# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_iu706
_database_code_depnum_ccdc_archive 'CCDC 1584197'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;

_audit_creation_date             2017-11-06T14:10:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C14 H19 N O3 S'
_chemical_formula_sum            'C14 H19 N O3 S'
_chemical_formula_weight         281.36
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a                   5.36821(6)
_cell_length_b                   11.71337(15)
_cell_length_c                   21.6232(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1359.66(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    6484
_cell_measurement_theta_min      4.068
_cell_measurement_theta_max      73.766
_cell_measurement_wavelength     1.54184

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.038
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -6 1 0.1451
-3 5 0 0.0962
-1 -7 2 0.1492
1 7 -2 0.1629
1 3 -1 0.1745
0 0 1 0.0183
0 0 -1 0.0197
1 -7 0 0.1635
3 -1 -1 0.105
-1 3 0 0.0712


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

_exptl_absorpt_coefficient_mu    2.157
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_T_max  0.922

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

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0546247
_diffrn_orient_matrix_ub_12      -0.0775688
_diffrn_orient_matrix_ub_13      -0.055911
_diffrn_orient_matrix_ub_21      -0.0258032
_diffrn_orient_matrix_ub_22      -0.1032992
_diffrn_orient_matrix_ub_23      0.0436324
_diffrn_orient_matrix_ub_31      -0.2805544
_diffrn_orient_matrix_ub_32      0.0245918
_diffrn_orient_matrix_ub_33      0.0068934
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.038
_diffrn_reflns_number            9152
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.089
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             2586
_reflns_number_gt                2520
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00 110.00   1.00    1.50    --   40.58  57.00 -60.00   94
  2  ω     -6.00  44.00   1.00    1.50    --   40.58 -57.00   0.00   50
  3  ω     25.00  72.00   1.00    2.00    --  108.36 -94.00 -30.00   47
  4  ω     80.00 108.00   1.00    2.00    --  108.36 -94.00 -30.00   28
  5  ω     42.00  68.00   1.00    2.00    --  108.36 -30.00  60.00   26
  6  ω     36.00  61.00   1.00    2.00    --  108.36 -45.00   0.00   25
  7  ω     34.00  71.00   1.00    2.00    --  108.36 -45.00 -30.00   37
  8  ω     25.00 133.00   1.00    2.00    --  108.36 -15.00  90.00  108
  9  ω    -28.00  65.00   1.00    1.50    --   40.58 -57.00 150.00   93
 10  ω      2.00  69.00   1.00    1.50    --   40.58 -57.00  30.00   67
 11  ω      5.00  32.00   1.00    1.50    --   40.58-125.00  30.00   27
 12  ω     35.00  61.00   1.00    2.00    --  108.36 -45.00-180.00   26
 13  ω     90.00 122.00   1.00    2.00    --  108.36-125.00 -60.00   32
 14  ω     40.00  77.00   1.00    2.00    --  108.36 -45.00  30.00   37
 15  ω     39.00  67.00   1.00    2.00    --  108.36-125.00 -60.00   28
 16  ω     77.00 108.00   1.00    2.00    --  108.36 -94.00  30.00   31
 17  ω     30.00 138.00   1.00    2.00    --  108.36 -77.00-180.00  108
 18  ω     35.00  74.00   1.00    2.00    --  108.36 -45.00 -60.00   39
 19  ω     41.00  69.00   1.00    2.00    --  108.36 -30.00  90.00   28
 20  ω     42.00  68.00   1.00    2.00    --  108.36 -45.00   0.00   26
 21  ω     49.00 104.00   1.00    2.00    --  108.36 -94.00 120.00   55
 22  ω     54.00 136.00   1.00    2.00    --  108.36  15.00   0.00   82
 23  ω     88.00 151.00   1.00    2.00    --  108.36   0.00 120.00   63
;

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   mixed

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

_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 > 2σ(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.
 There is a disorder along the structure in five atoms ring
 in two positions (more or less 84/16%).
   
