# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_EB326
_database_code_depnum_ccdc_archive 'CCDC 2040640'
loop_
_audit_author_name
_audit_author_address
'Mohamed Selkti'
;University of Paris
France
;
_audit_update_record             
;
2020-12-04 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H25 N3 O'
_chemical_formula_weight         443.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9992(4)
_cell_length_b                   10.1775(5)
_cell_length_c                   12.6396(6)
_cell_angle_alpha                69.319(5)
_cell_angle_beta                 80.319(4)
_cell_angle_gamma                84.713(4)
_cell_volume                     1185.52(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    291.43(10)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      4.1880
_cell_measurement_theta_max      30.3140

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_min  0.42649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.534
_oxdiff_exptl_absorpt_empirical_full_max 1.666
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      291.43(10)
_diffrn_ambient_environment      air
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_reflns_number            42173
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.6676
_diffrn_reflns_theta_max         30.1937
_diffrn_measured_fraction_theta_max 0.9100
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9971
_reflns_number_total             6403
_reflns_number_gt                4780
_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 1.171.39.32e (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0891P)²+0.1987P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6403
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1738
_refine_ls_wR_factor_gt          0.1600
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_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
N001 N 0.28243(11) 0.26091(11) 0.30327(9) 0.0329(2) Uani 1 1 d . . . . .
N002 N -0.00344(13) 0.26019(15) 0.57838(11) 0.0482(3) Uani 1 1 d . . . . .
O003 O 0.28249(16) 0.09789(15) -0.07572(11) 0.0697(4) Uani 1 1 d . . . . .
C004 C 0.21955(13) 0.38884(13) 0.30848(11) 0.0328(3) Uani 1 1 d . . . . .
C005 C 0.27392(12) 0.21647(13) 0.21077(10) 0.0317(3) Uani 1 1 d . . . . .
C006 C 0.25321(13) 0.51749(14) 0.20774(11) 0.0349(3) Uani 1 1 d . . . . .
N007 N 0.54427(15) 0.29480(19) 0.55185(14) 0.0611(4) Uani 1 1 d . . . . .
C008 C 0.35770(14) 0.10603(14) 0.19223(12) 0.0381(3) Uani 1 1 d . . . . .
H008 H 0.416536 0.058013 0.244077 0.046 Uiso 1 1 calc R U . . .
C009 C 0.14083(14) 0.39194(15) 0.40550(12) 0.0376(3) Uani 1 1 d . . . . .
H009 H 0.108595 0.477510 0.412689 0.045 Uiso 1 1 calc R U . . .
C00A C 0.18580(13) 0.13989(14) 0.50079(11) 0.0358(3) Uani 1 1 d . . . . .
C00B C 0.10638(14) 0.26114(15) 0.49896(11) 0.0378(3) Uani 1 1 d . . . . .
C00C C 0.18480(14) 0.28219(15) 0.13285(12) 0.0392(3) Uani 1 1 d . . . . .
H00C H 0.124350 0.352207 0.145194 0.047 Uiso 1 1 calc R U . . .
C00D C 0.31339(13) 0.15945(14) 0.41461(11) 0.0342(3) Uani 1 1 d . . . . .
H00D H 0.342288 0.068982 0.405378 0.041 Uiso 1 1 calc R U . . .
C00E C 0.38110(15) 0.52941(15) 0.14172(12) 0.0415(3) Uani 1 1 d . . . . .
H00E H 0.444385 0.455012 0.160250 0.050 Uiso 1 1 calc R U . . .
C00F C 0.55657(14) 0.26131(15) 0.38365(13) 0.0405(3) Uani 1 1 d . . . . .
C00G C 0.42778(14) 0.21284(15) 0.45091(12) 0.0388(3) Uani 1 1 d . . . . .
C00H C 0.14540(16) 0.01197(16) 0.58131(13) 0.0457(3) Uani 1 1 d . . . . .
H00H H 0.194305 -0.070654 0.582361 0.055 Uiso 1 1 calc R U . . .
C00I C 0.16083(16) 0.63048(16) 0.17802(14) 0.0470(4) Uani 1 1 d . . . . .
H00I H 0.074845 0.625520 0.220626 0.056 Uiso 1 1 calc R U . . .
C00J C 0.27082(18) 0.13851(16) 0.01858(13) 0.0481(4) Uani 1 1 d . . . . .
