# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_as868
_database_code_depnum_ccdc_archive 'CCDC 1963420'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'

# start Validation Reply Form
_vrf_PLAT973_as868               
;
PROBLEM: Check Calcd Positive Resid. Density on       Pd1       2.05 eA-3  
RESPONSE: Absorption correction was applied and this residual density
          is not certainly due to wrongly assigned atom types
		  or caused by unaccounted for twinning. It could be due to a 
		  very poor crystal quality, however, it represents the best
		  possible data after multiple recrystallization attempts.
;
_vrf_PLAT971_as868               
;
PROBLEM: Check Calcd Resid. Dens.  0.82A   From Pd1             2.55 eA-3  
RESPONSE: Absorption correction was applied and this residual density
          is not certainly due to wrongly assigned atom types
		  or caused by unaccounted for twinning. It could be due to a 
		  very poor crystal quality, however, it represents the best
		  possible data after multiple recrystallization attempts.
;
_chemical_name_common            (TolTr)2PdCl2
_chemical_name_systematic        AS868
_chemical_formula_moiety         'C22 H30 Cl2 N6 Pd'
_chemical_formula_sum            'C22 H30 Cl2 N6 Pd'
_chemical_formula_weight         555.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H30 N6 Cl2 Pd1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 '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                   9.2984(10)
_cell_length_b                   12.1013(13)
_cell_length_c                   12.2378(13)
_cell_angle_alpha                82.298(9)
_cell_angle_beta                 68.456(10)
_cell_angle_gamma                70.100(10)
_cell_volume                     1204.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3328
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.6280
_cell_measurement_theta_min      3.8500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.423
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.214
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics 
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0475
-1 0 1 0.0977
-2 5 -3 0.0830
1 5 1 0.0178
0 0 1 0.0838
-2 1 1 0.1023
0 3 -5 0.0844
-5 1 0 0.1398
0 2 5 0.0564
3 5 -1 0.0193
-3 -5 2 0.1035
-1 -5 -3 0.0638
0 0 -1 0.0805
1 1 2 0.0996
0 -1 -1 0.0533
1 0 0 0.1203

_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.101
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.9999 1.0000 0.1264 0.0856 0.1138
-1.0000 -0.0001 1.0000 0.1486 0.2201 -0.0237
-2.0000 4.9998 -3.0003 0.8336 -0.3585 -0.0421
1.0000 4.9998 0.9998 0.4548 -0.1602 0.4238
-0.0000 -0.0000 1.0000 0.0096 0.1227 0.0564
-2.0001 0.9998 1.0000 0.4045 0.2805 -0.0464
0.0001 3.0001 -5.0003 0.3027 -0.7246 -0.1095
-5.0001 0.9996 -0.0000 0.8120 0.4502 -0.3431
-0.0001 1.9997 5.0000 0.2816 0.5392 0.3968
3.0001 5.0000 -1.0003 0.1576 -0.6005 0.4713
-3.0001 -5.0001 2.0003 -0.1480 0.7232 -0.4149
-1.0000 -4.9998 -2.9998 -0.4739 -0.0851 -0.5366
0.0000 0.0000 -1.0000 -0.0096 -0.1227 -0.0564
1.0000 1.0000 2.0000 -0.0030 0.1108 0.2503
0.0000 -0.9999 -1.0000 -0.1264 -0.0856 -0.1138
1.0000 0.0001 0.0000 -0.1390 -0.0975 0.0801

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7530
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.580
_diffrn_reflns_theta_max         66.580
_diffrn_reflns_theta_min         3.884
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  35.00   1.00    4.00    --  -40.66  77.00 120.00   90
  2  ω   -113.00 -14.00   1.00    4.00    --  -40.66 -57.00   0.00   99
  3  ω    -41.00 -15.00   1.00    4.00    --  -40.66  57.00   0.00   26
  4  ω     46.00  95.00   1.00    4.00    --   40.66-125.00 -60.00   49
  5  ω     14.00  63.00   1.00    4.00    --   40.66  57.00-120.00   49
  6  ω     44.00 115.00   1.00    4.00    --   40.66  38.00 -90.00   71
  7  ω     44.00 134.00   1.00   16.00    --  107.03 -61.00 -30.00   90
  8  ω     82.00 178.00   1.00   16.00    --  107.03  61.00 -60.00   96
  9  ω     86.00 117.00   1.00   16.00    --  107.03-125.00-180.00   31
 10  ω    105.00 169.00   1.00   16.00    --  107.03 125.00-120.00   64
 11  ω     77.00 104.00   1.00   16.00    --  107.03-125.00  30.00   27
 12  ω     83.00 156.00   1.00   16.00    --  107.03  45.00   0.00   73
 13  ω     43.00  78.00   1.00   16.00    --  107.03 -94.00-180.00   35
 14  ω    101.00 157.00   1.00   16.00    --  107.03  30.00  90.00   56
 15  ω     34.00 130.00   1.00   16.00    --  107.03 -45.00 150.00   96
 16  ω     90.00 117.00   1.00   16.00    --  107.03-125.00  90.00   27
 17  ω     36.00  61.00   1.00   16.00    --  107.03-125.00  90.00   25
 18  ω     55.00 140.00   1.00   16.00    --  107.03 -77.00-150.00   85
 19  ω     44.00  71.00   1.00   16.00    --  107.03-125.00-180.00   27
 20  ω     93.00 118.00   1.00   16.00    --  107.03-125.00 -60.00   25
 21  ω    102.00 167.00   1.00   16.00    --  107.03  15.00  60.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1390341000
_diffrn_orient_matrix_UB_12      0.1168539000
_diffrn_orient_matrix_UB_13      0.0095779000
_diffrn_orient_matrix_UB_21      -0.0974579000
_diffrn_orient_matrix_UB_22      -0.0370814000
_diffrn_orient_matrix_UB_23      0.1226703000
_diffrn_orient_matrix_UB_31      0.0801049000
_diffrn_orient_matrix_UB_32      0.0574672000
_diffrn_orient_matrix_UB_33      0.0563873000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3447
_reflns_number_total             4181
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.430
_refine_diff_density_min         -1.475
_refine_diff_density_rms         0.276
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0935
_refine_ls_restrained_S_all      1.094
_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)+(0.1631P)²+2.7798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2469
_refine_ls_wR_factor_ref         0.2614
_refine_special_details          ?
_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.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C12(H12A,H12B), C13(H13A,
 H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Pd1 Pd 0.44531(8) 0.68559(5) 0.25318(5) 0.0346(3) Uani 1 1 d . . . . .
Cl1 Cl 0.6668(3) 0.6732(2) 0.08336(19) 0.0422(5) Uani 1 1 d . . . . .
Cl2 Cl 0.2301(3) 0.6899(2) 0.42591(19) 0.0445(6) Uani 1 1 d . . . . .
N1 N 0.2040(11) 0.6671(8) 0.1204(8) 0.0446(19) Uani 1 1 d . . . . .
N2 N 0.2904(11) 0.5673(7) 0.1475(7) 0.0410(18) Uani 1 1 d . . . . .
N3 N 0.3945(10) 0.5572(6) 0.1951(7) 0.0343(15) Uani 1 1 d . . . . .
N4 N 0.6544(11) 0.7570(7) 0.4011(7) 0.0418(18) Uani 1 1 d . . . . .
N5 N 0.5499(10) 0.8424(7) 0.3691(7) 0.0401(17) Uani 1 1 d . . . . .
N6 N 0.4714(10) 0.8267(7) 0.3103(7) 0.0362(16) Uani 1 1 d . . . . .
C1 C 0.2053(15) 0.7868(9) 0.1295(9) 0.048(2) Uani 1 1 d . . . . .
H1A H 0.313578 0.793227 0.089345 0.058 Uiso 1 1 calc R . . . .
H1B H 0.168677 0.808742 0.210947 0.058 Uiso 1 1 calc R . . . .
C2 C 0.0875(15) 0.8626(10) 0.0699(10) 0.054(3) Uani 1 1 d . . . . .
H2A H 0.028021 0.938353 0.107768 0.064 Uiso 1 1 calc R . . . .
H2B H 0.144618 0.874967 -0.012416 0.064 Uiso 1 1 calc R . . . .
C3 C -0.0263(17) 0.7933(11) 0.0838(13) 0.064(3) Uani 1 1 d . . . . .
H3A H -0.109542 0.803918 0.161301 0.076 Uiso 1 1 calc R . . . .
H3B H -0.078442 0.816693 0.025027 0.076 Uiso 1 1 calc R . . . .
C4 C 0.0848(16) 0.6681(11) 0.0666(12) 0.059(3) Uani 1 1 d . . . . .
H4A H 0.025689 0.613483 0.106431 0.071 Uiso 1 1 calc R . . . .
H4B H 0.137699 0.648787 -0.016101 0.071 Uiso 1 1 calc R . . . .
C5 C 0.4761(12) 0.4355(8) 0.2180(8) 0.0357(18) Uani 1 1 d . . . . .
C6 C 0.5527(13) 0.4119(9) 0.3024(9) 0.042(2) Uani 1 1 d . . . . .
H6 H 0.554213 0.473187 0.339927 0.050 Uiso 1 1 calc R . . . .
C7 C 0.6253(13) 0.2968(9) 0.3288(9) 0.043(2) Uani 1 1 d . . . . .
H7 H 0.674090 0.281040 0.385726 0.051 Uiso 1 1 calc R . . . .
C8 C 0.6273(14) 0.2039(9) 0.2722(9) 0.045(2) Uani 1 1 d . . . . .
C9 C 0.5530(14) 0.2303(10) 0.1892(10) 0.050(2) Uani 1 1 d . . . . .
H9 H 0.552827 0.168956 0.150821 0.060 Uiso 1 1 calc R . . . .
C10 C 0.4776(13) 0.3459(9) 0.1603(8) 0.042(2) Uani 1 1 d . . . . .
H10 H 0.429502 0.361385 0.102956 0.050 Uiso 1 1 calc R . . . .
C11 C 0.7097(17) 0.0778(9) 0.3025(11) 0.058(3) Uani 1 1 d . . . . .
H11A H 0.812898 0.071457 0.307367 0.087 Uiso 1 1 calc GR . . . .
H11B H 0.726304 0.026461 0.242539 0.087 Uiso 1 1 calc GR . . . .
H11C H 0.641747 0.055878 0.376672 0.087 Uiso 1 1 calc GR . . . .
C12 C 0.7084(14) 0.6307(8) 0.3778(9) 0.043(2) Uani 1 1 d . . . . .
H12A H 0.738507 0.616322 0.295031 0.051 Uiso 1 1 calc R . . . .
H12B H 0.624404 0.595684 0.423180 0.051 Uiso 1 1 calc R . . . .
C13 C 0.8566(15) 0.5836(9) 0.4176(11) 0.051(3) Uani 1 1 d . . . . .
H13A H 0.869433 0.503626 0.447221 0.061 Uiso 1 1 calc R . . . .
H13B H 0.955373 0.585182 0.353266 0.061 Uiso 1 1 calc R . . . .
C14 C 0.8189(14) 0.6662(9) 0.5141(9) 0.047(2) Uani 1 1 d . . . . .
H14A H 0.917527 0.664182 0.525697 0.056 Uiso 1 1 calc R . . . .
H14B H 0.744534 0.646807 0.587701 0.056 Uiso 1 1 calc R . . . .
C15 C 0.7394(14) 0.7865(10) 0.4670(10) 0.048(2) Uani 1 1 d . . . . .
H15A H 0.663801 0.839880 0.530543 0.058 Uiso 1 1 calc R . . . .
H15B H 0.820754 0.821587 0.416218 0.058 Uiso 1 1 calc R . . . .
C16 C 0.3609(12) 0.9355(8) 0.2862(8) 0.0382(19) Uani 1 1 d . . . . .
C17 C 0.2236(14) 0.9968(8) 0.3773(8) 0.044(2) Uani 1 1 d . . . . .
H17 H 0.201110 0.965735 0.453198 0.053 Uiso 1 1 calc R . . . .
C18 C 0.1219(13) 1.1030(8) 0.3549(9) 0.044(2) Uani 1 1 d . . . . .
H18 H 0.029633 1.142458 0.415643 0.053 Uiso 1 1 calc R . . . .
C19 C 0.1548(13) 1.1516(8) 0.2438(9) 0.041(2) Uani 1 1 d . . . . .
C20 C 0.2872(14) 1.0884(9) 0.1534(9) 0.048(2) Uani 1 1 d . . . . .
H20 H 0.307666 1.119057 0.077375 0.057 Uiso 1 1 calc R . . . .
C21 C 0.3904(13) 0.9803(9) 0.1736(9) 0.043(2) Uani 1 1 d . . . . .
H21 H 0.478472 0.938614 0.111725 0.052 Uiso 1 1 calc R . . . .
C22 C 0.0511(16) 1.2721(10) 0.2201(11) 0.060(3) Uani 1 1 d . . . . .
H22A H -0.012699 1.264723 0.176674 0.091 Uiso 1 1 calc GR . . . .
H22B H 0.120018 1.317863 0.175208 0.091 Uiso 1 1 calc GR . . . .
H22C H -0.020109 1.310247 0.293290 0.091 Uiso 1 1 calc GR . . . .


_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
Pd1 Cl1 2.305(2) . ?
Pd1 Cl2 2.308(2) . ?
Pd1 N3 2.045(7) . ?
Pd1 N6 2.046(7) . ?
N1 N2 1.282(12) . ?
N1 C1 1.471(13) . ?
N1 C4 1.479(13) . ?
N2 N3 1.267(11) . ?
N3 C5 1.452(12) . ?
N4 N5 1.286(12) . ?
N4 C12 1.470(12) . ?
N4 C15 1.462(12) . ?
N5 N6 1.266(11) . ?
N6 C16 1.441(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.515(15) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.511(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.506(17) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.406(13) . ?
C5 C10 1.365(13) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(14) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(14) . ?
C8 C9 1.376(16) . ?
C8 C11 1.521(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.399(15) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.531(14) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.514(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.534(14) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.398(15) . ?
C16 C21 1.375(14) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(15) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(14) . ?
C19 C20 1.381(15) . ?
C19 C22 1.508(14) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(14) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
Cl1 Pd1 Cl2 177.40(8) . . ?
N3 Pd1 Cl1 90.7(2) . . ?
N3 Pd1 Cl2 88.5(2) . . ?
N3 Pd1 N6 173.5(3) . . ?
N6 Pd1 Cl1 92.1(2) . . ?
N6 Pd1 Cl2 89.0(2) . . ?
N2 N1 C1 130.8(8) . . ?
N2 N1 C4 117.9(8) . . ?
C1 N1 C4 111.3(8) . . ?
N3 N2 N1 122.6(8) . . ?
N2 N3 Pd1 129.2(6) . . ?
N2 N3 C5 112.4(7) . . ?
C5 N3 Pd1 118.2(6) . . ?
N5 N4 C12 129.5(8) . . ?
N5 N4 C15 117.4(8) . . ?
C15 N4 C12 113.1(8) . . ?
N6 N5 N4 122.5(8) . . ?
N5 N6 Pd1 136.4(6) . . ?
N5 N6 C16 112.0(7) . . ?
C16 N6 Pd1 111.3(5) . . ?
N1 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
N1 C1 C2 103.6(8) . . ?
H1A C1 H1B 109.0 . . ?
C2 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.3(9) . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 C2 103.4(10) . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
N1 C4 C3 102.4(9) . . ?
N1 C4 H4A 111.3 . . ?
N1 C4 H4B 111.3 . . ?
C3 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C6 C5 N3 118.2(8) . . ?
C10 C5 N3 121.2(8) . . ?
C10 C5 C6 120.6(9) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.2(9) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.4(9) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C11 120.3(10) . . ?
C9 C8 C7 117.8(10) . . ?
C9 C8 C11 121.9(10) . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.4(10) . . ?
C10 C9 H9 118.8 . . ?
C5 C10 C9 118.6(9) . . ?
C5 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 111.3 . . ?
N4 C12 H12B 111.3 . . ?
N4 C12 C13 102.2(7) . . ?
H12A C12 H12B 109.2 . . ?
C13 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
C12 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C14 C13 C12 104.2(9) . . ?
C14 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
C13 C14 H14A 111.2 . . ?
C13 C14 H14B 111.2 . . ?
C13 C14 C15 102.8(8) . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
N4 C15 C14 102.5(8) . . ?
N4 C15 H15A 111.3 . . ?
N4 C15 H15B 111.3 . . ?
C14 C15 H15A 111.3 . . ?
C14 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C17 C16 N6 120.2(8) . . ?
C21 C16 N6 120.2(9) . . ?
C21 C16 C17 119.6(9) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(9) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.9(10) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 118.7(9) . . ?
C18 C19 C22 121.2(10) . . ?
C20 C19 C22 120.1(9) . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.4(9) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 C20 119.3(9) . . ?
C16 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Pd1 N3 C5 C6 15.6(11) . . . . ?
Pd1 N3 C5 C10 -165.0(8) . . . . ?
Pd1 N6 C16 C17 105.9(8) . . . . ?
Pd1 N6 C16 C21 -74.7(10) . . . . ?
N1 N2 N3 Pd1 5.1(14) . . . . ?
N1 N2 N3 C5 179.6(9) . . . . ?
N1 C1 C2 C3 26.0(12) . . . . ?
N2 N1 C1 C2 173.7(10) . . . . ?
N2 N1 C4 C3 162.4(10) . . . . ?
N2 N3 C5 C6 -159.6(9) . . . . ?
N2 N3 C5 C10 19.7(13) . . . . ?
N3 C5 C6 C7 177.5(9) . . . . ?
N3 C5 C10 C9 -177.7(9) . . . . ?
N4 N5 N6 Pd1 6.4(15) . . . . ?
N4 N5 N6 C16 179.5(9) . . . . ?
N4 C12 C13 C14 29.7(11) . . . . ?
N5 N4 C12 C13 168.7(10) . . . . ?
N5 N4 C15 C14 167.0(9) . . . . ?
N5 N6 C16 C17 -69.0(11) . . . . ?
N5 N6 C16 C21 110.4(10) . . . . ?
N6 C16 C17 C18 177.4(9) . . . . ?
N6 C16 C21 C20 -176.5(9) . . . . ?
C1 N1 N2 N3 3.4(17) . . . . ?
C1 N1 C4 C3 -19.7(14) . . . . ?
C1 C2 C3 C4 -38.6(13) . . . . ?
C2 C3 C4 N1 35.2(13) . . . . ?
C4 N1 N2 N3 -179.2(10) . . . . ?
C4 N1 C1 C2 -3.8(13) . . . . ?
C5 C6 C7 C8 1.3(17) . . . . ?
C6 C5 C10 C9 1.7(16) . . . . ?
C6 C7 C8 C9 -0.5(17) . . . . ?
C6 C7 C8 C11 179.5(10) . . . . ?
C7 C8 C9 C10 0.3(17) . . . . ?
C8 C9 C10 C5 -0.9(17) . . . . ?
C10 C5 C6 C7 -1.9(16) . . . . ?
C11 C8 C9 C10 -179.7(10) . . . . ?
C12 N4 N5 N6 1.5(16) . . . . ?
C12 N4 C15 C14 -15.1(12) . . . . ?
C12 C13 C14 C15 -39.4(11) . . . . ?
C13 C14 C15 N4 33.0(11) . . . . ?
C15 N4 N5 N6 178.9(9) . . . . ?
C15 N4 C12 C13 -8.9(12) . . . . ?
C16 C17 C18 C19 -1.3(15) . . . . ?
C17 C16 C21 C20 2.9(15) . . . . ?
C17 C18 C19 C20 3.7(15) . . . . ?
C17 C18 C19 C22 -175.4(10) . . . . ?
C18 C19 C20 C21 -2.8(16) . . . . ?
C19 C20 C21 C16 -0.5(17) . . . . ?
C21 C16 C17 C18 -2.1(15) . . . . ?
C22 C19 C20 C21 176.3(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 12.428
_oxdiff_exptl_absorpt_empirical_full_min 0.187
####################################################################### 
# 
# 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_il-2-250
_database_code_depnum_ccdc_archive 'CCDC 1966939'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-08-14
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.07.31 svn.r3643 for OlexSys, GUI svn.r5859)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H38 Cl2 N6 O4 Pd'
_chemical_formula_sum            'C28 H38 Cl2 N6 O4 Pd'
_chemical_formula_weight         699.94
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H38 Cl2 N6 O4 Pd'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 '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                   8.1628(4)
_cell_length_b                   8.4628(4)
_cell_length_c                   12.1951(6)
_cell_angle_alpha                98.576(4)
_cell_angle_beta                 106.738(4)
_cell_angle_gamma                90.520(4)
_cell_volume                     796.52(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4060
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      75.7560
_cell_measurement_theta_min      5.2700
_shelx_estimated_absorpt_T_max   0.631
_shelx_estimated_absorpt_T_min   0.121
_exptl_absorpt_coefficient_mu    6.588
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.313
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0460
0 -1 -2 0.0476
0 1 2 0.0525
-2 1 0 0.1582
2 1 0 0.3145
0 1 -2 0.0625
0 -2 1 0.0281
0 -1 2 0.0395
-1 0 1 0.1574
0 1 0 0.0364
-1 -1 -1 0.1115
1 -1 -2 0.2047

