# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mo_dr78f1_0m
_database_code_depnum_ccdc_archive 'CCDC 2349436'
loop_
_audit_author_name
_audit_author_address
'Cobo Justo'
;Universidad de Jaen
Spain
;
_audit_update_record             
;
2024-04-18 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;

_audit_creation_date             2024-04-18T18:27:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
(E)-4-Styryl-2-(4-(trifluoromethyl)phenyl)quinazoline
_chemical_name_common            ' '
_chemical_formula_structural     C23H15F3N2
_chemical_formula_iupac          ' '
_chemical_formula_moiety         C23H15F3N2
_chemical_formula_analytical     ' '
_chemical_formula_sum            'C23 H15 F3 N2'
_chemical_formula_weight         376.37
_chemical_melting_point          414.0(10)
_chemical_compound_source        'synthesized by authors'
_chemical_absolute_configuration syn

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.0188(6)
_cell_length_b                   13.9106(15)
_cell_length_c                   25.986(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1814.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    257
_cell_measurement_theta_min      2.70(10)
_cell_measurement_theta_max      28.00(10)
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.041
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method 
' slow evaporation from n-heptane-ethyl acetate (8:1) solution'

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

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   Multi--Scan
_exptl_absorpt_process_details   
;
SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.4180(10)
_exptl_absorpt_correction_T_max  0.7460(10)
_exptl_transmission_factor_max   0.4180(10)
_exptl_transmission_factor_min   0.7460(10)
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.996

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

_diffrn_source_type              
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_detector_type            'Bruker D8 VENTURE PHOTON-II'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_number            15905
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.145
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        27.496
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_coverage         0.691
_reflns_number_total             4131
_reflns_number_gt                3355
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 'SAINT V8.40B (Bruker AXS Inc., 2019)'

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

_computing_data_collection       'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 2.3'
_computing_publication_material  'Mercury 2.3'

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

_atom_sites_solution_primary     'SHELXT--2014/5 (Sheldrick, 2014)'
_atom_sites_solution_secondary   'SHELXL--2019/1 (Sheldrick, 2019)'
_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+2.0297P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_expression .
_refine_ls_extinction_coef       0
_refine_ls_number_reflns         4131
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0865
_refine_ls_wR_factor_ref         0.1951
_refine_ls_wR_factor_gt          0.1869
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_Flack   0.2(8)
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.088