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0264P)²+0.4076P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     191
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.062
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
The Friedel pair coverage of the experiment is almost complete (99%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2010).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-99. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=-0.001(8), which together with Flack
parameter value, indicate that the absolute structure has sureley been
determined correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
Dolomanov, O.V. (2009) OLEX2, J. Appl. Cryst., 42, 339-341. 
Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
Spek, A.L. (2009). Acta Cryst. D65, 148-155.
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   -0.005(9)
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.77933(12) 0.94492(6) 0.38698(3) 0.0154(2) Uani 0.836(3) d A 1
S1B S 0.3847(11) 0.8591(6) 0.4642(2) 0.0172(14) Uani 0.164(3) d A 2
O1 O 0.8752(3) 0.96532(12) 0.21928(7) 0.0183(3) Uani 1 d . .
O2 O 0.7550(3) 0.86199(11) 0.13838(6) 0.0164(3) Uani 1 d . .
O3 O 0.7260(3) 0.51737(12) 0.36039(7) 0.0236(3) Uani 1 d . .
H3 H 0.855167 0.523029 0.338677 0.035 Uiso 1 calc . .
N1 N 0.4291(3) 0.87380(14) 0.28042(8) 0.0145(3) Uani 1 d . .
C0BG C 0.786(3) 0.973(2) 0.4533(6) 0.0196(4) Uani 0.164(3) d A 2
H0BG H 0.929578 1.018313 0.461313 0.024 Uiso 0.164(3) calc A 2
C0BJ C 0.616(3) 0.9413(19) 0.4963(7) 0.0196(4) Uani 0.164(3) d A 2
H0BJ H 0.623501 0.961859 0.53873 0.024 Uiso 0.164(3) calc A 2
H1 H 0.287(3) 0.9068(19) 0.2683(11) 0.024 Uiso 1 d . .
C1 C 0.7470(4) 0.88954(16) 0.19818(9) 0.0143(4) Uani 1 d . .
C2 C 0.5709(4) 0.81082(16) 0.23389(9) 0.0128(4) Uani 1 d . .
C3 C 0.4012(4) 0.80617(16) 0.33784(9) 0.0147(4) Uani 1 d . .
H3A H 0.220038 0.791796 0.345297 0.018 Uiso 1 calc . .
C4 C 0.5302(4) 0.69163(17) 0.32270(9) 0.0148(4) Uani 1 d . .
H4 H 0.404287 0.640427 0.302885 0.018 Uiso 1 calc . .
C5 C 0.7203(4) 0.72589(15) 0.27331(9) 0.0141(4) Uani 1 d . .
H5A H 0.774088 0.659154 0.2486 0.017 Uiso 1 calc . .
H5B H 0.8683 0.762624 0.292011 0.017 Uiso 1 calc . .
C6 C 0.4233(4) 0.75354(17) 0.18134(9) 0.0148(4) Uani 1 d . .
H6A H 0.388314 0.672632 0.191318 0.018 Uiso 1 calc . .
H6B H 0.263472 0.793586 0.174234 0.018 Uiso 1 calc . .
C7 C 0.5917(4) 0.76266(16) 0.12447(9) 0.0154(4) Uani 1 d . .
C8 C 0.5081(3) 0.86791(17) 0.39292(9) 0.0147(4) Uani 1 d . .
C9 C 0.7780(7) 0.9744(4) 0.46536(11) 0.0196(4) Uani 0.836(3) d A 1
H9 H 0.903419 1.017104 0.486014 0.024 Uiso 0.836(3) calc A 1
C10 C 0.5749(6) 0.9289(4) 0.49370(15) 0.0196(4) Uani 0.836(3) d A 1
H10 H 0.539145 0.937335 0.536489 0.024 Uiso 0.836(3) calc A 1
C11 C 0.4253(9) 0.8684(4) 0.45232(19) 0.0214(10) Uani 0.836(3) d A 1
H11 H 0.277102 0.830431 0.464725 0.026 Uiso 0.836(3) calc A 1
C11B C 0.720(2) 0.9312(15) 0.3968(6) 0.0172(14) Uani 0.164(3) d A 2
H11B H 0.819696 0.94553 0.36124 0.021 Uiso 0.164(3) calc A 2
C12 C 0.6420(4) 0.62846(17) 0.37742(9) 0.0191(4) Uani 1 d . .
H12A H 0.783927 0.672913 0.394021 0.023 Uiso 1 calc . .
H12B H 0.515438 0.621685 0.410503 0.023 Uiso 1 calc . .
C13 C 0.7649(4) 0.66126(16) 0.11465(10) 0.0192(4) Uani 1 d . .
H13A H 0.880018 0.67802 0.080666 0.029 Uiso 1 calc . .
H13B H 0.666208 0.593474 0.104381 0.029 Uiso 1 calc . .
H13C H 0.859897 0.647054 0.152577 0.029 Uiso 1 calc . .
C14 C 0.4526(4) 0.78960(19) 0.06575(9) 0.0197(4) Uani 1 d . .
H14A H 0.356724 0.860052 0.071306 0.03 Uiso 1 calc . .
H14B H 0.339017 0.726653 0.055937 0.03 Uiso 1 calc . .
H14C H 0.571584 0.799606 0.031809 0.03 Uiso 1 calc . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.7176(19) . ?
S1 C9 1.730(2) . ?
S1B C0BJ 1.717(7) . ?
S1B C8 1.681(5) . ?
O1 C1 1.212(2) . ?
O2 C1 1.334(2) . ?
O2 C7 1.488(2) . ?
O3 H3 0.84 . ?
O3 C12 1.425(2) . ?
N1 H1 0.894(12) . ?
N1 C2 1.461(2) . ?
N1 C3 1.480(2) . ?
C0BG H0BG 0.95 . ?
C0BG C0BJ 1.356(7) . ?
C0BG C11B 1.363(7) . ?
C0BJ H0BJ 0.95 . ?
C1 C2 1.530(3) . ?
C2 C5 1.536(3) . ?
C2 C6 1.539(3) . ?
C3 H3A 1 . ?
C3 C4 1.545(3) . ?
C3 C8 1.507(3) . ?
C4 H4 1 . ?
C4 C5 1.531(3) . ?
C4 C12 1.519(3) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C6 C7 1.530(3) . ?
C7 C13 1.523(3) . ?
C7 C14 1.506(3) . ?
C8 C11 1.359(4) . ?
C8 C11B 1.362(6) . ?
C9 H9 0.95 . ?
C9 C10 1.359(3) . ?
C10 H10 0.95 . ?
C10 C11 1.396(4) . ?
C11 H11 0.95 . ?
C11B H11B 0.95 . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?

