# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_DD_NA_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1918563'
loop_
_audit_author_name
_audit_author_address
dd
;iit delhi
India
;
_audit_update_record             
;
2019-05-25 deposited with the CCDC.	2020-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '1,3-bis Indole'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2'
_chemical_formula_weight         336.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   15.931(2)
_cell_length_b                   14.7572(15)
_cell_length_c                   8.0025(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.219(4)
_cell_angle_gamma                90
_cell_volume                     1806.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1522
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      24.68

_exptl_crystal_description       'Rod Shape'
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      297(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            4820
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             1562
_reflns_number_gt                1054
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0837P)²+0.1404P] 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         1562
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
N1 N 0.20808(11) 0.28751(12) 0.2668(2) 0.0596(5) Uani 1 1 d . . . . .
C7 C 0.25667(13) 0.35538(13) 0.3655(2) 0.0512(6) Uani 1 1 d . . . . .
C8 C 0.34590(13) 0.33779(12) 0.3821(2) 0.0467(5) Uani 1 1 d . . . . .
C13 C 0.5000 0.25186(17) 0.2500 0.0487(7) Uani 1 2 d S T P . .
H13 H 0.5000 0.3149 0.2500 0.058 Uiso 1 2 calc R U P . .
C10 C 0.42668(13) 0.20649(13) 0.2696(2) 0.0517(6) Uani 1 1 d . . . . .
C2 C 0.34933(13) 0.25564(13) 0.2887(2) 0.0505(6) Uani 1 1 d . . . . .
C1 C 0.26435(15) 0.22861(14) 0.2232(2) 0.0598(6) Uani 1 1 d . . . . .
H1 H 0.2471 0.1765 0.1571 0.072 Uiso 1 1 calc R U . . .
C3 C 0.40798(15) 0.39715(13) 0.4828(3) 0.0594(6) Uani 1 1 d . . . . .
H3 H 0.4673 0.3872 0.4982 0.071 Uiso 1 1 calc R U . . .
C6 C 0.22904(17) 0.42966(16) 0.4429(3) 0.0673(7) Uani 1 1 d . . . . .
H6 H 0.1700 0.4402 0.4301 0.081 Uiso 1 1 calc R U . . .
C11 C 0.42805(16) 0.11240(14) 0.2698(3) 0.0726(7) Uani 1 1 d . . . . .
H11 H 0.3802 0.0802 0.2834 0.087 Uiso 1 1 calc R U . . .
C5 C 0.29212(18) 0.48689(17) 0.5389(3) 0.0769(8) Uani 1 1 d . . . . .
H5 H 0.2756 0.5374 0.5914 0.092 Uiso 1 1 calc R U . . .
C4 C 0.38019(18) 0.47070(15) 0.5589(3) 0.0740(7) Uani 1 1 d . . . . .
H4 H 0.4215 0.5105 0.6254 0.089 Uiso 1 1 calc R U . . .
C9 C 0.11336(15) 0.28173(19) 0.2137(3) 0.0855(8) Uani 1 1 d . . . . .
H9A H 0.0898 0.3289 0.1313 0.128 Uiso 1 1 calc R U . . .
H9B H 0.0919 0.2887 0.3137 0.128 Uiso 1 1 calc R U . . .
H9C H 0.0958 0.2238 0.1609 0.128 Uiso 1 1 calc R U . . .
C12 C 0.5000 0.0665(2) 0.2500 0.0851(12) Uani 1 2 d S T P . .
H12 H 0.5000 0.0035 0.2500 0.102 Uiso 1 2 calc R U P . .


_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
N1 C1 1.362(3) . ?
N1 C7 1.373(3) . ?
N1 C9 1.451(3) . ?
C7 C6 1.390(3) . ?
C7 C8 1.414(3) . ?
C8 C3 1.396(3) . ?
C8 C2 1.433(3) . ?
C13 C10 1.393(2) 2_655 ?
C13 C10 1.393(2) . ?
C13 H13 0.9300 . ?
C10 C11 1.389(3) . ?
C10 C2 1.474(3) . ?
C2 C1 1.368(3) . ?
C1 H1 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C6 C5 1.372(3) . ?
C6 H6 0.9300 . ?
C11 C12 1.378(2) . ?
C11 H11 0.9300 . ?
C5 C4 1.388(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 C11 1.378(2) 2_655 ?
C12 H12 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
C1 N1 C7 107.90(17) . . ?
C1 N1 C9 126.3(2) . . ?
C7 N1 C9 125.76(19) . . ?
N1 C7 C6 129.4(2) . . ?
N1 C7 C8 108.08(17) . . ?
C6 C7 C8 122.6(2) . . ?
C3 C8 C7 118.06(18) . . ?
C3 C8 C2 135.04(19) . . ?
C7 C8 C2 106.86(17) . . ?
C10 C13 C10 122.5(2) 2_655 . ?
C10 C13 H13 118.7 2_655 . ?
C10 C13 H13 118.7 . . ?
C11 C10 C13 117.87(19) . . ?
C11 C10 C2 120.33(18) . . ?
C13 C10 C2 121.80(17) . . ?
C1 C2 C8 105.60(18) . . ?
C1 C2 C10 125.67(19) . . ?
C8 C2 C10 128.69(18) . . ?
N1 C1 C2 111.55(19) . . ?
N1 C1 H1 124.2 . . ?
C2 C1 H1 124.2 . . ?
C4 C3 C8 119.1(2) . . ?
C4 C3 H3 120.4 . . ?
C8 C3 H3 120.4 . . ?
C5 C6 C7 117.5(2) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C12 C11 121.1(3) 2_655 . ?
C11 C12 H12 119.4 2_655 . ?
C11 C12 H12 119.4 . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

