# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_C6H2Br3OH_22BPE
_database_code_depnum_ccdc_archive 'CCDC 2337582'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_C6H2Br3OH_22BPE     
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2023-10-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
ryangroeneman19@webster.edu
daniel-unruh@uiowa.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2, 2(C6 H3 Br3 O)'
_chemical_formula_sum            'C24 H16 Br6 N2 O2'
_chemical_formula_weight         843.85
_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'
Br Br -0.2901 2.4595 '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/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                   15.2907(6)
_cell_length_b                   4.0298(2)
_cell_length_c                   22.1448(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.3530(10)
_cell_angle_gamma                90
_cell_volume                     1309.33(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    290.00
_cell_measurement_theta_max      28.012
_cell_measurement_theta_min      2.776
_shelx_estimated_absorpt_T_max   0.526
_shelx_estimated_absorpt_T_min   0.198
_exptl_absorpt_coefficient_mu    9.225
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.5660.
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    2.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            35054
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_min         2.777
_diffrn_ambient_temperature      290.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2497
_reflns_number_total             3113
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.021
_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)+(0.0288P)²+1.3713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0739
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Br1 Br 0.70863(2) 0.95730(10) 0.33499(2) 0.05511(13) Uani 1 1 d . . . . .
Br2 Br 0.35716(2) 0.36700(9) 0.25676(2) 0.05034(12) Uani 1 1 d . . . . .
Br3 Br 0.53491(3) 0.77102(13) 0.07754(2) 0.07816(16) Uani 1 1 d . . . . .
O1 O 0.52948(15) 0.6082(7) 0.34691(10) 0.0514(6) Uani 1 1 d . . . . .
H1 H 0.580449 0.628945 0.371534 0.077 Uiso 1 1 calc R U . . .
N1 N 0.65187(18) 0.6678(7) 0.46265(12) 0.0486(6) Uani 1 1 d . . . . .
C1 C 0.60602(19) 0.8052(7) 0.27133(14) 0.0395(6) Uani 1 1 d . . . . .
C2 C 0.53383(19) 0.6580(8) 0.28838(13) 0.0392(6) Uani 1 1 d . . . . .
C3 C 0.4598(2) 0.5561(7) 0.23836(14) 0.0384(6) Uani 1 1 d . . . . .
C4 C 0.4593(2) 0.5889(8) 0.17621(14) 0.0447(7) Uani 1 1 d . . . . .
H4 H 0.409971 0.514596 0.144012 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5333(2) 0.7336(8) 0.16272(15) 0.0470(7) Uani 1 1 d . . . . .
C6 C 0.6066(2) 0.8462(8) 0.20957(15) 0.0449(7) Uani 1 1 d . . . . .
H6 H 0.655604 0.947794 0.199911 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6122(2) 0.7670(8) 0.50638(14) 0.0457(7) Uani 1 1 d . . . . .
C8 C 0.7329(3) 0.5197(10) 0.48158(18) 0.0594(9) Uani 1 1 d . . . . .
H8 H 0.760442 0.453953 0.451056 0.071 Uiso 1 1 calc R U . . .
C9 C 0.7780(3) 0.4587(10) 0.54322(18) 0.0645(10) Uani 1 1 d . . . . .
H9 H 0.834686 0.355785 0.554298 0.077 Uiso 1 1 calc R U . . .
C10 C 0.7369(3) 0.5540(11) 0.58846(18) 0.0669(11) Uani 1 1 d . . . . .
H10 H 0.765494 0.515145 0.630834 0.080 Uiso 1 1 calc R U . . .
C11 C 0.6535(3) 0.7070(10) 0.57023(16) 0.0595(9) Uani 1 1 d . . . . .
H11 H 0.624618 0.770375 0.600164 0.071 Uiso 1 1 calc R U . . .
C12 C 0.5248(2) 0.9380(9) 0.48300(14) 0.0480(7) Uani 1 1 d . . . . .
H12 H 0.502160 0.960886 0.439591 0.058 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
Br1 C1 1.892(3) . ?
Br2 C3 1.889(3) . ?
Br3 C5 1.899(3) . ?
O1 H1 0.8200 . ?
O1 C2 1.332(4) . ?
N1 C7 1.341(4) . ?
N1 C8 1.332(5) . ?
C1 C2 1.395(4) . ?
