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#$Date: 2021-10-06 16:55:53 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269639 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/88/7128893.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_7128893
loop_
_publ_author_name
'Liu, Hua-Wei'
'Wang, Dian-Liang'
'Jiang, Nan-Quan'
'Li, Hai-Yan'
'Cai, Zhong-Jian'
'Ji, Shun-Jun'
_publ_section_title
;
 Divergent synthesis of α-functionalized amides through selective N-O/C-C
 or N-O/C-C/C-N cleavage of aza-cyclobutanone oxime esters.
;
_journal_issue                   75
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9618
_journal_page_last               9621
_journal_paper_doi               10.1039/d1cc03348d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc27xfzl
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.818(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.6297(8)
_cell_length_b                   6.39261(18)
_cell_length_c                   12.4690(3)
_cell_measurement_reflns_used    4992
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      77.1110
_cell_measurement_theta_min      3.7890
_cell_volume                     1854.26(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12743
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.285
_diffrn_reflns_theta_min         3.800
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85997
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+1.3788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                3422
_reflns_number_total             3720
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03348d2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7128893--7128894.cif.'
_cod_original_cell_volume        1854.25(10)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7128893
_shelx_shelxl_version_number     2018/3
_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   0.767
_shelx_estimated_absorpt_t_max   0.902
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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_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 0.37796(12) 1.2920(4) 0.7621(2) 0.0434(6) Uani 1 1 d . . . . .
O2 O 0.54667(13) 0.4835(5) 0.8515(2) 0.0533(8) Uani 1 1 d . . . . .
O3 O 0.57973(10) 0.4482(4) 0.5747(2) 0.0400(6) Uani 1 1 d . . . . .
C1 C 0.40298(13) 1.1126(5) 0.7493(3) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.38889(13) 1.0473(5) 0.6336(3) 0.0322(6) Uani 1 1 d . . . . .
H2 H 0.363210 1.126890 0.569969 0.039 Uiso 1 1 calc R U . . .
C3 C 0.41237(13) 0.8666(5) 0.6120(3) 0.0302(6) Uani 1 1 d . . . . .
H3 H 0.402383 0.824824 0.533516 0.036 Uiso 1 1 calc R U . . .
C4 C 0.45068(12) 0.7449(5) 0.7044(3) 0.0279(6) Uani 1 1 d . . . . .
C5 C 0.46463(14) 0.8103(6) 0.8199(3) 0.0339(7) Uani 1 1 d . . . . .
H5 H 0.490532 0.731264 0.883580 0.041 Uiso 1 1 calc R U . . .
C6 C 0.44069(14) 0.9907(6) 0.8419(3) 0.0353(7) Uani 1 1 d . . . . .
H6 H 0.450039 1.031173 0.920268 0.042 Uiso 1 1 calc R U . . .
C22 C 0.39779(18) 1.3745(6) 0.8785(4) 0.0467(9) Uani 1 1 d . . . . .
H22A H 0.385956 1.282991 0.926303 0.070 Uiso 1 1 calc R U . . .
H22B H 0.381522 1.512608 0.875449 0.070 Uiso 1 1 calc R U . . .
H22C H 0.439394 1.384221 0.913200 0.070 Uiso 1 1 calc R U . . .
N1 N 0.47277(11) 0.5619(4) 0.6756(2) 0.0304(5) Uani 1 1 d . . . . .
C7 C 0.51742(13) 0.4454(5) 0.7483(3) 0.0296(6) Uani 1 1 d . . . . .
C8 C 0.52868(12) 0.2480(5) 0.6917(3) 0.0291(6) Uani 1 1 d . . . . .
H8A H 0.515043 0.125328 0.719647 0.035 Uiso 1 1 calc R U . . .
H8B H 0.507033 0.256098 0.605740 0.035 Uiso 1 1 calc R U . . .
N2 N 0.59022(10) 0.2229(4) 0.7207(2) 0.0284(5) Uani 1 1 d . . . . .
C9 C 0.62598(13) 0.1291(5) 0.8322(3) 0.0292(6) Uani 1 1 d . . . . .
C10 C 0.61350(15) -0.0718(6) 0.8568(3) 0.0400(8) Uani 1 1 d . . . . .
H10 H 0.582357 -0.146075 0.800599 0.048 Uiso 1 1 calc R U . . .
C11 C 0.64737(19) -0.1618(8) 0.9648(4) 0.0541(11) Uani 1 1 d . . . . .
H11 H 0.638879 -0.297336 0.982016 0.065 Uiso 1 1 calc R U . . .
C12 C 0.69352(19) -0.0545(9) 1.0476(3) 0.0571(12) Uani 1 1 d . . . . .
