#------------------------------------------------------------------------------
#$Date: 2016-06-18 04:18:59 +0300 (Sat, 18 Jun 2016) $
#$Revision: 183678 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/17/2241721.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_2241721
loop_
_publ_author_name
'Sagar, Belakavadi K.'
'Yathirajan, Hemmige S.'
'Jasinski, Jerry P.'
'Glidewell, Christopher'
_publ_section_title
;
 Crystal structure of
 6-hydroxy-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4(3H)-one
;
_journal_coeditor_code           HB7590
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              969
_journal_page_last               971
_journal_paper_doi               10.1107/S2056989016009075
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C15 H12 N4 O4'
_chemical_formula_moiety         'C15 H12 N4 O4'
_chemical_formula_sum            'C15 H12 N4 O4'
_chemical_formula_weight         312.29
_chemical_name_systematic
;
6-Hydroxy-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4(3H)-one
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 105.412(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1863(9)
_cell_length_b                   10.7079(8)
_cell_length_c                   11.1726(8)
_cell_measurement_reflns_used    3266
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.20
_cell_measurement_theta_min      3.46
_cell_volume                     1405.48(19)
_computing_cell_refinement
;
CrysAlisPro (Agilent, 2014)
;
_computing_data_collection
;
CrysAlisPro (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlisPro (Agilent, 2014)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Agilent Xcalibur, Eos, Gemini CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7121
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         3.457
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0582P)²+0.1493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                2311
_reflns_number_total             3113
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7590sup1.cif
_cod_data_source_block           I
_cod_database_code               2241721
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.970
_shelxl_version_number           2.014
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_occupancy
N N11 0.18153(12) 0.35790(14) 0.63063(13) 0.0295(3) Uani d 1
H H11 0.1817(15) 0.3477(17) 0.7066(18) 0.035 Uiso d 1
C C12 0.14803(12) 0.47018(16) 0.58084(14) 0.0257(4) Uani d 1
N N13 0.15092(11) 0.50269(13) 0.46986(12) 0.0288(3) Uani d 1
C C14 0.19721(13) 0.41910(16) 0.40542(14) 0.0259(4) Uani d 1
C C15 0.23862(13) 0.30650(15) 0.45349(14) 0.0246(4) Uani d 1
C C16 0.22954(14) 0.26765(16) 0.57208(15) 0.0286(4) Uani d 1
O O14 0.20095(11) 0.45956(12) 0.29445(11) 0.0384(3) Uani d 1
H H14 0.2235(18) 0.405(2) 0.251(2) 0.058 Uiso d 1
O O15 0.29101(9) 0.22750(11) 0.38791(10) 0.0286(3) Uani d 1
O O16 0.26156(12) 0.16663(12) 0.62240(11) 0.0435(4) Uani d 1
N N21 0.10457(13) 0.51230(15) 0.77235(13) 0.0382(4) Uani d 1
C C22 0.11108(13) 0.55897(16) 0.66440(15) 0.0287(4) Uani d 1
N N23 0.09267(14) 0.67630(15) 0.62621(15) 0.0442(4) Uani d 1
C C24 0.06898(19) 0.7543(2) 0.7096(2) 0.0534(6) Uani d 1
H H24 0.0564 0.8380 0.6881 0.064 Uiso calc 1
C C25 0.06238(17) 0.7179(2) 0.8239(2) 0.0503(6) Uani d 1
H H25 0.0467 0.7743 0.8805 0.060 Uiso calc 1
C C26 0.07998(16) 0.5938(2) 0.85148(18) 0.0472(5) Uani d 1
H H26 0.0746 0.5653 0.9283 0.057 Uiso calc 1
C C31 0.41008(14) 0.22844(17) 0.42471(15) 0.0305(4) Uani d 1
C C32 0.46353(16) 0.1335(2) 0.37687(17) 0.0417(5) Uani d 1
C C33 0.58106(19) 0.1307(3) 0.4082(2) 0.0639(7) Uani d 1
H H33 0.6184 0.0678 0.3771 0.077 Uiso calc 1
C C34 0.64289(19) 0.2205(3) 0.4850(3) 0.0713(8) Uani d 1
H H34 0.7220 0.2185 0.5043 0.086 Uiso calc 1
C C35 0.59019(18) 0.3127(3) 0.5336(2) 0.0595(6) Uani d 1
H H35 0.6330 0.3720 0.5868 0.071 Uiso calc 1
C C36 0.47253(15) 0.3169(2) 0.50285(17) 0.0414(5) Uani d 1
H H36 0.4358 0.3795 0.5351 0.050 Uiso calc 1
O O32 0.39382(13) 0.05064(15) 0.30120(14) 0.0585(5) Uani d 1
C C37 0.4443(3) -0.0572(3) 0.2648(2) 0.0755(8) Uani d 1
H H37A 0.4889 -0.0336 0.2095 0.113 Uiso calc 1
H H37B 0.3857 -0.1143 0.2233 0.113 Uiso calc 1
H H37C 0.4923 -0.0968 0.3369 0.113 Uiso calc 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
_geom_angle_publ_flag
C12 N11 C16 123.44(14) ?
C12 N11 H11 116.5(13) ?
C16 N11 H11 119.4(13) ?
N13 C12 N11 123.65(15) ?
N13 C12 C22 121.28(15) ?
N11 C12 C22 115.02(14) ?
C12 N13 C14 116.70(14) ?
O14 C14 N13 113.69(14) n
O14 C14 C15 123.87(15) n
C15 C14 N13 122.41(14) ?
C14 C15 O15 120.54(13) ?
C14 C15 C16 120.98(15) ?
O15 C15 C16 118.47(14) ?
