# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2143927'
loop_
_audit_author_name
_audit_author_address
'Nivetha Narayanasamy'
;NITT
India
;
_audit_update_record             
;
2022-01-23 deposited with the CCDC.	2022-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
(1'R,2'S,3R)-2'-(benzo[d][1,3]dioxole-5-carbonyl)-1'-(3-fluorophenyl)-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 F N2 O4'
_chemical_formula_weight         470.48

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

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

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

_cell_length_a                   9.9780(11)
_cell_length_b                   10.7417(12)
_cell_length_c                   12.4901(14)
_cell_angle_alpha                104.108(7)
_cell_angle_beta                 91.854(7)
_cell_angle_gamma                117.657(8)
_cell_volume                     1133.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11034
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11826
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5167
_reflns_number_gt                4306
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0737P)²+0.4722P] 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         5167
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.32849(13) 0.53368(13) 0.00826(10) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.21198(14) 0.55766(14) 0.39529(10) 0.0294(3) Uani 1 1 d . . . . .
F1 F -0.18112(19) 0.79867(17) 0.22158(14) 0.0593(4) Uani 1 1 d . . . . .
N2 N 0.02887(14) 0.31052(14) 0.04191(11) 0.0181(3) Uani 1 1 d . . . . .
O3 O 0.73476(15) 1.03042(15) 0.52655(13) 0.0384(3) Uani 1 1 d . . . . .
O4 O 0.79187(16) 1.12702(15) 0.37727(14) 0.0441(4) Uani 1 1 d . . . . .
N1 N 0.41024(16) 0.41302(17) 0.09885(12) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.497370 0.437413 0.076792 0.029 Uiso 1 1 calc R U . . .
C18 C 0.21128(18) 0.30603(17) 0.19066(13) 0.0196(3) Uani 1 1 d . . . . .
C12 C 0.16873(17) 0.39105(17) 0.12734(13) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.14126(17) 0.51364(16) 0.20130(13) 0.0166(3) Uani 1 1 d . . . . .
H9 H 0.151681 0.582384 0.158846 0.020 Uiso 1 1 calc R U . . .
C23 C -0.10093(17) 0.51662(17) 0.26254(13) 0.0184(3) Uani 1 1 d . . . . .
C10 C -0.02875(17) 0.42570(16) 0.20979(13) 0.0170(3) Uani 1 1 d . . . . .
H10 H -0.039327 0.357904 0.253203 0.020 Uiso 1 1 calc R U . . .
C16 C 0.31090(17) 0.45615(17) 0.06960(13) 0.0191(3) Uani 1 1 d . . . . .
C8 C 0.24706(18) 0.60075(17) 0.31369(13) 0.0190(3) Uani 1 1 d . . . . .
C4 C 0.39056(18) 0.74034(17) 0.32306(14) 0.0203(3) Uani 1 1 d . . . . .
C28 C -0.16619(19) 0.49513(19) 0.35803(14) 0.0224(3) Uani 1 1 d . . . . .
H28 H -0.162723 0.426534 0.389668 0.027 Uiso 1 1 calc R U . . .
C11 C -0.09562(17) 0.33637(17) 0.08644(13) 0.0190(3) Uani 1 1 d . . . . .
H11 H -0.117989 0.394360 0.046481 0.023 Uiso 1 1 calc R U . . .
C17 C 0.35421(19) 0.32354(19) 0.16962(14) 0.0226(3) Uani 1 1 d . . . . .
C3 C 0.48898(19) 0.81270(18) 0.42760(15) 0.0231(3) Uani 1 1 d . . . . .
H3 H 0.465798 0.775162 0.488313 0.028 Uiso 1 1 calc R U . . .
C24 C -0.1054(2) 0.62087(19) 0.21645(15) 0.0252(4) Uani 1 1 d . . . . .
H24 H -0.062057 0.637736 0.153122 0.030 Uiso 1 1 calc R U . . .
