data_8_19srv190
_audit_creation_date               2019-06-04
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2017/1'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'Yufit, D.' d.s.yufit@durham.ac.uk
;

Durham University
Chemistry
South Rd.
Durham
DH1 3LE
UK
;

_publ_requested_journal           'Angewandte Chem.Int.Ed.'
_publ_section_title
;
Electrophilic Aromatic Substitution of Tetrafluoropyridyl Aryl
Ethers: A Simple and Efficient Route to Unsymmetrical Biaryls
;

_publ_contact_author_name         'Dmitry Yufit'
_publ_contact_author_address
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
_publ_contact_author_email        'd.s.yufit@durham.ac.uk'


_publ_contact_letter
;
The CIF file contains data for the structure 8 from
the paper 

"Electrophilic Aromatic Substitution of Tetrafluoropyridyl Aryl
Ethers: A Simple and Efficient Route to Unsymmetrical Biaryls"

by W.D.G.Brittain and S.L.Cobb. 

The paper will be submitted to Angewandte Chem.Int.Ed. shortly. 
;
loop_
_publ_author_name
_publ_author_address
'Brittain, William D.G.'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
'Cobb, Steven L.'
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;


_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C20 H13 F4 I2 N O2'
_chemical_formula_sum              'C20 H13 F4 I2 N O2'
_chemical_formula_weight           629.11
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C20 H13 N1 O2 F4 I2'
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'
 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 '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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     12.3523(3)
_cell_length_b                     12.7890(3)
_cell_length_c                     12.8327(3)
_cell_angle_alpha                  90
_cell_angle_beta                   94.170(2)
_cell_angle_gamma                  90
_cell_volume                       2021.86(9)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      6082
_cell_measurement_temperature      120.0
_cell_measurement_theta_max        32.5080
_cell_measurement_theta_min        2.2550
_shelx_estimated_absorpt_T_max     0.648
_shelx_estimated_absorpt_T_min     0.379
_exptl_absorpt_coefficient_mu      3.163
_exptl_absorpt_correction_T_max    0.784
_exptl_absorpt_correction_T_min    0.489
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      2.067
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               1192
_exptl_crystal_size_max            0.38
_exptl_crystal_size_mid            0.17
_exptl_crystal_size_min            0.15
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0394
_diffrn_reflns_av_unetI/netI       0.0384
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         17
_diffrn_reflns_limit_h_min         -16
_diffrn_reflns_limit_k_max         17
_diffrn_reflns_limit_k_min         -17
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              20412
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           29.497
_diffrn_reflns_theta_min           2.295
_diffrn_ambient_temperature        120.0
_diffrn_detector                   'CCD area detector'
_diffrn_detector_area_resol_mean   16.1511
_diffrn_detector_type              Sapphire3
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   37.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega   30.00   86.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega   64.00   97.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega   12.00   90.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   97.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
  6 omega   28.00   71.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega  -16.00   71.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000 -150.0000 87
;
