N2C N -0.03609(12) 0.24714(13) -0.22218(6) 0.0301(4) Uani 1 1 d . . .
C1 C 0.26575(14) 0.35140(16) -0.02343(7) 0.0282(4) Uani 1 1 d . . .
C2 C 0.25895(13) 0.41841(15) 0.02589(7) 0.0265(4) Uani 1 1 d . . .
C3 C 0.15869(14) 0.41923(15) 0.04814(7) 0.0259(4) Uani 1 1 d . . .
C4 C 0.06742(13) 0.34848(15) 0.02219(7) 0.0255(4) Uani 1 1 d . . .
C5 C 0.07645(14) 0.27386(15) -0.02419(7) 0.0268(4) Uani 1 1 d . . .
C6 C 0.17501(14) 0.27792(15) -0.04801(7) 0.0276(4) Uani 1 1 d . . .
C7 C 0.36993(15) 0.35811(19) -0.05096(9) 0.0415(5) Uani 1 1 d . . .
H7A H 0.3469 0.3670 -0.0924 0.062 Uiso 1 1 calc R . .
H7B H 0.4141 0.2843 -0.0426 0.062 Uiso 1 1 calc R . .
H7C H 0.4158 0.4273 -0.0356 0.062 Uiso 1 1 calc R . .
C8 C 0.35801(15) 0.49293(16) 0.05555(8) 0.0329(4) Uani 1 1 d . . .
H8A H 0.3647 0.4838 0.0974 0.040 Uiso 1 1 calc R . .
H8B H 0.4280 0.4613 0.0449 0.040 Uiso 1 1 calc R . .
C9 C 0.14496(15) 0.49695(16) 0.09864(7) 0.0334(4) Uani 1 1 d . . .
H9E H 0.1304 0.4471 0.1294 0.050 Uiso 1 1 d R . .
H9F H 0.0820 0.5500 0.0879 0.050 Uiso 1 1 d R . .
H9D H 0.2121 0.5431 0.1110 0.050 Uiso 1 1 d R . .
C10 C -0.04394(14) 0.35899(17) 0.04297(7) 0.0304(4) Uani 1 1 d . . .
H10A H -0.0565 0.4444 0.0516 0.036 Uiso 1 1 calc R . .
H10B H -0.1054 0.3341 0.0117 0.036 Uiso 1 1 calc R . .
C11 C -0.01855(15) 0.18940(17) -0.04892(8) 0.0350(4) Uani 1 1 d . . .
H11A H -0.0623 0.1691 -0.0193 0.053 Uiso 1 1 calc R . .
H11B H 0.0129 0.1159 -0.0623 0.053 Uiso 1 1 calc R . .
H11C H -0.0676 0.2286 -0.0810 0.053 Uiso 1 1 calc R . .
C12 C 0.18026(15) 0.20464(17) -0.10144(8) 0.0339(4) Uani 1 1 d . . .
H12A H 0.2572 0.2096 -0.1102 0.041 Uiso 1 1 calc R . .
H12B H 0.1646 0.1193 -0.0941 0.041 Uiso 1 1 calc R . .
C13A C 0.36121(15) 0.70819(16) 0.08240(8) 0.0334(4) Uani 1 1 d . . .
C14A C 0.32703(14) 0.66747(17) -0.01366(8) 0.0320(4) Uani 1 1 d . . .
H14A H 0.3154 0.6234 -0.0484 0.038 Uiso 1 1 calc R . .
C15A C 0.32633(15) 0.78765(17) -0.00787(8) 0.0340(4) Uani 1 1 d . . .
H15A H 0.3146 0.8452 -0.0379 0.041 Uiso 1 1 calc R . .
C16A C 0.35823(16) 0.93302(17) 0.07692(9) 0.0388(5) Uani 1 1 d . . .
C17A C 0.2935(2) 1.02498(19) 0.03555(10) 0.0550(6) Uani 1 1 d . . .
