# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_compound-3aa
_database_code_depnum_ccdc_archive 'CCDC 2108509'
loop_
_audit_author_name
_audit_author_address
'DEEVI BASAVAIAH'
;School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '4-phenyl-2,5-di(pyridin-2-yl)oxazole' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N3 O'
_chemical_formula_weight         299.32

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1025(3)
_cell_length_b                   8.5817(5)
_cell_length_c                   14.6868(9)
_cell_angle_alpha                86.201(5)
_cell_angle_beta                 80.086(5)
_cell_angle_gamma                76.138(5)
_cell_volume                     735.34(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    391(300)
_cell_measurement_reflns_used    4828
_cell_measurement_theta_min      2.4170
_cell_measurement_theta_max      26.6430

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      391(300)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8439
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_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         2.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2583
_reflns_number_gt                2035
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0762P)²+0.0651P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.043(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2583
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1360
_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
O1 O 0.3680(2) 0.51200(14) 0.64995(8) 0.0538(4) Uani 1 1 d . . .
N2 N 0.5517(3) 0.70525(18) 0.65059(10) 0.0520(4) Uani 1 1 d . . .
N1 N 0.6220(3) 0.2639(2) 0.82524(11) 0.0605(5) Uani 1 1 d . . .
C7 C 0.5930(3) 0.6014(2) 0.72579(12) 0.0492(5) Uani 1 1 d . . .
C14 C 0.4191(3) 0.6484(2) 0.60951(12) 0.0512(5) Uani 1 1 d . . .
C8 C 0.4818(3) 0.4821(2) 0.72478(12) 0.0485(5) Uani 1 1 d . . .
C6 C 0.7274(3) 0.6385(2) 0.79168(12) 0.0494(5) Uani 1 1 d . . .
C9 C 0.4521(3) 0.3379(2) 0.77926(12) 0.0500(5) Uani 1 1 d . . .
N3 N 0.1459(3) 0.6536(3) 0.50847(13) 0.0791(6) Uani 1 1 d . . .
C15 C 0.3114(3) 0.7173(2) 0.52937(12) 0.0516(5) Uani 1 1 d . . .
C16 C 0.3778(3) 0.8427(2) 0.48240(12) 0.0561(5) Uani 1 1 d . . .
H16 H 0.4957 0.8812 0.4984 0.067 Uiso 1 1 calc R . .
C1 C 0.8987(3) 0.7189(2) 0.76096(14) 0.0565(5) Uani 1 1 d . . .
H1 H 0.9283 0.7475 0.6987 0.068 Uiso 1 1 calc R . .
C5 C 0.6818(3) 0.6009(2) 0.88562(13) 0.0580(5) Uani 1 1 d . . .
H5 H 0.5656 0.5485 0.9077 0.070 Uiso 1 1 calc R . .
C10 C 0.2576(3) 0.2821(2) 0.78199(13) 0.0607(5) Uani 1 1 d . . .
H10 H 0.1401 0.3388 0.7515 0.073 Uiso 1 1 calc R . .
C2 C 1.0257(3) 0.7571(3) 0.82137(16) 0.0663(6) Uani 1 1 d . . .
H2 H 1.1426 0.8091 0.7997 0.080 Uiso 1 1 calc R . .
C13 C 0.5974(4) 0.1280(3) 0.87174(14) 0.0675(6) Uani 1 1 d . . .
H13 H 0.7130 0.0752 0.9043 0.081 Uiso 1 1 calc R . .
C4 C 0.8068(4) 0.6406(3) 0.94579(14) 0.0670(6) Uani 1 1 d . . .
H4 H 0.7750 0.6150 1.0085 0.080 Uiso 1 1 calc R . .
C3 C 0.9792(4) 0.7181(3) 0.91388(16) 0.0703(6) Uani 1 1 d . . .
H3 H 1.0643 0.7442 0.9549 0.084 Uiso 1 1 calc R . .
C12 C 0.4141(4) 0.0617(3) 0.87454(15) 0.0725(6) Uani 1 1 d . . .
H12 H 0.4083 -0.0355 0.9058 0.087 Uiso 1 1 calc R . .
C11 C 0.2385(4) 0.1423(3) 0.82991(15) 0.0730(6) Uani 1 1 d . . .
H11 H 0.1086 0.1027 0.8322 0.088 Uiso 1 1 calc R . .
C17 C 0.2703(4) 0.9116(3) 0.41164(15) 0.0714(6) Uani 1 1 d . . .
H17 H 0.3144 0.9983 0.3786 0.086 Uiso 1 1 calc R . .
C18 C 0.0985(4) 0.8550(3) 0.38861(14) 0.0742(6) Uani 1 1 d . . .
H18 H 0.0221 0.9033 0.3408 0.089 Uiso 1 1 calc R . .
C19 C 0.0401(4) 0.7258(3) 0.43688(16) 0.0840(7) Uani 1 1 d . . .
H19 H -0.0758 0.6854 0.4205 0.101 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 C14 1.356(2) . ?
O1 C8 1.377(2) . ?
N2 C14 1.286(2) . ?
N2 C7 1.391(2) . ?
N1 C13 1.339(2) . ?
N1 C9 1.343(2) . ?
C7 C8 1.359(2) . ?
C7 C6 1.466(2) . ?
C14 C15 1.468(2) . ?
C8 C9 1.460(2) . ?
C6 C1 1.383(3) . ?
C6 C5 1.392(3) . ?
C9 C10 1.376(3) . ?
N3 C15 1.344(2) . ?
N3 C19 1.364(3) . ?
C15 C16 1.346(2) . ?
C16 C17 1.352(3) . ?
C16 H16 0.9300 . ?
C1 C2 1.376(3) . ?
C1 H1 0.9300 . ?
C5 C4 1.369(3) . ?
C5 H5 0.9300 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9300 . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C13 C12 1.365(3) . ?
C13 H13 0.9300 . ?
C4 C3 1.376(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C12 C11 1.372(3) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C17 C18 1.355(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
C14 O1 C8 104.81(14) . . ?
C14 N2 C7 105.30(15) . . ?
C13 N1 C9 116.52(18) . . ?
C8 C7 N2 108.66(15) . . ?
C8 C7 C6 131.90(17) . . ?
N2 C7 C6 119.34(16) . . ?
N2 C14 O1 113.87(15) . . ?
N2 C14 C15 128.00(16) . . ?
