# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1590179'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_date             2017-12-08T19:59:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C18 H24 Cl N O2 S'
_chemical_formula_sum            'C18 H24 Cl N O2 S'
_chemical_formula_weight         353.89

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   10.3869(3)
_cell_length_b                   15.4759(3)
_cell_length_c                   11.2824(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.723(3)
_cell_angle_gamma                90
_cell_volume                     1745.75(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2819
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      26.98

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

_exptl_crystal_description       ' prism'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             752
_exptl_special_details           
;
  CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SCALE3
_exptl_absorpt_correction_T_min  0.98303
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.206
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         6987
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.041
_diffrn_reflns_number            7663
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.233
_diffrn_reflns_theta_max         29.183
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.841
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.841
_reflns_Friedel_coverage         0
_reflns_number_total             3974
_reflns_number_gt                3243
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3974
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.037
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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 0.16376(4) 0.08448(2) 0.11200(4) 0.01246(11) Uani 1 1 d . . . . .
Cl Cl -0.04884(5) 0.16328(3) 0.56954(4) 0.02768(13) Uani 1 1 d . . . . .
O1 O 0.05383(12) 0.10086(7) 0.00445(11) 0.0165(3) Uani 1 1 d . . . . .
O2 O 0.28394(12) 0.13426(7) 0.12845(11) 0.0154(3) Uani 1 1 d . . . . .
N1 N 0.19672(14) -0.01639(9) 0.10767(13) 0.0129(3) Uani 1 1 d . . . . .
H1 H 0.131(2) -0.0441(13) 0.0734(19) 0.023(6) Uiso 1 1 d . . . . .
C1 C 0.10355(16) 0.10530(10) 0.24210(15) 0.0136(3) Uani 1 1 d . . . . .
C2 C 0.00379(17) 0.05367(11) 0.26574(17) 0.0183(4) Uani 1 1 d . . . . .
H2 H -0.032(2) 0.0072(12) 0.2147(18) 0.019(5) Uiso 1 1 d . . . . .
C3 C -0.04367(18) 0.07141(11) 0.36664(17) 0.0200(4) Uani 1 1 d . . . . .
H3 H -0.109(2) 0.0380(12) 0.3863(18) 0.022(5) Uiso 1 1 d . . . . .
C4 C 0.00967(18) 0.14096(11) 0.44209(16) 0.0188(4) Uani 1 1 d . . . . .
C5 C 0.10803(19) 0.19268(11) 0.41886(18) 0.0216(4) Uani 1 1 d . . . . .
H5 H 0.144(2) 0.2394(13) 0.4722(18) 0.025(5) Uiso 1 1 d . . . . .
C6 C 0.15562(19) 0.17433(11) 0.31820(17) 0.0200(4) Uani 1 1 d . . . . .
H6 H 0.221(2) 0.2075(13) 0.3028(18) 0.027(6) Uiso 1 1 d . . . . .
C7 C 0.31348(16) -0.06336(10) 0.18708(14) 0.0113(3) Uani 1 1 d . . . . .
C8 C 0.34083(17) -0.03926(11) 0.32372(15) 0.0142(3) Uani 1 1 d . . . . .
H81 H 0.2609(18) -0.0496(11) 0.3542(16) 0.014(5) Uiso 1 1 d . . . . .
H82 H 0.361(2) 0.0210(13) 0.3348(18) 0.023(5) Uiso 1 1 d . . . . .
C9 C 0.45873(17) -0.09288(11) 0.39949(15) 0.0148(3) Uani 1 1 d . . . . .
H9 H 0.4730(18) -0.0798(11) 0.4888(17) 0.016(5) Uiso 1 1 d . . . . .
C10 C 0.58300(17) -0.07416(11) 0.35576(15) 0.0153(3) Uani 1 1 d . . . . .
H101 H 0.6580(19) -0.1071(11) 0.4067(16) 0.017(5) Uiso 1 1 d . . . . .
H102 H 0.6064(18) -0.0135(12) 0.3664(16) 0.015(5) Uiso 1 1 d . . . . .
C11 C 0.55818(16) -0.09864(11) 0.21941(15) 0.0141(3) Uani 1 1 d . . . . .
C12 C 0.43844(16) -0.04605(10) 0.14333(15) 0.0133(3) Uani 1 1 d . . . . .
H121 H 0.4629(18) 0.0175(11) 0.1502(16) 0.013(4) Uiso 1 1 d . . . . .
H122 H 0.4211(18) -0.0603(11) 0.0563(17) 0.014(5) Uiso 1 1 d . . . . .
C13 C 0.27884(17) -0.15985(10) 0.17121(16) 0.0145(3) Uani 1 1 d . . . . .
H131 H 0.2008(18) -0.1696(11) 0.2002(16) 0.010(4) Uiso 1 1 d . . . . .
H132 H 0.2589(19) -0.1743(11) 0.0812(18) 0.020(5) Uiso 1 1 d . . . . .
C14 C 0.39547(17) -0.21487(10) 0.24693(15) 0.0152(3) Uani 1 1 d . . . . .
C15 C 0.52117(17) -0.19496(11) 0.20507(16) 0.0156(3) Uani 1 1 d . . . . .
H151 H 0.5046(18) -0.2137(11) 0.1178(17) 0.014(5) Uiso 1 1 d . . . . .
H152 H 0.5959(19) -0.2296(11) 0.2519(16) 0.015(5) Uiso 1 1 d . . . . .
C16 C 0.42427(18) -0.18924(11) 0.38280(16) 0.0178(4) Uani 1 1 d . . . . .
H161 H 0.4952(19) -0.2263(11) 0.4303(17) 0.015(5) Uiso 1 1 d . . . . .
H162 H 0.3465(19) -0.2026(12) 0.4159(16) 0.017(5) Uiso 1 1 d . . . . .
C17 C 0.68173(19) -0.08066(13) 0.17507(19) 0.0222(4) Uani 1 1 d . . . . .
H171 H 0.665(2) -0.0988(13) 0.092(2) 0.028(6) Uiso 1 1 d . . . . .
H172 H 0.761(2) -0.1129(12) 0.2261(18) 0.021(5) Uiso 1 1 d . . . . .
H173 H 0.705(2) -0.0144(13) 0.1804(19) 0.031(6) Uiso 1 1 d . . . . .
C18 C 0.3607(2) -0.31098(12) 0.2305(2) 0.0251(4) Uani 1 1 d . . . . .
H181 H 0.433(2) -0.3446(12) 0.2772(18) 0.020(5) Uiso 1 1 d . . . . .
H182 H 0.341(2) -0.3275(13) 0.141(2) 0.027(6) Uiso 1 1 d . . . . .
H183 H 0.285(2) -0.3226(12) 0.2649(18) 0.025(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
S O2 1.4354(12) . ?
S O1 1.4455(12) . ?
S N1 1.6017(14) . ?
S C1 1.7740(17) . ?
Cl C4 1.7406(18) . ?
N1 C7 1.4876(19) . ?
N1 H1 0.81(2) . ?
C1 C6 1.385(2) . ?
C1 C2 1.390(2) . ?
C2 C3 1.385(3) . ?
C2 H2 0.933(19) . ?
C3 C4 1.391(2) . ?
C3 H3 0.92(2) . ?
C4 C5 1.378(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.95(2) . ?
C6 H6 0.91(2) . ?
C7 C12 1.532(2) . ?
C7 C13 1.535(2) . ?
C7 C8 1.536(2) . ?
C8 C9 1.534(2) . ?
C8 H81 0.994(19) . ?
C8 H82 0.957(19) . ?
C9 C10 1.529(2) . ?
C9 C16 1.533(2) . ?
C9 H9 0.998(18) . ?
C10 C11 1.537(2) . ?
C10 H101 0.977(18) . ?
C10 H102 0.969(18) . ?
C11 C17 1.524(2) . ?
C11 C15 1.537(2) . ?
C11 C12 1.539(2) . ?
C12 H121 1.013(17) . ?
C12 H122 0.974(18) . ?
C13 C14 1.537(2) . ?
C13 H131 0.965(18) . ?
C13 H132 1.005(19) . ?
C14 C18 1.530(2) . ?
C14 C16 1.532(2) . ?
C14 C15 1.535(2) . ?
C15 H151 0.995(18) . ?
C15 H152 0.973(18) . ?
C16 H161 0.972(19) . ?
C16 H162 0.999(19) . ?
C17 H171 0.95(2) . ?
C17 H172 1.00(2) . ?
C17 H173 1.05(2) . ?
C18 H181 0.95(2) . ?
C18 H182 1.00(2) . ?
C18 H183 0.99(2) . ?

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 118.42(7) . . ?
O2 S N1 109.96(7) . . ?
O1 S N1 105.78(7) . . ?
O2 S C1 106.55(7) . . ?
O1 S C1 106.70(8) . . ?
N1 S C1 109.17(7) . . ?
C7 N1 S 127.16(11) . . ?
C7 N1 H1 118.3(14) . . ?
S N1 H1 111.6(14) . . ?
C6 C1 C2 120.68(16) . . ?
C6 C1 S 119.14(13) . . ?
C2 C1 S 120.17(13) . . ?
C3 C2 C1 119.58(16) . . ?
C3 C2 H2 119.4(12) . . ?
C1 C2 H2 121.1(12) . . ?
C2 C3 C4 119.01(17) . . ?
C2 C3 H3 122.2(12) . . ?
C4 C3 H3 118.8(12) . . ?
C5 C4 C3 121.74(17) . . ?
C5 C4 Cl 118.99(14) . . ?
C3 C4 Cl 119.27(14) . . ?
C4 C5 C6 118.98(17) . . ?
C4 C5 H5 120.4(13) . . ?
C6 C5 H5 120.6(13) . . ?
C5 C6 C1 120.01(17) . . ?
C5 C6 H6 119.7(13) . . ?
C1 C6 H6 120.3(13) . . ?
N1 C7 C12 110.12(13) . . ?
N1 C7 C13 106.14(12) . . ?
C12 C7 C13 108.95(13) . . ?
N1 C7 C8 112.62(13) . . ?
C12 C7 C8 109.79(13) . . ?
C13 C7 C8 109.09(13) . . ?
C9 C8 C7 109.31(13) . . ?
C9 C8 H81 109.6(10) . . ?
C7 C8 H81 111.3(10) . . ?
C9 C8 H82 109.9(12) . . ?
C7 C8 H82 110.0(12) . . ?
H81 C8 H82 106.7(15) . . ?
C10 C9 C16 109.50(14) . . ?
C10 C9 C8 109.51(14) . . ?
C16 C9 C8 109.47(14) . . ?
C10 C9 H9 112.3(11) . . ?
C16 C9 H9 106.7(10) . . ?
C8 C9 H9 109.3(10) . . ?
C9 C10 C11 110.43(13) . . ?
C9 C10 H101 108.6(11) . . ?
C11 C10 H101 110.5(11) . . ?
C9 C10 H102 110.4(11) . . ?
C11 C10 H102 109.4(11) . . ?
H101 C10 H102 107.5(15) . . ?
C17 C11 C10 110.85(14) . . ?
C17 C11 C15 110.57(14) . . ?
C10 C11 C15 108.29(13) . . ?
C17 C11 C12 110.22(14) . . ?
C10 C11 C12 108.60(13) . . ?
C15 C11 C12 108.24(13) . . ?
C7 C12 C11 110.80(13) . . ?
C7 C12 H121 111.2(10) . . ?
C11 C12 H121 108.8(10) . . ?
C7 C12 H122 110.1(11) . . ?
C11 C12 H122 110.1(11) . . ?
H121 C12 H122 105.8(15) . . ?
C7 C13 C14 110.46(13) . . ?
C7 C13 H131 107.8(10) . . ?
C14 C13 H131 109.4(10) . . ?
C7 C13 H132 108.1(10) . . ?
C14 C13 H132 110.7(11) . . ?
H131 C13 H132 110.3(15) . . ?
C18 C14 C16 110.40(15) . . ?
C18 C14 C15 110.52(15) . . ?
C16 C14 C15 107.70(14) . . ?
C18 C14 C13 110.28(14) . . ?
C16 C14 C13 108.87(14) . . ?
C15 C14 C13 109.01(14) . . ?
C14 C15 C11 111.81(14) . . ?
C14 C15 H151 108.2(11) . . ?
C11 C15 H151 111.0(10) . . ?
C14 C15 H152 110.0(11) . . ?
C11 C15 H152 109.7(10) . . ?
H151 C15 H152 106.0(14) . . ?
C14 C16 C9 110.52(14) . . ?
C14 C16 H161 108.2(11) . . ?
C9 C16 H161 112.9(10) . . ?
C14 C16 H162 111.2(11) . . ?
C9 C16 H162 109.9(11) . . ?
H161 C16 H162 103.9(15) . . ?
C11 C17 H171 109.1(13) . . ?
C11 C17 H172 110.7(11) . . ?
H171 C17 H172 108.8(16) . . ?
C11 C17 H173 111.3(12) . . ?
H171 C17 H173 108.8(17) . . ?
H172 C17 H173 108.1(15) . . ?
C14 C18 H181 110.0(11) . . ?
C14 C18 H182 110.2(11) . . ?
H181 C18 H182 109.3(16) . . ?
C14 C18 H183 108.5(11) . . ?
H181 C18 H183 106.1(17) . . ?
H182 C18 H183 112.6(16) . . ?

