# Supplementary Information (SI) for CrystEngComm.
# 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. 
# 
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data_ETI_TFTI_meoh
_database_code_depnum_ccdc_archive 'CCDC 2413005'
loop_
_audit_author_name
_audit_author_address
'Lixing Song'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2024-12-26 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H14 N2 O2, C6 F3 I3'
_chemical_formula_sum            'C14 H14 F3 I3 N2 O2'
_chemical_formula_weight         679.97
_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'
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'

_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                   8.5467(4)
_cell_length_b                   9.5605(5)
_cell_length_c                   13.0160(7)
_cell_angle_alpha                93.461(5)
_cell_angle_beta                 95.913(4)
_cell_angle_gamma                111.472(5)
_cell_volume                     978.93(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4298
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3870
_cell_measurement_theta_min      2.7440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8685
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.301
_diffrn_reflns_theta_min         2.302
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3431
_reflns_number_total             4580
_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       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         1.731
_refine_diff_density_min         -1.197
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4580
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.024
_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)+(0.0305P)²+1.5120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0892
_refine_special_details          ?
_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
O3 O -0.0484(4) -0.0219(3) 0.1117(3) 0.0435(8) Uani 1 1 d . . . . .
C2 C -0.083(2) 0.0771(16) 0.0736(16) 0.029(4) Uani 0.60(5) 1 d D U P A 1
C4 C -0.257(2) 0.0410(19) 0.014(2) 0.042(5) Uani 0.60(5) 1 d D . P A 1
H4A H -0.2623 -0.0014 -0.0569 0.050 Uiso 0.60(5) 1 calc R U P A 1
H4B H -0.3439 -0.0306 0.0469 0.050 Uiso 0.60(5) 1 calc R U P A 1
C5 C -0.280(3) 0.189(3) 0.014(3) 0.094(9) Uani 0.60(5) 1 d D . P A 1
H5A H -0.3336 0.1984 -0.0532 0.113 Uiso 0.60(5) 1 calc R U P A 1
H5B H -0.3486 0.1986 0.0666 0.113 Uiso 0.60(5) 1 calc R U P A 1
C6 C -0.104(3) 0.3074(16) 0.038(4) 0.057(6) Uani 0.60(5) 1 d D . P A 1
H6A H -0.0618 0.3458 -0.0254 0.068 Uiso 0.60(5) 1 calc R U P A 1
H6B H -0.1026 0.3910 0.0844 0.068 Uiso 0.60(5) 1 calc R U P A 1
N1 N -0.0028(14) 0.2291(16) 0.0869(12) 0.035(5) Uani 0.60(5) 1 d D . P A 1
C2B C -0.117(3) 0.070(2) 0.086(2) 0.027(6) Uani 0.40(5) 1 d D U P A 2
C4B C -0.283(3) 0.063(3) 0.029(3) 0.047(9) Uani 0.40(5) 1 d D . P A 2
H4C H -0.3216 -0.0149 -0.0292 0.057 Uiso 0.40(5) 1 calc R U P A 2
H4D H -0.3692 0.0416 0.0751 0.057 Uiso 0.40(5) 1 calc R U P A 2
C5B C -0.248(5) 0.216(4) -0.008(5) 0.091(16) Uani 0.40(5) 1 d D . P A 2
H5C H -0.2431 0.2108 -0.0823 0.109 Uiso 0.40(5) 1 calc R U P A 2
H5D H -0.3356 0.2527 0.0065 0.109 Uiso 0.40(5) 1 calc R U P A 2
C6B C -0.080(5) 0.317(3) 0.050(5) 0.072(13) Uani 0.40(5) 1 d D . P A 2
H6C H -0.0094 0.3803 0.0040 0.087 Uiso 0.40(5) 1 calc R U P A 2
H6D H -0.0945 0.3806 0.1059 0.087 Uiso 0.40(5) 1 calc R U P A 2
N1B N -0.0039(15) 0.214(3) 0.091(2) 0.046(9) Uani 0.40(5) 1 d D . P A 2
C7 C 0.1659(6) 0.2944(5) 0.1480(4) 0.0386(11) Uani 1 1 d D . . . .
H7 H 0.1976 0.2110 0.1699 0.046 Uiso 1 1 calc R U . A 1
C8 C 0.2977(6) 0.3858(5) 0.0819(4) 0.0446(12) Uani 1 1 d . . . . .
O9 O 0.4136(5) 0.5036(4) 0.1203(3) 0.0631(12) Uani 1 1 d . . . . .
N10 N 0.2827(6) 0.3303(5) -0.0162(3) 0.0592(14) Uani 1 1 d . . . . .
H10A H 0.3556 0.3771 -0.0555 0.071 Uiso 1 1 calc R U . . .
H10B H 0.2000 0.2475 -0.0404 0.071 Uiso 1 1 calc R U . . .
C11 C 0.1632(7) 0.3902(6) 0.2454(4) 0.0499(14) Uani 1 1 d . . . . .
H11A H 0.2768 0.4337 0.2835 0.060 Uiso 1 1 calc R U . . .
H11B H 0.1308 0.4727 0.2250 0.060 Uiso 1 1 calc R U . . .
C12 C 0.0428(9) 0.3019(7) 0.3163(5) 0.072(2) Uani 1 1 d . . . . .
H12A H -0.0720 0.2735 0.2837 0.108 Uiso 1 1 calc R U . . .
H12B H 0.0591 0.3633 0.3806 0.108 Uiso 1 1 calc R U . . .
H12C H 0.0647 0.2126 0.3298 0.108 Uiso 1 1 calc R U . . .
C16 C 0.7845(6) 0.1067(5) 0.5412(4) 0.0400(11) Uani 1 1 d . . . . .
C15 C 0.7596(7) 0.2338(6) 0.5110(4) 0.0474(13) Uani 1 1 d . . . . .
C14 C 0.6724(7) 0.2372(6) 0.4171(4) 0.0481(13) Uani 1 1 d . . . . .
C13 C 0.6120(6) 0.1049(5) 0.3496(4) 0.0422(12) Uani 1 1 d . . . . .
C18 C 0.6327(6) -0.0252(5) 0.3743(4) 0.0398(11) Uani 1 1 d . . . . .
C17 C 0.7175(6) -0.0222(5) 0.4706(4) 0.0392(11) Uani 1 1 d . . . . .
I2 I 0.91179(5) 0.10434(5) 0.68595(3) 0.06069(14) Uani 1 1 d . . . . .
I1 I 0.64707(7) 0.43457(5) 0.37504(5) 0.08597(19) Uani 1 1 d . . . . .
I3 I 0.53742(4) -0.22298(4) 0.27162(3) 0.04954(12) Uani 1 1 d . . . . .
F2 F 0.8252(5) 0.3608(3) 0.5769(3) 0.0721(10) Uani 1 1 d . . . . .
F1 F 0.5306(4) 0.1052(4) 0.2552(3) 0.0675(10) Uani 1 1 d . . . . .
