# 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 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_test33
_database_code_depnum_ccdc_archive 'CCDC 1845856'
loop_
_audit_author_name
_audit_author_address
'Davi Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2018-05-28 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;

_audit_creation_date             2016-12-22T11:12:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '1,2-bis (4-phenylbenzamide) benzene'
_chemical_formula_moiety         'C32 H24 N2 O2'
_chemical_formula_sum            'C32 H24 N2 O2'
_chemical_formula_weight         468.53
_chemical_melting_point          534K
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.675(6)
_cell_length_b                   10.498(7)
_cell_length_c                   18.152(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.975(15)
_cell_angle_gamma                90
_cell_volume                     2406(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3820
_cell_measurement_theta_min      2.245
_cell_measurement_theta_max      29.93

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.128
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.8015
_exptl_absorpt_correction_T_max  0.8622

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_number            41516
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         30.23
_diffrn_reflns_theta_full        30.23
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             7127
_reflns_number_gt                6501
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Diamond (version 3.2i); Crystal Impact GbR, Bonn'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0538P)²+0.5341P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         7127
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1697
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.78746(10) 0.07893(13) 1.08011(7) 0.0498(4) Uani 1 1 d . . .
O1 O 0.81868(10) -0.08228(13) 0.82827(7) 0.0490(4) Uani 1 1 d . . .
N2 N 0.79383(11) 0.03497(14) 0.95901(8) 0.0383(4) Uani 1 1 d . . .
H2 H 0.7674 -0.0099 0.9223 0.046 Uiso 1 1 calc R . .
N1 N 0.97936(11) -0.04988(14) 0.88866(8) 0.0363(4) Uani 1 1 d . . .
H1 H 1.0389 -0.0858 0.9021 0.044 Uiso 1 1 calc R . .
C24 C 0.49897(13) -0.24492(18) 1.03820(10) 0.0376(4) Uani 1 1 d . . .
C2 C 0.87842(13) 0.11778(17) 0.94717(10) 0.0361(4) Uani 1 1 d . . .
C20 C 0.75203(13) 0.02203(18) 1.02420(10) 0.0364(4) Uani 1 1 d . . .
C11 C 0.99852(14) -0.49032(18) 0.77223(9) 0.0369(4) Uani 1 1 d . . .
C10 C 0.89857(14) -0.43945(19) 0.75517(10) 0.0413(5) Uani 1 1 d . . .
H10 H 0.8483 -0.4865 0.7264 0.05 Uiso 1 1 calc R . .
C8 C 0.94488(13) -0.24661(18) 0.82133(9) 0.0339(4) Uani 1 1 d . . .
C21 C 0.66317(13) -0.06930(18) 1.02625(10) 0.0360(4) Uani 1 1 d . . .
C22 C 0.64298(15) -0.1195(2) 1.09408(10) 0.0461(5) Uani 1 1 d . . .
H22 H 0.6843 -0.0942 1.1364 0.055 Uiso 1 1 calc R . .
C26 C 0.59848(14) -0.10593(19) 0.96476(10) 0.0428(5) Uani 1 1 d . . .
H26 H 0.6096 -0.0723 0.9187 0.051 Uiso 1 1 calc R . .
C9 C 0.87215(13) -0.32100(19) 0.77983(9) 0.0394(5) Uani 1 1 d . . .
H9 H 0.8039 -0.2902 0.7683 0.047 Uiso 1 1 calc R . .
C1 C 0.96622(13) 0.07626(17) 0.91375(9) 0.0333(4) Uani 1 1 d . . .
C14 C 1.02621(15) -0.61980(19) 0.74925(10) 0.0431(5) Uani 1 1 d . . .
C6 C 1.04951(15) 0.1598(2) 0.90705(10) 0.0447(5) Uani 1 1 d . . .
H6 H 1.1087 0.1326 0.8845 0.054 Uiso 1 1 calc R . .
C25 C 0.51763(14) -0.19178(19) 0.97100(10) 0.0444(5) Uani 1 1 d . . .
H25 H 0.4746 -0.2145 0.929 0.053 Uiso 1 1 calc R . .
