data_3f_19srv253
_audit_creation_date               2019-08-21
_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
Science Site, 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 3f 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           'C15 H6 F4 I N O'
_chemical_formula_sum              'C15 H6 F4 I N O'
_chemical_formula_weight           419.11
_chemical_absolute_configuration   ?
_chemical_melting_point            ?
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             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     4.6677(3)
_cell_length_b                     11.0185(7)
_cell_length_c                     13.0170(8)
_cell_angle_alpha                  90
_cell_angle_beta                   90.865(2)
_cell_angle_gamma                  90
_cell_volume                       669.40(7)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      9948
_cell_measurement_temperature      120.0
_cell_measurement_theta_max        31.55
_cell_measurement_theta_min        2.42
_shelx_estimated_absorpt_T_max     0.867
_shelx_estimated_absorpt_T_min     0.604
_exptl_absorpt_coefficient_mu      2.439
_exptl_absorpt_correction_T_max    0.9042
_exptl_absorpt_correction_T_min    0.6305
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;    
 SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1080 before and 0.0394 after correction. 
The Ratio of minimum to maximum transmission is 0.6973. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      2.079
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plank
_exptl_crystal_F_000               400
_exptl_crystal_size_max            0.23
_exptl_crystal_size_mid            0.1
_exptl_crystal_size_min            0.06
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0261
_diffrn_reflns_av_unetI/netI       0.0228
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.998
_diffrn_reflns_limit_h_max         6
_diffrn_reflns_limit_h_min         -6
_diffrn_reflns_limit_k_max         15
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -18
_diffrn_reflns_number              14627
_diffrn_reflns_point_group_measured_fraction_full  0.995
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           29.995
_diffrn_reflns_theta_min           3.130
_diffrn_ambient_temperature        120.0
_diffrn_detector                   'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean   10.4
_diffrn_detector_type              'CMOS sensor'
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_device         '3-circle diffractometer'
_diffrn_measurement_device_type    'Bruker D8 Venture'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    'focusing mirrors'
_diffrn_radiation_probe            X-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'microfocus sealed X-ray tube'
_diffrn_source_type                'Incoatec I\mS microsource'
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.905
_reflns_Friedel_fraction_full      0.994
_reflns_Friedel_fraction_max       0.996
_reflns_number_gt                  3752
_reflns_number_total               3908
_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_bruker_data_scaling     'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement         'SAINT v8.38A (Bruker AXS, 2016)'
_computing_data_collection         'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction          'SAINT v8.38A (Bruker AXS, 2016)'
_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      'XM (Sheldrick, 2008)'
_refine_diff_density_max           0.585
_refine_diff_density_min           -0.532
_refine_diff_density_rms           0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1735 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.044(7)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       199
_refine_ls_number_reflns           3908
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0176
_refine_ls_R_factor_gt             0.0163
_refine_ls_restrained_S_all        1.048
_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)+(0.0244P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0397
_refine_ls_wR_factor_ref           0.0401
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_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 0.66971(3) 0.17432(2) 0.27137(2) 0.01861(5) Uani 1 1 d . . . . .
 F1 F 1.1776(4) 0.29311(16) 0.48962(14) 0.0264(4) Uani 1 1 d . . . . .
 F2 F 0.8655(5) 0.3699(2) 0.64987(14) 0.0369(5) Uani 1 1 d . . . . .
 F3 F 0.3700(4) 0.63442(15) 0.45156(14) 0.0275(4) Uani 1 1 d . . . . .
 F4 F 0.6754(3) 0.57897(19) 0.28448(12) 0.0249(4) Uani 1 1 d . . . . .
 O1 O 1.1095(4) 0.39499(18) 0.30380(15) 0.0175(4) Uani 1 1 d . . . . .
 N1 N 0.6164(6) 0.5017(2) 0.55036(19) 0.0238(5) Uani 1 1 d . . . . .
 C1 C 0.8093(5) 0.3075(2) 0.1689(2) 0.0151(4) Uani 1 1 d . . . . .
 C2 C 1.0040(5) 0.3932(2) 0.20146(19) 0.0158(5) Uani 1 1 d . . . . .
 C3 C 1.1243(6) 0.4790(2) 0.1347(2) 0.0180(5) Uani 1 1 d . . . . .
 H3 H 1.263042 0.535424 0.159259 0.022 Uiso 1 1 calc R . . . .
 C4 C 1.0383(6) 0.4798(2) 0.0340(2) 0.0178(5) Uani 1 1 d . . . . .
 H4 H 1.120687 0.536527 -0.011942 0.021 Uiso 1 1 calc R . . . .
 C5 C 0.7315(6) 0.4018(3) -0.1073(2) 0.0199(5) Uani 1 1 d . . . . .
 H5 H 0.810350 0.459854 -0.152753 0.024 Uiso 1 1 calc R . . . .
 C6 C 0.5258(6) 0.3230(3) -0.1425(2) 0.0209(5) Uani 1 1 d . . . . .
 H6 H 0.462660 0.326590 -0.212135 0.025 Uiso 1 1 calc R . . . .
