#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:44:23 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178627 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/38/4073832.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_4073832
loop_
_publ_author_name
'Doherty, Simon'
'Knight, Julian G.'
'Smyth, Catherine H.'
'Harrington, Ross W.'
'Clegg, William'
_publ_section_title
;
 Metal-Dependent Reactivity of Electrophilic Platinum Group Metal Lewis
 Acid Catalysts:  Competitive Alkene Dimerization, Intramolecular
 Friedel−Crafts Alkylation, and Carbonyl-Ene Reactivity
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              5961
_journal_paper_doi               10.1021/om7006612
_journal_volume                  26
_journal_year                    2007
_chemical_formula_moiety         'C19 H19 Cl F6 O6'
_chemical_formula_sum            'C19 H19 Cl F6 O6'
_chemical_formula_weight         492.79
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.851(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.715(3)
_cell_length_b                   11.8054(15)
_cell_length_c                   16.619(4)
_cell_measurement_reflns_used    215
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.50
_cell_volume                     2175.1(8)
_computing_cell_refinement       EvalCCD
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_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  0.1048
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30409
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0670P)²+1.3643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                2956
_reflns_number_total             3810
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om7006612-file002.cif
_cod_data_source_block           sd234_compound_3b
_cod_original_cell_volume        2175.0(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4073832
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 1.05162(6) 0.53455(8) 0.69296(4) 0.0596(3) Uani 1 1 d .
O1 O 0.64168(16) 0.77430(14) 0.50439(10) 0.0368(4) Uani 1 1 d .
O2 O 0.54561(17) 0.62044(15) 0.53200(10) 0.0396(5) Uani 1 1 d .
O3 O 0.42200(15) 0.58740(16) 0.36930(11) 0.0353(4) Uani 1 1 d .
H3 H 0.437(3) 0.543(3) 0.410(2) 0.059(10) Uiso 1 1 d .
O4 O 0.42444(16) 0.51141(19) 0.21159(13) 0.0458(5) Uani 1 1 d .
H4 H 0.419(3) 0.513(3) 0.259(2) 0.048(9) Uiso 1 1 d .
O5 O 0.51989(19) 0.59653(18) 0.10177(14) 0.0564(6) Uani 1 1 d .
O6 O 0.67375(17) 0.47227(16) 0.13752(11) 0.0429(5) Uani 1 1 d .
F1 F 0.48379(15) 0.88162(13) 0.36413(10) 0.0499(4) Uani 1 1 d .
F2 F 0.35071(15) 0.80092(16) 0.40932(11) 0.0558(5) Uani 1 1 d .
F3 F 0.34634(15) 0.77653(15) 0.28023(10) 0.0562(5) Uani 1 1 d .
F4 F 0.45729(18) 0.28926(16) 0.24589(12) 0.0670(6) Uani 1 1 d .
F5 F 0.43843(18) 0.32227(15) 0.11448(10) 0.0630(5) Uani 1 1 d .
F6 F 0.61131(17) 0.27549(13) 0.20376(10) 0.0541(5) Uani 1 1 d .
C1 C 0.6454(3) 0.8786(3) 0.63000(19) 0.0549(8) Uani 1 1 d .
H1A H 0.6906 0.8925 0.6900 0.082 Uiso 1 1 calc R
H1B H 0.5643 0.8513 0.6248 0.082 Uiso 1 1 calc R
H1C H 0.6392 0.9492 0.5978 0.082 Uiso 1 1 calc R
C2 C 0.7091(2) 0.7920(2) 0.59564(15) 0.0398(6) Uani 1 1 d .
H2A H 0.7922 0.8178 0.6025 0.048 Uiso 1 1 calc R
H2B H 0.7142 0.7199 0.6271 0.048 Uiso 1 1 calc R
C3 C 0.5665(2) 0.6879(2) 0.48425(14) 0.0301(5) Uani 1 1 d .
C4 C 0.5014(2) 0.6814(2) 0.38688(14) 0.0300(5) Uani 1 1 d .
C5 C 0.4202(2) 0.7863(2) 0.36008(15) 0.0389(6) Uani 1 1 d .
C6 C 0.5900(2) 0.6744(2) 0.33540(14) 0.0304(5) Uani 1 1 d .
H6A H 0.5445 0.6799 0.2739 0.036 Uiso 1 1 calc R
H6B H 0.6469 0.7390 0.3508 0.036 Uiso 1 1 calc R
C7 C 0.6600(2) 0.5644(2) 0.35304(14) 0.0287(5) Uani 1 1 d .
C8 C 0.7593(2) 0.5559(2) 0.43660(14) 0.0295(5) Uani 1 1 d .
C9 C 0.7638(2) 0.4639(2) 0.49049(16) 0.0346(6) Uani 1 1 d .
H9A H 0.7052 0.4055 0.4729 0.042 Uiso 1 1 calc R
C10 C 0.8534(2) 0.4567(2) 0.57003(16) 0.0401(6) Uani 1 1 d .
