# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_CH_B2_0036
_database_code_depnum_ccdc_archive 'CCDC 2170565'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2018/3

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.1  (Andrew D. Bond, March 2019)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Maria Storer'
_cambridge_user_crsid            mcs92
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             MCS01
_cambridge_data_id               CH_B2_0036

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, 2(C3 H2 F6 O)'
_chemical_formula_sum            'C18 H12 F12 N2 O2'
_chemical_formula_weight         516.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.3987(2)
_cell_length_b                   16.0317(4)
_cell_length_c                   18.0020(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.6860(10)
_cell_angle_gamma                90
_cell_volume                     2110.79(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7678
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      66.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.621
_shelx_estimated_absorpt_T_min   0.642
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5009
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20234
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.711
_diffrn_reflns_theta_max         66.655
_diffrn_reflns_theta_full        66.656
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3709
_reflns_number_gt                3028
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1459P)²+1.9385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3709
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2655
_refine_ls_wR_factor_gt          0.2496
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.064

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
N1 N 0.3592(4) 0.65611(16) 0.55715(15) 0.0471(6) Uani 1 1 d . . . . .
N2 N 0.2532(3) 0.49867(15) 0.59214(13) 0.0393(6) Uani 1 1 d . . . . .
C1 C 0.4107(6) 0.7320(2) 0.5389(2) 0.0636(10) Uani 1 1 d . . . . .
H1A H 0.438845 0.771614 0.578185 0.076 Uiso 1 1 calc R U . . .
C2 C 0.4260(6) 0.7572(3) 0.4666(3) 0.0745(12) Uani 1 1 d . . . . .
H2A H 0.462458 0.812436 0.456801 0.089 Uiso 1 1 calc R U . . .
C3 C 0.3879(5) 0.7013(3) 0.4101(2) 0.0690(12) Uani 1 1 d . . . . .
H3A H 0.398432 0.717097 0.360117 0.083 Uiso 1 1 calc R U . . .
C4 C 0.3325(4) 0.6193(2) 0.42526(18) 0.0521(8) Uani 1 1 d . . . . .
C5 C 0.2913(5) 0.5574(3) 0.36877(19) 0.0665(11) Uani 1 1 d . . . . .
H5A H 0.302599 0.570591 0.318227 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2373(5) 0.4814(3) 0.38520(19) 0.0646(11) Uani 1 1 d . . . . .
H6A H 0.209589 0.441575 0.346048 0.077 Uiso 1 1 calc R U . . .
C7 C 0.2198(4) 0.4580(2) 0.46125(18) 0.0482(8) Uani 1 1 d . . . . .
C8 C 0.1604(5) 0.3797(2) 0.4807(2) 0.0599(10) Uani 1 1 d . . . . .
H8A H 0.129208 0.338519 0.443002 0.072 Uiso 1 1 calc R U . . .
C9 C 0.1470(5) 0.3619(2) 0.5539(2) 0.0598(9) Uani 1 1 d . . . . .