F3 F 0.7389(4) -0.1469(3) 0.4975(2) 0.0581(9) 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
O3 C2 1.210(14) . ?
O3 C2B 1.27(2) . ?
C2 C4 1.510(10) . ?
C2 N1 1.352(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.499(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.497(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.463(10) . ?
N1 C7 1.465(7) . ?
C2B C4B 1.508(11) . ?
C2B N1B 1.349(10) . ?
C4B H4C 0.9700 . ?
C4B H4D 0.9700 . ?
C4B C5B 1.497(19) . ?
C5B H5C 0.9700 . ?
C5B H5D 0.9700 . ?
C5B C6B 1.495(17) . ?
C6B H6C 0.9700 . ?
C6B H6D 0.9700 . ?
C6B N1B 1.462(11) . ?
N1B C7 1.463(9) . ?
C7 H7 0.9800 . ?
C7 C8 1.530(7) . ?
C7 C11 1.526(7) . ?
C8 O9 1.230(5) . ?
C8 N10 1.328(6) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.509(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C16 C15 1.381(7) . ?
C16 C17 1.389(6) . ?
C16 I2 2.082(5) . ?
C15 C14 1.373(8) . ?
C15 F2 1.342(6) . ?
C14 C13 1.390(7) . ?
C14 I1 2.075(5) . ?
C13 C18 1.371(7) . ?
C13 F1 1.349(6) . ?
C18 C17 1.374(6) . ?
C18 I3 2.091(4) . ?
C17 F3 1.332(5) . ?

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
O3 C2 C4 120.0(14) . . ?
O3 C2 N1 131.2(13) . . ?
N1 C2 C4 107.9(7) . . ?
C2 C4 H4A 110.7 . . ?
C2 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C5 C4 C2 105.2(8) . . ?
C5 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C4 C5 H5A 110.7 . . ?
C4 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 C4 105.3(14) . . ?
C6 C5 H5A 110.7 . . ?
C6 C5 H5B 110.7 . . ?
C5 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
N1 C6 C5 104.4(9) . . ?
N1 C6 H6A 110.9 . . ?
N1 C6 H6B 110.9 . . ?
C2 N1 C6 112.6(7) . . ?
C2 N1 C7 118.8(13) . . ?
C6 N1 C7 128.5(13) . . ?
O3 C2B C4B 137(2) . . ?
O3 C2B N1B 113(2) . . ?
N1B C2B C4B 108.1(9) . . ?
C2B C4B H4C 110.6 . . ?
C2B C4B H4D 110.6 . . ?
H4C C4B H4D 108.7 . . ?
C5B C4B C2B 105.7(9) . . ?
C5B C4B H4C 110.6 . . ?
C5B C4B H4D 110.6 . . ?
C4B C5B H5C 110.6 . . ?
C4B C5B H5D 110.6 . . ?
H5C C5B H5D 108.7 . . ?
C6B C5B C4B 105.9(16) . . ?
C6B C5B H5C 110.6 . . ?
C6B C5B H5D 110.6 . . ?
C5B C6B H6C 110.8 . . ?
C5B C6B H6D 110.8 . . ?
H6C C6B H6D 108.9 . . ?
N1B C6B C5B 104.7(11) . . ?
N1B C6B H6C 110.8 . . ?
N1B C6B H6D 110.8 . . ?
C2B N1B C6B 112.8(9) . . ?
C2B N1B C7 133(2) . . ?
C6B N1B C7 112(2) . . ?
N1 C7 H7 107.9 . . ?
N1 C7 C8 110.8(8) . . ?
N1 C7 C11 110.7(8) . . ?
N1B C7 C8 114.6(13) . . ?
N1B C7 C11 112.3(12) . . ?
C8 C7 H7 107.9 . . ?
C11 C7 H7 107.9 . . ?
C11 C7 C8 111.5(4) . . ?
O9 C8 C7 120.4(4) . . ?
O9 C8 N10 122.5(5) . . ?
N10 C8 C7 117.1(4) . . ?
C8 N10 H10A 120.0 . . ?
C8 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C7 C11 H11A 108.9 . . ?
C7 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C7 113.3(4) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C16 C17 116.7(4) . . ?
C15 C16 I2 122.3(4) . . ?
C17 C16 I2 121.0(4) . . ?
C14 C15 C16 123.5(5) . . ?
F2 C15 C16 118.1(5) . . ?
F2 C15 C14 118.5(5) . . ?
C15 C14 C13 116.6(5) . . ?
C15 C14 I1 121.3(4) . . ?
C13 C14 I1 122.0(4) . . ?
C18 C13 C14 123.0(4) . . ?
F1 C13 C14 118.4(4) . . ?
F1 C13 C18 118.7(4) . . ?
C13 C18 C17 117.6(4) . . ?
C13 C18 I3 121.9(3) . . ?
C17 C18 I3 120.5(4) . . ?
C18 C17 C16 122.7(4) . . ?
F3 C17 C16 118.1(4) . . ?
F3 C17 C18 119.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C2 C4 C5 159(3) . . . . ?
O3 C2 N1 C6 -171(3) . . . . ?
O3 C2 N1 C7 8(4) . . . . ?
O3 C2B C4B C5B -158(5) . . . . ?
O3 C2B N1B C6B 173(4) . . . . ?
O3 C2B N1B C7 -23(5) . . . . ?
C2 C4 C5 C6 20(4) . . . . ?
C2 N1 C7 C8 119.3(17) . . . . ?
C2 N1 C7 C11 -116.4(17) . . . . ?
C4 C2 N1 C6 -2(3) . . . . ?
C4 C2 N1 C7 176.9(16) . . . . ?
C4 C5 C6 N1 -21(5) . . . . ?
C5 C6 N1 C2 14(4) . . . . ?
C5 C6 N1 C7 -164(3) . . . . ?
C6 N1 C7 C8 -62(3) . . . . ?
C6 N1 C7 C11 62(3) . . . . ?
N1 C2 C4 C5 -12(3) . . . . ?
N1 C7 C8 O9 142.7(8) . . . . ?
N1 C7 C8 N10 -38.7(9) . . . . ?
N1 C7 C11 C12 59.9(10) . . . . ?
C2B C4B C5B C6B -14(6) . . . . ?
C2B N1B C7 C8 132(3) . . . . ?
C2B N1B C7 C11 -100(3) . . . . ?
C4B C2B N1B C6B 5(5) . . . . ?
C4B C2B N1B C7 170(3) . . . . ?
C4B C5B C6B N1B 17(7) . . . . ?
C5B C6B N1B C2B -14(7) . . . . ?
C5B C6B N1B C7 178(4) . . . . ?
C6B N1B C7 C8 -64(4) . . . . ?
C6B N1B C7 C11 65(4) . . . . ?
N1B C2B C4B C5B 6(5) . . . . ?
N1B C7 C8 O9 147.9(13) . . . . ?
N1B C7 C8 N10 -33.5(13) . . . . ?
N1B C7 C11 C12 53.5(14) . . . . ?
C8 C7 C11 C12 -176.3(5) . . . . ?