O1 C14 C15 118.05(16) . . ?
C7 C8 O1 107.35(15) . . ?
C7 C8 C9 138.16(17) . . ?
O1 C8 C9 114.49(15) . . ?
C1 C6 C5 118.54(17) . . ?
C1 C6 C7 119.57(17) . . ?
C5 C6 C7 121.83(17) . . ?
N1 C9 C10 122.48(17) . . ?
N1 C9 C8 117.02(17) . . ?
C10 C9 C8 120.50(17) . . ?
C15 N3 C19 116.35(19) . . ?
N3 C15 C16 123.43(18) . . ?
N3 C15 C14 117.62(17) . . ?
C16 C15 C14 118.93(16) . . ?
C15 C16 C17 118.96(18) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C2 C1 C6 120.87(19) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C4 C5 C6 120.49(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C11 C10 C9 119.41(19) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
N1 C13 C12 124.4(2) . . ?
N1 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C13 C12 C11 118.14(19) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C10 C11 C12 119.0(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 118.7(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 N3 122.2(2) . . ?
C18 C19 H19 118.9 . . ?
N3 C19 H19 118.9 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_compound-5aib
_database_code_depnum_ccdc_archive 'CCDC 2110003'
loop_
_audit_author_name
_audit_author_address
'Deevi Basavaiah'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '2-(pyridin-2-yl)-4-(p-tolyl)-5-(2,4,6-trifluorophenyl)oxazole' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H13 F3 N2 O'
_chemical_formula_weight         366.33

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'
F F 0.0171 0.0103 '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                   12.0851(4)
_cell_length_b                   7.7428(3)
_cell_length_c                   19.0267(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.465(4)
_cell_angle_gamma                90.00
_cell_volume                     1738.41(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(7)
_cell_measurement_reflns_used    7254
_cell_measurement_theta_min      2.2170
_cell_measurement_theta_max      26.0200

_exptl_crystal_description       blocks
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86343
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(7)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            14164
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3059
_reflns_number_gt                2276
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0580P)²+0.1115P] 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     SHELXL
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3059
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.66328(9) 0.53068(14) 0.33576(6) 0.0565(3) Uani 1 1 d . . .
F2 F 0.58220(9) 0.82066(14) 0.20414(6) 0.0836(4) Uani 1 1 d . . .
F3 F 0.61196(10) 0.22242(14) 0.20249(6) 0.0904(4) Uani 1 1 d . . .
F1 F 0.35546(10) 0.50177(18) 0.02045(6) 0.1033(5) Uani 1 1 d . . .
N2 N 0.85045(11) 0.55742(18) 0.35585(7) 0.0597(4) Uani 1 1 d . . .
N1 N 0.66393(12) 0.51634(18) 0.47948(8) 0.0617(4) Uani 1 1 d . . .
C5 C 0.76192(13) 0.5505(2) 0.46079(8) 0.0535(4) Uani 1 1 d . . .
C7 C 0.80749(13) 0.5458(2) 0.28171(8) 0.0544(4) Uani 1 1 d . . .
C16 C 0.60226(13) 0.5222(2) 0.20581(8) 0.0527(4) Uani 1 1 d . . .
C8 C 0.88472(14) 0.5492(2) 0.23195(8) 0.0564(4) Uani 1 1 d . . .
C15 C 0.69380(14) 0.5306(2) 0.26993(8) 0.0526(4) Uani 1 1 d . . .
C6 C 0.76286(13) 0.5473(2) 0.38422(8) 0.0541(4) Uani 1 1 d . . .
C4 C 0.86038(14) 0.5869(2) 0.51023(9) 0.0656(5) Uani 1 1 d . . .
H4 H 0.9269 0.6115 0.4952 0.079 Uiso 1 1 calc R . .
C21 C 0.54951(14) 0.6678(2) 0.17310(9) 0.0594(4) Uani 1 1 d . . .
C9 C 0.99265(14) 0.6142(2) 0.25490(9) 0.0653(5) Uani 1 1 d . . .
H9 H 1.0139 0.6618 0.3007 0.078 Uiso 1 1 calc R . .
C17 C 0.56429(14) 0.3688(2) 0.17221(9) 0.0615(4) Uani 1 1 d . . .
C10 C 1.06953(15) 0.6098(3) 0.21097(10) 0.0706(5) Uani 1 1 d . . .
H10 H 1.1418 0.6544 0.2279 0.085 Uiso 1 1 calc R . .
C18 C 0.48222(15) 0.3571(3) 0.11060(10) 0.0704(5) Uani 1 1 d . . .
H18 H 0.4588 0.2511 0.0895 0.084 Uiso 1 1 calc R . .
C20 C 0.46666(15) 0.6660(3) 0.11130(9) 0.0709(5) Uani 1 1 d . . .
H20 H 0.4328 0.7672 0.0907 0.085 Uiso 1 1 calc R . .
C19 C 0.43652(15) 0.5085(3) 0.08164(10) 0.0699(6) Uani 1 1 d . . .
C13 C 0.85580(16) 0.4819(2) 0.16278(10) 0.0696(5) Uani 1 1 d . . .
H13 H 0.7832 0.4386 0.1456 0.083 Uiso 1 1 calc R . .
C3 C 0.85858(16) 0.5862(3) 0.58212(9) 0.0735(5) Uani 1 1 d . . .
H3 H 0.9240 0.6100 0.6166 0.088 Uiso 1 1 calc R . .
C1 C 0.66502(16) 0.5173(2) 0.54979(10) 0.0703(5) Uani 1 1 d . . .
H1 H 0.5974 0.4944 0.5639 0.084 Uiso 1 1 calc R . .
C11 C 1.04224(17) 0.5414(3) 0.14282(10) 0.0712(5) Uani 1 1 d . . .
C2 C 0.75892(17) 0.5498(3) 0.60231(10) 0.0744(5) Uani 1 1 d . . .
H2 H 0.7554 0.5474 0.6506 0.089 Uiso 1 1 calc R . .
C12 C 0.93341(17) 0.4785(3) 0.11925(10) 0.0778(6) Uani 1 1 d . . .
H12 H 0.9121 0.4330 0.0731 0.093 Uiso 1 1 calc R . .
C14 C 1.1284(2) 0.5368(3) 0.09653(13) 0.1019(8) Uani 1 1 d . . .
H14A H 1.1268 0.6443 0.0712 0.153 Uiso 1 1 calc R . .
