# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_mx5178
_audit_block_doi                 10.5517/ccdc.csd.cc2bqs0w
_database_code_depnum_ccdc_archive 'CCDC 2166838'
loop_
_audit_author_name
_audit_author_address
'Geetha Bolla '
;ICCAS Beijing 
India
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-07-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H16 N2'
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39
_chemical_melting_point          559
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           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                   3.7587(8)
_cell_length_b                   11.009(2)
_cell_length_c                   19.568(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.97(3)
_cell_angle_gamma                90
_cell_volume                     809.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    177
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      1.0405
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_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            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8767
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.082
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1746
_reflns_number_total             1786
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.107
_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)+(0.0428P)²+0.2820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1047
_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:
 C11(H11), C12(H12), C7(H7), C8(H8), C5(H5), C2(H2), C25(H25), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
C11 C 0.1081(3) 0.17836(10) 0.10328(6) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.057131 0.159979 0.149524 0.026 Uiso 1 1 calc R U . . .
C10 C 0.0526(3) 0.08789(10) 0.05203(6) 0.0202(3) Uani 1 1 d . . . . .
C9 C 0.1344(3) 0.11528(10) -0.01769(6) 0.0206(3) Uani 1 1 d . . . . .
C12 C -0.0807(3) -0.02693(10) 0.06787(6) 0.0218(3) Uani 1 1 d . . . . .
H12 H -0.136187 -0.045272 0.113919 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3133(3) 0.31800(11) 0.01730(6) 0.0235(3) Uani 1 1 d . . . . .
H7 H 0.399079 0.396449 0.005835 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2338(3) 0.29133(11) 0.08693(6) 0.0216(3) Uani 1 1 d . . . . .
C8 C 0.2690(3) 0.23375(11) -0.03276(6) 0.0236(3) Uani 1 1 d . . . . .
H8 H 0.328209 0.253671 -0.078418 0.028 Uiso 1 1 calc R U . . .
C1 C 0.2871(3) 0.38508(10) 0.14040(6) 0.0219(3) Uani 1 1 d . . . . .
C5 C 0.4278(3) 0.35587(11) 0.20468(6) 0.0252(3) Uani 1 1 d . . . . .
H5 H 0.491993 0.274484 0.215313 0.030 Uiso 1 1 calc R U . . .
N1 N 0.3818(3) 0.56307(10) 0.24274(6) 0.0322(3) Uani 1 1 d . . . . .
C2 C 0.1980(3) 0.50656(11) 0.12877(7) 0.0261(3) Uani 1 1 d . . . . .
H2 H 0.106022 0.531774 0.085540 0.031 Uiso 1 1 calc R U . . .
C25 C 0.4728(3) 0.44676(12) 0.25276(7) 0.0290(3) Uani 1 1 d . . . . .
H25 H 0.575065 0.425271 0.295813 0.035 Uiso 1 1 calc R U . . .
C3 C 0.2459(4) 0.58969(12) 0.18121(7) 0.0309(3) Uani 1 1 d . . . . .
H3 H 0.176958 0.671416 0.172733 0.037 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
C11 H11 0.9500 . ?
C11 C10 1.4261(16) . ?
C11 C6 1.3701(16) . ?
C10 C9 1.4357(17) . ?
C10 C12 1.3965(16) . ?
C9 C12 1.3943(16) 3 ?
C9 C8 1.4315(16) . ?
C12 H12 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.4304(17) . ?
C7 C8 1.3572(17) . ?
C6 C1 1.4808(16) . ?
C8 H8 0.9500 . ?
C1 C5 1.3938(17) . ?
C1 C2 1.3964(17) . ?
C5 H5 0.9500 . ?
C5 C25 1.3818(17) . ?
N1 C25 1.3388(18) . ?
N1 C3 1.3328(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3843(18) . ?
C25 H25 0.9500 . ?
C3 H3 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
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C6 C11 C10 121.11(11) . . ?
C11 C10 C9 119.37(10) . . ?
C12 C10 C11 121.66(11) . . ?
C12 C10 C9 118.97(11) . . ?
C12 C9 C10 119.47(10) 3 . ?
C12 C9 C8 122.54(11) 3 . ?
C8 C9 C10 117.98(11) . . ?
C10 C12 H12 119.2 . . ?
C9 C12 C10 121.55(11) 3 . ?
C9 C12 H12 119.2 3 . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C8 C7 C6 121.48(11) . . ?
C11 C6 C7 119.15(11) . . ?
C11 C6 C1 120.72(11) . . ?
C7 C6 C1 120.13(10) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 C9 120.89(11) . . ?
C7 C8 H8 119.6 . . ?
C5 C1 C6 121.44(11) . . ?
C5 C1 C2 117.01(11) . . ?
C2 C1 C6 121.54(11) . . ?
C1 C5 H5 120.4 . . ?
C25 C5 C1 119.18(12) . . ?
C25 C5 H5 120.4 . . ?
C3 N1 C25 115.83(11) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.99(12) . . ?
C3 C2 H2 120.5 . . ?
C5 C25 H25 117.8 . . ?
N1 C25 C5 124.39(12) . . ?
N1 C25 H25 117.8 . . ?
N1 C3 C2 124.56(12) . . ?
N1 C3 H3 117.7 . . ?
C2 C3 H3 117.7 . . ?

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
C11 C10 C9 C12 179.91(10) . . . 3 ?
C11 C10 C9 C8 -0.11(16) . . . . ?
C11 C10 C12 C9 -179.91(10) . . . 3 ?
C11 C6 C1 C5 40.29(17) . . . . ?
C11 C6 C1 C2 -139.55(12) . . . . ?
C10 C11 C6 C7 -0.61(17) . . . . ?
C10 C11 C6 C1 179.38(10) . . . . ?
C10 C9 C8 C7 -0.87(17) . . . . ?
C9 C10 C12 C9 0.29(18) . . . 3 ?
C12 C10 C9 C12 -0.28(18) . . . 3 ?
C12 C10 C9 C8 179.70(10) . . . . ?
C12 C9 C8 C7 179.11(11) 3 . . . ?
C7 C6 C1 C5 -139.72(12) . . . . ?
C7 C6 C1 C2 40.44(16) . . . . ?
C6 C11 C10 C9 0.84(17) . . . . ?
C6 C11 C10 C12 -178.96(11) . . . . ?
C6 C7 C8 C9 1.13(18) . . . . ?
C6 C1 C5 C25 179.91(11) . . . . ?
C6 C1 C2 C3 178.46(11) . . . . ?
C8 C7 C6 C11 -0.38(17) . . . . ?
C8 C7 C6 C1 179.63(11) . . . . ?
C1 C5 C25 N1 1.7(2) . . . . ?
C1 C2 C3 N1 1.9(2) . . . . ?
C5 C1 C2 C3 -1.38(17) . . . . ?
C2 C1 C5 C25 -0.25(17) . . . . ?
C25 N1 C3 C2 -0.5(2) . . . . ?
C3 N1 C25 C5 -1.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
