#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/65/1506575.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_1506575
loop_
_publ_author_name
'Kashiwabara, Taigo'
'Kataoka, Kyoko'
'Hua, Ruimao'
'Shimada, Shigeru'
'Tanaka, Masato'
_publ_section_title
;
 CO-retentive addition reactions of fluorinated acid chlorides to alkynes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2241
_journal_page_last               2244
_journal_paper_doi               10.1021/ol050632w
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C14 H18 Cl2 F5 O2 P2 Rh '
_chemical_formula_sum            'C14 H18 Cl2 F5 O2 P2 Rh'
_chemical_formula_weight         549.05
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-11-06
_audit_creation_method           'by CrystalStructure 3.6.0'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.335(3)
_cell_length_b                   19.218(3)
_cell_length_c                   8.483(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    183(1)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.8
_cell_volume                     2010.9(8)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  SHELXL
_computing_structure_solution    'DIRDIF99 (PATTY)'
_diffrn_ambient_temperature      183(1)
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.9966
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2649
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.323
_exptl_absorpt_correction_T_max  0.673
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   psi-scans
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1088.00
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         2.08
_refine_diff_density_min         -2.54
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2626
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1401P)²+0.9351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1578
_reflns_number_gt                2571
_reflns_number_total             2626
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol050632wsi20050324_034620.cif
_cod_data_source_block           General
_cod_original_cell_volume        2011.0(7)
_cod_original_formula_sum        'C14 H18 Cl2 F5 O2 P2 Rh '
_cod_database_code               1506575
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-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
Rh(1) Rh 0.03839(3) 0.15226(2) 0.20491(5) 0.0126(2) Uani 1.00 1 d .
Cl(1) Cl 0.1333(1) 0.10760(9) 0.4277(2) 0.0254(4) Uani 1.00 1 d .
Cl(2) Cl 0.1854(1) 0.23866(8) 0.1528(2) 0.0261(4) Uani 1.00 1 d .
P(1) P -0.0485(1) 0.22628(9) 0.3880(2) 0.0194(4) Uani 1.00 1 d .
P(2) P 0.1427(1) 0.07428(8) 0.0511(2) 0.0165(3) Uani 1.00 1 d .
F(1) F -0.1011(3) 0.0745(3) -0.1097(6) 0.029(1) Uani 1.00 1 d .
F(2) F -0.2891(4) 0.0871(3) -0.2646(5) 0.031(1) Uani 1.00 1 d .
F(3) F -0.4784(4) 0.1057(3) -0.1062(7) 0.033(1) Uani 1.00 1 d .
F(4) F -0.4774(4) 0.1031(4) 0.2136(7) 0.045(1) Uani 1.00 1 d .
F(5) F -0.2914(4) 0.0902(4) 0.3718(6) 0.039(1) Uani 1.00 1 d .
O(1) O -0.0789(4) 0.0357(3) 0.3288(7) 0.029(1) Uani 1.00 1 d .
O(2) O -0.0501(5) 0.2299(3) -0.0709(7) 0.033(1) Uani 1.00 1 d .
C(1) C -0.0818(5) 0.0811(3) 0.2339(8) 0.017(1) Uani 1.00 1 d .
C(2) C -0.1880(6) 0.0867(3) 0.1370(9) 0.021(1) Uani 1.00 1 d .
C(3) C -0.1922(5) 0.0847(3) -0.0255(9) 0.018(1) Uani 1.00 1 d .
C(4) C -0.2878(6) 0.0898(4) -0.1099(9) 0.023(1) Uani 1.00 1 d .
C(5) C -0.3830(6) 0.0978(4) -0.0291(9) 0.022(1) Uani 1.00 1 d .
C(6) C -0.3846(6) 0.0974(4) 0.135(1) 0.029(2) Uani 1.00 1 d .
C(7) C -0.2876(6) 0.0905(4) 0.2165(9) 0.024(1) Uani 1.00 1 d .
C(8) C -0.0212(5) 0.1983(3) 0.0318(9) 0.019(1) Uani 1.00 1 d .
C(9) C -0.1071(7) 0.1832(5) 0.5533(9) 0.029(2) Uani 1.00 1 d .
C(10) C 0.0422(7) 0.2893(5) 0.474(1) 0.040(2) Uani 1.00 1 d .
C(11) C -0.1559(7) 0.2792(4) 0.307(1) 0.036(2) Uani 1.00 1 d .