O16 C16 N11 121.35(15) ?
O16 C16 C15 126.03(16) ?
N11 C16 C15 112.61(14) ?
C14 O14 H14 114.2(16) ?
C22 N21 C26 115.78(17) ?
N23 C22 N21 127.09(16) ?
N23 C22 C12 117.26(15) ?
N21 C22 C12 115.59(15) ?
C22 N23 C24 114.59(17) ?
N23 C24 C25 123.6(2) ?
N23 C24 H24 118.2 ?
C25 C24 H24 118.2 ?
C24 C25 C26 116.47(19) ?
C24 C25 H25 121.8 ?
C26 C25 H25 121.8 ?
N21 C26 C25 122.44(19) ?
N21 C26 H26 118.8 ?
C25 C26 H26 118.8 ?
C36 C31 C32 120.81(17) ?
O15 C31 C32 115.95(15) n
O15 C31 C36 123.24(16) n
O32 C32 C31 116.00(16) n
O32 C32 C33 125.34(19) n
C15 O15 C31 115.41(12) n
C32 O32 C37 117.65(18) n
C33 C32 C31 118.7(2) ?
C34 C33 C32 120.2(2) ?
C34 C33 H33 119.9 ?
C32 C33 H33 119.9 ?
C35 C34 C33 121.1(2) ?
C35 C34 H34 119.4 ?
C33 C34 H34 119.4 ?
C34 C35 C36 119.4(2) ?
C34 C35 H35 120.3 ?
C36 C35 H35 120.3 ?
C31 C36 C35 119.9(2) ?
C31 C36 H36 120.1 ?
C35 C36 H36 120.1 ?
O32 C37 H37A 109.5 ?
O32 C37 H37B 109.5 ?
H37A C37 H37B 109.5 ?
O32 C37 H37C 109.5 ?
H37A C37 H37C 109.5 ?
H37B C37 H37C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N11 C12 1.342(2) n
N11 H11 0.86(2) ?
C12 N13 1.297(2) n
C12 C22 1.484(2) ?
N13 C14 1.361(2) n
C14 C15 1.361(2) n
C15 C16 1.421(2) n
C16 N11 1.381(2) n
C14 O14 1.3255(19) n
C15 O15 1.3816(18) ?
O14 H14 0.85(2) ?
O15 C31 1.3990(19) ?
N21 C22 1.327(2) n
C22 N23 1.327(2) n
N23 C24 1.339(2) n
C24 C25 1.358(3) n
C24 H24 0.9300 ?
C25 C26 1.368(3) n
C25 H25 0.9300 ?
C26 N21 1.332(2) n
C16 O16 1.234(2) n
C26 H26 0.9300 ?
C31 C36 1.373(3) ?
C31 C32 1.389(3) ?
C32 O32 1.357(2) ?
C32 C33 1.381(3) ?
C33 C34 1.373(4) ?
C33 H33 0.9300 ?
C34 C35 1.367(4) ?
C34 H34 0.9300 ?
C35 C36 1.384(3) ?
C35 H35 0.9300 ?
C36 H36 0.9300 ?
O32 C37 1.418(3) ?
C37 H37A 0.9600 ?
C37 H37B 0.9600 ?
C37 H37C 0.9600 ?
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_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N11 H11 O15 4_566 0.855(19) 2.257(19) 2.9733(18) 141.4(17) y
O14 H14 O16 4_565 0.85(2) 1.80(2) 2.6117(18) 160(2) y
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
C16 N11 C12 N13 4.3(2)
C16 N11 C12 C22 -173.20(14)
N11 C12 N13 C14 -4.0(2)
C22 C12 N13 C14 173.33(13)
C12 N13 C14 O14 -177.94(14)
C12 N13 C14 C15 0.1(2)
O14 C14 C15 O15 1.7(2)
N13 C14 C15 O15 -176.13(13)
O14 C14 C15 C16 -178.56(15)
N13 C14 C15 C16 3.6(2)
C12 N11 C16 O16 178.32(16)
C12 N11 C16 C15 -0.4(2)
C14 C15 C16 O16 178.06(17)
O15 C15 C16 O16 -2.2(3)
C14 C15 C16 N11 -3.2(2)
O15 C15 C16 N11 176.48(13)
C14 C15 O15 C31 100.24(17)
C16 C15 O15 C31 -79.49(18)
C26 N21 C22 N23 -2.0(3)
C26 N21 C22 C12 175.03(15)
N13 C12 C22 N23 -6.9(2)
N11 C12 C22 N23 170.67(15)
N13 C12 C22 N21 175.73(14)
N11 C12 C22 N21 -6.7(2)
N21 C22 N23 C24 2.4(3)
C12 C22 N23 C24 -174.60(16)
C22 N23 C24 C25 -0.9(3)
N23 C24 C25 C26 -0.8(3)
C22 N21 C26 C25 0.0(3)
C24 C25 C26 N21 1.3(3)
C15 O15 C31 C36 -12.1(2)
C15 O15 C31 C32 168.10(14)
C36 C31 C32 O32 179.61(17)
O15 C31 C32 O32 -0.6(2)
C36 C31 C32 C33 -0.8(3)
O15 C31 C32 C33 178.93(17)
O32 C32 C33 C34 179.5(2)
C31 C32 C33 C34 -0.1(3)
C32 C33 C34 C35 1.1(4)
C33 C34 C35 C36 -1.2(4)
C32 C31 C36 C35 0.7(3)
O15 C31 C36 C35 -179.05(17)
C34 C35 C36 C31 0.3(3)
C33 C32 O32 C37 9.3(3)
C31 C32 O32 C37 -171.21(19)

_cod_database_fobs_code 2241721
