#------------------------------------------------------------------------------
#$Date: 2019-11-10 19:34:33 +0200 (Sun, 10 Nov 2019) $
#$Revision: 226058 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/60/4516017.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_4516017
loop_
_publ_author_name
'Dutta, Champak'
'Ghorai, Debasish'
'Choudhury, Joyanta'
_publ_section_title
;
 To "Rollover" or Not? Stereoelectronically Guided C-H
 Functionalization Pathways from Rhodium-Abnormal NHC Intermediates.
;
_journal_issue                   2
_journal_name_full               'ACS omega'
_journal_page_first              1614
_journal_page_last               1620
_journal_paper_doi               10.1021/acsomega.7b01846
_journal_volume                  3
_journal_year                    2018
_chemical_formula_sum            'C24 H22 F6 N3 P'
_chemical_formula_weight         497.41
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 116.068(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.1002(10)
_cell_length_b                   15.1276(6)
_cell_length_c                   13.5007(6)
_cell_measurement_reflns_used    8111
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.63
_cell_volume                     4421.4(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.0705
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26364
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.178
_diffrn_reflns_theta_min         2.628
_exptl_absorpt_coefficient_mu    0.193
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       plate
_exptl_crystal_F_000             2048
_refine_diff_density_max         1.336
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.313
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.313
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.2046
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3392
_reflns_number_total             4881
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            3a.cif
_cod_data_source_block           TR1_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4516017
_shelx_shelxl_version_number     2014/7
_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.
;
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
P001 P 0.5000 0.44183(7) 0.2500 0.0209(3) Uani 1 2 d S T P
P002 P 0.5000 0.97920(7) 0.2500 0.0248(3) Uani 1 2 d S T P
F003 F 0.42735(9) 0.97834(14) 0.21022(19) 0.0521(7) Uani 1 1 d . . .
N004 N 0.65722(10) 0.61042(15) 0.46082(19) 0.0195(5) Uani 1 1 d . . .
F005 F 0.5000 0.87350(18) 0.2500 0.0624(10) Uani 1 2 d S T P
F006 F 0.57321(9) 0.44136(17) 0.31503(19) 0.0612(7) Uani 1 1 d . . .
N007 N 0.57240(10) 0.67723(16) 0.43284(19) 0.0201(5) Uani 1 1 d . . .
F008 F 0.50974(12) 0.9790(2) 0.3734(2) 0.0722(8) Uani 1 1 d . . .
F009 F 0.5000 1.08381(18) 0.2500 0.0603(10) Uani 1 2 d S T P
N00A N 0.73971(12) 0.54093(17) 0.6054(2) 0.0276(6) Uani 1 1 d . . .
C00B C 0.65019(12) 0.67864(19) 0.3857(2) 0.0190(6) Uani 1 1 d . . .
C00C C 0.59655(13) 0.71916(19) 0.3692(2) 0.0213(6) Uani 1 1 d . . .
H00C H 0.5786 0.7682 0.3219 0.026 Uiso 1 1 calc R U .
C00D C 0.80492(13) 0.69344(19) 0.3654(2) 0.0215(7) Uani 1 1 d . . .
C00E C 0.70422(13) 0.54213(19) 0.4978(3) 0.0214(7) Uani 1 1 d . . .
C00F C 0.60980(12) 0.61139(19) 0.4877(2) 0.0205(6) Uani 1 1 d . . .
C00G C 0.66448(12) 0.73648(18) 0.2261(2) 0.0192(6) Uani 1 1 d . . .
C00H C 0.80635(13) 0.75778(19) 0.2928(2) 0.0235(7) Uani 1 1 d . . .
H00H H 0.7735 0.7991 0.2621 0.028 Uiso 1 1 calc R U .
C00I C 0.69399(13) 0.69961(18) 0.3399(2) 0.0183(6) Uani 1 1 d . . .
F00J F 0.50521(13) 0.3712(3) 0.1720(3) 0.1119(13) Uani 1 1 d . . .
