# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_f2_200k
_database_code_depnum_ccdc_archive 'CCDC 2151123'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-12-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H40 O2 S2, C12 H2 F2 N4'
_chemical_formula_sum            'C42 H42 F2 N4 O2 S2'
_chemical_formula_weight         736.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.1246 0.1234 '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                   6.990(3)
_cell_length_b                   7.879(3)
_cell_length_c                   18.150(5)
_cell_angle_alpha                88.77(2)
_cell_angle_beta                 83.18(3)
_cell_angle_gamma                72.80(3)
_cell_volume                     947.9(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    520
_cell_measurement_temperature    200
_cell_measurement_theta_max      24.6370
_cell_measurement_theta_min      3.4600
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull dark brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1625
_diffrn_reflns_av_unetI/netI     0.3081
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6028
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.392
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  25.00   1.00  275.00    --   18.39  77.00   0.00   32
  2  ω     -4.00  56.00   1.00  275.00    --   18.39  38.00-180.00   60
  3  ω    -10.00  35.00   1.00  275.00    --   18.39  77.00 120.00   45
  4  ω      3.00  38.00   1.00  275.00    --   18.39  77.00-150.00   35
  5  ω    -52.00  41.00   1.00  275.00    --   18.39 -38.00 -30.00   93
  6  ω    -50.00  37.00   1.00  275.00    --   18.39 -57.00-120.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0650043000
_diffrn_orient_matrix_UB_12      -0.0019404000
_diffrn_orient_matrix_UB_13      -0.0333036000
_diffrn_orient_matrix_UB_21      -0.0748151000
_diffrn_orient_matrix_UB_22      0.0712909000
_diffrn_orient_matrix_UB_23      -0.0138122000
_diffrn_orient_matrix_UB_31      0.0402664000
_diffrn_orient_matrix_UB_32      0.0616243000
_diffrn_orient_matrix_UB_33      0.0157953000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1175
_reflns_number_total             3344
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (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         0.619
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.2572
_refine_ls_R_factor_gt           0.1036
_refine_ls_restrained_S_all      0.953
_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)+(0.0800P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2105
_refine_ls_wR_factor_ref         0.3162
_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. Rigid body (RIGU) restrains
 C4, S001, C7, C3, C2, C5, H2, C1, C6, H5, H1, O1, C8, H8A, H8B, C9, H9A, H9B,
 C10, H10A, H10B, C11, C12, H11A, H11B, H12A, H12B, C13, H13A, H13B, C14, C15,
 H14A, H14B, H15A, H15B, H15C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C18, F1A, C19, H19, C17, H18, F1B, C16, C21, C20, N2, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H19)=Sof(F1B)=1-FVAR(1)
 Sof(F1A)=Sof(H18)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C5(H5), C2(H2), C19(H19), C1(H1)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.8931(3) 1.2792(3) 0.50521(12) 0.0309(7) Uani 1 1 d . U . . .
F1A F 0.7173(9) 0.8035(7) 0.3817(3) 0.0417(19) Uani 0.841(9) 1 d . U P A 1
O1 O 0.7979(9) 0.6270(7) 0.7628(3) 0.0417(16) Uani 1 1 d . U . . .
C17 C 0.4492(11) 0.9086(10) 0.5657(4) 0.0225(18) Uani 1 1 d . U . . .
C4 C 0.9758(12) 0.7795(11) 0.5831(4) 0.0262(19) Uani 1 1 d . U . . .
C6 C 0.8402(13) 0.7267(11) 0.7047(5) 0.031(2) Uani 1 1 d . U . . .
C7 C 0.9474(12) 1.0548(10) 0.5282(4) 0.0236(18) Uani 1 1 d . U . . .
C3 C 0.8958(12) 0.9633(10) 0.5940(4) 0.0233(18) Uani 1 1 d . U . . .
C18 C 0.5631(12) 0.8158(11) 0.5006(4) 0.0275(19) Uani 1 1 d . U . . .
H18 H 0.606459 0.692238 0.500695 0.033 Uiso 0.841(9) 1 calc R U P A 1
C5 C 0.9477(13) 0.6618(11) 0.6375(4) 0.032(2) Uani 1 1 d . U . . .
H5 H 1.000672 0.539981 0.628989 0.038 Uiso 1 1 calc R U . . .
C2 C 0.7806(12) 1.0288(11) 0.6616(4) 0.029(2) Uani 1 1 d . U . . .
H2 H 0.720801 1.150175 0.669385 0.035 Uiso 1 1 calc R U . . .
