#------------------------------------------------------------------------------
#$Date: 2022-08-06 14:39:05 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277095 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567098.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1567098
loop_
_publ_author_name
'Basavaiah, Deevi'
'Golime, Gangadhararao'
'Banoth, Shivalal'
'Todeti, Saidulu'
_publ_section_title
;
 An umpolung strategy for intermolecular [2 + 2 + 1] cycloaddition of aryl
 aldehydes and nitriles: a facile access to 2,4,5-trisubstituted oxazoles.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              8080
_journal_page_last               8087
_journal_paper_doi               10.1039/d2sc00046f
_journal_volume                  13
_journal_year                    2022
_chemical_formula_sum            'C21 H13 F3 N2 O'
_chemical_formula_weight         366.33
_chemical_name_systematic
; 
 '2-(pyridin-2-yl)-4-(p-tolyl)-5-(2,4,6-trifluorophenyl)oxazole' 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.465(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0851(4)
_cell_length_b                   7.7428(3)
_cell_length_c                   19.0267(8)
_cell_measurement_reflns_used    7254
_cell_measurement_temperature    297(7)
_cell_measurement_theta_max      26.0200
_cell_measurement_theta_min      2.2170
_cell_volume                     1738.41(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(7)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14164
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0580P)²+0.1115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                2276
_reflns_number_total             3059
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc00046f2.cif
_cod_data_source_block           compound-5aib
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1567097--1567102.cif.
;
_cod_original_cell_volume        1738.41(11)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1567098
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'
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 . .
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'
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 . . ?
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 . ?
