# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_LF_DMSO
_database_code_depnum_ccdc_archive 'CCDC 2222459'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2022-11-27 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_audit_creation_date             2022-09-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 F3 N2 O2, C2 H6 O S'
_chemical_formula_sum            'C14 H15 F3 N2 O3 S'
_chemical_formula_weight         348.34
_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                   7.9976(5)
_cell_length_b                   8.4028(5)
_cell_length_c                   12.3149(8)
_cell_angle_alpha                75.304(3)
_cell_angle_beta                 71.879(3)
_cell_angle_gamma                81.037(3)
_cell_volume                     758.14(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9690
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_correction_T_min  0.9367
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1592 before and 0.0820 after correction.
The Ratio of minimum to maximum transmission is 0.9566.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_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
-1.00 0.00 1.00 0.2050
-1.00 -1.00 0.00 0.2010
0.00 -1.00 -1.00 0.0760
1.00 0.00 -1.00 0.1710
1.00 1.00 0.00 0.2520
1.00 -1.00 -1.00 0.1770
-1.00 0.00 0.00 0.2720
1.00 0.00 0.00 0.2280
0.00 1.00 0.00 0.1160
0.00 -1.00 0.00 0.0610
-1.00 0.00 -1.00 0.2800
1.00 0.00 1.00 0.2340
0.00 1.00 -1.00 0.1300
0.00 -1.00 1.00 0.0500
0.00 0.00 -1.00 0.1200
0.00 0.00 1.00 0.0330
-1.00 -1.00 1.00 0.1390

_exptl_crystal_size_max          0.589
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.152
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            65255
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.050
_diffrn_reflns_theta_min         2.515
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3892
_reflns_number_total             4423
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.059(10)
_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   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.055
_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)+(0.0635P)²+0.1661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1002
_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 Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C7(H7), C10(H10), C4(H4)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.05876(3) 0.90919(3) 0.35128(2) 0.01570(9) Uani 1 1 d . . . . .
F1 F 0.81515(10) 0.10100(10) 0.10281(6) 0.02881(18) Uani 1 1 d . . . . .
F3 F 0.71626(11) 0.32259(9) 0.00202(6) 0.03140(19) Uani 1 1 d . . . . .
F2 F 0.56390(11) 0.11142(12) 0.07198(7) 0.0366(2) Uani 1 1 d . . . . .
O3 O 0.07343(11) 0.73259(10) 0.41739(7) 0.02089(17) Uani 1 1 d . . . . .
O2 O 0.03975(11) 0.55684(10) 0.86852(7) 0.01925(17) Uani 1 1 d . . . . .
O1 O 0.35096(13) 0.23380(10) 0.65585(7) 0.0256(2) Uani 1 1 d . . . . .
N1 N 0.29818(12) 0.44080(11) 0.50607(7) 0.01477(18) Uani 1 1 d . . . . .
N2 N -0.02279(13) 0.66988(12) 0.78010(8) 0.0202(2) Uani 1 1 d . . . . .
C6 C 0.51555(14) 0.23474(13) 0.41423(9) 0.0162(2) Uani 1 1 d . . . . .
H6 H 0.535426 0.178024 0.486935 0.019 Uiso 1 1 calc R U . . .
C9 C 0.45751(14) 0.40021(13) 0.20032(9) 0.0184(2) Uani 1 1 d . . . . .
H9 H 0.437142 0.455927 0.127572 0.022 Uiso 1 1 calc R U . . .
C8 C 0.57860(14) 0.26248(13) 0.20586(9) 0.0163(2) Uani 1 1 d . . . . .
C7 C 0.60680(14) 0.17968(13) 0.31245(9) 0.0169(2) Uani 1 1 d . . . . .
H7 H 0.688788 0.084991 0.315893 0.020 Uiso 1 1 calc R U . . .
C10 C 0.36669(14) 0.45587(13) 0.30124(9) 0.0174(2) Uani 1 1 d . . . . .
H10 H 0.284785 0.550574 0.297262 0.021 Uiso 1 1 calc R U . . .
C14 C 0.24139(15) 1.00154(14) 0.35699(10) 0.0213(2) Uani 1 1 d . . . . .