H14B H 1.1109 0.4440 0.0625 0.153 Uiso 1 1 calc R . .
H14C H 1.2025 0.5193 0.1263 0.153 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 C6 1.3549(18) . ?
O1 C15 1.3799(19) . ?
F2 C21 1.3432(19) . ?
F3 C17 1.3434(19) . ?
F1 C19 1.351(2) . ?
N2 C6 1.2903(19) . ?
N2 C7 1.3967(19) . ?
N1 C5 1.334(2) . ?
N1 C1 1.335(2) . ?
C5 C4 1.377(2) . ?
C5 C6 1.460(2) . ?
C7 C15 1.349(2) . ?
C7 C8 1.466(2) . ?
C16 C21 1.376(2) . ?
C16 C17 1.380(2) . ?
C16 C15 1.461(2) . ?
C8 C9 1.378(2) . ?
C8 C13 1.388(2) . ?
C4 C3 1.373(2) . ?
C4 H4 0.9300 . ?
C21 C20 1.370(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C17 C18 1.365(2) . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C18 C19 1.361(3) . ?
C18 H18 0.9300 . ?
C20 C19 1.360(3) . ?
C20 H20 0.9300 . ?
C13 C12 1.379(2) . ?
C13 H13 0.9300 . ?
C3 C2 1.370(3) . ?
C3 H3 0.9300 . ?
C1 C2 1.364(2) . ?
C1 H1 0.9300 . ?
C11 C12 1.383(3) . ?
C11 C14 1.502(3) . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C6 O1 C15 104.21(12) . . ?
C6 N2 C7 105.00(13) . . ?
C5 N1 C1 116.66(15) . . ?
N1 C5 C4 122.95(15) . . ?
N1 C5 C6 117.47(14) . . ?
C4 C5 C6 119.57(15) . . ?
C15 C7 N2 108.47(14) . . ?
C15 C7 C8 131.44(15) . . ?
N2 C7 C8 120.09(14) . . ?
C21 C16 C17 114.88(15) . . ?
C21 C16 C15 122.33(15) . . ?
C17 C16 C15 122.76(15) . . ?
C9 C8 C13 117.70(16) . . ?
C9 C8 C7 119.52(15) . . ?
C13 C8 C7 122.72(16) . . ?
C7 C15 O1 108.14(13) . . ?
C7 C15 C16 134.70(14) . . ?
O1 C15 C16 117.09(13) . . ?
N2 C6 O1 114.17(14) . . ?
N2 C6 C5 126.90(14) . . ?
O1 C6 C5 118.93(14) . . ?
C3 C4 C5 118.86(17) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
F2 C21 C20 118.53(16) . . ?
F2 C21 C16 117.34(14) . . ?
C20 C21 C16 124.13(17) . . ?
C10 C9 C8 120.99(17) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
F3 C17 C18 118.49(17) . . ?
F3 C17 C16 117.31(15) . . ?
C18 C17 C16 124.20(17) . . ?
C11 C10 C9 121.75(18) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C19 C18 C17 116.52(18) . . ?
C19 C18 H18 121.7 . . ?
C17 C18 H18 121.7 . . ?
C19 C20 C21 116.48(18) . . ?
C19 C20 H20 121.8 . . ?
C21 C20 H20 121.8 . . ?
F1 C19 C20 118.12(18) . . ?
F1 C19 C18 118.11(18) . . ?
C20 C19 C18 123.76(17) . . ?
C12 C13 C8 120.79(18) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C2 C3 C4 118.96(17) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
N1 C1 C2 124.18(17) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C10 C11 C12 117.37(17) . . ?
C10 C11 C14 120.46(19) . . ?
C12 C11 C14 122.18(18) . . ?
C1 C2 C3 118.38(17) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C13 C12 C11 121.40(18) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_compound-3bb
_database_code_depnum_ccdc_archive 'CCDC 2108510'
loop_
_audit_author_name
_audit_author_address
'DEEVI BASAVAIAH'
;School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '2,5-bis(6-methylpyridin-2-yl)-4-(p-tolyl)oxazole' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N3 O'
_chemical_formula_weight         341.40

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   I2/a

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

_cell_length_a                   21.1606(10)
_cell_length_b                   7.1694(3)
_cell_length_c                   25.5604(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.862(6)
_cell_angle_gamma                90.00
_cell_volume                     3623.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    201(130)
_cell_measurement_reflns_used    5613
_cell_measurement_theta_min      2.1390
_cell_measurement_theta_max      24.8630

_exptl_crystal_description       plates
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      201(130)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            13867
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3210
_reflns_number_gt                2137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0924P)²+0.0500P] 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     SHELXL
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3210
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.40024(6) 0.21323(19) 0.43845(5) 0.0547(4) Uani 1 1 d . . .
N3 N 0.26284(8) 0.1500(3) 0.40779(7) 0.0602(5) Uani 1 1 d . . .
N2 N 0.39380(8) 0.2329(2) 0.35021(7) 0.0556(5) Uani 1 1 d . . .
N1 N 0.57897(9) 0.2995(2) 0.50024(7) 0.0601(5) Uani 1 1 d . . .
C13 C 0.28928(10) 0.1589(3) 0.36753(9) 0.0524(5) Uani 1 1 d . . .
C14 C 0.36119(10) 0.2020(3) 0.38358(9) 0.0528(5) Uani 1 1 d . . .
C16 C 0.46472(10) 0.2528(3) 0.43926(9) 0.0508(5) Uani 1 1 d . . .
C15 C 0.46049(10) 0.2665(3) 0.38428(9) 0.0518(5) Uani 1 1 d . . .
C17 C 0.51546(10) 0.2588(3) 0.49561(9) 0.0506(5) Uani 1 1 d . . .
C5 C 0.50957(10) 0.3022(3) 0.35679(9) 0.0535(6) Uani 1 1 d . . .
C12 C 0.25214(11) 0.1300(3) 0.31161(9) 0.0625(6) Uani 1 1 d . . .
H12 H 0.2727 0.1326 0.2850 0.075 Uiso 1 1 calc R . .
C2 C 0.59995(11) 0.3601(3) 0.29868(10) 0.0638(6) Uani 1 1 d . . .
C9 C 0.19652(11) 0.1130(3) 0.39221(10) 0.0639(6) Uani 1 1 d . . .