C00K C 0.35455(17) 0.06720(16) 0.09858(13) 0.0452(3) Uani 1 1 d . . . . .
H00K H 0.409517 -0.007917 0.089249 0.054 Uiso 1 1 calc R U . . .
C00L C -0.03756(17) 0.1347(2) 0.65633(14) 0.0546(4) Uani 1 1 d . . . . .
H00L H -0.112538 0.132171 0.711561 0.065 Uiso 1 1 calc R U . . .
C00M C 0.62052(15) 0.26920(17) 0.27405(14) 0.0470(4) Uani 1 1 d . . . . .
H00M H 0.578911 0.234366 0.229394 0.056 Uiso 1 1 calc R U . . .
C00N C 0.62545(16) 0.31264(18) 0.44961(15) 0.0500(4) Uani 1 1 d . . . . .
C00O C 0.18394(17) 0.24557(17) 0.03662(13) 0.0480(4) Uani 1 1 d . . . . .
H00O H 0.125189 0.292838 -0.015506 0.058 Uiso 1 1 calc R U . . .
C00P C 0.41583(17) 0.64949(17) 0.04931(14) 0.0494(4) Uani 1 1 d . . . . .
H00P H 0.501970 0.655449 0.006824 0.059 Uiso 1 1 calc R U . . .
C00Q C 0.32303(19) 0.76029(17) 0.02008(14) 0.0540(4) Uani 1 1 d . . . . .
H00Q H 0.345543 0.840641 -0.042724 0.065 Uiso 1 1 calc R U . . .
C00R C 0.42539(17) 0.2361(2) 0.55143(14) 0.0526(4) Uani 1 1 d . . . . .
H00R H 0.353541 0.215251 0.611250 0.063 Uiso 1 1 calc R U . . .
C00S C 0.03007(18) 0.00972(19) 0.66061(14) 0.0544(4) Uani 1 1 d . . . . .
H00S H -0.000507 -0.074538 0.715257 0.065 Uiso 1 1 calc R U . . .
C00T C 0.19632(19) 0.75083(17) 0.08494(15) 0.0570(4) Uani 1 1 d . . . . .
H00T H 0.133851 0.825955 0.066132 0.068 Uiso 1 1 calc R U . . .
C00U C 0.74592(17) 0.3292(2) 0.23290(17) 0.0615(5) Uani 1 1 d . . . . .
H00U H 0.787840 0.335520 0.159852 0.074 Uiso 1 1 calc R U . . .
C00V C 0.75228(18) 0.3728(2) 0.40767(19) 0.0638(5) Uani 1 1 d . . . . .
H00V H 0.795943 0.406739 0.451704 0.077 Uiso 1 1 calc R U . . .
C00W C 0.81036(19) 0.3802(2) 0.2994(2) 0.0693(5) Uani 1 1 d . . . . .
H00W H 0.894606 0.420184 0.269692 0.083 Uiso 1 1 calc R U . . .
C00X C 0.5741(2) 0.3385(3) 0.6432(2) 0.0825(7) Uani 1 1 d . . . . .
H00A H 0.658702 0.295114 0.666649 0.124 Uiso 1 1 calc R U . . .
H00B H 0.502828 0.310401 0.706998 0.124 Uiso 1 1 calc R U . . .
H00F H 0.580443 0.438849 0.616094 0.124 Uiso 1 1 calc R U . . .
C00Y C 0.1921(3) 0.1557(3) -0.15284(19) 0.0911(8) Uani 1 1 d . . . . .
H00G H 0.208345 0.113505 -0.211023 0.137 Uiso 1 1 calc R U . . .
H00J H 0.204068 0.255119 -0.187350 0.137 Uiso 1 1 calc R U . . .
H00N H 0.100944 0.138641 -0.113760 0.137 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
N001 C004 1.4109(15) . ?
N001 C005 1.4116(15) . ?
N001 C00D 1.4845(16) . ?
N002 C00L 1.340(2) . ?
N002 C00B 1.3558(17) . ?
O003 C00J 1.3775(18) . ?
O003 C00Y 1.381(2) . ?
C004 C009 1.3500(18) . ?
C004 C006 1.4861(18) . ?
C005 C00C 1.3899(18) . ?
C005 C008 1.4024(17) . ?