H14A H 0.223105 1.013994 0.436969 0.032 Uiso 1 1 calc R U . . .
H14B H 0.251172 1.110285 0.303438 0.032 Uiso 1 1 calc R U . . .
H14C H 0.350170 0.931055 0.333692 0.032 Uiso 1 1 calc R U . . .
C1 C 0.27889(14) 0.36914(13) 0.62146(9) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.16584(13) 0.46834(12) 0.70431(9) 0.0152(2) Uani 1 1 d . . . . .
C4 C 0.05328(14) 0.61535(13) 0.68500(9) 0.0176(2) Uani 1 1 d . . . . .
H4 H 0.035702 0.667744 0.610919 0.021 Uiso 1 1 calc R U . . .
C5 C 0.39456(13) 0.37378(12) 0.40905(9) 0.01394(19) Uani 1 1 d . . . . .
C3 C 0.15079(14) 0.43810(13) 0.82139(9) 0.0164(2) Uani 1 1 d . . . . .
C11 C 0.22660(17) 0.30705(14) 0.90276(10) 0.0229(2) Uani 1 1 d . . . . .
H11A H 0.253213 0.355827 0.959206 0.034 Uiso 1 1 calc R U . . .
H11B H 0.335378 0.254250 0.858264 0.034 Uiso 1 1 calc R U . . .
H11C H 0.141368 0.224364 0.944625 0.034 Uiso 1 1 calc R U . . .
C12 C 0.66847(15) 0.19961(14) 0.09706(10) 0.0202(2) Uani 1 1 d . . . . .
C13 C 0.13389(19) 0.90612(15) 0.19932(10) 0.0271(3) Uani 1 1 d . . . . .
H13A H 0.253891 0.851983 0.180893 0.041 Uiso 1 1 calc R U . . .
H13B H 0.133986 1.019552 0.152699 0.041 Uiso 1 1 calc R U . . .
H13C H 0.055035 0.845130 0.180897 0.041 Uiso 1 1 calc R U . . .
H1 H 0.236(2) 0.532(2) 0.4880(14) 0.027(4) Uiso 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
S1 O3 1.5069(8) . ?
S1 C14 1.7846(11) . ?
S1 C13 1.7845(12) . ?
F1 C12 1.3367(14) . ?
F3 C12 1.3471(13) . ?
F2 C12 1.3467(14) . ?
O2 N2 1.4157(12) . ?
O2 C3 1.3484(13) . ?
O1 C1 1.2281(13) . ?
N1 C1 1.3653(13) . ?
N1 C5 1.4043(12) . ?
N1 H1 0.863(17) . ?
N2 C4 1.3015(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.3920(14) . ?
C6 C5 1.3978(14) . ?
C9 H9 0.9500 . ?
C9 C8 1.3906(15) . ?
C9 C10 1.3851(14) . ?
C8 C7 1.3891(15) . ?
C8 C12 1.4942(14) . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
C10 C5 1.3999(14) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C1 C2 1.4751(14) . ?
C2 C4 1.4250(14) . ?
C2 C3 1.3688(14) . ?
C4 H4 0.9500 . ?
C3 C11 1.4813(15) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 C14 105.98(5) . . ?
O3 S1 C13 106.66(5) . . ?
C13 S1 C14 97.46(6) . . ?
C3 O2 N2 109.12(8) . . ?
C1 N1 C5 127.20(9) . . ?
C1 N1 H1 119.0(11) . . ?
C5 N1 H1 113.3(11) . . ?
C4 N2 O2 105.17(8) . . ?
C7 C6 H6 120.1 . . ?
C7 C6 C5 119.74(10) . . ?
C5 C6 H6 120.1 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C10 C9 C8 119.77(10) . . ?
C9 C8 C12 118.85(10) . . ?
C7 C8 C9 120.15(10) . . ?
C7 C8 C12 120.89(10) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.35(10) . . ?
C8 C7 H7 119.8 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C5 120.57(10) . . ?
C5 C10 H10 119.7 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C1 N1 123.71(10) . . ?
