#------------------------------------------------------------------------------
#$Date: 2022-08-06 14:39:05 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277095 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/71/1567101.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_1567101
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            'C27 H17 N3 O'
_chemical_formula_weight         399.44
_chemical_name_systematic
; 
 '4-phenyl-2,5-di(quinolin-2-yl)oxazole' 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                90.00
_cell_angle_beta                 104.402(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3712(5)
_cell_length_b                   9.2050(4)
_cell_length_c                   19.1767(9)
_cell_measurement_reflns_used    7490
_cell_measurement_temperature    296.9(3)
_cell_measurement_theta_max      26.5750
_cell_measurement_theta_min      2.1890
_cell_volume                     1944.18(16)
_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      296.9(3)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    0.0323
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16503
_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    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0428
_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)+(0.0604P)²+0.1127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                2570
_reflns_number_total             3423
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc00046f2.cif
_cod_data_source_block           compound-3ea
_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        1944.18(15)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1567101
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'
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 . .
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
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 . . ?
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 . ?
