# 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 2020

####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 2027432'
loop_
_audit_author_name
_audit_author_address
'Davi Fernando Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;

_audit_creation_date             2016-06-20T15:53:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
(E)-3-phenyl-5-[5-(2-phenylethenyl)-1,3,4-oxadiazol-2-yl]-1,2,4-oxadiazole
;
_chemical_name_common            ' phenyl phenylethenyl oxadiazol oxadiazole'
_chemical_formula_moiety         'C18 H12 N4 O2'
_chemical_formula_sum            'C18 H12 N4 O2'
_chemical_formula_weight         316.32
_chemical_melting_point          none

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.8581(13)
_cell_length_b                   4.2689(3)
_cell_length_c                   22.0230(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.541(3)
_cell_angle_gamma                90
_cell_volume                     1486.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      2.341
_cell_measurement_theta_max      26.589

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

_exptl_crystal_description       tabular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_special_details           
;
 none
;

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

_exptl_absorpt_coefficient_mu    0.096
_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  0.6741
_exptl_absorpt_correction_T_max  0.862

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

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_number            12694
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_full        27.13
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3290
_reflns_number_gt                2103
_reflns_threshold_expression     >2sigma(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    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   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 > 2sigma(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)+(0.0504P)²+0.7209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3290
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.066

#----------------------------------------------------------------------------#
#                   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
O12 O -0.12647(8) 0.5831(4) 0.91707(7) 0.0194(4) Uani 1 1 d . . .
O1 O -0.30096(9) 0.7824(4) 1.00495(7) 0.0247(4) Uani 1 1 d . . .
N15 N -0.08828(10) 0.2332(5) 0.98885(9) 0.0214(5) Uani 1 1 d . . .
N14 N -0.16245(10) 0.3817(5) 1.00442(9) 0.0205(5) Uani 1 1 d . . .
N2 N -0.36967(10) 0.9840(5) 0.98863(9) 0.0249(5) Uani 1 1 d . . .
N4 N -0.28376(10) 0.9561(4) 0.91149(8) 0.0178(4) Uani 1 1 d . . .
C13 C -0.18136(12) 0.5809(5) 0.96172(10) 0.0184(5) Uani 1 1 d . . .
C6 C -0.41688(12) 1.2804(5) 0.89848(10) 0.0186(5) Uani 1 1 d . . .
C19 C 0.09966(12) 0.3947(6) 0.82278(11) 0.0213(5) Uani 1 1 d . . .
C5 C -0.25467(12) 0.7825(5) 0.95631(10) 0.0176(5) Uani 1 1 d . . .
C17 C 0.00420(12) 0.2930(5) 0.90559(10) 0.0207(5) Uani 1 1 d . . .
H17 H 0.0408 0.1364 0.9207 0.025 Uiso 1 1 calc R . .
C18 C 0.02283(12) 0.4429(5) 0.85498(10) 0.0203(5) Uani 1 1 d . . .
H18 H -0.016 0.5898 0.8388 0.024 Uiso 1 1 calc R . .
C3 C -0.35709(12) 1.0764(5) 0.93337(10) 0.0175(5) Uani 1 1 d . . .
C16 C -0.06899(12) 0.3592(5) 0.93793(10) 0.0185(5) Uani 1 1 d . . .
C8 C -0.55308(13) 1.5345(6) 0.88844(11) 0.0251(6) Uani 1 1 d . . .
H8 H -0.6047 1.5797 0.9037 0.03 Uiso 1 1 calc R . .
C7 C -0.49447(12) 1.3506(6) 0.92170(11) 0.0231(5) Uani 1 1 d . . .
H7 H -0.5065 1.2733 0.9595 0.028 Uiso 1 1 calc R . .
C10 C -0.45768(12) 1.5855(6) 0.80958(11) 0.0222(5) Uani 1 1 d . . .
H10 H -0.4453 1.6676 0.7722 0.027 Uiso 1 1 calc R . .
C20 C 0.10311(13) 0.5225(6) 0.76510(11) 0.0270(6) Uani 1 1 d . . .
H20 H 0.0572 0.6359 0.7479 0.032 Uiso 1 1 calc R . .
C9 C -0.53501(13) 1.6510(6) 0.83259(11) 0.0253(6) Uani 1 1 d . . .
H9 H -0.5746 1.7738 0.8102 0.03 Uiso 1 1 calc R . .
C11 C -0.39920(12) 1.3982(5) 0.84236(10) 0.0186(5) Uani 1 1 d . . .
H11 H -0.3479 1.3514 0.8266 0.022 Uiso 1 1 calc R . .
C21 C 0.17405(14) 0.4838(6) 0.73267(12) 0.0330(7) Uani 1 1 d . . .
H21 H 0.1751 0.5665 0.6937 0.04 Uiso 1 1 calc R . .
C22 C 0.24276(14) 0.3223(7) 0.75862(13) 0.0358(7) Uani 1 1 d . . .
H22 H 0.2907 0.2979 0.7373 0.043 Uiso 1 1 calc R . .
C24 C 0.16975(13) 0.2295(6) 0.84837(12) 0.0291(6) Uani 1 1 d . . .
H24 H 0.1687 0.1419 0.887 0.035 Uiso 1 1 calc R . .
C23 C 0.24069(14) 0.1962(7) 0.81628(13) 0.0374(7) Uani 1 1 d . . .
H23 H 0.2875 0.088 0.8337 0.045 Uiso 1 1 calc R . .



