# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1812327'
_audit_update_record             
;
2017-12-19 deposited with the CCDC.
2018-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H25 Cl N O, Cl'
_chemical_formula_sum            'C24 H25 Cl2 N O'
_chemical_formula_weight         414.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.7990(4)
_cell_length_b                   14.7395(6)
_cell_length_c                   16.0279(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2078.70(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      67.62

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    2.912
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison,
Wisconsin, USA.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20174
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.075
_diffrn_reflns_theta_max         67.698
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3741
_reflns_number_gt                3649
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.987

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.4173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3741
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.44403(11) 0.70934(4) 0.42008(4) 0.0669(3) Uani 1 1 d . . . . .
O1 O 0.15608(16) 0.33984(10) 0.28753(10) 0.0317(3) Uani 1 1 d . . . . .
H1B H 0.1462(4) 0.3199(7) 0.3395(19) 0.048 Uiso 1 1 d R U . . .
N1 N 0.61179(17) 0.30785(12) 0.37306(10) 0.0252(3) Uani 1 1 d . . . . .
H1A H 0.5691(12) 0.2749(9) 0.4199(13) 0.038 Uiso 1 1 d R U . . .
C1 C 0.4808(2) 0.33335(13) 0.31697(12) 0.0230(4) Uani 1 1 d . . . . .
H1 H 0.4131 0.3754 0.3489 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3874(2) 0.24863(13) 0.29456(12) 0.0241(4) Uani 1 1 d . . . . .
H2A H 0.4507 0.2065 0.2613 0.029 Uiso 1 1 calc R U . . .
H2B H 0.3563 0.2170 0.3463 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2461(2) 0.27483(13) 0.24454(12) 0.0242(4) Uani 1 1 d . . . . .
H3 H 0.2837 0.3055 0.1929 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1534(2) 0.19347(13) 0.21551(12) 0.0253(4) Uani 1 1 d . . . . .
C5 C 0.1061(2) 0.18935(16) 0.13330(13) 0.0336(5) Uani 1 1 d . . . . .
H5 H 0.1352 0.2362 0.0959 0.040 Uiso 1 1 calc R U . . .
C6 C 0.0176(3) 0.11876(18) 0.10420(15) 0.0427(6) Uani 1 1 d . . . . .
H6 H -0.0144 0.1179 0.0476 0.051 Uiso 1 1 calc R U . . .
C7 C -0.0245(3) 0.04950(16) 0.15717(17) 0.0424(6) Uani 1 1 d . . . . .
H7 H -0.0852 0.0006 0.1376 0.051 Uiso 1 1 calc R U . . .
C8 C 0.0229(3) 0.05240(17) 0.23848(18) 0.0477(6) Uani 1 1 d . . . . .
H8 H -0.0047 0.0046 0.2753 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1104(3) 0.12371(17) 0.26828(15) 0.0400(5) Uani 1 1 d . . . . .
H9 H 0.1409 0.1246 0.3251 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5413(2) 0.38457(13) 0.24273(12) 0.0244(4) Uani 1 1 d . . . . .
C11 C 0.4542(2) 0.45370(14) 0.20741(13) 0.0313(5) Uani 1 1 d . . . . .
H11 H 0.3596 0.4698 0.2319 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5043(3) 0.49885(17) 0.13715(15) 0.0414(6) Uani 1 1 d . . . . .
H12 H 0.4444 0.5458 0.1132 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6415(3) 0.47552(19) 0.10191(15) 0.0452(6) Uani 1 1 d . . . . .
H13 H 0.6751 0.5055 0.0528 0.054 Uiso 1 1 calc R U . . .
C14 C 0.7305(3) 0.40910(18) 0.13725(14) 0.0406(6) Uani 1 1 d . . . . .
H14 H 0.8256 0.3943 0.1127 0.049 Uiso 1 1 calc R U . . .
C15 C 0.6825(2) 0.36306(15) 0.20886(13) 0.0296(5) Uani 1 1 d . . . . .
C16 C 0.7865(2) 0.29551(18) 0.24967(15) 0.0392(5) Uani 1 1 d . . . . .
H16A H 0.8824 0.3268 0.2642 0.047 Uiso 1 1 calc R U . . .
H16B H 0.8114 0.2479 0.2083 0.047 Uiso 1 1 calc R U . . .
C17 C 0.7263(2) 0.24959(15) 0.32751(14) 0.0324(5) Uani 1 1 d . . . . .
H17A H 0.6780 0.1914 0.3118 0.039 Uiso 1 1 calc R U . . .
H17B H 0.8122 0.2359 0.3654 0.039 Uiso 1 1 calc R U . . .
C18 C 0.6895(2) 0.38958(15) 0.41130(13) 0.0297(4) Uani 1 1 d . . . . .
H18A H 0.7626 0.3690 0.4542 0.036 Uiso 1 1 calc R U . . .
H18B H 0.7472 0.4221 0.3675 0.036 Uiso 1 1 calc R U . . .
C19 C 0.5768(2) 0.45340(14) 0.45044(12) 0.0273(4) Uani 1 1 d . . . . .
C20 C 0.5656(3) 0.54152(15) 0.42116(12) 0.0324(4) Uani 1 1 d . . . . .
H20 H 0.6294 0.5622 0.3773 0.039 Uiso 1 1 calc R U . . .
C21 C 0.4597(3) 0.59882(15) 0.45715(14) 0.0374(5) Uani 1 1 d . . . . .
C22 C 0.3644(3) 0.57103(16) 0.51967(16) 0.0402(5) Uani 1 1 d . . . . .
H22 H 0.2904 0.6111 0.5422 0.048 Uiso 1 1 calc R U . . .
C23 C 0.3785(3) 0.48307(18) 0.54924(16) 0.0448(6) Uani 1 1 d . . . . .
H23 H 0.3147 0.4627 0.5932 0.054 Uiso 1 1 calc R U . . .
C24 C 0.4845(3) 0.42491(15) 0.51529(15) 0.0377(5) Uani 1 1 d . . . . .
H24 H 0.4942 0.3650 0.5365 0.045 Uiso 1 1 calc R U . . .
Cl2 Cl 0.56669(6) 0.18492(4) 0.52319(3) 0.03771(15) Uani 1 1 d . . . . .