N2 N 0.5050(12) 0.4812(10) 0.6343(4) 0.053(2) Uani 1 1 d . U . . .
C19 C 0.6095(12) 0.8991(11) 0.4402(5) 0.029(2) Uani 1 1 d . U . . .
H19 H 0.683430 0.831071 0.399387 0.035 Uiso 0.159(9) 1 calc R U P A 2
C1 C 0.7576(12) 0.9099(11) 0.7162(4) 0.034(2) Uani 1 1 d . U . . .
H1 H 0.685306 0.952498 0.761763 0.040 Uiso 1 1 calc R U . . .
C21 C 0.4586(14) 0.6310(12) 0.6312(5) 0.036(2) Uiso 1 1 d . U . . .
C16 C 0.4027(12) 0.8233(12) 0.6285(5) 0.032(2) Uani 1 1 d . U . . .
N1 N 0.2219(13) 0.9747(11) 0.7530(4) 0.058(3) Uani 1 1 d . U . . .
C20 C 0.2971(13) 0.9129(12) 0.6965(5) 0.034(2) Uani 1 1 d . U . . .
C8 C 0.8992(16) 0.4379(12) 0.7580(5) 0.055(3) Uani 1 1 d . U . . .
H8A H 1.044309 0.415631 0.751734 0.066 Uiso 1 1 calc R U . . .
H8B H 0.861919 0.385471 0.716063 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8323(16) 0.3591(13) 0.8302(5) 0.061(3) Uani 1 1 d . U . . .
H9A H 0.860188 0.421108 0.871389 0.073 Uiso 1 1 calc R U . . .
H9B H 0.911864 0.235496 0.831947 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6096(16) 0.3696(13) 0.8404(5) 0.060(3) Uani 1 1 d . U . . .
H10A H 0.528477 0.492257 0.836961 0.072 Uiso 1 1 calc R U . . .
H10B H 0.581543 0.301694 0.801259 0.072 Uiso 1 1 calc R U . . .
C12 C 0.3409(18) 0.2857(15) 0.9270(6) 0.074(4) Uani 1 1 d . U . . .
H12A H 0.328530 0.198773 0.892199 0.088 Uiso 1 1 calc R U . . .
H12B H 0.250332 0.399959 0.915534 0.088 Uiso 1 1 calc R U . . .
C15 C -0.0120(18) 0.1891(15) 1.0955(5) 0.079(4) Uani 1 1 d . U . . .
H15A H -0.145212 0.177118 1.097225 0.119 Uiso 1 1 calc GR U . . .
H15B H -0.014761 0.284820 1.127807 0.119 Uiso 1 1 calc GR U . . .
H15C H 0.077851 0.080584 1.111190 0.119 Uiso 1 1 calc GR U . . .
C11 C 0.5536(17) 0.2964(14) 0.9157(6) 0.077(4) Uani 1 1 d . U . . .
H11A H 0.645539 0.178505 0.920765 0.092 Uiso 1 1 calc R U . . .
H11B H 0.571021 0.371517 0.954481 0.092 Uiso 1 1 calc R U . . .
C13 C 0.2744(17) 0.2350(13) 1.0054(5) 0.069(3) Uani 1 1 d . U . . .
H13A H 0.362956 0.119469 1.016470 0.083 Uiso 1 1 calc R U . . .
H13B H 0.289249 0.320438 1.040297 0.083 Uiso 1 1 calc R U . . .
C14 C 0.061(2) 0.2284(17) 1.0165(5) 0.083(4) Uani 1 1 d . U . . .
H14A H 0.048480 0.137852 0.983587 0.100 Uiso 1 1 calc R U . . .
H14B H -0.026476 0.341611 1.002287 0.100 Uiso 1 1 calc R U . . .
F1B F 0.639(5) 0.636(4) 0.4998(14) 0.041(9) Uani 0.159(9) 1 d . U P A 2


_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
S001 C4 1.748(7) 2_776 ?
S001 C7 1.747(8) . ?
F1A C19 1.331(9) . ?
O1 C6 1.359(9) . ?
O1 C8 1.448(10) . ?
C17 C18 1.425(10) . ?
C17 C19 1.454(11) 2_676 ?
C17 C16 1.365(10) . ?
C4 C3 1.398(10) . ?
C4 C5 1.377(10) . ?
C6 C5 1.376(10) . ?
C6 C1 1.397(11) . ?
C7 C7 1.349(14) 2_776 ?
C7 C3 1.446(10) . ?
C3 C2 1.403(10) . ?
C18 C19 1.323(10) . ?
C18 F1B 1.36(3) . ?
