# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_b190401a_0m
_database_code_depnum_ccdc_archive 'CCDC 1907867'
loop_
_audit_author_name
_audit_author_address
'Lihua Qiu'
;Soochow University
China
;
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;
_audit_creation_date             2019-04-08
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H24 N4'
_chemical_formula_sum            'C32 H24 N4'
_chemical_formula_weight         464.55
_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'

_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                   12.4552(12)
_cell_length_b                   14.2434(14)
_cell_length_c                   13.5827(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.738(3)
_cell_angle_gamma                90
_cell_volume                     2359.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1379 before and 0.0685 after correction. The Ratio of minimum to maximum transmission is 0.9096. 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    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            54242
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_min         2.199
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                4289
_reflns_number_total             5452
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.833
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.086
_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)+(0.0857P)²+1.2886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1560
_refine_ls_wR_factor_ref         0.1731
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_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
N1 N 0.83659(12) 0.21791(10) 0.84633(11) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.80572(11) 0.15733(9) 0.69000(10) 0.0226(3) Uani 1 1 d . . . . .
N3 N 0.88825(13) 0.21378(11) 0.56092(11) 0.0313(4) Uani 1 1 d . . . . .
N4 N 0.67207(18) -0.15266(14) 0.33416(15) 0.0517(5) Uani 1 1 d . . . . .
C1 C 0.90936(14) 0.30329(12) 0.71471(12) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.94676(16) 0.38333(13) 0.77093(14) 0.0328(4) Uani 1 1 d . . . . .
H2 H 0.9336 0.3901 0.8356 0.039 Uiso 1 1 calc R . . . .
C3 C 1.00302(18) 0.45222(15) 0.73099(15) 0.0392(5) Uani 1 1 d . . . . .
H3A H 1.0270 0.5058 0.7681 0.047 Uiso 1 1 calc R . . . .
C4 C 1.02360(17) 0.44097(15) 0.63483(15) 0.0387(5) Uani 1 1 d . . . . .
H4 H 1.0634 0.4865 0.6086 0.046 Uiso 1 1 calc R . . . .
C5 C 0.98575(17) 0.36316(14) 0.57790(14) 0.0356(4) Uani 1 1 d . . . . .
H5 H 0.9995 0.3569 0.5134 0.043 Uiso 1 1 calc R . . . .
C6 C 0.92688(14) 0.29382(12) 0.61668(13) 0.0263(4) Uani 1 1 d . . . . .
C7 C 0.78898(16) 0.17146(14) 0.57994(13) 0.0319(4) Uani 1 1 d . . . . .
H7 H 0.7286 0.2160 0.5596 0.038 Uiso 1 1 calc R . . . .
C8 C 0.85235(13) 0.22784(11) 0.75431(12) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.77144(14) 0.13846(12) 0.84262(13) 0.0254(4) Uani 1 1 d . . . . .
C10 C 0.72715(17) 0.09773(14) 0.91866(14) 0.0335(4) Uani 1 1 d . . . . .
H10 H 0.7425 0.1220 0.9836 0.040 Uiso 1 1 calc R . . . .
C11 C 0.66020(17) 0.02085(14) 0.89551(16) 0.0376(5) Uani 1 1 d . . . . .
H11 H 0.6288 -0.0064 0.9451 0.045 Uiso 1 1 calc R . . . .
C12 C 0.63873(17) -0.01681(14) 0.79915(16) 0.0372(5) Uani 1 1 d . . . . .
H12 H 0.5928 -0.0687 0.7857 0.045 Uiso 1 1 calc R . . . .
C13 C 0.68373(16) 0.02076(13) 0.72257(14) 0.0318(4) Uani 1 1 d . . . . .
H13 H 0.6706 -0.0058 0.6587 0.038 Uiso 1 1 calc R . . . .
C14 C 0.74936(13) 0.09987(12) 0.74550(12) 0.0238(3) Uani 1 1 d . . . . .
C15 C 0.76185(17) 0.08235(13) 0.51912(13) 0.0327(4) Uani 1 1 d . . . . .