C1 C6 1.380(4) . ?
C2 C3 1.404(4) . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(5) . ?
C5 C6 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C11 1.398(4) . ?
C7 C12 1.462(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(6) . ?
C11 H11 0.9300 . ?
C12 C12 1.309(7) 3_676 ?
C12 H12 0.9300 . ?

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 . . ?
C8 N1 C7 118.5(3) . . ?
C2 C1 Br1 119.3(2) . . ?
C6 C1 Br1 117.7(2) . . ?
C6 C1 C2 123.0(3) . . ?
O1 C2 C1 126.0(3) . . ?
O1 C2 C3 118.3(3) . . ?
C1 C2 C3 115.7(3) . . ?
C2 C3 Br2 118.8(2) . . ?
C4 C3 Br2 118.8(2) . . ?
C4 C3 C2 122.4(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 Br3 119.3(3) . . ?
C6 C5 Br3 119.3(2) . . ?
C6 C5 C4 121.4(3) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 H6 120.7 . . ?
N1 C7 C11 120.7(3) . . ?
N1 C7 C12 116.1(3) . . ?
C11 C7 C12 123.2(3) . . ?
N1 C8 H8 118.1 . . ?
N1 C8 C9 123.9(4) . . ?
C9 C8 H8 118.1 . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.1(4) . . ?
C10 C9 H9 120.9 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C7 C11 H11 120.2 . . ?
C10 C11 C7 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C7 C12 H12 116.7 . . ?
C12 C12 C7 126.6(4) 3_676 . ?
C12 C12 H12 116.7 3_676 . ?

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 N1 0.82 2.01 2.725(3) 145.2 . 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
Br1 C1 C2 O1 -0.7(4) . . . . ?
Br1 C1 C2 C3 179.2(2) . . . . ?
Br1 C1 C6 C5 179.2(2) . . . . ?
Br2 C3 C4 C5 178.6(2) . . . . ?
Br3 C5 C6 C1 -177.4(2) . . . . ?
O1 C2 C3 Br2 1.8(4) . . . . ?
O1 C2 C3 C4 -178.1(3) . . . . ?
N1 C7 C11 C10 2.0(6) . . . . ?
N1 C7 C12 C12 -178.4(5) . . . 3_676 ?
N1 C8 C9 C10 0.4(7) . . . . ?
C1 C2 C3 Br2 -178.0(2) . . . . ?
C1 C2 C3 C4 2.1(4) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
C3 C4 C5 Br3 178.6(2) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C6 C1 C2 O1 179.3(3) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
C7 N1 C8 C9 0.8(6) . . . . ?
C8 N1 C7 C11 -2.0(5) . . . . ?
C8 N1 C7 C12 178.0(3) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C9 C10 C11 C7 -0.8(6) . . . . ?
C11 C7 C12 C12 1.6(7) . . . 3_676 ?
C12 C7 C11 C10 -178.0(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_C6H2CL3OH_22BPE
_database_code_depnum_ccdc_archive 'CCDC 2337583'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2023-10-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
ryangroeneman19@webster.edu
daniel-unruh@uiowa.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2, 2(C6 H3 Cl3 O)'
_chemical_formula_sum            'C24 H16 Cl6 N2 O2'
_chemical_formula_weight         577.09
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8425(3)
_cell_length_b                   11.4827(8)
_cell_length_c                   13.8828(9)
_cell_angle_alpha                94.128(2)
_cell_angle_beta                 94.256(2)
_cell_angle_gamma                95.001(2)
_cell_volume                     606.63(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5471
_cell_measurement_temperature    290.00
_cell_measurement_theta_max      27.227
_cell_measurement_theta_min      2.405
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6655
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0677 after correction.
The Ratio of minimum to maximum transmission is 0.8925.
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    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19706
_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         26.726
_diffrn_reflns_theta_min         2.225
_diffrn_ambient_temperature      290.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1985
_reflns_number_total             2566
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.035
_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)+(0.0395P)²+0.3354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1072
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Cl1 Cl 0.4802(2) 0.92238(6) 0.72854(5) 0.0640(2) Uani 1 1 d . . . . .
Cl2 Cl 0.0825(2) 0.49875(5) 0.84810(5) 0.0609(2) Uani 1 1 d . . . . .
Cl3 Cl 0.7636(2) 0.83578(7) 1.09937(5) 0.0642(2) Uani 1 1 d . . . . .
