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#$Date: 2024-01-06 11:34:43 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288882 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159660.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_7159660
loop_
_publ_author_name
'Martelli, Lorena S. R.'
'da Silva, Otavio A. M.'
'Zukerman-Schpector, Julio'
'Corrêa, Arlene G'
_publ_section_title
;
 One-pot synthesis of γ-lactams from ketoaziridines.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9128
_journal_page_last               9132
_journal_paper_doi               10.1039/d3ob01568h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2023-08-04 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.08(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.280(3)
_cell_length_b                   9.997(3)
_cell_length_c                   11.637(4)
_cell_measurement_reflns_used    1149
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      22.94
_cell_measurement_theta_min      2.73
_cell_volume                     1312.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    SIR2014
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.770
_diffrn_measured_fraction_theta_max 0.757
_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  0.0712
_diffrn_reflns_av_unetI/netI     0.1538
_diffrn_reflns_Laue_measured_fraction_full 0.770
_diffrn_reflns_Laue_measured_fraction_max 0.757
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4406
_diffrn_reflns_point_group_measured_fraction_full 0.770
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.655
_diffrn_reflns_theta_min         1.806
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       irregular
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.703
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.703
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0495
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                875
_reflns_number_total             2093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01568h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7159660.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159660
_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   0.974
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.1359(2) 0.8182(3) 0.3795(2) 0.0461(7) Uani 1 1 d . . . . .
C2 C 0.1134(2) 0.6765(3) 0.3643(2) 0.0450(7) Uani 1 1 d . . . . .
H2 H 0.0760 0.6395 0.2999 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1527(2) 0.6063(2) 0.4538(2) 0.0356(6) Uani 1 1 d . . . . .
C4 C 0.20156(19) 0.7038(2) 0.5392(2) 0.0377(6) Uani 1 1 d . . . . .
H4 H 0.1888 0.6878 0.6211 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3065(2) 0.7867(2) 0.5045(2) 0.0429(7) Uani 1 1 d . . . . .
H5 H 0.3437 0.7605 0.4325 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3841(2) 0.8567(3) 0.5879(2) 0.0443(7) Uani 1 1 d . . . . .
C7 C 0.5069(2) 0.8445(3) 0.5802(3) 0.0602(8) Uani 1 1 d . . . . .
H7 H 0.5399 0.7911 0.5237 0.072 Uiso 1 1 calc R U . . .
C8 C 0.5781(3) 0.9121(3) 0.6568(3) 0.0779(11) Uani 1 1 d . . . . .
H8 H 0.6600 0.9049 0.6518 0.093 Uiso 1 1 calc R U . . .
C9 C 0.5301(3) 0.9907(4) 0.7414(3) 0.0770(11) Uani 1 1 d . . . . .
H9 H 0.5798 1.0361 0.7927 0.092 Uiso 1 1 calc R U . . .
C10 C 0.4099(2) 1.0025(3) 0.7505(3) 0.0678(10) Uani 1 1 d . . . . .
H10 H 0.3775 1.0552 0.8078 0.081 Uiso 1 1 calc R U . . .
C11 C 0.3380(2) 0.9356(3) 0.6739(2) 0.0542(8) Uani 1 1 d . . . . .
H11 H 0.2562 0.9434 0.6798 0.065 Uiso 1 1 calc R U . . .
C12 C 0.15282(19) 0.4623(3) 0.4722(2) 0.0366(6) Uani 1 1 d . . . . .
C13 C 0.1059(2) 0.3751(3) 0.3904(2) 0.0455(7) Uani 1 1 d . . . . .
H13 H 0.0731 0.4091 0.3225 0.055 Uiso 1 1 calc R U . . .
C14 C 0.1074(2) 0.2389(3) 0.4085(3) 0.0541(8) Uani 1 1 d . . . . .
H14 H 0.0760 0.1821 0.3524 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1542(2) 0.1860(3) 0.5072(3) 0.0559(8) Uani 1 1 d . . . . .
H15 H 0.1549 0.0939 0.5186 0.067 Uiso 1 1 calc R U . . .
C16 C 0.2003(2) 0.2701(3) 0.5897(3) 0.0599(8) Uani 1 1 d . . . . .
H16 H 0.2323 0.2352 0.6576 0.072 Uiso 1 1 calc R U . . .
C17 C 0.1991(2) 0.4071(3) 0.5719(2) 0.0491(7) Uani 1 1 d . . . . .
