#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/76/7127671.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_7127671
loop_
_publ_author_name
'Dai, Ling'
'Yu, Shuling'
'Shao, Yinlin'
'Li, Renhao'
'Chen, Zhongyan'
'Lv, Ningning'
'Chen, Jiuxi'
_publ_section_title
;
 Palladium-catalyzed C-H activation of simple arenes and cascade reaction
 with nitriles: access to 2,4,5-trisubstituted oxazoles.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1376
_journal_page_last               1379
_journal_paper_doi               10.1039/d0cc07547g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C24 H21 N O'
_chemical_formula_weight         339.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-09-18 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.296(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.6175(15)
_cell_length_b                   14.6158(8)
_cell_length_c                   11.7728(7)
_cell_measurement_reflns_used    6501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.908
_cell_measurement_theta_min      4.602
_cell_volume                     3829.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18866
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.667
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0057(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0555P)²+1.5668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2627
_reflns_number_total             3769
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc07547g2.cif
_cod_data_source_block           mo_dd20173_0m
_cod_depositor_comments          'Adding full bibliography for 7127671.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7127671
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41136(5) 0.85446(7) 0.25259(10) 0.0572(3) Uani 1 1 d . . . . .
N1 N 0.34584(6) 0.75587(9) 0.15729(12) 0.0588(4) Uani 1 1 d . . . . .
C1 C 0.36745(8) 0.83795(11) 0.15989(14) 0.0550(4) Uani 1 1 d . . . . .
C2 C 0.37749(8) 0.71315(11) 0.25574(14) 0.0535(4) Uani 1 1 d . . . . .
C3 C 0.41756(8) 0.77301(11) 0.31408(14) 0.0531(4) Uani 1 1 d . . . . .
C4 C 0.46085(8) 0.77298(12) 0.42143(14) 0.0564(4) Uani 1 1 d . . . . .
C5 C 0.46919(9) 0.69603(13) 0.49148(16) 0.0682(5) Uani 1 1 d . . . . .
H5 H 0.4482 0.6426 0.4680 0.082 Uiso 1 1 calc R U . . .
C6 C 0.50824(11) 0.69801(17) 0.59527(18) 0.0859(7) Uani 1 1 d . . . . .
H6 H 0.5135 0.6458 0.6412 0.103 Uiso 1 1 calc R U . . .
C7 C 0.53960(10) 0.77596(19) 0.63190(19) 0.0890(7) Uani 1 1 d . . . . .
H7 H 0.5654 0.7770 0.7029 0.107 Uiso 1 1 calc R U . . .
C8 C 0.53273(10) 0.85253(17) 0.56333(19) 0.0862(7) Uani 1 1 d . . . . .
H8 H 0.5543 0.9054 0.5874 0.103 Uiso 1 1 calc R U . . .
C9 C 0.49389(9) 0.85106(14) 0.45877(18) 0.0736(6) Uani 1 1 d . . . . .
H9 H 0.4897 0.9031 0.4125 0.088 Uiso 1 1 calc R U . . .
C10 C 0.34978(8) 0.91230(11) 0.07850(15) 0.0569(4) Uani 1 1 d . . . . .
C11 C 0.37215(9) 1.00005(13) 0.10026(18) 0.0724(6) Uani 1 1 d . . . . .
H11 H 0.3986 1.0128 0.1684 0.087 Uiso 1 1 calc R U . . .
C12 C 0.35499(11) 1.06839(14) 0.0202(2) 0.0856(7) Uani 1 1 d . . . . .
H12 H 0.3696 1.1275 0.0352 0.103 Uiso 1 1 calc R U . . .
C13 C 0.31665(11) 1.04998(16) -0.0809(2) 0.0853(7) Uani 1 1 d . . . . .
H13 H 0.3059 1.0963 -0.1348 0.102 Uiso 1 1 calc R U . . .
C14 C 0.29403(11) 0.96345(16) -0.10294(18) 0.0819(6) Uani 1 1 d . . . . .
H14 H 0.2677 0.9512 -0.1714 0.098 Uiso 1 1 calc R U . . .
C15 C 0.31042(9) 0.89446(13) -0.02305(16) 0.0681(5) Uani 1 1 d . . . . .
H15 H 0.2949 0.8359 -0.0378 0.082 Uiso 1 1 calc R U . . .
C16 C 0.36347(8) 0.61687(11) 0.28054(14) 0.0534(4) Uani 1 1 d . . . . .
C17 C 0.38459(8) 0.54612(12) 0.21872(15) 0.0572(4) Uani 1 1 d . . . . .
C18 C 0.36780(9) 0.45707(12) 0.23865(16) 0.0649(5) Uani 1 1 d . . . . .
H18 H 0.3815 0.4098 0.1973 0.078 Uiso 1 1 calc R U . . .
C19 C 0.33138(8) 0.43606(12) 0.31780(17) 0.0650(5) Uani 1 1 d . . . . .
C20 C 0.31180(8) 0.50686(12) 0.37860(17) 0.0667(5) Uani 1 1 d . . . . .
H20 H 0.2878 0.4936 0.4329 0.080 Uiso 1 1 calc R U . . .
C21 C 0.32661(8) 0.59733(11) 0.36166(15) 0.0605(5) Uani 1 1 d . . . . .
C22 C 0.30248(11) 0.67255(14) 0.4284(2) 0.0875(7) Uani 1 1 d . . . . .
H22A H 0.3354 0.7052 0.4734 0.131 Uiso 1 1 calc R U . . .
H22B H 0.2780 0.6464 0.4787 0.131 Uiso 1 1 calc R U . . .
