#------------------------------------------------------------------------------
#$Date: 2018-08-23 04:40:54 +0300 (Thu, 23 Aug 2018) $
#$Revision: 210091 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/45/4024564.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_4024564
loop_
_publ_author_name
'Zhao, Baoguo'
'Du, Haifeng'
'Shi, Yian'
_publ_section_title
;
 Cu(I)-Catalyzed C--H α-Amination of Aryl Ketones: Direct Synthesis of
 Imidazolinones
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   11
_journal_name_full               'Journal of organic chemistry'
_journal_page_first              4411
_journal_page_last               4413
_journal_paper_doi               10.1021/jo9004553
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C13 H16 N2 O'
_chemical_formula_weight         216.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.330(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   10.3603(5)
_cell_length_b                   19.5772(9)
_cell_length_c                   18.0785(8)
_cell_measurement_reflns_used    9048
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.18
_cell_measurement_theta_min      2.22
_cell_volume                     3665.8(3)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_molecular_graphics    'APEX2 (Bruker, 2009)'
_computing_publication_material  'APEX2 (Bruker, 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0828
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            75621
_diffrn_reflns_theta_full        36.32
_diffrn_reflns_theta_max         36.32
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of Göttingen, Germany.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       ROD
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.051
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         17760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.2158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1554
_reflns_number_gt                8924
_reflns_number_total             17760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9004553_si_003.cif
_cod_data_source_block           ys191r_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4024564
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10299(8) 0.54948(4) 0.56543(5) 0.02910(19) Uani 1 1 d . . .
O2 O 0.87180(8) 0.13871(5) 0.27940(5) 0.0337(2) Uani 1 1 d . . .
O3 O 0.20765(8) 1.09496(4) 0.24416(4) 0.02663(18) Uani 1 1 d . . .
N1 N 0.29342(9) 0.48468(5) 0.57513(5) 0.02177(18) Uani 1 1 d . . .
N2 N 0.13546(9) 0.44585(5) 0.50479(5) 0.02408(19) Uani 1 1 d . . .
H2A H 0.0603 0.4420 0.4815 0.029 Uiso 1 1 calc R . .
N3 N 0.81659(9) 0.21906(5) 0.18732(5) 0.0249(2) Uani 1 1 d . . .
N4 N 1.01410(9) 0.17999(5) 0.19181(5) 0.0254(2) Uani 1 1 d . . .
H4B H 1.0837 0.1570 0.2053 0.031 Uiso 1 1 calc R . .
N5 N 0.24324(10) 0.99052(5) 0.30474(6) 0.0277(2) Uani 1 1 d . . .
N6 N 0.06000(9) 1.04265(5) 0.32130(5) 0.02338(19) Uani 1 1 d . . .
H6A H -0.0028 1.0729 0.3183 0.028 Uiso 1 1 calc R . .
C1 C 0.11769(12) 0.32326(6) 0.41060(6) 0.0276(2) Uani 1 1 d . . .
H1A H 0.0420 0.3501 0.4159 0.033 Uiso 1 1 calc R . .
C2 C 0.11717(13) 0.26912(6) 0.36132(7) 0.0337(3) Uani 1 1 d . . .
H2B H 0.0411 0.2594 0.3329 0.040 Uiso 1 1 calc R . .
C3 C 0.22573(13) 0.22902(6) 0.35281(7) 0.0337(3) Uani 1 1 d . . .
H3A H 0.2251 0.1926 0.3181 0.040 Uiso 1 1 calc R . .
C4 C 0.33570(12) 0.24272(6) 0.39561(7) 0.0293(3) Uani 1 1 d . . .
H4A H 0.4101 0.2148 0.3910 0.035 Uiso 1 1 calc R . .
C5 C 0.33767(11) 0.29675(6) 0.44502(6) 0.0250(2) Uani 1 1 d . . .
H5A H 0.4134 0.3055 0.4741 0.030 Uiso 1 1 calc R . .
C6 C 0.22908(11) 0.33874(5) 0.45262(6) 0.0220(2) Uani 1 1 d . . .
C7 C 0.23570(10) 0.39874(5) 0.50051(6) 0.0216(2) Uani 1 1 d . . .
C8 C 0.33241(10) 0.42273(5) 0.54490(6) 0.0214(2) Uani 1 1 d . . .
H8A H 0.4132 0.4010 0.5539 0.026 Uiso 1 1 calc R . .
C9 C 0.50776(11) 0.50442(6) 0.63179(7) 0.0293(3) Uani 1 1 d . . .