O1 C1 C2 121.37(9) . . ?
N1 C1 C2 114.91(9) . . ?
C4 C2 C1 130.34(9) . . ?
C3 C2 C1 125.89(10) . . ?
C3 C2 C4 103.75(9) . . ?
N2 C4 C2 112.52(10) . . ?
N2 C4 H4 123.7 . . ?
C2 C4 H4 123.7 . . ?
C6 C5 N1 124.19(9) . . ?
C10 C5 N1 116.39(9) . . ?
C10 C5 C6 119.42(9) . . ?
O2 C3 C2 109.44(9) . . ?
O2 C3 C11 116.29(9) . . ?
C2 C3 C11 134.27(10) . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F1 C12 F3 106.30(9) . . ?
F1 C12 F2 105.99(9) . . ?
F1 C12 C8 113.48(9) . . ?
F3 C12 C8 112.36(9) . . ?
F2 C12 F3 105.87(9) . . ?
F2 C12 C8 112.28(9) . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 N2 C4 C2 0.19(12) . . . . ?
O1 C1 C2 C4 -170.80(11) . . . . ?
O1 C1 C2 C3 11.11(17) . . . . ?
N1 C1 C2 C4 10.29(16) . . . . ?
N1 C1 C2 C3 -167.80(10) . . . . ?
N2 O2 C3 C2 0.45(12) . . . . ?
N2 O2 C3 C11 -178.98(9) . . . . ?
C9 C8 C7 C6 -0.64(16) . . . . ?
C9 C8 C12 F1 161.61(10) . . . . ?
C9 C8 C12 F3 40.99(14) . . . . ?
C9 C8 C12 F2 -78.22(13) . . . . ?
C9 C10 C5 N1 179.16(9) . . . . ?
C9 C10 C5 C6 0.14(16) . . . . ?
C8 C9 C10 C5 -0.58(16) . . . . ?
C7 C6 C5 N1 -178.89(9) . . . . ?
C7 C6 C5 C10 0.05(15) . . . . ?
C7 C8 C12 F1 -22.23(15) . . . . ?
C7 C8 C12 F3 -142.86(11) . . . . ?
C7 C8 C12 F2 97.94(12) . . . . ?
C10 C9 C8 C7 0.82(16) . . . . ?
C10 C9 C8 C12 177.01(10) . . . . ?
C1 N1 C5 C6 -13.23(16) . . . . ?
C1 N1 C5 C10 167.80(10) . . . . ?
C1 C2 C4 N2 -178.33(10) . . . . ?
C1 C2 C3 O2 178.18(9) . . . . ?
C1 C2 C3 C11 -2.5(2) . . . . ?
C4 C2 C3 O2 -0.32(12) . . . . ?
C4 C2 C3 C11 178.97(12) . . . . ?
C5 N1 C1 O1 2.47(17) . . . . ?
C5 N1 C1 C2 -178.65(9) . . . . ?
C5 C6 C7 C8 0.20(16) . . . . ?
C3 O2 N2 C4 -0.39(11) . . . . ?
C3 C2 C4 N2 0.07(13) . . . . ?
C12 C8 C7 C6 -176.74(10) . . . . ?

_olex2_submission_original_sample_id LF_DMSO
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LF5_MEOH
_database_code_depnum_ccdc_archive 'CCDC 2222460'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2022-11-27 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_LF5_MEOH            
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Due to weakly diffracting nature of crystal, the data 
quality is poor. Hence, high Rint is observed.
;
_vrf_PLAT020_LF5_MEOH            
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.391 Report
RESPONSE:  Due to weakly diffracting nature of crystal, the data 
quality is poor. Hence, high Rint is observed.
;
# end Validation Reply Form
_audit_creation_date             2022-09-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 F3 N2 O2, C4 H11 N2'
_chemical_formula_sum            'C16 H19 F3 N4 O2'
_chemical_formula_weight         356.35
_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'

_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                   10.8564(14)
_cell_length_b                   7.7062(9)
_cell_length_c                   38.699(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3237.6(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6540
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      20.30
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9577
_exptl_absorpt_correction_T_min  0.4545
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1743 before and 0.1174 after correction.