H22C H 0.2787 0.7139 0.3755 0.131 Uiso 1 1 calc R U . . .
C23 C 0.42433(10) 0.56591(14) 0.13193(17) 0.0779(6) Uani 1 1 d . . . . .
H23A H 0.4018 0.5987 0.0678 0.117 Uiso 1 1 calc R U . . .
H23B H 0.4386 0.5094 0.1052 0.117 Uiso 1 1 calc R U . . .
H23C H 0.4579 0.6023 0.1674 0.117 Uiso 1 1 calc R U . . .
C24 C 0.31340(10) 0.33860(13) 0.3373(2) 0.0898(7) Uani 1 1 d . . . . .
H24A H 0.3218 0.3007 0.2756 0.135 Uiso 1 1 calc R U . . .
H24B H 0.2712 0.3363 0.3395 0.135 Uiso 1 1 calc R U . . .
H24C H 0.3357 0.3169 0.4093 0.135 Uiso 1 1 calc R U . . .
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
C1 O1 C3 104.93(12) . . ?
C1 N1 C2 105.05(14) . . ?
N1 C1 O1 113.72(14) . . ?
N1 C1 C10 128.18(17) . . ?
O1 C1 C10 118.08(15) . . ?
C3 C2 N1 109.23(14) . . ?
C3 C2 C16 131.30(15) . . ?
N1 C2 C16 119.47(15) . . ?
C2 C3 O1 107.07(14) . . ?
C2 C3 C4 136.55(15) . . ?
O1 C3 C4 116.32(14) . . ?
C5 C4 C9 117.96(18) . . ?
C5 C4 C3 121.05(16) . . ?
C9 C4 C3 120.97(16) . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C15 C10 C11 119.48(17) . . ?
C15 C10 C1 119.14(16) . . ?
C11 C10 C1 121.38(18) . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.19(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.23(19) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C21 120.23(15) . . ?
C17 C16 C2 119.65(15) . . ?
C21 C16 C2 120.04(15) . . ?
C18 C17 C16 118.47(17) . . ?
C18 C17 C23 120.66(17) . . ?
C16 C17 C23 120.86(16) . . ?
C19 C18 C17 122.41(18) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C20 C19 C18 117.97(16) . . ?
C20 C19 C24 120.65(19) . . ?
C18 C19 C24 121.38(19) . . ?
C19 C20 C21 122.26(18) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C20 C21 C16 118.66(17) . . ?
C20 C21 C22 120.04(17) . . ?
C16 C21 C22 121.30(15) . . ?
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 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 C1 1.359(2) . ?
O1 C3 1.3873(18) . ?
N1 C1 1.294(2) . ?
N1 C2 1.396(2) . ?
C1 C10 1.457(2) . ?
C2 C3 1.355(2) . ?
C2 C16 1.483(2) . ?
C3 C4 1.454(2) . ?
C4 C5 1.387(2) . ?
C4 C9 1.391(3) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.382(3) . ?
C10 C11 1.386(2) . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.397(2) . ?
C16 C21 1.405(2) . ?
C17 C18 1.388(2) . ?
C17 C23 1.505(3) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(3) . ?
C19 C24 1.510(2) . ?
C20 C21 1.387(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.509(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 -0.04(19) . . . . ?
C2 N1 C1 C10 -178.87(16) . . . . ?
C3 O1 C1 N1 0.10(18) . . . . ?
C3 O1 C1 C10 179.07(14) . . . . ?
C1 N1 C2 C3 -0.05(18) . . . . ?
C1 N1 C2 C16 179.48(15) . . . . ?
N1 C2 C3 O1 0.11(18) . . . . ?
C16 C2 C3 O1 -179.35(16) . . . . ?
N1 C2 C3 C4 177.04(18) . . . . ?
C16 C2 C3 C4 -2.4(3) . . . . ?
C1 O1 C3 C2 -0.12(17) . . . . ?
C1 O1 C3 C4 -177.77(14) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
O1 C3 C4 C5 177.91(15) . . . . ?
C2 C3 C4 C9 -176.9(2) . . . . ?
O1 C3 C4 C9 -0.1(2) . . . . ?
C9 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C6 -177.06(17) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C4 0.5(3) . . . . ?
C5 C4 C9 C8 -1.4(3) . . . . ?
C3 C4 C9 C8 176.71(18) . . . . ?
N1 C1 C10 C15 -8.7(3) . . . . ?
O1 C1 C10 C15 172.52(15) . . . . ?
N1 C1 C10 C11 172.09(18) . . . . ?
O1 C1 C10 C11 -6.7(2) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C1 C10 C11 C12 179.08(18) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C1 C10 C15 C14 -178.52(17) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C3 C2 C16 C17 -103.8(2) . . . . ?
N1 C2 C16 C17 76.8(2) . . . . ?
C3 C2 C16 C21 79.4(2) . . . . ?
N1 C2 C16 C21 -99.98(19) . . . . ?
C21 C16 C17 C18 0.7(3) . . . . ?
C2 C16 C17 C18 -176.14(15) . . . . ?
C21 C16 C17 C23 -179.72(17) . . . . ?
C2 C16 C17 C23 3.5(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C23 C17 C18 C19 179.93(17) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C17 C18 C19 C24 179.59(18) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C24 C19 C20 C21 -178.96(18) . . . . ?
C19 C20 C21 C16 -0.8(3) . . . . ?
C19 C20 C21 C22 178.30(19) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
C2 C16 C21 C20 176.72(16) . . . . ?
C17 C16 C21 C22 -179.14(18) . . . . ?
C2 C16 C21 C22 -2.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352449