C11 C7 C8 O9 18.9(7) . . . . ?
C11 C7 C8 N10 -162.5(5) . . . . ?
C16 C15 C14 C13 -1.8(8) . . . . ?
C16 C15 C14 I1 -177.9(4) . . . . ?
C15 C16 C17 C18 1.1(8) . . . . ?
C15 C16 C17 F3 -179.7(5) . . . . ?
C15 C14 C13 C18 1.6(8) . . . . ?
C15 C14 C13 F1 -177.9(5) . . . . ?
C14 C13 C18 C17 -0.1(8) . . . . ?
C14 C13 C18 I3 179.2(4) . . . . ?
C13 C18 C17 C16 -1.3(8) . . . . ?
C13 C18 C17 F3 179.5(4) . . . . ?
C17 C16 C15 C14 0.6(8) . . . . ?
C17 C16 C15 F2 -179.0(5) . . . . ?
I2 C16 C15 C14 -178.3(4) . . . . ?
I2 C16 C15 F2 2.2(7) . . . . ?
I2 C16 C17 C18 180.0(4) . . . . ?
I2 C16 C17 F3 -0.9(7) . . . . ?
I1 C14 C13 C18 177.6(4) . . . . ?
I1 C14 C13 F1 -1.8(7) . . . . ?
I3 C18 C17 C16 179.4(4) . . . . ?
I3 C18 C17 F3 0.2(7) . . . . ?
F2 C15 C14 C13 177.7(5) . . . . ?
F2 C15 C14 I1 1.6(7) . . . . ?
F1 C13 C18 C17 179.4(5) . . . . ?
F1 C13 C18 I3 -1.4(7) . . . . ?

####################################################################### 
# 
# 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_ANI_TFTI_meoh
_database_code_depnum_ccdc_archive 'CCDC 2413007'
loop_
_audit_author_name
_audit_author_address
'Lixing Song'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2025-01-06 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_audit_creation_date             2025-01-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N O3, C6 F3 I3'
_chemical_formula_sum            'C18 H13 F3 I3 N O3'
_chemical_formula_weight         728.99
_chemical_absolute_configuration ?
_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'
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'

_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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   28.0048(13)
_cell_length_b                   4.8659(3)
_cell_length_c                   15.7552(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2146.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.2490
_cell_measurement_theta_min      3.1420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.411
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9956
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_min         2.967
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '125 images, ΔΦ 1.2° '
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.900
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                3440
_reflns_number_total             3675
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       MAR
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 1453 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.020
_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)+(0.0752P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H4A(0.121) H4B(0.121) H5A(0.129) H5B(0.129) H6A(0.086) H6B(0.086)
 H14(0.07) H13(0.078) H11(0.071) H10(0.067) H16A(0.141) H16B(0.141) H16C(0.141)
 Fixed X: H4A(0.3699) H4B(0.3555) H5A(0.4067) H5B(0.4246) H6A(0.4884)
 H6B(0.4704) H14(0.5329) H13(0.5198) H11(0.4022) H10(0.4154) H16A(0.4153)
 H16B(0.4158) H16C(0.3858)
 Fixed Y: H4A(0.4263) H4B(0.6722) H5A(0.9201) H5B(0.6661) H6A(0.6457)
 H6B(0.9005) H14(0.0604) H13(-0.185) H11(0.2624) H10(0.5054) H16A(0.0947) H16B(-
 0.2124) H16C(-0.1268)
 Fixed Z: H4A(0.2148) H4B(0.2746) H5A(0.2111) H5B(0.1581) H6A(0.2354)
 H6B(0.2885) H14(0.4638) H13(0.586) H11(0.6328) H10(0.509) H16A(0.7641)
 H16B(0.7942) H16C(0.7145)
;
_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
O3 O 0.3884(3) 0.241(2) 0.3706(5) 0.092(2) Uani 1 1 d . . . . .
C2 C 0.4053(4) 0.4227(19) 0.3269(7) 0.064(2) Uani 1 1 d . . . . .
C4 C 0.3820(5) 0.561(3) 0.2549(10) 0.101(4) Uani 1 1 d . . . . .
H4A H 0.3699 0.4263 0.2148 0.121 Uiso 1 1 calc R U . . .
H4B H 0.3555 0.6722 0.2746 0.121 Uiso 1 1 calc R U . . .
C5 C 0.4179(5) 0.732(4) 0.2150(9) 0.108(5) Uani 1 1 d . . . . .
H5A H 0.4067 0.9201 0.2111 0.129 Uiso 1 1 calc R U . . .
H5B H 0.4246 0.6661 0.1581 0.129 Uiso 1 1 calc R U . . .
C6 C 0.4618(4) 0.719(2) 0.2679(7) 0.072(2) Uani 1 1 d . . . . .
H6A H 0.4884 0.6457 0.2354 0.086 Uiso 1 1 calc R U . . .
H6B H 0.4704 0.9005 0.2885 0.086 Uiso 1 1 calc R U . . .
N1 N 0.4498(3) 0.5365(14) 0.3387(5) 0.0530(15) Uani 1 1 d . . . . .
C7 C 0.4863(3) 0.4650(16) 0.3945(6) 0.0537(18) Uani 1 1 d . . . . .
O8 O 0.5267(2) 0.5363(15) 0.3781(5) 0.0683(16) Uani 1 1 d . . . . .
C9 C 0.4748(2) 0.3058(15) 0.4730(5) 0.0479(14) Uani 1 1 d . . . . .
C14 C 0.5064(3) 0.0993(14) 0.4973(7) 0.058(2) Uani 1 1 d . . . . .
H14 H 0.5329 0.0604 0.4638 0.070 Uiso 1 1 calc R U . . .
C13 C 0.4987(4) -0.0464(18) 0.5704(7) 0.065(2) Uani 1 1 d . . . . .
H13 H 0.5198 -0.1850 0.5860 0.078 Uiso 1 1 calc R U . . .
C12 C 0.4596(3) 0.0118(17) 0.6212(6) 0.059(2) Uani 1 1 d . . . . .
C11 C 0.4282(3) 0.2207(19) 0.5986(6) 0.0588(19) Uani 1 1 d . . . . .
H11 H 0.4022 0.2624 0.6328 0.071 Uiso 1 1 calc R U . . .
C10 C 0.4363(3) 0.3655(17) 0.5245(6) 0.0559(19) Uani 1 1 d . . . . .
H10 H 0.4154 0.5054 0.5090 0.067 Uiso 1 1 calc R U . . .
O15 O 0.4545(3) -0.1453(15) 0.6929(5) 0.0783(19) Uani 1 1 d . . . . .
C16 C 0.4147(5) -0.093(2) 0.7456(9) 0.094(4) Uani 1 1 d . . . . .
H16A H 0.4153 0.0947 0.7641 0.141 Uiso 1 1 calc R U . . .
H16B H 0.4158 -0.2124 0.7942 0.141 Uiso 1 1 calc R U . . .