_exptl_crystal_size_max          0.554
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.077
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 1.0000 1.0000 0.1939 -0.1475 -0.0173
-0.0000 -1.0000 -2.0000 -0.2053 0.2805 0.0131
0.0000 1.0000 2.0000 0.2053 -0.2805 -0.0131
-2.0000 1.0000 -0.0000 0.2149 0.1162 0.3495
2.0000 1.0000 -0.0000 0.1502 -0.1451 -0.3927
-0.0000 1.0000 -2.0000 0.1598 0.2517 -0.0301
-0.0000 -2.0000 1.0000 -0.3537 -0.1042 0.0475
0.0000 -1.0000 2.0000 -0.1598 -0.2517 0.0301
-1.0000 0.0000 1.0000 0.0276 -0.0677 0.1898
0.0000 1.0000 -0.0000 0.1825 -0.0144 -0.0216
-1.0000 -1.0000 -1.0000 -0.1778 0.2128 0.2029
1.0000 -1.0000 -2.0000 -0.2215 0.2152 -0.1725

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.558
_diffrn_reflns_theta_min         3.833
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -94.00   1.00    1.00    --  -43.01 -99.00  90.00   26
  2  ω   -121.00 -94.00   1.00    1.00    --  -43.01 -99.00   0.00   27
  3  ω    -67.00  27.00   1.00    1.00    --  -43.01  37.00  30.00   94
  4  ω    -66.00  31.00   1.00    1.00    --  -43.01  37.00 120.00   97
  5  ω      7.00  32.00   1.00    1.00    --   43.01 -99.00-150.00   25
  6  ω     39.00  98.00   1.00    1.00    --   43.01-125.00-180.00   59
  7  ω     29.00  64.00   1.00    1.00    --   43.01-125.00 -60.00   35
  8  ω    138.00 177.00   1.00    4.00    --  112.00  15.00  90.00   39
  9  ω     60.00  89.00   1.00    4.00    --  112.00  15.00  90.00   29
 10  ω    100.00 147.00   1.00    4.00    --  112.00 111.00  30.00   47
 11  ω     80.00 178.00   1.00    4.00    --  112.00  77.00-150.00   98
 12  ω     63.00 120.00   1.00    4.00    --  112.00 178.00 120.00   57
 13  ω     83.00 148.00   1.00    4.00    --  112.00  61.00 120.00   65
 14  ω     76.00 104.00   1.00    4.00    --  112.00 -94.00-180.00   28
 15  ω    129.00 178.00   1.00    4.00    --  112.00 111.00 -90.00   49
 16  ω     71.00  99.00   1.00    4.00    --  112.00-111.00 -90.00   28
 17  ω     69.00 112.00   1.00    4.00    --  112.00-111.00 -30.00   43
 18  ω     39.00  65.00   1.00    4.00    --  112.00-111.00 -90.00   26
 19  ω     80.00 113.00   1.00    4.00    --  112.00-111.00  30.00   33
 20  ω     42.00 135.00   1.00    4.00    --  112.00 -45.00-120.00   93
 21  ω     76.00 113.00   1.00    4.00    --  112.00-111.00  90.00   37
 22  ω     37.00 100.00   1.00    4.00    --  112.00-111.00 150.00   63
 23  ω    111.00 137.00   1.00    4.00    --  112.00  61.00 -60.00   26
 24  ω    142.00 168.00   1.00    4.00    --  112.00  61.00 -60.00   26
 25  ω     42.00  83.00   1.00    4.00    --  112.00-111.00-150.00   41
 26  ω    112.00 177.00   1.00    4.00    --  112.00  61.00 -30.00   65
 27  ω     52.00  79.00   1.00    4.00    --  112.00 -77.00-120.00   27
 28  ω    115.00 141.00   1.00    4.00    --  112.00 -77.00-120.00   26
 29  ω     95.00 122.00   1.00    4.00    --  112.00 -77.00   0.00   27
 30  ω    130.00 170.00   1.00    4.00    --  112.00 111.00-180.00   40
 31  ω     63.00  88.00   1.00    4.00    --  112.00 -77.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0161666000
_diffrn_orient_matrix_UB_12      0.1825390000
_diffrn_orient_matrix_UB_13      0.0113888000
_diffrn_orient_matrix_UB_21      -0.0653251000
_diffrn_orient_matrix_UB_22      -0.0144027000
_diffrn_orient_matrix_UB_23      -0.1330485000
_diffrn_orient_matrix_UB_31      -0.1855510000
_diffrn_orient_matrix_UB_32      -0.0216069000
_diffrn_orient_matrix_UB_33      0.0042600000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3206
_reflns_number_total             3299
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.208
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.061
_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)+(0.0492P)²+0.7322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Pd1 Pd 0.500000 1.000000 1.000000 0.02545(11) Uani 1 2 d S . P . .
Cl1 Cl 0.37434(9) 0.86537(8) 1.11226(6) 0.03180(16) Uani 1 1 d . . . . .
O1 O 0.1516(3) 0.9873(3) 0.82695(19) 0.0396(5) Uani 1 1 d . . . . .
O2 O 0.0572(3) 0.6473(3) 0.6817(2) 0.0474(6) Uani 1 1 d . . . . .
N1 N 0.3897(3) 0.8405(3) 0.8561(2) 0.0276(5) Uani 1 1 d . . . . .
N2 N 0.4427(3) 0.7229(3) 0.7953(2) 0.0277(5) Uani 1 1 d . . . . .
N3 N 0.5881(3) 0.6645(3) 0.8296(2) 0.0313(5) Uani 1 1 d . . . . .
C1 C 0.2252(4) 0.8766(4) 0.7928(3) 0.0311(6) Uani 1 1 d . . . . .
C2 C 0.1403(4) 0.7656(4) 0.6782(3) 0.0345(7) Uani 1 1 d . . . . .
C3 C 0.1556(4) 0.8152(4) 0.5705(3) 0.0352(7) Uani 1 1 d . . . . .
C4 C 0.0688(5) 0.7248(5) 0.4640(3) 0.0490(9) Uani 1 1 d . . . . .
H4 H -0.001216 0.632991 0.460922 0.059 Uiso 1 1 calc R U . . .
C5 C 0.0846(6) 0.7690(6) 0.3626(3) 0.0636(13) Uani 1 1 d . . . . .
H5 H 0.025103 0.707508 0.289904 0.076 Uiso 1 1 calc R U . . .
C6 C 0.1858(6) 0.9012(7) 0.3666(4) 0.0633(13) Uani 1 1 d . . . . .
H6 H 0.195896 0.931271 0.296708 0.076 Uiso 1 1 calc R U . . .
C7 C 0.2732(6) 0.9908(6) 0.4721(4) 0.0599(10) Uani 1 1 d . . . . .
H7 H 0.344040 1.081779 0.474634 0.072 Uiso 1 1 calc R U . . .
C8 C 0.2577(5) 0.9485(5) 0.5740(3) 0.0465(8) Uani 1 1 d . . . . .
H8 H 0.317088 1.010782 0.646354 0.056 Uiso 1 1 calc R U . . .
C9 C 0.7252(4) 0.7100(4) 0.9428(3) 0.0333(6) Uani 1 1 d . . . . .
H9 H 0.685416 0.801712 0.988601 0.040 Uiso 1 1 calc R U . . .
C10 C 0.8886(4) 0.7653(5) 0.9233(4) 0.0507(9) Uani 1 1 d . . . . .
H10A H 0.928738 0.678443 0.876503 0.076 Uiso 1 1 calc R U . . .
H10B H 0.975882 0.795852 0.998161 0.076 Uiso 1 1 calc R U . . .
H10C H 0.867606 0.857844 0.882363 0.076 Uiso 1 1 calc R U . . .
C11 C 0.7481(5) 0.5726(5) 1.0104(3) 0.0525(9) Uani 1 1 d . . . . .
H11A H 0.639804 0.545679 1.024647 0.079 Uiso 1 1 calc R U . . .
H11B H 0.836818 0.603286 1.084675 0.079 Uiso 1 1 calc R U . . .
H11C H 0.782721 0.479402 0.965951 0.079 Uiso 1 1 calc R U . . .
C12 C 0.6181(4) 0.5378(4) 0.7387(3) 0.0419(8) Uani 1 1 d . . . . .
H12 H 0.724831 0.484304 0.774181 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4708(6) 0.4130(4) 0.6967(3) 0.0539(10) Uani 1 1 d . . . . .
H13A H 0.455833 0.367531 0.762777 0.081 Uiso 1 1 calc R U . . .
H13B H 0.495514 0.327860 0.640796 0.081 Uiso 1 1 calc R U . . .
H13C H 0.365620 0.462721 0.659344 0.081 Uiso 1 1 calc R U . . .
C14 C 0.6458(5) 0.6171(5) 0.6414(3) 0.0519(9) Uani 1 1 d . . . . .
H14A H 0.543159 0.672174 0.606655 0.078 Uiso 1 1 calc R U . . .
H14B H 0.668115 0.535521 0.582144 0.078 Uiso 1 1 calc R U . . .
H14C H 0.744115 0.694754 0.672379 0.078 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
Pd1 Cl1 2.3404(7) 2_677 ?
Pd1 Cl1 2.3404(7) . ?
Pd1 N1 2.018(2) 2_677 ?
Pd1 N1 2.018(2) . ?
O1 C1 1.204(4) . ?
O2 C2 1.217(4) . ?
N1 N2 1.304(3) . ?
N1 C1 1.405(4) . ?
N2 N3 1.270(3) . ?
N3 C9 1.500(4) . ?
N3 C12 1.498(4) . ?
C1 C2 1.535(4) . ?
C2 C3 1.474(5) . ?
C3 C4 1.392(4) . ?
C3 C8 1.385(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.371(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(6) . ?
C8 H8 0.9500 . ?
C9 H9 1.0000 . ?
C9 C10 1.503(5) . ?
C9 C11 1.506(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C12 C13 1.511(6) . ?
C12 C14 1.517(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Pd1 Cl1 180.00(3) 2_677 . ?
N1 Pd1 Cl1 91.80(7) . . ?
N1 Pd1 Cl1 91.80(7) 2_677 2_677 ?
N1 Pd1 Cl1 88.20(7) . 2_677 ?
N1 Pd1 Cl1 88.20(7) 2_677 . ?
N1 Pd1 N1 180.0 2_677 . ?
N2 N1 Pd1 135.28(18) . . ?
N2 N1 C1 109.0(2) . . ?
C1 N1 Pd1 114.67(18) . . ?
N3 N2 N1 123.6(2) . . ?
N2 N3 C9 128.5(2) . . ?
N2 N3 C12 111.7(2) . . ?
C12 N3 C9 119.7(2) . . ?
O1 C1 N1 122.2(3) . . ?
O1 C1 C2 120.9(3) . . ?
N1 C1 C2 116.9(2) . . ?
O2 C2 C1 117.8(3) . . ?
O2 C2 C3 124.5(3) . . ?
C3 C2 C1 117.6(3) . . ?
C4 C3 C2 119.5(3) . . ?
C8 C3 C2 121.0(3) . . ?
C8 C3 C4 119.5(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.1(4) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(5) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.0(4) . . ?
C7 C8 H8 120.0 . . ?
N3 C9 H9 107.8 . . ?
N3 C9 C10 110.7(3) . . ?
N3 C9 C11 109.8(3) . . ?
C10 C9 H9 107.8 . . ?
C10 C9 C11 112.9(3) . . ?
C11 C9 H9 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12 108.3 . . ?
N3 C12 C13 110.5(3) . . ?
N3 C12 C14 108.7(3) . . ?
C13 C12 H12 108.3 . . ?
C13 C12 C14 112.5(3) . . ?
C14 C12 H12 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Pd1 N1 N2 N3 12.3(5) . . . . ?
Pd1 N1 C1 O1 -5.4(4) . . . . ?
Pd1 N1 C1 C2 176.0(2) . . . . ?
O1 C1 C2 O2 -90.8(4) . . . . ?
O1 C1 C2 C3 85.3(4) . . . . ?
O2 C2 C3 C4 1.0(5) . . . . ?
O2 C2 C3 C8 -177.7(3) . . . . ?
N1 N2 N3 C9 1.7(5) . . . . ?
N1 N2 N3 C12 -176.5(3) . . . . ?
N1 C1 C2 O2 87.8(3) . . . . ?
N1 C1 C2 C3 -96.1(3) . . . . ?
N2 N1 C1 O1 -175.5(3) . . . . ?
N2 N1 C1 C2 5.9(4) . . . . ?
N2 N3 C9 C10 -120.3(4) . . . . ?
N2 N3 C9 C11 114.4(4) . . . . ?
N2 N3 C12 C13 -52.7(4) . . . . ?
N2 N3 C12 C14 71.2(4) . . . . ?
C1 N1 N2 N3 179.4(3) . . . . ?
C1 C2 C3 C4 -174.8(3) . . . . ?
C1 C2 C3 C8 6.5(4) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C2 C3 C8 C7 178.6(3) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C3 C8 C7 -0.1(5) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C5 C6 C7 C8 -0.6(7) . . . . ?
C6 C7 C8 C3 0.5(6) . . . . ?
C8 C3 C4 C5 -0.2(5) . . . . ?
C9 N3 C12 C13 129.0(3) . . . . ?
C9 N3 C12 C14 -107.1(3) . . . . ?
C12 N3 C9 C10 57.7(4) . . . . ?
C12 N3 C9 C11 -67.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.946
_oxdiff_exptl_absorpt_empirical_full_min 0.624
####################################################################### 
# 
# 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_il-2-250_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1966937'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 N3 O2, C F3 O3 S'
_chemical_formula_sum            'C15 H20 F3 N3 O5 S'
_chemical_formula_weight         411.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H20 N3 O5 F3 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.8991(5)
_cell_length_b                   10.8721(10)
_cell_length_c                   11.4526(9)
_cell_angle_alpha                117.321(9)
_cell_angle_beta                 91.458(6)
_cell_angle_gamma                97.837(6)
_cell_volume                     970.37(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2033
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.5440
_cell_measurement_theta_min      4.3270
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.615
_exptl_absorpt_coefficient_mu    2.033
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019).
 Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid.
 (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
 Empirical absorption correction using spherical harmonics as
 implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 -1 0.0792
-1 -1 1 0.1652
-1 1 0 0.0341
1 -1 0 0.0341
0 0 -1 0.0183
0 0 1 0.0183
2 1 2 0.0532
0 2 -1 0.0783
0 -2 1 0.1483

_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.037
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 1.0000 -1.0000 0.0800 -0.0634 0.2256
-1.0000 -1.0000 1.0000 -0.0800 0.0634 -0.2256
-1.0000 1.0000 -0.0000 0.1713 -0.0347 -0.1304
1.0000 -1.0000 0.0000 -0.1713 0.0347 0.1304
0.0000 -0.0000 -1.0000 -0.0616 -0.1372 0.0231
-0.0000 0.0000 1.0000 0.0616 0.1372 -0.0231
2.0000 1.0000 2.0000 0.2501 0.4023 0.3225
-0.0000 2.0000 -1.0000 0.2513 -0.0981 0.0952
0.0000 -2.0000 1.0000 -0.2513 0.0981 -0.0952

