# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_yuxu_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2084307'
loop_
_audit_author_name
_audit_author_address
'Xu Yu'
;Jilin University
China
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;
_audit_creation_date             2020-01-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yuxu19@mails.jlu.edu.cn
_chemical_name_common            ?
_chemical_name_systematic        
'Pyrene-Tetrachloroterephthalonitrile Cocrystal'
_chemical_formula_moiety         'C4 Cl2 N, C8 H5'
_chemical_formula_sum            'C12 H5 Cl2 N'
_chemical_formula_weight         234.07
_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'
Cl Cl 0.1484 0.1585 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1397(3)
_cell_length_b                   16.0756(6)
_cell_length_c                   8.9196(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.9830(10)
_cell_angle_gamma                90
_cell_volume                     988.94(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8674
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15405
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.534
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1656
_reflns_number_total             2258
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.135
_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)+(0.0002P)²+0.7901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0967
_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:
 C11(H00B), C12(H00C), C10(H00D), C6(H00E), C5(H00F)
;
_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
Cl01 Cl 0.63287(11) 0.58529(5) 0.82259(7) 0.0600(2) Uani 1 1 d . . . . .
Cl02 Cl 0.55585(11) 0.39262(5) 0.79768(7) 0.0592(2) Uani 1 1 d . . . . .
C003 C 0.5391(3) 0.58489(15) 0.5109(3) 0.0403(5) Uani 1 1 d . . . . .
C004 C 0.0250(3) 0.54273(15) 0.5105(3) 0.0406(5) Uani 1 1 d . . . . .
C005 C 0.5232(3) 0.45295(15) 0.6352(3) 0.0404(5) Uani 1 1 d . . . . .
C006 C 0.5609(3) 0.53754(15) 0.6457(3) 0.0402(5) Uani 1 1 d . . . . .
N007 N 0.6129(4) 0.74168(17) 0.5283(3) 0.0711(7) Uani 1 1 d . . . . .
C008 C 0.5804(4) 0.67239(17) 0.5210(3) 0.0496(6) Uani 1 1 d . . . . .
C009 C 0.0862(4) 0.57658(17) 0.6619(3) 0.0491(6) Uani 1 1 d . . . . .
C00A C 0.0146(3) 0.59465(17) 0.3793(3) 0.0483(6) Uani 1 1 d . . . . .
C00B C -0.0470(4) 0.5579(2) 0.2283(3) 0.0600(7) Uani 1 1 d . . . . .
H00B H -0.054048 0.591557 0.139510 0.072 Uiso 1 1 calc R U . . .
C00C C -0.0947(4) 0.4774(2) 0.2087(3) 0.0606(8) Uani 1 1 d . . . . .
H00C H -0.135157 0.455567 0.106467 0.073 Uiso 1 1 calc R U . . .
C00D C 0.1354(4) 0.6610(2) 0.6780(4) 0.0652(8) Uani 1 1 d . . . . .
H00D H 0.175464 0.684876 0.778668 0.078 Uiso 1 1 calc R U . . .
C00E C 0.0664(4) 0.67814(18) 0.4026(4) 0.0645(8) Uani 1 1 d . . . . .
H00E H 0.060189 0.713339 0.315891 0.077 Uiso 1 1 calc R U . . .
C00F C 0.1264(5) 0.7097(2) 0.5501(4) 0.0720(9) Uani 1 1 d . . . . .
H00F H 0.162555 0.766655 0.563970 0.086 Uiso 1 1 calc R U . . .


_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
Cl01 C006 1.710(2) . ?
Cl02 C005 1.709(2) . ?
C003 C005 1.402(3) 3_666 ?
C003 C006 1.397(3) . ?
C003 C008 1.435(4) . ?
C004 C004 1.420(5) 3_566 ?
C004 C009 1.416(3) . ?
C004 C00A 1.424(3) . ?
C005 C006 1.385(3) . ?
N007 C008 1.136(3) . ?
C009 C00C 1.433(4) 3_566 ?
C009 C00D 1.401(4) . ?
C00A C00B 1.432(4) . ?
