#------------------------------------------------------------------------------
#$Date: 2021-09-24 00:57:20 +0300 (Fri, 24 Sep 2021) $
#$Revision: 269259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128985.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_7128985
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            'C25 H25 Cl2 N3 O2'
_chemical_formula_weight         470.38
_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                93.664(11)
_cell_angle_beta                 116.197(9)
_cell_angle_gamma                115.492(9)
_cell_formula_units_Z            2
_cell_length_a                   11.279(3)
_cell_length_b                   11.539(4)
_cell_length_c                   11.879(4)
_cell_measurement_reflns_used    41856
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.988
_cell_measurement_theta_min      2.343
_cell_volume                     1189.1(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_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  0.0351
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41856
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.988
_diffrn_reflns_theta_min         2.343
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6837
_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    1.314
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0428
_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)+(0.0645P)²+0.3801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4429
_reflns_number_total             5673
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04695k2.cif
_cod_data_source_block           wl507
_cod_original_cell_volume        1189.0(7)
_cod_database_code               7128985
_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   0.889
_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
Cl1 Cl 0.44484(5) 0.12635(5) 0.49302(5) 0.04883(15) Uani 1 1 d . . . . .
O1 O 0.20471(17) 0.46670(14) 0.28955(12) 0.0487(3) Uani 1 1 d . . . . .
N1 N 0.25491(14) 0.48437(13) 0.64249(12) 0.0259(3) Uani 1 1 d . . . . .
C1 C -0.0332(2) 0.14832(18) 0.02542(18) 0.0374(4) Uani 1 1 d . . . . .
H1 H 0.015231 0.100654 0.067419 0.045 Uiso 1 1 calc R U . . .
Cl2 Cl 0.35183(6) 0.21355(5) 0.65993(5) 0.05019(15) Uani 1 1 d . . . . .
O2 O 0.19901(13) 0.27283(13) 0.29445(12) 0.0394(3) Uani 1 1 d . . . . .
N2 N 0.33637(15) 0.54171(14) 0.77247(12) 0.0289(3) Uani 1 1 d . . . . .
C2 C -0.1518(2) 0.0890(2) -0.1069(2) 0.0459(5) Uani 1 1 d . . . . .
H2 H -0.184035 0.001517 -0.154699 0.055 Uiso 1 1 calc R U . . .
N3 N 0.47937(14) 0.61352(14) 0.79880(12) 0.0280(3) Uani 1 1 d . . . . .
C3 C -0.2213(3) 0.1574(2) -0.1673(2) 0.0594(6) Uani 1 1 d . . . . .
H3 H -0.300904 0.117871 -0.257835 0.071 Uiso 1 1 calc R U . . .
C4 C -0.1769(3) 0.2837(3) -0.0979(2) 0.0819(9) Uani 1 1 d . . . . .
H4 H -0.227550 0.329806 -0.139921 0.098 Uiso 1 1 calc R U . . .
C5 C -0.0582(3) 0.3430(2) 0.0333(2) 0.0627(7) Uani 1 1 d . . . . .
H5 H -0.026732 0.430552 0.080352 0.075 Uiso 1 1 calc R U . . .
C6 C 0.0151(2) 0.27624(18) 0.09657(16) 0.0346(4) Uani 1 1 d . . . . .
C7 C 0.1514(2) 0.34482(17) 0.24030(17) 0.0326(3) Uani 1 1 d . . . . .
C8 C 0.34288(18) 0.51809(16) 0.58706(15) 0.0283(3) Uani 1 1 d . . . . .
H8 H 0.309187 0.488973 0.496262 0.034 Uiso 1 1 calc R U . . .
C9 C 0.48984(18) 0.60267(17) 0.68971(15) 0.0296(3) Uani 1 1 d . . . . .
H9 H 0.580444 0.645046 0.685631 0.035 Uiso 1 1 calc R U . . .
C10 C 0.60410(17) 0.69622(16) 0.93319(14) 0.0283(3) Uani 1 1 d . . . . .
C11 C 0.62447(19) 0.82084(18) 0.98141(16) 0.0351(4) Uani 1 1 d . . . . .
C12 C 0.7509(2) 0.90191(18) 1.10711(16) 0.0363(4) Uani 1 1 d . . . . .
H12 H 0.768579 0.987669 1.143125 0.044 Uiso 1 1 calc R U . . .
C13 C 0.85217(18) 0.86124(17) 1.18169(15) 0.0321(3) Uani 1 1 d . . . . .
