# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_boxd
_database_code_depnum_ccdc_archive 'CCDC 1448059'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,2-bis(phenyl)-bi-1,3,4-oxadiazole
_chemical_name_common            BOXD
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 N8 O4'
_chemical_formula_weight         580.56

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   8.632(2)
_cell_length_b                   5.2017(17)
_cell_length_c                   14.695(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.00(3)
_cell_angle_gamma                90.00
_cell_volume                     659.7(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1502
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5832
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1502
_reflns_number_gt                1041
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0237P)²+0.1817P] 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       ?
_refine_ls_number_reflns         1502
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42438(14) 0.7562(2) 0.07563(7) 0.0385(3) Uani 1 1 d . . .
N1 N 0.25777(19) 0.6350(3) -0.03253(9) 0.0452(4) Uani 1 1 d . . .
N2 N 0.34751(19) 0.8389(3) -0.06627(9) 0.0457(4) Uani 1 1 d . . .
C2 C 0.2654(2) 0.1962(4) 0.26081(11) 0.0451(5) Uani 1 1 d . . .
H2A H 0.3080 0.1849 0.3192 0.054 Uiso 1 1 calc R . .
C1 C 0.1522(2) 0.0247(4) 0.23348(12) 0.0450(5) Uani 1 1 d . . .
H1A H 0.1190 -0.1020 0.2733 0.054 Uiso 1 1 calc R . .
C6 C 0.0880(2) 0.0413(4) 0.14672(11) 0.0459(5) Uani 1 1 d . . .
H6A H 0.0112 -0.0738 0.1284 0.055 Uiso 1 1 calc R . .
C5 C 0.1376(2) 0.2283(3) 0.08732(11) 0.0412(4) Uani 1 1 d . . .
H5A H 0.0940 0.2396 0.0292 0.049 Uiso 1 1 calc R . .
C4 C 0.25359(19) 0.4005(3) 0.11471(10) 0.0348(4) Uani 1 1 d . . .
C3 C 0.3163(2) 0.3848(4) 0.20231(11) 0.0420(4) Uani 1 1 d . . .
H3A H 0.3922 0.5008 0.2214 0.050 Uiso 1 1 calc R . .
C7 C 0.3061(2) 0.5937(3) 0.05045(11) 0.0359(4) Uani 1 1 d . . .
C8 C 0.4411(2) 0.9011(3) -0.00057(10) 0.0375(4) 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 C8 1.3595(18) . ?
O1 C7 1.371(2) . ?
N1 C7 1.300(2) . ?
N1 N2 1.409(2) . ?
N2 C8 1.289(2) . ?
C2 C1 1.378(3) . ?
C2 C3 1.381(2) . ?
C2 H2A 0.9300 . ?
C1 C6 1.384(2) . ?
C1 H1A 0.9300 . ?
C6 C5 1.380(2) . ?
C6 H6A 0.9300 . ?
C5 C4 1.397(2) . ?
C5 H5A 0.9300 . ?
C4 C3 1.390(2) . ?
C4 C7 1.457(2) . ?
C3 H3A 0.9300 . ?
C8 C8 1.447(4) 3_675 ?

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 O1 C7 102.04(12) . . ?
C7 N1 N2 106.56(14) . . ?
C8 N2 N1 105.45(13) . . ?
C1 C2 C3 120.68(16) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C2 C1 C6 119.92(17) . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C5 C6 C1 120.20(18) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
C6 C5 C4 119.88(16) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C3 C4 C5 119.65(16) . . ?
C3 C4 C7 121.33(16) . . ?
C5 C4 C7 119.02(14) . . ?
C2 C3 C4 119.66(17) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
N1 C7 O1 112.13(15) . . ?
N1 C7 C4 128.57(16) . . ?
O1 C7 C4 119.28(14) . . ?
N2 C8 O1 113.82(15) . . ?
N2 C8 C8 128.19(18) . 3_675 ?
O1 C8 C8 117.98(18) . 3_675 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_boxd-m-f
_database_code_depnum_ccdc_archive 'CCDC 1448060'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,2-bis(3-fluorophenyl)-bi-1,3,4-oxadiazole
_chemical_name_common            BOXD-m-F
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 F2 N4 O2'
_chemical_formula_weight         326.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   6.7300(13)
_cell_length_b                   7.8225(16)
_cell_length_c                   13.239(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.76(3)
_cell_angle_gamma                90.00
_cell_volume                     696.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1591
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.47

