#------------------------------------------------------------------------------
#$Date: 2019-11-24 05:13:33 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/74/4087450.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_4087450
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_moiety         'C14 H10 F3 N3 O2'
_chemical_formula_sum            'C14 H10 F3 N3 O2'
_chemical_formula_weight         309.25
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/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                 97.305(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3131(3)
_cell_length_b                   13.1688(4)
_cell_length_c                   11.7048(4)
_cell_measurement_reflns_used    5118
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      2.34
_cell_volume                     1270.97(7)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0678
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20447
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2004/1
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0442
_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)+(0.0492P)²+0.6406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                1960
_reflns_number_total             2911
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00137_si_002.cif
_cod_data_source_block           Compound_2d-red
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4087450
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.4697(2) 0.63662(12) 0.51603(12) 0.0323(4) Uani 1 1 d .
O2 O 0.54750(19) 0.75609(10) 0.63794(13) 0.0276(4) Uani 1 1 d .
N1 N 0.0398(2) 0.34278(12) 1.02557(13) 0.0195(4) Uani 1 1 d .
N2 N 0.2166(2) 0.45733(12) 0.95787(13) 0.0189(4) Uani 1 1 d .
N3 N 0.4806(2) 0.67366(13) 0.61343(14) 0.0226(4) Uani 1 1 d .
F1 F -0.06770(17) 0.19898(9) 0.94799(11) 0.0365(4) Uani 1 1 d .
F2 F -0.05800(18) 0.21990(9) 1.13176(11) 0.0379(4) Uani 1 1 d .
F3 F 0.15867(18) 0.18529(9) 1.05782(12) 0.0398(4) Uani 1 1 d .
C1 C 0.1139(2) 0.40343(14) 1.11885(16) 0.0189(4) Uani 1 1 d .
C2 C 0.0865(3) 0.40292(16) 1.23249(17) 0.0238(5) Uani 1 1 d .
H2 H 0.0127 0.3562 1.2593 0.029 Uiso 1 1 calc R
C3 C 0.1701(3) 0.47301(16) 1.30691(17) 0.0253(5) Uani 1 1 d .
H3 H 0.1543 0.4738 1.3859 0.030 Uiso 1 1 calc R
C4 C 0.2754(3) 0.54102(16) 1.26708(17) 0.0245(5) Uani 1 1 d .
H4 H 0.3316 0.5880 1.3193 0.029 Uiso 1 1 calc R
C5 C 0.3017(3) 0.54257(15) 1.15119(17) 0.0222(4) Uani 1 1 d .
H5 H 0.3751 0.5896 1.1245 0.027 Uiso 1 1 calc R
C6 C 0.2179(2) 0.47385(15) 1.07672(17) 0.0193(4) Uani 1 1 d .
C7 C 0.1152(2) 0.36858(14) 0.92194(16) 0.0197(4) Uani 1 1 d .
H7A H 0.1820 0.3116 0.8992 0.024 Uiso 1 1 calc R
H7B H 0.0319 0.3857 0.8566 0.024 Uiso 1 1 calc R
C8 C 0.0191(3) 0.23891(16) 1.04124(19) 0.0276(5) Uani 1 1 d .
C9 C 0.2840(2) 0.51279(14) 0.87562(16) 0.0178(4) Uani 1 1 d .
C10 C 0.3540(3) 0.60871(15) 0.89732(17) 0.0220(4) Uani 1 1 d .
H10 H 0.3572 0.6380 0.9717 0.026 Uiso 1 1 calc R
C11 C 0.4184(3) 0.66090(15) 0.81187(17) 0.0219(4) Uani 1 1 d .
H11 H 0.4671 0.7255 0.8276 0.026 Uiso 1 1 calc R
C12 C 0.4119(2) 0.61898(14) 0.70305(16) 0.0193(4) Uani 1 1 d .
C13 C 0.3416(2) 0.52456(15) 0.67823(17) 0.0194(4) Uani 1 1 d .
H13 H 0.3370 0.4967 0.6030 0.023 Uiso 1 1 calc R
C14 C 0.2790(2) 0.47195(15) 0.76386(17) 0.0192(4) Uani 1 1 d .