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

_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
O12 C13 1.364(2) . ?
O12 C16 1.374(2) . ?
O1 C5 1.346(2) . ?
O1 N2 1.413(2) . ?
N15 C16 1.302(3) . ?
N15 N14 1.402(2) . ?
N14 C13 1.286(3) . ?
N2 C3 1.310(3) . ?
N4 C5 1.290(3) . ?
N4 C3 1.392(2) . ?
C13 C5 1.444(3) . ?
C6 C11 1.384(3) . ?
C6 C7 1.402(3) . ?
C6 C3 1.460(3) . ?
C19 C20 1.388(3) . ?
C19 C24 1.397(3) . ?
C19 C18 1.472(3) . ?
C17 C18 1.339(3) . ?
C17 C16 1.437(3) . ?
C8 C9 1.378(3) . ?
C8 C7 1.382(3) . ?
C10 C11 1.384(3) . ?
C10 C9 1.392(3) . ?
C20 C21 1.389(3) . ?
C21 C22 1.375(4) . ?
C22 C23 1.382(4) . ?
C24 C23 1.382(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
C13 O12 C16 101.45(16) . . ?
C5 O1 N2 104.81(16) . . ?
C16 N15 N14 106.42(18) . . ?
C13 N14 N15 105.77(17) . . ?
C3 N2 O1 104.41(16) . . ?
C5 N4 C3 101.83(17) . . ?
N14 C13 O12 113.99(18) . . ?
N14 C13 C5 126.46(19) . . ?
O12 C13 C5 119.49(19) . . ?
C11 C6 C7 119.6(2) . . ?
C11 C6 C3 121.18(18) . . ?
C7 C6 C3 119.2(2) . . ?
C20 C19 C24 118.7(2) . . ?
C20 C19 C18 118.7(2) . . ?
C24 C19 C18 122.6(2) . . ?
N4 C5 O1 115.14(18) . . ?
N4 C5 C13 129.97(19) . . ?
O1 C5 C13 114.87(19) . . ?
C18 C17 C16 124.0(2) . . ?
C17 C18 C19 125.4(2) . . ?
N2 C3 N4 113.8(2) . . ?
N2 C3 C6 121.88(18) . . ?
N4 C3 C6 124.29(19) . . ?
N15 C16 O12 112.36(17) . . ?
N15 C16 C17 126.9(2) . . ?
O12 C16 C17 120.75(19) . . ?
C9 C8 C7 119.98(19) . . ?
C8 C7 C6 120.1(2) . . ?
C11 C10 C9 120.0(2) . . ?
C19 C20 C21 121.1(2) . . ?
C8 C9 C10 120.3(2) . . ?
C10 C11 C6 120.09(18) . . ?
C22 C21 C20 119.6(2) . . ?
C21 C22 C23 120.1(2) . . ?
C23 C24 C19 120.0(2) . . ?
C22 C23 C24 120.6(2) . . ?