C7 C 0.90918(13) -0.11997(18) 0.84613(9) 0.0358(4) Uani 1 1 d . . .
C12 C 1.07102(14) -0.41497(19) 0.81404(11) 0.0468(5) Uani 1 1 d . . .
H12 H 1.1389 -0.4463 0.8263 0.056 Uiso 1 1 calc R . .
C27 C 0.41591(14) -0.34228(19) 1.04488(10) 0.0405(5) Uani 1 1 d . . .
C15 C 0.95013(18) -0.7152(2) 0.74254(12) 0.0574(6) Uani 1 1 d . . .
H15 H 0.8804 -0.6957 0.7503 0.069 Uiso 1 1 calc R . .
C3 C 0.87446(16) 0.24273(19) 0.97071(11) 0.0483(5) Uani 1 1 d . . .
H3 H 0.8143 0.272 0.9913 0.058 Uiso 1 1 calc R . .
C32 C 0.38486(16) -0.4238(2) 0.98694(12) 0.0528(5) Uani 1 1 d . . .
H32 H 0.4143 -0.4145 0.9421 0.063 Uiso 1 1 calc R . .
C13 C 1.04560(14) -0.29565(19) 0.83778(11) 0.0462(5) Uani 1 1 d . . .
H13 H 1.0965 -0.2473 0.8652 0.055 Uiso 1 1 calc R . .
C28 C 0.36845(16) -0.3589(2) 1.10987(11) 0.0536(6) Uani 1 1 d . . .
H28 H 0.3867 -0.3048 1.1496 0.064 Uiso 1 1 calc R . .
C19 C 1.12832(19) -0.6532(2) 0.73631(13) 0.0628(6) Uani 1 1 d . . .
H19 H 1.1811 -0.5914 0.7395 0.075 Uiso 1 1 calc R . .
C5 C 1.04578(17) 0.2819(2) 0.93317(12) 0.0536(6) Uani 1 1 d . . .
H5 H 1.1031 0.3362 0.9298 0.064 Uiso 1 1 calc R . .
C29 C 0.29539(18) -0.4526(2) 1.11733(14) 0.0642(7) Uani 1 1 d . . .
H29 H 0.2649 -0.4618 1.1618 0.077 Uiso 1 1 calc R . .
C30 C 0.26677(18) -0.5332(2) 1.05981(16) 0.0656(7) Uani 1 1 d . . .
H30 H 0.2175 -0.5975 1.065 0.079 Uiso 1 1 calc R . .
C23 C 0.56329(15) -0.2058(2) 1.09986(10) 0.0472(5) Uani 1 1 d . . .
H23 H 0.5519 -0.2389 1.146 0.057 Uiso 1 1 calc R . .
C17 C 1.0772(3) -0.8685(3) 0.71377(13) 0.0797(8) Uani 1 1 d . . .
H17 H 1.0946 -0.9521 0.7029 0.096 Uiso 1 1 calc R . .
C16 C 0.9756(3) -0.8375(2) 0.72473(13) 0.0731(7) Uani 1 1 d . . .
H16 H 0.9232 -0.8997 0.7201 0.088 Uiso 1 1 calc R . .
C31 C 0.31157(17) -0.5180(2) 0.99460(15) 0.0625(6) Uani 1 1 d . . .
H31 H 0.2922 -0.5719 0.9551 0.075 Uiso 1 1 calc R . .
C4 C 0.95745(18) 0.3240(2) 0.96424(13) 0.0580(6) Uani 1 1 d . . .
H4 H 0.9539 0.4075 0.9809 0.07 Uiso 1 1 calc R . .
C18 C 1.1533(2) -0.7767(3) 0.71870(14) 0.0784(8) Uani 1 1 d . . .
H18 H 1.2225 -0.7973 0.7101 0.094 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O2 C20 1.229(2) . ?
O1 C7 1.230(2) . ?
N2 C20 1.345(2) . ?
N2 C2 1.411(2) . ?
N1 C7 1.345(2) . ?
N1 C1 1.415(2) . ?
C24 C25 1.380(3) . ?