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F242 F 0.0102(9) 0.3998(3) 0.25720(13) 0.0479(11) Uani 1 1 d . . . . .
F241 F 0.0466(9) 0.5498(3) 0.24235(13) 0.0525(12) Uani 1 1 d . . . . .
F243 F -0.3384(8) 0.4891(3) 0.25519(12) 0.0449(10) Uani 1 1 d . . . . .
N3 N 0.2170(9) 0.5106(3) 0.51297(15) 0.0177(9) Uani 1 1 d . . . . .
N1 N -0.1290(10) 0.6295(3) 0.50805(15) 0.0201(10) Uani 1 1 d . . . . .
C424 C 1.2155(12) 0.2363(4) 0.6372(2) 0.0273(12) Uani 1 1 d . . . . .
H424 H 1.353425 0.19936 0.65262 0.033 Uiso 1 1 calc R U . . .
C423 C 1.0826(12) 0.3052(4) 0.6659(2) 0.0258(12) Uani 1 1 d . . . . .
H423 H 1.129306 0.315207 0.70095 0.031 Uiso 1 1 calc R U . . .
C422 C 0.8807(12) 0.3600(4) 0.6436(2) 0.0250(12) Uani 1 1 d . . . . .
H422 H 0.789552 0.406659 0.663705 0.03 Uiso 1 1 calc R U . . .
C421 C 0.8115(10) 0.3469(3) 0.59217(19) 0.0175(10) Uani 1 1 d . . . . .
C42 C 0.6057(11) 0.4039(4) 0.56693(18) 0.0194(10) Uani 1 1 d . . . . .
H42 H 0.571201 0.39076 0.531673 0.023 Uiso 1 1 calc R U . . .
C41 C 0.4613(10) 0.4731(3) 0.58931(18) 0.0173(10) Uani 1 1 d . . . . .
H41 H 0.495671 0.487816 0.62439 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2519(11) 0.5277(3) 0.56243(18) 0.0190(11) Uani 1 1 d . . . . .
C2 C 0.0263(10) 0.5622(3) 0.48808(18) 0.0176(10) Uani 1 1 d . . . . .
C21 C -0.0036(10) 0.5414(3) 0.43216(18) 0.0163(10) Uani 1 1 d . . . . .
C22 C -0.2096(11) 0.5844(3) 0.40427(19) 0.0195(11) Uani 1 1 d . . . . .
H22 H -0.331147 0.626234 0.421099 0.023 Uiso 1 1 calc R U . . .
C23 C -0.2371(11) 0.5660(4) 0.3520(2) 0.0219(11) Uani 1 1 d . . . . .
H23 H -0.376668 0.595599 0.333026 0.026 Uiso 1 1 calc R U . . .
C24 C -0.0606(11) 0.5046(4) 0.32759(18) 0.0224(11) Uani 1 1 d . . . . .
C241 C -0.0855(13) 0.4866(4) 0.2714(2) 0.0289(12) Uani 1 1 d . . . . .
C4A C 0.0923(11) 0.5977(3) 0.58937(18) 0.0197(10) Uani 1 1 d . . . . .
C5 C 0.1112(12) 0.6181(3) 0.64231(19) 0.0222(11) Uani 1 1 d . . . . .
H5 H 0.238125 0.585109 0.662879 0.027 Uiso 1 1 calc R U . . .
C6 C -0.0513(12) 0.6848(4) 0.6641(2) 0.0227(11) Uani 1 1 d . . . . .
H6 H -0.036426 0.698326 0.699858 0.027 Uiso 1 1 calc R U . . .
C7 C -0.2426(12) 0.7342(3) 0.6341(2) 0.0243(12) Uani 1 1 d . . . . .
H7 H -0.356192 0.780196 0.649857 0.029 Uiso 1 1 calc R U . . .
C8 C -0.2652(11) 0.7165(3) 0.5827(2) 0.0217(11) Uani 1 1 d . . . . .
H8 H -0.392603 0.750514 0.562782 0.026 Uiso 1 1 calc R U . . .
C8A C -0.0973(12) 0.6466(3) 0.55898(19) 0.0191(11) Uani 1 1 d . . . . .
C425 C 1.1486(12) 0.2212(4) 0.5869(2) 0.0276(12) Uani 1 1 d . . . . .
H425 H 1.239467 0.173546 0.567424 0.033 Uiso 1 1 calc R U . . .
C426 C 0.9465(11) 0.2759(4) 0.5637(2) 0.0210(11) Uani 1 1 d . . . . .
H426 H 0.900519 0.264884 0.52876 0.025 Uiso 1 1 calc R U . . .
C26 C 0.1726(11) 0.4798(3) 0.40714(19) 0.0206(11) Uani 1 1 d . . . . .
H26 H 0.312408 0.450015 0.425949 0.025 Uiso 1 1 calc R U . . .
C25 C 0.1453(11) 0.4616(4) 0.35508(19) 0.0228(11) Uani 1 1 d . . . . .
H25 H 0.26686 0.419927 0.338133 0.027 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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
F242 C241 1.352(7) . ?
F241 C241 1.335(7) . ?
F243 C241 1.338(7) . ?
N3 C4 1.319(6) . ?
N3 C2 1.359(6) . ?
N1 C2 1.324(7) . ?
N1 C8A 1.354(6) . ?
C424 C425 1.368(8) . ?
C424 C423 1.386(8) . ?
C424 H424 0.95 . ?
C423 C422 1.394(8) . ?
C423 H423 0.95 . ?
C422 C421 1.394(7) . ?
C422 H422 0.95 . ?
C421 C426 1.408(7) . ?
C421 C42 1.458(7) . ?
C42 C41 1.338(7) . ?
C42 H42 0.95 . ?
C41 C4 1.473(7) . ?
C41 H41 0.95 . ?
C4 C4A 1.442(7) . ?
C2 C21 1.489(6) . ?
C21 C26 1.393(7) . ?
C21 C22 1.397(7) . ?
C22 C23 1.389(7) . ?
C22 H22 0.95 . ?
C23 C24 1.385(8) . ?
C23 H23 0.95 . ?
C24 C25 1.392(8) . ?
C24 C241 1.486(7) . ?
C4A C5 1.408(7) . ?
C4A C8A 1.411(7) . ?
C5 C6 1.359(7) . ?
C5 H5 0.95 . ?
C6 C7 1.416(8) . ?
C6 H6 0.95 . ?
C7 C8 1.361(7) . ?
C7 H7 0.95 . ?
C8 C8A 1.427(7) . ?
C8 H8 0.95 . ?
C425 C426 1.403(8) . ?
C425 H425 0.95 . ?
C426 H426 0.95 . ?
C26 C25 1.383(7) . ?
C26 H26 0.95 . ?
C25 H25 0.95 . ?

