# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2386785'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2024-09-25 deposited with the CCDC.	2025-06-23 downloaded from the CCDC.
;
_audit_creation_date             2024-01-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H10 F6 N2'
_chemical_formula_sum            'C22 H10 F6 N2'
_chemical_formula_weight         416.32
_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 0.0181 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'
F F 0.0727 0.0534 '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'

_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                   13.8593(9)
_cell_length_b                   8.9825(6)
_cell_length_c                   7.7141(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.320(4)
_cell_angle_gamma                90
_cell_volume                     926.21(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.83
_cell_measurement_theta_min      3.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.148
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5221
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1509 before and 0.0917 after correction.
The Ratio of minimum to maximum transmission is 0.6937.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.901
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6884
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.982
_diffrn_reflns_theta_min         3.306
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'micro gap gas area detector'
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker X8  area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                981
_reflns_number_total             1510
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0783
_refine_ls_restrained_S_all      1.079
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2423
_refine_ls_wR_factor_ref         0.2885
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: F1(0.6) F1A(0.4) F2(0.6) F2A(0.4) F3(0.6) F3A(0.4)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.0496(12) 0.3513(12) 0.829(2) 0.124(3) Uani 0.6 1 d . . P . .
F1A F 0.114(2) 0.343(2) 0.947(4) 0.149(6) Uani 0.4 1 d . . P . .
F2 F 0.1534(6) 0.466(3) 1.0221(10) 0.147(4) Uani 0.6 1 d . . P . .
F2A F 0.125(2) 0.566(2) 0.979(3) 0.143(8) Uani 0.4 1 d . . P . .
F3 F 0.0410(10) 0.5788(11) 0.841(2) 0.120(3) Uani 0.6 1 d . . P . .
F3A F 0.0104(7) 0.480(5) 0.7790(17) 0.167(8) Uani 0.4 1 d . . P . .
N1 N 0.4957(2) 0.3727(3) 0.1026(4) 0.0664(9) Uani 1 1 d . . . . .
C1 C 0.5449(3) 0.3748(4) -0.0234(5) 0.0650(10) Uani 1 1 d . . . . .
H1 H 0.5779 0.2889 -0.0430 0.078 Uiso 1 1 calc R U . . .
C2 C 0.4509(3) 0.5008(3) 0.1270(5) 0.0587(10) Uani 1 1 d . . . . .
C3 C 0.3965(3) 0.5019(3) 0.2596(5) 0.0602(10) Uani 1 1 d . . . . .
C4 C 0.3481(3) 0.5020(3) 0.3684(5) 0.0605(10) Uani 1 1 d . . . . .
C5 C 0.2886(3) 0.4967(3) 0.4941(5) 0.0585(10) Uani 1 1 d . . . . .
C6 C 0.3085(2) 0.3939(4) 0.6319(5) 0.0616(10) Uani 1 1 d . . . . .
H6 H 0.3626 0.3295 0.6461 0.074 Uiso 1 1 calc R U . . .
C7 C 0.2488(3) 0.3862(4) 0.7486(5) 0.0660(10) Uani 1 1 d . . . . .
H7 H 0.2628 0.3169 0.8415 0.079 Uiso 1 1 calc R U . . .
C8 C 0.1685(3) 0.4804(4) 0.7286(5) 0.0614(10) Uani 1 1 d . . . . .
C9 C 0.1488(3) 0.5857(4) 0.5954(6) 0.0743(12) Uani 1 1 d . . . . .
H9 H 0.0958 0.6517 0.5845 0.089 Uiso 1 1 calc R U . . .
C10 C 0.2083(3) 0.5931(5) 0.4770(6) 0.0768(12) Uani 1 1 d . . . . .
H10 H 0.1944 0.6633 0.3851 0.092 Uiso 1 1 calc R U . . .
C11 C 0.1025(3) 0.4682(5) 0.8535(7) 0.0761(12) 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
F1 F1A 1.10(2) . ?
F1 F3A 1.29(2) . ?
F1 C11 1.266(7) . ?
F1A F2 1.30(2) . ?
F1A C11 1.325(11) . ?
F2 F2A 0.998(15) . ?
F2 C11 1.306(9) . ?
F2A F3 1.36(2) . ?
F2A C11 1.282(12) . ?
F3 F3A 1.05(2) . ?
F3 C11 1.296(7) . ?
F3A C11 1.258(11) . ?
N1 C1 1.326(5) . ?
N1 C2 1.344(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(5) 3_665 ?
C2 C1 1.384(5) 3_665 ?
C2 C3 1.422(5) . ?
C3 C4 1.205(5) . ?
C4 C5 1.430(5) . ?
C5 C6 1.380(5) . ?
C5 C10 1.388(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(5) . ?
C8 C9 1.370(5) . ?
C8 C11 1.497(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(5) . ?
C10 H10 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
F1A F1 F3A 119.7(12) . . ?
F1A F1 C11 67.7(8) . . ?
C11 F1 F3A 59.0(7) . . ?
F1 F1A F2 117.6(11) . . ?
F1 F1A C11 62.1(8) . . ?
F2 F1A C11 59.7(7) . . ?
F1A F2 C11 61.2(8) . . ?
F2A F2 F1A 122.4(15) . . ?
F2A F2 C11 66.1(10) . . ?
F2 F2A F3 121.2(14) . . ?
F2 F2A C11 68.5(8) . . ?
C11 F2A F3 58.7(8) . . ?
F3A F3 F2A 116.4(14) . . ?
F3A F3 C11 63.9(10) . . ?
