#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:19:13 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179104 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/66/4306654.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_4306654
loop_
_publ_author_name
'Stephen M. Mansell'
'Christopher A. Russell'
'Duncan F. Wass'
_publ_contact_author
; 
    Dr. Chris Russell
    School of Chemistry
    University of Bristol
    Cantock's Close
    BS8 1TS Bristol
    UK
;
_publ_contact_author_email       Chris.Russell@bristol.ac.uk
_publ_contact_author_fax         '0117 9290509'
_publ_contact_author_phone       '0117 9287599'
_publ_section_title
;
Synthesis and Structural Characterization of Tin Analogues of N-Heterocyclic
Carbenes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11367
_journal_page_last               11375
_journal_paper_doi               10.1021/ic801479g
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C26 H38 N2 Sn'
_chemical_formula_sum            'C26 H38 N2 Sn'
_chemical_formula_weight         497.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 102.82(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.165(4)
_cell_length_b                   6.5412(13)
_cell_length_c                   19.886(4)
_cell_measurement_reflns_used    3193
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.07
_cell_volume                     2557.6(9)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER sAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.5
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  '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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13985
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (BRUKER-AXS, 2003)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.151
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0417
_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)+(0.0241P)²+9.0235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                2829
_reflns_number_total             2937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801479g_si_001_1.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2557.7(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4306654
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Sn1 Sn 0.25835(2) 0.42435(7) 0.04825(3) 0.02601(14) Uani 0.50 1 d P . .
N1 N 0.24756(11) 0.1202(3) 0.05102(10) 0.0257(4) Uani 1 1 d . . .
C1 C 0.25307(12) -0.0221(3) 0.10603(11) 0.0200(4) Uani 1 1 d . . .
C2 C 0.31680(12) -0.0740(4) 0.14711(12) 0.0244(5) Uani 1 1 d . . .
C3 C 0.31938(14) -0.2101(4) 0.20163(12) 0.0308(6) Uani 1 1 d . . .
H3 H 0.3614 -0.2431 0.2296 0.037 Uiso 1 1 calc R . .
C4 C 0.26162(16) -0.2966(4) 0.21513(12) 0.0325(6) Uani 1 1 d . . .
H4 H 0.2646 -0.3857 0.2521 0.039 Uiso 1 1 calc R . .
C5 C 0.19935(14) -0.2503(4) 0.17333(12) 0.0294(5) Uani 1 1 d . . .
H5 H 0.1604 -0.3119 0.1817 0.035 Uiso 1 1 calc R . .
C6 C 0.19355(12) -0.1127(4) 0.11871(12) 0.0239(5) Uani 1 1 d . . .
C7 C 0.12417(14) -0.0563(5) 0.07561(14) 0.0373(7) Uani 1 1 d . . .
H7 H 0.1302 -0.0215 0.0294 0.045 Uiso 1 1 calc R . .
C8 C 0.0729(2) -0.2304(9) 0.0673(2) 0.0855(18) Uani 1 1 d . . .
H8A H 0.0910 -0.3478 0.0486 0.128 Uiso 1 1 calc R . .
H8B H 0.0313 -0.1889 0.0367 0.128 Uiso 1 1 calc R . .
H8C H 0.0641 -0.2643 0.1115 0.128 Uiso 1 1 calc R . .
C9 C 0.0985(2) 0.1356(10) 0.1053(2) 0.100(2) Uani 1 1 d . . .
H9A H 0.0861 0.1025 0.1479 0.150 Uiso 1 1 calc R . .
H9B H 0.0595 0.1880 0.0731 0.150 Uiso 1 1 calc R . .
H9C H 0.1337 0.2372 0.1136 0.150 Uiso 1 1 calc R . .
C10 C 0.38251(14) 0.0157(5) 0.13402(15) 0.0384(7) Uani 1 1 d . . .
H10 H 0.3714 0.0866 0.0895 0.046 Uiso 1 1 calc R . .
C11 C 0.43466(19) -0.1484(8) 0.1295(2) 0.0706(13) Uani 1 1 d . . .
H11A H 0.4504 -0.2100 0.1740 0.106 Uiso 1 1 calc R . .
H11B H 0.4724 -0.0879 0.1147 0.106 Uiso 1 1 calc R . .
H11C H 0.4141 -0.2509 0.0969 0.106 Uiso 1 1 calc R . .
C12 C 0.41256(16) 0.1743(7) 0.18949(17) 0.0545(10) Uani 1 1 d . . .
H12A H 0.4268 0.1072 0.2333 0.082 Uiso 1 1 calc R . .
H12B H 0.3787 0.2750 0.1924 0.082 Uiso 1 1 calc R . .
H12C H 0.4509 0.2397 0.1775 0.082 Uiso 1 1 calc R . .
C13 C 0.2731(4) 0.3359(11) 0.0764(3) 0.0354(13) Uani 0.50 1 d P . .
H13A H 0.2560 0.3735 0.1167 0.042 Uiso 0.50 1 calc PR . .
H13B H 0.3224 0.3386 0.0888 0.042 Uiso 0.50 1 calc PR . .
C14 C 0.2464(3) 0.4857(10) 0.0167(3) 0.0319(14) Uani 0.50 1 d P . .