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6630
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_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         3.03
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1591
_reflns_number_gt                1306
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0710P)²+0.0578P] 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       ?
_refine_ls_number_reflns         1591
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14998(19) 0.2529(2) 0.72219(11) 0.0470(4) Uani 1 1 d . . .
H1 H 0.0408 0.2717 0.7612 0.056 Uiso 1 1 calc R . .
C2 C 0.2887(2) 0.1308(2) 0.74874(11) 0.0447(4) Uani 1 1 d . . .
C3 C 0.45421(19) 0.09882(18) 0.69447(10) 0.0424(3) Uani 1 1 d . . .
H3 H 0.5465 0.0160 0.7152 0.051 Uiso 1 1 calc R . .
C4 C 0.47813(17) 0.19459(16) 0.60782(10) 0.0355(3) Uani 1 1 d . . .
C5 C 0.3400(2) 0.31921(18) 0.57809(11) 0.0429(3) Uani 1 1 d . . .
H5 H 0.3572 0.3831 0.5199 0.052 Uiso 1 1 calc R . .
C6 C 0.1768(2) 0.34743(19) 0.63572(12) 0.0483(4) Uani 1 1 d . . .
H6 H 0.0844 0.4308 0.6160 0.058 Uiso 1 1 calc R . .
C7 C 0.64907(18) 0.16685(16) 0.54572(10) 0.0358(3) Uani 1 1 d . . .
C8 C 0.91461(18) 0.05675(16) 0.49841(10) 0.0358(3) Uani 1 1 d . . .
F1 F 0.26137(16) 0.03455(16) 0.83188(8) 0.0723(4) Uani 1 1 d . . .
N1 N 0.69076(17) 0.24454(16) 0.46363(10) 0.0483(3) Uani 1 1 d . . .
N2 N 0.86759(17) 0.17094(16) 0.43232(9) 0.0462(3) Uani 1 1 d . . .
O1 O 0.78526(13) 0.04411(11) 0.57306(7) 0.0372(3) 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
C1 C2 1.369(2) . ?
C1 C6 1.382(2) . ?
C2 F1 1.3535(17) . ?
C2 C3 1.3776(18) . ?
C3 C4 1.3860(19) . ?
C4 C5 1.3906(19) . ?
C4 C7 1.4620(17) . ?
C5 C6 1.3850(18) . ?
C7 N1 1.2879(18) . ?
C7 O1 1.3642(15) . ?
C8 N2 1.2794(18) . ?
C8 O1 1.3517(15) . ?
C8 C8 1.451(2) 3_756 ?
N1 N2 1.4025(15) . ?

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
C2 C1 C6 118.11(12) . . ?
F1 C2 C1 118.64(12) . . ?
F1 C2 C3 117.90(13) . . ?
C1 C2 C3 123.46(14) . . ?
C2 C3 C4 117.55(13) . . ?
C3 C4 C5 120.70(12) . . ?
C3 C4 C7 120.74(12) . . ?
C5 C4 C7 118.57(12) . . ?
C6 C5 C4 119.53(13) . . ?
C1 C6 C5 120.65(13) . . ?
N1 C7 O1 112.65(11) . . ?
N1 C7 C4 127.87(12) . . ?
O1 C7 C4 119.48(11) . . ?
N2 C8 O1 113.85(11) . . ?
N2 C8 C8 128.05(15) . 3_756 ?
O1 C8 C8 118.10(15) . 3_756 ?
C7 N1 N2 106.15(11) . . ?
C8 N2 N1 105.66(11) . . ?
C8 O1 C7 101.69(10) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_boxd-o-f
_database_code_depnum_ccdc_archive 'CCDC 1448061'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,2-bis(2-fluorophenyl)-bi-1,3,4-oxadiazole
_chemical_name_common            BOXD-o-F
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 F2 N4 O2'
_chemical_formula_weight         326.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   8.0707(16)
_cell_length_b                   6.1870(12)
_cell_length_c                   13.704(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.88(3)
_cell_angle_gamma                90.00
_cell_volume                     680.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1538
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      27.46

