#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:10:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178711 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/22/4082210.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_4082210
loop_
_publ_author_name
'Kaplan, Peter T.'
'Xu, Long'
'Chen, Bo'
'McGarry, Katherine R.'
'Yu, Siqi'
'Wang, Huan'
'Vicic, David A.'
_publ_section_title
;
 Mild, Safe, and Versatile Reagents for (CF2)nTransfer and the
 Construction of Fluoroalkyl-Containing Rings
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              7552
_journal_paper_doi               10.1021/om401016k
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C30 H18 F12'
_chemical_formula_weight         606.44
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5726(7)
_cell_length_b                   29.691(3)
_cell_length_c                   5.6935(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1280.1(2)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            19493
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.020
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0341
_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)+(0.0399P)²+0.4281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.001
_reflns_number_gt                2458
_reflns_number_total             2612
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om401016k_si_002.cif
_cod_data_source_block           Compound19
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4082210
#BEGIN Tags that were not found in dictionaries:
_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   0.928
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 0.2824(2) 0.08182(5) -0.2361(3) 0.0381(4) Uani 1 1 d . U
F2 F 0.4121(2) 0.06241(5) 0.0912(3) 0.0347(4) Uani 1 1 d . U
F3 F -0.03283(19) 0.08054(5) -0.0293(3) 0.0359(4) Uani 1 1 d . U
F4 F 0.0836(2) 0.06914(5) 0.3148(3) 0.0317(4) Uani 1 1 d . U
F5 F 0.1874(2) -0.01035(5) 0.2168(3) 0.0374(4) Uani 1 1 d . U
F6 F 0.1706(2) -0.00072(5) -0.1609(3) 0.0426(4) Uani 1 1 d . U
C1 C 0.2737(3) 0.08556(8) 0.0010(4) 0.0253(5) Uani 1 1 d . U
C2 C 0.1036(3) 0.06136(8) 0.0834(4) 0.0239(5) Uani 1 1 d . U
C3 C 0.0954(3) 0.00957(8) 0.0449(4) 0.0262(5) Uani 1 1 d . U
C4 C 0.2788(3) 0.13427(8) 0.0732(4) 0.0216(5) Uani 1 1 d . U
C5 C 0.1989(3) 0.16698(8) -0.0658(4) 0.0241(5) Uani 1 1 d . U
H5A H 0.1433 0.1587 -0.2090 0.029 Uiso 1 1 calc R U
C6 C 0.2002(3) 0.21151(8) 0.0041(4) 0.0228(5) Uani 1 1 d . U
H6A H 0.1451 0.2335 -0.0927 0.027 Uiso 1 1 calc R U
C7 C 0.2807(3) 0.22523(7) 0.2143(4) 0.0187(5) Uani 1 1 d . U
C8 C 0.3609(3) 0.19160(8) 0.3503(4) 0.0227(5) Uani 1 1 d . U
H8A H 0.4178 0.1997 0.4928 0.027 Uiso 1 1 calc R U
C9 C 0.3589(3) 0.14677(8) 0.2817(4) 0.0235(5) Uani 1 1 d . U
H9A H 0.4128 0.1246 0.3782 0.028 Uiso 1 1 calc R U
C10 C 0.2797(3) 0.27324(7) 0.2908(4) 0.0187(4) Uani 1 1 d . U
C11 C 0.1999(3) 0.30684(8) 0.1544(4) 0.0237(5) Uani 1 1 d . U
H11A H 0.1442 0.2988 0.0108 0.028 Uiso 1 1 calc R U
C12 C 0.2008(3) 0.35154(8) 0.2250(5) 0.0261(5) Uani 1 1 d . U
H12A H 0.1466 0.3737 0.1288 0.031 Uiso 1 1 calc R U
C13 C 0.2798(3) 0.36429(8) 0.4342(5) 0.0255(5) Uani 1 1 d . U
H13A H 0.2801 0.3949 0.4823 0.031 Uiso 1 1 calc R U
C14 C 0.3586(3) 0.33135(8) 0.5720(4) 0.0261(5) Uani 1 1 d . U
H14A H 0.4132 0.3395 0.7160 0.031 Uiso 1 1 calc R U
C15 C 0.3581(3) 0.28673(8) 0.5014(4) 0.0228(5) Uani 1 1 d . U
H15A H 0.4125 0.2647 0.5987 0.027 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'
F F 0.0171 0.0103 '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
F2 C1 F1 107.4(2) . .
