#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:02:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178970 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/99/4119931.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_4119931
loop_
_publ_author_name
'Jian-Jun Dai'
'Chi Fang'
'Bin Xiao'
'Jun Yi'
'Jun Xu'
'Zhao-Jing Liu'
'Xi Lu'
'Lei Liu'
'Yao Fu'
_publ_section_title
;
 Copper-Promoted Sandmeyer Trifluoromethylation Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8436
_journal_page_last               8439
_journal_paper_doi               10.1021/ja404217t
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C19 H13 F3 Fe'
_chemical_formula_weight         354.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 97.321(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7098(4)
_cell_length_b                   8.8646(6)
_cell_length_c                   11.5586(5)
_cell_measurement_reflns_used    1287
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      67.4435
_cell_measurement_theta_min      3.8525
_cell_volume                     783.52(8)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3210
_diffrn_reflns_theta_full        25.22
_diffrn_reflns_theta_max         25.22
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.7559
_exptl_absorpt_correction_T_min  0.7236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1482
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0774
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0514P)²+2.7346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1775
_refine_ls_wR_factor_ref         0.1849
_reflns_number_gt                1228
_reflns_number_total             1482
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja404217t_si_003.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        783.52(7)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4119931
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe -0.10812(16) 0.2500 0.66543(10) 0.0649(5) Uani 1 2 d S . .
C1 C -0.3540(8) 0.1705(8) 0.6122(5) 0.0743(18) Uani 1 1 d . . .
H1 H -0.4212 0.1093 0.6541 0.089 Uiso 1 1 d R . .
C3 C -0.2345(8) 0.1195(8) 0.5354(5) 0.0670(16) Uani 1 1 d . . .
H3 H -0.2128 0.0171 0.5166 0.080 Uiso 1 1 d R . .
C4 C -0.1588(10) 0.2500 0.4882(6) 0.058(2) Uani 1 2 d S . .
C6 C -0.0299(11) 0.2500 0.4113(7) 0.060(2) Uani 1 2 d S . .
C7 C 0.0771(12) 0.2500 0.3456(7) 0.065(2) Uani 1 2 d S . .
C8 C 0.2088(11) 0.2500 0.2667(7) 0.060(2) Uani 1 2 d S . .
C9 C 0.1600(11) 0.2500 0.1477(7) 0.073(3) Uani 1 2 d S . .
H9 H 0.0421 0.2500 0.1179 0.088 Uiso 1 2 calc SR . .
C10 C 0.2860(12) 0.2500 0.0722(8) 0.080(3) Uani 1 2 d S . .
H10 H 0.2518 0.2500 -0.0079 0.096 Uiso 1 2 calc SR . .
C11 C 0.4593(11) 0.2500 0.1140(7) 0.070(2) Uani 1 2 d S A .
C12 C 0.5084(13) 0.2500 0.2334(8) 0.085(3) Uani 1 2 d S . .
H12 H 0.6263 0.2500 0.2632 0.102 Uiso 1 2 calc SR . .
C13 C 0.3834(12) 0.2500 0.3079(8) 0.079(3) Uani 1 2 d S . .
H13 H 0.4179 0.2500 0.3880 0.094 Uiso 1 2 calc SR . .
C14 C 0.6021(13) 0.2500 0.0284(9) 0.093(3) Uani 1 2 d SDU . .
C15 C 0.1574(11) 0.2500 0.7086(8) 0.078(3) Uani 1 2 d S . .
H15 H 0.2404 0.2500 0.6570 0.093 Uiso 1 2 d SR . .
C16 C 0.0833(9) 0.3786(9) 0.7543(6) 0.0789(19) Uani 1 1 d . . .
H16 H 0.1090 0.4781 0.7377 0.095 Uiso 1 1 d R . .
C17 C -0.0374(9) 0.3287(8) 0.8307(5) 0.080(2) Uani 1 1 d . . .
H17 H -0.1036 0.3905 0.8728 0.096 Uiso 1 1 d R . .