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6219
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         27.46
_reflns_number_total             1538
_reflns_number_gt                1039
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0974P)²+0.0000P] 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       ?
_refine_ls_number_reflns         1538
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1770
_refine_ls_wR_factor_gt          0.1578
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.10002(18) 0.2061(2) 1.01864(10) 0.0550(5) Uani 1 1 d . . .
O1 O 0.42018(18) -0.2690(2) 0.92934(11) 0.0390(5) Uani 1 1 d . . .
C7 C 0.3127(3) -0.1228(4) 0.96378(16) 0.0380(5) Uani 1 1 d . . .
C4 C 0.2559(3) 0.0551(4) 0.89871(16) 0.0384(5) Uani 1 1 d . . .
N1 N 0.2789(2) -0.1698(3) 1.05138(14) 0.0481(6) Uani 1 1 d . . .
C3 C 0.3078(3) 0.0720(4) 0.80537(16) 0.0440(6) Uani 1 1 d . . .
H3 H 0.3779 -0.0330 0.7836 0.053 Uiso 1 1 calc R . .
C5 C 0.1503(3) 0.2153(4) 0.92839(17) 0.0394(6) Uani 1 1 d . . .
C8 C 0.4442(3) -0.4081(3) 1.00518(16) 0.0386(5) Uani 1 1 d . . .
C1 C 0.1513(3) 0.3984(4) 0.77605(18) 0.0488(6) Uani 1 1 d . . .
H1 H 0.1166 0.5130 0.7350 0.059 Uiso 1 1 calc R . .
C2 C 0.2567(3) 0.2425(4) 0.74444(18) 0.0489(6) Uani 1 1 d . . .
H2 H 0.2931 0.2525 0.6824 0.059 Uiso 1 1 calc R . .
N2 N 0.3660(3) -0.3601(3) 1.07840(15) 0.0476(6) Uani 1 1 d . . .
C6 C 0.0972(3) 0.3846(4) 0.86831(18) 0.0470(6) Uani 1 1 d . . .
H6 H 0.0258 0.4887 0.8895 0.056 Uiso 1 1 calc R . .


_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
F1 C5 1.342(3) . ?
O1 C8 1.348(3) . ?
O1 C7 1.370(3) . ?
C7 N1 1.291(3) . ?
C7 C4 1.461(3) . ?
C4 C3 1.390(3) . ?
C4 C5 1.395(3) . ?
N1 N2 1.402(3) . ?
C3 C2 1.382(3) . ?
C5 C6 1.373(3) . ?
C8 N2 1.274(3) . ?
C8 C8 1.466(4) 3_647 ?
C1 C6 1.382(3) . ?
C1 C2 1.385(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 O1 C7 101.65(17) . . ?
N1 C7 O1 111.9(2) . . ?
N1 C7 C4 130.8(2) . . ?
O1 C7 C4 117.21(19) . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 C7 120.9(2) . . ?
C5 C4 C7 121.4(2) . . ?
C7 N1 N2 106.64(18) . . ?
C2 C3 C4 120.9(2) . . ?
F1 C5 C6 118.7(2) . . ?
F1 C5 C4 119.4(2) . . ?
C6 C5 C4 122.0(2) . . ?
N2 C8 O1 114.49(19) . . ?
N2 C8 C8 128.0(3) . 3_647 ?
O1 C8 C8 117.5(2) . 3_647 ?
C6 C1 C2 120.3(2) . . ?
C3 C2 C1 119.8(2) . . ?
C8 N2 N1 105.27(17) . . ?
C5 C6 C1 119.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_ooch3
_database_code_depnum_ccdc_archive 'CCDC 1448062'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2,2-bis(2-methyloxyphenyl)-bi-1,3,4-oxadiazole
_chemical_name_common            BOXD-o-OCH3
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N4 O4'
_chemical_formula_weight         350.33

