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#$Date: 2021-04-03 22:52:53 +0300 (Sat, 03 Apr 2021) $
#$Revision: 263559 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518599.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_4518599
loop_
_publ_author_name
'Tathe, Akash G.'
Urvashi,
'Yadav, Amit K.'
'Chintawar, Chetan C.'
'Patil, Nitin T.'
_publ_section_title
;
 Gold-Catalyzed 1,2-Aminoarylation of Alkenes with External Amines
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              4576
_journal_page_last               4582
_journal_paper_doi               10.1021/acscatal.1c00789
_journal_year                    2021
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.428(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5656(9)
_cell_length_b                   14.7742(15)
_cell_length_c                   7.8958(8)
_cell_measurement_reflns_used    7112
_cell_measurement_temperature    148(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.37
_cell_volume                     1228.8(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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      148(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.929
_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  0.1003
_diffrn_reflns_av_unetI/netI     0.1893
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7385
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.594
_diffrn_reflns_theta_min         2.375
_exptl_absorpt_coefficient_mu    0.093
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             536.0
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.2058
_refine_ls_R_factor_gt           0.0972
_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)+(0.0803P)²+3.0898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.2366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1829
_reflns_number_total             3768
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c00789_si_003.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518599
_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+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.2535(2) 0.60273(18) 0.4149(3) 0.0365(7) Uani 1 1 d . . . . .
N2 N 0.2678(2) 0.45339(19) 0.5998(3) 0.0219(6) Uani 1 1 d . . . . .
H5 H 0.301754 0.506983 0.585519 0.026 Uiso 1 1 calc R U . . .
O2 O 0.1293(3) 0.6084(2) 0.1840(3) 0.0485(8) Uani 1 1 d . . . . .
N1 N 0.1702(3) 0.5692(2) 0.3158(4) 0.0302(7) Uani 1 1 d . . . . .
C10 C 0.3738(3) 0.3788(2) 1.0322(4) 0.0176(7) Uani 1 1 d . . . . .
C11 C 0.4880(3) 0.3847(2) 0.9561(4) 0.0180(7) Uani 1 1 d . . . . .
C6 C 0.1670(3) 0.4294(2) 0.4932(4) 0.0184(7) Uani 1 1 d . . . . .
C5 C 0.1185(3) 0.4817(2) 0.3517(4) 0.0233(7) Uani 1 1 d . . . . .
C12 C 0.6013(3) 0.3595(2) 1.0456(4) 0.0217(7) Uani 1 1 d . . . . .
H11 H 0.679306 0.361736 0.993305 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3238(3) 0.3970(2) 0.7356(4) 0.0198(7) Uani 1 1 d . . . . .
H6 H 0.314132 0.332400 0.699118 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3713(3) 0.3506(2) 1.1992(4) 0.0217(7) Uani 1 1 d . . . . .
H14 H 0.293313 0.347211 1.251236 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4663(3) 0.4161(2) 0.7745(4) 0.0192(7) Uani 1 1 d . . . . .
H9 H 0.518427 0.381169 0.698525 0.023 Uiso 1 1 calc R U . . .
H10 H 0.485463 0.481390 0.763726 0.023 Uiso 1 1 calc R U . . .
C14 C 0.4851(3) 0.3274(2) 1.2895(4) 0.0243(8) Uani 1 1 d . . . . .
H13 H 0.484854 0.308758 1.404603 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2652(3) 0.4073(2) 0.9072(4) 0.0228(7) Uani 1 1 d . . . . .
H8 H 0.239452 0.470614 0.926758 0.027 Uiso 1 1 calc R U . . .
H7 H 0.190712 0.367114 0.914034 0.027 Uiso 1 1 calc R U . . .
C1 C 0.1046(3) 0.3457(2) 0.5146(4) 0.0246(8) Uani 1 1 d . . . . .
H1 H 0.130449 0.309065 0.609896 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5978(3) 0.3311(2) 1.2133(4) 0.0253(8) Uani 1 1 d . . . . .
H12 H 0.674391 0.314064 1.276136 0.030 Uiso 1 1 calc R U . . .
