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

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

data_dm-ii-253_sq
_database_code_depnum_ccdc_archive 'CCDC 1489617'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_dm-ii-253_sq        
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         39 %    
RESPONSE: The high angle data was extremely weak.  The diffraction poor
due to diffuse solvent.  The crystals may have lost solvent.
;
# end Validation Reply Form
_audit_creation_date             2016-06-23
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.05.11 svn.r3296 for OlexSys, GUI svn.r5177)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H34 N2 O6 S'
_chemical_formula_sum            'C29 H34 N2 O6 S'
_chemical_formula_weight         538.64
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   29.2891(19)
_cell_length_b                   29.2891(19)
_cell_length_c                   18.1917(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     15606(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2671
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      58.755
_cell_measurement_theta_min      2.860
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.714
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0998 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.7477.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.917
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irreg
_exptl_crystal_F_000             4576
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37725
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        65.078
_diffrn_reflns_theta_max         65.078
_diffrn_reflns_theta_min         2.859
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2484
_reflns_number_total             6404
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         6404
_refine_ls_number_restraints     249
_refine_ls_R_factor_all          0.1707
_refine_ls_R_factor_gt           0.0690
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0824P)²+3.5296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.2190
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C3, C10, C4, C17, C2, C1, N2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C3, C4, C9, N1, C10
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N1, C25, O3, C26, C9
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C9, C8, C7, C6, C5, C4, C3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C11, C12, O4, C13, C14, C15, C27, C28
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C28, O5, O6, C29, C14
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C18, C23, C22, C21, C20, C19, C24
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C10(H10), C15(H15), C14(H14), C11(H11), C13(H13), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C12(H12A,H12B), C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C7(H7), C6(H6), C23(H23), C22(H22), C19(H19), C20(H20)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.62547(6) 0.34724(5) 0.61468(8) 0.1054(5) Uani 1 1 d . . . . .
O4 O 0.58470(10) 0.55582(10) 0.42410(17) 0.0831(9) Uani 1 1 d . U . . .
O3 O 0.46611(10) 0.50818(10) 0.39411(18) 0.0893(10) Uani 1 1 d . U . . .
N1 N 0.51054(12) 0.44649(11) 0.37188(19) 0.0746(10) Uani 1 1 d . U . . .
O1 O 0.67112(13) 0.35734(13) 0.58964(19) 0.1169(13) Uani 1 1 d . . . . .
O6 O 0.71642(12) 0.51349(13) 0.4872(2) 0.1202(13) Uani 1 1 d . U . . .
N2 N 0.59097(13) 0.36393(12) 0.5498(2) 0.0881(11) Uani 1 1 d . U . . .
O2 O 0.61163(15) 0.30101(13) 0.63198(19) 0.1290(14) Uani 1 1 d . . . . .
O5 O 0.68750(13) 0.50333(15) 0.5991(3) 0.1346(15) Uani 1 1 d . U . . .
C9 C 0.52157(14) 0.40072(15) 0.3473(3) 0.0760(11) Uani 1 1 d . U . . .
C4 C 0.54823(14) 0.37921(15) 0.4002(2) 0.0748(11) Uani 1 1 d . U . . .
C10 C 0.54396(14) 0.45731(14) 0.4309(2) 0.0737(11) Uani 1 1 d . U . . .
H10 H 0.5317 0.4803 0.4664 0.088 Uiso 1 1 calc R . . . .
C15 C 0.63256(14) 0.46946(14) 0.4382(2) 0.0756(12) Uani 1 1 d . U . . .
H15 H 0.6585 0.4736 0.4032 0.091 Uiso 1 1 calc R . . . .
C25 C 0.47131(15) 0.47168(16) 0.3612(3) 0.0786(12) Uani 1 1 d . U . . .
C3 C 0.55158(14) 0.41068(15) 0.4671(3) 0.0743(10) Uani 1 1 d . U . . .
C5 C 0.56378(14) 0.33427(14) 0.3879(3) 0.0800(13) Uani 1 1 d . U . . .
H5 H 0.5821 0.3189 0.4232 0.096 Uiso 1 1 calc R . . . .