C11 F3 F2A 57.7(6) . . ?
F3 F3A F1 122.4(13) . . ?
F3 F3A C11 67.7(8) . . ?
C11 F3A F1 59.6(9) . . ?
C1 N1 C2 115.9(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.9(3) . 3_665 ?
C2 C1 H1 118.6 3_665 . ?
N1 C2 C1 121.2(3) . 3_665 ?
N1 C2 C3 117.3(3) . . ?
C1 C2 C3 121.4(3) 3_665 . ?
C4 C3 C2 178.3(4) . . ?
C3 C4 C5 177.6(3) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 C10 118.8(3) . . ?
C10 C5 C4 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C11 119.8(3) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 C11 119.9(3) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.5(3) . . ?
C10 C9 H9 120.3 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
F1 C11 F1A 50.2(10) . . ?
F1 C11 F2 106.0(7) . . ?
F1 C11 F2A 134.1(7) . . ?
F1 C11 F3 106.3(7) . . ?
F1 C11 C8 113.0(4) . . ?
F1A C11 C8 113.9(6) . . ?
F2 C11 F1A 59.1(10) . . ?
F2 C11 C8 112.4(5) . . ?
F2A C11 F1A 101.3(12) . . ?
F2A C11 F2 45.4(8) . . ?
F2A C11 F3 63.6(10) . . ?
F2A C11 C8 111.7(6) . . ?
F3 C11 F1A 132.5(6) . . ?
F3 C11 F2 104.9(7) . . ?
F3 C11 C8 113.5(5) . . ?
F3A C11 F1 61.4(12) . . ?
F3A C11 F1A 106.4(11) . . ?
F3A C11 F2 132.3(7) . . ?
F3A C11 F2A 107.7(13) . . ?
F3A C11 F3 48.4(12) . . ?
F3A C11 C8 114.7(6) . . ?

_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_co-1d
_database_code_depnum_ccdc_archive 'CCDC 2386790'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2024-09-25 deposited with the CCDC.	2025-06-23 downloaded from the CCDC.
;
_audit_creation_date             2023-03-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelxl_version_number           2013-4
loop_
_audit_author_email
anamaria.rfdez@uclm.es
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 F4 I2, C22 H16 N2 O2'
_chemical_formula_sum            'C28 H16 F4 I2 N2 O2'
_chemical_formula_weight         742.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.5640(18)
_cell_length_b                   8.794(2)
_cell_length_c                   10.735(3)
_cell_angle_alpha                98.860(3)
_cell_angle_beta                 109.775(3)
_cell_angle_gamma                97.838(3)
_cell_volume                     650.2(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1693
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      2.805
_cell_measurement_theta_min      24.484
_shelx_estimated_absorpt_T_max   0.755
_shelx_estimated_absorpt_T_min   0.544
_exptl_absorpt_coefficient_mu    2.477
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0820 before and 0.0341 after correction.
The Ratio of minimum to maximum transmission is 0.6770.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5454
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.536
_diffrn_reflns_theta_min         2.805
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             0.9
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2227
_reflns_number_total             3243
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         1.276
_refine_diff_density_min         -1.106
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      0.981
_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)+(0.0757P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1364
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.45402(5) 0.70580(5) 0.72123(4) 0.04907(18) Uani 1 1 d . . . . .
F1 F 0.0471(5) 0.8018(4) 0.6224(4) 0.0577(10) Uani 1 1 d . . . . .
F2 F -0.2972(5) 0.6490(4) 0.4568(4) 0.0612(10) Uani 1 1 d . . . . .
C12 C 0.1838(7) 0.5826(6) 0.5885(5) 0.0333(11) Uani 1 1 d . . . . .
C13 C 0.0283(8) 0.6525(6) 0.5626(6) 0.0388(12) Uani 1 1 d . . . . .
C14 C -0.1513(8) 0.5733(7) 0.4769(6) 0.0425(13) Uani 1 1 d . . . . .
O1 O 1.2572(6) 0.3836(5) 0.8690(5) 0.0551(11) Uani 1 1 d . . . . .
N1 N 0.8275(7) 0.8998(6) 0.9192(5) 0.0458(12) Uani 1 1 d . . . . .
C1 C 0.8353(8) 1.0475(7) 0.9699(6) 0.0425(13) Uani 1 1 d . . . . .
H1 H 0.7217 1.0849 0.9494 0.051 Uiso 1 1 calc R U . . .
C2 C 0.9942(8) 0.8497(6) 0.9472(5) 0.0365(12) Uani 1 1 d . . . . .
C3 C 0.9883(8) 0.6882(7) 0.8920(6) 0.0377(12) Uani 1 1 d . . . . .
C4 C 0.9763(8) 0.5578(7) 0.8460(6) 0.0414(13) Uani 1 1 d . . . . .
C5 C 0.9343(8) 0.3946(6) 0.7802(5) 0.0367(12) Uani 1 1 d . . . . .
C6 C 1.0774(7) 0.3022(6) 0.7897(5) 0.0376(12) Uani 1 1 d . . . . .
C7 C 1.0267(9) 0.1511(7) 0.7241(6) 0.0489(15) Uani 1 1 d . . . . .
H7 H 1.1196 0.0905 0.7298 0.059 Uiso 1 1 calc R U . . .
C8 C 0.8384(10) 0.0865(8) 0.6491(7) 0.0547(16) Uani 1 1 d . . . . .
H8 H 0.8064 -0.0185 0.6045 0.066 Uiso 1 1 calc R U . . .