C16 C 0.65355(18) 0.06492(14) 0.47752(15) 0.0383(5) Uani 1 1 d . . . . .
H16 H 0.5998 0.1063 0.4894 0.046 Uiso 1 1 calc R . . . .
C17 C 0.62379(18) -0.01322(15) 0.41841(15) 0.0399(5) Uani 1 1 d . . . . .
H17 H 0.5500 -0.0248 0.3921 0.048 Uiso 1 1 calc R . . . .
C18 C 0.70244(17) -0.07455(13) 0.39776(14) 0.0344(4) Uani 1 1 d . . . . .
C19 C 0.81214(17) -0.05833(14) 0.43946(15) 0.0347(4) Uani 1 1 d . . . . .
H19 H 0.8657 -0.0994 0.4267 0.042 Uiso 1 1 calc R . . . .
C20 C 0.84141(17) 0.01982(14) 0.50059(14) 0.0341(4) Uani 1 1 d . . . . .
H20 H 0.9148 0.0304 0.5293 0.041 Uiso 1 1 calc R . . . .
C21 C 0.72785(18) -0.17102(15) 0.25508(15) 0.0379(5) Uani 1 1 d . . . . .
C22 C 0.7555(2) -0.10007(17) 0.19581(18) 0.0518(6) Uani 1 1 d . . . . .
H22 H 0.7394 -0.0379 0.2082 0.062 Uiso 1 1 calc R . . . .
C23 C 0.8079(2) -0.1222(2) 0.11704(19) 0.0619(7) Uani 1 1 d . . . . .
H23 H 0.8270 -0.0746 0.0769 0.074 Uiso 1 1 calc R . . . .
C24 C 0.8314(2) -0.2145(2) 0.0986(2) 0.0615(7) Uani 1 1 d . . . . .
H24 H 0.8659 -0.2292 0.0460 0.074 Uiso 1 1 calc R . . . .
C25 C 0.80399(19) -0.28336(19) 0.1573(2) 0.0531(6) Uani 1 1 d . . . . .
H25 H 0.8189 -0.3455 0.1440 0.064 Uiso 1 1 calc R . . . .
C26 C 0.75453(18) -0.26282(16) 0.23615(17) 0.0437(5) Uani 1 1 d . . . . .
H26 H 0.7388 -0.3109 0.2773 0.052 Uiso 1 1 calc R . . . .
C27 C 0.58044(16) -0.20908(13) 0.34291(15) 0.0342(4) Uani 1 1 d . . . . .
C28 C 0.56851(17) -0.24166(16) 0.43582(16) 0.0409(5) Uani 1 1 d . . . . .
H28 H 0.6175 -0.2229 0.4936 0.049 Uiso 1 1 calc R . . . .
C29 C 0.4837(2) -0.30222(17) 0.44294(18) 0.0482(6) Uani 1 1 d . . . . .
H29 H 0.4763 -0.3241 0.5057 0.058 Uiso 1 1 calc R . . . .
C30 C 0.41042(18) -0.33042(16) 0.3586(2) 0.0482(6) Uani 1 1 d . . . . .
H30 H 0.3545 -0.3722 0.3639 0.058 Uiso 1 1 calc R . . . .
C31 C 0.42040(16) -0.29661(15) 0.26681(18) 0.0434(5) Uani 1 1 d . . . . .
H31 H 0.3700 -0.3146 0.2096 0.052 Uiso 1 1 calc R . . . .
C32 C 0.50464(18) -0.23591(14) 0.25802(16) 0.0392(5) Uani 1 1 d . . . . .
H32 H 0.5105 -0.2131 0.1952 0.047 Uiso 1 1 calc R . . . .
H3 H 0.8797(18) 0.2256(16) 0.4920(19) 0.039(6) 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
N1 C8 1.312(2) . ?
N1 C9 1.387(2) . ?
N2 C7 1.480(2) . ?
N2 C8 1.379(2) . ?
N2 C14 1.395(2) . ?
N3 C6 1.399(2) . ?
N3 C7 1.445(2) . ?
N4 C18 1.412(2) . ?