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
C4 N3 C2 117.5(4) . . ?
C2 N1 C8A 116.0(4) . . ?
C425 C424 C423 120.2(5) . . ?
C425 C424 H424 119.9 . . ?
C423 C424 H424 119.9 . . ?
C424 C423 C422 120.3(5) . . ?
C424 C423 H423 119.8 . . ?
C422 C423 H423 119.8 . . ?
C423 C422 C421 120.6(5) . . ?
C423 C422 H422 119.7 . . ?
C421 C422 H422 119.7 . . ?
C422 C421 C426 118.4(5) . . ?
C422 C421 C42 122.5(5) . . ?
C426 C421 C42 119.1(4) . . ?
C41 C42 C421 125.4(5) . . ?
C41 C42 H42 117.3 . . ?
C421 C42 H42 117.3 . . ?
C42 C41 C4 123.5(4) . . ?
C42 C41 H41 118.3 . . ?
C4 C41 H41 118.3 . . ?
N3 C4 C4A 121.4(5) . . ?
N3 C4 C41 117.6(4) . . ?
C4A C4 C41 121.0(4) . . ?
N1 C2 N3 126.9(4) . . ?
N1 C2 C21 117.4(4) . . ?
N3 C2 C21 115.6(4) . . ?
C26 C21 C22 119.4(4) . . ?
C26 C21 C2 120.7(5) . . ?
C22 C21 C2 119.8(4) . . ?
C23 C22 C21 120.2(5) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.8(5) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.3(4) . . ?
C23 C24 C241 120.0(5) . . ?
C25 C24 C241 119.6(5) . . ?
F241 C241 F243 106.0(5) . . ?
F241 C241 F242 104.9(5) . . ?
F243 C241 F242 105.9(5) . . ?
F241 C241 C24 113.8(5) . . ?
F243 C241 C24 112.6(5) . . ?
F242 C241 C24 112.9(5) . . ?
C5 C4A C8A 119.6(5) . . ?
C5 C4A C4 125.0(5) . . ?
C8A C4A C4 115.4(4) . . ?
C6 C5 C4A 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
C5 C6 C7 120.5(5) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 119.9(5) . . ?
C7 C8 H8 120 . . ?
C8A C8 H8 120 . . ?
N1 C8A C4A 122.8(5) . . ?
N1 C8A C8 118.3(5) . . ?
C4A C8A C8 119.0(4) . . ?
C424 C425 C426 120.3(5) . . ?
C424 C425 H425 119.9 . . ?
C426 C425 H425 119.9 . . ?
C425 C426 C421 120.3(5) . . ?
C425 C426 H426 119.9 . . ?
C421 C426 H426 119.9 . . ?
C25 C26 C21 120.4(5) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C26 C25 C24 119.8(5) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C425 C424 C423 C422 -0.3(9) . . . . ?
C424 C423 C422 C421 -0.6(9) . . . . ?
C423 C422 C421 C426 1.3(8) . . . . ?
C423 C422 C421 C42 -178.7(5) . . . . ?
C422 C421 C42 C41 -0.4(8) . . . . ?
C426 C421 C42 C41 179.6(5) . . . . ?
C421 C42 C41 C4 -178.9(5) . . . . ?
C2 N3 C4 C4A 0.7(7) . . . . ?