C9 C 0.6957(9) 0.1682(7) 0.6366(7) 0.0576(18) Uani 1 1 d . . . . .
H9 H 0.5685 0.1209 0.5849 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7460(9) 0.3239(7) 0.7033(6) 0.0479(14) Uani 1 1 d . . . . .
H10 H 0.6509 0.3824 0.6962 0.057 Uiso 1 1 calc R U . . .
C11 C 1.4094(9) 0.2991(9) 0.8817(8) 0.0616(18) Uani 1 1 d . . . . .
H11A H 1.3998 0.2478 0.7933 0.092 Uiso 1 1 calc R U . . .
H11B H 1.3996 0.2218 0.9345 0.092 Uiso 1 1 calc R U . . .
H11C H 1.5307 0.3710 0.9259 0.092 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
I1 C12 2.081(5) . ?
F1 C13 1.336(6) . ?
F2 C14 1.338(6) . ?
C12 C13 1.366(7) . ?
C12 C14 1.389(8) 2_566 ?
C13 C14 1.370(8) . ?
C14 C12 1.389(8) 2_566 ?
O1 C6 1.360(7) . ?
O1 C11 1.433(7) . ?
N1 C1 1.314(7) . ?
N1 C2 1.345(7) . ?
C1 C2 1.389(8) 2_777 ?
C2 C1 1.389(8) 2_777 ?
C2 C3 1.441(8) . ?
C3 C4 1.155(8) . ?
C4 C5 1.439(8) . ?
C5 C6 1.426(7) . ?
C5 C10 1.379(8) . ?
C6 C7 1.341(8) . ?
C7 C8 1.364(9) . ?
C8 C9 1.358(9) . ?
C9 C10 1.380(8) . ?

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
C13 C12 I1 120.9(4) . . ?
C13 C12 C14 116.7(5) . 2_566 ?
C14 C12 I1 122.4(4) 2_566 . ?
F1 C13 C12 120.4(5) . . ?
F1 C13 C14 117.5(5) . . ?
C12 C13 C14 122.0(5) . . ?
F2 C14 C12 120.0(5) . 2_566 ?
F2 C14 C13 118.8(5) . . ?
C13 C14 C12 121.3(5) . 2_566 ?
C6 O1 C11 116.3(5) . . ?
C1 N1 C2 117.5(5) . . ?
N1 C1 C2 122.8(5) . 2_777 ?
N1 C2 C1 119.7(5) . 2_777 ?
N1 C2 C3 118.2(5) . . ?
C1 C2 C3 122.1(5) 2_777 . ?
C4 C3 C2 177.5(6) . . ?
C3 C4 C5 172.3(6) . . ?
C6 C5 C4 123.4(5) . . ?
C10 C5 C4 118.4(5) . . ?
C10 C5 C6 118.2(5) . . ?
O1 C6 C5 113.0(5) . . ?
C7 C6 O1 127.2(5) . . ?
C7 C6 C5 119.8(5) . . ?
C6 C7 C8 119.8(5) . . ?
C9 C8 C7 123.1(6) . . ?
C8 C9 C10 117.6(6) . . ?
C5 C10 C9 121.4(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'


# start Validation Reply Form
_vrf_RINTA01_1c                  
;
PROBLEM:
RINTA01_ALERT_3_A The value of Rint is greater than 0.25
RESPONSE:For this alert and related:
The compound has diffracted very weakly. Although it has been measured 
with Cu radiation, no better data has been obtained. Nevertheless, 
we believe that the results are sufficient to carry out our study
;

# end Validation Reply Form
####################################################################### 
# 
# 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_Co_1b
_database_code_depnum_ccdc_archive 'CCDC 2386787'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2024-09-25 deposited with the CCDC.	2025-06-23 downloaded from the CCDC.
;
_audit_creation_date             2022-12-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 F4 I2, C22 H10 F6 N2'
_chemical_formula_sum            'C28 H10 F10 I2 N2'
_chemical_formula_weight         818.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.8345(6)
_cell_length_b                   10.8849(12)
_cell_length_c                   13.6831(15)
_cell_angle_alpha                104.169(4)
_cell_angle_beta                 99.308(4)
_cell_angle_gamma                98.754(4)
_cell_volume                     674.97(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4341
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.113
_cell_measurement_theta_min      2.837
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.572
_exptl_absorpt_coefficient_mu    2.421
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0876 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.7147.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5738
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         2.838
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2088
_reflns_number_total             2329
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -1.138
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.087
_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)+(0.0401P)²+0.7466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0977
_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:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.56954(7) 0.76917(3) 0.28200(2) 0.05323(17) Uani 1 1 d . . . . .
F4 F 0.5816(8) 1.0687(3) 0.3813(3) 0.0680(10) Uani 1 1 d . . . . .
F5 F 0.9083(7) 1.2447(3) 0.5437(3) 0.0634(9) Uani 1 1 d . . . . .
C12 C 0.8285(11) 0.9063(5) 0.4129(4) 0.0433(11) Uani 1 1 d . . . . .
C13 C 0.7898(11) 1.0325(5) 0.4391(4) 0.0466(12) Uani 1 1 d . . . . .
C14 C 0.9560(11) 1.1231(5) 0.5235(4) 0.0452(12) Uani 1 1 d . . . . .
F1 F 0.4763(8) 0.0979(4) 0.1206(4) 0.1053(16) Uani 1 1 d . . . . .
F2 F 0.7912(12) 0.1446(4) 0.0404(3) 0.1089(16) Uani 1 1 d . . . . .