C006 C00I 1.3902(19) . ?
C006 C00E 1.3944(19) . ?
N007 C00N 1.368(2) . ?
N007 C00R 1.380(2) . ?
N007 C00X 1.457(2) . ?
C008 C00K 1.3797(19) . ?
C008 H008 0.9300 . ?
C009 C00B 1.4570(19) . ?
C009 H009 0.9300 . ?
C00A C00H 1.385(2) . ?
C00A C00B 1.3997(19) . ?
C00A C00D 1.5100(18) . ?
C00C C00O 1.394(2) . ?
C00C H00C 0.9300 . ?
C00D C00G 1.5102(19) . ?
C00D H00D 0.9800 . ?
C00E C00P 1.383(2) . ?
C00E H00E 0.9300 . ?
C00F C00M 1.403(2) . ?
C00F C00N 1.418(2) . ?
C00F C00G 1.441(2) . ?
C00G C00R 1.368(2) . ?
C00H C00S 1.391(2) . ?
C00H H00H 0.9300 . ?
C00I C00T 1.390(2) . ?
C00I H00I 0.9300 . ?
C00J C00K 1.380(2) . ?
C00J C00O 1.389(2) . ?
C00K H00K 0.9300 . ?
C00L C00S 1.373(3) . ?
C00L H00L 0.9300 . ?
C00M C00U 1.383(2) . ?
C00M H00M 0.9300 . ?
C00N C00V 1.397(2) . ?
C00O H00O 0.9300 . ?
C00P C00Q 1.377(2) . ?
C00P H00P 0.9300 . ?
C00Q C00T 1.380(2) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U C00W 1.394(3) . ?
C00U H00U 0.9300 . ?
C00V C00W 1.373(3) . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00X H00A 0.9600 . ?
C00X H00B 0.9600 . ?
C00X H00F 0.9600 . ?
C00Y H00G 0.9600 . ?
C00Y H00J 0.9600 . ?
C00Y H00N 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
C004 N001 C005 120.87(10) . . ?
C004 N001 C00D 114.59(10) . . ?
C005 N001 C00D 121.30(10) . . ?
C00L N002 C00B 116.47(13) . . ?
C00J O003 C00Y 118.61(15) . . ?
C009 C004 N001 119.80(12) . . ?
C009 C004 C006 122.85(12) . . ?
N001 C004 C006 117.16(11) . . ?
C00C C005 C008 117.22(12) . . ?
C00C C005 N001 121.57(11) . . ?
C008 C005 N001 121.19(11) . . ?
C00I C006 C00E 117.97(13) . . ?
C00I C006 C004 121.62(12) . . ?
C00E C006 C004 120.39(12) . . ?
C00N N007 C00R 108.57(13) . . ?
C00N N007 C00X 125.85(17) . . ?
C00R N007 C00X 125.47(17) . . ?
C00K C008 C005 121.30(13) . . ?
C00K C008 H008 119.4 . . ?
C005 C008 H008 119.4 . . ?
C004 C009 C00B 119.96(12) . . ?
C004 C009 H009 120.0 . . ?
C00B C009 H009 120.0 . . ?
C00H C00A C00B 119.02(13) . . ?
C00H C00A C00D 124.32(12) . . ?
C00B C00A C00D 116.64(12) . . ?
N002 C00B C00A 122.53(13) . . ?
N002 C00B C009 119.06(12) . . ?
C00A C00B C009 118.37(12) . . ?
C005 C00C C00O 121.51(13) . . ?
C005 C00C H00C 119.2 . . ?
C00O C00C H00C 119.2 . . ?
N001 C00D C00A 108.67(10) . . ?
N001 C00D C00G 109.34(11) . . ?
C00A C00D C00G 112.28(11) . . ?
N001 C00D H00D 108.8 . . ?
C00A C00D H00D 108.8 . . ?
C00G C00D H00D 108.8 . . ?
C00P C00E C006 121.41(13) . . ?
C00P C00E H00E 119.3 . . ?
C006 C00E H00E 119.3 . . ?
C00M C00F C00N 118.19(14) . . ?
C00M C00F C00G 134.73(14) . . ?
C00N C00F C00G 107.07(13) . . ?
C00R C00G C00F 105.84(13) . . ?
C00R C00G C00D 126.62(13) . . ?
C00F C00G C00D 127.33(12) . . ?
