#------------------------------------------------------------------------------
#$Date: 2021-09-24 00:57:20 +0300 (Fri, 24 Sep 2021) $
#$Revision: 269259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128980.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_7128980
loop_
_publ_author_name
'Liang, Qiuming'
'Hayashi, Kasumi'
'li, Longfei longfei'
'Song, Datong'
_publ_section_title
;
 Dioxygenation of unprotected mesoionic N‑heterocyclic olefins
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC04695K
_journal_year                    2021
_chemical_formula_sum            'C19 H21 N3 O2'
_chemical_formula_weight         323.39
_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   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-08-19 deposited with the CCDC.	2021-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                96.293(19)
_cell_angle_beta                 90.202(18)
_cell_angle_gamma                99.553(18)
_cell_formula_units_Z            2
_cell_length_a                   7.554(5)
_cell_length_b                   7.800(5)
_cell_length_c                   15.305(10)
_cell_measurement_reflns_used    16545
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.464
_cell_measurement_theta_min      2.735
_cell_volume                     883.7(10)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.1033
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16545
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.464
_diffrn_reflns_theta_min         2.735
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.062(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0722P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2090
_reflns_number_total             3976
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04695k2.cif
_cod_data_source_block           wl419
_cod_database_code               7128980
_shelx_shelxl_version_number     2016/6
_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   0.969
_shelx_estimated_absorpt_t_max   0.996
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
C1 C 0.5665(3) 0.0556(3) 0.20553(14) 0.0387(6) Uani 1 1 d . . . . .
H1A H 0.659629 0.145109 0.230202 0.046 Uiso 1 1 calc R U . . .
O1 O 0.4999(2) 0.2278(2) 0.37140(10) 0.0545(5) Uani 1 1 d . . . . .
N1 N 0.8005(2) 0.8709(2) 0.39726(11) 0.0357(5) Uani 1 1 d . . . . .
C2 C 0.5808(3) -0.0225(3) 0.12100(14) 0.0426(6) Uani 1 1 d . . . . .
H2A H 0.683962 0.013527 0.088021 0.051 Uiso 1 1 calc R U . . .
N2 N 0.8875(2) 0.8017(2) 0.33241(11) 0.0371(5) Uani 1 1 d . . . . .
O2 O 0.298(5) -0.009(2) 0.3940(9) 0.060(5) Uani 0.50(8) 1 d . . P A 1
O2A O 0.256(3) 0.050(8) 0.3867(13) 0.078(8) Uani 0.50(8) 1 d . . P A 2
C3 C 0.4470(3) -0.1518(3) 0.08411(14) 0.0421(6) Uani 1 1 d . . . . .
H3A H 0.456919 -0.203925 0.025647 0.051 Uiso 1 1 calc R U . . .
N3 N 0.8203(2) 0.6328(2) 0.32638(10) 0.0326(4) Uani 1 1 d . . . . .
C4 C 0.2982(3) -0.2055(3) 0.13244(14) 0.0441(6) Uani 1 1 d . . . . .
H4A H 0.205428 -0.295014 0.107462 0.053 Uiso 1 1 calc R U . . .
C5 C 0.2848(3) -0.1290(3) 0.21682(14) 0.0442(6) Uani 1 1 d . . . . .
H5A H 0.182879 -0.167811 0.250070 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4172(3) 0.0041(3) 0.25458(13) 0.0357(5) Uani 1 1 d . . . . .
C7 C 0.3956(3) 0.0889(3) 0.34641(14) 0.0445(6) Uani 1 1 d . . . . .
C8 C 0.6792(3) 0.7519(3) 0.43196(14) 0.0428(6) Uani 1 1 d . . . . .
H8A H 0.601201 0.772842 0.479029 0.051 Uiso 1 1 calc R U . . .
C9 C 0.6916(3) 0.5954(3) 0.38569(13) 0.0399(6) Uani 1 1 d . . . . .
H9A H 0.624342 0.484121 0.393396 0.048 Uiso 1 1 calc R U . . .
C10 C 0.8999(3) 0.5177(2) 0.26364(13) 0.0316(5) Uani 1 1 d . . . . .
C11 C 1.0555(3) 0.4611(3) 0.28884(13) 0.0356(5) Uani 1 1 d . . . . .
C12 C 1.1338(3) 0.3577(3) 0.22570(14) 0.0416(6) Uani 1 1 d . . . . .
H12A H 1.238914 0.314743 0.241117 0.050 Uiso 1 1 calc R U . . .
C13 C 1.0638(3) 0.3152(3) 0.14135(14) 0.0387(6) Uani 1 1 d . . . . .