H17A H 0.2133 1.0041 0.0278 0.082 Uiso 1 1 calc R . .
H17B H 0.3226 1.0245 -0.0003 0.082 Uiso 1 1 calc R . .
H17C H 0.3032 1.1052 0.0527 0.082 Uiso 1 1 calc R . .
C18A C 0.48269(18) 0.9636(2) 0.08954(11) 0.0544(6) Uani 1 1 d . . .
H18A H 0.5230 0.9042 0.1161 0.082 Uiso 1 1 calc R . .
H18B H 0.4930 1.0437 0.1068 0.082 Uiso 1 1 calc R . .
H18C H 0.5125 0.9627 0.0539 0.082 Uiso 1 1 calc R . .
C19A C 0.30870(19) 0.9303(2) 0.13100(10) 0.0521(6) Uani 1 1 d . . .
H19A H 0.3497 0.8716 0.1577 0.078 Uiso 1 1 calc R . .
H19B H 0.2291 0.9074 0.1216 0.078 Uiso 1 1 calc R . .
H19C H 0.3153 1.0101 0.1487 0.078 Uiso 1 1 calc R . .
C13B C -0.11650(14) 0.32168(16) 0.13212(7) 0.0289(4) Uani 1 1 d . . .
C14B C -0.00883(14) 0.17176(16) 0.10377(7) 0.0301(4) Uani 1 1 d . . .
H14B H 0.0375 0.1296 0.0821 0.036 Uiso 1 1 calc R . .
C15B C -0.04636(15) 0.13100(16) 0.15013(7) 0.0304(4) Uani 1 1 d . . .
H15B H -0.0319 0.0546 0.1678 0.036 Uiso 1 1 calc R . .
C16B C -0.17776(17) 0.21092(18) 0.21332(8) 0.0395(5) Uani 1 1 d . . .
C17D C -0.21885(17) 0.08156(18) 0.21668(8) 0.100(6) Uiso 0.129(4) 1 d PR A 2
C18D C -0.27749(17) 0.29769(18) 0.20125(8) 0.100(6) Uiso 0.129(4) 1 d PR A 2
C19D C -0.10451(17) 0.24840(18) 0.27010(8) 0.100(6) Uiso 0.129(4) 1 d PR A 2
C17B C -0.2098(3) 0.3318(2) 0.23253(13) 0.0740(11) Uani 0.871(4) 1 d P A 1
H17D H -0.1416 0.3762 0.2493 0.111 Uiso 0.871(4) 1 calc PR A 1
H17E H -0.2579 0.3221 0.2613 0.111 Uiso 0.871(4) 1 calc PR A 1
H17F H -0.2508 0.3764 0.1997 0.111 Uiso 0.871(4) 1 calc PR A 1
C18B C -0.1140(2) 0.1361(3) 0.26227(10) 0.0529(8) Uani 0.871(4) 1 d P A 1
H18D H -0.0456 0.1788 0.2800 0.079 Uiso 0.871(4) 1 calc PR A 1
H18E H -0.0935 0.0586 0.2475 0.079 Uiso 0.871(4) 1 calc PR A 1
H18F H -0.1619 0.1226 0.2908 0.079 Uiso 0.871(4) 1 calc PR A 1
C19B C -0.2852(2) 0.1397(3) 0.18661(11) 0.0623(9) Uani 0.871(4) 1 d P A 1
H19D H -0.3281 0.1858 0.1548 0.093 Uiso 0.871(4) 1 calc PR A 1
H19E H -0.3318 0.1263 0.2157 0.093 Uiso 0.871(4) 1 calc PR A 1
H19F H -0.2634 0.0622 0.1725 0.093 Uiso 0.871(4) 1 calc PR A 1
C13C C 0.02675(15) 0.17037(16) -0.18456(7) 0.0308(4) Uani 1 1 d . . .
C14C C 0.08207(15) 0.36636(16) -0.16700(7) 0.0315(4) Uani 1 1 d . . .
