# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2063b
_database_code_depnum_ccdc_archive 'CCDC 1999363'
loop_
_audit_author_name
_audit_author_address
'Junko Nagaoka'
;Nagasaki University
Japan
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_moiety         'C12 H11 N O2'
_chemical_formula_weight         201.22
_chemical_melting_point          407-409

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   6.571(3)
_cell_length_b                   12.434(5)
_cell_length_c                   12.168(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.376(7)
_cell_angle_gamma                90.0000
_cell_volume                     992.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1938
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424.00
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.998

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            7993
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2275
_reflns_number_gt                1776
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1384
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2275
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0596P)²+0.2291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.5664(2) 0.33020(11) 0.83090(13) 0.0219(4) Uani 1 1 d . . . . .
O2 O 0.7048(2) 0.46215(11) 0.67980(13) 0.0243(4) Uani 1 1 d . . . . .
N1 N 0.2900(3) 0.43816(13) 0.85726(14) 0.0169(4) Uani 1 1 d . . . . .
C1 C 0.4696(3) 0.41281(16) 0.80688(17) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.5281(3) 0.49029(16) 0.72516(17) 0.0183(5) Uani 1 1 d . . . . .
C3 C 0.4158(3) 0.57957(17) 0.70008(17) 0.0205(5) Uani 1 1 d . . . . .
H3 H 0.4574 0.6283 0.6456 0.025 Uiso 1 1 calc R U . . .
C4 C 0.2361(3) 0.59944(17) 0.75566(18) 0.0228(5) Uani 1 1 d . . . . .
H4 H 0.1582 0.6624 0.7394 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1757(3) 0.52956(16) 0.83126(18) 0.0208(5) Uani 1 1 d . . . . .
H5 H 0.0538 0.5428 0.8673 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7762(4) 0.53515(19) 0.5995(2) 0.0289(6) Uani 1 1 d . . . . .
H6A H 0.9035 0.5078 0.5720 0.035 Uiso 1 1 calc R U . . .
H6B H 0.6733 0.5417 0.5382 0.035 Uiso 1 1 calc R U . . .
H6C H 0.8005 0.6059 0.6333 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2178(3) 0.36503(16) 0.93875(17) 0.0176(5) Uani 1 1 d . . . . .
C8 C 0.0209(3) 0.32461(16) 0.92539(17) 0.0183(5) Uani 1 1 d . . . . .
H8 H -0.0648 0.3441 0.8630 0.022 Uiso 1 1 calc R U . . .
C9 C -0.0496(3) 0.25515(17) 1.00449(18) 0.0222(5) Uani 1 1 d . . . . .
H9 H -0.1844 0.2275 0.9964 0.027 Uiso 1 1 calc R U . . .
C10 C 0.0764(4) 0.22621(18) 1.09493(18) 0.0239(5) Uani 1 1 d . . . . .
H10 H 0.0284 0.1778 1.1480 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2724(4) 0.26758(17) 1.10828(18) 0.0252(5) Uani 1 1 d . . . . .
H11 H 0.3577 0.2480 1.1708 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3442(3) 0.33750(16) 1.03040(18) 0.0217(5) Uani 1 1 d . . . . .
H12 H 0.4781 0.3662 1.0395 0.026 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O1 C1 1.234(2) . ?
O2 C2 1.361(2) . ?
O2 C6 1.433(3) . ?
N1 C5 1.388(3) . ?
N1 C1 1.398(3) . ?
N1 C7 1.446(3) . ?
C1 C2 1.452(3) . ?
C2 C3 1.358(3) . ?
C3 C4 1.416(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.342(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.388(3) . ?
C7 C12 1.394(3) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 O2 C6 115.81(16) . . ?
C5 N1 C1 122.96(17) . . ?
C5 N1 C7 118.42(17) . . ?
C1 N1 C7 118.61(16) . . ?
O1 C1 N1 121.37(19) . . ?
O1 C1 C2 124.10(19) . . ?
N1 C1 C2 114.52(17) . . ?
C3 C2 O2 125.78(19) . . ?
C3 C2 C1 122.28(19) . . ?
O2 C2 C1 111.94(18) . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 N1 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
N1 C5 H5 119.7 . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 120.8(2) . . ?
C8 C7 N1 119.25(19) . . ?
C12 C7 N1 119.92(19) . . ?
C7 C8 C9 119.3(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.3(2) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?