F3 F 0.8400(10) 0.0137(4) 0.1286(4) 0.0966(14) Uani 1 1 d . . . . .
N1 N 0.1736(9) 0.5823(4) 0.0917(3) 0.0418(10) Uani 1 1 d . . . . .
C1 C -0.0334(10) 0.6198(5) 0.0369(4) 0.0430(12) Uani 1 1 d . . . . .
H1 H -0.0634 0.7034 0.0604 0.052 Uiso 1 1 calc R U . . .
C2 C 0.2061(10) 0.4605(5) 0.0538(4) 0.0389(11) Uani 1 1 d . . . . .
C3 C 0.4258(11) 0.4157(5) 0.1109(4) 0.0441(12) Uani 1 1 d . . . . .
C4 C 0.6069(11) 0.3804(5) 0.1609(4) 0.0452(12) Uani 1 1 d . . . . .
C5 C 0.8299(11) 0.3529(5) 0.2313(4) 0.0450(12) Uani 1 1 d . . . . .
C6 C 0.9042(11) 0.2330(5) 0.2188(4) 0.0452(12) Uani 1 1 d . . . . .
C7 C 1.1164(11) 0.2129(6) 0.2882(4) 0.0501(13) Uani 1 1 d . . . . .
H7 H 1.1629 0.1316 0.2791 0.060 Uiso 1 1 calc R U . . .
C8 C 1.2637(13) 0.3150(6) 0.3732(5) 0.0650(17) Uani 1 1 d . . . . .
H8 H 1.4090 0.3018 0.4206 0.078 Uiso 1 1 calc R U . . .
C9 C 1.1940(13) 0.4345(6) 0.3866(5) 0.0674(18) Uani 1 1 d . . . . .
H9 H 1.2902 0.5024 0.4435 0.081 Uiso 1 1 calc R U . . .
C10 C 0.9815(13) 0.4538(6) 0.3156(4) 0.0584(15) Uani 1 1 d . . . . .
H10 H 0.9381 0.5356 0.3240 0.070 Uiso 1 1 calc R U . . .
C11 C 0.7505(12) 0.1224(6) 0.1271(4) 0.0527(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C12 2.098(5) . ?
F4 C13 1.345(5) . ?
F5 C14 1.348(6) . ?
C12 C13 1.382(7) . ?
C12 C14 1.374(7) 2_776 ?
C13 C14 1.362(7) . ?
C14 C12 1.374(7) 2_776 ?
F1 C11 1.296(7) . ?
F2 C11 1.307(7) . ?
F3 C11 1.324(7) . ?
N1 C1 1.327(6) . ?
N1 C2 1.344(6) . ?
C1 C2 1.383(7) 2_565 ?
C2 C1 1.383(7) 2_565 ?
C2 C3 1.432(6) . ?
C3 C4 1.192(7) . ?
C4 C5 1.443(7) . ?
C5 C6 1.383(7) . ?
C5 C10 1.392(7) . ?
C6 C7 1.363(7) . ?
C6 C11 1.504(7) . ?
C7 C8 1.398(8) . ?
C8 C9 1.370(8) . ?
C9 C10 1.373(7) . ?

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
C13 C12 I1 120.9(3) . . ?
C14 C12 I1 122.6(4) 2_776 . ?
C14 C12 C13 116.5(4) 2_776 . ?
F4 C13 C12 120.2(4) . . ?
F4 C13 C14 118.0(5) . . ?
C14 C13 C12 121.8(4) . . ?
F5 C14 C12 119.7(5) . 2_776 ?
F5 C14 C13 118.6(4) . . ?
C13 C14 C12 121.7(5) . 2_776 ?
C1 N1 C2 115.8(4) . . ?
N1 C1 C2 122.7(5) . 2_565 ?
N1 C2 C1 121.5(4) . 2_565 ?
N1 C2 C3 117.7(4) . . ?
C1 C2 C3 120.8(5) 2_565 . ?
C4 C3 C2 178.1(6) . . ?
C3 C4 C5 172.8(6) . . ?
C6 C5 C4 123.9(5) . . ?
C6 C5 C10 118.3(5) . . ?
C10 C5 C4 117.8(5) . . ?
C5 C6 C11 119.9(4) . . ?
C7 C6 C5 121.2(5) . . ?
C7 C6 C11 118.9(5) . . ?
C6 C7 C8 119.7(5) . . ?
C9 C8 C7 120.0(5) . . ?
C8 C9 C10 119.7(5) . . ?
C9 C10 C5 121.1(5) . . ?
F1 C11 F2 106.7(5) . . ?
F1 C11 F3 106.8(5) . . ?
F1 C11 C6 112.9(5) . . ?
F2 C11 F3 105.7(5) . . ?
F2 C11 C6 112.0(5) . . ?
F3 C11 C6 112.3(5) . . ?

_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_1b
_database_code_depnum_ccdc_archive 'CCDC 2386786'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2024-09-25 deposited with the CCDC.	2025-06-23 downloaded from the CCDC.
;
_audit_creation_date             2024-01-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H10 F6 N2'
_chemical_formula_sum            'C22 H10 F6 N2'
_chemical_formula_weight         416.32
_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 0.0181 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'
F F 0.0727 0.0534 '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'

_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   19.4412(16)
_cell_length_b                   6.8280(8)
_cell_length_c                   14.2271(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1888.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6090
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.95
_cell_measurement_theta_min      5.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.126
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5566
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1474 before and 0.0900 after correction.
