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#$Date: 2019-11-24 05:13:33 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/74/4087457.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_4087457
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         'C22 H21 Cl F3 N2 Rh, C H2 Cl2'
_chemical_formula_sum            'C23 H23 Cl3 F3 N2 Rh'
_chemical_formula_weight         593.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.1900(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.4563(10)
_cell_length_b                   20.0842(17)
_cell_length_c                   18.696(2)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.36
_cell_measurement_theta_min      2.30
_cell_volume                     4664.8(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-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35748
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.042
_diffrn_reflns_theta_min         1.928
_exptl_absorpt_coefficient_mu    1.114
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.8836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2012/1'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_description       plate
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.457
_exptl_crystal_size_min          0.121
_refine_diff_density_max         1.871
_refine_diff_density_min         -1.701
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0332P)²+20.3752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6205
_reflns_number_total             6840
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00137_si_002.cif
_cod_data_source_block           Compound_7a
_cod_original_cell_volume        4664.9(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4087457
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.592
_shelx_estimated_absorpt_t_max   0.877
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Rh1 Rh 0.75230(2) 1.02152(2) 0.53833(2) 0.01179(5) Uani 1 1 d . . .
Cl1 Cl 0.61205(4) 0.95943(3) 0.58842(3) 0.01578(9) Uani 1 1 d . . .
Cl2 Cl 0.61591(12) 0.79306(11) 0.76141(7) 0.1076(7) Uani 1 1 d . . .
Cl3 Cl 0.88427(6) 0.71973(4) 0.75647(4) 0.03912(16) Uani 1 1 d . . .
F1 F 0.91297(17) 0.96953(8) 0.65740(9) 0.0388(4) Uani 1 1 d . . .
F2 F 0.83177(14) 0.88092(11) 0.68702(8) 0.0401(4) Uani 1 1 d . . .
F3 F 0.99789(12) 0.87733(9) 0.66710(8) 0.0316(4) Uani 1 1 d . . .
N1 N 0.87802(15) 0.89060(9) 0.57207(9) 0.0152(3) Uani 1 1 d . . .
N2 N 0.80725(14) 0.89610(9) 0.46353(9) 0.0130(3) Uani 1 1 d . . .
C1 C 0.82253(16) 0.93262(10) 0.52407(11) 0.0136(4) Uani 1 1 d . . .
C2 C 0.90431(19) 0.90520(12) 0.64587(12) 0.0209(4) Uani 1 1 d . . .
C3 C 0.89284(17) 0.82721(11) 0.54226(12) 0.0164(4) Uani 1 1 d . . .
C4 C 0.93964(19) 0.76876(12) 0.56932(14) 0.0225(5) Uani 1 1 d . . .
H4 H 0.9731 0.7661 0.6165 0.027 Uiso 1 1 calc R U .
C5 C 0.9346(2) 0.71448(12) 0.52326(15) 0.0271(5) Uani 1 1 d . . .
H5 H 0.9650 0.6734 0.5398 0.032 Uiso 1 1 calc R U .
C6 C 0.8864(2) 0.71799(12) 0.45362(16) 0.0261(5) Uani 1 1 d . . .
H6 H 0.8845 0.6794 0.4241 0.031 Uiso 1 1 calc R U .
C7 C 0.84158(18) 0.77657(11) 0.42675(13) 0.0204(4) Uani 1 1 d . . .
H7 H 0.8089 0.7795 0.3793 0.024 Uiso 1 1 calc R U .
C8 C 0.84672(16) 0.83102(10) 0.47274(12) 0.0151(4) Uani 1 1 d . . .
C9 C 0.76033(17) 0.92122(10) 0.39639(11) 0.0141(4) Uani 1 1 d . . .
C10 C 0.82099(18) 0.91738(12) 0.33701(12) 0.0198(4) Uani 1 1 d . . .
H10 H 0.8899 0.8969 0.3407 0.024 Uiso 1 1 calc R U .
C11 C 0.7796(2) 0.94386(13) 0.27229(13) 0.0249(5) Uani 1 1 d . . .