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
C5 N1 C1 O1 -179.11(19) . . . . ?
C7 N1 C1 O1 -0.2(3) . . . . ?
C5 N1 C1 C2 0.3(3) . . . . ?
C7 N1 C1 C2 179.16(17) . . . . ?
C6 O2 C2 C3 0.6(3) . . . . ?
C6 O2 C2 C1 -178.96(18) . . . . ?
O1 C1 C2 C3 179.1(2) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
O1 C1 C2 O2 -1.3(3) . . . . ?
N1 C1 C2 O2 179.33(17) . . . . ?
O2 C2 C3 C4 -178.88(19) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 N1 1.1(3) . . . . ?
C1 N1 C5 C4 -0.7(3) . . . . ?
C7 N1 C5 C4 -179.61(19) . . . . ?
C5 N1 C7 C8 54.0(3) . . . . ?
C1 N1 C7 C8 -124.9(2) . . . . ?
C5 N1 C7 C12 -124.8(2) . . . . ?
C1 N1 C7 C12 56.3(3) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
N1 C7 C8 C9 -179.27(18) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C8 C7 C12 C11 0.9(3) . . . . ?
N1 C7 C12 C11 179.69(18) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        3-Methoxy-1-phenylpyridin-2(1H)-one
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2058c
_database_code_depnum_ccdc_archive 'CCDC 1999364'
loop_
_audit_author_name
_audit_author_address
'Junko Nagaoka'
;Nagasaki University
Japan
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_moiety         'C12 H11 N O2'
_chemical_formula_weight         201.22
_chemical_melting_point          378-380

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.935(5)
_cell_length_b                   7.985(4)
_cell_length_c                   13.410(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.758(9)
_cell_angle_gamma                90.0000
_cell_volume                     994.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2047
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424.00
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.998