C00A C00E 1.394(4) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.337(4) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9500 . ?
C00D C00F 1.371(4) . ?
C00E H00E 0.9500 . ?
C00E C00F 1.371(4) . ?
C00F H00F 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
C005 C003 C008 119.6(2) 3_666 . ?
C006 C003 C005 120.1(2) . 3_666 ?
C006 C003 C008 120.3(2) . . ?
C004 C004 C00A 120.0(3) 3_566 . ?
C009 C004 C004 120.2(3) . 3_566 ?
C009 C004 C00A 119.7(2) . . ?
C003 C005 Cl02 118.86(19) 3_666 . ?
C006 C005 Cl02 121.22(18) . . ?
C006 C005 C003 119.9(2) . 3_666 ?
C003 C006 Cl01 119.31(18) . . ?
C005 C006 Cl01 120.68(18) . . ?
C005 C006 C003 120.0(2) . . ?
N007 C008 C003 179.7(3) . . ?
C004 C009 C00C 118.3(2) . 3_566 ?
C00D C009 C004 118.5(3) . . ?
C00D C009 C00C 123.2(3) . 3_566 ?
C004 C00A C00B 118.0(2) . . ?
C00E C00A C004 119.1(3) . . ?
C00E C00A C00B 122.9(3) . . ?
C00A C00B H00B 119.1 . . ?
C00C C00B C00A 121.9(3) . . ?
C00C C00B H00B 119.1 . . ?
C009 C00C H00C 119.2 3_566 . ?
C00B C00C C009 121.6(3) . 3_566 ?
C00B C00C H00C 119.2 . . ?
C009 C00D H00D 119.6 . . ?
C00F C00D C009 120.8(3) . . ?
C00F C00D H00D 119.6 . . ?
C00A C00E H00E 119.8 . . ?
C00F C00E C00A 120.3(3) . . ?
C00F C00E H00E 119.8 . . ?
C00D C00F C00E 121.5(3) . . ?
C00D C00F H00F 119.3 . . ?
C00E C00F H00F 119.3 . . ?

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
Cl02 C005 C006 Cl01 -2.5(3) . . . . ?
Cl02 C005 C006 C003 177.90(18) . . . . ?
C003 C005 C006 Cl01 178.82(17) 3_666 . . . ?
C003 C005 C006 C003 -0.8(4) 3_666 . . . ?
C004 C004 C009 C00C -0.5(4) 3_566 . . 3_566 ?
C004 C004 C009 C00D 179.6(3) 3_566 . . . ?
C004 C004 C00A C00B 0.0(4) 3_566 . . . ?
C004 C004 C00A C00E -179.2(3) 3_566 . . . ?
C004 C009 C00D C00F -0.7(4) . . . . ?
C004 C00A C00B C00C 0.3(4) . . . . ?
C004 C00A C00E C00F -0.1(4) . . . . ?
C005 C003 C006 Cl01 -178.83(17) 3_666 . . . ?
C005 C003 C006 C005 0.8(4) 3_666 . . . ?
C008 C003 C006 Cl01 1.3(3) . . . . ?
C008 C003 C006 C005 -179.2(2) . . . . ?
C009 C004 C00A C00B 179.6(2) . . . . ?
C009 C004 C00A C00E 0.4(4) . . . . ?
C009 C00D C00F C00E 1.0(5) . . . . ?
C00A C004 C009 C00C 179.9(2) . . . 3_566 ?
C00A C004 C009 C00D 0.0(3) . . . . ?
C00A C00B C00C C009 -0.2(4) . . . 3_566 ?
C00A C00E C00F C00D -0.7(5) . . . . ?
C00B C00A C00E C00F -179.2(3) . . . . ?
C00C C009 C00D C00F 179.4(3) 3_566 . . . ?
C00E C00A C00B C00C 179.5(3) . . . . ?