F2 F 0.5309(14) 0.2500 -0.0768(8) 0.116(3) Uani 0.698(7) 2 d SPDU A 2
F1 F 0.6978(9) 0.1336(8) 0.0487(6) 0.114(2) Uani 0.698(7) 1 d PDU A 2
F1' F 0.566(2) 0.1461(16) -0.0469(12) 0.114(2) Uani 0.302(7) 1 d PDU A 1
F2' F 0.7540(18) 0.2500 0.0853(19) 0.116(3) Uani 0.302(7) 2 d SPDU A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3460 0.8440 '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
C4 Fe1 C16 122.8(3) . 4_565
C4 Fe1 C16 122.8(3) . .
C16 Fe1 C16 68.1(4) 4_565 .
C4 Fe1 C1 69.2(3) . .
C16 Fe1 C1 122.9(3) 4_565 .
C16 Fe1 C1 158.5(3) . .
C4 Fe1 C1 69.2(3) . 4_565
C16 Fe1 C1 158.5(3) 4_565 4_565
C16 Fe1 C1 122.9(3) . 4_565
C1 Fe1 C1 40.4(4) . 4_565
C4 Fe1 C17 159.3(2) . 4_565
C16 Fe1 C17 41.1(3) 4_565 4_565
C16 Fe1 C17 68.3(3) . 4_565
C1 Fe1 C17 106.9(3) . 4_565
C1 Fe1 C17 121.8(3) 4_565 4_565
C4 Fe1 C17 159.3(2) . .
C16 Fe1 C17 68.3(3) 4_565 .
C16 Fe1 C17 41.1(3) . .
C1 Fe1 C17 121.8(3) . .
C1 Fe1 C17 106.9(3) 4_565 .
C17 Fe1 C17 40.0(4) 4_565 .
C4 Fe1 C15 107.7(4) . .
C16 Fe1 C15 40.4(2) 4_565 .
C16 Fe1 C15 40.4(2) . .
C1 Fe1 C15 159.3(2) . .
C1 Fe1 C15 159.3(2) 4_565 .
C17 Fe1 C15 68.4(3) 4_565 .
C17 Fe1 C15 68.4(3) . .
C4 Fe1 C3 41.2(2) . .
C16 Fe1 C3 107.5(3) 4_565 .
C16 Fe1 C3 159.3(3) . .
C1 Fe1 C3 41.0(2) . .
C1 Fe1 C3 68.7(3) 4_565 .
C17 Fe1 C3 122.7(3) 4_565 .
C17 Fe1 C3 158.0(3) . .
C15 Fe1 C3 123.3(3) . .
C4 Fe1 C3 41.2(2) . 4_565
C16 Fe1 C3 159.3(3) 4_565 4_565
C16 Fe1 C3 107.5(3) . 4_565
C1 Fe1 C3 68.7(3) . 4_565
C1 Fe1 C3 41.0(2) 4_565 4_565
C17 Fe1 C3 158.0(3) 4_565 4_565
C17 Fe1 C3 122.7(3) . 4_565
C15 Fe1 C3 123.3(3) . 4_565
C3 Fe1 C3 69.0(4) . 4_565
C1 C1 C3 108.4(4) 4_565 .
C1 C1 Fe1 69.8(2) 4_565 .
C3 C1 Fe1 69.5(3) . .
C1 C1 H1 125.8 4_565 .
C3 C1 H1 125.8 . .
Fe1 C1 H1 127.1 . .
C1 C3 C4 107.9(6) . .
C1 C3 Fe1 69.5(3) . .
C4 C3 Fe1 69.2(4) . .
C1 C3 H3 126.0 . .
C4 C3 H3 126.1 . .
Fe1 C3 H3 128.7 . .
C6 C4 C3 126.2(4) . 4_565
C6 C4 C3 126.2(4) . .
C3 C4 C3 107.5(7) 4_565 .
C6 C4 Fe1 124.9(6) . .
C3 C4 Fe1 69.7(4) 4_565 .
C3 C4 Fe1 69.7(4) . .
C7 C6 C4 179.2(9) . .