C24 C23 1.389(3) . ?
C24 C27 1.480(3) . ?
C2 C3 1.382(3) . ?
C2 C1 1.383(2) . ?
C20 C21 1.482(3) . ?
C11 C10 1.385(3) . ?
C11 C12 1.387(3) . ?
C11 C14 1.473(3) . ?
C10 C9 1.373(3) . ?
C8 C9 1.381(2) . ?
C8 C13 1.385(3) . ?
C8 C7 1.487(3) . ?
C21 C26 1.381(2) . ?
C21 C22 1.383(3) . ?
C22 C23 1.367(3) . ?
C26 C25 1.377(3) . ?
C1 C6 1.386(3) . ?
C14 C19 1.380(3) . ?
C14 C15 1.389(3) . ?
C6 C5 1.369(3) . ?
C12 C13 1.372(3) . ?
C27 C28 1.381(3) . ?
C27 C32 1.387(3) . ?
C15 C16 1.370(3) . ?
C3 C4 1.367(3) . ?
C32 C31 1.372(3) . ?
C28 C29 1.366(3) . ?
C19 C18 1.379(3) . ?
C5 C4 1.370(3) . ?
C29 C30 1.368(3) . ?
C30 C31 1.366(3) . ?
C17 C16 1.359(4) . ?
C17 C18 1.361(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
C20 N2 C2 123.97(15) . . ?
C7 N1 C1 127.32(15) . . ?
C25 C24 C23 117.32(18) . . ?
C25 C24 C27 121.95(16) . . ?
C23 C24 C27 120.71(17) . . ?
C3 C2 C1 119.13(17) . . ?
C3 C2 N2 119.29(17) . . ?
C1 C2 N2 121.56(17) . . ?
O2 C20 N2 122.29(17) . . ?
O2 C20 C21 121.20(17) . . ?
N2 C20 C21 116.46(15) . . ?
C10 C11 C12 116.88(18) . . ?
C10 C11 C14 121.89(17) . . ?
C12 C11 C14 121.21(17) . . ?
C9 C10 C11 121.37(17) . . ?
C9 C8 C13 117.81(18) . . ?
C9 C8 C7 117.69(16) . . ?
C13 C8 C7 124.49(16) . . ?
C26 C21 C22 118.06(17) . . ?
C26 C21 C20 124.00(17) . . ?
C22 C21 C20 117.93(16) . . ?
C23 C22 C21 121.04(17) . . ?
C25 C26 C21 120.66(18) . . ?
C10 C9 C8 121.34(17) . . ?
C2 C1 C6 119.14(18) . . ?
C2 C1 N1 123.90(16) . . ?
C6 C1 N1 116.89(17) . . ?
C19 C14 C15 117.2(2) . . ?
C19 C14 C11 122.15(19) . . ?
C15 C14 C11 120.65(19) . . ?
C5 C6 C1 120.9(2) . . ?
C26 C25 C24 121.54(17) . . ?
O1 C7 N1 122.03(18) . . ?
O1 C7 C8 120.62(16) . . ?
N1 C7 C8 117.35(15) . . ?
C13 C12 C11 121.99(18) . . ?
C28 C27 C32 117.01(19) . . ?
C28 C27 C24 121.52(18) . . ?
C32 C27 C24 121.44(17) . . ?
C16 C15 C14 121.4(2) . . ?
C4 C3 C2 121.1(2) . . ?
C31 C32 C27 121.2(2) . . ?
C12 C13 C8 120.59(17) . . ?
C29 C28 C27 121.6(2) . . ?
C18 C19 C14 121.0(2) . . ?
C6 C5 C4 119.91(19) . . ?
C28 C29 C30 120.5(2) . . ?
C31 C30 C29 119.1(2) . . ?
C22 C23 C24 121.35(18) . . ?
C16 C17 C18 119.7(3) . . ?
C17 C16 C15 120.3(3) . . ?
C30 C31 C32 120.6(2) . . ?
C3 C4 C5 119.8(2) . . ?
C17 C18 C19 120.4(3) . . ?

# END of CIF
