#------------------------------------------------------------------------------
#$Date: 2016-03-04 11:11:07 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177395 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/49/4124916.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_4124916
loop_
_publ_author_name
'Kong, Wei-Jun'
'Liu, Yue-Jin'
'Xu, Hui'
'Chen, Yan-Qiao'
'Dai, Hui-Xiong'
'Yu, Jin-Quan'
_publ_section_title
;
 Pd-Catalyzed α-Selective C-H Functionalization of Olefins: En Route to
 4-Imino-β-Lactams.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2146
_journal_page_last               2149
_journal_paper_doi               10.1021/jacs.5b13353
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C15 H18 N2 O2'
_chemical_formula_weight         258.31
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 117.339(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3100(18)
_cell_length_b                   7.0317(13)
_cell_length_c                   10.730(2)
_cell_measurement_reflns_used    1335
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.940
_cell_measurement_theta_min      4.537
_cell_volume                     691.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3899
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.137
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.109(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0538
_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)+(0.0909P)²+0.0388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1128
_reflns_number_total             1401
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b13353_si_004.cif
_cod_data_source_block           cd214701
_cod_depositor_comments
'Adding full bibliography for 4124916--4124918.cif.'
_cod_database_code               4124916
_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. 
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
O1 O -0.01283(16) 0.7500 0.20078(15) 0.0671(5) Uani 1 2 d S T P
O2 O -0.21734(14) 0.7500 0.00016(15) 0.0560(5) Uani 1 2 d S T P
N1 N 0.22566(17) 0.7500 -0.03719(17) 0.0465(5) Uani 1 2 d S T P
N2 N 0.23930(18) 0.7500 0.18396(17) 0.0533(5) Uani 1 2 d S T P
H2A H 0.1903 0.7500 0.2331 0.064 Uiso 1 2 d R U P
C1 C 0.1434(2) 0.7500 -0.1791(2) 0.0442(5) Uani 1 2 d S T P
C2 C 0.2143(3) 0.7500 -0.2648(2) 0.0568(6) Uani 1 2 d S T P
H2 H 0.3158 0.7500 -0.2235 0.068 Uiso 1 2 calc R U P
C3 C 0.1360(3) 0.7500 -0.4067(3) 0.0689(7) Uani 1 2 d S T P
H3 H 0.1848 0.7500 -0.4612 0.083 Uiso 1 2 calc R U P
C4 C -0.0150(3) 0.7500 -0.4720(2) 0.0747(8) Uani 1 2 d S T P
H4 H -0.0668 0.7500 -0.5694 0.090 Uiso 1 2 calc R U P
C5 C -0.0874(3) 0.7500 -0.3931(2) 0.0660(7) Uani 1 2 d S T P
H5 H -0.1889 0.7500 -0.4371 0.079 Uiso 1 2 calc R U P
C6 C -0.0104(2) 0.7500 -0.2459(2) 0.0473(5) Uani 1 2 d S T P
C7 C -0.0782(2) 0.7500 -0.1578(2) 0.0461(5) Uani 1 2 d S T P
H7 H -0.1796 0.7500 -0.1979 0.055 Uiso 1 2 calc R U P
C8 C 0.0010(2) 0.7500 -0.01577(19) 0.0410(5) Uani 1 2 d S T P
C9 C 0.1597(2) 0.7500 0.0434(2) 0.0419(5) Uani 1 2 d S T P
C10 C -0.0726(2) 0.7500 0.0746(2) 0.0446(5) Uani 1 2 d S T P
C11 C -0.2980(2) 0.7500 0.0798(2) 0.0608(6) Uani 1 2 d S T P
H11A H -0.2544 0.6613 0.1560 0.091 Uiso 0.5 1 calc R U P
H11B H -0.3973 0.7135 0.0201 0.091 Uiso 0.5 1 calc R U P
H11C H -0.2961 0.8751 0.1164 0.091 Uiso 0.5 1 calc R U P
C12 C 0.3992(2) 0.7500 0.2683(2) 0.0489(5) Uani 1 2 d S T P
C13 C 0.4247(3) 0.7500 0.4197(2) 0.0647(6) Uani 1 2 d S T P
H13A H 0.5273 0.7500 0.4815 0.097 Uiso 1 2 d R U P
H13B H 0.3732 0.6454 0.4340 0.097 Uiso 0.5 1 d R U P
H13C H 0.3898 0.8673 0.4391 0.097 Uiso 0.5 1 d R U P
C14 C 0.46600(16) 0.9276(2) 0.24043(17) 0.0632(5) Uani 1 1 d . . .
H14A H 0.4485 0.9279 0.1445 0.095 Uiso 1 1 calc R U .
