#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/86/2208632.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_2208632
loop_
_publ_author_name
'Yuan-Xiang Li'
'Yan-Ping Luo'
_publ_section_title
;
 Methyl 2,6-bis(4,6-dimethoxypyrimidin-2-yloxy)benzoate
;
_journal_coeditor_code           IS2008
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1323
_journal_page_last               o1325
_journal_paper_doi               10.1107/S1600536806008178
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H20 N4 O8'
_chemical_formula_moiety         'C20 H20 N4 O8'
_chemical_formula_sum            'C20 H20 N4 O8'
_chemical_formula_weight         444.40
_chemical_name_systematic
;
Methyl 2,6-bis(4,6-dimethoxypyrimidin-2-yloxy)benzoate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 122.753(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.00(3)
_cell_length_b                   7.776(7)
_cell_length_c                   22.34(2)
_cell_measurement_reflns_used    1421
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      21.59
_cell_measurement_theta_min      2.75
_cell_volume                     4237(7)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11217
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0499
_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)+(0.0542P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                2544
_reflns_number_total             4161
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2008.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2208632
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_refinement_flags
_atom_site_occupancy
C C1 0.06652(11) 0.4384(3) 0.36591(13) 0.0617(7) Uani d . 1
H H1A 0.0304 0.4193 0.3249 0.093 Uiso calc R 1
H H1B 0.0689 0.3918 0.4073 0.093 Uiso calc R 1
H H1C 0.0929 0.3828 0.3592 0.093 Uiso calc R 1
C C2 0.10270(14) 1.2182(3) 0.23053(15) 0.0759(9) Uani d . 1
H H2A 0.1258 1.1555 0.2196 0.114 Uiso calc R 1
H H2B 0.1173 1.3315 0.2466 0.114 Uiso calc R 1
H H2C 0.0664 1.2264 0.1886 0.114 Uiso calc R 1
C C3 0.07544(9) 0.7071(3) 0.32202(12) 0.0461(6) Uani d . 1
C C4 0.08795(11) 0.8797(3) 0.33215(13) 0.0558(7) Uani d . 1
H H4 0.0969 0.9365 0.3738 0.067 Uiso calc R 1
C C5 0.08631(10) 0.9629(3) 0.27630(13) 0.0481(6) Uani d . 1
C C6 0.06103(9) 0.7203(3) 0.21318(12) 0.0399(6) Uani d . 1
C C7 0.04014(9) 0.7082(3) 0.09303(11) 0.0387(5) Uani d . 1
C C8 -0.01177(10) 0.7078(3) 0.03292(12) 0.0505(6) Uani d . 1
H H8 -0.0410 0.6659 0.0347 0.061 Uiso calc R 1
C C9 -0.02026(10) 0.7699(3) -0.03023(13) 0.0533(7) Uani d . 1
H H9 -0.0555 0.7704 -0.0709 0.064 Uiso calc R 1
C C10 0.02295(10) 0.8311(3) -0.03356(12) 0.0468(6) Uani d . 1
H H10 0.0171 0.8723 -0.0762 0.056 Uiso calc R 1
C C11 0.07456(9) 0.8303(3) 0.02691(12) 0.0387(5) Uani d . 1
C C12 0.08490(9) 0.7716(3) 0.09262(11) 0.0357(5) Uani d . 1
C C13 0.14113(10) 0.7808(3) 0.15826(12) 0.0436(6) Uani d . 1
C C14 0.20985(12) 0.6274(4) 0.25767(15) 0.0907(11) Uani d . 1
H H14A 0.2358 0.6359 0.2437 0.136 Uiso calc R 1
H H14B 0.2151 0.5207 0.2822 0.136 Uiso calc R 1
H H14C 0.2151 0.7215 0.2886 0.136 Uiso calc R 1
C C15 0.16295(9) 0.8125(3) 0.04406(12) 0.0401(5) Uani d . 1
