# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_CIYNAB01
_database_code_depnum_ccdc_archive 'CCDC 2149694'
loop_
_audit_author_name
_audit_author_address
'Massimo Moret'
;Department of Materials Science  University of Milano Bicocca
Italy
;
_audit_update_record             
;
2022-02-02 deposited with the CCDC.	2022-03-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_CIYNAB01            
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: Small poorly diffracting crystal 
;
_vrf_PLAT020_CIYNAB01            
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.127 Report
RESPONSE: Small poorly diffracting crystal
;
_vrf_PLAT026_CIYNAB01            
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        43% Check
RESPONSE: Small poorly diffracting crystal
;
_vrf_PLAT242_CIYNAB01            
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of          N Check
RESPONSE: Small poorly diffracting crystal
;
_vrf_PLAT340_CIYNAB01            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00456 Ang.
RESPONSE: Small poorly diffracting crystal
;
_vrf_PLAT906_CIYNAB01            
;
PROBLEM: Large K Value in the Analysis of Variance ......     78.421 Check
RESPONSE: Small poorly diffracting crystal
;
_vrf_PLAT906_CIYNAB01_2          
;
PROBLEM: Large K Value in the Analysis of Variance ......     10.106 Check
RESPONSE: Small poorly diffracting crystal
;
_vrf_PLAT906_CIYNAB01_3          
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.832 Check
RESPONSE: Small poorly diffracting crystal
;
_vrf_PLAT906_CIYNAB01_4          
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.057 Check
RESPONSE: Small poorly diffracting crystal
;
_vrf_PLAT911_CIYNAB01            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         83 Report
RESPONSE: Small poorly diffracting crystal
;
# Added during the CSD deposition process: Wednesday 02 February 2022 09:26 AM
# end Validation Reply Form


_audit_creation_method           
'SHELXL-2018/3 & Rigaku CrystalClear-SM Expert 2.0'

_chemical_name_systematic        
5,11-bis(4-nitrophenyl)-6,12-diphenyltetracene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H26 N2 O4'
_chemical_formula_sum            'C42 H26 N2 O4'
_chemical_formula_weight         622.65

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.15220(10)
_cell_length_b                   8.3752(2)
_cell_length_c                   13.2773(3)
_cell_angle_alpha                88.436(5)
_cell_angle_beta                 79.276(4)
_cell_angle_gamma                82.799(4)
_cell_volume                     775.26(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    32
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.9