H10A H 0.8554 0.3946 0.6069 0.048 Uiso 1 1 calc R
C11 C 0.9391(2) 0.5418(2) 0.59387(15) 0.0381(6) Uani 1 1 d .
C12 C 0.9376(2) 0.6332(2) 0.54172(16) 0.0405(6) Uani 1 1 d .
H12A H 0.9974 0.6906 0.5591 0.049 Uiso 1 1 calc R
C13 C 0.8469(2) 0.6400(2) 0.46323(15) 0.0352(6) Uani 1 1 d .
H13A H 0.8447 0.7030 0.4272 0.042 Uiso 1 1 calc R
C14 C 0.6362(2) 0.4745(2) 0.30109(15) 0.0326(6) Uani 1 1 d .
H14A H 0.6873 0.4106 0.3194 0.039 Uiso 1 1 calc R
C15 C 0.5361(2) 0.4634(2) 0.21587(15) 0.0342(6) Uani 1 1 d .
C16 C 0.5113(3) 0.3369(3) 0.19511(16) 0.0446(7) Uani 1 1 d .
C17 C 0.5742(2) 0.5198(2) 0.14436(15) 0.0346(6) Uani 1 1 d .
C18 C 0.7196(3) 0.5184(3) 0.07191(18) 0.0521(8) Uani 1 1 d .
H18A H 0.6512 0.5311 0.0191 0.062 Uiso 1 1 calc R
H18B H 0.7744 0.4625 0.0592 0.062 Uiso 1 1 calc R
C19 C 0.7852(3) 0.6265(3) 0.0986(2) 0.0677(10) Uani 1 1 d .
H19A H 0.8195 0.6514 0.0550 0.102 Uiso 1 1 calc R
H19B H 0.8502 0.6154 0.1526 0.102 Uiso 1 1 calc R
H19C H 0.7292 0.6843 0.1059 0.102 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'
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'
Cl Cl 0.1484 0.1585 '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
C2 O1 C3 117.42(19)
H3 O3 C4 112(2)
H4 O4 C15 109(2)
C17 O6 C18 116.6(2)
H1A C1 H1B 109.5
H1A C1 H1C 109.5
H1A C1 C2 109.5
H1B C1 H1C 109.5
H1B C1 C2 109.5
H1C C1 C2 109.5
O1 C2 C1 108.8(2)
O1 C2 H2A 109.9
O1 C2 H2B 109.9
C1 C2 H2A 109.9
C1 C2 H2B 109.9
H2A C2 H2B 108.3
O1 C3 O2 127.3(2)
O1 C3 C4 111.5(2)
O2 C3 C4 121.2(2)
O3 C4 C3 108.81(19)
O3 C4 C5 105.52(19)
O3 C4 C6 111.00(19)
C3 C4 C5 108.16(19)
C3 C4 C6 112.84(19)
C5 C4 C6 110.2(2)
F1 C5 F2 107.4(2)
F1 C5 F3 107.1(2)
F1 C5 C4 112.4(2)
F2 C5 F3 107.0(2)
F2 C5 C4 111.6(2)
F3 C5 C4 111.1(2)
C4 C6 H6A 109.5
C4 C6 H6B 109.5
C4 C6 C7 110.91(19)
H6A C6 H6B 108.0
H6A C6 C7 109.5
H6B C6 C7 109.5
C6 C7 C8 116.51(19)
C6 C7 C14 124.6(2)
C8 C7 C14 118.8(2)
C7 C8 C9 120.2(2)
C7 C8 C13 121.2(2)
C9 C8 C13 118.6(2)
C8 C9 H9A 119.5
C8 C9 C10 120.9(2)
H9A C9 C10 119.5
C9 C10 H10A 120.7
C9 C10 C11 118.6(2)
H10A C10 C11 120.7
Cl1 C11 C10 119.3(2)
Cl1 C11 C12 118.9(2)
C10 C11 C12 121.8(2)
C11 C12 H12A 120.5
C11 C12 C13 118.9(2)
H12A C12 C13 120.5
C8 C13 C12 121.2(2)
C8 C13 H13A 119.4
C12 C13 H13A 119.4
C7 C14 H14A 116.4
C7 C14 C15 127.2(2)
H14A C14 C15 116.4
O4 C15 C14 115.8(2)
O4 C15 C16 105.9(2)
O4 C15 C17 106.4(2)
C14 C15 C16 109.0(2)
C14 C15 C17 110.5(2)
C16 C15 C17 109.0(2)
F4 C16 F5 107.4(2)
F4 C16 F6 106.3(2)
F4 C16 C15 111.2(2)
F5 C16 F6 106.7(2)
F5 C16 C15 111.1(2)
F6 C16 C15 113.8(2)
O5 C17 O6 125.5(3)
O5 C17 C15 123.3(2)
O6 C17 C15 111.2(2)