C2 C 0.51578(15) 0.39469(15) 0.5249(2) 0.0827(12) Uani 1 1 d . U . . .
H2A H 0.5086 0.4193 0.5604 0.099 Uiso 1 1 calc R . . . .
H2B H 0.4872 0.3843 0.5011 0.099 Uiso 1 1 calc R . . . .
C8 C 0.51074(15) 0.38034(16) 0.2805(3) 0.0839(13) Uani 1 1 d . U . . .
H8 H 0.4936 0.3961 0.2441 0.101 Uiso 1 1 calc R . . . .
C14 C 0.63659(15) 0.50871(15) 0.4955(3) 0.0817(12) Uani 1 1 d . U . . .
H14 H 0.6119 0.5043 0.5329 0.098 Uiso 1 1 calc R . . . .
C16 C 0.63778(15) 0.42107(14) 0.4705(3) 0.0808(13) Uani 1 1 d . . . . .
H16A H 0.6419 0.3986 0.4304 0.097 Uiso 1 1 calc R . . . .
H16B H 0.6649 0.4198 0.5030 0.097 Uiso 1 1 calc R . . . .
C11 C 0.58843(14) 0.47463(14) 0.3922(2) 0.0750(12) Uani 1 1 d . U . . .
H11 H 0.5926 0.4552 0.3474 0.090 Uiso 1 1 calc R . . . .
C13 C 0.62891(16) 0.55559(15) 0.4587(3) 0.0875(13) Uani 1 1 d . U . . .
H13 H 0.6530 0.5606 0.4205 0.105 Uiso 1 1 calc R . . . .
C17 C 0.59489(14) 0.40988(14) 0.5141(2) 0.0764(11) Uani 1 1 d . U . . .
H17 H 0.5915 0.4335 0.5533 0.092 Uiso 1 1 calc R . . . .
C12 C 0.58249(16) 0.52358(15) 0.3649(3) 0.0841(13) Uani 1 1 d . U . . .
H12A H 0.6067 0.5306 0.3287 0.101 Uiso 1 1 calc R . . . .
H12B H 0.5526 0.5265 0.3398 0.101 Uiso 1 1 calc R . . . .
C7 C 0.52624(15) 0.33528(15) 0.2690(3) 0.0855(13) Uani 1 1 d . U . . .
H7 H 0.5193 0.3200 0.2243 0.103 Uiso 1 1 calc R . . . .
C28 C 0.68166(19) 0.50722(17) 0.5350(4) 0.0968(15) Uani 1 1 d . U . . .
C26 C 0.43523(15) 0.45361(16) 0.3102(3) 0.1000(17) Uani 1 1 d . U . . .
H26A H 0.4061 0.4688 0.3206 0.150 Uiso 1 1 calc GR . . . .
H26B H 0.4319 0.4206 0.3176 0.150 Uiso 1 1 calc GR . . . .
H26C H 0.4441 0.4596 0.2592 0.150 Uiso 1 1 calc GR . . . .
C6 C 0.55139(15) 0.31335(16) 0.3224(3) 0.0876(13) Uani 1 1 d . U . . .
H6 H 0.5606 0.2827 0.3140 0.105 Uiso 1 1 calc R . . . .
C27 C 0.62915(17) 0.59547(16) 0.5127(3) 0.1044(17) Uani 1 1 d . U . . .
H27A H 0.6254 0.6242 0.4857 0.157 Uiso 1 1 calc GR . . . .
H27B H 0.6582 0.5960 0.5393 0.157 Uiso 1 1 calc GR . . . .
H27C H 0.6040 0.5919 0.5477 0.157 Uiso 1 1 calc GR . . . .
C18 C 0.6153(2) 0.38139(19) 0.6930(3) 0.1020(16) Uani 1 1 d . U . . .
C23 C 0.63724(19) 0.4236(2) 0.6986(3) 0.1086(17) Uani 1 1 d . U . . .
H23 H 0.6569 0.4342 0.6607 0.130 Uiso 1 1 calc R . . . .
