# Supplementary Information (SI) for Chemical Communications.
# 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_RS_4Cl_CF2I_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2390118'
loop_
_audit_author_name
_audit_author_address
'Dr. Vivek Kumar Singh'
;Indian Institute of Technology Delhi
India
;
_audit_update_record             
;
2024-10-10 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_audit_creation_date             2024-09-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 Cl F2 I N O, C2 H3'
_chemical_formula_sum            'C12 H9 Cl F2 I N O'
_chemical_formula_weight         383.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.6441(15)
_cell_length_b                   11.7421(19)
_cell_length_c                   24.791(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2516.3(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7028
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.751
_shelx_estimated_absorpt_T_min   0.636
_exptl_absorpt_coefficient_mu    2.768
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1876 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.9071.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.025
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9805
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         2.873
_diffrn_ambient_temperature      302.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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           1.0
_diffrn_source_power             0.05
_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                2054
_reflns_number_total             2224
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.141
_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)+(0.0396P)²+15.4561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1269
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C8-C1 \\sim C8-C1A
 with sigma of 0.02
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H1AA(0.5) H1AB(0.5) H1AC(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.39669(6) 0.33008(4) 0.27572(2) 0.0530(2) Uani 1 1 d . . . . .
Cl1 Cl 0.6154(3) 0.1400(2) 0.48570(10) 0.0836(8) Uani 1 1 d . . . . .
F1 F 0.2081(4) 0.3740(4) 0.37035(18) 0.0569(11) Uani 1 1 d . . . . .
F2 F 0.2028(4) 0.5152(4) 0.31431(19) 0.0630(12) Uani 1 1 d . . . . .
O1 O 0.4848(6) 0.6540(4) 0.3089(2) 0.0644(15) Uani 1 1 d . . . . .
N1 N 0.6742(6) 0.5401(5) 0.3444(2) 0.0442(13) Uani 1 1 d . . . . .
C1 C 0.313(2) 0.581(3) 0.4210(10) 0.072(6) Uani 1 1 d D . . A 1
H1A H 0.222872 0.539016 0.431997 0.108 Uiso 0.5 1 calc R U P A 1
H1B H 0.282664 0.651739 0.405285 0.108 Uiso 0.5 1 calc R U P A 1
H1C H 0.377567 0.594622 0.451888 0.108 Uiso 0.5 1 calc R U P A 1
C1A C 0.352(2) 0.580(2) 0.4294(9) 0.058(4) Uani 1 1 d D . . B 2
H1AA H 0.263378 0.623998 0.419109 0.087 Uiso 0.5 1 calc R U P B 2
H1AB H 0.432977 0.630193 0.441315 0.087 Uiso 0.5 1 calc R U P B 2
H1AC H 0.324659 0.529202 0.458176 0.087 Uiso 0.5 1 calc R U P B 2
C2 C 0.5326(7) 0.4159(6) 0.3964(3) 0.0423(14) Uani 1 1 d . . . . .
C3 C 0.6819(7) 0.4446(6) 0.3785(3) 0.0429(15) Uani 1 1 d . . . . .
C4 C 0.8080(8) 0.3840(7) 0.3950(3) 0.059(2) Uani 1 1 d . . . . .
H4 H 0.906926 0.404003 0.383664 0.071 Uiso 1 1 calc R U . . .
C5 C 0.7844(9) 0.2902(7) 0.4295(3) 0.059(2) Uani 1 1 d . . . . .
H5 H 0.868914 0.248351 0.441667 0.071 Uiso 1 1 calc R U . . .
C6 C 0.6404(10) 0.2606(7) 0.4452(3) 0.0553(18) Uani 1 1 d . . . . .
C7 C 0.5117(9) 0.3227(6) 0.4299(3) 0.0495(16) Uani 1 1 d . . . . .
H7 H 0.413493 0.302429 0.441793 0.059 Uiso 1 1 calc R U . . .
C8 C 0.4193(7) 0.4985(5) 0.3722(3) 0.0409(14) Uani 1 1 d D . . . .
C9 C 0.5250(8) 0.5755(6) 0.3363(3) 0.0461(16) Uani 1 1 d . . . . .
C10 C 0.2994(7) 0.4401(6) 0.3377(3) 0.0455(15) Uani 1 1 d . . . . .
C11 C 0.8086(8) 0.5962(7) 0.3215(3) 0.060(2) Uani 1 1 d . . . . .
H11A H 0.860443 0.639007 0.349085 0.090 Uiso 1 1 calc R U . . .
H11B H 0.776314 0.646633 0.293181 0.090 Uiso 1 1 calc R U . . .
H11C H 0.877877 0.539999 0.307101 0.090 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 C10 2.176(7) . ?
Cl1 C6 1.749(8) . ?
F1 C10 1.371(8) . ?
F2 C10 1.345(7) . ?
O1 C9 1.198(8) . ?
N1 C3 1.407(9) . ?
N1 C9 1.370(9) . ?
N1 C11 1.450(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C8 1.798(13) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C1A C8 1.806(13) . ?
C2 C3 1.406(9) . ?
C2 C7 1.384(9) . ?
C2 C8 1.503(9) . ?