The Ratio of minimum to maximum transmission is 0.4746.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.084
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3910
_diffrn_reflns_av_unetI/netI     0.1898
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            123993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.080
_diffrn_reflns_theta_min         2.105
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2358
_reflns_number_total             4754
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       0.015(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   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4754
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1900
_refine_ls_R_factor_gt           0.0959
_refine_ls_restrained_S_all      1.036
_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)+(0.0695P)²+3.4303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2089
_refine_ls_wR_factor_ref         0.2374
_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. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C14(H14A,H14B), C13(H13A,H13B), C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C10(H10)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     DIRECT
_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
O1 O -0.0272(2) 0.2879(3) 0.38680(6) 0.0244(6) Uani 1 1 d . . . . .
O2 O 0.3217(2) 0.4896(3) 0.41113(6) 0.0239(6) Uani 1 1 d . . . . .
N3 N 0.5691(3) 0.4223(3) 0.41099(7) 0.0195(6) Uani 1 1 d . . . . .
N4 N 0.6954(2) 0.0923(4) 0.40897(7) 0.0218(7) Uani 1 1 d . . . . .
N1 N 0.1558(3) 0.3903(4) 0.36513(7) 0.0229(7) Uani 1 1 d . . . . .
N2 N -0.0277(3) 0.3149(4) 0.47499(8) 0.0293(7) Uani 1 1 d . . . . .
C3 C 0.2405(3) 0.4594(4) 0.43402(9) 0.0211(7) Uani 1 1 d . . . . .
C16 C 0.5748(3) 0.3126(4) 0.44263(9) 0.0233(8) Uani 1 1 d . . . . .
H16A H 0.499407 0.240809 0.444382 0.028 Uiso 1 1 calc R U . . .
H16B H 0.579632 0.387320 0.463392 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2741(3) 0.4881(4) 0.47135(9) 0.0229(8) Uani 1 1 d . . . . .
H4A H 0.303683 0.379025 0.481378 0.034 Uiso 1 1 calc R U . . .
H4B H 0.201453 0.528016 0.484092 0.034 Uiso 1 1 calc R U . . .
H4C H 0.339170 0.575992 0.472858 0.034 Uiso 1 1 calc R U . . .
C1 C 0.0766(3) 0.3528(4) 0.39145(9) 0.0198(7) Uani 1 1 d . . . . .
C2 C 0.1218(3) 0.3974(4) 0.42575(9) 0.0199(7) Uani 1 1 d . . . . .
C6 C 0.1419(3) 0.3642(4) 0.32955(9) 0.0213(7) Uani 1 1 d . . . . .
C5 C 0.0390(3) 0.3537(4) 0.45307(9) 0.0216(7) Uani 1 1 d . . . . .
C14 C 0.6759(3) 0.1981(4) 0.37770(9) 0.0221(7) Uani 1 1 d . . . . .
H14A H 0.667785 0.119651 0.357563 0.027 Uiso 1 1 calc R U . . .
H14B H 0.749547 0.271352 0.373899 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5635(3) 0.3139(4) 0.37932(9) 0.0235(8) Uani 1 1 d . . . . .
H13A H 0.560577 0.389369 0.358637 0.028 Uiso 1 1 calc R U . . .
H13B H 0.487920 0.241978 0.379651 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2409(3) 0.4144(4) 0.30873(9) 0.0258(8) Uani 1 1 d . . . . .
H7 H 0.312009 0.463639 0.319154 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1333(3) 0.3188(4) 0.25819(9) 0.0266(8) Uani 1 1 d . . . . .
C15 C 0.6879(3) 0.1958(4) 0.44077(9) 0.0247(8) Uani 1 1 d . . . . .
H15A H 0.762668 0.268713 0.442569 0.030 Uiso 1 1 calc R U . . .
H15B H 0.687110 0.116178 0.460848 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2374(3) 0.3938(4) 0.27355(9) 0.0263(8) Uani 1 1 d . . . . .
H8 H 0.304969 0.430095 0.259706 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0387(3) 0.2903(4) 0.31418(9) 0.0257(8) Uani 1 1 d . . . . .