C00A C00H C00S 118.55(14) . . ?
C00A C00H H00H 120.7 . . ?
C00S C00H H00H 120.7 . . ?
C00T C00I C006 120.34(14) . . ?
C00T C00I H00I 119.8 . . ?
C006 C00I H00I 119.8 . . ?
O003 C00J C00K 116.14(14) . . ?
O003 C00J C00O 124.81(15) . . ?
C00K C00J C00O 119.04(13) . . ?
C008 C00K C00J 120.79(13) . . ?
C008 C00K H00K 119.6 . . ?
C00J C00K H00K 119.6 . . ?
N002 C00L C00S 124.78(14) . . ?
N002 C00L H00L 117.6 . . ?
C00S C00L H00L 117.6 . . ?
C00U C00M C00F 119.51(16) . . ?
C00U C00M H00M 120.2 . . ?
C00F C00M H00M 120.2 . . ?
N007 C00N C00V 130.11(16) . . ?
N007 C00N C00F 107.84(14) . . ?
C00V C00N C00F 122.03(16) . . ?
C00J C00O C00C 120.00(14) . . ?
C00J C00O H00O 120.0 . . ?
C00C C00O H00O 120.0 . . ?
C00Q C00P C00E 120.09(14) . . ?
C00Q C00P H00P 120.0 . . ?
C00E C00P H00P 120.0 . . ?
C00P C00Q C00T 119.32(15) . . ?
C00P C00Q H00Q 120.3 . . ?
C00T C00Q H00Q 120.3 . . ?
C00G C00R N007 110.68(15) . . ?
C00G C00R H00R 124.7 . . ?
N007 C00R H00R 124.7 . . ?
C00L C00S C00H 118.47(15) . . ?
C00L C00S H00S 120.8 . . ?
C00H C00S H00S 120.8 . . ?
C00Q C00T C00I 120.86(15) . . ?
C00Q C00T H00T 119.6 . . ?
C00I C00T H00T 119.6 . . ?
C00M C00U C00W 120.92(18) . . ?
C00M C00U H00U 119.5 . . ?
C00W C00U H00U 119.5 . . ?
C00W C00V C00N 117.85(17) . . ?
C00W C00V H00V 121.1 . . ?
C00N C00V H00V 121.1 . . ?
C00V C00W C00U 121.49(18) . . ?
C00V C00W H00W 119.3 . . ?
C00U C00W H00W 119.3 . . ?
N007 C00X H00A 109.5 . . ?
N007 C00X H00B 109.5 . . ?
H00A C00X H00B 109.5 . . ?
N007 C00X H00F 109.5 . . ?
H00A C00X H00F 109.5 . . ?
H00B C00X H00F 109.5 . . ?
O003 C00Y H00G 109.5 . . ?
O003 C00Y H00J 109.5 . . ?
H00G C00Y H00J 109.5 . . ?
O003 C00Y H00N 109.5 . . ?
H00G C00Y H00N 109.5 . . ?
H00J C00Y H00N 109.5 . . ?

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2042160'
loop_
_audit_author_name
_audit_author_address
'Mohamed Selkti'
;University of Paris
France
;
_audit_update_record             
;
2020-12-04 deposited with the CCDC.	2020-12-18 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         ?
_chemical_formula_sum            'C23 H18 F3 N O4 S'
_chemical_formula_weight         461.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1265 0.1256 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.825(2)
_cell_length_b                   14.2553(12)
_cell_length_c                   13.0345(12)
_cell_angle_alpha                90
_cell_angle_beta                 112.464(3)
_cell_angle_gamma                90
_cell_volume                     4091.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      31.62
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.015
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.13

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    0.214
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8841
_exptl_absorpt_correction_T_max  0.9464
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            95674
_diffrn_reflns_av_unetI/netI     0.1850
_diffrn_reflns_av_R_equivalents  0.2816
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         32.711
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7497
_reflns_number_gt                3703
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0437P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7497
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1366
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_refine_ls_shift/su_max          0.000
_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
C1 C 0.36377(7) 0.87093(10) 0.17432(12) 0.0148(3) Uani 1 1 d . . . . .
H1 H 0.340326 0.818491 0.179265 0.018 Uiso 1 1 calc R U . . .