H16C H 0.3858 -0.1268 0.7145 0.141 Uiso 1 1 calc R U . . .
C18 C 0.6892(3) 0.5611(16) 0.5162(6) 0.0537(19) Uani 1 1 d . . . . .
C17 C 0.7008(3) 0.7056(17) 0.5875(5) 0.0554(18) Uani 1 1 d . . . . .
C22 C 0.7439(3) 0.6755(17) 0.6296(6) 0.0567(19) Uani 1 1 d . . . . .
C21 C 0.7765(3) 0.495(2) 0.5946(6) 0.0588(19) Uani 1 1 d . . . . .
C20 C 0.7676(3) 0.3493(16) 0.5211(6) 0.0528(18) Uani 1 1 d . . . . .
C19 C 0.7230(3) 0.3832(15) 0.4836(6) 0.0523(18) Uani 1 1 d . . . . .
I1 I 0.62147(2) 0.57951(12) 0.46118(4) 0.0692(2) Uani 1 1 d . . . . .
I3 I 0.75770(3) 0.88126(15) 0.74193(6) 0.0885(3) Uani 1 1 d . . . . .
I2 I 0.81889(2) 0.09433(10) 0.46601(5) 0.0642(2) Uani 1 1 d . . . . .
F1 F 0.6690(2) 0.8852(10) 0.6178(4) 0.0730(15) Uani 1 1 d . . . . .
F3 F 0.81974(18) 0.4670(14) 0.6313(5) 0.0771(16) Uani 1 1 d . . . . .
F2 F 0.71324(19) 0.2380(13) 0.4140(4) 0.0722(15) 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
O3 C2 1.218(12) . ?
C2 C4 1.472(18) . ?
C2 N1 1.376(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.449(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.486(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.466(12) . ?
N1 C7 1.393(12) . ?
C7 O8 1.211(10) . ?
C7 C9 1.495(12) . ?
C9 C14 1.394(11) . ?
C9 C10 1.380(12) . ?
C14 H14 0.9300 . ?
C14 C13 1.369(15) . ?
C13 H13 0.9300 . ?
C13 C12 1.386(15) . ?
C12 C11 1.390(13) . ?
C12 O15 1.371(12) . ?
C11 H11 0.9300 . ?
C11 C10 1.382(14) . ?
C10 H10 0.9300 . ?
O15 C16 1.414(16) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C17 1.365(13) . ?
C18 C19 1.381(12) . ?
C18 I1 2.088(9) . ?
C17 C22 1.386(13) . ?
C17 F1 1.334(10) . ?
C22 C21 1.381(14) . ?
C22 I3 2.070(9) . ?
C21 C20 1.381(13) . ?
C21 F3 1.349(10) . ?
C20 C19 1.390(12) . ?
C20 I2 2.088(8) . ?
C19 F2 1.333(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
O3 C2 C4 126.5(10) . . ?
O3 C2 N1 124.7(9) . . ?
N1 C2 C4 108.8(9) . . ?
C2 C4 H4A 110.4 . . ?
C2 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 C2 106.8(10) . . ?
C5 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
C4 C5 H5A 110.1 . . ?
C4 C5 H5B 110.1 . . ?
C4 C5 C6 107.9(10) . . ?
H5A C5 H5B 108.4 . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
C5 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
N1 C6 C5 105.2(8) . . ?
N1 C6 H6A 110.7 . . ?
N1 C6 H6B 110.7 . . ?
C2 N1 C6 110.4(7) . . ?
C2 N1 C7 130.5(8) . . ?
C7 N1 C6 117.6(7) . . ?
N1 C7 C9 119.5(7) . . ?
O8 C7 N1 118.7(8) . . ?
O8 C7 C9 121.8(8) . . ?
C14 C9 C7 117.6(7) . . ?
C10 C9 C7 123.1(7) . . ?
C10 C9 C14 119.2(8) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(8) . . ?
C13 C14 H14 119.9 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.3(8) . . ?
C12 C13 H13 119.8 . . ?
C13 C12 C11 120.1(9) . . ?
O15 C12 C13 116.4(8) . . ?
O15 C12 C11 123.5(9) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.1(8) . . ?
C10 C11 H11 120.4 . . ?
C9 C10 C11 121.1(8) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 O15 C16 117.8(8) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C18 C19 117.8(8) . . ?
C17 C18 I1 122.3(6) . . ?
C19 C18 I1 119.7(7) . . ?
C18 C17 C22 123.1(8) . . ?
F1 C17 C18 118.3(8) . . ?
F1 C17 C22 118.6(8) . . ?
C17 C22 I3 121.4(7) . . ?
C21 C22 C17 116.9(8) . . ?
C21 C22 I3 121.7(7) . . ?
C20 C21 C22 122.8(8) . . ?
F3 C21 C22 119.1(8) . . ?
F3 C21 C20 118.1(8) . . ?
C21 C20 C19 117.3(8) . . ?
C21 C20 I2 121.9(6) . . ?
C19 C20 I2 120.8(7) . . ?
C18 C19 C20 122.1(8) . . ?
F2 C19 C18 119.8(8) . . ?
F2 C19 C20 118.1(7) . . ?

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
O3 C2 C4 C5 -171.8(13) . . . . ?
O3 C2 N1 C6 171.5(10) . . . . ?
O3 C2 N1 C7 5.8(17) . . . . ?
C2 C4 C5 C6 -5.5(18) . . . . ?
C2 N1 C7 O8 158.5(10) . . . . ?
C2 N1 C7 C9 -22.1(13) . . . . ?
C4 C2 N1 C6 -9.7(13) . . . . ?
C4 C2 N1 C7 -175.3(10) . . . . ?
C4 C5 C6 N1 -0.1(17) . . . . ?
C5 C6 N1 C2 6.1(13) . . . . ?
C5 C6 N1 C7 173.8(10) . . . . ?
C6 N1 C7 O8 -6.3(12) . . . . ?
C6 N1 C7 C9 173.1(8) . . . . ?
N1 C2 C4 C5 9.4(16) . . . . ?
N1 C7 C9 C14 140.2(7) . . . . ?
N1 C7 C9 C10 -43.9(11) . . . . ?
C7 C9 C14 C13 177.5(8) . . . . ?
C7 C9 C10 C11 -177.0(7) . . . . ?
O8 C7 C9 C14 -40.5(11) . . . . ?
O8 C7 C9 C10 135.4(9) . . . . ?
C9 C14 C13 C12 -0.6(13) . . . . ?
C14 C9 C10 C11 -1.2(12) . . . . ?
C14 C13 C12 C11 -0.6(13) . . . . ?
C14 C13 C12 O15 179.6(8) . . . . ?
C13 C12 C11 C10 0.9(12) . . . . ?
C13 C12 O15 C16 -179.3(9) . . . . ?
C12 C11 C10 C9 0.0(13) . . . . ?
C11 C12 O15 C16 0.9(14) . . . . ?
C10 C9 C14 C13 1.5(12) . . . . ?
O15 C12 C11 C10 -179.3(8) . . . . ?