C2 C1 1.377(10) . ?
N2 C21 1.130(10) . ?
C21 C16 1.450(11) . ?
C16 C20 1.442(11) . ?
N1 C20 1.142(10) . ?
C8 C9 1.522(11) . ?
C9 C10 1.523(14) . ?
C10 C11 1.526(11) . ?
C12 C11 1.503(15) . ?
C12 C13 1.526(12) . ?
C15 C14 1.520(12) . ?
C13 C14 1.497(15) . ?

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
C4 S001 C7 90.1(4) 2_776 . ?
C6 O1 C8 117.0(6) . . ?
C18 C17 C19 114.3(7) . 2_676 ?
C16 C17 C18 122.6(8) . . ?
C16 C17 C19 123.1(8) . 2_676 ?
C3 C4 S001 113.0(6) . 2_776 ?
C5 C4 S001 125.3(6) . 2_776 ?
C5 C4 C3 121.7(7) . . ?
O1 C6 C5 125.7(8) . . ?
O1 C6 C1 114.4(7) . . ?
C5 C6 C1 119.8(8) . . ?
C7 C7 S001 113.0(8) 2_776 . ?
C7 C7 C3 113.8(9) 2_776 . ?
C3 C7 S001 133.2(6) . . ?
C4 C3 C7 110.1(7) . . ?
C2 C3 C4 119.0(7) . . ?
C2 C3 C7 130.9(8) . . ?
C19 C18 C17 122.4(8) . . ?
C19 C18 F1B 116.8(15) . . ?
F1B C18 C17 120.7(14) . . ?
C4 C5 C6 119.2(8) . . ?
C1 C2 C3 118.7(8) . . ?
F1A C19 C17 117.7(7) . 2_676 ?
C18 C19 F1A 119.0(8) . . ?
C18 C19 C17 123.3(8) . 2_676 ?
C2 C1 C6 121.5(8) . . ?
N2 C21 C16 178.5(10) . . ?
C17 C16 C21 121.3(8) . . ?
C17 C16 C20 124.1(8) . . ?
C20 C16 C21 114.6(8) . . ?
N1 C20 C16 175.3(10) . . ?
O1 C8 C9 106.6(7) . . ?
C8 C9 C10 113.9(9) . . ?
C11 C10 C9 110.4(9) . . ?
C11 C12 C13 114.1(10) . . ?
C12 C11 C10 113.6(10) . . ?
C14 C13 C12 113.7(10) . . ?
C13 C14 C15 114.4(10) . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2019-11-22
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.530
_oxdiff_exptl_absorpt_empirical_full_min 0.433
####################################################################### 
# 
# 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_f4_200k
_database_code_depnum_ccdc_archive 'CCDC 2151124'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-11-22
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H40 O2 S2, C12 F4 N4'
_chemical_formula_sum            'C42 H40 F4 N4 O2 S2'
_chemical_formula_weight         772.90
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.1246 0.1234 '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                   6.9205(16)
_cell_length_b                   8.0246(13)
_cell_length_c                   18.043(3)
_cell_angle_alpha                89.086(13)
_cell_angle_beta                 82.890(16)
_cell_angle_gamma                72.809(18)
_cell_volume                     949.7(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    849
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.6420
_cell_measurement_theta_min      3.5000
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull blackish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.2134
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.815
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7426
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.435
_diffrn_reflns_theta_min         3.414
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.815
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  11.00   1.00  150.00    --  -16.44 -77.00 120.00   42
  2  ω    -85.00   2.00   1.00  150.00    --  -16.44 -57.00   0.00   87
  3  ω     26.00  52.00   1.00  150.00    --  -16.44  57.00 150.00   26
  4  ω    -33.00  45.00   1.00  150.00    --  -16.44  38.00 150.00   78
  5  ω      8.00  37.00   1.00  150.00    --   17.92  77.00 -30.00   29
  6  ω    -17.00   9.00   1.00  150.00    --   17.92 -99.00-120.00   26
  7  ω    -19.00  58.00   1.00  150.00    --   17.92 -99.00 -90.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0142204000
_diffrn_orient_matrix_UB_12      0.0194639000
_diffrn_orient_matrix_UB_13      -0.0377895000
_diffrn_orient_matrix_UB_21      0.0940415000
_diffrn_orient_matrix_UB_22      -0.0636919000
_diffrn_orient_matrix_UB_23      -0.0118879000
_diffrn_orient_matrix_UB_31      -0.0514380000
_diffrn_orient_matrix_UB_32      -0.0642601000
_diffrn_orient_matrix_UB_33      -0.0009049000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2163
_reflns_number_total             4294
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1875
_refine_ls_R_factor_gt           0.0878
_refine_ls_restrained_S_all      0.993
_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)+(0.0351P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1780
_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:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C12(H12A,H12B),
 C11(H11A,H11B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C2(H2)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.88954(18) 0.77328(15) 0.50821(7) 0.0153(3) Uani 1 1 d . . . . .
