#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:40:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178476 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/97/4029767.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_4029767
loop_
_publ_author_name
'Petrov, Viacheslav A.'
'Marshall, Will'
_publ_section_title
;
 Acid catalyzed cyclodimerization of
 2,2-bis(trifluoromethyl)-4-alkoxy-oxetanes and -thietanes. Synthesis of
 2,2,6,6-tetrakis(trifluoromethyl)-4,8-dialkoxy-1,5-dioxocanes and
 3,3,7,7-tetrakis(trifluoromethyl)-9-oxa-2,6-dithia-bicyclo[3.3.1]nonane.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              46
_journal_paper_doi               10.3762/bjoc.6.46
_journal_volume                  6
_journal_year                    2010
_chemical_formula_sum            'C16 H20 F12 O4'
_chemical_formula_weight         504.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.015(6)
_cell_angle_beta                 105.203(6)
_cell_angle_gamma                92.977(6)
_cell_formula_units_Z            1
_cell_length_a                   5.564(2)
_cell_length_b                   9.647(4)
_cell_length_c                   9.926(4)
_cell_measurement_reflns_used    1074
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.10
_cell_measurement_theta_min      2.74
_cell_volume                     503.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5386
_diffrn_reflns_theta_full        28.02
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       oval.block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0607P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1263
_reflns_number_gt                1382
_reflns_number_total             2404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-6-46-S2.cif
_cod_data_source_block           08131
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        503.7(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029767
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O -0.1806(3) 0.87971(16) 0.06071(15) 0.0311(4) Uani 1 1 d
F1 F -0.0017(3) 1.07033(15) 0.30970(15) 0.0524(4) Uani 1 1 d
C1 C 0.0662(4) 0.8771(2) 0.1451(2) 0.0286(5) Uani 1 1 d
O2 O -0.4530(3) 0.80602(15) -0.16051(16) 0.0328(4) Uani 1 1 d
F2 F 0.2693(3) 0.93587(17) 0.39272(15) 0.0557(4) Uani 1 1 d
C2 C -0.2287(4) 0.8877(2) -0.0887(2) 0.0290(5) Uani 1 1 d
F3 F -0.1202(3) 0.86556(17) 0.33499(15) 0.0538(4) Uani 1 1 d
C3 C -0.2722(4) 1.0393(2) -0.1078(3) 0.0304(5) Uani 1 1 d
F4 F 0.3472(3) 0.70841(15) 0.21845(16) 0.0571(5) Uani 1 1 d
C4 C 0.0526(4) 0.9369(3) 0.2969(3) 0.0371(6) Uani 1 1 d
F5 F -0.0447(3) 0.63970(15) 0.16501(17) 0.0546(4) Uani 1 1 d
C5 C 0.1234(4) 0.7221(3) 0.1340(3) 0.0374(6) Uani 1 1 d
F6 F 0.1258(3) 0.66632(14) 0.00119(15) 0.0455(4) Uani 1 1 d
C6 C -0.4417(5) 0.6556(3) -0.1895(3) 0.0383(6) Uani 1 1 d
C7 C -0.6737(5) 0.5923(3) -0.3061(3) 0.0398(6) Uani 1 1 d
C8 C -0.6925(7) 0.6464(4) -0.4420(3) 0.0544(8) Uani 1 1 d
H3 H -0.302(4) 1.097(2) -0.022(3) 0.032(6) Uiso 1 1 d
H6' H -0.422(5) 0.617(3) -0.103(3) 0.050(7) Uiso 1 1 d
H7 H -0.826(5) 0.620(3) -0.267(3) 0.051(7) Uiso 1 1 d
H8' H -0.554(5) 0.630(3) -0.478(3) 0.055(9) Uiso 1 1 d
H3' H -0.424(4) 1.032(2) -0.185(3) 0.038(6) Uiso 1 1 d
H6 H -0.290(5) 0.638(2) -0.220(3) 0.042(7) Uiso 1 1 d
H7' H -0.665(5) 0.494(3) -0.326(3) 0.045(7) Uiso 1 1 d
H8 H -0.835(6) 0.596(3) -0.510(3) 0.072(10) Uiso 1 1 d
H8" H -0.706(6) 0.753(4) -0.429(3) 0.077(10) Uiso 1 1 d
H2 H -0.082(4) 0.852(2) -0.124(2) 0.029(6) Uiso 1 1 d
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'
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
C1 O1 C2 120.53(16) . .
