#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226817.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_2226817
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Yeap, Chin Sing'
'Rai, Sankappa'
'Isloor, Arun M.'
'Shetty, Prakash'
_publ_section_title
;
 4,6-Dimethoxy-2-(methylsulfonyl)pyrimidine
;
_journal_coeditor_code           CI5121
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1913
_journal_paper_doi               10.1107/S1600536810025067
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H10 N2 O4 S'
_chemical_formula_moiety         'C7 H10 N2 O4 S'
_chemical_formula_sum            'C7 H10 N2 O4 S'
_chemical_formula_weight         218.23
_chemical_name_systematic
;
4,6-Dimethoxy-2-(methylsulfonyl)pyrimidine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.457(8)
_cell_angle_beta                 92.774(8)
_cell_angle_gamma                98.504(8)
_cell_formula_units_Z            4
_cell_length_a                   8.349(2)
_cell_length_b                   11.067(3)
_cell_length_c                   11.438(3)
_cell_measurement_reflns_used    8362
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.12
_cell_measurement_theta_min      2.24
_cell_volume                     986.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29277
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.8885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.503
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         7063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0771P)²+0.1962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1560
_reflns_number_gt                4866
_reflns_number_total             7063
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5121.cif
_cod_data_source_block           I
_cod_original_cell_volume        986.4(4)
_cod_database_code               2226817
_cod_database_fobs_code          2226817
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1A -0.01034(4) 0.04422(4) 0.19330(4) 0.03856(12) Uani d . 1 . .
O O1A -0.02361(19) 0.10070(16) 0.32304(15) 0.0632(4) Uani d . 1 . .
O O2A -0.08995(15) 0.09457(13) 0.10934(15) 0.0518(3) Uani d . 1 . .
O O3A 0.50597(16) 0.29863(13) 0.14202(15) 0.0528(3) Uani d . 1 . .
O O4A 0.51835(16) -0.11116(13) 0.16945(16) 0.0543(3) Uani d . 1 . .
N N1A 0.26662(16) 0.17382(13) 0.16027(13) 0.0362(3) Uani d . 1 . .
N N2A 0.27464(15) -0.03547(13) 0.17789(13) 0.0364(3) Uani d . 1 . .
C C1A 0.20400(17) 0.06224(14) 0.17287(14) 0.0334(3) Uani d . 1 . .
C C2A 0.43408(19) -0.01755(16) 0.16718(16) 0.0386(3) Uani d . 1 . .
C C3A 0.51867(19) 0.09495(18) 0.15559(17) 0.0435(4) Uani d . 1 . .
H H3AA 0.6304 0.1068 0.1502 0.052 Uiso calc R 1 . .
C C4A 0.42742(19) 0.18858(16) 0.15246(15) 0.0378(3) Uani d . 1 . .
C C5A 0.4131(3) 0.3951(2) 0.1326(3) 0.0608(5) Uani d . 1 . .
H H5AA 0.4838 0.4653 0.1194 0.091 Uiso calc R 1 . .
H H5AB 0.3635 0.4268 0.2078 0.091 Uiso calc R 1 . .
H H5AC 0.3300 0.3577 0.0642 0.091 Uiso calc R 1 . .
C C6A 0.4289(3) -0.2300(2) 0.1768(3) 0.0630(6) Uani d . 1 . .
H H6AA 0.5032 -0.2872 0.1814 0.095 Uiso calc R 1 . .
H H6AB 0.3525 -0.2704 0.1045 0.095 Uiso calc R 1 . .
H H6AC 0.3714 -0.2116 0.2494 0.095 Uiso calc R 1 . .
C C7A -0.0758(2) -0.12239(17) 0.1485(2) 0.0476(4) Uani d . 1 . .
H H7AA -0.1909 -0.1400 0.1536 0.071 Uiso calc R 1 . .
H H7AB -0.0197 -0.1571 0.2024 0.071 Uiso calc R 1 . .
H H7AC -0.0529 -0.1618 0.0648 0.071 Uiso calc R 1 . .