_diffrn_measurement_device         '4-circle diffractometer'
_diffrn_measurement_device_type    'Xcalibur, Sapphire3'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_UB_11        -0.0090851000
_diffrn_orient_matrix_UB_12        0.0473006000
_diffrn_orient_matrix_UB_13        -0.0281390000
_diffrn_orient_matrix_UB_21        -0.0078383000
_diffrn_orient_matrix_UB_22        0.0266819000
_diffrn_orient_matrix_UB_23        0.0473534000
_diffrn_orient_matrix_UB_31        0.0562814000
_diffrn_orient_matrix_UB_32        0.0113597000
_diffrn_orient_matrix_UB_33        0.0061343000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'sealed tubeEnhance (Mo) X-ray Source'
_diffrn_source_target              Mo
_diffrn_source_type                'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  4454
_reflns_number_total               5635
_reflns_odcompleteness_completeness  99.96
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       31.44
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'XS (Sheldrick, 2008)'
_refine_diff_density_max           0.813
_refine_diff_density_min           -0.895
_refine_diff_density_rms           0.122
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       264
_refine_ls_number_reflns           5635
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0426
_refine_ls_R_factor_gt             0.0294
_refine_ls_restrained_S_all        1.024
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0290P)²+0.4130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0642
_refine_ls_wR_factor_ref           0.0711
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.c Idealised tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     ?
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
 I1 I -0.39515(2) 0.53278(2) 0.41553(2) 0.02312(6) Uani 1 1 d . . . . .
 I2 I -0.19491(2) 0.52730(2) -0.00032(2) 0.02189(6) Uani 1 1 d . . . . .
 F1 F 0.45417(14) 0.27143(13) 0.38300(13) 0.0225(4) Uani 1 1 d . . . . .
 F2 F 0.61773(15) 0.13314(14) 0.35370(13) 0.0271(4) Uani 1 1 d . . . . .
 F3 F 0.67089(15) 0.26115(15) 0.03428(14) 0.0293(4) Uani 1 1 d . . . . .
 F4 F 0.50169(14) 0.39952(13) 0.04199(13) 0.0254(4) Uani 1 1 d . . . . .
 O1 O -0.36585(16) 0.56926(16) 0.17701(16) 0.0227(5) Uani 1 1 d . . . . .
 H1 H -0.342269 0.622978 0.148564 0.034 Uiso 1 1 calc R . . . .
 O2 O 0.39125(15) 0.41153(15) 0.21832(16) 0.0208(4) Uani 1 1 d . . . . .
 N1 N 0.6427(2) 0.19851(19) 0.19448(19) 0.0212(5) Uani 1 1 d . . . . .
 C1 C -0.2770(2) 0.4781(2) 0.3194(2) 0.0173(6) Uani 1 1 d . . . . .
 C2 C -0.2805(2) 0.5087(2) 0.2146(2) 0.0174(6) Uani 1 1 d . . . . .
 C3 C -0.1968(2) 0.4750(2) 0.1555(2) 0.0164(6) Uani 1 1 d . . . . .
 C4 C -0.1150(2) 0.4092(2) 0.1974(2) 0.0182(6) Uani 1 1 d . . . . .
 H4 H -0.059391 0.387013 0.155047 0.022 Uiso 1 1 calc R . . . .
 C5 C -0.1138(2) 0.3753(2) 0.3017(2) 0.0184(6) Uani 1 1 d . . . . .
 C6 C -0.1950(2) 0.4118(2) 0.3620(2) 0.0202(6) Uani 1 1 d . . . . .
 H6 H -0.194821 0.391495 0.433213 0.024 Uiso 1 1 calc R . . . .
 C7 C -0.0292(2) 0.2940(2) 0.3431(2) 0.0213(6) Uani 1 1 d . . . . .
 C8 C -0.0189(3) 0.2899(3) 0.4642(2) 0.0305(8) Uani 1 1 d . . . . .
 H8A H -0.001733 0.359844 0.491949 0.046 Uiso 1 1 calc GR . . . .
 H8B H 0.039113 0.241278 0.487600 0.046 Uiso 1 1 calc GR . . . .
 H8C H -0.087707 0.266108 0.489518 0.046 Uiso 1 1 calc GR . . . .
 C9 C -0.0692(3) 0.1861(2) 0.3024(3) 0.0276(7) Uani 1 1 d . . . . .
 H9A H -0.141008 0.171725 0.326878 0.041 Uiso 1 1 calc GR . . . .
 H9B H -0.018068 0.131916 0.328554 0.041 Uiso 1 1 calc GR . . . .
 H9C H -0.073848 0.186059 0.225792 0.041 Uiso 1 1 calc GR . . . .
 C10 C 0.0829(2) 0.3230(2) 0.3055(2) 0.0182(6) Uani 1 1 d . . . . .
 C11 C 0.1441(2) 0.2539(2) 0.2502(2) 0.0209(6) Uani 1 1 d . . . . .
 H11 H 0.115513 0.186756 0.232351 0.025 Uiso 1 1 calc R . . . .
