#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:40:52 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243551 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556197.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_1556197
loop_
_publ_author_name
'Chun, Yu Sung'
'Xuan, Zi'
'Kim, Ju Hyun'
'Lee, Sang-gi'
_publ_section_title
;
 An expedient and divergent tandem one-pot synthesis of
 pyrimidin-2,4-diones using the Blaise reaction intermediate.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3162
_journal_page_last               3165
_journal_paper_doi               10.1021/ol401389j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_name_common            'U-5 Dr Jun'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 102.5580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1596(3)
_cell_length_b                   9.7432(3)
_cell_length_c                   13.8929(4)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      28.2661
_cell_measurement_theta_min      2.5741
_cell_volume                     1474.44(7)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'Bruker APEX-II'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0092
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25573
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0395
_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)+(0.0577P)²+0.5002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                3365
_reflns_number_total             3644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401389j_si_002.cif
_cod_data_source_block           I
_cod_database_code               1556197
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N2 0.04283(7) 0.18278(8) 0.96509(6) 0.01904(18) Uani d . 1
H H2 -0.0146 0.123 0.94 0.023 Uiso calc R 1
N N1 0.21371(8) 0.24310(9) 1.08551(6) 0.02022(18) Uani d . 1
O O1 0.12278(6) 0.03286(7) 1.08698(5) 0.02188(17) Uani d . 1
O O2 0.31173(8) 0.44524(9) 1.07240(6) 0.0355(2) Uani d . 1
C C4 0.04207(9) 0.30774(10) 0.91691(7) 0.01901(19) Uani d . 1
C C12 -0.06045(9) 0.32245(10) 0.82947(7) 0.0197(2) Uani d . 1
C C13 -0.17788(9) 0.27603(11) 0.83306(8) 0.0228(2) Uani d . 1
H H13 -0.1922 0.238 0.8925 0.027 Uiso calc R 1
C C6 0.29568(9) 0.21159(11) 1.17897(7) 0.0214(2) Uani d . 1
C C1 0.12552(8) 0.14598(10) 1.04794(7) 0.01774(19) Uani d . 1
C C17 -0.04125(10) 0.37697(10) 0.74090(7) 0.0231(2) Uani d . 1
H H17 0.0379 0.409 0.7368 0.028 Uiso calc R 1
C C16 -0.13787(10) 0.38434(11) 0.65882(8) 0.0253(2) Uani d . 1
H H16 -0.1236 0.4214 0.5991 0.03 Uiso calc R 1
C C2 0.22566(10) 0.37020(11) 1.03846(8) 0.0234(2) Uani d . 1
C C14 -0.27394(10) 0.28481(11) 0.75079(8) 0.0254(2) Uani d . 1
H H14 -0.3534 0.2538 0.7549 0.03 Uiso calc R 1
C C15 -0.25502(10) 0.33857(11) 0.66221(8) 0.0248(2) Uani d . 1
C C5 0.13821(12) 0.54186(12) 0.90779(9) 0.0331(3) Uani d . 1
H H5A 0.1958 0.5393 0.8637 0.05 Uiso calc R 1
H H5B 0.1671 0.6081 0.9608 0.05 Uiso calc R 1
H H5C 0.0569 0.5694 0.8704 0.05 Uiso calc R 1
C C3 0.13032(10) 0.40203(10) 0.95138(7) 0.0227(2) Uani d . 1
C C7 0.37379(10) 0.09996(12) 1.18677(8) 0.0271(2) Uani d . 1
H H7 0.3772 0.0467 1.1301 0.033 Uiso calc R 1
C C18 -0.35848(12) 0.34360(15) 0.57202(9) 0.0375(3) Uani d . 1
H H18A -0.4015 0.4316 0.57 0.056 Uiso calc R 1
H H18B -0.416 0.2685 0.5747 0.056 Uiso calc R 1
H H18C -0.3251 0.334 0.5127 0.056 Uiso calc R 1
C C11 0.29050(11) 0.29125(12) 1.26052(8) 0.0289(2) Uani d . 1
H H11 0.2371 0.3682 1.2547 0.035 Uiso calc R 1
C C8 0.44745(11) 0.06597(13) 1.27802(9) 0.0343(3) Uani d . 1
H H8 0.501 -0.0108 1.2838 0.041 Uiso calc R 1
C C9 0.44254(12) 0.14397(14) 1.36011(9) 0.0372(3) Uani d . 1
H H9 0.4923 0.1204 1.4225 0.045 Uiso calc R 1
C C10 0.36515(13) 0.25644(14) 1.35143(9) 0.0368(3) Uani d . 1
H H10 0.3628 0.3105 1.4079 0.044 Uiso calc R 1
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 N2 C4 124.89(8)
C1 N1 C2 123.59(8)
C1 N1 C6 116.86(8)
C2 N1 C6 119.54(8)
C3 C4 N2 119.74(9)
C3 C4 C12 126.54(9)
N2 C4 C12 113.72(8)
C13 C12 C17 118.59(9)
C13 C12 C4 120.11(9)
C17 C12 C4 121.24(9)
C14 C13 C12 120.83(9)
C7 C6 C11 120.95(10)
C7 C6 N1 120.07(9)
C11 C6 N1 118.93(10)
O1 C1 N2 122.16(8)
O1 C1 N1 121.99(9)
N2 C1 N1 115.85(8)
C16 C17 C12 120.08(10)
C17 C16 C15 121.48(10)
O2 C2 N1 119.37(10)
O2 C2 C3 124.38(10)
N1 C2 C3 116.24(8)
C13 C14 C15 120.74(10)
C16 C15 C14 118.27(9)
C16 C15 C18 121.08(10)
C14 C15 C18 120.63(11)
C4 C3 C2 119.42(9)
C4 C3 C5 125.05(10)
C2 C3 C5 115.52(9)
C6 C7 C8 119.70(11)
C6 C11 C10 118.78(11)
C9 C8 C7 119.95(12)
C8 C9 C10 119.97(11)
C9 C10 C11 120.65(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C1 1.3576(12)
N2 C4 1.3885(12)
N1 C1 1.3832(12)
N1 C2 1.4200(13)
N1 C6 1.4493(12)
O1 C1 1.2317(12)
O2 C2 1.2175(13)
C4 C3 1.3557(14)
C4 C12 1.4836(13)
C12 C13 1.3975(14)
C12 C17 1.3988(14)
C13 C14 1.3893(14)
C6 C7 1.3833(15)
C6 C11 1.3848(15)
C17 C16 1.3905(14)
C16 C15 1.3918(16)
C2 C3 1.4601(14)
C14 C15 1.3951(15)
C15 C18 1.5088(15)
C5 C3 1.5013(14)
C7 C8 1.3926(15)
C11 C10 1.3953(16)
C8 C9 1.3815(19)
C9 C10 1.384(2)
