#------------------------------------------------------------------------------
#$Date: 2022-06-29 00:54:15 +0300 (Wed, 29 Jun 2022) $
#$Revision: 276368 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/02/7130294.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_7130294
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            'C21 H27 Au Cl N3'
_chemical_formula_weight         553.87
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1502(11)
_cell_length_b                   15.359(2)
_cell_length_c                   17.032(2)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.57
_cell_measurement_theta_min      2.39
_cell_volume                     2132.0(5)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0843
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20519
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         1.785
_exptl_absorpt_coefficient_mu    7.035
_exptl_absorpt_correction_T_max  0.9014
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.100
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.155
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0412
_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)+(0.0424P)²+1.1572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3644
_reflns_number_total             3966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02303b2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7130294
_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
Au1 Au 0.57315(7) 0.38311(3) 0.33979(2) 0.03743(16) Uani 1 1 d . . . . .
Cl1 Cl 0.7393(6) 0.4883(2) 0.3875(2) 0.0642(12) Uani 1 1 d . . . . .
N1 N 0.4637(13) 0.2504(6) 0.2265(5) 0.035(3) Uani 1 1 d . . . . .
N2 N 0.3496(11) 0.2254(5) 0.3375(6) 0.0300(19) Uani 1 1 d . . . . .
N3 N 0.3026(15) 0.3091(7) 0.4505(5) 0.044(3) Uani 1 1 d . . . . .
C1 C 0.4405(17) 0.2847(6) 0.2996(6) 0.032(2) Uani 1 1 d . . . . .
C2 C 0.3886(15) 0.1707(7) 0.2210(7) 0.035(3) Uani 1 1 d . . . . .
H2 H 0.385615 0.135558 0.176518 0.042 Uiso 1 1 calc R U . . .
C3 C 0.3209(15) 0.1521(7) 0.2899(6) 0.032(3) Uani 1 1 d . . . . .
C4 C 0.2422(18) 0.0783(8) 0.3217(7) 0.045(3) Uani 1 1 d . . . . .
H4 H 0.222090 0.029260 0.291184 0.054 Uiso 1 1 calc R U . . .
C5 C 0.197(2) 0.0813(9) 0.3983(8) 0.052(4) Uani 1 1 d . . . . .
H5 H 0.153281 0.031805 0.421884 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2143(19) 0.1573(8) 0.4422(8) 0.049(3) Uani 1 1 d . . . . .
H6 H 0.176365 0.157697 0.493660 0.059 Uiso 1 1 calc R U . . .
C7 C 0.2834(18) 0.2299(8) 0.4136(7) 0.039(3) Uani 1 1 d . . . . .
C8 C 0.200(2) 0.3778(10) 0.4195(8) 0.063(4) Uani 1 1 d . . . . .
H8A H 0.216980 0.382333 0.363855 0.095 Uiso 1 1 calc R U . . .
H8B H 0.229046 0.431939 0.444089 0.095 Uiso 1 1 calc R U . . .
H8C H 0.087303 0.364745 0.429959 0.095 Uiso 1 1 calc R U . . .
C9 C 0.285(3) 0.3045(11) 0.5375(8) 0.072(5) Uani 1 1 d . . . . .
H9A H 0.176243 0.284553 0.550436 0.109 Uiso 1 1 calc R U . . .
H9B H 0.301792 0.361196 0.559691 0.109 Uiso 1 1 calc R U . . .
H9C H 0.364152 0.264650 0.558461 0.109 Uiso 1 1 calc R U . . .
C10 C 0.5602(18) 0.2873(7) 0.1645(7) 0.040(3) Uani 1 1 d . . . . .
C11 C 0.4877(15) 0.3487(8) 0.1170(7) 0.035(3) Uani 1 1 d . . . . .
C12 C 0.5821(19) 0.3793(8) 0.0554(7) 0.048(3) Uani 1 1 d . . . . .
H12 H 0.538582 0.420491 0.021219 0.057 Uiso 1 1 calc R U . . .
C13 C 0.739(2) 0.3497(8) 0.0439(7) 0.057(4) Uani 1 1 d . . . . .
H13 H 0.799636 0.370857 0.001772 0.069 Uiso 1 1 calc R U . . .
C14 C 0.807(2) 0.2902(9) 0.0925(8) 0.052(4) Uani 1 1 d . . . . .
H14 H 0.913800 0.271231 0.083377 0.063 Uiso 1 1 calc R U . . .
C15 C 0.7198(15) 0.2569(7) 0.1563(8) 0.038(3) Uani 1 1 d . . . . .
C16 C 0.3234(19) 0.3850(9) 0.1296(8) 0.060(4) Uani 1 1 d . . . . .
H16 H 0.268206 0.347993 0.168332 0.071 Uiso 1 1 calc R U . . .
C17 C 0.330(2) 0.4762(11) 0.1635(13) 0.086(6) Uani 1 1 d . . . . .
H17A H 0.394585 0.475773 0.210738 0.130 Uiso 1 1 calc R U . . .
