#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:01:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180219 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/05/7110571.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110571
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Brooke, Gerald M.'
'Holling, Darren'
'Kenwright, Alan M.'
_publ_section_title
;
 Pyrolysis reactions of 4-nonafluorobiphenyl prop-2-enyl ether: a
 remarkable rearrangement reaction
;
_journal_issue                   16
_journal_name_full               'Chemical Communications'
_journal_page_first              1549
_journal_paper_doi               10.1039/a903209f
_journal_year                    1999
_chemical_formula_sum            'C15 H5 F9 O'
_chemical_formula_weight         372.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.413(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.4461(15)
_cell_length_b                   11.0332(14)
_cell_length_c                   19.2485(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      22
_cell_volume                     2709.4(5)
_computing_cell_refinement       AFC/MSC
_computing_data_collection       AFC/MSC
_computing_data_reduction        TEXSAN
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.854
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device_type  'Rigaku AFC6S 4-circle diffractometer'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5009
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         3.46
_diffrn_standards_decay_%        2.5
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.812
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8667
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'T_max,min from psi-scans'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0462
_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)+(0.0274P)²+3.5829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                3238
_reflns_number_total             4172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            903209fsup1.cif
_cod_data_source_block           (16)
_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_sg_symbol_H-M      P2/c
_cod_database_code               7110571
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
O1 O 0.56889(19) 0.9383(2) 0.19298(13) 0.0375(6) Uani 1 1 d
F2 F 0.39724(16) 1.1097(2) 0.15325(13) 0.0537(6) Uani 1 1 d
F5 F 0.72666(18) 1.32607(19) 0.01231(11) 0.0468(6) Uani 1 1 d
F6 F 0.70319(17) 1.09215(18) -0.00818(10) 0.0392(5) Uani 1 1 d
F7A F 0.75950(14) 1.07567(18) 0.24019(9) 0.0337(5) Uani 1 1 d
F12 F 0.90406(14) 0.95964(17) 0.18066(11) 0.0357(5) Uani 1 1 d
F13 F 0.94627(15) 0.72182(19) 0.17417(11) 0.0393(5) Uani 1 1 d
F14 F 0.79598(16) 0.56809(17) 0.09540(11) 0.0361(5) Uani 1 1 d
F15 F 0.59998(15) 0.65171(18) 0.02456(11) 0.0410(5) Uani 1 1 d
F16 F 0.55589(14) 0.88929(18) 0.03093(11) 0.0390(5) Uani 1 1 d
C1 C 0.5772(3) 1.0444(3) 0.17954(17) 0.0292(8) Uani 1 1 d
C2 C 0.4978(3) 1.1382(3) 0.16157(19) 0.0330(8) Uani 1 1 d
C3 C 0.5367(3) 1.2484(4) 0.15993(19) 0.0354(9) Uani 1 1 d
H3 H 0.494(3) 1.325(4) 0.147(2) 0.046(11) Uiso 1 1 d
C3A C 0.6539(3) 1.2445(3) 0.17740(19) 0.0287(7) Uani 1 1 d