H9A H 0.5471 0.5029 0.5830 0.044 Uiso 1 1 calc R . .
H9B H 0.5061 0.4583 0.6529 0.044 Uiso 1 1 calc R . .
H9C H 0.5585 0.5346 0.6645 0.044 Uiso 1 1 calc R . .
C10 C 0.30743(12) 0.53445(7) 0.69934(6) 0.0300(3) Uani 1 1 d . . .
H10A H 0.3066 0.4886 0.7211 0.045 Uiso 1 1 calc R . .
H10B H 0.2186 0.5512 0.6935 0.045 Uiso 1 1 calc R . .
H10C H 0.3567 0.5654 0.7319 0.045 Uiso 1 1 calc R . .
C11 C 0.37366(12) 0.60218(6) 0.58794(7) 0.0282(2) Uani 1 1 d . . .
H11A H 0.4148 0.5989 0.5398 0.042 Uiso 1 1 calc R . .
H11B H 0.4231 0.6336 0.6199 0.042 Uiso 1 1 calc R . .
H11C H 0.2853 0.6194 0.5811 0.042 Uiso 1 1 calc R . .
C12 C 0.37021(10) 0.53160(6) 0.62381(6) 0.0225(2) Uani 1 1 d . . .
C13 C 0.16992(11) 0.49858(6) 0.54991(6) 0.0233(2) Uani 1 1 d . . .
C14 C 1.22800(12) 0.20071(7) 0.08828(7) 0.0337(3) Uani 1 1 d . . .
H14A H 1.2366 0.1651 0.1238 0.040 Uiso 1 1 calc R . .
C15 C 1.32747(13) 0.21359(8) 0.03980(8) 0.0409(3) Uani 1 1 d . . .
H15A H 1.4034 0.1864 0.0423 0.049 Uiso 1 1 calc R . .
C16 C 1.31723(14) 0.26531(8) -0.01193(8) 0.0408(3) Uani 1 1 d . . .
H16A H 1.3854 0.2737 -0.0450 0.049 Uiso 1 1 calc R . .
C17 C 1.20635(14) 0.30488(7) -0.01505(7) 0.0385(3) Uani 1 1 d . . .
H17A H 1.1988 0.3407 -0.0503 0.046 Uiso 1 1 calc R . .
C18 C 1.10689(13) 0.29261(6) 0.03263(7) 0.0323(3) Uani 1 1 d . . .
H18A H 1.0316 0.3202 0.0299 0.039 Uiso 1 1 calc R . .
C19 C 1.11544(11) 0.24010(6) 0.08489(6) 0.0268(2) Uani 1 1 d . . .
C20 C 1.00755(11) 0.22624(6) 0.13318(6) 0.0243(2) Uani 1 1 d . . .
C21 C 0.88478(12) 0.24987(6) 0.13093(6) 0.0257(2) Uani 1 1 d . . .
H21A H 0.8507 0.2822 0.0965 0.031 Uiso 1 1 calc R . .
C22 C 0.62025(13) 0.28127(7) 0.15132(8) 0.0409(3) Uani 1 1 d . . .
H22A H 0.6276 0.2661 0.0999 0.061 Uiso 1 1 calc R . .
H22B H 0.6675 0.3242 0.1584 0.061 Uiso 1 1 calc R . .
H22C H 0.5291 0.2883 0.1624 0.061 Uiso 1 1 calc R . .
C23 C 0.60979(13) 0.15928(7) 0.18886(9) 0.0429(3) Uani 1 1 d . . .
H23A H 0.6199 0.1459 0.1371 0.064 Uiso 1 1 calc R . .
H23B H 0.5178 0.1637 0.1993 0.064 Uiso 1 1 calc R . .
H23C H 0.6485 0.1244 0.2212 0.064 Uiso 1 1 calc R . .
C24 C 0.66462(16) 0.25137(9) 0.28260(8) 0.0520(4) Uani 1 1 d . . .
H24A H 0.7093 0.2952 0.2891 0.078 Uiso 1 1 calc R . .
H24B H 0.7036 0.2174 0.3161 0.078 Uiso 1 1 calc R . .
H24C H 0.5732 0.2570 0.2939 0.078 Uiso 1 1 calc R . .
C25 C 0.67682(12) 0.22737(6) 0.20278(6) 0.0294(3) Uani 1 1 d . . .
C26 C 0.89844(12) 0.17529(6) 0.22513(6) 0.0261(2) Uani 1 1 d . . .
