data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_requested_category         FO
loop_
_publ_author_name
'Sylvie Derien'
'Mathieu Achard'
'Christian Bruneau'
_publ_contact_author_name        'Sylvie Derien'
_publ_contact_author_email       derien@univ-rennes1.fr

data_MSM106
_database_code_depnum_ccdc_archive 'CCDC 874665'
#TrackingRef '- CIF file ID CC-COM-04-2012-032497.cif'

_audit_creation_date             2012-02-29T10:34:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C13 H14 N1 O2 S1'
_chemical_formula_sum            'C13 H14 N1 O2 S1'
_chemical_formula_weight         248.31
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F 2 d d'
_symmetry_space_group_name_Hall  'F -2d 2'
_symmetry_Int_Tables_number      43
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, -z'
'x+1/4, -y+1/4, z+1/4'
'x+1/4, y+1/4, -z+1/4'
'x, y+1/2, z+1/2'
'x, -y+1/2, -z+1/2'
'x+1/4, -y+3/4, z+3/4'
'x+1/4, y+3/4, -z+3/4'
'x+1/2, y, z+1/2'
'x+1/2, -y, -z+1/2'
'x+3/4, -y+1/4, z+3/4'
'x+3/4, y+1/4, -z+3/4'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'x+3/4, -y+3/4, z+1/4'
'x+3/4, y+3/4, -z+1/4'

_cell_length_a                   8.2634(3)
_cell_length_b                   20.1251(7)
_cell_length_c                   30.4131(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5057.8(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4148
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.44
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.26
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_T_max  0.938

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_number            9705
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2577
_reflns_number_gt                2455
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999),
CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+4.4419P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2577
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0837
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(7)
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S1 S 0.48912(6) 0.19854(2) 0.653564(15) 0.02154(12) Uani 1 1 d . . .
C1 C 0.3338(4) -0.00899(12) 0.79101(7) 0.0426(6) Uani 1 1 d . . .
H1A H 0.2672 -0.0458 0.7837 0.051 Uiso 1 1 calc R . .
H1B H 0.3753 -0.0046 0.82 0.051 Uiso 1 1 calc R . .
C2 C 0.3740(3) 0.04245(10) 0.75666(7) 0.0276(5) Uani 1 1 d . . .
C3 C 0.4697(3) 0.09718(9) 0.76711(6) 0.0247(4) Uani 1 1 d . . .
H3 H 0.5123 0.1013 0.796 0.03 Uiso 1 1 calc R . .
C4 C 0.5042(3) 0.14564(9) 0.73625(6) 0.0236(4) Uani 1 1 d . . .
H4 H 0.5696 0.1828 0.7438 0.028 Uiso 1 1 calc R . .
C5 C 0.4412(2) 0.13909(9) 0.69394(6) 0.0206(4) Uani 1 1 d . . .
C6 C 0.3464(3) 0.08460(10) 0.68260(6) 0.0237(4) Uani 1 1 d . . .
H6 H 0.3044 0.0803 0.6537 0.028 Uiso 1 1 calc R . .
C7 C 0.3143(3) 0.03679(10) 0.71400(7) 0.0284(5) Uani 1 1 d . . .
H7 H 0.2503 -0.0007 0.7063 0.034 Uiso 1 1 calc R . .
O8 O 0.53450(19) 0.25913(6) 0.67486(5) 0.0309(4) Uani 1 1 d . . .
O9 O 0.36218(19) 0.19845(6) 0.62157(4) 0.0281(3) Uani 1 1 d . . .
N10 N 0.6513(2) 0.17143(8) 0.62786(6) 0.0259(4) Uani 1 1 d . . .
C11 C 0.8038(3) 0.18026(12) 0.64849(8) 0.0352(5) Uani 1 1 d . . .
H11 H 0.8131 0.2113 0.6719 0.042 Uiso 1 1 calc R . .
C12 C 0.9324(3) 0.14678(14) 0.63618(10) 0.0510(7) Uani 1 1 d . . .
H12 H 1.0313 0.1551 0.6511 0.061 Uiso 1 1 calc R . .
C13 C 0.9325(4) 0.09644(15) 0.60014(11) 0.0607(9) Uani 1 1 d . . .
H13A H 0.9463 0.0516 0.6129 0.073 Uiso 1 1 calc R . .
H13B H 1.0251 0.105 0.5803 0.073 Uiso 1 1 calc R . .
C14 C 0.7785(3) 0.09857(11) 0.57425(9) 0.0465(7) Uani 1 1 d . . .
C15 C 0.6299(3) 0.10955(11) 0.60207(7) 0.0352(5) Uani 1 1 d . . .
H15A H 0.5332 0.1134 0.583 0.042 Uiso 1 1 calc R . .
H15B H 0.614 0.0714 0.6222 0.042 Uiso 1 1 calc R . .
C16 C 0.7683(5) 0.08997(13) 0.53113(9) 0.0624(9) Uani 1 1 d . . .
H16A H 0.8632 0.0817 0.5144 0.075 Uiso 1 1 calc R . .
H16B H 0.6659 0.092 0.517 0.075 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0246(2) 0.0181(2) 0.0220(2) 0.00059(18) -0.0010(2) 0.00534(19)
C1 0.0641(18) 0.0358(12) 0.0280(10) 0.0075(9) -0.0084(12) -0.0185(12)
C2 0.0319(12) 0.0246(10) 0.0262(10) 0.0016(8) 0.0005(9) 0.0017(9)
C3 0.0261(11) 0.0275(9) 0.0206(9) -0.0021(7) -0.0048(8) 0.0032(9)
C4 0.0242(11) 0.0221(8) 0.0244(9) -0.0039(7) -0.0021(9) 0.0013(8)
C5 0.0208(10) 0.0197(9) 0.0214(9) 0.0001(7) 0.0005(8) 0.0036(7)
C6 0.0250(11) 0.0265(9) 0.0196(8) -0.0023(7) -0.0023(9) 0.0011(8)
C7 0.0295(12) 0.0268(10) 0.0289(10) -0.0026(8) -0.0011(9) -0.0053(9)
O8 0.0446(11) 0.0178(6) 0.0303(7) -0.0007(6) -0.0009(7) 0.0022(6)
O9 0.0267(8) 0.0332(8) 0.0243(7) 0.0020(6) -0.0022(6) 0.0087(6)
N10 0.0224(9) 0.0221(8) 0.0331(9) 0.0018(7) 0.0026(7) 0.0040(7)
C11 0.0252(12) 0.0369(12) 0.0434(13) 0.0176(10) -0.0023(10) -0.0013(10)
C12 0.0275(13) 0.0601(17) 0.0653(17) 0.0345(15) 0.0083(12) 0.0077(12)
C13 0.0477(18) 0.0604(17) 0.074(2) 0.0389(16) 0.0364(15) 0.0338(14)
C14 0.0577(19) 0.0249(10) 0.0570(15) 0.0103(10) 0.0331(14) 0.0164(11)
C15 0.0398(14) 0.0258(10) 0.0401(12) -0.0041(9) 0.0168(11) 0.0058(10)
C16 0.077(2) 0.0529(16) 0.0574(17) -0.0057(13) 0.0348(17) 0.0069(16)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1 O9 1.4308(15) . ?
S1 O8 1.4308(14) . ?
S1 N10 1.6445(18) . ?
S1 C5 1.7595(19) . ?
C1 C2 1.508(3) . ?
C1 H1A 0.95 . ?
C1 H1B 0.95 . ?
C2 C7 1.392(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.95 . ?
C4 C5 1.394(3) . ?
C4 H4 0.95 . ?
C5 C6 1.391(3) . ?
C6 C7 1.382(3) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
N10 C11 1.419(3) . ?
N10 C15 1.482(3) . ?
C11 C12 1.313(4) . ?
C11 H11 0.95 . ?
C12 C13 1.492(4) . ?
C12 H12 0.95 . ?
C13 C14 1.497(4) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C16 1.325(4) . ?
C14 C15 1.508(3) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 H16A 0.95 . ?
C16 H16B 0.95 . ?

