#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/05/7110570.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_7110570
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
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                 93.05(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.242(3)
_cell_length_b                   6.219(2)
_cell_length_c                   20.254(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34
_cell_measurement_theta_min      22
_cell_volume                     2671.8(10)
_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 0.869
_diffrn_measured_fraction_theta_max 0.869
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3080
_diffrn_reflns_theta_full        74.92
_diffrn_reflns_theta_max         74.92
_diffrn_reflns_theta_min         4.17
_diffrn_standards_decay_%        3.5
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.838
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'ψ-curves of 3 reflections (108 scans) measured'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.00042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0367
_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)+(0.0533P)²+2.5305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                1926
_reflns_number_total             2394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            903209fsup1.cif
_cod_data_source_block           (12)
_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        2671.8(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7110570
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
F2 F 0.44755(6) 0.3006(2) 0.15782(6) 0.0320(3) Uani 1 1 d
F4 F 0.24241(6) 0.2564(2) 0.23720(6) 0.0325(3) Uani 1 1 d
F5 F 0.20409(6) 0.1326(2) 0.11680(7) 0.0341(3) Uani 1 1 d
F7 F 0.37933(6) 0.5653(2) 0.06426(6) 0.0339(3) Uani 1 1 d
F32 F 0.40694(7) 0.6938(2) 0.21971(6) 0.0378(4) Uani 1 1 d
F33 F 0.46869(7) 0.8264(2) 0.33293(7) 0.0417(4) Uani 1 1 d
F34 F 0.47146(7) 0.5707(3) 0.44127(7) 0.0460(4) Uani 1 1 d
F35 F 0.41176(8) 0.1843(3) 0.43740(7) 0.0519(5) Uani 1 1 d
F36 F 0.34903(7) 0.0527(2) 0.32518(7) 0.0398(4) Uani 1 1 d
O O 0.25228(8) 0.4664(3) 0.04757(8) 0.0357(4) Uani 1 1 d
C1 C 0.37534(10) 0.0401(4) 0.10632(10) 0.0255(5) Uani 1 1 d
H1 H 0.4061(11) -0.066(4) 0.1180(11) 0.020(6) Uiso 1 1 d
C2 C 0.38456(9) 0.2576(4) 0.14486(10) 0.0250(5) Uani 1 1 d
C3 C 0.34721(10) 0.2937(4) 0.20555(10) 0.0244(5) Uani 1 1 d
C4 C 0.28703(10) 0.2450(4) 0.19313(10) 0.0254(5) Uani 1 1 d
C5 C 0.26777(10) 0.1674(4) 0.12424(10) 0.0267(5) Uani 1 1 d
C6 C 0.28781(10) 0.3506(4) 0.07856(10) 0.0259(5) Uani 1 1 d
C7 C 0.35957(10) 0.3631(4) 0.07960(10) 0.0255(5) Uani 1 1 d
C8 C 0.38386(11) 0.1686(4) 0.04163(11) 0.0291(5) Uani 1 1 d
H81 H 0.3608(11) 0.125(4) 0.0007(12) 0.026(6) Uiso 1 1 d