H11 H -0.029457 0.255191 0.327897 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0363(3) 0.2683(5) 0.27868(10) 0.0286(8) Uani 1 1 d . . . . .
H10 H -0.034103 0.217138 0.268232 0.034 Uiso 1 1 calc R U . . .
C12 C 0.1294(4) 0.2934(5) 0.21999(10) 0.0319(9) Uani 1 1 d . . . . .
F2 F 0.0632(7) 0.4163(7) 0.20501(12) 0.054(3) Uani 0.574(14) 1 d . . P A 1
F1 F 0.0749(8) 0.1455(8) 0.21150(13) 0.054(2) Uani 0.574(14) 1 d . . P A 1
F3 F 0.2368(4) 0.2955(14) 0.20524(12) 0.064(4) Uani 0.574(14) 1 d . . P A 1
F1A F 0.1661(11) 0.4341(8) 0.20122(15) 0.057(4) Uani 0.426(14) 1 d . . P A 2
F2A F 0.0232(6) 0.2520(18) 0.20668(17) 0.064(5) Uani 0.426(14) 1 d . . P A 2
F3A F 0.2108(11) 0.1693(14) 0.20875(17) 0.065(4) Uani 0.426(14) 1 d . . P A 2
H3A H 0.500(3) 0.492(5) 0.4125(9) 0.033(10) Uiso 1 1 d . . . . .
H4 H 0.639(3) 0.012(5) 0.4082(9) 0.033(11) Uiso 1 1 d . . . . .
H3B H 0.644(3) 0.493(5) 0.4101(9) 0.027(9) Uiso 1 1 d . . . . .
H1 H 0.237(4) 0.421(5) 0.3759(9) 0.035(10) Uiso 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
O1 C1 1.246(4) . ?
O2 C3 1.271(4) . ?
N3 C16 1.489(4) . ?
N3 C13 1.484(4) . ?
N3 H3A 0.92(4) . ?
N3 H3B 0.98(4) . ?
N4 C14 1.474(4) . ?
N4 C15 1.469(4) . ?
N4 H4 0.88(4) . ?
N1 C1 1.364(4) . ?
N1 C6 1.400(4) . ?
N1 H1 1.00(4) . ?
N2 C5 1.155(4) . ?
C3 C4 1.506(5) . ?
C3 C2 1.411(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.524(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C1 C2 1.456(5) . ?
C2 C5 1.428(5) . ?
C6 C7 1.398(5) . ?
C6 C11 1.391(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.513(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C7 H7 0.9500 . ?
C7 C8 1.371(5) . ?
C9 C8 1.402(5) . ?
C9 C10 1.375(5) . ?
C9 C12 1.492(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.384(5) . ?
C10 H10 0.9500 . ?
C12 F2 1.323(6) . ?
C12 F1 1.325(6) . ?
C12 F3 1.298(6) . ?
C12 F1A 1.365(7) . ?
C12 F2A 1.303(7) . ?
C12 F3A 1.372(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
C16 N3 H3A 108(2) . . ?
C16 N3 H3B 108(2) . . ?
C13 N3 C16 111.2(3) . . ?
C13 N3 H3A 110(2) . . ?
C13 N3 H3B 108(2) . . ?
H3A N3 H3B 111(3) . . ?
C14 N4 H4 105(2) . . ?
C15 N4 C14 112.3(3) . . ?
C15 N4 H4 112(2) . . ?
C1 N1 C6 129.5(3) . . ?
C1 N1 H1 107(2) . . ?
C6 N1 H1 123(2) . . ?
O2 C3 C4 118.2(3) . . ?
O2 C3 C2 122.5(3) . . ?
C2 C3 C4 119.2(3) . . ?
N3 C16 H16A 109.8 . . ?
N3 C16 H16B 109.8 . . ?
N3 C16 C15 109.3(3) . . ?
H16A C16 H16B 108.3 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C1 N1 123.2(3) . . ?
O1 C1 C2 122.1(3) . . ?
N1 C1 C2 114.7(3) . . ?
C3 C2 C1 126.4(3) . . ?