C3 C 0.61369(11) 0.4248(3) 0.35288(10) 0.0687(7) Uani 1 1 d . . .
H3 H 0.6539 0.4889 0.3706 0.082 Uiso 1 1 calc R . .
C21 C 0.62646(11) 0.3068(3) 0.55140(10) 0.0637(6) Uani 1 1 d . . .
C6 C 0.49513(11) 0.2407(3) 0.30229(9) 0.0630(6) Uani 1 1 d . . .
H6 H 0.4545 0.1791 0.2842 0.076 Uiso 1 1 calc R . .
C4 C 0.57009(11) 0.3978(3) 0.38145(9) 0.0649(6) Uani 1 1 d . . .
H4 H 0.5813 0.4442 0.4176 0.078 Uiso 1 1 calc R . .
C10 C 0.15616(11) 0.0886(3) 0.33681(11) 0.0695(7) Uani 1 1 d . . .
H10 H 0.1101 0.0661 0.3271 0.083 Uiso 1 1 calc R . .
C11 C 0.18412(11) 0.0975(3) 0.29626(10) 0.0720(7) Uani 1 1 d . . .
H11 H 0.1574 0.0817 0.2588 0.086 Uiso 1 1 calc R . .
C18 C 0.49783(12) 0.2240(3) 0.54139(10) 0.0654(6) Uani 1 1 d . . .
H18 H 0.4533 0.1955 0.5370 0.079 Uiso 1 1 calc R . .
C7 C 0.53889(12) 0.2678(3) 0.27415(10) 0.0698(7) Uani 1 1 d . . .
H7 H 0.5273 0.2232 0.2378 0.084 Uiso 1 1 calc R . .
C20 C 0.61175(13) 0.2738(3) 0.59895(10) 0.0728(7) Uani 1 1 d . . .
H20 H 0.6457 0.2800 0.6341 0.087 Uiso 1 1 calc R . .
C19 C 0.54694(13) 0.2319(4) 0.59399(10) 0.0761(7) Uani 1 1 d . . .
H19 H 0.5361 0.2091 0.6256 0.091 Uiso 1 1 calc R . .
C1 C 0.64938(12) 0.3871(4) 0.26952(11) 0.0846(8) Uani 1 1 d . . .
H1A H 0.6620 0.5162 0.2713 0.127 Uiso 1 1 calc R . .
H1B H 0.6289 0.3498 0.2311 0.127 Uiso 1 1 calc R . .
H1C H 0.6889 0.3126 0.2875 0.127 Uiso 1 1 calc R . .
C22 C 0.69660(12) 0.3522(4) 0.55372(12) 0.0947(9) Uani 1 1 d . . .
H22A H 0.7072 0.2781 0.5266 0.142 Uiso 1 1 calc R . .
H22B H 0.7284 0.3254 0.5905 0.142 Uiso 1 1 calc R . .
H22C H 0.6991 0.4820 0.5455 0.142 Uiso 1 1 calc R . .
C8 C 0.16670(14) 0.1009(5) 0.43697(12) 0.1031(10) Uani 1 1 d . . .
H8A H 0.1830 -0.0094 0.4589 0.155 Uiso 1 1 calc R . .
H8B H 0.1183 0.0956 0.4201 0.155 Uiso 1 1 calc R . .
H8C H 0.1796 0.2088 0.4606 0.155 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 C14 1.353(2) . ?
O1 C16 1.387(2) . ?
N3 C13 1.337(2) . ?
N3 C9 1.342(2) . ?
N2 C14 1.293(2) . ?
N2 C15 1.390(3) . ?
N1 C21 1.337(3) . ?
N1 C17 1.339(3) . ?
C13 C12 1.380(3) . ?
C13 C14 1.461(3) . ?
C16 C15 1.379(3) . ?
C16 C17 1.459(3) . ?
C15 C5 1.469(3) . ?
C17 C18 1.372(3) . ?
C5 C6 1.388(3) . ?
C5 C4 1.390(3) . ?
C12 C11 1.370(3) . ?
C12 H12 0.9300 . ?
C2 C7 1.387(3) . ?
C2 C3 1.390(3) . ?
C2 C1 1.497(3) . ?
C9 C10 1.380(3) . ?
C9 C8 1.493(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C21 C20 1.378(3) . ?
C21 C22 1.500(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?
C10 C11 1.366(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C7 H7 0.9300 . ?
C20 C19 1.365(3) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
C14 O1 C16 105.19(16) . . ?
C13 N3 C9 117.47(19) . . ?
C14 N2 C15 106.12(18) . . ?
C21 N1 C17 118.5(2) . . ?
N3 C13 C12 123.4(2) . . ?
N3 C13 C14 118.27(18) . . ?
C12 C13 C14 118.34(19) . . ?
N2 C14 O1 113.65(18) . . ?
N2 C14 C13 126.74(19) . . ?
O1 C14 C13 119.61(18) . . ?
C15 C16 O1 107.03(17) . . ?
C15 C16 C17 139.62(19) . . ?
O1 C16 C17 113.27(18) . . ?
C16 C15 N2 108.00(18) . . ?
C16 C15 C5 134.37(19) . . ?
N2 C15 C5 117.61(19) . . ?
N1 C17 C18 122.3(2) . . ?
N1 C17 C16 117.16(19) . . ?
C18 C17 C16 120.58(19) . . ?
C6 C5 C4 116.7(2) . . ?
C6 C5 C15 119.0(2) . . ?
C4 C5 C15 124.3(2) . . ?
C11 C12 C13 118.4(2) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C7 C2 C3 116.1(2) . . ?
C7 C2 C1 122.7(2) . . ?
C3 C2 C1 121.2(2) . . ?
N3 C9 C10 122.0(2) . . ?
N3 C9 C8 117.8(2) . . ?
C10 C9 C8 120.2(2) . . ?
C4 C3 C2 122.6(2) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
N1 C21 C20 121.9(2) . . ?
N1 C21 C22 115.8(2) . . ?
C20 C21 C22 122.2(2) . . ?