C18 C17 C22 C21 1.9(14) . . . . ?
C18 C17 C22 I3 -175.9(7) . . . . ?
C17 C18 C19 C20 -0.1(13) . . . . ?
C17 C18 C19 F2 180.0(8) . . . . ?
C17 C22 C21 C20 0.1(14) . . . . ?
C17 C22 C21 F3 177.4(8) . . . . ?
C22 C21 C20 C19 -1.9(14) . . . . ?
C22 C21 C20 I2 176.6(7) . . . . ?
C21 C20 C19 C18 1.9(13) . . . . ?
C21 C20 C19 F2 -178.1(8) . . . . ?
C19 C18 C17 C22 -2.0(13) . . . . ?
C19 C18 C17 F1 177.7(8) . . . . ?
I1 C18 C17 C22 173.5(7) . . . . ?
I1 C18 C17 F1 -6.9(11) . . . . ?
I1 C18 C19 C20 -175.6(7) . . . . ?
I1 C18 C19 F2 4.4(11) . . . . ?
I3 C22 C21 C20 178.0(7) . . . . ?
I3 C22 C21 F3 -4.7(13) . . . . ?
I2 C20 C19 C18 -176.6(6) . . . . ?
I2 C20 C19 F2 3.3(11) . . . . ?
F1 C17 C22 C21 -177.7(8) . . . . ?
F1 C17 C22 I3 4.4(11) . . . . ?
F3 C21 C20 C19 -179.3(8) . . . . ?
F3 C21 C20 I2 -0.7(12) . . . . ?

_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_ETI_DTFB_meoh
_database_code_depnum_ccdc_archive 'CCDC 2413006'
loop_
_audit_author_name
_audit_author_address
'Lixing Song'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2024-12-26 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C6 F4 I2), 2(C8 H14 N2 O2)'
_chemical_formula_sum            'C34 H28 F12 I6 N4 O4'
_chemical_formula_weight         1546.00
_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'
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'

_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                   8.8594(5)
_cell_length_b                   10.1598(7)
_cell_length_c                   12.8080(10)
_cell_angle_alpha                92.855(6)
_cell_angle_beta                 95.703(5)
_cell_angle_gamma                99.376(5)
_cell_volume                     1129.25(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4945
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.5510
_cell_measurement_theta_min      3.1970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             718
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9585
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.364
_diffrn_reflns_theta_min         2.036
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4160
_reflns_number_total             5281
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.541
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.048
_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)+(0.0279P)²+0.3443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0753
_refine_special_details          ?
_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
O3 O 0.8339(3) 1.0301(2) -0.02998(19) 0.0387(6) Uani 1 1 d . . . . .
C2 C 0.8353(4) 0.9897(3) 0.0589(3) 0.0327(8) Uani 1 1 d . . . . .
C4 C 0.8772(5) 1.0741(4) 0.1603(3) 0.0485(10) Uani 1 1 d . . . . .
H4A H 0.9849 1.1149 0.1674 0.058 Uiso 1 1 calc R U . . .
H4B H 0.8151 1.1442 0.1633 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8458(5) 0.9804(4) 0.2452(3) 0.0549(12) Uani 1 1 d . . . . .
H5A H 0.9350 0.9891 0.2970 0.066 Uiso 1 1 calc R U . . .
H5B H 0.7591 1.0002 0.2801 0.066 Uiso 1 1 calc R U . . .
C6 C 0.8108(6) 0.8427(4) 0.1937(3) 0.0580(12) Uani 1 1 d . . . . .
H6A H 0.8917 0.7923 0.2144 0.070 Uiso 1 1 calc R U . . .
H6B H 0.7139 0.7955 0.2122 0.070 Uiso 1 1 calc R U . . .
N1 N 0.8017(3) 0.8615(3) 0.0812(2) 0.0307(6) Uani 1 1 d . . . . .
C7 C 0.7475(4) 0.7504(3) 0.0028(2) 0.0292(7) Uani 1 1 d . . . . .
H7 H 0.7499 0.7876 -0.0663 0.035 Uiso 1 1 calc R U . . .
C8 C 0.8558(4) 0.6466(3) 0.0063(2) 0.0304(7) Uani 1 1 d . . . . .
O9 O 0.8018(3) 0.5268(2) -0.0131(2) 0.0396(6) Uani 1 1 d . . . . .
N10 N 1.0051(3) 0.6904(3) 0.0268(2) 0.0389(7) Uani 1 1 d . . . . .
H10A H 1.0687 0.6348 0.0271 0.047 Uiso 1 1 calc R U . . .
H10B H 1.0387 0.7744 0.0400 0.047 Uiso 1 1 calc R U . . .
C11 C 0.5814(4) 0.6876(3) 0.0109(3) 0.0404(9) Uani 1 1 d . . . . .
H11A H 0.5524 0.6118 -0.0403 0.049 Uiso 1 1 calc R U . . .
H11B H 0.5738 0.6544 0.0802 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4693(5) 0.7842(5) -0.0074(4) 0.0634(13) Uani 1 1 d . . . . .
H12A H 0.4946 0.8576 0.0449 0.095 Uiso 1 1 calc R U . . .
H12B H 0.3665 0.7388 -0.0026 0.095 Uiso 1 1 calc R U . . .
H12C H 0.4758 0.8172 -0.0760 0.095 Uiso 1 1 calc R U . . .
C19 C 0.5709(4) 1.0063(4) 0.6039(3) 0.0438(9) Uani 1 1 d . . . . .
C20 C 0.4522(5) 0.9034(4) 0.5651(3) 0.0446(9) Uani 1 1 d . . . . .
C21 C 0.3845(5) 0.8990(4) 0.4644(3) 0.0465(10) Uani 1 1 d . . . . .
I3 I 0.67523(3) 1.01457(3) 0.75725(2) 0.05488(10) Uani 1 1 d . . . . .
F5 F 0.4043(3) 0.8065(3) 0.62796(19) 0.0671(7) Uani 1 1 d . . . . .
F6 F 0.2718(3) 0.7950(3) 0.4316(2) 0.0703(7) Uani 1 1 d . . . . .
C16 C 0.5710(5) 0.5006(5) 0.6037(3) 0.0487(10) Uani 1 1 d . . . . .
C17 C 0.4591(5) 0.3951(5) 0.5601(3) 0.0533(11) Uani 1 1 d . . . . .
C18 C 0.3915(5) 0.3952(5) 0.4589(3) 0.0503(11) Uani 1 1 d . . . . .
I2 I 0.67385(3) 0.50025(4) 0.75598(2) 0.06189(11) Uani 1 1 d . . . . .
F3 F 0.4164(3) 0.2902(3) 0.6163(2) 0.0705(7) Uani 1 1 d . . . . .
F4 F 0.2851(3) 0.2889(3) 0.4202(2) 0.0678(7) Uani 1 1 d . . . . .
C13 C 0.9307(4) 0.4839(3) 0.3958(3) 0.0358(8) Uani 1 1 d . . . . .