_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
Cl1 C21 1.739(2) . ?
O1 C3 1.422(2) . ?
O1 H1B 0.89(3) . ?
N1 C1 1.509(2) . ?
N1 C17 1.512(3) . ?
N1 C18 1.515(3) . ?
N1 H1A 0.97(3) . ?
C1 C10 1.506(3) . ?
C1 C2 1.538(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.528(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.383(3) . ?
C4 C9 1.384(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.369(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.392(3) . ?
C10 C11 1.395(3) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.502(3) . ?
C16 C17 1.515(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.504(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.384(3) . ?
C19 C24 1.384(3) . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.369(4) . ?
C22 C23 1.386(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1B 106.6 . . ?
C1 N1 C17 111.26(15) . . ?
C1 N1 C18 112.80(15) . . ?
C17 N1 C18 110.27(15) . . ?
C1 N1 H1A 106.9 . . ?
C17 N1 H1A 110.4 . . ?
C18 N1 H1A 105.0 . . ?
C10 C1 N1 109.00(15) . . ?
C10 C1 C2 114.30(15) . . ?
N1 C1 C2 110.19(15) . . ?
C10 C1 H1 107.7 . . ?
N1 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
C3 C2 C1 110.61(16) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
O1 C3 C4 112.35(16) . . ?
O1 C3 C2 111.67(16) . . ?
C4 C3 C2 113.37(16) . . ?
O1 C3 H3 106.3 . . ?
C4 C3 H3 106.3 . . ?
C2 C3 H3 106.3 . . ?
C5 C4 C9 117.84(19) . . ?
C5 C4 C3 119.13(18) . . ?
C9 C4 C3 123.01(18) . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 118.8(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C8 120.3(2) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C15 C10 C11 119.90(19) . . ?
C15 C10 C1 120.61(18) . . ?
C11 C10 C1 119.48(17) . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 118.6(2) . . ?
C10 C15 C16 121.65(19) . . ?
C14 C15 C16 119.7(2) . . ?
C15 C16 C17 116.21(17) . . ?
C15 C16 H16A 108.2 . . ?
C17 C16 H16A 108.2 . . ?
C15 C16 H16B 108.2 . . ?
C17 C16 H16B 108.2 . . ?
H16A C16 H16B 107.4 . . ?
N1 C17 C16 112.14(18) . . ?
N1 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
N1 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 N1 111.63(16) . . ?
C19 C18 H18A 109.3 . . ?
N1 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
N1 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C24 119.8(2) . . ?
C20 C19 C18 119.47(19) . . ?
C24 C19 C18 120.69(19) . . ?
C21 C20 C19 118.6(2) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C21 C20 122.3(2) . . ?
C22 C21 Cl1 118.79(18) . . ?
C20 C21 Cl1 118.85(18) . . ?
C21 C22 C23 118.4(2) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C24 C23 C22 120.5(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 120.3(2) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_lz155
_database_code_depnum_ccdc_archive 'CCDC 1812328'
_audit_update_record             
;
2017-12-19 deposited with the CCDC.
2018-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C22 H23 N O S'
_chemical_formula_sum            'C22 H23 N O S'
_chemical_formula_weight         349.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.6782(2)
_cell_length_b                   8.5568(3)
_cell_length_c                   38.5091(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1871.05(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    5460
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      66.27