C27 C -0.16849(12) 0.99843(7) 0.40638(7) 0.0347(3) Uani 1 1 d . . .
H27A H -0.1805 1.0354 0.3729 0.042 Uiso 1 1 calc R . .
C28 C -0.26850(14) 0.97885(8) 0.45191(8) 0.0432(3) Uani 1 1 d . . .
H28A H -0.3481 1.0029 0.4497 0.052 Uiso 1 1 calc R . .
C29 C -0.25291(14) 0.92462(8) 0.50034(7) 0.0395(3) Uani 1 1 d . . .
H29A H -0.3220 0.9110 0.5307 0.047 Uiso 1 1 calc R . .
C30 C -0.13664(14) 0.89046(7) 0.50429(7) 0.0360(3) Uani 1 1 d . . .
H30A H -0.1253 0.8533 0.5376 0.043 Uiso 1 1 calc R . .
C31 C -0.03658(13) 0.91023(6) 0.45985(7) 0.0306(3) Uani 1 1 d . . .
H31A H 0.0435 0.8867 0.4635 0.037 Uiso 1 1 calc R . .
C32 C -0.05066(11) 0.96398(6) 0.40978(6) 0.0252(2) Uani 1 1 d . . .
C33 C 0.05672(11) 0.98294(6) 0.36331(6) 0.0240(2) Uani 1 1 d . . .
C34 C 0.17031(12) 0.95110(6) 0.35267(7) 0.0297(3) Uani 1 1 d . . .
H34A H 0.1963 0.9089 0.3742 0.036 Uiso 1 1 calc R . .
C35 C 0.41984(17) 0.90683(9) 0.30628(12) 0.0639(5) Uani 1 1 d . . .
H35A H 0.3630 0.8721 0.2841 0.096 Uiso 1 1 calc R . .
H35B H 0.4153 0.9045 0.3603 0.096 Uiso 1 1 calc R . .
H35C H 0.5088 0.8986 0.2914 0.096 Uiso 1 1 calc R . .
C36 C 0.37912(15) 0.97985(8) 0.19569(8) 0.0474(4) Uani 1 1 d . . .
H36A H 0.3230 0.9439 0.1751 0.071 Uiso 1 1 calc R . .
H36B H 0.4676 0.9727 0.1793 0.071 Uiso 1 1 calc R . .
H36C H 0.3482 1.0245 0.1785 0.071 Uiso 1 1 calc R . .
C37 C 0.46405(13) 1.03212(9) 0.31411(8) 0.0455(4) Uani 1 1 d . . .
H37A H 0.4354 1.0772 0.2969 0.068 Uiso 1 1 calc R . .
H37B H 0.5532 1.0243 0.2993 0.068 Uiso 1 1 calc R . .
H37C H 0.4596 1.0300 0.3682 0.068 Uiso 1 1 calc R . .
C38 C 0.37693(12) 0.97735(7) 0.27998(7) 0.0342(3) Uani 1 1 d . . .
C39 C 0.17340(11) 1.04761(6) 0.28585(6) 0.0232(2) Uani 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 0.0033 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
C13 N1 C8 108.54(9) . . ?
C13 N1 C12 123.63(9) . . ?
C8 N1 C12 127.77(9) . . ?
C13 N2 C7 110.53(9) . . ?
C26 N3 C21 108.44(10) . . ?
C26 N3 C25 124.41(10) . . ?
C21 N3 C25 127.04(9) . . ?
C26 N4 C20 110.71(9) . . ?
C39 N5 C34 108.39(10) . . ?
C39 N5 C38 123.78(10) . . ?
C34 N5 C38 127.75(10) . . ?
C39 N6 C33 110.49(9) . . ?
C2 C1 C6 120.38(11) . . ?
C3 C2 C1 121.00(11) . . ?
C2 C3 C4 119.17(11) . . ?
C5 C4 C3 120.45(12) . . ?
C4 C5 C6 120.73(11) . . ?
C1 C6 C5 118.23(10) . . ?
C1 C6 C7 121.51(10) . . ?
C5 C6 C7 120.19(10) . . ?
C8 C7 N2 106.27(9) . . ?
C8 C7 C6 130.91(10) . . ?
N2 C7 C6 122.75(9) . . ?
C7 C8 N1 108.49(9) . . ?
N1 C12 C9 109.02(9) . . ?
N1 C12 C10 108.55(9) . . ?
C9 C12 C10 110.16(9) . . ?
N1 C12 C11 108.94(9) . . ?
C9 C12 C11 108.95(10) . . ?
