#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:21:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178779 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/33/4103330.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_4103330
loop_
_publ_author_name
'Jun Hee Lee'
'Yandong Zhang'
'Samuel J. Danishefsky'
_publ_section_title
;
 A Straightforward Route to Functionalizedtrans-Diels-Alder Motifs
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14330
_journal_page_last               14333
_journal_paper_doi               10.1021/ja1073855
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C19 H24 O2 S'
_chemical_formula_weight         316.44
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.897(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.757(3)
_cell_length_b                   22.315(5)
_cell_length_c                   7.0957(16)
_cell_measurement_reflns_used    4763
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      29.53
_cell_measurement_theta_min      2.64
_cell_volume                     1697.1(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.1515
_diffrn_reflns_av_sigmaI/netI    0.1244
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22349
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9400
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.1757
_refine_ls_R_factor_gt           0.0867
_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)+(0.0205P)²+6.0504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.1964
_reflns_number_gt                2280
_reflns_number_total             4220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1073855_si_003.cif
_cod_data_source_block           juws10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'EMPIRICAL' changed to
'empirical' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to the built-in table from CIF Core 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_cell_volume        1697.0(7)
_cod_database_code               4103330
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_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
S1 S 0.26086(12) 0.32920(5) 0.42008(15) 0.0216(3) Uani 1 1 d .
O1 O -0.0704(3) 0.38135(16) 0.3288(5) 0.0314(9) Uani 1 1 d .
O2 O 0.1755(3) 0.27662(16) 0.4367(5) 0.0328(9) Uani 1 1 d .
C1 C 0.2788(5) 0.5407(2) 0.3811(7) 0.0326(12) Uani 1 1 d .
H1A H 0.3304 0.5715 0.3280 0.049 Uiso 1 1 calc R
H1B H 0.3296 0.5177 0.4768 0.049 Uiso 1 1 calc R
H1C H 0.2096 0.5598 0.4396 0.049 Uiso 1 1 calc R
C2 C 0.3491(5) 0.5444(2) -0.0284(7) 0.0332(12) Uani 1 1 d .
H2B H 0.4059 0.5593 0.0766 0.050 Uiso 1 1 calc R
H2C H 0.3039 0.5782 -0.0902 0.050 Uiso 1 1 calc R
H2D H 0.3972 0.5238 -0.1202 0.050 Uiso 1 1 calc R
C3 C 0.2274(5) 0.4992(2) 0.2252(7) 0.0244(10) Uani 1 1 d .
C4 C 0.2571(4) 0.5012(2) 0.0463(6) 0.0222(10) Uani 1 1 d .
C5 C 0.2000(5) 0.4587(2) -0.1045(6) 0.0227(10) Uani 1 1 d .
H5A H 0.1731 0.4822 -0.2189 0.027 Uiso 1 1 calc R
H5B H 0.2653 0.4304 -0.1387 0.027 Uiso 1 1 calc R
C6 C 0.0892(4) 0.4227(2) -0.0479(6) 0.0202(10) Uani 1 1 d .
H6A H 0.0167 0.4508 -0.0521 0.024 Uiso 1 1 calc R
C7 C 0.0522(5) 0.3719(2) -0.1870(6) 0.0234(10) Uani 1 1 d .
H7A H 0.0358 0.3888 -0.3157 0.028 Uiso 1 1 calc R
H7B H 0.1227 0.3434 -0.1892 0.028 Uiso 1 1 calc R
C8 C -0.0623(5) 0.3384(2) -0.1354(6) 0.0259(11) Uani 1 1 d .
H8A H -0.0782 0.3042 -0.2230 0.031 Uiso 1 1 calc R
H8B H -0.1355 0.3654 -0.1504 0.031 Uiso 1 1 calc R
C9 C -0.0467(5) 0.3148(2) 0.0711(6) 0.0249(11) Uani 1 1 d .
H9A H -0.1267 0.2979 0.1060 0.030 Uiso 1 1 calc R
H9B H 0.0168 0.2826 0.0819 0.030 Uiso 1 1 calc R
C10 C -0.0065(4) 0.3655(2) 0.2035(6) 0.0221(10) Uani 1 1 d .
