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#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/52/1545236.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_1545236
loop_
_publ_author_name
'Bao, Deng-Hui'
'Gu, Xue-Song'
'Xie, Jian-Hua'
'Zhou, Qi-Lin'
_publ_section_title
;
 Iridium-Catalyzed Asymmetric Hydrogenation of Racemic β-Keto Lactams via
 Dynamic Kinetic Resolution.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              118
_journal_page_last               121
_journal_paper_doi               10.1021/acs.orglett.6b03397
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C13 H17 N O2'
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.27
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.517(2)
_cell_length_b                   7.786(2)
_cell_length_c                   27.221(8)
_cell_measurement_reflns_used    1359
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      78.70
_cell_measurement_theta_min      30.10
_cell_volume                     1169.3(6)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            12610
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         79.444
_diffrn_reflns_theta_min         3.247
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       0.0045(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0290
_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)+(0.0458P)²+0.0794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0794
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2379
_reflns_number_total             2475
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b03397_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               1545236
_shelx_shelxl_version_number     2014/7
_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   0.824
_shelx_estimated_absorpt_t_max   0.889
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
O1 O 0.5131(3) 0.01913(14) 0.04507(4) 0.0451(3) Uani 1 1 d . .
O2 O 0.8275(2) 0.41872(16) 0.04644(4) 0.0421(3) Uani 1 1 d . .
N1 N 0.7356(2) 0.08975(16) 0.11276(4) 0.0322(3) Uani 1 1 d . .
C1 C 0.5703(3) 0.12217(18) 0.07737(5) 0.0311(3) Uani 1 1 d . .
C2 C 0.4740(3) 0.30346(18) 0.08349(5) 0.0302(3) Uani 1 1 d . .
H2 H 0.2927 0.3025 0.0831 0.036 Uiso 1 1 calc R U
C3 C 0.5661(3) 0.3551(2) 0.13482(5) 0.0357(4) Uani 1 1 d . .
H3A H 0.6156 0.4773 0.1353 0.043 Uiso 1 1 calc R U
H3B H 0.4389 0.3369 0.1599 0.043 Uiso 1 1 calc R U
C4 C 0.7841(3) 0.2376(2) 0.14432(5) 0.0349(4) Uani 1 1 d . .
H4A H 0.9377 0.2947 0.1350 0.042 Uiso 1 1 calc R U
H4B H 0.7925 0.2032 0.1793 0.042 Uiso 1 1 calc R U
C5 C 0.5699(3) 0.41531(19) 0.04154(5) 0.0325(3) Uani 1 1 d . .
H5 H 0.5275 0.3596 0.0096 0.039 Uiso 1 1 calc R U
C6 C 0.4643(4) 0.5951(2) 0.04227(6) 0.0439(4) Uani 1 1 d . .
H6A H 0.5074 0.6517 0.0732 0.053 Uiso 1 1 calc R U
H6B H 0.2875 0.5886 0.0394 0.053 Uiso 1 1 calc R U
H6C H 0.5298 0.6613 0.0147 0.053 Uiso 1 1 calc R U
C7 C 0.8910(3) -0.0606(2) 0.11180(5) 0.0345(3) Uani 1 1 d . .
H7A H 1.0616 -0.0225 0.1089 0.041 Uiso 1 1 calc R U
H7B H 0.8520 -0.1292 0.0822 0.041 Uiso 1 1 calc R U
C8 C 0.8670(3) -0.17461(18) 0.15685(5) 0.0288(3) Uani 1 1 d . .
C9 C 0.6674(3) -0.1655(2) 0.18788(5) 0.0332(3) Uani 1 1 d . .
H9 H 0.5425 -0.0846 0.1814 0.040 Uiso 1 1 calc R U
C10 C 0.6487(3) -0.2743(2) 0.22841(5) 0.0393(4) Uani 1 1 d . .
H10 H 0.5116 -0.2670 0.2494 0.047 Uiso 1 1 calc R U
C11 C 0.8294(3) -0.3927(2) 0.23812(5) 0.0416(4) Uani 1 1 d . .
H11 H 0.8172 -0.4664 0.2658 0.050 Uiso 1 1 calc R U
C12 C 1.0275(3) -0.4031(2) 0.20731(6) 0.0415(4) Uani 1 1 d . .
H12 H 1.1516 -0.4847 0.2138 0.050 Uiso 1 1 calc R U
C13 C 1.0465(3) -0.2949(2) 0.16688(5) 0.0362(3) Uani 1 1 d . .
