# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_SM_1_rpt1_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2175052'
loop_
_audit_author_name
_audit_author_address
'Muhammad Usman Anwar'
;University of Nizwa
Oman
;
_audit_update_record             
;
2022-05-26 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N O3'
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.912(2)
_cell_length_b                   6.7346(16)
_cell_length_c                   22.581(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.102(14)
_cell_angle_gamma                90
_cell_volume                     1347.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6995
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      26.10

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5381
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            24086
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.1087
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.076
_diffrn_reflns_theta_max         26.566
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2791
_reflns_number_gt                1868
_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    '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)+(0.0605P)²+1.8509P] 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         2791
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2120
_refine_ls_wR_factor_gt          0.1912
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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
O1 O 0.2438(3) 0.4801(4) 0.13897(11) 0.0533(7) Uani 1 1 d . . . . .
O2 O 0.0519(3) 0.2275(4) -0.03545(12) 0.0594(7) Uani 1 1 d . . . . .
O3 O 0.2989(3) 0.2683(4) -0.11159(11) 0.0655(8) Uani 1 1 d . . . . .
N1 N 0.2504(3) 0.2237(4) 0.03862(11) 0.0393(6) Uani 1 1 d . . . . .
C1 C 0.1646(4) 0.1866(5) 0.08888(15) 0.0430(8) Uani 1 1 d . . . . .
H1A H 0.226850 0.111813 0.118889 0.052 Uiso 1 1 calc R U . . .
H1B H 0.077343 0.105899 0.075586 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1125(4) 0.3731(5) 0.11643(15) 0.0463(8) Uani 1 1 d . . . . .
H2A H 0.051888 0.451756 0.086878 0.056 Uiso 1 1 calc R U . . .
H2B H 0.051928 0.341534 0.148392 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2276(4) 0.6497(5) 0.17117(14) 0.0460(8) Uani 1 1 d . . . . .
C4 C 0.3615(5) 0.7399(6) 0.19250(17) 0.0622(10) Uani 1 1 d . . . . .
H4 H 0.453012 0.688406 0.183290 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3584(6) 0.9068(8) 0.2275(2) 0.0815(14) Uani 1 1 d . . . . .
H5 H 0.448495 0.967997 0.241996 0.098 Uiso 1 1 calc R U . . .
C6 C 0.2232(7) 0.9843(7) 0.2415(2) 0.0856(15) Uani 1 1 d . . . . .
H6 H 0.221864 1.093861 0.266460 0.103 Uiso 1 1 calc R U . . .
C7 C 0.0910(6) 0.8978(7) 0.21800(18) 0.0715(13) Uani 1 1 d . . . . .
H7 H -0.000384 0.952819 0.226013 0.086 Uiso 1 1 calc R U . . .
C8 C 0.0909(5) 0.7291(5) 0.18236(15) 0.0531(9) Uani 1 1 d . . . . .
H8 H 0.000722 0.671365 0.166473 0.064 Uiso 1 1 calc R U . . .
C9 C 0.1854(4) 0.2349(5) -0.01854(15) 0.0438(8) Uani 1 1 d . . . . .
C10 C 0.3173(4) 0.2559(5) -0.05798(15) 0.0448(8) Uani 1 1 d . . . . .
C11 C 0.4532(4) 0.2517(4) -0.01632(15) 0.0409(8) Uani 1 1 d . . . . .
C12 C 0.4094(3) 0.2348(4) 0.04077(14) 0.0370(7) Uani 1 1 d . . . . .
C13 C 0.5135(4) 0.2290(5) 0.09019(17) 0.0486(8) Uani 1 1 d . . . . .
H13 H 0.483762 0.218851 0.128323 0.058 Uiso 1 1 calc R U . . .
C14 C 0.6650(4) 0.2389(6) 0.08094(19) 0.0587(10) Uani 1 1 d . . . . .