The Ratio of minimum to maximum transmission is 0.7392.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.909
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16421
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.981
_diffrn_reflns_theta_min         6.221
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'micro gap gas area detector'
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker X8  area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1319
_reflns_number_total             1692
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0756
_refine_ls_restrained_S_all      1.155
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2542
_refine_ls_wR_factor_ref         0.2723
_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:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C20(H20),
 C21(H21), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.51511(19) 0.7500 0.0163(3) 0.155(2) Uani 1 2 d S T P . .
F2 F 0.52387(12) 0.9054(6) 0.1453(2) 0.1448(14) Uani 1 1 d . . . . .
F3 F 0.81135(13) 0.5959(5) 0.69072(16) 0.1206(12) Uani 1 1 d . . . . .
F4 F 0.88843(14) 0.7500 0.7672(3) 0.161(2) Uani 1 2 d S T P . .
N1 N 0.62320(17) 0.7500 0.4950(2) 0.0654(11) Uani 1 2 d S T P . .
N2 N 0.48079(15) 0.7500 0.5239(2) 0.0538(9) Uani 1 2 d S T P . .
C1 C 0.5786(2) 0.7500 0.4242(3) 0.0665(13) Uani 1 2 d S T P . .
H1 H 0.5955 0.7500 0.3631 0.080 Uiso 1 2 calc R U P . .
C2 C 0.50770(17) 0.7500 0.4377(2) 0.0458(9) Uani 1 2 d S T P . .
C3 C 0.46250(19) 0.7500 0.3585(3) 0.0535(11) Uani 1 2 d S T P . .
C4 C 0.42945(19) 0.7500 0.2885(3) 0.0527(10) Uani 1 2 d S T P . .
C5 C 0.38875(17) 0.7500 0.2045(3) 0.0480(10) Uani 1 2 d S T P . .
C6 C 0.4187(2) 0.7500 0.1148(3) 0.0588(11) Uani 1 2 d S T P . .
C7 C 0.3778(3) 0.7500 0.0359(3) 0.0678(13) Uani 1 2 d S T P . .
H7 H 0.3978 0.7500 -0.0234 0.081 Uiso 1 2 calc R U P . .
C8 C 0.3069(2) 0.7500 0.0444(3) 0.0657(13) Uani 1 2 d S T P . .
H8 H 0.2796 0.7500 -0.0092 0.079 Uiso 1 2 calc R U P . .
C9 C 0.27700(19) 0.7500 0.1313(3) 0.0598(11) Uani 1 2 d S T P . .
H9 H 0.2293 0.7500 0.1371 0.072 Uiso 1 2 calc R U P . .
C10 C 0.3178(2) 0.7500 0.2102(3) 0.0528(10) Uani 1 2 d S T P . .
H10 H 0.2970 0.7500 0.2691 0.063 Uiso 1 2 calc R U P . .
C11 C 0.4950(3) 0.7500 0.1047(4) 0.102(2) Uani 1 2 d S T P . .
C13 C 0.59593(17) 0.7500 0.5809(2) 0.0467(10) Uani 1 2 d S T P . .
C14 C 0.64028(18) 0.7500 0.6617(3) 0.0526(11) Uani 1 2 d S T P . .
C15 C 0.67213(19) 0.7500 0.7329(3) 0.0510(10) Uani 1 2 d S T P . .
C16 C 0.70604(18) 0.7500 0.8227(2) 0.0455(9) Uani 1 2 d S T P . .
C17 C 0.77825(19) 0.7500 0.8311(3) 0.0549(11) Uani 1 2 d S T P . .
C18 C 0.8073(2) 0.7500 0.9200(3) 0.0679(13) Uani 1 2 d S T P . .
H18 H 0.8549 0.7500 0.9267 0.082 Uiso 1 2 calc R U P . .
C19 C 0.7661(3) 0.7500 0.9981(3) 0.0787(15) Uani 1 2 d S T P . .
H19 H 0.7860 0.7500 1.0576 0.094 Uiso 1 2 calc R U P . .
C20 C 0.6962(3) 0.7500 0.9897(3) 0.0731(14) Uani 1 2 d S T P . .
H20 H 0.6687 0.7500 1.0432 0.088 Uiso 1 2 calc R U P . .
C21 C 0.6665(2) 0.7500 0.9027(3) 0.0591(11) Uani 1 2 d S T P . .
H21 H 0.6188 0.7500 0.8975 0.071 Uiso 1 2 calc R U P . .
C22 C 0.8231(2) 0.7500 0.7472(3) 0.0807(16) Uani 1 2 d S T P . .
C12 C 0.52532(19) 0.7500 0.5943(3) 0.0523(10) Uani 1 2 d S T P . .
H12 H 0.5085 0.7500 0.6554 0.063 Uiso 1 2 calc R U P . .


_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 C11 1.317(6) . ?
F2 C11 1.332(4) . ?
F3 C22 1.343(3) . ?
F4 C22 1.302(6) . ?
N1 C1 1.328(5) . ?
N1 C13 1.332(5) . ?
N2 C2 1.332(5) . ?
N2 C12 1.324(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.392(5) . ?
C2 C3 1.430(5) . ?
C3 C4 1.184(5) . ?
C4 C5 1.434(5) . ?
C5 C6 1.403(5) . ?
C5 C10 1.382(5) . ?
C6 C7 1.377(6) . ?
C6 C11 1.491(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(5) . ?
C10 H10 0.9300 . ?
C11 F2 1.332(4) 7_575 ?
C13 C14 1.436(5) . ?
C13 C12 1.386(5) . ?
C14 C15 1.188(5) . ?