C3 C4 1.364(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.411(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.349(12) . ?
C6 C7 1.384(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.564(9) . ?
C8 C10 1.509(9) . ?
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
C3 N1 C11 124.0(6) . . ?
C9 N1 C3 111.9(5) . . ?
C9 N1 C11 124.0(6) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C8 C1 H1A 109.5 . . ?
C8 C1 H1B 109.5 . . ?
C8 C1 H1C 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C8 C1A H1AA 109.5 . . ?
C8 C1A H1AB 109.5 . . ?
C8 C1A H1AC 109.5 . . ?
C3 C2 C8 108.5(6) . . ?
C7 C2 C3 119.9(6) . . ?
C7 C2 C8 131.6(6) . . ?
C2 C3 N1 109.8(6) . . ?
C4 C3 N1 129.3(6) . . ?
C4 C3 C2 120.9(7) . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.3(7) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(7) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 Cl1 119.2(6) . . ?
C5 C6 C7 121.8(7) . . ?
C7 C6 Cl1 119.0(6) . . ?
C2 C7 H7 120.8 . . ?
C6 C7 C2 118.4(7) . . ?
C6 C7 H7 120.8 . . ?
C2 C8 C1 114.2(11) . . ?
C2 C8 C1A 103.8(10) . . ?
C2 C8 C9 102.7(5) . . ?
C2 C8 C10 112.4(5) . . ?
C9 C8 C1 111.8(12) . . ?
C9 C8 C1A 109.1(10) . . ?
C10 C8 C1 106.0(8) . . ?
C10 C8 C1A 117.7(8) . . ?
C10 C8 C9 109.9(6) . . ?
O1 C9 N1 126.1(6) . . ?
O1 C9 C8 126.8(6) . . ?
N1 C9 C8 107.0(5) . . ?
F1 C10 I1 107.7(4) . . ?
F1 C10 C8 108.5(6) . . ?
F2 C10 I1 109.0(5) . . ?
F2 C10 F1 105.6(5) . . ?
F2 C10 C8 111.9(5) . . ?
C8 C10 I1 113.8(4) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
Cl1 C6 C7 C2 -178.0(5) . . . . ?
N1 C3 C4 C5 -179.8(7) . . . . ?
C1 C8 C9 O1 -57.3(12) . . . . ?
C1 C8 C9 N1 119.4(10) . . . . ?
C1 C8 C10 I1 -178.5(12) . . . . ?
C1 C8 C10 F1 -58.6(13) . . . . ?
C1 C8 C10 F2 57.4(14) . . . . ?
C1A C8 C9 O1 -70.5(12) . . . . ?
C1A C8 C9 N1 106.2(9) . . . . ?
C1A C8 C10 I1 -173.6(12) . . . . ?
C1A C8 C10 F1 -53.8(13) . . . . ?
C1A C8 C10 F2 62.3(13) . . . . ?
C2 C3 C4 C5 1.3(11) . . . . ?
C2 C8 C9 O1 179.9(7) . . . . ?
C2 C8 C9 N1 -3.4(7) . . . . ?
C2 C8 C10 I1 -53.2(6) . . . . ?
C2 C8 C10 F1 66.7(7) . . . . ?
C2 C8 C10 F2 -177.2(5) . . . . ?
C3 N1 C9 O1 -179.5(7) . . . . ?
C3 N1 C9 C8 3.7(7) . . . . ?
C3 C2 C7 C6 0.5(10) . . . . ?
C3 C2 C8 C1 -119.2(12) . . . . ?
C3 C2 C8 C1A -111.7(10) . . . . ?
C3 C2 C8 C9 2.0(7) . . . . ?
C3 C2 C8 C10 120.1(6) . . . . ?
C3 C4 C5 C6 0.9(11) . . . . ?
C4 C5 C6 Cl1 177.2(6) . . . . ?
C4 C5 C6 C7 -2.5(12) . . . . ?
C5 C6 C7 C2 1.7(11) . . . . ?
C7 C2 C3 N1 178.9(6) . . . . ?
C7 C2 C3 C4 -2.0(10) . . . . ?
C7 C2 C8 C1 62.2(14) . . . . ?
C7 C2 C8 C1A 69.7(12) . . . . ?
C7 C2 C8 C9 -176.6(7) . . . . ?
C7 C2 C8 C10 -58.5(10) . . . . ?
C8 C2 C3 N1 0.1(8) . . . . ?
C8 C2 C3 C4 179.2(6) . . . . ?
C8 C2 C7 C6 179.0(7) . . . . ?
C9 N1 C3 C2 -2.5(8) . . . . ?
C9 N1 C3 C4 178.5(7) . . . . ?
C9 C8 C10 I1 60.6(6) . . . . ?
C9 C8 C10 F1 -179.6(5) . . . . ?
C9 C8 C10 F2 -63.5(7) . . . . ?
C10 C8 C9 O1 60.1(9) . . . . ?
C10 C8 C9 N1 -123.2(6) . . . . ?
C11 N1 C3 C2 176.1(6) . . . . ?
C11 N1 C3 C4 -2.9(11) . . . . ?
