#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/60/1506000.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_1506000
loop_
_publ_author_name
'Fritz, Jonathan A.'
'Nakhla, Josephine S.'
'Wolfe, John P.'
_publ_section_title
;
 A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of
 N-allylureas.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2531
_journal_page_last               2534
_journal_paper_doi               10.1021/ol060707b
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C36 H31 N3 O'
_chemical_formula_sum            'C36 H31 N3 O'
_chemical_formula_weight         521.64
_chemical_name_systematic
;
 ?
;
_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                 99.739(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.551(3)
_cell_length_b                   17.594(4)
_cell_length_c                   13.979(3)
_cell_measurement_reflns_used    5910
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.31
_cell_volume                     2800.0(11)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            54303
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2.10) Bruker/Siemens area
  detector absorption and other corrections, University of
  Gottingen, Germany 2003.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0416P)²+0.8492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                5006
_reflns_number_total             6969
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060707bsi20060322_075909.cif
_cod_data_source_block           jng
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1506000
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
O1 O 0.40462(8) 0.10582(6) -0.19506(6) 0.0291(2) Uani 1 1 d .
N1 N 0.49393(8) 0.11373(6) -0.03312(7) 0.0217(2) Uani 1 1 d .
N2 N 0.60615(8) 0.09537(6) -0.14613(7) 0.0215(2) Uani 1 1 d .
N3 N 1.01647(10) 0.13356(7) 0.34884(8) 0.0291(3) Uani 1 1 d .
C1 C 0.49148(10) 0.10493(7) -0.13196(8) 0.0210(2) Uani 1 1 d .
C2 C 0.68785(10) 0.09059(7) -0.05365(8) 0.0214(3) Uani 1 1 d .
H2A H 0.7039 0.0359 -0.0367 0.026 Uiso 1 1 calc R
C3 C 0.61411(10) 0.12511(8) 0.01712(9) 0.0235(3) Uani 1 1 d .
H3B H 0.6281 0.0983 0.0803 0.028 Uiso 1 1 calc R
H3C H 0.6317 0.1798 0.0280 0.028 Uiso 1 1 calc R
C4 C 0.39519(10) 0.13337(7) 0.00923(8) 0.0208(2) Uani 1 1 d .
C5 C 0.41030(11) 0.17621(7) 0.09428(9) 0.0256(3) Uani 1 1 d .
H5A H 0.4867 0.1918 0.1239 0.031 Uiso 1 1 calc R
C6 C 0.31318(12) 0.19599(8) 0.13559(10) 0.0305(3) Uani 1 1 d .
H6A H 0.3240 0.2248 0.1939 0.037 Uiso 1 1 calc R
C7 C 0.20090(12) 0.17435(8) 0.09313(10) 0.0311(3) Uani 1 1 d .
H7A H 0.1348 0.1893 0.1209 0.037 Uiso 1 1 calc R
C8 C 0.18645(11) 0.13053(8) 0.00942(10) 0.0277(3) Uani 1 1 d .
H8A H 0.1098 0.1149 -0.0197 0.033 Uiso 1 1 calc R
C9 C 0.28209(11) 0.10921(7) -0.03236(9) 0.0234(3) Uani 1 1 d .
H9A H 0.2711 0.0784 -0.0889 0.028 Uiso 1 1 calc R
C10 C 0.63220(10) 0.06435(7) -0.23467(8) 0.0220(3) Uani 1 1 d .
C11 C 0.58535(12) 0.09808(8) -0.32274(9) 0.0288(3) Uani 1 1 d .
H11A H 0.5387 0.1427 -0.3240 0.035 Uiso 1 1 calc R
C12 C 0.60713(13) 0.06617(9) -0.40884(9) 0.0347(3) Uani 1 1 d .
H12A H 0.5733 0.0882 -0.4692 0.042 Uiso 1 1 calc R
C13 C 0.67773(12) 0.00255(9) -0.40745(10) 0.0346(3) Uani 1 1 d .
H13A H 0.6924 -0.0189 -0.4666 0.042 Uiso 1 1 calc R
C14 C 0.72687(12) -0.02979(9) -0.31983(10) 0.0319(3) Uani 1 1 d .
