# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mo_IRSHAD_IIIM_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2378048'
loop_
_audit_author_name
_audit_author_address
'Irshad Ahmad Zargar'
;CSIR Indian Institute of Integrative Medicine
India
;
_audit_update_record             
;
2024-08-16 deposited with the CCDC.	2024-10-09 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            'C2.40 H2.67 F0.13 N0.13 O0.93'
_chemical_formula_weight         50.85

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.1122(10)
_cell_length_b                   13.527(3)
_cell_length_c                   26.011(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1798.7(7)
_cell_formula_units_Z            30
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9655
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.07

_exptl_crystal_description       ,
_exptl_crystal_colour            ,
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42680
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.172
_diffrn_reflns_theta_max         25.116
_diffrn_reflns_theta_full        25.116
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3191
_reflns_number_gt                3123
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0442P)²+0.2839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1246 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration ,
_refine_ls_number_reflns         3191
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.2837(3) 0.95219(9) 0.57636(5) 0.0434(4) Uani 1 1 d . . . . .
O1 O 0.7271(3) 0.43709(9) 0.65311(5) 0.0211(3) Uani 1 1 d . . . . .
O2 O 0.4386(2) 0.42161(9) 0.52594(5) 0.0221(3) Uani 1 1 d . . . . .
O3 O 0.6667(3) 0.31300(11) 0.47853(5) 0.0297(3) Uani 1 1 d . . . . .
O4 O 0.2674(3) 0.34429(9) 0.68092(5) 0.0252(3) Uani 1 1 d . . . . .
O5 O 0.0071(3) 0.21319(11) 0.66955(6) 0.0347(4) Uani 1 1 d . . . . .
O6 O 0.7015(3) 0.60226(9) 0.68054(5) 0.0198(3) Uani 1 1 d . . . . .
O7 O 0.2671(3) 0.56910(10) 0.73593(5) 0.0260(3) Uani 1 1 d . . . . .
N1 N 0.7072(3) 0.57700(13) 0.73264(6) 0.0219(3) Uani 1 1 d . . . . .
H1 H 0.859(5) 0.5766(18) 0.7456(10) 0.033 Uiso 1 1 d . U . . .
C1 C 0.9844(4) 0.67203(14) 0.59240(7) 0.0211(4) Uani 1 1 d . . . . .
C2 C 1.1941(4) 0.70286(15) 0.62265(7) 0.0246(4) Uani 1 1 d . . . . .
H2 H 1.266878 0.659060 0.647357 0.029 Uiso 1 1 calc R U . . .
C3 C 1.2971(4) 0.79695(16) 0.61693(8) 0.0295(5) Uani 1 1 d . . . . .
H3 H 1.443017 0.817721 0.636797 0.035 Uiso 1 1 calc R U . . .
C4 C 1.1834(5) 0.85938(14) 0.58192(8) 0.0296(5) Uani 1 1 d . . . . .
C5 C 0.9740(4) 0.83280(15) 0.55198(7) 0.0289(4) Uani 1 1 d . . . . .
H5 H 0.898775 0.878067 0.528294 0.035 Uiso 1 1 calc R U . . .
C6 C 0.8759(4) 0.73811(14) 0.55732(7) 0.0243(4) Uani 1 1 d . . . . .
H6 H 0.732156 0.717803 0.536727 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8699(4) 0.57189(13) 0.59780(7) 0.0198(4) Uani 1 1 d . . . . .
C8 C 0.7937(4) 0.51710(14) 0.55808(7) 0.0214(4) Uani 1 1 d . . . . .
H8 H 0.836331 0.538796 0.524369 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6433(4) 0.42247(14) 0.56414(7) 0.0210(4) Uani 1 1 d . . . . .
H9 H 0.760997 0.363955 0.559988 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5178(4) 0.42294(13) 0.61704(7) 0.0202(4) Uani 1 1 d . . . . .
H10 H 0.391029 0.479018 0.619624 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8453(4) 0.53016(13) 0.65138(7) 0.0187(4) Uani 1 1 d . . . . .
H11 H 1.024648 0.524459 0.666448 0.022 Uiso 1 1 calc R U . . .
C12 C 0.4803(4) 0.36592(12) 0.48344(7) 0.0192(4) Uani 1 1 d . . . . .
C13 C 0.3838(4) 0.32762(14) 0.63137(7) 0.0239(4) Uani 1 1 d . . . . .
H13A H 0.248116 0.310609 0.605704 0.029 Uiso 1 1 calc R U . . .
H13B H 0.512014 0.272858 0.633098 0.029 Uiso 1 1 calc R U . . .
C14 C 0.0762(4) 0.28189(14) 0.69532(8) 0.0240(4) Uani 1 1 d . . . . .
