#------------------------------------------------------------------------------
#$Date: 2022-08-06 14:39:05 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277095 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/71/1567102.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_1567102
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 H16 N2 O'
_chemical_formula_weight         312.36
_chemical_name_systematic
; 
 '5-phenyl-2-(pyridin-2-yl)-4-(p-tolyl)oxazole' 
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4535(11)
_cell_length_b                   11.5915(16)
_cell_length_c                   18.893(3)
_cell_measurement_reflns_used    4475
_cell_measurement_temperature    198(140)
_cell_measurement_theta_max      25.6610
_cell_measurement_theta_min      2.0620
_cell_volume                     1632.3(4)
_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      198(140)
_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  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7704
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.16
_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    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42983
_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    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_extinction_coef       0.011(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   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0574
_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)+(0.0690P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1461
_reflns_number_gt                2086
_reflns_number_total             2816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc00046f2.cif
_cod_data_source_block           compound-5aab
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' 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_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1567102
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'
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 . .
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'
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 . . ?
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 . ?
