# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_test_a
_database_code_depnum_ccdc_archive 'CCDC 2151577'
loop_
_audit_author_name
_audit_author_address
'Davi Fernando Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;

_audit_creation_date             2021-09-09T16:30:18-00:00
_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        
;
        3-(4-chlorophenyl)-5-phenyl-4-(phenylsalanyl)oxazol-3(3H)-one
;
_chemical_name_common            'chlorophenyl phenyl phenylsalanyl oxazol'
_chemical_formula_moiety         'C21 H14 Cl N O2 Se'
_chemical_formula_sum            'C21 H14 Cl N O2 Se'
_chemical_formula_weight         426.74
_chemical_melting_point          435K
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc



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

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                   14.6927(6)
_cell_length_b                   6.0979(2)
_cell_length_c                   20.1721(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.3330(10)
_cell_angle_gamma                90
_cell_volume                     1751.06(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.805
_cell_measurement_theta_max      28.314

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

_exptl_crystal_description       tabular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_special_details           
;
 none
;

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

_exptl_absorpt_coefficient_mu    2.312
_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  0.4758
_exptl_absorpt_correction_T_max  0.7631

#----------------------------------------------------------------------------#
#                   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  0.0226
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_number            59681
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             4362
_reflns_number_gt                4125
_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    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   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)+(0.0232P)²+1.0940P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4362
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0479
_refine_ls_wR_factor_gt          0.0466
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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
C2 C 0.80041(8) 0.56957(19) 0.38067(6) 0.0128(2) Uani 1 1 d . . .
C3 C 0.85818(8) 0.73724(19) 0.37554(6) 0.0136(2) Uani 1 1 d . . .
C5 C 0.90051(8) 0.6212(2) 0.48499(6) 0.0156(2) Uani 1 1 d . . .
C7 C 0.86986(8) 0.8903(2) 0.32252(6) 0.0147(2) Uani 1 1 d . . .
C8 C 0.78388(8) 0.3303(2) 0.48133(6) 0.0139(2) Uani 1 1 d . . .
C9 C 0.83914(8) 0.1640(2) 0.51806(6) 0.0179(2) Uani 1 1 d . . .
H9 H 0.9049 0.1616 0.522 0.021 Uiso 1 1 calc R . .
C10 C 0.79742(9) 0.0014(2) 0.54888(6) 0.0193(2) Uani 1 1 d . . .
H10 H 0.8345 -0.1112 0.5749 0.023 Uiso 1 1 calc R . .
C11 C 0.70091(9) 0.0057(2) 0.54114(6) 0.0168(2) Uani 1 1 d . . .
C12 C 0.64550(8) 0.1734(2) 0.50606(6) 0.0162(2) Uani 1 1 d . . .
H12 H 0.5797 0.1753 0.5021 0.019 Uiso 1 1 calc R . .
C13 C 0.68768(8) 0.3383(2) 0.47678(6) 0.0151(2) Uani 1 1 d . . .
H13 H 0.651 0.4565 0.4537 0.018 Uiso 1 1 calc R . .
C15 C 0.83052(8) 0.8546(2) 0.25252(6) 0.0182(2) Uani 1 1 d . . .
H15 H 0.7959 0.7244 0.2379 0.022 Uiso 1 1 calc R . .
C16 C 0.84208(9) 1.0087(2) 0.20465(7) 0.0222(3) Uani 1 1 d . . .
H16 H 0.8145 0.9842 0.1574 0.027 Uiso 1 1 calc R . .
C17 C 0.89380(9) 1.1992(2) 0.22514(7) 0.0229(3) Uani 1 1 d . . .
H17 H 0.9017 1.3038 0.1921 0.027 Uiso 1 1 calc R . .
C18 C 0.93370(9) 1.2347(2) 0.29430(7) 0.0218(3) Uani 1 1 d . . .
H18 H 0.9693 1.3639 0.3085 0.026 Uiso 1 1 calc R . .
C19 C 0.92192(8) 1.0827(2) 0.34264(7) 0.0184(2) Uani 1 1 d . . .
H19 H 0.9493 1.1089 0.3898 0.022 Uiso 1 1 calc R . .
C21 C 0.59828(8) 0.55687(18) 0.32636(5) 0.0107(2) Uani 1 1 d . . .
C22 C 0.59711(8) 0.76507(19) 0.35444(6) 0.0137(2) Uani 1 1 d . . .
H22 H 0.6532 0.8491 0.3673 0.016 Uiso 1 1 calc R . .
C23 C 0.51265(9) 0.8487(2) 0.36343(6) 0.0161(2) Uani 1 1 d . . .
H23 H 0.5116 0.989 0.3837 0.019 Uiso 1 1 calc R . .
C24 C 0.43000(8) 0.7284(2) 0.34295(6) 0.0163(2) Uani 1 1 d . . .
H24 H 0.3726 0.7872 0.3488 0.02 Uiso 1 1 calc R . .
C25 C 0.43150(8) 0.5219(2) 0.31393(6) 0.0148(2) Uani 1 1 d . . .
H25 H 0.3749 0.4407 0.2992 0.018 Uiso 1 1 calc R . .
C26 C 0.51600(8) 0.43414(18) 0.30645(6) 0.0120(2) Uani 1 1 d . . .
H26 H 0.5175 0.2914 0.2879 0.014 Uiso 1 1 calc R . .
Cl14 Cl 0.64801(2) -0.20412(5) 0.576773(17) 0.02326(7) Uani 1 1 d . . .
N1 N 0.82662(7) 0.49715(17) 0.44974(5) 0.01409(19) Uani 1 1 d . . .
O4 O 0.91930(6) 0.77139(14) 0.43985(4) 0.01560(17) Uani 1 1 d . . .
O6 O 0.94301(6) 0.61339(16) 0.54447(5) 0.02012(19) Uani 1 1 d . . .
Se20 Se 0.710702(7) 0.423438(18) 0.312025(5) 0.01194(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   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
C2 C3 1.3491(16) . ?
C2 N1 1.4209(15) . ?
C2 Se20 1.8828(11) . ?
C3 O4 1.3985(13) . ?
C3 C7 1.4613(17) . ?
C5 O6 1.2086(15) . ?
C5 O4 1.3672(16) . ?
C5 N1 1.3690(15) . ?
C7 C19 1.4041(16) . ?
C7 C15 1.4041(17) . ?
C8 C9 1.3924(16) . ?
C8 C13 1.3945(16) . ?
C8 N1 1.4260(16) . ?
C9 C10 1.3908(19) . ?
C10 C11 1.3879(17) . ?
C11 C12 1.3870(17) . ?
C11 Cl14 1.7419(13) . ?
C12 C13 1.3875(17) . ?
C15 C16 1.3880(19) . ?
C16 C17 1.3933(19) . ?
C17 C18 1.390(2) . ?
C18 C19 1.3870(19) . ?
C21 C22 1.3920(16) . ?
C21 C26 1.3937(15) . ?
C21 Se20 1.9263(11) . ?
C22 C23 1.3944(16) . ?
C23 C24 1.3911(17) . ?
C24 C25 1.3913(18) . ?
C25 C26 1.3940(16) . ?