C00K C 0.75481(13) 0.68304(18) 0.3983(2) 0.0201(6) Uani 1 1 d . . .
H00K H 0.7669 0.6616 0.4710 0.024 Uiso 1 1 calc R U .
C00L C 0.63825(13) 0.8210(2) 0.2050(3) 0.0262(7) Uani 1 1 d . . .
H00L H 0.6415 0.8575 0.2646 0.031 Uiso 1 1 calc R U .
C00M C 0.85570(13) 0.6355(2) 0.4126(2) 0.0241(7) Uani 1 1 d . . .
H00M H 0.8570 0.5933 0.4657 0.029 Uiso 1 1 calc R U .
C00N C 0.66039(14) 0.6857(2) 0.1375(3) 0.0252(7) Uani 1 1 d . . .
H00N H 0.6786 0.6286 0.1503 0.030 Uiso 1 1 calc R U .
C00O C 0.90360(14) 0.7027(2) 0.3090(3) 0.0311(8) Uani 1 1 d . . .
H00O H 0.9366 0.7054 0.2886 0.037 Uiso 1 1 calc R U .
F00P F 0.49446(14) 0.5134(2) 0.3268(3) 0.1285(17) Uani 1 1 d . . .
C00Q C 0.51323(13) 0.7003(2) 0.4325(3) 0.0265(7) Uani 1 1 d . . .
H00A H 0.4802 0.6648 0.3770 0.040 Uiso 1 1 calc R U .
H00B H 0.5047 0.7632 0.4150 0.040 Uiso 1 1 calc R U .
H00D H 0.5153 0.6884 0.5054 0.040 Uiso 1 1 calc R U .
C00R C 0.59985(14) 0.5479(2) 0.5618(3) 0.0269(7) Uani 1 1 d . . .
H00E H 0.5969 0.4879 0.5326 0.040 Uiso 1 1 calc R U .
H00F H 0.5615 0.5627 0.5665 0.040 Uiso 1 1 calc R U .
H00G H 0.6346 0.5511 0.6355 0.040 Uiso 1 1 calc R U .
C00S C 0.70940(14) 0.4871(2) 0.4215(3) 0.0288(7) Uani 1 1 d . . .
H00S H 0.6815 0.4907 0.3454 0.035 Uiso 1 1 calc R U .
C00T C 0.85496(14) 0.7623(2) 0.2647(3) 0.0288(7) Uani 1 1 d . . .
H00T H 0.8551 0.8065 0.2148 0.035 Uiso 1 1 calc R U .
C00U C 0.90366(14) 0.6392(2) 0.3829(3) 0.0300(8) Uani 1 1 d . . .
H00U H 0.9367 0.5981 0.4133 0.036 Uiso 1 1 calc R U .
C00V C 0.60758(14) 0.8520(2) 0.0979(3) 0.0330(8) Uani 1 1 d . . .
H00V H 0.5896 0.9093 0.0844 0.040 Uiso 1 1 calc R U .
C00W C 0.78480(15) 0.4797(2) 0.6404(3) 0.0334(8) Uani 1 1 d . . .
H00W H 0.8107 0.4755 0.7173 0.040 Uiso 1 1 calc R U .
C00X C 0.60308(15) 0.8000(3) 0.0108(3) 0.0377(9) Uani 1 1 d . . .
H00X H 0.5815 0.8212 -0.0627 0.045 Uiso 1 1 calc R U .
C00Y C 0.62980(15) 0.7177(2) 0.0302(3) 0.0343(8) Uani 1 1 d . . .
H00Y H 0.6274 0.6824 -0.0298 0.041 Uiso 1 1 calc R U .
C00Z C 0.79563(15) 0.4230(2) 0.5715(3) 0.0358(8) Uani 1 1 d . . .
H00Z H 0.8291 0.3824 0.6000 0.043 Uiso 1 1 calc R U .
C010 C 0.75691(15) 0.4262(2) 0.4600(3) 0.0367(9) Uani 1 1 d . . .
