#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/36/2233631.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_2233631
loop_
_publ_author_name
'He, Xue-Jun'
'Song, Jun-Song'
'Huang, Qin-Qin'
'Wang, De-Cai'
'Ou-yang, Ping-Kai'
_publ_section_title
;
 2-[(4,6-Dimethoxypyrimidin-2-yl)oxy]benzaldehyde
;
_journal_coeditor_code           SU2359
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o423
_journal_paper_doi               10.1107/S1600536812000840
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H12 N2 O4'
_chemical_formula_moiety         'C13 H12 N2 O4'
_chemical_formula_sum            'C13 H12 N2 O4'
_chemical_formula_weight         260.25
_chemical_name_systematic
;
2-[(4,6-Dimethoxypyrimidin-2-yl)oxy]benzaldehyde
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.87(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.9920(8)
_cell_length_b                   7.3670(15)
_cell_length_c                   20.885(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     612.0(2)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            2563
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.141
_refine_ls_abs_structure_details 'none; 1023 Friedel pairs merged'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2227
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0850P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                1790
_reflns_number_total             2227
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2359.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2233631
_cod_database_fobs_code          2233631
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 1.4553(7) 0.5127(4) 0.39674(15) 0.0925(11) Uani d . 1.000
O O2 0.8453(6) 0.7927(3) 0.27202(8) 0.0581(7) Uani d . 1.000
O O3 0.7500(5) 0.7425(3) 0.05537(8) 0.0591(8) Uani d . 1.000
O O4 1.2359(6) 1.2581(3) 0.15175(9) 0.0598(8) Uani d . 1.000
N N1 0.7955(6) 0.7671(3) 0.16578(10) 0.0457(8) Uani d . 1.000
N N2 1.0511(6) 1.0293(3) 0.21505(10) 0.0460(7) Uani d . 1.000
C C1 0.8229(7) 1.0480(4) 0.34509(13) 0.0503(9) Uani d . 1.000
C C2 0.9064(7) 1.1207(4) 0.40473(14) 0.0515(10) Uani d . 1.000
C C3 1.1033(7) 1.0252(4) 0.44989(14) 0.0518(10) Uani d . 1.000
C C4 1.2202(7) 0.8574(4) 0.43577(13) 0.0460(9) Uani d . 1.000
C C5 1.1421(7) 0.7798(4) 0.37569(12) 0.0413(8) Uani d . 1.000
C C6 0.9419(7) 0.8792(4) 0.33036(12) 0.0411(8) Uani d . 1.000
C C7 1.2647(9) 0.5998(4) 0.36179(17) 0.0638(11) Uani d . 1.000
C C8 0.9023(7) 0.8697(4) 0.21501(12) 0.0432(9) Uani d . 1.000
C C9 0.8461(7) 0.8376(4) 0.10859(12) 0.0444(9) Uani d . 1.000
C C10 0.9930(7) 1.0035(4) 0.10102(13) 0.0501(10) Uani d . 1.000
C C11 1.0929(7) 1.0950(4) 0.15650(13) 0.0433(8) Uani d . 1.000
C C12 0.5970(8) 0.5691(5) 0.06309(14) 0.0629(11) Uani d . 1.000
C C13 1.3137(9) 1.3609(4) 0.20875(15) 0.0583(11) Uani d . 1.000
H H1B 0.68640 1.11240 0.31480 0.0600 Uiso c R 1.000
H H2B 0.82900 1.23560 0.41460 0.0620 Uiso c R 1.000
H H3A 1.15740 1.07510 0.49040 0.0620 Uiso c R 1.000
H H4A 1.35410 0.79390 0.46680 0.0550 Uiso c R 1.000
H H7A 1.18890 0.54810 0.32260 0.0760 Uiso c R 1.000
