# 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. 
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data_mo_jd090823_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2356047'
loop_
_audit_author_name
_audit_author_address
'Jyotirmayee Dash'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-05-17 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_audit_creation_date             2024-03-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        SPIROOXINDOLE1
_chemical_formula_moiety         'C20 H18 N3.985 O2'
_chemical_formula_sum            'C20 H18 N4 O2'
_chemical_formula_weight         346.38
_chemical_absolute_configuration ?
_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'
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.083(15)
_cell_length_b                   19.232(17)
_cell_length_c                   5.595(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1731(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7252
_cell_measurement_temperature    169.04
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1387 before and 0.0969 after correction.
The Ratio of minimum to maximum transmission is 0.8422.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_preparation       'Slow evaporation'
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            17927
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.711
_diffrn_reflns_theta_min         2.468
_diffrn_ambient_temperature      169.04
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          multiscan
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_full    0.783
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                2497
_reflns_number_total             2941
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 878 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       0.041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.063
_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)+(0.0339P)²+0.3624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C14(H14A,H14B)
1.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C16(H16), C10(H10), C20(H20), C19(H19), C17(H17), C18(H18)
1.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O2 O 0.41089(13) 0.51086(12) 1.0440(4) 0.0526(6) Uani 1 1 d . . . . .
O1 O 0.11562(13) 0.49561(12) 0.0911(5) 0.0559(6) Uani 1 1 d . . . . .
N2 N 0.32679(14) 0.57900(12) 0.8106(5) 0.0419(6) Uani 1 1 d . . . . .
N3 N 0.31366(16) 0.34080(12) 0.7044(5) 0.0442(10) Uani 0.985(9) 1 d . . . . .
N1 N 0.28943(18) 0.27380(13) 0.6981(6) 0.0555(8) Uani 1 1 d . . . . .
N4 N 0.33202(18) 0.24623(14) 0.5173(6) 0.0575(8) Uani 1 1 d . . . . .
C2 C 0.39813(18) 0.42851(15) 0.5665(7) 0.0411(7) Uani 1 1 d . . . . .
C12 C 0.26907(17) 0.56854(14) 0.6228(5) 0.0375(7) Uani 1 1 d . . . . .
C7 C 0.26419(15) 0.49786(14) 0.5707(6) 0.0338(6) Uani 1 1 d . . . . .
C C 0.36987(17) 0.35585(15) 0.5397(6) 0.0414(7) Uani 1 1 d . . . A 2
C15 C 0.38921(18) 0.69569(15) 0.7546(6) 0.0414(7) Uani 1 1 d . . . B 1
C6 C 0.36033(18) 0.51831(15) 0.8828(5) 0.0394(7) Uani 1 1 d . . . . .
C4 C 0.32704(16) 0.46021(13) 0.7234(5) 0.0350(7) Uani 1 1 d . . . . .
C8 C 0.21195(17) 0.47454(15) 0.3956(6) 0.0380(7) Uani 1 1 d . . . . .
H8 H 0.207569 0.426305 0.361221 0.046 Uiso 1 1 calc R U . . .
C9 C 0.16506(17) 0.52334(16) 0.2682(6) 0.0400(7) Uani 1 1 d . . . . .
C11 C 0.22341(19) 0.61664(15) 0.5002(6) 0.0466(8) Uani 1 1 d . . . . .
H11 H 0.227316 0.664752 0.537051 0.056 Uiso 1 1 calc R U . . .
C16 C 0.4324(2) 0.67355(17) 0.5545(7) 0.0527(8) Uani 1 1 d . . . B 1
H16 H 0.434540 0.625384 0.517307 0.063 Uiso 1 1 calc R U . B 1
C5 C 0.29196(18) 0.39805(15) 0.8658(6) 0.0423(7) Uani 1 1 d . . . . .
H5A H 0.319404 0.393140 1.023268 0.051 Uiso 1 1 calc R U . . .
