#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/43/4024300.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024300
loop_
_publ_author_name
'Eric Fillion'
'Ashraf Wilsily'
'Dan Fishlock'
_publ_section_title
;
Probing Persistent Intramolecular C-H...X (X = O, S, Br, Cl, and F)
Bonding in Solution Using Benzyl Meldrum's Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1259
_journal_page_last               1267
_journal_paper_doi               10.1021/jo802311w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C16 H20 O4 S'
_chemical_formula_weight         308.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   constr
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.6108(6)
_cell_length_b                   9.9743(6)
_cell_length_c                   33.578(2)
_cell_measurement_temperature    180(2)
_cell_volume                     3218.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            29314
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_correction_T_min  0.9427
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'APEX II'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.044
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0458
_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)+(0.0249P)²+1.3626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                3947
_reflns_number_total             4676
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802311w_si_009.cif
_cod_data_source_block           aw-2-260-3_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4024300
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S18 S 0.23233(5) 0.74731(4) 0.328101(13) 0.04529(12) Uani 1 1 d . . .
O9 O -0.03040(12) 0.71286(11) 0.45146(4) 0.0455(3) Uani 1 1 d . . .
O10 O 0.03096(14) 1.10687(10) 0.39028(3) 0.0475(3) Uani 1 1 d . . .
O1 O 0.17420(12) 1.05271(9) 0.43837(3) 0.0350(2) Uani 1 1 d . . .
O3 O 0.13206(11) 0.84944(10) 0.47205(3) 0.0350(2) Uani 1 1 d . . .
C17 C 0.10837(17) 0.86724(15) 0.31047(4) 0.0377(3) Uani 1 1 d . . .
C12 C -0.01367(16) 0.89993(16) 0.33156(4) 0.0366(3) Uani 1 1 d . . .
C13 C -0.10192(19) 0.99438(19) 0.31402(5) 0.0495(4) Uani 1 1 d . . .
H13 H -0.1859 1.0174 0.3273 0.059 Uiso 1 1 calc R . .
C14 C -0.0718(2) 1.0557(2) 0.27805(6) 0.0598(5) Uani 1 1 d . . .
H14 H -0.1341 1.1199 0.2672 0.072 Uiso 1 1 calc R . .
C15 C 0.0485(2) 1.0234(2) 0.25810(5) 0.0593(5) Uani 1 1 d . . .
H15 H 0.0709 1.0663 0.2337 0.071 Uiso 1 1 calc R . .
C16 C 0.1361(2) 0.92835(19) 0.27394(5) 0.0509(4) Uani 1 1 d . . .
H16 H 0.2175 0.9036 0.2597 0.061 Uiso 1 1 calc R . .
C19 C 0.3937(2) 0.8339(2) 0.32071(7) 0.0640(6) Uani 1 1 d . . .
H19Z H 0.4708 0.7770 0.3296 0.096 Uiso 1 1 calc R . .
H19Y H 0.3934 0.9173 0.3362 0.096 Uiso 1 1 calc R . .
H19X H 0.4050 0.8549 0.2924 0.096 Uiso 1 1 calc R . .
C11 C -0.05380(15) 0.83539(15) 0.37185(4) 0.0349(3) Uani 1 1 d . . .
C21 C -0.0651(2) 0.68218(17) 0.36543(5) 0.0500(4) Uani 1 1 d . . .
H21Z H -0.1381 0.6634 0.3458 0.075 Uiso 1 1 calc R . .
H21Y H -0.0885 0.6386 0.3907 0.075 Uiso 1 1 calc R . .
H21X H 0.0240 0.6475 0.3557 0.075 Uiso 1 1 calc R . .
C20 C -0.19607(17) 0.8831(2) 0.38731(5) 0.0508(4) Uani 1 1 d . . .
H20Z H -0.1933 0.9802 0.3918 0.076 Uiso 1 1 calc R . .
H20Y H -0.2176 0.8374 0.4124 0.076 Uiso 1 1 calc R . .
H20X H -0.2680 0.8622 0.3676 0.076 Uiso 1 1 calc R . .
C5 C 0.06085(14) 0.86958(12) 0.40292(4) 0.0274(3) Uani 1 1 d . . .
H5 H 0.1496 0.8348 0.3913 0.033 Uiso 1 1 calc R . .
C4 C 0.04749(15) 0.80259(13) 0.44320(4) 0.0320(3) Uani 1 1 d . . .
C2 C 0.23444(16) 0.95148(13) 0.46385(4) 0.0317(3) Uani 1 1 d . . .
C8 C 0.26045(19) 1.02081(16) 0.50317(4) 0.0429(4) Uani 1 1 d . . .
H8Z H 0.1727 1.0571 0.5134 0.064 Uiso 1 1 calc R . .
H8Y H 0.3271 1.0940 0.4993 0.064 Uiso 1 1 calc R . .
H8X H 0.2984 0.9562 0.5223 0.064 Uiso 1 1 calc R . .
C7 C 0.36418(16) 0.89202(15) 0.44596(5) 0.0380(3) Uani 1 1 d . . .