H14 H 0.2316 0.4071 0.7475 0.023 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'
F F 0.0171 0.0103 '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
C8 N1 C1 119.80(16)
C8 N1 C7 114.01(16)
C1 N1 C7 108.23(15)
C9 N2 C6 130.84(17)
C9 N2 C7 119.27(15)
C6 N2 C7 109.75(15)
O1 N3 O2 122.68(17)
O1 N3 C12 118.93(17)
O2 N3 C12 118.39(16)
C2 C1 C6 121.93(19)
C2 C1 N1 128.83(19)
C6 C1 N1 109.10(16)
C1 C2 C3 118.0(2)
C4 C3 C2 120.56(19)
C3 C4 C5 121.5(2)
C6 C5 C4 118.2(2)
C5 C6 C1 119.73(18)
C5 C6 N2 131.70(19)
C1 C6 N2 108.56(17)
N2 C7 N1 103.65(15)
F2 C8 F1 108.18(18)
F2 C8 F3 106.21(17)
F1 C8 F3 106.02(17)
F2 C8 N1 111.70(17)
F1 C8 N1 109.96(17)
F3 C8 N1 114.42(19)
N2 C9 C10 123.10(17)
N2 C9 C14 118.53(17)
C10 C9 C14 118.35(18)
C11 C10 C9 120.63(18)
C10 C11 C12 119.78(19)
C11 C12 C13 121.08(18)
C11 C12 N3 119.73(18)
C13 C12 N3 119.19(17)
C14 C13 C12 119.15(18)
C13 C14 C9 121.00(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.233(2)
O2 N3 1.237(2)
N1 C8 1.394(3)
N1 C1 1.428(2)
N1 C7 1.474(2)
N2 C9 1.383(2)
N2 C6 1.407(2)
N2 C7 1.471(2)
N3 C12 1.448(2)
F1 C8 1.337(3)
F2 C8 1.330(2)
F3 C8 1.351(3)
C1 C2 1.378(3)
C1 C6 1.400(3)
C2 C3 1.393(3)
C3 C4 1.374(3)
C4 C5 1.401(3)
C5 C6 1.382(3)
C9 C10 1.401(3)
C9 C14 1.410(3)
C10 C11 1.376(3)
C11 C12 1.383(3)
C12 C13 1.389(3)
C13 C14 1.374(3)
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
C8 N1 C1 C2 -44.5(3)
C7 N1 C1 C2 -177.6(2)
C8 N1 C1 C6 139.79(19)
C7 N1 C1 C6 6.8(2)
C6 C1 C2 C3 -2.2(3)
N1 C1 C2 C3 -177.36(19)
C1 C2 C3 C4 0.7(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C6 0.4(3)
C4 C5 C6 C1 -1.8(3)
C4 C5 C6 N2 179.3(2)
C2 C1 C6 C5 2.8(3)
N1 C1 C6 C5 178.83(17)
C2 C1 C6 N2 -178.07(18)
N1 C1 C6 N2 -2.0(2)
C9 N2 C6 C5 -8.9(4)
C7 N2 C6 C5 175.5(2)
C9 N2 C6 C1 172.11(19)
C7 N2 C6 C1 -3.5(2)
C9 N2 C7 N1 -168.87(16)
C6 N2 C7 N1 7.3(2)
C8 N1 C7 N2 -144.45(18)
C1 N1 C7 N2 -8.4(2)
C1 N1 C8 F2 53.2(3)
C7 N1 C8 F2 -176.26(17)
C1 N1 C8 F1 173.33(17)
C7 N1 C8 F1 -56.1(2)
C1 N1 C8 F3 -67.5(2)
C7 N1 C8 F3 63.0(2)
C6 N2 C9 C10 -8.5(3)
C7 N2 C9 C10 166.82(18)
C6 N2 C9 C14 172.97(19)
C7 N2 C9 C14 -11.7(3)
N2 C9 C10 C11 -179.51(19)
C14 C9 C10 C11 -0.9(3)
C9 C10 C11 C12 0.9(3)
C10 C11 C12 C13 -0.2(3)
C10 C11 C12 N3 -179.56(18)
O1 N3 C12 C11 -177.92(18)
O2 N3 C12 C11 1.8(3)
O1 N3 C12 C13 2.7(3)
O2 N3 C12 C13 -177.64(18)
C11 C12 C13 C14 -0.5(3)
N3 C12 C13 C14 178.87(18)
C12 C13 C14 C9 0.5(3)
N2 C9 C14 C13 178.87(18)
C10 C9 C14 C13 0.2(3)