C11 N1 C9 O1 1.8(11) . . . . ?
C11 N1 C9 C8 -174.9(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_RSK-40
_database_code_depnum_ccdc_archive 'CCDC 2413454'
loop_
_audit_author_name
_audit_author_address
'Vivek Kumar Singh'
;Indian Institute of Technology Delhi
India
;
_audit_update_record             
;
2024-12-28 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_audit_creation_date             2024-12-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C10.90 H8.80 F3 I0.94 N O'
_chemical_formula_sum            'C10.90 H8.80 F3 I0.94 N O'
_chemical_formula_weight         346.58
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
I -0.29566 6.85062 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07120 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.28658(18)
_cell_length_b                   12.1890(2)
_cell_length_c                   12.0734(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.993(2)
_cell_angle_gamma                90
_cell_volume                     1214.85(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6805
_cell_measurement_temperature    299.99(18)
_cell_measurement_theta_max      80.8110
_cell_measurement_theta_min      5.1490
_exptl_absorpt_coefficient_mu    19.840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Rigaku Oxford Diffraction, 2022)'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_description       block
_exptl_crystal_F_000             664.9
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.1029
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.9927
_diffrn_reflns_Laue_measured_fraction_max 0.9671
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8187
_diffrn_reflns_point_group_measured_fraction_full 0.9927
_diffrn_reflns_point_group_measured_fraction_max 0.9671
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         80.99
_diffrn_reflns_theta_min         5.17
_diffrn_ambient_temperature      299.99(18)
_diffrn_measured_fraction_theta_full 0.9927
_diffrn_measured_fraction_theta_max 0.9671
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -7
_reflns_number_gt                2376
_reflns_number_total             2670
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_diff_density_max         2.1489
_refine_diff_density_min         -2.4152
_refine_diff_density_rms         0.2668
_refine_ls_d_res_high            0.7805
_refine_ls_d_res_low             8.5613
_refine_ls_goodness_of_fit_ref   1.0300
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0879
_refine_ls_restrained_S_all      1.0300
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1844P)²+5.5655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2539
_refine_ls_wR_factor_ref         0.2567
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C7)
2. Others
 Sof(C10)=Sof(H10a)=Sof(H10b)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
3.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
I1 I -0.01789(6) 0.17749(5) 0.42778(5) 0.0492(3) Uani 0.944(10) . P 1
F13 F 0.5968(7) 0.2468(4) 0.6128(5) 0.0603(16) Uani 1.000000 . . .
F14 F 0.4883(8) 0.0905(5) 0.6426(6) 0.0655(17) Uani 1.000000 . . .
F15 F 0.5641(8) 0.1255(5) 0.4829(6) 0.0632(16) Uani 1.000000 . . .
O16 O 0.2215(9) 0.2320(5) 0.7131(5) 0.0515(16) Uani 1.000000 . . .
N9 N 0.2419(9) 0.3838(5) 0.6032(5) 0.0392(15) Uani 1.000000 . . .
C1 C 0.2891(8) 0.4059(5) 0.4972(5) 0.0300(14) Uani 1.000000 . . .
C2 C 0.2859(11) 0.5054(6) 0.4406(7) 0.0450(19) Uani 1.000000 . . .
H2 H 0.2511(11) 0.5695(6) 0.4729(7) 0.054(2) Uiso 1.000000 R . .
C3 C 0.3360(13) 0.5053(7) 0.3354(7) 0.052(2) Uani 1.000000 . . .
H3 H 0.3348(13) 0.5708(7) 0.2959(7) 0.062(3) Uiso 1.000000 R . .
C4 C 0.3882(12) 0.4110(8) 0.2863(7) 0.050(2) Uani 1.000000 . . .
H4 H 0.4224(12) 0.4143(8) 0.2150(7) 0.059(3) Uiso 1.000000 R . .
C5 C 0.3903(12) 0.3109(7) 0.3419(7) 0.0437(19) Uani 1.000000 . . .
H5 H 0.4235(12) 0.2470(7) 0.3085(7) 0.052(2) Uiso 1.000000 R . .
C6 C 0.3411(9) 0.3098(5) 0.4490(6) 0.0302(15) Uani 1.000000 . . .
C7 C 0.3274(9) 0.2174(5) 0.5309(6) 0.0350(13) Uani 1.000000 . . .
C8 C 0.2586(9) 0.2758(6) 0.6308(6) 0.0337(15) Uani 1.000000 . . .
C10 C 0.2174(10) 0.1230(6) 0.4890(7) 0.035(3) Uani 0.90(4) . P 1
H10a H 0.2075(10) 0.0714(6) 0.5492(7) 0.041(3) Uiso 0.90(4) R P 1
H10b H 0.2668(10) 0.0848(6) 0.4301(7) 0.041(3) Uiso 0.90(4) R P 1
C12 C 0.5087(9) 0.1665(5) 0.5755(6) 0.0350(13) Uani 1.000000 . . .
C17 C 0.1758(13) 0.4666(8) 0.6742(8) 0.056(2) Uani 1.000000 . . .
H17a H 0.253(5) 0.525(4) 0.687(6) 0.084(4) Uiso 1.000000 GR . .
