# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2015167
_database_code_depnum_ccdc_archive 'CCDC 1465160'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2-phenyl-5-(tosylmethyl)oxazol
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H15 N O3 S'
_chemical_formula_sum            'C17 H15 N O3 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'Light yellow'

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         313.36

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0578(6)
_cell_length_b                   11.1512(14)
_cell_length_c                   11.9001(15)
_cell_angle_alpha                71.535(12)
_cell_angle_beta                 86.207(9)
_cell_angle_gamma                89.004(9)
_cell_volume                     760.81(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1151
_cell_measurement_theta_min      3.5160
_cell_measurement_theta_max      24.7250
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5916
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         29.20
_reflns_number_total             3490
_reflns_number_gt                1988
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0471P)²+0.0000P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         3490
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.27134(12) 0.49539(7) 0.32857(7) 0.0491(2) Uani 1 1 d . . .
O1 O 0.4451(3) 0.57217(19) 0.34697(18) 0.0679(7) Uani 1 1 d . . .
O2 O 0.0582(3) 0.55118(19) 0.30050(19) 0.0650(6) Uani 1 1 d . . .
O3 O 0.0979(3) 0.19999(17) 0.38523(15) 0.0433(5) Uani 1 1 d . . .
N N -0.2426(4) 0.1570(2) 0.4704(2) 0.0482(6) Uani 1 1 d . . .
C1 C 0.3644(4) 0.4294(2) 0.2181(2) 0.0407(6) Uani 1 1 d . . .
C2 C 0.5766(5) 0.3817(3) 0.2196(2) 0.0488(7) Uani 1 1 d . . .
H2B H 0.6738 0.3923 0.2730 0.059 Uiso 1 1 calc R . .
C3 C 0.6420(5) 0.3184(3) 0.1411(3) 0.0554(8) Uani 1 1 d . . .
H3A H 0.7839 0.2848 0.1433 0.066 Uiso 1 1 calc R . .
C4 C 0.5040(5) 0.3031(3) 0.0590(3) 0.0532(8) Uani 1 1 d . . .
C5 C 0.2954(5) 0.3559(3) 0.0561(3) 0.0573(9) Uani 1 1 d . . .
H5A H 0.2016 0.3499 -0.0007 0.069 Uiso 1 1 calc R . .
C6 C 0.2238(5) 0.4173(3) 0.1355(3) 0.0518(8) Uani 1 1 d . . .
H6A H 0.0816 0.4505 0.1335 0.062 Uiso 1 1 calc R . .
C7 C 0.5812(6) 0.2303(3) -0.0238(3) 0.0818(11) Uani 1 1 d . . .
H7A H 0.7302 0.2021 -0.0087 0.123 Uiso 1 1 calc R . .
H7B H 0.5760 0.2840 -0.1045 0.123 Uiso 1 1 calc R . .
H7C H 0.4864 0.1584 -0.0107 0.123 Uiso 1 1 calc R . .
C8 C 0.2369(4) 0.3616(3) 0.4605(2) 0.0482(7) Uani 1 1 d . . .
H8A H 0.3750 0.3152 0.4724 0.058 Uiso 1 1 calc R . .
H8B H 0.2055 0.3915 0.5280 0.058 Uiso 1 1 calc R . .
C9 C 0.0593(4) 0.2750(2) 0.4571(2) 0.0406(6) Uani 1 1 d . . .
C10 C -0.1444(4) 0.2482(3) 0.5076(2) 0.0475(7) Uani 1 1 d . . .
H10A H -0.2118 0.2856 0.5607 0.057 Uiso 1 1 calc R . .
C11 C -0.0932(4) 0.1320(2) 0.3983(2) 0.0385(6) Uani 1 1 d . . .
C12 C -0.1041(4) 0.0464(2) 0.3283(2) 0.0409(6) Uani 1 1 d . . .
C13 C -0.2944(5) -0.0251(3) 0.3370(3) 0.0539(8) Uani 1 1 d . . .
H13A H -0.4146 -0.0183 0.3874 0.065 Uiso 1 1 calc R . .
C14 C -0.3043(6) -0.1061(3) 0.2708(3) 0.0670(10) Uani 1 1 d . . .
H14A H -0.4315 -0.1538 0.2766 0.080 Uiso 1 1 calc R . .
C15 C -0.1260(6) -0.1168(3) 0.1956(3) 0.0759(11) Uani 1 1 d . . .
H15A H -0.1331 -0.1721 0.1517 0.091 Uiso 1 1 calc R . .
C16 C 0.0607(5) -0.0460(3) 0.1859(3) 0.0709(10) Uani 1 1 d . . .
H16A H 0.1795 -0.0525 0.1346 0.085 Uiso 1 1 calc R . .
C17 C 0.0734(5) 0.0353(3) 0.2524(3) 0.0534(8) Uani 1 1 d . . .
H17A H 0.2012 0.0826 0.2462 0.064 Uiso 1 1 calc R . .


_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 O2 1.436(2) . ?
S1 O1 1.4387(19) . ?
S1 C1 1.758(3) . ?
S1 C8 1.794(3) . ?
O3 C9 1.380(3) . ?
O3 C11 1.368(3) . ?
N C11 1.294(3) . ?
N C10 1.388(3) . ?
C1 C6 1.381(3) . ?
C1 C2 1.382(4) . ?
C2 C3 1.374(4) . ?
C2 H2B 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(4) . ?
C4 C7 1.510(4) . ?
C5 C6 1.376(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.469(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.332(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.457(4) . ?
C12 C17 1.387(4) . ?
C12 C13 1.393(4) . ?
C13 C14 1.378(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.385(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.368(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.386(4) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?

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
O2 S1 O1 118.84(13) . . ?
O2 S1 C1 108.59(13) . . ?
O1 S1 C1 108.95(13) . . ?
O2 S1 C8 108.43(13) . . ?
O1 S1 C8 107.02(12) . . ?
C1 S1 C8 104.00(13) . . ?
C9 O3 C11 104.6(2) . . ?
C11 N C10 104.0(2) . . ?
C6 C1 C2 120.0(3) . . ?
C6 C1 S1 120.8(2) . . ?
C2 C1 S1 119.0(2) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2B 120.5 . . ?
C1 C2 H2B 120.5 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C7 120.3(3) . . ?
C5 C4 C7 122.0(3) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 113.75(18) . . ?
C9 C8 H8A 108.8 . . ?
S1 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
S1 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 O3 107.0(2) . . ?
C10 C9 C8 135.6(3) . . ?
O3 C9 C8 117.4(2) . . ?
C9 C10 N 110.8(2) . . ?
C9 C10 H10A 124.6 . . ?
N C10 H10A 124.6 . . ?
N C11 O3 113.6(2) . . ?
N C11 C12 129.2(2) . . ?
O3 C11 C12 117.1(2) . . ?
C17 C12 C13 119.3(3) . . ?
C17 C12 C11 120.7(2) . . ?
C13 C12 C11 120.0(3) . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C12 120.2(3) . . ?
C16 C17 H17A 119.9 . . ?
C12 C17 H17A 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.843
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.058


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2015178
_database_code_depnum_ccdc_archive 'CCDC 1465161'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2-phenyl-5-((phenylsulfonyl)methyl)oxazole
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H13 N O3 S'
_chemical_formula_sum            'C16 H13 N O3 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'Light brown'

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         299.33

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8951(3)
_cell_length_b                   10.7554(8)
_cell_length_c                   11.3589(8)
_cell_angle_alpha                75.588(3)
_cell_angle_beta                 86.378(2)
_cell_angle_gamma                81.134(2)
_cell_volume                     688.97(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4666
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      26.36
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9023
_exptl_absorpt_correction_T_max  0.9643
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12062
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         26.39
_reflns_number_total             2809
_reflns_number_gt                2256
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0600P)²+0.3157P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         2809
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S S 0.30226(8) 0.82004(5) 0.47343(4) 0.02148(16) Uani 1 1 d . . .
O1 O 0.0874(2) 0.80044(14) 0.53814(13) 0.0303(4) Uani 1 1 d . . .
O2 O 0.4937(3) 0.83186(14) 0.54017(14) 0.0327(4) Uani 1 1 d . . .
O3 O 0.1203(2) 0.88074(12) 0.19190(12) 0.0194(3) Uani 1 1 d . . .
N N -0.2404(3) 0.97806(15) 0.16213(15) 0.0212(4) Uani 1 1 d . . .
C1 C 0.3824(3) 0.69163(18) 0.40084(17) 0.0201(4) Uani 1 1 d . . .
C2 C 0.2384(3) 0.59942(19) 0.41044(18) 0.0240(4) Uani 1 1 d . . .
H2B H 0.0951 0.6064 0.4532 0.029 Uiso 1 1 calc R . .
C3 C 0.3063(4) 0.4965(2) 0.35678(19) 0.0295(5) Uani 1 1 d . . .
H3A H 0.2113 0.4309 0.3649 0.035 Uiso 1 1 calc R . .
C4 C 0.5112(4) 0.4894(2) 0.29182(19) 0.0322(5) Uani 1 1 d . . .
H4A H 0.5559 0.4192 0.2545 0.039 Uiso 1 1 calc R . .
C5 C 0.6525(4) 0.5833(2) 0.2805(2) 0.0336(5) Uani 1 1 d . . .
H5A H 0.7920 0.5784 0.2341 0.040 Uiso 1 1 calc R . .
C6 C 0.5906(3) 0.68476(19) 0.33672(19) 0.0266(5) Uani 1 1 d . . .
H6A H 0.6888 0.7483 0.3314 0.032 Uiso 1 1 calc R . .
C7 C 0.2564(3) 0.96363(18) 0.35131(18) 0.0210(4) Uani 1 1 d . . .
H7A H 0.2175 1.0403 0.3860 0.025 Uiso 1 1 calc R . .
H7B H 0.4008 0.9731 0.3026 0.025 Uiso 1 1 calc R . .
C8 C 0.0714(3) 0.96124(17) 0.27055(17) 0.0186(4) Uani 1 1 d . . .
C9 C -0.1451(3) 1.01981(19) 0.25191(18) 0.0213(4) Uani 1 1 d . . .
H9A H -0.2223 1.0809 0.2938 0.026 Uiso 1 1 calc R . .
C10 C -0.0770(3) 0.89604(17) 0.13036(17) 0.0173(4) Uani 1 1 d . . .
C11 C -0.0806(3) 0.81766(17) 0.04312(17) 0.0187(4) Uani 1 1 d . . .
C12 C -0.2752(3) 0.83060(19) -0.02460(19) 0.0247(4) Uani 1 1 d . . .
H12A H -0.4061 0.8909 -0.0142 0.030 Uiso 1 1 calc R . .
C13 C -0.2778(4) 0.7554(2) -0.1072(2) 0.0319(5) Uani 1 1 d . . .
H13A H -0.4100 0.7652 -0.1542 0.038 Uiso 1 1 calc R . .
C14 C -0.0890(4) 0.6664(2) -0.1217(2) 0.0347(5) Uani 1 1 d . . .
H14A H -0.0920 0.6147 -0.1781 0.042 Uiso 1 1 calc R . .
C15 C 0.1042(4) 0.6525(2) -0.0540(2) 0.0309(5) Uani 1 1 d . . .
H15A H 0.2335 0.5910 -0.0640 0.037 Uiso 1 1 calc R . .
C16 C 0.1102(3) 0.72754(19) 0.02815(18) 0.0234(4) Uani 1 1 d . . .
H16A H 0.2435 0.7179 0.0743 0.028 Uiso 1 1 calc R . .