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
O2 S N1 C7 41.58(16) . . . . ?
O1 S N1 C7 170.55(13) . . . . ?
C1 S N1 C7 -74.97(15) . . . . ?
O2 S C1 C6 14.02(16) . . . . ?
O1 S C1 C6 -113.38(14) . . . . ?
N1 S C1 C6 132.73(14) . . . . ?
O2 S C1 C2 -167.06(13) . . . . ?
O1 S C1 C2 65.54(15) . . . . ?
N1 S C1 C2 -48.35(15) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
S C1 C2 C3 -179.07(13) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C2 C3 C4 Cl -179.65(13) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
Cl C4 C5 C6 179.30(14) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
S C1 C6 C5 178.72(14) . . . . ?
S N1 C7 C12 -77.52(17) . . . . ?
S N1 C7 C13 164.70(13) . . . . ?
S N1 C7 C8 45.39(19) . . . . ?
N1 C7 C8 C9 177.79(13) . . . . ?
C12 C7 C8 C9 -59.11(17) . . . . ?
C13 C7 C8 C9 60.22(17) . . . . ?
C7 C8 C9 C10 59.94(17) . . . . ?
C7 C8 C9 C16 -60.12(18) . . . . ?
C16 C9 C10 C11 59.41(17) . . . . ?
C8 C9 C10 C11 -60.63(17) . . . . ?
C9 C10 C11 C17 -179.71(14) . . . . ?
C9 C10 C11 C15 -58.26(17) . . . . ?
C9 C10 C11 C12 59.07(17) . . . . ?
N1 C7 C12 C11 -176.46(12) . . . . ?
C13 C7 C12 C11 -60.43(17) . . . . ?
C8 C7 C12 C11 58.98(17) . . . . ?
C17 C11 C12 C7 -179.89(14) . . . . ?
C10 C11 C12 C7 -58.29(17) . . . . ?
C15 C11 C12 C7 59.07(17) . . . . ?
N1 C7 C13 C14 178.30(13) . . . . ?
C12 C7 C13 C14 59.74(17) . . . . ?
C8 C7 C13 C14 -60.10(18) . . . . ?
C7 C13 C14 C18 -179.82(15) . . . . ?
C7 C13 C14 C16 58.92(18) . . . . ?
C7 C13 C14 C15 -58.32(18) . . . . ?
C18 C14 C15 C11 179.52(14) . . . . ?
C16 C14 C15 C11 -59.80(17) . . . . ?
C13 C14 C15 C11 58.17(18) . . . . ?
C17 C11 C15 C14 -179.01(14) . . . . ?
C10 C11 C15 C14 59.37(17) . . . . ?
C12 C11 C15 C14 -58.19(18) . . . . ?
C18 C14 C16 C9 -179.81(15) . . . . ?
C15 C14 C16 C9 59.44(17) . . . . ?
C13 C14 C16 C9 -58.62(18) . . . . ?
C10 C9 C16 C14 -60.28(18) . . . . ?
C8 C9 C16 C14 59.79(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.81(2) 2.07(2) 2.8806(18) 171(2) 3
C12 H121 O2 1.013(17) 2.556(17) 3.201(2) 121.2(13) .

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1590180'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_date             2017-12-08T23:09:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C16 H20 Br N O2 S'
_chemical_formula_sum            'C16 H20 Br N O2 S'
_chemical_formula_weight         370.3

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   11.0548(8)
_cell_length_b                   6.4659(4)
_cell_length_c                   21.6540(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.382(2)
_cell_angle_gamma                90
_cell_volume                     1511.81(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4551
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      31.89

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             760

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

_exptl_absorpt_coefficient_mu    2.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.3513
_exptl_absorpt_correction_T_max  0.7463

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_number            16988
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         32.078
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_reflns_Friedel_coverage         0
_reflns_number_total             5149
_reflns_number_gt                3856
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5149
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.111

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
Br1 Br 0.33783(2) 0.76048(4) 0.52132(2) 0.03437(8) Uani 1 1 d . . . . .
S1 S 0.39074(4) 0.15644(7) 0.29393(2) 0.01741(10) Uani 1 1 d . . . . .
O2 O 0.31862(13) -0.0243(2) 0.29847(6) 0.0263(3) Uani 1 1 d . . . . .
O1 O 0.52344(12) 0.1372(2) 0.30286(6) 0.0271(3) Uani 1 1 d . . . . .
N1 N 0.34757(13) 0.2576(2) 0.22464(7) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.36665(15) 0.3309(3) 0.35346(8) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.42285(19) 0.5244(3) 0.35833(9) 0.0233(4) Uani 1 1 d . . . . .
C3 C 0.4138(2) 0.6526(3) 0.40807(10) 0.0255(4) Uani 1 1 d . . . . .
C4 C 0.34866(16) 0.5855(3) 0.45230(9) 0.0222(4) Uani 1 1 d . . . . .
C5 C 0.29194(19) 0.3941(4) 0.44772(10) 0.0287(4) Uani 1 1 d . . . . .
C6 C 0.30109(19) 0.2654(3) 0.39776(10) 0.0248(4) Uani 1 1 d . . . . .
C7 C 0.21934(14) 0.2875(2) 0.18713(8) 0.0124(3) Uani 1 1 d . . . . .
C8 C 0.23734(16) 0.3456(3) 0.12076(8) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.11158(16) 0.3830(3) 0.07629(8) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.03428(17) 0.1839(3) 0.07138(9) 0.0216(4) Uani 1 1 d . . . . .
C11 C 0.01612(16) 0.1258(3) 0.13725(9) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.14227(16) 0.0889(3) 0.18221(9) 0.0175(3) Uani 1 1 d . . . . .
C13 C 0.15126(16) 0.4630(3) 0.21297(8) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.02481(16) 0.4995(3) 0.16805(8) 0.0173(3) Uani 1 1 d . . . . .
C15 C -0.05235(16) 0.3009(3) 0.16335(10) 0.0202(4) Uani 1 1 d . . . . .
C16 C 0.04405(17) 0.5582(3) 0.10249(8) 0.0192(3) Uani 1 1 d . . . . .
H1 H 0.397(2) 0.348(4) 0.2187(11) 0.024(6) Uiso 1 1 d . . . . .
H2 H 0.469(2) 0.567(4) 0.3286(11) 0.026(6) Uiso 1 1 d . . . . .
H3 H 0.450(2) 0.784(3) 0.4122(11) 0.023(6) Uiso 1 1 d . . . . .
H4 H 0.251(2) 0.354(4) 0.4809(12) 0.037(7) Uiso 1 1 d . . . . .
H5 H 0.262(3) 0.137(4) 0.3941(12) 0.041(7) Uiso 1 1 d . . . . .
H6 H 0.285(2) 0.472(4) 0.1261(11) 0.025(6) Uiso 1 1 d . . . . .
H7 H 0.279(2) 0.235(3) 0.1059(12) 0.026(6) Uiso 1 1 d . . . . .
H8 H 0.1278(18) 0.426(3) 0.0343(10) 0.018(5) Uiso 1 1 d . . . . .
H9 H -0.045(2) 0.203(3) 0.0438(11) 0.019(5) Uiso 1 1 d . . . . .
H10 H 0.077(2) 0.069(3) 0.0534(10) 0.022(5) Uiso 1 1 d . . . . .
H11 H -0.035(2) -0.005(4) 0.1362(11) 0.028(6) Uiso 1 1 d . . . . .
H12 H 0.1301(19) 0.044(3) 0.2245(10) 0.020(5) Uiso 1 1 d . . . . .
H13 H 0.186(2) -0.015(3) 0.1684(11) 0.022(5) Uiso 1 1 d . . . . .
H14 H 0.199(2) 0.583(4) 0.2183(10) 0.020(5) Uiso 1 1 d . . . . .
H15 H 0.1383(19) 0.428(3) 0.2569(10) 0.019(5) Uiso 1 1 d . . . . .
H16 H -0.023(2) 0.617(4) 0.1843(10) 0.025(6) Uiso 1 1 d . . . . .
H17 H -0.132(2) 0.318(3) 0.1339(10) 0.020(5) Uiso 1 1 d . . . . .
H18 H -0.072(2) 0.260(3) 0.2047(12) 0.026(6) Uiso 1 1 d . . . . .
H19 H 0.089(2) 0.681(4) 0.1036(11) 0.027(6) Uiso 1 1 d . . . . .
H20 H -0.039(2) 0.584(3) 0.0731(10) 0.022(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
Br1 C4 1.8984(18) . ?
S1 O2 1.4300(15) . ?
S1 O1 1.4433(13) . ?
S1 N1 1.6123(16) . ?
S1 C1 1.7757(18) . ?
N1 C7 1.488(2) . ?
N1 H1 0.83(2) . ?
C1 C6 1.387(3) . ?
C1 C2 1.391(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.95(2) . ?
C3 C4 1.385(3) . ?
C3 H3 0.93(2) . ?
C4 C5 1.382(3) . ?
C5 C6 1.385(3) . ?
C5 H4 0.96(3) . ?
C6 H5 0.93(3) . ?
C7 C13 1.532(2) . ?
C7 C12 1.532(2) . ?
C7 C8 1.539(2) . ?
C8 C9 1.531(2) . ?
C8 H6 0.97(2) . ?
C8 H7 0.95(2) . ?
C9 C16 1.531(3) . ?
C9 C10 1.536(3) . ?
C9 H8 1.00(2) . ?
C10 C11 1.529(3) . ?
C10 H9 0.96(2) . ?
C10 H10 1.00(2) . ?
C11 C15 1.536(3) . ?
C11 C12 1.539(2) . ?
C11 H11 1.02(2) . ?
C12 H12 1.00(2) . ?
C12 H13 0.91(2) . ?
C13 C14 1.540(2) . ?
C13 H14 0.93(2) . ?
C13 H15 1.02(2) . ?
C14 C16 1.528(3) . ?
C14 C15 1.533(3) . ?
C14 H16 1.03(2) . ?
C15 H17 0.98(2) . ?
C15 H18 1.00(3) . ?
C16 H19 0.93(2) . ?
C16 H20 1.01(2) . ?

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 119.07(9) . . ?
O2 S1 N1 109.71(8) . . ?
O1 S1 N1 104.43(8) . . ?
O2 S1 C1 107.27(9) . . ?
O1 S1 C1 105.30(8) . . ?
N1 S1 C1 110.94(8) . . ?
C7 N1 S1 128.18(12) . . ?
C7 N1 H1 114.0(16) . . ?
S1 N1 H1 110.9(16) . . ?
C6 C1 C2 120.90(17) . . ?
C6 C1 S1 119.35(15) . . ?
C2 C1 S1 119.50(14) . . ?
C3 C2 C1 119.55(18) . . ?
C3 C2 H2 119.7(14) . . ?
C1 C2 H2 120.7(14) . . ?
C2 C3 C4 119.18(19) . . ?
C2 C3 H3 121.3(15) . . ?
C4 C3 H3 119.5(15) . . ?
C5 C4 C3 121.73(18) . . ?
C5 C4 Br1 119.09(15) . . ?
C3 C4 Br1 119.18(15) . . ?
C4 C5 C6 119.07(18) . . ?
C4 C5 H4 117.8(16) . . ?
C6 C5 H4 123.0(16) . . ?
C5 C6 C1 119.56(18) . . ?
C5 C6 H5 119.5(16) . . ?
C1 C6 H5 120.9(16) . . ?
N1 C7 C13 112.48(13) . . ?
N1 C7 C12 112.29(13) . . ?
C13 C7 C12 109.67(14) . . ?
N1 C7 C8 104.05(13) . . ?
C13 C7 C8 109.42(14) . . ?
C12 C7 C8 108.72(14) . . ?
C9 C8 C7 110.12(14) . . ?
C9 C8 H6 110.1(13) . . ?
C7 C8 H6 105.8(14) . . ?
C9 C8 H7 110.6(16) . . ?
C7 C8 H7 107.6(15) . . ?
H6 C8 H7 112.5(19) . . ?
C8 C9 C16 109.43(14) . . ?
C8 C9 C10 109.15(15) . . ?
C16 C9 C10 109.73(15) . . ?
C8 C9 H8 107.4(11) . . ?
C16 C9 H8 109.1(12) . . ?
C10 C9 H8 112.0(12) . . ?
C11 C10 C9 108.88(14) . . ?
C11 C10 H9 109.1(13) . . ?
C9 C10 H9 110.9(13) . . ?
C11 C10 H10 110.4(13) . . ?
C9 C10 H10 110.3(12) . . ?
H9 C10 H10 107.4(18) . . ?
C10 C11 C15 109.62(15) . . ?
C10 C11 C12 110.23(15) . . ?
C15 C11 C12 109.44(15) . . ?
C10 C11 H11 111.6(13) . . ?
C15 C11 H11 107.9(13) . . ?
C12 C11 H11 108.0(13) . . ?
C7 C12 C11 109.20(14) . . ?
C7 C12 H12 111.4(13) . . ?
C11 C12 H12 110.1(12) . . ?
C7 C12 H13 108.5(14) . . ?
C11 C12 H13 112.0(14) . . ?
H12 C12 H13 105.6(19) . . ?
C7 C13 C14 109.48(13) . . ?
C7 C13 H14 110.5(14) . . ?
C14 C13 H14 111.5(13) . . ?
C7 C13 H15 110.7(12) . . ?
C14 C13 H15 109.5(12) . . ?
H14 C13 H15 105.1(18) . . ?
C16 C14 C15 109.43(15) . . ?
C16 C14 C13 109.67(14) . . ?
C15 C14 C13 109.26(14) . . ?
C16 C14 H16 108.6(12) . . ?
C15 C14 H16 108.8(12) . . ?
C13 C14 H16 111.0(12) . . ?
C14 C15 C11 109.33(14) . . ?
C14 C15 H17 111.1(13) . . ?
C11 C15 H17 107.0(13) . . ?
C14 C15 H18 112.7(13) . . ?
C11 C15 H18 110.4(13) . . ?
H17 C15 H18 106.2(19) . . ?
C14 C16 C9 109.68(14) . . ?
C14 C16 H19 111.4(15) . . ?
C9 C16 H19 109.8(15) . . ?
C14 C16 H20 109.9(12) . . ?
C9 C16 H20 109.7(12) . . ?
H19 C16 H20 106.2(19) . . ?

