#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/29/7102977.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_7102977
loop_
_publ_author_name
'Cui, Lu'
'Gadde, Suresh'
'Shukla, Atindra D'
'Sun, Hao'
'Mague, Joel T'
'Kaifer, Angel E'
_publ_section_title
;
 Dimerization of aromatic ureido pyrimidinedione derivatives:
 observation of an unexpected tautomer in the solid state.
;
_journal_issue                   12
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1446
_journal_page_last               1448
_journal_paper_doi               10.1039/b717285k
_journal_year                    2008
_chemical_formula_moiety         'C17 H18 N4 O3'
_chemical_formula_sum            'C17 H18 N4 O3'
_chemical_formula_weight         326.35
_chemical_name_systematic
;
1-(5,5-Diaalyl-4,6-dioxo-1,4,5,6-tetrahydropyrimidin-
2-yl)-3-phenylurea
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.003(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8599(5)
_cell_length_b                   16.4465(8)
_cell_length_c                   10.6945(5)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.35
_cell_volume                     1649.32(14)
_computing_cell_refinement       'Bruker APEX2 (Bruker-AXS, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'Bruker SAINT+ (Bruker-AXS, 2006a)'
_computing_molecular_graphics    'Bruker APEX2 (Bruker-AXS, 2006)'
_computing_publication_material  'Bruker APEX2 (Bruker-AXS, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      102(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-AXS Smart APEX 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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28739
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0407
_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)+(0.0448P)²+0.5796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                3275
_reflns_number_total             4112
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b717285k.txt
_cod_data_source_block           aek004_0m
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7102977
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.80221(10) 1.01593(6) 0.27948(9) 0.0260(2) Uani 1 1 d . . .
O2 O 0.51288(10) 0.85507(6) 0.02785(9) 0.0304(2) Uani 1 1 d . . .
O3 O 0.22639(10) 0.87281(6) 0.30807(9) 0.0294(2) Uani 1 1 d . . .
N1 N 0.85479(11) 1.08134(7) 0.47741(10) 0.0195(2) Uani 1 1 d . . .
N2 N 0.65050(11) 1.00495(7) 0.40596(10) 0.0186(2) Uani 1 1 d . . .
N3 N 0.57360(12) 0.92999(7) 0.21298(10) 0.0216(2) Uani 1 1 d . . .
N4 N 0.43572(11) 0.93966(6) 0.35986(10) 0.0192(2) Uani 1 1 d . . .
C1 C 0.98450(12) 1.12001(8) 0.48207(12) 0.0199(3) Uani 1 1 d . . .
C2 C 1.04742(14) 1.11554(9) 0.38213(13) 0.0284(3) Uani 1 1 d . . .
H2 H 1.0033 1.0852 0.3046 0.034 Uiso 1 1 calc R . .
C3 C 1.17549(15) 1.15589(10) 0.39708(15) 0.0335(3) Uani 1 1 d . . .
H3 H 1.2186 1.1524 0.3291 0.040 Uiso 1 1 calc R . .
C4 C 1.24162(14) 1.20093(9) 0.50846(15) 0.0311(3) Uani 1 1 d . . .
H4 H 1.3282 1.2290 0.5167 0.037 Uiso 1 1 calc R . .
C5 C 1.17901(14) 1.20430(9) 0.60776(15) 0.0303(3) Uani 1 1 d . . .
H5 H 1.2240 1.2343 0.6854 0.036 Uiso 1 1 calc R . .
C6 C 1.05163(14) 1.16445(8) 0.59542(14) 0.0264(3) Uani 1 1 d . . .
H6 H 1.0099 1.1674 0.6644 0.032 Uiso 1 1 calc R . .
C7 C 0.77448(13) 1.03382(7) 0.38034(12) 0.0192(2) Uani 1 1 d . . .
C8 C 0.54925(13) 0.95703(7) 0.32414(11) 0.0178(2) Uani 1 1 d . . .
C9 C 0.33173(13) 0.89242(8) 0.27687(12) 0.0205(3) Uani 1 1 d . . .
C10 C 0.33806(13) 0.86456(8) 0.14253(12) 0.0198(3) Uani 1 1 d . . .
C11 C 0.48065(13) 0.88061(8) 0.12118(12) 0.0213(3) Uani 1 1 d . . .
C12 C 0.30152(13) 0.77311(8) 0.12243(12) 0.0214(3) Uani 1 1 d . . .
H12A H 0.2027 0.7644 0.1240 0.026 Uiso 1 1 calc R . .
H12B H 0.3058 0.7564 0.0348 0.026 Uiso 1 1 calc R . .
C13 C 0.40075(14) 0.72067(8) 0.22543(13) 0.0252(3) Uani 1 1 d . . .
H13 H 0.3941 0.7231 0.3121 0.030 Uiso 1 1 calc R . .