H010 H 0.7629 0.3870 0.4105 0.044 Uiso 1 1 calc R U .
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'
P P 0.1023 0.0942 '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
F00J P001 F00J 92.3(3) . 2_655
F00J P001 F00P 179.3(3) . .
F00J P001 F00P 88.3(2) 2_655 .
F00J P001 F00P 88.3(2) . 2_655
F00J P001 F00P 179.3(3) 2_655 2_655
F00P P001 F00P 91.0(4) . 2_655
F00J P001 F006 91.34(14) . 2_655
F00J P001 F006 88.30(15) 2_655 2_655
F00P P001 F006 88.36(15) . 2_655
F00P P001 F006 92.00(15) 2_655 2_655
F00J P001 F006 88.30(15) . .
F00J P001 F006 91.35(14) 2_655 .
F00P P001 F006 92.00(15) . .
F00P P001 F006 88.36(15) 2_655 .
F006 P001 F006 179.5(2) 2_655 .
F008 P002 F008 179.8(2) . 2_655
F008 P002 F009 90.08(12) . .
F008 P002 F009 90.08(12) 2_655 .
F008 P002 F003 89.28(13) . .
F008 P002 F003 90.72(13) 2_655 .
F009 P002 F003 90.47(8) . .
F008 P002 F003 90.72(13) . 2_655
F008 P002 F003 89.28(13) 2_655 2_655
F009 P002 F003 90.47(8) . 2_655
F003 P002 F003 179.07(17) . 2_655
F008 P002 F005 89.92(12) . .
F008 P002 F005 89.92(12) 2_655 .
F009 P002 F005 180.0 . .
F003 P002 F005 89.53(8) . .
F003 P002 F005 89.53(8) 2_655 .
C00F N004 C00B 109.9(2) . .
C00F N004 C00E 123.0(2) . .
C00B N004 C00E 126.9(2) . .
C00F N007 C00C 108.8(2) . .
C00F N007 C00Q 126.9(2) . .
C00C N007 C00Q 124.2(2) . .
C00E N00A C00W 115.3(3) . .
C00C C00B N004 104.7(2) . .
C00C C00B C00I 129.8(3) . .
N004 C00B C00I 125.5(2) . .
C00B C00C N007 108.7(2) . .
C00B C00C H00C 125.6 . .
N007 C00C H00C 125.6 . .
C00H C00D C00M 117.9(3) . .
C00H C00D C00K 124.5(3) . .
C00M C00D C00K 117.6(3) . .
N00A C00E C00S 126.0(3) . .
N00A C00E N004 114.7(3) . .
C00S C00E N004 119.3(3) . .
N007 C00F N004 107.9(2) . .
N007 C00F C00R 126.2(3) . .
N004 C00F C00R 125.8(3) . .
C00N C00G C00L 118.4(3) . .
C00N C00G C00I 120.2(3) . .
C00L C00G C00I 121.4(3) . .
C00T C00H C00D 120.9(3) . .
C00T C00H H00H 119.5 . .
C00D C00H H00H 119.5 . .
C00K C00I C00B 120.7(3) . .
C00K C00I C00G 125.2(3) . .
C00B C00I C00G 114.1(2) . .
C00I C00K C00D 129.2(3) . .
C00I C00K H00K 115.4 . .
C00D C00K H00K 115.4 . .
C00V C00L C00G 120.5(3) . .
C00V C00L H00L 119.7 . .
C00G C00L H00L 119.7 . .
C00U C00M C00D 121.0(3) . .
C00U C00M H00M 119.5 . .
C00D C00M H00M 119.5 . .
C00G C00N C00Y 120.6(3) . .
C00G C00N H00N 119.7 . .
C00Y C00N H00N 119.7 . .
C00U C00O C00T 119.6(3) . .
C00U C00O H00O 120.2 . .
C00T C00O H00O 120.2 . .
N007 C00Q H00A 109.5 . .
N007 C00Q H00B 109.5 . .
H00A C00Q H00B 109.5 . .
N007 C00Q H00D 109.5 . .