C(12) C 0.2862(6) 0.0759(4) 0.105(1) 0.029(2) Uani 1.00 1 d .
C(13) C 0.1449(7) 0.0923(4) -0.1559(9) 0.030(2) Uani 1.00 1 d .
C(14) C 0.1042(6) -0.0161(3) 0.070(1) 0.025(1) Uani 1.00 1 d .
H(9A) H -0.0526 0.1533 0.6030 0.035 Uiso 1.00 1 c R
H(9B) H -0.1685 0.1548 0.5182 0.035 Uiso 1.00 1 c R
H(9C) H -0.1324 0.2179 0.6296 0.035 Uiso 1.00 1 c R
H(10A) H 0.1041 0.2652 0.5220 0.049 Uiso 1.00 1 c R
H(10B) H 0.0036 0.3157 0.5557 0.049 Uiso 1.00 1 c R
H(10C) H 0.0681 0.3211 0.3925 0.049 Uiso 1.00 1 c R
H(11A) H -0.1287 0.3047 0.2154 0.043 Uiso 1.00 1 c R
H(11B) H -0.1809 0.3123 0.3872 0.043 Uiso 1.00 1 c R
H(11C) H -0.2163 0.2493 0.2751 0.043 Uiso 1.00 1 c R
H(12A) H 0.2937 0.0668 0.2180 0.035 Uiso 1.00 1 c R
H(12B) H 0.3167 0.1217 0.0802 0.035 Uiso 1.00 1 c R
H(12C) H 0.3251 0.0401 0.0453 0.035 Uiso 1.00 1 c R
H(13A) H 0.1650 0.1410 -0.1730 0.036 Uiso 1.00 1 c R
H(13B) H 0.0728 0.0837 -0.2005 0.036 Uiso 1.00 1 c R
H(13C) H 0.1979 0.0619 -0.2075 0.036 Uiso 1.00 1 c R
H(14A) H 0.1023 -0.0290 0.1817 0.030 Uiso 1.00 1 c R
H(14B) H 0.1571 -0.0453 0.0148 0.030 Uiso 1.00 1 c R
H(14C) H 0.0322 -0.0231 0.0235 0.030 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.017 0.010
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.102 0.094
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Rh Rh -1.118 0.919
;
International Tables for Crystallography
(1992, 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
Cl(2) Rh(1) Cl(1) 91.32(6)
P(1) Rh(1) Cl(1) 85.31(6)
P(2) Rh(1) Cl(1) 86.67(6)
C(1) Rh(1) Cl(1) 91.1(2)
C(8) Rh(1) Cl(1) 171.4(2)
P(1) Rh(1) Cl(2) 92.60(6)
P(2) Rh(1) Cl(2) 85.91(6)
C(1) Rh(1) Cl(2) 176.8(2)
C(8) Rh(1) Cl(2) 80.3(2)
P(2) Rh(1) P(1) 171.81(6)
C(1) Rh(1) P(1) 89.7(2)
C(8) Rh(1) P(1) 93.0(2)
Rh(1) P(1) C(9) 115.0(3)
Rh(1) P(1) C(10) 112.9(3)
Rh(1) P(1) C(11) 115.0(3)
C(1) Rh(1) P(2) 92.1(2)
C(8) Rh(1) P(2) 94.6(2)
Rh(1) P(2) C(12) 112.2(3)
Rh(1) P(2) C(13) 115.2(3)
Rh(1) P(2) C(14) 114.6(3)
Rh(1) C(1) O(1) 123.7(5)
Rh(1) C(1) C(2) 120.4(5)
C(8) Rh(1) C(1) 97.3(3)
Rh(1) C(8) O(2) 174.2(6)
C(10) P(1) C(9) 104.1(4)
C(11) P(1) C(9) 105.3(4)
C(11) P(1) C(10) 103.4(4)
C(13) P(2) C(12) 103.1(4)
C(14) P(2) C(12) 104.4(3)
C(14) P(2) C(13) 106.0(4)
F(1) C(3) C(2) 120.1(6)
F(1) C(3) C(4) 116.6(6)
F(2) C(4) C(3) 121.7(7)
F(2) C(4) C(5) 119.7(7)
F(3) C(5) C(4) 121.0(7)
F(3) C(5) C(6) 118.0(6)