H9A H 0.105004 0.308850 0.567524 0.072 Uiso 1 1 calc R U . . .
C10 C 0.1962(4) 0.4233(2) 0.6084(2) 0.0495(8) Uani 1 1 d . . . . .
H10A H 0.188545 0.410502 0.659324 0.059 Uiso 1 1 calc R U . . .
C11 C 0.3215(4) 0.59986(19) 0.50108(16) 0.0402(7) Uani 1 1 d . . . . .
C12 C 0.2645(4) 0.51720(18) 0.51923(15) 0.0377(6) Uani 1 1 d . . . . .
O1 O 0.3774(4) 0.57266(16) 0.71927(13) 0.0617(7) Uani 1 1 d . . . . .
H1 H 0.335(8) 0.553(3) 0.670(3) 0.093 Uiso 1 1 d . U . . .
C13 C 0.3373(5) 0.6561(2) 0.72966(18) 0.0544(8) Uani 1 1 d . . . . .
H13A H 0.295126 0.681869 0.679457 0.065 Uiso 1 1 calc R U . . .
C14 C 0.5098(6) 0.6995(3) 0.7652(3) 0.0729(11) Uani 1 1 d . . . . .
C15 C 0.1876(6) 0.6640(4) 0.7769(3) 0.0876(15) Uani 1 1 d . . . . .
F1 F 0.5746(5) 0.6667(2) 0.83245(17) 0.1085(11) Uani 1 1 d . . . . .
F2 F 0.4898(5) 0.77962(18) 0.7761(2) 0.1065(10) Uani 1 1 d . . . . .
F3 F 0.6374(4) 0.6935(3) 0.7215(2) 0.1216(13) Uani 1 1 d . . . . .
F4 F 0.2280(6) 0.6278(3) 0.84402(16) 0.1314(14) Uani 1 1 d . . . . .
F5 F 0.1481(5) 0.7460(3) 0.7873(2) 0.1278(14) Uani 1 1 d . . . . .
F6 F 0.0381(5) 0.6285(3) 0.7429(2) 0.1486(18) Uani 1 1 d . . . . .
O2 O 0.5511(8) 0.4499(2) 0.79940(18) 0.1153(17) Uani 1 1 d . . . . .
H2 H 0.473(13) 0.486(6) 0.771(5) 0.173 Uiso 1 1 d . U . . .
C16 C 0.5658(6) 0.4552(2) 0.8752(2) 0.0640(10) Uani 1 1 d . . . . .
H16A H 0.503345 0.507476 0.887800 0.077 Uiso 1 1 calc R U . . .
C17 C 0.7693(13) 0.4601(5) 0.9118(6) 0.142(3) Uani 1 1 d . . . . .
C18 C 0.4699(13) 0.3824(5) 0.9045(4) 0.123(2) Uani 1 1 d . . . . .
F7 F 0.8577(8) 0.3979(4) 0.8920(5) 0.233(4) Uani 1 1 d . . . . .
F8 F 0.8354(8) 0.5267(4) 0.8883(7) 0.285(5) Uani 1 1 d . . . . .
F9 F 0.7682(12) 0.4569(5) 0.9886(4) 0.236(4) Uani 1 1 d . . . . .
F10 F 0.5313(10) 0.3106(2) 0.8870(3) 0.190(3) Uani 1 1 d . . . . .
F11 F 0.4790(12) 0.3842(4) 0.9773(3) 0.227(4) Uani 1 1 d . . . . .
F12 F 0.2977(10) 0.3839(5) 0.8734(6) 0.252(4) Uani 1 1 d . . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.331(5) . ?
N1 C11 1.351(4) . ?
N2 C10 1.326(4) . ?
N2 C12 1.360(4) . ?
C1 C2 1.384(6) . ?
C1 H1A 0.9500 . ?
C2 C3 1.352(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.415(6) . ?
C3 H3A 0.9500 . ?
C4 C11 1.414(4) . ?
C4 C5 1.421(6) . ?
C5 C6 1.330(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.444(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.393(5) . ?
C7 C12 1.412(4) . ?
C8 C9 1.366(6) . ?
C8 H8A 0.9500 . ?
C9 C10 1.399(5) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.443(4) . ?
O1 C13 1.388(4) . ?
O1 H1 0.94(6) . ?
C13 C15 1.500(6) . ?
C13 C14 1.508(6) . ?
C13 H13A 1.0000 . ?
C14 F2 1.311(5) . ?
C14 F3 1.320(6) . ?
C14 F1 1.341(6) . ?
C15 F6 1.311(6) . ?
C15 F4 1.333(7) . ?
C15 F5 1.365(7) . ?
O2 C16 1.354(5) . ?
O2 H2 0.91(9) . ?
C16 C18 1.502(8) . ?
C16 C17 1.552(11) . ?
C16 H16A 1.0000 . ?
C17 F8 1.273(9) . ?
C17 F7 1.273(10) . ?
C17 F9 1.385(12) . ?
C18 F10 1.294(9) . ?
C18 F11 1.302(9) . ?
C18 F12 1.312(10) . ?

