# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
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data_nami15101121_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1442788'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2015-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H4 N O3 S, C21 H33 N2 O'
_chemical_formula_sum            'C28 H37 N3 O4 S'
_chemical_formula_weight         511.67
_chemical_absolute_configuration ad
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8028(6)
_cell_length_b                   17.6121(12)
_cell_length_c                   18.6177(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2558.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8826
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.47
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12193
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.19
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4743
_reflns_number_total             5189
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5189
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0425P)²+0.6363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0860
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 N3, S1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N2, C22, C18, C17, C16
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
N3 \\sim S1: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.002
N2 \\sim C22 \\sim C18 \\sim C17 \\sim C16: within 2A with sigma of 0.002 and
sigma for terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C12(H12A,
 H12B), C13(H13A,H13B), C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C18(H18), C24(H24), C25(H25), C26(H26), C27(H27)
4.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S -0.54883(6) 0.78934(3) 0.38436(2) 0.02964(12) Uani 1 d . . . U
O1 O 0.75017(18) 0.33623(8) 0.66292(6) 0.0277(3) Uani 1 d . . . .
H1 H 0.8377 0.3148 0.6765 0.042 Uiso 1 calc . . GR .
O2 O -0.4739(2) 0.86219(9) 0.39884(9) 0.0482(4) Uani 1 d . . . .
O3 O -0.5423(2) 0.73564(10) 0.44203(8) 0.0519(4) Uani 1 d . . . .
O4 O -0.5531(2) 0.72818(11) 0.19692(8) 0.0510(5) Uani 1 d . . . .
N1 N -0.1000(2) 0.62373(8) 0.28557(8) 0.0243(3) Uani 1 d . . . .
H1A H -0.1238 0.6215 0.2405 0.029 Uiso 1 calc . . R .
N2 N -0.1965(2) 0.65760(9) 0.33603(8) 0.0264(3) Uani 1 d . . . U
N3 N -0.4688(2) 0.75220(9) 0.31208(8) 0.0290(3) Uani 1 d . . . U
C1 C 0.0397(3) 0.59384(10) 0.31694(9) 0.0226(4) Uani 1 d . . . .
C2 C 0.1774(2) 0.54806(11) 0.28188(9) 0.0265(4) Uani 1 d . . . .
H2A H 0.2217 0.5754 0.2406 0.032 Uiso 1 calc . . R .
H2B H 0.1300 0.5004 0.2651 0.032 Uiso 1 calc . . R .
C3 C 0.3247(2) 0.53214(10) 0.33515(9) 0.0214(4) Uani 1 d . . . .
H3 H 0.3936 0.5785 0.3383 0.026 Uiso 1 calc . . R .
C4 C 0.4410(3) 0.46962(11) 0.30566(9) 0.0270(4) Uani 1 d . . . .
H4A H 0.3728 0.4245 0.2970 0.032 Uiso 1 calc . . R .
H4B H 0.4878 0.4860 0.2600 0.032 Uiso 1 calc . . R .
C5 C 0.5886(2) 0.44938(11) 0.35610(9) 0.0239(4) Uani 1 d . . . .
H5A H 0.6675 0.4918 0.3588 0.029 Uiso 1 calc . . R .
H5B H 0.6505 0.4062 0.3368 0.029 Uiso 1 calc . . R .
C6 C 0.5240(2) 0.43016(9) 0.43173(8) 0.0169(3) Uani 1 d . . . .
H6 H 0.4482 0.3859 0.4284 0.020 Uiso 1 calc . . R .
C7 C 0.6704(2) 0.41107(9) 0.48285(9) 0.0164(3) Uani 1 d . . . .
H7 H 0.7490 0.4545 0.4823 0.020 Uiso 1 calc . . R .
C8 C 0.7780(2) 0.34023(10) 0.46764(9) 0.0202(4) Uani 1 d . . . .
H8A H 0.8620 0.3501 0.4304 0.024 Uiso 1 calc . . R .
H8B H 0.7060 0.2982 0.4528 0.024 Uiso 1 calc . . R .
C9 C 0.8670(2) 0.32293(11) 0.54055(9) 0.0240(4) Uani 1 d . . . .
H9A H 0.8492 0.2703 0.5540 0.029 Uiso 1 calc . . R .
H9B H 0.9893 0.3322 0.5371 0.029 Uiso 1 calc . . R .
C10 C 0.7847(2) 0.37677(10) 0.59692(9) 0.0202(4) Uani 1 d . . . .
C11 C 0.6130(2) 0.39982(9) 0.56140(9) 0.0172(3) Uani 1 d . . . .