C14 C 0.82351(18) 0.73442(17) 1.12936(15) 0.0312(3) Uani 1 1 d . . . . .
H14 H 0.891031 0.705331 1.180947 0.037 Uiso 1 1 calc R U . . .
C15 C 0.69929(18) 0.64858(16) 1.00400(15) 0.0285(3) Uani 1 1 d . . . . .
C16 C 0.5167(3) 0.8671(2) 0.9015(2) 0.0552(6) Uani 1 1 d . . . . .
H16A H 0.495138 0.848544 0.810797 0.083 Uiso 1 1 calc R U . . .
H16B H 0.564442 0.964383 0.941090 0.083 Uiso 1 1 calc R U . . .
H16C H 0.420353 0.818360 0.900633 0.083 Uiso 1 1 calc R U . . .
C17 C 0.9914(2) 0.95415(19) 1.31532(17) 0.0410(4) Uani 1 1 d . . . . .
H17A H 1.057813 0.915661 1.347637 0.062 Uiso 1 1 calc R U . . .
H17B H 0.958556 0.964512 1.377280 0.062 Uiso 1 1 calc R U . . .
H17C H 1.048350 1.042727 1.308018 0.062 Uiso 1 1 calc R U . . .
C18 C 0.6707(2) 0.51187(18) 0.94904(17) 0.0372(4) Uani 1 1 d . . . . .
H18A H 0.565206 0.442458 0.920477 0.056 Uiso 1 1 calc R U . . .
H18B H 0.743302 0.493486 1.017438 0.056 Uiso 1 1 calc R U . . .
H18C H 0.684823 0.510606 0.873385 0.056 Uiso 1 1 calc R U . . .
C19 C 0.09090(17) 0.39496(16) 0.57845(15) 0.0265(3) Uani 1 1 d . . . . .
C20 C 0.01835(18) 0.28697(17) 0.46792(16) 0.0322(3) Uani 1 1 d . . . . .
H20 H 0.074299 0.273137 0.433165 0.039 Uiso 1 1 calc R U . . .
C21 C -0.1391(2) 0.19921(19) 0.40920(17) 0.0386(4) Uani 1 1 d . . . . .
H21 H -0.192181 0.124870 0.332381 0.046 Uiso 1 1 calc R U . . .
C22 C -0.21914(19) 0.21922(19) 0.46168(17) 0.0381(4) Uani 1 1 d . . . . .
H22 H -0.326173 0.157203 0.421970 0.046 Uiso 1 1 calc R U . . .
C23 C -0.14444(19) 0.32889(19) 0.57159(17) 0.0352(4) Uani 1 1 d . . . . .
H23 H -0.200409 0.342388 0.606508 0.042 Uiso 1 1 calc R U . . .
C24 C 0.01248(19) 0.41933(17) 0.63091(16) 0.0305(3) Uani 1 1 d . . . . .
H24 H 0.064730 0.495849 0.705460 0.037 Uiso 1 1 calc R U . . .
C25 C 0.4327(2) 0.25926(18) 0.56045(17) 0.0355(4) Uani 1 1 d . . . . .
H25A H 0.536852 0.340493 0.614300 0.043 Uiso 1 1 calc R U . . .
H25B H 0.368624 0.282215 0.487812 0.043 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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C8 112.98(13) . . ?
N2 N1 C19 118.70(12) . . ?
C8 N1 C19 128.31(13) . . ?
C6 C1 C2 120.83(17) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
N3 N2 N1 103.32(12) . . ?
C3 C2 C1 119.63(18) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
N2 N3 C9 113.07(13) . . ?
N2 N3 C10 119.96(12) . . ?
C9 N3 C10 126.93(13) . . ?
C2 C3 C4 120.50(19) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.41(16) . . ?
C5 C6 C7 120.65(16) . . ?
C1 C6 C7 120.88(15) . . ?
O1 C7 O2 126.51(17) . . ?
O1 C7 C6 117.02(15) . . ?
O2 C7 C6 116.45(15) . . ?
N1 C8 C9 105.20(14) . . ?
N1 C8 H8 127.4 . . ?
C9 C8 H8 127.4 . . ?
N3 C9 C8 105.44(14) . . ?
N3 C9 H9 127.3 . . ?
C8 C9 H9 127.3 . . ?
C15 C10 C11 124.09(14) . . ?
C15 C10 N3 117.99(14) . . ?
C11 C10 N3 117.88(14) . . ?
C12 C11 C10 116.68(15) . . ?