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
O9 S1 O8 120.07(8) . . ?
O9 S1 N10 105.88(9) . . ?
O8 S1 N10 106.52(9) . . ?
O9 S1 C5 107.99(9) . . ?
O8 S1 C5 108.82(9) . . ?
N10 S1 C5 106.82(9) . . ?
C2 C1 H1A 120 . . ?
C2 C1 H1B 120 . . ?
H1A C1 H1B 120 . . ?
C7 C2 C3 118.58(19) . . ?
C7 C2 C1 120.77(19) . . ?
C3 C2 C1 120.64(19) . . ?
C4 C3 C2 121.30(18) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.88(18) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.89(17) . . ?
C6 C5 S1 119.32(14) . . ?
C4 C5 S1 119.73(15) . . ?
C7 C6 C5 119.06(17) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.28(19) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C11 N10 C15 116.43(18) . . ?
C11 N10 S1 118.17(15) . . ?
C15 N10 S1 115.66(15) . . ?
C12 C11 N10 121.9(3) . . ?
C12 C11 H11 119 . . ?
N10 C11 H11 119 . . ?
C11 C12 C13 123.9(3) . . ?
C11 C12 H12 118 . . ?
C13 C12 H12 118 . . ?
C12 C13 C14 111.5(2) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108 . . ?
C16 C14 C13 124.8(3) . . ?
C16 C14 C15 121.5(3) . . ?
C13 C14 C15 113.7(2) . . ?
N10 C15 C14 108.8(2) . . ?
N10 C15 H15A 109.9 . . ?
C14 C15 H15A 109.9 . . ?
N10 C15 H15B 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C14 C16 H16A 120 . . ?
C14 C16 H16B 120 . . ?
H16A C16 H16B 120 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -178.3(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 C5 S1 -177.76(15) . . . . ?
O9 S1 C5 C6 27.79(18) . . . . ?
O8 S1 C5 C6 159.64(16) . . . . ?
N10 S1 C5 C6 -85.71(17) . . . . ?
O9 S1 C5 C4 -154.94(16) . . . . ?
O8 S1 C5 C4 -23.09(19) . . . . ?
N10 S1 C5 C4 91.55(17) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
S1 C5 C6 C7 177.56(16) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?
C3 C2 C7 C6 -1.0(3) . . . . ?
C1 C2 C7 C6 178.1(2) . . . . ?
O9 S1 N10 C11 166.01(14) . . . . ?
O8 S1 N10 C11 37.12(17) . . . . ?
C5 S1 N10 C11 -79.06(17) . . . . ?
O9 S1 N10 C15 -49.16(17) . . . . ?
O8 S1 N10 C15 -178.05(14) . . . . ?
C5 S1 N10 C15 65.77(17) . . . . ?
C15 N10 C11 C12 18.5(3) . . . . ?
S1 N10 C11 C12 163.07(18) . . . . ?
N10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 11.2(3) . . . . ?
C12 C13 C14 C16 142.5(3) . . . . ?
C12 C13 C14 C15 -39.3(3) . . . . ?
C11 N10 C15 C14 -44.9(3) . . . . ?
S1 N10 C15 C14 169.69(16) . . . . ?
C16 C14 C15 N10 -125.8(3) . . . . ?
C13 C14 C15 N10 56.0(3) . . . . ?