#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:47:15 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179596 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/60/4506051.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_4506051
loop_
_publ_author_name
'Jarzembska, Katarzyna N.'
'Kubsik, Marcin'
'Kamiński, Radosław'
'Woźniak, Krzysztof'
'Dominiak, Paulina M.'
_publ_section_title
;
 From a Single Molecule to Molecular Crystal Architectures: Structural and
 Energetic Studies of Selected Uracil Derivatives
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2508
_journal_paper_doi               10.1021/cg300129z
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C6 H8 N2 O2'
_chemical_formula_sum            'C6 H8 N2 O2'
_chemical_formula_weight         140.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 91.743(7)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   7.1769(5)
_cell_length_b                   12.1325(7)
_cell_length_c                   7.5571(6)
_cell_measurement_temperature    100(2)
_cell_volume                     657.72(8)
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device
'Agilent Technologies KM4CCD κ-axis diffractometer'
_diffrn_measurement_device_type  'Opal CCD detector'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11143
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         45.786
_diffrn_reflns_theta_min         3.299
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Absorption correction done by SORTAV
 Blessing, R. H.: (1995) Acta Cryst. A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       unspecified
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         +0.23
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.389
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    0
_refine_ls_number_parameters     123
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
w=1/[σ²(Fo)]
;
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0308
_refine_ls_wR_factor_ref         0.0308
_reflns_number_gt                3592
_reflns_number_total             5486
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            cg300129z_si_012.cif
_cod_data_source_block           15dmU
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4506051
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_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_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N N3 0.70121(5) 0.06252(3) 0.89249(5) 0.01582(4) Uani 1 d . .
H H3 0.6544(10) -0.0133(3) 0.9330(9) 0.0238(3) Uiso 1 d D U
N N1 0.93271(5) 0.16529(3) 0.75709(5) 0.01735(4) Uani 1 d . .
C C2 0.86895(6) 0.06242(3) 0.80786(5) 0.01702(5) Uani 1 d . .
C C6 0.83344(6) 0.25915(3) 0.79295(5) 0.01599(5) Uani 1 d . .
H H6 0.8944(8) 0.3359(3) 0.7499(8) 0.0196(3) Uiso 1 d D U
C C4 0.59364(6) 0.15364(3) 0.92865(5) 0.01378(4) Uani 1 d . .
C C5 0.66833(6) 0.25833(3) 0.87660(5) 0.01462(4) Uani 1 d . .
O O2 0.95265(5) -0.02340(3) 0.77853(5) 0.02620(5) Uani 1 d . .
O O4 0.44238(4) 0.14273(2) 1.00090(4) 0.01756(4) Uani 1 d . .
C C8 0.56263(7) 0.36141(3) 0.91575(6) 0.02077(6) Uani 1 d . .
H H8A 0.6393(8) 0.4319(3) 0.8709(8) 0.0258(3) Uiso 1 d D U
H H8B 0.5410(10) 0.3666(6) 1.0559(3) 0.0257(3) Uiso 1 d D U
H H8C 0.4275(4) 0.3593(5) 0.8500(8) 0.0258(3) Uiso 1 d D U
C C7 1.10972(6) 0.17057(4) 0.66440(6) 0.02285(5) Uani 1 d . .
H H7A 1.1372(9) 0.2552(2) 0.6312(9) 0.0282(4) Uiso 1 d D U
H H7B 1.099(1) 0.1229(4) 0.5443(5) 0.0282(4) Uiso 1 d D U
H H7C 1.2210(6) 0.1385(5) 0.7482(7) 0.0285(4) Uiso 1 d D U
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 'Su & Coppens, Acta. Cryst. (1997) A53, 749'
H H 0.0000 0.0000 'Su & Coppens, Acta. Cryst. (1997) A53, 749'
N N 0.0061 0.0033 'Su & Coppens, Acta. Cryst. (1997) A53, 749'
O O 0.0106 0.0060 'Su & Coppens, Acta. Cryst. (1997) A53, 749'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 C2 O2 121.58(4)
N3 C2 N1 115.28(4)
N3 C4 O4 120.34(4)
N3 C4 C5 115.97(3)
H3 N3 C2 115.7(4)
H3 N3 C4 117.9(4)
N1 C2 O2 123.14(5)
N1 C6 C5 123.34(5)
N1 C6 H6 115.9(3)
N1 C7 H7C 109.9(4)
N1 C7 H7B 109.7(4)
N1 C7 H7A 108.7(4)
C2 N1 C6 120.89(3)
C2 N1 C7 117.89(4)
C2 N3 C4 126.39(4)
C6 N1 C7 121.21(4)
C6 C5 C4 118.10(4)
C6 C5 C8 122.66(4)
H6 C6 C5 120.8(3)
C4 C5 C8 119.24(3)
C5 C4 O4 123.69(4)
C5 C8 H8C 110.1(4)
C5 C8 H8B 109.4(4)
C5 C8 H8A 109.5(3)
H8A C8 H8C 109.6(5)
H8A C8 H8B 110.7(5)
H8B C8 H8C 107.5(5)
H7A C7 H7C 110.1(5)
H7A C7 H7B 108.9(5)
H7B C7 H7C 109.5(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 C2 1.3803(5)
N3 C4 1.3805(5)
N3 H3 1.029(1)
N1 C2 1.3874(5)
N1 C6 1.3746(5)
N1 C7 1.4706(6)
C2 O2 1.2256(5)
C6 C5 1.3600(6)
C6 H6 1.083(1)
C4 O4 1.2370(5)
C4 C5 1.4381(5)
C5 C8 1.4969(6)
C8 H8C 1.077(1)
C8 H8B 1.077(1)
C8 H8A 1.077(1)
C7 H7C 1.076(1)
C7 H7B 1.077(1)
C7 H7A 1.077(1)
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 H3 O4 1.029(1) 1.794(2) 2.8218(5) 176.2(1) 3_657
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N3 C2 N1 C6 0.87(3)
N3 C2 N1 C7 -179.30(4)
N3 C4 C5 C6 1.77(3)
N3 C4 C5 C8 -178.31(4)
H3 N3 C2 O2 2.3(4)
H3 N3 C2 N1 -178.7(1)
H3 N3 C4 O4 -3.0(4)
H3 N3 C4 C5 177.4(1)
N1 C2 N3 C4 0.55(3)
N1 C6 C5 C4 -0.52(3)
N1 C6 C5 C8 179.57(4)
C2 N1 C6 C5 -0.88(4)
C2 N1 C6 H6 179.3(2)
C2 N1 C7 H7C -61.1(4)
C2 N1 C7 H7B 59.4(3)
C2 N1 C7 H7A 178.4(2)
C2 N3 C4 O4 177.80(4)
C2 N3 C4 C5 -1.87(3)
C6 N1 C2 O2 179.92(4)
C6 N1 C7 H7C 118.7(4)
C6 N1 C7 H7B -120.8(4)
C6 N1 C7 H7A -1.8(4)
C6 C5 C4 O4 -177.89(4)
C6 C5 C8 H8C 119.2(3)
C6 C5 C8 H8B -122.9(4)
C6 C5 C8 H8A -1.4(3)
H6 C6 N1 C7 -0.5(3)
H6 C6 C5 C4 179.3(1)
H6 C6 C5 C8 -0.6(3)
C4 N3 C2 O2 -178.50(4)
C4 C5 C8 H8C -60.7(4)
C4 C5 C8 H8B 57.2(4)
C4 C5 C8 H8A 178.7(2)
C5 C6 N1 C7 179.30(4)
O2 C2 N1 C7 -0.26(4)
O4 C4 C5 C8 2.03(3)
