#------------------------------------------------------------------------------
#$Date: 2019-11-24 05:13:33 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/74/4087451.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_4087451
loop_
_publ_author_name
'Engl, Pascal S.'
'Senn, Remo'
'Otth, Elisabeth'
'Togni, Antonio'
_publ_section_title
;
 Synthesis and Characterization of N-Trifluoromethyl N-Heterocyclic
 Carbene Ligands and Their Complexes
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1384
_journal_paper_doi               10.1021/acs.organomet.5b00137
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C9 H7 F3 N2 Se'
_chemical_formula_weight         279.13
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5169(3)
_cell_length_b                   13.2863(10)
_cell_length_c                   15.8699(12)
_cell_measurement_reflns_used    5184
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      32.28
_cell_measurement_theta_min      2.57
_cell_volume                     952.40(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      99(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10495
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    3.953
_exptl_absorpt_correction_T_max  0.7832
_exptl_absorpt_correction_T_min  0.3635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2004/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0334
_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)+(0.0392P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0757
_reflns_number_gt                2482
_reflns_number_total             2793
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00137_si_002.cif
_cod_data_source_block           Compound_6a
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4087451
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 1.11886(7) 0.39436(2) 0.27075(2) 0.01791(9) Uani 1 1 d .
F1 F 0.7279(5) 0.35945(15) 0.00404(13) 0.0277(5) Uani 1 1 d .
F2 F 0.7195(4) 0.27683(13) 0.11973(14) 0.0228(4) Uani 1 1 d .
F3 F 1.1252(5) 0.33901(13) 0.07519(14) 0.0274(4) Uani 1 1 d .
N1 N 0.7450(5) 0.55658(17) 0.22616(18) 0.0133(5) Uani 1 1 d .
N2 N 0.7745(6) 0.44780(17) 0.12373(17) 0.0136(5) Uani 1 1 d .
C1 C 0.5623(6) 0.5919(2) 0.16223(19) 0.0125(6) Uani 1 1 d .
C2 C 0.3857(8) 0.67776(19) 0.15867(19) 0.0161(6) Uani 1 1 d .
H2 H 0.3760 0.7238 0.2044 0.019 Uiso 1 1 calc R
C3 C 0.2266(7) 0.6927(2) 0.0862(2) 0.0168(6) Uani 1 1 d .
H3 H 0.1014 0.7499 0.0818 0.020 Uiso 1 1 calc R
C4 C 0.2449(8) 0.6256(2) 0.0188(2) 0.0181(7) Uani 1 1 d .
H4 H 0.1333 0.6387 -0.0307 0.022 Uiso 1 1 calc R
C5 C 0.4219(7) 0.5403(2) 0.0223(2) 0.0163(6) Uani 1 1 d .
H5 H 0.4356 0.4952 -0.0240 0.020 Uiso 1 1 calc R
C6 C 0.5773(6) 0.5240(2) 0.09604(19) 0.0131(6) Uani 1 1 d .
C7 C 0.8384(7) 0.3566(2) 0.0810(2) 0.0177(6) Uani 1 1 d .
C8 C 0.7779(8) 0.6053(3) 0.3086(2) 0.0227(6) Uani 1 1 d .
H8A H 0.6424 0.5739 0.3491 0.034 Uiso 1 1 calc R
H8B H 0.7310 0.6771 0.3035 0.034 Uiso 1 1 calc R
H8C H 0.9822 0.5975 0.3284 0.034 Uiso 1 1 calc R
C9 C 0.8712(7) 0.46846(18) 0.20493(18) 0.0130(5) 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'
F F 0.0171 0.0103 '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
C9 N1 C1 111.3(3)
C9 N1 C8 124.4(3)
C1 N1 C8 124.2(2)
C9 N2 C7 123.3(2)
C9 N2 C6 110.1(2)
C7 N2 C6 126.1(3)
C6 C1 N1 107.7(2)
C6 C1 C2 122.0(3)
N1 C1 C2 130.3(3)
C3 C2 C1 116.9(3)
C2 C3 C4 121.3(3)
C5 C4 C3 121.7(3)
C6 C5 C4 117.0(3)
C5 C6 C1 121.0(3)
C5 C6 N2 133.9(3)
C1 C6 N2 105.1(2)
F3 C7 F1 108.1(3)
F3 C7 F2 106.6(3)
F1 C7 F2 107.2(3)
F3 C7 N2 112.6(3)
F1 C7 N2 109.9(3)
F2 C7 N2 112.1(3)
N1 C9 N2 105.7(2)
N1 C9 Se1 126.0(2)
N2 C9 Se1 128.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C9 1.820(3)
F1 C7 1.320(4)
F2 C7 1.338(4)
F3 C7 1.320(4)
N1 C9 1.345(3)
N1 C1 1.390(4)
N1 C8 1.468(4)
N2 C9 1.388(4)
N2 C7 1.418(4)
N2 C6 1.419(4)
C1 C6 1.386(4)
C1 C2 1.393(4)
C2 C3 1.371(5)
C3 C4 1.394(5)
C4 C5 1.388(4)
C5 C6 1.382(4)
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
C9 N1 C1 C6 -1.3(3)
C8 N1 C1 C6 -177.0(3)
C9 N1 C1 C2 178.2(3)
C8 N1 C1 C2 2.6(5)
C6 C1 C2 C3 -0.2(5)
N1 C1 C2 C3 -179.7(3)
C1 C2 C3 C4 -0.9(5)
C2 C3 C4 C5 0.7(5)
C3 C4 C5 C6 0.7(5)
C4 C5 C6 C1 -1.9(4)
C4 C5 C6 N2 179.6(3)
N1 C1 C6 C5 -178.7(3)
C2 C1 C6 C5 1.7(4)
N1 C1 C6 N2 0.1(3)
C2 C1 C6 N2 -179.4(3)
C9 N2 C6 C5 179.7(3)
C7 N2 C6 C5 -8.0(5)
C9 N2 C6 C1 1.0(3)
C7 N2 C6 C1 173.4(3)
C9 N2 C7 F3 -57.0(4)
C6 N2 C7 F3 131.5(3)
C9 N2 C7 F1 -177.7(3)
C6 N2 C7 F1 10.9(4)
C9 N2 C7 F2 63.2(4)
C6 N2 C7 F2 -108.3(3)
C1 N1 C9 N2 1.9(3)
C8 N1 C9 N2 177.5(3)
C1 N1 C9 Se1 -178.5(2)
C8 N1 C9 Se1 -2.8(4)
C7 N2 C9 N1 -174.4(3)
C6 N2 C9 N1 -1.8(3)
C7 N2 C9 Se1 6.0(4)
C6 N2 C9 Se1 178.6(2)