H14 H 0.737625 0.234914 0.113690 0.070 Uiso 1 1 calc R U . . .
C15 C 0.7112(4) 0.2546(5) 0.0245(2) 0.0581(10) Uani 1 1 d . . . . .
H15 H 0.813475 0.259682 0.019682 0.070 Uiso 1 1 calc R U . . .
C16 C 0.6049(4) 0.2628(5) -0.02470(18) 0.0523(9) Uani 1 1 d . . . . .
H16 H 0.634644 0.275520 -0.062775 0.063 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
O1 C3 1.370(4) . ?
O1 C2 1.421(4) . ?
O2 C9 1.212(4) . ?
O3 C10 1.207(4) . ?
N1 C9 1.359(4) . ?
N1 C12 1.415(4) . ?
N1 C1 1.456(4) . ?
C1 C2 1.497(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.378(5) . ?
C3 C4 1.380(5) . ?
C4 C5 1.377(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.554(5) . ?
C10 C11 1.453(5) . ?
C11 C16 1.387(5) . ?
C11 C12 1.391(5) . ?
C12 C13 1.374(5) . ?
C13 C14 1.389(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
C3 O1 C2 118.9(3) . . ?
C9 N1 C12 110.7(3) . . ?
C9 N1 C1 122.9(3) . . ?
C12 N1 C1 126.1(3) . . ?
N1 C1 C2 113.1(3) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
O1 C2 C1 107.1(3) . . ?
O1 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
O1 C3 C8 124.5(3) . . ?
O1 C3 C4 114.6(3) . . ?
C8 C3 C4 120.9(4) . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.2(4) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 118.5(4) . . ?
C3 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
O2 C9 N1 127.0(3) . . ?
O2 C9 C10 126.9(3) . . ?
N1 C9 C10 106.1(3) . . ?
O3 C10 C11 131.7(3) . . ?
O3 C10 C9 123.4(3) . . ?
C11 C10 C9 104.9(3) . . ?
C16 C11 C12 120.3(3) . . ?
C16 C11 C10 132.0(3) . . ?
C12 C11 C10 107.7(3) . . ?
C13 C12 C11 121.6(3) . . ?
C13 C12 N1 127.9(3) . . ?
C11 C12 N1 110.6(3) . . ?
C12 C13 C14 117.3(3) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 H13 121.3 . . ?
C15 C14 C13 122.1(4) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 118.9(4) . . ?
C15 C16 H16 120.6 . . ?
C11 C16 H16 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 -91.2(4) . . . . ?
C12 N1 C1 C2 94.9(4) . . . . ?
C3 O1 C2 C1 -174.4(3) . . . . ?
N1 C1 C2 O1 -62.7(4) . . . . ?
C2 O1 C3 C8 -1.8(5) . . . . ?
C2 O1 C3 C4 178.3(3) . . . . ?
O1 C3 C4 C5 -177.3(4) . . . . ?
C8 C3 C4 C5 2.8(6) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C4 C5 C6 C7 -2.6(8) . . . . ?
C5 C6 C7 C8 2.5(7) . . . . ?
O1 C3 C8 C7 177.2(3) . . . . ?
C4 C3 C8 C7 -2.9(5) . . . . ?
C6 C7 C8 C3 0.2(6) . . . . ?
C12 N1 C9 O2 179.1(3) . . . . ?
C1 N1 C9 O2 4.4(5) . . . . ?
C12 N1 C9 C10 -0.1(3) . . . . ?
C1 N1 C9 C10 -174.8(3) . . . . ?
O2 C9 C10 O3 0.3(5) . . . . ?
N1 C9 C10 O3 179.5(3) . . . . ?
O2 C9 C10 C11 -178.4(3) . . . . ?
N1 C9 C10 C11 0.8(3) . . . . ?
O3 C10 C11 C16 0.9(6) . . . . ?
C9 C10 C11 C16 179.5(3) . . . . ?