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
C3 C2 N1 106.72(10) . . ?
C3 C2 Se20 129.90(9) . . ?
N1 C2 Se20 122.99(8) . . ?
C2 C3 O4 108.27(10) . . ?
C2 C3 C7 136.91(11) . . ?
O4 C3 C7 114.77(10) . . ?
O6 C5 O4 123.21(11) . . ?
O6 C5 N1 129.97(12) . . ?
O4 C5 N1 106.80(10) . . ?
C19 C7 C15 118.65(12) . . ?
C19 C7 C3 118.45(11) . . ?
C15 C7 C3 122.90(11) . . ?
C9 C8 C13 120.56(11) . . ?
C9 C8 N1 119.61(10) . . ?
C13 C8 N1 119.81(10) . . ?
C10 C9 C8 119.58(11) . . ?
C11 C10 C9 119.16(11) . . ?
C12 C11 C10 121.71(12) . . ?
C12 C11 Cl14 119.11(10) . . ?
C10 C11 Cl14 119.17(10) . . ?
C11 C12 C13 118.94(11) . . ?
C12 C13 C8 119.93(11) . . ?
C16 C15 C7 120.25(12) . . ?
C15 C16 C17 120.65(13) . . ?
C18 C17 C16 119.42(13) . . ?
C19 C18 C17 120.43(12) . . ?
C18 C19 C7 120.59(12) . . ?
C22 C21 C26 120.66(10) . . ?
C22 C21 Se20 122.94(9) . . ?
C26 C21 Se20 116.40(8) . . ?
C21 C22 C23 119.18(11) . . ?
C24 C23 C22 120.53(11) . . ?
C23 C24 C25 119.91(11) . . ?
C24 C25 C26 120.03(11) . . ?
C21 C26 C25 119.65(11) . . ?
C5 N1 C2 108.99(10) . . ?
C5 N1 C8 122.84(10) . . ?
C2 N1 C8 128.13(9) . . ?
C5 O4 C3 109.21(9) . . ?
C2 Se20 C21 99.20(5) . . ?

# END of CIF