C C16 0.21137(10) 0.5705(3) 0.08429(12) 0.0431(6) Uani d . 1
C C17 0.25704(10) 0.6560(3) 0.09607(13) 0.0512(6) Uani d . 1
H H17 0.2910 0.6024 0.1165 0.061 Uiso calc R 1
C C18 0.24935(10) 0.8260(3) 0.07566(12) 0.0460(6) Uani d . 1
C C19 0.16735(11) 0.3135(3) 0.08546(15) 0.0689(8) Uani d . 1
H H19A 0.1509 0.3736 0.1069 0.103 Uiso calc R 1
H H19B 0.1768 0.1990 0.1044 0.103 Uiso calc R 1
H H19C 0.1418 0.3083 0.0349 0.103 Uiso calc R 1
C C20 0.28368(11) 1.0882(3) 0.05991(16) 0.0691(8) Uani d . 1
H H20A 0.2520 1.0943 0.0122 0.104 Uiso calc R 1
H H20B 0.3152 1.1294 0.0606 0.104 Uiso calc R 1
H H20C 0.2779 1.1580 0.0907 0.104 Uiso calc R 1
N N1 0.06231(7) 0.6225(2) 0.26262(9) 0.0429(5) Uani d . 1
N N2 0.07191(8) 0.8859(2) 0.21481(10) 0.0443(5) Uani d . 1
N N3 0.20236(8) 0.9094(2) 0.04937(10) 0.0442(5) Uani d . 1
N N4 0.16292(7) 0.6471(2) 0.05725(9) 0.0400(5) Uani d . 1
O O1 0.07756(7) 0.6202(2) 0.37546(8) 0.0571(5) Uani d . 1
O O2 0.10052(8) 1.1298(2) 0.28556(9) 0.0669(5) Uani d . 1
O O3 0.04586(6) 0.62940(19) 0.15297(8) 0.0458(4) Uani d . 1
O O4 0.17031(7) 0.9035(2) 0.17434(9) 0.0607(5) Uani d . 1
O O5 0.15474(6) 0.6337(2) 0.19496(8) 0.0539(5) Uani d . 1
O O6 0.11557(6) 0.90235(18) 0.01983(8) 0.0458(4) Uani d . 1
O O7 0.21589(7) 0.4028(2) 0.10073(9) 0.0569(5) Uani d . 1
O O8 0.29265(7) 0.9127(2) 0.08409(10) 0.0625(5) Uani d . 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
O1 C1 H1A 109.5 ?
O1 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
O1 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O2 C2 H2A 109.5 ?
O2 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
O2 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
N1 C3 O1 119.0(2) ?
N1 C3 C4 123.4(2) ?
O1 C3 C4 117.6(2) ?
C3 C4 C5 115.5(2) ?
C3 C4 H4 122.2 ?
C5 C4 H4 122.2 ?
N2 C5 O2 119.3(2) ?
N2 C5 C4 123.7(2) ?
O2 C5 C4 117.1(2) ?
N2 C6 N1 129.6(2) ?
N2 C6 O3 118.5(2) yes
N1 C6 O3 111.9(2) yes
C8 C7 C12 121.9(2) ?
C8 C7 O3 115.8(2) yes
C12 C7 O3 122.2(2) yes
C7 C8 C9 119.6(2) ?
C7 C8 H8 120.2 ?
C9 C8 H8 120.2 ?
C10 C9 C8 120.7(2) ?
C10 C9 H9 119.7 ?
C8 C9 H9 119.7 ?
C11 C10 C9 119.0(2) ?
C11 C10 H10 120.5 ?
C9 C10 H10 120.5 ?
C10 C11 O6 115.4(2) ?
C10 C11 C12 122.2(2) ?
O6 C11 C12 122.3(2) ?
C7 C12 C11 116.6(2) ?
C7 C12 C13 122.5(2) ?
C11 C12 C13 120.8(2) ?
O4 C13 O5 125.0(2) ?
O4 C13 C12 123.6(2) ?
O5 C13 C12 111.4(2) yes
O5 C14 H14A 109.5 ?
O5 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O5 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
N4 C15 N3 129.9(2) ?
N4 C15 O6 117.7(2) ?
N3 C15 O6 112.4(2) ?
N4 C16 O7 118.8(2) ?
N4 C16 C17 122.8(2) ?
O7 C16 C17 118.4(2) ?
C16 C17 C18 115.7(2) ?
C16 C17 H17 122.1 ?
C18 C17 H17 122.1 ?
N3 C18 O8 118.4(2) ?
N3 C18 C17 124.1(2) ?
O8 C18 C17 117.6(2) ?
O7 C19 H19A 109.5 ?
O7 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
O7 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
O8 C20 H20A 109.5 ?
O8 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
O8 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C6 N1 C3 114.1(2) ?
C6 N2 C5 113.6(2) ?
C15 N3 C18 113.2(2) ?
C15 N4 C16 114.1(2) ?
C3 O1 C1 117.55(19) ?
C5 O2 C2 118.78(19) ?
C6 O3 C7 121.62(19) ?
C13 O5 C14 115.3(2) ?
C15 O6 C11 119.01(18) ?