O1 O 0.1279(5) 0.67330(15) 0.70970(11) 0.0524(4) Uani 1 1 d . . . . .
H1 H 0.185743 0.717740 0.668826 0.079 Uiso 1 1 calc R U . . .
N1 N 0.2444(6) 0.73773(16) 0.52987(14) 0.0451(5) Uani 1 1 d . . . . .
C1 C 0.4529(6) 0.82629(19) 0.81907(16) 0.0420(5) Uani 1 1 d . . . . .
C2 C 0.2848(6) 0.71421(19) 0.79664(15) 0.0397(5) Uani 1 1 d . . . . .
C3 C 0.2758(6) 0.64071(19) 0.87216(16) 0.0422(5) Uani 1 1 d . . . . .
C4 C 0.4196(6) 0.6765(2) 0.96467(17) 0.0473(5) Uani 1 1 d . . . . .
H4 H 0.407450 0.625693 1.013815 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5819(6) 0.7888(2) 0.98321(17) 0.0447(5) Uani 1 1 d . . . . .
C6 C 0.6014(6) 0.8648(2) 0.91125(17) 0.0444(5) Uani 1 1 d . . . . .
H6 H 0.711680 0.940323 0.924063 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3469(6) 0.64980(18) 0.47202(15) 0.0386(5) Uani 1 1 d . . . . .
C8 C 0.1399(7) 0.8317(2) 0.48850(19) 0.0532(6) Uani 1 1 d . . . . .
H8 H 0.066702 0.892000 0.528242 0.064 Uiso 1 1 calc R U . . .
C9 C 0.1342(7) 0.8445(2) 0.3912(2) 0.0546(6) Uani 1 1 d . . . . .
H9 H 0.060402 0.911837 0.365773 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2401(7) 0.7554(2) 0.33203(19) 0.0566(7) Uani 1 1 d . . . . .
H10 H 0.240482 0.761527 0.265599 0.068 Uiso 1 1 calc R U . . .
C11 C 0.3458(7) 0.6571(2) 0.37250(17) 0.0489(6) Uani 1 1 d . . . . .
H11 H 0.416145 0.595646 0.333397 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4592(6) 0.54955(19) 0.52121(16) 0.0430(5) Uani 1 1 d . . . . .
H12 H 0.474443 0.556353 0.588578 0.052 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
Cl1 C1 1.734(2) . ?
Cl2 C3 1.730(2) . ?
Cl3 C5 1.738(2) . ?
O1 H1 0.8200 . ?
O1 C2 1.342(3) . ?
N1 C7 1.349(3) . ?
N1 C8 1.336(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 C6 1.375(3) . ?
C6 H6 0.9300 . ?
C7 C11 1.390(3) . ?
C7 C12 1.461(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C12 1.317(4) 2_666 ?
C12 H12 0.9300 . ?

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 . . ?
C8 N1 C7 118.0(2) . . ?
C2 C1 Cl1 119.04(17) . . ?
C6 C1 Cl1 118.21(18) . . ?
C6 C1 C2 122.8(2) . . ?
O1 C2 C1 125.4(2) . . ?
O1 C2 C3 118.4(2) . . ?
C1 C2 C3 116.3(2) . . ?
C2 C3 Cl2 118.53(18) . . ?
C4 C3 Cl2 119.04(18) . . ?
C4 C3 C2 122.4(2) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 Cl3 119.72(19) . . ?
C6 C5 Cl3 119.16(19) . . ?
C6 C5 C4 121.1(2) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 H6 120.8 . . ?
N1 C7 C11 121.0(2) . . ?
N1 C7 C12 115.57(19) . . ?
C11 C7 C12 123.4(2) . . ?
N1 C8 H8 118.0 . . ?
N1 C8 C9 123.9(2) . . ?
C9 C8 H8 118.0 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.3(2) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C7 C11 H11 120.1 . . ?
C10 C11 C7 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C7 C12 H12 117.0 . . ?
C12 C12 C7 125.9(3) 2_666 . ?
C12 C12 H12 117.0 2_666 . ?

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 N1 0.82 1.99 2.712(3) 147.2 . 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
Cl1 C1 C2 O1 -2.2(3) . . . . ?
Cl1 C1 C2 C3 179.15(17) . . . . ?