H14C H 0.1223 0.4341 -0.1497 0.038 Uiso 1 1 calc R . .
C15C C -0.00301(16) 0.36638(16) -0.21203(8) 0.0338(4) Uani 1 1 d . . .
H15C H -0.0347 0.4346 -0.2330 0.041 Uiso 1 1 calc R . .
C16C C -0.13064(16) 0.20861(17) -0.26778(8) 0.0361(5) Uani 1 1 d . . .
C17C C -0.09647(19) 0.22965(19) -0.32551(8) 0.0449(5) Uani 1 1 d . . .
H17G H -0.0293 0.1819 -0.3280 0.067 Uiso 1 1 calc R . .
H17H H -0.0798 0.3150 -0.3296 0.067 Uiso 1 1 calc R . .
H17I H -0.1583 0.2056 -0.3561 0.067 Uiso 1 1 calc R . .
C18C C -0.23547(18) 0.2820(2) -0.26220(10) 0.0502(6) Uani 1 1 d . . .
H18G H -0.2557 0.2669 -0.2248 0.075 Uiso 1 1 calc R . .
H18H H -0.2982 0.2584 -0.2924 0.075 Uiso 1 1 calc R . .
H18I H -0.2196 0.3677 -0.2659 0.075 Uiso 1 1 calc R . .
C19C C -0.15459(18) 0.07596(18) -0.26020(9) 0.0448(5) Uani 1 1 d . . .
H19G H -0.0877 0.0287 -0.2637 0.067 Uiso 1 1 calc R . .
H19H H -0.2179 0.0508 -0.2897 0.067 Uiso 1 1 calc R . .
H19I H -0.1736 0.0630 -0.2223 0.067 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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
C13A N1A C14A 112.88(15) . . ?
C13A N1A C8 121.84(15) . . ?
C14A N1A C8 125.27(15) . . ?
C13A N2A C15A 112.11(15) . . ?
C13A N2A C16A 122.14(15) . . ?
C15A N2A C16A 125.61(15) . . ?
C13B N1B C14B 112.60(14) . . ?
C13B N1B C10 121.50(14) . . ?
C14B N1B C10 125.13(14) . . ?
C13B N2B C15B 112.65(14) . . ?
C13B N2B C16B 123.26(14) . . ?
C15B N2B C16B 123.65(14) . . ?
C13C N1C C14C 112.90(15) . . ?
C13C N1C C12 122.05(15) . . ?
C14C N1C C12 124.95(15) . . ?
C13C N2C C15C 112.04(15) . . ?
C13C N2C C16C 124.00(15) . . ?
C15C N2C C16C 123.94(15) . . ?
C2 C1 C6 119.74(15) . . ?
C2 C1 C7 120.78(15) . . ?
C6 C1 C7 119.48(15) . . ?
C1 C2 C3 120.18(15) . . ?
C1 C2 C8 121.10(15) . . ?
C3 C2 C8 118.71(15) . . ?
C4 C3 C2 119.46(15) . . ?
C4 C3 C9 118.62(15) . . ?
C2 C3 C9 121.90(15) . . ?
C5 C4 C3 120.77(15) . . ?
C5 C4 C10 120.15(15) . . ?
C3 C4 C10 118.99(15) . . ?
C4 C5 C6 119.36(15) . . ?
C4 C5 C11 120.73(15) . . ?
C6 C5 C11 119.91(15) . . ?
C1 C6 C5 120.18(15) . . ?
C1 C6 C12 120.74(15) . . ?
C5 C6 C12 119.05(15) . . ?
N1A C8 C2 113.45(14) . . ?
N1B C10 C4 114.36(14) . . ?
N1C C12 C6 112.04(14) . . ?
N1A C13A N2A 102.04(15) . . ?
C15A C14A N1A 106.20(16) . . ?
C14A C15A N2A 106.77(16) . . ?
