#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:47:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178824 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/78/4107883.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_4107883
loop_
_publ_author_name
'Baoguo Zhao'
'Haifeng Du'
'Yian Shi'
_publ_section_title
;
 A Cu(I)-Catalyzed C-H α-Amination of Esters. Direct Synthesis of
 Hydantoins
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7220
_journal_page_last               7221
_journal_paper_doi               10.1021/ja802242h
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C15 H18 N2 O3'
_chemical_formula_weight         274.31
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Bruker SHELXTL'
_cell_angle_alpha                90.00
_cell_angle_beta                 103.533(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4261(3)
_cell_length_b                   19.5939(6)
_cell_length_c                   7.9784(2)
_cell_measurement_reflns_used    6666
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.05
_cell_measurement_theta_min      2.82
_cell_volume                     1432.65(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker-Axs Apex2 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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21456
_diffrn_reflns_theta_full        33.21
_diffrn_reflns_theta_max         33.21
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       Cube
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0790P)²+0.0580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1540
_reflns_number_gt                3597
_reflns_number_total             5385
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja802242h-file005.cif
_cod_data_source_block           ys183
_cod_database_code               4107883
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.67112(10) 0.34771(5) -0.09952(13) 0.0134(2) Uani 1 1 d .
N2 N 0.47899(10) 0.35775(5) 0.02205(13) 0.0125(2) Uani 1 1 d .
O1 O 0.70849(10) 0.38987(5) 0.18089(12) 0.0234(2) Uani 1 1 d .
O2 O 0.56566(9) 0.27788(5) -0.33139(12) 0.0190(2) Uani 1 1 d .
O3 O 0.26750(9) 0.34320(5) 0.10026(13) 0.0204(2) Uani 1 1 d .
C1 C 0.62947(12) 0.36814(6) 0.05104(16) 0.0141(2) Uani 1 1 d .
C2 C 0.42171(12) 0.32208(6) -0.13963(15) 0.0128(2) Uani 1 1 d .
H2A H 0.3798 0.2770 -0.1172 0.015 Uiso 1 1 calc R
C3 C 0.55892(12) 0.31151(6) -0.20606(16) 0.0138(2) Uani 1 1 d .
C4 C 0.39274(13) 0.36369(6) 0.14222(16) 0.0153(2) Uani 1 1 d .
C5 C 0.45798(14) 0.39514(8) 0.31375(17) 0.0236(3) Uani 1 1 d .
H5A H 0.3852 0.3958 0.3836 0.035 Uiso 1 1 calc R
H5B H 0.4888 0.4419 0.2972 0.035 Uiso 1 1 calc R
H5C H 0.5427 0.3683 0.3729 0.035 Uiso 1 1 calc R
C6 C 0.82132(12) 0.35578(7) -0.13310(16) 0.0156(2) Uani 1 1 d .
C7 C 0.90377(14) 0.28874(8) -0.0878(2) 0.0265(3) Uani 1 1 d .
H7A H 0.9131 0.2786 0.0346 0.040 Uiso 1 1 calc R
H7B H 1.0011 0.2928 -0.1109 0.040 Uiso 1 1 calc R
H7C H 0.8500 0.2518 -0.1580 0.040 Uiso 1 1 calc R
C8 C 0.90444(15) 0.41441(8) -0.0271(2) 0.0282(3) Uani 1 1 d .
H8A H 0.9174 0.4045 0.0960 0.042 Uiso 1 1 calc R
H8B H 0.8490 0.4569 -0.0554 0.042 Uiso 1 1 calc R
H8C H 1.0002 0.4194 -0.0539 0.042 Uiso 1 1 calc R
C9 C 0.80372(14) 0.37360(8) -0.32306(18) 0.0239(3) Uani 1 1 d .
H9A H 0.7504 0.4167 -0.3484 0.036 Uiso 1 1 calc R
H9B H 0.7492 0.3373 -0.3947 0.036 Uiso 1 1 calc R
H9C H 0.9002 0.3783 -0.3481 0.036 Uiso 1 1 calc R
C10 C 0.31083(12) 0.36230(6) -0.27143(15) 0.0125(2) Uani 1 1 d .
C11 C 0.21636(12) 0.32733(6) -0.40461(16) 0.0149(2) Uani 1 1 d .
H11A H 0.2162 0.2789 -0.4063 0.018 Uiso 1 1 calc R
C12 C 0.12250(12) 0.36344(7) -0.53470(16) 0.0167(3) Uani 1 1 d .
H12A H 0.0588 0.3395 -0.6256 0.020 Uiso 1 1 calc R
C13 C 0.12143(13) 0.43436(7) -0.53245(17) 0.0172(3) Uani 1 1 d .
H13A H 0.0584 0.4589 -0.6226 0.021 Uiso 1 1 calc R
C14 C 0.21293(13) 0.46919(7) -0.39776(16) 0.0173(2) Uani 1 1 d .
H14A H 0.2104 0.5176 -0.3941 0.021 Uiso 1 1 calc R
C15 C 0.30817(13) 0.43326(6) -0.26833(16) 0.0158(2) Uani 1 1 d .
H15A H 0.3717 0.4573 -0.1774 0.019 Uiso 1 1 calc R
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
C3 N1 C1 110.11(10)
C3 N1 C6 123.86(10)
C1 N1 C6 125.64(9)
C1 N2 C4 127.18(10)
C1 N2 C2 111.61(10)
C4 N2 C2 119.51(10)
O1 C1 N2 126.42(12)
O1 C1 N1 126.56(11)
N2 C1 N1 107.01(9)
N2 C2 C10 114.66(10)
N2 C2 C3 101.81(9)
C10 C2 C3 109.43(10)
O2 C3 N1 127.18(11)
O2 C3 C2 125.04(10)
N1 C3 C2 107.77(10)
O3 C4 N2 117.75(11)
O3 C4 C5 123.52(12)
N2 C4 C5 118.73(11)
N1 C6 C7 108.34(10)
N1 C6 C9 108.16(9)
C7 C6 C9 111.30(12)
N1 C6 C8 111.15(11)
C7 C6 C8 110.42(11)
C9 C6 C8 107.46(11)
C15 C10 C11 119.55(11)
C15 C10 C2 121.26(10)
C11 C10 C2 119.06(11)
C12 C11 C10 120.00(12)
C11 C12 C13 120.31(11)
C14 C13 C12 119.74(11)
C13 C14 C15 120.11(12)
C14 C15 C10 120.26(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.3868(15)
N1 C1 1.4064(16)
N1 C6 1.5095(15)
N2 C1 1.3976(14)
N2 C4 1.3995(16)
N2 C2 1.4553(15)
O1 C1 1.2034(14)
O2 C3 1.2116(15)
O3 C4 1.2173(14)
C2 C10 1.5181(16)
C2 C3 1.5223(17)
C4 C5 1.4957(18)
C6 C7 1.5259(18)
C6 C9 1.5260(19)
C6 C8 1.5295(19)
C10 C15 1.3910(17)
C10 C11 1.3959(16)
C11 C12 1.3895(17)
C12 C13 1.3899(19)
C13 C14 1.3894(17)
C14 C15 1.3907(17)