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            7957
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_min         2.218
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2276
_reflns_number_gt                1494
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1159
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2276
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0459P)²+0.4141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.84378(17) -0.09237(18) 0.23560(11) 0.0255(4) Uani 1 1 d . . . . .
O2 O 0.75783(17) 0.04306(18) 0.04644(11) 0.0256(4) Uani 1 1 d . . . . .
N1 N 0.7792(2) -0.2062(2) -0.03680(14) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.7924(2) -0.1245(3) 0.05090(17) 0.0207(5) Uani 1 1 d . . . . .
C2 C 0.8392(2) -0.1955(3) 0.15358(17) 0.0214(5) Uani 1 1 d . . . . .
C3 C 0.8759(2) -0.3634(3) 0.16181(18) 0.0257(5) Uani 1 1 d . . . . .
H3 H 0.9089 -0.4173 0.2293 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8639(3) -0.4522(3) 0.06956(19) 0.0291(6) Uani 1 1 d . . . . .
H4 H 0.8889 -0.5674 0.0734 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8155(2) -0.3709(3) -0.02665(18) 0.0266(5) Uani 1 1 d . . . . .
H5 H 0.8070 -0.4327 -0.0892 0.032 Uiso 1 1 calc R U . . .
C6 C 0.9041(3) -0.1612(3) 0.34125(17) 0.0301(6) Uani 1 1 d . . . . .
H6A H 0.9018 -0.0764 0.3935 0.036 Uiso 1 1 calc R U . . .
H6B H 0.8476 -0.2588 0.3472 0.036 Uiso 1 1 calc R U . . .
H6C H 1.0038 -0.1952 0.3551 0.036 Uiso 1 1 calc R U . . .
C7 C 0.7069(2) 0.1201(3) -0.05467(17) 0.0209(5) Uani 1 1 d . . . . .
C8 C 0.5629(2) 0.1598(3) -0.09746(17) 0.0232(5) Uani 1 1 d . . . . .
H8 H 0.4996 0.1280 -0.0618 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5109(2) 0.2468(3) -0.19323(18) 0.0251(5) Uani 1 1 d . . . . .
H9 H 0.4118 0.2751 -0.2233 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6040(3) 0.2923(3) -0.24482(18) 0.0261(5) Uani 1 1 d . . . . .
H10 H 0.5685 0.3516 -0.3104 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7494(3) 0.2516(3) -0.20091(18) 0.0266(5) Uani 1 1 d . . . . .
H11 H 0.8128 0.2823 -0.2367 0.032 Uiso 1 1 calc R U . . .
C12 C 0.8017(2) 0.1660(3) -0.10470(17) 0.0249(5) Uani 1 1 d . . . . .
H12 H 0.9011 0.1394 -0.0736 0.030 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O1 C2 1.362(3) . ?
O1 C6 1.438(3) . ?
O2 C1 1.377(3) . ?
O2 C7 1.409(3) . ?
N1 C1 1.310(3) . ?
N1 C5 1.358(3) . ?
C1 C2 1.407(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.376(3) . ?
C7 C12 1.386(3) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 C6 116.59(17) . . ?
C1 O2 C7 117.68(16) . . ?
C1 N1 C5 117.00(19) . . ?
N1 C1 O2 120.05(19) . . ?
N1 C1 C2 124.8(2) . . ?
O2 C1 C2 115.15(19) . . ?
O1 C2 C3 126.1(2) . . ?
O1 C2 C1 116.81(19) . . ?
C3 C2 C1 117.1(2) . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 123.0(2) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 121.4(2) . . ?
C8 C7 O2 117.90(19) . . ?
C12 C7 O2 120.5(2) . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C7 C12 C11 119.1(2) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?

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
C5 N1 C1 O2 179.9(2) . . . . ?
C5 N1 C1 C2 -0.9(3) . . . . ?
C7 O2 C1 N1 0.8(3) . . . . ?
C7 O2 C1 C2 -178.45(18) . . . . ?
C6 O1 C2 C3 5.7(3) . . . . ?
C6 O1 C2 C1 -174.44(19) . . . . ?
N1 C1 C2 O1 -178.7(2) . . . . ?
O2 C1 C2 O1 0.5(3) . . . . ?
N1 C1 C2 C3 1.1(3) . . . . ?
O2 C1 C2 C3 -179.62(19) . . . . ?
O1 C2 C3 C4 179.4(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C1 N1 C5 C4 0.1(3) . . . . ?
C3 C4 C5 N1 0.5(4) . . . . ?
C1 O2 C7 C8 107.2(2) . . . . ?
C1 O2 C7 C12 -77.9(3) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
O2 C7 C8 C9 175.28(18) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C8 C7 C12 C11 -1.1(3) . . . . ?
O2 C7 C12 C11 -175.75(19) . . . . ?
C10 C11 C12 C7 1.0(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        3-Methoxy-2-phenoxypyridine
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1929a
_database_code_depnum_ccdc_archive 'CCDC 1999366'
loop_
_audit_author_name
_audit_author_address
'Junko Nagaoka'
;Nagasaki University
Japan
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H13 F3 I N O'
_chemical_formula_moiety         'C18 H13 F3 I N O'
_chemical_formula_weight         443.21
_chemical_melting_point          416-417

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   6.0218(15)
_cell_length_b                   15.569(4)
_cell_length_c                   17.415(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.278(5)
_cell_angle_gamma                90.0000
_cell_volume                     1632.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4663
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864.00
_exptl_absorpt_coefficient_mu    1.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.942

