#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:29:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178653 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/64/4076478.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_4076478
loop_
_publ_author_name
'Braun, Markus'
'Frank, Walter'
'Ganter, Christian'
_publ_section_title
;
 Reactivity of an Oxalamide-Based N-Heterocyclic Carbene
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1927
_journal_paper_doi               10.1021/om201235c
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C21 H22 N2 O2 Se'
_chemical_formula_sum            'C21 H22 N2 O2 Se'
_chemical_formula_weight         413.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.2248(5)
_cell_length_b                   32.4746(18)
_cell_length_c                   11.1989(5)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      22.20
_cell_measurement_theta_min      4.90
_cell_volume                     4082.2(3)
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_collection       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       φ-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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12952
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.856
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       isometric
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.016(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1806
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0296
_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)+(0.0350P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0645
_reflns_number_gt                1470
_reflns_number_total             1806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om201235c_si_001.cif
_cod_data_source_block           opus1146b_compound_7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_database_code               4076478
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
Se1 Se 0.0000 0.0000 -0.00106(3) 0.08419(19) Uani 1 2 d S
N1 N 0.06432(19) 0.02609(6) 0.22978(19) 0.0561(5) Uani 1 1 d .
C1 C 0.0000 0.0000 0.1576(3) 0.0545(9) Uani 1 2 d S
C3 C 0.1461(2) 0.05726(8) 0.1872(2) 0.0551(7) Uani 1 1 d .
O1 O 0.0831(2) 0.03597(8) 0.4329(2) 0.0875(7) Uani 1 1 d .
C4 C 0.1066(3) 0.09743(9) 0.1745(3) 0.0594(7) Uani 1 1 d .
C2 C 0.0434(3) 0.01828(9) 0.3485(3) 0.0634(7) Uani 1 1 d .
C8 C 0.2621(3) 0.04552(9) 0.1616(3) 0.0621(7) Uani 1 1 d .
C9 C -0.0206(3) 0.10909(11) 0.2054(3) 0.0839(10) Uani 1 1 d .
H9A H -0.0377 0.1360 0.1745 0.126 Uiso 1 1 calc R
H9B H -0.0302 0.1092 0.2906 0.126 Uiso 1 1 calc R
H9C H -0.0744 0.0895 0.1708 0.126 Uiso 1 1 calc R
C5 C 0.1862(3) 0.12617(9) 0.1334(3) 0.0687(8) Uani 1 1 d .
H5A H 0.1615 0.1534 0.1252 0.082 Uiso 1 1 calc R
C6 C 0.3023(3) 0.11596(10) 0.1038(3) 0.0729(8) Uani 1 1 d .
C7 C 0.3371(3) 0.07552(10) 0.1182(3) 0.0726(8) Uani 1 1 d .
H7A H 0.4145 0.0682 0.0977 0.087 Uiso 1 1 calc R
C10 C 0.3875(4) 0.14835(12) 0.0584(4) 0.1050(13) Uani 1 1 d .
H10A H 0.4651 0.1364 0.0485 0.157 Uiso 1 1 calc R
H10B H 0.3917 0.1706 0.1147 0.157 Uiso 1 1 calc R
H10C H 0.3597 0.1586 -0.0171 0.157 Uiso 1 1 calc R
C11 C 0.3043(4) 0.00192(10) 0.1829(4) 0.0887(10) Uani 1 1 d .
H11A H 0.3865 -0.0004 0.1604 0.133 Uiso 1 1 calc R
H11B H 0.2575 -0.0168 0.1358 0.133 Uiso 1 1 calc R
H11C H 0.2956 -0.0048 0.2659 0.133 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
C2 N1 C1 111.4(2) . .
C2 N1 C3 123.8(2) . .
C1 N1 C3 124.7(2) . .
N1 C1 N1 108.0(3) . 2
N1 C1 Se1 125.98(15) . .
N1 C1 Se1 125.98(15) 2 .
C8 C3 C4 122.6(2) . .
C8 C3 N1 118.1(2) . .
C4 C3 N1 119.3(2) . .
C5 C4 C3 117.8(3) . .
C5 C4 C9 121.3(3) . .
C3 C4 C9 120.9(3) . .
O1 C2 N1 127.9(3) . .
O1 C2 C2 127.55(18) . 2
N1 C2 C2 104.55(15) . 2
C7 C8 C3 116.9(3) . .
C7 C8 C11 121.8(3) . .
C3 C8 C11 121.3(3) . .
C4 C9 H9A 109.5 . .
C4 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C4 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C4 C5 C6 122.0(3) . .
C4 C5 H5A 119.0 . .
C6 C5 H5A 119.0 . .
C5 C6 C7 117.8(3) . .
C5 C6 C10 120.6(3) . .
C7 C6 C10 121.6(3) . .
C8 C7 C6 122.8(3) . .
C8 C7 H7A 118.6 . .
C6 C7 H7A 118.6 . .
C6 C10 H10A 109.5 . .
C6 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C6 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C1 1.777(4) .
N1 C2 1.374(4) .
N1 C1 1.376(3) .
N1 C3 1.447(3) .
C1 N1 1.376(3) 2
C3 C8 1.387(4) .
C3 C4 1.385(4) .
O1 C2 1.192(3) .
C4 C5 1.372(4) .
C4 C9 1.517(4) .
C2 C2 1.536(6) 2
C8 C7 1.376(4) .
C8 C11 1.512(4) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C5 C6 1.385(5) .
C5 H5A 0.9300 .
C6 C7 1.379(4) .
C6 C10 1.510(4) .
C7 H7A 0.9300 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