_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
S O2 1.4368(15) . ?
S O1 1.4412(15) . ?
S C1 1.7683(19) . ?
S C7 1.799(2) . ?
O3 C10 1.362(2) . ?
O3 C8 1.381(2) . ?
N C10 1.300(2) . ?
N C9 1.391(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.388(3) . ?
C2 H2B 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.476(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.338(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.455(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.399(3) . ?
C12 C13 1.385(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?

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
O2 S O1 118.41(10) . . ?
O2 S C1 108.86(9) . . ?
O1 S C1 107.85(9) . . ?
O2 S C7 107.14(9) . . ?
O1 S C7 108.94(9) . . ?
C1 S C7 104.83(9) . . ?
C10 O3 C8 104.69(14) . . ?
C10 N C9 104.33(15) . . ?
C2 C1 C6 121.42(18) . . ?
C2 C1 S 119.42(15) . . ?
C6 C1 S 119.15(15) . . ?
C3 C2 C1 119.06(19) . . ?
C3 C2 H2B 120.5 . . ?
C1 C2 H2B 120.5 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.64(19) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 118.7(2) . . ?
C1 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
C8 C7 S 112.99(13) . . ?
C8 C7 H7A 109.0 . . ?
S C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
S C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 O3 107.37(16) . . ?
C9 C8 C7 135.77(18) . . ?
O3 C8 C7 116.86(15) . . ?
C8 C9 N 110.03(17) . . ?
C8 C9 H9A 125.0 . . ?
N C9 H9A 125.0 . . ?
N C10 O3 113.58(16) . . ?
N C10 C11 129.07(17) . . ?
O3 C10 C11 117.32(16) . . ?
C12 C11 C16 119.62(18) . . ?
C12 C11 C10 120.19(17) . . ?
C16 C11 C10 120.18(17) . . ?
C13 C12 C11 119.90(19) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C11 119.76(19) . . ?
C15 C16 H16A 120.1 . . ?
C11 C16 H16A 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.065


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rp2921
_database_code_depnum_ccdc_archive 'CCDC 1465162'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(E)-2-phenyl-4-(tosylmethylene)-3-oxa-1-azaspiro[4.5]dec-1-ene
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H23 N O3 S'
_chemical_formula_sum            'C22 H23 N O3 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            Yellow

_diffrn_ambient_temperature      302(2)
_chemical_formula_weight         381.47

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_int_tables_number      9
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   9.8639(12)
_cell_length_b                   21.953(3)
_cell_length_c                   10.1344(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.004(4)
_cell_angle_gamma                90.00
_cell_volume                     1988.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    6343
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      26.21
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9119
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15215
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3891
_reflns_number_gt                3417
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0482P)²+0.4191P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_number_reflns         3891
_refine_ls_number_parameters     244
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S S 1.01537(6) 0.28317(2) 0.70882(6) 0.04294(14) Uani 1 1 d . . .
O1 O 1.0061(2) 0.31277(9) 0.57950(18) 0.0610(5) Uani 1 1 d . . .
O2 O 1.05836(19) 0.22020(7) 0.7314(2) 0.0636(5) Uani 1 1 d . . .
O3 O 1.02582(14) 0.41828(6) 0.78385(14) 0.0380(3) Uani 1 1 d . . .
N N 1.14626(17) 0.47942(7) 0.97874(17) 0.0349(4) Uani 1 1 d . . .
C1 C 0.8407(2) 0.29050(9) 0.7150(2) 0.0393(5) Uani 1 1 d . . .
C2 C 0.7359(3) 0.33133(11) 0.6265(3) 0.0529(6) Uani 1 1 d . . .
H2B H 0.7558 0.3549 0.5605 0.064 Uiso 1 1 calc R . .
C3 C 0.6010(3) 0.33709(13) 0.6363(3) 0.0639(7) Uani 1 1 d . . .
H3A H 0.5313 0.3654 0.5779 0.077 Uiso 1 1 calc R . .
C4 C 0.5677(3) 0.30136(13) 0.7315(3) 0.0600(7) Uani 1 1 d . . .
C5 C 0.6729(3) 0.26093(12) 0.8185(3) 0.0601(7) Uani 1 1 d . . .
H5A H 0.6518 0.2368 0.8829 0.072 Uiso 1 1 calc R . .
C6 C 0.8100(3) 0.25516(10) 0.8130(3) 0.0511(6) Uani 1 1 d . . .
H6A H 0.8809 0.2279 0.8741 0.061 Uiso 1 1 calc R . .
C7 C 0.4188(4) 0.3086(2) 0.7398(5) 0.0982(12) Uani 1 1 d . . .
H7A H 0.4133 0.2805 0.8099 0.147 Uiso 1 1 calc R . .
H7B H 0.3391 0.3003 0.6460 0.147 Uiso 1 1 calc R . .
H7C H 0.4095 0.3495 0.7685 0.147 Uiso 1 1 calc R . .
C8 C 1.1378(2) 0.32225(9) 0.8630(2) 0.0385(4) Uani 1 1 d . . .
H8A H 1.2137 0.3001 0.9347 0.046 Uiso 1 1 calc R . .
C9 C 1.1301(2) 0.38133(8) 0.8847(2) 0.0326(4) Uani 1 1 d . . .
C10 C 1.0439(2) 0.47532(8) 0.8519(2) 0.0333(4) Uani 1 1 d . . .
C11 C 1.2215(2) 0.41976(8) 1.0173(2) 0.0325(4) Uani 1 1 d . . .
C12 C 1.2153(2) 0.39411(10) 1.1545(2) 0.0400(5) Uani 1 1 d . . .
H12A H 1.1123 0.3934 1.1420 0.048 Uiso 1 1 calc R . .
H12B H 1.2520 0.3525 1.1691 0.048 Uiso 1 1 calc R . .
C13 C 1.3086(3) 0.43180(12) 1.2885(2) 0.0521(6) Uani 1 1 d . . .
H13A H 1.2648 0.4720 1.2790 0.062 Uiso 1 1 calc R . .
H13B H 1.3070 0.4127 1.3741 0.062 Uiso 1 1 calc R . .
C14 C 1.4687(3) 0.43784(12) 1.3083(3) 0.0560(6) Uani 1 1 d . . .
H14A H 1.5160 0.3981 1.3280 0.067 Uiso 1 1 calc R . .
H14B H 1.5233 0.4639 1.3913 0.067 Uiso 1 1 calc R . .
C15 C 1.4759(2) 0.46485(11) 1.1722(3) 0.0524(6) Uani 1 1 d . . .
H15A H 1.5791 0.4666 1.1855 0.063 Uiso 1 1 calc R . .
H15B H 1.4366 0.5060 1.1572 0.063 Uiso 1 1 calc R . .
C16 C 1.3849(2) 0.42601(10) 1.0393(2) 0.0394(5) Uani 1 1 d . . .
H16A H 1.4297 0.3859 1.0513 0.047 Uiso 1 1 calc R . .
H16B H 1.3875 0.4444 0.9534 0.047 Uiso 1 1 calc R . .
C17 C 0.9434(2) 0.52357(9) 0.7632(2) 0.0344(4) Uani 1 1 d . . .
C18 C 0.9364(2) 0.57796(9) 0.8297(2) 0.0415(5) Uani 1 1 d . . .
H18A H 0.9927 0.5828 0.9293 0.050 Uiso 1 1 calc R . .
C19 C 0.8466(3) 0.62474(10) 0.7492(3) 0.0502(6) Uani 1 1 d . . .
H19A H 0.8395 0.6606 0.7947 0.060 Uiso 1 1 calc R . .
C20 C 0.7674(3) 0.61830(11) 0.6011(3) 0.0547(6) Uani 1 1 d . . .
H20A H 0.7086 0.6503 0.5463 0.066 Uiso 1 1 calc R . .
C21 C 0.7748(3) 0.56475(12) 0.5335(3) 0.0549(6) Uani 1 1 d . . .
H21A H 0.7217 0.5609 0.4331 0.066 Uiso 1 1 calc R . .
C22 C 0.8609(2) 0.51651(11) 0.6142(2) 0.0444(5) Uani 1 1 d . . .
H22A H 0.8633 0.4799 0.5690 0.053 Uiso 1 1 calc R . .


_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
S O2 1.4356(16) . ?
S O1 1.4307(18) . ?
S C8 1.744(2) . ?
S C1 1.758(2) . ?
O3 C9 1.368(2) . ?
O3 C10 1.404(2) . ?
N C10 1.258(2) . ?
N C11 1.474(2) . ?
C1 C2 1.376(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.381(4) . ?
C2 H2B 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.367(4) . ?
C4 C7 1.515(4) . ?
C5 C6 1.382(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.323(3) . ?
C8 H8A 0.9300 . ?
C9 C11 1.519(3) . ?
C10 C17 1.469(3) . ?
C11 C16 1.537(3) . ?
C11 C12 1.525(3) . ?
C12 C13 1.523(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.511(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.530(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.525(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.389(3) . ?
C17 C18 1.387(3) . ?
C18 C19 1.376(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.375(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.378(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.387(3) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?

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
O2 S O1 118.90(12) . . ?
O2 S C8 106.57(11) . . ?
O1 S C8 110.43(11) . . ?
O2 S C1 108.09(10) . . ?
O1 S C1 107.87(11) . . ?
C8 S C1 103.97(10) . . ?
C9 O3 C10 105.24(14) . . ?
C10 N C11 107.71(15) . . ?
C2 C1 C6 119.9(2) . . ?
C2 C1 S 120.94(17) . . ?
C6 C1 S 119.14(17) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2B 120.2 . . ?
C1 C2 H2B 120.2 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 C7 121.5(3) . . ?
C3 C4 C7 120.0(3) . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 H6A 120.3 . . ?
C5 C6 H6A 120.3 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S 124.37(16) . . ?
C9 C8 H8A 117.8 . . ?
S C8 H8A 117.8 . . ?
C8 C9 O3 122.34(18) . . ?
C8 C9 C11 129.59(18) . . ?
O3 C9 C11 108.02(14) . . ?
N C10 O3 116.47(16) . . ?
N C10 C17 128.03(17) . . ?
O3 C10 C17 115.46(16) . . ?
N C11 C9 102.40(14) . . ?
N C11 C16 109.80(16) . . ?
C9 C11 C16 111.81(15) . . ?
N C11 C12 111.11(16) . . ?
C9 C11 C12 111.37(16) . . ?
C16 C11 C12 110.13(16) . . ?
C13 C12 C11 111.74(18) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 111.69(18) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 110.98(19) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 110.20(19) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C11 111.56(17) . . ?
C15 C16 H16A 109.3 . . ?
C11 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C11 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C22 C17 C18 119.87(19) . . ?
C22 C17 C10 121.25(19) . . ?
C18 C17 C10 118.83(18) . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19A 120.1 . . ?
C18 C19 H19A 120.1 . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C17 C22 C21 119.2(2) . . ?
C17 C22 H22A 120.4 . . ?
C21 C22 H22A 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.038

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rp2009
_database_code_depnum_ccdc_archive 'CCDC 1465163'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5-(((4-fluorophenyl)sulfonyl)methyl)-2-phenyloxazole
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H12 F N O3 S'
_chemical_formula_sum            'C16 H12 F N O3 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         317.33