C2 C 0.0078(3) 0.3158(3) 0.4017(5) 0.0328(9) Uani 1 1 d . . . . .
H2 H -0.030928 0.259022 0.420185 0.039 Uiso 1 1 calc R U . . .
C4 C 0.0202(3) 0.4499(3) 0.2392(4) 0.0331(9) Uani 1 1 d . . . . .
H4 H -0.009500 0.486509 0.145479 0.040 Uiso 1 1 calc R U . . .
C3 C -0.0342(3) 0.3674(3) 0.2611(5) 0.0368(10) Uani 1 1 d . . . . .
H3 H -0.099337 0.345564 0.181894 0.044 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
C6 N2 C7 124.5(3) . . ?
C6 N2 H5 117.7 . . ?
C7 N2 H5 117.7 . . ?
O1 N1 O2 121.9(3) . . ?
O1 N1 C5 119.9(3) . . ?
O2 N1 C5 118.2(3) . . ?
C15 C10 C11 120.7(3) . . ?
C15 C10 C8 129.4(3) . . ?
C11 C10 C8 109.9(3) . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 C9 110.9(3) . . ?
C12 C11 C9 128.7(3) . . ?
N2 C6 C1 120.4(3) . . ?
N2 C6 C5 124.4(3) . . ?
C1 C6 C5 115.2(3) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 N1 116.9(3) . . ?
C6 C5 N1 121.6(3) . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 H11 120.7 . . ?
C11 C12 H11 120.7 . . ?
N2 C7 C9 112.3(3) . . ?
N2 C7 C8 115.2(3) . . ?
C9 C7 C8 105.1(2) . . ?
N2 C7 H6 108.0 . . ?
C9 C7 H6 108.0 . . ?
C8 C7 H6 108.0 . . ?
C10 C15 C14 118.8(3) . . ?
C10 C15 H14 120.6 . . ?
C14 C15 H14 120.6 . . ?
C11 C9 C7 101.9(3) . . ?
C11 C9 H9 111.4 . . ?
C7 C9 H9 111.4 . . ?
C11 C9 H10 111.4 . . ?
C7 C9 H10 111.4 . . ?
H9 C9 H10 109.2 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H13 119.7 . . ?
C15 C14 H13 119.7 . . ?
C10 C8 C7 102.1(2) . . ?
C10 C8 H8 111.3 . . ?
C7 C8 H8 111.3 . . ?
C10 C8 H7 111.3 . . ?
C7 C8 H7 111.3 . . ?
H8 C8 H7 109.2 . . ?
C2 C1 C6 122.1(3) . . ?
C2 C1 H1 118.9 . . ?
C6 C1 H1 118.9 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H12 119.5 . . ?
C12 C13 H12 119.5 . . ?
C1 C2 C3 121.1(4) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
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 N1 1.236(4) . ?
N2 C6 1.353(4) . ?
N2 C7 1.448(4) . ?
N2 H5 0.8800 . ?
O2 N1 1.240(4) . ?
N1 C5 1.439(5) . ?
C10 C15 1.385(4) . ?
C10 C11 1.391(4) . ?
C10 C8 1.514(4) . ?
C11 C12 1.393(4) . ?
C11 C9 1.508(4) . ?
C6 C1 1.417(5) . ?
C6 C5 1.421(4) . ?
C5 C4 1.395(5) . ?
C12 C13 1.393(5) . ?
C12 H11 0.9500 . ?
C7 C9 1.540(4) . ?
C7 C8 1.540(4) . ?
C7 H6 1.0000 . ?
C15 C14 1.392(4) . ?
C15 H14 0.9500 . ?
C9 H9 0.9900 . ?
C9 H10 0.9900 . ?
C14 C13 1.376(5) . ?
C14 H13 0.9500 . ?
C8 H8 0.9900 . ?
C8 H7 0.9900 . ?
C1 C2 1.376(4) . ?
C1 H1 0.9500 . ?
C13 H12 0.9500 . ?
C2 C3 1.390(5) . ?
C2 H2 0.9500 . ?
C4 C3 1.365(6) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