O3 C10 C11 C12 -179.7(4) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C16 C11 C12 C13 0.1(5) . . . . ?
C10 C11 C12 C13 -179.4(3) . . . . ?
C16 C11 C12 N1 -179.4(3) . . . . ?
C10 C11 C12 N1 1.2(3) . . . . ?
C9 N1 C12 C13 179.9(3) . . . . ?
C1 N1 C12 C13 -5.6(5) . . . . ?
C9 N1 C12 C11 -0.7(3) . . . . ?
C1 N1 C12 C11 173.8(3) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
N1 C12 C13 C14 178.8(3) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C14 C15 C16 C11 -1.1(5) . . . . ?
C12 C11 C16 C15 0.7(5) . . . . ?
C10 C11 C16 C15 -180.0(3) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_SM_8_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 2175053'
loop_
_audit_author_name
_audit_author_address
'Muhammad Usman Anwar'
;University of Nizwa
Oman
;
_audit_update_record             
;
2022-05-26 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 Cl F N O3'
_chemical_formula_sum            'C16 H11 Cl F N O3'
_chemical_formula_weight         319.71

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'
Cl Cl 0.1484 0.1585 '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'
F F 0.0171 0.0103 '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                   8.324(10)
_cell_length_b                   8.326(10)
_cell_length_c                   12.233(16)
_cell_angle_alpha                92.36(5)
_cell_angle_beta                 106.63(4)
_cell_angle_gamma                116.57(4)
_cell_volume                     712.2(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4619
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      24.47

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.291
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6735
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            16520
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.845
_diffrn_reflns_theta_max         26.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2928
_reflns_number_gt                1822
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0619P)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         2928
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Cl1 Cl 0.28927(10) 0.62311(10) 0.73392(6) 0.0585(2) Uani 1 1 d . . . . .
F1 F -0.2403(3) -0.0057(2) -0.14843(16) 0.0929(6) Uani 1 1 d . . . . .
O2 O 0.3178(2) 0.5986(2) 0.17792(12) 0.0420(4) Uani 1 1 d . . . . .
O3 O 0.9399(2) 0.8471(2) 0.37826(13) 0.0480(4) Uani 1 1 d . . . . .
O4 O 0.9415(2) 0.7351(2) 0.60351(14) 0.0495(5) Uani 1 1 d . . . . .
N1 N 0.6489(2) 0.8197(2) 0.37383(14) 0.0342(4) Uani 1 1 d . . . . .
C1 C -0.0962(4) 0.1439(4) -0.0680(2) 0.0551(7) Uani 1 1 d . . . . .
C2 C -0.1132(4) 0.1739(4) 0.0379(2) 0.0553(7) Uani 1 1 d . . . . .
H2 H -0.219356 0.092096 0.054787 0.066 Uiso 1 1 calc R U . . .
C3 C 0.0298(3) 0.3275(3) 0.1192(2) 0.0447(6) Uani 1 1 d . . . . .
H3 H 0.021104 0.350464 0.191705 0.054 Uiso 1 1 calc R U . . .
C4 C 0.1865(3) 0.4474(3) 0.09231(17) 0.0338(5) Uani 1 1 d . . . . .
C5 C 0.2017(4) 0.4122(3) -0.01471(18) 0.0442(6) Uani 1 1 d . . . . .
H5 H 0.308623 0.491642 -0.031892 0.053 Uiso 1 1 calc R U . . .
C6 C 0.0572(4) 0.2584(4) -0.0959(2) 0.0547(7) Uani 1 1 d . . . . .
H6 H 0.064780 0.233693 -0.168542 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4893(3) 0.7216(3) 0.16106(18) 0.0416(6) Uani 1 1 d . . . . .
H7A H 0.460934 0.766316 0.089828 0.050 Uiso 1 1 calc R U . . .
H7B H 0.563190 0.660672 0.155534 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5995(3) 0.8780(3) 0.26427(17) 0.0427(6) Uani 1 1 d . . . . .