C3 C2 C5 119.1(3) . . ?
C5 C2 C1 114.1(3) . . ?
C7 C6 N1 116.4(3) . . ?
C11 C6 N1 124.5(3) . . ?
C11 C6 C7 119.1(3) . . ?
N2 C5 C2 178.6(4) . . ?
N4 C14 H14A 108.7 . . ?
N4 C14 H14B 108.7 . . ?
N4 C14 C13 114.1(3) . . ?
H14A C14 H14B 107.6 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
N3 C13 C14 109.5(3) . . ?
N3 C13 H13A 109.8 . . ?
N3 C13 H13B 109.8 . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C8 C9 C12 119.8(3) . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 C12 120.8(3) . . ?
N4 C15 C16 113.9(3) . . ?
N4 C15 H15A 108.8 . . ?
N4 C15 H15B 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C6 C11 H11 120.3 . . ?
C10 C11 C6 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
F2 C12 C9 110.8(3) . . ?
F2 C12 F1 105.3(5) . . ?
F1 C12 C9 111.8(4) . . ?
F3 C12 C9 114.1(4) . . ?
F3 C12 F2 106.6(5) . . ?
F3 C12 F1 107.6(5) . . ?
F1A C12 C9 114.5(4) . . ?
F1A C12 F3A 101.4(6) . . ?
F2A C12 C9 116.7(4) . . ?
F2A C12 F1A 104.0(6) . . ?
F2A C12 F3A 105.9(6) . . ?
F3A C12 C9 112.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 175.1(3) . . . . ?
O1 C1 C2 C5 2.3(4) . . . . ?
O2 C3 C2 C1 2.7(5) . . . . ?
O2 C3 C2 C5 175.1(3) . . . . ?
N3 C16 C15 N4 -53.6(4) . . . . ?
N4 C14 C13 N3 53.8(4) . . . . ?
N1 C1 C2 C3 -5.8(5) . . . . ?
N1 C1 C2 C5 -178.6(3) . . . . ?
N1 C6 C7 C8 179.7(3) . . . . ?
N1 C6 C11 C10 -178.9(3) . . . . ?
C16 N3 C13 C14 -58.9(3) . . . . ?
C4 C3 C2 C1 -176.1(3) . . . . ?
C4 C3 C2 C5 -3.6(4) . . . . ?
C1 N1 C6 C7 -179.2(3) . . . . ?
C1 N1 C6 C11 -0.3(5) . . . . ?
C6 N1 C1 O1 -1.2(5) . . . . ?
C6 N1 C1 C2 179.8(3) . . . . ?
C6 C7 C8 C9 -0.9(5) . . . . ?
C6 C11 C10 C9 -0.4(5) . . . . ?
C14 N4 C15 C16 48.8(4) . . . . ?
C13 N3 C16 C15 58.7(3) . . . . ?
C7 C6 C11 C10 -0.1(5) . . . . ?
C15 N4 C14 C13 -49.0(4) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C8 C9 C12 F2 -100.8(5) . . . . ?
C8 C9 C12 F1 142.1(6) . . . . ?
C8 C9 C12 F3 19.6(7) . . . . ?
C8 C9 C12 F1A -46.5(7) . . . . ?
C8 C9 C12 F2A -168.3(8) . . . . ?
C8 C9 C12 F3A 68.8(8) . . . . ?
C11 C6 C7 C8 0.8(5) . . . . ?
C10 C9 C8 C7 0.5(5) . . . . ?
C10 C9 C12 F2 79.7(6) . . . . ?
C10 C9 C12 F1 -37.4(7) . . . . ?
C10 C9 C12 F3 -159.9(6) . . . . ?
C10 C9 C12 F1A 134.0(6) . . . . ?
C10 C9 C12 F2A 12.2(9) . . . . ?
C10 C9 C12 F3A -110.8(8) . . . . ?
C12 C9 C8 C7 -179.1(3) . . . . ?
C12 C9 C10 C11 179.7(3) . . . . ?

_olex2_submission_original_sample_id LF5_MeOH
_olex2_submission_special_instructions 'No special instructions were received'