H5B H 0.231085 0.401873 0.888530 0.051 Uiso 1 1 calc R U . . .
C14 C 0.3442(2) 0.64590(15) 0.9176(6) 0.0479(8) Uani 1 1 d . . . . .
H14A H 0.378241 0.638626 1.062920 0.057 Uiso 1 1 calc R U . B 1
H14B H 0.291068 0.667375 0.967839 0.057 Uiso 1 1 calc R U . B 1
C3 C 0.3815(2) 0.29545(17) 0.4184(7) 0.0491(8) Uani 1 1 d . . . . .
C10 C 0.17085(18) 0.59301(16) 0.3191(7) 0.0467(8) Uani 1 1 d . . . . .
H10 H 0.138772 0.625442 0.230263 0.056 Uiso 1 1 calc R U . . .
C20 C 0.3874(2) 0.76582(16) 0.8067(8) 0.0551(9) Uani 1 1 d . . . B 1
H20 H 0.358132 0.781759 0.943620 0.066 Uiso 1 1 calc R U . B 1
C13 C 0.0687(2) 0.5434(2) -0.0506(7) 0.0657(11) Uani 1 1 d . . . . .
H13A H 0.038022 0.517821 -0.173688 0.099 Uiso 1 1 calc R U . . .
H13B H 0.106582 0.576579 -0.126993 0.099 Uiso 1 1 calc R U . . .
H13C H 0.029485 0.568546 0.051710 0.099 Uiso 1 1 calc R U . . .
C19 C 0.4279(2) 0.81315(18) 0.6608(9) 0.0672(12) Uani 1 1 d . . . B 1
H19 H 0.426201 0.861343 0.697710 0.081 Uiso 1 1 calc R U . B 1
C17 C 0.4725(2) 0.7208(2) 0.4083(7) 0.0647(10) Uani 1 1 d . . . B 1
H17 H 0.501303 0.705222 0.270161 0.078 Uiso 1 1 calc R U . B 1
C18 C 0.4705(2) 0.7906(2) 0.4631(8) 0.0673(11) Uani 1 1 d . . . B 1
H18 H 0.498591 0.823046 0.363992 0.081 Uiso 1 1 calc R U . B 1
H3 H 0.417(2) 0.287(2) 0.272(8) 0.080(13) Uiso 1 1 d . . . . .
H2A H 0.4071(19) 0.4537(16) 0.401(7) 0.052(9) Uiso 1 1 d . . . . .
H2B H 0.450(2) 0.4292(16) 0.654(7) 0.061(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
O2 C6 1.223(4) . ?
O1 C9 1.378(4) . ?
O1 C13 1.429(4) . ?
N2 C12 1.416(4) . ?
N2 C6 1.348(4) . ?
N2 C14 1.447(4) . ?
N3 N1 1.347(3) . ?
N3 C 1.323(4) . ?
N3 C5 1.466(4) . ?
N1 N4 1.332(4) . ?
N4 C3 1.354(4) . ?
C2 C 1.477(4) . ?
C2 C4 1.565(4) . ?
C2 H2A 1.06(4) . ?
C2 H2B 0.97(4) . ?
C12 C7 1.392(4) . ?
C12 C11 1.366(4) . ?
C7 C4 1.509(4) . ?
C7 C8 1.366(4) . ?
C C3 1.358(5) . ?
C15 C16 1.385(5) . ?
C15 C14 1.508(4) . ?
C15 C20 1.380(4) . ?
C6 C4 1.527(4) . ?
C4 C5 1.543(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.399(4) . ?
C9 C10 1.373(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.395(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C3 H3 1.01(4) . ?
C10 H10 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.386(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C18 1.371(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(6) . ?
C18 H18 0.9500 . ?

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
C9 O1 C13 117.0(3) . . ?
C12 N2 C14 124.1(3) . . ?
C6 N2 C12 111.2(2) . . ?
C6 N2 C14 124.6(3) . . ?
