#------------------------------------------------------------------------------
#$Date: 2017-07-25 13:41:59 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/67/1546716.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_1546716
loop_
_publ_author_name
'Olszowy, Aleksandra'
'Siodłak, Dawid'
'Zarychta, Bartosz'
_publ_section_title
;
 3,5-Dimethoxyphenyl 4-methylbenzenesulfonate
;
_journal_coeditor_code           BT4054
_journal_issue                   7
_journal_name_full               IUCrData
_journal_page_first              x170980
_journal_paper_doi               10.1107/S2414314617009804
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C15 H16 O5 S'
_chemical_formula_moiety         'C15 H16 O5 S'
_chemical_formula_sum            'C15 H16 O5 S'
_chemical_formula_weight         308.34
_chemical_name_systematic
;
3,5-Dimethoxyphenyl 4-methylbenzenesulfonate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                106.583(2)
_cell_angle_beta                 94.701(2)
_cell_angle_gamma                111.358(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8066(2)
_cell_length_b                   8.9238(2)
_cell_length_c                   11.9303(3)
_cell_measurement_reflns_used    4805
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.998
_cell_measurement_theta_min      3.058
_cell_volume                     725.58(4)
_computing_cell_refinement
;
CrysAlisCCD (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlisCCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlisRed (Oxford Diffraction, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω--scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4805
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.058
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.349
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0286
_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)+(0.0437P)²+0.0255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                2316
_reflns_number_total             2795
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4054sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        725.58(3)
_cod_database_code               1546716
_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.
;
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_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_occupancy
S S1 0.73013(5) 0.83595(4) 0.47367(3) 0.01539(11) Uani d 1
O O1 0.81146(14) 0.96873(12) 0.42577(9) 0.0195(2) Uani d 1
C C1 0.80548(19) 0.67126(18) 0.41824(12) 0.0147(3) Uani d 1
C C2 0.91926(19) 0.68105(18) 0.33471(12) 0.0157(3) Uani d 1
H H2 0.9673 0.7794 0.3145 0.019 Uiso calc 1
O O2 0.73567(14) 0.87416(13) 0.59863(9) 0.0217(2) Uani d 1
O O3 0.50777(13) 0.74229(12) 0.41772(8) 0.0157(2) Uani d 1
C C3 0.95988(19) 0.54111(18) 0.28197(12) 0.0168(3) Uani d 1
H H3 1.0349 0.5460 0.2253 0.020 Uiso calc 1
C C4 0.89064(19) 0.39332(18) 0.31217(12) 0.0166(3) Uani d 1
O O4 0.26779(15) 0.29839(13) 0.04463(9) 0.0234(3) Uani d 1
C C5 0.78274(19) 0.39000(18) 0.39973(12) 0.0173(3) Uani d 1
H H5 0.7394 0.2940 0.4229 0.021 Uiso calc 1
O O5 0.32254(15) 0.85268(13) 0.06289(9) 0.0221(2) Uani d 1
C C6 0.7393(2) 0.52739(18) 0.45258(12) 0.0165(3) Uani d 1
H H6 0.6665 0.5236 0.5105 0.020 Uiso calc 1
C C8 0.44594(18) 0.69113(18) 0.29240(12) 0.0148(3) Uani d 1
C C7 0.9329(2) 0.24146(19) 0.25186(14) 0.0224(3) Uani d 1
H H7A 0.8954 0.2084 0.1667 0.034 Uiso calc 1
H H7B 0.8649 0.1479 0.2774 0.034 Uiso calc 1
H H7C 1.0653 0.2714 0.2730 0.034 Uiso calc 1
C C9 0.39824(19) 0.52299(18) 0.22586(12) 0.0163(3) Uani d 1
H H9 0.4173 0.4479 0.2607 0.020 Uiso calc 1
C C10 0.3204(2) 0.46833(18) 0.10448(13) 0.0173(3) Uani d 1
C C11 0.29768(19) 0.58182(18) 0.05261(12) 0.0172(3) Uani d 1
H H11 0.2472 0.5449 -0.0287 0.021 Uiso calc 1
C C12 0.3511(2) 0.75243(19) 0.12328(13) 0.0163(3) Uani d 1
C C13 0.42417(19) 0.80989(18) 0.24526(12) 0.0157(3) Uani d 1