H17b H 0.077(6) 0.495(5) 0.638(3) 0.084(4) Uiso 1.000000 GR . .
H17c H 0.154(10) 0.4339(19) 0.744(3) 0.084(4) Uiso 1.000000 GR . .


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 C10 2.130(8) . ?
F13 C12 1.278(8) . ?
F14 C12 1.252(9) . ?
F15 C12 1.342(9) . ?
O16 C8 1.192(11) . ?
N9 C1 1.396(9) . ?
N9 C8 1.363(11) . ?
N9 C17 1.461(10) . ?
C1 C2 1.392(10) . ?
C1 C6 1.393(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(11) . ?
C6 C7 1.509(9) . ?
C7 C8 1.551(10) . ?
C7 C10 1.526(9) . ?
C7 C12 1.670(11) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C17 H17a 0.9600 . ?
C17 H17b 0.9600 . ?
C17 H17c 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 N9 C1 112.3(6) . . ?
C17 N9 C1 123.7(7) . . ?
C17 N9 C8 124.0(7) . . ?
C2 C1 N9 128.5(7) . . ?
C6 C1 N9 110.0(6) . . ?
C6 C1 C2 121.4(7) . . ?
H2 C2 C1 121.3(5) . . ?
C3 C2 C1 117.4(8) . . ?
C3 C2 H2 121.3(5) . . ?
H3 C3 C2 119.0(5) . . ?
C4 C3 C2 122.1(7) . . ?
C4 C3 H3 119.0(5) . . ?
H4 C4 C3 119.5(5) . . ?
C5 C4 C3 120.9(8) . . ?
C5 C4 H4 119.5(5) . . ?
H5 C5 C4 121.1(5) . . ?
C6 C5 C4 117.7(8) . . ?
C6 C5 H5 121.1(4) . . ?
C5 C6 C1 120.4(6) . . ?
C7 C6 C1 108.1(6) . . ?
C7 C6 C5 131.5(7) . . ?
C8 C7 C6 102.7(5) . . ?
C10 C7 C6 114.9(6) . . ?
C10 C7 C8 110.8(6) . . ?
C12 C7 C6 111.8(6) . . ?
C12 C7 C8 107.5(6) . . ?
C12 C7 C10 108.8(5) . . ?
N9 C8 O16 127.5(8) . . ?
C7 C8 O16 125.6(8) . . ?
C7 C8 N9 106.8(6) . . ?
C7 C10 I1 112.4(5) . . ?
H10a C10 I1 109.1(2) . . ?
H10a C10 C7 109.1(4) . . ?
H10b C10 I1 109.1(2) . . ?
H10b C10 C7 109.1(4) . . ?
H10b C10 H10a 107.8 . . ?
F14 C12 F13 116.4(7) . . ?
F15 C12 F13 110.6(7) . . ?
F15 C12 F14 109.8(6) . . ?
C7 C12 F13 107.4(5) . . ?
C7 C12 F14 108.4(6) . . ?
C7 C12 F15 103.5(6) . . ?
H17a C17 N9 109.5 . . ?
H17b C17 N9 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 N9 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?

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
I1 C10 C7 C6 -53.2(6) . . . . ?
I1 C10 C7 C8 62.7(6) . . . . ?
I1 C10 C7 C12 -179.4(5) . . . . ?
F13 C12 C7 C6 53.7(7) . . . . ?
F13 C12 C7 C8 -58.4(6) . . . . ?
F13 C12 C7 C10 -178.4(6) . . . . ?
F14 C12 C7 C6 -179.8(6) . . . . ?
F14 C12 C7 C8 68.1(6) . . . . ?
F14 C12 C7 C10 -51.9(7) . . . . ?
F15 C12 C7 C6 -63.3(6) . . . . ?
F15 C12 C7 C8 -175.4(5) . . . . ?
F15 C12 C7 C10 64.6(6) . . . . ?
O16 C8 N9 C1 -176.4(9) . . . . ?
O16 C8 N9 C17 1.1(12) . . . . ?
O16 C8 C7 C6 176.3(9) . . . . ?
O16 C8 C7 C10 53.1(10) . . . . ?
O16 C8 C7 C12 -65.6(9) . . . . ?
N9 C1 C2 C3 -178.6(9) . . . . ?
N9 C1 C6 C5 178.4(7) . . . . ?
N9 C1 C6 C7 -0.3(7) . . . . ?
N9 C8 C7 C6 -0.7(6) . . . . ?
N9 C8 C7 C10 -124.0(6) . . . . ?
N9 C8 C7 C12 117.3(6) . . . . ?
C1 C2 C3 C4 -0.1(10) . . . . ?
C1 C6 C5 C4 1.1(9) . . . . ?
C1 C6 C7 C8 0.6(6) . . . . ?
C1 C6 C7 C10 121.0(6) . . . . ?
C1 C6 C7 C12 -114.4(6) . . . . ?
C2 C3 C4 C5 0.7(12) . . . . ?
C3 C4 C5 C6 -1.2(11) . . . . ?
C4 C5 C6 C7 179.4(7) . . . . ?
C5 C6 C7 C8 -177.9(10) . . . . ?