_exptl_crystal_description       wedge
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_specimen_support Fiber
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            13362
_diffrn_reflns_av_unetI/netI     0.1337
_diffrn_reflns_av_R_equivalents  0.1274
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.451
_diffrn_reflns_theta_max         27.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3490
_reflns_number_gt                1505
_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       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_structure_solution    
'SIR14 (Burla et al, J. Appl. Cryst. 2015 48 306-309)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller, 1999)'
_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)+(0.0323P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3490
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1705
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.2186
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_restrained_S_all      0.944
_refine_ls_shift/su_max          0.001
_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 -0.4792(7) 0.3171(5) 0.5692(3) 0.1600(18) Uani 1 1 d . . . . .
N N -0.3535(7) 0.2070(6) 0.5423(3) 0.0999(12) Uani 1 1 d . . . . .
O2 O -0.2584(6) 0.1335(6) 0.6001(3) 0.1446(16) Uani 1 1 d . . . . .
C1 C 0.0531(4) 0.2744(3) 0.1546(2) 0.0515(7) Uani 1 1 d . . . . .
C2 C -0.0550(5) 0.4200(4) 0.1412(3) 0.0664(9) Uani 1 1 d . . . . .
H1 H -0.101521 0.439931 0.080575 0.080 Uiso 1 1 calc R U . . .
C3 C -0.0945(6) 0.5359(4) 0.2166(3) 0.0832(12) Uani 1 1 d . . . . .
H2 H -0.167181 0.633073 0.206440 0.100 Uiso 1 1 calc R U . . .
C4 C -0.0276(6) 0.5089(4) 0.3061(3) 0.0852(12) Uani 1 1 d . . . . .
H3 H -0.056875 0.586382 0.357316 0.102 Uiso 1 1 calc R U . . .
C5 C 0.0832(6) 0.3667(4) 0.3202(3) 0.0754(10) Uani 1 1 d . . . . .
H4 H 0.131086 0.349048 0.380580 0.090 Uiso 1 1 calc R U . . .
C6 C 0.1243(5) 0.2489(4) 0.2447(2) 0.0627(9) Uani 1 1 d . . . . .
H5 H 0.199540 0.152965 0.254694 0.075 Uiso 1 1 calc R U . . .
C7 C -0.2287(4) 0.0706(3) 0.2307(2) 0.0517(7) Uani 1 1 d . . . . .
C8 C -0.3558(5) 0.2091(4) 0.2628(3) 0.0624(9) Uani 1 1 d . . . . .
H6 H -0.412001 0.271983 0.215048 0.075 Uiso 1 1 calc R U . . .
C9 C -0.3977(5) 0.2523(4) 0.3641(3) 0.0712(10) Uani 1 1 d . . . . .
H7 H -0.480101 0.345049 0.385148 0.085 Uiso 1 1 calc R U . . .
C10 C -0.3164(5) 0.1568(5) 0.4343(3) 0.0709(10) Uani 1 1 d . . . . .
C11 C -0.1952(6) 0.0179(4) 0.4058(3) 0.0723(10) Uani 1 1 d . . . . .
H8 H -0.143418 -0.046486 0.454448 0.087 Uiso 1 1 calc R U . . .
C12 C -0.1526(5) -0.0235(4) 0.3039(3) 0.0631(9) Uani 1 1 d . . . . .
H9 H -0.070829 -0.116950 0.283771 0.076 Uiso 1 1 calc R U . . .
C13 C 0.1031(4) 0.1559(3) 0.0674(2) 0.0508(7) Uani 1 1 d . . . . .
C14 C -0.0217(4) 0.0432(3) 0.0492(2) 0.0485(7) Uani 1 1 d . . . . .
C15 C -0.1873(4) 0.0136(3) 0.1217(2) 0.0498(7) Uani 1 1 d . . . . .
C16 C -0.3156(4) -0.0877(3) 0.0971(2) 0.0494(7) Uani 1 1 d . . . . .
C17 C -0.4852(5) -0.1175(4) 0.1690(3) 0.0619(8) Uani 1 1 d . . . . .
H10 H -0.512105 -0.066929 0.232497 0.074 Uiso 1 1 calc R U . . .
C18 C -0.6060(5) -0.2173(4) 0.1464(3) 0.0658(9) Uani 1 1 d . . . . .
H11 H -0.715120 -0.233953 0.193851 0.079 Uiso 1 1 calc R U . . .
C19 C -0.5668(5) -0.2960(4) 0.0511(3) 0.0676(9) Uani 1 1 d . . . . .
H12 H -0.653055 -0.361361 0.035135 0.081 Uiso 1 1 calc R U . . .
C20 C -0.4053(5) -0.2779(4) -0.0179(3) 0.0606(8) Uani 1 1 d . . . . .
H13 H -0.379319 -0.335655 -0.078821 0.073 Uiso 1 1 calc R U . . .
C21 C -0.2732(4) -0.1711(3) 0.0013(2) 0.0517(7) 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
O1 N 1.215(5) . ?
N O2 1.221(5) . ?
N C10 1.473(5) . ?
C1 C2 1.386(4) . ?
C1 C6 1.386(4) . ?
C1 C13 1.508(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.364(5) . ?
C4 C5 1.374(5) . ?
C5 C6 1.391(4) . ?
C7 C12 1.382(4) . ?
C7 C8 1.404(4) . ?
C7 C15 1.501(4) . ?
C8 C9 1.371(4) . ?
C9 C10 1.374(5) . ?
C10 C11 1.377(5) . ?
C11 C12 1.375(4) . ?
C13 C21 1.395(4) 2 ?
C13 C14 1.432(4) . ?
C14 C15 1.424(4) . ?
C14 C14 1.473(5) 2 ?
C15 C16 1.411(4) . ?
C16 C17 1.442(4) . ?
C16 C21 1.432(4) . ?
C17 C18 1.351(4) . ?
C18 C19 1.408(4) . ?
C19 C20 1.356(4) . ?
C20 C21 1.439(4) . ?

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
O1 N O2 123.9(4) . . ?
O1 N C10 118.0(4) . . ?
O2 N C10 118.0(4) . . ?
C2 C1 C6 118.5(3) . . ?
C2 C1 C13 118.9(3) . . ?
C6 C1 C13 122.4(3) . . ?
C1 C2 C3 120.8(3) . . ?
C4 C3 C2 120.4(4) . . ?
C3 C4 C5 119.7(3) . . ?
C4 C5 C6 120.4(3) . . ?
C5 C6 C1 120.0(3) . . ?
C12 C7 C8 118.5(3) . . ?
C12 C7 C15 119.0(3) . . ?
C8 C7 C15 122.3(3) . . ?
C9 C8 C7 120.5(3) . . ?
C10 C9 C8 119.2(3) . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 N 119.3(4) . . ?
C11 C10 N 118.8(4) . . ?
C10 C11 C12 118.5(4) . . ?
C11 C12 C7 121.5(3) . . ?
C21 C13 C14 120.8(3) 2 . ?
C21 C13 C1 115.8(3) 2 . ?
C14 C13 C1 123.1(3) . . ?
C15 C14 C13 122.5(3) . . ?
C15 C14 C14 118.9(3) . 2 ?
C13 C14 C14 118.6(3) . 2 ?
C16 C15 C14 120.6(3) . . ?
C16 C15 C7 115.1(3) . . ?
C14 C15 C7 124.0(2) . . ?
C15 C16 C17 121.5(3) . . ?
C15 C16 C21 120.1(3) . . ?
C17 C16 C21 118.4(3) . . ?
C18 C17 C16 121.5(3) . . ?
C17 C18 C19 120.1(3) . . ?
C20 C19 C18 121.1(3) . . ?
C19 C20 C21 121.3(3) . . ?
C13 C21 C16 120.4(3) 2 . ?
C13 C21 C20 121.8(3) 2 . ?
C16 C21 C20 117.7(3) . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method Sublimation
_chemical_properties_physical    Oxygen-sensitive,Light-sensitive
_exptl_crystal_preparation       semiconductor
