# 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 2017

####################################################################### 
# 
# 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 1529923'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;

_audit_creation_date             2016-11-09T08:53:29-00:00
_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        
;
2-((1H-tetrazol-5-ylselanyl)methyl)-5-(p-tolyl)-1,3,4-oxadiazole
;
_chemical_name_common'tetrazol   ylselanyl
_chemical_formula_moiety         'C11 H10 N6 O Se'
_chemical_formula_sum            'C11 H10 N6 O Se'
_chemical_formula_weight         321.21
_chemical_melting_point          426K
_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                   6.246(2)
_cell_length_b                   23.899(7)
_cell_length_c                   8.301(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.582(13)
_cell_angle_gamma                90
_cell_volume                     1228.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      29.612

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_special_details           
;
 none
;

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

_exptl_absorpt_coefficient_mu    3.059
_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  0.3742
_exptl_absorpt_correction_T_max  0.7296

#----------------------------------------------------------------------------#
#                   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 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_number            8786
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         29.63
_diffrn_reflns_theta_full        29.63
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3453
_reflns_number_gt                2966
_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-2008 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR, Bo'

#----------------------------------------------------------------------------#
#                   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)+(0.0808P)²+0.3748P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3453
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.138
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.81
_refine_diff_density_rms         0.18

#----------------------------------------------------------------------------#
#                   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'
Se Se -0.0929 2.2259 '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
Se Se 1.06314(4) 0.679620(13) 0.19005(4) 0.01279(13) Uani 1 1 d . . .
O O 0.7406(3) 0.56005(9) 0.1491(2) 0.0120(4) Uani 1 1 d . . .
N3 N 0.8587(4) 0.77567(11) 0.3095(3) 0.0122(5) Uani 1 1 d . . .
H3 H 0.9578 0.7789 0.3948 0.015 Uiso 1 1 calc R . .
N6 N 0.6826(4) 0.74466(11) 0.0855(3) 0.0142(5) Uani 1 1 d . . .
N5 N 0.5824(4) 0.79080(12) 0.1395(3) 0.0163(5) Uani 1 1 d . . .
N2 N 0.3923(4) 0.58044(12) 0.0997(3) 0.0147(5) Uani 1 1 d . . .
N4 N 0.6873(4) 0.80981(13) 0.2735(3) 0.0168(5) Uani 1 1 d . . .
N1 N 0.5090(4) 0.62183(11) 0.0279(3) 0.0142(5) Uani 1 1 d . . .
C4 C 0.5348(4) 0.54507(14) 0.1689(3) 0.0119(5) Uani 1 1 d . . .
C13 C 0.8544(5) 0.73610(13) 0.1947(3) 0.0111(5) Uani 1 1 d . . .
C12 C 0.8996(4) 0.63721(13) 0.0119(3) 0.0124(5) Uani 1 1 d . . .
H12A H 0.8504 0.6632 -0.0784 0.015 Uiso 1 1 calc R . .
H12B H 0.9965 0.6093 -0.029 0.015 Uiso 1 1 calc R . .
C9 C 0.6439(5) 0.41870(14) 0.4320(4) 0.0144(6) Uani 1 1 d . . .
H9 H 0.7646 0.4005 0.4914 0.017 Uiso 1 1 calc R . .
C1 C 0.7102(5) 0.60801(13) 0.0609(3) 0.0116(5) Uani 1 1 d . . .
C10 C 0.6760(4) 0.46697(14) 0.3456(3) 0.0131(5) Uani 1 1 d . . .
H10 H 0.8178 0.4814 0.3459 0.016 Uiso 1 1 calc R . .
C5 C 0.5001(4) 0.49459(13) 0.2578(3) 0.0110(5) Uani 1 1 d . . .
C7 C 0.2630(5) 0.42470(13) 0.3460(4) 0.0135(6) Uani 1 1 d . . .
H7 H 0.1211 0.4105 0.3464 0.016 Uiso 1 1 calc R . .
C8 C 0.4376(5) 0.39642(13) 0.4334(3) 0.0125(5) Uani 1 1 d . . .
C6 C 0.2924(5) 0.47297(13) 0.2589(4) 0.0141(6) Uani 1 1 d . . .
H6 H 0.1716 0.4913 0.2001 0.017 Uiso 1 1 calc R . .
C11 C 0.4022(5) 0.34438(14) 0.5262(4) 0.0165(6) Uani 1 1 d . . .
H11A H 0.2478 0.3354 0.5127 0.025 Uiso 1 1 calc R . .
H11B H 0.4534 0.3503 0.6417 0.025 Uiso 1 1 calc R . .
H11C H 0.4822 0.3134 0.4852 0.025 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
Se C13 1.881(3) . ?
Se C12 1.964(3) . ?
O C1 1.360(4) . ?
O C4 1.365(3) . ?
N3 C13 1.340(4) . ?
N3 N4 1.348(4) . ?
N6 C13 1.327(4) . ?
N6 N5 1.372(4) . ?
N5 N4 1.296(4) . ?
N2 C4 1.305(4) . ?
N2 N1 1.407(4) . ?
N1 C1 1.294(4) . ?
C4 C5 1.446(4) . ?
C12 C1 1.476(4) . ?
C9 C10 1.387(4) . ?
C9 C8 1.396(4) . ?
C10 C5 1.401(4) . ?
C5 C6 1.397(4) . ?
C7 C6 1.386(4) . ?
C7 C8 1.402(4) . ?
C8 C11 1.495(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
C13 Se C12 95.33(13) . . ?
C1 O C4 102.6(2) . . ?
C13 N3 N4 109.2(2) . . ?
C13 N6 N5 105.3(2) . . ?
N4 N5 N6 111.2(2) . . ?
C4 N2 N1 106.3(2) . . ?
N5 N4 N3 105.9(3) . . ?
C1 N1 N2 105.9(3) . . ?
N2 C4 O 112.1(3) . . ?
N2 C4 C5 128.7(3) . . ?
O C4 C5 119.2(3) . . ?
N6 C13 N3 108.4(3) . . ?
N6 C13 Se 126.7(2) . . ?
N3 C13 Se 124.9(2) . . ?
C1 C12 Se 113.1(2) . . ?
C10 C9 C8 121.2(3) . . ?
N1 C1 O 113.1(2) . . ?
N1 C1 C12 127.8(3) . . ?
O C1 C12 119.1(2) . . ?
C9 C10 C5 120.3(3) . . ?
C6 C5 C10 119.2(3) . . ?
C6 C5 C4 120.9(3) . . ?
C10 C5 C4 119.9(3) . . ?
C6 C7 C8 121.6(3) . . ?
C9 C8 C7 117.9(3) . . ?
C9 C8 C11 121.4(3) . . ?
C7 C8 C11 120.7(3) . . ?
C7 C6 C5 119.9(3) . . ?

# END of CIF
_chemical_name_common            
'tetrazol ylselanyl methyl (p-tolyl) oxadiazole'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/MeOH'