N1 N3 C5 131.7(3) . . ?
C N3 N1 112.9(3) . . ?
C N3 C5 115.3(2) . . ?
N4 N1 N3 104.6(3) . . ?
N1 N4 C3 109.5(3) . . ?
C C2 C4 101.6(2) . . ?
C C2 H2A 112.7(18) . . ?
C C2 H2B 109.2(18) . . ?
C4 C2 H2A 114.4(17) . . ?
C4 C2 H2B 110(2) . . ?
H2A C2 H2B 109(3) . . ?
C7 C12 N2 109.3(2) . . ?
C11 C12 N2 129.0(3) . . ?
C11 C12 C7 121.7(3) . . ?
C12 C7 C4 108.2(2) . . ?
C8 C7 C12 120.4(3) . . ?
C8 C7 C4 131.3(3) . . ?
N3 C C2 110.3(3) . . ?
N3 C C3 104.8(3) . . ?
C3 C C2 144.8(3) . . ?
C16 C15 C14 122.3(3) . . ?
C20 C15 C16 118.8(3) . . ?
C20 C15 C14 118.9(3) . . ?
O2 C6 N2 126.1(3) . . ?
O2 C6 C4 125.3(3) . . ?
N2 C6 C4 108.6(3) . . ?
C7 C4 C2 111.0(3) . . ?
C7 C4 C6 102.4(2) . . ?
C7 C4 C5 114.8(2) . . ?
C6 C4 C2 110.9(2) . . ?
C6 C4 C5 113.2(3) . . ?
C5 C4 C2 104.8(2) . . ?
C7 C8 H8 120.8 . . ?
C7 C8 C9 118.5(3) . . ?
C9 C8 H8 120.8 . . ?
O1 C9 C8 114.7(3) . . ?
C10 C9 O1 124.5(3) . . ?
C10 C9 C8 120.8(3) . . ?
C12 C11 H11 121.0 . . ?
C12 C11 C10 118.0(3) . . ?
C10 C11 H11 121.0 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
N3 C5 C4 100.2(2) . . ?
N3 C5 H5A 111.7 . . ?
N3 C5 H5B 111.7 . . ?
C4 C5 H5A 111.7 . . ?
C4 C5 H5B 111.7 . . ?
H5A C5 H5B 109.5 . . ?
N2 C14 C15 114.0(3) . . ?
N2 C14 H14A 108.7 . . ?
N2 C14 H14B 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
N4 C3 C 108.2(3) . . ?
N4 C3 H3 123(2) . . ?
C C3 H3 128(2) . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C15 C20 H20 119.7 . . ?
C15 C20 C19 120.5(4) . . ?
C19 C20 H20 119.7 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C20 C19 H19 119.9 . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 119.9 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?

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 C6 C4 C2 -64.8(4) . . . . ?
O2 C6 C4 C7 176.7(3) . . . . ?
O2 C6 C4 C5 52.6(4) . . . . ?
O1 C9 C10 C11 -179.2(3) . . . . ?
N2 C12 C7 C4 -3.9(3) . . . . ?
N2 C12 C7 C8 179.6(3) . . . . ?
N2 C12 C11 C10 179.4(3) . . . . ?
N2 C6 C4 C2 113.1(3) . . . . ?
N2 C6 C4 C7 -5.4(3) . . . . ?
N2 C6 C4 C5 -129.5(3) . . . . ?
N3 N1 N4 C3 0.6(3) . . . . ?
N3 C C3 N4 -0.6(3) . . . . ?
N1 N3 C C2 -176.1(3) . . . . ?
N1 N3 C C3 1.0(3) . . . . ?
N1 N3 C5 C4 -167.1(3) . . . . ?
N1 N4 C3 C 0.0(4) . . . . ?
C2 C C3 N4 174.7(4) . . . . ?
C2 C4 C5 N3 -25.8(3) . . . . ?
C12 N2 C6 O2 -178.7(3) . . . . ?