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 N1 C11 117.4(3) . . ?
C10 N2 C12 118.6(3) . . ?
N1 C1 C2 124.5(4) . . ?
N1 C1 H1A 117.8 . . ?
C2 C1 H1A 117.8 . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C11 C4 C3 116.8(3) . . ?
C11 C4 C5 120.0(3) . . ?
C3 C4 C5 123.2(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C8 C7 C12 117.9(3) . . ?
C8 C7 C6 123.3(3) . . ?
C12 C7 C6 118.8(3) . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 118.7(3) . . ?
C8 C9 H9A 120.7 . . ?
C10 C9 H9A 120.7 . . ?
N2 C10 C9 123.0(3) . . ?
N2 C10 H10A 118.5 . . ?
C9 C10 H10A 118.5 . . ?
N1 C11 C4 122.6(3) . . ?
N1 C11 C12 118.6(2) . . ?
C4 C11 C12 118.8(3) . . ?
N2 C12 C7 121.7(3) . . ?
N2 C12 C11 118.8(2) . . ?
C7 C12 C11 119.5(3) . . ?
C13 O1 H1 113(3) . . ?
O1 C13 C15 110.4(4) . . ?
O1 C13 C14 108.5(3) . . ?
C15 C13 C14 111.7(3) . . ?
O1 C13 H13A 108.7 . . ?
C15 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
F2 C14 F3 105.5(4) . . ?
F2 C14 F1 106.4(4) . . ?
F3 C14 F1 108.5(4) . . ?
F2 C14 C13 114.1(4) . . ?
F3 C14 C13 110.5(3) . . ?
F1 C14 C13 111.5(4) . . ?
F6 C15 F4 107.0(5) . . ?
F6 C15 F5 107.4(5) . . ?
F4 C15 F5 108.6(4) . . ?
F6 C15 C13 110.0(4) . . ?
F4 C15 C13 113.1(4) . . ?
F5 C15 C13 110.6(5) . . ?
C16 O2 H2 118(6) . . ?
O2 C16 C18 109.6(5) . . ?
O2 C16 C17 110.9(5) . . ?
C18 C16 C17 111.7(5) . . ?
O2 C16 H16A 108.2 . . ?
C18 C16 H16A 108.2 . . ?
C17 C16 H16A 108.2 . . ?
F8 C17 F7 108.9(9) . . ?
F8 C17 F9 115.1(11) . . ?
F7 C17 F9 109.4(7) . . ?
F8 C17 C16 107.4(6) . . ?
F7 C17 C16 110.3(8) . . ?
F9 C17 C16 105.7(7) . . ?
F10 C18 F11 107.4(6) . . ?
F10 C18 F12 105.4(8) . . ?
F11 C18 F12 109.2(9) . . ?
F10 C18 C16 113.8(7) . . ?
F11 C18 C16 112.4(6) . . ?
F12 C18 C16 108.3(6) . . ?

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
C11 N1 C1 C2 0.8(5) . . . . ?
N1 C1 C2 C3 -0.6(6) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C2 C3 C4 C11 -0.6(5) . . . . ?
C2 C3 C4 C5 -179.7(4) . . . . ?
C11 C4 C5 C6 1.8(5) . . . . ?
C3 C4 C5 C6 -179.1(3) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C5 C6 C7 C8 178.7(3) . . . . ?
C5 C6 C7 C12 -1.1(5) . . . . ?
C12 C7 C8 C9 -0.1(4) . . . . ?
C6 C7 C8 C9 -179.9(3) . . . . ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C12 N2 C10 C9 0.0(4) . . . . ?
C8 C9 C10 N2 1.0(5) . . . . ?
C1 N1 C11 C4 -0.9(4) . . . . ?
C1 N1 C11 C12 -179.7(3) . . . . ?
C3 C4 C11 N1 0.8(4) . . . . ?
C5 C4 C11 N1 179.9(3) . . . . ?
C3 C4 C11 C12 179.6(3) . . . . ?
C5 C4 C11 C12 -1.3(4) . . . . ?
C10 N2 C12 C7 -1.0(4) . . . . ?
C10 N2 C12 C11 178.3(2) . . . . ?
C8 C7 C12 N2 1.0(4) . . . . ?
C6 C7 C12 N2 -179.1(3) . . . . ?
C8 C7 C12 C11 -178.2(3) . . . . ?
C6 C7 C12 C11 1.6(4) . . . . ?
N1 C11 C12 N2 -0.9(4) . . . . ?
C4 C11 C12 N2 -179.7(2) . . . . ?
N1 C11 C12 C7 178.4(3) . . . . ?
C4 C11 C12 C7 -0.5(4) . . . . ?
O1 C13 C14 F2 178.4(4) . . . . ?
C15 C13 C14 F2 -59.6(6) . . . . ?
O1 C13 C14 F3 59.7(5) . . . . ?
C15 C13 C14 F3 -178.3(4) . . . . ?
O1 C13 C14 F1 -61.1(4) . . . . ?
C15 C13 C14 F1 61.0(5) . . . . ?
O1 C13 C15 F6 -61.7(6) . . . . ?
C14 C13 C15 F6 177.4(5) . . . . ?
O1 C13 C15 F4 57.9(5) . . . . ?
C14 C13 C15 F4 -63.0(6) . . . . ?
O1 C13 C15 F5 179.9(3) . . . . ?
C14 C13 C15 F5 59.0(5) . . . . ?
O2 C16 C17 F8 62.4(10) . . . . ?
C18 C16 C17 F8 -175.0(8) . . . . ?
O2 C16 C17 F7 -56.1(8) . . . . ?
C18 C16 C17 F7 66.5(9) . . . . ?
O2 C16 C17 F9 -174.2(6) . . . . ?
C18 C16 C17 F9 -51.7(8) . . . . ?
O2 C16 C18 F10 57.8(7) . . . . ?
C17 C16 C18 F10 -65.5(8) . . . . ?
O2 C16 C18 F11 -179.8(7) . . . . ?
C17 C16 C18 F11 56.9(10) . . . . ?
O2 C16 C18 F12 -59.1(9) . . . . ?
C17 C16 C18 F12 177.6(8) . . . . ?