O6 C18 H18A 109.2
O6 C18 H18B 109.2
O6 C18 C19 112.1(2)
H18A C18 H18B 107.9
H18A C18 C19 109.2
H18B C18 C19 109.2
C18 C19 H19A 109.5
C18 C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19B 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C11 1.748(2)
O1 C2 1.481(3)
O1 C3 1.318(3)
O2 C3 1.204(3)
O3 H3 0.83(4)
O3 C4 1.416(3)
O4 H4 0.81(3)
O4 C15 1.406(3)
O5 C17 1.199(3)
O6 C17 1.331(3)
O6 C18 1.467(3)
F1 C5 1.339(3)
F2 C5 1.339(3)
F3 C5 1.335(3)
F4 C16 1.332(3)
F5 C16 1.347(3)
F6 C16 1.346(4)
C1 H1A 0.980
C1 H1B 0.980
C1 H1C 0.980
C1 C2 1.485(4)
C2 H2A 0.990
C2 H2B 0.990
C3 C4 1.552(3)
C4 C5 1.538(3)
C4 C6 1.546(3)
C6 H6A 0.990
C6 H6B 0.990
C6 C7 1.514(3)
C7 C8 1.499(3)
C7 C14 1.339(3)
C8 C9 1.398(4)
C8 C13 1.393(3)
C9 H9A 0.950
C9 C10 1.400(3)
C10 H10A 0.950
C10 C11 1.385(4)
C11 C12 1.380(4)
C12 H12A 0.950
C12 C13 1.393(3)
C13 H13A 0.950
C14 H14A 0.950
C14 C15 1.525(3)
C15 C16 1.539(4)
C15 C17 1.549(4)
C18 H18A 0.990
C18 H18B 0.990
C18 C19 1.482(5)
C19 H19A 0.980
C19 H19B 0.980
C19 H19C 0.980
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.83(4) 2.14(4) 2.907(3) 154(3) 3_666
O3 H3 O2 0.83(4) 2.21(4) 2.651(2) 114(3) .
O4 H4 O3 0.81(3) 2.03(4) 2.779(3) 154(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
C3 O1 C2 C1 -97.2(3)
C2 O1 C3 O2 0.1(4)
C2 O1 C3 C4 179.20(19)
O1 C3 C4 O3 -179.83(18)
O1 C3 C4 C5 -65.7(3)
O1 C3 C4 C6 56.5(3)
O2 C3 C4 O3 -0.7(3)
O2 C3 C4 C5 113.5(3)
O2 C3 C4 C6 -124.4(2)
O3 C4 C5 F1 -172.98(19)
O3 C4 C5 F2 66.3(2)
O3 C4 C5 F3 -53.0(3)
C3 C4 C5 F1 70.7(3)
C3 C4 C5 F2 -50.0(3)
C3 C4 C5 F3 -169.3(2)
C6 C4 C5 F1 -53.1(3)
C6 C4 C5 F2 -173.8(2)
C6 C4 C5 F3 66.9(3)
O3 C4 C6 C7 -56.5(2)
C3 C4 C6 C7 65.9(2)
C5 C4 C6 C7 -173.03(19)
C4 C6 C7 C8 -75.5(2)
C4 C6 C7 C14 101.9(3)
C6 C7 C8 C9 127.6(2)
C6 C7 C8 C13 -50.8(3)
C14 C7 C8 C9 -49.9(3)
C14 C7 C8 C13 131.7(3)
C7 C8 C9 C10 -177.8(2)
C13 C8 C9 C10 0.7(4)
C8 C9 C10 C11 -1.0(4)
C9 C10 C11 Cl1 179.9(2)
C9 C10 C11 C12 0.5(4)
Cl1 C11 C12 C13 -179.09(19)
C10 C11 C12 C13 0.4(4)
C7 C8 C13 C12 178.6(2)
C9 C8 C13 C12 0.1(4)
C11 C12 C13 C8 -0.7(4)
C6 C7 C14 C15 -0.4(4)
C8 C7 C14 C15 176.9(2)
C7 C14 C15 O4 -39.4(4)
C7 C14 C15 C16 -158.7(3)
C7 C14 C15 C17 81.6(3)
O4 C15 C16 F4 -54.4(3)
O4 C15 C16 F5 65.1(3)
O4 C15 C16 F6 -174.4(2)
C14 C15 C16 F4 70.8(3)
C14 C15 C16 F5 -169.6(2)
C14 C15 C16 F6 -49.2(3)
C17 C15 C16 F4 -168.6(2)
C17 C15 C16 F5 -49.0(3)
C17 C15 C16 F6 71.5(3)
C18 O6 C17 O5 -0.2(4)
C18 O6 C17 C15 -179.9(2)
O4 C15 C17 O5 6.3(3)
O4 C15 C17 O6 -174.00(19)
C14 C15 C17 O5 -120.2(3)
C14 C15 C17 O6 59.5(3)
C16 C15 C17 O5 120.1(3)
C16 C15 C17 O6 -60.2(3)
C17 O6 C18 C19 77.9(3)