C2 C 0.62022(19) 0.94080(18) 0.43544(16) 0.0256(4) Uani 1 1 d . . . . .
C19 C 0.1372(2) 0.22043(19) 0.25921(15) 0.0253(4) Uani 1 1 d . . . . .
H19 H 0.042324 0.208159 0.275541 0.030 Uiso 1 1 calc R U . . .
C15 C -0.0333(2) 0.15162(18) -0.00868(15) 0.0261(4) Uani 1 1 d . . . . .
H15A H 0.042290 0.122630 0.006829 0.031 Uiso 1 1 calc R U . . .
H15B H -0.062144 0.125130 -0.089191 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6555(2) 0.99888(19) 0.34644(17) 0.0299(4) Uani 1 1 d . . . . .
C5 C 0.4272(2) 0.79968(19) 0.23438(15) 0.0288(4) Uani 1 1 d . . . . .
H5 H 0.360676 0.750449 0.166106 0.035 Uiso 1 1 calc R U . . .
C22 C 0.4258(2) 0.2592(2) 0.21355(16) 0.0295(4) Uani 1 1 d . . . . .
H22 H 0.521904 0.273559 0.198785 0.035 Uiso 1 1 calc R U . . .
C20 C 0.2064(2) 0.1528(2) 0.30348(15) 0.0295(4) Uani 1 1 d . . . . .
H20 H 0.156560 0.094190 0.348769 0.035 Uiso 1 1 calc R U . . .
C13 C -0.23690(19) 0.18358(19) 0.06364(16) 0.0278(4) Uani 1 1 d . . . . .
H13A H -0.290430 0.177567 0.127236 0.033 Uiso 1 1 calc R U . . .
H13B H -0.307375 0.162181 -0.002041 0.033 Uiso 1 1 calc R U . . .
C27 C -0.2363(2) 0.5753(2) 0.40624(16) 0.0302(4) Uani 1 1 d . . . . .
H27 H -0.279316 0.559956 0.469943 0.036 Uiso 1 1 calc R U . . .
C26 C -0.2427(2) 0.6776(2) 0.36042(18) 0.0353(5) Uani 1 1 d . . . . .
H26 H -0.290592 0.730824 0.391575 0.042 Uiso 1 1 calc R U . . .
C21 C 0.3485(2) 0.1723(2) 0.28062(16) 0.0321(4) Uani 1 1 d . . . . .
H21 H 0.392805 0.126221 0.310746 0.038 Uiso 1 1 calc R U . . .
C25 C -0.1756(2) 0.6979(2) 0.26711(18) 0.0332(4) Uani 1 1 d . . . . .
C6 C 0.5611(2) 0.9313(2) 0.24478(18) 0.0377(5) Uani 1 1 d . . . . .
H6 H 0.584973 0.971201 0.185250 0.045 Uiso 1 1 calc R U . . .
C1 C 0.8510(2) 1.1404(2) 0.4876(2) 0.0432(5) Uani 1 1 d . . . . .
H1A H 0.941151 1.127871 0.486512 0.052 Uiso 1 1 calc R U . . .
H1B H 0.880145 1.237169 0.537148 0.052 Uiso 1 1 calc R U . . .
C14 C -0.1733(2) 0.0773(2) 0.0445(2) 0.0395(5) Uani 1 1 d . . . . .
H14A H -0.144528 0.065190 0.114610 0.047 Uiso 1 1 calc R U . . .
H14B H -0.247469 -0.018038 -0.005440 0.047 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 C16 1.2229(19) . ?
O2 C8 1.2159(19) . ?
F1 C25 1.360(2) . ?
N2 C15 1.471(2) . ?
N2 C12 1.472(2) . ?
N2 C11 1.4896(19) . ?
O3 C2 1.374(2) . ?
O3 C1 1.422(3) . ?
O4 C7 1.365(2) . ?
O4 C1 1.428(3) . ?
N1 C16 1.348(2) . ?
N1 C17 1.402(2) . ?
N1 H1 0.8600 . ?
C18 C19 1.385(2) . ?
C18 C17 1.392(2) . ?
C18 C12 1.527(2) . ?
C12 C16 1.553(2) . ?
C12 C9 1.556(2) . ?
C9 C8 1.519(2) . ?
C9 C10 1.534(2) . ?
C9 H9 0.9800 . ?
C23 C28 1.395(2) . ?
C23 C24 1.395(2) . ?
C23 C10 1.509(2) . ?
C10 C11 1.535(2) . ?
C10 H10 0.9800 . ?
C8 C4 1.491(2) . ?
C4 C5 1.386(2) . ?
C4 C3 1.410(2) . ?
C28 C27 1.388(2) . ?
C28 H28 0.9300 . ?
C11 C13 1.536(2) . ?
C11 H11 0.9800 . ?
C17 C22 1.381(2) . ?
C3 C2 1.368(2) . ?
C3 H3 0.9300 . ?
C24 C25 1.374(2) . ?
C24 H24 0.9300 . ?
C2 C7 1.381(3) . ?
C19 C20 1.395(2) . ?
C19 H19 0.9300 . ?
C15 C14 1.520(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C7 C6 1.366(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C22 C21 1.387(3) . ?
C22 H22 0.9300 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C13 C14 1.521(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C27 C26 1.382(3) . ?
