# Electronic Supplementary Material (ESI) for ChemComm.
# 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_KB658_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2234910'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-01-07 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(Z)-2-(1-methyl-3-oxo-1-phenyl-3,10-dihydrofuro[3',4':5,6]pyrano[4,3-b]indol-5(1H)-ylidene)acetonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 N2 O3'
_chemical_formula_sum            'C22 H14 N2 O3'
_chemical_formula_weight         354.35

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   9.8625(12)
_cell_length_b                   24.973(3)
_cell_length_c                   7.5384(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.143(4)
_cell_angle_gamma                90
_cell_volume                     1731.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6240
_cell_measurement_theta_min      2.359
_cell_measurement_theta_max      21.916

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6367
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22582
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.055
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             3617
_reflns_number_gt                2359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_max     0.825
_reflns_Friedel_fraction_full    0.875

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0436P)²] 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 896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3617
_refine_ls_number_parameters     249
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.58891(19) 0.57657(8) 0.5502(3) 0.0420(6) Uani 1 1 d . . . . .
O2 O 0.1486(2) 0.65966(8) 0.1876(3) 0.0589(7) Uani 1 1 d . . . . .
O3 O 0.3744(2) 0.69091(8) 0.3416(3) 0.0504(6) Uani 1 1 d . . . . .
N1 N 0.1845(3) 0.52010(10) 0.2164(4) 0.0408(7) Uani 1 1 d . . . . .
N2 N 0.8993(3) 0.52910(14) 0.8980(5) 0.0725(10) Uani 1 1 d . . . . .
C1 C 0.2038(3) 0.46504(12) 0.2381(4) 0.0379(7) Uani 1 1 d . . . . .
C2 C 0.1061(3) 0.42421(13) 0.1578(5) 0.0506(9) Uani 1 1 d . . . . .
H2 H 0.012516 0.431547 0.073674 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1516(4) 0.37261(13) 0.2063(5) 0.0574(10) Uani 1 1 d . . . . .
H3 H 0.087237 0.344538 0.156020 0.069 Uiso 1 1 calc R U . . .
C4 C 0.2925(4) 0.36139(14) 0.3292(5) 0.0551(9) Uani 1 1 d . . . . .
H4 H 0.320909 0.325951 0.357938 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3900(3) 0.40171(12) 0.4087(5) 0.0461(8) Uani 1 1 d . . . . .
H5 H 0.483783 0.393705 0.490592 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3469(3) 0.45497(11) 0.3654(4) 0.0360(7) Uani 1 1 d . . . . .
C7 C 0.4127(3) 0.50660(11) 0.4190(4) 0.0336(7) Uani 1 1 d . . . . .
C8 C 0.3092(3) 0.54433(12) 0.3234(4) 0.0339(7) Uani 1 1 d . . . . .
C9 C 0.5538(3) 0.52217(11) 0.5451(4) 0.0364(7) Uani 1 1 d . . . . .
C10 C 0.6604(3) 0.49146(12) 0.6649(5) 0.0448(8) Uani 1 1 d . . . . .
H10 H 0.646295 0.454624 0.663898 0.054 Uiso 1 1 calc R U . . .
C11 C 0.7918(4) 0.51280(14) 0.7911(5) 0.0526(9) Uani 1 1 d . . . . .
C12 C 0.4859(3) 0.61165(12) 0.4502(4) 0.0381(7) Uani 1 1 d . . . . .
C13 C 0.3487(3) 0.59964(11) 0.3446(4) 0.0358(7) Uani 1 1 d . . . . .
C14 C 0.2736(3) 0.65013(12) 0.2778(4) 0.0440(8) Uani 1 1 d . . . . .
C15 C 0.5196(3) 0.67002(12) 0.4461(4) 0.0427(8) Uani 1 1 d . . . . .
C16 C 0.5795(4) 0.69517(14) 0.6405(5) 0.0591(9) Uani 1 1 d . . . . .
H16A H 0.591758 0.732939 0.627995 0.089 Uiso 1 1 calc R U . . .
H16B H 0.671696 0.679286 0.711978 0.089 Uiso 1 1 calc R U . . .
H16C H 0.513065 0.689314 0.705492 0.089 Uiso 1 1 calc R U . . .
C17 C 0.6173(3) 0.68125(12) 0.3322(4) 0.0426(7) Uani 1 1 d . . . . .
C18 C 0.7448(3) 0.65249(14) 0.3692(5) 0.0600(10) Uani 1 1 d . . . . .
H18 H 0.770500 0.626200 0.462847 0.072 Uiso 1 1 calc R U . . .
C19 C 0.8340(4) 0.66273(16) 0.2671(6) 0.0656(10) Uani 1 1 d . . . . .
H19 H 0.918548 0.642847 0.291844 0.079 Uiso 1 1 calc R U . . .
C20 C 0.7995(4) 0.70148(16) 0.1313(5) 0.0618(10) Uani 1 1 d . . . . .
H20 H 0.859495 0.707961 0.062633 0.074 Uiso 1 1 calc R U . . .
C21 C 0.6745(5) 0.73101(14) 0.0966(5) 0.0615(10) Uani 1 1 d . . . . .
H21 H 0.651783 0.758210 0.006283 0.074 Uiso 1 1 calc R U . . .
C22 C 0.5822(4) 0.72081(12) 0.1942(5) 0.0522(9) Uani 1 1 d . . . . .
H22 H 0.497024 0.740445 0.167165 0.063 Uiso 1 1 calc R U . . .
H1N H 0.100(5) 0.5346(17) 0.134(7) 0.102(15) 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 C12 1.347(3) . ?
O1 C9 1.399(3) . ?
O2 C14 1.198(4) . ?
O3 C14 1.382(4) . ?
O3 C15 1.460(3) . ?
N1 C8 1.347(4) . ?
N1 C1 1.390(4) . ?
N2 C11 1.150(4) . ?
C1 C2 1.384(4) . ?
C1 C6 1.413(4) . ?
C2 C3 1.370(4) . ?
C3 C4 1.392(5) . ?
C4 C5 1.372(5) . ?
C5 C6 1.399(4) . ?
C6 C7 1.435(4) . ?
C7 C8 1.385(4) . ?
C7 C9 1.427(4) . ?
C8 C13 1.428(4) . ?
C9 C10 1.351(4) . ?
C10 C11 1.407(5) . ?
C12 C13 1.333(4) . ?
C12 C15 1.498(4) . ?
C13 C14 1.457(4) . ?
C15 C16 1.505(5) . ?
C15 C17 1.530(4) . ?
C17 C22 1.385(4) . ?
C17 C18 1.386(4) . ?
C18 C19 1.386(5) . ?
C19 C20 1.360(5) . ?
C20 C21 1.378(5) . ?
C21 C22 1.385(5) . ?