C1 C 0.54088(16) 0.35503(16) 0.5623(3) 0.0953(14) Uani 1 1 d . U . . .
H1A H 0.5339 0.3542 0.6155 0.114 Uiso 1 1 calc R . . . .
H1B H 0.5318 0.3255 0.5402 0.114 Uiso 1 1 calc R . . . .
C22 C 0.6295(2) 0.4500(2) 0.7622(3) 0.1225(19) Uani 1 1 d . U . . .
H22 H 0.6444 0.4786 0.7670 0.147 Uiso 1 1 calc R . . . .
C29 C 0.76274(18) 0.5123(2) 0.5185(4) 0.159(3) Uani 1 1 d . U . . .
H29A H 0.7852 0.5115 0.4786 0.239 Uiso 1 1 calc GR . . . .
H29B H 0.7661 0.4850 0.5492 0.239 Uiso 1 1 calc GR . . . .
H29C H 0.7677 0.5396 0.5485 0.239 Uiso 1 1 calc GR . . . .
C19 C 0.5861(2) 0.3661(2) 0.7484(3) 0.139(2) Uani 1 1 d . U . . .
H19 H 0.5713 0.3374 0.7446 0.167 Uiso 1 1 calc R . . . .
C21 C 0.6007(3) 0.4355(2) 0.8177(4) 0.147(2) Uani 1 1 d . U . . .
C20 C 0.5792(3) 0.3936(2) 0.8089(4) 0.163(3) Uani 1 1 d . U . . .
H20 H 0.5589 0.3835 0.8461 0.196 Uiso 1 1 calc R . . . .
C24 C 0.5932(4) 0.4649(2) 0.8862(4) 0.213(4) Uani 1 1 d . U . . .
H24A H 0.6190 0.4858 0.8923 0.320 Uiso 1 1 calc GR . . . .
H24B H 0.5907 0.4452 0.9295 0.320 Uiso 1 1 calc GR . . . .
H24C H 0.5650 0.4826 0.8805 0.320 Uiso 1 1 calc GR . . . .


_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 1.443(4) . ?
S1 N2 1.629(4) . ?
S1 O2 1.448(4) . ?
S1 C18 1.766(5) . ?
O4 C13 1.440(5) . ?
O4 C12 1.433(5) . ?
O3 C25 1.235(5) . ?
N1 C9 1.450(5) . ?
N1 C10 1.487(5) . ?
N1 C25 1.379(5) . ?
O6 C28 1.353(6) . ?
O6 C29 1.472(6) . ?
N2 C17 1.499(5) . ?
N2 C1 1.507(5) . ?
O5 C28 1.183(6) . ?
C9 C4 1.390(6) . ?
C9 C8 1.391(5) . ?
C4 C3 1.531(5) . ?
C4 C5 1.411(5) . ?
C10 H10 1.0000 . ?
C10 C3 1.533(5) . ?
C10 C11 1.565(5) . ?
C15 H15 1.0000 . ?
C15 C14 1.557(5) . ?
C15 C16 1.542(5) . ?
C15 C11 1.547(5) . ?
C25 C26 1.502(6) . ?
C3 C2 1.557(6) . ?
C3 C17 1.529(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.533(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.411(5) . ?
C14 H14 1.0000 . ?
C14 C13 1.545(6) . ?
C14 C28 1.504(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.522(5) . ?
C11 H11 1.0000 . ?
C11 C12 1.527(6) . ?
C13 H13 1.0000 . ?
C13 C27 1.526(6) . ?
C17 H17 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C7 H7 0.9500 . ?
C7 C6 1.378(6) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C6 H6 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C18 C23 1.397(7) . ?
C18 C19 1.396(7) . ?
C23 H23 0.9500 . ?
C23 C22 1.409(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C22 H22 0.9500 . ?
C22 C21 1.383(8) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.378(8) . ?
C21 C20 1.387(8) . ?
C21 C24 1.531(8) . ?
C20 H20 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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 N2 106.5(2) . . ?
O1 S1 O2 121.3(2) . . ?
O1 S1 C18 107.1(3) . . ?
