#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:52:38 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/79/2007971.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2007971
loop_
_publ_author_name
'Lowe, Philip R.'
'Schwalbe, Carl H.'
_publ_section_title
;
 Classical Packing and Stacking in 6-Phenyl-5-azauracil
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1936
_journal_page_last               1938
_journal_paper_doi               10.1107/S010827019800969X
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C9 H7 N3 O2'
_chemical_formula_weight         189.18
_chemical_melting_point          566.5(5)
_chemical_name_common            6-phenyl-5-azauracil
_chemical_name_systematic
;
 6-phenyl-1,3,5-triazin-2,4[1H,3H]-dione
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.050(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2990(10)
_cell_length_b                   7.279(3)
_cell_length_c                   12.4040(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.41
_cell_measurement_theta_min      8.68
_cell_volume                     839.6(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'DATRED (Brookhaven National Laboratory & Birmingham University, 1986)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and PLUTO (Motherwell & Clegg, 1978)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_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  0.028
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1921
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        1.4
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      1.50
_exptl_crystal_density_method    'flotation in butan-1-ol and CCl~4~'
_exptl_crystal_description       'Transparent lath'
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.171
_refine_ls_extinction_coef       0.054(4)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   1.042
_refine_ls_goodness_of_fit_obs   1.168
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_restrained_S_obs      1.168
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_obs          0.034
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.1588P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.096
_refine_ls_wR_factor_obs         0.093
_reflns_number_observed          1396
_reflns_number_total             1812
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            ka1294.cif
_cod_data_source_block           jrt
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '566-567K' was changed to '566.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '566-567K' was changed to '566.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.1588P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.1588P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2007971
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0260(5) 0.0399(6) 0.0226(5) -0.0046(4) 0.0017(4) -0.0017(4)
C2 0.0260(6) 0.0336(7) 0.0265(6) -0.0014(5) 0.0005(4) 0.0017(5)
N3 0.0276(5) 0.0420(7) 0.0252(5) -0.0076(5) -0.0012(4) 0.0006(5)
C4 0.0333(6) 0.0328(6) 0.0243(6) -0.0010(5) 0.0018(5) 0.0024(5)
N5 0.0302(5) 0.0374(6) 0.0255(5) -0.0048(5) 0.0040(4) 0.0000(4)
C6 0.0263(6) 0.0261(6) 0.0269(6) 0.0005(5) 0.0037(4) 0.0013(5)
O2 0.0281(5) 0.0649(7) 0.0287(4) -0.0113(4) 0.0033(3) 0.0005(4)
O4 0.0449(6) 0.0578(7) 0.0225(4) -0.0091(5) -0.0018(4) 0.0028(4)
C1' 0.0250(6) 0.0271(6) 0.0325(6) -0.0010(5) 0.0028(5) -0.0004(5)
C2' 0.0334(7) 0.0402(7) 0.0347(7) -0.0042(6) 0.0065(5) 0.0006(6)
C3' 0.0306(7) 0.0537(9) 0.0529(9) -0.0096(6) 0.0102(6) 0.0041(7)
C4' 0.0300(7) 0.0481(9) 0.0596(9) -0.0109(6) -0.0040(6) 0.0001(7)
