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#$Date: 2022-06-29 00:54:15 +0300 (Wed, 29 Jun 2022) $
#$Revision: 276368 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/02/7130299.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_7130299
loop_
_publ_author_name
'Pedrazzani, Riccardo'
'Pinosa, Emanuele'
'Bertuzzi, Giulio'
'MONARI, MAGDA'
'Lauzon, Samuel'
'Ollevier, Thierry'
'Bandini, Marco'
_publ_section_title
;
 Convenient synthesis of tricyclic N(1)-C(2)-fused oxazino-indolones via
 [Au(I)] catalyzed hydrocarboxylation of allenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02303B
_journal_year                    2022
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-04-19 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.5420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8360(12)
_cell_length_b                   7.3826(5)
_cell_length_c                   17.1906(11)
_cell_measurement_reflns_used    7851
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.63
_cell_measurement_theta_min      2.40
_cell_volume                     2156.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.973
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12671
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.397
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9114
_exptl_absorpt_correction_T_min  0.7326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       Needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0641
_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)+(0.0506P)²+4.0562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1747
_reflns_number_total             1957
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02303b2.cif
_cod_data_source_block           shelx_CCDC6
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7130299
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O1 O 0.71576(10) 0.4260(3) 0.71833(11) 0.0526(5) Uani 1 1 d . . . . .
O2 O 0.78132(11) 0.4129(3) 0.63932(13) 0.0634(6) Uani 1 1 d . . . . .
N1 N 0.58049(11) 0.3060(3) 0.58186(13) 0.0397(5) Uani 1 1 d . . . . .
C6 C 0.55899(15) 0.2083(4) 0.45019(16) 0.0438(6) Uani 1 1 d . . . . .
C8 C 0.65088(14) 0.3074(3) 0.57545(15) 0.0408(6) Uani 1 1 d . . . . .
C1 C 0.52315(14) 0.2484(3) 0.50487(16) 0.0414(6) Uani 1 1 d . . . . .
C10 C 0.57401(15) 0.3695(4) 0.65802(16) 0.0458(6) Uani 1 1 d . . . . .
H10A H 0.533812 0.301304 0.666350 0.055 Uiso 1 1 calc R U . . .
H10B H 0.559210 0.496426 0.651517 0.055 Uiso 1 1 calc R U . . .
C7 C 0.63986(15) 0.2470(4) 0.49649(16) 0.0468(7) Uani 1 1 d . . . . .
H7 H 0.678356 0.233529 0.476659 0.056 Uiso 1 1 calc R U . . .
C9 C 0.72112(15) 0.3822(4) 0.64488(17) 0.0461(6) Uani 1 1 d . . . . .
C11 C 0.65254(15) 0.3449(4) 0.73479(16) 0.0457(6) Uani 1 1 d . . . . .
H11 H 0.662949 0.215205 0.746032 0.055 Uiso 1 1 calc R U . . .
C2 C 0.44244(15) 0.2265(4) 0.47857(19) 0.0540(7) Uani 1 1 d . . . . .
H2 H 0.419074 0.252642 0.515147 0.065 Uiso 1 1 calc R U . . .
C5 C 0.51224(18) 0.1440(4) 0.36655(18) 0.0569(8) Uani 1 1 d . . . . .
H5 H 0.534690 0.115455 0.329368 0.068 Uiso 1 1 calc R U . . .
C3 C 0.39931(17) 0.1648(4) 0.3963(2) 0.0632(9) Uani 1 1 d . . . . .
H3 H 0.345343 0.149241 0.376779 0.076 Uiso 1 1 calc R U . . .
C12 C 0.65625(18) 0.4348(4) 0.81422(19) 0.0600(8) Uani 1 1 d . . . . .
H12 H 0.646787 0.558704 0.812164 0.072 Uiso 1 1 calc R U . . .
C4 C 0.43359(19) 0.1245(4) 0.34107(19) 0.0631(9) Uani 1 1 d . . . . .
H4 H 0.402070 0.083330 0.285638 0.076 Uiso 1 1 calc R U . . .
C13 C 0.6718(2) 0.3510(6) 0.8854(2) 0.0846(12) Uani 1 1 d . . . . .
H13A H 0.681482 0.227079 0.889460 0.101 Uiso 1 1 calc R U . . .
H13B H 0.673242 0.414521 0.932832 0.101 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
C9 O1 C11 118.5(2) . . ?
C1 N1 C8 108.1(2) . . ?
C1 N1 C10 129.7(2) . . ?
C8 N1 C10 122.0(2) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 133.9(3) . . ?
C1 C6 C7 107.1(2) . . ?
C7 C8 N1 109.9(2) . . ?
C7 C8 C9 129.6(2) . . ?
N1 C8 C9 120.2(2) . . ?
N1 C1 C2 130.2(3) . . ?
N1 C1 C6 107.8(2) . . ?
C2 C1 C6 122.0(2) . . ?
N1 C10 C11 108.6(2) . . ?
N1 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
N1 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
C8 C7 C6 107.0(2) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
O2 C9 O1 119.0(2) . . ?
O2 C9 C8 124.2(3) . . ?
O1 C9 C8 116.8(2) . . ?
O1 C11 C12 105.9(2) . . ?
O1 C11 C10 110.7(2) . . ?
C12 C11 C10 112.8(2) . . ?
O1 C11 H11 109.1 . . ?
C12 C11 H11 109.1 . . ?
C10 C11 H11 109.1 . . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C13 C12 C11 124.0(3) . . ?
C13 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
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
O1 C9 1.349(3) . ?
O1 C11 1.465(3) . ?
O2 C9 1.200(3) . ?
N1 C1 1.366(3) . ?
N1 C8 1.377(3) . ?
N1 C10 1.445(3) . ?
C6 C5 1.406(4) . ?
C6 C1 1.405(4) . ?
C6 C7 1.411(4) . ?
C8 C7 1.357(4) . ?
C8 C9 1.455(4) . ?
C1 C2 1.396(4) . ?
C10 C11 1.510(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 H7 0.9300 . ?
C11 C12 1.492(4) . ?
C11 H11 0.9800 . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C5 C4 1.360(4) . ?
C5 H5 0.9300 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9300 . ?
C12 C13 1.287(4) . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