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6582
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.411
_diffrn_reflns_theta_min         4.367
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -129.00  42.00   1.00    9.00    --  -42.88   0.00 -90.00  171
  2  ω      0.00  52.00   1.00    9.00    --   42.88 -37.00   0.00   52
  3  ω     32.00  76.00   1.00    9.00    --   42.88-125.00-150.00   44
  4  ω     31.00  87.00   1.00    9.00    --   42.88-125.00   0.00   56
  5  ω     47.00 133.00   1.00   32.50    --  105.68 -30.00   0.00   86
  6  ω     78.00 171.00   1.00   32.50    --  105.68  30.00   0.00   93
  7  ω     92.00 118.00   1.00   32.50    --  105.68-125.00  60.00   26
  8  ω     97.00 128.00   1.00   32.50    --  105.68 -61.00 150.00   31
  9  ω     80.00 114.00   1.00   32.50    --  105.68 163.00-101.00   34
 10  ω     92.00 148.00   1.00   32.50    --  105.68  61.00  30.00   56
 11  ω     38.00 137.00   1.00   32.50    --  105.68 -77.00 -30.00   99
 12  ω     40.00 109.00   1.00   32.50    --  105.68-125.00 -90.00   69
 13  ω     57.00 118.00   1.00   32.50    --  105.68-125.00-180.00   61
 14  ω     98.00 132.00   1.00   32.50    --  105.68  77.00-120.00   34
 15  ω     96.00 177.00   1.00   32.50    --  105.68 125.00  60.00   81
 16  ω     35.00  77.00   1.00   32.50    --  105.68 -61.00 150.00   42
 17  ω     37.00  64.00   1.00   32.50    --  105.68-125.00  60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0148291000
_diffrn_orient_matrix_UB_12      0.1564707000
_diffrn_orient_matrix_UB_13      0.0616400000
_diffrn_orient_matrix_UB_21      0.0542103000
_diffrn_orient_matrix_UB_22      0.0195508000
_diffrn_orient_matrix_UB_23      0.1371873000
_diffrn_orient_matrix_UB_31      0.1663930000
_diffrn_orient_matrix_UB_32      0.0360327000
_diffrn_orient_matrix_UB_33      -0.0231379000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2904
_reflns_number_total             3768
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3768
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.033
_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)+(0.0582P)²+0.1181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
S1 S 0.75897(6) 0.68807(6) 0.71609(5) 0.03693(16) Uani 1 1 d . . . . .
F1 F 0.8812(3) 0.9416(2) 0.8927(2) 0.0873(7) Uani 1 1 d . . . . .
F2 F 0.8034(3) 0.8045(3) 0.97420(16) 0.0835(7) Uani 1 1 d . . . . .
F3 F 0.6427(2) 0.8901(3) 0.90025(17) 0.0882(8) Uani 1 1 d . . . . .
O3 O 0.72454(19) 0.7481(2) 0.63070(17) 0.0455(4) Uani 1 1 d . . . . .
O4 O 0.90883(19) 0.6526(2) 0.71111(18) 0.0495(4) Uani 1 1 d . . . . .
O5 O 0.6370(2) 0.5878(2) 0.71567(19) 0.0547(5) Uani 1 1 d . . . . .
C15 C 0.7722(3) 0.8385(3) 0.8795(3) 0.0587(8) Uani 1 1 d . . . . .
O1 O 0.68247(19) 0.7309(2) 0.32260(17) 0.0468(4) Uani 1 1 d . . . . .
O2 O 0.4911(2) 0.94821(19) 0.32796(17) 0.0472(4) Uani 1 1 d . . . . .
N1 N 0.49693(19) 0.75470(19) 0.46084(17) 0.0315(4) Uani 1 1 d . . . . .
H1 H 0.556(3) 0.744(3) 0.516(3) 0.041(7) Uiso 1 1 d . . . . .
N2 N 0.35388(19) 0.77459(19) 0.46917(16) 0.0321(4) Uani 1 1 d . . . . .
N3 N 0.28236(19) 0.7738(2) 0.56207(17) 0.0333(4) Uani 1 1 d . . . . .
C1 C 0.5589(2) 0.7607(2) 0.3520(2) 0.0350(4) Uani 1 1 d . . . . .
C2 C 0.4653(2) 0.8214(2) 0.2820(2) 0.0358(5) Uani 1 1 d . . . . .
C3 C 0.3597(2) 0.7252(3) 0.1649(2) 0.0378(5) Uani 1 1 d . . . . .
C4 C 0.2627(3) 0.7820(4) 0.1125(3) 0.0540(7) Uani 1 1 d . . . . .
H4 H 0.265296 0.880700 0.152366 0.065 Uiso 1 1 calc R . . . .
C5 C 0.1628(3) 0.6935(5) 0.0019(3) 0.0695(10) Uani 1 1 d . . . . .
H5 H 0.095307 0.731217 -0.033618 0.083 Uiso 1 1 calc R . . . .
C6 C 0.1609(4) 0.5515(5) -0.0566(3) 0.0709(10) Uani 1 1 d . . . . .
H6 H 0.093224 0.491747 -0.133661 0.085 Uiso 1 1 calc R . . . .
C7 C 0.2554(4) 0.4941(4) -0.0056(3) 0.0651(8) Uani 1 1 d . . . . .
H7 H 0.252768 0.395372 -0.047032 0.078 Uiso 1 1 calc R . . . .
C8 C 0.3551(3) 0.5814(3) 0.1074(2) 0.0459(5) Uani 1 1 d . . . . .
H8 H 0.419286 0.542589 0.144407 0.055 Uiso 1 1 calc R . . . .
C9 C 0.1178(2) 0.7907(3) 0.5521(2) 0.0386(5) Uani 1 1 d . . . . .
H9 H 0.061796 0.755330 0.608257 0.046 Uiso 1 1 calc R . . . .
C10 C 0.1081(3) 0.9457(3) 0.6064(3) 0.0528(6) Uani 1 1 d . . . . .
H10A H 0.155694 0.997382 0.697639 0.079 Uiso 1 1 calc GR . . . .
H10B H 0.000882 0.957189 0.604439 0.079 Uiso 1 1 calc GR . . . .
H10C H 0.161420 0.982255 0.552148 0.079 Uiso 1 1 calc GR . . . .
C11 C 0.0464(3) 0.7028(3) 0.4103(3) 0.0481(6) Uani 1 1 d . . . . .
H11A H 0.091944 0.742301 0.355232 0.072 Uiso 1 1 calc GR . . . .
H11B H -0.063660 0.703407 0.407056 0.072 Uiso 1 1 calc GR . . . .
H11C H 0.064840 0.606123 0.377199 0.072 Uiso 1 1 calc GR . . . .
C12 C 0.3445(2) 0.7507(3) 0.6721(2) 0.0376(5) Uani 1 1 d . . . . .
H12 H 0.458225 0.764499 0.675106 0.045 Uiso 1 1 calc R . . . .
C13 C 0.3008(3) 0.8575(3) 0.8035(2) 0.0466(6) Uani 1 1 d . . . . .
H13A H 0.338234 0.952574 0.816899 0.070 Uiso 1 1 calc GR . . . .
H13B H 0.346451 0.844886 0.875225 0.070 Uiso 1 1 calc GR . . . .
H13C H 0.189605 0.843927 0.803045 0.070 Uiso 1 1 calc GR . . . .
C14 C 0.2872(3) 0.6002(3) 0.6409(2) 0.0447(5) Uani 1 1 d . . . . .
H14A H 0.175538 0.584017 0.634756 0.067 Uiso 1 1 calc GR . . . .
H14B H 0.327863 0.582681 0.711213 0.067 Uiso 1 1 calc GR . . . .
H14C H 0.321039 0.536541 0.556616 0.067 Uiso 1 1 calc GR . . . .


_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
S1 O3 1.4492(18) . ?
S1 O4 1.4334(17) . ?
S1 O5 1.428(2) . ?
S1 C15 1.822(3) . ?
F1 C15 1.327(4) . ?
F2 C15 1.331(4) . ?
F3 C15 1.329(3) . ?
O1 C1 1.201(3) . ?
O2 C2 1.213(3) . ?
N1 H1 0.87(3) . ?
N1 N2 1.319(2) . ?
N1 C1 1.401(3) . ?
N2 N3 1.256(2) . ?
N3 C9 1.509(3) . ?
N3 C12 1.500(3) . ?
C1 C2 1.541(3) . ?
C2 C3 1.468(3) . ?
C3 C4 1.396(3) . ?
C3 C8 1.384(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.395(4) . ?
C8 H8 0.9500 . ?
C9 H9 1.0000 . ?
C9 C10 1.521(4) . ?
C9 C11 1.521(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C12 C13 1.521(3) . ?
C12 C14 1.514(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 C15 102.05(13) . . ?
O4 S1 O3 114.52(11) . . ?
O4 S1 C15 102.40(12) . . ?
O5 S1 O3 113.89(11) . . ?
O5 S1 O4 116.59(12) . . ?
O5 S1 C15 104.89(15) . . ?
F1 C15 S1 111.2(2) . . ?
F1 C15 F2 107.6(2) . . ?
F1 C15 F3 106.9(3) . . ?
F2 C15 S1 111.5(2) . . ?
F3 C15 S1 111.00(18) . . ?
F3 C15 F2 108.4(3) . . ?
N2 N1 H1 128.2(18) . . ?
N2 N1 C1 113.39(17) . . ?
C1 N1 H1 118.3(18) . . ?
N3 N2 N1 121.18(17) . . ?
N2 N3 C9 114.01(17) . . ?
N2 N3 C12 125.82(17) . . ?
C12 N3 C9 120.09(17) . . ?
O1 C1 N1 121.7(2) . . ?
O1 C1 C2 122.6(2) . . ?
N1 C1 C2 115.42(17) . . ?
O2 C2 C1 115.2(2) . . ?
O2 C2 C3 125.4(2) . . ?
C3 C2 C1 119.3(2) . . ?
C4 C3 C2 118.4(2) . . ?
C8 C3 C2 121.3(2) . . ?
C8 C3 C4 120.3(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.7(3) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 119.4(3) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
N3 C9 H9 108.1 . . ?
N3 C9 C10 109.42(19) . . ?
N3 C9 C11 110.13(18) . . ?
C10 C9 H9 108.1 . . ?
C11 C9 H9 108.1 . . ?
C11 C9 C10 112.8(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12 108.4 . . ?
N3 C12 C13 110.05(19) . . ?
N3 C12 C14 108.25(18) . . ?
C13 C12 H12 108.4 . . ?
C14 C12 H12 108.4 . . ?
C14 C12 C13 113.2(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O3 S1 C15 F1 -60.1(2) . . . . ?
O3 S1 C15 F2 179.8(2) . . . . ?
O3 S1 C15 F3 58.8(3) . . . . ?
O4 S1 C15 F1 58.7(2) . . . . ?
O4 S1 C15 F2 -61.4(3) . . . . ?
O4 S1 C15 F3 177.6(2) . . . . ?
O5 S1 C15 F1 -179.11(18) . . . . ?
O5 S1 C15 F2 60.8(2) . . . . ?
O5 S1 C15 F3 -60.2(3) . . . . ?
O1 C1 C2 O2 -87.7(3) . . . . ?
O1 C1 C2 C3 89.8(3) . . . . ?
O2 C2 C3 C4 -10.5(3) . . . . ?
O2 C2 C3 C8 169.7(2) . . . . ?
N1 N2 N3 C9 -177.00(19) . . . . ?
N1 N2 N3 C12 -0.3(3) . . . . ?
N1 C1 C2 O2 86.5(3) . . . . ?
N1 C1 C2 C3 -96.0(2) . . . . ?
N2 N1 C1 O1 -172.4(2) . . . . ?
N2 N1 C1 C2 13.3(3) . . . . ?
N2 N3 C9 C10 -82.4(2) . . . . ?
N2 N3 C9 C11 42.1(3) . . . . ?
N2 N3 C12 C13 135.0(2) . . . . ?
N2 N3 C12 C14 -100.8(2) . . . . ?
C1 N1 N2 N3 -179.30(19) . . . . ?
C1 C2 C3 C4 172.4(2) . . . . ?
C1 C2 C3 C8 -7.4(3) . . . . ?
C2 C3 C4 C5 179.7(2) . . . . ?
C2 C3 C8 C7 -178.6(2) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C3 C8 C7 1.6(4) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C6 C7 C8 C3 -1.3(4) . . . . ?
C8 C3 C4 C5 -0.5(4) . . . . ?
C9 N3 C12 C13 -48.5(3) . . . . ?
C9 N3 C12 C14 75.8(2) . . . . ?
C12 N3 C9 C10 100.7(2) . . . . ?
C12 N3 C9 C11 -134.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.629
####################################################################### 
# 
# 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_il310
_database_code_depnum_ccdc_archive 'CCDC 1966935'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-08-15
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.07.31 svn.r3643 for OlexSys, GUI svn.r5859)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H20 N3, C F3 O3 S'
_chemical_formula_sum            'C13 H20 F3 N3 O3 S'
_chemical_formula_weight         355.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H20 N3 O3 F3 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0352(3)
_cell_length_b                   25.0842(6)
_cell_length_c                   8.6190(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.100(3)
_cell_angle_gamma                90
_cell_volume                     1732.76(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3838
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      75.5540
_cell_measurement_theta_min      5.4060
_shelx_estimated_absorpt_T_max   0.867
_shelx_estimated_absorpt_T_min   0.664
_exptl_absorpt_coefficient_mu    2.095
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019)
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0586
4 -5 2 0.0271
-2 -2 -5 0.0525
2 0 -1 0.0330
-2 2 1 0.0800
1 2 2 0.0068
-1 -2 1 0.0426
0 1 0 0.1363

_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 -1.0007 0.0003 -0.0093 0.0261 0.0549
4.0017 -4.9927 1.9987 0.8138 0.1448 0.4138
-2.0053 -2.0166 -5.0001 -0.8181 -0.5326 0.2501
1.9990 0.0003 -1.0025 0.2454 -0.2815 0.1746
-1.9988 2.0010 1.0019 -0.2268 0.2294 -0.2844
1.0022 2.0077 1.9995 0.3722 0.1680 -0.1537
-0.9991 -2.0002 1.0022 -0.0951 0.2651 -0.0037
0.0001 1.0007 -0.0003 0.0093 -0.0261 -0.0549

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16441
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.837
_diffrn_reflns_theta_min         5.439
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -15.00   1.00    5.00    --  -43.01 -57.00 120.00  100
  2  ω   -118.00 -84.00   1.00    5.00    --  -43.01 -99.00-150.00   34
  3  ω   -107.00 -10.00   1.00    5.00    --  -43.01 -77.00-120.00   97
  4  ω   -123.00 -88.00   1.00    5.00    --  -43.01 -99.00 -90.00   35
  5  ω     49.00  76.00   1.00    5.00    --   43.01-125.00-180.00   27
  6  ω      1.00  58.00   1.00    5.00    --   43.01 -99.00   0.00   57
  7  ω     28.00  91.00   1.00    5.00    --   43.01-125.00  90.00   63
  8  ω     37.00 138.00   1.00   20.00    --  112.00 -30.00 -60.00  101
  9  ω     34.00  82.00   1.00   20.00    --  112.00 -94.00 -60.00   48
 10  ω     73.00 108.00   1.00   20.00    --  112.00 -94.00  60.00   35
 11  ω    131.00 164.00   1.00   20.00    --  112.00 -15.00 120.00   33
 12  ω     65.00 113.00   1.00   20.00    --  112.00-111.00  60.00   48
 13  ω     84.00 110.00   1.00   20.00    --  112.00-111.00 -90.00   26
 14  ω     29.00  95.00   1.00   20.00    --  112.00 -94.00 -30.00   66
 15  ω     30.00 107.00   1.00   20.00    --  112.00 -15.00 120.00   77
 16  ω     44.00 111.00   1.00   20.00    --  112.00-111.00 150.00   67
 17  ω    109.00 135.00   1.00   20.00    --  112.00 -45.00 120.00   26
 18  ω    147.00 173.00   1.00   20.00    --  112.00  45.00 -60.00   26
 19  ω     58.00 108.00   1.00   20.00    --  112.00-111.00  30.00   50
 20  ω     44.00 110.00   1.00   20.00    --  112.00 -94.00 150.00   66
 21  ω     36.00  63.00   1.00   20.00    --  112.00-111.00 -30.00   27
 22  ω     87.00 113.00   1.00   20.00    --  112.00-111.00 -30.00   26
 23  ω     91.00 177.00   1.00   20.00    --  112.00  15.00  60.00   86
 24  ω     47.00 109.00   1.00   20.00    --  112.00-111.00-120.00   62
 25  ω     45.00  74.00   1.00   20.00    --  112.00 -61.00  30.00   29
 26  ω     50.00  76.00   1.00   20.00    --  112.00 -61.00 150.00   26
 27  ω     90.00 135.00   1.00   20.00    --  112.00 -61.00 150.00   45
 28  ω     40.00  68.00   1.00   20.00    --  112.00 -45.00 120.00   28
 29  ω     36.00  80.00   1.00   20.00    --  112.00-111.00 120.00   44
 30  ω     93.00 174.00   1.00   20.00    --  112.00  45.00 120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1689572000
_diffrn_orient_matrix_UB_12      0.0093033000
_diffrn_orient_matrix_UB_13      0.0921056000
_diffrn_orient_matrix_UB_21      -0.0683823000
_diffrn_orient_matrix_UB_22      -0.0259975000
_diffrn_orient_matrix_UB_23      0.1444216000
_diffrn_orient_matrix_UB_31      0.0610686000
_diffrn_orient_matrix_UB_32      -0.0548896000
_diffrn_orient_matrix_UB_33      -0.0523715000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2746
_reflns_number_total             3623
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.046
_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)+(0.0540P)²+0.4878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
S1 S 0.79329(7) 0.35056(2) 0.17407(6) 0.03711(15) Uani 1 1 d . . . . .
F1 F 1.1126(2) 0.36563(9) 0.1551(3) 0.0829(6) Uani 1 1 d . . . . .
F2 F 0.9626(3) 0.43058(8) 0.0710(3) 0.0823(6) Uani 1 1 d . . . . .
F3 F 1.0044(3) 0.41688(11) 0.3137(2) 0.0939(8) Uani 1 1 d . . . . .
O1 O 0.6614(2) 0.38693(6) 0.2103(2) 0.0432(4) Uani 1 1 d . . . . .
O2 O 0.8362(3) 0.31192(7) 0.2936(2) 0.0554(5) Uani 1 1 d . . . . .
O3 O 0.7807(3) 0.33048(7) 0.0182(2) 0.0563(5) Uani 1 1 d . . . . .
C13 C 0.9762(3) 0.39338(10) 0.1780(3) 0.0470(5) Uani 1 1 d . . . . .
N1 N 0.4156(2) 0.41765(6) 0.4172(2) 0.0319(4) Uani 1 1 d . . . . .
H1 H 0.495(4) 0.4020(10) 0.361(3) 0.038(6) Uiso 1 1 d . . . . .
N2 N 0.3475(2) 0.39635(6) 0.5338(2) 0.0349(4) Uani 1 1 d . . . . .
N3 N 0.3961(2) 0.35008(6) 0.5821(2) 0.0355(4) Uani 1 1 d . . . . .
C1 C 0.3599(3) 0.46936(7) 0.3670(2) 0.0319(4) Uani 1 1 d . . . . .
C2 C 0.4064(4) 0.48643(9) 0.2255(3) 0.0484(6) Uani 1 1 d . . . . .
H2 H 0.473998 0.464552 0.165566 0.058 Uiso 1 1 calc R U . . .
C3 C 0.3532(4) 0.53646(10) 0.1702(3) 0.0572(7) Uani 1 1 d . . . . .
H3 H 0.384458 0.548687 0.072117 0.069 Uiso 1 1 calc R U . . .
C4 C 0.2559(4) 0.56796(8) 0.2574(3) 0.0461(6) Uani 1 1 d . . . . .
H4 H 0.219432 0.601867 0.219527 0.055 Uiso 1 1 calc R U . . .
C5 C 0.2115(3) 0.55041(8) 0.3994(3) 0.0409(5) Uani 1 1 d . . . . .
H5 H 0.144586 0.572439 0.459481 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2631(3) 0.50080(8) 0.4567(2) 0.0366(4) Uani 1 1 d . . . . .
H6 H 0.232529 0.488797 0.555251 0.044 Uiso 1 1 calc R U . . .
C7 C 0.5249(3) 0.31829(7) 0.5084(3) 0.0355(4) Uani 1 1 d . . . . .
H7 H 0.605805 0.343726 0.465669 0.043 Uiso 1 1 calc R U . . .
C8 C 0.4394(4) 0.28776(9) 0.3724(3) 0.0503(6) Uani 1 1 d . . . . .
H8A H 0.367102 0.260187 0.411934 0.075 Uiso 1 1 calc R U . . .
H8B H 0.523998 0.271016 0.311953 0.075 Uiso 1 1 calc R U . . .
H8C H 0.372147 0.312422 0.305767 0.075 Uiso 1 1 calc R U . . .
C9 C 0.6220(3) 0.28224(8) 0.6254(3) 0.0442(5) Uani 1 1 d . . . . .
H9A H 0.664523 0.303416 0.715180 0.066 Uiso 1 1 calc R U . . .
H9B H 0.715656 0.265927 0.576074 0.066 Uiso 1 1 calc R U . . .
H9C H 0.548065 0.254228 0.659931 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2952(3) 0.32773(9) 0.7065(3) 0.0508(6) Uani 1 1 d . . . . .
H10 H 0.311669 0.288219 0.708465 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3593(5) 0.34945(16) 0.8635(4) 0.0783(10) Uani 1 1 d . . . . .
H11A H 0.479499 0.342739 0.879565 0.117 Uiso 1 1 calc R U . . .
H11B H 0.301535 0.331742 0.945585 0.117 Uiso 1 1 calc R U . . .
H11C H 0.338528 0.387909 0.866986 0.117 Uiso 1 1 calc R U . . .
C12 C 0.1124(4) 0.33831(14) 0.6715(5) 0.0797(12) Uani 1 1 d . . . . .
H12A H 0.093071 0.376866 0.666404 0.120 Uiso 1 1 calc R U . . .
H12B H 0.049443 0.322903 0.753851 0.120 Uiso 1 1 calc R U . . .
H12C H 0.075513 0.322077 0.571518 0.120 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
S1 O1 1.4493(16) . ?
S1 O2 1.4385(17) . ?
S1 O3 1.4314(18) . ?
S1 C13 1.819(3) . ?
F1 C13 1.325(3) . ?
F2 C13 1.311(3) . ?
F3 C13 1.315(3) . ?
N1 H1 0.92(3) . ?
N1 N2 1.294(3) . ?
N1 C1 1.429(2) . ?
N2 N3 1.284(2) . ?
N3 C7 1.484(3) . ?
N3 C10 1.499(3) . ?
C1 C2 1.370(3) . ?
C1 C6 1.382(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.522(3) . ?
C7 C9 1.526(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.515(5) . ?
C10 C12 1.501(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C13 103.11(11) . . ?
O2 S1 O1 114.29(11) . . ?
O2 S1 C13 103.45(12) . . ?
O3 S1 O1 114.84(12) . . ?
O3 S1 O2 115.61(12) . . ?
O3 S1 C13 103.18(12) . . ?
F1 C13 S1 111.28(19) . . ?
F2 C13 S1 112.4(2) . . ?
F2 C13 F1 107.3(2) . . ?
F2 C13 F3 107.9(2) . . ?
F3 C13 S1 111.64(19) . . ?
F3 C13 F1 106.1(2) . . ?
N2 N1 H1 125.6(16) . . ?
N2 N1 C1 117.98(18) . . ?
C1 N1 H1 116.4(16) . . ?
N3 N2 N1 119.29(19) . . ?
N2 N3 C7 123.51(18) . . ?
N2 N3 C10 113.71(18) . . ?
C7 N3 C10 122.30(16) . . ?
C2 C1 N1 116.99(19) . . ?
C2 C1 C6 121.34(18) . . ?
C6 C1 N1 121.67(18) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N3 C7 H7 107.8 . . ?
N3 C7 C8 108.05(19) . . ?
N3 C7 C9 112.03(18) . . ?
C8 C7 H7 107.8 . . ?
C8 C7 C9 113.05(18) . . ?
C9 C7 H7 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10 107.8 . . ?
N3 C10 C11 109.7(2) . . ?
N3 C10 C12 111.2(2) . . ?
C11 C10 H10 107.8 . . ?
C12 C10 H10 107.8 . . ?
C12 C10 C11 112.4(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.92(3) 1.97(3) 2.859(3) 164(2) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C13 F1 176.61(18) . . . . ?
O1 S1 C13 F2 -63.1(2) . . . . ?
O1 S1 C13 F3 58.3(2) . . . . ?
O2 S1 C13 F1 57.3(2) . . . . ?
O2 S1 C13 F2 177.6(2) . . . . ?
O2 S1 C13 F3 -61.0(2) . . . . ?
O3 S1 C13 F1 -63.6(2) . . . . ?
O3 S1 C13 F2 56.8(2) . . . . ?
O3 S1 C13 F3 178.2(2) . . . . ?
N1 N2 N3 C7 -1.7(3) . . . . ?
N1 N2 N3 C10 -174.0(2) . . . . ?
N1 C1 C2 C3 179.2(3) . . . . ?
N1 C1 C6 C5 -179.1(2) . . . . ?
N2 N1 C1 C2 -166.6(2) . . . . ?
N2 N1 C1 C6 13.3(3) . . . . ?
N2 N3 C7 C8 -84.5(2) . . . . ?
N2 N3 C7 C9 150.3(2) . . . . ?
N2 N3 C10 C11 -83.7(3) . . . . ?
N2 N3 C10 C12 41.3(3) . . . . ?
C1 N1 N2 N3 -179.47(18) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C7 N3 C10 C11 103.9(3) . . . . ?
C7 N3 C10 C12 -131.0(3) . . . . ?
C10 N3 C7 C8 87.1(2) . . . . ?
C10 N3 C7 C9 -38.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.857
_oxdiff_exptl_absorpt_empirical_full_min 0.489
####################################################################### 
# 
# 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_il343
_database_code_depnum_ccdc_archive 'CCDC 1966938'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H19 B F15 N3'
_chemical_formula_sum            'C30 H19 B F15 N3'
_chemical_formula_weight         717.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H19 B F15 N3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           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                   18.9040(6)
_cell_length_b                   16.3612(6)
_cell_length_c                   19.3108(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5972.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6416
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.1820
_cell_measurement_theta_min      4.2210
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.666
_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.62a (Rigaku Oxford Diffraction, 2019)
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0865
0 -1 -1 0.1113
1 -2 2 0.0805
1 2 -1 0.0656
1 0 -1 0.1027
-2 0 1 0.0936
0 1 0 0.0647
-1 -2 0 0.0684
-1 1 0 0.0943
1 -1 0 0.0348
1 1 2 0.1509
0 2 -1 0.0666
0 -2 1 0.0614
0 0 -1 0.1519
0 0 1 0.1482
1 0 0 0.0498

