#------------------------------------------------------------------------------
#$Date: 2022-06-06 05:07:07 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566794.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_1566794
loop_
_publ_author_name
'Sathe, Devavrat'
'Zhou, Junfeng'
'Chen, Hanlin'
'Schrage, Briana R.'
'Yoon, Seiyoung'
'Wang, Zeyu'
'Ziegler, Christopher J.'
'Wang, Junpeng'
_publ_section_title
;
 Depolymerizable semi-fluorinated polymers for sustainable functional
 materials
;
_journal_issue                   18
_journal_name_full               'Polymer Chemistry'
_journal_page_first              2608
_journal_page_last               2614
_journal_paper_doi               10.1039/D2PY00240J
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_sum            'C14 H12 F6 O'
_chemical_formula_weight         310.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-10 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8199(8)
_cell_length_b                   11.7062(14)
_cell_length_c                   18.082(2)
_cell_measurement_reflns_used    3723
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      2.85
_cell_volume                     1231.9(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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.034
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_min         2.072
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
; 
 Flack x determined using 596 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0775
_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)+(0.1042P)²+3.5614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2160
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1789
_reflns_number_total             2168
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2py00240j2.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1566794.cif.
;
_cod_database_code               1566794
_shelx_shelxl_version_number     2018/3
_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   0.961
_shelx_estimated_absorpt_t_max   0.980
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5547(15) 0.5897(7) 0.5605(5) 0.036(2) Uani 1 1 d . . . . .
C2 C 0.7663(17) 0.6288(7) 0.5500(5) 0.036(2) Uani 1 1 d . . . . .
C3 C 0.5851(14) 0.5724(7) 0.6415(5) 0.0323(19) Uani 1 1 d . . . . .
C4 C 0.8392(15) 0.6198(6) 0.6280(5) 0.0348(19) Uani 1 1 d . . . . .
C5 C 0.5355(13) 0.6750(6) 0.6910(4) 0.0290(17) Uani 1 1 d . . . . .
C6 C 0.7849(13) 0.7197(6) 0.6772(5) 0.0289(17) Uani 1 1 d . . . . .
C7 C 0.8367(14) 0.6999(7) 0.7614(5) 0.0334(18) Uani 1 1 d . . . . .
H7 H 0.938785 0.632090 0.768483 0.040 Uiso 1 1 calc R U . . .
C8 C 0.9271(16) 0.8023(7) 0.8038(5) 0.0371(19) Uani 1 1 d . . . . .
H8A H 0.847722 0.872208 0.786612 0.045 Uiso 1 1 calc R U . . .
H8B H 1.093343 0.811415 0.793893 0.045 Uiso 1 1 calc R U . . .
C9 C 0.887(3) 0.7869(10) 0.8911(7) 0.088(5) Uani 1 1 d . . . . .
H9A H 0.973725 0.846959 0.917521 0.106 Uiso 1 1 calc R U . . .
H9B H 0.721604 0.798621 0.901867 0.106 Uiso 1 1 calc R U . . .
C10 C 0.9529(19) 0.6801(10) 0.9187(6) 0.056(3) Uani 1 1 d . . . . .
H10 H 1.118954 0.661099 0.911598 0.067 Uiso 1 1 calc R U . . .
C11 C 0.793(2) 0.5773(11) 0.9203(7) 0.071(4) Uani 1 1 d . . . . .
H11 H 0.867694 0.500826 0.915294 0.085 Uiso 1 1 calc R U . . .
C12 C 0.556(2) 0.5819(11) 0.9030(6) 0.071(4) Uani 1 1 d . . . . .
H12A H 0.493388 0.657358 0.917382 0.086 Uiso 1 1 calc R U . . .
H12B H 0.472864 0.522642 0.931564 0.086 Uiso 1 1 calc R U . . .
C13 C 0.5154(17) 0.5624(7) 0.8195(5) 0.040(2) Uani 1 1 d . . . . .
H13A H 0.607982 0.496317 0.802774 0.048 Uiso 1 1 calc R U . . .
H13B H 0.351443 0.544176 0.810929 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5809(13) 0.6676(7) 0.7742(4) 0.0299(18) Uani 1 1 d . . . . .
H14 H 0.504583 0.734909 0.797746 0.036 Uiso 1 1 calc R U . . .