_exptl_crystal_description       needle
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    1.591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13731
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         5.295
_diffrn_reflns_theta_max         66.732
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3298
_reflns_number_gt                2978
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.997

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.2619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
;
 Flack x determined using 1104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3298
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.042

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 0.84267(16) 0.93439(9) 0.29127(2) 0.0526(2) Uani 1 1 d . . . . .
O1 O 0.9357(5) 0.8858(3) 0.38516(5) 0.0666(8) Uani 1 1 d . . . . .
H1A H 0.891675 0.845965 0.366301 0.100 Uiso 1 1 calc R U . . .
N1 N 0.6498(4) 0.6978(2) 0.34636(5) 0.0290(4) Uani 1 1 d . . . . .
C1 C 0.9143(6) 0.9307(4) 0.24801(8) 0.0578(9) Uani 1 1 d . . . . .
H1 H 1.031543 0.994525 0.237599 0.069 Uiso 1 1 calc R U . . .
C2 C 0.7832(6) 0.8257(4) 0.23082(8) 0.0549(8) Uani 1 1 d . . . . .
H2 H 0.796645 0.808077 0.206540 0.066 Uiso 1 1 calc R U . . .
C3 C 0.6213(6) 0.7430(4) 0.25245(7) 0.0476(7) Uani 1 1 d . . . . .
H3 H 0.516987 0.664519 0.244200 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6333(5) 0.7890(3) 0.28605(6) 0.0379(6) Uani 1 1 d . . . . .
C5 C 0.4952(5) 0.7313(3) 0.31664(6) 0.0370(6) Uani 1 1 d . . . . .
H5A H 0.377796 0.811212 0.323407 0.044 Uiso 1 1 calc R U . . .
H5B H 0.409105 0.635103 0.310083 0.044 Uiso 1 1 calc R U . . .
C6 C 0.8211(5) 0.5724(3) 0.33938(6) 0.0347(6) Uani 1 1 d . . . . .
H6A H 0.928830 0.563401 0.359490 0.042 Uiso 1 1 calc R U . . .
H6B H 0.916723 0.601839 0.318904 0.042 Uiso 1 1 calc R U . . .
C7 C 0.7087(5) 0.4144(3) 0.33272(7) 0.0441(7) Uani 1 1 d . . . . .
H7A H 0.640317 0.413146 0.309075 0.053 Uiso 1 1 calc R U . . .
H7B H 0.831145 0.332234 0.333860 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5186(5) 0.3789(3) 0.35882(6) 0.0369(6) Uani 1 1 d . . . . .
C9 C 0.4301(6) 0.2272(3) 0.36170(8) 0.0511(8) Uani 1 1 d . . . . .
H9 H 0.491696 0.147533 0.347125 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2561(6) 0.1905(4) 0.38512(9) 0.0560(9) Uani 1 1 d . . . . .
H10 H 0.196009 0.087037 0.386290 0.067 Uiso 1 1 calc R U . . .
C11 C 0.1690(6) 0.3050(4) 0.40697(8) 0.0501(8) Uani 1 1 d . . . . .
H11 H 0.051496 0.280097 0.423624 0.060 Uiso 1 1 calc R U . . .
C12 C 0.2538(5) 0.4556(3) 0.40444(7) 0.0377(6) Uani 1 1 d . . . . .
H12 H 0.192605 0.533962 0.419404 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4274(4) 0.4952(3) 0.38038(6) 0.0282(5) Uani 1 1 d . . . . .
C14 C 0.5131(4) 0.6634(3) 0.37832(6) 0.0277(5) Uani 1 1 d . . . . .
H14 H 0.369820 0.731323 0.377721 0.033 Uiso 1 1 calc R U . . .
C15 C 0.6533(5) 0.7092(3) 0.41111(6) 0.0299(5) Uani 1 1 d . . . . .
H15A H 0.549917 0.698212 0.431662 0.036 Uiso 1 1 calc R U . . .
H15B H 0.786627 0.635760 0.413959 0.036 Uiso 1 1 calc R U . . .
C16 C 0.7492(5) 0.8758(3) 0.40996(7) 0.0395(6) Uani 1 1 d . . . . .
H16 H 0.619488 0.947540 0.402595 0.047 Uiso 1 1 calc R U . . .
C17 C 0.8421(5) 0.9301(3) 0.44467(6) 0.0349(6) Uani 1 1 d . . . . .
C18 C 1.0509(5) 0.8714(4) 0.45780(7) 0.0447(7) Uani 1 1 d . . . . .
H18 H 1.138913 0.798367 0.444495 0.054 Uiso 1 1 calc R U . . .
C19 C 1.1331(6) 0.9174(4) 0.48999(8) 0.0493(7) Uani 1 1 d . . . . .
H19 H 1.275530 0.874755 0.498815 0.059 Uiso 1 1 calc R U . . .
C20 C 1.0093(6) 1.0246(3) 0.50923(7) 0.0467(7) Uani 1 1 d . . . . .
H20 H 1.066212 1.056983 0.531286 0.056 Uiso 1 1 calc R U . . .
C21 C 0.8022(6) 1.0850(4) 0.49635(8) 0.0523(8) Uani 1 1 d . . . . .
H21 H 0.715452 1.158966 0.509581 0.063 Uiso 1 1 calc R U . . .
C22 C 0.7203(5) 1.0381(3) 0.46417(7) 0.0452(7) Uani 1 1 d . . . . .
H22 H 0.577913 1.080967 0.455395 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.715(3) . ?
S1 C4 1.733(3) . ?
O1 C16 1.429(4) . ?
N1 C5 1.470(3) . ?
N1 C6 1.473(3) . ?
N1 C14 1.485(3) . ?
C1 C2 1.342(5) . ?
C2 C3 1.428(5) . ?
C3 C4 1.354(4) . ?
C4 C5 1.499(4) . ?
C6 C7 1.517(4) . ?
C7 C8 1.506(4) . ?
C8 C13 1.396(4) . ?
C8 C9 1.396(4) . ?
C9 C10 1.374(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.378(4) . ?
C12 C13 1.395(4) . ?
C13 C14 1.521(3) . ?
C14 C15 1.544(3) . ?
C15 C16 1.526(3) . ?
C16 C17 1.510(4) . ?
C17 C22 1.377(4) . ?
C17 C18 1.383(4) . ?
C18 C19 1.382(4) . ?
C19 C20 1.373(4) . ?
C20 C21 1.377(5) . ?
C21 C22 1.383(4) . ?

