# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
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data_2-12-1
_audit_block_doi                 10.5517/ccdc.csd.cc269j9c
_database_code_depnum_ccdc_archive 'CCDC 2034942'
loop_
_audit_author_name
_audit_author_address
'Ye Tao'
;Guangxi Normal University
China
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2022-04-28 downloaded from the CCDC.
;
_audit_creation_date             2019-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
2-(4-(3,3-dicyano-1-(1H-indol-1-yl)allylidene)cyclohexa-2,5-dien-1-ylidene)malononitrile
_chemical_name_systematic        'MJ 2-12-1'
_chemical_formula_moiety         'C22 H11 N5'
_chemical_formula_sum            'C22 H11 N5'
_chemical_formula_weight         345.36
_chemical_melting_point          '148.1 oC'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   16.161(3)
_cell_length_b                   11.810(2)
_cell_length_c                   18.957(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.689(3)
_cell_angle_gamma                90
_cell_volume                     3555.4(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5191
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.561
_cell_measurement_theta_min      2.517
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1714
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21880
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.460
_diffrn_reflns_theta_min         2.149
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2348
_reflns_number_total             3669
_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 v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      0.946
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0772P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1459
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C15(H15), C16(H16),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.07555(11) 1.11038(15) 0.02759(9) 0.0893(5) Uani 1 1 d . . . . .
N2 N 0.29027(10) 0.96223(14) 0.16426(9) 0.0848(5) Uani 1 1 d . . . . .
N3 N 0.17713(7) 0.75431(11) 0.20884(7) 0.0612(4) Uani 1 1 d . . . . .
N4 N -0.02931(13) 0.16237(18) 0.15992(12) 0.1078(6) Uani 1 1 d . . . . .
N5 N -0.18643(15) 0.3339(2) -0.02113(11) 0.1187(8) Uani 1 1 d . . . . .
C1 C 0.24877(10) 0.68893(14) 0.20764(9) 0.0652(4) Uani 1 1 d . . . . .
H1 H 0.257420 0.642768 0.169925 0.078 Uiso 1 1 calc R . . . .
C2 C 0.30314(10) 0.70336(14) 0.26962(10) 0.0661(4) Uani 1 1 d . . . . .
H2 H 0.356096 0.670274 0.281753 0.079 Uiso 1 1 calc R . . . .
C3 C 0.26581(9) 0.77802(13) 0.31358(9) 0.0593(4) Uani 1 1 d . . . . .
C4 C 0.28913(12) 0.82060(17) 0.38324(10) 0.0761(5) Uani 1 1 d . . . . .
H4 H 0.340687 0.800991 0.411192 0.091 Uiso 1 1 calc R . . . .
C5 C 0.23518(13) 0.89166(18) 0.41001(10) 0.0852(6) Uani 1 1 d . . . . .
H5 H 0.250460 0.919354 0.456532 0.102 Uiso 1 1 calc R . . . .
C6 C 0.15863(12) 0.92282(16) 0.36919(10) 0.0797(5) Uani 1 1 d . . . . .
H6 H 0.123761 0.971889 0.388554 0.096 Uiso 1 1 calc R . . . .
C7 C 0.13310(10) 0.88294(15) 0.30084(9) 0.0672(4) Uani 1 1 d . . . . .
H7 H 0.081626 0.904044 0.273341 0.081 Uiso 1 1 calc R . . . .
C8 C 0.18720(9) 0.80957(13) 0.27409(8) 0.0565(4) Uani 1 1 d . . . . .
C9 C 0.22033(11) 0.95102(14) 0.14187(9) 0.0626(4) Uani 1 1 d . . . . .
C10 C 0.13283(10) 0.94423(13) 0.11046(8) 0.0595(4) Uani 1 1 d . . . . .
C11 C 0.10123(11) 1.03777(16) 0.06501(9) 0.0685(5) Uani 1 1 d . . . . .
C12 C 0.08118(10) 0.85654(13) 0.11680(9) 0.0634(4) Uani 1 1 d . . . . .
H12 H 0.025720 0.863328 0.092850 0.076 Uiso 1 1 calc R . . . .
C13 C 0.10258(9) 0.75439(14) 0.15636(8) 0.0608(4) Uani 1 1 d . . . . .
C14 C 0.05542(10) 0.65597(14) 0.14325(8) 0.0618(4) Uani 1 1 d . . . . .
C15 C 0.07798(10) 0.55589(15) 0.18515(9) 0.0659(4) Uani 1 1 d . . . . .
