#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:12:46 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278965 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567759.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_1567759
loop_
_publ_author_name
'Tien, Chieh-Hung'
'Lough, Alan J.'
'Yudin, Andrei K.'
_publ_section_title
;
 Iminologous epoxide ring-closure
;
_journal_issue                   41
_journal_name_full               'Chemical Science'
_journal_page_first              12175
_journal_page_last               12179
_journal_paper_doi               10.1039/D2SC04496J
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C13 H20 N2 O2, 0.098(H2 O)'
_chemical_formula_sum            'C13 H20.2 N2 O2.1'
_chemical_formula_weight         238.11
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-02 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                83.662(4)
_cell_angle_beta                 89.167(5)
_cell_angle_gamma                86.054(4)
_cell_formula_units_Z            2
_cell_length_a                   5.7302(7)
_cell_length_b                   9.9783(12)
_cell_length_c                   11.5048(17)
_cell_measurement_reflns_used    4547
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.56
_cell_volume                     652.23(15)
_computing_cell_refinement       APEX4
_computing_data_collection       'APEX4 (Bruker AXS, 2021)'
_computing_data_reduction        APEX4
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11552
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_min         1.781
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             258
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0367
_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)+(0.0399P)²+0.1488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2396
_reflns_number_total             2971
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04496j2.cif
_cod_data_source_block           d21126_a
_cod_depositor_comments
'Adding full bibliography for 1567759--1567762.cif.'
_cod_original_formula_sum        'C13 H20.20 N2 O2.10'
_cod_database_code               1567759
_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   0.974
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_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_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 0.66624(13) 0.65045(7) 0.90090(6) 0.02417(19) Uani 1 1 d . . . . .
O2 O 0.77628(14) 0.58545(8) 0.67789(7) 0.0289(2) Uani 1 1 d . . . . .
N1 N 0.46566(16) 0.71264(9) 0.60051(8) 0.0238(2) Uani 1 1 d . . . . .
N2 N 0.1402(2) 0.11900(10) 0.77715(10) 0.0385(3) Uani 1 1 d . . . . .
C1 C 0.48720(18) 0.66336(10) 0.81274(9) 0.0192(2) Uani 1 1 d . . . . .
C2 C 0.53985(18) 0.78142(10) 0.87273(9) 0.0217(2) Uani 1 1 d . . . . .
C3 C 0.3817(2) 0.82920(11) 0.96767(10) 0.0272(3) Uani 1 1 d . . . . .
H3A H 0.296719 0.753496 1.004432 0.041 Uiso 1 1 calc R U . . .
H3B H 0.269659 0.901044 0.933734 0.041 Uiso 1 1 calc R U . . .
H3C H 0.475658 0.864138 1.026625 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6879(2) 0.88795(11) 0.81257(11) 0.0300(3) Uani 1 1 d . . . . .
H4A H 0.785792 0.848938 0.752599 0.045 Uiso 1 1 calc R U . . .
H4B H 0.787890 0.920848 0.870185 0.045 Uiso 1 1 calc R U . . .
H4C H 0.586199 0.963323 0.775836 0.045 Uiso 1 1 calc R U . . .
C5 C 0.58947(18) 0.65121(10) 0.69112(9) 0.0206(2) Uani 1 1 d . . . . .
C6 C 0.2435(2) 0.79621(12) 0.60346(10) 0.0286(3) Uani 1 1 d . . . . .
H6A H 0.250454 0.864297 0.659502 0.034 Uiso 1 1 calc R U . . .
H6B H 0.110471 0.739806 0.624611 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2236(2) 0.86326(13) 0.47773(11) 0.0342(3) Uani 1 1 d . . . . .
H7A H 0.057891 0.884907 0.455469 0.041 Uiso 1 1 calc R U . . .
H7B H 0.307770 0.947174 0.467119 0.041 Uiso 1 1 calc R U . . .
C8 C 0.3381(2) 0.75613(14) 0.40635(11) 0.0371(3) Uani 1 1 d . . . . .
H8A H 0.230244 0.684901 0.396477 0.044 Uiso 1 1 calc R U . . .
H8B H 0.387790 0.796788 0.328305 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5470(2) 0.69995(13) 0.47977(10) 0.0313(3) Uani 1 1 d . . . . .
H9A H 0.588498 0.604333 0.468255 0.038 Uiso 1 1 calc R U . . .
H9B H 0.684583 0.753229 0.460328 0.038 Uiso 1 1 calc R U . . .
C10 C 0.27643(18) 0.58234(10) 0.84429(9) 0.0215(2) Uani 1 1 d . . . . .
H10A H 0.134634 0.633050 0.810054 0.026 Uiso 1 1 calc R U . . .
H10B H 0.256313 0.571532 0.930356 0.026 Uiso 1 1 calc R U . . .
C11 C 0.29927(19) 0.44319(11) 0.80092(10) 0.0240(2) Uani 1 1 d . . . . .
H11A H 0.447583 0.394751 0.829442 0.029 Uiso 1 1 calc R U . . .
H11B H 0.303720 0.453293 0.714354 0.029 Uiso 1 1 calc R U . . .
C12 C 0.09330(19) 0.36077(11) 0.84430(10) 0.0238(2) Uani 1 1 d . . . . .