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
O2 S1 N1 C7 42.61(16) . . . . ?
O1 S1 N1 C7 171.31(14) . . . . ?
C1 S1 N1 C7 -75.73(16) . . . . ?
O2 S1 C1 C6 7.92(17) . . . . ?
O1 S1 C1 C6 -119.86(16) . . . . ?
N1 S1 C1 C6 127.73(15) . . . . ?
O2 S1 C1 C2 -177.70(14) . . . . ?
O1 S1 C1 C2 54.52(16) . . . . ?
N1 S1 C1 C2 -57.89(16) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
S1 C1 C2 C3 -173.98(15) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 Br1 179.24(15) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
Br1 C4 C5 C6 -179.24(15) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
S1 C1 C6 C5 173.99(16) . . . . ?
S1 N1 C7 C13 73.58(18) . . . . ?
S1 N1 C7 C12 -50.7(2) . . . . ?
S1 N1 C7 C8 -168.11(13) . . . . ?
N1 C7 C8 C9 -179.68(13) . . . . ?
C13 C7 C8 C9 -59.28(18) . . . . ?
C12 C7 C8 C9 60.48(18) . . . . ?
C7 C8 C9 C16 59.39(19) . . . . ?
C7 C8 C9 C10 -60.70(19) . . . . ?
C8 C9 C10 C11 59.89(19) . . . . ?
C16 C9 C10 C11 -60.02(18) . . . . ?
C9 C10 C11 C15 60.32(18) . . . . ?
C9 C10 C11 C12 -60.22(19) . . . . ?
N1 C7 C12 C11 -174.13(14) . . . . ?
C13 C7 C12 C11 60.04(18) . . . . ?
C8 C7 C12 C11 -59.56(18) . . . . ?
C10 C11 C12 C7 60.45(19) . . . . ?
C15 C11 C12 C7 -60.19(19) . . . . ?
N1 C7 C13 C14 174.22(14) . . . . ?
C12 C7 C13 C14 -60.06(18) . . . . ?
C8 C7 C13 C14 59.11(18) . . . . ?
C7 C13 C14 C16 -59.91(18) . . . . ?
C7 C13 C14 C15 60.03(18) . . . . ?
C16 C14 C15 C11 59.86(19) . . . . ?
C13 C14 C15 C11 -60.24(19) . . . . ?
C10 C11 C15 C14 -60.52(19) . . . . ?
C12 C11 C15 C14 60.50(19) . . . . ?
C15 C14 C16 C9 -59.71(18) . . . . ?
C13 C14 C16 C9 60.14(18) . . . . ?
C8 C9 C16 C14 -59.77(19) . . . . ?
C10 C9 C16 C14 59.96(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.83(2) 2.16(2) 2.963(2) 163(2) 2_655
C8 H6 Br1 0.97(2) 3.01(2) 3.6582(18) 125.8(16) 4_575
C8 H6 O1 0.97(2) 2.57(2) 3.377(2) 141.7(18) 2_655
C12 H12 O2 1.00(2) 2.38(2) 2.927(2) 113.6(15) .

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1590183'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_date             2017-12-09T12:11:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C19 H24 F3 N O2 S'
_chemical_formula_sum            'C19 H24 F3 N O2 S'
_chemical_formula_weight         387.45

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   10.7288(4)
_cell_length_b                   15.5406(6)
_cell_length_c                   11.6218(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.4540(10)
_cell_angle_gamma                90
_cell_volume                     1858.37(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9718
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      31.99

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             816

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

_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6772
_exptl_absorpt_correction_T_max  0.7463

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_number            27756
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         32.029
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             6393
_reflns_number_gt                5285
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   mixed

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6393
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.078

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
S1 S 0.33513(3) 0.41656(2) 0.39446(3) 0.01835(9) Uani 1 1 d . . . . .
F1 F 0.57976(13) 0.26524(7) -0.03404(11) 0.0523(3) Uani 1 1 d . . . . .
F2 F 0.63779(15) 0.39559(10) -0.03323(13) 0.0652(4) Uani 1 1 d . . . . .
F3 F 0.44760(13) 0.35896(11) -0.13208(10) 0.0637(4) Uani 1 1 d . . . . .
O1 O 0.22011(9) 0.36537(6) 0.37808(9) 0.02343(19) Uani 1 1 d . . . . .
O2 O 0.44272(9) 0.40379(6) 0.50062(9) 0.0243(2) Uani 1 1 d . . . . .
N1 N 0.29885(10) 0.51687(7) 0.39348(10) 0.0202(2) Uani 1 1 d . . . . .
H1 H 0.368(2) 0.5467(14) 0.425(2) 0.036(5) Uiso 1 1 d . . . . .
C1 C 0.39557(12) 0.39495(8) 0.26988(12) 0.0204(2) Uani 1 1 d . . . . .
C2 C 0.50079(14) 0.44239(9) 0.25616(14) 0.0272(3) Uani 1 1 d . . . . .
H2 H 0.5406(19) 0.4810(13) 0.3129(18) 0.032(5) Uiso 1 1 d . . . . .
C3 C 0.54737(15) 0.42549(10) 0.15859(15) 0.0289(3) Uani 1 1 d . . . . .
H3 H 0.616(2) 0.4575(16) 0.153(2) 0.054(7) Uiso 1 1 d . . . . .
C4 C 0.49026(14) 0.36180(9) 0.07713(13) 0.0254(3) Uani 1 1 d . . . . .
C5 C 0.38622(16) 0.31394(10) 0.09175(15) 0.0316(3) Uani 1 1 d . . . . .
H4 H 0.349(2) 0.2671(14) 0.040(2) 0.039(5) Uiso 1 1 d . . . . .
C6 C 0.33820(15) 0.33115(9) 0.18846(14) 0.0289(3) Uani 1 1 d . . . . .
H5 H 0.270(2) 0.3002(15) 0.198(2) 0.047(6) Uiso 1 1 d . . . . .
C7 C 0.18158(11) 0.56060(7) 0.31561(10) 0.0168(2) Uani 1 1 d . . . . .
C8 C 0.21288(14) 0.65696(8) 0.32619(15) 0.0281(3) Uani 1 1 d . . . . .
H6 H 0.2319(18) 0.6730(13) 0.4140(18) 0.030(5) Uiso 1 1 d . . . . .
H7 H 0.287(2) 0.6677(15) 0.299(2) 0.045(6) Uiso 1 1 d . . . . .
C9 C 0.09649(14) 0.70992(9) 0.25232(14) 0.0281(3) Uani 1 1 d . . . . .
C10 C -0.02129(14) 0.69083(10) 0.29767(13) 0.0281(3) Uani 1 1 d . . . . .
H8 H -0.0955(19) 0.7232(13) 0.2516(18) 0.032(5) Uiso 1 1 d . . . . .
H9 H -0.004(2) 0.7092(15) 0.382(2) 0.043(6) Uiso 1 1 d . . . . .
C11 C -0.05495(13) 0.59470(10) 0.28896(12) 0.0247(3) Uani 1 1 d . . . . .
C12 C 0.06426(12) 0.54390(9) 0.36271(11) 0.0219(2) Uani 1 1 d . . . . .
H10 H 0.084(2) 0.5595(14) 0.447(2) 0.038(5) Uiso 1 1 d . . . . .
H11 H 0.0449(19) 0.4830(13) 0.3618(17) 0.031(5) Uiso 1 1 d . . . . .
C13 C 0.14950(14) 0.53326(9) 0.18378(11) 0.0238(2) Uani 1 1 d . . . . .
H12 H 0.1279(19) 0.4695(13) 0.1760(18) 0.032(5) Uiso 1 1 d . . . . .
H13 H 0.220(2) 0.5449(13) 0.1481(19) 0.036(5) Uiso 1 1 d . . . . .
C14 C 0.03244(15) 0.58570(9) 0.11034(12) 0.0262(3) Uani 1 1 d . . . . .
H14 H 0.0176(19) 0.5711(12) 0.0299(18) 0.029(5) Uiso 1 1 d . . . . .
C15 C -0.08455(13) 0.56748(9) 0.15698(13) 0.0268(3) Uani 1 1 d . . . . .
H15 H -0.165(2) 0.6008(14) 0.1065(19) 0.039(5) Uiso 1 1 d . . . . .
H16 H -0.1066(18) 0.5076(12) 0.1539(17) 0.028(4) Uiso 1 1 d . . . . .
C16 C 0.06414(16) 0.68163(10) 0.12106(14) 0.0304(3) Uani 1 1 d . . . . .
H18 H -0.011(2) 0.7166(14) 0.0701(19) 0.037(5) Uiso 1 1 d . . . . .
H17 H 0.137(2) 0.6925(14) 0.089(2) 0.042(6) Uiso 1 1 d . . . . .
C17 C 0.1279(2) 0.80587(11) 0.2641(2) 0.0553(6) Uani 1 1 d . . . . .
H17A H 0.202977 0.817639 0.234288 0.083 Uiso 1 1 calc R U . . .
H17B H 0.148181 0.822814 0.348646 0.083 Uiso 1 1 calc R U . . .
H17C H 0.052795 0.838748 0.217047 0.083 Uiso 1 1 calc R U . . .
C18 C -0.17071(16) 0.57623(15) 0.33696(18) 0.0454(5) Uani 1 1 d . . . . .
H18A H -0.186932 0.514115 0.334856 0.068 Uiso 1 1 calc R U . . .
H18B H -0.247807 0.60583 0.287062 0.068 Uiso 1 1 calc R U . . .
H18C H -0.151719 0.596894 0.419805 0.068 Uiso 1 1 calc R U . . .
C19 C 0.53780(16) 0.34450(10) -0.03037(14) 0.0308(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O1 1.4348(9) . ?
S1 O2 1.4447(10) . ?
S1 N1 1.6060(11) . ?
S1 C1 1.7781(13) . ?
F1 C19 1.3163(18) . ?
F2 C19 1.343(2) . ?
F3 C19 1.3176(19) . ?
N1 C7 1.4896(15) . ?
N1 H1 0.87(2) . ?
C1 C6 1.3882(18) . ?
C1 C2 1.3948(18) . ?
C2 C3 1.388(2) . ?
C2 H2 0.90(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.91(3) . ?
C4 C5 1.391(2) . ?
C4 C19 1.501(2) . ?
C5 C6 1.389(2) . ?
C5 H4 0.95(2) . ?
C6 H5 0.91(2) . ?
C7 C12 1.5302(17) . ?
C7 C8 1.5320(17) . ?
C7 C13 1.5322(17) . ?
C8 C9 1.5383(19) . ?
C8 H6 1.01(2) . ?
C8 H7 0.95(2) . ?
C9 C17 1.526(2) . ?
C9 C10 1.530(2) . ?
C9 C16 1.530(2) . ?
C10 C11 1.534(2) . ?
C10 H8 0.97(2) . ?
C10 H9 0.99(2) . ?
C11 C18 1.526(2) . ?
C11 C15 1.535(2) . ?
C11 C12 1.5403(18) . ?
C12 H10 0.97(2) . ?
C12 H11 0.97(2) . ?
C13 C14 1.5371(19) . ?
C13 H12 1.02(2) . ?
C13 H13 0.98(2) . ?
C14 C16 1.526(2) . ?
C14 C15 1.528(2) . ?
C14 H14 0.93(2) . ?
C15 H15 1.04(2) . ?
C15 H16 0.958(19) . ?
C16 H18 1.01(2) . ?
C16 H17 0.97(2) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 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
O1 S1 O2 119.10(6) . . ?
O1 S1 N1 109.85(6) . . ?
O2 S1 N1 105.83(6) . . ?
O1 S1 C1 106.59(6) . . ?
O2 S1 C1 106.38(6) . . ?
N1 S1 C1 108.73(6) . . ?
C7 N1 S1 127.48(8) . . ?
C7 N1 H1 119.4(15) . . ?
S1 N1 H1 109.8(14) . . ?
C6 C1 C2 121.10(13) . . ?
C6 C1 S1 119.76(10) . . ?
C2 C1 S1 119.14(10) . . ?
C3 C2 C1 118.94(13) . . ?
C3 C2 H2 121.1(13) . . ?
C1 C2 H2 119.8(13) . . ?
C4 C3 C2 120.08(13) . . ?
C4 C3 H3 123.3(16) . . ?
C2 C3 H3 116.6(16) . . ?
C3 C4 C5 120.86(13) . . ?
C3 C4 C19 120.48(13) . . ?
C5 C4 C19 118.64(13) . . ?
C6 C5 C4 119.36(13) . . ?
C6 C5 H4 118.2(13) . . ?
C4 C5 H4 122.3(13) . . ?
C1 C6 C5 119.66(13) . . ?
C1 C6 H5 120.7(15) . . ?
C5 C6 H5 119.6(15) . . ?
N1 C7 C12 110.13(10) . . ?
N1 C7 C8 105.61(9) . . ?
C12 C7 C8 108.72(11) . . ?
N1 C7 C13 113.13(10) . . ?
C12 C7 C13 109.64(10) . . ?
C8 C7 C13 109.47(11) . . ?
C7 C8 C9 110.69(11) . . ?
C7 C8 H6 107.3(11) . . ?
C9 C8 H6 109.3(11) . . ?
C7 C8 H7 109.2(14) . . ?
C9 C8 H7 110.1(14) . . ?
H6 C8 H7 110.2(18) . . ?
C17 C9 C10 109.97(14) . . ?
C17 C9 C16 110.63(15) . . ?
C10 C9 C16 108.16(12) . . ?
C17 C9 C8 110.41(12) . . ?
C10 C9 C8 108.85(12) . . ?
C16 C9 C8 108.77(12) . . ?
C9 C10 C11 111.61(11) . . ?
C9 C10 H8 109.9(12) . . ?
C11 C10 H8 109.2(12) . . ?
C9 C10 H9 110.3(13) . . ?
C11 C10 H9 108.7(13) . . ?
H8 C10 H9 107.0(17) . . ?
C18 C11 C10 111.09(14) . . ?
C18 C11 C15 110.74(13) . . ?
C10 C11 C15 108.21(11) . . ?
C18 C11 C12 109.49(11) . . ?
C10 C11 C12 108.64(11) . . ?
C15 C11 C12 108.60(11) . . ?
C7 C12 C11 110.58(10) . . ?
C7 C12 H10 110.6(12) . . ?
C11 C12 H10 110.0(13) . . ?
C7 C12 H11 110.9(12) . . ?
C11 C12 H11 110.7(12) . . ?
H10 C12 H11 103.9(17) . . ?
C7 C13 C14 108.97(10) . . ?
C7 C13 H12 109.9(11) . . ?
C14 C13 H12 109.7(11) . . ?
C7 C13 H13 113.0(12) . . ?
C14 C13 H13 106.0(12) . . ?
H12 C13 H13 109.1(17) . . ?
C16 C14 C15 109.78(12) . . ?
C16 C14 C13 110.14(12) . . ?
C15 C14 C13 109.20(11) . . ?
C16 C14 H14 106.9(12) . . ?
C15 C14 H14 112.8(12) . . ?
C13 C14 H14 108.0(12) . . ?
C14 C15 C11 110.19(11) . . ?
C14 C15 H15 110.2(12) . . ?
C11 C15 H15 109.3(12) . . ?
C14 C15 H16 112.7(11) . . ?
C11 C15 H16 106.5(11) . . ?
H15 C15 H16 107.8(16) . . ?
C14 C16 C9 110.14(11) . . ?
C14 C16 H18 110.7(12) . . ?
C9 C16 H18 110.3(12) . . ?
C14 C16 H17 108.8(13) . . ?
C9 C16 H17 110.9(13) . . ?
H18 C16 H17 105.9(18) . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F1 C19 F3 107.55(14) . . ?
F1 C19 F2 105.64(14) . . ?
F3 C19 F2 105.42(14) . . ?
F1 C19 C4 113.23(12) . . ?
F3 C19 C4 112.31(13) . . ?
F2 C19 C4 112.14(14) . . ?