S S1B 0.91824(6) 0.54889(4) 0.18573(4) 0.04122(12) Uani d . 1 . .
O O1B 1.0732(2) 0.63051(15) 0.21079(16) 0.0655(4) Uani d . 1 . .
O O2B 0.8041(2) 0.56321(17) 0.09628(13) 0.0639(4) Uani d . 1 . .
O O3B 0.7212(2) 0.42513(15) 0.54172(14) 0.0673(5) Uani d . 1 . .
O O4B 0.6688(2) 0.83263(14) 0.52687(15) 0.0629(4) Uani d . 1 . .
N N1B 0.78624(19) 0.69578(14) 0.36974(14) 0.0437(3) Uani d . 1 . .
N N2B 0.81160(19) 0.48548(14) 0.37722(13) 0.0414(3) Uani d . 1 . .
C C1B 0.8263(2) 0.57971(16) 0.32927(15) 0.0382(3) Uani d . 1 . .
C C2B 0.7173(2) 0.71868(18) 0.47615(17) 0.0471(4) Uani d . 1 . .
C C3B 0.6896(3) 0.6287(2) 0.53590(18) 0.0574(5) Uani d . 1 . .
H H3BA 0.6383 0.6454 0.6084 0.069 Uiso calc R 1 . .
C C4B 0.7415(3) 0.51237(18) 0.48331(17) 0.0479(4) Uani d . 1 . .
C C5B 0.7711(4) 0.3023(2) 0.4853(2) 0.0658(6) Uani d . 1 . .
H H5BA 0.7710 0.2564 0.5438 0.099 Uiso calc R 1 . .
H H5BB 0.8787 0.3163 0.4607 0.099 Uiso calc R 1 . .
H H5BC 0.6967 0.2525 0.4138 0.099 Uiso calc R 1 . .
C C6B 0.7263(4) 0.9364(2) 0.4804(2) 0.0717(7) Uani d . 1 . .
H H6BA 0.7075 1.0168 0.5370 0.108 Uiso calc R 1 . .
H H6BB 0.6689 0.9210 0.4009 0.108 Uiso calc R 1 . .
H H6BC 0.8408 0.9406 0.4725 0.108 Uiso calc R 1 . .
C C7B 0.9425(3) 0.38667(19) 0.1441(2) 0.0596(6) Uani d . 1 . .
H H7BA 0.9860 0.3620 0.0655 0.089 Uiso calc R 1 . .
H H7BB 0.8389 0.3332 0.1384 0.089 Uiso calc R 1 . .
H H7BC 1.0160 0.3758 0.2058 0.089 Uiso calc R 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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1A S1A O2A . . 117.87(10) ?
O1A S1A C7A . . 109.37(10) ?
O2A S1A C7A . . 109.13(9) ?
O1A S1A C1A . . 107.07(8) ?
O2A S1A C1A . . 108.07(8) ?
C7A S1A C1A . . 104.49(8) ?
C4A O3A C5A . . 118.66(14) ?
C2A O4A C6A . . 117.66(14) ?
C1A N1A C4A . . 113.74(14) ?
C1A N2A C2A . . 113.88(14) ?
N2A C1A N1A . . 130.25(14) ?
N2A C1A S1A . . 115.13(11) ?
N1A C1A S1A . . 114.55(11) ?
N2A C2A O4A . . 119.16(15) ?
N2A C2A C3A . . 123.00(15) ?
O4A C2A C3A . . 117.83(15) ?
C4A C3A C2A . . 116.11(15) ?
C4A C3A H3AA . . 121.9 ?
C2A C3A H3AA . . 121.9 ?
O3A C4A N1A . . 119.54(15) ?
O3A C4A C3A . . 117.47(15) ?
N1A C4A C3A . . 122.99(15) ?
O3A C5A H5AA . . 109.5 ?
O3A C5A H5AB . . 109.5 ?
H5AA C5A H5AB . . 109.5 ?
O3A C5A H5AC . . 109.5 ?