C15 C 0.4807(4) 0.56327(13) 0.75707(7) 0.0198(4) Uani 1 1 d . . . . .
C16 C 0.2671(4) 0.37962(15) 0.44522(8) 0.0271(4) Uani 1 1 d . . . . .
H16A H 0.318093 0.349330 0.412497 0.041 Uiso 1 1 calc R U . . .
H16B H 0.235625 0.450396 0.440070 0.041 Uiso 1 1 calc R U . . .
H16C H 0.106891 0.348154 0.457907 0.041 Uiso 1 1 calc R U . . .
C17 C -0.0325(5) 0.30910(16) 0.74672(9) 0.0356(5) Uani 1 1 d . . . . .
H17A H -0.223858 0.305156 0.745683 0.053 Uiso 1 1 calc R U . . .
H17B H 0.020536 0.376677 0.755421 0.053 Uiso 1 1 calc R U . . .
H17C H 0.034439 0.263298 0.772783 0.053 Uiso 1 1 calc R U . . .
C18 C 0.5099(5) 0.54041(16) 0.81342(7) 0.0302(5) Uani 1 1 d . . . . .
H18A H 0.695020 0.544003 0.823016 0.045 Uiso 1 1 calc R U . . .
H18B H 0.443503 0.473756 0.820338 0.045 Uiso 1 1 calc R U . . .
H18C H 0.410107 0.588591 0.833601 0.045 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
F1 C4 1.364(2) . ?
O1 C11 1.397(2) . ?
O1 C10 1.436(2) . ?
O2 C12 1.355(2) . ?
O2 C9 1.443(2) . ?
O3 C12 1.199(2) . ?
O4 C14 1.344(2) . ?
O4 C13 1.437(2) . ?
O5 C14 1.199(2) . ?
O6 N1 1.398(2) . ?
O6 C11 1.438(2) . ?
O7 C15 1.225(2) . ?
N1 C15 1.334(3) . ?
N1 H1 0.85(3) . ?
C1 C6 1.392(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.482(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(3) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.330(3) . ?
C7 C11 1.509(2) . ?
C8 C9 1.501(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.518(3) . ?
C9 H9 1.0000 . ?
C10 C13 1.507(3) . ?
C10 H10 1.0000 . ?
C11 H11 1.0000 . ?
C12 C16 1.487(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C17 1.494(3) . ?
C15 C18 1.506(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C11 O1 C10 114.93(13) . . ?
C12 O2 C9 116.90(14) . . ?
C14 O4 C13 116.90(15) . . ?
N1 O6 C11 109.57(13) . . ?
C15 N1 O6 118.53(15) . . ?
C15 N1 H1 127.3(17) . . ?
O6 N1 H1 114.0(18) . . ?
C6 C1 C2 118.96(18) . . ?
C6 C1 C7 119.45(18) . . ?
C2 C1 C7 121.57(17) . . ?
C3 C2 C1 120.44(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
F1 C4 C3 118.6(2) . . ?
F1 C4 C5 118.32(19) . . ?
C3 C4 C5 123.12(19) . . ?
C4 C5 C6 117.96(19) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 121.07(19) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C1 123.45(17) . . ?
C8 C7 C11 118.99(17) . . ?
C1 C7 C11 117.54(16) . . ?
C7 C8 C9 122.93(17) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
O2 C9 C8 107.81(15) . . ?
O2 C9 C10 108.52(15) . . ?
C8 C9 C10 107.94(15) . . ?
O2 C9 H9 110.8 . . ?
C8 C9 H9 110.8 . . ?
C10 C9 H9 110.8 . . ?
O1 C10 C13 106.93(14) . . ?
O1 C10 C9 106.13(15) . . ?
C13 C10 C9 114.37(15) . . ?
O1 C10 H10 109.8 . . ?
C13 C10 H10 109.8 . . ?
C9 C10 H10 109.8 . . ?
O1 C11 O6 111.89(14) . . ?
O1 C11 C7 113.75(14) . . ?
O6 C11 C7 106.03(14) . . ?
O1 C11 H11 108.3 . . ?
O6 C11 H11 108.3 . . ?
C7 C11 H11 108.3 . . ?
O3 C12 O2 122.95(17) . . ?
O3 C12 C16 125.89(17) . . ?
O2 C12 C16 111.16(16) . . ?
O4 C13 C10 106.01(14) . . ?
O4 C13 H13A 110.5 . . ?
C10 C13 H13A 110.5 . . ?
O4 C13 H13B 110.5 . . ?
C10 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
O5 C14 O4 123.03(19) . . ?
O5 C14 C17 125.55(19) . . ?
O4 C14 C17 111.42(17) . . ?
O7 C15 N1 123.44(16) . . ?
O7 C15 C18 122.58(18) . . ?
N1 C15 C18 113.98(18) . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.052