C12 N2 C6 C4 3.3(3) . . . . ?
C12 N2 C14 C15 -68.9(4) . . . . ?
C12 C7 C4 C2 -112.9(3) . . . . ?
C12 C7 C4 C6 5.5(3) . . . . ?
C12 C7 C4 C5 128.6(3) . . . . ?
C12 C7 C8 C9 1.2(4) . . . . ?
C12 C11 C10 C9 0.5(5) . . . . ?
C7 C12 C11 C10 0.1(4) . . . . ?
C7 C4 C5 N3 96.2(3) . . . . ?
C7 C8 C9 O1 178.5(3) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C N3 N1 N4 -1.0(3) . . . . ?
C N3 C5 C4 16.2(3) . . . . ?
C C2 C4 C7 -97.5(3) . . . . ?
C C2 C4 C6 149.4(2) . . . . ?
C C2 C4 C5 27.0(3) . . . . ?
C15 C16 C17 C18 0.9(6) . . . . ?
C15 C20 C19 C18 -0.2(6) . . . . ?
C6 N2 C12 C7 0.4(3) . . . . ?
C6 N2 C12 C11 -178.9(3) . . . . ?
C6 N2 C14 C15 114.2(3) . . . . ?
C6 C4 C5 N3 -146.7(2) . . . . ?
C4 C2 C N3 -17.9(3) . . . . ?
C4 C2 C C3 167.0(4) . . . . ?
C4 C7 C8 C9 -174.3(3) . . . . ?
C8 C7 C4 C2 63.0(4) . . . . ?
C8 C7 C4 C6 -178.6(3) . . . . ?
C8 C7 C4 C5 -55.5(4) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C11 C12 C7 C4 175.4(3) . . . . ?
C11 C12 C7 C8 -1.0(4) . . . . ?
C16 C15 C14 N2 -19.2(4) . . . . ?
C16 C15 C20 C19 0.2(5) . . . . ?
C16 C17 C18 C19 -0.9(6) . . . . ?
C5 N3 N1 N4 -177.8(3) . . . . ?
C5 N3 C C2 1.2(3) . . . . ?
C5 N3 C C3 178.3(2) . . . . ?
C14 N2 C12 C7 -176.9(3) . . . . ?
C14 N2 C12 C11 3.8(5) . . . . ?
C14 N2 C6 O2 -1.5(5) . . . . ?
C14 N2 C6 C4 -179.4(3) . . . . ?
C14 C15 C16 C17 179.6(3) . . . . ?
C14 C15 C20 C19 -179.9(3) . . . . ?
C20 C15 C16 C17 -0.5(5) . . . . ?
C20 C15 C14 N2 160.9(3) . . . . ?
C20 C19 C18 C17 0.5(6) . . . . ?
C13 O1 C9 C8 -177.7(3) . . . . ?
C13 O1 C9 C10 1.2(4) . . . . ?

_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_mo_jd260923_0m
_database_code_depnum_ccdc_archive 'CCDC 2356048'
loop_
_audit_author_name
_audit_author_address
'Jyotirmayee Dash'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-05-17 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_audit_creation_date             2024-02-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        Spirooxindole2
_chemical_formula_moiety         'C17 H18 N4 O'
_chemical_formula_sum            'C17 H18 N4 O'
_chemical_formula_weight         294.35
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.422(4)
_cell_length_b                   20.895(10)
_cell_length_c                   7.919(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.630(18)
_cell_angle_gamma                90
_cell_volume                     1493.7(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5827
_cell_measurement_temperature    229.07
_cell_measurement_theta_max      28.378
_cell_measurement_theta_min      2.272
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1690 before and 0.1211 after correction.
The Ratio of minimum to maximum transmission is 0.3615.
The λ/2 correction factor is Not present.