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            13311
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         1.755
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3666
_reflns_number_gt                3118
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0888
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3666
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0446P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.90
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.73615(5) 0.10642(2) 0.51481(2) 0.01436(12) Uani 1 1 d . . . . .
F1 F 0.6231(6) 0.0505(2) 0.1361(2) 0.0475(10) Uani 1 1 d . . . . .
F2 F 0.8255(6) 0.1572(3) 0.1073(2) 0.0602(13) Uani 1 1 d . . . . .
F3 F 0.5473(5) 0.1737(2) 0.17981(17) 0.0323(8) Uani 1 1 d . . . . .
O1 O 1.2234(6) 0.0512(2) 0.42750(18) 0.0193(7) Uani 1 1 d . . . . .
N1 N 0.9089(7) 0.1055(3) 0.3706(2) 0.0176(9) Uani 1 1 d . . . . .
C1 C 0.6656(8) 0.2335(3) 0.4796(3) 0.0155(10) Uani 1 1 d . . . . .
C2 C 0.4596(8) 0.2519(3) 0.4464(3) 0.0181(10) Uani 1 1 d . . . . .
H2 H 0.3538 0.2076 0.4369 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4120(8) 0.3366(3) 0.4273(3) 0.0202(11) Uani 1 1 d . . . . .
H3 H 0.2717 0.3506 0.4046 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5668(10) 0.4007(3) 0.4409(3) 0.0260(12) Uani 1 1 d . . . . .
H4 H 0.5324 0.4584 0.4274 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7699(9) 0.3813(3) 0.4739(3) 0.0249(12) Uani 1 1 d . . . . .
H5 H 0.8751 0.4256 0.4837 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8215(8) 0.2969(3) 0.4929(3) 0.0196(11) Uani 1 1 d . . . . .
H6 H 0.9629 0.2830 0.5148 0.024 Uiso 1 1 calc R U . . .
C7 C 0.5705(8) 0.1292(3) 0.6196(3) 0.0162(10) Uani 1 1 d . . . . .
C8 C 0.6788(8) 0.1771(3) 0.6758(3) 0.0187(10) Uani 1 1 d . . . . .
H8 H 0.8232 0.1994 0.6676 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5725(9) 0.1920(3) 0.7444(3) 0.0258(12) Uani 1 1 d . . . . .
H9 H 0.6420 0.2262 0.7832 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3637(10) 0.1568(3) 0.7560(3) 0.0265(12) Uani 1 1 d . . . . .
H10 H 0.2922 0.1659 0.8034 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2599(9) 0.1090(3) 0.6995(3) 0.0254(12) Uani 1 1 d . . . . .
H11 H 0.1179 0.0850 0.7086 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3600(8) 0.0952(3) 0.6289(3) 0.0200(11) Uani 1 1 d . . . . .
H12 H 0.2867 0.0639 0.5890 0.024 Uiso 1 1 calc R U . . .
C13 C 1.1139(8) 0.0687(3) 0.3652(3) 0.0172(10) Uani 1 1 d . . . . .
C14 C 1.1991(8) 0.0527(3) 0.2909(3) 0.0179(10) Uani 1 1 d . . . . .
H14 H 1.3440 0.0294 0.2864 0.022 Uiso 1 1 calc R U . . .
C15 C 1.0754(8) 0.0704(3) 0.2261(3) 0.0198(11) Uani 1 1 d . . . . .
H15 H 1.1327 0.0595 0.1766 0.024 Uiso 1 1 calc R U . . .
C16 C 0.8611(8) 0.1052(3) 0.2340(3) 0.0177(10) Uani 1 1 d . . . . .
C17 C 0.7884(8) 0.1214(3) 0.3064(3) 0.0164(10) Uani 1 1 d . . . . .
H17 H 0.6443 0.1452 0.3116 0.020 Uiso 1 1 calc R U . . .
C18 C 0.7165(9) 0.1217(4) 0.1650(3) 0.0241(12) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 2.112(5) . ?
I1 C7 2.129(5) . ?
F1 C18 1.335(6) . ?
F2 C18 1.333(6) . ?
F3 C18 1.332(6) . ?
O1 C13 1.287(6) . ?
N1 C17 1.342(6) . ?
N1 C13 1.366(6) . ?
C1 C6 1.378(7) . ?
C1 C2 1.387(6) . ?
C2 C3 1.388(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.382(7) . ?
C7 C12 1.387(7) . ?
C8 C9 1.388(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.424(7) . ?
C14 C15 1.367(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.409(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.368(7) . ?
C16 C18 1.490(7) . ?
C17 H17 0.9500 . ?