H14B H 0.5693 0.9286 0.3013 0.095 Uiso 1 1 calc R U .
H14C H 0.4225 1.0384 0.2579 0.095 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
C10 O2 C11 115.94(16) . .
C9 N1 C1 119.18(16) . .
C9 N2 C12 128.57(16) . .
C9 N2 H2A 116.6 . .
C12 N2 H2A 114.8 . .
N1 C1 C6 123.21(17) . .
N1 C1 C2 119.00(18) . .
C6 C1 C2 117.79(19) . .
C3 C2 C1 120.7(2) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C4 121.4(2) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C5 C4 C3 119.7(2) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
C4 C5 C6 120.7(2) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C5 C6 C1 119.71(19) . .
C5 C6 C7 123.7(2) . .
C1 C6 C7 116.54(18) . .
C8 C7 C6 121.61(18) . .
C8 C7 H7 119.2 . .
C6 C7 H7 119.2 . .
C7 C8 C9 117.70(18) . .
C7 C8 C10 120.64(17) . .
C9 C8 C10 121.66(17) . .
N1 C9 N2 120.00(16) . .
N1 C9 C8 121.77(17) . .
N2 C9 C8 118.23(17) . .
O1 C10 O2 122.01(17) . .
O1 C10 C8 125.83(18) . .
O2 C10 C8 112.16(16) . .
O2 C11 H11A 109.5 . .
O2 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
O2 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N2 C12 C14 111.09(10) . 4_575
N2 C12 C14 111.09(10) . .
C14 C12 C14 110.41(17) 4_575 .
N2 C12 C13 104.60(16) . .
C14 C12 C13 109.74(11) 4_575 .
C14 C12 C13 109.75(11) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 114.0 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 104.8 . .
H13B C13 H13C 109.5 . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.202(2) .
O2 C10 1.330(2) .
O2 C11 1.440(2) .
N1 C9 1.323(2) .
N1 C1 1.361(3) .
N2 C9 1.346(2) .
N2 C12 1.472(2) .
N2 H2A 0.8816 .
C1 C6 1.408(3) .
C1 C2 1.414(3) .
C2 C3 1.357(3) .
C2 H2 0.9300 .
C3 C4 1.382(4) .
C3 H3 0.9300 .
C4 C5 1.362(3) .
C4 H4 0.9300 .
C5 C6 1.404(3) .
C5 H5 0.9300 .
C6 C7 1.411(3) .
C7 C8 1.359(3) .
C7 H7 0.9300 .
C8 C9 1.458(3) .
C8 C10 1.481(3) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C14 1.5206(19) 4_575
C12 C14 1.5206(19) .
C12 C13 1.522(3) .
C13 H13A 0.9559 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A O1 0.88 1.96 2.687(2) 138.9
C14 H14A N1 0.96 2.55 3.129(2) 118.5
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
_geom_torsion_site_symmetry_4
C9 N1 C1 C6 0.000(0) .
C9 N1 C1 C2 180.000(0) .
N1 C1 C2 C3 180.000(1) .
C6 C1 C2 C3 0.000(1) .
C1 C2 C3 C4 0.000(1) .
C2 C3 C4 C5 0.000(1) .
C3 C4 C5 C6 0.000(1) .
C4 C5 C6 C1 0.000(1) .
C4 C5 C6 C7 180.000(1) .
N1 C1 C6 C5 180.000(0) .
C2 C1 C6 C5 0.000(1) .
N1 C1 C6 C7 0.000(0) .
C2 C1 C6 C7 180.000(0) .
C5 C6 C7 C8 180.000(0) .
C1 C6 C7 C8 0.000(0) .
C6 C7 C8 C9 0.000(0) .
C6 C7 C8 C10 180.000(0) .
C1 N1 C9 N2 180.000(0) .
C1 N1 C9 C8 0.000(0) .
C12 N2 C9 N1 0.000(0) .
C12 N2 C9 C8 180.000(0) .
C7 C8 C9 N1 0.000(0) .
C10 C8 C9 N1 180.0 .
C7 C8 C9 N2 180.000(0) .
C10 C8 C9 N2 0.000(0) .
C11 O2 C10 O1 0.000(0) .
C11 O2 C10 C8 180.0 .
C7 C8 C10 O1 180.000(0) .
C9 C8 C10 O1 0.000(0) .
C7 C8 C10 O2 0.000(0) .
C9 C8 C10 O2 180.0 .
C9 N2 C12 C14 -61.66(12) 4_575
C9 N2 C12 C14 61.66(12) .
C9 N2 C12 C13 180.000(0) .