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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P2(1)/n

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                   3.9373(8)
_cell_length_b                   11.632(2)
_cell_length_c                   16.943(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.33(3)
_cell_angle_gamma                90.00
_cell_volume                     771.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1744
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7218
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1744
_reflns_number_gt                1461
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0693P)²+0.0599P] 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       ?
_refine_ls_number_reflns         1744
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0446(2) 0.89705(7) 0.42173(5) 0.0267(2) Uani 1 1 d . . .
O2 O 0.7633(3) 0.55300(7) 0.41777(5) 0.0337(3) Uani 1 1 d . . .
C5 C 0.8789(3) 0.59754(10) 0.35228(7) 0.0246(3) Uani 1 1 d . . .
C4 C 0.9630(3) 0.71522(9) 0.35432(7) 0.0235(3) Uani 1 1 d . . .
C6 C 0.9202(3) 0.53400(11) 0.28400(7) 0.0297(3) Uani 1 1 d . . .
H6 H 0.8644 0.4563 0.2820 0.036 Uiso 1 1 calc R . .
C7 C 0.9137(3) 0.78753(9) 0.42236(7) 0.0239(3) Uani 1 1 d . . .
N1 N 0.7557(3) 0.76942(9) 0.48441(6) 0.0320(3) Uani 1 1 d . . .
C3 C 1.0925(3) 0.76447(11) 0.28824(7) 0.0283(3) Uani 1 1 d . . .
H3 H 1.1526 0.8418 0.2896 0.034 Uiso 1 1 calc R . .
C1 C 1.0432(4) 0.58548(11) 0.21936(7) 0.0330(3) Uani 1 1 d . . .
H1 H 1.0662 0.5422 0.1741 0.040 Uiso 1 1 calc R . .
N2 N 0.7812(3) 0.87150(9) 0.52897(6) 0.0325(3) Uani 1 1 d . . .
C8 C 0.9514(3) 0.94122(10) 0.48998(7) 0.0253(3) Uani 1 1 d . . .
C2 C 1.1326(4) 0.70050(11) 0.22116(7) 0.0330(3) Uani 1 1 d . . .
H2 H 1.2185 0.7344 0.1778 0.040 Uiso 1 1 calc R . .
C9 C 0.6803(4) 0.43320(11) 0.41732(8) 0.0347(3) Uani 1 1 d . . .
H9A H 0.5048 0.4176 0.3747 0.052 Uiso 1 1 calc R . .
H9B H 0.6004 0.4128 0.4670 0.052 Uiso 1 1 calc R . .
H9C H 0.8802 0.3889 0.4100 0.052 Uiso 1 1 calc R . .


_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 C8 1.3526(13) . ?
O1 C7 1.3749(13) . ?
O2 C5 1.3484(14) . ?
O2 C9 1.4311(15) . ?
C5 C6 1.3974(16) . ?
C5 C4 1.4078(16) . ?
C4 C3 1.4026(16) . ?
C4 C7 1.4572(15) . ?
C6 C1 1.3818(18) . ?
C7 N1 1.2963(15) . ?
N1 N2 1.4047(14) . ?
C3 C2 1.3820(17) . ?
C1 C2 1.3828(19) . ?
N2 C8 1.2810(15) . ?
C8 C8 1.450(2) 3_776 ?