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
C1 S1 C4 92.12(15) . . ?
C5 N1 C6 113.21(19) . . ?
C5 N1 C14 111.8(2) . . ?
C6 N1 C14 110.60(18) . . ?
C2 C1 S1 111.1(2) . . ?
C1 C2 C3 113.6(3) . . ?
C4 C3 C2 112.4(3) . . ?
C3 C4 C5 129.0(3) . . ?
C3 C4 S1 110.7(2) . . ?
C5 C4 S1 120.29(19) . . ?
N1 C5 C4 111.3(2) . . ?
N1 C6 C7 113.7(2) . . ?
C8 C7 C6 111.6(2) . . ?
C13 C8 C9 118.8(3) . . ?
C13 C8 C7 121.3(2) . . ?
C9 C8 C7 119.9(3) . . ?
C10 C9 C8 121.6(3) . . ?
C9 C10 C11 119.6(3) . . ?
C12 C11 C10 119.6(3) . . ?
C11 C12 C13 121.4(3) . . ?
C12 C13 C8 119.0(2) . . ?
C12 C13 C14 119.4(2) . . ?
C8 C13 C14 121.6(2) . . ?
N1 C14 C13 113.47(19) . . ?
N1 C14 C15 110.98(18) . . ?
C13 C14 C15 111.26(19) . . ?
C16 C15 C14 113.4(2) . . ?
O1 C16 C17 108.3(2) . . ?
O1 C16 C15 109.9(2) . . ?
C17 C16 C15 112.7(2) . . ?
C22 C17 C18 118.4(3) . . ?
C22 C17 C16 120.9(3) . . ?
C18 C17 C16 120.7(3) . . ?
C19 C18 C17 120.9(3) . . ?
C20 C19 C18 120.1(3) . . ?
C19 C20 C21 119.6(3) . . ?
C20 C21 C22 120.1(3) . . ?
C17 C22 C21 121.0(3) . . ?