_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.128
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -0.0000 -0.0000 0.0099 0.0723 -0.0362
0.0001 -1.0000 -1.0000 -0.0813 -0.0322 -0.0870
1.0001 -1.9998 2.0000 -0.2175 0.0097 0.1420
0.9998 2.0000 -1.0000 0.1864 -0.1177 0.0003
0.9999 0.0000 -1.0000 0.0013 -0.1089 -0.0338
-1.9999 -0.0001 1.0000 0.0087 0.1812 -0.0024
-0.0001 1.0000 0.0000 0.0926 -0.0044 0.0171
-0.9999 -2.0000 -0.0001 -0.1752 0.0811 -0.0703
-1.0000 0.9999 0.0000 0.1025 0.0679 -0.0191
1.0000 -0.9999 -0.0000 -0.1025 -0.0679 0.0191
0.9999 1.0002 2.0001 0.0602 -0.0035 0.1931
-0.0001 1.9999 -1.0000 0.1964 -0.0454 -0.0358
0.0001 -1.9999 1.0000 -0.1964 0.0454 0.0358
-0.0000 -0.0000 -1.0000 0.0112 -0.0366 -0.0700
0.0000 0.0000 1.0000 -0.0112 0.0366 0.0700
1.0000 0.0000 0.0000 -0.0099 -0.0723 0.0362

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15890
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.428
_diffrn_reflns_theta_min         4.244
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  32.00   1.00    4.60    --  -43.01  77.00   0.00   93
  2  ω   -113.00 -84.00   1.00    4.60    --  -43.01 -99.00 120.00   29
  3  ω     53.00  94.00   1.00    4.60    --   43.01-125.00-150.00   41
  4  ω    101.00 178.00   1.00   18.40    --  103.18 111.00-150.00   77
  5  ω     81.00 175.00   1.00   18.40    --  103.18  61.00  30.00   94
  6  ω     29.00  76.00   1.00   18.40    --  103.18-111.00-180.00   47
  7  ω     88.00 113.00   1.00   18.40    --  103.18-111.00-180.00   25
  8  ω    101.00 143.00   1.00   18.40    --  103.18 111.00 150.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0099510000
_diffrn_orient_matrix_UB_12      0.0925663000
_diffrn_orient_matrix_UB_13      -0.0112318000
_diffrn_orient_matrix_UB_21      -0.0723132000
_diffrn_orient_matrix_UB_22      -0.0044222000
_diffrn_orient_matrix_UB_23      0.0365970000
_diffrn_orient_matrix_UB_31      0.0361708000
_diffrn_orient_matrix_UB_32      0.0170619000
_diffrn_orient_matrix_UB_33      0.0699571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4910
_reflns_number_total             5770
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.62a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.00015(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     468
_refine_ls_number_reflns         5770
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.060
_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)+(0.0696P)²+5.1386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1510
_refine_special_details          ?
_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
 C11A-C12A \\sim C11B-C12B
 with sigma of 0.02
 C11A-C10 \\sim C11B-C10 \\sim C12A-C10 \\sim C12B-C10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11A \\sim C11B \\sim C12A \\sim C12B: within 2A with sigma of 0.005
and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(H10A)=Sof(C11B)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C12B)=Sof(H12D)=
 Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(H10)=Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12A)=Sof(H12A)=
 Sof(H12B)=Sof(H12C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C10(H10A)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11A(H11A,H11B,H11C), C11B(H11D,H11E,H11F),
 C12A(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.58544(8) 0.46591(10) 0.44566(8) 0.0425(4) Uani 1 1 d . . . . .
F2 F 0.61637(12) 0.53860(15) 0.32690(10) 0.0694(6) Uani 1 1 d . . . . .
F3 F 0.75153(13) 0.53741(16) 0.27779(10) 0.0766(7) Uani 1 1 d . . . . .
F4 F 0.85624(10) 0.46668(15) 0.35518(10) 0.0650(6) Uani 1 1 d . . . . .
F5 F 0.82740(7) 0.39806(10) 0.47468(7) 0.0389(4) Uani 1 1 d . . . . .
F6 F 0.71103(8) 0.21062(9) 0.59468(8) 0.0399(4) Uani 1 1 d . . . . .
F7 F 0.81130(10) 0.17493(12) 0.68473(9) 0.0564(5) Uani 1 1 d . . . . .
F8 F 0.90529(10) 0.29078(15) 0.72728(9) 0.0644(6) Uani 1 1 d . . . . .
F9 F 0.89207(8) 0.44723(13) 0.67994(8) 0.0517(5) Uani 1 1 d . . . . .
F10 F 0.78670(8) 0.48651(9) 0.59443(8) 0.0395(4) Uani 1 1 d . . . . .
F11 F 0.64186(9) 0.56770(10) 0.53783(10) 0.0474(4) Uani 1 1 d . . . . .
F12 F 0.55761(10) 0.64203(11) 0.62618(12) 0.0658(6) Uani 1 1 d . . . . .
F13 F 0.50686(11) 0.56226(16) 0.73960(13) 0.0787(7) Uani 1 1 d . . . . .
F14 F 0.54128(10) 0.40184(15) 0.75935(9) 0.0641(6) Uani 1 1 d . . . . .
F15 F 0.62096(8) 0.32384(10) 0.66892(7) 0.0389(4) Uani 1 1 d . . . . .
N1 N 0.63472(10) 0.30865(12) 0.50915(10) 0.0279(4) Uani 1 1 d . . . . .
N2 N 0.57679(10) 0.28791(12) 0.54012(10) 0.0284(4) Uani 1 1 d . . . . .
N3 N 0.54187(11) 0.22217(13) 0.52682(11) 0.0317(4) Uani 1 1 d . . . . .
C1 C 0.65694(13) 0.27504(16) 0.44250(13) 0.0341(5) Uani 1 1 d . . . . .
C2 C 0.61308(14) 0.28816(18) 0.38571(13) 0.0392(6) Uani 1 1 d . . . . .
H2 H 0.568941 0.315002 0.391727 0.047 Uiso 1 1 calc R U . . .
C3 C 0.63348(16) 0.2623(2) 0.32058(14) 0.0482(7) Uani 1 1 d . . . . .
H3 H 0.603063 0.270532 0.282043 0.058 Uiso 1 1 calc R U . . .
C4 C 0.69790(17) 0.2246(2) 0.31158(16) 0.0571(9) Uani 1 1 d . . . . .
H4 H 0.711820 0.206303 0.266920 0.068 Uiso 1 1 calc R U . . .
C5 C 0.74217(15) 0.2134(2) 0.36747(16) 0.0523(8) Uani 1 1 d . . . . .
H5 H 0.786974 0.188273 0.360761 0.063 Uiso 1 1 calc R U . . .
C6 C 0.72239(13) 0.23806(19) 0.43323(15) 0.0409(6) Uani 1 1 d . . . . .
H6 H 0.753160 0.229838 0.471494 0.049 Uiso 1 1 calc R U . . .
C7 C 0.56211(14) 0.14678(17) 0.48741(15) 0.0402(6) Uani 1 1 d . . . . .
H7 H 0.609611 0.156661 0.466208 0.048 Uiso 1 1 calc R U . . .
C8 C 0.51094(18) 0.1293(2) 0.42956(16) 0.0556(8) Uani 1 1 d . . . . .
H8A H 0.464662 0.115182 0.449058 0.083 Uiso 1 1 calc R U . . .
H8B H 0.528548 0.083493 0.401774 0.083 Uiso 1 1 calc R U . . .
H8C H 0.506285 0.177844 0.400180 0.083 Uiso 1 1 calc R U . . .
C9 C 0.56948(18) 0.07610(19) 0.5381(2) 0.0577(8) Uani 1 1 d . . . . .
H9A H 0.600149 0.092525 0.576548 0.087 Uiso 1 1 calc R U . . .
H9B H 0.590307 0.028982 0.514286 0.087 Uiso 1 1 calc R U . . .
H9C H 0.522721 0.061262 0.556028 0.087 Uiso 1 1 calc R U . . .
C10 C 0.47299(15) 0.21911(18) 0.56502(16) 0.0453(7) Uani 1 1 d D U . . .
H10 H 0.450403 0.165480 0.553712 0.054 Uiso 0.706(17) 1 calc R U P A 1
H10A H 0.441282 0.175132 0.546865 0.054 Uiso 0.294(17) 1 calc R U P A 2
C11A C 0.4252(3) 0.2861(4) 0.5350(5) 0.0551(18) Uani 0.706(17) 1 d D U P A 1
H11A H 0.447062 0.339624 0.542723 0.083 Uiso 0.706(17) 1 calc R U P A 1
H11B H 0.378996 0.284294 0.557902 0.083 Uiso 0.706(17) 1 calc R U P A 1
H11C H 0.419117 0.277070 0.485185 0.083 Uiso 0.706(17) 1 calc R U P A 1
C11B C 0.4350(8) 0.3021(8) 0.5689(12) 0.058(3) Uani 0.294(17) 1 d D U P A 2
H11D H 0.468361 0.344104 0.584449 0.087 Uiso 0.294(17) 1 calc R U P A 2
H11E H 0.395582 0.298495 0.601728 0.087 Uiso 0.294(17) 1 calc R U P A 2
H11F H 0.416813 0.316592 0.522983 0.087 Uiso 0.294(17) 1 calc R U P A 2
C12A C 0.4787(5) 0.2237(6) 0.6420(3) 0.0579(18) Uani 0.706(17) 1 d D U P A 1
H12A H 0.513849 0.184055 0.658219 0.087 Uiso 0.706(17) 1 calc R U P A 1
H12B H 0.432668 0.211253 0.662827 0.087 Uiso 0.706(17) 1 calc R U P A 1
H12C H 0.493358 0.278908 0.655596 0.087 Uiso 0.706(17) 1 calc R U P A 1
C12B C 0.4975(10) 0.2013(12) 0.6406(7) 0.053(3) Uani 0.294(17) 1 d D U P A 2
H12D H 0.531155 0.155749 0.640472 0.080 Uiso 0.294(17) 1 calc R U P A 2
H12E H 0.456423 0.187002 0.669014 0.080 Uiso 0.294(17) 1 calc R U P A 2
H12F H 0.520433 0.250071 0.659743 0.080 Uiso 0.294(17) 1 calc R U P A 2
C13 C 0.70470(13) 0.43235(15) 0.46975(12) 0.0303(5) Uani 1 1 d . . . . .
C14 C 0.65427(14) 0.46817(17) 0.42696(14) 0.0378(6) Uani 1 1 d . . . . .
C15 C 0.66862(17) 0.5040(2) 0.36432(15) 0.0501(7) Uani 1 1 d . . . . .
C16 C 0.73675(19) 0.5038(2) 0.33960(15) 0.0547(8) Uani 1 1 d . . . . .
C17 C 0.78888(16) 0.4686(2) 0.37842(15) 0.0467(7) Uani 1 1 d . . . . .
C18 C 0.77224(14) 0.43408(16) 0.44179(13) 0.0349(5) Uani 1 1 d . . . . .
C19 C 0.74523(11) 0.35094(15) 0.58791(11) 0.0267(5) Uani 1 1 d . . . . .
C20 C 0.75469(12) 0.27220(16) 0.61333(12) 0.0316(5) Uani 1 1 d . . . . .
C21 C 0.80724(14) 0.25139(18) 0.66022(13) 0.0392(6) Uani 1 1 d . . . . .
C22 C 0.85396(13) 0.3101(2) 0.68236(13) 0.0425(7) Uani 1 1 d . . . . .
C23 C 0.84689(13) 0.38923(19) 0.65907(13) 0.0373(6) Uani 1 1 d . . . . .
C24 C 0.79281(12) 0.40786(16) 0.61392(12) 0.0315(5) Uani 1 1 d . . . . .
C25 C 0.63056(12) 0.43845(15) 0.59372(12) 0.0294(5) Uani 1 1 d . . . . .
C26 C 0.61480(13) 0.52108(16) 0.58899(14) 0.0368(6) Uani 1 1 d . . . . .
C27 C 0.57275(14) 0.56243(18) 0.63640(18) 0.0486(8) Uani 1 1 d . . . . .
C28 C 0.54705(15) 0.5218(2) 0.69367(17) 0.0518(8) Uani 1 1 d . . . . .
C29 C 0.56392(14) 0.4421(2) 0.70279(14) 0.0456(7) Uani 1 1 d . . . . .
C30 C 0.60494(13) 0.40262(17) 0.65421(13) 0.0351(5) Uani 1 1 d . . . . .
B1 B 0.67933(13) 0.38445(16) 0.54011(13) 0.0259(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.351(3) . ?
F2 C15 1.348(4) . ?
F3 C16 1.344(3) . ?
F4 C17 1.351(3) . ?
F5 C18 1.356(3) . ?
F6 C20 1.351(3) . ?
F7 C21 1.340(3) . ?
F8 C22 1.339(3) . ?
F9 C23 1.339(3) . ?
F10 C24 1.346(3) . ?
F11 C26 1.349(3) . ?
F12 C27 1.348(4) . ?
F13 C28 1.342(3) . ?
F14 C29 1.346(4) . ?
F15 C30 1.354(3) . ?
N1 N2 1.293(3) . ?
N1 C1 1.461(3) . ?
N1 B1 1.615(3) . ?
N2 N3 1.288(3) . ?
N3 C7 1.499(3) . ?
N3 C10 1.498(3) . ?
C1 C2 1.392(4) . ?
C1 C6 1.389(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.505(4) . ?
C7 C9 1.521(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 H10A 1.0000 . ?
C10 C11A 1.533(6) . ?
C10 C11B 1.538(11) . ?
C10 C12A 1.493(7) . ?
C10 C12B 1.558(12) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13 C14 1.391(4) . ?
C13 C18 1.387(4) . ?
C13 B1 1.640(3) . ?
C14 C15 1.371(4) . ?
C15 C16 1.374(5) . ?
C16 C17 1.365(5) . ?
C17 C18 1.384(4) . ?
C19 C20 1.390(3) . ?
C19 C24 1.389(3) . ?
C19 B1 1.644(3) . ?
C20 C21 1.387(3) . ?
C21 C22 1.373(4) . ?
C22 C23 1.377(4) . ?
C23 C24 1.378(3) . ?
C25 C26 1.387(4) . ?
C25 C30 1.394(4) . ?
C25 B1 1.644(3) . ?
C26 C27 1.388(4) . ?
C27 C28 1.379(5) . ?
C28 C29 1.354(5) . ?
C29 C30 1.378(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
N2 N1 C1 123.51(19) . . ?
N2 N1 B1 118.21(19) . . ?
C1 N1 B1 117.71(18) . . ?
N3 N2 N1 124.1(2) . . ?
N2 N3 C7 131.1(2) . . ?
N2 N3 C10 112.0(2) . . ?
C10 N3 C7 116.4(2) . . ?
C2 C1 N1 117.7(2) . . ?
C6 C1 N1 122.2(2) . . ?
C6 C1 C2 119.8(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
N3 C7 H7 107.7 . . ?
N3 C7 C8 111.7(2) . . ?
N3 C7 C9 108.8(2) . . ?
C8 C7 H7 107.7 . . ?
C8 C7 C9 113.1(3) . . ?
C9 C7 H7 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10 107.0 . . ?
N3 C10 H10A 111.9 . . ?
N3 C10 C11A 107.6(3) . . ?
N3 C10 C11B 113.6(6) . . ?
N3 C10 C12B 102.0(8) . . ?
C11A C10 H10 107.0 . . ?
C11B C10 H10A 111.9 . . ?
C11B C10 C12B 105.0(8) . . ?
C12A C10 N3 115.2(4) . . ?
C12A C10 H10 107.0 . . ?
C12A C10 C11A 112.5(4) . . ?
C12B C10 H10A 111.9 . . ?
C10 C11A H11A 109.5 . . ?
C10 C11A H11B 109.5 . . ?
C10 C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10 C11B H11D 109.5 . . ?
C10 C11B H11E 109.5 . . ?
C10 C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10 C12A H12A 109.5 . . ?
C10 C12A H12B 109.5 . . ?
C10 C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C10 C12B H12D 109.5 . . ?
C10 C12B H12E 109.5 . . ?
C10 C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C14 C13 B1 119.5(2) . . ?
C18 C13 C14 113.0(2) . . ?
C18 C13 B1 127.0(2) . . ?
F1 C14 C13 119.3(2) . . ?
F1 C14 C15 116.0(2) . . ?
C15 C14 C13 124.6(3) . . ?
F2 C15 C14 120.5(3) . . ?
F2 C15 C16 120.1(3) . . ?
C14 C15 C16 119.4(3) . . ?
F3 C16 C15 120.2(3) . . ?
F3 C16 C17 120.7(3) . . ?
C17 C16 C15 119.1(3) . . ?
F4 C17 C16 120.5(3) . . ?
F4 C17 C18 119.9(3) . . ?
C16 C17 C18 119.6(3) . . ?
F5 C18 C13 121.1(2) . . ?
F5 C18 C17 114.6(2) . . ?
C17 C18 C13 124.2(3) . . ?
C20 C19 B1 127.2(2) . . ?
C24 C19 C20 114.2(2) . . ?
C24 C19 B1 118.0(2) . . ?
F6 C20 C19 121.2(2) . . ?
F6 C20 C21 115.4(2) . . ?
C21 C20 C19 123.4(2) . . ?
F7 C21 C20 120.1(3) . . ?
F7 C21 C22 120.4(2) . . ?
C22 C21 C20 119.5(3) . . ?
F8 C22 C21 120.1(3) . . ?
F8 C22 C23 120.3(3) . . ?
C21 C22 C23 119.6(2) . . ?
F9 C23 C22 120.4(2) . . ?
F9 C23 C24 120.5(3) . . ?
C22 C23 C24 119.1(3) . . ?
F10 C24 C19 119.0(2) . . ?
F10 C24 C23 116.9(2) . . ?
C23 C24 C19 124.1(2) . . ?
C26 C25 C30 113.0(2) . . ?
C26 C25 B1 127.1(2) . . ?
C30 C25 B1 119.8(2) . . ?
F11 C26 C25 121.2(2) . . ?
F11 C26 C27 115.1(3) . . ?
C25 C26 C27 123.7(3) . . ?
F12 C27 C26 119.7(3) . . ?
F12 C27 C28 120.6(3) . . ?
C28 C27 C26 119.7(3) . . ?
F13 C28 C27 119.5(3) . . ?
F13 C28 C29 121.5(3) . . ?
C29 C28 C27 119.1(3) . . ?
F14 C29 C28 120.2(3) . . ?
F14 C29 C30 120.1(3) . . ?
C28 C29 C30 119.7(3) . . ?
F15 C30 C25 119.9(2) . . ?
F15 C30 C29 115.4(2) . . ?
C29 C30 C25 124.7(3) . . ?
N1 B1 C13 102.30(18) . . ?
N1 B1 C19 110.33(18) . . ?
N1 B1 C25 110.67(18) . . ?
C13 B1 C19 113.75(19) . . ?
C13 B1 C25 115.4(2) . . ?
C25 B1 C19 104.51(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C14 C15 F2 3.7(4) . . . . ?
F1 C14 C15 C16 -175.7(3) . . . . ?
F2 C15 C16 F3 -0.5(5) . . . . ?
F2 C15 C16 C17 179.8(3) . . . . ?
F3 C16 C17 F4 -0.3(5) . . . . ?
F3 C16 C17 C18 -179.7(3) . . . . ?
F4 C17 C18 F5 -1.9(4) . . . . ?
F4 C17 C18 C13 -179.4(3) . . . . ?
F6 C20 C21 F7 -1.2(3) . . . . ?
F6 C20 C21 C22 -179.8(2) . . . . ?
F7 C21 C22 F8 1.9(4) . . . . ?
F7 C21 C22 C23 -177.0(2) . . . . ?
F8 C22 C23 F9 1.4(4) . . . . ?
F8 C22 C23 C24 -178.7(2) . . . . ?
F9 C23 C24 F10 -2.2(3) . . . . ?
F9 C23 C24 C19 177.7(2) . . . . ?
F11 C26 C27 F12 4.8(4) . . . . ?
F11 C26 C27 C28 -174.9(2) . . . . ?
F12 C27 C28 F13 -0.2(4) . . . . ?
F12 C27 C28 C29 -179.3(2) . . . . ?
F13 C28 C29 F14 -1.0(4) . . . . ?
F13 C28 C29 C30 179.6(3) . . . . ?
F14 C29 C30 F15 -1.5(4) . . . . ?
F14 C29 C30 C25 179.5(2) . . . . ?
N1 N2 N3 C7 14.4(4) . . . . ?
N1 N2 N3 C10 -173.6(2) . . . . ?
N1 C1 C2 C3 175.9(3) . . . . ?
N1 C1 C6 C5 -175.0(3) . . . . ?
N2 N1 C1 C2 61.1(3) . . . . ?
N2 N1 C1 C6 -125.1(3) . . . . ?
N2 N1 B1 C13 -139.57(19) . . . . ?
N2 N1 B1 C19 99.1(2) . . . . ?
N2 N1 B1 C25 -16.1(3) . . . . ?
N2 N3 C7 C8 -124.2(3) . . . . ?
N2 N3 C7 C9 110.3(3) . . . . ?
N2 N3 C10 C11A 67.9(5) . . . . ?
N2 N3 C10 C11B 39.2(11) . . . . ?
N2 N3 C10 C12A -58.5(5) . . . . ?
N2 N3 C10 C12B -73.2(8) . . . . ?
C1 N1 N2 N3 19.1(3) . . . . ?
C1 N1 B1 C13 32.1(3) . . . . ?
C1 N1 B1 C19 -89.3(2) . . . . ?
C1 N1 B1 C25 155.5(2) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C6 C1 C2 C3 2.0(4) . . . . ?
C7 N3 C10 C11A -118.8(4) . . . . ?
C7 N3 C10 C11B -147.5(10) . . . . ?
C7 N3 C10 C12A 114.8(5) . . . . ?
C7 N3 C10 C12B 100.1(8) . . . . ?
C10 N3 C7 C8 64.1(3) . . . . ?
C10 N3 C7 C9 -61.4(3) . . . . ?
C13 C14 C15 F2 -178.8(3) . . . . ?
C13 C14 C15 C16 1.8(5) . . . . ?
C14 C13 C18 F5 -176.5(2) . . . . ?
C14 C13 C18 C17 0.9(4) . . . . ?
C14 C13 B1 N1 65.0(3) . . . . ?
C14 C13 B1 C19 -176.0(2) . . . . ?
C14 C13 B1 C25 -55.2(3) . . . . ?
C14 C15 C16 F3 178.9(3) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 F4 179.3(3) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C16 C17 C18 F5 177.5(3) . . . . ?
C16 C17 C18 C13 0.0(5) . . . . ?
C18 C13 C14 F1 175.6(2) . . . . ?
C18 C13 C14 C15 -1.8(4) . . . . ?
C18 C13 B1 N1 -106.7(3) . . . . ?
C18 C13 B1 C19 12.3(3) . . . . ?
C18 C13 B1 C25 133.1(3) . . . . ?
C19 C20 C21 F7 177.2(2) . . . . ?
C19 C20 C21 C22 -1.5(4) . . . . ?
C20 C19 C24 F10 -177.8(2) . . . . ?
C20 C19 C24 C23 2.3(3) . . . . ?
C20 C19 B1 N1 -14.2(3) . . . . ?
C20 C19 B1 C13 -128.5(2) . . . . ?
C20 C19 B1 C25 104.8(3) . . . . ?
C20 C21 C22 F8 -179.5(2) . . . . ?
C20 C21 C22 C23 1.6(4) . . . . ?
C21 C22 C23 F9 -179.8(2) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 F10 177.9(2) . . . . ?
C22 C23 C24 C19 -2.2(4) . . . . ?
C24 C19 C20 F6 177.8(2) . . . . ?
C24 C19 C20 C21 -0.5(3) . . . . ?
C24 C19 B1 N1 174.64(19) . . . . ?
C24 C19 B1 C13 60.4(3) . . . . ?
C24 C19 B1 C25 -66.4(2) . . . . ?
C25 C26 C27 F12 -177.1(2) . . . . ?
C25 C26 C27 C28 3.1(4) . . . . ?
C26 C25 C30 F15 -174.7(2) . . . . ?
C26 C25 C30 C29 4.3(4) . . . . ?
C26 C25 B1 N1 -122.3(2) . . . . ?
C26 C25 B1 C13 -6.8(3) . . . . ?
C26 C25 B1 C19 118.9(2) . . . . ?
C26 C27 C28 F13 179.5(2) . . . . ?
C26 C27 C28 C29 0.5(4) . . . . ?
C27 C28 C29 F14 178.0(3) . . . . ?
C27 C28 C29 C30 -1.4(4) . . . . ?
C28 C29 C30 F15 177.9(2) . . . . ?
C28 C29 C30 C25 -1.1(4) . . . . ?
C30 C25 C26 F11 172.7(2) . . . . ?
C30 C25 C26 C27 -5.2(4) . . . . ?
C30 C25 B1 N1 62.9(3) . . . . ?
C30 C25 B1 C13 178.5(2) . . . . ?
C30 C25 B1 C19 -55.8(3) . . . . ?
B1 N1 N2 N3 -169.8(2) . . . . ?
B1 N1 C1 C2 -110.0(3) . . . . ?
B1 N1 C1 C6 63.8(3) . . . . ?
B1 C13 C14 F1 2.8(4) . . . . ?
B1 C13 C14 C15 -174.6(3) . . . . ?
B1 C13 C18 F5 -4.3(4) . . . . ?
B1 C13 C18 C17 173.0(3) . . . . ?
B1 C19 C20 F6 6.4(4) . . . . ?
B1 C19 C20 C21 -171.9(2) . . . . ?
B1 C19 C24 F10 -5.5(3) . . . . ?
B1 C19 C24 C23 174.5(2) . . . . ?
B1 C25 C26 F11 -2.3(4) . . . . ?
B1 C25 C26 C27 179.7(2) . . . . ?
B1 C25 C30 F15 0.7(3) . . . . ?
B1 C25 C30 C29 179.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.819
####################################################################### 
# 
# 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_fmc144
_database_code_depnum_ccdc_archive 'CCDC 1967012'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;EPFL
Switzerland
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H23 B F15 N3'
_chemical_formula_sum            'C30 H23 B F15 N3'
_chemical_formula_weight         721.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, 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                   19.1659(5)
_cell_length_b                   18.1081(5)
_cell_length_c                   35.2711(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12241.1(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    11612
_cell_measurement_theta_min      5.0070
_cell_measurement_theta_max      74.1240