N4 C21 1.417(3) . ?
N4 C27 1.420(3) . ?
C1 C2 1.398(2) . ?
C1 C6 1.399(2) . ?
C1 C8 1.450(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.396(3) . ?
C7 C15 1.515(3) . ?
C9 C10 1.393(2) . ?
C9 C14 1.404(2) . ?
C10 C11 1.374(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.390(2) . ?
C15 C16 1.375(3) . ?
C15 C20 1.393(3) . ?
C16 C17 1.378(3) . ?
C17 C18 1.383(3) . ?
C18 C19 1.388(3) . ?
C19 C20 1.392(3) . ?
C21 C22 1.379(3) . ?
C21 C26 1.386(3) . ?
C22 C23 1.398(4) . ?
C23 C24 1.381(4) . ?
C24 C25 1.351(4) . ?
C25 C26 1.372(3) . ?
C27 C28 1.381(3) . ?
C27 C32 1.387(3) . ?
C28 C29 1.382(3) . ?
C29 C30 1.371(3) . ?
C30 C31 1.366(4) . ?
C31 C32 1.383(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 C9 104.66(14) . . ?
C8 N2 C7 119.68(14) . . ?
C8 N2 C14 106.15(13) . . ?
C14 N2 C7 129.97(14) . . ?
C6 N3 C7 117.11(15) . . ?
C18 N4 C21 119.83(17) . . ?
C18 N4 C27 120.95(17) . . ?
C21 N4 C27 119.03(16) . . ?
C2 C1 C6 119.95(16) . . ?
C2 C1 C8 122.38(15) . . ?
C6 C1 C8 117.67(15) . . ?
C3 C2 C1 120.31(17) . . ?
C2 C3 C4 119.53(18) . . ?
C5 C4 C3 120.81(17) . . ?
C4 C5 C6 120.21(17) . . ?
N3 C6 C1 119.40(15) . . ?
C5 C6 N3 121.45(16) . . ?
C5 C6 C1 119.12(16) . . ?
N2 C7 C15 114.01(15) . . ?
N3 C7 N2 106.70(14) . . ?
N3 C7 C15 110.85(15) . . ?
N1 C8 N2 113.55(14) . . ?
N1 C8 C1 127.78(15) . . ?
N2 C8 C1 118.65(14) . . ?
N1 C9 C10 129.04(16) . . ?
N1 C9 C14 110.78(14) . . ?
C10 C9 C14 120.16(16) . . ?
C11 C10 C9 118.43(18) . . ?
C10 C11 C12 120.99(18) . . ?
C13 C12 C11 121.91(18) . . ?
C12 C13 C14 117.01(17) . . ?
N2 C14 C9 104.73(14) . . ?
C13 C14 N2 133.81(16) . . ?
C13 C14 C9 121.47(16) . . ?
C16 C15 C7 117.83(18) . . ?
C16 C15 C20 119.00(17) . . ?
C20 C15 C7 123.13(18) . . ?
C15 C16 C17 120.69(19) . . ?
C16 C17 C18 120.70(19) . . ?
C17 C18 N4 120.60(19) . . ?
C17 C18 C19 119.42(18) . . ?
C19 C18 N4 119.98(19) . . ?
C18 C19 C20 119.54(18) . . ?
C19 C20 C15 120.63(18) . . ?
C22 C21 N4 121.8(2) . . ?
C22 C21 C26 119.0(2) . . ?
C26 C21 N4 119.2(2) . . ?
C21 C22 C23 119.5(2) . . ?
C24 C23 C22 120.1(2) . . ?
C25 C24 C23 119.8(2) . . ?
C24 C25 C26 120.9(2) . . ?
C25 C26 C21 120.6(2) . . ?
C28 C27 N4 120.29(18) . . ?
C28 C27 C32 119.05(19) . . ?
C32 C27 N4 120.59(19) . . ?
C27 C28 C29 120.0(2) . . ?
C30 C29 C28 120.8(2) . . ?
C31 C30 C29 119.4(2) . . ?
C30 C31 C32 120.7(2) . . ?
C31 C32 C27 120.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