C2 N3 C4 C41 -179.0(4) . . . . ?
C42 C41 C4 N3 -3.9(7) . . . . ?
C42 C41 C4 C4A 176.4(5) . . . . ?
C8A N1 C2 N3 -1.7(7) . . . . ?
C8A N1 C2 C21 179.9(4) . . . . ?
C4 N3 C2 N1 0.8(7) . . . . ?
C4 N3 C2 C21 179.2(4) . . . . ?
N1 C2 C21 C26 172.6(5) . . . . ?
N3 C2 C21 C26 -6.0(6) . . . . ?
N1 C2 C21 C22 -7.1(7) . . . . ?
N3 C2 C21 C22 174.3(4) . . . . ?
C26 C21 C22 C23 -0.3(7) . . . . ?
C2 C21 C22 C23 179.4(4) . . . . ?
C21 C22 C23 C24 0.3(7) . . . . ?
C22 C23 C24 C25 -0.4(7) . . . . ?
C22 C23 C24 C241 -178.5(5) . . . . ?
C23 C24 C241 F241 87.7(7) . . . . ?
C25 C24 C241 F241 -90.4(6) . . . . ?
C23 C24 C241 F243 -33.0(7) . . . . ?
C25 C24 C241 F243 148.9(5) . . . . ?
C23 C24 C241 F242 -152.8(5) . . . . ?
C25 C24 C241 F242 29.1(7) . . . . ?
N3 C4 C4A C5 177.9(5) . . . . ?
C41 C4 C4A C5 -2.4(8) . . . . ?
N3 C4 C4A C8A -1.0(7) . . . . ?
C41 C4 C4A C8A 178.6(5) . . . . ?
C8A C4A C5 C6 -0.3(8) . . . . ?
C4 C4A C5 C6 -179.2(5) . . . . ?
C4A C5 C6 C7 0.4(8) . . . . ?
C5 C6 C7 C8 -0.6(8) . . . . ?
C6 C7 C8 C8A 0.8(8) . . . . ?
C2 N1 C8A C4A 1.2(7) . . . . ?
C2 N1 C8A C8 -178.2(5) . . . . ?
C5 C4A C8A N1 -179.0(5) . . . . ?
C4 C4A C8A N1 0.1(7) . . . . ?
C5 C4A C8A C8 0.4(8) . . . . ?
C4 C4A C8A C8 179.4(5) . . . . ?
C7 C8 C8A N1 178.7(5) . . . . ?
C7 C8 C8A C4A -0.7(8) . . . . ?
C423 C424 C425 C426 0.4(8) . . . . ?
C424 C425 C426 C421 0.2(8) . . . . ?
C422 C421 C426 C425 -1.1(8) . . . . ?
C42 C421 C426 C425 178.9(5) . . . . ?
C22 C21 C26 C25 0.4(7) . . . . ?
C2 C21 C26 C25 -179.3(4) . . . . ?
C21 C26 C25 C24 -0.5(7) . . . . ?
C23 C24 C25 C26 0.5(7) . . . . ?
C241 C24 C25 C26 178.6(5) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2349522'
loop_
_audit_author_name
_audit_author_address
'Cobo Justo'
;Universidad de Jaen
Spain
;
_audit_update_record             
;
2024-04-19 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(E)â\/E?4â\/E?(4â\/E?(Trifluoromethyl)styryl)quinazoline
_chemical_name_common            ?
_chemical_melting_point          429(1)
_chemical_formula_moiety         'C17 H11 F3 N2'
_chemical_formula_sum            'C17 H11 F3 N2'
_chemical_formula_weight         300.28