C15 C16 1.437(5) . ?
C16 C17 1.409(5) . ?
C16 C21 1.373(5) . ?
C17 C18 1.385(5) . ?
C17 C22 1.478(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.365(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.366(6) . ?
C21 H21 0.9300 . ?
C22 F3 1.343(3) 7_575 ?
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
C1 N1 C13 115.8(3) . . ?
C12 N2 C2 116.0(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.8(4) . . ?
C2 C1 H1 118.6 . . ?
N2 C2 C1 121.1(3) . . ?
N2 C2 C3 119.0(3) . . ?
C1 C2 C3 120.0(3) . . ?
C4 C3 C2 174.9(4) . . ?
C3 C4 C5 179.4(4) . . ?
C6 C5 C4 122.0(3) . . ?
C10 C5 C4 120.1(3) . . ?
C10 C5 C6 117.9(3) . . ?
C5 C6 C11 120.1(4) . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 C11 119.8(4) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.3(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C5 C10 H10 119.1 . . ?
C9 C10 C5 121.9(4) . . ?
C9 C10 H10 119.1 . . ?
F1 C11 F2 106.8(3) . . ?
F1 C11 F2 106.8(3) . 7_575 ?
F1 C11 C6 112.8(4) . . ?
F2 C11 F2 105.6(5) . 7_575 ?
F2 C11 C6 112.1(3) 7_575 . ?
F2 C11 C6 112.1(3) . . ?
N1 C13 C14 119.7(3) . . ?
N1 C13 C12 121.3(3) . . ?
C12 C13 C14 119.0(3) . . ?
C15 C14 C13 174.5(4) . . ?
C14 C15 C16 175.9(4) . . ?
C17 C16 C15 122.2(3) . . ?
C21 C16 C15 118.7(3) . . ?
C21 C16 C17 119.1(3) . . ?
C16 C17 C22 121.2(3) . . ?
C18 C17 C16 119.0(4) . . ?
C18 C17 C22 119.8(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.7(4) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.0(4) . . ?
C20 C21 H21 119.5 . . ?
F3 C22 F3 103.1(4) . 7_575 ?
F3 C22 C17 112.5(3) 7_575 . ?
F3 C22 C17 112.5(3) . . ?
F4 C22 F3 107.2(3) . . ?
F4 C22 F3 107.2(3) . 7_575 ?
F4 C22 C17 113.5(4) . . ?
N2 C12 C13 123.0(3) . . ?
N2 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?

_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_1d
_database_code_depnum_ccdc_archive 'CCDC 2386789'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2024-09-25 deposited with the CCDC.	2025-06-23 downloaded from the CCDC.
;
_audit_creation_date             2024-01-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H16 N2 O2'
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37
_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'
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                   4.0430(14)
_cell_length_b                   15.296(5)
_cell_length_c                   13.818(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.957(4)
_cell_angle_gamma                90
_cell_volume                     854.0(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    964
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.68
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0695 before and 0.0403 after correction.
The Ratio of minimum to maximum transmission is 0.8645.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6209
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.594
_diffrn_reflns_theta_min         2.663
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1211
_reflns_number_total             2228
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    ?
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0674
_refine_ls_restrained_S_all      1.059
_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)+(0.0557P)²+0.2067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1845
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.7268(5) 0.24121(11) 0.72995(13) 0.0691(6) Uani 1 1 d . . . . .
N1 N 0.1622(5) 0.55704(13) 0.56448(15) 0.0605(6) Uani 1 1 d . . . . .
C1 C 0.0032(6) 0.58408(15) 0.48414(18) 0.0585(7) Uani 1 1 d . . . . .
H1 H 0.0013 0.6436 0.4706 0.070 Uiso 1 1 calc R U . . .
C2 C 0.1587(6) 0.47116(15) 0.58010(17) 0.0483(6) Uani 1 1 d . . . . .
C3 C 0.3303(6) 0.43764(16) 0.66420(18) 0.0541(6) Uani 1 1 d . . . . .
C4 C 0.4698(6) 0.40558(15) 0.73197(18) 0.0539(6) Uani 1 1 d . . . . .
C5 C 0.6358(6) 0.36982(15) 0.81572(17) 0.0506(6) Uani 1 1 d . . . . .
C6 C 0.7646(6) 0.28505(15) 0.81493(17) 0.0522(6) Uani 1 1 d . . . . .
C7 C 0.9154(7) 0.25111(16) 0.89720(18) 0.0583(7) Uani 1 1 d . . . . .
H7 H 1.0003 0.1946 0.8967 0.070 Uiso 1 1 calc R U . . .
C8 C 0.9414(7) 0.30028(17) 0.98022(19) 0.0636(7) Uani 1 1 d . . . . .
H8 H 1.0418 0.2765 1.0358 0.076 Uiso 1 1 calc R U . . .
C9 C 0.8210(7) 0.38401(17) 0.98210(19) 0.0643(8) Uani 1 1 d . . . . .
H9 H 0.8406 0.4172 1.0384 0.077 Uiso 1 1 calc R U . . .
C10 C 0.6709(7) 0.41830(16) 0.89985(18) 0.0600(7) Uani 1 1 d . . . . .
H10 H 0.5913 0.4753 0.9008 0.072 Uiso 1 1 calc R U . . .
C11 C 0.8628(9) 0.15512(19) 0.7268(2) 0.0863(11) Uani 1 1 d . . . . .
H11A H 0.8342 0.1320 0.6624 0.129 Uiso 1 1 calc R U . . .