H3A H 0.686(2) 1.277(3) 0.2288(18) 0.027(9) Uiso 1 1 d
C4 C 0.6957(3) 1.3215(3) 0.1272(2) 0.0337(8) Uani 1 1 d
H41 H 0.669(3) 1.405(4) 0.1252(19) 0.039(10) Uiso 1 1 d
H42 H 0.772(3) 1.321(4) 0.148(2) 0.051(12) Uiso 1 1 d
C5 C 0.6679(3) 1.2693(3) 0.05117(19) 0.0318(8) Uani 1 1 d
H5 H 0.599(3) 1.283(4) 0.028(2) 0.039(11) Uiso 1 1 d
C6 C 0.6929(3) 1.1358(3) 0.05485(17) 0.0282(8) Uani 1 1 d
C7 C 0.7033(2) 1.0635(3) 0.11016(17) 0.0238(7) Uani 1 1 d
C7A C 0.6784(2) 1.1074(3) 0.17710(16) 0.0251(7) Uani 1 1 d
C11 C 0.7278(2) 0.9316(3) 0.10663(16) 0.0240(7) Uani 1 1 d
C12 C 0.8276(2) 0.8855(3) 0.14209(17) 0.0259(7) Uani 1 1 d
C13 C 0.8502(2) 0.7643(3) 0.13895(17) 0.0273(7) Uani 1 1 d
C14 C 0.7741(3) 0.6855(3) 0.09949(17) 0.0271(7) Uani 1 1 d
C15 C 0.6748(3) 0.7284(3) 0.06366(17) 0.0283(7) Uani 1 1 d
C16 C 0.6534(2) 0.8500(3) 0.06743(17) 0.0268(7) Uani 1 1 d
O1' O 0.38493(18) 0.4422(2) 0.20451(13) 0.0381(6) Uani 1 1 d
F2' F 0.49403(16) 0.6243(2) 0.14586(12) 0.0525(6) Uani 1 1 d
F5' F 0.03037(16) 0.83354(18) 0.06292(11) 0.0411(5) Uani 1 1 d
F6' F 0.03451(16) 0.60909(18) 0.02749(11) 0.0452(6) Uani 1 1 d
F7A' F 0.24148(15) 0.55865(18) 0.26266(9) 0.0334(5) Uani 1 1 d
F12' F 0.00977(16) 0.46256(19) 0.18381(12) 0.0441(5) Uani 1 1 d
F13' F -0.04680(18) 0.2274(2) 0.16878(14) 0.0567(7) Uani 1 1 d
F14' F 0.04940(18) 0.07242(19) 0.10104(14) 0.0544(6) Uani 1 1 d
F15' F 0.19847(17) 0.15466(19) 0.04541(11) 0.0466(6) Uani 1 1 d
F16' F 0.25529(15) 0.39014(19) 0.06039(10) 0.0373(5) Uani 1 1 d
C1' C 0.3578(2) 0.5467(3) 0.19166(16) 0.0290(8) Uani 1 1 d
C2' C 0.4096(3) 0.6463(4) 0.16700(18) 0.0339(9) Uani 1 1 d
C3' C 0.3684(3) 0.7523(4) 0.17334(18) 0.0319(8) Uani 1 1 d
H3' H 0.392(2) 0.830(3) 0.1637(17) 0.025(9) Uiso 1 1 d
C3A' C 0.2783(3) 0.7402(3) 0.20316(17) 0.0279(7) Uani 1 1 d
H3A' H 0.307(2) 0.759(3) 0.2572(17) 0.022(8) Uiso 1 1 d
C4' C 0.1835(3) 0.8191(3) 0.16666(19) 0.0316(8) Uani 1 1 d
H41' H 0.132(3) 0.813(3) 0.1943(18) 0.027(9) Uiso 1 1 d
H42' H 0.203(2) 0.902(3) 0.1655(17) 0.024(9) Uiso 1 1 d
C5' C 0.1287(3) 0.7791(3) 0.08902(18) 0.0290(8) Uani 1 1 d
H5' H 0.166(3) 0.802(3) 0.0577(18) 0.025(9) Uiso 1 1 d
C6' C 0.1128(2) 0.6450(3) 0.08623(17) 0.0270(7) Uani 1 1 d
C7' C 0.1655(2) 0.5640(3) 0.13404(16) 0.0218(7) Uani 1 1 d
C7A' C 0.2571(2) 0.6023(3) 0.19869(15) 0.0240(7) Uani 1 1 d
C11' C 0.1378(2) 0.4325(3) 0.12569(16) 0.0238(7) Uani 1 1 d
C12' C 0.0595(3) 0.3871(3) 0.15179(18) 0.0305(8) Uani 1 1 d
C13' C 0.0304(3) 0.2672(3) 0.1441(2) 0.0365(9) Uani 1 1 d
C14' C 0.0779(3) 0.1895(3) 0.1091(2) 0.0369(9) Uani 1 1 d
C15' C 0.1548(3) 0.2305(3) 0.08159(18) 0.0317(8) Uani 1 1 d
C16' C 0.1827(2) 0.3510(3) 0.08984(16) 0.0271(7) 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.075
1.00 0.00 0.00 0.075
0.00 1.00 0.00 0.175
0.00 -1.00 0.00 0.175
0.00 0.00 1.00 0.040
0.00 0.00 -1.00 0.040
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C2 129.1(3)
O1 C1 C7A 125.7(3)
C2 C1 C7A 105.2(3)
C3 C2 F2 126.8(3)
C3 C2 C1 113.1(3)
F2 C2 C1 119.9(3)
C2 C3 C3A 111.2(3)
C2 C3 H3 125(2)
C3A C3 H3 123(2)
C3 C3A C4 114.4(3)
C3 C3A C7A 103.7(3)
C4 C3A C7A 114.9(3)
C3 C3A H3A 107.8(18)
C4 C3A H3A 106.7(19)
C7A C3A H3A 109.1(19)
C5 C4 C3A 112.0(3)
C5 C4 H41 110(2)