H5AA C5A H5AC . . 109.5 ?
H5AB C5A H5AC . . 109.5 ?
O4A C6A H6AA . . 109.5 ?
O4A C6A H6AB . . 109.5 ?
H6AA C6A H6AB . . 109.5 ?
O4A C6A H6AC . . 109.5 ?
H6AA C6A H6AC . . 109.5 ?
H6AB C6A H6AC . . 109.5 ?
S1A C7A H7AA . . 109.5 ?
S1A C7A H7AB . . 109.5 ?
H7AA C7A H7AB . . 109.5 ?
S1A C7A H7AC . . 109.5 ?
H7AA C7A H7AC . . 109.5 ?
H7AB C7A H7AC . . 109.5 ?
O1B S1B O2B . . 117.30(11) ?
O1B S1B C7B . . 110.02(12) ?
O2B S1B C7B . . 109.13(12) ?
O1B S1B C1B . . 107.47(9) ?
O2B S1B C1B . . 107.25(9) ?
C7B S1B C1B . . 104.92(9) ?
C4B O3B C5B . . 118.20(16) ?
C2B O4B C6B . . 117.81(17) ?
C1B N1B C2B . . 113.47(15) ?
C1B N2B C4B . . 113.85(15) ?
N2B C1B N1B . . 130.63(16) ?
N2B C1B S1B . . 115.98(12) ?
N1B C1B S1B . . 113.38(13) ?
N1B C2B O4B . . 119.64(18) ?
N1B C2B C3B . . 122.83(17) ?
O4B C2B C3B . . 117.51(17) ?
C2B C3B C4B . . 116.88(17) ?
C2B C3B H3BA . . 121.6 ?
C4B C3B H3BA . . 121.6 ?
O3B C4B N2B . . 119.62(17) ?
O3B C4B C3B . . 118.09(17) ?
N2B C4B C3B . . 122.29(17) ?
O3B C5B H5BA . . 109.5 ?
O3B C5B H5BB . . 109.5 ?
H5BA C5B H5BB . . 109.5 ?
O3B C5B H5BC . . 109.5 ?
H5BA C5B H5BC . . 109.5 ?
H5BB C5B H5BC . . 109.5 ?
O4B C6B H6BA . . 109.5 ?
O4B C6B H6BB . . 109.5 ?
H6BA C6B H6BB . . 109.5 ?
O4B C6B H6BC . . 109.5 ?
H6BA C6B H6BC . . 109.5 ?
H6BB C6B H6BC . . 109.5 ?
S1B C7B H7BA . . 109.5 ?
S1B C7B H7BB . . 109.5 ?
H7BA C7B H7BB . . 109.5 ?
S1B C7B H7BC . . 109.5 ?
H7BA C7B H7BC . . 109.5 ?
H7BB C7B H7BC . . 109.5 ?
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
S1A O1A . 1.4334(16) ?
S1A O2A . 1.4356(14) ?
S1A C7A . 1.7429(18) ?
S1A C1A . 1.8059(15) ?
O3A C4A . 1.338(2) ?
O3A C5A . 1.436(3) ?
O4A C2A . 1.342(2) ?
O4A C6A . 1.443(2) ?
N1A C1A . 1.322(2) ?
N1A C4A . 1.339(2) ?
N2A C1A . 1.321(2) ?
N2A C2A . 1.334(2) ?
C2A C3A . 1.386(2) ?
C3A C4A . 1.382(2) ?
C3A H3AA . 0.93 ?
C5A H5AA . 0.96 ?
C5A H5AB . 0.96 ?
C5A H5AC . 0.96 ?
C6A H6AA . 0.96 ?
C6A H6AB . 0.96 ?
C6A H6AC . 0.96 ?
C7A H7AA . 0.96 ?
C7A H7AB . 0.96 ?
C7A H7AC . 0.96 ?
S1B O1B . 1.4234(16) ?
S1B O2B . 1.4260(16) ?
S1B C7B . 1.751(2) ?
S1B C1B . 1.8018(17) ?