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.1299(8)
_cell_length_b                   13.2052(9)
_cell_length_c                   7.7725(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.083(2)
_cell_angle_gamma                90
_cell_volume                     1342.32(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.1

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   Multi--Scan
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_measurement_device_type  'CPAD technology'
_diffrn_measurement_device       'Bruker D8 VENTURE PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30816
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.192
_diffrn_reflns_theta_max         27.145
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2951
_reflns_number_gt                2229
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX4 v2021.10-0 (Bruker Nano Inc., 2021)'
_computing_bruker_data_scaling   
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_computing.cell_refinement       'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing.data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+1.6974P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2951
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F433 F 0.44629(14) -0.18025(12) 0.6369(2) 0.0545(5) Uani 1 1 d . . . . .
F431 F 0.42932(15) -0.12740(16) 0.8897(2) 0.0685(7) Uani 1 1 d . . . . .
F432 F 0.55389(11) -0.07661(12) 0.7545(3) 0.0495(5) Uani 1 1 d . . . . .
N3 N 0.07559(14) 0.37323(14) 0.2876(2) 0.0218(4) Uani 1 1 d . . . . .
N1 N 0.00797(14) 0.54075(14) 0.2392(2) 0.0236(4) Uani 1 1 d . . . . .
C43 C 0.45446(17) -0.09763(18) 0.7372(3) 0.0266(5) Uani 1 1 d . . . . .
C424 C 0.39074(16) -0.01140(16) 0.6651(3) 0.0220(5) Uani 1 1 d . . . . .
C423 C 0.41800(17) 0.08758(17) 0.7105(3) 0.0265(5) Uani 1 1 d . . . . .
H423 H 0.478089 0.100285 0.784664 0.032 Uiso 1 1 calc R U . . .
C422 C 0.35755(17) 0.16729(17) 0.6475(3) 0.0253(5) Uani 1 1 d . . . . .
H422 H 0.376492 0.234655 0.679047 0.030 Uiso 1 1 calc R U . . .
C421 C 0.26876(16) 0.15021(16) 0.5377(3) 0.0202(4) Uani 1 1 d . . . . .
C42 C 0.20217(16) 0.23151(16) 0.4663(3) 0.0220(5) Uani 1 1 d . . . . .
H42 H 0.143736 0.211624 0.393239 0.026 Uiso 1 1 calc R U . . .
C41 C 0.21495(16) 0.33070(16) 0.4930(3) 0.0223(5) Uani 1 1 d . . . . .
H41 H 0.270757 0.353047 0.569731 0.027 Uiso 1 1 calc R U . . .
C4 C 0.14597(16) 0.40645(16) 0.4081(3) 0.0202(4) Uani 1 1 d . . . . .
C4A C 0.15307(16) 0.51167(16) 0.4510(3) 0.0197(4) Uani 1 1 d . . . . .
C5 C 0.22580(17) 0.55444(17) 0.5758(3) 0.0242(5) Uani 1 1 d . . . . .
H5 H 0.276926 0.512661 0.633470 0.029 Uiso 1 1 calc R U . . .
C6 C 0.22288(18) 0.65582(17) 0.6140(3) 0.0262(5) Uani 1 1 d . . . . .
H6 H 0.272031 0.683817 0.697742 0.031 Uiso 1 1 calc R U . . .
C7 C 0.14726(17) 0.71869(17) 0.5295(3) 0.0254(5) Uani 1 1 d . . . . .
H7 H 0.145176 0.788510 0.558410 0.030 Uiso 1 1 calc R U . . .
C425 C 0.30343(17) -0.02984(17) 0.5563(3) 0.0239(5) Uani 1 1 d . . . . .
H425 H 0.285135 -0.097295 0.524251 0.029 Uiso 1 1 calc R U . . .
C426 C 0.24290(16) 0.05028(16) 0.4944(3) 0.0226(5) Uani 1 1 d . . . . .
H426 H 0.182625 0.037044 0.420946 0.027 Uiso 1 1 calc R U . . .
C2 C 0.01208(17) 0.44257(17) 0.2094(3) 0.0242(5) Uani 1 1 d . . . . .
H2 H -0.036088 0.417479 0.121252 0.029 Uiso 1 1 calc R U . . .
C8A C 0.07912(16) 0.57645(17) 0.3640(3) 0.0207(4) Uani 1 1 d . . . . .
C8 C 0.07710(17) 0.68028(16) 0.4066(3) 0.0234(5) Uani 1 1 d . . . . .
H8 H 0.026914 0.723416 0.349744 0.028 Uiso 1 1 calc R U . . .