C5 C6 C7 C10 -57.5(10) . . . . ?
C5 C6 C7 C12 67.1(10) . . . . ?


_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_RSK-MF-S1_auto
_database_code_depnum_ccdc_archive 'CCDC 2412900'
loop_
_audit_author_name
_audit_author_address
'Vivek Kumar Singh'
;Indian Institute of Technology Delhi
India
;
_audit_update_record             
;
2024-12-25 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_chemical_formula_moiety         'C11 H11 F I N O'
_chemical_formula_sum            'C11 H11 F I N O'
_chemical_formula_weight         319.11
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
I -0.29566 6.85062 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07120 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.1305(4)
_cell_length_b                   11.7122(2)
_cell_length_c                   16.4642(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.747(3)
_cell_angle_gamma                90
_cell_volume                     2335.05(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5148
_cell_measurement_temperature    297.06(10)
_cell_measurement_theta_max      81.35
_cell_measurement_theta_min      3.65
_exptl_absorpt_coefficient_mu    21.475
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_F_000             1232.0
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_description       block
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.1651
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 0.9983
_diffrn_reflns_Laue_measured_fraction_max 0.9747
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16979
_diffrn_reflns_point_group_measured_fraction_full 0.9983
_diffrn_reflns_point_group_measured_fraction_max 0.9747
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         81.35
_diffrn_reflns_theta_min         3.65
_diffrn_ambient_temperature      297.06(10)
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_exptl_absorpt_correction_T_max  0.061
_exptl_absorpt_correction_T_min  0.040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Rigaku Oxford Diffraction, 2022)'
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9747
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4272
_reflns_number_total             5148
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         2.1941
_refine_diff_density_min         -2.3702
_refine_diff_density_rms         0.3504
_refine_ls_d_res_high            0.7798
_refine_ls_d_res_low             12.1092
_refine_ls_goodness_of_fit_ref   1.2405
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     287
_refine_ls_number_reflns         5017
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.1050
_refine_ls_restrained_S_all      1.2399
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2914
_refine_ls_wR_factor_ref         0.2995
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25-I3 \\sim C25-I3a
 with sigma of 0.02
 C10-I2 \\sim C10-I2a
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C25) = Uanis(I3a)
4. Others
 Fixed Sof: I2(0.5) I3(0.5) I3a(0.5) I2a(0.5) H10(0.5) H10a(0.5) H25(0.5)
 H25a(0.5)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C10(H10a), C25(H25), C25(H25a)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C2(H2), C20(H20), C19(H19), C18(H18), C17(H17)
5.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C29(H29a,H29b,H29c), C30(H30a,H30b,
 H30c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
I2 I 0.9117(3) 0.7856(3) 0.6013(2) 0.088(2) Uani 0.500000 D P 1
I2a I 0.90975(17) 0.78736(15) 0.59856(10) 0.0341(6) Uani 0.500000 D P 2
F12 F 1.0251(5) 0.5973(5) 0.5619(4) 0.0634(15) Uani 1.000000 . . .
O13 O 0.7381(5) 0.5488(7) 0.6231(5) 0.0696(19) Uani 1.000000 . . .
N9 N 0.8699(6) 0.5750(6) 0.7626(4) 0.0479(16) Uani 1.000000 . . .
C1 C 0.9856(7) 0.5774(7) 0.8012(5) 0.0428(17) Uani 1.000000 . . .
C2 C 1.0534(11) 0.5946(10) 0.8898(6) 0.069(3) Uani 1.000000 . . .
H2 H 1.0237(11) 0.6083(10) 0.9318(6) 0.083(4) Uiso 1.000000 R . .
C3 C 1.1649(11) 0.5903(9) 0.9120(7) 0.075(3) Uani 1.000000 . . .
H3 H 1.2117(11) 0.6006(9) 0.9707(7) 0.090(4) Uiso 1.000000 R . .
C4 C 1.2095(9) 0.5715(10) 0.8514(9) 0.077(4) Uani 1.000000 . . .
H4 H 1.2859(9) 0.5712(10) 0.8690(9) 0.092(4) Uiso 1.000000 R . .
C5 C 1.1422(7) 0.5525(8) 0.7624(7) 0.060(2) Uani 1.000000 . . .
H5 H 1.1729(7) 0.5385(8) 0.7210(7) 0.072(3) Uiso 1.000000 R . .
C6 C 1.0284(6) 0.5554(6) 0.7380(5) 0.0376(15) Uani 1.000000 . . .
C7 C 0.9351(7) 0.5313(6) 0.6521(5) 0.0410(16) Uani 1.000000 . . .
C8 C 0.8344(6) 0.5511(7) 0.6751(5) 0.0416(16) Uani 1.000000 . . .
C10 C 0.9305(7) 0.6076(6) 0.5766(5) 0.0403(17) Uani 1.000000 D . .
H10 H 0.8680(7) 0.5841(6) 0.5233(5) 0.048(2) Uiso 0.500000 R P 1
H10a H 0.8684(7) 0.5832(6) 0.5234(5) 0.048(2) Uiso 0.500000 R P 2
C14 C 0.7989(11) 0.5934(9) 0.8109(8) 0.070(3) Uani 1.000000 . . .