C14 C 0.9704(4) 0.3773(3) 0.4475(3) 0.0365(8) Uani 1 1 d . . . . .
C15 C 1.0370(4) 0.3921(3) 0.5495(3) 0.0385(8) Uani 1 1 d . . . . .
I1 I 0.83116(3) 0.46184(3) 0.24102(2) 0.05007(9) Uani 1 1 d . . . . .
F1 F 0.9432(3) 0.2544(2) 0.39804(17) 0.0538(6) Uani 1 1 d . . . . .
F2 F 1.0716(3) 0.2841(2) 0.59623(17) 0.0555(6) 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
O3 C2 1.229(4) . ?
C2 C4 1.499(5) . ?
C2 N1 1.339(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.497(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.489(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.458(4) . ?
N1 C7 1.459(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.537(4) . ?
C7 C11 1.521(5) . ?
C8 O9 1.236(4) . ?
C8 N10 1.321(4) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.516(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C19 C20 1.389(6) . ?
C19 C21 1.371(6) 2_676 ?
C19 I3 2.078(4) . ?
C20 C21 1.362(5) . ?
C20 F5 1.345(5) . ?
C21 C19 1.371(6) 2_676 ?
C21 F6 1.348(4) . ?
C16 C17 1.389(6) . ?
C16 C18 1.377(6) 2_666 ?
C16 I2 2.069(4) . ?
C17 C18 1.372(6) . ?
C17 F3 1.340(5) . ?
C18 C16 1.377(6) 2_666 ?
C18 F4 1.350(5) . ?
C13 C14 1.374(5) . ?
C13 C15 1.384(5) 2_766 ?
C13 I1 2.074(3) . ?
C14 C15 1.369(5) . ?
C14 F1 1.346(4) . ?
C15 C13 1.384(5) 2_766 ?
C15 F2 1.339(4) . ?

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
O3 C2 C4 126.2(3) . . ?
O3 C2 N1 125.3(3) . . ?
N1 C2 C4 108.5(3) . . ?
C2 C4 H4A 110.6 . . ?
C2 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
C5 C4 C2 105.5(3) . . ?
C5 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C4 C5 H5A 110.3 . . ?
C4 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?
C6 C5 C4 107.0(3) . . ?
C6 C5 H5A 110.3 . . ?
C6 C5 H5B 110.3 . . ?
C5 C6 H6A 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
N1 C6 C5 104.8(3) . . ?
N1 C6 H6A 110.8 . . ?
N1 C6 H6B 110.8 . . ?
C2 N1 C6 113.6(3) . . ?
C2 N1 C7 124.4(3) . . ?
C6 N1 C7 121.8(3) . . ?
N1 C7 H7 106.8 . . ?
N1 C7 C8 111.6(3) . . ?
N1 C7 C11 112.1(3) . . ?
C8 C7 H7 106.8 . . ?
C11 C7 H7 106.8 . . ?
C11 C7 C8 112.2(3) . . ?
O9 C8 C7 119.6(3) . . ?
O9 C8 N10 122.4(3) . . ?
N10 C8 C7 118.0(3) . . ?
C8 N10 H10A 120.0 . . ?
C8 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C7 C11 H11A 108.9 . . ?
C7 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C7 113.2(3) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C20 C19 I3 121.5(3) . . ?
C21 C19 C20 116.4(4) 2_676 . ?
C21 C19 I3 122.0(3) 2_676 . ?
C21 C20 C19 121.1(4) . . ?
F5 C20 C19 119.3(4) . . ?
F5 C20 C21 119.6(4) . . ?
C20 C21 C19 122.5(4) . 2_676 ?
F6 C21 C19 119.7(3) . 2_676 ?
F6 C21 C20 117.8(4) . . ?
C17 C16 I2 121.1(4) . . ?
C18 C16 C17 116.7(4) 2_666 . ?
C18 C16 I2 122.2(3) 2_666 . ?
C18 C17 C16 121.0(4) . . ?
F3 C17 C16 120.2(4) . . ?
F3 C17 C18 118.8(4) . . ?
C17 C18 C16 122.2(4) . 2_666 ?
F4 C18 C16 119.4(4) . 2_666 ?
F4 C18 C17 118.4(4) . . ?
C14 C13 C15 117.2(3) . 2_766 ?
C14 C13 I1 121.7(2) . . ?
C15 C13 I1 121.1(3) 2_766 . ?
C15 C14 C13 121.7(3) . . ?
F1 C14 C13 119.9(3) . . ?
F1 C14 C15 118.4(3) . . ?
C14 C15 C13 121.1(3) . 2_766 ?
F2 C15 C13 119.9(3) . 2_766 ?
F2 C15 C14 118.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C2 C4 C5 174.5(4) . . . . ?
O3 C2 N1 C6 -179.3(4) . . . . ?
O3 C2 N1 C7 -4.5(5) . . . . ?
C2 C4 C5 C6 8.6(5) . . . . ?
C2 N1 C7 C8 121.1(3) . . . . ?
C2 N1 C7 C11 -112.0(4) . . . . ?
C4 C2 N1 C6 1.7(4) . . . . ?
C4 C2 N1 C7 176.5(3) . . . . ?
C4 C5 C6 N1 -7.6(5) . . . . ?
C5 C6 N1 C2 3.8(5) . . . . ?
C5 C6 N1 C7 -171.1(3) . . . . ?
C6 N1 C7 C8 -64.5(4) . . . . ?
C6 N1 C7 C11 62.4(4) . . . . ?
N1 C2 C4 C5 -6.5(4) . . . . ?
N1 C7 C8 O9 145.9(3) . . . . ?
N1 C7 C8 N10 -36.3(4) . . . . ?
N1 C7 C11 C12 61.4(4) . . . . ?
C8 C7 C11 C12 -172.1(3) . . . . ?
C11 C7 C8 O9 19.1(4) . . . . ?
C11 C7 C8 N10 -163.1(3) . . . . ?
C19 C20 C21 C19 0.4(7) . . . 2_676 ?
C19 C20 C21 F6 178.9(3) . . . . ?
C21 C19 C20 C21 -0.4(6) 2_676 . . . ?
C21 C19 C20 F5 179.2(3) 2_676 . . . ?
I3 C19 C20 C21 180.0(3) . . . . ?
I3 C19 C20 F5 -0.4(5) . . . . ?
F5 C20 C21 C19 -179.2(4) . . . 2_676 ?
F5 C20 C21 F6 -0.7(6) . . . . ?
C16 C17 C18 C16 -0.8(7) . . . 2_666 ?
C16 C17 C18 F4 179.0(3) . . . . ?
C18 C16 C17 C18 0.7(6) 2_666 . . . ?
C18 C16 C17 F3 -179.9(3) 2_666 . . . ?
I2 C16 C17 C18 -179.7(3) . . . . ?
I2 C16 C17 F3 -0.3(5) . . . . ?
F3 C17 C18 C16 179.9(4) . . . 2_666 ?
F3 C17 C18 F4 -0.4(6) . . . . ?