H11 H 0.8200 0.9412 0.2312 0.030 Uiso 1 1 calc R U .
C12 C 0.6791(2) 0.97422(13) 0.26732(13) 0.0246(5) Uani 1 1 d . . .
H12 H 0.6518 0.9933 0.2232 0.030 Uiso 1 1 calc R U .
C13 C 0.61868(19) 0.97669(12) 0.32684(12) 0.0207(4) Uani 1 1 d . . .
H13 H 0.5496 0.9970 0.3230 0.025 Uiso 1 1 calc R U .
C14 C 0.65842(17) 0.94969(11) 0.39202(11) 0.0155(4) Uani 1 1 d . . .
H14 H 0.6168 0.9507 0.4326 0.019 Uiso 1 1 calc R U .
C16 C 0.68965(17) 1.11688(11) 0.57676(12) 0.0174(4) Uani 1 1 d . . .
H16 H 0.6438 1.1129 0.6183 0.021 Uiso 1 1 calc R U .
C17 C 0.63824(17) 1.10114(11) 0.51107(12) 0.0171(4) Uani 1 1 d . . .
H17 H 0.5611 1.0880 0.5133 0.020 Uiso 1 1 calc R U .
C18 C 0.66401(18) 1.13122(12) 0.44021(13) 0.0205(4) Uani 1 1 d . . .
H18A H 0.6376 1.1777 0.4380 0.025 Uiso 1 1 calc R U .
H18B H 0.6247 1.1062 0.4009 0.025 Uiso 1 1 calc R U .
C19 C 0.78512(19) 1.13095(12) 0.42781(13) 0.0222(4) Uani 1 1 d . . .
H19A H 0.7938 1.1277 0.3757 0.027 Uiso 1 1 calc R U .
H19B H 0.8173 1.1736 0.4450 0.027 Uiso 1 1 calc R U .
C20 C 0.84563(17) 1.07378(11) 0.46593(12) 0.0168(4) Uani 1 1 d . . .
H20 H 0.8843 1.0442 0.4333 0.020 Uiso 1 1 calc R U .
C21 C 0.89481(17) 1.07775(11) 0.53621(12) 0.0175(4) Uani 1 1 d . . .
H21 H 0.9621 1.0508 0.5439 0.021 Uiso 1 1 calc R U .
C22 C 0.89092(18) 1.13744(12) 0.58539(13) 0.0216(4) Uani 1 1 d . . .
H22A H 0.9417 1.1716 0.5701 0.026 Uiso 1 1 calc R U .
H22B H 0.9153 1.1237 0.6348 0.026 Uiso 1 1 calc R U .
C23 C 0.77798(19) 1.16853(12) 0.58604(14) 0.0222(4) Uani 1 1 d . . .
H23A H 0.7720 1.1922 0.6320 0.027 Uiso 1 1 calc R U .
H23B H 0.7683 1.2017 0.5469 0.027 Uiso 1 1 calc R U .
C24 C 1.0000 0.6708(2) 0.7500 0.0487(12) Uani 1 2 d S T P
H24A H 0.9900 0.6418 0.7072 0.058 Uiso 0.5 1 calc R U P
H24B H 1.0100 0.6418 0.7928 0.058 Uiso 0.5 1 calc R U P
C25 C 0.5000 0.8433(3) 0.7500 0.088(3) Uani 1 2 d S T P
H25A H 0.4952 0.8722 0.7925 0.105 Uiso 0.5 1 calc R U P
H25B H 0.5048 0.8722 0.7075 0.105 Uiso 0.5 1 calc R U P
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 '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
C1 Rh1 C21 95.62(8) . .
C1 Rh1 C20 95.19(8) . .
C21 Rh1 C20 38.95(9) . .
C1 Rh1 C17 154.58(8) . .
C21 Rh1 C17 97.95(8) . .
C20 Rh1 C17 82.29(8) . .
C1 Rh1 C16 168.26(8) . .
C21 Rh1 C16 81.92(8) . .
C20 Rh1 C16 90.09(8) . .
C17 Rh1 C16 36.69(8) . .
C1 Rh1 Cl1 85.78(6) . .