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 0.94(6) 2.65(5) 3.195(4) 118(4) . yes
O1 H1 N2 0.94(6) 1.69(6) 2.618(3) 167(5) . yes
O2 H2 O1 0.91(9) 1.77(9) 2.655(4) 164(9) . yes

####################################################################### 
# 
# 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_CH_B2_0037
_database_code_depnum_ccdc_archive 'CCDC 2170566'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2018/3

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.1  (Andrew D. Bond, March 2019)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Maria Chiara Storer'
_cambridge_user_crsid            mcs92
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             MCS92
_cambridge_data_id               CH_B2_0037

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, C4 H4 F6 O'
_chemical_formula_sum            'C16 H12 F6 N2 O'
_chemical_formula_weight         362.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   11.1618(7)
_cell_length_b                   12.3056(7)
_cell_length_c                   11.4093(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.225(3)
_cell_angle_gamma                90
_cell_volume                     1554.65(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9203
_cell_measurement_theta_min      3.99
_cell_measurement_theta_max      66.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.308
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6215
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13952
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.992
_diffrn_reflns_theta_max         66.575
_diffrn_reflns_theta_full        66.575
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2719
_reflns_number_gt                2449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.9186P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     296
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.045

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
N1 N 0.53045(13) 0.74681(12) 0.51880(13) 0.0343(4) Uani 1 1 d . . . . .
N2 N 0.63763(13) 0.60010(12) 0.68051(12) 0.0323(4) Uani 1 1 d . . . . .
C1 C 0.47655(19) 0.81669(16) 0.44110(17) 0.0419(5) Uani 1 1 d . . . . .
H1A H 0.523484 0.874622 0.415985 0.050 Uiso 1 1 calc R U . . .
C2 C 0.35469(19) 0.81069(18) 0.39354(18) 0.0466(5) Uani 1 1 d . . . . .
H2A H 0.320484 0.863400 0.338351 0.056 Uiso 1 1 calc R U . . .
C3 C 0.28635(17) 0.72776(18) 0.42804(17) 0.0435(5) Uani 1 1 d . . . . .
H3A H 0.203441 0.722143 0.397290 0.052 Uiso 1 1 calc R U . . .
C4 C 0.33918(16) 0.65049(15) 0.50943(15) 0.0340(4) Uani 1 1 d . . . . .
C5 C 0.27339(17) 0.55972(17) 0.54679(17) 0.0407(5) Uani 1 1 d . . . . .
H5A H 0.190473 0.551429 0.517187 0.049 Uiso 1 1 calc R U . . .
C6 C 0.32698(18) 0.48588(16) 0.62313(17) 0.0399(5) Uani 1 1 d . . . . .
H6A H 0.281582 0.425929 0.646022 0.048 Uiso 1 1 calc R U . . .