N2 S1 C18 108.0(2) . . ?
O2 S1 N2 105.3(2) . . ?
O2 S1 C18 107.9(3) . . ?
C12 O4 C13 111.4(3) . . ?
C9 N1 C10 105.9(3) . . ?
C25 N1 C9 129.6(4) . . ?
C25 N1 C10 122.4(4) . . ?
C28 O6 C29 116.2(5) . . ?
C17 N2 S1 122.4(3) . . ?
C17 N2 C1 107.2(3) . . ?
C1 N2 S1 116.3(3) . . ?
C4 C9 N1 109.3(4) . . ?
C4 C9 C8 122.6(4) . . ?
C8 C9 N1 128.0(4) . . ?
C9 C4 C3 108.3(4) . . ?
C9 C4 C5 119.7(4) . . ?
C5 C4 C3 131.8(4) . . ?
N1 C10 H10 111.9 . . ?
N1 C10 C3 102.5(3) . . ?
N1 C10 C11 107.0(4) . . ?
C3 C10 H10 111.9 . . ?
C3 C10 C11 111.2(3) . . ?
C11 C10 H10 111.9 . . ?
C14 C15 H15 106.2 . . ?
C16 C15 H15 106.2 . . ?
C16 C15 C14 114.6(4) . . ?
C16 C15 C11 112.3(3) . . ?
C11 C15 H15 106.2 . . ?
C11 C15 C14 110.7(3) . . ?
O3 C25 N1 119.8(4) . . ?
O3 C25 C26 121.2(4) . . ?
N1 C25 C26 119.0(4) . . ?
C4 C3 C10 100.6(4) . . ?
C4 C3 C2 108.3(3) . . ?
C10 C3 C2 117.4(4) . . ?
C17 C3 C4 119.2(4) . . ?
C17 C3 C10 112.0(4) . . ?
C17 C3 C2 100.2(4) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 C4 117.6(5) . . ?
C6 C5 H5 121.2 . . ?
C3 C2 H2A 111.4 . . ?
C3 C2 H2B 111.4 . . ?
H2A C2 H2B 109.3 . . ?
C1 C2 C3 101.8(4) . . ?
C1 C2 H2A 111.4 . . ?
C1 C2 H2B 111.4 . . ?
C9 C8 H8 121.4 . . ?
C9 C8 C7 117.2(5) . . ?
C7 C8 H8 121.4 . . ?
C15 C14 H14 107.8 . . ?
C13 C14 C15 110.8(4) . . ?
C13 C14 H14 107.8 . . ?
C28 C14 C15 111.4(4) . . ?
C28 C14 H14 107.8 . . ?
C28 C14 C13 111.2(4) . . ?
C15 C16 H16A 110.0 . . ?
C15 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C17 C16 C15 108.3(4) . . ?
C17 C16 H16A 110.0 . . ?
C17 C16 H16B 110.0 . . ?
C10 C11 H11 106.4 . . ?
C15 C11 C10 114.9(4) . . ?
C15 C11 H11 106.4 . . ?
C12 C11 C10 110.8(4) . . ?
C12 C11 C15 111.3(3) . . ?
C12 C11 H11 106.4 . . ?
O4 C13 C14 109.0(4) . . ?
O4 C13 H13 109.3 . . ?
O4 C13 C27 106.4(4) . . ?
C14 C13 H13 109.3 . . ?
C27 C13 C14 113.6(4) . . ?
C27 C13 H13 109.3 . . ?
N2 C17 C3 101.1(3) . . ?
N2 C17 C16 118.9(4) . . ?
N2 C17 H17 107.8 . . ?
C3 C17 H17 107.8 . . ?
C16 C17 C3 113.0(4) . . ?
C16 C17 H17 107.8 . . ?
O4 C12 C11 111.7(4) . . ?
O4 C12 H12A 109.3 . . ?
O4 C12 H12B 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.3(5) . . ?
C6 C7 H7 119.9 . . ?
O6 C28 C14 110.4(5) . . ?
O5 C28 O6 122.6(5) . . ?
O5 C28 C14 126.9(6) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C5 C6 H6 118.7 . . ?