C12 C 0.5303(2) 0.47329(10) 0.58710(9) 0.0229(4) Uani 1 d . . . .
H12A H 0.6128 0.5144 0.5843 0.027 Uiso 1 calc . . R .
H12B H 0.4953 0.4679 0.6368 0.027 Uiso 1 calc . . R .
C13 C 0.3741(2) 0.49232(11) 0.54071(9) 0.0241(4) Uani 1 d . . . .
H13A H 0.3259 0.5403 0.5565 0.029 Uiso 1 calc . . R .
H13B H 0.2875 0.4534 0.5473 0.029 Uiso 1 calc . . R .
C14 C 0.4191(2) 0.49796(9) 0.46020(9) 0.0179(3) Uani 1 d . . . .
H14 H 0.4933 0.5426 0.4553 0.022 Uiso 1 calc . . R .
C15 C 0.2602(2) 0.51363(10) 0.41227(8) 0.0179(3) Uani 1 d . . . .
C16 C 0.1643(3) 0.58365(11) 0.44203(10) 0.0260(4) Uani 1 d . . . U
H16A H 0.1097 0.5707 0.4872 0.031 Uiso 1 calc . . R .
H16B H 0.2453 0.6243 0.4510 0.031 Uiso 1 calc . . R .
C17 C 0.0315(2) 0.60986(10) 0.38943(9) 0.0249(3) Uani 1 d . . . U
C18 C -0.1188(3) 0.65049(11) 0.39924(10) 0.0277(4) Uani 1 d . . . U
H18 H -0.1587 0.6696 0.4427 0.033 Uiso 1 calc . . R .
C19 C 0.9015(2) 0.44298(11) 0.61500(11) 0.0308(4) Uani 1 d . . . .
H19A H 0.8478 0.4744 0.6506 0.046 Uiso 1 calc . . GR .
H19B H 0.9224 0.4724 0.5725 0.046 Uiso 1 calc . . GR .
H19C H 1.0083 0.4241 0.6333 0.046 Uiso 1 calc . . GR .
C20 C 0.4851(2) 0.33402(10) 0.56920(9) 0.0245(4) Uani 1 d . . . .
H20A H 0.3972 0.3387 0.5334 0.037 Uiso 1 calc . . GR .
H20B H 0.4342 0.3356 0.6161 0.037 Uiso 1 calc . . GR .
H20C H 0.5441 0.2866 0.5630 0.037 Uiso 1 calc . . GR .
C21 C 0.1363(2) 0.44600(11) 0.41120(10) 0.0245(4) Uani 1 d . . . .
H21A H 0.0350 0.4595 0.3849 0.037 Uiso 1 calc . . GR .
H21B H 0.1055 0.4328 0.4595 0.037 Uiso 1 calc . . GR .
H21C H 0.1907 0.4034 0.3885 0.037 Uiso 1 calc . . GR .
C22 C -0.5829(3) 0.75249(11) 0.25776(10) 0.0279(4) Uani 1 d . . . U
C23 C -0.7540(2) 0.78280(10) 0.27871(9) 0.0222(4) Uani 1 d . . . .
C24 C -0.9000(3) 0.79113(11) 0.23702(11) 0.0287(4) Uani 1 d . . . .
H24 H -0.8987 0.7788 0.1884 0.034 Uiso 1 calc . . R .
C25 C -1.0474(3) 0.81812(11) 0.26925(12) 0.0335(5) Uani 1 d . . . .
H25 H -1.1464 0.8242 0.2420 0.040 Uiso 1 calc . . R .
C26 C -1.0498(3) 0.83621(11) 0.34146(12) 0.0377(5) Uani 1 d . . . .
H26 H -1.1508 0.8539 0.3620 0.045 Uiso 1 calc . . R .
C27 C -0.9051(3) 0.82854(12) 0.38379(12) 0.0349(5) Uani 1 d . . . .
H27 H -0.9065 0.8406 0.4324 0.042 Uiso 1 calc . . R .
C28 C -0.7584(2) 0.80220(10) 0.35052(10) 0.0239(4) Uani 1 d . . . .
H2 H -0.291(3) 0.6843(12) 0.3265(11) 0.029 Uiso 1 d . . R .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4354(16) . ?
S1 O3 1.4317(16) . ?
S1 N3 1.6215(16) . ?
S1 C28 1.7667(19) . ?
O1 H1 0.8200 . ?
O1 C10 1.446(2) . ?
O4 C22 1.233(2) . ?
N1 H1A 0.8600 . ?