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             5824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.093
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 -1 8 0.0318
-12 0 -8 0.0513
-8 2 17 0.0530
-6 2 -19 0.0758
11 -3 -11 0.0313
4 -1 21 0.0302
9 8 6 0.1059
-6 10 -3 0.1750
-1 -12 -2 0.2348
4 2 -22 0.0855
4 -1 -22 0.0590
7 2 19 0.0417
2 5 20 0.0741
10 -1 14 0.0228
-5 -1 20 0.0527
_exptl_absorpt_coefficient_mu    1.404
_shelx_estimated_absorpt_T_min   0.583
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_T_min  0.401
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.1333
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -18.00   1.00   10.00    --  -42.20 -37.00  90.00   99
  2  ω    -66.00  24.00   1.00   10.00    --  -42.20  37.00 -90.00   90
  3  ω   -116.00 -24.00   1.00   10.00    --  -42.20 -37.00   0.00   92
  4  ω      1.00  81.00   1.00   10.00    --   42.20 -99.00 -30.00   80
  5  ω     50.00  86.00   1.00   10.00    --   42.20-125.00-180.00   36
  6  ω     50.00  77.00   1.00   10.00    --   42.20-125.00 -90.00   27
  7  ω     94.00 121.00   1.00   40.00    --  110.51-125.00 -60.00   27
  8  ω    100.00 143.00   1.00   40.00    --  110.51  45.00   0.00   43
  9  ω     52.00 109.00   1.00   40.00    --  110.51 -94.00   0.00   57
 10  ω     39.00 140.00   1.00   40.00    --  110.51 -61.00   0.00  101
 11  ω     49.00 139.00   1.00   40.00    --  110.51 -30.00 120.00   90
 12  ω     38.00 132.00   1.00   40.00    --  110.51 -45.00-120.00   94
 13  ω     68.00 104.00   1.00   40.00    --  110.51 -94.00 -90.00   36
 14  ω     97.00 124.00   1.00   40.00    --  110.51  61.00 -90.00   27
 15  ω    106.00 177.00   1.00   40.00    --  110.51  61.00 -60.00   71
 16  ω     36.00 138.00   1.00   40.00    --  110.51 -77.00 150.00  102
 17  ω     48.00 122.00   1.00   40.00    --  110.51-125.00-180.00   74
 18  ω     29.00 149.00   1.00   40.00    --  110.51 -15.00 -30.00  120
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            91492
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.584
_diffrn_reflns_theta_max         76.291
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12733
_reflns_number_gt                8559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 4.2.0 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+5.4552P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.000034(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         12733
_refine_ls_number_parameters     949
_refine_ls_number_restraints     128
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.71755(8) 0.34229(9) 0.55601(4) 0.0339(3) Uani 1 1 d . . . . .
F2 F 0.81998(10) 0.32348(11) 0.60676(5) 0.0460(4) Uani 1 1 d . . . . .
F3 F 0.90222(10) 0.20115(12) 0.60373(5) 0.0512(5) Uani 1 1 d . . . . .
F4 F 0.87908(9) 0.09722(11) 0.54954(5) 0.0466(4) Uani 1 1 d . . . . .
F5 F 0.78249(8) 0.11734(9) 0.49710(4) 0.0339(3) Uani 1 1 d . . . . .
F6 F 0.56006(7) 0.14564(9) 0.46626(4) 0.0306(3) Uani 1 1 d . . . . .
F7 F 0.56174(8) 0.06941(9) 0.40241(5) 0.0367(4) Uani 1 1 d . . . . .
F8 F 0.67429(9) 0.07315(9) 0.35540(5) 0.0377(4) Uani 1 1 d . . . . .
F9 F 0.78791(8) 0.15604(8) 0.37489(4) 0.0292(3) Uani 1 1 d . . . . .
F10 F 0.78870(7) 0.23168(8) 0.43989(4) 0.0278(3) Uani 1 1 d . . . . .
F11 F 0.56219(7) 0.30346(8) 0.45219(4) 0.0285(3) Uani 1 1 d . . . . .
F12 F 0.55143(9) 0.43134(9) 0.41549(5) 0.0401(4) Uani 1 1 d . . . . .
F13 F 0.65837(10) 0.53120(9) 0.41732(5) 0.0453(4) Uani 1 1 d . . . . .
F14 F 0.77722(9) 0.49742(8) 0.45643(5) 0.0378(4) Uani 1 1 d . . . . .
F15 F 0.79134(8) 0.36900(8) 0.49056(4) 0.0307(3) Uani 1 1 d . . . . .
N1 N 0.61496(11) 0.23538(12) 0.52197(6) 0.0243(4) Uani 1 1 d . . . . .
N2 N 0.57979(11) 0.29451(12) 0.53084(6) 0.0255(4) Uani 1 1 d . . . . .
N3 N 0.52983(11) 0.29876(13) 0.55474(6) 0.0296(5) Uani 1 1 d . . . . .
C1 C 0.50327(15) 0.37693(16) 0.55775(8) 0.0355(6) Uani 1 1 d D U . . .
H1B H 0.456216 0.373208 0.569852 0.043 Uiso 0.25 1 calc R U P A 2
H1A H 0.479208 0.383811 0.582655 0.043 Uiso 0.75 1 calc R U P B 1
C2 C 0.5486(5) 0.4130(5) 0.5861(3) 0.051(3) Uani 0.346(8) 1 d D U P C 2
H2A H 0.547369 0.384892 0.609818 0.076 Uiso 0.346(8) 1 calc R U P C 2
H2B H 0.531950 0.463399 0.590741 0.076 Uiso 0.346(8) 1 calc R U P C 2
H2C H 0.596593 0.414781 0.576535 0.076 Uiso 0.346(8) 1 calc R U P C 2
C3 C 0.5643(3) 0.4339(2) 0.55410(16) 0.0442(14) Uani 0.654(8) 1 d D U P C 1
H3A H 0.602190 0.419988 0.571317 0.066 Uiso 0.654(8) 1 calc R U P C 1
H3B H 0.547264 0.483288 0.560747 0.066 Uiso 0.654(8) 1 calc R U P C 1
H3C H 0.581582 0.434180 0.527956 0.066 Uiso 0.654(8) 1 calc R U P C 1
C4 C 0.4918(10) 0.4127(8) 0.5213(3) 0.072(4) Uani 0.346(8) 1 d D U P C 2
H4A H 0.536207 0.432105 0.511741 0.108 Uiso 0.346(8) 1 calc R U P C 2
H4B H 0.458607 0.453389 0.524438 0.108 Uiso 0.346(8) 1 calc R U P C 2
H4C H 0.473026 0.376740 0.503254 0.108 Uiso 0.346(8) 1 calc R U P C 2
C5 C 0.4519(3) 0.3898(3) 0.52582(16) 0.0414(13) Uani 0.654(8) 1 d D U P C 1
H5A H 0.474600 0.379514 0.501486 0.062 Uiso 0.654(8) 1 calc R U P C 1
H5B H 0.436098 0.441235 0.526323 0.062 Uiso 0.654(8) 1 calc R U P C 1
H5C H 0.411702 0.356872 0.528971 0.062 Uiso 0.654(8) 1 calc R U P C 1
C6 C 0.49298(15) 0.23527(17) 0.57355(9) 0.0357(6) Uani 1 1 d . . . . .
H6 H 0.529190 0.199593 0.582564 0.043 Uiso 1 1 calc R U . . .
C7 C 0.45121(17) 0.2610(2) 0.60795(10) 0.0454(8) Uani 1 1 d . . . . .
H7A H 0.481345 0.290245 0.624644 0.068 Uiso 1 1 calc R U . . .
H7B H 0.433620 0.217940 0.621794 0.068 Uiso 1 1 calc R U . . .
H7C H 0.411847 0.291384 0.599502 0.068 Uiso 1 1 calc R U . . .
C8 C 0.44751(17) 0.1959(2) 0.54453(11) 0.0511(9) Uani 1 1 d . . . . .
H8A H 0.410187 0.229078 0.536153 0.077 Uiso 1 1 calc R U . . .
H8B H 0.426999 0.151685 0.556064 0.077 Uiso 1 1 calc R U . . .
H8C H 0.476055 0.181509 0.522692 0.077 Uiso 1 1 calc R U . . .
C9 C 0.61160(13) 0.16745(15) 0.53913(7) 0.0270(5) Uani 1 1 d . . . . .
C10 C 0.61931(14) 0.10590(15) 0.54995(8) 0.0312(6) Uani 1 1 d . . . . .
C11 C 0.62497(17) 0.02987(16) 0.56435(9) 0.0384(7) Uani 1 1 d . . . . .
C12 C 0.5919(2) 0.02533(19) 0.60356(10) 0.0545(9) Uani 1 1 d . . . . .
H12A H 0.617740 0.057015 0.621170 0.082 Uiso 1 1 calc R U . . .
H12B H 0.593361 -0.025835 0.612572 0.082 Uiso 1 1 calc R U . . .
H12C H 0.543280 0.041909 0.602158 0.082 Uiso 1 1 calc R U . . .
C13 C 0.5877(2) -0.02257(18) 0.53698(11) 0.0519(8) Uani 1 1 d . . . . .
H13A H 0.538152 -0.009452 0.535598 0.078 Uiso 1 1 calc R U . . .
H13B H 0.592397 -0.073449 0.546098 0.078 Uiso 1 1 calc R U . . .
H13C H 0.608669 -0.018368 0.511735 0.078 Uiso 1 1 calc R U . . .
C14 C 0.70299(18) 0.00948(18) 0.56645(11) 0.0502(8) Uani 1 1 d . . . . .
H14A H 0.723151 0.010557 0.540927 0.075 Uiso 1 1 calc R U . . .
H14B H 0.707998 -0.040192 0.577148 0.075 Uiso 1 1 calc R U . . .
H14C H 0.727398 0.045101 0.582626 0.075 Uiso 1 1 calc R U . . .
C15 C 0.74652(13) 0.23311(15) 0.52259(7) 0.0248(5) Uani 1 1 d . . . . .
C16 C 0.75846(14) 0.28203(15) 0.55250(8) 0.0294(5) Uani 1 1 d . . . . .
C17 C 0.80991(15) 0.27313(17) 0.57929(8) 0.0349(6) Uani 1 1 d . . . . .
C18 C 0.85167(15) 0.21155(19) 0.57773(8) 0.0373(7) Uani 1 1 d . . . . .
C19 C 0.84068(14) 0.15945(17) 0.55004(8) 0.0348(6) Uani 1 1 d . . . . .
C20 C 0.78933(13) 0.17143(15) 0.52302(7) 0.0287(5) Uani 1 1 d . . . . .
C21 C 0.67591(12) 0.19086(13) 0.45751(7) 0.0225(5) Uani 1 1 d . . . . .
C22 C 0.61970(12) 0.14864(14) 0.44568(7) 0.0245(5) Uani 1 1 d . . . . .
C23 C 0.61863(13) 0.10849(14) 0.41231(7) 0.0266(5) Uani 1 1 d . . . . .
C24 C 0.67534(14) 0.11066(14) 0.38814(7) 0.0270(5) Uani 1 1 d . . . . .
C25 C 0.73256(13) 0.15250(13) 0.39818(7) 0.0242(5) Uani 1 1 d . . . . .
C26 C 0.73155(12) 0.19085(13) 0.43189(7) 0.0232(5) Uani 1 1 d . . . . .
C27 C 0.67601(13) 0.33008(14) 0.47502(7) 0.0246(5) Uani 1 1 d . . . . .
C28 C 0.61701(13) 0.35048(14) 0.45439(7) 0.0257(5) Uani 1 1 d . . . . .
C29 C 0.60991(14) 0.41663(15) 0.43525(8) 0.0311(6) Uani 1 1 d . . . . .
C30 C 0.66397(16) 0.46653(15) 0.43600(8) 0.0334(6) Uani 1 1 d . . . . .
C31 C 0.72363(15) 0.44920(14) 0.45563(8) 0.0307(6) Uani 1 1 d . . . . .
C32 C 0.72900(13) 0.38205(14) 0.47387(7) 0.0269(5) Uani 1 1 d . . . . .
B1 B 0.68049(14) 0.24720(15) 0.49370(8) 0.0232(6) Uani 1 1 d . . . . .
F16 F 0.43130(8) 0.36030(9) 0.22063(4) 0.0319(3) Uani 1 1 d . . . . .
F17 F 0.43127(9) 0.43812(9) 0.15729(5) 0.0369(4) Uani 1 1 d . . . . .
F18 F 0.32558(9) 0.42621(9) 0.10639(5) 0.0377(4) Uani 1 1 d . . . . .
F19 F 0.21640(8) 0.33331(9) 0.12144(4) 0.0326(3) Uani 1 1 d . . . . .
F20 F 0.21438(8) 0.25460(8) 0.18549(4) 0.0283(3) Uani 1 1 d . . . . .
F21 F 0.20233(8) 0.36927(9) 0.23950(5) 0.0340(3) Uani 1 1 d . . . . .
F22 F 0.09989(9) 0.38698(11) 0.28819(6) 0.0486(5) Uani 1 1 d . . . . .
F23 F 0.08367(10) 0.29329(13) 0.34795(6) 0.0566(5) Uani 1 1 d . . . . .
F24 F 0.17500(10) 0.17901(12) 0.35729(5) 0.0503(5) Uani 1 1 d . . . . .
F25 F 0.28022(8) 0.15994(9) 0.30832(4) 0.0349(4) Uani 1 1 d . . . . .
F26 F 0.21251(8) 0.12112(9) 0.24121(5) 0.0334(3) Uani 1 1 d . . . . .
F27 F 0.23096(10) -0.00557(9) 0.20615(5) 0.0411(4) Uani 1 1 d . . . . .
F28 F 0.35182(11) -0.03367(9) 0.16740(5) 0.0485(5) Uani 1 1 d . . . . .
F29 F 0.45525(10) 0.07046(11) 0.16681(5) 0.0472(4) Uani 1 1 d . . . . .
F30 F 0.43893(8) 0.19750(9) 0.20374(4) 0.0326(3) Uani 1 1 d . . . . .
N4 N 0.37799(11) 0.26399(12) 0.27361(6) 0.0249(4) Uani 1 1 d . . . . .
N5 N 0.41668(11) 0.20708(13) 0.28275(6) 0.0266(4) Uani 1 1 d . . . . .
N6 N 0.46558(11) 0.20690(13) 0.30765(6) 0.0293(5) Uani 1 1 d . . . . .
C33 C 0.49751(15) 0.13047(17) 0.31165(8) 0.0378(7) Uani 1 1 d . . . . .
H33 H 0.513858 0.125241 0.338439 0.045 Uiso 1 1 calc R U . . .
C34 C 0.44538(19) 0.07042(19) 0.30446(11) 0.0538(9) Uani 1 1 d . . . . .
H34A H 0.432406 0.070385 0.277583 0.081 Uiso 1 1 calc R U . . .
H34B H 0.403736 0.079017 0.319966 0.081 Uiso 1 1 calc R U . . .
H34C H 0.465898 0.022580 0.311125 0.081 Uiso 1 1 calc R U . . .
C35 C 0.56099(18) 0.1248(2) 0.28629(11) 0.0536(9) Uani 1 1 d . . . . .
H35A H 0.594044 0.164102 0.292717 0.080 Uiso 1 1 calc R U . . .
H35B H 0.546684 0.129849 0.259746 0.080 Uiso 1 1 calc R U . . .
H35C H 0.583332 0.076616 0.289998 0.080 Uiso 1 1 calc R U . . .
C36 C 0.49883(14) 0.27353(17) 0.32522(8) 0.0332(6) Uani 1 1 d . . . . .
H36 H 0.460458 0.306402 0.334408 0.040 Uiso 1 1 calc R U . . .
C37 C 0.54404(16) 0.2538(2) 0.35944(9) 0.0437(8) Uani 1 1 d . . . . .
H37A H 0.583800 0.223856 0.351098 0.066 Uiso 1 1 calc R U . . .