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
C8 S1 C9 91.62(13) . . ?
C8 S1B C0BJ 92.9(5) . . ?
C1 O2 C7 111.49(15) . . ?
C12 O3 H3 109.5 . . ?
C2 N1 H1 117.4(16) . . ?
C2 N1 C3 111.11(15) . . ?
C3 N1 H1 113.0(16) . . ?
C0BJ C0BG H0BG 125 . . ?
C0BJ C0BG C11B 109.9(12) . . ?
C11B C0BG H0BG 125 . . ?
S1B C0BJ H0BJ 124.3 . . ?
C0BG C0BJ S1B 111.4(10) . . ?
C0BG C0BJ H0BJ 124.3 . . ?
O1 C1 O2 121.60(18) . . ?
O1 C1 C2 127.03(17) . . ?
O2 C1 C2 111.31(16) . . ?
N1 C2 C1 111.41(16) . . ?
N1 C2 C5 102.51(15) . . ?
N1 C2 C6 117.41(16) . . ?
C1 C2 C5 110.36(16) . . ?
C1 C2 C6 102.02(15) . . ?
C5 C2 C6 113.33(16) . . ?
N1 C3 H3A 108.9 . . ?
N1 C3 C4 103.98(15) . . ?
N1 C3 C8 111.56(16) . . ?
C4 C3 H3A 108.9 . . ?
C8 C3 H3A 108.9 . . ?
C8 C3 C4 114.43(16) . . ?
C3 C4 H4 108 . . ?
C5 C4 C3 102.65(15) . . ?
C5 C4 H4 108 . . ?
C12 C4 C3 115.79(16) . . ?
C12 C4 H4 108 . . ?
C12 C4 C5 114.05(17) . . ?
C2 C5 H5A 111.4 . . ?
C2 C5 H5B 111.4 . . ?
C4 C5 C2 102.06(15) . . ?
C4 C5 H5A 111.4 . . ?
C4 C5 H5B 111.4 . . ?
H5A C5 H5B 109.2 . . ?
C2 C6 H6A 110.7 . . ?
C2 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C7 C6 C2 105.01(16) . . ?
C7 C6 H6A 110.7 . . ?
C7 C6 H6B 110.7 . . ?
O2 C7 C6 103.91(15) . . ?
O2 C7 C13 106.15(15) . . ?
O2 C7 C14 107.38(16) . . ?
C13 C7 C6 114.72(17) . . ?
C14 C7 C6 113.54(17) . . ?
C14 C7 C13 110.38(17) . . ?
C3 C8 S1 121.05(14) . . ?
C3 C8 S1B 123.0(2) . . ?
C11 C8 S1 110.2(2) . . ?
C11 C8 C3 128.6(2) . . ?
C11B C8 S1B 107.9(6) . . ?
C11B C8 C3 128.9(6) . . ?
S1 C9 H9 124.2 . . ?
C10 C9 S1 111.5(2) . . ?
C10 C9 H9 124.2 . . ?
C9 C10 H10 124.1 . . ?
C9 C10 C11 111.8(3) . . ?
C11 C10 H10 124.1 . . ?
C8 C11 C10 114.8(4) . . ?
C8 C11 H11 122.6 . . ?
C10 C11 H11 122.6 . . ?
C0BG C11B H11B 121.1 . . ?
C8 C11B C0BG 117.9(10) . . ?
C8 C11B H11B 121.1 . . ?
O3 C12 C4 111.62(17) . . ?
O3 C12 H12A 109.3 . . ?
O3 C12 H12B 109.3 . . ?
C4 C12 H12A 109.3 . . ?
C4 C12 H12B 109.3 . . ?
H12A C12 H12B 108 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C8 C11 C10 -0.2(5) . . . . ?