;
_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    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16226
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.388
_diffrn_reflns_theta_min         2.256
_diffrn_ambient_temperature      229.07
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_special_details          Multiscan
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2752
_reflns_number_total             3717
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0672
_refine_ls_restrained_S_all      1.032
_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)+(0.0902P)²+0.4189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1874
_refine_special_details          Multiscan
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C14(H14), C6(H6), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.26577(17) 0.49743(7) 0.3631(2) 0.0439(4) Uani 1 1 d . . . . .
N1 N 0.08112(17) 0.42885(7) 0.3889(2) 0.0275(4) Uani 1 1 d . . . . .
N2 N 0.59876(17) 0.36238(8) 0.8807(2) 0.0287(4) Uani 1 1 d . . . . .
N3 N 0.6511(2) 0.33324(9) 1.0398(2) 0.0374(4) Uani 1 1 d . . . . .
N4 N 0.5819(2) 0.35891(9) 1.1467(2) 0.0412(5) Uani 1 1 d . . . . .
C8 C 0.2244(2) 0.45038(9) 0.4291(3) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.2117(2) 0.35875(8) 0.6028(2) 0.0241(4) Uani 1 1 d . . . . .
C3 C 0.0708(2) 0.37374(8) 0.4897(2) 0.0253(4) Uani 1 1 d . . . . .
C11 C 0.4120(2) 0.44521(9) 0.7261(3) 0.0277(4) Uani 1 1 d . . . . .
H11A H 0.482963 0.472086 0.689175 0.033 Uiso 1 1 calc R U . . .
H11B H 0.342841 0.473706 0.761318 0.033 Uiso 1 1 calc R U . . .
C7 C 0.32402(19) 0.40462(8) 0.5664(2) 0.0244(4) Uani 1 1 d . . . . .
C1 C 0.2261(2) 0.30679(9) 0.7164(3) 0.0292(4) Uani 1 1 d . . . . .
H1 H 0.318785 0.296430 0.794607 0.035 Uiso 1 1 calc R U . . .
C4 C -0.0550(2) 0.33767(9) 0.4823(3) 0.0311(4) Uani 1 1 d . . . . .
H4 H -0.147869 0.348130 0.404636 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4944(2) 0.40655(9) 0.8831(3) 0.0275(4) Uani 1 1 d . . . . .
C5 C -0.0366(2) 0.28485(9) 0.5965(3) 0.0335(5) Uani 1 1 d . . . . .
H5 H -0.118717 0.258969 0.594303 0.040 Uiso 1 1 calc R U . . .
C9 C 0.4283(2) 0.37195(9) 0.4709(2) 0.0292(4) Uani 1 1 d . . . . .
H9A H 0.366231 0.352487 0.362131 0.035 Uiso 1 1 calc R U . . .
H9B H 0.487262 0.405484 0.436517 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4846(2) 0.40357(10) 1.0530(3) 0.0343(5) Uani 1 1 d . . . . .
H14 H 0.420678 0.428495 1.097998 0.041 Uiso 1 1 calc R U . . .
C6 C 0.1009(2) 0.27012(9) 0.7128(3) 0.0338(5) Uani 1 1 d . . . . .
H6 H 0.109817 0.235143 0.789740 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5351(2) 0.32050(10) 0.5727(3) 0.0329(4) Uani 1 1 d . . . . .
H10A H 0.477299 0.287679 0.611922 0.039 Uiso 1 1 calc R U . . .
H10B H 0.582584 0.299966 0.491671 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6565(2) 0.34446(10) 0.7335(3) 0.0342(5) Uani 1 1 d . . . . .
H12A H 0.731144 0.310825 0.772769 0.041 Uiso 1 1 calc R U . . .
H12B H 0.705192 0.381674 0.699272 0.041 Uiso 1 1 calc R U . . .
C15 C -0.0420(2) 0.45800(10) 0.2553(3) 0.0352(5) Uani 1 1 d . . . . .
H15A H -0.027309 0.504454 0.257573 0.042 Uiso 1 1 calc R U . . .
