#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/84/2208483.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_2208483
loop_
_publ_author_name
'Zeller, Matthias'
'Hunter, Allen D.'
'Sampson, Paul'
'Chumachenko, Nataliya'
_publ_section_title
;
 1-[(E)-Butadienylsulfonyl]-3,3-dimethylbut-2-yl methacrylate
;
_journal_coeditor_code           AT2014
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1369
_journal_page_last               o1370
_journal_paper_doi               10.1107/S1600536806008014
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H22 O4 S'
_chemical_formula_moiety         'C14 H22 O4 S'
_chemical_formula_sum            'C14 H22 O4 S'
_chemical_formula_weight         286.38
_chemical_name_systematic
;
1-[(E)-Butadienylsulfonyl]-3,3-dimethylbut-2-yl methacrylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8062(5)
_cell_length_b                   16.8880(10)
_cell_length_c                   10.6858(6)
_cell_measurement_reflns_used    5932
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      2.26
_cell_volume                     1586.85(16)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16205
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SAINT-Plus; Bruker,  2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0350
_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)+(0.0536P)²+0.4386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                3607
_reflns_number_total             3945
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2014.cif
_cod_data_source_block           I
_cod_original_cell_volume        1586.9(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208483
_cod_database_fobs_code          2208483
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
C C1 0.38702(11) 0.11749(6) 0.95398(10) 0.0194(2) Uani d . 1
H H1A 0.3652 0.0606 0.9398 0.023 Uiso calc R 1
H H1B 0.3622 0.1301 1.0410 0.023 Uiso calc R 1
C C2 0.28394(11) 0.16558(6) 0.86488(9) 0.01773(19) Uani d . 1
H H2 0.3214 0.1621 0.7784 0.021 Uiso calc R 1
C C3 0.11579(12) 0.13997(6) 0.86252(10) 0.0212(2) Uani d . 1
C C4 0.05587(14) 0.13956(8) 0.99403(12) 0.0321(3) Uani d . 1
H H4A 0.0714 0.1918 1.0324 0.048 Uiso calc R 1
H H4B 0.1106 0.0996 1.0453 0.048 Uiso calc R 1
H H4C -0.0529 0.1270 0.9887 0.048 Uiso calc R 1
C C5 0.10063(14) 0.05714(7) 0.80474(12) 0.0306(3) Uani d . 1
H H5A -0.0070 0.0423 0.7963 0.046 Uiso calc R 1
H H5B 0.1559 0.0189 0.8591 0.046 Uiso calc R 1
H H5C 0.1433 0.0572 0.7219 0.046 Uiso calc R 1
C C6 0.02243(13) 0.19767(8) 0.77878(12) 0.0308(3) Uani d . 1
H H6A -0.0841 0.1806 0.7727 0.046 Uiso calc R 1
H H6B 0.0624 0.1984 0.6950 0.046 Uiso calc R 1
H H6C 0.0292 0.2509 0.8151 0.046 Uiso calc R 1
C C7 0.33767(11) 0.30301(6) 0.82837(9) 0.0196(2) Uani d . 1
C C8 0.35105(12) 0.38288(6) 0.88768(10) 0.0226(2) Uani d . 1
C C9 0.34282(16) 0.39078(7) 1.01140(11) 0.0318(3) Uani d . 1
H H9A 0.3565 0.4413 1.0493 0.038 Uiso calc R 1
H H9B 0.3233 0.3458 1.0615 0.038 Uiso calc R 1
C C10 0.38095(18) 0.44932(7) 0.80140(12) 0.0352(3) Uani d . 1
H H10A 0.3886 0.4989 0.8489 0.053 Uiso calc R 1
H H10B 0.2975 0.4532 0.7372 0.053 Uiso calc R 1
H H10C 0.4766 0.4397 0.7611 0.053 Uiso calc R 1
C C11 0.62538(12) 0.22577(6) 1.00759(10) 0.0216(2) Uani d . 1
H H11 0.5946 0.2366 1.0897 0.026 Uiso calc R 1