C11 C 0.1117(4) 0.4001(2) 0.1613(6) 0.0193(10) Uani 1 1 d .
C12 C 0.1317(4) 0.4549(2) 0.2890(6) 0.0214(10) Uani 1 1 d .
H12A H 0.0510 0.4758 0.2942 0.026 Uiso 1 1 calc R
H12B H 0.1591 0.4412 0.4187 0.026 Uiso 1 1 calc R
C13 C 0.2280(4) 0.3587(2) 0.1820(6) 0.0203(10) Uani 1 1 d .
H13A H 0.3015 0.3814 0.1467 0.024 Uiso 1 1 calc R
H13B H 0.2148 0.3247 0.0926 0.024 Uiso 1 1 calc R
C14 C 0.4128(4) 0.3003(2) 0.3821(6) 0.0200(10) Uani 1 1 d .
C15 C 0.5119(5) 0.3399(2) 0.3818(6) 0.0245(11) Uani 1 1 d .
H15A H 0.4991 0.3817 0.3951 0.029 Uiso 1 1 calc R
C16 C 0.6307(5) 0.3171(3) 0.3615(7) 0.0327(13) Uani 1 1 d .
H16A H 0.6998 0.3435 0.3595 0.039 Uiso 1 1 calc R
C17 C 0.6477(5) 0.2556(3) 0.3441(7) 0.0367(14) Uani 1 1 d .
H17A H 0.7287 0.2402 0.3302 0.044 Uiso 1 1 calc R
C18 C 0.5477(5) 0.2169(2) 0.3469(7) 0.0347(13) Uani 1 1 d .
H18A H 0.5605 0.1750 0.3361 0.042 Uiso 1 1 calc R
C19 C 0.4292(5) 0.2388(2) 0.3652(6) 0.0239(11) Uani 1 1 d .
H19A H 0.3602 0.2122 0.3663 0.029 Uiso 1 1 calc R
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
O2 S1 C14 107.5(2)
O2 S1 C13 106.5(2)
C14 S1 C13 95.6(2)
C4 C3 C1 124.9(5)
C4 C3 C12 121.8(4)
C1 C3 C12 113.3(4)
C3 C4 C2 124.9(4)
C3 C4 C5 122.1(4)
C2 C4 C5 112.9(4)
C6 C5 C4 115.1(4)
C5 C6 C7 112.8(4)
C5 C6 C11 111.0(4)
C7 C6 C11 112.5(4)
C8 C7 C6 112.4(4)
C7 C8 C9 111.8(4)
C10 C9 C8 109.5(4)
O1 C10 C9 121.4(4)
O1 C10 C11 121.5(4)
C9 C10 C11 116.9(4)
C12 C11 C10 111.3(4)
C12 C11 C13 110.5(4)
C10 C11 C13 110.8(4)
C12 C11 C6 107.9(4)
C10 C11 C6 106.4(4)
C13 C11 C6 109.8(3)
C3 C12 C11 114.1(4)
C11 C13 S1 113.2(3)
C15 C14 C19 121.8(4)
C15 C14 S1 118.7(4)
C19 C14 S1 119.4(4)
C14 C15 C16 118.7(5)
C17 C16 C15 119.8(5)
C18 C17 C16 120.4(5)
C19 C18 C17 120.5(5)
C18 C19 C14 118.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.501(4)
S1 C14 1.799(5)
S1 C13 1.819(4)
O1 C10 1.222(5)
C1 C3 1.511(6)
C2 C4 1.510(7)
C3 C4 1.337(6)
C3 C12 1.523(7)
C4 C5 1.520(6)
C5 C6 1.519(6)
C6 C7 1.532(6)
C6 C11 1.567(6)
C7 C8 1.512(6)
C8 C9 1.553(6)
C9 C10 1.510(6)
C10 C11 1.539(6)
C11 C12 1.525(6)
C11 C13 1.553(6)
C14 C15 1.384(6)
C14 C19 1.391(6)
C15 C16 1.394(7)
C16 C17 1.390(8)
C17 C18 1.381(8)
C18 C19 1.381(7)