C12 C11 C16 121.23(16) . . ?
C10 C11 C16 122.09(16) . . ?
C13 C12 C11 121.95(16) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 118.62(15) . . ?
C12 C13 C17 120.41(16) . . ?
C14 C13 C17 120.96(16) . . ?
C13 C14 C15 122.26(15) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 116.37(15) . . ?
C10 C15 C18 122.22(14) . . ?
C14 C15 C18 121.40(15) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 122.61(15) . . ?
C20 C19 N1 118.41(14) . . ?
C24 C19 N1 118.97(14) . . ?
C19 C20 C21 117.91(15) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C22 C21 C20 120.58(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.50(16) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 120.03(15) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 118.32(16) . . ?
C19 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
Cl2 C25 Cl1 111.34(10) . . ?
Cl2 C25 H25A 109.4 . . ?
Cl1 C25 H25A 109.4 . . ?
Cl2 C25 H25B 109.4 . . ?
Cl1 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
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
Cl1 C25 1.7701(19) . ?
O1 C7 1.240(2) . ?
N1 N2 1.3265(18) . ?
N1 C8 1.359(2) . ?
N1 C19 1.4421(19) . ?
C1 C6 1.390(2) . ?
C1 C2 1.396(3) . ?
C1 H1 0.9500 . ?
Cl2 C25 1.7674(18) . ?
O2 C7 1.241(2) . ?
N2 N3 1.3256(19) . ?
C2 C3 1.364(3) . ?
C2 H2 0.9500 . ?
N3 C9 1.355(2) . ?
N3 C10 1.451(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.539(2) . ?
C8 C9 1.363(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.390(2) . ?
C10 C11 1.394(2) . ?
C11 C12 1.390(2) . ?
C11 C16 1.506(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(2) . ?
C13 C17 1.506(2) . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C15 C18 1.504(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.382(2) . ?
C19 C24 1.389(2) . ?
C20 C21 1.391(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
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
C8 N1 N2 N3 0.11(16) . . . . ?
C19 N1 N2 N3 178.86(12) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
N1 N2 N3 C9 -0.12(17) . . . . ?
N1 N2 N3 C10 177.84(13) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C7 177.3(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C1 C6 C7 -176.78(16) . . . . ?
C5 C6 C7 O1 -9.4(3) . . . . ?
C1 C6 C7 O1 167.80(17) . . . . ?
C5 C6 C7 O2 171.96(19) . . . . ?
C1 C6 C7 O2 -10.8(2) . . . . ?
N2 N1 C8 C9 -0.06(18) . . . . ?
C19 N1 C8 C9 -178.66(14) . . . . ?
N2 N3 C9 C8 0.09(18) . . . . ?
C10 N3 C9 C8 -177.70(15) . . . . ?
N1 C8 C9 N3 -0.02(17) . . . . ?
N2 N3 C10 C15 103.36(17) . . . . ?
C9 N3 C10 C15 -79.0(2) . . . . ?
N2 N3 C10 C11 -79.03(19) . . . . ?
C9 N3 C10 C11 98.6(2) . . . . ?
C15 C10 C11 C12 1.6(3) . . . . ?
N3 C10 C11 C12 -175.81(15) . . . . ?
C15 C10 C11 C16 -179.07(18) . . . . ?
N3 C10 C11 C16 3.5(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C16 C11 C12 C13 -179.45(18) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C11 C12 C13 C17 177.56(16) . . . . ?
C12 C13 C14 C15 1.6(2) . . . . ?
C17 C13 C14 C15 -177.36(15) . . . . ?
C11 C10 C15 C14 -1.5(2) . . . . ?
N3 C10 C15 C14 175.98(13) . . . . ?
C11 C10 C15 C18 178.55(16) . . . . ?
N3 C10 C15 C18 -4.0(2) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C13 C14 C15 C18 179.78(15) . . . . ?
N2 N1 C19 C20 -147.27(15) . . . . ?
C8 N1 C19 C20 31.3(2) . . . . ?
N2 N1 C19 C24 31.8(2) . . . . ?
C8 N1 C19 C24 -149.64(16) . . . . ?
C24 C19 C20 C21 -0.9(2) . . . . ?
N1 C19 C20 C21 178.20(14) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23 1.6(3) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C20 C19 C24 C23 1.9(2) . . . . ?
N1 C19 C24 C23 -177.20(14) . . . . ?
C22 C23 C24 C19 -1.1(2) . . . . ?