H14A H 0.2730 0.6106 0.0232 0.038 Uiso 0.50 1 calc PR . .
H14B H 0.1993 0.5203 0.0152 0.038 Uiso 0.50 1 calc PR . .
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'
Sn Sn -0.6537 1.4246 '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
N1 Sn1 N1 84.15(8) 7 . ?
N1 Sn1 Sn1 42.47(6) 7 7 ?
N1 Sn1 Sn1 41.68(6) . 7 ?
C1 N1 C14 111.7(3) . 7 ?
C1 N1 C13 112.5(3) . . ?
C14 N1 C13 127.5(4) 7 . ?
C1 N1 Sn1 130.57(16) . 7 ?
C14 N1 Sn1 19.8(3) 7 7 ?
C13 N1 Sn1 113.8(3) . 7 ?
C1 N1 Sn1 132.91(16) . . ?
C14 N1 Sn1 113.0(3) 7 . ?
C13 N1 Sn1 22.1(3) . . ?
Sn1 N1 Sn1 95.85(8) 7 . ?
C2 C1 C6 120.0(2) . . ?
C2 C1 N1 120.8(2) . . ?
C6 C1 N1 119.2(2) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 C10 119.7(2) . . ?
C1 C2 C10 121.7(2) . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 120.3(2) . . ?
C1 C6 C7 120.8(2) . . ?
C6 C7 C8 113.5(3) . . ?
C6 C7 C9 109.3(2) . . ?
C8 C7 C9 112.1(4) . . ?
C6 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
C9 C7 H7 107.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C2 112.2(3) . . ?
C11 C10 C12 110.6(3) . . ?
C2 C10 C12 110.9(2) . . ?
C11 C10 H10 107.7 . . ?
C2 C10 H10 107.7 . . ?
C12 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 107.1(5) . . ?
C14 C13 H13A 110.3 . . ?
N1 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
N1 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
C13 C14 N1 107.8(4) . 7 ?
C13 C14 H14A 110.2 . . ?
N1 C14 H14A 110.2 7 . ?
C13 C14 H14B 110.2 . . ?
N1 C14 H14B 110.2 7 . ?
H14A C14 H14B 108.5 . . ?
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
Sn1 N1 1.973(2) 7 ?
Sn1 N1 2.004(2) . ?
Sn1 Sn1 2.9516(8) 7 ?
N1 C1 1.421(3) . ?
N1 C14 1.543(6) 7 ?
N1 C13 1.548(6) . ?
N1 Sn1 1.973(2) 7 ?
C1 C2 1.403(3) . ?
C1 C6 1.411(3) . ?
C2 C3 1.395(3) . ?
C2 C10 1.524(4) . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(4) . ?
C7 C8 1.522(5) . ?
C7 C9 1.526(5) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.519(5) . ?
C10 C12 1.537(5) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.542(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.543(6) 7 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Sn1 N1 C1 171.0(3) 7 . . . ?
Sn1 Sn1 N1 C1 171.0(3) 7 . . . ?
N1 Sn1 N1 C14 10.3(3) 7 . . 7 ?
Sn1 Sn1 N1 C14 10.3(3) 7 . . 7 ?
N1 Sn1 N1 C13 145.6(6) 7 . . . ?
Sn1 Sn1 N1 C13 145.6(6) 7 . . . ?
N1 Sn1 N1 Sn1 0.0 7 . . 7 ?
C14 N1 C1 C2 87.9(4) 7 . . . ?
C13 N1 C1 C2 -63.0(4) . . . . ?
Sn1 N1 C1 C2 95.1(3) 7 . . . ?
Sn1 N1 C1 C2 -73.1(3) . . . . ?
C14 N1 C1 C6 -91.6(4) 7 . . . ?
C13 N1 C1 C6 117.5(4) . . . . ?
Sn1 N1 C1 C6 -84.3(3) 7 . . . ?
Sn1 N1 C1 C6 107.5(3) . . . . ?
C6 C1 C2 C3 -2.3(3) . . . . ?
N1 C1 C2 C3 178.3(2) . . . . ?
C6 C1 C2 C10 178.3(2) . . . . ?
N1 C1 C2 C10 -1.1(3) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C10 C2 C3 C4 -179.4(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -177.0(2) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
N1 C1 C6 C5 -179.2(2) . . . . ?
C2 C1 C6 C7 179.1(2) . . . . ?
N1 C1 C6 C7 -1.5(3) . . . . ?
C5 C6 C7 C8 -33.3(4) . . . . ?
C1 C6 C7 C8 149.0(3) . . . . ?
C5 C6 C7 C9 92.7(4) . . . . ?
C1 C6 C7 C9 -85.0(4) . . . . ?
C3 C2 C10 C11 51.7(4) . . . . ?
C1 C2 C10 C11 -128.9(3) . . . . ?
C3 C2 C10 C12 -72.5(4) . . . . ?
C1 C2 C10 C12 106.9(3) . . . . ?
C1 N1 C13 C14 -164.4(4) . . . . ?
C14 N1 C13 C14 50.3(8) 7 . . . ?
Sn1 N1 C13 C14 33.6(5) 7 . . . ?
Sn1 N1 C13 C14 -4.3(3) . . . . ?
N1 C13 C14 N1 -39.9(6) . . . 7 ?