C7 C 0.45171(17) 0.49649(14) 0.67042(15) 0.0333(4) Uani 1 1 d . . . . .
C8 C 0.5095(2) 0.42157(16) 0.75079(17) 0.0419(5) Uani 1 1 d . . . . .
H8A H 0.466179 0.361232 0.776012 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6284(2) 0.43580(17) 0.79268(17) 0.0452(5) Uani 1 1 d . . . . .
H9A H 0.669263 0.385036 0.846299 0.054 Uiso 1 1 calc R U . . .
C10 C 0.68895(18) 0.52630(16) 0.75536(16) 0.0396(5) Uani 1 1 d . . . . .
H10A H 0.771660 0.535524 0.785310 0.047 Uiso 1 1 calc R U . . .
C11 C 0.46264(15) 0.66405(14) 0.55295(14) 0.0287(4) Uani 1 1 d . . . . .
C12 C 0.51971(15) 0.58570(14) 0.63680(14) 0.0286(4) Uani 1 1 d . . . . .
O1 O 0.78727(12) 0.77711(11) 0.70907(11) 0.0381(3) Uani 0.810(3) 1 d D . P A 1
H1 H 0.738(2) 0.727(2) 0.678(2) 0.057 Uiso 0.810(3) 1 d . U P A 1
F1 F 0.92108(17) 0.61578(13) 0.6164(2) 0.0786(7) Uani 0.810(3) 1 d D . P A 1
F2 F 1.01704(16) 0.69380(16) 0.7588(2) 0.1005(7) Uani 0.810(3) 1 d D . P A 1
F3 F 1.0612(2) 0.72696(19) 0.5886(3) 0.0943(9) Uani 0.810(3) 1 d D . P A 1
F4 F 0.85719(16) 0.98704(12) 0.6724(2) 0.0932(6) Uani 0.810(3) 1 d D . P A 1
F5 F 0.9676(2) 0.9050(2) 0.7989(3) 0.0885(9) Uani 0.810(3) 1 d D . P A 1
F6 F 1.02709(17) 0.93558(16) 0.6288(2) 0.0856(8) Uani 0.810(3) 1 d D . P A 1
C13 C 0.87436(16) 0.79992(15) 0.63475(16) 0.0355(4) Uani 0.810(3) 1 d D . P A 1
C14 C 0.9705(2) 0.7098(2) 0.6510(3) 0.0498(7) Uani 0.810(3) 1 d D . P A 1
C15 C 0.9320(2) 0.9082(2) 0.6830(3) 0.0532(8) Uani 0.810(3) 1 d D . P A 1
C16 C 0.8267(3) 0.8122(4) 0.5068(2) 0.0651(10) Uani 0.810(3) 1 d D . P A 1
H16A H 0.893662 0.827402 0.461369 0.098 Uiso 0.810(3) 1 calc R U P A 1
H16B H 0.768726 0.872327 0.497221 0.098 Uiso 0.810(3) 1 calc R U P A 1
H16C H 0.786371 0.744782 0.478014 0.098 Uiso 0.810(3) 1 calc R U P A 1
O1' O 0.78727(12) 0.77711(11) 0.70907(11) 0.0381(3) Uani 0.190(3) 1 d D . P A 2
H1' H 0.738(2) 0.727(2) 0.678(2) 0.057 Uiso 0.190(3) 1 d . U P A 2
F1' F 1.0110(9) 0.8457(11) 0.7956(8) 0.108(5) Uani 0.190(3) 1 d D U P A 2
F2' F 1.01704(16) 0.69380(16) 0.7588(2) 0.1005(7) Uani 0.190(3) 1 d D U P A 2
F3' F 1.0795(8) 0.8014(14) 0.6322(10) 0.136(5) Uani 0.190(3) 1 d D U P A 2
F4' F 0.85719(16) 0.98704(12) 0.6724(2) 0.0932(6) Uani 0.190(3) 1 d D U P A 2
F5' F 0.9200(12) 0.9490(9) 0.5206(10) 0.133(5) Uani 0.190(3) 1 d D U P A 2
F6' F 0.7332(8) 0.9366(8) 0.5513(9) 0.109(4) Uani 0.190(3) 1 d D U P A 2
C13' C 0.87436(16) 0.79992(15) 0.63475(16) 0.0355(4) Uani 0.190(3) 1 d D . P A
2
C14' C 0.9968(7) 0.7816(8) 0.7019(9) 0.085(5) Uani 0.190(3) 1 d D . P A 2
C15' C 0.8471(8) 0.9180(6) 0.5961(7) 0.075(5) Uani 0.190(3) 1 d D . P A 2
C16' C 0.8492(14) 0.7324(12) 0.5215(10) 0.070(4) Uani 0.190(3) 1 d D . P A 2
H16D H 0.904042 0.755023 0.465392 0.105 Uiso 0.190(3) 1 calc R U P A 2
H16E H 0.765476 0.743618 0.486257 0.105 Uiso 0.190(3) 1 calc R U P A 2
H16F H 0.862116 0.655229 0.540444 0.105 Uiso 0.190(3) 1 calc R U P A 2