H H13 0.4570 0.9227 0.2931 0.019 Uiso calc 1
C C14 0.1783(2) 0.2341(2) -0.07898(13) 0.0261(4) Uani d 1
H H14A 0.2629 0.2905 -0.1225 0.039 Uiso calc 1
H H14B 0.0668 0.2557 -0.0868 0.039 Uiso calc 1
H H14C 0.1451 0.1132 -0.1106 0.039 Uiso calc 1
C C15 0.3825(2) 1.0314(2) 0.12916(14) 0.0275(4) Uani d 1
H H15A 0.3640 1.0896 0.0759 0.041 Uiso calc 1
H H15B 0.5134 1.0791 0.1661 0.041 Uiso calc 1
H H15C 0.3102 1.0449 0.1897 0.041 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'
O O 0.0106 0.0060 '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'
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_3
_geom_angle
O2 S1 O1 . 120.88(6)
O2 S1 O3 . 102.37(6)
O1 S1 O3 . 108.43(5)
O2 S1 C1 . 110.89(6)
O1 S1 C1 . 110.05(6)
O3 S1 C1 . 102.28(6)
O2 S1 O1 2_776 80.61(5)
O1 S1 O1 2_776 68.92(5)
O3 S1 O1 2_776 176.85(4)
C1 S1 O1 2_776 77.41(5)
C2 C1 C6 . 121.02(13)
C2 C1 S1 . 119.61(11)
C6 C1 S1 . 119.22(11)
C1 C2 C3 . 118.68(13)
C1 C2 H2 . 120.7
C3 C2 H2 . 120.7
C8 O3 S1 . 118.80(8)
C2 C3 C4 . 121.42(13)
C2 C3 H3 . 119.3
C4 C3 H3 . 119.3
C5 C4 C3 . 118.48(13)
C5 C4 C7 . 120.97(13)
C3 C4 C7 . 120.55(13)
C10 O4 C14 . 117.21(11)
C6 C5 C4 . 120.99(13)
C6 C5 H5 . 119.5
C4 C5 H5 . 119.5
C12 O5 C15 . 117.31(12)
C5 C6 C1 . 119.33(13)
C5 C6 H6 . 120.3
C1 C6 H6 . 120.3
C9 C8 C13 . 123.77(13)
C9 C8 O3 . 117.73(12)
C13 C8 O3 . 118.33(12)
C4 C7 H7A . 109.5
C4 C7 H7B . 109.5
H7A C7 H7B . 109.5
C4 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
C8 C9 C10 . 117.91(13)
C8 C9 H9 . 121.0
C10 C9 H9 . 121.0
O4 C10 C11 . 124.24(13)
O4 C10 C9 . 115.06(12)
C11 C10 C9 . 120.70(13)
C10 C11 C12 . 119.46(13)
C10 C11 H11 . 120.3
C12 C11 H11 . 120.3
O5 C12 C13 . 124.31(13)
O5 C12 C11 . 114.44(13)
C13 C12 C11 . 121.24(13)
C8 C13 C12 . 116.89(13)
C8 C13 H13 . 121.6
C12 C13 H13 . 121.6
O4 C14 H14A . 109.5
O4 C14 H14B . 109.5
H14A C14 H14B . 109.5
O4 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 109.5
O5 C15 H15A . 109.5
O5 C15 H15B . 109.5
H15A C15 H15B . 109.5
O5 C15 H15C . 109.5
H15A C15 H15C . 109.5
H15B C15 H15C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O2 . 1.4244(10)
S1 O1 . 1.4254(10)
S1 O3 . 1.6101(10)
S1 C1 . 1.7556(14)
S1 O1 2_776 3.2929(10)
C1 C2 . 1.3885(19)
C1 C6 . 1.3910(19)
C2 C3 . 1.3887(19)
C2 H2 . 0.9300
O3 C8 . 1.4171(15)
C3 C4 . 1.395(2)
C3 H3 . 0.9300
C4 C5 . 1.3947(19)
C4 C7 . 1.5070(19)
O4 C10 . 1.3633(17)
O4 C14 . 1.4313(17)
C5 C6 . 1.383(2)
C5 H5 . 0.9300
O5 C12 . 1.3623(17)
O5 C15 . 1.4366(18)
C6 H6 . 0.9300
C8 C9 . 1.373(2)
C8 C13 . 1.3871(19)
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C9 C10 . 1.3931(19)
C9 H9 . 0.9300
C10 C11 . 1.382(2)
C11 C12 . 1.396(2)
C11 H11 . 0.9300
C12 C13 . 1.3896(19)
C13 H13 . 0.9300
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 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
C15 H15A O4 1_565 0.96 2.35 3.2051(18) 147.3
C15 H15C O2 2_676 0.96 2.51 3.4063(19) 154.6
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
O2 S1 C1 C2 . -139.74(11)
O1 S1 C1 C2 . -3.35(13)
O3 S1 C1 C2 . 111.74(11)
O1 S1 C1 C2 2_776 -65.06(11)
O2 S1 C1 C6 . 44.73(13)
O1 S1 C1 C6 . -178.88(11)
O3 S1 C1 C6 . -63.80(12)
O1 S1 C1 C6 2_776 119.40(11)
C6 C1 C2 C3 . 2.6(2)
S1 C1 C2 C3 . -172.83(10)
O2 S1 O3 C8 . 177.23(9)
O1 S1 O3 C8 . 48.40(11)
C1 S1 O3 C8 . -67.86(10)
C1 C2 C3 C4 . -0.7(2)
C2 C3 C4 C5 . -1.7(2)
C2 C3 C4 C7 . 178.63(13)
C3 C4 C5 C6 . 2.3(2)
C7 C4 C5 C6 . -178.07(13)
C4 C5 C6 C1 . -0.4(2)
C2 C1 C6 C5 . -2.1(2)
S1 C1 C6 C5 . 173.38(11)
S1 O3 C8 C9 . 98.87(13)
S1 O3 C8 C13 . -85.70(13)
C13 C8 C9 C10 . -1.2(2)
O3 C8 C9 C10 . 173.96(11)
C14 O4 C10 C11 . -2.0(2)
C14 O4 C10 C9 . 176.90(13)
C8 C9 C10 O4 . -176.98(12)
C8 C9 C10 C11 . 1.9(2)
O4 C10 C11 C12 . 177.91(12)
C9 C10 C11 C12 . -0.9(2)
C15 O5 C12 C13 . 3.8(2)
C15 O5 C12 C11 . -177.20(12)
C10 C11 C12 O5 . 179.96(12)
C10 C11 C12 C13 . -1.0(2)
C9 C8 C13 C12 . -0.6(2)
O3 C8 C13 C12 . -175.70(11)
O5 C12 C13 C8 . -179.37(13)
C11 C12 C13 C8 . 1.7(2)

_cod_database_fobs_code 1546716