H17 H 0.2304 0.4632 0.6285 0.059 Uiso 1 1 calc R U . . .
N N 0.18247(18) 0.8385(2) 0.49341(19) 0.0405(5) Uani 1 1 d . . . . .
O O 0.12087(17) 0.91028(19) 0.31248(17) 0.0662(6) Uani 1 1 d . . . . .
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
O C1 N 122.1(3) . . ?
O C1 C2 129.7(3) . . ?
N C1 C2 108.2(2) . . ?
C3 C2 C1 111.5(2) . . ?
C3 C2 H2 124.3 . . ?
C1 C2 H2 124.3 . . ?
C2 C3 C12 129.7(2) . . ?
C2 C3 C4 107.0(2) . . ?
C12 C3 C4 123.3(2) . . ?
N C4 C3 108.0(2) . . ?
N C4 C5 60.46(15) . . ?
C3 C4 C5 117.6(2) . . ?
N C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 N 115.9(2) . . ?
C6 C5 C4 123.0(2) . . ?
N C5 C4 58.30(14) . . ?
C6 C5 H5 115.7 . . ?
N C5 H5 115.7 . . ?
C4 C5 H5 115.7 . . ?
C11 C6 C7 118.9(3) . . ?
C11 C6 C5 121.4(2) . . ?
C7 C6 C5 119.6(2) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C6 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
C6 C11 H11 119.2 . . ?
C17 C12 C13 117.3(2) . . ?
C17 C12 C3 121.3(2) . . ?
C13 C12 C3 121.4(2) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 121.7(3) . . ?
C12 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C1 N C4 104.9(2) . . ?
C1 N C5 111.0(2) . . ?
C4 N C5 61.23(15) . . ?
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
C1 O 1.216(3) . ?
C1 N 1.430(3) . ?
C1 C2 1.450(3) . ?
C2 C3 1.326(3) . ?
C2 H2 0.9300 . ?
C3 C12 1.455(3) . ?
C3 C4 1.491(3) . ?
C4 N 1.462(3) . ?
C4 C5 1.507(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.471(4) . ?
C5 N 1.495(3) . ?
C5 H5 0.9800 . ?
C6 C11 1.384(3) . ?
C6 C7 1.395(3) . ?
C7 C8 1.367(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.378(4) . ?
C12 C13 1.388(3) . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
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
O C1 C2 C3 173.6(3) . . . . ?
N C1 C2 C3 -6.3(3) . . . . ?
C1 C2 C3 C12 -177.2(2) . . . . ?
C1 C2 C3 C4 2.3(3) . . . . ?
C2 C3 C4 N 2.4(3) . . . . ?
C12 C3 C4 N -178.0(2) . . . . ?
C2 C3 C4 C5 -63.1(3) . . . . ?
C12 C3 C4 C5 116.5(2) . . . . ?
N C4 C5 C6 102.1(3) . . . . ?
C3 C4 C5 C6 -161.9(2) . . . . ?
C3 C4 C5 N 96.0(2) . . . . ?
N C5 C6 C11 18.9(4) . . . . ?
C4 C5 C6 C11 -48.7(4) . . . . ?
N C5 C6 C7 -160.6(2) . . . . ?
C4 C5 C6 C7 131.8(3) . . . . ?
C11 C6 C7 C8 -0.8(4) . . . . ?
C5 C6 C7 C8 178.7(3) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C6 0.0(5) . . . . ?
C7 C6 C11 C10 0.6(4) . . . . ?
C5 C6 C11 C10 -178.9(3) . . . . ?
C2 C3 C12 C17 179.5(3) . . . . ?
C4 C3 C12 C17 0.0(3) . . . . ?
C2 C3 C12 C13 -0.8(4) . . . . ?
C4 C3 C12 C13 179.7(2) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
C3 C12 C13 C14 179.5(2) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C13 C12 C17 C16 0.7(4) . . . . ?
C3 C12 C17 C16 -179.5(2) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
O C1 N C4 -172.6(2) . . . . ?
C2 C1 N C4 7.3(3) . . . . ?
O C1 N C5 -108.1(3) . . . . ?
C2 C1 N C5 71.8(2) . . . . ?
C3 C4 N C1 -6.0(3) . . . . ?
C5 C4 N C1 106.1(2) . . . . ?
C3 C4 N C5 -112.1(2) . . . . ?
C6 C5 N C1 149.7(2) . . . . ?
C4 C5 N C1 -95.9(2) . . . . ?
C6 C5 N C4 -114.4(3) . . . . ?