C7 C6 C5 122.2(2) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.0(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C17 C18 C19 119.0(2) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C6 C7 C2 121.6(2) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C19 C20 C21 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C19 C18 118.9(2) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_compound-5afv
_database_code_depnum_ccdc_archive 'CCDC 2110002'
loop_
_audit_author_name
_audit_author_address
'Deevi Basavaiah'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '5-(4-chlorophenyl)-4-cyclopropyl-2-(pyridin-2-yl)oxazole' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Cl N2 O'
_chemical_formula_weight         296.74

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'
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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   5.7112(16)
_cell_length_b                   23.177(8)
_cell_length_c                   10.865(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.891(13)
_cell_angle_gamma                90.00
_cell_volume                     1438.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8717
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.47

_exptl_crystal_description       blocks
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.2593
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1808 before and 0.1108 after correction. The Ratio of minimum to maximum transmission is 0.3478. The λ/2 correction factor is Not present.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12472
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2422
_reflns_number_gt                2173
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0740P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(6)
_refine_ls_number_reflns         2422
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
Cl1 Cl 1.23123(12) 0.45889(4) 0.13968(7) 0.0685(3) Uani 1 1 d . . .
O1 O 0.4566(3) 0.32795(8) 0.50633(15) 0.0444(4) Uani 1 1 d . . .
N2 N 0.1013(4) 0.24907(11) 0.4993(2) 0.0545(6) Uani 1 1 d . . .
N1 N 0.4015(4) 0.34979(9) 0.70355(19) 0.0454(5) Uani 1 1 d . . .
C12 C 0.7733(5) 0.38973(11) 0.4426(2) 0.0424(6) Uani 1 1 d . . .
C5 C 0.1394(5) 0.27655(10) 0.6057(2) 0.0421(6) Uani 1 1 d . . .
C16 C 1.1249(5) 0.43846(12) 0.3778(3) 0.0508(6) Uani 1 1 d . . .
H16 H 1.2646 0.4572 0.3974 0.061 Uiso 1 1 calc R . .
C17 C 0.9859(5) 0.41733(12) 0.4696(3) 0.0502(6) Uani 1 1 d . . .
H17 H 1.0342 0.4215 0.5512 0.060 Uiso 1 1 calc R . .
C11 C 0.6183(5) 0.36970(10) 0.5387(2) 0.0431(6) Uani 1 1 d . . .
C6 C 0.3336(4) 0.31825(10) 0.6109(2) 0.0431(6) Uani 1 1 d . . .
C14 C 0.8487(5) 0.40420(12) 0.2251(2) 0.0511(7) Uani 1 1 d . . .
H14 H 0.8037 0.3998 0.1430 0.061 Uiso 1 1 calc R . .
C7 C 0.5851(5) 0.38331(10) 0.6594(2) 0.0450(6) Uani 1 1 d . . .
C13 C 0.7084(5) 0.38309(12) 0.3178(2) 0.0489(6) Uani 1 1 d . . .
H13 H 0.5694 0.3643 0.2973 0.059 Uiso 1 1 calc R . .
C8 C 0.7093(5) 0.42537(12) 0.7393(3) 0.0564(7) Uani 1 1 d . . .
H8 H 0.7932 0.4559 0.6959 0.068 Uiso 1 1 calc R . .
C15 C 1.0554(5) 0.43171(11) 0.2557(2) 0.0477(6) Uani 1 1 d . . .
C4 C 0.0001(5) 0.26881(11) 0.7086(2) 0.0488(6) Uani 1 1 d . . .
H4 H 0.0331 0.2884 0.7816 0.059 Uiso 1 1 calc R . .
C1 C -0.0830(5) 0.21329(14) 0.4940(3) 0.0612(7) Uani 1 1 d . . .
H1 H -0.1126 0.1938 0.4206 0.073 Uiso 1 1 calc R . .
C2 C -0.2319(5) 0.20356(13) 0.5908(3) 0.0556(7) Uani 1 1 d . . .
H2 H -0.3587 0.1787 0.5820 0.067 Uiso 1 1 calc R . .
C9 C 0.6152(6) 0.44205(14) 0.8614(3) 0.0651(9) Uani 1 1 d . . .
H9A H 0.6360 0.4817 0.8876 0.078 Uiso 1 1 calc R . .
H9B H 0.4694 0.4245 0.8864 0.078 Uiso 1 1 calc R . .
C3 C -0.1886(5) 0.23138(12) 0.7001(3) 0.0534(7) Uani 1 1 d . . .
H3 H -0.2843 0.2253 0.7674 0.064 Uiso 1 1 calc R . .
C10 C 0.8225(7) 0.40545(16) 0.8580(3) 0.0773(10) Uani 1 1 d . . .
H10A H 0.8048 0.3652 0.8805 0.093 Uiso 1 1 calc R . .
H10B H 0.9716 0.4225 0.8818 0.093 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
Cl1 C15 1.742(3) . ?
O1 C6 1.364(3) . ?
O1 C11 1.379(3) . ?
N2 C5 1.335(3) . ?
N2 C1 1.341(4) . ?
N1 C6 1.298(3) . ?
N1 C7 1.396(3) . ?
C12 C17 1.400(4) . ?
C12 C13 1.409(4) . ?
C12 C11 1.456(4) . ?
C5 C4 1.394(3) . ?
C5 C6 1.471(4) . ?
C16 C17 1.374(4) . ?
C16 C15 1.387(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C11 C7 1.365(4) . ?
C14 C15 1.378(4) . ?
C14 C13 1.386(4) . ?
C14 H14 0.9300 . ?
C7 C8 1.479(4) . ?
C13 H13 0.9300 . ?
C8 C9 1.490(4) . ?
C8 C10 1.507(5) . ?
C8 H8 0.9800 . ?
C4 C3 1.385(4) . ?
C4 H4 0.9300 . ?
C1 C2 1.381(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C9 C10 1.458(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
C6 O1 C11 104.74(19) . . ?
C5 N2 C1 116.7(2) . . ?
C6 N1 C7 105.3(2) . . ?
C17 C12 C13 117.8(2) . . ?
C17 C12 C11 122.1(2) . . ?
C13 C12 C11 120.1(3) . . ?
N2 C5 C4 123.1(2) . . ?
N2 C5 C6 117.3(2) . . ?
C4 C5 C6 119.5(2) . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
C7 C11 O1 107.8(2) . . ?
C7 C11 C12 135.3(2) . . ?
O1 C11 C12 116.9(2) . . ?
N1 C6 O1 113.7(2) . . ?
N1 C6 C5 128.0(2) . . ?
O1 C6 C5 118.3(2) . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C11 C7 N1 108.5(2) . . ?
C11 C7 C8 130.1(3) . . ?
N1 C7 C8 121.4(2) . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 C10 119.7(3) . . ?