F(4) C(6) C(5) 120.9(7)
F(4) C(6) C(7) 120.1(8)
F(5) C(7) C(2) 120.7(7)
F(5) C(7) C(6) 117.8(7)
O(1) C(1) C(2) 115.7(6)
C(1) C(2) C(3) 124.0(6)
C(1) C(2) C(7) 119.3(6)
C(2) C(3) C(4) 123.2(6)
C(7) C(2) C(3) 116.7(6)
C(2) C(7) C(6) 121.4(7)
C(3) C(4) C(5) 118.6(7)
C(4) C(5) C(6) 120.9(7)
C(5) C(6) C(7) 119.0(7)
P(1) C(9) H(9A) 109.4682
P(1) C(9) H(9B) 109.4763
P(1) C(9) H(9C) 109.4719
P(1) C(10) H(10A) 109.4723
P(1) C(10) H(10C) 109.4742
P(1) C(10) H(10B) 109.4738
P(1) C(11) H(11A) 109.4704
P(1) C(11) H(11B) 109.4732
P(1) C(11) H(11C) 109.4670
P(2) C(12) H(12A) 109.4707
P(2) C(12) H(12B) 109.4782
P(2) C(12) H(12C) 109.4692
P(2) C(13) H(13A) 109.4748
P(2) C(13) H(13B) 109.4696
P(2) C(13) H(13C) 109.4686
P(2) C(14) H(14A) 109.4644
P(2) C(14) H(14B) 109.4703
P(2) C(14) H(14C) 109.4676
H(9B) C(9) H(9A) 109.4669
H(9C) C(9) H(9A) 109.4708
H(9C) C(9) H(9B) 109.4733
H(10C) C(10) H(10A) 109.4720
H(10B) C(10) H(10A) 109.4703
H(10C) C(10) H(10B) 109.4647
H(11B) C(11) H(11A) 109.4835
H(11C) C(11) H(11A) 109.4631
H(11C) C(11) H(11B) 109.4701
H(12B) C(12) H(12A) 109.4766
H(12C) C(12) H(12A) 109.4646
H(12C) C(12) H(12B) 109.4680
H(13B) C(13) H(13A) 109.4685
H(13C) C(13) H(13A) 109.4772
H(13C) C(13) H(13B) 109.4686
H(14B) C(14) H(14A) 109.4787
H(14C) C(14) H(14A) 109.4710
H(14C) C(14) H(14B) 109.4754
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Rh(1) Cl(1) 2.383(2)
Rh(1) Cl(2) 2.498(2)
Rh(1) P(1) 2.363(2)
Rh(1) P(2) 2.367(2)
Rh(1) C(1) 2.031(6)
Rh(1) C(8) 1.866(7)
P(1) C(9) 1.781(8)
P(1) C(10) 1.80(1)
P(1) C(11) 1.805(9)
P(2) C(12) 1.827(7)
P(2) C(13) 1.790(8)
P(2) C(14) 1.808(7)
F(1) C(3) 1.347(8)
F(2) C(4) 1.313(9)
F(3) C(5) 1.356(8)
F(4) C(6) 1.328(9)
F(5) C(7) 1.318(9)
O(1) C(1) 1.188(9)
O(2) C(8) 1.119(9)
C(1) Rh(1) 2.031(6)
C(1) O(1) 1.188(9)
C(1) C(2) 1.55(1)
C(2) C(1) 1.55(1)
C(2) C(3) 1.38(1)
C(2) C(7) 1.40(1)
C(3) F(1) 1.347(8)
C(3) C(2) 1.38(1)
C(3) C(4) 1.38(1)
C(4) C(3) 1.38(1)
C(4) C(5) 1.37(1)
C(5) C(6) 1.39(1)
C(6) C(7) 1.39(1)
C(9) H(9A) 0.9800
C(9) H(9B) 0.9800
C(9) H(9C) 0.9799
C(10) H(10A) 0.9800
C(10) H(10B) 0.9800
C(10) H(10C) 0.9801
C(11) H(11A) 0.9799
C(11) H(11B) 0.9799
C(11) H(11C) 0.9801
C(12) H(12A) 0.9800
C(12) H(12B) 0.9799
C(12) H(12C) 0.9801
C(13) H(13A) 0.9800
C(13) H(13B) 0.9799
C(13) H(13C) 0.9800
C(14) H(14A) 0.9800
C(14) H(14B) 0.9799
C(14) H(14C) 0.9800