H37B H 0.516219 0.225599 0.377731 0.066 Uiso 1 1 calc R U . . .
H37C H 0.561083 0.299117 0.371429 0.066 Uiso 1 1 calc R U . . .
C38 C 0.53960(16) 0.3161(2) 0.29516(10) 0.0460(8) Uani 1 1 d . . . . .
H38A H 0.509471 0.325418 0.273220 0.069 Uiso 1 1 calc R U . . .
H38B H 0.580161 0.287064 0.287200 0.069 Uiso 1 1 calc R U . . .
H38C H 0.555350 0.363318 0.305755 0.069 Uiso 1 1 calc R U . . .
C39 C 0.37469(13) 0.33040(15) 0.29200(7) 0.0272(5) Uani 1 1 d . . . . .
C40 C 0.35950(15) 0.38928(16) 0.30434(8) 0.0318(6) Uani 1 1 d . . . . .
C41 C 0.34469(18) 0.46289(16) 0.31933(9) 0.0414(7) Uani 1 1 d D U . . .
C45 C 0.32131(12) 0.30460(13) 0.20729(7) 0.0223(5) Uani 1 1 d . . . . .
C46 C 0.37516(13) 0.35199(14) 0.19785(7) 0.0245(5) Uani 1 1 d . . . . .
C47 C 0.37712(13) 0.39337(14) 0.16478(8) 0.0275(5) Uani 1 1 d . . . . .
C48 C 0.32370(14) 0.38731(14) 0.13881(7) 0.0271(5) Uani 1 1 d . . . . .
C49 C 0.26880(13) 0.34017(14) 0.14658(7) 0.0254(5) Uani 1 1 d . . . . .
C50 C 0.26913(12) 0.30019(13) 0.17986(7) 0.0238(5) Uani 1 1 d . . . . .
C51 C 0.24577(13) 0.26135(14) 0.27023(7) 0.0259(5) Uani 1 1 d . . . . .
C52 C 0.19794(14) 0.31846(15) 0.26735(8) 0.0293(5) Uani 1 1 d . . . . .
C53 C 0.14373(14) 0.32954(17) 0.29281(9) 0.0362(6) Uani 1 1 d . . . . .
C54 C 0.13591(15) 0.28236(19) 0.32296(9) 0.0410(7) Uani 1 1 d . . . . .
C55 C 0.18233(15) 0.22557(18) 0.32771(8) 0.0371(7) Uani 1 1 d . . . . .
C56 C 0.23569(13) 0.21603(15) 0.30180(8) 0.0300(6) Uani 1 1 d . . . . .
C57 C 0.32562(13) 0.16583(14) 0.22549(7) 0.0248(5) Uani 1 1 d . . . . .
C58 C 0.27504(14) 0.11123(15) 0.22430(7) 0.0283(5) Uani 1 1 d . . . . .
C59 C 0.28293(15) 0.04424(14) 0.20582(8) 0.0309(6) Uani 1 1 d . . . . .
C60 C 0.34375(17) 0.03001(15) 0.18643(8) 0.0356(6) Uani 1 1 d . . . . .
C61 C 0.39570(15) 0.08270(16) 0.18631(8) 0.0339(6) Uani 1 1 d . . . . .
C62 C 0.38602(14) 0.14815(15) 0.20554(7) 0.0281(5) Uani 1 1 d . . . . .
C66 C 0.3858(11) 0.5244(11) 0.3022(5) 0.046(4) Uani 0.346(8) 1 d D U P C 2
H66A H 0.379487 0.524118 0.274595 0.069 Uiso 0.346(8) 1 calc R U P C 2
H66B H 0.435385 0.517744 0.308141 0.069 Uiso 0.346(8) 1 calc R U P C 2
H66C H 0.369678 0.571617 0.312484 0.069 Uiso 0.346(8) 1 calc R U P C 2
C67 C 0.2647(6) 0.4751(12) 0.3110(6) 0.035(3) Uani 0.346(8) 1 d D U P C 2
H67A H 0.237446 0.436275 0.323472 0.052 Uiso 0.346(8) 1 calc R U P C 2
H67B H 0.256546 0.473256 0.283592 0.052 Uiso 0.346(8) 1 calc R U P C 2
H67C H 0.250289 0.523442 0.320783 0.052 Uiso 0.346(8) 1 calc R U P C 2
C68 C 0.3512(9) 0.4583(10) 0.3628(3) 0.052(4) Uani 0.346(8) 1 d D U P C 2
H68A H 0.399195 0.444943 0.369571 0.079 Uiso 0.346(8) 1 calc R U P C 2
H68B H 0.319078 0.420689 0.372463 0.079 Uiso 0.346(8) 1 calc R U P C 2
H68C H 0.339636 0.506297 0.373939 0.079 Uiso 0.346(8) 1 calc R U P C 2
C72 C 0.3826(6) 0.5161(5) 0.2916(2) 0.042(2) Uani 0.654(8) 1 d D U P C 1
H72A H 0.364125 0.509279 0.265970 0.063 Uiso 0.654(8) 1 calc R U P C 1
H72B H 0.432750 0.505352 0.291740 0.063 Uiso 0.654(8) 1 calc R U P C 1
H72C H 0.374978 0.567245 0.299709 0.063 Uiso 0.654(8) 1 calc R U P C 1
C73 C 0.2670(4) 0.4808(8) 0.3202(3) 0.049(3) Uani 0.654(8) 1 d D U P C 1
H73A H 0.242640 0.444462 0.335961 0.074 Uiso 0.654(8) 1 calc R U P C 1
H73B H 0.248245 0.479064 0.294321 0.074 Uiso 0.654(8) 1 calc R U P C 1
H73C H 0.260080 0.530288 0.330732 0.074 Uiso 0.654(8) 1 calc R U P C 1
C74 C 0.3781(6) 0.4731(6) 0.3587(2) 0.066(3) Uani 0.654(8) 1 d D U P C 1
H74A H 0.428175 0.462396 0.357179 0.100 Uiso 0.654(8) 1 calc R U P C 1
H74B H 0.356149 0.439245 0.376816 0.100 Uiso 0.654(8) 1 calc R U P C 1
H74C H 0.371336 0.524113 0.367217 0.100 Uiso 0.654(8) 1 calc R U P C 1
B2 B 0.31561(14) 0.24880(16) 0.24367(8) 0.0238(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
F1 C16 1.349(3) . ?
F2 C17 1.344(3) . ?
F3 C18 1.347(3) . ?
F4 C19 1.346(3) . ?
F5 C20 1.346(3) . ?
F6 C22 1.355(3) . ?
F7 C23 1.346(3) . ?
F8 C24 1.340(3) . ?
F9 C25 1.343(3) . ?
F10 C26 1.351(3) . ?
F11 C28 1.355(3) . ?
F12 C29 1.346(3) . ?
F13 C30 1.348(3) . ?
F14 C31 1.348(3) . ?
F15 C32 1.353(3) . ?
N1 N2 1.303(3) . ?
N1 C9 1.373(3) . ?
N1 B1 1.618(3) . ?
N2 N3 1.278(3) . ?
N3 C6 1.504(4) . ?
N3 C1 1.508(3) . ?
C1 C4 1.456(9) . ?
C1 C2 1.477(9) . ?
C1 C5 1.514(5) . ?
C1 C3 1.565(5) . ?
C6 C8 1.522(5) . ?
C6 C7 1.527(4) . ?
C9 C10 1.187(4) . ?
C10 C11 1.471(4) . ?
C11 C12 1.524(4) . ?
C11 C13 1.531(5) . ?
C11 C14 1.542(4) . ?
C15 C20 1.386(4) . ?
C15 C16 1.396(4) . ?
C15 B1 1.645(4) . ?
C16 C17 1.375(4) . ?
C17 C18 1.374(5) . ?
C18 C19 1.374(5) . ?
C19 C20 1.387(4) . ?
C21 C22 1.385(3) . ?
C21 C26 1.398(3) . ?
C21 B1 1.636(4) . ?
C22 C23 1.384(4) . ?
C23 C24 1.382(4) . ?
C24 C25 1.379(4) . ?
C25 C26 1.377(4) . ?
C27 C32 1.385(4) . ?
C27 C28 1.394(4) . ?
C27 B1 1.641(4) . ?
C28 C29 1.382(4) . ?
C29 C30 1.375(4) . ?
C30 C31 1.373(4) . ?
C31 C32 1.380(4) . ?
F16 C46 1.351(3) . ?
F17 C47 1.343(3) . ?
F18 C48 1.343(3) . ?
F19 C49 1.345(3) . ?
F20 C50 1.350(3) . ?
F21 C52 1.348(3) . ?
F22 C53 1.347(4) . ?
F23 C54 1.349(3) . ?
F24 C55 1.349(3) . ?
F25 C56 1.346(3) . ?
F26 C58 1.351(3) . ?
F27 C59 1.344(3) . ?
F28 C60 1.343(3) . ?
F29 C61 1.351(3) . ?
F30 C62 1.353(3) . ?
N4 N5 1.310(3) . ?
N4 C39 1.368(3) . ?
N4 B2 1.619(3) . ?
N5 N6 1.284(3) . ?
N6 C36 1.499(4) . ?
N6 C33 1.520(4) . ?
C33 C34 1.498(5) . ?
C33 C35 1.513(4) . ?
C36 C38 1.527(4) . ?
C36 C37 1.528(4) . ?
C39 C40 1.188(4) . ?
C40 C41 1.462(4) . ?
C41 C66 1.493(11) . ?
C41 C73 1.525(9) . ?
C41 C68 1.540(11) . ?
C41 C74 1.541(8) . ?
C41 C72 1.553(7) . ?
C41 C67 1.577(10) . ?
C45 C46 1.383(3) . ?
C45 C50 1.394(3) . ?
C45 B2 1.637(4) . ?
C46 C47 1.387(4) . ?
C47 C48 1.378(4) . ?
C48 C49 1.382(4) . ?
C49 C50 1.379(4) . ?
C51 C52 1.386(4) . ?
C51 C56 1.397(4) . ?
C51 B2 1.650(4) . ?
C52 C53 1.388(4) . ?
C53 C54 1.372(5) . ?
C54 C55 1.370(5) . ?
C55 C56 1.382(4) . ?
C57 C58 1.385(4) . ?
C57 C62 1.392(4) . ?
C57 B2 1.645(4) . ?
C58 C59 1.385(4) . ?
C59 C60 1.376(4) . ?
C60 C61 1.379(4) . ?
C61 C62 1.378(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
N2 N1 C9 127.3(2) . . ?
N2 N1 B1 116.2(2) . . ?
C9 N1 B1 115.3(2) . . ?
N3 N2 N1 126.5(2) . . ?
N2 N3 C6 126.6(2) . . ?
N2 N3 C1 110.8(2) . . ?
C6 N3 C1 121.9(2) . . ?
C4 C1 C2 119.3(9) . . ?
C4 C1 N3 114.0(5) . . ?
C2 C1 N3 105.3(4) . . ?
N3 C1 C5 108.1(3) . . ?
N3 C1 C3 111.2(3) . . ?
C5 C1 C3 108.9(4) . . ?
N3 C6 C8 109.3(3) . . ?
N3 C6 C7 111.3(3) . . ?
C8 C6 C7 112.2(3) . . ?
C10 C9 N1 167.8(3) . . ?
C9 C10 C11 176.8(3) . . ?
C10 C11 C12 109.4(3) . . ?
C10 C11 C13 109.2(3) . . ?
C12 C11 C13 110.2(3) . . ?
C10 C11 C14 108.2(2) . . ?
C12 C11 C14 110.3(3) . . ?
C13 C11 C14 109.5(3) . . ?
C20 C15 C16 114.0(2) . . ?
C20 C15 B1 126.0(2) . . ?
C16 C15 B1 119.7(2) . . ?
F1 C16 C17 116.6(2) . . ?
F1 C16 C15 119.2(2) . . ?
C17 C16 C15 124.2(3) . . ?
F2 C17 C18 119.7(3) . . ?
F2 C17 C16 121.2(3) . . ?
C18 C17 C16 119.0(3) . . ?
F3 C18 C17 120.3(3) . . ?
F3 C18 C19 119.9(3) . . ?
C17 C18 C19 119.8(3) . . ?
F4 C19 C18 120.0(3) . . ?
F4 C19 C20 120.7(3) . . ?
C18 C19 C20 119.3(3) . . ?
F5 C20 C15 121.4(2) . . ?
F5 C20 C19 115.0(2) . . ?
C15 C20 C19 123.6(3) . . ?
C22 C21 C26 113.5(2) . . ?
C22 C21 B1 128.4(2) . . ?
C26 C21 B1 117.6(2) . . ?
F6 C22 C23 115.0(2) . . ?
F6 C22 C21 121.1(2) . . ?
C23 C22 C21 123.9(2) . . ?
F7 C23 C24 119.5(2) . . ?
F7 C23 C22 120.6(2) . . ?
C24 C23 C22 119.9(2) . . ?
F8 C24 C25 120.8(2) . . ?
F8 C24 C23 120.4(2) . . ?
C25 C24 C23 118.9(2) . . ?
F9 C25 C26 121.0(2) . . ?
F9 C25 C24 119.8(2) . . ?
C26 C25 C24 119.2(2) . . ?
F10 C26 C25 116.4(2) . . ?
F10 C26 C21 118.9(2) . . ?
C25 C26 C21 124.7(2) . . ?
C32 C27 C28 113.5(2) . . ?
C32 C27 B1 126.5(2) . . ?
C28 C27 B1 119.6(2) . . ?
F11 C28 C29 116.1(2) . . ?
F11 C28 C27 119.5(2) . . ?
C29 C28 C27 124.4(2) . . ?
F12 C29 C30 120.5(3) . . ?
F12 C29 C28 120.4(3) . . ?
C30 C29 C28 119.1(3) . . ?
F13 C30 C31 120.8(3) . . ?
F13 C30 C29 120.1(3) . . ?
C31 C30 C29 119.2(3) . . ?
F14 C31 C30 119.8(2) . . ?
F14 C31 C32 120.3(3) . . ?
C30 C31 C32 119.9(3) . . ?
F15 C32 C31 115.0(2) . . ?
F15 C32 C27 121.1(2) . . ?
C31 C32 C27 123.9(3) . . ?
N1 B1 C21 110.89(19) . . ?
N1 B1 C27 109.1(2) . . ?
C21 B1 C27 104.7(2) . . ?
N1 B1 C15 101.3(2) . . ?
C21 B1 C15 115.3(2) . . ?
C27 B1 C15 115.5(2) . . ?
N5 N4 C39 127.0(2) . . ?
N5 N4 B2 116.4(2) . . ?
C39 N4 B2 115.1(2) . . ?
N6 N5 N4 125.7(2) . . ?
N5 N6 C36 126.2(2) . . ?
N5 N6 C33 111.1(2) . . ?
C36 N6 C33 121.6(2) . . ?
C34 C33 C35 112.7(3) . . ?
C34 C33 N6 112.1(2) . . ?
C35 C33 N6 109.3(3) . . ?
N6 C36 C38 109.7(2) . . ?
N6 C36 C37 112.3(3) . . ?
C38 C36 C37 112.1(2) . . ?
C40 C39 N4 167.0(3) . . ?
C39 C40 C41 177.0(3) . . ?
C40 C41 C66 115.5(9) . . ?
C40 C41 C73 113.0(6) . . ?
C40 C41 C68 107.1(8) . . ?
C66 C41 C68 113.6(8) . . ?
C40 C41 C74 110.8(5) . . ?
C73 C41 C74 111.3(6) . . ?
C40 C41 C72 104.3(5) . . ?
C73 C41 C72 109.7(6) . . ?
C74 C41 C72 107.3(5) . . ?
C40 C41 C67 104.4(8) . . ?
C66 C41 C67 109.5(9) . . ?
C68 C41 C67 105.8(8) . . ?
C46 C45 C50 113.8(2) . . ?
C46 C45 B2 128.4(2) . . ?
C50 C45 B2 117.4(2) . . ?
F16 C46 C45 121.3(2) . . ?
F16 C46 C47 114.7(2) . . ?
C45 C46 C47 123.9(2) . . ?
F17 C47 C48 119.4(2) . . ?
F17 C47 C46 120.8(2) . . ?
C48 C47 C46 119.7(2) . . ?
F18 C48 C47 120.3(2) . . ?
F18 C48 C49 120.9(2) . . ?
C47 C48 C49 118.9(2) . . ?
F19 C49 C50 121.1(2) . . ?
F19 C49 C48 119.6(2) . . ?
C50 C49 C48 119.3(2) . . ?
F20 C50 C49 116.3(2) . . ?
F20 C50 C45 119.4(2) . . ?
C49 C50 C45 124.3(2) . . ?
C52 C51 C56 113.9(2) . . ?
C52 C51 B2 126.7(2) . . ?
C56 C51 B2 118.9(2) . . ?
F21 C52 C51 121.4(2) . . ?
F21 C52 C53 114.8(2) . . ?
C51 C52 C53 123.8(3) . . ?
F22 C53 C54 120.4(3) . . ?
F22 C53 C52 120.0(3) . . ?
C54 C53 C52 119.6(3) . . ?
F23 C54 C55 120.8(3) . . ?
F23 C54 C53 119.8(3) . . ?
C55 C54 C53 119.4(3) . . ?
F24 C55 C54 119.8(3) . . ?
F24 C55 C56 120.7(3) . . ?
C54 C55 C56 119.6(3) . . ?
F25 C56 C55 116.8(3) . . ?
F25 C56 C51 119.4(2) . . ?
C55 C56 C51 123.8(3) . . ?
C58 C57 C62 113.7(2) . . ?
C58 C57 B2 125.6(2) . . ?
C62 C57 B2 120.3(2) . . ?
F26 C58 C59 114.9(2) . . ?
F26 C58 C57 120.8(2) . . ?
C59 C58 C57 124.3(3) . . ?
F27 C59 C60 120.4(2) . . ?
F27 C59 C58 120.2(3) . . ?
C60 C59 C58 119.4(3) . . ?
F28 C60 C59 120.4(3) . . ?
F28 C60 C61 120.6(3) . . ?
C59 C60 C61 118.9(3) . . ?
F29 C61 C62 120.4(3) . . ?
F29 C61 C60 119.9(3) . . ?
C62 C61 C60 119.8(3) . . ?
F30 C62 C61 116.4(2) . . ?
F30 C62 C57 119.7(2) . . ?
C61 C62 C57 124.0(3) . . ?
N4 B2 C45 110.93(19) . . ?
N4 B2 C57 108.9(2) . . ?
C45 B2 C57 104.5(2) . . ?
N4 B2 C51 101.9(2) . . ?
C45 B2 C51 114.5(2) . . ?
C57 B2 C51 116.2(2) . . ?