C6 C7 C8 179.4(9) . .
C13 C8 C9 118.5(8) . .
C13 C8 C7 121.2(8) . .
C9 C8 C7 120.3(8) . .
C8 C9 C10 120.3(8) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
C11 C10 C9 120.8(8) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C10 C11 C12 119.0(8) . .
C10 C11 C14 120.7(8) . .
C12 C11 C14 120.3(8) . .
C13 C12 C11 120.1(9) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C12 C13 C8 121.3(8) . .
C12 C13 H13 119.3 . .
C8 C13 H13 119.3 . .
F2 C14 F2' 139.1(17) . .
F2 C14 F1' 46.7(9) . 4_565
F2' C14 F1' 117.5(12) . 4_565
F2 C14 F1' 46.7(9) . .
F2' C14 F1' 117.5(12) . .
F1' C14 F1' 92.7(18) 4_565 .
F2 C14 F1 110.3(8) . 4_565
F2' C14 F1 55.2(5) . 4_565
F1' C14 F1 67.2(9) 4_565 4_565
F1' C14 F1 141.7(14) . 4_565
F2 C14 F1 110.3(8) . .
F2' C14 F1 55.2(5) . .
F1' C14 F1 141.7(14) 4_565 .
F1' C14 F1 67.2(9) . .
F1 C14 F1 108.3(10) 4_565 .
F2 C14 C11 110.5(9) . .
F2' C14 C11 110.4(14) . .
F1' C14 C11 108.7(10) 4_565 .
F1' C14 C11 108.7(10) . .
F1 C14 C11 108.6(7) 4_565 .
F1 C14 C11 108.6(7) . .
C16 C15 C16 108.2(8) 4_565 .
C16 C15 Fe1 69.5(4) 4_565 .
C16 C15 Fe1 69.5(4) . .
C16 C15 H15 125.9 4_565 .
C16 C15 H15 125.9 . .
Fe1 C15 H15 126.4 . .
C15 C16 C17 107.9(7) . .
C15 C16 Fe1 70.1(5) . .
C17 C16 Fe1 69.7(4) . .
C15 C16 H16 125.7 . .
C17 C16 H16 126.4 . .
Fe1 C16 H16 125.9 . .
C17 C17 C16 108.0(4) 4_565 .
C17 C17 Fe1 70.0(2) 4_565 .
C16 C17 Fe1 69.2(4) . .
C17 C17 H17 126.2 4_565 .
C16 C17 H17 125.8 . .
Fe1 C17 H17 126.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C4 2.036(7) .
Fe1 C16 2.036(6) 4_565
Fe1 C16 2.036(7) .
Fe1 C1 2.042(6) .
Fe1 C1 2.042(6) 4_565
Fe1 C17 2.042(6) 4_565
Fe1 C17 2.042(6) .
Fe1 C15 2.044(9) .
Fe1 C3 2.043(6) .
Fe1 C3 2.043(6) 4_565
C1 C1 1.410(14) 4_565
C1 C3 1.431(8) .
C1 H1 0.9280 .
C3 C4 1.435(8) .
C3 H3 0.9527 .
C4 C6 1.415(11) .
C4 C3 1.435(8) 4_565
C6 C7 1.190(11) .
C7 C8 1.449(12) .
C8 C13 1.370(12) .
C8 C9 1.379(11) .
C9 C10 1.385(12) .
C9 H9 0.9300 .
C10 C11 1.362(12) .
C10 H10 0.9300 .
C11 C12 1.384(12) .
C11 C14 1.572(15) .
C12 C13 1.371(13) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 F2 1.268(7) .
C14 F2' 1.268(7) .
C14 F1' 1.273(7) 4_565
C14 F1' 1.273(7) .
C14 F1 1.273(6) 4_565
C14 F1 1.273(6) .
C15 C16 1.408(9) 4_565
C15 C16 1.408(9) .
C15 H15 0.9292 .
C16 C17 1.432(9) .
C16 H16 0.9291 .
C17 C17 1.396(14) 4_565
C17 H17 0.9276 .
