#------------------------------------------------------------------------------
#$Date: 2022-08-06 14:39:05 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277095 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567097.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_1567097
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            'C19 H13 N3 O'
_chemical_formula_weight         299.32
_chemical_name_systematic
; 
 '4-phenyl-2,5-di(pyridin-2-yl)oxazole' 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-09-08 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                86.201(5)
_cell_angle_beta                 80.086(5)
_cell_angle_gamma                76.138(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1025(3)
_cell_length_b                   8.5817(5)
_cell_length_c                   14.6868(9)
_cell_measurement_reflns_used    4828
_cell_measurement_temperature    391(300)
_cell_measurement_theta_max      26.6430
_cell_measurement_theta_min      2.4170
_cell_volume                     735.34(7)
_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      391(300)
_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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8439
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.45
_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    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.043(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0483
_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)+(0.0762P)²+0.0651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                2035
_reflns_number_total             2583
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc00046f2.cif
_cod_data_source_block           compound-3aa
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' 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      P-1
_cod_database_code               1567097
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.3680(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 . .
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
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 . . ?
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 . ?