H14A H 0.7764 -0.0730 -0.3188 0.038 Uiso 1 1 calc R
C15 C 0.70401(11) 0.00077(8) -0.23304(9) 0.0262(3) Uani 1 1 d .
H15A H 0.7374 -0.0217 -0.1729 0.031 Uiso 1 1 calc R
C16 C 0.80550(11) 0.13213(8) -0.05511(9) 0.0246(3) Uani 1 1 d .
H16A H 0.8534 0.0994 -0.0920 0.030 Uiso 1 1 calc R
C17 C 0.78860(13) 0.20837(9) -0.10734(10) 0.0351(3) Uani 1 1 d .
H17A H 0.7321 0.2391 -0.0792 0.053 Uiso 1 1 calc R
H17B H 0.7588 0.1999 -0.1764 0.053 Uiso 1 1 calc R
H17C H 0.8640 0.2351 -0.1000 0.053 Uiso 1 1 calc R
C18 C 0.86989(10) 0.13616(7) 0.04943(9) 0.0228(3) Uani 1 1 d .
C19 C 0.92136(11) 0.07075(8) 0.09446(9) 0.0250(3) Uani 1 1 d .
H19A H 0.9227 0.0256 0.0573 0.030 Uiso 1 1 calc R
C20 C 0.97069(11) 0.07001(8) 0.19227(9) 0.0264(3) Uani 1 1 d .
H20A H 1.0072 0.0252 0.2208 0.032 Uiso 1 1 calc R
C21 C 0.96648(10) 0.13502(8) 0.24833(9) 0.0251(3) Uani 1 1 d .
C22 C 0.91871(11) 0.20129(8) 0.20426(9) 0.0272(3) Uani 1 1 d .
H22A H 0.9181 0.2465 0.2413 0.033 Uiso 1 1 calc R
C23 C 0.87165(11) 0.20152(8) 0.10567(9) 0.0261(3) Uani 1 1 d .
H23A H 0.8400 0.2474 0.0762 0.031 Uiso 1 1 calc R
C24 C 0.94783(11) 0.13177(7) 0.41194(9) 0.0230(3) Uani 1 1 d .
C25 C 0.81668(11) 0.12825(7) 0.38467(8) 0.0228(3) Uani 1 1 d .
C26 C 0.76266(13) 0.06207(9) 0.34553(10) 0.0358(3) Uani 1 1 d .
H26A H 0.8088 0.0185 0.3378 0.043 Uiso 1 1 calc R
C27 C 0.64138(15) 0.05930(11) 0.31761(11) 0.0475(5) Uani 1 1 d .
H27A H 0.6049 0.0137 0.2913 0.057 Uiso 1 1 calc R
C28 C 0.57386(14) 0.12230(11) 0.32789(10) 0.0459(4) Uani 1 1 d .
H28A H 0.4911 0.1203 0.3082 0.055 Uiso 1 1 calc R
C29 C 0.62656(13) 0.18819(10) 0.36672(12) 0.0434(4) Uani 1 1 d .
H29A H 0.5801 0.2317 0.3737 0.052 Uiso 1 1 calc R
C30 C 0.74762(12) 0.19098(8) 0.39566(11) 0.0335(3) Uani 1 1 d .
H30A H 0.7834 0.2363 0.4232 0.040 Uiso 1 1 calc R
C31 C 1.00082(11) 0.13254(7) 0.51689(9) 0.0243(3) Uani 1 1 d .
C32 C 1.12219(12) 0.13990(8) 0.54524(10) 0.0316(3) Uani 1 1 d .
H32A H 1.1712 0.1438 0.4973 0.038 Uiso 1 1 calc R
C33 C 1.17160(14) 0.14156(9) 0.64272(11) 0.0385(4) Uani 1 1 d .
H33A H 1.2542 0.1465 0.6612 0.046 Uiso 1 1 calc R
C34 C 1.10112(15) 0.13600(8) 0.71320(10) 0.0384(4) Uani 1 1 d .
H34A H 1.1351 0.1381 0.7800 0.046 Uiso 1 1 calc R
C35 C 0.98121(14) 0.12744(8) 0.68624(10) 0.0370(3) Uani 1 1 d .