O3B C4B . 1.333(2) ?
O3B C5B . 1.441(3) ?
O4B C2B . 1.342(2) ?
O4B C6B . 1.442(3) ?
N1B C1B . 1.320(2) ?
N1B C2B . 1.339(2) ?
N2B C1B . 1.317(2) ?
N2B C4B . 1.340(2) ?
C2B C3B . 1.375(3) ?
C3B C4B . 1.381(3) ?
C3B H3BA . 0.93 ?
C5B H5BA . 0.96 ?
C5B H5BB . 0.96 ?
C5B H5BC . 0.96 ?
C6B H6BA . 0.96 ?
C6B H6BB . 0.96 ?
C6B H6BC . 0.96 ?
C7B H7BA . 0.96 ?
C7B H7BB . 0.96 ?
C7B H7BC . 0.96 ?
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
C3A H3AA O2A 1_655 0.93 2.42 3.336(2) 169 yes
C5A H5AC O2B 2_665 0.96 2.55 3.303(3) 135 yes
C7A H7AA O4A 1_455 0.96 2.50 3.426(2) 161 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2A N2A C1A N1A . . . . -0.7(3) ?
C2A N2A C1A S1A . . . . -177.62(12) ?
C4A N1A C1A N2A . . . . -0.6(3) ?
C4A N1A C1A S1A . . . . 176.33(12) ?
O1A S1A C1A N2A . . . . 91.31(14) ?
O2A S1A C1A N2A . . . . -140.77(13) ?
C7A S1A C1A N2A . . . . -24.64(15) ?
O1A S1A C1A N1A . . . . -86.07(14) ?
O2A S1A C1A N1A . . . . 41.86(14) ?
C7A S1A C1A N1A . . . . 157.98(13) ?
C1A N2A C2A O4A . . . . -179.19(16) ?
C1A N2A C2A C3A . . . . 1.8(2) ?
C6A O4A C2A N2A . . . . 3.3(3) ?
C6A O4A C2A C3A . . . . -177.70(18) ?
N2A C2A C3A C4A . . . . -1.6(3) ?
O4A C2A C3A C4A . . . . 179.42(16) ?
C5A O3A C4A N1A . . . . -3.4(3) ?
C5A O3A C4A C3A . . . . 177.06(19) ?
C1A N1A C4A O3A . . . . -178.65(15) ?
C1A N1A C4A C3A . . . . 0.8(2) ?
C2A C3A C4A O3A . . . . 179.63(16) ?
C2A C3A C4A N1A . . . . 0.1(3) ?
C4B N2B C1B N1B . . . . 1.4(3) ?
C4B N2B C1B S1B . . . . -179.50(13) ?
C2B N1B C1B N2B . . . . -1.2(3) ?
C2B N1B C1B S1B . . . . 179.75(13) ?
O1B S1B C1B N2B . . . . -110.99(15) ?
O2B S1B C1B N2B . . . . 122.06(15) ?
C7B S1B C1B N2B . . . . 6.09(18) ?
O1B S1B C1B N1B . . . . 68.23(16) ?
O2B S1B C1B N1B . . . . -58.72(16) ?
C7B S1B C1B N1B . . . . -174.69(15) ?
C1B N1B C2B O4B . . . . -179.21(18) ?
C1B N1B C2B C3B . . . . -0.8(3) ?
C6B O4B C2B N1B . . . . -14.0(3) ?
C6B O4B C2B C3B . . . . 167.5(2) ?
N1B C2B C3B C4B . . . . 2.1(3) ?
O4B C2B C3B C4B . . . . -179.4(2) ?
C5B O3B C4B N2B . . . . -2.2(3) ?
C5B O3B C4B C3B . . . . 178.3(2) ?
C1B N2B C4B O3B . . . . -179.31(19) ?
C1B N2B C4B C3B . . . . 0.2(3) ?
C2B C3B C4B O3B . . . . 177.7(2) ?
C2B C3B C4B N2B . . . . -1.8(3) ?