H14a H 0.812(5) 0.534(4) 0.854(4) 0.104(5) Uiso 1.000000 GR . .
H14b H 0.815(5) 0.666(3) 0.839(5) 0.104(5) Uiso 1.000000 GR . .
H14c H 0.7230(11) 0.591(7) 0.7707(11) 0.104(5) Uiso 1.000000 GR . .
C15 C 0.9349(10) 0.4003(8) 0.6257(6) 0.057(2) Uani 1.000000 . . .
H15a H 1.001(3) 0.3835(18) 0.617(5) 0.086(4) Uiso 1.000000 GR . .
H15b H 0.931(7) 0.3531(8) 0.672(2) 0.086(4) Uiso 1.000000 GR . .
H15c H 0.872(4) 0.3855(18) 0.572(3) 0.086(4) Uiso 1.000000 GR . .
I3 I 0.5759(2) 0.8931(3) 0.4058(2) 0.082(2) Uani 0.500000 D P 1
I3a I 0.57916(18) 0.89257(16) 0.40697(10) 0.0369(6) Uani 0.500000 D P 2
F27 F 0.4975(5) 0.7038(5) 0.4765(3) 0.0659(16) Uani 1.000000 . . .
O28 O 0.7337(5) 0.6282(6) 0.3634(4) 0.0560(16) Uani 1.000000 . . .
N24 N 0.5847(5) 0.6708(6) 0.2371(4) 0.0411(14) Uani 1.000000 . . .
C16 C 0.4710(6) 0.6852(6) 0.2124(4) 0.0349(14) Uani 1.000000 . . .
C17 C 0.3910(8) 0.7196(7) 0.1315(5) 0.050(2) Uani 1.000000 . . .
H17 H 0.4092(8) 0.7326(7) 0.0831(5) 0.060(2) Uiso 1.000000 R . .
C18 C 0.2840(9) 0.7336(9) 0.1259(7) 0.063(3) Uani 1.000000 . . .
H18 H 0.2300(9) 0.7581(9) 0.0731(7) 0.076(3) Uiso 1.000000 R . .
C19 C 0.2559(8) 0.7126(8) 0.1954(7) 0.063(3) Uani 1.000000 . . .
H19 H 0.1826(8) 0.7203(8) 0.1887(7) 0.076(3) Uiso 1.000000 R . .
C20 C 0.3349(6) 0.6795(8) 0.2774(6) 0.0502(19) Uani 1.000000 . . .
H20 H 0.3155(6) 0.6663(8) 0.3253(6) 0.060(2) Uiso 1.000000 R . .
C21 C 0.4429(6) 0.6671(6) 0.2844(5) 0.0374(15) Uani 1.000000 . . .
C22 C 0.5456(6) 0.6341(6) 0.3622(4) 0.0320(13) Uani 1.000000 . . .
C23 C 0.6354(6) 0.6443(6) 0.3237(4) 0.0346(14) Uani 1.000000 . . .
C25 C 0.5754(7) 0.7133(6) 0.4414(5) 0.0369(6) Uani 1.000000 D . .
H25 H 0.6479(7) 0.6923(6) 0.4857(5) 0.0443(8) Uiso 0.500000 R P 1
H25a H 0.6476(7) 0.6914(6) 0.4857(5) 0.0443(8) Uiso 0.500000 R P 2
C29 C 0.6425(8) 0.6827(9) 0.1771(6) 0.057(2) Uani 1.000000 . . .
H29a H 0.619(5) 0.624(4) 0.133(3) 0.085(3) Uiso 1.000000 GR . .
H29b H 0.626(5) 0.756(3) 0.149(4) 0.085(3) Uiso 1.000000 GR . .
H29c H 0.7207(9) 0.676(7) 0.2098(10) 0.085(3) Uiso 1.000000 GR . .
C30 C 0.5419(9) 0.5093(8) 0.3921(6) 0.052(2) Uani 1.000000 . . .
H30a H 0.482(4) 0.5009(17) 0.412(5) 0.078(3) Uiso 1.000000 GR . .
H30b H 0.531(6) 0.4585(9) 0.3437(15) 0.078(3) Uiso 1.000000 GR . .
H30c H 0.610(3) 0.491(2) 0.440(3) 0.078(3) Uiso 1.000000 GR . .


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
I2 C10 2.157(8) . ?
I2a C10 2.171(7) . ?
F12 C10 1.360(9) . ?
O13 C8 1.222(10) . ?
N9 C1 1.402(11) . ?
N9 C8 1.361(11) . ?
N9 C14 1.457(11) . ?
C1 C2 1.398(12) . ?
C1 C6 1.384(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.406(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(11) . ?
C6 C7 1.497(10) . ?
C7 C8 1.528(10) . ?
C7 C10 1.513(10) . ?
C7 C15 1.594(11) . ?
C10 H10 0.9800 . ?
C10 H10a 0.9800 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?
I3 C25 2.187(8) . ?
I3a C25 2.181(7) . ?
F27 C25 1.359(8) . ?
O28 C23 1.215(9) . ?