H13 H 1.1835 -0.3033 0.1459 0.043 Uiso 1 1 calc R U
H1 H 0.892(4) 0.439(3) 0.0180(9) 0.059(6) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 O2 H1 109.1(16)
C1 N1 C7 122.48(12)
C1 N1 C4 113.32(12)
C7 N1 C4 122.55(12)
O1 C1 N1 124.12(14)
O1 C1 C2 126.48(13)
N1 C1 C2 109.40(12)
C1 C2 C5 109.04(11)
C1 C2 C3 103.10(12)
C5 C2 C3 114.47(12)
C1 C2 H2 110.0
C5 C2 H2 110.0
C3 C2 H2 110.0
C4 C3 C2 104.85(12)
C4 C3 H3A 110.8
C2 C3 H3A 110.8
C4 C3 H3B 110.8
C2 C3 H3B 110.8
H3A C3 H3B 108.9
N1 C4 C3 103.14(12)
N1 C4 H4A 111.1
C3 C4 H4A 111.1
N1 C4 H4B 111.1
C3 C4 H4B 111.1
H4A C4 H4B 109.1
O2 C5 C6 111.34(13)
O2 C5 C2 106.55(12)
C6 C5 C2 112.50(13)
O2 C5 H5 108.8
C6 C5 H5 108.8
C2 C5 H5 108.8
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N1 C7 C8 113.93(12)
N1 C7 H7A 108.8
C8 C7 H7A 108.8
N1 C7 H7B 108.8
C8 C7 H7B 108.8
H7A C7 H7B 107.7
C9 C8 C13 118.64(13)
C9 C8 C7 121.97(13)
C13 C8 C7 119.37(13)
C8 C9 C10 120.56(14)
C8 C9 H9 119.7
C10 C9 H9 119.7
C11 C10 C9 120.18(15)
C11 C10 H10 119.9
C9 C10 H10 119.9
C12 C11 C10 119.58(14)
C12 C11 H11 120.2
C10 C11 H11 120.2
C11 C12 C13 120.34(16)
C11 C12 H12 119.8
C13 C12 H12 119.8
C12 C13 C8 120.69(15)
C12 C13 H13 119.7
C8 C13 H13 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2316(18)
O2 C5 1.428(2)
O2 H1 0.87(3)
N1 C1 1.3503(19)
N1 C7 1.451(2)
N1 C4 1.4611(19)
C1 C2 1.517(2)
C2 C5 1.5305(19)
C2 C3 1.5401(19)
C2 H2 1.0000
C3 C4 1.533(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.517(2)
C5 H5 1.0000
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.5198(19)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.390(2)
C8 C13 1.390(2)
C9 C10 1.394(2)
C9 H9 0.9500
C10 C11 1.383(3)
C10 H10 0.9500
C11 C12 1.380(3)
C11 H11 0.9500
C12 C13 1.390(2)
C12 H12 0.9500
C13 H13 0.9500
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
C7 N1 C1 O1 10.0(2)
C4 N1 C1 O1 175.60(14)
C7 N1 C1 C2 -168.93(13)
C4 N1 C1 C2 -3.29(17)
O1 C1 C2 C5 -69.40(19)
N1 C1 C2 C5 109.45(14)
O1 C1 C2 C3 168.57(15)
N1 C1 C2 C3 -12.57(15)
C1 C2 C3 C4 22.54(15)
C5 C2 C3 C4 -95.75(15)
C1 N1 C4 C3 17.75(16)
C7 N1 C4 C3 -176.63(12)
C2 C3 C4 N1 -24.33(15)
C1 C2 C5 O2 -62.81(15)
C3 C2 C5 O2 52.07(16)
C1 C2 C5 C6 174.92(12)
C3 C2 C5 C6 -70.21(17)
C1 N1 C7 C8 -121.98(15)
C4 N1 C7 C8 73.70(18)
N1 C7 C8 C9 18.6(2)
N1 C7 C8 C13 -163.04(13)
C13 C8 C9 C10 0.4(2)
C7 C8 C9 C10 178.79(14)
C8 C9 C10 C11 0.0(2)
C9 C10 C11 C12 -0.3(2)
C10 C11 C12 C13 0.3(2)
C11 C12 C13 C8 0.1(2)
C9 C8 C13 C12 -0.5(2)
C7 C8 C13 C12 -178.86(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10889408