C14 C 0.49652(15) 0.67141(9) 0.20385(15) 0.0318(3) Uani 1 1 d . . .
H14A H 0.5060 0.6675 0.1183 0.038 Uiso 1 1 calc R . .
H14B H 0.5561 0.6398 0.2738 0.038 Uiso 1 1 calc R . .
C15 C 0.22293(14) 0.91369(8) 0.03617(13) 0.0247(3) Uani 1 1 d . . .
H15A H 0.2212 0.8942 -0.0519 0.030 Uiso 1 1 calc R . .
H15B H 0.1282 0.9023 0.0462 0.030 Uiso 1 1 calc R . .
C16 C 0.24661(16) 1.00380(9) 0.04276(14) 0.0313(3) Uani 1 1 d . . .
H16 H 0.3245 1.0246 0.0180 0.038 Uiso 1 1 calc R . .
C17 C 0.16624(18) 1.05566(10) 0.08074(17) 0.0436(4) Uani 1 1 d . . .
H17A H 0.0876 1.0367 0.1061 0.052 Uiso 1 1 calc R . .
H17B H 0.1867 1.1122 0.0829 0.052 Uiso 1 1 calc R . .
H3N H 0.6564(18) 0.9441(10) 0.2045(16) 0.031(4) Uiso 1 1 d . . .
H2N H 0.6288(16) 1.0206(10) 0.4751(16) 0.026(4) Uiso 1 1 d . . .
H1N H 0.8240(17) 1.0914(10) 0.5443(16) 0.028(4) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 126.77(11) . . ?
C7 N1 H1N 118.1(11) . . ?
C1 N1 H1N 115.1(11) . . ?
C8 N2 C7 125.25(11) . . ?
C8 N2 H2N 113.2(10) . . ?
C7 N2 H2N 121.3(10) . . ?
C8 N3 C11 123.83(11) . . ?
C8 N3 H3N 115.1(11) . . ?
C11 N3 H3N 121.0(11) . . ?
C8 N4 C9 117.79(10) . . ?
C2 C1 C6 119.34(12) . . ?
C2 C1 N1 124.12(12) . . ?
C6 C1 N1 116.55(11) . . ?
C3 C2 C1 119.34(13) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 121.60(14) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.61(13) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 120.91(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 120.20(13) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 N1 125.44(11) . . ?
O1 C7 N2 122.01(11) . . ?
N1 C7 N2 112.55(10) . . ?
N4 C8 N2 117.34(11) . . ?
N4 C8 N3 125.25(11) . . ?
N2 C8 N3 117.41(11) . . ?
O3 C9 N4 119.92(11) . . ?
O3 C9 C10 117.42(11) . . ?
N4 C9 C10 122.62(11) . . ?
C11 C10 C9 113.51(10) . . ?
C11 C10 C12 109.61(10) . . ?
C9 C10 C12 110.32(10) . . ?
C11 C10 C15 107.43(10) . . ?
C9 C10 C15 107.35(10) . . ?
C12 C10 C15 108.45(10) . . ?
O2 C11 N3 120.25(12) . . ?
O2 C11 C10 123.72(11) . . ?
N3 C11 C10 115.98(10) . . ?
C13 C12 C10 112.73(10) . . ?
C13 C12 H12A 109.0 . . ?
C10 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C10 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 124.42(13) . . ?
C14 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C16 C15 C10 114.20(11) . . ?
C16 C15 H15A 108.7 . . ?
C10 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C10 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 123.89(16) . . ?
C17 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2277(15) . ?
O2 C11 1.2123(15) . ?
O3 C9 1.2282(15) . ?
N1 C7 1.3445(16) . ?
N1 C1 1.4153(15) . ?
N1 H1N 0.875(17) . ?
N2 C8 1.3577(15) . ?
N2 C7 1.4149(15) . ?
N2 H2N 0.870(16) . ?
N3 C8 1.3584(16) . ?
N3 C11 1.3811(16) . ?
N3 H3N 0.879(17) . ?
N4 C8 1.3210(16) . ?
N4 C9 1.3711(15) . ?
C1 C2 1.3937(18) . ?
C1 C6 1.3949(18) . ?
C2 C3 1.3913(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3863(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C9 C10 1.5275(17) . ?
C10 C11 1.5156(17) . ?
C10 C12 1.5460(17) . ?
C10 C15 1.5611(17) . ?
C12 C13 1.4995(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.318(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?
C15 C16 1.4986(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.311(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N O1 0.879(17) 1.842(17) 2.5676(14) 138.4(15) .
N2 H2N N4 0.870(16) 2.154(16) 3.0233(15) 177.1(14) 3_676
N1 H1N O3 0.875(17) 1.889(17) 2.7582(14) 171.6(15) 3_676
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21118636