C9 C8 C10 58.2(2) . . ?
C7 C8 H8 115.3 . . ?
C9 C8 H8 115.3 . . ?
C10 C8 H8 115.3 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 Cl1 119.6(2) . . ?
C16 C15 Cl1 119.4(2) . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N2 C1 C2 124.1(3) . . ?
N2 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C10 C9 C8 61.5(2) . . ?
C10 C9 H9A 117.6 . . ?
C8 C9 H9A 117.6 . . ?
C10 C9 H9B 117.6 . . ?
C8 C9 H9B 117.6 . . ?
H9A C9 H9B 114.7 . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C9 C10 C8 60.3(2) . . ?
C9 C10 H10A 117.7 . . ?
C8 C10 H10A 117.7 . . ?
C9 C10 H10B 117.7 . . ?
C8 C10 H10B 117.7 . . ?
H10A C10 H10B 114.9 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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_compound-3ea
_database_code_depnum_ccdc_archive 'CCDC 2108511'
loop_
_audit_author_name
_audit_author_address
'DEEVI BASAVAIAH'
;School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '4-phenyl-2,5-di(quinolin-2-yl)oxazole' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H17 N3 O'
_chemical_formula_weight         399.44

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                   11.3712(5)
_cell_length_b                   9.2050(4)
_cell_length_c                   19.1767(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.402(5)
_cell_angle_gamma                90.00
_cell_volume                     1944.18(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296.9(3)
_cell_measurement_reflns_used    7490
_cell_measurement_theta_min      2.1890
_cell_measurement_theta_max      26.5750

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.16858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296.9(3)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            16503
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3423
_reflns_number_gt                2570
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0604P)²+0.1127P] 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     SHELXL
_refine_ls_extinction_coef       0.0050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3423
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.63679(9) 0.39471(11) 0.52983(5) 0.0441(3) Uani 1 1 d . . .
N3 N 0.43029(11) 0.12804(13) 0.43549(7) 0.0436(3) Uani 1 1 d . . .
N1 N 0.76122(11) 0.59751(13) 0.61882(7) 0.0430(3) Uani 1 1 d . . .
N2 N 0.74372(11) 0.42327(13) 0.44875(7) 0.0458(4) Uani 1 1 d . . .
C10 C 0.58493(13) 0.30653(16) 0.47221(8) 0.0408(4) Uani 1 1 d . . .
C7 C 0.48057(13) 0.22536(16) 0.48359(8) 0.0407(4) Uani 1 1 d . . .
C11 C 0.65018(13) 0.32456(16) 0.42140(8) 0.0418(4) Uani 1 1 d . . .
C18 C 0.73112(13) 0.45960(16) 0.51167(8) 0.0421(4) Uani 1 1 d . . .
C23 C 0.82590(14) 0.69584(16) 0.66643(8) 0.0437(4) Uani 1 1 d . . .
C19 C 0.80356(13) 0.56224(16) 0.56304(8) 0.0419(4) Uani 1 1 d . . .
C6 C 0.33177(13) 0.05285(16) 0.44553(8) 0.0430(4) Uani 1 1 d . . .
C12 C 0.63887(13) 0.26912(17) 0.34797(8) 0.0440(4) Uani 1 1 d . . .
C22 C 0.93673(14) 0.75498(17) 0.65909(9) 0.0467(4) Uani 1 1 d . . .
C5 C 0.28467(14) 0.07493(18) 0.50628(9) 0.0485(4) Uani 1 1 d . . .
C1 C 0.27656(15) -0.04874(18) 0.39340(9) 0.0527(4) Uani 1 1 d . . .
H1 H 0.3079 -0.0646 0.3537 0.063 Uiso 1 1 calc R . .
C9 C 0.34272(15) 0.1781(2) 0.55680(9) 0.0562(5) Uani 1 1 d . . .
H9 H 0.3151 0.1950 0.5978 0.067 Uiso 1 1 calc R . .
C21 C 0.97848(15) 0.71103(18) 0.59917(9) 0.0546(5) Uani 1 1 d . . .
H21 H 1.0518 0.7464 0.5929 0.065 Uiso 1 1 calc R . .
C8 C 0.43920(14) 0.25359(18) 0.54602(9) 0.0512(4) Uani 1 1 d . . .
H8 H 0.4776 0.3229 0.5792 0.061 Uiso 1 1 calc R . .
C24 C 0.77875(16) 0.74105(18) 0.72414(9) 0.0546(5) Uani 1 1 d . . .
H24 H 0.7056 0.7030 0.7293 0.065 Uiso 1 1 calc R . .
C20 C 0.91200(15) 0.61741(18) 0.55073(9) 0.0519(4) Uani 1 1 d . . .
H20 H 0.9374 0.5901 0.5101 0.062 Uiso 1 1 calc R . .
C17 C 0.69915(16) 0.3429(2) 0.30389(9) 0.0582(5) Uani 1 1 d . . .
H17 H 0.7465 0.4233 0.3220 0.070 Uiso 1 1 calc R . .
C27 C 0.99808(17) 0.85562(19) 0.71089(10) 0.0611(5) Uani 1 1 d . . .
H27 H 1.0721 0.8940 0.7074 0.073 Uiso 1 1 calc R . .
C4 C 0.18239(15) -0.0067(2) 0.51229(11) 0.0621(5) Uani 1 1 d . . .
H4 H 0.1506 0.0056 0.5521 0.075 Uiso 1 1 calc R . .
C26 C 0.94996(19) 0.8969(2) 0.76579(10) 0.0679(6) Uani 1 1 d . . .
H26 H 0.9911 0.9639 0.7994 0.081 Uiso 1 1 calc R . .
C2 C 0.17729(16) -0.12455(19) 0.40032(11) 0.0616(5) Uani 1 1 d . . .
H2 H 0.1406 -0.1909 0.3650 0.074 Uiso 1 1 calc R . .
C3 C 0.13047(16) -0.1031(2) 0.46020(12) 0.0657(5) Uani 1 1 d . . .
H3 H 0.0627 -0.1555 0.4645 0.079 Uiso 1 1 calc R . .
C15 C 0.62143(18) 0.1816(2) 0.20605(10) 0.0687(6) Uani 1 1 d . . .
H15 H 0.6145 0.1529 0.1587 0.082 Uiso 1 1 calc R . .
C25 C 0.83959(19) 0.8401(2) 0.77243(9) 0.0659(5) Uani 1 1 d . . .