N2A C16A C19A 108.56(15) . . ?
N2A C16A C18A 107.82(16) . . ?
C19A C16A C18A 111.53(18) . . ?
N2A C16A C17A 109.59(16) . . ?
C19A C16A C17A 108.94(18) . . ?
C18A C16A C17A 110.37(18) . . ?
N2B C13B N1B 101.97(14) . . ?
C15B C14B N1B 106.65(15) . . ?
C14B C15B N2B 106.11(15) . . ?
N2B C16B C17B 110.44(16) . . ?
N2B C16B C18B 110.44(16) . . ?
C17B C16B C18B 112.5(2) . . ?
N2B C16B C18D 108.62(9) . . ?
C17B C16B C18D 41.42(17) . . ?
C18B C16B C18D 139.50(11) . . ?
N2B C16B C17D 110.57(9) . . ?
C17B C16B C17D 136.64(13) . . ?
C18B C16B C17D 64.43(13) . . ?
C18D C16B C17D 110.6 . . ?
N2B C16B C19D 108.81(10) . . ?
C17B C16B C19D 67.98(17) . . ?
C18B C16B C19D 49.01(13) . . ?
C18D C16B C19D 107.6 . . ?
C17D C16B C19D 110.6 . . ?
N2B C16B C19B 105.74(16) . . ?
C17B C16B C19B 109.9(2) . . ?
C18B C16B C19B 107.57(19) . . ?
C18D C16B C19B 71.05(14) . . ?
C17D C16B C19B 44.49(14) . . ?
C19D C16B C19B 143.58(11) . . ?
N2C C13C N1C 102.25(14) . . ?
C15C C14C N1C 105.86(15) . . ?
C14C C15C N2C 106.95(16) . . ?
N2C C16C C19C 109.31(15) . . ?
N2C C16C C17C 108.37(16) . . ?
C19C C16C C17C 110.17(16) . . ?
N2C C16C C18C 108.64(15) . . ?
C19C C16C C18C 109.21(17) . . ?
C17C C16C C18C 111.11(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C13A 1.368(2) . ?
N1A C14A 1.381(2) . ?
N1A C8 1.467(2) . ?
N2A C13A 1.372(2) . ?
N2A C15A 1.387(2) . ?
N2A C16A 1.490(2) . ?
N1B C13B 1.370(2) . ?
N1B C14B 1.384(2) . ?
N1B C10 1.464(2) . ?
N2B C13B 1.369(2) . ?
N2B C15B 1.391(2) . ?
N2B C16B 1.487(2) . ?
N1C C13C 1.369(2) . ?
N1C C14C 1.387(2) . ?
N1C C12 1.466(2) . ?
N2C C13C 1.363(2) . ?
N2C C15C 1.394(2) . ?
N2C C16C 1.487(2) . ?
C1 C2 1.405(2) . ?
C1 C6 1.406(2) . ?
C1 C7 1.522(2) . ?
C2 C3 1.407(2) . ?
C2 C8 1.520(2) . ?
C3 C4 1.403(2) . ?
C3 C9 1.514(2) . ?
C4 C5 1.401(2) . ?
C4 C10 1.520(2) . ?
C5 C6 1.409(2) . ?
C5 C11 1.516(2) . ?
C6 C12 1.521(2) . ?
C14A C15A 1.345(3) . ?
C16A C19A 1.514(3) . ?
C16A C18A 1.517(3) . ?
C16A C17A 1.532(3) . ?
C14B C15B 1.345(2) . ?
C16B C17B 1.494(3) . ?
C16B C18B 1.521(3) . ?
C16B C18D 1.5296 . ?
C16B C17D 1.5298 . ?
C16B C19D 1.5310 . ?
C16B C19B 1.553(3) . ?
C14C C15C 1.342(3) . ?
C16C C19C 1.522(3) . ?
C16C C17C 1.522(3) . ?
C16C C18C 1.532(3) . ?