H15 H 0.121653 0.559435 0.224660 0.079 Uiso 1 1 calc R . . . .
C16 C 0.03783(10) 0.45728(14) 0.16893(9) 0.0657(4) Uani 1 1 d . . . . .
H16 H 0.053923 0.394204 0.197569 0.079 Uiso 1 1 calc R . . . .
C17 C -0.02932(10) 0.44731(14) 0.10836(9) 0.0640(4) Uani 1 1 d . . . . .
C18 C -0.05481(10) 0.54840(15) 0.06823(10) 0.0718(5) Uani 1 1 d . . . . .
H18 H -0.099907 0.545174 0.029862 0.086 Uiso 1 1 calc R . . . .
C19 C -0.01537(10) 0.64732(15) 0.08456(10) 0.0703(5) Uani 1 1 d . . . . .
H19 H -0.033858 0.711401 0.057702 0.084 Uiso 1 1 calc R . . . .
C20 C -0.04703(12) 0.24433(19) 0.12885(12) 0.0807(5) Uani 1 1 d . . . . .
C21 C -0.06943(11) 0.34574(16) 0.08931(9) 0.0701(5) Uani 1 1 d . . . . .
C22 C -0.13544(14) 0.33836(18) 0.02864(11) 0.0842(6) Uani 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
N1 C11 1.141(2) . ?
N2 C9 1.139(2) . ?
N3 C1 1.3954(19) . ?
N3 C8 1.381(2) . ?
N3 C13 1.4130(18) . ?
N4 C20 1.142(3) . ?
N5 C22 1.133(3) . ?
C1 C2 1.341(2) . ?
C2 C3 1.422(3) . ?
C3 C4 1.398(2) . ?
C3 C8 1.400(2) . ?
C4 C5 1.373(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.368(2) . ?
C7 C8 1.392(2) . ?
C9 C10 1.431(2) . ?
C10 C11 1.435(2) . ?
C10 C12 1.349(2) . ?
C12 C13 1.429(2) . ?
C13 C14 1.387(2) . ?
C14 C15 1.433(2) . ?
C14 C19 1.444(2) . ?
C15 C16 1.341(2) . ?
C16 C17 1.431(2) . ?
C17 C18 1.434(2) . ?
C17 C21 1.379(2) . ?
C18 C19 1.339(2) . ?
C20 C21 1.424(3) . ?
C21 C22 1.419(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
C1 N3 C13 126.19(13) . . ?
C8 N3 C1 108.41(12) . . ?
C8 N3 C13 125.01(13) . . ?
C2 C1 N3 109.03(15) . . ?
C1 C2 C3 108.17(14) . . ?
C4 C3 C2 135.01(15) . . ?
C4 C3 C8 117.92(16) . . ?
C8 C3 C2 107.05(14) . . ?
C5 C4 C3 119.37(16) . . ?
C4 C5 C6 121.30(18) . . ?
C7 C6 C5 121.33(18) . . ?
C6 C7 C8 117.38(15) . . ?
N3 C8 C3 107.32(13) . . ?
N3 C8 C7 130.01(14) . . ?
C7 C8 C3 122.68(15) . . ?
N2 C9 C10 175.72(19) . . ?
C9 C10 C11 114.88(14) . . ?
C12 C10 C9 125.86(15) . . ?
C12 C10 C11 119.14(14) . . ?
N1 C11 C10 178.40(18) . . ?
C10 C12 C13 126.96(14) . . ?
N3 C13 C12 117.51(13) . . ?
C14 C13 N3 119.61(13) . . ?
C14 C13 C12 122.83(13) . . ?
C13 C14 C15 121.14(14) . . ?
C13 C14 C19 121.86(14) . . ?
C15 C14 C19 116.90(14) . . ?
C16 C15 C14 121.79(15) . . ?
C15 C16 C17 121.20(15) . . ?
C16 C17 C18 117.23(14) . . ?
C21 C17 C16 122.08(16) . . ?
C21 C17 C18 120.68(15) . . ?
C19 C18 C17 121.72(15) . . ?
C18 C19 C14 120.99(16) . . ?
N4 C20 C21 179.3(2) . . ?
C17 C21 C20 122.18(16) . . ?
C17 C21 C22 120.78(17) . . ?
C22 C21 C20 117.04(16) . . ?
N5 C22 C21 177.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate, n-hexane'
_exptl_crystal_preparation       Luminescent