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2389(3)
_cell_length_b                   9.1551(6)
_cell_length_c                   13.2937(8)
_cell_angle_alpha                72.550(2)
_cell_angle_beta                 81.797(2)
_cell_angle_gamma                75.434(2)
_cell_volume                     699.22(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6858
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      26.41
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9004
_exptl_absorpt_correction_T_max  0.9676
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17166
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         26.44
_reflns_number_total             2880
_reflns_number_gt                2446
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0455P)²+0.3946P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         2880
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S S 0.31576(7) 0.80788(5) 0.95036(3) 0.02002(13) Uani 1 1 d . . .
F F 0.4100(2) 0.32729(14) 0.73223(10) 0.0408(3) Uani 1 1 d . . .
O1 O 0.5266(2) 0.80761(15) 0.98190(10) 0.0289(3) Uani 1 1 d . . .
O2 O 0.1327(2) 0.79206(15) 1.02926(9) 0.0273(3) Uani 1 1 d . . .
O3 O 0.11199(18) 0.90938(13) 0.70936(9) 0.0182(3) Uani 1 1 d . . .
N N -0.2570(2) 0.97038(18) 0.72830(12) 0.0245(3) Uani 1 1 d . . .
C1 C 0.3485(3) 0.65881(19) 0.88711(13) 0.0199(3) Uani 1 1 d . . .
C2 C 0.5456(3) 0.6182(2) 0.82893(14) 0.0250(4) Uani 1 1 d . . .
H2B H 0.6654 0.6666 0.8256 0.030 Uiso 1 1 calc R . .
C3 C 0.5654(3) 0.5061(2) 0.77573(15) 0.0292(4) Uani 1 1 d . . .
H3A H 0.6982 0.4767 0.7348 0.035 Uiso 1 1 calc R . .
C4 C 0.3887(3) 0.4385(2) 0.78349(14) 0.0267(4) Uani 1 1 d . . .
C5 C 0.1919(3) 0.4764(2) 0.84098(14) 0.0261(4) Uani 1 1 d . . .
H5A H 0.0737 0.4263 0.8448 0.031 Uiso 1 1 calc R . .
C6 C 0.1714(3) 0.5897(2) 0.89301(13) 0.0223(4) Uani 1 1 d . . .
H6A H 0.0369 0.6202 0.9326 0.027 Uiso 1 1 calc R . .
C7 C 0.2339(3) 0.98626(19) 0.84784(13) 0.0189(3) Uani 1 1 d . . .
H7A H 0.1859 1.0755 0.8794 0.023 Uiso 1 1 calc R . .
H7B H 0.3632 1.0047 0.7970 0.023 Uiso 1 1 calc R . .
C8 C 0.0510(3) 0.97960(19) 0.79103(12) 0.0179(3) Uani 1 1 d . . .
C9 C -0.1707(3) 1.0161(2) 0.80175(14) 0.0228(4) Uani 1 1 d . . .
H9A H -0.2565 1.0659 0.8522 0.027 Uiso 1 1 calc R . .
C10 C -0.0835(3) 0.90798(19) 0.67667(13) 0.0183(3) Uani 1 1 d . . .
C11 C -0.0756(3) 0.83506(19) 0.59210(13) 0.0192(3) Uani 1 1 d . . .
C12 C -0.2721(3) 0.8416(2) 0.55099(14) 0.0253(4) Uani 1 1 d . . .
H12A H -0.4103 0.8909 0.5793 0.030 Uiso 1 1 calc R . .
C13 C -0.2663(3) 0.7764(2) 0.46909(15) 0.0298(4) Uani 1 1 d . . .
H13A H -0.4004 0.7823 0.4406 0.036 Uiso 1 1 calc R . .
C14 C -0.0658(3) 0.7026(2) 0.42845(15) 0.0294(4) Uani 1 1 d . . .
H14A H -0.0623 0.6575 0.3724 0.035 Uiso 1 1 calc R . .
C15 C 0.1299(3) 0.6946(2) 0.46964(15) 0.0307(4) Uani 1 1 d . . .
H15A H 0.2675 0.6439 0.4417 0.037 Uiso 1 1 calc R . .
C16 C 0.1260(3) 0.7600(2) 0.55127(14) 0.0248(4) Uani 1 1 d . . .
H16A H 0.2607 0.7539 0.5795 0.030 Uiso 1 1 calc R . .


_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
S O1 1.4356(13) . ?
S O2 1.4406(13) . ?
S C1 1.7636(17) . ?
S C7 1.7970(17) . ?
F C4 1.357(2) . ?
O3 C10 1.3562(19) . ?
O3 C8 1.3835(19) . ?
N C10 1.296(2) . ?
N C9 1.388(2) . ?
C1 C6 1.387(2) . ?
C1 C2 1.385(2) . ?
C2 C3 1.384(3) . ?
C2 H2B 0.9500 . ?
C3 C4 1.372(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.374(3) . ?
C5 C6 1.382(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.478(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.336(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.459(2) . ?
C11 C12 1.393(2) . ?
C11 C16 1.394(2) . ?
C12 C13 1.382(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?

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
O1 S O2 118.90(8) . . ?
O1 S C1 109.58(8) . . ?
O2 S C1 107.36(8) . . ?
O1 S C7 107.75(8) . . ?
O2 S C7 108.35(8) . . ?
C1 S C7 103.88(8) . . ?
C10 O3 C8 104.36(12) . . ?
C10 N C9 104.32(14) . . ?
C6 C1 C2 121.46(16) . . ?
C6 C1 S 118.85(13) . . ?
C2 C1 S 119.62(13) . . ?
C3 C2 C1 119.03(17) . . ?
C3 C2 H2B 120.5 . . ?
C1 C2 H2B 120.5 . . ?
C4 C3 C2 118.45(17) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 120.8 . . ?
F C4 C3 118.19(16) . . ?
F C4 C5 118.24(16) . . ?
C3 C4 C5 123.57(17) . . ?
C4 C5 C6 117.91(16) . . ?
C4 C5 H5A 121.0 . . ?
C6 C5 H5A 121.0 . . ?
C5 C6 C1 119.56(16) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
C8 C7 S 111.73(11) . . ?
C8 C7 H7A 109.3 . . ?
S C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
S C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 O3 107.45(14) . . ?
C9 C8 C7 136.11(16) . . ?
O3 C8 C7 116.26(13) . . ?
C8 C9 N 109.93(15) . . ?
C8 C9 H9A 125.0 . . ?
N C9 H9A 125.0 . . ?
N C10 O3 113.94(14) . . ?
N C10 C11 128.16(15) . . ?
O3 C10 C11 117.88(14) . . ?
C12 C11 C16 119.51(16) . . ?
C12 C11 C10 119.56(15) . . ?
C16 C11 C10 120.93(15) . . ?
C13 C12 C11 120.09(17) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 120.24(17) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C13 C14 C15 119.90(17) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 120.33(17) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C11 119.92(17) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.052


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2015174
_database_code_depnum_ccdc_archive 'CCDC 1465164'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5-(((4-bromophenyl)sulfonyl)methyl)-2-phenyloxazole
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H12 Br N O3 S'
_chemical_formula_sum            'C16 H12 Br N O3 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            Brown

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         378.24

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0573(8)
_cell_length_b                   9.8062(15)
_cell_length_c                   13.5008(17)
_cell_angle_alpha                70.435(13)
_cell_angle_beta                 82.679(10)
_cell_angle_gamma                82.699(11)
_cell_volume                     746.41(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1213
_cell_measurement_theta_min      3.6060
_cell_measurement_theta_max      26.2610
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    2.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6732
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0938
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         29.31
_reflns_number_total             3452
_reflns_number_gt                2269
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0948P)²+0.0000P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         3452
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1985
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br Br 0.98901(11) 0.35904(7) 0.21392(5) 0.0453(3) Uani 1 1 d . . .
S S 0.8301(2) 0.81552(15) 0.46556(11) 0.0276(4) Uani 1 1 d . . .
O1 O 0.6291(7) 0.7879(5) 0.5343(3) 0.0388(10) Uani 1 1 d . . .
O2 O 1.0325(7) 0.8229(5) 0.5073(3) 0.0395(11) Uani 1 1 d . . .
O3 O 0.6428(5) 0.9099(4) 0.2265(3) 0.0228(8) Uani 1 1 d . . .
N N 0.2899(7) 1.0057(6) 0.2182(4) 0.0287(11) Uani 1 1 d . . .
C1 C 0.8787(9) 0.6828(6) 0.4017(4) 0.0238(11) Uani 1 1 d . . .
C2 C 0.7092(9) 0.5978(7) 0.4049(5) 0.0286(12) Uani 1 1 d . . .
H2B H 0.5733 0.6071 0.4438 0.034 Uiso 1 1 calc R . .
C3 C 0.7425(9) 0.5000(6) 0.3504(4) 0.0289(12) Uani 1 1 d . . .
H3A H 0.6296 0.4432 0.3518 0.035 Uiso 1 1 calc R . .
C4 C 0.9464(10) 0.4872(6) 0.2935(4) 0.0283(12) Uani 1 1 d . . .
C5 C 1.1179(9) 0.5689(7) 0.2917(5) 0.0329(14) Uani 1 1 d . . .
H5A H 1.2543 0.5585 0.2534 0.039 Uiso 1 1 calc R . .
C6 C 1.0840(9) 0.6659(7) 0.3472(5) 0.0327(14) Uani 1 1 d . . .
H6A H 1.1990 0.7199 0.3481 0.039 Uiso 1 1 calc R . .
C7 C 0.7846(9) 0.9822(6) 0.3607(4) 0.0251(12) Uani 1 1 d . . .
H7A H 0.7519 1.0608 0.3903 0.030 Uiso 1 1 calc R . .
H7B H 0.9212 0.9999 0.3142 0.030 Uiso 1 1 calc R . .
C8 C 0.5994(8) 0.9849(6) 0.2973(4) 0.0235(11) Uani 1 1 d . . .
C9 C 0.3871(9) 1.0416(7) 0.2920(5) 0.0328(14) Uani 1 1 d . . .
H9A H 0.3150 1.0973 0.3324 0.039 Uiso 1 1 calc R . .
C10 C 0.4471(8) 0.9276(6) 0.1826(4) 0.0222(11) Uani 1 1 d . . .
C11 C 0.4363(8) 0.8509(6) 0.1071(4) 0.0238(12) Uani 1 1 d . . .
C12 C 0.2390(9) 0.8670(7) 0.0582(4) 0.0283(12) Uani 1 1 d . . .
H12A H 0.1163 0.9264 0.0734 0.034 Uiso 1 1 calc R . .
C13 C 0.2275(9) 0.7948(7) -0.0121(4) 0.0319(14) Uani 1 1 d . . .
H13A H 0.0973 0.8061 -0.0450 0.038 Uiso 1 1 calc R . .
C14 C 0.4098(10) 0.7050(7) -0.0342(5) 0.0367(15) Uani 1 1 d . . .
H14A H 0.4022 0.6577 -0.0828 0.044 Uiso 1 1 calc R . .
C15 C 0.6022(9) 0.6856(7) 0.0158(5) 0.0341(14) Uani 1 1 d . . .
H15A H 0.7227 0.6237 0.0021 0.041 Uiso 1 1 calc R . .
C16 C 0.6152(9) 0.7586(6) 0.0863(4) 0.0258(12) Uani 1 1 d . . .
H16A H 0.7449 0.7456 0.1198 0.031 Uiso 1 1 calc R . .


_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
Br C4 1.884(5) . ?
S O1 1.430(4) . ?
S O2 1.432(4) . ?
S C1 1.764(6) . ?
S C7 1.785(5) . ?
O3 C10 1.358(6) . ?
O3 C8 1.372(6) . ?
N C10 1.292(7) . ?
N C9 1.379(7) . ?
C1 C6 1.383(8) . ?
C1 C2 1.391(7) . ?
C2 C3 1.374(8) . ?
C2 H2B 0.9300 . ?
C3 C4 1.384(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(8) . ?
C5 C6 1.378(8) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.488(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.336(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.467(7) . ?
C11 C16 1.384(7) . ?
C11 C12 1.405(7) . ?
C12 C13 1.372(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.389(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.381(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.383(7) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?