C5' 0.0372(7) 0.0523(9) 0.0390(8) -0.0090(7) -0.0062(6) -0.0024(7)
C6' 0.0304(6) 0.0453(8) 0.0333(7) -0.0067(6) 0.0027(5) -0.0006(6)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.31895(10) 0.1863(2) 0.57491(8) 0.0295(3) Uani d . 1 . N
C2 0.18931(12) 0.1122(2) 0.54342(9) 0.0287(3) Uani d . 1 . C
N3 0.17708(11) 0.0871(2) 0.43500(8) 0.0316(3) Uani d . 1 . N
C4 0.28125(13) 0.1348(2) 0.36058(9) 0.0301(3) Uani d . 1 . C
N5 0.41208(11) 0.1956(2) 0.39967(8) 0.0311(3) Uani d . 1 . N
C6 0.42628(12) 0.2212(2) 0.50258(9) 0.0264(3) Uani d . 1 . C
O2 0.09549(9) 0.0749(2) 0.60795(7) 0.0405(3) Uani d . 1 . O
O4 0.25648(10) 0.1203(2) 0.26455(7) 0.0417(3) Uani d . 1 . O
C1' 0.56586(12) 0.2877(2) 0.54521(9) 0.0282(3) Uani d . 1 . C
C2' 0.67072(14) 0.3431(2) 0.47209(11) 0.0361(3) Uani d . 1 . C
C3' 0.80369(15) 0.4011(2) 0.50883(13) 0.0457(4) Uani d . 1 . C
C4' 0.8327(2) 0.4070(2) 0.61773(13) 0.0459(4) Uani d . 1 . C
C5' 0.7286(2) 0.3556(2) 0.69050(12) 0.0428(4) Uani d . 1 . C
C6' 0.59548(14) 0.2944(2) 0.65491(11) 0.0363(3) Uani d . 1 . C
H1 0.3217(16) 0.227(2) 0.6459(12) 0.044(4) Uiso d . 1 . H
H3 0.0969(18) 0.039(2) 0.4136(12) 0.044(4) Uiso d . 1 . H
H2' 0.6489(15) 0.340(2) 0.3969(12) 0.037(4) Uiso d . 1 . H
H3' 0.8742(19) 0.439(2) 0.4559(14) 0.054(5) Uiso d . 1 . H
H4' 0.927(2) 0.453(3) 0.6432(15) 0.060(5) Uiso d . 1 . H
H5' 0.7475(17) 0.365(3) 0.7689(14) 0.055(5) Uiso d . 1 . H
H6' 0.5254(17) 0.254(2) 0.7084(12) 0.048(4) Uiso d . 1 . H
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
C6 N1 C2 121.76(10)
C6 N1 H1 123.0(9)
C2 N1 H1 114.6(9)
O2 C2 N3 124.12(11)
O2 C2 N1 121.97(11)
N3 C2 N1 113.91(10)
C2 N3 C4 124.57(11)
C2 N3 H3 115.4(10)
C4 N3 H3 120.1(10)
O4 C4 N5 122.45(11)
O4 C4 N3 119.95(12)
N5 C4 N3 117.59(10)
C6 N5 C4 118.70(10)
N5 C6 N1 123.08(11)
N5 C6 C1' 119.11(10)
N1 C6 C1' 117.80(10)
C6' C1' C2' 119.32(12)
C6' C1' C6 122.27(11)
C2' C1' C6 118.41(11)
C3' C2' C1' 120.01(13)
C3' C2' H2' 121.3(9)
C1' C2' H2' 118.7(9)
C4' C3' C2' 120.46(13)
C4' C3' H3' 121.5(11)
C2' C3' H3' 118.0(10)
C3' C4' C5' 119.79(14)
C3' C4' H4' 119.8(11)
C5' C4' H4' 120.4(11)
C4' C5' C6' 120.45(13)
C4' C5' H5' 120.1(10)
C6' C5' H5' 119.4(10)
C5' C6' C1' 119.95(12)
C5' C6' H6' 118.5(9)
C1' C6' H6' 121.5(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 . 1.3665(14) yes
N1 C2 . 1.377(2) yes
N1 H1 . 0.93(2) ?
C2 O2 . 1.2153(14) yes
C2 N3 . 1.3619(15) yes
N3 C4 . 1.383(2) yes
N3 H3 . 0.86(2) ?
C4 O4 . 1.2176(15) yes
C4 N5 . 1.382(2) yes
N5 C6 . 1.2966(15) yes
C6 C1' . 1.482(2) yes
C1' C6' . 1.389(2) ?
C1' C2' . 1.392(2) ?
C2' C3' . 1.383(2) ?
C2' H2' . 0.954(15) ?
C3' C4' . 1.378(2) ?
C3' H3' . 0.97(2) ?
C4' C5' . 1.376(2) ?
C4' H4' . 0.99(2) ?
C5' C6' . 1.387(2) ?
C5' H5' . 0.99(2) ?
C6' H6' . 0.98(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O4 2 1.94(2) 2.8030(10) 153.0(10)
N3 H3 O2 3_556 1.99(2) 2.8450(10) 170(2)
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
_geom_torsion_publ_flag
C6 N1 C2 O2 177.33(12) ?
C6 N1 C2 N3 -3.1(2) ?
O2 C2 N3 C4 177.73(13) ?
N1 C2 N3 C4 -1.8(2) ?
C2 N3 C4 O4 -174.27(13) ?
C2 N3 C4 N5 6.6(2) ?
O4 C4 N5 C6 174.56(13) ?
N3 C4 N5 C6 -6.3(2) ?
C4 N5 C6 N1 1.7(2) ?
C4 N5 C6 C1' -179.58(11) ?
C2 N1 C6 N5 3.2(2) ?
C2 N1 C6 C1' -175.45(11) ?
N5 C6 C1' C6' -171.05(12) ?
N1 C6 C1' C6' 7.7(2) ?
N5 C6 C1' C2' 8.3(2) ?
N1 C6 C1' C2' -173.00(12) yes
C6' C1' C2' C3' 1.1(2) ?
C6 C1' C2' C3' -178.19(13) ?
C1' C2' C3' C4' -0.9(2) ?
C2' C3' C4' C5' -0.2(3) ?
C3' C4' C5' C6' 1.2(3) ?
C4' C5' C6' C1' -1.0(2) ?
C2' C1' C6' C5' -0.2(2) ?
C6 C1' C6' C5' 179.14(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 22469
2 PubChem 24036