_olex2_submission_original_sample_id 
'Pyrene-Tetrachloroterephthalonitrile Cocrystal'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_yuxu_0927_0m
_database_code_depnum_ccdc_archive 'CCDC 2084309'
loop_
_audit_author_name
_audit_author_address
'Xu Yu'
;Jilin University
China
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;
_audit_creation_date             2020-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yuxu19@mails.jlu.edu.cn
_chemical_name_common            ?
_chemical_name_systematic        cocrystal
_chemical_formula_moiety         'C4 F2 N, C8 H5'
_chemical_formula_sum            'C12 H5 F2 N'
_chemical_formula_weight         201.17
_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'
N N 0.0061 0.0033 '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                   7.1268(11)
_cell_length_b                   8.6732(14)
_cell_length_c                   15.297(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.303(6)
_cell_angle_gamma                90
_cell_volume                     923.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7366
_cell_measurement_temperature    98.0
_cell_measurement_theta_max      26.662
_cell_measurement_theta_min      2.9255
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16599
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.717
_diffrn_reflns_theta_min         2.925
_diffrn_ambient_temperature      98.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1420
_reflns_number_total             1946
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1946
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.088
_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)+(0.0515P)²+0.2410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1325
_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:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F)
;
_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
F001 F 0.63381(17) 0.53992(15) 0.67761(7) 0.0842(4) Uani 1 1 d . . . . .
F002 F 0.50312(18) 0.26092(14) 0.61404(8) 0.0860(4) Uani 1 1 d . . . . .
C003 C 0.0415(2) 0.5586(2) 0.53013(11) 0.0533(4) Uani 1 1 d . . . . .
N004 N 0.3072(3) 0.0921(3) 0.40213(15) 0.0992(7) Uani 1 1 d . . . . .
C005 C 0.0712(2) 0.7085(2) 0.49819(13) 0.0649(5) Uani 1 1 d . . . . .
C006 C 0.5012(2) 0.3787(2) 0.55777(12) 0.0605(5) Uani 1 1 d . . . . .
C007 C 0.5677(2) 0.5202(2) 0.59006(11) 0.0603(4) Uani 1 1 d . . . . .
C008 C 0.4318(2) 0.3559(2) 0.46679(12) 0.0583(4) Uani 1 1 d . . . . .
C009 C 0.0970(2) 0.5254(2) 0.62325(12) 0.0655(5) Uani 1 1 d . . . . .
C00A C 0.3629(3) 0.2082(2) 0.43177(15) 0.0723(5) Uani 1 1 d . . . . .
C00B C 0.1560(3) 0.8211(3) 0.55967(17) 0.0829(6) Uani 1 1 d . . . . .
H00B H 0.177340 0.921856 0.539501 0.099 Uiso 1 1 calc R U . . .
C00C C -0.0143(3) 0.2623(3) 0.59538(15) 0.0761(6) Uani 1 1 d . . . . .
H00C H -0.033244 0.162507 0.617550 0.091 Uiso 1 1 calc R U . . .
C00D C 0.1806(3) 0.6417(3) 0.68152(14) 0.0845(7) Uani 1 1 d . . . . .
H00D H 0.218403 0.621085 0.743789 0.101 Uiso 1 1 calc R U . . .
C00E C 0.0654(3) 0.3725(3) 0.65279(14) 0.0771(6) Uani 1 1 d . . . . .
H00E H 0.102012 0.348741 0.714706 0.093 Uiso 1 1 calc R U . . .
C00F C 0.2087(3) 0.7857(3) 0.64958(18) 0.0922(8) Uani 1 1 d . . . . .
H00F H 0.265965 0.863344 0.690466 0.111 Uiso 1 1 calc R U . . .


_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
F001 C007 1.333(2) . ?
F002 C006 1.334(2) . ?
C003 C003 1.415(3) 3_566 ?
C003 C005 1.420(3) . ?
C003 C009 1.424(2) . ?
N004 C00A 1.140(3) . ?
C005 C00B 1.400(3) . ?
C005 C00C 1.425(3) 3_566 ?
C006 C007 1.370(3) . ?
C006 C008 1.388(2) . ?
C007 C008 1.382(2) 3_666 ?
C008 C00A 1.434(3) . ?