C13 C14 C15 C13 -1.0(7) . . . 2_766 ?
C13 C14 C15 F2 179.3(3) . . . . ?
C15 C13 C14 C15 1.0(6) 2_766 . . . ?
C15 C13 C14 F1 -179.4(3) 2_766 . . . ?
I1 C13 C14 C15 179.6(3) . . . . ?
I1 C13 C14 F1 -0.8(5) . . . . ?
F1 C14 C15 C13 179.3(3) . . . 2_766 ?
F1 C14 C15 F2 -0.4(5) . . . . ?

####################################################################### 
# 
# 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_NEFI_DTFB_meoh
_database_code_depnum_ccdc_archive 'CCDC 2413008'
loop_
_audit_author_name
_audit_author_address
'Lixing Song'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2024-12-26 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 N2 O2, C6 F4 I2'
_chemical_formula_sum            'C20 H18 F4 I2 N2 O2'
_chemical_formula_weight         648.16
_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'
I I -0.4742 1.8119 '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'

_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 21/c'
_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                   6.0245(3)
_cell_length_b                   9.3655(4)
_cell_length_c                   38.7258(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.090(4)
_cell_angle_gamma                90
_cell_volume                     2183.56(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7178
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.3300
_cell_measurement_theta_min      2.9740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       thick-plate
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            17564
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         3.027
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, ΔΦ 1.2° '
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3659
_reflns_number_total             3953
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       MAR
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         1.661
_refine_diff_density_min         -1.528
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       0.0089(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.048
_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)+(0.0822P)²+3.4205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_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
O3 O 0.2975(6) 0.7426(5) 0.64684(10) 0.0604(9) Uani 1 1 d . . . . .
C2 C 0.4810(7) 0.7963(5) 0.65155(11) 0.0399(9) Uani 1 1 d . . . . .
C4 C 0.6192(9) 0.8689(6) 0.62540(13) 0.0561(13) Uani 1 1 d . . . . .
H4A H 0.5330 0.9409 0.6129 0.067 Uiso 1 1 calc R U . . .
H4B H 0.6735 0.8002 0.6090 0.067 Uiso 1 1 calc R U . . .
C5 C 0.8092(9) 0.9362(6) 0.64564(14) 0.0564(12) Uani 1 1 d . . . . .
H5A H 0.7849 1.0378 0.6484 0.068 Uiso 1 1 calc R U . . .
H5B H 0.9478 0.9218 0.6341 0.068 Uiso 1 1 calc R U . . .
C6 C 0.8138(9) 0.8608(6) 0.68049(14) 0.0520(12) Uani 1 1 d . . . . .
H6A H 0.9278 0.7877 0.6817 0.062 Uiso 1 1 calc R U . . .
H6B H 0.8405 0.9282 0.6992 0.062 Uiso 1 1 calc R U . . .
N1 N 0.5938(6) 0.7982(4) 0.68202(9) 0.0387(8) Uani 1 1 d . . . . .
C7 C 0.5204(10) 0.7189(5) 0.71121(12) 0.0479(11) Uani 1 1 d . . . . .
H7A H 0.6348 0.6509 0.7182 0.057 Uiso 1 1 calc R U . . .
H7B H 0.3883 0.6653 0.7043 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4688(7) 0.8123(4) 0.74172(10) 0.0353(8) Uani 1 1 d . . . . .
O9 O 0.4714(6) 0.9423(3) 0.74019(8) 0.0470(8) Uani 1 1 d . . . . .
N10 N 0.4187(6) 0.7382(4) 0.77017(9) 0.0379(8) Uani 1 1 d . . . . .
H10 H 0.4116 0.6467 0.7688 0.046 Uiso 1 1 calc R U . . .
C11 C 0.3767(7) 0.8048(4) 0.80252(10) 0.0347(8) Uani 1 1 d . . . . .
C16 C 0.5234(8) 0.7761(4) 0.83059(11) 0.0396(9) Uani 1 1 d . . . . .
C15 C 0.4850(10) 0.8462(6) 0.86174(12) 0.0523(12) Uani 1 1 d . . . . .
H15 H 0.5804 0.8300 0.8807 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3116(10) 0.9374(6) 0.86484(13) 0.0588(14) Uani 1 1 d . . . . .
H14 H 0.2926 0.9850 0.8856 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1639(10) 0.9595(5) 0.83742(14) 0.0549(12) Uani 1 1 d . . . . .
H13 H 0.0425 1.0192 0.8401 0.066 Uiso 1 1 calc R U . . .
C12 C 0.1935(8) 0.8939(5) 0.80574(12) 0.0415(9) Uani 1 1 d . . . . .
C18 C 0.7111(9) 0.6725(6) 0.82807(15) 0.0546(12) Uani 1 1 d . . . . .
H18A H 0.6575 0.5857 0.8175 0.082 Uiso 1 1 calc R U . . .
H18B H 0.7719 0.6521 0.8508 0.082 Uiso 1 1 calc R U . . .
H18C H 0.8243 0.7131 0.8143 0.082 Uiso 1 1 calc R U . . .
C17 C 0.0292(9) 0.9176(6) 0.77633(15) 0.0581(13) Uani 1 1 d . . . . .
H17A H 0.0754 0.9975 0.7628 0.087 Uiso 1 1 calc R U . . .
H17B H -0.1144 0.9368 0.7853 0.087 Uiso 1 1 calc R U . . .
H17C H 0.0212 0.8338 0.7621 0.087 Uiso 1 1 calc R U . . .
I1 I 0.16778(5) 0.64131(4) 0.57992(2) 0.05008(18) Uani 1 1 d . . . . .
C19 C 0.0692(7) 0.5584(5) 0.53165(11) 0.0419(9) Uani 1 1 d . . . . .
C20 C 0.1969(8) 0.4598(6) 0.51510(12) 0.0477(11) Uani 1 1 d . . . . .
C21 C 0.1288(8) 0.4025(6) 0.48408(13) 0.0488(11) Uani 1 1 d . . . . .
F1 F 0.3906(6) 0.4169(5) 0.52990(10) 0.0804(11) Uani 1 1 d . . . . .
F2 F 0.2587(6) 0.3061(4) 0.46907(10) 0.0797(11) Uani 1 1 d . . . . .
I2 I -0.14032(8) 0.20696(4) 0.57036(2) 0.0725(2) Uani 1 1 d . . . . .
C22 C -0.0540(9) 0.0844(5) 0.52845(13) 0.0498(11) Uani 1 1 d . . . . .
C23 C 0.1415(9) 0.0090(6) 0.52800(13) 0.0519(11) Uani 1 1 d . . . . .
C24 C 0.1964(9) -0.0728(6) 0.50032(14) 0.0531(12) Uani 1 1 d . . . . .
F3 F 0.2860(6) 0.0186(4) 0.55503(9) 0.0778(10) Uani 1 1 d . . . . .
F4 F 0.3889(6) -0.1429(4) 0.50152(11) 0.0775(10) 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
O3 C2 1.222(6) . ?