C14 C 0.9089(3) 0.3754(3) 0.11957(13) 0.0373(6) Uani 1 1 d . . . . .
H14A H 0.861175 0.347170 0.061289 0.045 Uiso 1 1 calc R U . . .
C15 C 0.8211(3) 0.4755(3) 0.18002(13) 0.0351(5) Uani 1 1 d . . . . .
C16 C 1.1401(3) 0.5134(3) 0.37879(14) 0.0519(7) Uani 1 1 d . . . . .
H16A H 1.233188 0.442775 0.387440 0.078 Uiso 1 1 calc R U . . .
H16B H 1.048105 0.494276 0.423319 0.078 Uiso 1 1 calc R U . . .
H16C H 1.194048 0.637478 0.384336 0.078 Uiso 1 1 calc R U . . .
C17 C 1.1578(4) 0.2094(3) 0.07317(16) 0.0592(7) Uani 1 1 d . . . . .
H17A H 1.101349 0.207899 0.015278 0.089 Uiso 1 1 calc R U . . .
H17B H 1.148225 0.089370 0.088286 0.089 Uiso 1 1 calc R U . . .
H17C H 1.284678 0.262292 0.071755 0.089 Uiso 1 1 calc R U . . .
C18 C 0.6493(3) 0.5340(3) 0.15760(16) 0.0565(7) Uani 1 1 d . . . . .
H18A H 0.657164 0.658735 0.177811 0.085 Uiso 1 1 calc R U . . .
H18B H 0.549623 0.466760 0.186540 0.085 Uiso 1 1 calc R U . . .
H18C H 0.628565 0.514904 0.093769 0.085 Uiso 1 1 calc R U . . .
C19 C 0.8457(3) 1.0608(3) 0.42344(15) 0.0468(6) Uani 1 1 d . . . . .
H19A H 0.834377 1.084751 0.487205 0.070 Uiso 1 1 calc R U . . .
H19B H 0.763374 1.121022 0.393439 0.070 Uiso 1 1 calc R U . . .
H19C H 0.969309 1.102853 0.407095 0.070 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
C2 C1 C6 120.4(2) . . ?
N2 N1 C8 112.79(17) . . ?
N2 N1 C19 118.45(17) . . ?
C8 N1 C19 128.76(19) . . ?
C3 C2 C1 120.6(2) . . ?
N1 N2 N3 103.93(16) . . ?
C2 C3 C4 119.6(2) . . ?
N2 N3 C9 112.54(16) . . ?
N2 N3 C10 117.18(16) . . ?
C9 N3 C10 130.15(18) . . ?
C5 C4 C3 119.7(2) . . ?
C4 C5 C6 121.4(2) . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 C7 121.8(2) . . ?
C5 C6 C7 119.99(19) . . ?
O2A C7 O1 119.3(18) . . ?
O1 C7 O2 127.1(7) . . ?
O2A C7 C6 120.8(11) . . ?
O1 C7 C6 117.5(2) . . ?
O2 C7 C6 113.8(7) . . ?
N1 C8 C9 105.75(19) . . ?
N3 C9 C8 104.97(19) . . ?
C11 C10 C15 123.51(19) . . ?
C11 C10 N3 118.15(19) . . ?
C15 C10 N3 118.3(2) . . ?
C12 C11 C10 116.8(2) . . ?
C12 C11 C16 121.0(2) . . ?
C10 C11 C16 122.2(2) . . ?
C13 C12 C11 122.1(2) . . ?
C12 C13 C14 118.8(2) . . ?
C12 C13 C17 120.5(2) . . ?
C14 C13 C17 120.6(2) . . ?
C13 C14 C15 122.2(2) . . ?
C14 C15 C10 116.6(2) . . ?
C14 C15 C18 122.2(2) . . ?
C10 C15 C18 121.2(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
C1 C2 1.381(3) . ?
C1 C6 1.385(3) . ?
O1 C7 1.251(3) . ?
N1 N2 1.309(2) . ?
N1 C8 1.346(3) . ?
N1 C19 1.474(3) . ?
C2 C3 1.375(3) . ?
N2 N3 1.324(2) . ?
O2 C7 1.262(16) . ?
O2A C7 1.234(15) . ?
C3 C4 1.379(3) . ?
N3 C9 1.351(3) . ?
N3 C10 1.443(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.508(3) . ?
C8 C9 1.359(3) . ?
C10 C11 1.391(3) . ?
C10 C15 1.392(3) . ?
C11 C12 1.388(3) . ?
C11 C16 1.501(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.383(3) . ?
C13 C17 1.512(3) . ?
C14 C15 1.387(3) . ?
C15 C18 1.496(3) . ?