C10 C12 C11 111.18(10) . . ?
O1 C13 N2 126.98(10) . . ?
O1 C13 N1 126.87(10) . . ?
N2 C13 N1 106.16(9) . . ?
C15 C14 C19 120.11(13) . . ?
C16 C15 C14 120.87(13) . . ?
C15 C16 C17 119.23(13) . . ?
C18 C17 C16 120.51(13) . . ?
C17 C18 C19 120.92(13) . . ?
C18 C19 C14 118.36(12) . . ?
C18 C19 C20 120.24(11) . . ?
C14 C19 C20 121.38(11) . . ?
C21 C20 N4 105.90(10) . . ?
C21 C20 C19 130.60(11) . . ?
N4 C20 C19 123.43(10) . . ?
C20 C21 N3 108.83(10) . . ?
N3 C25 C22 108.93(10) . . ?
N3 C25 C23 108.37(10) . . ?
C22 C25 C23 109.87(11) . . ?
N3 C25 C24 108.26(10) . . ?
C22 C25 C24 109.07(11) . . ?
C23 C25 C24 112.26(12) . . ?
O2 C26 N4 126.90(11) . . ?
O2 C26 N3 126.98(11) . . ?
N4 C26 N3 106.12(10) . . ?
C28 C27 C32 120.22(12) . . ?
C29 C28 C27 120.54(13) . . ?
C30 C29 C28 119.63(13) . . ?
C29 C30 C31 120.05(12) . . ?
C30 C31 C32 121.37(12) . . ?
C31 C32 C27 118.18(11) . . ?
C31 C32 C33 119.80(11) . . ?
C27 C32 C33 122.03(11) . . ?
C34 C33 N6 106.09(10) . . ?
C34 C33 C32 130.11(11) . . ?
N6 C33 C32 123.77(10) . . ?
C33 C34 N5 108.64(10) . . ?
N5 C38 C37 107.65(11) . . ?
N5 C38 C35 109.27(11) . . ?
C37 C38 C35 110.23(13) . . ?
N5 C38 C36 109.30(11) . . ?
C37 C38 C36 111.09(12) . . ?
C35 C38 C36 109.27(13) . . ?
O3 C39 N6 126.82(10) . . ?
O3 C39 N5 126.79(11) . . ?
N6 C39 N5 106.39(10) . . ?
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 C13 1.2498(14) . ?
O2 C26 1.2507(14) . ?
O3 C39 1.2512(14) . ?
N1 C13 1.3754(14) . ?
N1 C8 1.3939(14) . ?
N1 C12 1.4896(14) . ?
N2 C13 1.3583(14) . ?
N2 C7 1.3924(14) . ?
N3 C26 1.3761(14) . ?
N3 C21 1.3913(15) . ?
N3 C25 1.4900(15) . ?
N4 C26 1.3566(15) . ?
N4 C20 1.3946(14) . ?
N5 C39 1.3704(14) . ?
N5 C34 1.3956(16) . ?
N5 C38 1.4880(16) . ?
N6 C39 1.3549(15) . ?
N6 C33 1.3948(14) . ?
C1 C2 1.3846(17) . ?
C1 C6 1.4000(15) . ?
C2 C3 1.3831(19) . ?
C3 C4 1.3883(18) . ?
C4 C5 1.3844(16) . ?
C5 C6 1.4026(16) . ?
C6 C7 1.4599(15) . ?
C7 C8 1.3532(15) . ?
C9 C12 1.5249(16) . ?
C10 C12 1.5271(16) . ?
C11 C12 1.5271(16) . ?
C14 C15 1.3913(19) . ?
C14 C19 1.3983(18) . ?
C15 C16 1.381(2) . ?
C16 C17 1.386(2) . ?
C17 C18 1.3798(18) . ?
C18 C19 1.3975(17) . ?
C19 C20 1.4596(17) . ?
C20 C21 1.3531(17) . ?
C22 C25 1.5157(17) . ?
C23 C25 1.5214(19) . ?
C24 C25 1.5255(18) . ?
C27 C28 1.3920(19) . ?
C27 C32 1.3949(18) . ?
C28 C29 1.383(2) . ?
C29 C30 1.378(2) . ?
C30 C31 1.3815(19) . ?
C31 C32 1.3935(17) . ?
C32 C33 1.4576(17) . ?
C33 C34 1.3495(17) . ?
C35 C38 1.5232(19) . ?
C36 C38 1.5253(19) . ?
C37 C38 1.523(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658957