H00A C00Q H00D 109.5 . .
H00B C00Q H00D 109.5 . .
C00F C00R H00E 109.5 . .
C00F C00R H00F 109.5 . .
H00E C00R H00F 109.5 . .
C00F C00R H00G 109.5 . .
H00E C00R H00G 109.5 . .
H00F C00R H00G 109.5 . .
C00E C00S C010 117.2(3) . .
C00E C00S H00S 121.4 . .
C010 C00S H00S 121.4 . .
C00H C00T C00O 120.4(3) . .
C00H C00T H00T 119.8 . .
C00O C00T H00T 119.8 . .
C00M C00U C00O 120.1(3) . .
C00M C00U H00U 120.0 . .
C00O C00U H00U 120.0 . .
C00X C00V C00L 120.3(3) . .
C00X C00V H00V 119.9 . .
C00L C00V H00V 119.9 . .
N00A C00W C00Z 123.9(3) . .
N00A C00W H00W 118.0 . .
C00Z C00W H00W 118.0 . .
C00Y C00X C00V 120.0(3) . .
C00Y C00X H00X 120.0 . .
C00V C00X H00X 120.0 . .
C00X C00Y C00N 120.2(3) . .
C00X C00Y H00Y 119.9 . .
C00N C00Y H00Y 119.9 . .
C00W C00Z C010 118.6(3) . .
C00W C00Z H00Z 120.7 . .
C010 C00Z H00Z 120.7 . .
C00Z C010 C00S 119.0(3) . .
C00Z C010 H010 120.5 . .
C00S C010 H010 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P001 F00J 1.544(3) .
P001 F00J 1.544(3) 2_655
P001 F00P 1.544(3) .
P001 F00P 1.544(3) 2_655
P001 F006 1.5883(19) 2_655
P001 F006 1.588(2) .
P002 F008 1.578(2) .
P002 F008 1.578(2) 2_655
P002 F009 1.583(3) .
P002 F003 1.5898(18) .
P002 F003 1.5898(18) 2_655
P002 F005 1.599(3) .
N004 C00F 1.342(3) .
N004 C00B 1.404(3) .
N004 C00E 1.450(4) .
N007 C00F 1.329(4) .
N007 C00C 1.385(4) .
N007 C00Q 1.466(3) .
N00A C00E 1.324(4) .
N00A C00W 1.346(4) .
C00B C00C 1.358(4) .
C00B C00I 1.473(4) .
C00C H00C 0.9500 .
C00D C00H 1.393(4) .
C00D C00M 1.409(4) .
C00D C00K 1.467(4) .
C00E C00S 1.372(4) .
C00F C00R 1.481(4) .
C00G C00N 1.388(4) .
C00G C00L 1.399(4) .
C00G C00I 1.489(4) .
C00H C00T 1.383(4) .
C00H H00H 0.9500 .
C00I C00K 1.348(4) .
C00K H00K 0.9500 .
C00L C00V 1.385(4) .
C00L H00L 0.9500 .
C00M C00U 1.381(4) .
C00M H00M 0.9500 .
C00N C00Y 1.392(4) .
C00N H00N 0.9500 .
C00O C00U 1.385(5) .
C00O C00T 1.389(5) .
C00O H00O 0.9500 .
C00Q H00A 0.9800 .
C00Q H00B 0.9800 .
C00Q H00D 0.9800 .
C00R H00E 0.9800 .
C00R H00F 0.9800 .
C00R H00G 0.9800 .
C00S C010 1.381(4) .
C00S H00S 0.9500 .
C00T H00T 0.9500 .
C00U H00U 0.9500 .
C00V C00X 1.378(5) .
C00V H00V 0.9500 .
C00W C00Z 1.371(5) .
C00W H00W 0.9500 .
C00X C00Y 1.374(5) .
C00X H00X 0.9500 .
C00Y H00Y 0.9500 .
C00Z C010 1.380(5) .
C00Z H00Z 0.9500 .
C010 H010 0.9500 .