H82 H 0.4275(12) 0.187(4) 0.0335(12) 0.032(7) Uiso 1 1 d
C9 C 0.30685(11) -0.0353(4) 0.11066(11) 0.0277(5) Uani 1 1 d
H91 H 0.3021(11) -0.143(4) 0.1460(11) 0.022(6) Uiso 1 1 d
H92 H 0.2916(11) -0.100(4) 0.0688(13) 0.029(6) Uiso 1 1 d
C31 C 0.37729(10) 0.3683(4) 0.26887(10) 0.0248(5) Uani 1 1 d
C32 C 0.40795(10) 0.5649(4) 0.27322(10) 0.0279(5) Uani 1 1 d
C33 C 0.43918(10) 0.6350(4) 0.33055(11) 0.0294(5) Uani 1 1 d
C34 C 0.43987(10) 0.5066(4) 0.38588(11) 0.0319(5) Uani 1 1 d
C35 C 0.40962(11) 0.3106(4) 0.38383(11) 0.0328(6) Uani 1 1 d
C36 C 0.37840(10) 0.2441(4) 0.32593(11) 0.0286(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 0.0181 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 0.030
1.00 0.00 0.00 0.030
0.00 1.00 0.00 0.300
0.00 -1.00 0.00 0.300
0.00 0.00 1.00 0.030
0.00 0.00 -1.00 0.030
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 C1 C8 111.02(19)
C9 C1 C2 109.19(17)
C8 C1 C2 87.65(17)
C9 C1 H1 114.5(14)
C8 C1 H1 117.2(14)
C2 C1 H1 114.2(14)
F2 C2 C3 111.25(17)
F2 C2 C7 111.55(17)
C3 C2 C7 117.43(18)
F2 C2 C1 110.90(17)
C3 C2 C1 118.32(18)
C7 C2 C1 84.97(16)
C4 C3 C31 127.24(19)
C4 C3 C2 110.73(18)
C31 C3 C2 122.01(18)
C3 C4 F4 124.89(19)
C3 C4 C5 117.32(18)
F4 C4 C5 117.78(18)
F5 C5 C4 111.65(17)
F5 C5 C6 110.69(18)
C4 C5 C6 104.38(17)
F5 C5 C9 112.87(18)
C4 C5 C9 107.68(18)
C6 C5 C9 109.18(17)
O C6 C7 125.3(2)
O C6 C5 125.0(2)
C7 C6 C5 109.70(18)
F7 C7 C6 111.26(18)
F7 C7 C8 119.67(17)
C6 C7 C8 108.35(18)
F7 C7 C2 119.33(18)
C6 C7 C2 106.73(16)
C8 C7 C2 89.12(17)
C7 C8 C1 85.73(16)
C7 C8 H81 118.3(14)
C1 C8 H81 119.9(15)
C7 C8 H82 110.3(16)
C1 C8 H82 111.3(15)
H81 C8 H82 109(2)
C1 C9 C5 106.32(18)
C1 C9 H91 112.5(13)
C5 C9 H91 110.3(13)
C1 C9 H92 110.4(14)
C5 C9 H92 109.4(15)
H91 C9 H92 108(2)
C32 C31 C36 116.8(2)
C32 C31 C3 120.82(19)
C36 C31 C3 122.4(2)
F32 C32 C33 118.4(2)
F32 C32 C31 119.11(19)
C33 C32 C31 122.5(2)
F33 C33 C34 120.0(2)
F33 C33 C32 120.9(2)
C34 C33 C32 119.1(2)
F34 C34 C33 119.6(2)
F34 C34 C35 120.1(2)
C33 C34 C35 120.3(2)
F35 C35 C34 120.0(2)
F35 C35 C36 120.5(2)
C34 C35 C36 119.5(2)
F36 C36 C35 118.5(2)
F36 C36 C31 119.7(2)
C35 C36 C31 121.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F2 C2 1.376(2)
F4 C4 1.338(2)
F5 C5 1.370(2)
F7 C7 1.367(2)
F32 C32 1.347(3)
F33 C33 1.345(3)
F34 C34 1.337(3)
F35 C35 1.338(3)
F36 C36 1.343(3)
O C6 1.197(3)
C1 C9 1.535(3)
C1 C8 1.553(3)
C1 C2 1.569(3)
C1 H1 0.95(2)
C2 C3 1.515(3)
C2 C7 1.544(3)
C3 C4 1.325(3)
C3 C31 1.477(3)
C4 C5 1.512(3)
C5 C6 1.542(3)
C5 C9 1.542(3)
C6 C7 1.525(3)
C7 C8 1.537(3)
C8 H81 0.98(2)
C8 H82 0.96(3)
C9 H91 0.99(2)
C9 H92 0.98(3)
C31 C32 1.386(3)
C31 C36 1.389(3)
C32 C33 1.377(3)
C33 C34 1.375(3)
C34 C35 1.378(4)
C35 C36 1.380(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139183763