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
O1 S O2 119.7(3) . . ?
O1 S C1 107.8(3) . . ?
O2 S C1 108.4(3) . . ?
O1 S C7 109.2(3) . . ?
O2 S C7 106.6(3) . . ?
C1 S C7 104.0(2) . . ?
C10 O3 C8 104.2(4) . . ?
C10 N C9 104.0(4) . . ?
C6 C1 C2 120.4(5) . . ?
C6 C1 S 119.7(4) . . ?
C2 C1 S 119.9(4) . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2B 120.0 . . ?
C1 C2 H2B 120.0 . . ?
C2 C3 C4 119.1(5) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 121.5(5) . . ?
C5 C4 Br 119.2(4) . . ?
C3 C4 Br 119.3(4) . . ?
C6 C5 C4 119.2(5) . . ?
C6 C5 H5A 120.4 . . ?
C4 C5 H5A 120.4 . . ?
C5 C6 C1 119.8(5) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
C8 C7 S 114.0(4) . . ?
C8 C7 H7A 108.7 . . ?
S C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
S C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 O3 107.3(4) . . ?
C9 C8 C7 135.8(5) . . ?
O3 C8 C7 116.8(4) . . ?
C8 C9 N 110.3(5) . . ?
C8 C9 H9A 124.8 . . ?
N C9 H9A 124.8 . . ?
N C10 O3 114.1(4) . . ?
N C10 C11 128.6(5) . . ?
O3 C10 C11 117.2(4) . . ?
C16 C11 C12 119.5(5) . . ?
C16 C11 C10 120.9(4) . . ?
C12 C11 C10 119.6(5) . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C12 C13 C14 120.2(5) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C15 C14 C13 120.2(5) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C16 C15 C14 119.9(5) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C11 120.3(5) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.843
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.608
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.164


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rp2011
_database_code_depnum_ccdc_archive 'CCDC 1465165'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-phenyl-5-(((4-(trifluoromethyl)phenyl)sulfonyl)methyl)oxazole
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H12 F3 N O3 S'
_chemical_formula_sum            'C17 H12 F3 N O3 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         367.34

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1164(12)
_cell_length_b                   9.942(3)
_cell_length_c                   13.652(3)
_cell_angle_alpha                72.21(2)
_cell_angle_beta                 84.375(18)
_cell_angle_gamma                87.05(2)
_cell_volume                     786.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1048
_cell_measurement_theta_min      4.0970
_cell_measurement_theta_max      27.7140
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5845
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         29.17
_reflns_number_total             3584
_reflns_number_gt                2191
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1369P)²+0.0000P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         3584
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0895
_refine_ls_wR_factor_ref         0.2694
_refine_ls_wR_factor_gt          0.2170
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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
S S 0.28829(16) 0.30949(10) 0.47033(7) 0.0482(4) Uani 1 1 d . . .
F1 F 0.5021(6) -0.0231(3) 0.1280(2) 0.0918(10) Uani 1 1 d . . .
F2 F 0.7461(6) -0.1331(4) 0.2257(3) 0.1042(12) Uani 1 1 d . . .
F3 F 0.4200(6) -0.2084(3) 0.2506(2) 0.0972(11) Uani 1 1 d . . .
O1 O 0.4675(5) 0.3228(3) 0.5257(3) 0.0680(9) Uani 1 1 d . . .
O2 O 0.0752(5) 0.2768(3) 0.5232(2) 0.0699(10) Uani 1 1 d . . .
O3 O 0.1224(4) 0.4044(3) 0.2313(2) 0.0433(6) Uani 1 1 d . . .
N N -0.2165(5) 0.4961(4) 0.2214(3) 0.0531(9) Uani 1 1 d . . .
C1 C 0.3634(6) 0.1827(4) 0.4059(3) 0.0404(8) Uani 1 1 d . . .
C2 C 0.5774(6) 0.1768(4) 0.3651(3) 0.0505(10) Uani 1 1 d . . .
H2B H 0.6832 0.2334 0.3760 0.061 Uiso 1 1 calc R . .
C3 C 0.6316(7) 0.0857(5) 0.3080(4) 0.0569(11) Uani 1 1 d . . .
H3A H 0.7746 0.0827 0.2783 0.068 Uiso 1 1 calc R . .
C4 C 0.4759(7) -0.0016(4) 0.2942(3) 0.0470(9) Uani 1 1 d . . .
C5 C 0.2663(7) -0.0004(4) 0.3395(4) 0.0535(10) Uani 1 1 d . . .
H5A H 0.1637 -0.0626 0.3334 0.064 Uiso 1 1 calc R . .
C6 C 0.2086(6) 0.0937(4) 0.3945(3) 0.0520(10) Uani 1 1 d . . .
H6A H 0.0654 0.0972 0.4238 0.062 Uiso 1 1 calc R . .
C7 C 0.5340(9) -0.0936(5) 0.2260(4) 0.0645(12) Uani 1 1 d . . .
C8 C 0.2651(6) 0.4730(4) 0.3688(3) 0.0473(9) Uani 1 1 d . . .
H8A H 0.2399 0.5495 0.3991 0.057 Uiso 1 1 calc R . .
H8B H 0.4031 0.4897 0.3259 0.057 Uiso 1 1 calc R . .
C9 C 0.0873(6) 0.4752(4) 0.3035(3) 0.0432(9) Uani 1 1 d . . .
C10 C -0.1175(6) 0.5309(4) 0.2966(3) 0.0495(10) Uani 1 1 d . . .
H10A H -0.1829 0.5851 0.3367 0.059 Uiso 1 1 calc R . .
C11 C -0.0681(6) 0.4214(4) 0.1852(3) 0.0403(8) Uani 1 1 d . . .
C12 C -0.0837(6) 0.3522(4) 0.1067(3) 0.0415(8) Uani 1 1 d . . .
C13 C -0.2741(6) 0.3684(5) 0.0561(3) 0.0539(10) Uani 1 1 d . . .
H13A H -0.3913 0.4230 0.0729 0.065 Uiso 1 1 calc R . .
C14 C -0.2898(7) 0.3040(5) -0.0189(4) 0.0644(12) Uani 1 1 d . . .
H14A H -0.4166 0.3158 -0.0534 0.077 Uiso 1 1 calc R . .
C15 C -0.1170(8) 0.2220(5) -0.0427(4) 0.0645(12) Uani 1 1 d . . .
H15A H -0.1275 0.1787 -0.0935 0.077 Uiso 1 1 calc R . .
C16 C 0.0698(8) 0.2036(5) 0.0076(4) 0.0655(13) Uani 1 1 d . . .
H16A H 0.1853 0.1475 -0.0088 0.079 Uiso 1 1 calc R . .
C17 C 0.0874(7) 0.2678(5) 0.0822(3) 0.0519(10) Uani 1 1 d . . .
H17A H 0.2146 0.2546 0.1165 0.062 Uiso 1 1 calc R . .


_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
S O1 1.425(3) . ?
S O2 1.429(3) . ?
S C1 1.764(4) . ?
S C8 1.795(4) . ?
F1 C7 1.335(5) . ?
F2 C7 1.336(5) . ?
F3 C7 1.305(5) . ?
O3 C11 1.357(4) . ?
O3 C9 1.372(4) . ?
N C11 1.299(5) . ?
N C10 1.379(5) . ?
C1 C2 1.377(5) . ?
C1 C6 1.380(5) . ?
C2 C3 1.374(6) . ?
C2 H2B 0.9300 . ?
C3 C4 1.385(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.369(5) . ?
C4 C7 1.500(6) . ?
C5 C6 1.381(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C8 C9 1.467(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.343(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.452(5) . ?
C12 C17 1.387(5) . ?
C12 C13 1.389(5) . ?
C13 C14 1.377(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.375(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.366(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.372(6) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?

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
O1 S O2 120.0(2) . . ?
O1 S C1 108.15(18) . . ?
O2 S C1 108.32(18) . . ?
O1 S C8 106.76(19) . . ?
O2 S C8 107.9(2) . . ?
C1 S C8 104.65(17) . . ?
C11 O3 C9 104.9(3) . . ?
C11 N C10 104.4(3) . . ?
C2 C1 C6 120.8(4) . . ?
C2 C1 S 118.9(3) . . ?
C6 C1 S 120.3(3) . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2B 120.6 . . ?
C1 C2 H2B 120.6 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 C7 120.0(4) . . ?
C5 C4 C7 119.8(4) . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
F3 C7 F2 107.2(4) . . ?
F3 C7 F1 106.8(4) . . ?
F2 C7 F1 105.7(4) . . ?
F3 C7 C4 114.1(4) . . ?
F2 C7 C4 112.0(4) . . ?
F1 C7 C4 110.5(4) . . ?
C9 C8 S 113.3(3) . . ?
C9 C8 H8A 108.9 . . ?
S C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
S C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 O3 107.1(3) . . ?
C10 C9 C8 135.0(4) . . ?
O3 C9 C8 117.8(3) . . ?
C9 C10 N 110.1(3) . . ?
C9 C10 H10A 124.9 . . ?
N C10 H10A 124.9 . . ?
N C11 O3 113.5(3) . . ?
N C11 C12 128.8(3) . . ?
O3 C11 C12 117.7(3) . . ?
C17 C12 C13 119.1(4) . . ?
C17 C12 C11 121.1(3) . . ?
C13 C12 C11 119.8(4) . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C15 119.7(4) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C12 120.3(4) . . ?
C16 C17 H17A 119.9 . . ?
C12 C17 H17A 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.841
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.971
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.121


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rp2007
_database_code_depnum_ccdc_archive 'CCDC 1465166'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-(((4-methoxyphenyl)sulfonyl)methyl)-2-phenyloxazole
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H15 N O4 S'
_chemical_formula_sum            'C17 H15 N O4 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            Yellow
_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         329.36