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
C1 I1 C7 89.88(17) . . ?
C17 N1 C13 119.5(4) . . ?
C6 C1 C2 121.5(5) . . ?
C6 C1 I1 119.4(4) . . ?
C2 C1 I1 119.1(4) . . ?
C1 C2 C3 118.3(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.3(5) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C12 122.7(4) . . ?
C8 C7 I1 118.3(3) . . ?
C12 C7 I1 119.0(4) . . ?
C7 C8 C9 118.7(5) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 121.0(5) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 117.2(5) . . ?
C7 C12 H12 121.4 . . ?
C11 C12 H12 121.4 . . ?
O1 C13 N1 118.5(4) . . ?
O1 C13 C14 122.7(4) . . ?
N1 C13 C14 118.8(4) . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 118.7(4) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 118.3(4) . . ?
C17 C16 C18 121.2(4) . . ?
C15 C16 C18 120.5(5) . . ?
N1 C17 C16 123.8(4) . . ?
N1 C17 H17 118.1 . . ?
C16 C17 H17 118.1 . . ?
F3 C18 F2 106.6(5) . . ?
F3 C18 F1 105.1(4) . . ?
F2 C18 F1 105.7(5) . . ?
F3 C18 C16 112.6(4) . . ?
F2 C18 C16 113.0(4) . . ?
F1 C18 C16 113.3(5) . . ?

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
C6 C1 C2 C3 -0.8(7) . . . . ?
I1 C1 C2 C3 176.7(3) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
C3 C4 C5 C6 0.8(8) . . . . ?
C2 C1 C6 C5 1.3(7) . . . . ?
I1 C1 C6 C5 -176.2(4) . . . . ?
C4 C5 C6 C1 -1.2(8) . . . . ?
C12 C7 C8 C9 -0.1(7) . . . . ?
I1 C7 C8 C9 -179.8(4) . . . . ?
C7 C8 C9 C10 1.8(7) . . . . ?
C8 C9 C10 C11 -1.4(8) . . . . ?
C9 C10 C11 C12 -0.6(8) . . . . ?
C8 C7 C12 C11 -1.9(7) . . . . ?
I1 C7 C12 C11 177.8(3) . . . . ?
C10 C11 C12 C7 2.2(7) . . . . ?
C17 N1 C13 O1 -177.5(4) . . . . ?
C17 N1 C13 C14 3.6(7) . . . . ?
O1 C13 C14 C15 178.5(5) . . . . ?
N1 C13 C14 C15 -2.7(7) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 1.4(7) . . . . ?
C14 C15 C16 C18 -177.1(5) . . . . ?
C13 N1 C17 C16 -2.1(7) . . . . ?
C15 C16 C17 N1 -0.4(7) . . . . ?
C18 C16 C17 N1 178.0(5) . . . . ?
C17 C16 C18 F3 17.7(7) . . . . ?
C15 C16 C18 F3 -163.8(4) . . . . ?
C17 C16 C18 F2 138.5(5) . . . . ?
C15 C16 C18 F2 -43.0(7) . . . . ?
C17 C16 C18 F1 -101.4(6) . . . . ?
C15 C16 C18 F1 77.1(6) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'Diphenyliodonium 2-oxo-5-(trifluoromethyl)-2H-pyridin-1-ide'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