 C12 C 0.2467(2) 0.2813(2) 0.2204(2) 0.0198(6) Uani 1 1 d . . . . .
 H12 H 0.287062 0.233725 0.181517 0.024 Uiso 1 1 calc R . . . .
 C13 C 0.2889(2) 0.3776(2) 0.2478(2) 0.0180(6) Uani 1 1 d . . . . .
 C14 C 0.2302(2) 0.4501(2) 0.3013(2) 0.0201(6) Uani 1 1 d . . . . .
 H14 H 0.259180 0.517312 0.318167 0.024 Uiso 1 1 calc R . . . .
 C15 C 0.1275(2) 0.4211(2) 0.3296(2) 0.0212(6) Uani 1 1 d . . . . .
 H15 H 0.086543 0.469718 0.366539 0.025 Uiso 1 1 calc R . . . .
 C16 C 0.4711(2) 0.3384(2) 0.2117(2) 0.0181(6) Uani 1 1 d . . . . .
 C17 C 0.5038(2) 0.2696(2) 0.2931(2) 0.0172(6) Uani 1 1 d . . . . .
 C18 C 0.5879(2) 0.2011(2) 0.2782(2) 0.0184(6) Uani 1 1 d . . . . .
 C19 C 0.6134(2) 0.2649(2) 0.1194(2) 0.0197(6) Uani 1 1 d . . . . .
 C20 C 0.5286(2) 0.3346(2) 0.1228(2) 0.0186(6) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
 I1 C1 2.099(3) . ?
 I2 C3 2.110(3) . ?
 F1 C17 1.345(3) . ?
 F2 C18 1.333(3) . ?
 F3 C19 1.346(3) . ?
 F4 C20 1.350(3) . ?
 O1 H1 0.8400 . ?
 O1 C2 1.368(3) . ?
 O2 C13 1.414(3) . ?
 O2 C16 1.366(3) . ?
 N1 C18 1.312(4) . ?
 N1 C19 1.316(4) . ?
 C1 C2 1.398(4) . ?
 C1 C6 1.401(4) . ?
 C2 C3 1.395(4) . ?
 C3 C4 1.392(4) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.406(4) . ?
 C5 C6 1.391(4) . ?
 C5 C7 1.541(4) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.551(4) . ?
 C7 C9 1.545(4) . ?
 C7 C10 1.544(4) . ?
 C8 H8A 0.9800 . ?
 C8 H8B 0.9800 . ?
 C8 H8C 0.9800 . ?
 C9 H9A 0.9800 . ?
 C9 H9B 0.9800 . ?
 C9 H9C 0.9800 . ?
 C10 C11 1.391(4) . ?
 C10 C15 1.396(4) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.395(4) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.373(4) . ?
 C13 C14 1.389(4) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.395(4) . ?
 C15 H15 0.9500 . ?
 C16 C17 1.402(4) . ?
 C16 C20 1.389(4) . ?
 C17 C18 1.383(4) . ?
 C19 C20 1.379(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
 C2 O1 H1 109.5 . . ?
 C16 O2 C13 118.0(2) . . ?
 C18 N1 C19 117.0(3) . . ?
 C2 C1 I1 119.8(2) . . ?
 C2 C1 C6 121.1(3) . . ?
 C6 C1 I1 119.1(2) . . ?
 O1 C2 C1 117.9(3) . . ?
 O1 C2 C3 124.5(3) . . ?
 C3 C2 C1 117.7(3) . . ?
 C2 C3 I2 118.5(2) . . ?
 C4 C3 I2 120.0(2) . . ?
 C4 C3 C2 121.5(3) . . ?
 C3 C4 H4 119.6 . . ?
 C3 C4 C5 120.8(3) . . ?
 C5 C4 H4 119.6 . . ?
 C4 C5 C7 119.8(3) . . ?
 C6 C5 C4 117.9(3) . . ?
 C6 C5 C7 122.2(3) . . ?
 C1 C6 H6 119.5 . . ?
 C5 C6 C1 121.1(3) . . ?
 C5 C6 H6 119.5 . . ?
 C5 C7 C8 111.8(3) . . ?
 C5 C7 C9 107.1(2) . . ?
 C5 C7 C10 109.4(2) . . ?
 C9 C7 C8 108.0(3) . . ?
 C10 C7 C8 108.2(2) . . ?
 C10 C7 C9 112.4(3) . . ?
 C7 C8 H8A 109.5 . . ?
 C7 C8 H8B 109.5 . . ?
 C7 C8 H8C 109.5 . . ?
 H8A C8 H8B 109.5 . . ?
 H8A C8 H8C 109.5 . . ?
 H8B C8 H8C 109.5 . . ?
 C7 C9 H9A 109.5 . . ?
 C7 C9 H9B 109.5 . . ?
 C7 C9 H9C 109.5 . . ?
 H9A C9 H9B 109.5 . . ?
 H9A C9 H9C 109.5 . . ?
 H9B C9 H9C 109.5 . . ?
 C11 C10 C7 122.7(3) . . ?
 C11 C10 C15 117.6(3) . . ?
 C15 C10 C7 119.7(3) . . ?
 C10 C11 H11 119.4 . . ?
 C10 C11 C12 121.3(3) . . ?
 C12 C11 H11 119.4 . . ?
 C11 C12 H12 120.3 . . ?
 C13 C12 C11 119.3(3) . . ?
 C13 C12 H12 120.3 . . ?
 C12 C13 O2 122.5(3) . . ?
 C12 C13 C14 121.6(3) . . ?
 C14 C13 O2 115.8(3) . . ?
 C13 C14 H14 121.1 . . ?
 C13 C14 C15 117.9(3) . . ?
 C15 C14 H14 121.1 . . ?
 C10 C15 H15 118.9 . . ?
 C14 C15 C10 122.2(3) . . ?
 C14 C15 H15 118.9 . . ?
 O2 C16 C17 123.6(3) . . ?
 O2 C16 C20 119.3(3) . . ?
 C20 C16 C17 117.0(3) . . ?
 F1 C17 C16 120.2(2) . . ?
 F1 C17 C18 121.5(3) . . ?
 C18 C17 C16 118.3(3) . . ?
 F2 C18 C17 118.9(3) . . ?
 N1 C18 F2 116.5(2) . . ?
 N1 C18 C17 124.5(3) . . ?
 F3 C19 C20 119.7(3) . . ?
 N1 C19 F3 116.0(3) . . ?
 N1 C19 C20 124.3(3) . . ?
 F4 C20 C16 119.8(3) . . ?
 F4 C20 C19 121.2(3) . . ?
 C19 C20 C16 118.9(3) . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
  _geom_hbond_publ_flag
 O1 H1 F1 0.84 2.37 2.889(3) 120.9 2 yes