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
O1 S1 N1 C7 -38.89(12) . . . . ?
O2 S1 N1 C7 -168.66(10) . . . . ?
C1 S1 N1 C7 77.41(12) . . . . ?
O1 S1 C1 C6 -6.43(13) . . . . ?
O2 S1 C1 C6 121.63(12) . . . . ?
N1 S1 C1 C6 -124.80(12) . . . . ?
O1 S1 C1 C2 173.92(11) . . . . ?
O2 S1 C1 C2 -58.02(12) . . . . ?
N1 S1 C1 C2 55.56(12) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
S1 C1 C2 C3 -179.80(11) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C19 178.48(14) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C19 C4 C5 C6 -177.81(14) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
S1 C1 C6 C5 -179.50(12) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
S1 N1 C7 C12 78.05(13) . . . . ?
S1 N1 C7 C8 -164.74(10) . . . . ?
S1 N1 C7 C13 -45.03(15) . . . . ?
N1 C7 C8 C9 -178.16(12) . . . . ?
C12 C7 C8 C9 -60.00(15) . . . . ?
C13 C7 C8 C9 59.74(15) . . . . ?
C7 C8 C9 C17 179.51(15) . . . . ?
C7 C8 C9 C10 58.71(16) . . . . ?
C7 C8 C9 C16 -58.92(16) . . . . ?
C17 C9 C10 C11 -179.20(13) . . . . ?
C16 C9 C10 C11 59.89(14) . . . . ?
C8 C9 C10 C11 -58.13(15) . . . . ?
C9 C10 C11 C18 178.77(12) . . . . ?
C9 C10 C11 C15 -59.46(14) . . . . ?
C9 C10 C11 C12 58.27(14) . . . . ?
N1 C7 C12 C11 175.47(10) . . . . ?
C8 C7 C12 C11 60.21(14) . . . . ?
C13 C7 C12 C11 -59.43(14) . . . . ?
C18 C11 C12 C7 179.46(14) . . . . ?
C10 C11 C12 C7 -59.06(14) . . . . ?
C15 C11 C12 C7 58.43(14) . . . . ?
N1 C7 C13 C14 -176.72(11) . . . . ?
C12 C7 C13 C14 59.94(14) . . . . ?
C8 C7 C13 C14 -59.24(14) . . . . ?
C7 C13 C14 C16 59.83(14) . . . . ?
C7 C13 C14 C15 -60.80(14) . . . . ?
C16 C14 C15 C11 -59.69(15) . . . . ?
C13 C14 C15 C11 61.16(14) . . . . ?
C18 C11 C15 C14 -179.58(12) . . . . ?
C10 C11 C15 C14 58.43(14) . . . . ?
C12 C11 C15 C14 -59.32(15) . . . . ?
C15 C14 C16 C9 60.14(15) . . . . ?
C13 C14 C16 C9 -60.14(15) . . . . ?
C17 C9 C16 C14 -179.80(14) . . . . ?
C10 C9 C16 C14 -59.31(15) . . . . ?
C8 C9 C16 C14 58.77(16) . . . . ?
C3 C4 C19 F1 120.42(16) . . . . ?
C5 C4 C19 F1 -60.94(19) . . . . ?
C3 C4 C19 F3 -117.52(17) . . . . ?
C5 C4 C19 F3 61.12(19) . . . . ?
C3 C4 C19 F2 1.0(2) . . . . ?
C5 C4 C19 F2 179.63(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.87(2) 2.11(2) 2.9647(15) 168(2) 3_666
C8 H6 F1 1.01(2) 2.55(2) 3.2514(18) 126.3(14) 2_655
C12 H11 O1 0.97(2) 2.59(2) 3.2181(16) 122.7(15) .
C13 H13 F2 0.98(2) 2.47(2) 3.4284(18) 165.5(17) 3_665

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1590185'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_date             2017-12-09T12:38:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C18 H24 N2 O4 S'
_chemical_formula_sum            'C18 H24 N2 O4 S'
_chemical_formula_weight         364.45

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   10.5834(3)
_cell_length_b                   15.2084(5)
_cell_length_c                   11.6137(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.1010(10)
_cell_angle_gamma                90
_cell_volume                     1786.66(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7513
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      31.45

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             776

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

_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.5501
_exptl_absorpt_correction_T_max  0.6481

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.031
_diffrn_reflns_number            21605
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         31.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.955
_reflns_Friedel_coverage         0
_reflns_number_total             5681
_reflns_number_gt                4776
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5681
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.115
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.06

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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
S1 S 0.16395(2) 0.08537(2) 0.10846(2) 0.01415(8) Uani 1 1 d . . . . .
O1 O 0.05326(8) 0.10183(6) 0.00296(8) 0.01894(17) Uani 1 1 d . . . . .
O2 O 0.28110(8) 0.13767(5) 0.12746(8) 0.01830(17) Uani 1 1 d . . . . .
O3 O 0.02650(15) 0.19204(9) 0.61353(12) 0.0537(4) Uani 1 1 d . . . . .
O4 O -0.14078(12) 0.10797(10) 0.53223(11) 0.0480(3) Uani 1 1 d . . . . .
N1 N 0.19913(9) -0.01676(6) 0.10350(9) 0.01551(18) Uani 1 1 d . . . . .
N2 N -0.03830(13) 0.14543(9) 0.53187(11) 0.0315(3) Uani 1 1 d . . . . .
C1 C 0.10437(10) 0.10287(7) 0.23483(10) 0.0163(2) Uani 1 1 d . . . . .
C2 C -0.00016(12) 0.05151(8) 0.24733(12) 0.0223(2) Uani 1 1 d . . . . .
C3 C -0.04768(12) 0.06597(9) 0.34498(12) 0.0248(3) Uani 1 1 d . . . . .
C4 C 0.01120(12) 0.13088(8) 0.42701(11) 0.0228(2) Uani 1 1 d . . . . .
C5 C 0.11442(13) 0.18261(8) 0.41601(12) 0.0250(3) Uani 1 1 d . . . . .
C6 C 0.16127(12) 0.16788(8) 0.31777(11) 0.0218(2) Uani 1 1 d . . . . .
C7 C 0.31733(10) -0.06340(7) 0.18199(10) 0.01363(19) Uani 1 1 d . . . . .
C8 C 0.35224(12) -0.03443(8) 0.31413(10) 0.0196(2) Uani 1 1 d . . . . .
C9 C 0.47030(13) -0.08902(8) 0.38869(11) 0.0222(2) Uani 1 1 d . . . . .
C10 C 0.58887(12) -0.07290(8) 0.34173(12) 0.0224(2) Uani 1 1 d . . . . .
C11 C 0.55608(11) -0.10181(8) 0.20938(11) 0.0189(2) Uani 1 1 d . . . . .
C12 C 0.43599(11) -0.04893(8) 0.13426(10) 0.0171(2) Uani 1 1 d . . . . .
C13 C 0.28119(11) -0.16112(8) 0.17321(12) 0.0210(2) Uani 1 1 d . . . . .
C14 C 0.39883(11) -0.21651(7) 0.24759(12) 0.0212(2) Uani 1 1 d . . . . .
C15 C 0.51812(12) -0.19969(8) 0.20130(11) 0.0206(2) Uani 1 1 d . . . . .
C16 C 0.43447(13) -0.18662(9) 0.37878(11) 0.0243(3) Uani 1 1 d . . . . .
C17 C 0.36328(16) -0.31409(9) 0.23762(19) 0.0396(4) Uani 1 1 d . . . . .
C18 C 0.67432(14) -0.08660(11) 0.16183(16) 0.0338(3) Uani 1 1 d . . . . .
H1 H 0.1304(18) -0.0482(12) 0.0722(16) 0.029(4) Uiso 1 1 d . . . . .
H2 H -0.0408(17) 0.0078(11) 0.1890(16) 0.029(4) Uiso 1 1 d . . . . .
H3 H -0.1161(19) 0.0306(13) 0.3561(17) 0.041(5) Uiso 1 1 d . . . . .
H4 H 0.1541(17) 0.2279(12) 0.4741(16) 0.034(5) Uiso 1 1 d . . . . .
H5 H 0.2350(16) 0.2013(11) 0.3096(15) 0.028(4) Uiso 1 1 d . . . . .
H6 H 0.2742(16) -0.0427(11) 0.3451(16) 0.028(4) Uiso 1 1 d . . . . .
H7 H 0.3765(15) 0.0292(10) 0.3214(14) 0.020(4) Uiso 1 1 d . . . . .
H8 H 0.4909(18) -0.0724(12) 0.4745(17) 0.036(5) Uiso 1 1 d . . . . .
H9 H 0.6659(16) -0.1087(11) 0.3903(15) 0.028(4) Uiso 1 1 d . . . . .
H10 H 0.6151(16) -0.0091(11) 0.3480(15) 0.025(4) Uiso 1 1 d . . . . .
H11 H 0.4589(16) 0.0141(11) 0.1349(15) 0.025(4) Uiso 1 1 d . . . . .
H12 H 0.4101(15) -0.0681(11) 0.0509(15) 0.022(4) Uiso 1 1 d . . . . .
H13 H 0.2607(16) -0.1790(11) 0.0893(15) 0.027(4) Uiso 1 1 d . . . . .
H14 H 0.2049(16) -0.1698(11) 0.2017(15) 0.028(4) Uiso 1 1 d . . . . .
H15 H 0.5002(16) -0.2219(11) 0.1194(16) 0.030(4) Uiso 1 1 d . . . . .
H16 H 0.5950(16) -0.2363(11) 0.2510(15) 0.026(4) Uiso 1 1 d . . . . .
H17 H 0.5073(18) -0.2227(13) 0.4266(17) 0.039(5) Uiso 1 1 d . . . . .
H18 H 0.3585(18) -0.1995(12) 0.4131(16) 0.035(5) Uiso 1 1 d . . . . .
H19 H 0.339(2) -0.3340(15) 0.150(2) 0.056(6) Uiso 1 1 d . . . . .
H20 H 0.438(2) -0.3483(14) 0.2854(19) 0.051(6) Uiso 1 1 d . . . . .
H21 H 0.288(2) -0.3244(14) 0.2698(19) 0.051(6) Uiso 1 1 d . . . . .
H22 H 0.6506(19) -0.1089(13) 0.0811(18) 0.037(5) Uiso 1 1 d . . . . .
H23 H 0.6915(19) -0.0245(14) 0.1584(19) 0.044(5) Uiso 1 1 d . . . . .
H24 H 0.7509(18) -0.1171(12) 0.2117(17) 0.037(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O2 1.4344(8) . ?
S1 O1 1.4464(8) . ?
S1 N1 1.6022(10) . ?
S1 C1 1.7795(12) . ?
O3 N2 1.2205(18) . ?
O4 N2 1.2262(17) . ?
N1 C7 1.4928(13) . ?
N1 H1 0.857(18) . ?
N2 C4 1.4770(16) . ?
C1 C6 1.3881(16) . ?
C1 C2 1.3961(16) . ?
C2 C3 1.3868(18) . ?
C2 H2 0.957(17) . ?
C3 C4 1.3861(19) . ?
C3 H3 0.94(2) . ?
C4 C5 1.3824(18) . ?
C5 C6 1.3894(18) . ?
C5 H4 0.969(18) . ?
C6 H5 0.959(17) . ?
C7 C12 1.5304(15) . ?
C7 C13 1.5305(15) . ?
C7 C8 1.5338(15) . ?
C8 C9 1.5375(16) . ?
C8 H6 1.001(17) . ?
C8 H7 0.998(16) . ?
C9 C10 1.5280(19) . ?
C9 C16 1.5280(18) . ?
C9 H8 0.988(19) . ?
C10 C11 1.5371(18) . ?
C10 H9 1.005(16) . ?
C10 H10 1.006(16) . ?
C11 C18 1.5267(17) . ?
C11 C15 1.5376(17) . ?
C11 C12 1.5398(15) . ?
C12 H11 0.989(17) . ?
C12 H12 0.971(16) . ?
C13 C14 1.5406(16) . ?
C13 H13 0.972(17) . ?
C13 H14 0.967(16) . ?
C14 C17 1.5270(18) . ?
C14 C16 1.5272(19) . ?
C14 C15 1.5321(17) . ?
C15 H15 0.974(17) . ?
C15 H16 1.014(16) . ?
C16 H17 0.976(19) . ?
C16 H18 1.016(18) . ?
C17 H19 1.02(2) . ?
C17 H20 0.97(2) . ?
C17 H21 0.98(2) . ?
C18 H22 0.96(2) . ?
C18 H23 0.96(2) . ?
C18 H24 0.965(19) . ?