H17B H 0.221094 0.495671 0.175274 0.130 Uiso 1 1 calc R U . . .
H17C H 0.379505 0.514829 0.126007 0.130 Uiso 1 1 calc R U . . .
C18 C 0.217(2) 0.3864(13) 0.0565(10) 0.076(5) Uani 1 1 d . . . . .
H18A H 0.263292 0.425581 0.018618 0.115 Uiso 1 1 calc R U . . .
H18B H 0.108294 0.405515 0.070031 0.115 Uiso 1 1 calc R U . . .
H18C H 0.211386 0.328887 0.034487 0.115 Uiso 1 1 calc R U . . .
C19 C 0.801(2) 0.1953(10) 0.2128(8) 0.056(4) Uani 1 1 d . . . . .
H19 H 0.717386 0.176627 0.250626 0.067 Uiso 1 1 calc R U . . .
C20 C 0.935(2) 0.2435(12) 0.2589(9) 0.079(5) Uani 1 1 d . . . . .
H20A H 1.028210 0.252969 0.225495 0.119 Uiso 1 1 calc R U . . .
H20B H 0.967345 0.209137 0.303349 0.119 Uiso 1 1 calc R U . . .
H20C H 0.893300 0.298557 0.276623 0.119 Uiso 1 1 calc R U . . .
C21 C 0.865(3) 0.1161(11) 0.1740(11) 0.103(7) Uani 1 1 d . . . . .
H21A H 0.784324 0.093562 0.138546 0.155 Uiso 1 1 calc R U . . .
H21B H 0.890569 0.073047 0.213010 0.155 Uiso 1 1 calc R U . . .
H21C H 0.963083 0.130494 0.145304 0.155 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'
Au Au -2.0133 8.8022 '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'
N N 0.0061 0.0033 '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 Au1 Cl1 175.8(4) . . ?
C1 N1 C2 110.2(9) . . ?
C1 N1 C10 126.5(9) . . ?
C2 N1 C10 123.2(9) . . ?
C1 N2 C3 111.1(9) . . ?
C1 N2 C7 128.5(10) . . ?
C3 N2 C7 120.4(9) . . ?
C7 N3 C8 114.4(11) . . ?
C7 N3 C9 113.6(11) . . ?
C8 N3 C9 110.0(12) . . ?
N2 C1 N1 104.7(9) . . ?
N2 C1 Au1 130.9(8) . . ?
N1 C1 Au1 122.3(8) . . ?
C3 C2 N1 108.5(10) . . ?
C3 C2 H2 125.8 . . ?
N1 C2 H2 125.8 . . ?
C2 C3 N2 105.6(9) . . ?
C2 C3 C4 134.5(11) . . ?
N2 C3 C4 119.9(10) . . ?
C5 C4 C3 117.8(12) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 121.0(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 123.0(12) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 N3 128.0(12) . . ?
C6 C7 N2 117.1(11) . . ?
N3 C7 N2 114.8(10) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 125.0(12) . . ?
C11 C10 N1 117.9(12) . . ?
C15 C10 N1 117.1(11) . . ?
C10 C11 C12 116.0(12) . . ?
C10 C11 C16 124.5(11) . . ?
C12 C11 C16 119.4(11) . . ?
C13 C12 C11 121.0(12) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 121.3(13) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 121.0(15) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 115.6(12) . . ?
C10 C15 C19 124.0(12) . . ?
C14 C15 C19 120.3(12) . . ?
C11 C16 C18 114.0(13) . . ?
C11 C16 C17 111.9(14) . . ?
C18 C16 C17 108.7(13) . . ?
C11 C16 H16 107.3 . . ?
C18 C16 H16 107.3 . . ?
C17 C16 H16 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 C15 112.8(12) . . ?
C21 C19 C20 111.8(16) . . ?
C15 C19 C20 109.7(12) . . ?
C21 C19 H19 107.4 . . ?
C15 C19 H19 107.4 . . ?
C20 C19 H19 107.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
Au1 C1 1.980(12) . ?
Au1 Cl1 2.259(3) . ?
N1 C1 1.366(13) . ?
N1 C2 1.372(14) . ?
N1 C10 1.434(15) . ?
N2 C1 1.339(14) . ?
N2 C3 1.406(14) . ?
N2 C7 1.406(15) . ?
N3 C7 1.378(16) . ?
N3 C8 1.444(18) . ?
N3 C9 1.491(16) . ?
C2 C3 1.328(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(16) . ?
C4 C5 1.357(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.340(18) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.376(17) . ?
C10 C15 1.389(18) . ?
C11 C12 1.384(17) . ?
C11 C16 1.466(19) . ?
C12 C13 1.37(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.35(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(19) . ?
C14 H14 0.9300 . ?
C15 C19 1.503(17) . ?
C16 C18 1.52(2) . ?
C16 C17 1.52(2) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C21 1.48(2) . ?
C19 C20 1.54(2) . ?
C19 H19 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