C009 C00D 1.393(3) . ?
C009 C00E 1.434(3) . ?
C00B H00B 0.9500 . ?
C00B C00F 1.381(4) . ?
C00C H00C 0.9500 . ?
C00C C00E 1.340(3) . ?
C00D H00D 0.9500 . ?
C00D C00F 1.371(4) . ?
C00E H00E 0.9500 . ?
C00F H00F 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
C003 C003 C005 120.4(2) 3_566 . ?
C003 C003 C009 119.6(2) 3_566 . ?
C005 C003 C009 119.96(16) . . ?
C003 C005 C00C 118.48(17) . 3_566 ?
C00B C005 C003 118.79(19) . . ?
C00B C005 C00C 122.7(2) . 3_566 ?
F002 C006 C007 119.89(16) . . ?
F002 C006 C008 119.38(17) . . ?
C007 C006 C008 120.72(16) . . ?
F001 C007 C006 119.88(17) . . ?
F001 C007 C008 119.01(17) . 3_666 ?
C006 C007 C008 121.11(16) . 3_666 ?
C006 C008 C00A 121.46(17) . . ?
C007 C008 C006 118.17(16) 3_666 . ?
C007 C008 C00A 120.37(17) 3_666 . ?
C003 C009 C00E 118.26(17) . . ?
C00D C009 C003 118.9(2) . . ?
C00D C009 C00E 122.8(2) . . ?
N004 C00A C008 178.5(3) . . ?
C005 C00B H00B 120.0 . . ?
C00F C00B C005 120.1(2) . . ?
C00F C00B H00B 120.0 . . ?
C005 C00C H00C 119.3 3_566 . ?
C00E C00C C005 121.5(2) . 3_566 ?
C00E C00C H00C 119.3 . . ?
C009 C00D H00D 119.8 . . ?
C00F C00D C009 120.4(2) . . ?
C00F C00D H00D 119.8 . . ?
C009 C00E H00E 119.1 . . ?
C00C C00E C009 121.75(19) . . ?
C00C C00E H00E 119.1 . . ?
C00B C00F H00F 119.1 . . ?
C00D C00F C00B 121.9(2) . . ?
C00D C00F H00F 119.1 . . ?

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
F002 C006 C007 F001 -0.1(2) . . . . ?
F002 C006 C007 C008 179.70(15) . . . 3_666 ?
F002 C006 C008 C007 -179.70(14) . . . 3_666 ?
F002 C006 C008 C00A -0.3(3) . . . . ?
C003 C003 C005 C00B -179.19(18) 3_566 . . . ?
C003 C003 C005 C00C 0.4(3) 3_566 . . 3_566 ?
C003 C003 C009 C00D 179.26(19) 3_566 . . . ?
C003 C003 C009 C00E -0.2(3) 3_566 . . . ?
C003 C005 C00B C00F -0.2(3) . . . . ?
C003 C009 C00D C00F 0.1(3) . . . . ?
C003 C009 C00E C00C -0.1(3) . . . . ?
C005 C003 C009 C00D -0.2(2) . . . . ?
C005 C003 C009 C00E -179.73(16) . . . . ?
C005 C00B C00F C00D 0.1(3) . . . . ?
C005 C00C C00E C009 0.2(3) 3_566 . . . ?
C007 C006 C008 C007 0.1(3) . . . 3_666 ?
C007 C006 C008 C00A 179.53(16) . . . . ?
C008 C006 C007 F001 -179.98(15) . . . . ?
C008 C006 C007 C008 -0.1(3) . . . 3_666 ?
C009 C003 C005 C00B 0.3(2) . . . . ?
C009 C003 C005 C00C 179.91(15) . . . 3_566 ?
C009 C00D C00F C00B 0.0(3) . . . . ?
C00C C005 C00B C00F -179.80(19) 3_566 . . . ?
C00D C009 C00E C00C -179.60(19) . . . . ?
C00E C009 C00D C00F 179.54(19) . . . . ?

_olex2_submission_original_sample_id 1
_olex2_submission_special_instructions 'No special instructions were received'