H H10A 1.02300 1.05120 0.06070 0.0600 Uiso c R 1.000
H H12A 0.54180 0.51540 0.02160 0.0940 Uiso c R 1.000
H H12B 0.39590 0.58390 0.08470 0.0940 Uiso c R 1.000
H H12C 0.75070 0.49160 0.08810 0.0940 Uiso c R 1.000
H H13A 1.41400 1.47410 0.19800 0.0880 Uiso c R 1.000
H H13B 1.46830 1.29400 0.23750 0.0880 Uiso c R 1.000
H H13C 1.11130 1.38390 0.22920 0.0880 Uiso c R 1.000
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
C6 O2 C8 121.3(2) no
C9 O3 C12 117.9(2) no
C11 O4 C13 118.7(2) no
C8 N1 C9 114.3(2) no
C8 N2 C11 114.4(2) no
C2 C1 C6 119.6(3) no
C1 C2 C3 120.4(3) no
C2 C3 C4 120.3(3) no
C3 C4 C5 120.9(3) no
C4 C5 C6 118.0(3) no
C4 C5 C7 120.2(3) no
C6 C5 C7 121.9(3) no
O2 C6 C1 122.1(2) no
O2 C6 C5 116.9(3) no
C1 C6 C5 120.8(2) no
O1 C7 C5 125.2(3) no
O2 C8 N1 112.2(2) no
O2 C8 N2 118.8(2) no
N1 C8 N2 129.0(2) no
O3 C9 N1 119.0(3) no
O3 C9 C10 117.7(2) no
N1 C9 C10 123.3(2) no
C9 C10 C11 116.0(3) no
O4 C11 N2 118.7(2) no
O4 C11 C10 118.3(2) no
N2 C11 C10 123.0(3) no
C2 C1 H1B 120.00 no
C6 C1 H1B 120.00 no
C1 C2 H2B 120.00 no
C3 C2 H2B 120.00 no
C2 C3 H3A 120.00 no
C4 C3 H3A 120.00 no
C3 C4 H4A 120.00 no
C5 C4 H4A 120.00 no
O1 C7 H7A 117.00 no
C5 C7 H7A 117.00 no
C9 C10 H10A 122.00 no
C11 C10 H10A 122.00 no
O3 C12 H12A 109.00 no
O3 C12 H12B 109.00 no
O3 C12 H12C 109.00 no
H12A C12 H12B 109.00 no
H12A C12 H12C 109.00 no
H12B C12 H12C 109.00 no
O4 C13 H13A 109.00 no
O4 C13 H13B 109.00 no
O4 C13 H13C 110.00 no
H13A C13 H13B 109.00 no
H13A C13 H13C 110.00 no
H13B C13 H13C 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.196(5) no
O2 C6 1.400(3) no
O2 C8 1.355(3) no
O3 C9 1.342(3) no
O3 C12 1.431(4) no
O4 C11 1.338(4) no
O4 C13 1.423(4) no
N1 C8 1.318(3) no
N1 C9 1.334(3) no
N2 C8 1.317(4) no
N2 C11 1.339(3) no
C1 C2 1.371(4) no
C1 C6 1.375(4) no
C2 C3 1.370(4) no
C3 C4 1.362(4) no
C4 C5 1.390(4) no
C5 C6 1.394(4) no
C5 C7 1.451(4) no
C9 C10 1.371(4) no
C10 C11 1.370(4) no
C1 H1B 0.9300 no
C2 H2B 0.9300 no
C3 H3A 0.9300 no
C4 H4A 0.9300 no
C7 H7A 0.9300 no
C10 H10A 0.9300 no
C12 H12A 0.9600 no
C12 H12B 0.9600 no
C12 H12C 0.9600 no
C13 H13A 0.9600 no
C13 H13B 0.9600 no
C13 H13C 0.9600 no
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
C2 H2B O1 1_465 0.93 2.54 3.400(4) 154 yes
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
C8 O2 C6 C5 -126.4(3) no
C6 O2 C8 N1 179.6(2) no
C6 O2 C8 N2 -0.1(4) no
C8 O2 C6 C1 59.2(4) no
C12 O3 C9 C10 179.9(3) no
C12 O3 C9 N1 0.0(4) no
C13 O4 C11 C10 174.6(3) no
C13 O4 C11 N2 -4.8(4) no
C9 N1 C8 N2 -0.4(4) no
C8 N1 C9 O3 179.2(2) no
C8 N1 C9 C10 -0.7(4) no
C9 N1 C8 O2 179.9(2) no
C11 N2 C8 N1 1.0(4) no
C8 N2 C11 C10 -0.7(4) no
C11 N2 C8 O2 -179.3(3) no
C8 N2 C11 O4 178.7(3) no
C2 C1 C6 C5 1.0(4) no
C2 C1 C6 O2 175.3(3) no
C6 C1 C2 C3 -0.9(4) no
C1 C2 C3 C4 0.5(4) no
C2 C3 C4 C5 -0.2(4) no
C3 C4 C5 C6 0.3(4) no
C3 C4 C5 C7 -179.1(3) no
C4 C5 C6 O2 -175.2(3) no
C6 C5 C7 O1 174.6(3) no
C7 C5 C6 C1 178.6(3) no
C4 C5 C7 O1 -6.1(5) no
C4 C5 C6 C1 -0.7(4) no
C7 C5 C6 O2 4.1(4) no
O3 C9 C10 C11 -178.9(3) no
N1 C9 C10 C11 1.0(4) no
C9 C10 C11 N2 -0.2(4) no
C9 C10 C11 O4 -179.6(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 716981