C3A C4 H41 110(2)
C5 C4 H42 107(2)
C3A C4 H42 107(2)
H41 C4 H42 110(3)
F5 C5 C4 109.9(3)
F5 C5 C6 108.0(3)
C4 C5 C6 110.2(3)
F5 C5 H5 109(2)
C4 C5 H5 108(2)
C6 C5 H5 112(3)
C7 C6 F6 120.0(3)
C7 C6 C5 127.0(3)
F6 C6 C5 113.0(3)
C6 C7 C11 121.8(3)
C6 C7 C7A 120.3(3)
C11 C7 C7A 117.5(3)
F7A C7A C7 109.8(2)
F7A C7A C1 108.3(2)
C7 C7A C1 108.5(3)
F7A C7A C3A 110.5(3)
C7 C7A C3A 114.9(3)
C1 C7A C3A 104.5(3)
C16 C11 C12 116.7(3)
C16 C11 C7 121.8(3)
C12 C11 C7 121.5(3)
F12 C12 C13 118.4(3)
F12 C12 C11 120.0(3)
C13 C12 C11 121.6(3)
F13 C13 C14 119.2(3)
F13 C13 C12 120.6(3)
C14 C13 C12 120.2(3)
F14 C14 C13 120.4(3)
F14 C14 C15 120.0(3)
C13 C14 C15 119.5(3)
F15 C15 C14 119.8(3)
F15 C15 C16 120.6(3)
C14 C15 C16 119.6(3)
F16 C16 C15 118.1(3)
F16 C16 C11 119.5(3)
C15 C16 C11 122.4(3)
O1' C1' C2' 129.8(3)
O1' C1' C7A' 125.6(3)
C2' C1' C7A' 104.7(3)
C3' C2' F2' 127.5(3)
C3' C2' C1' 112.4(3)
F2' C2' C1' 119.9(3)
C2' C3' C3A' 111.8(3)
C2' C3' H3' 128(2)
C3A' C3' H3' 120(2)
C3' C3A' C4' 115.7(3)
C3' C3A' C7A' 102.8(3)
C4' C3A' C7A' 115.2(3)
C3' C3A' H3A' 106.6(17)
C4' C3A' H3A' 110.2(18)
C7A' C3A' H3A' 105.5(18)
C5' C4' C3A' 111.5(3)
C5' C4' H41' 107.7(19)
C3A' C4' H41' 109.7(19)
C5' C4' H42' 108.0(19)
C3A' C4' H42' 111(2)
H41' C4' H42' 109(3)
F5' C5' C6' 107.8(3)
F5' C5' C4' 110.0(3)
C6' C5' C4' 110.1(3)
F5' C5' H5' 107(2)
C6' C5' H5' 110(2)
C4' C5' H5' 112(2)
C7' C6' F6' 119.6(3)
C7' C6' C5' 127.4(3)
F6' C6' C5' 112.9(3)
C6' C7' C11' 121.5(3)
C6' C7' C7A' 120.3(3)
C11' C7' C7A' 118.2(3)
F7A' C7A' C7' 108.6(2)
F7A' C7A' C1' 108.8(3)
C7' C7A' C1' 109.2(2)
F7A' C7A' C3A' 111.5(3)
C7' C7A' C3A' 114.2(3)
C1' C7A' C3A' 104.3(3)
C16' C11' C12' 116.4(3)
C16' C11' C7' 123.5(3)
C12' C11' C7' 120.1(3)
F12' C12' C13' 118.9(3)
F12' C12' C11' 119.2(3)
C13' C12' C11' 121.9(3)
F13' C13' C14' 120.2(3)
F13' C13' C12' 120.1(3)
C14' C13' C12' 119.7(3)
F14' C14' C13' 120.0(3)
F14' C14' C15' 119.5(3)
C13' C14' C15' 120.5(3)
F15' C15' C16' 121.0(3)
F15' C15' C14' 120.1(3)
C16' C15' C14' 118.9(3)
F16' C16' C15' 117.9(3)
F16' C16' C11' 119.4(3)
C15' C16' C11' 122.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.212(4)
F2 C2 1.347(4)
F5 C5 1.396(4)
F6 C6 1.353(4)
F7A C7A 1.396(3)
F12 C12 1.339(4)
F13 C13 1.340(4)
F14 C14 1.336(4)
F15 C15 1.348(4)
F16 C16 1.348(4)
C1 C2 1.449(5)
C1 C7A 1.542(5)
C2 C3 1.328(5)
C3 C3A 1.505(5)
C3 H3 1.00(4)
C3A C4 1.522(5)
C3A C7A 1.548(5)
C3A H3A 1.01(3)
C4 C5 1.505(5)
C4 H41 0.99(4)
C4 H42 0.97(4)
C5 C6 1.507(5)
C5 H5 0.91(4)
C6 C7 1.303(4)
C7 C11 1.498(5)
C7 C7A 1.510(4)
C11 C16 1.380(5)
C11 C12 1.395(4)
C12 C13 1.377(5)
C13 C14 1.375(5)
C14 C15 1.378(5)
C15 C16 1.379(5)
O1' C1' 1.211(4)
F2' C2' 1.343(4)
F5' C5' 1.393(4)
F6' C6' 1.339(3)
F7A' C7A' 1.399(3)
F12' C12' 1.335(4)
F13' C13' 1.344(4)
F14' C14' 1.343(4)
F15' C15' 1.338(4)
F16' C16' 1.346(4)
C1' C2' 1.459(5)
C1' C7A' 1.531(5)
C2' C3' 1.316(5)
C3' C3A' 1.503(5)
C3' H3' 0.95(3)
C3A' C4' 1.519(5)
C3A' C7A' 1.545(5)
C3A' H3A' 1.01(3)
C4' C5' 1.508(4)
C4' H41' 1.00(3)
C4' H42' 0.95(4)
C5' C6' 1.493(5)
C5' H5' 0.93(3)
C6' C7' 1.318(4)
C7' C11' 1.494(4)
C7' C7A' 1.508(4)
C11' C16' 1.382(5)
C11' C12' 1.395(5)
C12' C13' 1.374(5)
C13' C14' 1.367(5)
C14' C15' 1.378(5)
C15' C16' 1.377(5)