C21 Rh1 Cl1 158.01(6) . .
C20 Rh1 Cl1 162.94(6) . .
C17 Rh1 Cl1 89.53(6) . .
C16 Rh1 Cl1 92.25(6) . .
C1 N1 C3 111.69(18) . .
C1 N1 C2 124.92(18) . .
C3 N1 C2 122.83(18) . .
C1 N2 C8 112.12(17) . .
C1 N2 C9 124.38(17) . .
C8 N2 C9 123.44(17) . .
N2 C1 N1 104.24(17) . .
N2 C1 Rh1 123.81(15) . .
N1 C1 Rh1 131.12(15) . .
F1 C2 F2 108.6(2) . .
F1 C2 F3 107.8(2) . .
F2 C2 F3 107.05(19) . .
F1 C2 N1 111.82(19) . .
F2 C2 N1 111.7(2) . .
F3 C2 N1 109.71(19) . .
C8 C3 C4 121.5(2) . .
C8 C3 N1 105.34(18) . .
C4 C3 N1 133.1(2) . .
C5 C4 C3 116.0(2) . .
C4 C5 C6 122.4(2) . .
C7 C6 C5 121.2(2) . .
C6 C7 C8 116.5(2) . .
C3 C8 C7 122.3(2) . .
C3 C8 N2 106.52(18) . .
C7 C8 N2 131.1(2) . .
C14 C9 C10 121.6(2) . .
C14 C9 N2 120.50(18) . .
C10 C9 N2 117.92(19) . .
C11 C10 C9 119.1(2) . .
C10 C11 C12 120.2(2) . .
C11 C12 C13 120.0(2) . .
C12 C13 C14 120.6(2) . .
C9 C14 C13 118.5(2) . .
C17 C16 C23 123.1(2) . .
C17 C16 Rh1 70.35(12) . .
C23 C16 Rh1 111.15(14) . .
C16 C17 C18 125.0(2) . .
C16 C17 Rh1 72.97(12) . .
C18 C17 Rh1 108.80(14) . .
C17 C18 C19 113.75(18) . .
C20 C19 C18 112.86(19) . .
C21 C20 C19 124.1(2) . .
C21 C20 Rh1 69.83(12) . .
C19 C20 Rh1 113.31(14) . .
C20 C21 C22 125.4(2) . .
C20 C21 Rh1 71.22(12) . .
C22 C21 Rh1 110.41(14) . .
C21 C22 C23 113.31(18) . .
C16 C23 C22 112.22(18) . .
Cl3 C24 Cl3 111.9(3) . 2_756
Cl2 C25 Cl2 110.1(4) 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Rh1 C1 2.014(2) .
Rh1 C21 2.107(2) .
Rh1 C20 2.125(2) .
Rh1 C17 2.175(2) .
Rh1 C16 2.208(2) .
Rh1 Cl1 2.3923(5) .
Cl2 C25 1.761(4) .
Cl3 C24 1.756(3) .
F1 C2 1.313(3) .
F2 C2 1.322(3) .
F3 C2 1.327(3) .
N1 C1 1.380(3) .
N1 C3 1.407(3) .
N1 C2 1.425(3) .
N2 C1 1.351(3) .
N2 C8 1.403(3) .
N2 C9 1.437(3) .
C3 C8 1.384(3) .
C3 C4 1.390(3) .
C4 C5 1.388(4) .
C5 C6 1.395(4) .
C6 C7 1.381(3) .
C7 C8 1.390(3) .
C9 C14 1.389(3) .
C9 C10 1.390(3) .
C10 C11 1.386(3) .
C11 C12 1.389(4) .
C12 C13 1.389(3) .
C13 C14 1.391(3) .
C16 C17 1.380(3) .
C16 C23 1.513(3) .
C17 C18 1.512(3) .
C18 C19 1.543(3) .
C19 C20 1.522(3) .
C20 C21 1.411(3) .
C21 C22 1.514(3) .
C22 C23 1.540(3) .
C24 Cl3 1.757(3) 2_756
C25 Cl2 1.761(4) 2_656