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 O1 C7 102.00(8) . . ?
C5 O2 C9 117.86(9) . . ?
O2 C5 C6 123.97(11) . . ?
O2 C5 C4 116.95(10) . . ?
C6 C5 C4 119.08(11) . . ?
C3 C4 C5 118.86(10) . . ?
C3 C4 C7 119.18(10) . . ?
C5 C4 C7 121.95(10) . . ?
C1 C6 C5 120.66(11) . . ?
N1 C7 O1 111.76(10) . . ?
N1 C7 C4 131.72(11) . . ?
O1 C7 C4 116.48(10) . . ?
C7 N1 N2 106.64(10) . . ?
C2 C3 C4 121.40(11) . . ?
C6 C1 C2 120.82(11) . . ?
C8 N2 N1 105.56(10) . . ?
N2 C8 O1 114.03(10) . . ?
N2 C8 C8 128.01(13) . 3_776 ?
O1 C8 C8 117.95(12) . 3_776 ?
C3 C2 C1 119.16(11) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_boxd-p-f
_database_code_depnum_ccdc_archive 'CCDC 1448063'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,2-bis(4-fluorophenyl)-bi-1,3,4-oxadiazole
_chemical_name_common            BOXD-p-F
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 F2 N4 O2'
_chemical_formula_weight         326.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   13.425(3)
_cell_length_b                   3.8641(8)
_cell_length_c                   27.628(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.63(3)
_cell_angle_gamma                90.00
_cell_volume                     1413.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3188
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12410
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3188
_reflns_number_gt                1688
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0557P)²+0.0000P] 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       ?
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38372(8) 0.1121(3) 0.45959(4) 0.0458(3) Uani 1 1 d . . .
C7 C 0.36259(13) 0.0043(4) 0.41192(6) 0.0430(4) Uani 1 1 d . . .
C4 C 0.26673(12) 0.1053(4) 0.38276(6) 0.0424(4) Uani 1 1 d . . .
F1 F -0.00536(8) 0.3593(4) 0.30032(5) 0.0887(5) Uani 1 1 d . . .
N1 N 0.43356(11) -0.1860(4) 0.39981(5) 0.0549(4) Uani 1 1 d . . .
O2 O 0.91537(11) 0.0122(3) 0.44155(5) 0.0633(4) Uani 1 1 d . . .
N2 N 0.50912(11) -0.2082(4) 0.44183(6) 0.0536(4) Uani 1 1 d . . .
C8 C 0.47599(12) -0.0304(4) 0.47493(6) 0.0443(4) Uani 1 1 d . . .
C2 C 0.10185(14) 0.3596(5) 0.37629(7) 0.0554(5) Uani 1 1 d . . .
H2 H 0.0527 0.4739 0.3903 0.066 Uiso 1 1 calc R . .
C5 C 0.24692(14) 0.0233(5) 0.33296(6) 0.0523(5) Uani 1 1 d . . .
H5 H 0.2958 -0.0883 0.3184 0.063 Uiso 1 1 calc R . .
C16 C 0.95164(16) 0.0714(5) 0.48984(8) 0.0621(5) Uani 1 1 d . . .
C3 C 0.19396(13) 0.2734(5) 0.40415(7) 0.0479(4) Uani 1 1 d . . .
H3 H 0.2071 0.3286 0.4374 0.057 Uiso 1 1 calc R . .
C12 C 0.76270(16) 0.1866(5) 0.38685(8) 0.0590(5) Uani 1 1 d . . .
C1 C 0.08502(14) 0.2727(5) 0.32784(7) 0.0579(5) Uani 1 1 d . . .
C15 C 0.82410(16) 0.1830(5) 0.43506(8) 0.0609(5) Uani 1 1 d . . .
N4 N 0.89252(15) 0.2556(5) 0.51127(7) 0.0741(5) Uani 1 1 d . . .
N3 N 0.80821(15) 0.3307(5) 0.47521(7) 0.0751(5) Uani 1 1 d . . .
C6 C 0.15472(15) 0.1077(5) 0.30512(7) 0.0587(5) Uani 1 1 d . . .
H6 H 0.1405 0.0538 0.2719 0.070 Uiso 1 1 calc R . .
C13 C 0.66499(17) 0.3255(5) 0.38080(9) 0.0690(6) Uani 1 1 d . . .
H13 H 0.6396 0.4073 0.4080 0.083 Uiso 1 1 calc R . .
F2 F 0.59001(11) 0.2404(4) 0.25022(6) 0.1052(5) Uani 1 1 d . . .
C11 C 0.79948(17) 0.0623(5) 0.34626(8) 0.0665(6) Uani 1 1 d . . .
H11 H 0.8638 -0.0340 0.3500 0.080 Uiso 1 1 calc R . .
C10 C 0.74075(19) 0.0811(6) 0.30012(9) 0.0740(6) Uani 1 1 d . . .
H10 H 0.7653 0.0015 0.2726 0.089 Uiso 1 1 calc R . .
C9 C 0.64593(19) 0.2192(6) 0.29586(9) 0.0740(6) Uani 1 1 d . . .
C14 C 0.60636(18) 0.3421(6) 0.33506(10) 0.0745(6) Uani 1 1 d . . .
H14 H 0.5415 0.4343 0.3309 0.089 Uiso 1 1 calc R . .