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1602(11)
_cell_length_b                   10.664(2)
_cell_length_c                   13.258(3)
_cell_angle_alpha                103.005(18)
_cell_angle_beta                 102.402(16)
_cell_angle_gamma                106.112(16)
_cell_volume                     778.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5542
_diffrn_reflns_av_unetI/netI     0.1303
_diffrn_reflns_av_R_equivalents  0.1224
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         29.180
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3550
_reflns_number_gt                2033
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3550
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2094
_refine_ls_R_factor_gt           0.1740
_refine_ls_wR_factor_ref         0.4576
_refine_ls_wR_factor_gt          0.4311
_refine_ls_goodness_of_fit_ref   1.377
_refine_ls_restrained_S_all      1.377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.2310(3) 0.30606(17) 0.03510(14) 0.0479(6) Uani 1 1 d . . . . .
O1 O -0.0002(8) 0.3117(5) 0.0002(5) 0.0634(15) Uani 1 1 d . . . . .
O2 O 0.3640(9) 0.2915(6) -0.0406(4) 0.0630(14) Uani 1 1 d . . . . .
O3 O 0.2332(9) -0.1070(6) 0.2650(4) 0.0622(14) Uani 1 1 d . . . . .
O4 O 0.6363(7) 0.3951(5) 0.2802(4) 0.0464(11) Uani 1 1 d . . . . .
N N 1.0078(10) 0.4919(7) 0.2804(5) 0.0587(16) Uani 1 1 d . . . . .
C1 C 0.2235(10) 0.1762(6) 0.0960(5) 0.0425(14) Uani 1 1 d . . . . .
C2 C 0.0684(11) 0.1484(7) 0.1585(7) 0.0504(17) Uani 1 1 d . . . . .
H2B H -0.0404 0.1934 0.1628 0.061 Uiso 1 1 calc R U . . .
C3 C 0.0799(12) 0.0537(8) 0.2135(7) 0.0565(18) Uani 1 1 d . . . . .
H3A H -0.0204 0.0361 0.2559 0.068 Uiso 1 1 calc R U . . .
C4 C 0.2375(11) -0.0152(7) 0.2064(5) 0.0461(15) Uani 1 1 d . . . . .
C5 C 0.3889(12) 0.0108(7) 0.1444(6) 0.0482(15) Uani 1 1 d . . . . .
H5A H 0.4945 -0.0362 0.1391 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3822(12) 0.1089(8) 0.0894(6) 0.0523(17) Uani 1 1 d . . . . .
H6A H 0.4856 0.1280 0.0486 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3856(15) -0.1857(9) 0.2547(8) 0.072(2) Uani 1 1 d . . . . .
H7A H 0.3671 -0.2455 0.2990 0.109 Uiso 1 1 calc R U . . .
H7B H 0.3450 -0.2392 0.1804 0.109 Uiso 1 1 calc R U . . .
H7C H 0.5468 -0.1252 0.2778 0.109 Uiso 1 1 calc R U . . .
C8 C 0.3979(10) 0.4629(7) 0.1441(5) 0.0449(14) Uani 1 1 d . . . . .
H8A H 0.4200 0.5389 0.1140 0.054 Uiso 1 1 calc R U . . .
H8B H 0.3055 0.4756 0.1938 0.054 Uiso 1 1 calc R U . . .
C9 C 0.6308(10) 0.4682(7) 0.2055(5) 0.0437(14) Uani 1 1 d . . . . .
C10 C 0.8526(12) 0.5234(9) 0.2055(7) 0.059(2) Uani 1 1 d . . . . .
H10A H 0.8979 0.5760 0.1615 0.071 Uiso 1 1 calc R U . . .
C11 C 0.8683(11) 0.4133(7) 0.3192(6) 0.0484(15) Uani 1 1 d . . . . .
C12 C 0.9302(12) 0.3404(7) 0.3986(6) 0.0467(15) Uani 1 1 d . . . . .
C13 C 1.1671(13) 0.3648(9) 0.4467(7) 0.0602(19) Uani 1 1 d . . . . .
H13A H 1.2837 0.4280 0.4315 0.072 Uiso 1 1 calc R U . . .
C14 C 1.2289(15) 0.2941(11) 0.5178(7) 0.072(2) Uani 1 1 d . . . . .
H14A H 1.3877 0.3090 0.5493 0.086 Uiso 1 1 calc R U . . .
C15 C 1.0559(17) 0.2015(10) 0.5422(7) 0.076(2) Uani 1 1 d . . . . .
H15A H 1.0974 0.1551 0.5907 0.091 Uiso 1 1 calc R U . . .
C16 C 0.8198(16) 0.1791(9) 0.4930(8) 0.073(2) Uani 1 1 d . . . . .
H16A H 0.7018 0.1174 0.5086 0.087 Uiso 1 1 calc R U . . .
C17 C 0.7594(13) 0.2482(8) 0.4211(6) 0.0561(18) Uani 1 1 d . . . . .
H17A H 0.6008 0.2317 0.3878 0.067 Uiso 1 1 calc R U . . .


_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
S O1 1.422(5) . ?
S O2 1.434(5) . ?
S C1 1.748(7) . ?
S C8 1.806(7) . ?
O3 C4 1.379(8) . ?
O3 C7 1.430(9) . ?
O4 C11 1.353(7) . ?
O4 C9 1.392(8) . ?
N C11 1.299(9) . ?
N C10 1.390(9) . ?
C1 C6 1.370(9) . ?
C1 C2 1.408(9) . ?
C2 C3 1.380(10) . ?
C2 H2B 0.9300 . ?
C3 C4 1.377(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(9) . ?
C5 C6 1.408(10) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.469(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.329(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.489(10) . ?
C12 C17 1.362(10) . ?
C12 C13 1.385(9) . ?
C13 C14 1.388(11) . ?
C13 H13A 0.9300 . ?
C14 C15 1.387(12) . ?
C14 H14A 0.9300 . ?
C15 C16 1.388(12) . ?
C15 H15A 0.9300 . ?
C16 C17 1.381(11) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?

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
O1 S O2 119.8(4) . . ?
O1 S C1 110.0(3) . . ?
O2 S C1 107.6(3) . . ?
O1 S C8 105.6(3) . . ?
O2 S C8 108.2(3) . . ?
C1 S C8 104.7(3) . . ?
C4 O3 C7 117.1(6) . . ?
C11 O4 C9 104.0(5) . . ?
C11 N C10 103.3(5) . . ?
C6 C1 C2 120.1(6) . . ?
C6 C1 S 119.5(5) . . ?
C2 C1 S 120.2(5) . . ?
C3 C2 C1 119.2(6) . . ?
C3 C2 H2B 120.4 . . ?
C1 C2 H2B 120.4 . . ?
C4 C3 C2 120.9(7) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 O3 115.7(6) . . ?
C5 C4 O3 124.2(6) . . ?
C4 C5 C6 119.6(6) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C1 C6 C5 120.0(6) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S 114.8(4) . . ?
C9 C8 H8A 108.6 . . ?
S C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
S C8 H8B 108.6 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 O4 107.1(5) . . ?
C10 C9 C8 135.4(7) . . ?
O4 C9 C8 117.4(5) . . ?
C9 C10 N 110.8(7) . . ?
C9 C10 H10A 124.6 . . ?
N C10 H10A 124.6 . . ?
N C11 O4 114.7(6) . . ?
N C11 C12 128.7(6) . . ?
O4 C11 C12 116.7(6) . . ?
C17 C12 C13 120.3(7) . . ?
C17 C12 C11 121.3(6) . . ?
C13 C12 C11 118.4(6) . . ?
C12 C13 C14 119.4(8) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
C13 C14 C15 120.6(7) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 118.8(8) . . ?
C16 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
C17 C16 C15 120.3(8) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C12 C17 C16 120.6(8) . . ?
C12 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?

_refine_diff_density_max         0.882
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.167

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rp2109
_database_code_depnum_ccdc_archive 'CCDC 1465167'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(4-chlorophenyl)-5-(tosylmethyl)oxazole
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H18 Cl N O3 S'
_chemical_formula_sum            'C23 H18 Cl N O3 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'Light yellow'
_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         423.89

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.752(3)
_cell_length_b                   8.4132(13)
_cell_length_c                   19.307(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.58(2)
_cell_angle_gamma                90
_cell_volume                     2091.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.307
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10104
_diffrn_reflns_av_unetI/netI     0.1126
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.892
_diffrn_reflns_theta_max         29.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4749
_reflns_number_gt                2502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1830P)²+2.1706P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4749
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1700
_refine_ls_R_factor_gt           0.1164
_refine_ls_wR_factor_ref         0.3860
_refine_ls_wR_factor_gt          0.3575
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl -0.1213(2) 0.5787(3) 0.22952(15) 0.0898(8) Uani 1 1 d . . . . .
S S 0.45959(13) 0.67624(19) 0.06864(9) 0.0484(5) Uani 1 1 d . . . . .
O1 O 0.4831(4) 0.5428(5) 0.1182(3) 0.0650(14) Uani 1 1 d . . . . .
O2 O 0.5358(4) 0.7285(6) 0.0387(3) 0.0643(14) Uani 1 1 d . . . . .
O3 O 0.2140(4) 0.5862(5) 0.0477(2) 0.0479(11) Uani 1 1 d . . . . .
N N 0.1706(5) 0.3320(6) 0.0285(3) 0.0559(14) Uani 1 1 d . . . . .
C1 C 0.4245(5) 0.8400(7) 0.1123(3) 0.0427(13) Uani 1 1 d . . . . .
C2 C 0.3830(6) 0.8145(8) 0.1667(4) 0.0531(16) Uani 1 1 d . . . . .
H2B H 0.3727 0.7117 0.1805 0.064 Uiso 1 1 calc R U . . .
C3 C 0.3569(6) 0.9434(9) 0.2004(4) 0.0600(18) Uani 1 1 d . . . . .
H3A H 0.3290 0.9266 0.2372 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3711(5) 1.0963(8) 0.1809(4) 0.0522(16) Uani 1 1 d . . . . .
C5 C 0.4157(6) 1.1200(8) 0.1279(4) 0.0555(17) Uani 1 1 d . . . . .
H5A H 0.4279 1.2230 0.1154 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4426(5) 0.9923(7) 0.0931(4) 0.0476(15) Uani 1 1 d . . . . .
H6A H 0.4723 1.0089 0.0573 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3425(7) 1.2385(10) 0.2174(4) 0.075(2) Uani 1 1 d . . . . .
H7A H 0.3582 1.3342 0.1963 0.112 Uiso 1 1 calc R U . . .
H7B H 0.2697 1.2353 0.2096 0.112 Uiso 1 1 calc R U . . .
H7C H 0.3816 1.2363 0.2695 0.112 Uiso 1 1 calc R U . . .
C8 C 0.3464(5) 0.6200(7) -0.0112(3) 0.0428(13) Uani 1 1 d . . . . .
H8A H 0.3741 0.5489 -0.0400 0.051 Uiso 1 1 calc R U . . .
C9 C 0.2720(5) 0.5211(7) 0.0090(3) 0.0432(13) Uani 1 1 d . . . . .
C10 C 0.2451(6) 0.3689(7) -0.0019(4) 0.0538(16) Uani 1 1 d . . . . .
H10A H 0.2726 0.2969 -0.0266 0.065 Uiso 1 1 calc R U . . .
C11 C 0.1548(5) 0.4631(7) 0.0571(3) 0.0461(14) Uani 1 1 d . . . . .
C12 C 0.0856(5) 0.4973(7) 0.0980(3) 0.0451(14) Uani 1 1 d . . . . .
C13 C 0.0808(6) 0.6466(8) 0.1265(4) 0.0579(17) Uani 1 1 d . . . . .
H13A H 0.1207 0.7293 0.1189 0.069 Uiso 1 1 calc R U . . .
C14 C 0.0164(6) 0.6726(8) 0.1666(4) 0.0613(18) Uani 1 1 d . . . . .
H14A H 0.0120 0.7732 0.1852 0.074 Uiso 1 1 calc R U . . .
C15 C -0.0418(6) 0.5481(8) 0.1790(4) 0.0571(17) Uani 1 1 d . . . . .
C16 C -0.0382(6) 0.4015(9) 0.1499(4) 0.0601(18) Uani 1 1 d . . . . .
H16A H -0.0792 0.3198 0.1571 0.072 Uiso 1 1 calc R U . . .
C17 C 0.0262(6) 0.3728(8) 0.1097(4) 0.0575(17) Uani 1 1 d . . . . .
H17A H 0.0296 0.2721 0.0908 0.069 Uiso 1 1 calc R U . . .
C18 C 0.3004(5) 0.7582(7) -0.0629(3) 0.0441(14) Uani 1 1 d . . . . .
C19 C 0.3286(6) 0.7748(9) -0.1252(4) 0.0601(18) Uani 1 1 d . . . . .
H19A H 0.3753 0.7038 -0.1333 0.072 Uiso 1 1 calc R U . . .
C20 C 0.2874(7) 0.8958(11) -0.1748(4) 0.075(2) Uani 1 1 d . . . . .
H20A H 0.3069 0.9073 -0.2161 0.090 Uiso 1 1 calc R U . . .
C21 C 0.2170(7) 1.0004(10) -0.1632(5) 0.076(2) Uani 1 1 d . . . . .
H21A H 0.1871 1.0801 -0.1975 0.091 Uiso 1 1 calc R U . . .
C22 C 0.1911(7) 0.9863(7) -0.1006(4) 0.065(2) Uani 1 1 d . . . . .
H22A H 0.1455 1.0585 -0.0919 0.077 Uiso 1 1 calc R U . . .
C23 C 0.2326(6) 0.8657(7) -0.0510(4) 0.0549(17) Uani 1 1 d . . . . .
H23A H 0.2146 0.8566 -0.0091 0.066 Uiso 1 1 calc R U . . .


