#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:47:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178824 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/78/4107882.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_4107882
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            'C17 H24 N2 O2'
_chemical_formula_weight         288.38
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 104.9510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.2815(3)
_cell_length_b                   10.8506(2)
_cell_length_c                   20.2006(3)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.27
_cell_measurement_theta_min      2.76
_cell_volume                     3236.14(10)
_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 0.914
_diffrn_measured_fraction_theta_max 0.95
_diffrn_measurement_device_type  'Bruker Apex2 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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            28041
_diffrn_reflns_theta_full        36.32
_diffrn_reflns_theta_max         36.32
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       cube
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.055
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         7172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0443
_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)+(0.0776P)²+1.0075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                5784
_reflns_number_total             7172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja802242h-file004.cif
_cod_data_source_block           ys174_0m
_cod_database_code               4107882
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.15613(5) 0.54166(5) 0.42890(3) 0.02065(12) Uani 1 1 d .
O2 O 0.12210(5) 0.81930(6) 0.25360(3) 0.02334(13) Uani 1 1 d .
N1 N 0.16843(5) 0.66860(5) 0.33780(3) 0.01487(11) Uani 1 1 d .
N2 N 0.09966(4) 0.74098(5) 0.41733(3) 0.01420(11) Uani 1 1 d .
C1 C 0.12476(5) 0.77418(7) 0.30942(3) 0.01582(13) Uani 1 1 d .
C2 C 0.07535(5) 0.82735(6) 0.35978(3) 0.01464(12) Uani 1 1 d .
H2A H 0.0086 0.8216 0.3388 0.018 Uiso 1 1 calc R
C3 C 0.14251(5) 0.64025(6) 0.39910(3) 0.01459(12) Uani 1 1 d .
C4 C 0.21636(6) 0.57906(7) 0.30208(4) 0.01722(13) Uani 1 1 d .
C5 C 0.14477(8) 0.49224(9) 0.25930(5) 0.0327(2) Uani 1 1 d .
H5A H 0.0993 0.5404 0.2264 0.049 Uiso 1 1 calc R
H5B H 0.1154 0.4468 0.2896 0.049 Uiso 1 1 calc R
H5C H 0.1738 0.4339 0.2346 0.049 Uiso 1 1 calc R
C6 C 0.26531(8) 0.64895(9) 0.25643(6) 0.0344(2) Uani 1 1 d .
H6A H 0.2212 0.6968 0.2223 0.052 Uiso 1 1 calc R
H6B H 0.2958 0.5901 0.2331 0.052 Uiso 1 1 calc R
H6C H 0.3102 0.7047 0.2847 0.052 Uiso 1 1 calc R
C7 C 0.28867(6) 0.50640(8) 0.35414(4) 0.02265(16) Uani 1 1 d .
H7A H 0.3339 0.5635 0.3808 0.034 Uiso 1 1 calc R
H7B H 0.3182 0.4480 0.3299 0.034 Uiso 1 1 calc R
H7C H 0.2601 0.4612 0.3850 0.034 Uiso 1 1 calc R
C8 C 0.04227(5) 0.72775(6) 0.46692(3) 0.01544(12) Uani 1 1 d .
C9 C 0.00283(6) 0.85360(7) 0.47703(4) 0.02150(15) Uani 1 1 d .
H9A H -0.0356 0.8828 0.4332 0.032 Uiso 1 1 calc R
H9B H 0.0522 0.9124 0.4940 0.032 Uiso 1 1 calc R
H9C H -0.0335 0.8464 0.5104 0.032 Uiso 1 1 calc R
C10 C -0.03481(6) 0.63668(8) 0.43851(4) 0.02363(16) Uani 1 1 d .
H10A H -0.0714 0.6663 0.3942 0.035 Uiso 1 1 calc R
H10B H -0.0730 0.6297 0.4706 0.035 Uiso 1 1 calc R
H10C H -0.0094 0.5557 0.4326 0.035 Uiso 1 1 calc R
C11 C 0.10204(6) 0.68529(7) 0.53647(4) 0.01980(14) Uani 1 1 d .
H11A H 0.1506 0.7454 0.5531 0.030 Uiso 1 1 calc R
H11B H 0.1285 0.6048 0.5312 0.030 Uiso 1 1 calc R
H11C H 0.0651 0.6786 0.5694 0.030 Uiso 1 1 calc R
C12 C 0.09999(5) 0.96157(6) 0.37536(3) 0.01526(12) Uani 1 1 d .
C13 C 0.04183(6) 1.05226(7) 0.33945(4) 0.01752(13) Uani 1 1 d .
H13A H -0.0130 1.0293 0.3075 0.021 Uiso 1 1 calc R
C14 C 0.06435(7) 1.17666(7) 0.35057(4) 0.02227(16) Uani 1 1 d .
H14A H 0.0250 1.2381 0.3257 0.027 Uiso 1 1 calc R
C15 C 0.14403(7) 1.21109(7) 0.39791(4) 0.02452(17) Uani 1 1 d .
H15A H 0.1593 1.2957 0.4054 0.029 Uiso 1 1 calc R
C16 C 0.20135(7) 1.12032(8) 0.43429(5) 0.02433(16) Uani 1 1 d .
H16A H 0.2556 1.1434 0.4669 0.029 Uiso 1 1 calc R
C17 C 0.17951(6) 0.99584(7) 0.42302(4) 0.02010(14) Uani 1 1 d .
H17A H 0.2189 0.9345 0.4479 0.024 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C3 109.14(6)
C1 N1 C4 125.53(5)
C3 N1 C4 123.64(6)
C3 N2 C2 109.73(5)
C3 N2 C8 120.33(6)
C2 N2 C8 121.30(6)
O2 C1 N1 128.07(7)
O2 C1 C2 124.01(7)
N1 C1 C2 107.89(5)
N2 C2 C12 116.81(6)
N2 C2 C1 102.66(5)
C12 C2 C1 111.22(6)
O1 C3 N2 126.81(6)
O1 C3 N1 124.56(6)
N2 C3 N1 108.63(6)
N1 C4 C6 110.02(6)
N1 C4 C5 107.58(7)
C6 C4 C5 110.74(8)
N1 C4 C7 110.88(6)
C6 C4 C7 106.89(8)
C5 C4 C7 110.77(7)
N2 C8 C9 108.84(6)
N2 C8 C10 109.73(6)
C9 C8 C10 109.58(7)
N2 C8 C11 109.13(6)
C9 C8 C11 107.93(6)
C10 C8 C11 111.57(6)
C17 C12 C13 119.72(7)
C17 C12 C2 121.71(6)
C13 C12 C2 118.55(7)
C14 C13 C12 119.99(8)
C15 C14 C13 120.37(8)
C14 C15 C16 119.46(8)
C15 C16 C17 120.41(8)
C12 C17 C16 120.04(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.2187(8)
O2 C1 1.2203(8)
N1 C1 1.3744(9)
N1 C3 1.4277(9)
N1 C4 1.5079(9)
N2 C3 1.3723(9)
N2 C2 1.4646(9)
N2 C8 1.4989(9)
C1 C2 1.5278(10)
C2 C12 1.5168(10)
C4 C6 1.5299(12)
C4 C5 1.5308(13)
C4 C7 1.5326(11)
C8 C9 1.5275(10)
C8 C10 1.5312(12)
C8 C11 1.5356(10)
C12 C17 1.3922(12)
C12 C13 1.3971(10)
C13 C14 1.3968(11)
C14 C15 1.3914(14)
C15 C16 1.3948(13)
C16 C17 1.3959(12)