C27 H27 0.9300 . ?
C26 C25 1.376(3) . ?
C26 H26 0.9300 . ?
C21 H21 0.9300 . ?
C6 H6 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
C15 N2 C12 118.53(13) . . ?
C15 N2 C11 108.62(12) . . ?
C12 N2 C11 110.07(12) . . ?
C2 O3 C1 105.63(16) . . ?
C7 O4 C1 105.46(16) . . ?
C16 N1 C17 111.74(13) . . ?
C16 N1 H1 124.1 . . ?
C17 N1 H1 124.1 . . ?
C19 C18 C17 118.60(15) . . ?
C19 C18 C12 133.14(14) . . ?
C17 C18 C12 108.25(13) . . ?
N2 C12 C18 118.95(13) . . ?
N2 C12 C16 109.05(12) . . ?
C18 C12 C16 101.31(12) . . ?
N2 C12 C9 100.81(11) . . ?
C18 C12 C9 115.38(13) . . ?
C16 C12 C9 111.54(12) . . ?
C8 C9 C10 114.16(12) . . ?
C8 C9 C12 115.92(12) . . ?
C10 C9 C12 101.25(12) . . ?
C8 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C12 C9 H9 108.4 . . ?
C28 C23 C24 119.25(14) . . ?
C28 C23 C10 119.69(14) . . ?
C24 C23 C10 121.05(14) . . ?
C23 C10 C9 115.24(13) . . ?
C23 C10 C11 115.32(13) . . ?
C9 C10 C11 100.14(12) . . ?
C23 C10 H10 108.6 . . ?
C9 C10 H10 108.6 . . ?
C11 C10 H10 108.6 . . ?
O1 C16 N1 126.29(14) . . ?
O1 C16 C12 125.19(14) . . ?
N1 C16 C12 108.51(13) . . ?
O2 C8 C4 120.86(15) . . ?
O2 C8 C9 119.66(14) . . ?
C4 C8 C9 119.46(13) . . ?
C5 C4 C3 120.37(15) . . ?
C5 C4 C8 122.42(15) . . ?
C3 C4 C8 117.21(14) . . ?
C27 C28 C23 120.54(16) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
N2 C11 C10 104.62(12) . . ?
N2 C11 C13 105.93(12) . . ?
C10 C11 C13 116.67(13) . . ?
N2 C11 H11 109.8 . . ?
C10 C11 H11 109.8 . . ?
C13 C11 H11 109.8 . . ?
C22 C17 C18 123.15(16) . . ?
C22 C17 N1 126.67(15) . . ?
C18 C17 N1 110.18(14) . . ?
C2 C3 C4 116.78(16) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C25 C24 C23 118.23(16) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C3 C2 O3 128.15(17) . . ?
C3 C2 C7 122.34(17) . . ?
O3 C2 C7 109.51(15) . . ?
C18 C19 C20 119.31(16) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
N2 C15 C14 105.84(14) . . ?
N2 C15 H15A 110.6 . . ?
C14 C15 H15A 110.6 . . ?
N2 C15 H15B 110.6 . . ?
C14 C15 H15B 110.6 . . ?
H15A C15 H15B 108.7 . . ?
O4 C7 C6 127.99(18) . . ?
O4 C7 C2 110.17(17) . . ?
C6 C7 C2 121.84(16) . . ?
C4 C5 C6 121.78(17) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C17 C22 C21 117.21(16) . . ?
C17 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C21 C20 C19 120.59(17) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C14 C13 C11 104.96(14) . . ?
C14 C13 H13A 110.8 . . ?
C11 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C11 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C26 C27 C28 120.58(16) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C25 C26 C27 117.68(16) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C20 C21 C22 121.12(16) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
F1 C25 C24 118.22(17) . . ?
F1 C25 C26 118.06(16) . . ?
C24 C25 C26 123.72(17) . . ?
C7 C6 C5 116.89(18) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
O3 C1 O4 108.34(15) . . ?
O3 C1 H1A 110.0 . . ?
O4 C1 H1A 110.0 . . ?
O3 C1 H1B 110.0 . . ?
O4 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C15 C14 C13 103.16(15) . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?

_refine_diff_density_max         1.231
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