Cl1 C1 C6 C5 -179.72(18) . . . . ?
Cl2 C3 C4 C5 178.35(18) . . . . ?
Cl3 C5 C6 C1 -179.55(17) . . . . ?
O1 C2 C3 Cl2 3.2(3) . . . . ?
O1 C2 C3 C4 -177.8(2) . . . . ?
N1 C7 C11 C10 0.3(4) . . . . ?
N1 C7 C12 C12 173.9(3) . . . 2_666 ?
N1 C8 C9 C10 0.4(4) . . . . ?
C1 C2 C3 Cl2 -178.06(17) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 Cl3 179.82(18) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C6 C1 C2 O1 178.0(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C7 N1 C8 C9 -0.7(4) . . . . ?
C8 N1 C7 C11 0.4(3) . . . . ?
C8 N1 C7 C12 179.8(2) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C9 C10 C11 C7 -0.6(4) . . . . ?
C11 C7 C12 C12 -6.7(5) . . . 2_666 ?
C12 C7 C11 C10 -179.1(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_C6H2F3OH_22BPE
_database_code_depnum_ccdc_archive 'CCDC 2337585'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT334_C6H2F3OH_22BPE      
;
PROBLEM: Small <C-C> Benzene Dist.   C1       -C6       .       1.37 Ang.  
RESPONSE: Due to back donation of electron density from the 3 fluorine 
          atoms bound to the phenyl ring.
;
_vrf_PLAT911_C6H2F3OH_22BPE      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2023-10-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
ryangroeneman19@webster.edu
daniel-unruh@uiowa.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2, 2(C6 H3 F3 O)'
_chemical_formula_sum            'C24 H16 F6 N2 O2'
_chemical_formula_weight         478.39
_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'
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/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                   16.4149(11)
_cell_length_b                   3.8067(4)
_cell_length_c                   17.2311(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.309(2)
_cell_angle_gamma                90
_cell_volume                     1062.53(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3911
_cell_measurement_temperature    290.00
_cell_measurement_theta_max      24.772
_cell_measurement_theta_min      2.396
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1179 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.6859.
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    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.075
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24075
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.871
_diffrn_ambient_temperature      290.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1668
_reflns_number_total             2171
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.067
_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)+(0.0489P)²+0.2114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
F1 F 0.57066(8) 0.5679(4) 0.33155(6) 0.0911(11) Uani 1 1 d . . . . .
F2 F 0.44891(8) 0.8701(4) 0.07687(6) 0.0948(11) Uani 1 1 d . . . . .
F3 F 0.71566(8) 0.3929(4) 0.12204(8) 0.1014(11) Uani 1 1 d . . . . .
O1 O 0.43843(8) 0.8498(5) 0.22950(8) 0.0791(11) Uani 1 1 d . . . . .
H1 H 0.437375 0.785268 0.274733 0.119 Uiso 1 1 calc R U . . .
C1 C 0.57448(11) 0.5893(5) 0.25393(10) 0.0609(11) Uani 1 1 d . . . . .
C2 C 0.50677(10) 0.7258(5) 0.20563(10) 0.0586(11) Uani 1 1 d . . . . .
C3 C 0.51392(11) 0.7397(6) 0.12684(10) 0.0652(11) Uani 1 1 d . . . . .
C4 C 0.58213(13) 0.6320(6) 0.09729(11) 0.0730(11) Uani 1 1 d . . . . .
H4 H 0.584588 0.647211 0.043852 0.088 Uiso 1 1 calc R U . . .
C5 C 0.64670(12) 0.5009(6) 0.14942(12) 0.0691(11) Uani 1 1 d . . . . .
C6 C 0.64481(11) 0.4762(5) 0.22823(11) 0.0656(11) Uani 1 1 d . . . . .
H6 H 0.689280 0.386630 0.262899 0.079 Uiso 1 1 calc R U . . .
N1 N 0.38304(8) 0.7208(4) 0.36285(8) 0.0541(11) Uani 1 1 d . . . . .
C7 C 0.40077(9) 0.8117(4) 0.43904(9) 0.0490(11) Uani 1 1 d . . . . .
C8 C 0.30890(10) 0.5803(5) 0.33650(11) 0.0610(11) Uani 1 1 d . . . . .
H8 H 0.297137 0.514796 0.283881 0.073 Uiso 1 1 calc R U . . .