H11B H 0.7512 0.1182 0.7714 0.129 Uiso 1 1 calc R U . . .
H11C H 1.0944 0.1573 0.7444 0.129 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
O1 C6 1.356(3) . ?
O1 C11 1.428(3) . ?
N1 C1 1.330(3) . ?
N1 C2 1.331(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.375(3) 3_566 ?
C2 C1 1.375(3) 3_566 ?
C2 C3 1.428(3) . ?
C3 C4 1.183(3) . ?
C4 C5 1.427(3) . ?
C5 C6 1.398(3) . ?
C5 C10 1.382(3) . ?
C6 C7 1.373(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C6 O1 C11 116.75(19) . . ?
C1 N1 C2 115.8(2) . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.6(2) . 3_566 ?
C2 C1 H1 118.2 3_566 . ?
N1 C2 C1 120.6(2) . 3_566 ?
N1 C2 C3 118.6(2) . . ?
C1 C2 C3 120.8(2) 3_566 . ?
C4 C3 C2 176.5(3) . . ?
C3 C4 C5 177.9(3) . . ?
C6 C5 C4 121.0(2) . . ?
C10 C5 C4 120.6(2) . . ?
C10 C5 C6 118.5(2) . . ?
O1 C6 C5 115.7(2) . . ?
O1 C6 C7 124.3(2) . . ?
C7 C6 C5 120.0(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
C5 C10 H10 119.3 . . ?
C9 C10 C5 121.4(2) . . ?
C9 C10 H10 119.3 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_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_1c
_database_code_depnum_ccdc_archive 'CCDC 2386788'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2024-09-25 deposited with the CCDC.	2025-06-23 downloaded from the CCDC.
;
_audit_creation_date             2024-01-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C11 H8 N O)'
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37
_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 0.0181 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'

_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                   7.810(4)
_cell_length_b                   8.569(4)
_cell_length_c                   13.576(7)
_cell_angle_alpha                100.06(3)
_cell_angle_beta                 95.24(3)
_cell_angle_gamma                90.03(3)
_cell_volume                     890.8(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    954
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      57.99
_cell_measurement_theta_min      3.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3336
_diffrn_reflns_av_unetI/netI     0.2157
_diffrn_reflns_Laue_measured_fraction_full 0.847
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8756
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.299
_diffrn_reflns_theta_min         3.320
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.847
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1275
_reflns_number_total             2727
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.226
_refine_ls_extinction_coef       0.16(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2438
_refine_ls_R_factor_gt           0.1641
_refine_ls_restrained_S_all      1.062
_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)+(0.1884P)²+1.3766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3724
_refine_ls_wR_factor_ref         0.4360
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C1A(H1A), C6A(H6A), C7A(H7A),
 C9A(H9A), C10A(H10A)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C11A(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O -0.0665(9) 0.3798(9) 0.5908(5) 0.073(2) Uani 1 1 d . . . . .
N1 N 0.9007(10) 0.6326(9) 0.9887(6) 0.058(2) Uani 1 1 d . . . . .
C1 C 1.0510(12) 0.6465(11) 1.0448(7) 0.056(2) Uani 1 1 d . . . . .
H1 H 1.0873 0.7455 1.0803 0.068 Uiso 1 1 calc R U . . .
C2 C 0.8460(12) 0.4828(10) 0.9486(7) 0.053(2) Uani 1 1 d . . . . .
C3 C 0.6824(12) 0.4646(10) 0.8875(7) 0.055(2) Uani 1 1 d . . . . .
C4 C 0.5487(12) 0.4479(11) 0.8387(7) 0.053(2) Uani 1 1 d . . . . .
C5 C 0.3880(12) 0.4315(10) 0.7783(7) 0.053(2) Uani 1 1 d . . . . .
C6 C 0.2513(12) 0.5346(10) 0.7994(7) 0.051(2) Uani 1 1 d . . . . .
H6 H 0.2648 0.6156 0.8550 0.061 Uiso 1 1 calc R U . . .
C7 C 0.1016(11) 0.5190(10) 0.7413(6) 0.047(2) Uani 1 1 d . . . . .
H7 H 0.0119 0.5858 0.7599 0.057 Uiso 1 1 calc R U . . .
C8 C 0.0766(11) 0.4064(9) 0.6542(6) 0.047(2) Uani 1 1 d . . . . .
C9 C 0.2122(13) 0.3024(11) 0.6306(8) 0.067(3) Uani 1 1 d . . . . .
H9 H 0.1988 0.2247 0.5732 0.081 Uiso 1 1 calc R U . . .
C10 C 0.3639(15) 0.3139(11) 0.6911(9) 0.071(3) Uani 1 1 d . . . . .
H10 H 0.4517 0.2437 0.6745 0.085 Uiso 1 1 calc R U . . .
C11 C -0.2011(15) 0.4871(17) 0.6079(10) 0.096(4) Uani 1 1 d . . . . .
H11A H -0.3037 0.4448 0.5677 0.144 Uiso 1 1 calc R U . . .
H11B H -0.1705 0.5863 0.5900 0.144 Uiso 1 1 calc R U . . .
H11C H -0.2211 0.5035 0.6776 0.144 Uiso 1 1 calc R U . . .
O1A O 0.5695(9) 0.1050(9) 0.4054(5) 0.072(2) Uani 1 1 d . . . . .
N1A N -0.3986(9) 0.1375(8) 0.0084(6) 0.051(2) Uani 1 1 d . . . . .
C1A C -0.5525(11) 0.1205(12) -0.0435(7) 0.055(2) Uani 1 1 d . . . . .
