#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:32:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178786 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/40/4104047.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_4104047
loop_
_publ_author_name
'J. Craig Ruble'
'Alexander R. Hurd'
'Timothy A. Johnson'
'Debra A. Sherry'
'Michael R. Barbachyn'
'Peter L. Toogood'
'Gordon L. Bundy'
'David R. Graber'
'Gregg M. Kamilar'
_publ_section_title
;
 Synthesis of (-)-PNU-286607 by Asymmetric Cyclization of Alkylidene
 Barbiturates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3991
_journal_page_last               3997
_journal_paper_doi               10.1021/ja808014h
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C17 H18 N4 O6'
_chemical_formula_weight         374.35
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.324(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.5453(7)
_cell_length_b                   10.6236(3)
_cell_length_c                   17.5931(6)
_cell_measurement_temperature    293(2)
_cell_volume                     3776.8(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10412
_diffrn_reflns_theta_full        58.87
_diffrn_reflns_theta_max         58.87
_diffrn_reflns_theta_min         4.38
_exptl_absorpt_coefficient_mu    0.859
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00016(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         2623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.864
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1926
_reflns_number_total             2623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808014h_si_001.cif
_cod_data_source_block           drg10a
_cod_database_code               4104047
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 0.10444(7) 0.19256(13) 0.05610(10) 0.0236(4) Uani 1 1 d .
O2 O 0.16725(7) 0.80606(14) -0.04511(10) 0.0256(4) Uani 1 1 d .
O3 O 0.23167(7) 0.39931(13) -0.02597(10) 0.0239(4) Uani 1 1 d .
O4 O 0.24243(9) 0.29426(15) -0.34494(11) 0.0360(5) Uani 1 1 d .
O5 O 0.27677(9) 0.10418(16) -0.30508(11) 0.0376(5) Uani 1 1 d .
O6 O 0.00587(7) 0.51141(14) -0.13232(10) 0.0264(4) Uani 1 1 d .
N1 N 0.11345(9) 0.19505(15) -0.09850(12) 0.0225(5) Uani 1 1 d .
N2 N 0.24532(10) 0.19859(18) -0.30335(13) 0.0261(5) Uani 1 1 d .
N3 N 0.08708(9) 0.65661(16) -0.08929(11) 0.0219(5) Uani 1 1 d .
H3A H 0.0579 0.7148 -0.1005 0.026 Uiso 1 1 calc R
N4 N 0.19815(9) 0.60125(16) -0.03380(12) 0.0216(5) Uani 1 1 d .
H4A H 0.2389 0.6240 -0.0079 0.026 Uiso 1 1 calc R
C1 C 0.14492(11) 0.30132(19) -0.19561(15) 0.0210(6) Uani 1 1 d .
C2 C 0.15225(11) 0.6944(2) -0.05582(15) 0.0208(6) Uani 1 1 d .
C3 C 0.20885(11) 0.0861(2) -0.21007(14) 0.0236(6) Uani 1 1 d .
H3B H 0.2296 0.0139 -0.2163 0.028 Uiso 1 1 calc R
C4 C 0.09777(11) 0.31102(19) -0.06506(15) 0.0209(6) Uani 1 1 d .
H4B H 0.0497 0.3112 -0.0846 0.025 Uiso 1 1 calc R
C5 C 0.14485(11) 0.19143(19) -0.14957(14) 0.0202(6) Uani 1 1 d .
C6 C 0.09355(12) 0.0822(2) -0.06812(15) 0.0243(6) Uani 1 1 d .
H6A H 0.1075 0.0082 -0.0882 0.029 Uiso 1 1 calc R
H6B H 0.0457 0.0801 -0.0913 0.029 Uiso 1 1 calc R
C7 C 0.21108(11) 0.1964(2) -0.25109(15) 0.0227(6) Uani 1 1 d .
C8 C 0.11467(10) 0.43395(19) -0.09862(14) 0.0192(5) Uani 1 1 d .
C9 C 0.12944(11) 0.30324(19) 0.03234(14) 0.0223(6) Uani 1 1 d .
H9A H 0.1776 0.2963 0.0544 0.027 Uiso 1 1 calc R
C10 C 0.09940(11) -0.0316(2) 0.06066(15) 0.0270(6) Uani 1 1 d .
H10A H 0.1202 -0.0299 0.1215 0.041 Uiso 1 1 calc R
H10B H 0.1105 -0.1087 0.0415 0.041 Uiso 1 1 calc R
H10C H 0.0523 -0.0264 0.0400 0.041 Uiso 1 1 calc R
C11 C 0.12330(11) 0.0784(2) 0.02767(15) 0.0237(6) Uani 1 1 d .