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
C12 O1 C9 119.1(2) . . ?
C14 O3 C15 111.5(2) . . ?
C8 N1 C1 108.5(3) . . ?
C2 C1 N1 129.3(3) . . ?
C2 C1 C6 122.2(3) . . ?
N1 C1 C6 108.5(3) . . ?
C3 C2 C1 117.8(3) . . ?
C2 C3 C4 121.3(3) . . ?
C5 C4 C3 121.1(3) . . ?
C4 C5 C6 119.3(3) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 136.1(3) . . ?
C1 C6 C7 105.7(2) . . ?
C8 C7 C9 121.3(2) . . ?
C8 C7 C6 106.9(2) . . ?
C9 C7 C6 131.8(3) . . ?
N1 C8 C7 110.4(2) . . ?
N1 C8 C13 130.9(3) . . ?
C7 C8 C13 118.7(2) . . ?
C10 C9 O1 114.0(3) . . ?
C10 C9 C7 128.9(3) . . ?
O1 C9 C7 117.1(2) . . ?
C9 C10 C11 122.8(3) . . ?
N2 C11 C10 178.0(4) . . ?
C13 C12 O1 125.9(3) . . ?
C13 C12 C15 113.1(3) . . ?
O1 C12 C15 121.1(3) . . ?
C12 C13 C8 117.5(2) . . ?
C12 C13 C14 106.9(3) . . ?
C8 C13 C14 135.6(3) . . ?
O2 C14 O3 121.0(3) . . ?
O2 C14 C13 131.2(3) . . ?
O3 C14 C13 107.8(3) . . ?
O3 C15 C12 100.2(2) . . ?
O3 C15 C16 109.9(3) . . ?
C12 C15 C16 113.4(3) . . ?
O3 C15 C17 109.0(2) . . ?
C12 C15 C17 112.3(3) . . ?
C16 C15 C17 111.4(2) . . ?
C22 C17 C18 118.9(3) . . ?
C22 C17 C15 121.0(3) . . ?
C18 C17 C15 120.1(3) . . ?
C19 C18 C17 120.3(3) . . ?
C20 C19 C18 120.9(3) . . ?
C19 C20 C21 119.2(3) . . ?
C20 C21 C22 121.0(3) . . ?
C21 C22 C17 119.8(3) . . ?

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
