#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:49:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180317 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/31/7153158.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_7153158
loop_
_publ_author_name
'Ponomarenko, Maxim V.'
'Lummer, Katrin'
'Fokin, Andrey A.'
'Serguchev, Yurii A.'
'Bassil, Bassem S.'
'Röschenthaler, Gerd-Volker'
_publ_section_title
;
 Preparations of SF5- and CF3-substituted arenes utilizing the
 7-oxabicyclo[2.2.1]hept-2-ene synthones.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8103
_journal_page_last               8112
_journal_paper_doi               10.1039/c3ob41560k
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C11 H12 F3 I O5'
_chemical_formula_weight         408.11
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.274(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7331(12)
_cell_length_b                   11.849(2)
_cell_length_c                   15.250(3)
_cell_measurement_reflns_used    8079
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.09
_cell_measurement_theta_min      2.20
_cell_volume                     1365.4(4)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            71720
_diffrn_reflns_theta_full        33.14
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  0.4474
_exptl_absorpt_correction_T_min  0.2712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         1.323
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0282
_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)+(0.0400P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                4491
_reflns_number_total             5126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41560k.txt
_cod_data_source_block           try
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_cell_volume        1365.5(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153158
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.1167(3) 0.31228(18) 0.01769(13) 0.0209(4) Uani 1 1 d .
H11 H 0.019(4) 0.368(3) 0.002(2) 0.021(7) Uiso 1 1 d .
C2 C 0.2801(4) 0.5417(3) 0.2285(2) 0.0415(7) Uani 1 1 d .
H2A H 0.2353 0.6163 0.2070 0.062 Uiso 1 1 calc R
H2B H 0.4088 0.5397 0.2346 0.062 Uiso 1 1 calc R
H2C H 0.2510 0.5268 0.2869 0.062 Uiso 1 1 calc R
C3 C 0.2231(3) 0.14626(18) 0.00522(12) 0.0188(3) Uani 1 1 d .
H13 H 0.209(3) 0.072(2) -0.0194(17) 0.013(6) Uiso 1 1 d .
C4 C 0.1489(3) 0.2706(2) 0.11485(13) 0.0217(4) Uani 1 1 d .
H14 H 0.038(4) 0.256(3) 0.125(2) 0.031(8) Uiso 1 1 d .
C5 C 0.1517(3) 0.0584(2) 0.14314(13) 0.0226(4) Uani 1 1 d .
C6 C 0.2479(3) 0.3503(2) 0.18505(14) 0.0256(4) Uani 1 1 d .
C7 C 0.2965(3) 0.33992(18) -0.00651(13) 0.0188(3) Uani 1 1 d .
H17 H 0.379(3) 0.374(2) 0.0433(18) 0.012(6) Uiso 1 1 d .
C8 C 0.2425(3) 0.15619(19) 0.10824(13) 0.0202(4) Uani 1 1 d .
H18 H 0.369(4) 0.151(3) 0.137(2) 0.025(7) Uiso 1 1 d .
C9 C 0.3570(2) 0.22008(18) -0.02822(12) 0.0185(3) Uani 1 1 d .
H19 H 0.349(4) 0.207(2) -0.0922(19) 0.017(6) Uiso 1 1 d .
C10 C 0.1980(4) -0.1183(2) 0.21500(17) 0.0319(5) Uani 1 1 d .
H310 H 0.128(5) -0.168(3) 0.168(2) 0.033(9) Uiso 1 1 d .
H210 H 0.296(5) -0.162(3) 0.236(3) 0.040(10) Uiso 1 1 d .
H110 H 0.137(5) -0.100(3) 0.255(3) 0.045(10) Uiso 1 1 d .
C11 C 0.2771(3) 0.4198(2) -0.08440(15) 0.0266(4) Uani 1 1 d .
O1 O 0.1987(2) 0.45599(17) 0.16455(13) 0.0333(4) Uani 1 1 d .
O2 O -0.0066(2) 0.04930(17) 0.13444(13) 0.0316(4) Uani 1 1 d .
O3 O 0.2692(2) -0.01743(16) 0.18185(11) 0.0271(3) Uani 1 1 d .
O4 O 0.3558(3) 0.32158(18) 0.25016(12) 0.0413(5) Uani 1 1 d .
O5 O 0.06447(19) 0.20934(15) -0.03006(10) 0.0231(3) Uani 1 1 d .
F1 F 0.2214(3) 0.52144(14) -0.06340(11) 0.0398(4) Uani 1 1 d .
F2 F 0.4311(2) 0.43625(15) -0.10909(11) 0.0374(4) Uani 1 1 d .
F3 F 0.1611(2) 0.38393(15) -0.15681(9) 0.0363(4) Uani 1 1 d .
I1 I 0.629125(16) 0.181621(12) 0.026129(9) 0.02268(5) Uani 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'
I I -0.4742 1.8119 '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
O5 C1 C4 100.81(17)
O5 C1 C7 103.26(15)
C4 C1 C7 109.25(15)
O5 C3 C9 99.35(17)
O5 C3 C8 103.31(15)
C9 C3 C8 111.69(16)
C6 C4 C1 116.0(2)
C6 C4 C8 114.82(18)
C1 C4 C8 101.59(15)
O2 C5 O3 124.9(2)
O2 C5 C8 124.5(2)
O3 C5 C8 110.57(18)
O4 C6 O1 125.1(2)
O4 C6 C4 124.6(2)
O1 C6 C4 110.26(19)
C11 C7 C1 112.25(17)
C11 C7 C9 113.07(17)
C1 C7 C9 100.60(17)
C5 C8 C3 110.31(17)
C5 C8 C4 112.97(18)
C3 C8 C4 100.75(16)
C3 C9 C7 101.35(16)
C3 C9 I1 115.47(13)
C7 C9 I1 115.34(13)
F3 C11 F2 107.16(19)
F3 C11 F1 106.85(18)
F2 C11 F1 106.7(2)
F3 C11 C7 112.9(2)
F2 C11 C7 111.70(18)
F1 C11 C7 111.12(18)
C6 O1 C2 116.1(2)
C5 O3 C10 116.00(19)
C1 O5 C3 97.25(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O5 1.434(2)
C1 C4 1.531(3)
C1 C7 1.547(3)
C2 O1 1.455(3)
C3 O5 1.440(2)
C3 C9 1.524(3)
C3 C8 1.551(3)
C4 C6 1.508(3)
C4 C8 1.550(3)
C5 O2 1.207(3)
C5 O3 1.324(3)
C5 C8 1.509(3)
C6 O4 1.202(3)
C6 O1 1.327(3)
C7 C11 1.501(3)
C7 C9 1.553(3)
C9 I1 2.1407(18)
C10 O3 1.451(3)
C11 F3 1.336(3)
C11 F2 1.337(3)
C11 F1 1.341(3)