_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
Cl C15 1.722(7) . ?
S O2 1.432(5) . ?
S O1 1.436(5) . ?
S C1 1.769(6) . ?
S C8 1.827(6) . ?
O3 C11 1.368(7) . ?
O3 C9 1.382(7) . ?
N C11 1.285(8) . ?
N C10 1.383(8) . ?
C1 C2 1.378(8) . ?
C1 C6 1.381(8) . ?
C2 C3 1.374(9) . ?
C2 H2B 0.9300 . ?
C3 C4 1.374(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(9) . ?
C4 C7 1.509(9) . ?
C5 C6 1.384(8) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.474(8) . ?
C8 C18 1.518(8) . ?
C8 H8A 0.9800 . ?
C9 C10 1.329(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.464(9) . ?
C12 C13 1.383(9) . ?
C12 C17 1.394(9) . ?
C13 C14 1.382(10) . ?
C13 H13A 0.9300 . ?
C14 C15 1.389(10) . ?
C14 H14A 0.9300 . ?
C15 C16 1.363(10) . ?
C16 C17 1.389(10) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C23 1.375(9) . ?
C18 C19 1.395(9) . ?
C19 C20 1.376(11) . ?
C19 H19A 0.9300 . ?
C20 C21 1.385(12) . ?
C20 H20A 0.9300 . ?
C21 C22 1.381(12) . ?
C21 H21A 0.9300 . ?
C22 C23 1.373(9) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?

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
O2 S O1 118.9(3) . . ?
O2 S C1 108.3(3) . . ?
O1 S C1 109.0(3) . . ?
O2 S C8 105.5(3) . . ?
O1 S C8 106.6(3) . . ?
C1 S C8 108.0(3) . . ?
C11 O3 C9 104.7(4) . . ?
C11 N C10 104.6(5) . . ?
C2 C1 C6 120.8(5) . . ?
C2 C1 S 119.9(5) . . ?
C6 C1 S 119.3(4) . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 H2B 120.5 . . ?
C1 C2 H2B 120.5 . . ?
C2 C3 C4 121.6(6) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C3 C4 C5 118.8(6) . . ?
C3 C4 C7 121.9(6) . . ?
C5 C4 C7 119.3(7) . . ?
C4 C5 C6 120.8(6) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C18 116.1(5) . . ?
C9 C8 S 112.8(4) . . ?
C18 C8 S 113.0(4) . . ?
C9 C8 H8A 104.5 . . ?
C18 C8 H8A 104.5 . . ?
S C8 H8A 104.5 . . ?
C10 C9 O3 106.7(5) . . ?
C10 C9 C8 133.0(6) . . ?
O3 C9 C8 120.4(5) . . ?
C9 C10 N 110.8(6) . . ?
C9 C10 H10A 124.6 . . ?
N C10 H10A 124.6 . . ?
N C11 O3 113.3(5) . . ?
N C11 C12 129.8(6) . . ?
O3 C11 C12 116.9(5) . . ?
C13 C12 C17 120.3(6) . . ?
C13 C12 C11 121.7(6) . . ?
C17 C12 C11 118.0(6) . . ?
C12 C13 C14 119.7(6) . . ?
C12 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
C13 C14 C15 119.9(7) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 120.3(7) . . ?
C16 C15 Cl 119.4(5) . . ?
C14 C15 Cl 120.3(5) . . ?
C15 C16 C17 120.7(7) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C16 C17 C12 119.0(6) . . ?
C16 C17 H17A 120.5 . . ?
C12 C17 H17A 120.5 . . ?
C23 C18 C19 119.2(6) . . ?
C23 C18 C8 123.0(6) . . ?
C19 C18 C8 117.8(6) . . ?
C20 C19 C18 120.2(7) . . ?
C20 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
C19 C20 C21 119.8(8) . . ?
C19 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C22 C21 C20 119.9(7) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C23 C22 C21 120.1(8) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C22 C23 C18 120.7(7) . . ?
C22 C23 H23A 119.7 . . ?
C18 C23 H23A 119.7 . . ?

_refine_diff_density_max         0.684
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.099

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rp2148
_database_code_depnum_ccdc_archive 'CCDC 1473425'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H15 I N2 O5 S'
_chemical_formula_sum            'C17 H15 I N2 O5 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         486.27

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3360(7)
_cell_length_b                   13.7149(9)
_cell_length_c                   14.1776(8)
_cell_angle_alpha                85.839(5)
_cell_angle_beta                 74.352(6)
_cell_angle_gamma                76.639(6)
_cell_volume                     1882.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3032
_cell_measurement_theta_min      3.2720
_cell_measurement_theta_max      25.4800
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.842
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15464
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.854
_diffrn_reflns_theta_max         29.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8636
_reflns_number_gt                5253
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0826P)²+2.7803P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8636
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1979
_refine_ls_wR_factor_gt          0.1621
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.21518(5) 0.60542(4) 0.14603(4) 0.05450(19) Uani 1 1 d . . . . .
S1 S 0.0117(2) 0.33855(19) 0.12953(18) 0.0700(7) Uani 1 1 d . . . . .
O1 O 0.0029(8) 0.2907(6) 0.2210(5) 0.096(2) Uani 1 1 d . . . . .
O2 O -0.1125(6) 0.3782(6) 0.0985(6) 0.114(3) Uani 1 1 d . . . . .
O3 O -0.1611(5) 0.5491(4) 0.3638(4) 0.0588(15) Uani 1 1 d . . . . .
O4 O -0.3051(10) 0.9446(6) 0.6849(7) 0.135(4) Uani 1 1 d . . . . .
O5 O -0.1459(9) 1.0000(6) 0.5857(6) 0.110(3) Uani 1 1 d . . . . .
N1 N 0.0605(5) 0.5326(4) 0.3603(4) 0.0395(13) Uani 1 1 d . . . . .
H1A H 0.1185 0.5530 0.3833 0.029(17) Uiso 1 1 calc R . . . .
N2 N -0.2100(9) 0.9359(6) 0.6126(6) 0.074(2) Uani 1 1 d . . . . .
C1 C 0.1234(7) 0.2534(6) 0.0389(6) 0.0486(19) Uani 1 1 d . . . . .
C2 C 0.2137(9) 0.1717(7) 0.0650(7) 0.064(2) Uani 1 1 d . . . . .
H2B H 0.2169 0.1606 0.1299 0.076 Uiso 1 1 calc R U . . .
C3 C 0.3003(9) 0.1058(7) -0.0085(8) 0.071(3) Uani 1 1 d . . . . .
H3B H 0.3625 0.0507 0.0076 0.085 Uiso 1 1 calc R U . . .
C4 C 0.2942(9) 0.1220(6) -0.1042(7) 0.063(2) Uani 1 1 d . . . . .
C5 C 0.2020(9) 0.2039(7) -0.1268(6) 0.065(2) Uani 1 1 d . . . . .
H5A H 0.1975 0.2151 -0.1914 0.078 Uiso 1 1 calc R U . . .
C6 C 0.1161(8) 0.2696(7) -0.0554(7) 0.064(2) Uani 1 1 d . . . . .
H6A H 0.0538 0.3245 -0.0717 0.077 Uiso 1 1 calc R U . . .
C7 C 0.3896(12) 0.0503(8) -0.1849(9) 0.105(4) Uani 1 1 d . . . . .
H7A H 0.4469 -0.0023 -0.1565 0.158 Uiso 1 1 calc R U . . .
H7B H 0.3352 0.0219 -0.2158 0.158 Uiso 1 1 calc R U . . .
H7C H 0.4464 0.0865 -0.2326 0.158 Uiso 1 1 calc R U . . .
C8 C 0.0932(7) 0.4380(6) 0.1185(6) 0.0502(19) Uani 1 1 d . . . . .
H8A H 0.1173 0.4652 0.0559 0.060 Uiso 1 1 calc R U . . .
C9 C 0.1256(6) 0.4802(5) 0.1885(5) 0.0382(15) Uani 1 1 d . . . . .
C10 C 0.1098(7) 0.4486(5) 0.2938(5) 0.0413(15) Uani 1 1 d . . . . .
H10A H 0.0458 0.4045 0.3111 0.050 Uiso 1 1 calc R U . . .
H10B H 0.1981 0.4111 0.3018 0.050 Uiso 1 1 calc R U . . .
C11 C -0.0728(7) 0.5794(6) 0.3869(5) 0.0436(17) Uani 1 1 d . . . . .
C12 C -0.1064(6) 0.6732(5) 0.4460(5) 0.0381(15) Uani 1 1 d . . . . .
C13 C -0.2272(7) 0.6931(5) 0.5201(5) 0.0445(17) Uani 1 1 d . . . . .
H13A H -0.2863 0.6491 0.5327 0.053 Uiso 1 1 calc R U . . .
C14 C -0.2600(8) 0.7795(6) 0.5757(5) 0.054(2) Uani 1 1 d . . . . .
H14A H -0.3393 0.7924 0.6272 0.065 Uiso 1 1 calc R U . . .
C15 C -0.1755(7) 0.8440(5) 0.5539(5) 0.0465(17) Uani 1 1 d . . . . .
C16 C -0.0549(8) 0.8289(6) 0.4795(6) 0.055(2) Uani 1 1 d . . . . .
H16A H 0.0012 0.8750 0.4655 0.066 Uiso 1 1 calc R U . . .
C17 C -0.0220(8) 0.7403(6) 0.4265(5) 0.0519(19) Uani 1 1 d . . . . .
H17A H 0.0592 0.7264 0.3767 0.062 Uiso 1 1 calc R U . . .
I2 I 0.38529(6) 0.40341(4) 0.86544(4) 0.0671(2) Uani 1 1 d . . . . .
S2 S 0.47715(17) 0.72406(13) 0.82752(13) 0.0428(4) Uani 1 1 d . . . . .
O6 O 0.6146(5) 0.7236(5) 0.8319(4) 0.0660(16) Uani 1 1 d . . . . .
O7 O 0.4362(5) 0.7599(4) 0.7400(3) 0.0529(13) Uani 1 1 d . . . . .
O8 O 0.6620(5) 0.4731(4) 0.6157(4) 0.0508(13) Uani 1 1 d . . . . .
O9 O 0.6441(9) 0.0051(6) 0.4228(6) 0.108(3) Uani 1 1 d . . . . .
O10 O 0.8155(9) 0.0534(6) 0.3277(6) 0.117(3) Uani 1 1 d . . . . .
N3 N 0.4385(5) 0.4747(4) 0.6411(4) 0.0408(13) Uani 1 1 d . . . . .
H3A H 0.3777 0.4484 0.6278 0.031(17) Uiso 1 1 calc R . . . .
N4 N 0.7143(9) 0.0660(6) 0.3966(6) 0.074(2) Uani 1 1 d . . . . .
C18 C 0.3587(6) 0.7912(5) 0.9275(5) 0.0383(15) Uani 1 1 d . . . . .
C19 C 0.4015(8) 0.8027(6) 1.0093(5) 0.0514(19) Uani 1 1 d . . . . .
H19A H 0.4929 0.7788 1.0105 0.062 Uiso 1 1 calc R U . . .
C20 C 0.3045(10) 0.8512(7) 1.0902(6) 0.066(2) Uani 1 1 d . . . . .
H20A H 0.3323 0.8591 1.1458 0.080 Uiso 1 1 calc R U . . .
C21 C 0.1679(9) 0.8880(6) 1.0901(6) 0.062(2) Uani 1 1 d . . . . .
C22 C 0.1304(9) 0.8777(6) 1.0066(7) 0.065(2) Uani 1 1 d . . . . .
H22A H 0.0399 0.9040 1.0042 0.077 Uiso 1 1 calc R U . . .
C23 C 0.2240(7) 0.8290(6) 0.9256(6) 0.0516(19) Uani 1 1 d . . . . .
H23A H 0.1958 0.8218 0.8700 0.062 Uiso 1 1 calc R U . . .
C24 C 0.0641(12) 0.9395(8) 1.1798(8) 0.099(4) Uani 1 1 d . . . . .
H24A H 0.1091 0.9396 1.2308 0.149 Uiso 1 1 calc R U . . .
H24B H 0.0265 1.0072 1.1630 0.149 Uiso 1 1 calc R U . . .
H24C H -0.0087 0.9040 1.2021 0.149 Uiso 1 1 calc R U . . .
C25 C 0.4517(7) 0.6016(5) 0.8569(5) 0.0422(16) Uani 1 1 d . . . . .
H25A H 0.4623 0.5762 0.9176 0.051 Uiso 1 1 calc R U . . .
C26 C 0.4192(6) 0.5420(5) 0.8020(5) 0.0388(15) Uani 1 1 d . . . . .
C27 C 0.3923(7) 0.5628(5) 0.7028(5) 0.0416(16) Uani 1 1 d . . . . .
H27A H 0.2943 0.5881 0.7108 0.050 Uiso 1 1 calc R U . . .
H27B H 0.4390 0.6146 0.6703 0.050 Uiso 1 1 calc R U . . .
C28 C 0.5702(6) 0.4337(5) 0.6047(5) 0.0379(15) Uani 1 1 d . . . . .
C29 C 0.6061(6) 0.3369(5) 0.5516(5) 0.0363(14) Uani 1 1 d . . . . .
C30 C 0.5247(8) 0.2680(6) 0.5767(6) 0.0523(19) Uani 1 1 d . . . . .
H30A H 0.4449 0.2816 0.6277 0.063 Uiso 1 1 calc R U . . .
C31 C 0.5603(8) 0.1778(6) 0.5266(6) 0.056(2) Uani 1 1 d . . . . .
H31A H 0.5060 0.1305 0.5436 0.068 Uiso 1 1 calc R U . . .
C32 C 0.6782(8) 0.1614(6) 0.4516(5) 0.0477(18) Uani 1 1 d . . . . .
C33 C 0.7628(7) 0.2280(6) 0.4247(5) 0.0517(19) Uani 1 1 d . . . . .
H33A H 0.8423 0.2140 0.3734 0.062 Uiso 1 1 calc R U . . .
C34 C 0.7271(7) 0.3163(5) 0.4756(5) 0.0424(16) Uani 1 1 d . . . . .
H34A H 0.7834 0.3622 0.4594 0.051 Uiso 1 1 calc R U . . .