_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 C8 1.3570(19) . ?
O1 C7 1.365(2) . ?
C7 N1 1.291(2) . ?
C7 C4 1.453(2) . ?
C4 C3 1.385(2) . ?
C4 C5 1.393(2) . ?
F1 C1 1.361(2) . ?
N1 N2 1.411(2) . ?
O2 C16 1.361(2) . ?
O2 C15 1.377(2) . ?
N2 C8 1.281(2) . ?
C8 C8 1.446(3) 3_656 ?
C2 C1 1.362(3) . ?
C2 C3 1.383(2) . ?
C5 C6 1.382(3) . ?
C16 N4 1.282(3) . ?
C16 C16 1.436(4) 3_756 ?
C12 C11 1.384(3) . ?
C12 C13 1.401(3) . ?
C12 C15 1.445(3) . ?
C1 C6 1.368(3) . ?
C15 N3 1.296(3) . ?
N4 N3 1.407(3) . ?
C13 C14 1.374(3) . ?
F2 C9 1.358(3) . ?
C11 C10 1.384(3) . ?
C10 C9 1.367(3) . ?
C9 C14 1.369(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 O1 C7 102.07(14) . . ?
N1 C7 O1 112.37(15) . . ?
N1 C7 C4 129.26(16) . . ?
O1 C7 C4 118.35(16) . . ?
C3 C4 C5 119.75(16) . . ?
C3 C4 C7 120.79(16) . . ?
C5 C4 C7 119.44(17) . . ?
C7 N1 N2 106.35(14) . . ?
C16 O2 C15 102.21(16) . . ?
C8 N2 N1 105.49(14) . . ?
N2 C8 O1 113.72(14) . . ?
N2 C8 C8 128.2(2) . 3_656 ?
O1 C8 C8 118.1(2) . 3_656 ?
C1 C2 C3 118.26(19) . . ?
C6 C5 C4 120.06(19) . . ?
N4 C16 O2 113.48(19) . . ?
N4 C16 C16 128.5(3) . 3_756 ?
O2 C16 C16 118.1(2) . 3_756 ?
C2 C3 C4 120.26(17) . . ?
C11 C12 C13 119.3(2) . . ?
C11 C12 C15 121.2(2) . . ?
C13 C12 C15 119.47(19) . . ?
F1 C1 C2 118.3(2) . . ?
F1 C1 C6 118.19(18) . . ?
C2 C1 C6 123.50(17) . . ?
N3 C15 O2 111.7(2) . . ?
N3 C15 C12 129.4(2) . . ?
O2 C15 C12 118.85(17) . . ?
C16 N4 N3 105.91(18) . . ?
C15 N3 N4 106.68(18) . . ?
C1 C6 C5 118.17(18) . . ?
C14 C13 C12 120.6(2) . . ?
C10 C11 C12 120.2(2) . . ?
C9 C10 C11 118.6(2) . . ?
F2 C9 C10 117.8(2) . . ?
F2 C9 C14 119.1(2) . . ?
C10 C9 C14 123.1(2) . . ?
C9 C14 C13 118.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_tboxd
_database_code_depnum_ccdc_archive 'CCDC 1448064'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,2-bis(thienyl)-bi-1,3,4-oxadiazole
_chemical_name_common            TBOXD
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 N4 O2 S2'
_chemical_formula_weight         302.33