H8A H 0.715835 0.967059 0.253776 0.051 Uiso 1 1 calc R U . . .
H8B H 0.523755 0.937704 0.267846 0.051 Uiso 1 1 calc R U . . .
C9 C 0.8155(3) 0.8131(3) 0.42051(18) 0.0355(5) Uani 1 1 d . . . . .
C10 C 0.8160(3) 0.7569(3) 0.53977(18) 0.0334(5) Uani 1 1 d . . . . .
C11 C 0.6380(3) 0.7364(3) 0.55087(16) 0.0293(5) Uani 1 1 d . . . . .
C12 C 0.5411(3) 0.7732(3) 0.45008(17) 0.0309(5) Uani 1 1 d . . . . .
C13 C 0.3665(3) 0.7638(3) 0.43531(19) 0.0396(6) Uani 1 1 d . . . . .
H13 H 0.301266 0.787932 0.368219 0.048 Uiso 1 1 calc R U . . .
C14 C 0.2913(3) 0.7171(3) 0.5241(2) 0.0410(6) Uani 1 1 d . . . . .
H14 H 0.173711 0.709959 0.516277 0.049 Uiso 1 1 calc R U . . .
C15 C 0.3884(3) 0.6808(3) 0.62422(19) 0.0359(5) Uani 1 1 d . . . . .
C16 C 0.5630(3) 0.6889(3) 0.63945(17) 0.0330(5) Uani 1 1 d . . . . .
H16 H 0.627457 0.663588 0.706260 0.040 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
Cl1 C15 1.745(3) . ?
F1 C1 1.359(3) . ?
O2 C4 1.372(3) . ?
O2 C7 1.417(3) . ?
O3 C9 1.214(3) . ?
O4 C10 1.203(3) . ?
N1 C9 1.368(3) . ?
N1 C12 1.422(3) . ?
N1 C8 1.455(3) . ?
C1 C6 1.358(4) . ?
C1 C2 1.368(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.383(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.381(4) . ?
C7 C8 1.505(3) . ?
C9 C10 1.550(4) . ?
C10 C11 1.461(3) . ?
C11 C16 1.386(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.389(4) . ?
C15 C16 1.381(3) . ?

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 O2 C7 118.66(18) . . ?
C9 N1 C12 110.60(19) . . ?
C9 N1 C8 123.16(19) . . ?
C12 N1 C8 126.14(19) . . ?
C6 C1 F1 119.1(3) . . ?
C6 C1 C2 122.6(2) . . ?
F1 C1 C2 118.3(3) . . ?
C1 C2 C3 118.8(3) . . ?
C2 C3 C4 119.7(2) . . ?
O2 C4 C3 115.0(2) . . ?
O2 C4 C5 124.6(2) . . ?
C3 C4 C5 120.4(2) . . ?
C6 C5 C4 119.6(2) . . ?
C1 C6 C5 118.9(2) . . ?
O2 C7 C8 107.11(19) . . ?
N1 C8 C7 112.9(2) . . ?
O3 C9 N1 127.2(2) . . ?
O3 C9 C10 126.7(2) . . ?
N1 C9 C10 106.17(19) . . ?
O4 C10 C11 131.1(2) . . ?
O4 C10 C9 123.7(2) . . ?
C11 C10 C9 105.17(18) . . ?
C16 C11 C12 121.6(2) . . ?
C16 C11 C10 130.8(2) . . ?
C12 C11 C10 107.57(19) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 N1 128.7(2) . . ?
C11 C12 N1 110.5(2) . . ?
C12 C13 C14 117.7(2) . . ?
C15 C14 C13 121.2(2) . . ?
C16 C15 C14 121.5(2) . . ?
C16 C15 Cl1 118.74(18) . . ?
C14 C15 Cl1 119.80(19) . . ?
C15 C16 C11 117.2(2) . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.066