H12A H 0.085595 0.353977 0.930758 0.029 Uiso 1 1 calc R U . . .
H12B H -0.054274 0.408043 0.813503 0.029 Uiso 1 1 calc R U . . .
C13 C 0.11577(19) 0.22478(11) 0.80715(10) 0.0259(2) Uani 1 1 d . . . . .
O1W O 0.062(2) 0.5483(15) 0.4985(15) 0.086(7) Uani 0.098(4) 1 d D . P A -1
H1WA H 0.06(4) 0.49(2) 0.448(15) 0.128 Uiso 0.098(4) 1 d D U P A -1
H1WB H -0.06(2) 0.55(2) 0.540(17) 0.128 Uiso 0.098(4) 1 d D U P A -1
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 C2 61.39(6) . . ?
C5 N1 C9 120.26(9) . . ?
C5 N1 C6 127.85(9) . . ?
C9 N1 C6 111.88(9) . . ?
O1 C1 C2 59.76(6) . . ?
O1 C1 C10 114.90(8) . . ?
C2 C1 C10 122.49(9) . . ?
O1 C1 C5 111.97(8) . . ?
C2 C1 C5 118.58(8) . . ?
C10 C1 C5 115.44(9) . . ?
O1 C2 C1 58.85(6) . . ?
O1 C2 C3 115.77(9) . . ?
C1 C2 C3 121.14(9) . . ?
O1 C2 C4 113.85(9) . . ?
C1 C2 C4 120.07(9) . . ?
C3 C2 C4 114.51(9) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 N1 122.08(10) . . ?
O2 C5 C1 120.91(9) . . ?
N1 C5 C1 117.00(9) . . ?
N1 C6 C7 102.43(9) . . ?
N1 C6 H6A 111.3 . . ?
C7 C6 H6A 111.3 . . ?
N1 C6 H6B 111.3 . . ?
C7 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C8 C7 C6 103.24(10) . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C6 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C9 C8 C7 103.07(10) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N1 C9 C8 103.37(9) . . ?
N1 C9 H9A 111.1 . . ?
C8 C9 H9A 111.1 . . ?
N1 C9 H9B 111.1 . . ?
C8 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C1 C10 C11 112.65(9) . . ?
C1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 110.64(9) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 111.62(9) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 C12 177.93(12) . . ?
H1WA O1W H1WB 113(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 1.4426(12) . ?
O1 C2 1.4562(13) . ?
O2 C5 1.2330(13) . ?
N1 C5 1.3366(14) . ?
N1 C9 1.4748(14) . ?
N1 C6 1.4754(15) . ?
N2 C13 1.1453(15) . ?
C1 C2 1.4797(14) . ?
C1 C10 1.5169(14) . ?
C1 C5 1.5230(15) . ?
C2 C3 1.5063(15) . ?
C2 C4 1.5077(15) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.5276(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5262(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5146(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5232(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5311(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4639(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O1W H1WA 0.841(10) . ?
O1W H1WB 0.840(10) . ?
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 O1 C1 C10 -114.52(10) . . . . ?
C2 O1 C1 C5 111.22(9) . . . . ?
C1 O1 C2 C3 112.28(10) . . . . ?
C1 O1 C2 C4 -111.90(10) . . . . ?
C10 C1 C2 O1 101.92(10) . . . . ?
C5 C1 C2 O1 -100.11(10) . . . . ?
O1 C1 C2 C3 -103.20(11) . . . . ?
C10 C1 C2 C3 -1.28(15) . . . . ?
C5 C1 C2 C3 156.69(10) . . . . ?
O1 C1 C2 C4 101.31(11) . . . . ?
C10 C1 C2 C4 -156.78(10) . . . . ?
C5 C1 C2 C4 1.19(15) . . . . ?
C9 N1 C5 O2 1.83(16) . . . . ?
C6 N1 C5 O2 -178.69(10) . . . . ?
C9 N1 C5 C1 -176.96(9) . . . . ?
C6 N1 C5 C1 2.52(16) . . . . ?
O1 C1 C5 O2 27.39(13) . . . . ?
C2 C1 C5 O2 93.89(12) . . . . ?
C10 C1 C5 O2 -106.61(12) . . . . ?
O1 C1 C5 N1 -153.81(9) . . . . ?
C2 C1 C5 N1 -87.30(12) . . . . ?
C10 C1 C5 N1 72.19(12) . . . . ?
C5 N1 C6 C7 166.93(11) . . . . ?
C9 N1 C6 C7 -13.55(12) . . . . ?
N1 C6 C7 C8 32.83(12) . . . . ?
C6 C7 C8 C9 -40.50(13) . . . . ?
C5 N1 C9 C8 168.18(10) . . . . ?
C6 N1 C9 C8 -11.38(13) . . . . ?
C7 C8 C9 N1 31.62(13) . . . . ?
O1 C1 C10 C11 -92.80(11) . . . . ?
C2 C1 C10 C11 -161.54(9) . . . . ?
C5 C1 C10 C11 39.85(13) . . . . ?
C1 C10 C11 C12 174.87(9) . . . . ?
C10 C11 C12 C13 -177.97(9) . . . . ?