O1 C1 C3 116.09(17) . 2_575
O1 C1 C5 108.18(17) . .
C3 C1 C5 108.44(18) 2_575 .
O1 C1 C4 103.27(17) . .
C3 C1 C4 111.06(19) 2_575 .
C5 C1 C4 109.59(17) . .
C2 O2 C6 116.08(17) . .
O2 C2 O1 107.17(16) . .
O2 C2 C3 105.92(17) . .
O1 C2 C3 109.74(19) . .
C1 C3 C2 116.69(19) 2_575 .
F3 C4 F2 107.07(19) . .
F3 C4 F1 106.52(19) . .
F2 C4 F1 106.9(2) . .
F3 C4 C1 113.1(2) . .
F2 C4 C1 111.54(19) . .
F1 C4 C1 111.28(17) . .
F5 C5 F4 107.42(18) . .
F5 C5 F6 106.2(2) . .
F4 C5 F6 106.50(19) . .
F5 C5 C1 113.4(2) . .
F4 C5 C1 112.42(19) . .
F6 C5 C1 110.52(18) . .
O2 C6 C7 107.24(19) . .
C6 C7 C8 112.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.413(2) .
O1 C2 1.453(3) .
F1 C4 1.330(3) .
C1 C3 1.527(3) 2_575
C1 C5 1.536(3) .
C1 C4 1.540(3) .
O2 C2 1.387(3) .
O2 C6 1.437(3) .
F2 C4 1.327(2) .
C2 C3 1.530(3) .
F3 C4 1.324(3) .
C3 C1 1.527(3) 2_575
F4 C5 1.333(3) .
F5 C5 1.327(3) .
C5 F6 1.338(3) .
C6 C7 1.506(3) .
C7 C8 1.510(4) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 O1 C1 C3 32.9(3) . 2_575
C2 O1 C1 C5 -89.2(2) . .
C2 O1 C1 C4 154.72(18) . .
C6 O2 C2 O1 -78.4(2) . .
C6 O2 C2 C3 164.5(2) . .
C1 O1 C2 O2 143.75(18) . .
C1 O1 C2 C3 -101.7(2) . .
O2 C2 C3 C1 -135.6(2) . 2_575
O1 C2 C3 C1 109.0(2) . 2_575
O1 C1 C4 F3 56.3(2) . .
C3 C1 C4 F3 -178.65(17) 2_575 .
C5 C1 C4 F3 -58.9(2) . .
O1 C1 C4 F2 177.04(17) . .
C3 C1 C4 F2 -57.9(2) 2_575 .
C5 C1 C4 F2 61.9(2) . .
O1 C1 C4 F1 -63.6(2) . .
C3 C1 C4 F1 61.5(2) 2_575 .
C5 C1 C4 F1 -178.75(18) . .
O1 C1 C5 F5 -53.5(2) . .
C3 C1 C5 F5 179.79(19) 2_575 .
C4 C1 C5 F5 58.4(2) . .
O1 C1 C5 F4 -175.62(18) . .
C3 C1 C5 F4 57.7(2) 2_575 .
C4 C1 C5 F4 -63.7(2) . .
O1 C1 C5 F6 65.5(2) . .
C3 C1 C5 F6 -61.2(2) 2_575 .
C4 C1 C5 F6 177.46(17) . .
C2 O2 C6 C7 -161.5(2) . .
O2 C6 C7 C8 60.7(3) . .