C2 C4 1.498(7) . ?
C2 N1 1.340(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.502(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.522(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.453(6) . ?
N1 C7 1.436(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.511(6) . ?
C8 O9 1.220(5) . ?
C8 N10 1.346(5) . ?
N10 H10 0.8600 . ?
N10 C11 1.430(5) . ?
C11 C16 1.402(6) . ?
C11 C12 1.393(6) . ?
C16 C15 1.400(7) . ?
C16 C18 1.496(7) . ?
C15 H15 0.9300 . ?
C15 C14 1.358(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.376(9) . ?
C13 H13 0.9300 . ?
C13 C12 1.390(7) . ?
C12 C17 1.498(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
I1 C19 2.090(4) . ?
C19 C20 1.375(7) . ?
C19 C21 1.369(7) 3_566 ?
C20 C21 1.365(7) . ?
C20 F1 1.343(5) . ?
C21 C19 1.369(7) 3_566 ?
C21 F2 1.341(6) . ?
I2 C22 2.070(5) . ?
C22 C23 1.374(7) . ?
C22 C24 1.385(8) 3_556 ?
C23 C24 1.368(8) . ?
C23 F3 1.340(6) . ?
C24 C22 1.385(8) 3_556 ?
C24 F4 1.332(6) . ?

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
O3 C2 C4 127.5(4) . . ?
O3 C2 N1 124.3(4) . . ?
N1 C2 C4 108.2(4) . . ?
C2 C4 H4A 110.6 . . ?
C2 C4 H4B 110.6 . . ?
C2 C4 C5 105.7(4) . . ?
H4A C4 H4B 108.7 . . ?
C5 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
C4 C5 C6 104.9(4) . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
N1 C6 C5 103.7(4) . . ?
N1 C6 H6A 111.0 . . ?
N1 C6 H6B 111.0 . . ?
C2 N1 C6 113.8(4) . . ?
C2 N1 C7 121.7(4) . . ?
C7 N1 C6 123.3(4) . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
N1 C7 C8 113.2(4) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
O9 C8 C7 122.5(4) . . ?
O9 C8 N10 123.9(4) . . ?
N10 C8 C7 113.6(3) . . ?
C8 N10 H10 118.5 . . ?
C8 N10 C11 123.0(3) . . ?
C11 N10 H10 118.5 . . ?
C16 C11 N10 118.0(4) . . ?
C12 C11 N10 120.4(4) . . ?
C12 C11 C16 121.7(4) . . ?
C11 C16 C18 122.1(4) . . ?
C15 C16 C11 117.3(4) . . ?
C15 C16 C18 120.6(5) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 C16 121.6(5) . . ?
C14 C15 H15 119.2 . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.3(5) . . ?
C13 C14 H14 119.9 . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C12 121.0(5) . . ?
C12 C13 H13 119.5 . . ?
C11 C12 C17 121.7(4) . . ?
C13 C12 C11 118.1(5) . . ?
C13 C12 C17 120.2(5) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C19 I1 121.4(3) . . ?
C21 C19 I1 120.9(4) 3_566 . ?
C21 C19 C20 117.7(4) 3_566 . ?
C21 C20 C19 121.3(4) . . ?
F1 C20 C19 119.6(4) . . ?
F1 C20 C21 119.1(4) . . ?
C20 C21 C19 121.0(4) . 3_566 ?
F2 C21 C19 120.0(5) . 3_566 ?
F2 C21 C20 119.0(4) . . ?
C23 C22 I2 122.3(4) . . ?
C23 C22 C24 117.1(5) . 3_556 ?
C24 C22 I2 120.6(4) 3_556 . ?
C24 C23 C22 122.0(5) . . ?
F3 C23 C22 119.2(5) . . ?
F3 C23 C24 118.8(5) . . ?
C23 C24 C22 120.9(5) . 3_556 ?
F4 C24 C22 120.1(5) . 3_556 ?
F4 C24 C23 118.9(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C2 C4 C5 170.8(5) . . . . ?
O3 C2 N1 C6 176.5(5) . . . . ?
O3 C2 N1 C7 8.8(7) . . . . ?
C2 C4 C5 C6 17.7(6) . . . . ?
C2 N1 C7 C8 -118.8(5) . . . . ?
C4 C2 N1 C6 -3.0(5) . . . . ?
C4 C2 N1 C7 -170.8(4) . . . . ?
C4 C5 C6 N1 -19.0(6) . . . . ?
C5 C6 N1 C2 14.2(6) . . . . ?
C5 C6 N1 C7 -178.3(4) . . . . ?
C6 N1 C7 C8 74.6(6) . . . . ?
N1 C2 C4 C5 -9.7(6) . . . . ?
N1 C7 C8 O9 6.0(7) . . . . ?
N1 C7 C8 N10 -174.5(4) . . . . ?
C7 C8 N10 C11 176.4(4) . . . . ?
C8 N10 C11 C16 -116.0(5) . . . . ?
C8 N10 C11 C12 64.7(6) . . . . ?
O9 C8 N10 C11 -4.1(7) . . . . ?
N10 C11 C16 C15 177.7(4) . . . . ?
N10 C11 C16 C18 -3.8(6) . . . . ?
N10 C11 C12 C13 -178.0(4) . . . . ?
N10 C11 C12 C17 3.0(6) . . . . ?
C11 C16 C15 C14 0.6(7) . . . . ?
C16 C11 C12 C13 2.7(6) . . . . ?
C16 C11 C12 C17 -176.3(4) . . . . ?
C16 C15 C14 C13 2.2(8) . . . . ?
C15 C14 C13 C12 -2.6(8) . . . . ?
C14 C13 C12 C11 0.2(7) . . . . ?
C14 C13 C12 C17 179.1(5) . . . . ?
C12 C11 C16 C15 -3.0(6) . . . . ?
C12 C11 C16 C18 175.5(4) . . . . ?
C18 C16 C15 C14 -178.0(5) . . . . ?
I1 C19 C20 C21 177.9(4) . . . . ?
I1 C19 C20 F1 -0.9(7) . . . . ?
C19 C20 C21 C19 0.1(9) . . . 3_566 ?
C19 C20 C21 F2 -179.6(5) . . . . ?
C21 C19 C20 C21 -0.1(9) 3_566 . . . ?
C21 C19 C20 F1 -178.9(5) 3_566 . . . ?
F1 C20 C21 C19 178.9(5) . . . 3_566 ?
F1 C20 C21 F2 -0.7(8) . . . . ?
I2 C22 C23 C24 179.4(4) . . . . ?
I2 C22 C23 F3 -2.5(7) . . . . ?
C22 C23 C24 C22 -0.9(9) . . . 3_556 ?
C22 C23 C24 F4 179.8(5) . . . . ?
C24 C22 C23 C24 0.8(8) 3_556 . . . ?
C24 C22 C23 F3 179.0(5) 3_556 . . . ?
F3 C23 C24 C22 -179.0(5) . . . 3_556 ?
F3 C23 C24 F4 1.7(8) . . . . ?