H35A H 0.9329 0.1229 0.7346 0.044 Uiso 1 1 calc R
C36 C 0.93073(13) 0.12543(8) 0.58841(9) 0.0304(3) Uani 1 1 d .
H36A H 0.8482 0.1192 0.5704 0.036 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
C1 N1 C4 124.26(10)
C1 N1 C3 110.63(9)
C4 N1 C3 122.27(10)
C1 N2 C10 121.15(10)
C1 N2 C2 111.69(9)
C10 N2 C2 122.82(10)
C24 N3 C21 118.93(11)
O1 C1 N2 126.11(11)
O1 C1 N1 126.55(11)
N2 C1 N1 107.34(10)
N2 C2 C3 101.57(9)
N2 C2 C16 113.38(10)
C3 C2 C16 113.96(10)
N1 C3 C2 102.81(9)
C5 C4 C9 119.40(11)
C5 C4 N1 119.73(11)
C9 C4 N1 120.86(11)
C6 C5 C4 119.76(12)
C7 C6 C5 121.07(13)
C6 C7 C8 118.97(12)
C9 C8 C7 121.00(12)
C8 C9 C4 119.75(12)
C15 C10 C11 119.96(11)
C15 C10 N2 120.33(11)
C11 C10 N2 119.71(11)
C12 C11 C10 119.60(13)
C13 C12 C11 120.51(13)
C14 C13 C12 119.89(12)
C13 C14 C15 120.21(13)
C10 C15 C14 119.79(12)
C17 C16 C18 114.86(11)
C17 C16 C2 112.38(11)
C18 C16 C2 107.25(10)
C23 C18 C19 117.53(11)
C23 C18 C16 122.55(12)
C19 C18 C16 119.69(11)
C20 C19 C18 121.61(12)
C19 C20 C21 119.91(12)
C22 C21 C20 119.29(12)
C22 C21 N3 121.10(12)
C20 C21 N3 119.53(12)
C21 C22 C23 120.04(12)
C18 C23 C22 121.50(12)
N3 C24 C31 118.55(11)
N3 C24 C25 122.80(11)
C31 C24 C25 118.64(11)
C30 C25 C26 118.87(13)
C30 C25 C24 120.98(11)
C26 C25 C24 120.13(12)
C25 C26 C27 120.28(15)
C28 C27 C26 120.28(14)
C27 C28 C29 119.89(14)
C28 C29 C30 120.03(16)
C25 C30 C29 120.64(14)
C36 C31 C32 118.79(12)
C36 C31 C24 120.87(12)
C32 C31 C24 120.34(12)
C33 C32 C31 120.50(14)
C34 C33 C32 120.31(14)
C35 C34 C33 119.82(13)
C34 C35 C36 120.30(14)
C35 C36 C31 120.27(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2188(14)
N1 C1 1.3858(15)
N1 C4 1.4140(15)
N1 C3 1.4597(15)
N2 C1 1.3823(15)
N2 C10 1.4306(15)
N2 C2 1.4683(15)
N3 C24 1.2823(16)
N3 C21 1.4261(16)
C2 C3 1.5356(16)
C2 C16 1.5462(17)
C4 C5 1.3935(17)
C4 C9 1.4030(17)
C5 C6 1.3901(18)
C6 C7 1.385(2)
C7 C8 1.3875(19)
C8 C9 1.3859(18)
C10 C15 1.3904(18)
C10 C11 1.3911(17)
C11 C12 1.3892(19)
C12 C13 1.383(2)
C13 C14 1.382(2)
C14 C15 1.3924(18)
C16 C17 1.5238(19)
C16 C18 1.5251(17)
C18 C23 1.3912(18)
C18 C19 1.3956(18)
C19 C20 1.3895(18)
C20 C21 1.3920(19)
C21 C22 1.3887(19)
C22 C23 1.3932(18)
C24 C31 1.4910(17)
C24 C25 1.4997(18)
C25 C30 1.3855(19)
C25 C26 1.3888(18)
C26 C27 1.390(2)
C27 C28 1.377(3)
C28 C29 1.377(2)
C29 C30 1.389(2)
C31 C36 1.3944(19)
C31 C32 1.3970(19)
C32 C33 1.3857(19)
C33 C34 1.384(2)
C34 C35 1.381(2)
C35 C36 1.3935(19)