F2 C1 C4 111.4(2) . .
F1 C1 C4 110.4(2) . .
F2 C1 C2 107.06(18) . .
F1 C1 C2 107.7(2) . .
C4 C1 C2 112.6(2) . .
F3 C2 F4 108.0(2) . .
F3 C2 C1 107.37(18) . .
F4 C2 C1 108.1(2) . .
F3 C2 C3 108.72(19) . .
F4 C2 C3 107.7(2) . .
C1 C2 C3 116.7(2) . .
F6 C3 F5 108.5(2) . .
F6 C3 C3 108.21(15) . 2
F5 C3 C3 108.82(17) . 2
F6 C3 C2 109.4(2) . .
F5 C3 C2 108.22(19) . .
C3 C3 C2 113.6(2) 2 .
C9 C4 C5 119.4(2) . .
C9 C4 C1 120.2(2) . .
C5 C4 C1 120.3(2) . .
C6 C5 C4 120.1(2) . .
C6 C5 H5A 120.0 . .
C4 C5 H5A 120.0 . .
C5 C6 C7 121.8(2) . .
C5 C6 H6A 119.1 . .
C7 C6 H6A 119.1 . .
C8 C7 C6 116.9(2) . .
C8 C7 C10 121.5(2) . .
C6 C7 C10 121.6(2) . .
C9 C8 C7 121.6(2) . .
C9 C8 H8A 119.2 . .
C7 C8 H8A 119.2 . .
C4 C9 C8 120.2(2) . .
C4 C9 H9A 119.9 . .
C8 C9 H9A 119.9 . .
C15 C10 C11 117.1(2) . .
C15 C10 C7 121.5(2) . .
C11 C10 C7 121.4(2) . .
C12 C11 C10 121.2(2) . .
C12 C11 H11A 119.4 . .
C10 C11 H11A 119.4 . .
C13 C12 C11 120.9(2) . .
C13 C12 H12A 119.6 . .
C11 C12 H12A 119.6 . .
C12 C13 C14 118.6(2) . .
C12 C13 H13A 120.7 . .
C14 C13 H13A 120.7 . .
C15 C14 C13 120.6(2) . .
C15 C14 H14A 119.7 . .
C13 C14 H14A 119.7 . .
C14 C15 C10 121.6(2) . .
C14 C15 H15A 119.2 . .
C10 C15 H15A 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.356(3) .
F2 C1 1.354(3) .
F3 C2 1.343(3) .
F4 C2 1.346(3) .
F5 C3 1.340(3) .
F6 C3 1.338(3) .
C1 C4 1.504(3) .
C1 C2 1.547(3) .
C2 C3 1.555(3) .
C3 C3 1.552(5) 2
C4 C9 1.384(3) .
C4 C5 1.391(3) .
C5 C6 1.381(3) .
C5 H5A 0.9500 .
C6 C7 1.403(3) .
C6 H6A 0.9500 .
C7 C8 1.402(3) .
C7 C10 1.490(3) .
C8 C9 1.387(3) .
C8 H8A 0.9500 .
C9 H9A 0.9500 .
C10 C15 1.397(3) .
C10 C11 1.401(3) .
C11 C12 1.387(3) .
C11 H11A 0.9500 .
C12 C13 1.385(4) .
C12 H12A 0.9500 .
C13 C14 1.389(3) .
C13 H13A 0.9500 .
C14 C15 1.384(3) .
C14 H14A 0.9500 .
C15 H15A 0.9500 .