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
C9 N1 N2 N3 -8.0(4) . . . . ?
B1 N1 N2 N3 -174.4(2) . . . . ?
N1 N2 N3 C6 -10.1(4) . . . . ?
N1 N2 N3 C1 178.9(2) . . . . ?
N2 N3 C1 C4 46.5(9) . . . . ?
C6 N3 C1 C4 -125.0(9) . . . . ?
N2 N3 C1 C2 -86.1(5) . . . . ?
C6 N3 C1 C2 102.4(5) . . . . ?
N2 N3 C1 C5 83.2(4) . . . . ?
C6 N3 C1 C5 -88.3(4) . . . . ?
N2 N3 C1 C3 -36.3(4) . . . . ?
C6 N3 C1 C3 152.2(3) . . . . ?
N2 N3 C6 C8 -71.5(3) . . . . ?
C1 N3 C6 C8 98.6(3) . . . . ?
N2 N3 C6 C7 164.0(3) . . . . ?
C1 N3 C6 C7 -25.9(4) . . . . ?
N2 N1 C9 C10 -169.8(13) . . . . ?
B1 N1 C9 C10 -3.3(15) . . . . ?
C20 C15 C16 F1 -176.8(2) . . . . ?
B1 C15 C16 F1 -3.3(4) . . . . ?
C20 C15 C16 C17 3.1(4) . . . . ?
B1 C15 C16 C17 176.5(2) . . . . ?
F1 C16 C17 F2 -2.1(4) . . . . ?
C15 C16 C17 F2 178.0(2) . . . . ?
F1 C16 C17 C18 178.0(2) . . . . ?
C15 C16 C17 C18 -1.9(4) . . . . ?
F2 C17 C18 F3 0.5(4) . . . . ?
C16 C17 C18 F3 -179.6(2) . . . . ?
F2 C17 C18 C19 178.9(3) . . . . ?
C16 C17 C18 C19 -1.2(4) . . . . ?
F3 C18 C19 F4 1.8(4) . . . . ?
C17 C18 C19 F4 -176.6(3) . . . . ?
F3 C18 C19 C20 -178.8(2) . . . . ?
C17 C18 C19 C20 2.7(4) . . . . ?
C16 C15 C20 F5 177.1(2) . . . . ?
B1 C15 C20 F5 4.1(4) . . . . ?
C16 C15 C20 C19 -1.4(4) . . . . ?
B1 C15 C20 C19 -174.4(2) . . . . ?
F4 C19 C20 F5 -0.7(4) . . . . ?
C18 C19 C20 F5 180.0(2) . . . . ?
F4 C19 C20 C15 177.9(2) . . . . ?
C18 C19 C20 C15 -1.4(4) . . . . ?
C26 C21 C22 F6 -176.6(2) . . . . ?
B1 C21 C22 F6 -5.4(4) . . . . ?
C26 C21 C22 C23 1.6(4) . . . . ?
B1 C21 C22 C23 172.9(2) . . . . ?
F6 C22 C23 F7 -0.8(4) . . . . ?
C21 C22 C23 F7 -179.2(2) . . . . ?
F6 C22 C23 C24 176.7(2) . . . . ?
C21 C22 C23 C24 -1.7(4) . . . . ?
F7 C23 C24 F8 -1.2(4) . . . . ?
C22 C23 C24 F8 -178.7(2) . . . . ?
F7 C23 C24 C25 178.3(2) . . . . ?
C22 C23 C24 C25 0.8(4) . . . . ?
F8 C24 C25 F9 0.2(4) . . . . ?
C23 C24 C25 F9 -179.2(2) . . . . ?
F8 C24 C25 C26 179.4(2) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
F9 C25 C26 F10 0.1(3) . . . . ?
C24 C25 C26 F10 -179.1(2) . . . . ?
F9 C25 C26 C21 179.3(2) . . . . ?
C24 C25 C26 C21 0.1(4) . . . . ?
C22 C21 C26 F10 178.3(2) . . . . ?
B1 C21 C26 F10 6.0(3) . . . . ?
C22 C21 C26 C25 -0.8(4) . . . . ?
B1 C21 C26 C25 -173.1(2) . . . . ?
C32 C27 C28 F11 177.9(2) . . . . ?
B1 C27 C28 F11 4.4(3) . . . . ?
C32 C27 C28 C29 -1.7(4) . . . . ?
B1 C27 C28 C29 -175.2(2) . . . . ?
F11 C28 C29 F12 -0.7(4) . . . . ?
C27 C28 C29 F12 178.9(2) . . . . ?
F11 C28 C29 C30 -179.3(2) . . . . ?
C27 C28 C29 C30 0.3(4) . . . . ?
F12 C29 C30 F13 0.9(4) . . . . ?
C28 C29 C30 F13 179.6(2) . . . . ?
F12 C29 C30 C31 -178.4(2) . . . . ?
C28 C29 C30 C31 0.2(4) . . . . ?
F13 C30 C31 F14 0.3(4) . . . . ?
C29 C30 C31 F14 179.6(2) . . . . ?
F13 C30 C31 C32 -178.5(2) . . . . ?
C29 C30 C31 C32 0.8(4) . . . . ?
F14 C31 C32 F15 -2.3(3) . . . . ?
C30 C31 C32 F15 176.5(2) . . . . ?
F14 C31 C32 C27 178.7(2) . . . . ?
C30 C31 C32 C27 -2.4(4) . . . . ?
C28 C27 C32 F15 -176.1(2) . . . . ?
B1 C27 C32 F15 -3.2(4) . . . . ?
C28 C27 C32 C31 2.8(4) . . . . ?
B1 C27 C32 C31 175.7(2) . . . . ?
N2 N1 B1 C21 -127.8(2) . . . . ?
C9 N1 B1 C21 64.1(3) . . . . ?
N2 N1 B1 C27 -13.0(3) . . . . ?
C9 N1 B1 C27 178.9(2) . . . . ?
N2 N1 B1 C15 109.3(2) . . . . ?
C9 N1 B1 C15 -58.8(3) . . . . ?
C22 C21 B1 N1 13.4(4) . . . . ?
C26 C21 B1 N1 -175.6(2) . . . . ?
C22 C21 B1 C27 -104.2(3) . . . . ?
C26 C21 B1 C27 66.8(3) . . . . ?
C22 C21 B1 C15 127.7(3) . . . . ?
C26 C21 B1 C15 -61.3(3) . . . . ?
C32 C27 B1 N1 129.4(3) . . . . ?
C28 C27 B1 N1 -58.0(3) . . . . ?
C32 C27 B1 C21 -111.8(3) . . . . ?
C28 C27 B1 C21 60.7(3) . . . . ?
C32 C27 B1 C15 16.2(4) . . . . ?
C28 C27 B1 C15 -171.3(2) . . . . ?
C20 C15 B1 N1 107.0(3) . . . . ?
C16 C15 B1 N1 -65.7(3) . . . . ?
C20 C15 B1 C21 -12.8(4) . . . . ?
C16 C15 B1 C21 174.6(2) . . . . ?
C20 C15 B1 C27 -135.3(3) . . . . ?
C16 C15 B1 C27 52.1(3) . . . . ?
C39 N4 N5 N6 -10.1(4) . . . . ?
B2 N4 N5 N6 -175.4(2) . . . . ?
N4 N5 N6 C36 -14.0(4) . . . . ?
N4 N5 N6 C33 178.0(2) . . . . ?
N5 N6 C33 C34 -31.6(3) . . . . ?
C36 N6 C33 C34 159.8(3) . . . . ?
N5 N6 C33 C35 94.1(3) . . . . ?
C36 N6 C33 C35 -74.4(3) . . . . ?
N5 N6 C36 C38 -66.6(3) . . . . ?
C33 N6 C36 C38 100.2(3) . . . . ?
N5 N6 C36 C37 168.0(2) . . . . ?
C33 N6 C36 C37 -25.2(4) . . . . ?
N5 N4 C39 C40 -159.8(12) . . . . ?
B2 N4 C39 C40 5.7(14) . . . . ?
C50 C45 C46 F16 -177.2(2) . . . . ?
B2 C45 C46 F16 -3.8(4) . . . . ?
C50 C45 C46 C47 1.7(4) . . . . ?
B2 C45 C46 C47 175.2(2) . . . . ?
F16 C46 C47 F17 -0.7(4) . . . . ?
C45 C46 C47 F17 -179.7(2) . . . . ?
F16 C46 C47 C48 177.8(2) . . . . ?
C45 C46 C47 C48 -1.2(4) . . . . ?
F17 C47 C48 F18 -0.4(4) . . . . ?
C46 C47 C48 F18 -178.9(2) . . . . ?
F17 C47 C48 C49 179.0(2) . . . . ?
C46 C47 C48 C49 0.5(4) . . . . ?
F18 C48 C49 F19 -0.3(4) . . . . ?
C47 C48 C49 F19 -179.7(2) . . . . ?
F18 C48 C49 C50 179.0(2) . . . . ?
C47 C48 C49 C50 -0.4(4) . . . . ?
F19 C49 C50 F20 -0.1(3) . . . . ?
C48 C49 C50 F20 -179.3(2) . . . . ?
F19 C49 C50 C45 -179.7(2) . . . . ?
C48 C49 C50 C45 1.1(4) . . . . ?
C46 C45 C50 F20 178.7(2) . . . . ?
B2 C45 C50 F20 4.5(3) . . . . ?
C46 C45 C50 C49 -1.7(4) . . . . ?
B2 C45 C50 C49 -175.9(2) . . . . ?
C56 C51 C52 F21 176.9(2) . . . . ?
B2 C51 C52 F21 4.3(4) . . . . ?
C56 C51 C52 C53 -1.3(4) . . . . ?
B2 C51 C52 C53 -173.9(3) . . . . ?
F21 C52 C53 F22 1.0(4) . . . . ?
C51 C52 C53 F22 179.3(2) . . . . ?
F21 C52 C53 C54 -177.9(3) . . . . ?
C51 C52 C53 C54 0.4(4) . . . . ?
F22 C53 C54 F23 0.5(5) . . . . ?
C52 C53 C54 F23 179.4(3) . . . . ?
F22 C53 C54 C55 -178.1(3) . . . . ?
C52 C53 C54 C55 0.8(5) . . . . ?
F23 C54 C55 F24 1.4(5) . . . . ?
C53 C54 C55 F24 180.0(3) . . . . ?
F23 C54 C55 C56 -179.5(3) . . . . ?
C53 C54 C55 C56 -0.9(5) . . . . ?
F24 C55 C56 F25 -1.8(4) . . . . ?
C54 C55 C56 F25 179.0(3) . . . . ?
F24 C55 C56 C51 179.0(3) . . . . ?
C54 C55 C56 C51 -0.1(4) . . . . ?
C52 C51 C56 F25 -178.0(2) . . . . ?
B2 C51 C56 F25 -4.7(4) . . . . ?
C52 C51 C56 C55 1.2(4) . . . . ?
B2 C51 C56 C55 174.4(2) . . . . ?
C62 C57 C58 F26 -177.7(2) . . . . ?
B2 C57 C58 F26 -4.9(4) . . . . ?
C62 C57 C58 C59 1.2(4) . . . . ?
B2 C57 C58 C59 174.0(2) . . . . ?
F26 C58 C59 F27 -1.0(3) . . . . ?
C57 C58 C59 F27 -180.0(2) . . . . ?
F26 C58 C59 C60 177.4(2) . . . . ?
C57 C58 C59 C60 -1.5(4) . . . . ?
F27 C59 C60 F28 0.4(4) . . . . ?
C58 C59 C60 F28 -178.1(2) . . . . ?
F27 C59 C60 C61 179.3(2) . . . . ?
C58 C59 C60 C61 0.8(4) . . . . ?
F28 C60 C61 F29 0.2(4) . . . . ?
C59 C60 C61 F29 -178.7(2) . . . . ?
F28 C60 C61 C62 179.0(2) . . . . ?
C59 C60 C61 C62 0.1(4) . . . . ?
F29 C61 C62 F30 -0.4(4) . . . . ?
C60 C61 C62 F30 -179.2(2) . . . . ?
F29 C61 C62 C57 178.3(2) . . . . ?
C60 C61 C62 C57 -0.5(4) . . . . ?
C58 C57 C62 F30 178.5(2) . . . . ?
B2 C57 C62 F30 5.3(4) . . . . ?
C58 C57 C62 C61 -0.2(4) . . . . ?
B2 C57 C62 C61 -173.4(2) . . . . ?
N5 N4 B2 C45 -125.2(2) . . . . ?
C39 N4 B2 C45 67.8(3) . . . . ?
N5 N4 B2 C57 -10.7(3) . . . . ?
C39 N4 B2 C57 -177.7(2) . . . . ?
N5 N4 B2 C51 112.6(2) . . . . ?
C39 N4 B2 C51 -54.5(3) . . . . ?
C46 C45 B2 N4 9.5(4) . . . . ?
C50 C45 B2 N4 -177.2(2) . . . . ?
C46 C45 B2 C57 -107.7(3) . . . . ?
C50 C45 B2 C57 65.6(3) . . . . ?
C46 C45 B2 C51 124.1(3) . . . . ?
C50 C45 B2 C51 -62.6(3) . . . . ?
C58 C57 B2 N4 127.6(3) . . . . ?
C62 C57 B2 N4 -60.0(3) . . . . ?
C58 C57 B2 C45 -113.8(3) . . . . ?
C62 C57 B2 C45 58.6(3) . . . . ?
C58 C57 B2 C51 13.4(4) . . . . ?
C62 C57 B2 C51 -174.2(2) . . . . ?
C52 C51 B2 N4 111.4(3) . . . . ?
C56 C51 B2 N4 -60.8(3) . . . . ?
C52 C51 B2 C45 -8.3(4) . . . . ?
C56 C51 B2 C45 179.4(2) . . . . ?
C52 C51 B2 C57 -130.4(3) . . . . ?
C56 C51 B2 C57 57.3(3) . . . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_il-1-83
_database_code_depnum_ccdc_archive 'CCDC 1966936'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H24 N3 O, C F3 O3 S'
_chemical_formula_sum            'C13 H24 F3 N3 O4 S'
_chemical_formula_weight         375.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H24 N3 O4 F3 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.05100(19)
_cell_length_b                   10.81512(18)
_cell_length_c                   15.9625(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.2766(16)
_cell_angle_gamma                90
_cell_volume                     1864.18(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13102
_cell_measurement_temperature    139.98(11)
_cell_measurement_theta_max      76.0250
_cell_measurement_theta_min      4.0990
_shelx_estimated_absorpt_T_max   0.526
_shelx_estimated_absorpt_T_min   0.351
_exptl_absorpt_coefficient_mu    2.013
_exptl_absorpt_correction_T_max  0.584
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019).
 Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid.
 (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
 Empirical absorption correction using spherical harmonics as
 implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 2 0.1114
-1 2 -2 0.3316
1 2 2 0.1733
0 -1 0 0.1957
0 1 2 0.1294
0 -1 -2 0.2365
1 0 -1 0.1494
-1 0 1 0.3462
0 -1 2 0.1685
-1 0 2 0.2752
-2 -3 5 0.2690
-1 1 1 0.3285
0 1 1 0.1577
1 2 -1 0.2496