C2 C 0.39143(7) 0.87029(11) 0.09847(13) 0.0170(4) Uani 1 1 d . . . . .
H2 H 0.387312 0.817239 0.052038 0.020 Uiso 1 1 calc R U . . .
C3 C 0.42519(7) 0.94701(11) 0.09009(13) 0.0178(4) Uani 1 1 d . . . . .
H3 H 0.444329 0.946379 0.038138 0.021 Uiso 1 1 calc R U . . .
C4 C 0.43102(7) 1.02452(11) 0.15734(13) 0.0163(4) Uani 1 1 d . . . . .
H4 H 0.453701 1.077404 0.150852 0.020 Uiso 1 1 calc R U . . .
C5 C 0.40374(7) 1.02497(10) 0.23428(12) 0.0138(3) Uani 1 1 d . . . . .
H5 H 0.408109 1.078095 0.280705 0.017 Uiso 1 1 calc R U . . .
C6 C 0.37009(7) 0.94833(10) 0.24388(12) 0.0117(3) Uani 1 1 d . . . . .
C7 C 0.33835(7) 0.95475(10) 0.32199(12) 0.0115(3) Uani 1 1 d . . . . .
C8 C 0.30696(7) 1.03343(10) 0.32764(12) 0.0123(3) Uani 1 1 d . . . . .
H8 H 0.307316 1.086051 0.283171 0.015 Uiso 1 1 calc R U . . .
C9 C 0.27413(7) 1.03923(10) 0.39705(12) 0.0125(3) Uani 1 1 d . . . . .
C10 C 0.24217(7) 1.12029(11) 0.40606(13) 0.0155(4) Uani 1 1 d . . . . .
H10 H 0.243527 1.175587 0.366385 0.019 Uiso 1 1 calc R U . . .
C11 C 0.20921(7) 1.11886(11) 0.47222(13) 0.0194(4) Uani 1 1 d . . . . .
H11 H 0.187480 1.173334 0.477394 0.023 Uiso 1 1 calc R U . . .
C12 C 0.20701(8) 1.03782(11) 0.53282(13) 0.0188(4) Uani 1 1 d . . . . .
H12 H 0.183473 1.038075 0.577465 0.023 Uiso 1 1 calc R U . . .
C13 C 0.23840(7) 0.95923(11) 0.52771(13) 0.0159(4) Uani 1 1 d . . . . .
H13 H 0.237178 0.905092 0.569305 0.019 Uiso 1 1 calc R U . . .
C14 C 0.27267(7) 0.95876(10) 0.46036(12) 0.0121(3) Uani 1 1 d . . . . .
C15 C 0.30691(7) 0.88068(10) 0.45545(12) 0.0121(3) Uani 1 1 d . . . . .
H15 H 0.307512 0.827243 0.499408 0.014 Uiso 1 1 calc R U . . .
C16 C 0.37688(7) 0.79689(10) 0.39650(12) 0.0112(3) Uani 1 1 d . . . . .
C17 C 0.34926(7) 0.71102(10) 0.36067(12) 0.0136(3) Uani 1 1 d . . . . .
H17 H 0.306477 0.704577 0.337164 0.016 Uiso 1 1 calc R U . . .
C18 C 0.38495(7) 0.63459(10) 0.35961(13) 0.0155(3) Uani 1 1 d . . . . .
H18 H 0.366628 0.575438 0.333832 0.019 Uiso 1 1 calc R U . . .
C19 C 0.44771(7) 0.64459(10) 0.39638(13) 0.0149(3) Uani 1 1 d . . . . .
C20 C 0.47497(7) 0.73041(10) 0.43632(13) 0.0154(4) Uani 1 1 d . . . . .
H20 H 0.517912 0.736606 0.464186 0.018 Uiso 1 1 calc R U . . .
C21 C 0.43876(7) 0.80688(10) 0.43501(12) 0.0138(3) Uani 1 1 d . . . . .
H21 H 0.456808 0.866202 0.460787 0.017 Uiso 1 1 calc R U . . .
C22 C 0.54270(8) 0.57293(12) 0.41995(16) 0.0282(4) Uani 1 1 d . . . . .
H22A H 0.558851 0.512028 0.409514 0.042 Uiso 1 1 calc R U . . .
H22B H 0.561906 0.591673 0.498020 0.042 Uiso 1 1 calc R U . . .