H11A H 0.1716 0.0749 0.0510 0.028 Uiso 1 1 calc R
C12 C 0.17620(11) 0.0833(2) -0.16049(14) 0.0217(6) Uani 1 1 d .
H12A H 0.1747 0.0088 -0.1336 0.026 Uiso 1 1 calc R
C13 C 0.11328(12) 0.4138(2) 0.07346(16) 0.0298(6) Uani 1 1 d .
H13A H 0.1347 0.4035 0.1339 0.045 Uiso 1 1 calc R
H13B H 0.0663 0.4185 0.0540 0.045 Uiso 1 1 calc R
H13C H 0.1286 0.4899 0.0586 0.045 Uiso 1 1 calc R
C14 C 0.17807(11) 0.3036(2) -0.24437(15) 0.0226(6) Uani 1 1 d .
H14A H 0.1786 0.3767 -0.2731 0.027 Uiso 1 1 calc R
C15 C 0.06432(11) 0.5349(2) -0.10645(14) 0.0215(6) Uani 1 1 d .
C16 C 0.18635(11) 0.4739(2) -0.04857(14) 0.0194(6) Uani 1 1 d .
C17 C 0.10462(11) 0.4107(2) -0.19118(14) 0.0219(6) Uani 1 1 d .
H17A H 0.0582 0.3946 -0.2275 0.026 Uiso 1 1 calc R
H17B H 0.1173 0.4857 -0.2119 0.026 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C9 O1 C11 111.74(17)
C5 N1 C6 123.28(17)
C5 N1 C4 124.80(17)
C6 N1 C4 111.89(18)
O4 N2 O5 122.2(2)
O4 N2 C7 119.26(19)
O5 N2 C7 118.59(19)
C2 N3 C15 126.23(19)
C2 N4 C16 126.95(19)
C14 C1 C5 120.8(2)
C14 C1 C17 122.2(2)
C5 C1 C17 117.0(2)
O2 C2 N4 122.6(2)
O2 C2 N3 121.1(2)
N4 C2 N3 116.3(2)
C12 C3 C7 120.2(2)
N1 C4 C9 108.94(17)
N1 C4 C8 114.17(19)
C9 C4 C8 113.50(17)
N1 C5 C12 123.41(19)
N1 C5 C1 118.85(19)
C12 C5 C1 117.7(2)
N1 C6 C11 111.87(18)
C3 C7 C14 120.1(2)
C3 C7 N2 119.9(2)
C14 C7 N2 119.9(2)
C16 C8 C15 114.49(18)
C16 C8 C4 113.17(18)
C15 C8 C4 109.18(18)
C16 C8 C17 105.91(17)
C15 C8 C17 105.04(17)
C4 C8 C17 108.52(17)
O1 C9 C13 106.71(18)
O1 C9 C4 108.56(17)
C13 C9 C4 113.66(19)
O1 C11 C10 107.88(18)
O1 C11 C6 108.06(17)
C10 C11 C6 113.08(19)
C3 C12 C5 121.0(2)
C1 C14 C7 120.0(2)
O6 C15 N3 120.8(2)
O6 C15 C8 122.09(19)
N3 C15 C8 116.87(19)
O3 C16 N4 121.0(2)
O3 C16 C8 122.18(19)
N4 C16 C8 116.74(19)
C1 C17 C8 111.48(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.444(2)
O1 C11 1.446(3)
O2 C2 1.225(2)
O3 C16 1.213(2)
O4 N2 1.237(2)
O5 N2 1.236(2)
O6 C15 1.214(2)
N1 C5 1.369(3)
N1 C6 1.462(3)
N1 C4 1.474(3)
N2 C7 1.439(3)
N3 C2 1.378(3)
N3 C15 1.375(3)
N4 C2 1.358(3)
N4 C16 1.381(3)
C1 C14 1.365(3)
C1 C5 1.421(3)
C1 C17 1.498(3)
C3 C12 1.369(3)
C3 C7 1.388(3)
C4 C9 1.539(3)
C4 C8 1.549(3)
C5 C12 1.406(3)
C6 C11 1.513(3)
C7 C14 1.394(3)
C8 C16 1.518(3)
C8 C15 1.523(3)
C8 C17 1.561(3)
C9 C13 1.507(3)
C10 C11 1.507(3)