F002 F 0.6376(4) 1.1463(3) 0.49705(15) 0.0237(7) Uani 1 1 d . . . . .
F003 F 0.7215(4) 1.3136(3) 0.37740(15) 0.0228(7) Uani 1 1 d . . . . .
O1 O 0.8071(5) 0.1257(4) 0.76160(18) 0.0245(8) Uani 1 1 d . . . . .
C16 C 0.4528(7) 1.4065(6) 0.5664(3) 0.0153(11) Uani 1 1 d . . . . .
C3 C 0.8954(6) 0.4626(5) 0.5947(3) 0.0144(10) Uani 1 1 d . . . . .
N2 N 0.5082(6) 0.9828(5) 0.6418(2) 0.0323(12) Uani 1 1 d . . . . .
C4 C 0.9783(6) 0.2811(6) 0.5817(2) 0.0127(10) Uani 1 1 d . . . . .
C1 C 0.7618(6) 0.4082(6) 0.7177(3) 0.0164(11) Uani 1 1 d . . . . .
H1 H 0.689206 0.449377 0.765307 0.020 Uiso 1 1 calc R . . . .
C17 C 0.5677(6) 1.3213(6) 0.4985(3) 0.0166(11) Uani 1 1 d . . . . .
C18 C 0.6091(6) 1.4062(6) 0.4371(3) 0.0176(11) Uani 1 1 d . . . . .
C5 C 0.9567(7) 0.1619(6) 0.6362(3) 0.0182(11) Uani 1 1 d . . . . .
H5 H 1.016161 0.040018 0.627182 0.022 Uiso 1 1 calc R . . . .
N1 N 0.2241(7) 1.4630(6) 0.7554(3) 0.0366(12) Uani 1 1 d . . . . .
C6 C 0.8463(7) 0.2258(6) 0.7038(3) 0.0191(11) Uani 1 1 d . . . . .
C21 C 0.4668(7) 1.1298(6) 0.6337(3) 0.0201(11) Uani 1 1 d . . . . .
C7 C 0.9440(7) 0.5516(5) 0.5288(3) 0.0159(11) Uani 1 1 d . . . . .
C19 C 0.4100(7) 1.3174(6) 0.6293(3) 0.0188(11) Uani 1 1 d . . . . .
C20 C 0.3049(7) 1.4044(6) 0.6981(3) 0.0220(12) Uani 1 1 d . . . . .
C2 C 0.7832(7) 0.5257(6) 0.6638(3) 0.0186(11) Uani 1 1 d . . . . .
H2 H 0.723402 0.647423 0.673134 0.022 Uiso 1 1 calc R . . . .
C8 C 0.9090(8) -0.0611(6) 0.7550(3) 0.0305(14) Uani 1 1 d . . . . .
H8A H 1.058804 -0.084113 0.747444 0.037 Uiso 1 1 calc R . . . .
H8B H 0.868297 -0.112091 0.711994 0.037 Uiso 1 1 calc R . . . .
C9 C 0.8442(8) -0.1395(6) 0.8271(3) 0.0387(16) Uani 1 1 d . . . . .
H9A H 0.926680 -0.263367 0.827573 0.046 Uiso 1 1 calc R . . . .
H9B H 0.875149 -0.078456 0.869287 0.046 Uiso 1 1 calc R . . . .
C10 C 0.6230(8) -0.1301(7) 0.8394(3) 0.0403(16) Uani 1 1 d . . . . .
H10A H 0.593054 -0.196481 0.798802 0.048 Uiso 1 1 calc R . . . .
H10B H 0.539918 -0.006899 0.836680 0.048 Uiso 1 1 calc R . . . .
C13 C 0.2732(8) -0.2615(7) 1.0032(3) 0.0477(18) Uani 1 1 d . . . . .
H13A H 0.362601 -0.378780 1.013375 0.057 Uiso 1 1 calc R . . . .
H13B H 0.289717 -0.179129 1.040472 0.057 Uiso 1 1 calc R . . . .
C12 C 0.3469(9) -0.2092(8) 0.9261(3) 0.0506(18) Uani 1 1 d . . . . .
H12A H 0.332061 -0.292655 0.889003 0.061 Uiso 1 1 calc R . . . .