C9 C 0.24952(11) 0.5277(5) 0.38254(12) 0.0659(11) Uani 1 1 d . . . . .
H9 H 0.198367 0.433684 0.361656 0.079 Uiso 1 1 calc R U . . .
C10 C 0.26785(11) 0.6183(5) 0.46087(12) 0.0678(11) Uani 1 1 d . . . . .
H10 H 0.229266 0.582878 0.494120 0.081 Uiso 1 1 calc R U . . .
C11 C 0.34366(10) 0.7614(5) 0.48940(10) 0.0585(11) Uani 1 1 d . . . . .
H11 H 0.356662 0.824359 0.542103 0.070 Uiso 1 1 calc R U . . .
C12 C 0.48248(10) 0.9659(5) 0.46364(9) 0.0528(11) Uani 1 1 d . . . . .
H12 H 0.512662 1.021370 0.424046 0.063 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
F1 C1 1.351(2) . ?
F2 C3 1.353(2) . ?
F3 C5 1.359(2) . ?
O1 H1 0.8200 . ?
O1 C2 1.342(2) . ?
C1 C2 1.378(2) . ?
C1 C6 1.371(3) . ?
C2 C3 1.383(2) . ?
C3 C4 1.366(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(3) . ?
C5 C6 1.366(3) . ?
C6 H6 0.9300 . ?
N1 C7 1.343(2) . ?
N1 C8 1.340(2) . ?
C7 C11 1.390(2) . ?
C7 C12 1.463(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(3) . ?
C11 H11 0.9300 . ?
C12 C12 1.317(3) 3_676 ?
C12 H12 0.9300 . ?

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 . . ?
F1 C1 C2 117.29(16) . . ?
F1 C1 C6 118.50(16) . . ?
C6 C1 C2 124.22(17) . . ?
O1 C2 C1 125.47(16) . . ?
O1 C2 C3 119.71(15) . . ?
C1 C2 C3 114.79(16) . . ?
F2 C3 C2 117.10(17) . . ?
F2 C3 C4 118.88(17) . . ?
C4 C3 C2 124.02(17) . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.36(18) . . ?
C5 C4 H4 121.3 . . ?
F3 C5 C4 118.88(18) . . ?
F3 C5 C6 118.57(18) . . ?
C6 C5 C4 122.55(18) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 C1 117.07(17) . . ?
C5 C6 H6 121.5 . . ?
C8 N1 C7 118.39(15) . . ?
N1 C7 C11 120.89(14) . . ?
N1 C7 C12 115.48(14) . . ?
C11 C7 C12 123.63(15) . . ?
N1 C8 H8 118.1 . . ?
N1 C8 C9 123.75(17) . . ?
C9 C8 H8 118.1 . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 117.93(16) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.41(18) . . ?
C11 C10 H10 120.3 . . ?
C7 C11 H11 120.2 . . ?
C10 C11 C7 119.63(17) . . ?
C10 C11 H11 120.2 . . ?
C7 C12 H12 116.8 . . ?
C12 C12 C7 126.4(2) 3_676 . ?
C12 C12 H12 116.8 3_676 . ?

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 N1 0.82 1.90 2.6501(19) 152.2 . 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
F1 C1 C2 O1 2.3(3) . . . . ?
F1 C1 C2 C3 -179.66(17) . . . . ?
F1 C1 C6 C5 179.91(18) . . . . ?
F2 C3 C4 C5 -179.89(19) . . . . ?
F3 C5 C6 C1 179.65(18) . . . . ?
O1 C2 C3 F2 -2.1(3) . . . . ?
O1 C2 C3 C4 177.6(2) . . . . ?
C1 C2 C3 F2 179.69(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 F3 -179.71(19) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C6 C1 C2 O1 -177.50(19) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
N1 C7 C11 C10 -0.3(3) . . . . ?
N1 C7 C12 C12 -170.9(2) . . . 3_676 ?
N1 C8 C9 C10 -1.3(3) . . . . ?
C7 N1 C8 C9 0.9(3) . . . . ?
C8 N1 C7 C11 0.0(2) . . . . ?
C8 N1 C7 C12 -179.53(15) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C7 -0.2(3) . . . . ?
C11 C7 C12 C12 9.6(3) . . . 3_676 ?
C12 C7 C11 C10 179.19(17) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