H22C H 0.551357 0.620014 0.373197 0.042 Uiso 1 1 calc R U . . .
C23 C 0.40696(8) 0.31794(11) 0.22228(14) 0.0185(4) Uani 1 1 d . . . . .
N1 N 0.33890(6) 0.87899(8) 0.39057(10) 0.0106(3) Uani 1 1 d . . . . .
O1 O 0.47815(5) 0.56573(7) 0.38933(10) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.31863(6) 0.38782(8) 0.26342(9) 0.0269(3) Uani 1 1 d . . . . .
O3 O 0.30372(5) 0.23560(7) 0.17347(9) 0.0207(3) Uani 1 1 d . . . . .
O4 O 0.36937(5) 0.25009(8) 0.36738(9) 0.0262(3) Uani 1 1 d . . . . .
F1 F 0.43468(5) 0.23874(7) 0.21552(11) 0.0438(3) Uani 1 1 d . . . . .
F2 F 0.44774(5) 0.37268(7) 0.29486(9) 0.0360(3) Uani 1 1 d . . . . .
F3 F 0.38964(5) 0.35869(8) 0.12353(9) 0.0400(3) Uani 1 1 d . . . . .
S1 S 0.34253(2) 0.29580(3) 0.26147(3) 0.01470(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(2) . ?
C1 C6 1.399(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.485(2) . ?
C7 C8 1.366(2) . ?
C7 N1 1.3987(18) . ?
C8 C9 1.406(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(2) . ?
C9 C14 1.421(2) . ?
C10 C11 1.370(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.412(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.363(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.409(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(2) . ?
C15 N1 1.3376(19) . ?
C15 H15 0.9500 . ?
C16 C21 1.371(2) . ?
C16 C17 1.384(2) . ?
C16 N1 1.4632(19) . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(2) . ?
C18 H18 0.9500 . ?
C19 O1 1.3598(18) . ?
C19 C20 1.390(2) . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O1 1.437(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 F2 1.3212(18) . ?
C23 F3 1.3261(19) . ?
C23 F1 1.3278(18) . ?
C23 S1 1.8209(18) . ?
O2 S1 1.4342(11) . ?
O3 S1 1.4480(11) . ?
O4 S1 1.4369(11) . ?

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
C2 C1 C6 120.40(15) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.05(15) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.04(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.00(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.48(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.00(15) . . ?
C5 C6 C7 118.43(13) . . ?
C1 C6 C7 122.40(14) . . ?
C8 C7 N1 118.13(14) . . ?
C8 C7 C6 121.36(13) . . ?
N1 C7 C6 120.51(13) . . ?
C7 C8 C9 122.25(14) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C10 123.45(14) . . ?
C8 C9 C14 117.97(13) . . ?
C10 C9 C14 118.57(14) . . ?
C11 C10 C9 119.77(15) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.14(15) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.46(16) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.60(15) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 121.36(14) . . ?
C15 C14 C9 118.20(14) . . ?
C13 C14 C9 120.43(14) . . ?
N1 C15 C14 121.84(14) . . ?
N1 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C21 C16 C17 121.45(14) . . ?
C21 C16 N1 119.53(13) . . ?
C17 C16 N1 119.01(13) . . ?
C16 C17 C18 118.97(15) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C19 119.91(14) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
O1 C19 C20 124.62(15) . . ?
O1 C19 C18 114.99(14) . . ?
C20 C19 C18 120.39(14) . . ?
C21 C20 C19 119.21(15) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C16 C21 C20 119.99(14) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F2 C23 F3 107.89(13) . . ?
F2 C23 F1 107.54(14) . . ?
F3 C23 F1 106.64(14) . . ?
F2 C23 S1 111.69(11) . . ?
F3 C23 S1 111.42(12) . . ?
F1 C23 S1 111.42(11) . . ?
C15 N1 C7 121.44(13) . . ?
C15 N1 C16 118.12(12) . . ?
C7 N1 C16 120.39(12) . . ?
C19 O1 C22 117.63(13) . . ?
O2 S1 O4 115.57(7) . . ?
O2 S1 O3 114.74(7) . . ?
O4 S1 O3 114.03(7) . . ?
O2 S1 C23 103.27(7) . . ?
O4 S1 C23 103.58(7) . . ?
O3 S1 C23 103.42(7) . . ?

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.102