S1 C9 C10 C11 1.4(6) . . . . ?
S1B C8 C11B C0BG -1(2) . . . . ?
O1 C1 C2 N1 41.9(3) . . . . ?
O1 C1 C2 C5 -71.3(2) . . . . ?
O1 C1 C2 C6 168.01(19) . . . . ?
O2 C1 C2 N1 -140.99(16) . . . . ?
O2 C1 C2 C5 105.82(18) . . . . ?
O2 C1 C2 C6 -14.9(2) . . . . ?
N1 C2 C5 C4 39.14(18) . . . . ?
N1 C2 C6 C7 145.49(16) . . . . ?
N1 C3 C4 C5 26.70(19) . . . . ?
N1 C3 C4 C12 151.61(17) . . . . ?
N1 C3 C8 S1 -39.0(2) . . . . ?
N1 C3 C8 S1B 145.4(3) . . . . ?
N1 C3 C8 C11 144.9(3) . . . . ?
N1 C3 C8 C11B -39.9(12) . . . . ?
C0BJ S1B C8 C3 176.6(9) . . . . ?
C0BJ S1B C8 C11B 0.9(13) . . . . ?
C0BJ C0BG C11B C8 0(3) . . . . ?
C1 O2 C7 C6 15.7(2) . . . . ?
C1 O2 C7 C13 -105.69(18) . . . . ?
C1 O2 C7 C14 136.24(17) . . . . ?
C1 C2 C5 C4 157.90(15) . . . . ?
C1 C2 C6 C7 23.43(19) . . . . ?
C2 N1 C3 C4 -2.1(2) . . . . ?
C2 N1 C3 C8 121.68(17) . . . . ?
C2 C6 C7 O2 -24.10(19) . . . . ?
C2 C6 C7 C13 91.33(19) . . . . ?
C2 C6 C7 C14 -140.44(17) . . . . ?
C3 N1 C2 C1 -141.21(16) . . . . ?
C3 N1 C2 C5 -23.2(2) . . . . ?
C3 N1 C2 C6 101.71(19) . . . . ?
C3 C4 C5 C2 -40.59(18) . . . . ?
C3 C4 C12 O3 172.01(16) . . . . ?
C3 C8 C11 C10 176.2(3) . . . . ?
C3 C8 C11B C0BG -176.1(15) . . . . ?
C4 C3 C8 S1 78.7(2) . . . . ?
C4 C3 C8 S1B -96.9(4) . . . . ?
C4 C3 C8 C11 -97.4(4) . . . . ?
C4 C3 C8 C11B 77.8(12) . . . . ?
C5 C2 C6 C7 -95.20(19) . . . . ?
C5 C4 C12 O3 -69.2(2) . . . . ?
C6 C2 C5 C4 -88.40(18) . . . . ?
C7 O2 C1 O1 176.93(17) . . . . ?
C7 O2 C1 C2 -0.3(2) . . . . ?
C8 S1 C9 C10 -1.3(4) . . . . ?
C8 S1B C0BJ C0BG -1(2) . . . . ?
C8 C3 C4 C5 -95.24(19) . . . . ?
C8 C3 C4 C12 29.7(2) . . . . ?
C9 S1 C8 C3 -175.9(2) . . . . ?
C9 S1 C8 C11 0.9(3) . . . . ?
C9 C10 C11 C8 -0.8(6) . . . . ?
C11B C0BG C0BJ S1B 1(3) . . . . ?
C12 C4 C5 C2 -166.64(17) . . . . ?




# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_systematic        
(2R,4S,5R)-3-(Hydroxymethyl)-8,8-dimethyl-2-(thiophen-2-yl)-7-oxa-1-azaspiro[4.4]nonan-6-one