H25 H 0.8074 0.8701 0.8101 0.079 Uiso 1 1 calc R . .
C16 C 0.69038(18) 0.2996(2) 0.23406(10) 0.0690(6) Uani 1 1 d . . .
H16 H 0.7316 0.3509 0.2057 0.083 Uiso 1 1 calc R . .
C13 C 0.57121(18) 0.1493(2) 0.31925(10) 0.0666(5) Uani 1 1 d . . .
H13 H 0.5307 0.0966 0.3475 0.080 Uiso 1 1 calc R . .
C14 C 0.56269(19) 0.1066(2) 0.24916(11) 0.0782(6) Uani 1 1 d . . .
H14 H 0.5163 0.0256 0.2309 0.094 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 C18 1.3469(16) . ?
O1 C10 1.3796(17) . ?
N3 C7 1.3107(18) . ?
N3 C6 1.3706(18) . ?
N1 C19 1.3182(18) . ?
N1 C23 1.3638(19) . ?
N2 C18 1.2939(18) . ?
N2 C11 1.3981(19) . ?
C10 C11 1.3738(19) . ?
C10 C7 1.464(2) . ?
C7 C8 1.415(2) . ?
C11 C12 1.473(2) . ?
C18 C19 1.462(2) . ?
C23 C24 1.407(2) . ?
C23 C22 1.412(2) . ?
C19 C20 1.407(2) . ?
C6 C1 1.399(2) . ?
C6 C5 1.413(2) . ?
C12 C13 1.378(2) . ?
C12 C17 1.390(2) . ?
C22 C21 1.407(2) . ?
C22 C27 1.410(2) . ?
C5 C9 1.399(2) . ?
C5 C4 1.413(2) . ?
C1 C2 1.361(2) . ?
C1 H1 0.9300 . ?
C9 C8 1.357(2) . ?
C9 H9 0.9300 . ?
C21 C20 1.352(2) . ?
C21 H21 0.9300 . ?
C8 H8 0.9300 . ?
C24 C25 1.359(2) . ?
C24 H24 0.9300 . ?
C20 H20 0.9300 . ?
C17 C16 1.377(2) . ?
C17 H17 0.9300 . ?
C27 C26 1.356(3) . ?
C27 H27 0.9300 . ?
C4 C3 1.356(2) . ?
C4 H4 0.9300 . ?
C26 C25 1.395(3) . ?
C26 H26 0.9300 . ?
C2 C3 1.395(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C15 C16 1.368(3) . ?
C15 C14 1.372(3) . ?
C15 H15 0.9300 . ?
C25 H25 0.9300 . ?
C16 H16 0.9300 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
C18 O1 C10 105.26(11) . . ?
C7 N3 C6 118.36(13) . . ?
C19 N1 C23 117.50(13) . . ?
C18 N2 C11 105.51(12) . . ?
C11 C10 O1 107.35(13) . . ?
C11 C10 C7 140.20(14) . . ?
O1 C10 C7 112.45(12) . . ?
N3 C7 C8 122.84(14) . . ?
N3 C7 C10 118.15(13) . . ?
C8 C7 C10 119.00(14) . . ?
C10 C11 N2 107.89(13) . . ?
C10 C11 C12 134.60(14) . . ?
N2 C11 C12 117.46(13) . . ?
N2 C18 O1 113.98(13) . . ?
N2 C18 C19 128.37(14) . . ?
O1 C18 C19 117.63(13) . . ?
N1 C23 C24 118.37(14) . . ?
N1 C23 C22 122.37(14) . . ?
C24 C23 C22 119.25(15) . . ?
N1 C19 C20 124.02(15) . . ?
N1 C19 C18 116.59(13) . . ?
C20 C19 C18 119.39(14) . . ?
N3 C6 C1 118.33(14) . . ?
N3 C6 C5 122.27(15) . . ?
C1 C6 C5 119.40(14) . . ?
C13 C12 C17 117.27(15) . . ?
C13 C12 C11 124.49(15) . . ?
C17 C12 C11 118.23(15) . . ?
C21 C22 C27 123.78(16) . . ?
C21 C22 C23 117.48(15) . . ?
C27 C22 C23 118.73(16) . . ?
C9 C5 C6 117.27(14) . . ?
C9 C5 C4 124.10(16) . . ?
C6 C5 C4 118.63(16) . . ?
C2 C1 C6 120.58(17) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C8 C9 C5 120.13(15) . . ?
C8 C9 H9 119.9 . . ?
C5 C9 H9 119.9 . . ?
C20 C21 C22 119.98(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C9 C8 C7 119.10(16) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C25 C24 C23 120.33(17) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C21 C20 C19 118.59(15) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C16 C17 C12 121.50(18) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
C26 C27 C22 120.45(17) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?
C3 C4 C5 120.27(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C27 C26 C25 120.80(18) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C1 C2 C3 120.20(18) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.91(17) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C16 C15 C14 118.71(17) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C24 C25 C26 120.42(17) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C15 C16 C17 120.48(18) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C13 C14 120.92(18) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 121.10(19) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_compound-5aab
_database_code_depnum_ccdc_archive 'CCDC 2110001'
loop_
_audit_author_name
_audit_author_address
'Deevi Basavaiah'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '5-phenyl-2-(pyridin-2-yl)-4-(p-tolyl)oxazole' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.4535(11)
_cell_length_b                   11.5915(16)
_cell_length_c                   18.893(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1632.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    198(140)
_cell_measurement_reflns_used    4475
_cell_measurement_theta_min      2.0620
_cell_measurement_theta_max      25.6610

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      198(140)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7704
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2816
_reflns_number_gt                2086
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0690P)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     SHELXL
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_number_reflns         2816
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.4956(3) 0.46221(16) 0.61055(9) 0.0612(5) Uani 1 1 d . . .
N1 N 0.5361(3) 0.2732(2) 0.60238(12) 0.0588(6) Uani 1 1 d . . .
N2 N 0.5720(4) 0.4719(2) 0.74927(12) 0.0706(8) Uani 1 1 d . . .
C10 C 0.4321(4) 0.5289(2) 0.49315(14) 0.0547(7) Uani 1 1 d . . .
C5 C 0.5027(4) 0.2416(2) 0.47306(13) 0.0533(7) Uani 1 1 d . . .
C16 C 0.5346(4) 0.3614(3) 0.64366(15) 0.0581(7) Uani 1 1 d . . .