N1 N2 1.344(2) . ?
N1 C1 1.344(2) . ?
N2 C18 1.329(2) . ?
N2 H2 0.89(2) . ?
N3 C22 1.347(2) . ?
C1 C2 1.494(3) . ?
C1 C17 1.380(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.544(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.529(3) . ?
C3 C15 1.556(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.528(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.533(2) . ?
C6 H6 0.9800 . ?
C6 C7 1.524(2) . ?
C6 C14 1.542(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.530(2) . ?
C7 C11 1.542(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.555(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.553(2) . ?
C10 C11 1.549(2) . ?
C10 C19 1.518(3) . ?
C11 C12 1.523(2) . ?
C11 C20 1.536(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.531(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.543(2) . ?
C14 H14 0.9800 . ?
C14 C15 1.552(2) . ?
C15 C16 1.545(2) . ?
C15 C21 1.534(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.499(2) . ?
C17 C18 1.386(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.490(3) . ?
C23 C24 1.386(3) . ?
C23 C28 1.380(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.382(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.384(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.382(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 S1 N3 111.07(10) . . ?
O2 S1 C28 109.23(9) . . ?
O3 S1 O2 115.80(10) . . ?
O3 S1 N3 110.01(10) . . ?
O3 S1 C28 112.64(10) . . ?
N3 S1 C28 96.45(8) . . ?
C10 O1 H1 109.5 . . ?
N2 N1 H1A 125.5 . . ?
N2 N1 C1 108.94(14) . . ?
C1 N1 H1A 125.5 . . ?
N1 N2 H2 123.9(13) . . ?
C18 N2 N1 108.76(16) . . ?
C18 N2 H2 127.1(13) . . ?
C22 N3 S1 111.52(13) . . ?
N1 C1 C2 127.23(15) . . ?
N1 C1 C17 107.89(16) . . ?
C17 C1 C2 124.83(16) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.66(14) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C2 C3 H3 107.2 . . ?
C2 C3 C15 112.98(15) . . ?
C4 C3 C2 109.99(15) . . ?
C4 C3 H3 107.2 . . ?
C4 C3 C15 111.87(14) . . ?
C15 C3 H3 107.2 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.25(15) . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.59(15) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 H6 108.4 . . ?
C5 C6 C14 108.62(13) . . ?
C7 C6 C5 112.06(14) . . ?
C7 C6 H6 108.4 . . ?
C7 C6 C14 110.73(13) . . ?
C14 C6 H6 108.4 . . ?
C6 C7 H7 106.9 . . ?
C6 C7 C8 118.39(14) . . ?
C6 C7 C11 113.74(14) . . ?
C8 C7 H7 106.9 . . ?
C8 C7 C11 103.30(13) . . ?
C11 C7 H7 106.9 . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
C7 C8 C9 104.08(13) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C8 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C10 C9 C8 106.59(14) . . ?
C10 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
O1 C10 C9 110.47(14) . . ?
O1 C10 C11 109.32(14) . . ?
O1 C10 C19 107.62(14) . . ?
C11 C10 C9 103.26(14) . . ?
C19 C10 C9 111.75(16) . . ?
C19 C10 C11 114.38(14) . . ?
C7 C11 C10 100.78(13) . . ?
C12 C11 C7 108.17(14) . . ?
C12 C11 C10 117.09(14) . . ?
C12 C11 C20 109.64(15) . . ?
C20 C11 C7 112.04(14) . . ?
C20 C11 C10 108.90(14) . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C11 C12 C13 110.25(14) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C12 C13 C14 112.38(14) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C6 C14 C13 113.90(13) . . ?
C6 C14 H14 106.0 . . ?
C6 C14 C15 111.35(13) . . ?
C13 C14 H14 106.0 . . ?
C13 C14 C15 112.82(14) . . ?
C15 C14 H14 106.0 . . ?
C14 C15 C3 108.03(14) . . ?
C16 C15 C3 108.68(14) . . ?
C16 C15 C14 108.83(14) . . ?
C21 C15 C3 110.75(14) . . ?
C21 C15 C14 111.90(14) . . ?
C21 C15 C16 108.59(15) . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 C15 110.27(14) . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C1 C17 C16 122.94(17) . . ?
C1 C17 C18 105.89(16) . . ?
C18 C17 C16 131.15(17) . . ?
N2 C18 C17 108.53(17) . . ?
N2 C18 H18 125.7 . . ?
C17 C18 H18 125.7 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 N3 124.34(18) . . ?
O4 C22 C23 122.24(17) . . ?