H12B H 0.256059 -0.092751 0.915729 0.061 Uiso 1 1 calc R . . . .
C11 C 0.5600(9) -0.2022(7) 0.9145(3) 0.0518(19) Uani 1 1 d . . . . .
H11A H 0.652307 -0.321543 0.918930 0.062 Uiso 1 1 calc R . . . .
H11B H 0.579665 -0.129162 0.954922 0.062 Uiso 1 1 calc R . . . .
C15 C -0.0194(9) -0.3073(7) 1.0928(3) 0.0512(18) Uani 1 1 d . . . . .
H15A H -0.163668 -0.300559 1.094729 0.077 Uiso 1 1 calc GR . . . .
H15B H -0.004609 -0.222800 1.128667 0.077 Uiso 1 1 calc GR . . . .
H15C H 0.058587 -0.425176 1.105416 0.077 Uiso 1 1 calc GR . . . .
C14 C 0.0600(10) -0.2659(8) 1.0149(3) 0.058(2) Uani 1 1 d . . . . .
H14A H 0.045878 -0.353770 0.979691 0.069 Uiso 1 1 calc R . . . .
H14B H -0.028446 -0.150931 1.001497 0.069 Uiso 1 1 calc R . . . .


_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 C4 1.755(5) 2_766 ?
S1 C7 1.749(4) . ?
F002 C17 1.343(5) . ?
F003 C18 1.339(5) . ?
O1 C6 1.357(5) . ?
O1 C8 1.455(5) . ?
C16 C17 1.438(6) . ?
C16 C18 1.438(6) 2_686 ?
C16 C19 1.380(6) . ?
C3 C4 1.410(6) . ?
C3 C7 1.433(6) . ?
C3 C2 1.402(6) . ?
N2 C21 1.140(5) . ?
C4 C5 1.386(5) . ?
C1 C6 1.420(6) . ?
C1 C2 1.369(6) . ?
C17 C18 1.337(6) . ?
C5 C6 1.375(6) . ?
N1 C20 1.148(6) . ?
C21 C19 1.442(6) . ?
C7 C7 1.347(9) 2_766 ?
C19 C20 1.435(7) . ?
C8 C9 1.511(6) . ?
C9 C10 1.499(7) . ?
C10 C11 1.528(7) . ?
C13 C12 1.518(7) . ?
C13 C14 1.475(7) . ?
C12 C11 1.482(7) . ?
C15 C14 1.513(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C4 90.0(2) . 2_766 ?
C6 O1 C8 117.5(4) . . ?
C17 C16 C18 113.4(4) . 2_686 ?
C19 C16 C17 123.3(4) . . ?
C19 C16 C18 123.4(4) . 2_686 ?
C4 C3 C7 109.1(4) . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 C7 131.3(4) . . ?
C3 C4 S1 113.0(3) . 2_766 ?
C5 C4 S1 125.0(4) . 2_766 ?
C5 C4 C3 122.0(4) . . ?
C2 C1 C6 121.1(4) . . ?
F002 C17 C16 117.8(4) . . ?
C18 C17 F002 118.4(4) . . ?
C18 C17 C16 123.8(4) . . ?
F003 C18 C16 118.4(4) . 2_686 ?
C17 C18 F003 118.7(4) . . ?
C17 C18 C16 122.8(5) . 2_686 ?
C6 C5 C4 117.8(4) . . ?
O1 C6 C1 114.4(4) . . ?
O1 C6 C5 124.6(4) . . ?
C5 C6 C1 121.0(4) . . ?
N2 C21 C19 175.8(5) . . ?
C3 C7 S1 132.2(3) . . ?
C7 C7 S1 112.3(4) 2_766 . ?
C7 C7 C3 115.5(5) 2_766 . ?
C16 C19 C21 124.3(4) . . ?
C16 C19 C20 122.6(4) . . ?
C20 C19 C21 113.1(4) . . ?
N1 C20 C19 175.3(5) . . ?
C1 C2 C3 118.6(4) . . ?
O1 C8 C9 106.6(4) . . ?
C10 C9 C8 114.6(4) . . ?
C9 C10 C11 113.4(5) . . ?
C14 C13 C12 115.9(5) . . ?
C11 C12 C13 116.2(5) . . ?
C12 C11 C10 115.1(5) . . ?
C13 C14 C15 116.5(5) . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2019-11-20
_olex2_exptl_crystal_mounting_method oil
_olex2_submission_original_sample_id F4-C8OBTBT
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.855
_oxdiff_exptl_absorpt_empirical_full_min 0.668