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 118.85(5) . . ?
O2 S1 N1 110.10(5) . . ?
O1 S1 N1 106.03(5) . . ?
O2 S1 C1 106.86(5) . . ?
O1 S1 C1 106.12(5) . . ?
N1 S1 C1 108.49(5) . . ?
C7 N1 S1 126.91(7) . . ?
C7 N1 H1 116.6(12) . . ?
S1 N1 H1 112.3(12) . . ?
O3 N2 O4 124.24(13) . . ?
O3 N2 C4 118.24(13) . . ?
O4 N2 C4 117.50(13) . . ?
C6 C1 C2 121.44(11) . . ?
C6 C1 S1 119.48(9) . . ?
C2 C1 S1 119.07(9) . . ?
C3 C2 C1 119.04(12) . . ?
C3 C2 H2 119.6(10) . . ?
C1 C2 H2 121.4(10) . . ?
C4 C3 C2 118.50(12) . . ?
C4 C3 H3 121.4(12) . . ?
C2 C3 H3 120.0(12) . . ?
C5 C4 C3 123.34(12) . . ?
C5 C4 N2 118.19(12) . . ?
C3 C4 N2 118.47(12) . . ?
C4 C5 C6 117.82(12) . . ?
C4 C5 H4 122.2(10) . . ?
C6 C5 H4 120.0(10) . . ?
C1 C6 C5 119.87(11) . . ?
C1 C6 H5 120.5(10) . . ?
C5 C6 H5 119.6(10) . . ?
N1 C7 C12 109.88(9) . . ?
N1 C7 C13 105.82(8) . . ?
C12 C7 C13 109.33(9) . . ?
N1 C7 C8 112.74(9) . . ?
C12 C7 C8 109.83(9) . . ?
C13 C7 C8 109.12(9) . . ?
C7 C8 C9 108.98(9) . . ?
C7 C8 H6 110.0(10) . . ?
C9 C8 H6 110.4(10) . . ?
C7 C8 H7 110.1(9) . . ?
C9 C8 H7 109.3(9) . . ?
H6 C8 H7 108.1(13) . . ?
C10 C9 C16 109.92(10) . . ?
C10 C9 C8 109.21(10) . . ?
C16 C9 C8 109.85(10) . . ?
C10 C9 H8 111.0(11) . . ?
C16 C9 H8 107.5(11) . . ?
C8 C9 H8 109.4(10) . . ?
C9 C10 C11 110.09(10) . . ?
C9 C10 H9 109.2(10) . . ?
C11 C10 H9 108.3(10) . . ?
C9 C10 H10 111.5(9) . . ?
C11 C10 H10 108.9(9) . . ?
H9 C10 H10 108.8(13) . . ?
C18 C11 C10 110.51(11) . . ?
C18 C11 C15 110.60(11) . . ?
C10 C11 C15 108.42(10) . . ?
C18 C11 C12 110.11(10) . . ?
C10 C11 C12 108.86(10) . . ?
C15 C11 C12 108.28(9) . . ?
C7 C12 C11 110.38(9) . . ?
C7 C12 H11 111.3(9) . . ?
C11 C12 H11 110.0(9) . . ?
C7 C12 H12 107.3(9) . . ?
C11 C12 H12 110.6(9) . . ?
H11 C12 H12 107.2(14) . . ?
C7 C13 C14 110.41(9) . . ?
C7 C13 H13 108.4(10) . . ?
C14 C13 H13 108.3(10) . . ?
C7 C13 H14 109.1(10) . . ?
C14 C13 H14 110.6(10) . . ?
H13 C13 H14 110.0(13) . . ?
C17 C14 C16 110.36(12) . . ?
C17 C14 C15 110.23(12) . . ?
C16 C14 C15 108.25(10) . . ?
C17 C14 C13 110.39(10) . . ?
C16 C14 C13 108.57(10) . . ?
C15 C14 C13 108.99(10) . . ?
C14 C15 C11 111.58(9) . . ?
C14 C15 H15 109.9(10) . . ?
C11 C15 H15 111.6(10) . . ?
C14 C15 H16 108.3(9) . . ?
C11 C15 H16 110.2(9) . . ?
H15 C15 H16 105.0(14) . . ?
C14 C16 C9 110.32(10) . . ?
C14 C16 H17 108.8(11) . . ?
C9 C16 H17 111.5(11) . . ?
C14 C16 H18 110.0(10) . . ?
C9 C16 H18 111.4(11) . . ?
H17 C16 H18 104.7(15) . . ?
C14 C17 H19 110.4(13) . . ?
C14 C17 H20 109.6(13) . . ?
H19 C17 H20 109.6(18) . . ?
C14 C17 H21 109.6(13) . . ?
H19 C17 H21 109.6(17) . . ?
H20 C17 H21 107.9(17) . . ?
C11 C18 H22 107.0(11) . . ?
C11 C18 H23 110.4(12) . . ?
H22 C18 H23 107.7(17) . . ?
C11 C18 H24 110.1(11) . . ?
H22 C18 H24 110.5(16) . . ?
H23 C18 H24 111.1(16) . . ?

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
O2 S1 N1 C7 40.85(11) . . . . ?
O1 S1 N1 C7 170.61(9) . . . . ?
C1 S1 N1 C7 -75.77(10) . . . . ?
O2 S1 C1 C6 8.72(11) . . . . ?
O1 S1 C1 C6 -119.04(10) . . . . ?
N1 S1 C1 C6 127.40(10) . . . . ?
O2 S1 C1 C2 -172.18(9) . . . . ?
O1 S1 C1 C2 60.06(10) . . . . ?
N1 S1 C1 C2 -53.50(11) . . . . ?
C6 C1 C2 C3 -0.08(19) . . . . ?
S1 C1 C2 C3 -179.16(10) . . . . ?
C1 C2 C3 C4 -0.30(19) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 N2 -179.19(11) . . . . ?
O3 N2 C4 C5 -11.43(19) . . . . ?
O4 N2 C4 C5 170.23(13) . . . . ?
O3 N2 C4 C3 168.34(14) . . . . ?
O4 N2 C4 C3 -10.01(19) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
N2 C4 C5 C6 179.35(11) . . . . ?
C2 C1 C6 C5 0.23(19) . . . . ?
S1 C1 C6 C5 179.31(10) . . . . ?
C4 C5 C6 C1 0.00(19) . . . . ?
S1 N1 C7 C12 -81.86(11) . . . . ?
S1 N1 C7 C13 160.21(9) . . . . ?
S1 N1 C7 C8 41.01(13) . . . . ?
N1 C7 C8 C9 177.21(9) . . . . ?
C12 C7 C8 C9 -59.90(12) . . . . ?
C13 C7 C8 C9 59.94(12) . . . . ?
C7 C8 C9 C10 60.73(12) . . . . ?
C7 C8 C9 C16 -59.88(13) . . . . ?
C16 C9 C10 C11 59.50(13) . . . . ?
C8 C9 C10 C11 -61.08(13) . . . . ?
C9 C10 C11 C18 -179.58(10) . . . . ?
C9 C10 C11 C15 -58.21(12) . . . . ?
C9 C10 C11 C12 59.38(12) . . . . ?
N1 C7 C12 C11 -176.18(9) . . . . ?
C13 C7 C12 C11 -60.45(12) . . . . ?
C8 C7 C12 C11 59.25(12) . . . . ?
C18 C11 C12 C7 -179.62(11) . . . . ?
C10 C11 C12 C7 -58.34(12) . . . . ?
C15 C11 C12 C7 59.34(12) . . . . ?
N1 C7 C13 C14 177.88(10) . . . . ?
C12 C7 C13 C14 59.59(13) . . . . ?
C8 C7 C13 C14 -60.55(12) . . . . ?
C7 C13 C14 C17 -179.34(12) . . . . ?
C7 C13 C14 C16 59.56(13) . . . . ?
C7 C13 C14 C15 -58.14(13) . . . . ?
C17 C14 C15 C11 179.66(11) . . . . ?
C16 C14 C15 C11 -59.55(12) . . . . ?
C13 C14 C15 C11 58.36(13) . . . . ?
C18 C11 C15 C14 -179.53(11) . . . . ?
C10 C11 C15 C14 59.16(12) . . . . ?
C12 C11 C15 C14 -58.80(12) . . . . ?
C17 C14 C16 C9 179.89(11) . . . . ?
C15 C14 C16 C9 59.17(12) . . . . ?
C13 C14 C16 C9 -59.00(13) . . . . ?
C10 C9 C16 C14 -60.15(13) . . . . ?
C8 C9 C16 C14 60.04(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.857(18) 2.051(18) 2.8975(12) 169.2(17) 3
C8 H6 O4 1.001(17) 2.488(18) 3.4339(17) 157.4(13) 3_556
C12 H11 O2 0.989(17) 2.642(16) 3.2666(14) 121.2(12) .

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1590182'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_date             2017-12-09T00:25:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C17 H20 F3 N O2 S'
_chemical_formula_sum            'C17 H20 F3 N O2 S'
_chemical_formula_weight         359.4

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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'
'-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                   29.081(2)
_cell_length_b                   6.8576(6)
_cell_length_c                   19.1376(16)
_cell_angle_alpha                90
_cell_angle_beta                 123.701(2)
_cell_angle_gamma                90
_cell_volume                     3175.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3798
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.87

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1504

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

_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_T_max  0.7459

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_number            21520
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.145
_diffrn_reflns_theta_max         29.588
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             4464
_reflns_number_gt                3495
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4464
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1875
_refine_ls_wR_factor_gt          0.1774
_refine_ls_goodness_of_fit_ref   1.277
_refine_ls_restrained_S_all      1.277
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.224
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.113

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
N1 N 0.21265(7) 0.4496(3) 0.25842(11) 0.0197(4) Uani 1 1 d . . . . .
H1 H 0.2394(13) 0.353(5) 0.282(2) 0.055(9) Uiso 1 1 d . . . . .
S1 S 0.19542(2) 0.50516(7) 0.16553(3) 0.01582(16) Uani 1 1 d . . . . .
F1 F 0.00852(8) 0.0231(3) -0.17038(10) 0.0562(6) Uani 1 1 d . . . . .
F2 F 0.01143(7) -0.1731(2) -0.08120(11) 0.0590(6) Uani 1 1 d . . . . .
F3 F -0.04229(6) 0.0716(3) -0.12413(11) 0.0472(5) Uani 1 1 d . . . . .
O2 O 0.17781(7) 0.7052(2) 0.14792(10) 0.0268(4) Uani 1 1 d . . . . .
O1 O 0.24127(7) 0.4493(3) 0.16111(10) 0.0283(4) Uani 1 1 d . . . . .
C1 C 0.13806(8) 0.3615(3) 0.09121(12) 0.0185(4) Uani 1 1 d . . . . .
C2 C 0.14624(9) 0.1628(3) 0.08861(13) 0.0205(4) Uani 1 1 d . . . . .
H2 H 0.1790(11) 0.096(4) 0.1238(17) 0.0317(17) Uiso 1 1 d . U . . .
C3 C 0.10361(9) 0.0487(3) 0.02668(13) 0.0210(4) Uani 1 1 d . . . . .
H3 H 0.1077(11) -0.076(4) 0.0248(17) 0.0317(17) Uiso 1 1 d . U . . .
C4 C 0.05305(8) 0.1361(3) -0.03184(12) 0.0207(4) Uani 1 1 d . . . . .
C5 C 0.04456(9) 0.3335(3) -0.02779(14) 0.0235(5) Uani 1 1 d . . . . .
H4 H 0.0112(11) 0.407(4) -0.0695(17) 0.0317(17) Uiso 1 1 d . U . . .
C6 C 0.08742(9) 0.4482(3) 0.03404(14) 0.0221(4) Uani 1 1 d . . . . .
H5 H 0.0838(10) 0.598(4) 0.0339(16) 0.0317(17) Uiso 1 1 d . U . . .
C7 C 0.17938(8) 0.4645(3) 0.29600(13) 0.0189(4) Uani 1 1 d . . . . .
C8 C 0.14406(10) 0.2811(4) 0.27645(15) 0.0270(5) Uani 1 1 d . . . . .
H6 H 0.1686(10) 0.156(4) 0.2968(16) 0.0317(17) Uiso 1 1 d . U . . .
H7 H 0.1149(11) 0.272(4) 0.2131(17) 0.0317(17) Uiso 1 1 d . U . . .
C9 C 0.11414(11) 0.2924(4) 0.32211(16) 0.0329(6) Uani 1 1 d . . . . .
H8 H 0.0931(11) 0.173(4) 0.3122(16) 0.0317(17) Uiso 1 1 d . U . . .
C10 C 0.15677(11) 0.3053(4) 0.41687(16) 0.0331(6) Uani 1 1 d . . . . .
H9 H 0.1800(11) 0.193(4) 0.4346(17) 0.0317(17) Uiso 1 1 d . U . . .
H10 H 0.1393(11) 0.309(4) 0.4475(17) 0.0317(17) Uiso 1 1 d . U . . .
C11 C 0.19265(10) 0.4872(4) 0.43725(15) 0.0283(5) Uani 1 1 d . . . . .
H11 H 0.2212(12) 0.489(4) 0.4981(19) 0.0317(17) Uiso 1 1 d . U . . .
C12 C 0.22238(9) 0.4758(4) 0.39148(13) 0.0234(5) Uani 1 1 d . . . . .
H12 H 0.2446(11) 0.584(4) 0.4023(17) 0.0317(17) Uiso 1 1 d . U . . .
H13 H 0.2474(11) 0.350(4) 0.4112(17) 0.0317(17) Uiso 1 1 d . U . . .
C13 C 0.14333(10) 0.6453(4) 0.26704(15) 0.0266(5) Uani 1 1 d . . . . .
H14 H 0.1596(11) 0.757(4) 0.2705(17) 0.0317(17) Uiso 1 1 d . U . . .
H15 H 0.1174(11) 0.629(4) 0.2079(17) 0.0317(17) Uiso 1 1 d . U . . .
C14 C 0.11392(11) 0.6574(4) 0.31326(16) 0.0346(6) Uani 1 1 d . . . . .
H16 H 0.0927(11) 0.780(4) 0.2986(16) 0.0317(17) Uiso 1 1 d . U . . .
C15 C 0.15667(11) 0.6692(4) 0.40806(16) 0.0339(6) Uani 1 1 d . . . . .
H17 H 0.1789(11) 0.796(4) 0.4189(18) 0.0317(17) Uiso 1 1 d . U . . .
H18 H 0.1392(11) 0.687(4) 0.4382(17) 0.0317(17) Uiso 1 1 d . U . . .
C16 C 0.07785(11) 0.4752(5) 0.29347(18) 0.0391(7) Uani 1 1 d . . . . .
H19 H 0.0490(12) 0.464(4) 0.2349(19) 0.0317(17) Uiso 1 1 d . U . . .
H20 H 0.0611(12) 0.482(3) 0.3232(18) 0.0317(17) Uiso 1 1 d . U . . .
C17 C 0.00810(10) 0.0147(3) -0.10180(15) 0.0252(5) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
N1 C7 1.495(3) . ?
N1 S1 1.6025(18) . ?
N1 H1 0.93(3) . ?
S1 O1 1.4343(17) . ?
S1 O2 1.4376(16) . ?
S1 C1 1.773(2) . ?
F1 C17 1.320(3) . ?
F2 C17 1.335(3) . ?
F3 C17 1.337(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.390(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.93(3) . ?
C3 C4 1.396(3) . ?
C3 H3 0.86(3) . ?
C4 C5 1.386(3) . ?
C4 C17 1.501(3) . ?
C5 C6 1.391(3) . ?
C5 H4 0.99(3) . ?
C6 H5 1.03(3) . ?
C7 C13 1.516(3) . ?
C7 C8 1.533(3) . ?
C7 C12 1.540(3) . ?
C8 C9 1.539(3) . ?
C8 H6 1.04(3) . ?
C8 H7 1.03(3) . ?
C9 C10 1.529(4) . ?
C9 C16 1.531(4) . ?
C9 H8 0.98(3) . ?
C10 C11 1.532(4) . ?
C10 H9 0.95(3) . ?
C10 H10 0.97(3) . ?
C11 C15 1.522(4) . ?
C11 C12 1.536(3) . ?
C11 H11 0.99(3) . ?
C12 H12 0.93(3) . ?
C12 H13 1.05(3) . ?
C13 C14 1.536(3) . ?
C13 H14 0.89(3) . ?
C13 H15 0.96(3) . ?
C14 C15 1.530(4) . ?
C14 C16 1.537(4) . ?
C14 H16 0.99(3) . ?
C15 H17 1.03(3) . ?
C15 H18 0.97(3) . ?
C16 H19 0.96(3) . ?
C16 H20 0.93(3) . ?

