#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/82/1508234.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_1508234
loop_
_publ_author_name
'Voica, Ana-Florina'
'Mendoza, Abraham'
'Gutekunst, Will R.'
'Fraga, Jorge Otero'
'Baran, Phil S.'
_publ_section_title
;
 Guided desaturation of unactivated aliphatics.
;
_journal_issue                   8
_journal_name_full               'Nature chemistry'
_journal_page_first              629
_journal_page_last               635
_journal_paper_doi               10.1038/nchem.1385
_journal_volume                  4
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C17 H24 O3 S'
_chemical_formula_weight         308.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9123(3)
_cell_length_b                   15.7609(7)
_cell_length_c                   17.3746(7)
_cell_measurement_reflns_used    6076
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.58
_cell_volume                     1619.02(13)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8652
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.9290
_exptl_absorpt_correction_T_min  0.9142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.2200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0775
_reflns_number_gt                2880
_reflns_number_total             2946
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.1385-s4.cif
_cod_data_source_block           baran200
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1508234
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 -0.20704(6) 0.39484(2) 0.24884(2) 0.02118(11) Uani 1 1 d .
O1 O -0.44863(19) 0.39979(7) 0.24724(7) 0.0288(3) Uani 1 1 d .
O2 O -0.0778(2) 0.43695(7) 0.19092(6) 0.0270(3) Uani 1 1 d .
O3 O -0.15698(16) 0.29667(6) 0.24734(6) 0.0210(2) Uani 1 1 d .
C1 C -0.1252(3) 0.14816(12) 0.39523(10) 0.0303(4) Uani 1 1 d .
C2 C 0.0458(3) 0.19291(9) 0.36662(9) 0.0235(3) Uani 1 1 d .
C3 C 0.1923(4) 0.24670(11) 0.41642(10) 0.0293(4) Uani 1 1 d .
C4 C 0.1052(3) 0.18517(9) 0.28185(8) 0.0203(3) Uani 1 1 d .
H4A H 0.0009 0.1423 0.2585 0.024 Uiso 1 1 calc R
C5 C 0.3496(3) 0.15341(10) 0.27009(9) 0.0236(3) Uani 1 1 d .
H5A H 0.4564 0.1955 0.2918 0.028 Uiso 1 1 calc R
H5B H 0.3704 0.0994 0.2983 0.028 Uiso 1 1 calc R
C6 C 0.4038(3) 0.13955(10) 0.18518(9) 0.0249(3) Uani 1 1 d .
H6A H 0.3097 0.0925 0.1652 0.030 Uiso 1 1 calc R
H6B H 0.5644 0.1227 0.1800 0.030 Uiso 1 1 calc R
C7 C 0.3612(3) 0.21894(9) 0.13684(9) 0.0221(3) Uani 1 1 d .
H7A H 0.4716 0.2635 0.1532 0.027 Uiso 1 1 calc R
C8 C 0.1215(3) 0.25302(10) 0.15080(9) 0.0216(3) Uani 1 1 d .
H8A H 0.1012 0.3070 0.1224 0.026 Uiso 1 1 calc R
H8B H 0.0094 0.2118 0.1310 0.026 Uiso 1 1 calc R
C9 C 0.0803(3) 0.26792(9) 0.23614(8) 0.0191(3) Uani 1 1 d .
H9A H 0.1878 0.3116 0.2562 0.023 Uiso 1 1 calc R
C10 C 0.3999(3) 0.20043(11) 0.05145(9) 0.0279(4) Uani 1 1 d .
H10A H 0.5536 0.1786 0.0440 0.042 Uiso 1 1 calc R
H10B H 0.3807 0.2528 0.0217 0.042 Uiso 1 1 calc R
H10C H 0.2902 0.1580 0.0339 0.042 Uiso 1 1 calc R
C11 C -0.1125(3) 0.42992(9) 0.33977(9) 0.0205(3) Uani 1 1 d .