 C7 C 0.4079(6) 0.2369(3) -0.0757(2) 0.0199(5) Uani 1 1 d . . . . .
 H7 H 0.263650 0.183114 -0.100569 0.024 Uiso 1 1 calc R . . . .
 C8 C 0.4983(5) 0.2293(2) 0.0253(2) 0.0169(5) Uani 1 1 d . . . . .
 H8 H 0.417912 0.169801 0.069180 0.020 Uiso 1 1 calc R . . . .
 C9 C 0.7108(5) 0.3098(2) 0.06418(19) 0.0144(4) Uani 1 1 d . . . . .
 C10 C 0.8287(6) 0.3975(2) -0.0029(2) 0.0161(5) Uani 1 1 d . . . . .
 C11 C 0.9342(5) 0.4307(2) 0.37995(19) 0.0155(5) Uani 1 1 d . . . . .
 C12 C 0.9811(6) 0.3786(3) 0.4768(2) 0.0192(5) Uani 1 1 d . . . . .
 C13 C 0.8178(7) 0.4185(3) 0.5581(2) 0.0238(6) Uani 1 1 d . . . . .
 C14 C 0.5754(6) 0.5502(2) 0.4594(2) 0.0203(5) Uani 1 1 d . . . . .
 C15 C 0.7267(6) 0.5209(3) 0.3727(2) 0.0173(5) 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 2.094(3) . ?
 F1 C12 1.324(3) . ?
 F2 C13 1.325(4) . ?
 F3 C14 1.337(3) . ?
 F4 C15 1.333(3) . ?
 O1 C2 1.413(3) . ?
 O1 C11 1.353(3) . ?
 N1 C13 1.316(4) . ?
 N1 C14 1.310(4) . ?
 C1 C2 1.373(4) . ?
 C1 C9 1.432(3) . ?
 C2 C3 1.407(4) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.365(4) . ?
 C4 H4 0.9500 . ?
 C4 C10 1.413(4) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.368(4) . ?
 C5 C10 1.426(4) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.405(4) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.378(4) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.418(4) . ?
 C9 C10 1.420(4) . ?
 C11 C12 1.399(4) . ?
 C11 C15 1.390(4) . ?
 C12 C13 1.386(4) . ?
 C14 C15 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
 C11 O1 C2 119.25(19) . . ?
 C14 N1 C13 116.6(3) . . ?
 C2 C1 I1 119.76(19) . . ?
 C2 C1 C9 118.9(2) . . ?
 C9 C1 I1 121.33(19) . . ?
 C1 C2 O1 121.3(2) . . ?
 C1 C2 C3 122.7(2) . . ?
 C3 C2 O1 115.9(2) . . ?
 C2 C3 H3 120.5 . . ?
 C4 C3 C2 118.9(2) . . ?
 C4 C3 H3 120.5 . . ?
 C3 C4 H4 119.5 . . ?
 C3 C4 C10 121.0(2) . . ?
 C10 C4 H4 119.5 . . ?
 C6 C5 H5 119.7 . . ?
 C6 C5 C10 120.7(3) . . ?
 C10 C5 H5 119.7 . . ?
 C5 C6 H6 120.0 . . ?
 C5 C6 C7 120.0(3) . . ?
 C7 C6 H6 120.0 . . ?
 C6 C7 H7 119.5 . . ?
 C8 C7 C6 121.0(3) . . ?
 C8 C7 H7 119.5 . . ?
 C7 C8 H8 119.8 . . ?
 C7 C8 C9 120.3(2) . . ?
 C9 C8 H8 119.8 . . ?
 C8 C9 C1 122.8(2) . . ?
 C8 C9 C10 118.8(2) . . ?
 C10 C9 C1 118.4(2) . . ?
 C4 C10 C5 120.8(2) . . ?
 C4 C10 C9 120.0(2) . . ?
 C9 C10 C5 119.2(2) . . ?
 O1 C11 C12 116.9(2) . . ?
 O1 C11 C15 125.9(2) . . ?
 C15 C11 C12 117.0(2) . . ?
 F1 C12 C11 120.3(2) . . ?
 F1 C12 C13 121.1(3) . . ?
 C13 C12 C11 118.5(3) . . ?
 F2 C13 C12 118.3(3) . . ?
 N1 C13 F2 117.4(3) . . ?
 N1 C13 C12 124.3(3) . . ?
 F3 C14 C15 118.4(3) . . ?
 N1 C14 F3 116.6(3) . . ?
 N1 C14 C15 125.1(3) . . ?
 F4 C15 C11 121.2(2) . . ?
 F4 C15 C14 120.3(2) . . ?
 C14 C15 C11 118.5(2) . . ?

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
 C1 C2 O1 C11 -71.8(3) . . . . ?
 C3 C2 O1 C11 112.1(3) . . . . ?
 C12 C11 O1 C2 149.4(2) . . . . ?
 C15 C11 O1 C2 -35.8(4) . . . . ?


_olex2_submission_special_instructions  'No special instructions were received'