N3 C22 C23 113.38(15) . . ?
C24 C23 C22 128.89(16) . . ?
C28 C23 C22 111.38(16) . . ?
C28 C23 C24 119.71(17) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 C23 118.53(18) . . ?
C25 C24 H24 120.7 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.9(2) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 119.3 . . ?
C25 C26 C27 121.4(2) . . ?
C27 C26 H26 119.3 . . ?
C26 C27 H27 121.5 . . ?
C28 C27 C26 116.98(18) . . ?
C28 C27 H27 121.5 . . ?
C23 C28 S1 106.90(14) . . ?
C23 C28 C27 122.54(18) . . ?
C27 C28 S1 130.53(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
O1 H1 O4 0.82 1.88 2.6974(19) 172.3 2_565
N1 H1A O1 0.86 1.90 2.6617(19) 146.7 2_564
N2 H2 N3 0.89(2) 1.85(2) 2.736(2) 171(2) .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nami-150528akmm
_database_code_depnum_ccdc_archive 'CCDC 1442789'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2015-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H33 N2 O, C4 H4 N O4 S'
_chemical_formula_sum            'C25 H37 N3 O5 S'
_chemical_formula_weight         491.64
_chemical_absolute_configuration ad
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   7.3761(5)
_cell_length_b                   17.7987(15)
_cell_length_c                   9.5359(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.633(6)
_cell_angle_gamma                90.00
_cell_volume                     1237.73(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1872
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      27.1630
_cell_measurement_theta_min      3.4700
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8262
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.02
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   65.00   92.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  178.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   14.00   56.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  -99.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00   75.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889    0.0000 -180.0000 140

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00  -19.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -37.0000  120.0000 72
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0336647000
_diffrn_orient_matrix_UB_12      -0.0308106000
_diffrn_orient_matrix_UB_13      0.0358509000
_diffrn_orient_matrix_UB_21      0.0164176000
_diffrn_orient_matrix_UB_22      0.0201730000
_diffrn_orient_matrix_UB_23      0.0646978000
_diffrn_orient_matrix_UB_31      -0.0897449000
_diffrn_orient_matrix_UB_32      0.0152314000
_diffrn_orient_matrix_UB_33      -0.0136807000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3506
_reflns_number_total             4381
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.18(10)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4381
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      0.824
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1345
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13), C14(H14), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
 C18(H18A,H18B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), N1(H1), N2(H2), C2(H2A)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C4(H4A,H4B,H4C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C0AA C 0.6489(4) 0.52856(19) 0.8421(3) 0.0277(7) Uani 1 d . . .
C5 C 1.3114(5) 0.7243(2) 0.1628(4) 0.0374(8) Uani 1 d . . .
H5 H 1.3864 0.6827 0.1578 0.045 Uiso 1 calc . . R
C6 C 1.1634(5) 0.72816(19) 0.2381(4) 0.0332(8) Uani 1 d . . .
C7 C 1.0935(5) 0.80009(19) 0.2169(4) 0.0324(8) Uani 1 d . . .
C8 C 0.9420(5) 0.83268(19) 0.2835(4) 0.0337(8) Uani 1 d . . .
H8A H 0.8518 0.8552 0.2112 0.040 Uiso 1 calc . . R
H8B H 0.9898 0.8717 0.3500 0.040 Uiso 1 calc . . R
C9 C 0.8506(4) 0.77072(19) 0.3621(4) 0.0280(7) Uani 1 d . . .
H9 H 0.7714 0.7413 0.2906 0.034 Uiso 1 calc . . R
C10 C 0.9917(4) 0.71553(18) 0.4456(4) 0.0256(7) Uani 1 d . . .
C11 C 1.0901(5) 0.67298(19) 0.3358(4) 0.0377(9) Uani 1 d . . .
H11A H 1.1903 0.6434 0.3852 0.045 Uiso 1 calc . . R
H11B H 1.0045 0.6390 0.2808 0.045 Uiso 1 calc . . R
C12 C 1.1353(4) 0.75763(19) 0.5490(4) 0.0329(8) Uani 1 d . . .
H12A H 1.1949 0.7944 0.4981 0.049 Uiso 1 calc . . GR
H12B H 1.2247 0.7227 0.5941 0.049 Uiso 1 calc . . GR
H12C H 1.0765 0.7822 0.6196 0.049 Uiso 1 calc . . GR
C13 C 0.8852(4) 0.65724(17) 0.5240(4) 0.0252(7) Uani 1 d . . .