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
C7 N1 S1 129.03(14) . . ?
C7 N1 H1 114(2) . . ?
S1 N1 H1 112(2) . . ?
O1 S1 O2 117.57(10) . . ?
O1 S1 N1 105.86(10) . . ?
O2 S1 N1 109.78(10) . . ?
O1 S1 C1 107.21(10) . . ?
O2 S1 C1 106.75(10) . . ?
N1 S1 C1 109.50(10) . . ?
C2 C1 C6 121.3(2) . . ?
C2 C1 S1 118.07(15) . . ?
C6 C1 S1 120.54(17) . . ?
C3 C2 C1 119.66(19) . . ?
C3 C2 H2 114.2(18) . . ?
C1 C2 H2 126.1(18) . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.9(18) . . ?
C4 C3 H3 119.9(18) . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 C17 119.87(19) . . ?
C3 C4 C17 119.0(2) . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H4 125.3(16) . . ?
C6 C5 H4 114.6(16) . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 H5 119.3(14) . . ?
C5 C6 H5 121.2(14) . . ?
N1 C7 C13 112.38(18) . . ?
N1 C7 C8 110.57(17) . . ?
C13 C7 C8 110.35(19) . . ?
N1 C7 C12 104.95(17) . . ?
C13 C7 C12 109.52(18) . . ?
C8 C7 C12 108.90(18) . . ?
C7 C8 C9 109.49(19) . . ?
C7 C8 H6 110.8(14) . . ?
C9 C8 H6 108.4(14) . . ?
C7 C8 H7 109.9(15) . . ?
C9 C8 H7 108.5(15) . . ?
H6 C8 H7 110(2) . . ?
C10 C9 C16 108.7(2) . . ?
C10 C9 C8 109.5(2) . . ?
C16 C9 C8 109.4(2) . . ?
C10 C9 H8 106.7(16) . . ?
C16 C9 H8 112.6(16) . . ?
C8 C9 H8 109.8(16) . . ?
C9 C10 C11 109.8(2) . . ?
C9 C10 H9 109.0(17) . . ?
C11 C10 H9 108.5(16) . . ?
C9 C10 H10 111.6(16) . . ?
C11 C10 H10 109.6(16) . . ?
H9 C10 H10 108(2) . . ?
C15 C11 C10 110.0(2) . . ?
C15 C11 C12 108.8(2) . . ?
C10 C11 C12 109.4(2) . . ?
C15 C11 H11 112.4(15) . . ?
C10 C11 H11 108.6(15) . . ?
C12 C11 H11 107.5(17) . . ?
C11 C12 C7 109.61(18) . . ?
C11 C12 H12 111.9(18) . . ?
C7 C12 H12 108.2(17) . . ?
C11 C12 H13 109.4(15) . . ?
C7 C12 H13 109.1(15) . . ?
H12 C12 H13 109(2) . . ?
C7 C13 C14 109.08(19) . . ?
C7 C13 H14 116.6(18) . . ?
C14 C13 H14 110.9(18) . . ?
C7 C13 H15 105.7(17) . . ?
C14 C13 H15 111.3(16) . . ?
H14 C13 H15 103(2) . . ?
C15 C14 C13 109.9(2) . . ?
C15 C14 C16 109.2(2) . . ?
C13 C14 C16 109.6(2) . . ?
C15 C14 H16 105.1(15) . . ?
C13 C14 H16 109.9(16) . . ?
C16 C14 H16 113.0(16) . . ?
C11 C15 C14 109.4(2) . . ?
C11 C15 H17 113.0(15) . . ?
C14 C15 H17 106.8(16) . . ?
C11 C15 H18 111.7(17) . . ?
C14 C15 H18 111.4(16) . . ?
H17 C15 H18 104(2) . . ?
C9 C16 C14 109.7(2) . . ?
C9 C16 H19 109.6(16) . . ?
C14 C16 H19 112.8(16) . . ?
C9 C16 H20 108.1(16) . . ?
C14 C16 H20 109.1(16) . . ?
H19 C16 H20 107(2) . . ?
F1 C17 F2 107.3(2) . . ?
F1 C17 F3 106.4(2) . . ?
F2 C17 F3 105.2(2) . . ?
F1 C17 C4 112.3(2) . . ?
F2 C17 C4 112.80(19) . . ?
F3 C17 C4 112.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 S1 O1 -175.99(18) . . . . ?
C7 N1 S1 O2 56.2(2) . . . . ?
C7 N1 S1 C1 -60.7(2) . . . . ?
O1 S1 C1 C2 45.91(19) . . . . ?
O2 S1 C1 C2 172.73(16) . . . . ?
N1 S1 C1 C2 -68.49(18) . . . . ?
O1 S1 C1 C6 -130.23(18) . . . . ?
O2 S1 C1 C6 -3.4(2) . . . . ?
N1 S1 C1 C6 115.37(18) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
S1 C1 C2 C3 -174.54(16) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C2 C3 C4 C17 176.4(2) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C17 C4 C5 C6 -176.0(2) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
S1 C1 C6 C5 174.80(16) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
S1 N1 C7 C13 -37.9(3) . . . . ?
S1 N1 C7 C8 85.9(2) . . . . ?
S1 N1 C7 C12 -156.81(17) . . . . ?
N1 C7 C8 C9 175.15(18) . . . . ?
C13 C7 C8 C9 -59.9(2) . . . . ?
C12 C7 C8 C9 60.3(2) . . . . ?
C7 C8 C9 C10 -60.2(3) . . . . ?
C7 C8 C9 C16 58.9(3) . . . . ?
C16 C9 C10 C11 -59.8(3) . . . . ?
C8 C9 C10 C11 59.7(3) . . . . ?
C9 C10 C11 C15 59.9(3) . . . . ?
C9 C10 C11 C12 -59.6(3) . . . . ?
C15 C11 C12 C7 -60.3(3) . . . . ?
C10 C11 C12 C7 60.0(3) . . . . ?
N1 C7 C12 C11 -178.78(18) . . . . ?
C13 C7 C12 C11 60.4(2) . . . . ?
C8 C7 C12 C11 -60.4(2) . . . . ?
N1 C7 C13 C14 -175.87(19) . . . . ?
C8 C7 C13 C14 60.2(2) . . . . ?
C12 C7 C13 C14 -59.7(2) . . . . ?
C7 C13 C14 C15 60.1(3) . . . . ?
C7 C13 C14 C16 -60.0(3) . . . . ?
C10 C11 C15 C14 -59.5(3) . . . . ?
C12 C11 C15 C14 60.3(3) . . . . ?
C13 C14 C15 C11 -60.6(3) . . . . ?
C16 C14 C15 C11 59.7(3) . . . . ?
C10 C9 C16 C14 60.4(3) . . . . ?
C8 C9 C16 C14 -59.2(3) . . . . ?
C15 C14 C16 C9 -60.5(3) . . . . ?
C13 C14 C16 C9 59.9(3) . . . . ?
C5 C4 C17 F1 84.6(3) . . . . ?
C3 C4 C17 F1 -93.3(3) . . . . ?
C5 C4 C17 F2 -154.1(2) . . . . ?
C3 C4 C17 F2 28.1(3) . . . . ?
C5 C4 C17 F3 -35.3(3) . . . . ?
C3 C4 C17 F3 146.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.93(3) 2.86(4) 3.773(2) 169(3) 4_545
N1 H1 O2 0.93(3) 2.25(3) 3.136(2) 161(3) 4_545
C6 H5 F2 1.03(3) 2.57(3) 3.329(3) 130.1(19) 1_565

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1590181'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_date             2017-12-08T21:18:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C18 H24 Br N O2 S'
_chemical_formula_sum            'C18 H24 Br N O2 S'
_chemical_formula_weight         398.35

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   10.5014(3)
_cell_length_b                   15.4718(4)
_cell_length_c                   11.3326(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.420(3)
_cell_angle_gamma                90
_cell_volume                     1766.17(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4153
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      35.75

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

_exptl_crystal_description       ' prism'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824
_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_exptl_absorpt_coefficient_mu    2.455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SCALE3
_exptl_absorpt_correction_T_min  0.8678
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.206
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         16653
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.039
_diffrn_reflns_number            16291
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.232
_diffrn_reflns_theta_max         35.839
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.921
_reflns_Friedel_coverage         0
_reflns_number_total             7633
_reflns_number_gt                5678
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7633
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.08