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   3.8535(8)
_cell_length_b                   15.665(3)
_cell_length_c                   10.114(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.98(3)
_cell_angle_gamma                90.00
_cell_volume                     604.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1370
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      27.47

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5755
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1370
_reflns_number_gt                1105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0664P)²+0.1083P] 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       ?
_refine_ls_number_reflns         1370
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.04876(14) 0.31861(4) 0.30952(5) 0.0303(2) Uani 1 1 d . . .
O1 O 0.4727(4) 0.11568(9) 0.51087(14) 0.0260(3) Uani 1 1 d . . .
C7 C 0.2579(5) 0.16278(14) 0.41902(19) 0.0256(4) Uani 1 1 d . . .
N1 N 0.0812(5) 0.11614(12) 0.32714(18) 0.0305(4) Uani 1 1 d . . .
C4 C 0.2566(5) 0.25422(14) 0.43456(19) 0.0242(4) Uani 1 1 d . . .
N2 N 0.1827(5) 0.03120(11) 0.35665(18) 0.0308(4) Uani 1 1 d . . .
C3 C 0.4092(5) 0.30134(13) 0.5437(2) 0.0246(4) Uani 1 1 d . . .
H3 H 0.5334 0.2779 0.6205 0.029 Uiso 1 1 calc R . .
C8 C 0.4098(5) 0.03456(12) 0.4637(2) 0.0256(4) Uani 1 1 d . . .
C2 C 0.3504(6) 0.39012(13) 0.5225(2) 0.0278(5) Uani 1 1 d . . .
H2 H 0.4326 0.4318 0.5846 0.033 Uiso 1 1 calc R . .
C1 C 0.1601(6) 0.40777(14) 0.4012(2) 0.0305(5) Uani 1 1 d . . .
H1 H 0.0983 0.4627 0.3720 0.037 Uiso 1 1 calc R . .


_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
S1 C1 1.698(2) . ?
S1 C4 1.725(2) . ?
O1 C8 1.367(2) . ?
O1 C7 1.371(2) . ?
C7 N1 1.298(3) . ?
C7 C4 1.441(3) . ?
N1 N2 1.407(3) . ?
C4 C3 1.389(3) . ?
N2 C8 1.295(3) . ?
C3 C2 1.420(3) . ?
C8 C8 1.433(4) 3_656 ?
C2 C1 1.368(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
C1 S1 C4 91.39(11) . . ?
C8 O1 C7 101.69(15) . . ?
N1 C7 O1 112.93(19) . . ?
N1 C7 C4 128.90(19) . . ?
O1 C7 C4 118.17(17) . . ?
C7 N1 N2 106.11(17) . . ?
C3 C4 C7 127.40(19) . . ?
C3 C4 S1 111.97(16) . . ?
C7 C4 S1 120.63(15) . . ?
C8 N2 N1 105.93(16) . . ?
C4 C3 C2 111.07(18) . . ?
N2 C8 O1 113.34(18) . . ?
N2 C8 C8 128.4(2) . 3_656 ?
O1 C8 C8 118.3(2) . 3_656 ?
C1 C2 C3 112.80(19) . . ?
C2 C1 S1 112.77(16) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.080