H12 H 0.716205 -0.116672 1.120783 0.068 Uiso 1 1 calc R U . . .
C13 C 0.70615(16) 0.1444(8) 1.0223(3) 0.0479(10) Uani 1 1 d . . . . .
H13 H 0.738025 0.216426 1.077792 0.057 Uiso 1 1 calc R U . . .
C14 C 0.67185(13) 0.2390(6) 0.9148(3) 0.0353(7) Uani 1 1 d . . . . .
H14 H 0.679777 0.376035 0.898606 0.042 Uiso 1 1 calc R U . . .
C15 C 0.61075(13) 0.3250(5) 0.6507(2) 0.0281(6) Uani 1 1 d . . . . .
C16 C 0.66996(13) 0.2765(5) 0.6600(2) 0.0293(6) Uani 1 1 d . . . . .
C17 C 0.69830(15) 0.4333(6) 0.6283(3) 0.0363(7) Uani 1 1 d . . . . .
H17 H 0.681751 0.567111 0.608981 0.044 Uiso 1 1 calc R U . . .
C18 C 0.75090(16) 0.3941(7) 0.6248(3) 0.0455(9) Uani 1 1 d . . . . .
H18 H 0.769957 0.501196 0.603819 0.055 Uiso 1 1 calc R U . . .
C19 C 0.77497(16) 0.1981(7) 0.6523(3) 0.0455(9) Uani 1 1 d . . . . .
H19 H 0.810691 0.171625 0.650573 0.055 Uiso 1 1 calc R U . . .
C20 C 0.74680(16) 0.0398(7) 0.6824(3) 0.0430(8) Uani 1 1 d . . . . .
H20 H 0.763232 -0.094374 0.699892 0.052 Uiso 1 1 calc R U . . .
C21 C 0.69448(14) 0.0777(6) 0.6871(3) 0.0342(7) Uani 1 1 d . . . . .
H21 H 0.675667 -0.029949 0.708321 0.041 Uiso 1 1 calc R U . . .
H1 H 0.457(2) 0.522(7) 0.602(4) 0.041 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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 C22 116.7(3) . . ?
O1 C1 C6 125.1(3) . . ?
O1 C1 C2 116.4(3) . . ?
C6 C1 C2 118.5(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 N1 123.7(3) . . ?
C3 C4 N1 118.1(3) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C7 N1 C4 127.3(3) . . ?
C7 N1 H1 116(3) . . ?
C4 N1 H1 117(3) . . ?
O2 C7 N1 125.1(3) . . ?
O2 C7 C8 120.2(3) . . ?
N1 C7 C8 114.6(3) . . ?
N2 C8 C7 111.5(2) . . ?
N2 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C15 N2 C9 124.0(2) . . ?
C15 N2 C8 117.0(2) . . ?
C9 N2 C8 117.8(2) . . ?
C14 C9 C10 120.5(3) . . ?
C14 C9 N2 120.4(3) . . ?
C10 C9 N2 119.2(3) . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 119.4(4) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
O3 C15 N2 120.1(3) . . ?
O3 C15 C16 119.6(3) . . ?
N2 C15 C16 120.1(3) . . ?
C17 C16 C21 119.3(3) . . ?
C17 C16 C15 117.4(3) . . ?
C21 C16 C15 122.9(3) . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 120.5(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 119.6(3) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
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 1.356(4) . ?
O1 C22 1.423(5) . ?
O2 C7 1.211(4) . ?
O3 C15 1.233(4) . ?
C1 C6 1.392(5) . ?
C1 C2 1.396(4) . ?
C2 C3 1.380(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.396(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.394(4) . ?
C4 N1 1.410(4) . ?
C5 C6 1.386(5) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
N1 C7 1.347(4) . ?
N1 H1 0.87(5) . ?
C7 C8 1.532(4) . ?
C8 N2 1.471(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
N2 C15 1.360(4) . ?
N2 C9 1.436(4) . ?
C9 C14 1.386(5) . ?
C9 C10 1.389(5) . ?
C10 C11 1.384(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.382(7) . ?
C11 H11 0.9400 . ?
C12 C13 1.381(7) . ?
C12 H12 0.9400 . ?
C13 C14 1.395(5) . ?
C13 H13 0.9400 . ?
C14 H14 0.9400 . ?
C15 C16 1.505(4) . ?
C16 C17 1.389(5) . ?
C16 C21 1.395(5) . ?
C17 C18 1.389(5) . ?
C17 H17 0.9400 . ?
C18 C19 1.375(6) . ?
C18 H18 0.9400 . ?
C19 C20 1.384(6) . ?
C19 H19 0.9400 . ?
C20 C21 1.388(5) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