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_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 C4 C5 C7 C8 163.9(3) . . . . ?
 C4 C5 C7 C9 -77.9(3) . . . . ?
 C4 C5 C7 C10 44.1(4) . . . . ?
 C5 C7 C10 C11 -124.9(3) . . . . ?
 C5 C7 C10 C15 57.0(3) . . . . ?
 C6 C5 C7 C8 -20.7(4) . . . . ?
 C6 C5 C7 C9 97.5(3) . . . . ?
 C6 C5 C7 C10 -140.5(3) . . . . ?
 C8 C7 C10 C11 113.1(3) . . . . ?
 C8 C7 C10 C15 -65.1(3) . . . . ?
 C9 C7 C10 C11 -6.1(4) . . . . ?
 C9 C7 C10 C15 175.8(3) . . . . ?
 C12 C13 O2 C16 -33.6(4) . . . . ?
 C14 C13 O2 C16 150.0(3) . . . . ?
 C17 C16 O2 C13 -53.6(4) . . . . ?
 C20 C16 O2 C13 130.5(3) . . . . ?

loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 -1 -5 1 0.0684 -1.0000 -5.0000 1.0000 -0.2556 -0.0782 -0.1069
 5 4 -1 0.0323 5.0000 4.0001 -1.0000 0.1719 0.0202 0.3207
 -5 2 2 0.0372 -5.0000 1.9999 2.0000 0.0837 0.1873 -0.2464
 0 0 -1 0.1263 -0.0000 0.0000 -1.0000 0.0281 -0.0474 -0.0061
 0 0 1 0.1984 0.0000 -0.0000 1.0000 -0.0281 0.0474 0.0061
 5 -2 -1 0.0905 5.0000 -1.9999 -1.0000 -0.1119 -0.1399 0.2526


_olex2_submission_special_instructions  'No special instructions were received'