C7 C6 C5 122.6(5) . . ?
C7 C6 H6 118.7 . . ?
C13 C27 H27A 109.5 . . ?
C13 C27 H27B 109.5 . . ?
C13 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C23 C18 S1 118.9(5) . . ?
C19 C18 S1 120.3(5) . . ?
C19 C18 C23 120.8(6) . . ?
C18 C23 H23 120.9 . . ?
C18 C23 C22 118.2(6) . . ?
C22 C23 H23 120.9 . . ?
N2 C1 C2 105.6(4) . . ?
N2 C1 H1A 110.6 . . ?
N2 C1 H1B 110.6 . . ?
C2 C1 H1A 110.6 . . ?
C2 C1 H1B 110.6 . . ?
H1A C1 H1B 108.8 . . ?
C23 C22 H22 119.0 . . ?
C21 C22 C23 121.9(7) . . ?
C21 C22 H22 119.0 . . ?
O6 C29 H29A 109.5 . . ?
O6 C29 H29B 109.5 . . ?
O6 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.6(7) . . ?
C20 C19 H19 120.7 . . ?
C22 C21 C20 117.6(7) . . ?
C22 C21 C24 120.6(7) . . ?
C20 C21 C24 121.8(7) . . ?
C19 C20 C21 122.9(7) . . ?
C19 C20 H20 118.6 . . ?
C21 C20 H20 118.6 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N2 C17 C3 -172.2(3) . . . . ?
S1 N2 C17 C16 63.6(5) . . . . ?
S1 N2 C1 C2 147.3(3) . . . . ?
S1 C18 C23 C22 -178.8(4) . . . . ?
S1 C18 C19 C20 179.6(5) . . . . ?
N1 C9 C4 C3 5.5(5) . . . . ?
N1 C9 C4 C5 -179.2(4) . . . . ?
N1 C9 C8 C7 178.8(4) . . . . ?
N1 C10 C3 C4 35.1(4) . . . . ?
N1 C10 C3 C2 -82.0(4) . . . . ?
N1 C10 C3 C17 162.8(3) . . . . ?
N1 C10 C11 C15 -156.7(3) . . . . ?
N1 C10 C11 C12 76.2(4) . . . . ?
O1 S1 N2 C17 -47.7(4) . . . . ?
O1 S1 N2 C1 177.6(3) . . . . ?
O1 S1 C18 C23 29.7(5) . . . . ?
O1 S1 C18 C19 -149.7(5) . . . . ?
N2 S1 C18 C23 -84.7(5) . . . . ?
N2 S1 C18 C19 95.8(5) . . . . ?
O2 S1 N2 C17 -177.8(3) . . . . ?
O2 S1 N2 C1 47.5(4) . . . . ?
O2 S1 C18 C23 161.9(4) . . . . ?
O2 S1 C18 C19 -17.6(6) . . . . ?
C9 N1 C10 C3 -33.6(4) . . . . ?
C9 N1 C10 C11 83.5(4) . . . . ?
C9 N1 C25 O3 171.2(4) . . . . ?
C9 N1 C25 C26 -7.8(7) . . . . ?
C9 C4 C3 C10 -25.6(4) . . . . ?
C9 C4 C3 C2 98.1(4) . . . . ?
C9 C4 C3 C17 -148.5(4) . . . . ?
C9 C4 C5 C6 -0.1(6) . . . . ?
C9 C8 C7 C6 -0.6(7) . . . . ?
C4 C9 C8 C7 2.9(7) . . . . ?
C4 C3 C2 C1 81.5(4) . . . . ?
C4 C3 C17 N2 -69.9(5) . . . . ?
C4 C3 C17 C16 58.2(5) . . . . ?
C4 C5 C6 C7 2.3(7) . . . . ?
C10 N1 C9 C4 18.1(5) . . . . ?
C10 N1 C9 C8 -158.3(4) . . . . ?
C10 N1 C25 O3 10.3(7) . . . . ?
C10 N1 C25 C26 -168.7(4) . . . . ?