C8 C 0.4977(4) 0.3170(2) 0.53511(13) 0.0541(7) Uani 1 1 d . . .
C17 C 0.5751(4) 0.3668(3) 0.71950(14) 0.0598(7) Uani 1 1 d . . .
C9 C 0.4702(4) 0.4329(2) 0.54050(14) 0.0550(7) Uani 1 1 d . . .
C15 C 0.5011(4) 0.6370(2) 0.50793(16) 0.0644(8) Uani 1 1 d . . .
H15 H 0.5687 0.6479 0.5488 0.077 Uiso 1 1 calc R . .
C13 C 0.3744(5) 0.7137(3) 0.40292(17) 0.0759(10) Uani 1 1 d . . .
H13 H 0.3574 0.7753 0.3722 0.091 Uiso 1 1 calc R . .
C2 C 0.5227(4) 0.0923(3) 0.35549(15) 0.0633(8) Uani 1 1 d . . .
C12 C 0.3018(4) 0.6075(3) 0.38745(17) 0.0714(9) Uani 1 1 d . . .
H12 H 0.2336 0.5980 0.3467 0.086 Uiso 1 1 calc R . .
C6 C 0.4510(4) 0.1270(3) 0.47816(15) 0.0609(8) Uani 1 1 d . . .
H6 H 0.4095 0.0982 0.5211 0.073 Uiso 1 1 calc R . .
C11 C 0.3296(4) 0.5152(3) 0.43205(14) 0.0617(8) Uani 1 1 d . . .
H11 H 0.2799 0.4437 0.4214 0.074 Uiso 1 1 calc R . .
C14 C 0.4715(5) 0.7282(3) 0.46347(16) 0.0775(10) Uani 1 1 d . . .
H14 H 0.5178 0.8004 0.4746 0.093 Uiso 1 1 calc R . .
C4 C 0.5641(4) 0.2793(3) 0.40766(14) 0.0638(8) Uani 1 1 d . . .
H4 H 0.5995 0.3558 0.4025 0.077 Uiso 1 1 calc R . .
C7 C 0.4610(4) 0.0554(3) 0.41993(16) 0.0682(9) Uani 1 1 d . . .
H7 H 0.4243 -0.0209 0.4246 0.082 Uiso 1 1 calc R . .
C3 C 0.5740(4) 0.2067(3) 0.35050(16) 0.0680(9) Uani 1 1 d . . .
H3 H 0.6160 0.2349 0.3075 0.082 Uiso 1 1 calc R . .
C19 C 0.6662(5) 0.3844(4) 0.85726(17) 0.0878(12) Uani 1 1 d . . .
H19 H 0.7009 0.3935 0.9042 0.105 Uiso 1 1 calc R . .
C18 C 0.6170(5) 0.4772(4) 0.81745(17) 0.0813(11) Uani 1 1 d . . .
H18 H 0.6147 0.5491 0.8393 0.098 Uiso 1 1 calc R . .
C20 C 0.6632(5) 0.2774(3) 0.82647(17) 0.0842(11) Uani 1 1 d . . .
H20 H 0.6921 0.2121 0.8527 0.101 Uiso 1 1 calc R . .
C21 C 0.6165(5) 0.2679(3) 0.75586(15) 0.0766(10) Uani 1 1 d . . .
H21 H 0.6133 0.1964 0.7336 0.092 Uiso 1 1 calc R . .
C1 C 0.5400(5) 0.0117(3) 0.29314(16) 0.0906(11) Uani 1 1 d . . .
H1A H 0.6638 -0.0086 0.2867 0.136 Uiso 1 1 calc R . .
H1B H 0.4963 0.0493 0.2513 0.136 Uiso 1 1 calc R . .
H1C H 0.4710 -0.0568 0.3018 0.136 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 C16 1.357(3) . ?
O1 C9 1.379(3) . ?
N1 C16 1.286(3) . ?
N1 C8 1.398(3) . ?
N2 C18 1.332(4) . ?
N2 C17 1.342(4) . ?
C10 C15 1.383(4) . ?
C10 C11 1.393(4) . ?
C10 C9 1.456(4) . ?
C5 C6 1.387(4) . ?
C5 C4 1.388(3) . ?
C5 C8 1.462(3) . ?
C16 C17 1.466(4) . ?
C8 C9 1.363(4) . ?
C17 C21 1.371(4) . ?
C15 C14 1.368(4) . ?
C15 H15 0.9300 . ?
C13 C14 1.364(4) . ?
C13 C12 1.376(5) . ?
C13 H13 0.9300 . ?
C2 C7 1.370(4) . ?
C2 C3 1.383(4) . ?
C2 C1 1.509(4) . ?
C12 C11 1.378(4) . ?
C12 H12 0.9300 . ?
C6 C7 1.380(4) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C4 C3 1.371(4) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C19 C18 1.363(5) . ?
C19 C20 1.370(5) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C16 O1 C9 105.0(2) . . ?
C16 N1 C8 105.1(2) . . ?
C18 N2 C17 116.3(3) . . ?
C15 C10 C11 118.3(3) . . ?
C15 C10 C9 119.7(3) . . ?
C11 C10 C9 121.9(3) . . ?
C6 C5 C4 117.0(3) . . ?
C6 C5 C8 120.6(2) . . ?
C4 C5 C8 122.3(3) . . ?
N1 C16 O1 114.0(2) . . ?
N1 C16 C17 128.7(3) . . ?
O1 C16 C17 117.2(3) . . ?
C9 C8 N1 108.7(2) . . ?
C9 C8 C5 130.7(3) . . ?
N1 C8 C5 120.4(2) . . ?
N2 C17 C21 123.5(3) . . ?
N2 C17 C16 116.4(3) . . ?
C21 C17 C16 120.0(3) . . ?
C8 C9 O1 107.1(2) . . ?
C8 C9 C10 137.5(3) . . ?
O1 C9 C10 115.4(2) . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C7 C2 C3 116.9(3) . . ?
C7 C2 C1 121.9(3) . . ?
C3 C2 C1 121.1(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C2 C7 C6 122.6(3) . . ?
C2 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C18 C19 C20 118.4(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
N2 C18 C19 124.4(4) . . ?
N2 C18 H18 117.8 . . ?
C19 C18 H18 117.8 . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C17 C21 C20 118.3(3) . . ?
C17 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.052