N24 C16 1.397(9) . ?
N24 C23 1.356(9) . ?
N24 C29 1.467(9) . ?
C16 C17 1.399(11) . ?
C16 C21 1.388(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(15) . ?
C18 H18 0.9300 . ?
C18 C19 1.354(17) . ?
C19 H19 0.9300 . ?
C19 C20 1.402(14) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(10) . ?
C21 C22 1.507(10) . ?
C22 C23 1.544(9) . ?
C22 C25 1.524(9) . ?
C22 C30 1.549(11) . ?
C25 H25 0.9800 . ?
C25 H25a 0.9800 . ?
C29 H29a 0.9600 . ?
C29 H29b 0.9600 . ?
C29 H29c 0.9600 . ?
C30 H30a 0.9600 . ?
C30 H30b 0.9600 . ?
C30 H30c 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 N9 C1 110.6(6) . . ?
C14 N9 C1 124.1(8) . . ?
C14 N9 C8 125.3(8) . . ?
C2 C1 N9 128.0(8) . . ?
C6 C1 N9 109.8(6) . . ?
C6 C1 C2 122.1(9) . . ?
H2 C2 C1 121.4(6) . . ?
C3 C2 C1 117.3(10) . . ?
C3 C2 H2 121.4(7) . . ?
H3 C3 C2 118.9(7) . . ?
C4 C3 C2 122.1(10) . . ?
C4 C3 H3 118.9(6) . . ?
H4 C4 C3 119.5(6) . . ?
C5 C4 C3 121.1(10) . . ?
C5 C4 H4 119.5(7) . . ?
H5 C5 C4 121.0(7) . . ?
C6 C5 C4 118.0(10) . . ?
C6 C5 H5 121.0(6) . . ?
C5 C6 C1 119.4(8) . . ?
C7 C6 C1 108.9(7) . . ?
C7 C6 C5 131.5(8) . . ?
C8 C7 C6 102.0(6) . . ?
C10 C7 C6 115.1(6) . . ?
C10 C7 C8 110.5(7) . . ?
C15 C7 C6 110.7(7) . . ?
C15 C7 C8 107.6(7) . . ?
C15 C7 C10 110.5(6) . . ?
N9 C8 O13 125.7(8) . . ?
C7 C8 O13 125.7(7) . . ?
C7 C8 N9 108.5(6) . . ?
I2a C10 I2 1.18(13) . . ?
F12 C10 I2 107.4(5) . . ?
F12 C10 I2a 107.3(5) . . ?
C7 C10 I2 112.8(5) . . ?
C7 C10 I2a 113.8(5) . . ?
C7 C10 F12 110.1(7) . . ?
H10 C10 I2 108.8(2) . . ?
H10 C10 I2a 107.8(2) . . ?
H10 C10 F12 108.8(4) . . ?
H10 C10 C7 108.8(4) . . ?
H10a C10 I2 109.5(2) . . ?
H10a C10 I2a 108.5(2) . . ?
H10a C10 F12 108.5(4) . . ?
H10a C10 C7 108.5(4) . . ?
H10a C10 H10 0.7 . . ?
H14a C14 N9 109.5 . . ?
H14b C14 N9 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 N9 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H15a C15 C7 109.5 . . ?
H15b C15 C7 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C7 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
C23 N24 C16 111.6(5) . . ?
C29 N24 C16 124.5(6) . . ?
C29 N24 C23 123.9(7) . . ?
C17 C16 N24 129.5(7) . . ?
C21 C16 N24 109.9(6) . . ?
C21 C16 C17 120.5(7) . . ?
H17 C17 C16 121.0(5) . . ?
C18 C17 C16 117.9(8) . . ?
C18 C17 H17 121.0(6) . . ?
H18 C18 C17 119.2(6) . . ?
C19 C18 C17 121.6(9) . . ?
C19 C18 H18 119.2(6) . . ?
H19 C19 C18 119.3(6) . . ?
C20 C19 C18 121.5(9) . . ?
C20 C19 H19 119.3(6) . . ?
H20 C20 C19 121.3(6) . . ?
C21 C20 C19 117.5(9) . . ?
C21 C20 H20 121.3(5) . . ?
C20 C21 C16 121.0(7) . . ?
C22 C21 C16 108.6(6) . . ?
C22 C21 C20 130.4(7) . . ?
C23 C22 C21 101.9(5) . . ?
C25 C22 C21 114.9(6) . . ?
C25 C22 C23 108.7(6) . . ?
C30 C22 C21 112.6(6) . . ?
C30 C22 C23 109.0(6) . . ?
C30 C22 C25 109.3(6) . . ?
N24 C23 O28 126.1(6) . . ?
C22 C23 O28 126.0(6) . . ?
C22 C23 N24 107.8(6) . . ?
I3a C25 I3 1.04(13) . . ?
F27 C25 I3 105.9(5) . . ?
F27 C25 I3a 106.6(5) . . ?
C22 C25 I3 112.5(5) . . ?
C22 C25 I3a 112.8(5) . . ?
C22 C25 F27 109.1(6) . . ?
H25 C25 I3 109.8(2) . . ?