H15B H -0.133942 0.449596 0.285890 0.042 Uiso 1 1 calc R U . . .
C16 C -0.0596(3) 0.43423(10) 0.0710(3) 0.0404(5) Uani 1 1 d . . . . .
H16 H -0.139836 0.450610 -0.018393 0.048 Uiso 1 1 calc R U . . .
C17 C 0.0259(3) 0.39305(12) 0.0235(4) 0.0472(6) Uani 1 1 d . . . . .
H17A H 0.004(4) 0.3803(15) -0.101(5) 0.077(10) Uiso 1 1 d . . . . .
H17B H 0.111(3) 0.3727(12) 0.112(3) 0.044(7) 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
O2 C8 1.228(2) . ?
N1 C8 1.371(2) . ?
N1 C3 1.420(2) . ?
N1 C15 1.461(2) . ?
N2 N3 1.358(2) . ?
N2 C13 1.352(2) . ?
N2 C12 1.469(2) . ?
N3 N4 1.322(3) . ?
N4 C14 1.368(3) . ?
C8 C7 1.547(3) . ?
C2 C3 1.408(3) . ?
C2 C7 1.515(2) . ?
C2 C1 1.392(3) . ?
C3 C4 1.392(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C7 1.551(3) . ?
C11 C13 1.499(3) . ?
C7 C9 1.558(3) . ?
C1 H1 0.9400 . ?
C1 C6 1.400(3) . ?
C4 H4 0.9400 . ?
C4 C5 1.406(3) . ?
C13 C14 1.376(3) . ?
C5 H5 0.9400 . ?
C5 C6 1.392(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 C10 1.535(3) . ?
C14 H14 0.9400 . ?
C6 H6 0.9400 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 C12 1.531(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 C16 1.504(3) . ?
C16 H16 0.9400 . ?
C16 C17 1.305(4) . ?
C17 H17A 0.98(4) . ?
C17 H17B 1.00(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
C8 N1 C3 110.91(15) . . ?
C8 N1 C15 123.78(16) . . ?
C3 N1 C15 125.28(16) . . ?
N3 N2 C12 120.20(16) . . ?
C13 N2 N3 111.44(16) . . ?
C13 N2 C12 128.36(17) . . ?
N4 N3 N2 107.29(17) . . ?
N3 N4 C14 107.84(17) . . ?
O2 C8 N1 125.15(18) . . ?
O2 C8 C7 126.22(17) . . ?
N1 C8 C7 108.61(15) . . ?
C3 C2 C7 108.72(15) . . ?
C1 C2 C3 118.97(17) . . ?
C1 C2 C7 132.26(17) . . ?
C2 C3 N1 109.53(15) . . ?
C4 C3 N1 127.57(17) . . ?
C4 C3 C2 122.90(17) . . ?
H11A C11 H11B 107.6 . . ?
C7 C11 H11A 108.7 . . ?
C7 C11 H11B 108.7 . . ?
C13 C11 H11A 108.7 . . ?
C13 C11 H11B 108.7 . . ?
C13 C11 C7 114.24(16) . . ?
C8 C7 C11 108.08(15) . . ?
C8 C7 C9 105.65(15) . . ?
C2 C7 C8 102.03(14) . . ?
C2 C7 C11 115.44(15) . . ?
C2 C7 C9 112.76(15) . . ?
C11 C7 C9 111.81(15) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.22(18) . . ?
C6 C1 H1 120.4 . . ?
C3 C4 H4 121.6 . . ?
C3 C4 C5 116.83(18) . . ?
C5 C4 H4 121.6 . . ?
N2 C13 C11 124.22(17) . . ?
N2 C13 C14 103.59(17) . . ?
C14 C13 C11 132.15(18) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.26(18) . . ?
C6 C5 H5 119.4 . . ?
C7 C9 H9A 107.9 . . ?
C7 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 C7 117.50(16) . . ?
C10 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
N4 C14 C13 109.83(18) . . ?