C12 C -0.2530(3) 0.41890(9) 0.40343(9) 0.0247(3) Uani 1 1 d .
H12A H -0.3916 0.3889 0.3987 0.030 Uiso 1 1 calc R
C13 C -0.1873(3) 0.45246(10) 0.47387(9) 0.0261(4) Uani 1 1 d .
H13A H -0.2823 0.4451 0.5175 0.031 Uiso 1 1 calc R
C14 C 0.0155(3) 0.49675(10) 0.48179(10) 0.0239(3) Uani 1 1 d .
C15 C 0.1559(3) 0.50437(10) 0.41761(9) 0.0244(3) Uani 1 1 d .
H15A H 0.2973 0.5324 0.4227 0.029 Uiso 1 1 calc R
C16 C 0.0932(3) 0.47171(9) 0.34616(9) 0.0221(3) Uani 1 1 d .
H16A H 0.1893 0.4780 0.3027 0.027 Uiso 1 1 calc R
C17 C 0.0777(4) 0.53807(11) 0.55710(10) 0.0328(4) Uani 1 1 d .
H17A H 0.0084 0.5065 0.5996 0.049 Uiso 1 1 calc R
H17B H 0.0226 0.5967 0.5575 0.049 Uiso 1 1 calc R
H17C H 0.2425 0.5378 0.5631 0.049 Uiso 1 1 calc R
H1A H -0.212(4) 0.1122(12) 0.3639(12) 0.033(5) Uiso 1 1 d .
H3A H 0.196(4) 0.3037(15) 0.3984(13) 0.054(7) Uiso 1 1 d .
H1B H -0.156(3) 0.1522(12) 0.4486(12) 0.035(5) Uiso 1 1 d .
H3B H 0.124(4) 0.2511(14) 0.4674(14) 0.051(6) Uiso 1 1 d .
H3C H 0.344(4) 0.2213(14) 0.4160(14) 0.049(6) Uiso 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
O2 S1 O1 119.71(7)
O2 S1 O3 110.14(6)
O1 S1 O3 103.93(6)
O2 S1 C11 108.41(7)
O1 S1 C11 108.46(8)
O3 S1 C11 105.24(6)
C9 O3 S1 118.60(8)
C1 C2 C3 121.81(16)
C1 C2 C4 119.71(15)
C3 C2 C4 118.35(15)
C2 C4 C9 114.30(12)
C2 C4 C5 111.77(13)
C9 C4 C5 107.28(12)
C6 C5 C4 111.81(13)
C5 C6 C7 112.31(12)
C6 C7 C10 110.64(12)
C6 C7 C8 110.60(13)
C10 C7 C8 110.98(14)
C9 C8 C7 110.84(13)
O3 C9 C8 109.00(12)
O3 C9 C4 106.36(12)
C8 C9 C4 110.99(11)
C16 C11 C12 121.20(14)
C16 C11 S1 119.87(12)
C12 C11 S1 118.84(13)
C13 C12 C11 119.01(15)
C12 C13 C14 121.22(15)
C13 C14 C15 118.41(15)
C13 C14 C17 120.78(16)
C15 C14 C17 120.77(16)
C16 C15 C14 121.44(15)
C11 C16 C15 118.67(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4273(12)
S1 O1 1.4307(12)
S1 O3 1.5756(10)
S1 C11 1.7648(15)
O3 C9 1.4871(17)
C1 C2 1.329(3)
C2 C3 1.489(2)
C2 C4 1.519(2)
C4 C9 1.534(2)
C4 C5 1.543(2)
C5 C6 1.526(2)
C6 C7 1.528(2)
C7 C10 1.529(2)
C7 C8 1.535(2)
C8 C9 1.521(2)
C11 C16 1.387(2)
C11 C12 1.394(2)
C12 C13 1.389(2)
C13 C14 1.394(2)
C14 C15 1.395(2)
C14 C17 1.507(2)
C15 C16 1.394(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651964