H25 C25 I3a 108.8(2) . . ?
H25 C25 F27 109.8(4) . . ?
H25 C25 C22 109.8(4) . . ?
H25a C25 I3 110.4(2) . . ?
H25a C25 I3a 109.4(2) . . ?
H25a C25 F27 109.4(4) . . ?
H25a C25 C22 109.4(4) . . ?
H25a C25 H25 0.7 . . ?
H29a C29 N24 109.5 . . ?
H29b C29 N24 109.5 . . ?
H29b C29 H29a 109.5 . . ?
H29c C29 N24 109.5 . . ?
H29c C29 H29a 109.5 . . ?
H29c C29 H29b 109.5 . . ?
H30a C30 C22 109.5 . . ?
H30b C30 C22 109.5 . . ?
H30b C30 H30a 109.5 . . ?
H30c C30 C22 109.5 . . ?
H30c C30 H30a 109.5 . . ?
H30c C30 H30b 109.5 . . ?

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
I2 C10 C7 C6 -60.4(6) . . . . ?
I2 C10 C7 C8 54.5(6) . . . . ?
I2 C10 C7 C15 173.4(6) . . . . ?
I2a C10 C7 C6 -61.0(6) . . . . ?
I2a C10 C7 C8 53.8(6) . . . . ?
I2a C10 C7 C15 172.8(6) . . . . ?
F12 C10 C7 C6 59.5(7) . . . . ?
F12 C10 C7 C8 174.4(6) . . . . ?
F12 C10 C7 C15 -66.7(7) . . . . ?
O13 C8 N9 C1 -176.2(9) . . . . ?
O13 C8 N9 C14 5.0(11) . . . . ?
O13 C8 C7 C6 174.8(9) . . . . ?
O13 C8 C7 C10 52.0(9) . . . . ?
O13 C8 C7 C15 -68.7(9) . . . . ?
N9 C1 C2 C3 178.3(10) . . . . ?
N9 C1 C6 C5 -179.3(6) . . . . ?
N9 C1 C6 C7 -2.7(7) . . . . ?
N9 C8 C7 C6 -3.5(7) . . . . ?
N9 C8 C7 C10 -126.3(7) . . . . ?
N9 C8 C7 C15 113.0(7) . . . . ?
C1 C2 C3 C4 0.7(13) . . . . ?
C1 C6 C5 C4 0.5(9) . . . . ?
C1 C6 C7 C8 3.7(6) . . . . ?
C1 C6 C7 C10 123.4(6) . . . . ?
C1 C6 C7 C15 -110.5(7) . . . . ?
C2 C3 C4 C5 -1.7(13) . . . . ?
C3 C4 C5 C6 1.0(13) . . . . ?
C4 C5 C6 C7 -175.2(8) . . . . ?
C5 C6 C7 C8 179.7(9) . . . . ?
C5 C6 C7 C10 -60.6(9) . . . . ?
C5 C6 C7 C15 65.5(10) . . . . ?
I3 C25 C22 C21 -49.7(5) . . . . ?
I3 C25 C22 C23 63.6(5) . . . . ?
I3 C25 C22 C30 -177.5(6) . . . . ?
I3a C25 C22 C21 -50.8(6) . . . . ?
I3a C25 C22 C23 62.5(6) . . . . ?
I3a C25 C22 C30 -178.6(6) . . . . ?
F27 C25 C22 C21 67.5(7) . . . . ?
F27 C25 C22 C23 -179.2(6) . . . . ?
F27 C25 C22 C30 -60.3(7) . . . . ?
O28 C23 N24 C16 -179.1(8) . . . . ?
O28 C23 N24 C29 0.9(11) . . . . ?
O28 C23 C22 C21 178.2(8) . . . . ?
O28 C23 C22 C25 56.5(9) . . . . ?
O28 C23 C22 C30 -62.6(9) . . . . ?
N24 C16 C17 C18 -176.2(9) . . . . ?
N24 C16 C21 C20 178.2(6) . . . . ?
N24 C16 C21 C22 -2.1(6) . . . . ?
N24 C23 C22 C21 -3.7(7) . . . . ?
N24 C23 C22 C25 -125.4(6) . . . . ?
N24 C23 C22 C30 115.5(7) . . . . ?
C16 C17 C18 C19 -1.4(10) . . . . ?
C16 C21 C20 C19 -1.0(9) . . . . ?
C16 C21 C22 C23 3.5(6) . . . . ?
C16 C21 C22 C25 120.7(6) . . . . ?
C16 C21 C22 C30 -113.2(6) . . . . ?
C17 C18 C19 C20 2.3(12) . . . . ?
C18 C19 C20 C21 -1.0(11) . . . . ?
C19 C20 C21 C22 179.4(7) . . . . ?
C20 C21 C22 C23 -176.9(9) . . . . ?
C20 C21 C22 C25 -59.6(9) . . . . ?
C20 C21 C22 C30 66.4(10) . . . . ?


loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C10 I2 1 2
C10 I2a 1 2
C25 I3 1 1
C25 I3a 1 1

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 2.1837 0.0030 0.0030
2 0.0200 2.1639 0.0071 0.0071