C10 C3 C2 C1 -165.5(4) . . . . ?
C10 C3 C17 N2 173.1(3) . . . . ?
C10 C3 C17 C16 -58.8(5) . . . . ?
C10 C11 C12 O4 75.5(4) . . . . ?
C15 C14 C13 O4 57.7(5) . . . . ?
C15 C14 C13 C27 176.1(4) . . . . ?
C15 C14 C28 O6 62.6(6) . . . . ?
C15 C14 C28 O5 -120.7(6) . . . . ?
C15 C16 C17 N2 178.5(4) . . . . ?
C15 C16 C17 C3 60.4(5) . . . . ?
C15 C11 C12 O4 -53.6(5) . . . . ?
C25 N1 C9 C4 -145.2(4) . . . . ?
C25 N1 C9 C8 38.4(7) . . . . ?
C25 N1 C10 C3 131.2(4) . . . . ?
C25 N1 C10 C11 -111.8(4) . . . . ?
C3 C4 C5 C6 174.0(4) . . . . ?
C3 C10 C11 C15 -45.5(5) . . . . ?
C3 C10 C11 C12 -172.6(4) . . . . ?
C3 C2 C1 N2 23.6(5) . . . . ?
C5 C4 C3 C10 159.8(5) . . . . ?
C5 C4 C3 C2 -76.5(6) . . . . ?
C5 C4 C3 C17 36.9(7) . . . . ?
C2 C3 C17 N2 47.8(4) . . . . ?
C2 C3 C17 C16 176.0(3) . . . . ?
C8 C9 C4 C3 -177.9(4) . . . . ?
C8 C9 C4 C5 -2.5(7) . . . . ?
C8 C7 C6 C5 -2.0(7) . . . . ?
C14 C15 C16 C17 72.6(5) . . . . ?
C14 C15 C11 C10 -80.0(5) . . . . ?
C14 C15 C11 C12 46.9(5) . . . . ?
C16 C15 C14 C13 -177.6(4) . . . . ?
C16 C15 C14 C28 58.0(6) . . . . ?
C16 C15 C11 C10 49.4(5) . . . . ?
C16 C15 C11 C12 176.4(4) . . . . ?
C11 C10 C3 C4 -78.9(4) . . . . ?
C11 C10 C3 C2 163.9(4) . . . . ?
C11 C10 C3 C17 48.8(5) . . . . ?
C11 C15 C14 C13 -49.4(5) . . . . ?
C11 C15 C14 C28 -173.8(4) . . . . ?
C11 C15 C16 C17 -54.8(5) . . . . ?
C13 O4 C12 C11 63.7(5) . . . . ?
C13 C14 C28 O6 -61.5(5) . . . . ?
C13 C14 C28 O5 115.2(7) . . . . ?
C17 N2 C1 C2 6.2(5) . . . . ?
C17 C3 C2 C1 -44.0(4) . . . . ?
C12 O4 C13 C14 -65.0(5) . . . . ?
C12 O4 C13 C27 172.2(4) . . . . ?
C28 C14 C13 O4 -177.8(4) . . . . ?
C28 C14 C13 C27 -59.5(6) . . . . ?
C18 S1 N2 C17 67.1(4) . . . . ?
C18 S1 N2 C1 -67.6(4) . . . . ?
C18 C23 C22 C21 -0.7(9) . . . . ?
C18 C19 C20 C21 -1.2(12) . . . . ?
C23 C18 C19 C20 0.2(10) . . . . ?
C23 C22 C21 C20 -0.2(11) . . . . ?
C23 C22 C21 C24 179.7(6) . . . . ?
C1 N2 C17 C3 -34.0(4) . . . . ?
C1 N2 C17 C16 -158.2(4) . . . . ?
C22 C21 C20 C19 1.2(12) . . . . ?
C29 O6 C28 O5 3.8(8) . . . . ?
C29 O6 C28 C14 -179.3(4) . . . . ?
C19 C18 C23 C22 0.7(8) . . . . ?
C24 C21 C20 C19 -178.7(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id DM-II-253
_olex2_submission_special_instructions 'No special instructions were received'