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
Br Br 0.04606(2) 0.66763(2) 0.92323(2) 0.02965(5) Uani 1 1 d . . . . .
S S -0.16457(3) 0.58420(2) 1.39032(3) 0.01354(6) Uani 1 1 d . . . . .
O1 O -0.05438(10) 0.59986(7) 1.49795(10) 0.0191(2) Uani 1 1 d . . . . .
O2 O -0.28337(10) 0.63412(7) 1.37433(9) 0.01736(19) Uani 1 1 d . . . . .
N1 N -0.19732(11) 0.48340(7) 1.39357(11) 0.0148(2) Uani 1 1 d . . . . .
H1A H -0.132(2) 0.4533(13) 1.4265(18) 0.025(5) Uiso 1 1 d . . . . .
C1 C -0.10640(13) 0.60565(9) 1.26074(13) 0.0149(2) Uani 1 1 d . . . . .
C2 C -0.00505(14) 0.55571(10) 1.23905(14) 0.0203(3) Uani 1 1 d . . . . .
H2A H 0.031(2) 0.5094(14) 1.2892(19) 0.030(5) Uiso 1 1 d . . . . .
C3 C 0.04050(15) 0.57378(11) 1.13783(15) 0.0226(3) Uani 1 1 d . . . . .
H3A H 0.114(2) 0.5391(15) 1.123(2) 0.035(6) Uiso 1 1 d . . . . .
C4 C -0.01517(15) 0.64211(10) 1.06136(14) 0.0199(3) Uani 1 1 d . . . . .
C5 C -0.11558(16) 0.69255(11) 1.08250(15) 0.0233(3) Uani 1 1 d . . . . .
H5A H -0.156(2) 0.7362(16) 1.025(2) 0.041(6) Uiso 1 1 d . . . . .
C6 C -0.16161(16) 0.67352(10) 1.18295(15) 0.0209(3) Uani 1 1 d . . . . .
H6A H -0.230(2) 0.7074(14) 1.2019(18) 0.028(5) Uiso 1 1 d . . . . .
C7 C -0.31453(12) 0.43685(8) 1.31403(11) 0.0126(2) Uani 1 1 d . . . . .
C8 C -0.34293(14) 0.46154(10) 1.17783(12) 0.0160(2) Uani 1 1 d . . . . .
H8A H -0.3648(17) 0.5240(12) 1.1661(16) 0.014(4) Uiso 1 1 d . . . . .
H8B H -0.2662(18) 0.4504(12) 1.1483(17) 0.019(4) Uiso 1 1 d . . . . .
C9 C -0.46067(14) 0.40796(10) 1.10186(12) 0.0180(3) Uani 1 1 d . . . . .
H9A H -0.4761(19) 0.4226(13) 1.0149(17) 0.024(5) Uiso 1 1 d . . . . .
C10 C -0.58289(14) 0.42728(10) 1.14544(13) 0.0184(3) Uani 1 1 d . . . . .
H10A H -0.6610(18) 0.3947(12) 1.0969(16) 0.018(4) Uiso 1 1 d . . . . .
H10B H -0.6049(18) 0.4898(12) 1.1351(17) 0.018(4) Uiso 1 1 d . . . . .
C11 C -0.55697(13) 0.40219(9) 1.28158(12) 0.0159(2) Uani 1 1 d . . . . .
C12 C -0.43744(13) 0.45471(9) 1.35781(12) 0.0148(2) Uani 1 1 d . . . . .
H12A H -0.4582(18) 0.5169(12) 1.3535(17) 0.018(4) Uiso 1 1 d . . . . .
H12B H -0.4176(18) 0.4384(13) 1.4452(17) 0.022(5) Uiso 1 1 d . . . . .
C13 C -0.28055(14) 0.34054(9) 1.32932(13) 0.0168(2) Uani 1 1 d . . . . .
H13A H -0.267(2) 0.3261(12) 1.418(2) 0.027(5) Uiso 1 1 d . . . . .
H13B H -0.2006(19) 0.3292(12) 1.3029(18) 0.019(5) Uiso 1 1 d . . . . .
C14 C -0.39732(14) 0.28576(9) 1.25379(13) 0.0182(3) Uani 1 1 d . . . . .
C15 C -0.52118(15) 0.30593(10) 1.29550(13) 0.0184(3) Uani 1 1 d . . . . .
H15A H -0.5896(18) 0.2725(12) 1.2448(17) 0.021(5) Uiso 1 1 d . . . . .
H15B H -0.501(2) 0.2898(13) 1.3825(19) 0.027(5) Uiso 1 1 d . . . . .
C16 C -0.42718(16) 0.31181(10) 1.11796(13) 0.0205(3) Uani 1 1 d . . . . .
H16A H -0.351(2) 0.3008(13) 1.0869(18) 0.026(5) Uiso 1 1 d . . . . .
H16B H -0.499(2) 0.2745(13) 1.0672(17) 0.024(5) Uiso 1 1 d . . . . .
C17 C -0.36329(19) 0.18990(11) 1.26960(19) 0.0306(4) Uani 1 1 d . . . . .
H17A H -0.284(2) 0.1781(13) 1.2387(19) 0.025(5) Uiso 1 1 d . . . . .
H17B H -0.437(2) 0.1549(15) 1.221(2) 0.043(7) Uiso 1 1 d . . . . .
H17C H -0.343(2) 0.1707(14) 1.354(2) 0.037(6) Uiso 1 1 d . . . . .
C18 C -0.67866(16) 0.42088(13) 1.32551(17) 0.0269(3) Uani 1 1 d . . . . .
H18A H -0.763(2) 0.3901(14) 1.2707(18) 0.028(5) Uiso 1 1 d . . . . .
H18B H -0.703(2) 0.4836(15) 1.320(2) 0.034(6) Uiso 1 1 d . . . . .
H18C H -0.661(2) 0.4023(17) 1.407(2) 0.053(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
Br C4 1.8944(15) . ?
S O2 1.4346(10) . ?
S O1 1.4448(10) . ?
S N1 1.5996(12) . ?
S C1 1.7740(14) . ?
N1 C7 1.4897(17) . ?
N1 H1A 0.82(2) . ?
C1 C6 1.388(2) . ?
C1 C2 1.392(2) . ?
C2 C3 1.390(2) . ?
C2 H2A 0.93(2) . ?
C3 C4 1.387(2) . ?
C3 H3A 0.99(2) . ?
C4 C5 1.386(2) . ?
C5 C6 1.388(2) . ?
C5 H5A 0.95(2) . ?
C6 H6A 0.96(2) . ?
C7 C13 1.5306(19) . ?
C7 C12 1.5331(19) . ?
C7 C8 1.5353(18) . ?
C8 C9 1.5347(19) . ?
C8 H8A 0.993(18) . ?
C8 H8B 0.972(19) . ?
C9 C16 1.528(2) . ?
C9 C10 1.529(2) . ?
C9 H9A 0.979(19) . ?
C10 C11 1.5388(19) . ?
C10 H10A 0.987(18) . ?
C10 H10B 0.994(19) . ?
C11 C18 1.524(2) . ?
C11 C15 1.533(2) . ?
C11 C12 1.5392(19) . ?
C12 H12A 0.984(18) . ?
C12 H12B 0.985(19) . ?
C13 C14 1.5366(19) . ?
C13 H13A 1.00(2) . ?
C13 H13B 0.98(2) . ?
C14 C17 1.524(2) . ?
C14 C16 1.535(2) . ?
C14 C15 1.536(2) . ?
C15 H15A 0.938(19) . ?
C15 H15B 0.98(2) . ?
C16 H16A 0.97(2) . ?
C16 H16B 0.99(2) . ?
C17 H17A 1.01(2) . ?
C17 H17B 0.98(2) . ?
C17 H17C 0.97(2) . ?
C18 H18A 1.04(2) . ?
C18 H18B 1.00(2) . ?
C18 H18C 0.93(3) . ?

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 118.47(6) . . ?
O2 S N1 110.05(6) . . ?
O1 S N1 105.67(6) . . ?
O2 S C1 106.58(6) . . ?
O1 S C1 106.65(7) . . ?
N1 S C1 109.15(6) . . ?
C7 N1 S 127.13(9) . . ?
C7 N1 H1A 116.0(14) . . ?
S N1 H1A 114.0(15) . . ?
C6 C1 C2 120.71(14) . . ?
C6 C1 S 119.18(11) . . ?
C2 C1 S 120.11(11) . . ?
C3 C2 C1 119.50(14) . . ?
C3 C2 H2A 119.0(14) . . ?
C1 C2 H2A 121.5(14) . . ?
C4 C3 C2 119.10(14) . . ?
C4 C3 H3A 121.3(13) . . ?
C2 C3 H3A 119.6(13) . . ?
C5 C4 C3 121.87(14) . . ?
C5 C4 Br 118.55(12) . . ?
C3 C4 Br 119.57(12) . . ?
C4 C5 C6 118.72(14) . . ?
C4 C5 H5A 119.3(14) . . ?
C6 C5 H5A 121.8(14) . . ?
C1 C6 C5 120.10(14) . . ?
C1 C6 H6A 118.4(13) . . ?
C5 C6 H6A 121.5(12) . . ?
N1 C7 C13 106.01(10) . . ?
N1 C7 C12 110.14(11) . . ?
C13 C7 C12 109.24(11) . . ?
N1 C7 C8 112.36(11) . . ?
C13 C7 C8 109.20(11) . . ?
C12 C7 C8 109.78(11) . . ?
C9 C8 C7 109.05(11) . . ?
C9 C8 H8A 109.3(10) . . ?
C7 C8 H8A 110.4(10) . . ?
C9 C8 H8B 109.1(11) . . ?
C7 C8 H8B 111.0(11) . . ?
H8A C8 H8B 108.0(15) . . ?
C16 C9 C10 109.73(12) . . ?
C16 C9 C8 109.71(12) . . ?
C10 C9 C8 109.26(12) . . ?
C16 C9 H9A 108.2(12) . . ?
C10 C9 H9A 111.4(11) . . ?
C8 C9 H9A 108.5(12) . . ?
C9 C10 C11 110.35(11) . . ?
C9 C10 H10A 111.2(11) . . ?
C11 C10 H10A 108.3(11) . . ?
C9 C10 H10B 109.9(11) . . ?
C11 C10 H10B 109.5(11) . . ?
H10A C10 H10B 107.6(15) . . ?
C18 C11 C15 110.76(12) . . ?
C18 C11 C10 110.65(12) . . ?
C15 C11 C10 108.47(11) . . ?
C18 C11 C12 110.03(12) . . ?
C15 C11 C12 108.53(11) . . ?
C10 C11 C12 108.34(11) . . ?
C7 C12 C11 110.54(11) . . ?
C7 C12 H12A 110.8(11) . . ?
C11 C12 H12A 110.7(10) . . ?
C7 C12 H12B 108.7(11) . . ?
C11 C12 H12B 109.6(11) . . ?
H12A C12 H12B 106.4(16) . . ?
C7 C13 C14 110.49(11) . . ?
C7 C13 H13A 107.2(11) . . ?
C14 C13 H13A 107.6(12) . . ?
C7 C13 H13B 109.3(11) . . ?
C14 C13 H13B 110.3(11) . . ?
H13A C13 H13B 111.9(17) . . ?
C17 C14 C16 110.36(13) . . ?
C17 C14 C15 110.63(13) . . ?
C16 C14 C15 107.72(12) . . ?
C17 C14 C13 110.33(12) . . ?
C16 C14 C13 108.57(12) . . ?
C15 C14 C13 109.17(12) . . ?
C11 C15 C14 111.71(11) . . ?
C11 C15 H15A 110.4(12) . . ?
C14 C15 H15A 105.5(12) . . ?
C11 C15 H15B 109.1(12) . . ?
C14 C15 H15B 107.4(12) . . ?
H15A C15 H15B 112.6(17) . . ?
C9 C16 C14 110.50(12) . . ?
C9 C16 H16A 108.2(12) . . ?
C14 C16 H16A 111.2(12) . . ?
C9 C16 H16B 112.8(11) . . ?
C14 C16 H16B 109.6(12) . . ?
H16A C16 H16B 104.5(17) . . ?
C14 C17 H17A 109.0(11) . . ?
C14 C17 H17B 110.6(14) . . ?
H17A C17 H17B 107.8(19) . . ?
C14 C17 H17C 113.2(13) . . ?
H17A C17 H17C 108.2(18) . . ?
H17B C17 H17C 108(2) . . ?
C11 C18 H18A 111.6(12) . . ?
C11 C18 H18B 112.4(13) . . ?
H18A C18 H18B 104.4(16) . . ?
C11 C18 H18C 108.4(16) . . ?
H18A C18 H18C 110.2(19) . . ?
H18B C18 H18C 110(2) . . ?

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
O2 S N1 C7 41.21(13) . . . . ?
O1 S N1 C7 170.22(11) . . . . ?
C1 S N1 C7 -75.43(13) . . . . ?
O2 S C1 C6 11.91(13) . . . . ?
O1 S C1 C6 -115.54(12) . . . . ?
N1 S C1 C6 130.74(12) . . . . ?
O2 S C1 C2 -169.17(11) . . . . ?
O1 S C1 C2 63.38(13) . . . . ?
N1 S C1 C2 -50.34(13) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
S C1 C2 C3 -179.36(12) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C2 C3 C4 Br 179.90(12) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
Br C4 C5 C6 179.38(12) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
S C1 C6 C5 178.64(12) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
S N1 C7 C13 165.07(10) . . . . ?
S N1 C7 C12 -76.87(14) . . . . ?
S N1 C7 C8 45.85(16) . . . . ?
N1 C7 C8 C9 177.46(11) . . . . ?
C13 C7 C8 C9 60.13(14) . . . . ?
C12 C7 C8 C9 -59.61(15) . . . . ?
C7 C8 C9 C16 -59.98(15) . . . . ?
C7 C8 C9 C10 60.35(15) . . . . ?
C16 C9 C10 C11 59.17(15) . . . . ?
C8 C9 C10 C11 -61.15(15) . . . . ?
C9 C10 C11 C18 -179.74(13) . . . . ?
C9 C10 C11 C15 -58.06(15) . . . . ?
C9 C10 C11 C12 59.57(15) . . . . ?
N1 C7 C12 C11 -176.28(11) . . . . ?
C13 C7 C12 C11 -60.23(14) . . . . ?
C8 C7 C12 C11 59.48(14) . . . . ?
C18 C11 C12 C7 -179.69(12) . . . . ?
C15 C11 C12 C7 58.97(14) . . . . ?
C10 C11 C12 C7 -58.61(15) . . . . ?
N1 C7 C13 C14 178.23(11) . . . . ?
C12 C7 C13 C14 59.57(14) . . . . ?
C8 C7 C13 C14 -60.50(15) . . . . ?
C7 C13 C14 C17 -179.81(14) . . . . ?
C7 C13 C14 C16 59.14(15) . . . . ?
C7 C13 C14 C15 -58.04(15) . . . . ?
C18 C11 C15 C14 -179.04(12) . . . . ?
C10 C11 C15 C14 59.34(14) . . . . ?
C12 C11 C15 C14 -58.16(14) . . . . ?
C17 C14 C15 C11 179.52(12) . . . . ?
C16 C14 C15 C11 -59.79(15) . . . . ?
C13 C14 C15 C11 57.92(15) . . . . ?
C10 C9 C16 C14 -60.18(15) . . . . ?
C8 C9 C16 C14 59.87(15) . . . . ?
C17 C14 C16 C9 -179.72(13) . . . . ?
C15 C14 C16 C9 59.42(15) . . . . ?
C13 C14 C16 C9 -58.68(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.82(2) 2.07(2) 2.8845(15) 168(2) 3_568
C12 H12A O2 0.984(18) 2.544(18) 3.1917(17) 123.3(13) .

