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#$Date: 2021-04-03 22:53:19 +0300 (Sat, 03 Apr 2021) $
#$Revision: 263561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/86/4518600.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_4518600
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 N3 O2'
_chemical_formula_weight         270.28
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3825(10)
_cell_length_b                   9.8600(11)
_cell_length_c                   13.8680(12)
_cell_measurement_reflns_used    4767
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.53
_cell_volume                     1282.9(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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.1360
_diffrn_reflns_av_unetI/netI     0.1127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21814
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.148
_diffrn_reflns_theta_min         2.535
_exptl_absorpt_coefficient_mu    0.099
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             568
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0639
_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)+(0.0342P)²+0.3473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2272
_reflns_number_total             3450
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c00789_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4518600
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.5139(2) 0.8701(2) 0.60805(15) 0.0238(6) Uani 1 1 d . . . . .
O2 O 0.1762(3) 0.8902(3) -0.00444(16) 0.0332(6) Uani 1 1 d . . . . .
O3 O 0.3344(3) 0.7358(3) -0.03058(16) 0.0385(7) Uani 1 1 d . . . . .
N2 N 0.2747(3) 0.8163(3) 0.02350(19) 0.0243(7) Uani 1 1 d . . . . .
N1 N 0.4540(3) 0.8617(3) 0.40561(17) 0.0210(6) Uani 1 1 d . . . . .
H14 H 0.400189 0.910298 0.444446 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2446(3) 0.9093(3) 0.1862(2) 0.0198(8) Uani 1 1 d . . . . .
H12 H 0.162669 0.957514 0.165121 0.024 Uiso 1 1 calc R U . . .
C13 C 0.3201(3) 0.8271(3) 0.1224(2) 0.0175(7) Uani 1 1 d . . . . .
C6 C 0.4674(3) 0.7401(3) 0.6290(2) 0.0178(7) Uani 1 1 d . . . . .
C11 C 0.2901(3) 0.9196(3) 0.2796(2) 0.0184(8) Uani 1 1 d . . . . .
H13 H 0.239042 0.975486 0.323453 0.022 Uiso 1 1 calc R U . . .
C1 C 0.4005(3) 0.7251(4) 0.7176(2) 0.0207(8) Uani 1 1 d . . . . .
H1 H 0.390965 0.800608 0.759693 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4115(3) 0.8485(3) 0.3120(2) 0.0169(7) Uani 1 1 d . . . . .
C5 C 0.4823(3) 0.6316(4) 0.5655(2) 0.0189(7) Uani 1 1 d . . . . .
C8 C 0.5824(3) 0.8010(3) 0.4455(2) 0.0188(7) Uani 1 1 d . . . . .
H7 H 0.661328 0.809118 0.397363 0.023 Uiso 1 1 calc R U . . .
C15 C 0.4854(3) 0.7658(3) 0.2458(2) 0.0208(7) Uani 1 1 d . . . . .
H10 H 0.567001 0.716549 0.266221 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4275(4) 0.5076(4) 0.5945(2) 0.0246(8) Uani 1 1 d . . . . .
H4 H 0.435432 0.431944 0.552373 0.029 Uiso 1 1 calc R U . . .
C14 C 0.4399(4) 0.7562(3) 0.1519(2) 0.0219(8) Uani 1 1 d . . . . .
H11 H 0.490447 0.701116 0.107370 0.026 Uiso 1 1 calc R U . . .
C2 C 0.3480(3) 0.6002(4) 0.7441(2) 0.0240(8) Uani 1 1 d . . . . .
H2 H 0.302340 0.589266 0.804723 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5606(4) 0.6503(4) 0.4706(2) 0.0261(8) Uani 1 1 d . . . . .
H6 H 0.505553 0.606135 0.418400 0.031 Uiso 1 1 calc R U . . .
H5 H 0.654608 0.605104 0.474536 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3616(4) 0.4908(4) 0.6826(2) 0.0289(9) Uani 1 1 d . . . . .
H3 H 0.325771 0.404405 0.700849 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6238(3) 0.8767(4) 0.5366(2) 0.0258(8) Uani 1 1 d . . . . .
H8 H 0.712425 0.836996 0.563157 0.031 Uiso 1 1 calc R U . . .
H9 H 0.643045 0.972768 0.520609 0.031 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 O1 C9 114.5(3) . . ?
O3 N2 O2 122.0(3) . . ?
O3 N2 C13 119.6(3) . . ?
O2 N2 C13 118.4(3) . . ?
C10 N1 C8 124.3(3) . . ?
C10 N1 H14 117.8 . . ?
C8 N1 H14 117.8 . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 N2 119.0(3) . . ?
C12 C13 N2 119.8(3) . . ?
O1 C6 C1 115.3(3) . . ?
O1 C6 C5 123.2(3) . . ?
C1 C6 C5 121.5(3) . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H13 119.5 . . ?
C10 C11 H13 119.5 . . ?
C2 C1 C6 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
N1 C10 C15 122.1(3) . . ?
N1 C10 C11 119.4(3) . . ?
C15 C10 C11 118.5(3) . . ?
C4 C5 C6 117.2(3) . . ?
C4 C5 C7 122.6(3) . . ?
C6 C5 C7 120.2(3) . . ?
N1 C8 C9 109.0(3) . . ?
N1 C8 C7 111.9(3) . . ?
C9 C8 C7 108.6(3) . . ?
N1 C8 H7 109.1 . . ?
C9 C8 H7 109.1 . . ?
C7 C8 H7 109.1 . . ?
C14 C15 C10 120.3(3) . . ?
C14 C15 H10 119.9 . . ?
C10 C15 H10 119.9 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H11 120.1 . . ?
C13 C14 H11 120.1 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C7 C8 112.2(3) . . ?
C5 C7 H6 109.2 . . ?
C8 C7 H6 109.2 . . ?
C5 C7 H5 109.2 . . ?
C8 C7 H5 109.2 . . ?
H6 C7 H5 107.9 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O1 C9 C8 111.7(3) . . ?
O1 C9 H8 109.3 . . ?
C8 C9 H8 109.3 . . ?
O1 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
H8 C9 H9 107.9 . . ?
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 C6 1.385(4) . ?
O1 C9 1.431(4) . ?
O2 N2 1.239(4) . ?
O3 N2 1.228(3) . ?
N2 C13 1.440(4) . ?
N1 C10 1.364(4) . ?
N1 C8 1.454(4) . ?
N1 H14 0.8800 . ?
C12 C11 1.368(4) . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C6 C1 1.388(4) . ?
C6 C5 1.393(4) . ?
C11 C10 1.411(4) . ?
C11 H13 0.9500 . ?
C1 C2 1.376(5) . ?
C1 H1 0.9500 . ?
C10 C15 1.409(4) . ?
C5 C4 1.386(5) . ?
C5 C7 1.518(4) . ?
C8 C9 1.518(4) . ?
C8 C7 1.540(5) . ?
C8 H7 1.0000 . ?
C15 C14 1.373(5) . ?
C15 H10 0.9500 . ?
C4 C3 1.379(5) . ?
C4 H4 0.9500 . ?
C14 H11 0.9500 . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C7 H6 0.9900 . ?
C7 H5 0.9900 . ?
C3 H3 0.9500 . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