F1 F 0.3671(8) 0.5837(4) 0.5207(3) 0.0391(12) Uani 1 1 d . . . . .
F2 F 0.8656(9) 0.6809(4) 0.4929(3) 0.0441(13) Uani 1 1 d . . . . .
F3 F 0.5552(8) 0.4647(3) 0.6694(3) 0.0365(12) Uani 1 1 d . . . . .
F4 F 1.0252(8) 0.5551(4) 0.6444(3) 0.0388(12) Uani 1 1 d . . . . .
F5 F 0.3428(8) 0.7364(3) 0.6700(2) 0.0326(11) Uani 1 1 d . . . . .
F6 F 0.8343(8) 0.8269(3) 0.6508(2) 0.0315(11) Uani 1 1 d . . . . .
O1 O 0.8604(13) 0.6475(7) 0.9892(3) 0.061(2) 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'
F F 0.0171 0.0103 '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'
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
_geom_angle_publ_flag
F1 C1 C2 135.4(8) . . ?
F1 C1 C3 129.2(8) . . ?
C2 C1 C3 94.5(8) . . ?
C1 C2 F2 132.3(9) . . ?
C1 C2 C4 96.0(7) . . ?
F2 C2 C4 130.5(8) . . ?
F3 C3 C1 118.2(7) . . ?
F3 C3 C5 119.0(7) . . ?
C1 C3 C5 116.6(7) . . ?
F3 C3 C4 119.5(6) . . ?
C1 C3 C4 85.0(6) . . ?
C5 C3 C4 89.5(6) . . ?
F4 C4 C2 118.7(7) . . ?
F4 C4 C6 118.2(7) . . ?
C2 C4 C6 116.7(7) . . ?
F4 C4 C3 120.8(6) . . ?
C2 C4 C3 84.6(6) . . ?
C6 C4 C3 89.1(6) . . ?
F5 C5 C3 113.6(6) . . ?
F5 C5 C14 116.1(7) . . ?
C3 C5 C14 120.0(6) . . ?
F5 C5 C6 122.3(6) . . ?
C3 C5 C6 89.7(6) . . ?
C14 C5 C6 90.9(6) . . ?
F6 C6 C4 117.4(6) . . ?
F6 C6 C5 123.8(6) . . ?
C4 C6 C5 91.7(6) . . ?
F6 C6 C7 115.6(6) . . ?
C4 C6 C7 114.8(6) . . ?
C5 C6 C7 88.5(6) . . ?
C8 C7 C14 116.7(7) . . ?
C8 C7 C6 116.2(6) . . ?
C14 C7 C6 89.8(6) . . ?
C7 C8 C9 111.0(7) . . ?
C10 C9 C8 114.3(11) . . ?
C9 C10 O1 116.9(11) . . ?
C9 C10 C11 122.9(11) . . ?
O1 C10 C11 62.8(7) . . ?
C12 C11 C10 124.2(11) . . ?
C12 C11 O1 114.0(11) . . ?
C10 C11 O1 55.8(7) . . ?
C11 C12 C13 111.0(11) . . ?
C14 C13 C12 111.5(8) . . ?
C13 C14 C5 122.0(7) . . ?
C13 C14 C7 121.1(7) . . ?
C5 C14 C7 90.3(6) . . ?
C10 O1 C11 61.4(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.310(10) . ?
C1 C2 1.328(13) . ?
C1 C3 1.488(12) . ?
C2 F2 1.330(9) . ?
C2 C4 1.477(12) . ?
C3 F3 1.370(9) . ?
C3 C5 1.526(11) . ?
C3 C4 1.598(11) . ?
C4 F4 1.354(10) . ?
C4 C6 1.504(11) . ?
C5 F5 1.385(9) . ?
C5 C14 1.530(11) . ?
C5 C6 1.563(10) . ?
C6 F6 1.373(8) . ?
C6 C7 1.569(12) . ?
C7 C8 1.517(11) . ?
C7 C14 1.554(11) . ?
C8 C9 1.606(16) . ?
C9 C10 1.401(15) . ?
C10 O1 1.434(12) . ?
C10 C11 1.523(18) . ?
C11 C12 1.416(18) . ?
C11 O1 1.543(16) . ?
C12 C13 1.545(14) . ?
C13 C14 1.526(11) . ?