C C12 0.69963(12) 0.28070(6) 0.94572(11) 0.0234(2) Uani d . 1
H H12 0.7191 0.2708 0.8606 0.028 Uiso calc R 1
C C13 0.75245(13) 0.35494(7) 1.00118(12) 0.0278(2) Uani d . 1
H H13 0.7260 0.3673 1.0840 0.033 Uiso calc R 1
C C14 0.83615(17) 0.40607(8) 0.94064(16) 0.0423(3) Uani d . 1
H H14A 0.8637 0.3947 0.8578 0.051 Uiso calc R 1
H H14B 0.8685 0.4540 0.9801 0.051 Uiso calc R 1
O O1 0.29568(8) 0.24705(4) 0.90888(6) 0.01848(16) Uani d . 1
O O2 0.36294(10) 0.29046(5) 0.72036(7) 0.02818(19) Uani d . 1
O O3 0.61579(10) 0.13718(5) 0.80823(9) 0.0349(2) Uani d . 1
O O4 0.66169(10) 0.07499(5) 1.01659(11) 0.0420(3) Uani d . 1
S S1 0.58416(3) 0.133785(15) 0.93886(3) 0.02410(9) 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'
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
C2 C1 S1 114.55(7)
C2 C1 H1A 108.6
S1 C1 H1A 108.6
C2 C1 H1B 108.6
S1 C1 H1B 108.6
H1A C1 H1B 107.6
O1 C2 C1 105.89(8)
O1 C2 C3 108.77(8)
C1 C2 C3 113.71(8)
O1 C2 H2 109.5
C1 C2 H2 109.5
C3 C2 H2 109.5
C4 C3 C6 109.82(10)
C4 C3 C5 109.86(9)
C6 C3 C5 108.25(9)
C4 C3 C2 111.44(9)
C6 C3 C2 108.41(9)
C5 C3 C2 108.99(9)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C3 C5 H5A 109.5
C3 C5 H5B 109.5
H5A C5 H5B 109.5
C3 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C3 C6 H6A 109.5
C3 C6 H6B 109.5
H6A C6 H6B 109.5
C3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
O2 C7 O1 124.11(9)
O2 C7 C8 123.43(9)
O1 C7 C8 112.46(9)
C9 C8 C10 124.09(10)
C9 C8 C7 120.26(10)
C10 C8 C7 115.59(9)
C8 C9 H9A 120.0
C8 C9 H9B 120.0
H9A C9 H9B 120.0
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 S1 120.47(9)
C12 C11 H11 119.8
S1 C11 H11 119.8
C11 C12 C13 123.64(11)
C11 C12 H12 118.2
C13 C12 H12 118.2
C14 C13 C12 122.49(13)
C14 C13 H13 118.8
C12 C13 H13 118.8
C13 C14 H14A 120.0
C13 C14 H14B 120.0
H14A C14 H14B 120.0
C7 O1 C2 118.37(8)
O3 S1 O4 118.40(6)
O3 S1 C11 108.99(5)
O4 S1 C11 106.78(6)
O3 S1 C1 109.65(5)
O4 S1 C1 106.01(5)
C11 S1 C1 106.36(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.5155(14) ?
C1 S1 1.7738(10) ?
C1 H1A 0.9900 ?
C1 H1B 0.9900 ?
C2 O1 1.4560(11) ?
C2 C3 1.5414(14) ?
C2 H2 1.0000 ?
C3 C4 1.5277(16) ?
C3 C6 1.5318(15) ?
C3 C5 1.5320(15) ?
C4 H4A 0.9800 ?
C4 H4B 0.9800 ?
C4 H4C 0.9800 ?
C5 H5A 0.9800 ?
C5 H5B 0.9800 ?
C5 H5C 0.9800 ?
C6 H6A 0.9800 ?
C6 H6B 0.9800 ?
C6 H6C 0.9800 ?
C7 O2 1.2060(13) y
C7 O1 1.3433(12) y
C7 C8 1.4922(14) y
C8 C9 1.3346(16) y
C8 C10 1.4849(16) y
C9 H9A 0.9500 ?
C9 H9B 0.9500 ?
C10 H10A 0.9800 ?
C10 H10B 0.9800 ?
C10 H10C 0.9800 ?
C11 C12 1.3313(15) y
C11 S1 1.7480(11) y
C11 H11 0.9500 y
C12 C13 1.4524(15) y
C12 H12 0.9500 ?
C13 C14 1.3264(18) y
C13 H13 0.9500 ?
C14 H14A 0.9500 ?
C14 H14B 0.9500 ?
O3 S1 1.4392(10) y
O4 S1 1.4425(9) 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
S1 C1 C2 O1 -71.07(9)
S1 C1 C2 C3 169.56(7)
O1 C2 C3 C4 -63.85(11)
C1 C2 C3 C4 53.87(12)
O1 C2 C3 C6 57.12(11)
C1 C2 C3 C6 174.84(9)
O1 C2 C3 C5 174.75(8)
C1 C2 C3 C5 -67.53(11)
O2 C7 C8 C9 -170.38(12)
O1 C7 C8 C9 9.14(15)
O2 C7 C8 C10 6.74(16)
O1 C7 C8 C10 -173.75(10)
S1 C11 C12 C13 -173.04(8)
C11 C12 C13 C14 174.75(12)
O2 C7 O1 C2 1.87(15)
C8 C7 O1 C2 -177.64(8)
C1 C2 O1 C7 123.99(9)
C3 C2 O1 C7 -113.44(9)
C12 C11 S1 O3 -10.82(11)
C12 C11 S1 O4 118.17(10)
C12 C11 S1 C1 -128.96(9)
C2 C1 S1 O3 -42.68(9)
C2 C1 S1 O4 -171.57(8)
C2 C1 S1 C11 75.02(8)