_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
N1 C1 1.324(2) . ?
N1 C11 1.355(2) . ?
N2 C10 1.326(2) . ?
N2 C12 1.359(2) . ?
C1 C2 1.402(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.362(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.406(3) . ?
C3 H3A 0.9500 . ?
C4 C11 1.415(2) . ?
C4 C5 1.431(3) . ?
C5 C6 1.346(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.434(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.399(3) . ?
C7 C12 1.415(2) . ?
C8 C9 1.364(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.397(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.448(2) . ?
O1 C13 1.396(2) . ?
O1 H1 0.87(3) . ?
F1 C14 1.321(3) . ?
F2 C14 1.288(3) . ?
F3 C14 1.326(3) . ?
F4 C15 1.276(3) . ?
F5 C15 1.333(4) . ?
F6 C15 1.337(3) . ?
C13 C16 1.497(3) . ?
C13 C14 1.538(3) . ?
C13 C15 1.550(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O1' C13' 1.396(2) . ?
O1' H1' 0.87(3) . ?
F1' C14' 1.321(9) . ?
F2' C14' 1.267(8) . ?
F3' C14' 1.315(9) . ?
F4' C15' 1.211(8) . ?
F5' C15' 1.314(9) . ?
F6' C15' 1.329(9) . ?
C13' C14' 1.497(8) . ?
C13' C16' 1.532(8) . ?
C13' C15' 1.537(8) . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 0.9800 . ?

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 N1 C11 117.22(16) . . ?
C10 N2 C12 117.83(16) . . ?
N1 C1 C2 124.21(19) . . ?
N1 C1 H1A 117.9 . . ?
C2 C1 H1A 117.9 . . ?
C3 C2 C1 118.64(18) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 119.61(18) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C11 117.47(17) . . ?
C3 C4 C5 122.44(17) . . ?
C11 C4 C5 120.08(17) . . ?
C6 C5 C4 121.13(17) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C7 120.89(17) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C8 C7 C12 118.05(17) . . ?
C8 C7 C6 122.13(17) . . ?
C12 C7 C6 119.81(17) . . ?
C9 C8 C7 119.53(18) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 118.84(18) . . ?
C8 C9 H9A 120.6 . . ?
C10 C9 H9A 120.6 . . ?
N2 C10 C9 123.76(18) . . ?
N2 C10 H10A 118.1 . . ?
C9 C10 H10A 118.1 . . ?
N1 C11 C4 122.85(16) . . ?
N1 C11 C12 118.37(15) . . ?
C4 C11 C12 118.78(15) . . ?
N2 C12 C7 121.97(16) . . ?
N2 C12 C11 118.74(15) . . ?
C7 C12 C11 119.29(15) . . ?
C13 O1 H1 109.9(17) . . ?
O1 C13 C16 115.02(18) . . ?
O1 C13 C14 108.07(17) . . ?
C16 C13 C14 110.3(2) . . ?
O1 C13 C15 104.26(16) . . ?
C16 C13 C15 109.9(2) . . ?
C14 C13 C15 108.95(18) . . ?
F2 C14 F1 104.8(3) . . ?
F2 C14 F3 107.1(2) . . ?
F1 C14 F3 107.3(2) . . ?
F2 C14 C13 114.6(2) . . ?
F1 C14 C13 109.7(2) . . ?
F3 C14 C13 112.9(2) . . ?
F4 C15 F5 103.1(3) . . ?
F4 C15 F6 108.2(2) . . ?
F5 C15 F6 108.1(3) . . ?
F4 C15 C13 112.5(2) . . ?
F5 C15 C13 112.7(2) . . ?
F6 C15 C13 111.7(2) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13' O1' H1' 109.9(17) . . ?
O1' C13' C14' 108.6(4) . . ?
O1' C13' C16' 109.6(5) . . ?
C14' C13' C16' 114.1(7) . . ?
O1' C13' C15' 103.7(3) . . ?
C14' C13' C15' 115.1(5) . . ?
C16' C13' C15' 105.2(7) . . ?
F2' C14' F3' 111.9(10) . . ?
F2' C14' F1' 95.7(9) . . ?
F3' C14' F1' 110.9(10) . . ?
F2' C14' C13' 118.9(7) . . ?
F3' C14' C13' 109.1(8) . . ?
F1' C14' C13' 109.5(7) . . ?
F4' C15' F5' 104.9(8) . . ?
F4' C15' F6' 98.8(8) . . ?
F5' C15' F6' 109.8(10) . . ?
F4' C15' C13' 117.4(6) . . ?
F5' C15' C13' 110.2(7) . . ?
F6' C15' C13' 114.7(7) . . ?
C13' C16' H16D 109.5 . . ?
C13' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C13' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?

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^a H1^a N2 0.87(3) 1.93(3) 2.739(2) 155(2) . yes