_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
F433 C43 1.340(3) . ?
F431 C43 1.318(3) . ?
F432 C43 1.330(3) . ?
N3 C4 1.330(3) . ?
N3 C2 1.347(3) . ?
N1 C2 1.319(3) . ?
N1 C8A 1.370(3) . ?
C43 C424 1.493(3) . ?
C424 C425 1.384(3) . ?
C424 C423 1.392(3) . ?
C423 C422 1.382(3) . ?
C423 H423 0.9500 . ?
C422 C421 1.401(3) . ?
C422 H422 0.9500 . ?
C421 C426 1.397(3) . ?
C421 C42 1.463(3) . ?
C42 C41 1.334(3) . ?
C42 H42 0.9500 . ?
C41 C4 1.466(3) . ?
C41 H41 0.9500 . ?
C4 C4A 1.430(3) . ?
C4A C5 1.417(3) . ?
C4A C8A 1.419(3) . ?
C5 C6 1.373(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.411(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.364(3) . ?
C7 H7 0.9500 . ?
C425 C426 1.384(3) . ?
C425 H425 0.9500 . ?
C426 H426 0.9500 . ?
C2 H2 0.9500 . ?
C8A C8 1.411(3) . ?
C8 H8 0.9500 . ?

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
C4 N3 C2 117.20(19) . . ?
C2 N1 C8A 115.26(19) . . ?
F431 C43 F432 107.1(2) . . ?
F431 C43 F433 105.5(2) . . ?
F432 C43 F433 104.83(19) . . ?
F431 C43 C424 112.86(19) . . ?
F432 C43 C424 113.03(19) . . ?
F433 C43 C424 112.92(19) . . ?
C425 C424 C423 120.0(2) . . ?
C425 C424 C43 120.1(2) . . ?
C423 C424 C43 119.9(2) . . ?
C422 C423 C424 119.9(2) . . ?
C422 C423 H423 120.0 . . ?
C424 C423 H423 120.0 . . ?
C423 C422 C421 120.9(2) . . ?
C423 C422 H422 119.5 . . ?
C421 C422 H422 119.5 . . ?
C426 C421 C422 118.1(2) . . ?
C426 C421 C42 118.52(19) . . ?
C422 C421 C42 123.4(2) . . ?
C41 C42 C421 126.8(2) . . ?
C41 C42 H42 116.6 . . ?
C421 C42 H42 116.6 . . ?
C42 C41 C4 122.4(2) . . ?
C42 C41 H41 118.8 . . ?
C4 C41 H41 118.8 . . ?
N3 C4 C4A 120.75(19) . . ?
N3 C4 C41 117.03(19) . . ?
C4A C4 C41 122.22(19) . . ?
C5 C4A C8A 118.47(19) . . ?
C5 C4A C4 124.9(2) . . ?
C8A C4A C4 116.55(19) . . ?
C6 C5 C4A 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C426 C425 C424 119.8(2) . . ?
C426 C425 H425 120.1 . . ?
C424 C425 H425 120.1 . . ?
C425 C426 C421 121.2(2) . . ?
C425 C426 H426 119.4 . . ?
C421 C426 H426 119.4 . . ?
N1 C2 N3 128.5(2) . . ?
N1 C2 H2 115.7 . . ?
N3 C2 H2 115.7 . . ?
N1 C8A C8 118.34(19) . . ?
N1 C8A C4A 121.64(19) . . ?
C8 C8A C4A 120.0(2) . . ?
C7 C8 C8A 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C8A C8 H8 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F431 C43 C424 C425 -93.0(3) . . . . ?
F432 C43 C424 C425 145.3(2) . . . . ?
F433 C43 C424 C425 26.5(3) . . . . ?
F431 C43 C424 C423 85.5(3) . . . . ?
F432 C43 C424 C423 -36.1(3) . . . . ?
F433 C43 C424 C423 -154.9(2) . . . . ?
C425 C424 C423 C422 0.3(3) . . . . ?
C43 C424 C423 C422 -178.3(2) . . . . ?
C424 C423 C422 C421 -0.1(4) . . . . ?
C423 C422 C421 C426 0.2(3) . . . . ?
C423 C422 C421 C42 -179.6(2) . . . . ?
C426 C421 C42 C41 -179.8(2) . . . . ?
C422 C421 C42 C41 0.1(4) . . . . ?
C421 C42 C41 C4 177.0(2) . . . . ?
C2 N3 C4 C4A -0.2(3) . . . . ?
C2 N3 C4 C41 179.98(19) . . . . ?
C42 C41 C4 N3 -7.1(3) . . . . ?
C42 C41 C4 C4A 173.0(2) . . . . ?
N3 C4 C4A C5 -179.4(2) . . . . ?
C41 C4 C4A C5 0.5(3) . . . . ?
N3 C4 C4A C8A 2.5(3) . . . . ?
C41 C4 C4A C8A -177.60(19) . . . . ?
C8A C4A C5 C6 1.5(3) . . . . ?
C4 C4A C5 C6 -176.6(2) . . . . ?
C4A C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C423 C424 C425 C426 -0.7(3) . . . . ?
C43 C424 C425 C426 177.9(2) . . . . ?
C424 C425 C426 C421 0.8(3) . . . . ?
C422 C421 C426 C425 -0.6(3) . . . . ?
C42 C421 C426 C425 179.3(2) . . . . ?
C8A N1 C2 N3 1.3(3) . . . . ?
C4 N3 C2 N1 -2.0(3) . . . . ?
C2 N1 C8A C8 -178.0(2) . . . . ?
C2 N1 C8A C4A 1.5(3) . . . . ?
C5 C4A C8A N1 178.53(19) . . . . ?
C4 C4A C8A N1 -3.2(3) . . . . ?
C5 C4A C8A C8 -2.0(3) . . . . ?
C4 C4A C8A C8 176.20(19) . . . . ?
C6 C7 C8 C8A 0.6(3) . . . . ?
N1 C8A C8 C7 -179.5(2) . . . . ?
C4A C8A C8 C7 1.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8 N3 0.95 2.57 3.501(3) 166.1 2 yes
C8 H8 N3 0.95 2.57 3.501(3) 166.1 2 yes

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.055



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane-Ethy acetate mixture (9:1)'
_chemical_compound_source        Synthetic
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2349524'
loop_
_audit_author_name
_audit_author_address
'Cobo Justo'
;Universidad de Jaen
Spain
;
_audit_update_record             
;
2024-04-19 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        (E)--4--(4--Methoxystyryl)quinazoline
_chemical_name_common            ?
_chemical_melting_point          367(1)
_chemical_formula_moiety         'C17 H14 N2 O'
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.30

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   24.6763(13)
_cell_length_b                   3.9753(2)
_cell_length_c                   13.3702(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1311.56(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8910
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.12