H7Z H 0.3412 0.8490 0.4206 0.057 Uiso 1 1 calc R . .
H7Y H 0.4030 0.8252 0.4642 0.057 Uiso 1 1 calc R . .
H7X H 0.4327 0.9632 0.4414 0.057 Uiso 1 1 calc R . .
C6 C 0.08402(16) 1.01884(13) 0.40904(4) 0.0318(3) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 S18 C19 102.01(9) . . ?
C6 O1 C2 120.84(10) . . ?
C4 O3 C2 121.25(10) . . ?
C16 C17 C12 119.99(16) . . ?
C16 C17 S18 117.12(14) . . ?
C12 C17 S18 122.88(12) . . ?
C13 C12 C17 116.70(15) . . ?
C13 C12 C11 119.85(15) . . ?
C17 C12 C11 123.44(14) . . ?
C14 C13 C12 122.59(19) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C15 C14 C13 119.83(19) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.21(17) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 121.64(18) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
S18 C19 H19Z 109.5 . . ?
S18 C19 H19Y 109.5 . . ?
H19Z C19 H19Y 109.5 . . ?
S18 C19 H19X 109.5 . . ?
H19Z C19 H19X 109.5 . . ?
H19Y C19 H19X 109.5 . . ?
C20 C11 C12 112.83(14) . . ?
C20 C11 C21 106.87(14) . . ?
C12 C11 C21 107.86(12) . . ?
C20 C11 C5 109.61(12) . . ?
C12 C11 C5 108.58(11) . . ?
C21 C11 C5 111.10(13) . . ?
C11 C21 H21Z 109.5 . . ?
C11 C21 H21Y 109.5 . . ?
H21Z C21 H21Y 109.5 . . ?
C11 C21 H21X 109.5 . . ?
H21Z C21 H21X 109.5 . . ?
H21Y C21 H21X 109.5 . . ?
C11 C20 H20Z 109.5 . . ?
C11 C20 H20Y 109.5 . . ?
H20Z C20 H20Y 109.5 . . ?
C11 C20 H20X 109.5 . . ?
H20Z C20 H20X 109.5 . . ?
H20Y C20 H20X 109.5 . . ?
C4 C5 C6 108.90(11) . . ?
C4 C5 C11 116.25(11) . . ?
C6 C5 C11 114.17(11) . . ?
C4 C5 H5 105.5 . . ?
C6 C5 H5 105.5 . . ?
C11 C5 H5 105.5 . . ?
O9 C4 O3 117.96(13) . . ?
O9 C4 C5 126.08(14) . . ?
O3 C4 C5 115.97(12) . . ?
O3 C2 O1 109.44(11) . . ?
O3 C2 C7 111.30(11) . . ?
O1 C2 C7 111.77(12) . . ?
O3 C2 C8 105.61(12) . . ?
O1 C2 C8 105.30(11) . . ?
C7 C2 C8 113.07(13) . . ?
C2 C8 H8Z 109.5 . . ?
C2 C8 H8Y 109.5 . . ?
H8Z C8 H8Y 109.5 . . ?
C2 C8 H8X 109.5 . . ?
H8Z C8 H8X 109.5 . . ?
H8Y C8 H8X 109.5 . . ?
C2 C7 H7Z 109.5 . . ?
C2 C7 H7Y 109.5 . . ?
H7Z C7 H7Y 109.5 . . ?
C2 C7 H7X 109.5 . . ?
H7Z C7 H7X 109.5 . . ?
H7Y C7 H7X 109.5 . . ?
O10 C6 O1 118.23(12) . . ?
O10 C6 C5 125.88(13) . . ?
O1 C6 C5 115.89(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S18 C17 1.7891(17) . ?
S18 C19 1.792(2) . ?
O9 C4 1.1993(17) . ?
O10 C6 1.1950(16) . ?
O1 C6 1.3547(16) . ?
O1 C2 1.4447(16) . ?
O3 C4 1.3481(18) . ?
O3 C2 1.4422(17) . ?
C17 C16 1.395(2) . ?
C17 C12 1.408(2) . ?
C12 C13 1.398(2) . ?
C12 C11 1.547(2) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C19 H19Z 0.9800 . ?
C19 H19Y 0.9800 . ?
C19 H19X 0.9800 . ?
C11 C20 1.538(2) . ?
C11 C21 1.547(2) . ?
C11 C5 1.5551(19) . ?
C21 H21Z 0.9800 . ?
C21 H21Y 0.9800 . ?
C21 H21X 0.9800 . ?
C20 H20Z 0.9800 . ?
C20 H20Y 0.9800 . ?
C20 H20X 0.9800 . ?
C5 C4 1.5140(18) . ?
C5 C6 1.5193(18) . ?
C5 H5 1.0000 . ?
C2 C7 1.506(2) . ?
C2 C8 1.5112(19) . ?
C8 H8Z 0.9800 . ?
C8 H8Y 0.9800 . ?
C8 H8X 0.9800 . ?
C7 H7Z 0.9800 . ?
C7 H7Y 0.9800 . ?
C7 H7X 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658884