H1A H -0.5917 0.2016 -0.0767 0.066 Uiso 1 1 calc R U . . .
C2A C -0.3436(11) 0.0114(9) 0.0505(7) 0.046(2) Uani 1 1 d . . . . .
C3A C -0.1814(13) 0.0266(10) 0.1092(6) 0.053(2) Uani 1 1 d . . . . .
C4A C -0.0462(13) 0.0380(9) 0.1584(7) 0.053(2) Uani 1 1 d . . . . .
C5A C 0.1153(12) 0.0545(10) 0.2185(6) 0.051(2) Uani 1 1 d . . . . .
C6A C 0.2488(11) 0.1477(10) 0.1966(7) 0.050(2) Uani 1 1 d . . . . .
H6A H 0.2342 0.1985 0.1413 0.061 Uiso 1 1 calc R U . . .
C7A C 0.4011(12) 0.1645(9) 0.2564(6) 0.048(2) Uani 1 1 d . . . . .
H7A H 0.4907 0.2235 0.2398 0.057 Uiso 1 1 calc R U . . .
C8A C 0.4229(10) 0.0959(10) 0.3399(6) 0.045(2) Uani 1 1 d . . . . .
C9A C 0.2931(12) 0.0013(12) 0.3652(7) 0.059(3) Uani 1 1 d . . . . .
H9A H 0.3092 -0.0477 0.4212 0.070 Uiso 1 1 calc R U . . .
C10A C 0.1411(13) -0.0167(11) 0.3045(8) 0.063(3) Uani 1 1 d . . . . .
H10A H 0.0527 -0.0777 0.3206 0.076 Uiso 1 1 calc R U . . .
C11A C 0.7095(16) 0.1852(15) 0.3791(9) 0.083(4) Uani 1 1 d . . . . .
H11D H 0.7251 0.1485 0.3096 0.125 Uiso 1 1 calc R U . . .
H11E H 0.8113 0.1653 0.4199 0.125 Uiso 1 1 calc R U . . .
H11F H 0.6882 0.2969 0.3896 0.125 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
O1 C8 1.341(10) . ?
O1 C11 1.405(13) . ?
N1 C1 1.333(12) . ?
N1 C2 1.356(12) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(12) 2_767 ?
C2 C1 1.380(12) 2_767 ?
C2 C3 1.451(13) . ?
C3 C4 1.179(12) . ?
C4 C5 1.428(13) . ?
C5 C6 1.403(13) . ?
C5 C10 1.413(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.343(12) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(12) . ?
C8 C9 1.408(13) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(14) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O1A C8A 1.378(10) . ?
O1A C11A 1.397(13) . ?
N1A C1A 1.332(11) . ?
N1A C2A 1.359(10) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.376(12) 2_455 ?
C2A C1A 1.376(12) 2_455 ?
C2A C3A 1.427(12) . ?
C3A C4A 1.191(12) . ?
C4A C5A 1.432(13) . ?
C5A C6A 1.397(13) . ?
C5A C10A 1.408(13) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.370(12) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.363(11) . ?
C8A C9A 1.401(13) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.375(13) . ?
C10A H10A 0.9300 . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?

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
C8 O1 C11 117.0(8) . . ?
C1 N1 C2 116.2(7) . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.5(9) . 2_767 ?
C2 C1 H1 119.2 2_767 . ?
N1 C2 C1 121.9(9) . 2_767 ?
N1 C2 C3 117.2(8) . . ?
C1 C2 C3 120.5(8) 2_767 . ?
C4 C3 C2 178.9(10) . . ?
C3 C4 C5 178.3(10) . . ?
C6 C5 C4 122.2(8) . . ?
C6 C5 C10 117.2(9) . . ?
C10 C5 C4 120.5(9) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(8) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.0(8) . . ?
C8 C7 H7 119.0 . . ?
O1 C8 C7 127.3(8) . . ?
O1 C8 C9 115.1(7) . . ?
C7 C8 C9 117.5(8) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(9) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.6(10) . . ?
C9 C10 H10 119.7 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8A O1A C11A 115.6(8) . . ?
C1A N1A C2A 115.9(7) . . ?
N1A C1A H1A 118.4 . . ?
N1A C1A C2A 123.1(9) . 2_455 ?
C2A C1A H1A 118.4 2_455 . ?
N1A C2A C1A 120.9(8) . 2_455 ?
N1A C2A C3A 117.6(7) . . ?
C1A C2A C3A 121.3(8) 2_455 . ?
C4A C3A C2A 179.4(10) . . ?
C3A C4A C5A 178.9(9) . . ?
C6A C5A C4A 121.2(8) . . ?
C6A C5A C10A 118.0(8) . . ?
C10A C5A C4A 120.7(9) . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A C5A 120.2(8) . . ?
C7A C6A H6A 119.9 . . ?
C6A C7A H7A 119.6 . . ?
C8A C7A C6A 120.8(9) . . ?
C8A C7A H7A 119.6 . . ?
O1A C8A C9A 112.9(7) . . ?
C7A C8A O1A 125.9(8) . . ?
C7A C8A C9A 121.2(8) . . ?
C8A C9A H9A 121.1 . . ?
C10A C9A C8A 117.8(8) . . ?
C10A C9A H9A 121.1 . . ?
C5A C10A H10A 119.1 . . ?
C9A C10A C5A 121.9(9) . . ?
C9A C10A H10A 119.1 . . ?
O1A C11A H11D 109.5 . . ?
O1A C11A H11E 109.5 . . ?
O1A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