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1590184'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_date             2017-12-09T12:25:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C16 H20 N2 O4 S'
_chemical_formula_sum            'C16 H20 N2 O4 S'
_chemical_formula_weight         336.4

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   11.0672(8)
_cell_length_b                   6.4621(5)
_cell_length_c                   21.5494(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.132(2)
_cell_angle_gamma                90
_cell_volume                     1500.85(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3720
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      29.81

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             712

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

_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.6524
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.043
_diffrn_reflns_number            18790
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.382
_diffrn_reflns_theta_max         30.066
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             4388
_reflns_number_gt                3378
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   difmap

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4388
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1
_refine_ls_restrained_S_all      1
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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
S1 S 0.10469(4) 0.17262(6) 0.20605(2) 0.01872(10) Uani 1 1 d . . . . .
O1 O -0.02797(11) 0.1585(2) 0.19781(6) 0.0287(3) Uani 1 1 d . . . . .
O2 O 0.17481(12) -0.01003(17) 0.20135(5) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.21274(14) 0.6535(2) -0.04822(6) 0.0380(3) Uani 1 1 d . . . . .
O4 O 0.12732(18) 0.9033(2) -0.00813(8) 0.0562(5) Uani 1 1 d . . . . .
N1 N 0.15275(12) 0.2775(2) 0.27481(6) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.16382(14) 0.7261(2) -0.00763(7) 0.0253(3) Uani 1 1 d . . . . .
C1 C 0.12699(14) 0.3429(2) 0.14471(7) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.06953(17) 0.5354(3) 0.13754(8) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.08150(17) 0.6619(3) 0.08762(8) 0.0248(3) Uani 1 1 d . . . . .
C4 C 0.15033(14) 0.5914(2) 0.04566(7) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.20757(16) 0.4009(3) 0.05185(8) 0.0259(4) Uani 1 1 d . . . . .
C6 C 0.19618(16) 0.2758(3) 0.10243(8) 0.0244(3) Uani 1 1 d . . . . .
C7 C 0.28214(13) 0.3052(2) 0.31277(6) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.34984(14) 0.4799(2) 0.28621(7) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.47699(14) 0.5162(2) 0.33126(7) 0.0176(3) Uani 1 1 d . . . . .
C10 C 0.45975(15) 0.5775(2) 0.39728(7) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.39310(14) 0.4024(2) 0.42417(7) 0.0183(3) Uani 1 1 d . . . . .
C12 C 0.26631(14) 0.3659(2) 0.37950(7) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.35835(14) 0.1058(2) 0.31811(8) 0.0178(3) Uani 1 1 d . . . . .
C14 C 0.48574(14) 0.1430(2) 0.36297(8) 0.0199(3) Uani 1 1 d . . . . .
C15 C 0.46966(15) 0.2032(3) 0.42960(8) 0.0217(3) Uani 1 1 d . . . . .
C16 C 0.55397(14) 0.3171(3) 0.33658(8) 0.0208(3) Uani 1 1 d . . . . .
H1 H 0.1040(17) 0.368(3) 0.2798(9) 0.020(5) Uiso 1 1 d . . . . .
H2 H 0.0225(19) 0.583(3) 0.1676(10) 0.040(6) Uiso 1 1 d . . . . .
H3 H 0.046(2) 0.791(3) 0.0823(10) 0.039(6) Uiso 1 1 d . . . . .
H4 H 0.2542(19) 0.362(3) 0.0201(10) 0.035(6) Uiso 1 1 d . . . . .
H5 H 0.2376(19) 0.151(3) 0.1075(10) 0.032(5) Uiso 1 1 d . . . . .
H6 H 0.3003(16) 0.606(3) 0.2815(8) 0.017(4) Uiso 1 1 d . . . . .
H7 H 0.3614(16) 0.440(3) 0.2447(9) 0.024(5) Uiso 1 1 d . . . . .
H8 H 0.5190(16) 0.620(3) 0.3162(9) 0.019(4) Uiso 1 1 d . . . . .
H9 H 0.4117(18) 0.700(3) 0.3962(9) 0.027(5) Uiso 1 1 d . . . . .
H10 H 0.5396(17) 0.605(3) 0.4265(9) 0.021(5) Uiso 1 1 d . . . . .
H11 H 0.3802(16) 0.447(3) 0.4652(9) 0.019(4) Uiso 1 1 d . . . . .
H12 H 0.2197(17) 0.257(3) 0.3951(9) 0.021(5) Uiso 1 1 d . . . . .
H13 H 0.2149(18) 0.489(3) 0.3763(9) 0.029(5) Uiso 1 1 d . . . . .
H14 H 0.3116(16) -0.004(3) 0.3332(8) 0.020(4) Uiso 1 1 d . . . . .
H15 H 0.3689(16) 0.059(3) 0.2771(9) 0.020(5) Uiso 1 1 d . . . . .
H16 H 0.5347(17) 0.018(3) 0.3650(9) 0.026(5) Uiso 1 1 d . . . . .
H17 H 0.4264(17) 0.094(3) 0.4451(9) 0.028(5) Uiso 1 1 d . . . . .
H18 H 0.5511(18) 0.230(3) 0.4582(9) 0.023(5) Uiso 1 1 d . . . . .
H19 H 0.6378(16) 0.340(3) 0.3651(9) 0.020(5) Uiso 1 1 d . . . . .
H20 H 0.5671(18) 0.279(3) 0.2957(10) 0.029(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 O2 1.4287(12) . ?
S1 O1 1.4411(12) . ?
S1 N1 1.6060(13) . ?
S1 C1 1.7797(15) . ?
O3 N2 1.2221(19) . ?
O4 N2 1.213(2) . ?
N1 C7 1.4898(18) . ?
N1 H1 0.819(19) . ?
N2 C4 1.475(2) . ?
C1 C6 1.386(2) . ?
C1 C2 1.390(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.97(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.92(2) . ?
C4 C5 1.377(2) . ?
C5 C6 1.386(2) . ?
C5 H4 0.98(2) . ?
C6 H5 0.92(2) . ?
C7 C13 1.530(2) . ?
C7 C8 1.536(2) . ?
C7 C12 1.539(2) . ?
C8 C9 1.535(2) . ?
C8 H6 0.975(18) . ?
C8 H7 0.967(19) . ?
C9 C10 1.530(2) . ?
C9 C16 1.533(2) . ?
C9 H8 0.919(19) . ?
C10 C11 1.534(2) . ?
C10 H9 0.95(2) . ?
C10 H10 0.978(18) . ?
C11 C12 1.529(2) . ?
C11 C15 1.531(2) . ?
C11 H11 0.972(18) . ?
C12 H12 0.977(19) . ?
C12 H13 0.97(2) . ?
C13 C14 1.536(2) . ?
C13 H14 0.978(18) . ?
C13 H15 0.965(18) . ?
C14 C16 1.534(2) . ?
C14 C15 1.536(2) . ?
C14 H16 0.966(19) . ?
C15 H17 0.95(2) . ?
C15 H18 0.984(19) . ?
C16 H19 1.001(18) . ?
C16 H20 0.96(2) . ?

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 119.57(8) . . ?
O2 S1 N1 110.04(7) . . ?
O1 S1 N1 104.77(7) . . ?
O2 S1 C1 106.79(7) . . ?
O1 S1 C1 104.88(7) . . ?
N1 S1 C1 110.59(7) . . ?
C7 N1 S1 129.25(10) . . ?
C7 N1 H1 115.0(13) . . ?
S1 N1 H1 109.4(13) . . ?
O4 N2 O3 123.83(15) . . ?
O4 N2 C4 118.12(14) . . ?
O3 N2 C4 118.05(14) . . ?
C6 C1 C2 120.94(15) . . ?
C6 C1 S1 119.03(12) . . ?
C2 C1 S1 119.93(12) . . ?
C3 C2 C1 119.59(15) . . ?
C3 C2 H2 119.7(13) . . ?
C1 C2 H2 120.7(13) . . ?
C2 C3 C4 118.58(16) . . ?
C2 C3 H3 121.3(14) . . ?
C4 C3 H3 120.1(14) . . ?
C5 C4 C3 122.67(15) . . ?
C5 C4 N2 118.50(14) . . ?
C3 C4 N2 118.83(15) . . ?
C4 C5 C6 118.41(15) . . ?
C4 C5 H4 117.8(12) . . ?
C6 C5 H4 123.8(12) . . ?
C5 C6 C1 119.80(16) . . ?
C5 C6 H5 118.2(13) . . ?
C1 C6 H5 121.9(13) . . ?
N1 C7 C13 112.65(12) . . ?
N1 C7 C8 111.91(11) . . ?
C13 C7 C8 109.87(12) . . ?
N1 C7 C12 104.15(11) . . ?
C13 C7 C12 108.80(12) . . ?
C8 C7 C12 109.24(12) . . ?
C9 C8 C7 109.34(12) . . ?
C9 C8 H6 110.6(10) . . ?
C7 C8 H6 110.1(10) . . ?
C9 C8 H7 109.3(11) . . ?
C7 C8 H7 109.0(11) . . ?
H6 C8 H7 108.5(15) . . ?
C10 C9 C16 109.41(12) . . ?
C10 C9 C8 109.72(12) . . ?
C16 C9 C8 109.48(12) . . ?
C10 C9 H8 108.7(11) . . ?
C16 C9 H8 108.9(11) . . ?
C8 C9 H8 110.6(11) . . ?
C9 C10 C11 109.43(12) . . ?
C9 C10 H9 112.4(12) . . ?
C11 C10 H9 108.0(12) . . ?
C9 C10 H10 111.1(11) . . ?
C11 C10 H10 109.3(11) . . ?
H9 C10 H10 106.5(16) . . ?
C12 C11 C15 109.33(13) . . ?
C12 C11 C10 109.11(12) . . ?
C15 C11 C10 110.10(13) . . ?
C12 C11 H11 108.4(10) . . ?
C15 C11 H11 112.0(11) . . ?
C10 C11 H11 107.9(11) . . ?
C11 C12 C7 110.17(12) . . ?
C11 C12 H12 112.0(11) . . ?
C7 C12 H12 108.6(11) . . ?
C11 C12 H13 110.9(11) . . ?
C7 C12 H13 109.4(11) . . ?
H12 C12 H13 105.6(15) . . ?
C7 C13 C14 109.09(12) . . ?
C7 C13 H14 108.2(10) . . ?
C14 C13 H14 112.6(10) . . ?
C7 C13 H15 111.8(11) . . ?
C14 C13 H15 109.9(10) . . ?
H14 C13 H15 105.2(15) . . ?
C16 C14 C15 109.40(13) . . ?
C16 C14 C13 109.88(13) . . ?
C15 C14 C13 110.07(13) . . ?
C16 C14 H16 108.1(11) . . ?
C15 C14 H16 110.5(12) . . ?
C13 C14 H16 108.9(11) . . ?
C11 C15 C14 108.71(12) . . ?
C11 C15 H17 109.5(11) . . ?
C14 C15 H17 108.4(12) . . ?
C11 C15 H18 108.2(11) . . ?
C14 C15 H18 110.2(11) . . ?
H17 C15 H18 111.8(16) . . ?
C9 C16 C14 109.34(12) . . ?
C9 C16 H19 110.0(10) . . ?
C14 C16 H19 110.4(10) . . ?
C9 C16 H20 110.1(12) . . ?
C14 C16 H20 110.2(12) . . ?
H19 C16 H20 106.9(15) . . ?

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
O2 S1 N1 C7 41.07(15) . . . . ?
O1 S1 N1 C7 170.82(12) . . . . ?
C1 S1 N1 C7 -76.67(14) . . . . ?
O2 S1 C1 C6 3.73(15) . . . . ?
O1 S1 C1 C6 -124.11(14) . . . . ?
N1 S1 C1 C6 123.45(13) . . . . ?
O2 S1 C1 C2 -179.90(13) . . . . ?
O1 S1 C1 C2 52.25(14) . . . . ?
N1 S1 C1 C2 -60.19(14) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
S1 C1 C2 C3 -176.32(13) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 N2 -179.78(15) . . . . ?
O4 N2 C4 C5 -170.50(17) . . . . ?
O3 N2 C4 C5 8.5(2) . . . . ?
O4 N2 C4 C3 9.1(2) . . . . ?
O3 N2 C4 C3 -171.96(16) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
N2 C4 C5 C6 179.14(15) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
S1 C1 C6 C5 175.70(13) . . . . ?
S1 N1 C7 C13 -49.08(17) . . . . ?
S1 N1 C7 C8 75.31(16) . . . . ?
S1 N1 C7 C12 -166.81(11) . . . . ?
N1 C7 C8 C9 173.98(12) . . . . ?
C13 C7 C8 C9 -60.10(15) . . . . ?
C12 C7 C8 C9 59.18(15) . . . . ?
C7 C8 C9 C10 -60.14(16) . . . . ?
C7 C8 C9 C16 59.94(15) . . . . ?
C16 C9 C10 C11 -59.55(16) . . . . ?
C8 C9 C10 C11 60.58(16) . . . . ?
C9 C10 C11 C12 -60.13(16) . . . . ?
C9 C10 C11 C15 59.86(16) . . . . ?
C15 C11 C12 C7 -60.54(16) . . . . ?
C10 C11 C12 C7 59.93(16) . . . . ?
N1 C7 C12 C11 -179.33(12) . . . . ?
C13 C7 C12 C11 60.32(16) . . . . ?
C8 C7 C12 C11 -59.62(15) . . . . ?
N1 C7 C13 C14 -174.72(12) . . . . ?
C8 C7 C13 C14 59.78(15) . . . . ?
C12 C7 C13 C14 -59.77(15) . . . . ?
C7 C13 C14 C16 -59.80(16) . . . . ?
C7 C13 C14 C15 60.74(16) . . . . ?
C12 C11 C15 C14 59.83(16) . . . . ?
C10 C11 C15 C14 -60.02(16) . . . . ?
C16 C14 C15 C11 60.42(16) . . . . ?
C13 C14 C15 C11 -60.41(16) . . . . ?
C10 C9 C16 C14 60.32(16) . . . . ?
C8 C9 C16 C14 -59.95(16) . . . . ?
C15 C14 C16 C9 -60.91(16) . . . . ?
C13 C14 C16 C9 60.03(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.819(19) 2.16(2) 2.9476(18) 162.3(18) 2
C12 H13 O1 0.97(2) 2.56(2) 3.3634(19) 140.7(15) 2
C13 H15 O2 0.965(18) 2.426(17) 2.9488(19) 113.7(12) .