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.745
_exptl.absorpt_process_details   
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_exptl.absorpt_correction_type   Multi--Scan
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON-II-CPAD Technology'
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24495
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         27.134
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2885
_reflns_number_gt                2668
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX4 v2021.10-0 (Bruker Nano Inc., 2021)'
_computing_bruker_data_scaling   
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_computing.cell_refinement       'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing.data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+0.3624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1187 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2885
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O43 O 0.53845(6) 0.2583(4) 0.24899(12) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.21007(7) 0.8223(5) 0.74263(13) 0.0220(4) Uani 1 1 d . . . . .
N3 N 0.29545(7) 0.6181(5) 0.68087(12) 0.0211(4) Uani 1 1 d . . . . .
C7 C 0.13629(8) 1.2416(5) 0.54196(16) 0.0235(5) Uani 1 1 d . . . . .
H7 H 0.102140 1.345941 0.531280 0.028 Uiso 1 1 calc R U . . .
C8 C 0.14857(8) 1.1115(5) 0.63391(17) 0.0227(4) Uani 1 1 d . . . . .
H8 H 0.123191 1.128222 0.687115 0.027 Uiso 1 1 calc R U . . .
C8A C 0.19922(8) 0.9517(5) 0.64972(15) 0.0189(4) Uani 1 1 d . . . . .
C4A C 0.23710(8) 0.9270(5) 0.57017(15) 0.0170(4) Uani 1 1 d . . . . .
C4 C 0.28655(8) 0.7492(5) 0.59047(15) 0.0175(4) Uani 1 1 d . . . . .
C41 C 0.32778(8) 0.7001(5) 0.51334(16) 0.0200(4) Uani 1 1 d . . . . .
H41 H 0.321619 0.791595 0.448691 0.024 Uiso 1 1 calc R U . . .
C42 C 0.37405(8) 0.5309(5) 0.53008(15) 0.0198(4) Uani 1 1 d . . . . .
H42 H 0.379276 0.444288 0.595589 0.024 Uiso 1 1 calc R U . . .
C421 C 0.41717(8) 0.4669(5) 0.45739(15) 0.0196(4) Uani 1 1 d . . . . .
C426 C 0.41344(8) 0.5658(5) 0.35646(16) 0.0212(4) Uani 1 1 d . . . . .
H426 H 0.382106 0.681744 0.333761 0.025 Uiso 1 1 calc R U . . .
C425 C 0.45468(8) 0.4961(5) 0.29043(16) 0.0220(4) Uani 1 1 d . . . . .
H425 H 0.451809 0.566766 0.222756 0.026 Uiso 1 1 calc R U . . .
C424 C 0.50077(8) 0.3221(5) 0.32222(18) 0.0209(4) Uani 1 1 d . . . . .
C43 C 0.58607(8) 0.0787(6) 0.27823(19) 0.0276(5) Uani 1 1 d . . . . .
H43A H 0.605095 0.204760 0.330523 0.041 Uiso 1 1 calc R U . . .
H43B H 0.609952 0.051281 0.220233 0.041 Uiso 1 1 calc R U . . .
H43C H 0.575817 -0.143188 0.303985 0.041 Uiso 1 1 calc R U . . .
C2 C 0.25679(9) 0.6653(5) 0.75073(16) 0.0218(4) Uani 1 1 d . . . . .
H2 H 0.264344 0.572359 0.814687 0.026 Uiso 1 1 calc R U . . .
C6 C 0.17389(9) 1.2221(5) 0.46311(16) 0.0222(4) Uani 1 1 d . . . . .
H6 H 0.164855 1.313922 0.399670 0.027 Uiso 1 1 calc R U . . .
C5 C 0.22350(8) 1.0720(5) 0.47656(15) 0.0192(4) Uani 1 1 d . . . . .
H5 H 0.248769 1.065302 0.423000 0.023 Uiso 1 1 calc R U . . .
C422 C 0.46404(8) 0.2980(5) 0.48794(17) 0.0226(4) Uani 1 1 d . . . . .
H422 H 0.467384 0.230843 0.555845 0.027 Uiso 1 1 calc R U . . .
C423 C 0.50592(8) 0.2255(5) 0.42162(18) 0.0233(4) Uani 1 1 d . . . . .
H423 H 0.537534 0.111803 0.443992 0.028 Uiso 1 1 calc R U . . .


_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
O43 C424 1.374(3) . ?
O43 C43 1.430(3) . ?
N1 C2 1.315(3) . ?
N1 C8A 1.371(3) . ?
N3 C4 1.334(3) . ?
N3 C2 1.348(3) . ?
C7 C8 1.368(3) . ?
C7 C6 1.407(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.418(3) . ?
C8 H8 0.9500 . ?
C8A C4A 1.419(3) . ?
C4A C5 1.418(3) . ?
C4A C4 1.436(3) . ?
C4 C41 1.462(3) . ?
C41 C42 1.344(3) . ?
C41 H41 0.9500 . ?
C42 C421 1.463(3) . ?
C42 H42 0.9500 . ?
C421 C422 1.398(3) . ?
C421 C426 1.409(3) . ?
C426 C425 1.375(3) . ?
C426 H426 0.9500 . ?
C425 C424 1.397(3) . ?
C425 H425 0.9500 . ?
C424 C423 1.389(3) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C2 H2 0.9500 . ?
C6 C5 1.374(3) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C422 C423 1.392(3) . ?
C422 H422 0.9500 . ?
C423 H423 0.9500 . ?