_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
I1 C9 2.111(7) . ?
S1 O1 1.400(8) . ?
S1 O2 1.444(8) . ?
S1 C8 1.738(8) . ?
S1 C1 1.772(7) . ?
O3 C11 1.213(8) . ?
O4 N2 1.205(10) . ?
O5 N2 1.201(11) . ?
N1 C11 1.341(8) . ?
N1 C10 1.449(8) . ?
N1 H1A 0.8600 . ?
N2 C15 1.482(10) . ?
C1 C6 1.359(12) . ?
C1 C2 1.382(12) . ?
C2 C3 1.401(11) . ?
C2 H2B 0.9300 . ?
C3 C4 1.375(13) . ?
C3 H3B 0.9300 . ?
C4 C5 1.374(13) . ?
C4 C7 1.534(11) . ?
C5 C6 1.379(11) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.336(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.500(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.507(9) . ?
C12 C17 1.373(10) . ?
C12 C13 1.383(9) . ?
C13 C14 1.396(10) . ?
C13 H13A 0.9300 . ?
C14 C15 1.345(11) . ?
C14 H14A 0.9300 . ?
C15 C16 1.383(10) . ?
C16 C17 1.401(10) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
I2 C26 2.106(7) . ?
S2 O7 1.435(5) . ?
S2 O6 1.437(6) . ?
S2 C18 1.757(6) . ?
S2 C25 1.762(7) . ?
O8 C28 1.243(8) . ?
O9 N4 1.205(11) . ?
O10 N4 1.212(10) . ?
N3 C28 1.321(8) . ?
N3 C27 1.454(8) . ?
N3 H3A 0.8600 . ?
N4 C32 1.491(10) . ?
C18 C23 1.376(10) . ?
C18 C19 1.379(10) . ?
C19 C20 1.395(10) . ?
C19 H19A 0.9300 . ?
C20 C21 1.386(13) . ?
C20 H20A 0.9300 . ?
C21 C22 1.367(13) . ?
C21 C24 1.520(11) . ?
C22 C23 1.383(10) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.322(10) . ?
C25 H25A 0.9300 . ?
C26 C27 1.500(9) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.494(9) . ?
C29 C30 1.373(10) . ?
C29 C34 1.400(9) . ?
C30 C31 1.395(10) . ?
C30 H30A 0.9300 . ?
C31 C32 1.370(10) . ?
C31 H31A 0.9300 . ?
C32 C33 1.373(11) . ?
C33 C34 1.378(10) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?

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
O1 S1 O2 119.4(5) . . ?
O1 S1 C8 111.6(4) . . ?
O2 S1 C8 105.4(5) . . ?
O1 S1 C1 108.1(5) . . ?
O2 S1 C1 107.4(4) . . ?
C8 S1 C1 103.9(3) . . ?
C11 N1 C10 121.9(6) . . ?
C11 N1 H1A 119.0 . . ?
C10 N1 H1A 119.0 . . ?
O5 N2 O4 122.3(8) . . ?
O5 N2 C15 119.6(7) . . ?
O4 N2 C15 118.1(8) . . ?
C6 C1 C2 121.3(7) . . ?
C6 C1 S1 118.6(7) . . ?
C2 C1 S1 120.0(6) . . ?
C1 C2 C3 118.5(9) . . ?
C1 C2 H2B 120.8 . . ?
C3 C2 H2B 120.8 . . ?
C4 C3 C2 120.5(9) . . ?
C4 C3 H3B 119.7 . . ?
C2 C3 H3B 119.7 . . ?
C5 C4 C3 119.0(7) . . ?
C5 C4 C7 120.4(10) . . ?
C3 C4 C7 120.6(9) . . ?
C4 C5 C6 121.3(9) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C1 C6 C5 119.3(8) . . ?
C1 C6 H6A 120.3 . . ?
C5 C6 H6A 120.3 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 128.2(6) . . ?
C9 C8 H8A 115.9 . . ?
S1 C8 H8A 115.9 . . ?
C8 C9 C10 128.4(7) . . ?
C8 C9 I1 116.4(6) . . ?
C10 C9 I1 115.2(4) . . ?
N1 C10 C9 113.0(6) . . ?
N1 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
O3 C11 N1 122.2(6) . . ?
O3 C11 C12 121.8(6) . . ?
N1 C11 C12 116.1(6) . . ?
C17 C12 C13 119.5(6) . . ?
C17 C12 C11 121.6(6) . . ?
C13 C12 C11 118.8(6) . . ?
C12 C13 C14 119.7(7) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C15 C14 C13 119.2(6) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C14 C15 C16 123.6(7) . . ?
C14 C15 N2 119.4(7) . . ?
C16 C15 N2 117.0(7) . . ?
C15 C16 C17 116.2(7) . . ?
C15 C16 H16A 121.9 . . ?
C17 C16 H16A 121.9 . . ?
C12 C17 C16 121.8(6) . . ?
C12 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
O7 S2 O6 119.0(4) . . ?
O7 S2 C18 108.5(3) . . ?
O6 S2 C18 109.1(3) . . ?
O7 S2 C25 110.6(3) . . ?
O6 S2 C25 107.0(4) . . ?
C18 S2 C25 101.2(3) . . ?
C28 N3 C27 122.5(6) . . ?
C28 N3 H3A 118.8 . . ?
C27 N3 H3A 118.8 . . ?
O9 N4 O10 123.2(8) . . ?
O9 N4 C32 119.4(7) . . ?
O10 N4 C32 117.4(9) . . ?
C23 C18 C19 120.3(6) . . ?
C23 C18 S2 120.6(5) . . ?
C19 C18 S2 119.1(5) . . ?
C18 C19 C20 118.4(7) . . ?
C18 C19 H19A 120.8 . . ?
C20 C19 H19A 120.8 . . ?
C21 C20 C19 121.9(8) . . ?
C21 C20 H20A 119.0 . . ?
C19 C20 H20A 119.0 . . ?
C22 C21 C20 117.9(7) . . ?
C22 C21 C24 121.4(9) . . ?
C20 C21 C24 120.7(9) . . ?
C21 C22 C23 121.4(8) . . ?
C21 C22 H22A 119.3 . . ?
C23 C22 H22A 119.3 . . ?
C18 C23 C22 120.0(8) . . ?
C18 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 S2 127.1(6) . . ?
C26 C25 H25A 116.4 . . ?
S2 C25 H25A 116.4 . . ?
C25 C26 C27 128.6(6) . . ?
C25 C26 I2 116.3(5) . . ?
C27 C26 I2 115.0(5) . . ?
N3 C27 C26 113.0(6) . . ?
N3 C27 H27A 109.0 . . ?
C26 C27 H27A 109.0 . . ?
N3 C27 H27B 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
O8 C28 N3 121.2(6) . . ?
O8 C28 C29 120.8(6) . . ?
N3 C28 C29 118.0(6) . . ?
C30 C29 C34 119.8(6) . . ?
C30 C29 C28 121.6(6) . . ?
C34 C29 C28 118.6(6) . . ?
C29 C30 C31 120.8(7) . . ?
C29 C30 H30A 119.6 . . ?
C31 C30 H30A 119.6 . . ?
C32 C31 C30 117.4(7) . . ?
C32 C31 H31A 121.3 . . ?
C30 C31 H31A 121.3 . . ?
C31 C32 C33 123.5(7) . . ?
C31 C32 N4 117.4(7) . . ?
C33 C32 N4 119.1(7) . . ?
C32 C33 C34 118.3(6) . . ?
C32 C33 H33A 120.9 . . ?
C34 C33 H33A 120.9 . . ?
C33 C34 C29 120.1(7) . . ?
C33 C34 H34A 120.0 . . ?
C29 C34 H34A 120.0 . . ?