_exptl_crystal_size_max          0.658
_exptl_crystal_size_mid          0.443
_exptl_crystal_size_min          0.366
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -2.0000 1.9999 0.3495 -0.1422 0.1005
-1.0000 2.0000 -1.9999 -0.3495 0.1422 -0.1005
1.0000 2.0000 2.0000 -0.1262 0.0205 0.3691
0.0000 -1.0000 -0.0000 0.1189 -0.0407 -0.0671
0.0000 1.0000 2.0000 -0.0854 -0.0937 0.2080
-0.0000 -1.0000 -2.0000 0.0854 0.0937 -0.2080
1.0000 -0.0000 -1.0000 0.0614 0.1407 0.0236
-1.0000 0.0000 1.0000 -0.0614 -0.1407 -0.0236
0.0000 -1.0000 2.0000 0.1524 -0.1750 0.0737
-1.0000 0.0000 2.0000 -0.0447 -0.2078 0.0468
-2.0000 -3.0000 4.9999 0.2841 -0.6049 -0.0373
-1.0000 1.0000 1.0000 -0.1804 -0.1000 0.0436
0.0000 1.0000 1.0000 -0.1022 -0.0265 0.1375
1.0000 2.0000 -1.0000 -0.1764 0.2220 0.1578

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16719
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.004
_diffrn_reflns_theta_min         4.457
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  31.00   1.00    1.00    --  -40.85  57.00  30.00   93
  2  ω   -115.00 -22.00   1.00    1.00    --  -40.85 -38.00-120.00   93
  3  ω   -113.00 -22.00   1.00    1.00    --  -40.85 -38.00 150.00   91
  4  ω     50.00  92.00   1.00    1.00    --   40.85-125.00-120.00   42
  5  ω      2.00  81.00   1.00    1.00    --   40.85 -99.00 120.00   79
  6  ω     87.00 129.00   1.00    4.00    --  112.00 -30.00 -60.00   42
  7  ω     45.00  71.00   1.00    4.00    --  112.00 -30.00 -60.00   26
  8  ω     42.00  68.00   1.00    4.00    --  112.00 -94.00 -30.00   26
  9  ω    119.00 178.00   1.00    4.00    --  112.00 111.00  60.00   59
 10  ω     36.00 112.00   1.00    4.00    --  112.00-111.00  60.00   76
 11  ω     90.00 137.00   1.00    4.00    --  112.00 -61.00 -30.00   47
 12  ω     37.00  68.00   1.00    4.00    --  112.00-111.00 -60.00   31
 13  ω     80.00 112.00   1.00    4.00    --  112.00-111.00 -60.00   32
 14  ω     30.00  82.00   1.00    4.00    --  112.00 -94.00   0.00   52
 15  ω     91.00 160.00   1.00    4.00    --  112.00  30.00 120.00   69
 16  ω     95.00 140.00   1.00    4.00    --  112.00 -61.00 120.00   45
 17  ω     60.00 113.00   1.00    4.00    --  112.00-111.00-150.00   53
 18  ω     95.00 139.00   1.00    4.00    --  112.00 -77.00 150.00   44
 19  ω     30.00 168.00   1.00    4.00    --  112.00   0.00 -90.00  138
 20  ω     40.00  68.00   1.00    4.00    --  112.00 -94.00 120.00   28
 21  ω     36.00 123.00   1.00    4.00    --  112.00 -30.00 120.00   87
 22  ω     56.00  83.00   1.00    4.00    --  112.00 -61.00 -30.00   27
 23  ω     96.00 123.00   1.00    4.00    --  112.00-132.00 177.59   27
 24  ω     37.00 109.00   1.00    4.00    --  112.00-111.00-180.00   72
 25  ω     88.00 113.00   1.00    4.00    --  112.00-111.00 -90.00   25
 26  ω     85.00 140.00   1.00    4.00    --  112.00 -77.00  30.00   55
 27  ω     73.00 109.00   1.00    4.00    --  112.00-111.00   0.00   36
 28  ω     62.00  92.00   1.00    4.00    --  112.00  15.00  30.00   30
 29  ω     97.00 122.00   1.00    4.00    --  112.00  15.00  30.00   25
 30  ω     41.00  66.00   1.00    4.00    --  112.00-111.00-120.00   25
 31  ω     50.00  86.00   1.00    4.00    --  112.00-132.00 177.59   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0781912000
_diffrn_orient_matrix_UB_12      -0.1189321000
_diffrn_orient_matrix_UB_13      0.0167462000
_diffrn_orient_matrix_UB_21      0.0734915000
_diffrn_orient_matrix_UB_22      0.0406853000
_diffrn_orient_matrix_UB_23      -0.0671744000
_diffrn_orient_matrix_UB_31      0.0939659000
_diffrn_orient_matrix_UB_32      0.0671372000
_diffrn_orient_matrix_UB_33      0.0704068000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3730
_reflns_number_total             3844
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.068
_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)+(0.0667P)²+1.0802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1265
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H6D)=Sof(H6E)=Sof(H6F)=1-FVAR(1)
 Sof(H6A)=Sof(H6B)=Sof(H6C)=FVAR(1)
 Sof(H4D)=Sof(H4E)=Sof(H4F)=1-FVAR(2)
 Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
3.b Disordered Me refined as rotating group:
 C4(H4A,H4B,H4C,H4D,H4E,H4F), C6(H6A,H6B,H6C,H6D,H6E,H6F)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C),
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
S1 S 0.29975(4) 0.80986(4) 0.43787(2) 0.02723(15) Uani 1 1 d . . . . .
F1 F 0.24858(15) 0.7769(2) 0.58998(9) 0.0705(5) Uani 1 1 d . . . . .
F2 F 0.13441(14) 0.91086(17) 0.51121(11) 0.0684(5) Uani 1 1 d . . . . .
F3 F 0.10647(15) 0.7174(2) 0.48511(13) 0.0816(6) Uani 1 1 d . . . . .
O2 O 0.22111(13) 0.84532(14) 0.35800(9) 0.0401(3) Uani 1 1 d . . . . .
O3 O 0.35227(16) 0.68842(13) 0.44144(11) 0.0462(4) Uani 1 1 d . . . . .
O4 O 0.38610(11) 0.90451(12) 0.47721(8) 0.0324(3) Uani 1 1 d . . . . .
C13 C 0.19211(19) 0.8033(2) 0.50993(15) 0.0452(5) Uani 1 1 d . . . . .
O1 O 0.56488(15) 0.88198(17) 0.33253(9) 0.0503(4) Uani 1 1 d . . . . .
N1 N 0.63209(13) 0.83813(13) 0.47177(8) 0.0247(3) Uani 1 1 d . . . . .
H1 H 0.563(2) 0.868(2) 0.4844(15) 0.036(6) Uiso 1 1 d . . . . .
N2 N 0.73038(13) 0.80755(12) 0.52969(9) 0.0233(3) Uani 1 1 d . . . . .
N3 N 0.72737(12) 0.81082(12) 0.60843(8) 0.0234(3) Uani 1 1 d . . . . .
C1 C 0.64339(17) 0.83181(17) 0.38478(11) 0.0312(4) Uani 1 1 d . . . . .
C2 C 0.75220(17) 0.76433(19) 0.36604(11) 0.0337(4) Uani 1 1 d . . . . .
C3 C 0.75866(18) 0.6421(2) 0.37475(12) 0.0389(4) Uani 1 1 d . . . . .
C4 C 0.8418(2) 0.8455(3) 0.33280(18) 0.0552(6) Uani 1 1 d . . . . .
H4A H 0.805462 0.870335 0.273774 0.066 Uiso 0.61(3) 1 calc GR . P . .
H4B H 0.918767 0.799816 0.333966 0.066 Uiso 0.61(3) 1 calc GR . P . .
H4C H 0.859751 0.919256 0.368966 0.066 Uiso 0.61(3) 1 calc GR . P . .
H4D H 0.917191 0.855936 0.377363 0.066 Uiso 0.39(3) 1 calc GR . P . .
H4E H 0.803886 0.926456 0.317171 0.066 Uiso 0.39(3) 1 calc GR . P . .
H4F H 0.862903 0.807015 0.282172 0.066 Uiso 0.39(3) 1 calc GR . P . .
C5 C 0.6616(2) 0.56571(19) 0.40331(16) 0.0470(5) Uani 1 1 d . . . . .
H5A H 0.696786 0.528202 0.459066 0.071 Uiso 1 1 calc GR . . . .
H5B H 0.633218 0.500454 0.361116 0.071 Uiso 1 1 calc GR . . . .
H5C H 0.591509 0.618515 0.408425 0.071 Uiso 1 1 calc GR . . . .
C6 C 0.8646(2) 0.5682(3) 0.35473(19) 0.0613(7) Uani 1 1 d . . . . .
H6A H 0.876251 0.589929 0.297358 0.074 Uiso 0.30(3) 1 calc GR . P . .
H6B H 0.846042 0.479799 0.356676 0.074 Uiso 0.30(3) 1 calc GR . P . .
H6C H 0.940474 0.586891 0.397142 0.074 Uiso 0.30(3) 1 calc GR . P . .
H6D H 0.898927 0.514483 0.403426 0.074 Uiso 0.70(3) 1 calc GR . P . .
H6E H 0.929136 0.624613 0.344108 0.074 Uiso 0.70(3) 1 calc GR . P . .
H6F H 0.834704 0.517521 0.303642 0.074 Uiso 0.70(3) 1 calc GR . P . .
C7 C 0.84572(15) 0.76784(17) 0.66591(10) 0.0285(4) Uani 1 1 d . . . . .
H7 H 0.828207 0.747186 0.723240 0.034 Uiso 1 1 calc R . . . .
C8 C 0.89211(19) 0.6521(2) 0.62931(12) 0.0391(4) Uani 1 1 d . . . . .
H8A H 0.826685 0.589264 0.619794 0.059 Uiso 1 1 calc GR . . . .
H8B H 0.964831 0.620241 0.669750 0.059 Uiso 1 1 calc GR . . . .
H8C H 0.914785 0.671871 0.574740 0.059 Uiso 1 1 calc GR . . . .
C9 C 0.93958(18) 0.8717(2) 0.67747(14) 0.0440(5) Uani 1 1 d . . . . .
H9A H 0.956677 0.894271 0.621656 0.066 Uiso 1 1 calc GR . . . .
H9B H 1.016389 0.844540 0.715794 0.066 Uiso 1 1 calc GR . . . .
H9C H 0.906451 0.943682 0.702444 0.066 Uiso 1 1 calc GR . . . .
C10 C 0.61603(15) 0.83924(18) 0.64414(10) 0.0303(4) Uani 1 1 d . . . . .
H10 H 0.558975 0.892065 0.601773 0.036 Uiso 1 1 calc R . . . .
C11 C 0.65051(19) 0.91009(18) 0.72790(12) 0.0367(4) Uani 1 1 d . . . . .
H11A H 0.700272 0.857055 0.771900 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.574983 0.935367 0.746211 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.698526 0.983596 0.719688 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.55129(19) 0.7173(2) 0.65192(13) 0.0433(5) Uani 1 1 d . . . . .
H12A H 0.531548 0.676502 0.595827 0.065 Uiso 1 1 calc GR . . . .
H12B H 0.474689 0.732660 0.671861 0.065 Uiso 1 1 calc GR . . . .
H12C H 0.605867 0.663859 0.693082 0.065 Uiso 1 1 calc GR . . . .


_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
S1 O2 1.4342(13) . ?
S1 O3 1.4322(14) . ?
S1 O4 1.4484(12) . ?
S1 C13 1.823(2) . ?
F1 C13 1.328(3) . ?
F2 C13 1.329(3) . ?
F3 C13 1.325(3) . ?
O1 C1 1.198(2) . ?
N1 H1 0.89(3) . ?
N1 N2 1.3104(19) . ?
N1 C1 1.422(2) . ?
N2 N3 1.2649(19) . ?
N3 C7 1.5027(19) . ?
N3 C10 1.494(2) . ?
C1 C2 1.490(2) . ?
C2 C3 1.329(3) . ?
C2 C4 1.502(3) . ?
C3 C5 1.499(3) . ?
C3 C6 1.507(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
C4 H4F 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 H6D 0.9800 . ?
C6 H6E 0.9800 . ?
C6 H6F 0.9800 . ?
C7 H7 1.0000 . ?
C7 C8 1.516(3) . ?
C7 C9 1.514(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.518(3) . ?
C10 C12 1.518(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O4 114.54(8) . . ?
O2 S1 C13 102.59(9) . . ?
O3 S1 O2 116.39(9) . . ?
O3 S1 O4 114.00(9) . . ?
O3 S1 C13 104.62(11) . . ?
O4 S1 C13 102.24(9) . . ?
F1 C13 S1 112.28(15) . . ?
F1 C13 F2 107.6(2) . . ?
F2 C13 S1 110.80(15) . . ?
F3 C13 S1 111.03(18) . . ?
F3 C13 F1 107.2(2) . . ?
F3 C13 F2 107.68(19) . . ?
N2 N1 H1 123.7(15) . . ?
N2 N1 C1 116.43(14) . . ?
C1 N1 H1 119.7(15) . . ?
N3 N2 N1 120.07(13) . . ?
N2 N3 C7 113.25(13) . . ?
N2 N3 C10 125.64(13) . . ?
C10 N3 C7 120.74(12) . . ?
O1 C1 N1 117.20(16) . . ?
O1 C1 C2 125.30(16) . . ?
N1 C1 C2 117.50(14) . . ?
C1 C2 C4 113.93(19) . . ?
C3 C2 C1 119.58(18) . . ?
C3 C2 C4 126.4(2) . . ?
C2 C3 C5 123.63(18) . . ?
C2 C3 C6 122.1(2) . . ?
C5 C3 C6 114.2(2) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
C2 C4 H4D 109.5 . . ?
C2 C4 H4E 109.5 . . ?
C2 C4 H4F 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4A C4 H4D 141.1 . . ?
H4A C4 H4E 56.3 . . ?
H4A C4 H4F 56.3 . . ?
H4B C4 H4C 109.5 . . ?
H4B C4 H4D 56.3 . . ?
H4B C4 H4E 141.1 . . ?
H4B C4 H4F 56.3 . . ?
H4C C4 H4D 56.3 . . ?
H4C C4 H4E 56.3 . . ?
H4C C4 H4F 141.1 . . ?
H4D C4 H4E 109.5 . . ?
H4D C4 H4F 109.5 . . ?
H4E C4 H4F 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
C3 C6 H6D 109.5 . . ?
C3 C6 H6E 109.5 . . ?
C3 C6 H6F 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6A C6 H6D 141.1 . . ?
H6A C6 H6E 56.3 . . ?
H6A C6 H6F 56.3 . . ?
H6B C6 H6C 109.5 . . ?
H6B C6 H6D 56.3 . . ?
H6B C6 H6E 141.1 . . ?
H6B C6 H6F 56.3 . . ?
H6C C6 H6D 56.3 . . ?
H6C C6 H6E 56.3 . . ?
H6C C6 H6F 141.1 . . ?
H6D C6 H6E 109.5 . . ?
H6D C6 H6F 109.5 . . ?
H6E C6 H6F 109.5 . . ?
N3 C7 H7 108.4 . . ?
N3 C7 C8 109.99(14) . . ?
N3 C7 C9 109.25(14) . . ?
C8 C7 H7 108.4 . . ?
C9 C7 H7 108.4 . . ?
C9 C7 C8 112.39(16) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10 108.1 . . ?
N3 C10 C11 111.54(15) . . ?
N3 C10 C12 107.04(15) . . ?
C11 C10 H10 108.1 . . ?
C11 C10 C12 113.65(15) . . ?
C12 C10 H10 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O2 S1 C13 F1 -177.12(17) . . . . ?
O2 S1 C13 F2 -56.77(18) . . . . ?
O2 S1 C13 F3 62.84(18) . . . . ?
O3 S1 C13 F1 60.9(2) . . . . ?
O3 S1 C13 F2 -178.70(15) . . . . ?
O3 S1 C13 F3 -59.09(18) . . . . ?
O4 S1 C13 F1 -58.18(19) . . . . ?
O4 S1 C13 F2 62.17(17) . . . . ?
O4 S1 C13 F3 -178.22(16) . . . . ?
O1 C1 C2 C3 -110.9(2) . . . . ?
O1 C1 C2 C4 65.4(3) . . . . ?
N1 N2 N3 C7 177.52(14) . . . . ?
N1 N2 N3 C10 4.5(2) . . . . ?
N1 C1 C2 C3 69.6(2) . . . . ?
N1 C1 C2 C4 -114.1(2) . . . . ?
N2 N1 C1 O1 -165.51(18) . . . . ?
N2 N1 C1 C2 14.0(2) . . . . ?
N2 N3 C7 C8 -43.8(2) . . . . ?
N2 N3 C7 C9 80.02(18) . . . . ?
N2 N3 C10 C11 -145.22(16) . . . . ?
N2 N3 C10 C12 89.89(18) . . . . ?
C1 N1 N2 N3 -179.97(15) . . . . ?
C1 C2 C3 C5 -0.3(3) . . . . ?
C1 C2 C3 C6 178.47(19) . . . . ?
C4 C2 C3 C5 -176.1(2) . . . . ?
C4 C2 C3 C6 2.7(3) . . . . ?
C7 N3 C10 C11 42.2(2) . . . . ?
C7 N3 C10 C12 -82.69(18) . . . . ?
C10 N3 C7 C8 129.66(17) . . . . ?
C10 N3 C7 C9 -106.54(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 17.741
_oxdiff_exptl_absorpt_empirical_full_min 0.453