C16 O7 C19 117.84(19) ?
C18 O8 C20 117.2(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.440(3) yes
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 O2 1.439(3) ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 N1 1.338(3) ?
C3 O1 1.344(3) yes
C3 C4 1.377(3) ?
C4 C5 1.383(3) ?
C4 H4 0.9300 ?
C5 N2 1.341(3) ?
C5 O2 1.343(3) ?
C6 N2 1.321(3) ?
C6 N1 1.325(3) yes
C6 O3 1.364(3) yes
C7 C8 1.372(3) ?
C7 C12 1.393(3) ?
C7 O3 1.399(3) ?
C8 C9 1.381(3) ?
C8 H8 0.9300 ?
C9 C10 1.380(3) ?
C9 H9 0.9300 ?
C10 C11 1.370(3) ?
C10 H10 0.9300 ?
C11 O6 1.399(3) ?
C11 C12 1.406(3) ?
C12 C13 1.492(3) ?
C13 O4 1.194(3) yes
C13 O5 1.337(3) yes
C14 O5 1.448(3) ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 N4 1.319(3) ?
C15 N3 1.320(3) ?
C15 O6 1.366(3) ?
C16 N4 1.332(3) ?
C16 O7 1.342(3) ?
C16 C17 1.374(3) ?
C17 C18 1.377(3) ?
C17 H17 0.9300 ?
C18 N3 1.325(3) ?
C18 O8 1.345(3) ?
C19 O7 1.435(3) ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 O8 1.439(3) ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 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
C14 H14C O7 4 0.96 2.60 3.444(4) 147
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
N1 C3 C4 C5 -0.1(4)
O1 C3 C4 C5 178.7(2)
C3 C4 C5 N2 2.1(4)
C3 C4 C5 O2 -177.3(2)
C12 C7 C8 C9 0.7(4)
O3 C7 C8 C9 -174.6(2)
C7 C8 C9 C10 0.5(4)
C8 C9 C10 C11 -0.3(4)
C9 C10 C11 O6 -176.9(2)
C9 C10 C11 C12 -1.0(3)
C8 C7 C12 C11 -1.9(3)
O3 C7 C12 C11 173.05(18)
C8 C7 C12 C13 177.0(2)
O3 C7 C12 C13 -8.0(3)
C10 C11 C12 C7 2.1(3)
O6 C11 C12 C7 177.72(18)
C10 C11 C12 C13 -176.8(2)
O6 C11 C12 C13 -1.2(3)
C7 C12 C13 O4 -134.7(2)
C11 C12 C13 O4 44.1(3)
C7 C12 C13 O5 47.0(3)
C11 C12 C13 O5 -134.1(2)
N4 C16 C17 C18 -2.3(4)
O7 C16 C17 C18 177.6(2)
C16 C17 C18 N3 3.2(4)
C16 C17 C18 O8 -177.8(2)
N2 C6 N1 C3 1.7(3)
O3 C6 N1 C3 -178.14(18)
O1 C3 N1 C6 179.56(19)
C4 C3 N1 C6 -1.6(3)
N1 C6 N2 C5 0.1(3)
O3 C6 N2 C5 179.90(19)
O2 C5 N2 C6 177.3(2)
C4 C5 N2 C6 -2.1(3)
N4 C15 N3 C18 -4.0(3)
O6 C15 N3 C18 177.32(19)
O8 C18 N3 C15 -179.4(2)
C17 C18 N3 C15 -0.4(3)
N3 C15 N4 C16 4.8(3)
O6 C15 N4 C16 -176.57(19)
O7 C16 N4 C15 178.87(19)
C17 C16 N4 C15 -1.2(3)
N1 C3 O1 C1 1.3(3)
C4 C3 O1 C1 -177.7(2)
N2 C5 O2 C2 -3.4(4)
C4 C5 O2 C2 176.1(2)
N2 C6 O3 C7 -1.9(3)
N1 C6 O3 C7 178.00(18)
C8 C7 O3 C6 -116.0(2)
C12 C7 O3 C6 68.7(3)
O4 C13 O5 C14 -1.4(3)
C12 C13 O5 C14 176.8(2)
N4 C15 O6 C11 15.9(3)
N3 C15 O6 C11 -165.23(18)
C10 C11 O6 C15 -130.6(2)
C12 C11 O6 C15 53.6(3)
N4 C16 O7 C19 2.4(3)
C17 C16 O7 C19 -177.5(2)
N3 C18 O8 C20 -3.5(3)
C17 C18 O8 C20 177.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3767912