_refine_diff_density_max         3.028
_refine_diff_density_min         -1.062
_refine_diff_density_rms         0.139

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2015188
_database_code_depnum_ccdc_archive 'CCDC 1486532'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        N-(2-hydroxy-3-tosylpropyl)benzamide
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H19 N O4 S'
_chemical_formula_sum            'C17 H19 N O4 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         333.39

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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'

_cell_length_a                   17.8165(19)
_cell_length_b                   11.3743(8)
_cell_length_c                   8.1626(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.490(9)
_cell_angle_gamma                90.00
_cell_volume                     1651.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    968
_cell_measurement_theta_min      3.2150
_cell_measurement_theta_max      24.7450
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7016
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0980
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         29.00
_reflns_number_total             3783
_reflns_number_gt                1933
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0835P)²+0.0199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3783
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1752
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.1906
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.002

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 0.26675(7) 0.61591(11) 1.05019(15) 0.0535(4) Uani 1 1 d . A .
O1 O 0.2553(2) 0.7311(3) 1.1161(5) 0.0835(12) Uani 1 1 d . . .
O2 O 0.2759(2) 0.5180(4) 1.1606(4) 0.0859(12) Uani 1 1 d . . .
O3 O 0.09894(18) 0.5553(3) 1.0946(4) 0.0462(9) Uani 1 1 d . . .
H3A H 0.080(2) 0.592(3) 1.146(5) 0.037(14) Uiso 1 1 d . . .
O4 O 0.01646(17) 0.8512(2) 0.8357(4) 0.0502(8) Uani 1 1 d . A .
N N -0.0159(2) 0.6630(3) 0.8668(4) 0.0398(9) Uani 1 1 d . A .
H0A H -0.048(2) 0.612(3) 0.896(4) 0.028(10) Uiso 1 1 d . . .
C1 C 0.3476(2) 0.6198(4) 0.9386(6) 0.0475(11) Uani 1 1 d . . .
C2 C 0.3733(10) 0.7282(19) 0.908(3) 0.070(2) Uani 0.491(18) 1 d P A 1
H2B H 0.3510 0.7993 0.9339 0.084 Uiso 0.491(18) 1 calc PR A 1
C3 C 0.4554(8) 0.7089(13) 0.812(2) 0.070(2) Uani 0.491(18) 1 d P A 1
C4 C 0.4775(9) 0.6047(13) 0.764(2) 0.070(2) Uani 0.491(18) 1 d P A 1
C5 C 0.4335(8) 0.5144(12) 0.774(2) 0.070(2) Uani 0.491(18) 1 d P A 1
H5A H 0.4451 0.4458 0.7188 0.084 Uiso 0.491(18) 1 calc PR A 1
C6 C 0.3698(8) 0.5163(15) 0.8637(19) 0.070(2) Uani 0.491(18) 1 d P A 1
H6A H 0.3418 0.4480 0.8739 0.084 Uiso 0.491(18) 1 calc PR A 1
C7 C 0.5501(6) 0.5921(16) 0.6742(16) 0.070(2) Uani 0.491(18) 1 d P A 1
H7A H 0.5622 0.5103 0.6639 0.105 Uiso 0.491(18) 1 calc PR A 1
H7B H 0.5903 0.6315 0.7355 0.105 Uiso 0.491(18) 1 calc PR A 1
H7C H 0.5432 0.6266 0.5670 0.105 Uiso 0.491(18) 1 calc PR A 1
C2' C 0.3877(10) 0.719(2) 0.896(3) 0.077(2) Uani 0.509(18) 1 d P A 2
H2'A H 0.3658 0.7870 0.9349 0.092 Uiso 0.509(18) 1 calc PR A 2
C3' C 0.4386(8) 0.7410(14) 0.828(2) 0.077(2) Uani 0.509(18) 1 d P A 2
H3'A H 0.4517 0.8178 0.8034 0.092 Uiso 0.509(18) 1 calc PR A 2
C4' C 0.4794(9) 0.6473(14) 0.785(2) 0.077(2) Uani 0.509(18) 1 d P A 2
C5' C 0.4567(8) 0.5330(13) 0.8405(19) 0.077(2) Uani 0.509(18) 1 d P A 2
H5'A H 0.4872 0.4677 0.8274 0.092 Uiso 0.509(18) 1 calc PR A 2
C6' C 0.3885(8) 0.5216(16) 0.9143(19) 0.077(2) Uani 0.509(18) 1 d P A 2
H6'A H 0.3715 0.4482 0.9462 0.092 Uiso 0.509(18) 1 calc PR A 2
C7' C 0.5523(6) 0.6624(16) 0.6967(16) 0.077(2) Uani 0.509(18) 1 d P A 2
H7'A H 0.5556 0.7416 0.6574 0.115 Uiso 0.509(18) 1 calc PR A 2
H7'B H 0.5523 0.6089 0.6056 0.115 Uiso 0.509(18) 1 calc PR A 2
H7'C H 0.5945 0.6460 0.7718 0.115 Uiso 0.509(18) 1 calc PR A 2
C8 C 0.1919(2) 0.5888(3) 0.9023(5) 0.0422(10) Uani 1 1 d . . .
H8A H 0.2018 0.6299 0.8017 0.051 Uiso 1 1 calc R A .
H8B H 0.1900 0.5053 0.8782 0.051 Uiso 1 1 calc R . .
C9 C 0.1163(2) 0.6277(3) 0.9589(5) 0.0359(9) Uani 1 1 d . A .
H9A H 0.1201 0.7097 0.9956 0.043 Uiso 1 1 calc R . .
C10 C 0.0563(2) 0.6187(3) 0.8227(5) 0.0406(10) Uani 1 1 d . . .
H10A H 0.0721 0.6622 0.7286 0.049 Uiso 1 1 calc R A .
H10B H 0.0507 0.5369 0.7904 0.049 Uiso 1 1 calc R . .
C11 C -0.0314(2) 0.7776(3) 0.8677(5) 0.0382(10) Uani 1 1 d . . .
C12 C -0.1082(2) 0.8135(3) 0.9084(5) 0.0373(10) Uani 1 1 d . A .
C13 C -0.1709(3) 0.7451(4) 0.8734(6) 0.0559(13) Uani 1 1 d . . .
H13A H -0.1656 0.6710 0.8272 0.067 Uiso 1 1 calc R A .
C14 C -0.2416(3) 0.7851(5) 0.9060(7) 0.0734(16) Uani 1 1 d . A .
H14A H -0.2836 0.7387 0.8800 0.088 Uiso 1 1 calc R . .
C15 C -0.2497(3) 0.8939(5) 0.9771(7) 0.0695(16) Uani 1 1 d . . .
H15A H -0.2973 0.9215 0.9986 0.083 Uiso 1 1 calc R A .
C16 C -0.1877(3) 0.9608(4) 1.0157(5) 0.0567(13) Uani 1 1 d . A .
H16A H -0.1932 1.0334 1.0659 0.068 Uiso 1 1 calc R . .
C17 C -0.1172(3) 0.9224(4) 0.9815(5) 0.0445(11) Uani 1 1 d . . .
H17A H -0.0755 0.9694 1.0074 0.053 Uiso 1 1 calc R A .


_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 O2 1.435(4) . ?
S1 O1 1.435(3) . ?
S1 C1 1.750(4) . ?
S1 C8 1.770(4) . ?
O3 C9 1.430(5) . ?
O3 H3A 0.70(4) . ?
O4 C11 1.235(4) . ?
N C11 1.332(5) . ?
N C10 1.448(5) . ?
N H0A 0.87(4) . ?
C1 C2 1.34(2) . ?
C1 C6' 1.356(17) . ?
C1 C2' 1.39(2) . ?
C1 C6 1.396(17) . ?
C2 C3 1.71(2) . ?
C2 H2B 0.9300 . ?
C3 C4 1.318(16) . ?
C3 C5 2.265(19) . ?
C4 C5 1.297(18) . ?
C4 C7 1.531(16) . ?
C5 C6 1.388(16) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C2' C3' 1.12(2) . ?
C2' H2'A 0.9300 . ?
C3' C4' 1.350(16) . ?
C3' H3'A 0.9300 . ?
C4' C7' 1.530(18) . ?
C4' C5' 1.44(2) . ?
C5' C6' 1.395(17) . ?
C5' H5'A 0.9300 . ?
C6' H6'A 0.9300 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8 C9 1.516(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.499(6) . ?
C9 H9A 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.485(6) . ?
C12 C13 1.377(6) . ?
C12 C17 1.389(6) . ?
C13 C14 1.380(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.378(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.362(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.375(6) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?

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
O2 S1 O1 119.1(3) . . ?
O2 S1 C1 106.3(2) . . ?
O1 S1 C1 108.2(2) . . ?
O2 S1 C8 110.2(2) . . ?
O1 S1 C8 107.2(2) . . ?
C1 S1 C8 105.0(2) . . ?
C9 O3 H3A 105(3) . . ?
C11 N C10 122.0(3) . . ?
C11 N H0A 121(2) . . ?
C10 N H0A 117(2) . . ?
C2 C1 C6' 122.4(10) . . ?
C2 C1 C2' 12.4(11) . . ?
C6' C1 C2' 110.0(10) . . ?
C2 C1 C6 125.7(10) . . ?
C6' C1 C6 21.7(8) . . ?
C2' C1 C6 114.2(11) . . ?
C2 C1 S1 114.8(7) . . ?
C6' C1 S1 121.5(7) . . ?
C2' C1 S1 127.0(7) . . ?
C6 C1 S1 118.1(7) . . ?
C1 C2 C3 106.1(13) . . ?
C1 C2 H2B 127.0 . . ?
C3 C2 H2B 127.0 . . ?
C4 C3 C2 122.1(14) . . ?
C4 C3 C5 29.7(8) . . ?
C2 C3 C5 92.5(11) . . ?
C3 C4 C5 120.0(13) . . ?
C3 C4 C7 120.3(12) . . ?
C5 C4 C7 119.2(11) . . ?
C4 C5 C6 122.5(12) . . ?
C4 C5 C3 30.2(7) . . ?
C6 C5 C3 92.9(9) . . ?
C4 C5 H5A 118.7 . . ?
C6 C5 H5A 118.7 . . ?
C3 C5 H5A 147.7 . . ?
C5 C6 C1 120.5(12) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3' C2' C1 138(2) . . ?
C3' C2' H2'A 110.8 . . ?
C1 C2' H2'A 110.8 . . ?
C2' C3' C4' 114.9(19) . . ?
C2' C3' H3'A 122.6 . . ?
C4' C3' H3'A 122.6 . . ?
C7' C4' C3' 121.4(12) . . ?
C7' C4' C5' 120.7(12) . . ?
C3' C4' C5' 117.5(13) . . ?
C6' C5' C4' 119.2(13) . . ?
C6' C5' H5'A 120.4 . . ?
C4' C5' H5'A 120.4 . . ?
C1 C6' C5' 118.5(13) . . ?
C1 C6' H6'A 120.7 . . ?
C5' C6' H6'A 120.7 . . ?
C4' C7' H7'A 109.5 . . ?
C4' C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
C4' C7' H7'C 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C9 C8 S1 112.8(3) . . ?
C9 C8 H8A 109.0 . . ?
S1 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
S1 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O3 C9 C10 110.9(3) . . ?
O3 C9 C8 107.8(3) . . ?
C10 C9 C8 111.2(3) . . ?
O3 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
N C10 C9 113.3(3) . . ?
N C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
O4 C11 N 121.1(4) . . ?
O4 C11 C12 121.2(4) . . ?
N C11 C12 117.7(3) . . ?
C13 C12 C17 118.7(4) . . ?
C13 C12 C11 123.0(4) . . ?
C17 C12 C11 118.3(4) . . ?
C12 C13 C14 120.8(4) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C17 120.9(5) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C16 C17 C12 120.1(4) . . ?
C16 C17 H17A 119.9 . . ?
C12 C17 H17A 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.862
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.059