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
C424 O43 C43 116.98(18) . . ?
C2 N1 C8A 115.08(18) . . ?
C4 N3 C2 117.18(17) . . ?
C8 C7 C6 120.45(19) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C8A 119.91(19) . . ?
C7 C8 H8 120.0 . . ?
C8A C8 H8 120.0 . . ?
N1 C8A C8 118.39(18) . . ?
N1 C8A C4A 121.62(18) . . ?
C8 C8A C4A 119.99(19) . . ?
C5 C4A C8A 118.51(17) . . ?
C5 C4A C4 124.60(18) . . ?
C8A C4A C4 116.88(18) . . ?
N3 C4 C4A 120.21(18) . . ?
N3 C4 C41 118.18(17) . . ?
C4A C4 C41 121.60(18) . . ?
C42 C41 C4 122.73(19) . . ?
C42 C41 H41 118.6 . . ?
C4 C41 H41 118.6 . . ?
C41 C42 C421 126.46(19) . . ?
C41 C42 H42 116.8 . . ?
C421 C42 H42 116.8 . . ?
C422 C421 C426 117.90(19) . . ?
C422 C421 C42 119.41(19) . . ?
C426 C421 C42 122.69(18) . . ?
C425 C426 C421 120.69(19) . . ?
C425 C426 H426 119.7 . . ?
C421 C426 H426 119.7 . . ?
C426 C425 C424 120.4(2) . . ?
C426 C425 H425 119.8 . . ?
C424 C425 H425 119.8 . . ?
O43 C424 C423 124.67(19) . . ?
O43 C424 C425 115.2(2) . . ?
C423 C424 C425 120.15(19) . . ?
O43 C43 H43A 109.5 . . ?
O43 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
O43 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N1 C2 N3 128.99(19) . . ?
N1 C2 H2 115.5 . . ?
N3 C2 H2 115.5 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C5 C4A 120.20(19) . . ?
C6 C5 H5 119.9 . . ?
C4A C5 H5 119.9 . . ?
C423 C422 C421 121.8(2) . . ?
C423 C422 H422 119.1 . . ?
C421 C422 H422 119.1 . . ?
C424 C423 C422 118.97(19) . . ?
C424 C423 H423 120.5 . . ?
C422 C423 H423 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C7 C8 C8A -0.8(3) . . . . ?
C2 N1 C8A C8 177.26(18) . . . . ?
C2 N1 C8A C4A -2.4(3) . . . . ?
C7 C8 C8A N1 -179.61(19) . . . . ?
C7 C8 C8A C4A 0.0(3) . . . . ?
N1 C8A C4A C5 -178.90(18) . . . . ?
C8 C8A C4A C5 1.5(3) . . . . ?
N1 C8A C4A C4 2.2(3) . . . . ?
C8 C8A C4A C4 -177.40(18) . . . . ?
C2 N3 C4 C4A -1.0(3) . . . . ?
C2 N3 C4 C41 -179.74(18) . . . . ?
C5 C4A C4 N3 -179.26(18) . . . . ?
C8A C4A C4 N3 -0.4(3) . . . . ?
C5 C4A C4 C41 -0.6(3) . . . . ?
C8A C4A C4 C41 178.26(17) . . . . ?
N3 C4 C41 C42 -0.4(3) . . . . ?
C4A C4 C41 C42 -179.09(19) . . . . ?
C4 C41 C42 C421 179.37(19) . . . . ?
C41 C42 C421 C422 177.3(2) . . . . ?
C41 C42 C421 C426 -3.4(3) . . . . ?
C422 C421 C426 C425 0.3(3) . . . . ?
C42 C421 C426 C425 -179.1(2) . . . . ?
C421 C426 C425 C424 0.8(3) . . . . ?
C43 O43 C424 C423 0.2(3) . . . . ?
C43 O43 C424 C425 -179.58(19) . . . . ?
C426 C425 C424 O43 178.10(19) . . . . ?
C426 C425 C424 C423 -1.7(3) . . . . ?
C8A N1 C2 N3 0.8(3) . . . . ?
C4 N3 C2 N1 0.9(3) . . . . ?
C8 C7 C6 C5 0.1(3) . . . . ?
C7 C6 C5 C4A 1.4(3) . . . . ?
C8A C4A C5 C6 -2.2(3) . . . . ?
C4 C4A C5 C6 176.60(19) . . . . ?
C426 C421 C422 C423 -0.5(3) . . . . ?
C42 C421 C422 C423 178.92(19) . . . . ?
O43 C424 C423 C422 -178.29(19) . . . . ?
C425 C424 C423 C422 1.5(3) . . . . ?
C421 C422 C423 C424 -0.4(3) . . . . ?

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane-Ethy acetate mixture (9:1)'
_chemical_compound_source        Synthetic