N4 C14 H14 125.1 . . ?
C13 C14 H14 125.1 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.78(18) . . ?
C5 C6 H6 119.6 . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C12 C10 C9 115.43(17) . . ?
C12 C10 H10A 108.4 . . ?
C12 C10 H10B 108.4 . . ?
N2 C12 C10 112.67(16) . . ?
N2 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C10 C12 H12A 109.1 . . ?
C10 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N1 C15 H15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
N1 C15 C16 114.17(18) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16 116.9 . . ?
C17 C16 C15 126.2(2) . . ?
C17 C16 H16 116.9 . . ?
C16 C17 H17A 119.8(19) . . ?
C16 C17 H17B 121.4(15) . . ?
H17A C17 H17B 119(2) . . ?

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 C8 C7 C2 177.58(19) . . . . ?
O2 C8 C7 C11 55.5(3) . . . . ?
O2 C8 C7 C9 -64.4(2) . . . . ?
N1 C8 C7 C2 -3.93(19) . . . . ?
N1 C8 C7 C11 -126.04(16) . . . . ?
N1 C8 C7 C9 114.14(17) . . . . ?
N1 C3 C4 C5 -179.96(17) . . . . ?
N1 C15 C16 C17 -2.3(3) . . . . ?
N2 N3 N4 C14 0.8(2) . . . . ?
N2 C13 C14 N4 0.3(2) . . . . ?
N3 N2 C13 C11 -177.88(17) . . . . ?
N3 N2 C13 C14 0.2(2) . . . . ?
N3 N2 C12 C10 121.5(2) . . . . ?
N3 N4 C14 C13 -0.7(2) . . . . ?
C8 N1 C3 C2 1.0(2) . . . . ?
C8 N1 C3 C4 -178.23(18) . . . . ?
C8 N1 C15 C16 85.0(2) . . . . ?
C8 C7 C9 C10 -176.61(16) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C7 C9 C10 -66.0(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C3 N1 C8 O2 -179.46(19) . . . . ?
C3 N1 C8 C7 2.0(2) . . . . ?
C3 N1 C15 C16 -92.7(2) . . . . ?
C3 C2 C7 C8 4.48(19) . . . . ?
C3 C2 C7 C11 121.40(17) . . . . ?
C3 C2 C7 C9 -108.38(17) . . . . ?
C3 C2 C1 C6 1.3(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C11 C7 C9 C10 66.1(2) . . . . ?
C11 C13 C14 N4 178.16(19) . . . . ?
C7 C2 C3 N1 -3.6(2) . . . . ?
C7 C2 C3 C4 175.65(16) . . . . ?
C7 C2 C1 C6 -175.72(19) . . . . ?
C7 C11 C13 N2 58.5(2) . . . . ?
C7 C11 C13 C14 -119.0(2) . . . . ?
C7 C9 C10 C12 -66.4(2) . . . . ?
C1 C2 C3 N1 178.76(16) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
C1 C2 C7 C8 -178.31(19) . . . . ?
C1 C2 C7 C11 -61.4(3) . . . . ?
C1 C2 C7 C9 68.8(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C13 N2 N3 N4 -0.6(2) . . . . ?
C13 N2 C12 C10 -58.6(3) . . . . ?
C13 C11 C7 C8 170.26(15) . . . . ?
C13 C11 C7 C2 56.8(2) . . . . ?
C13 C11 C7 C9 -73.9(2) . . . . ?
C9 C10 C12 N2 71.6(2) . . . . ?
C12 N2 N3 N4 179.28(17) . . . . ?
C12 N2 C13 C11 2.2(3) . . . . ?
C12 N2 C13 C14 -179.73(19) . . . . ?
C15 N1 C8 O2 2.6(3) . . . . ?
C15 N1 C8 C7 -175.92(17) . . . . ?
C15 N1 C3 C2 178.87(17) . . . . ?
C15 N1 C3 C4 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