H13 H 0.7974 0.6329 0.4506 0.030 Uiso 1 calc . . R
C14 C 0.7699(4) 0.69600(17) 0.6258(4) 0.0261(7) Uani 1 d . . .
H14 H 0.8522 0.7241 0.6974 0.031 Uiso 1 calc . . R
C15 C 0.6348(4) 0.75105(19) 0.5421(4) 0.0334(8) Uani 1 d . . .
H15A H 0.5455 0.7229 0.4777 0.040 Uiso 1 calc . . R
H15B H 0.5694 0.7778 0.6076 0.040 Uiso 1 calc . . R
C16 C 0.7280(4) 0.80739(19) 0.4580(4) 0.0335(8) Uani 1 d . . .
H16A H 0.8015 0.8411 0.5233 0.040 Uiso 1 calc . . R
H16B H 0.6351 0.8372 0.4003 0.040 Uiso 1 calc . . R
C17 C 1.0058(4) 0.59435(18) 0.5977(4) 0.0319(8) Uani 1 d . . .
H17A H 1.0669 0.5689 0.5279 0.038 Uiso 1 calc . . R
H17B H 1.0996 0.6165 0.6677 0.038 Uiso 1 calc . . R
C18 C 0.8982(5) 0.53640(18) 0.6710(4) 0.0321(8) Uani 1 d . . .
H18A H 0.9820 0.4995 0.7194 0.039 Uiso 1 calc . . R
H18B H 0.8120 0.5104 0.6006 0.039 Uiso 1 calc . . R
C19 C 0.7939(4) 0.57543(18) 0.7785(4) 0.0253(7) Uani 1 d . . .
C20 C 0.6696(4) 0.63606(18) 0.7002(4) 0.0265(7) Uani 1 d . . .
H20 H 0.5870 0.6101 0.6256 0.032 Uiso 1 calc . . R
C21 C 0.9323(5) 0.6083(2) 0.9007(4) 0.0351(8) Uani 1 d . . .
H21A H 0.8671 0.6319 0.9686 0.053 Uiso 1 calc . . GR
H21B H 1.0084 0.6447 0.8635 0.053 Uiso 1 calc . . GR
H21C H 1.0076 0.5686 0.9461 0.053 Uiso 1 calc . . GR
C22 C 0.5509(5) 0.6613(2) 0.8119(4) 0.0362(8) Uani 1 d . . .
H22A H 0.6100 0.7018 0.8697 0.043 Uiso 1 calc . . R
H22B H 0.4313 0.6782 0.7666 0.043 Uiso 1 calc . . R
C23 C 0.5337(5) 0.5909(2) 0.9019(4) 0.0355(8) Uani 1 d . . .
H23A H 0.4065 0.5756 0.8946 0.043 Uiso 1 calc . . R
H23B H 0.5806 0.6006 1.0008 0.043 Uiso 1 calc . . R
C24 C 0.5258(5) 0.4789(2) 0.7372(4) 0.0408(9) Uani 1 d . . .
H24A H 0.4558 0.5099 0.6664 0.061 Uiso 1 calc . . GR
H24B H 0.4440 0.4509 0.7869 0.061 Uiso 1 calc . . GR
H24C H 0.6002 0.4448 0.6925 0.061 Uiso 1 calc . . GR
N1 N 1.3272(4) 0.78973(16) 0.0995(4) 0.0398(8) Uani 1 d . . .
H1 H 1.4081 0.8006 0.0465 0.048 Uiso 1 calc . . R
N2 N 1.1950(4) 0.83677(16) 0.1320(3) 0.0357(7) Uani 1 d . . .
H2 H 1.1785 0.8824 0.1033 0.043 Uiso 1 calc . . R
O5 O 0.7408(3) 0.47954(13) 0.9527(2) 0.0301(5) Uani 1 d . . .
H5A H 0.6707 0.4698 1.0093 0.045 Uiso 1 calc . . GR
C1 C 0.3595(4) 0.38350(19) 0.0948(4) 0.0309(8) Uani 1 d . . .
C2 C 0.1871(4) 0.3849(2) 0.1504(4) 0.0326(8) Uani 1 d . . .
H2A H 0.1075 0.3445 0.1300 0.039 Uiso 1 calc . . R
C3 C 0.1359(5) 0.4407(2) 0.2289(4) 0.0336(8) Uani 1 d . . .
C4 C -0.0437(4) 0.4511(2) 0.2777(4) 0.0411(9) Uani 1 d . . .
H4A H -0.1258 0.4119 0.2395 0.062 Uiso 1 calc . . GR
H4B H -0.0940 0.4990 0.2460 0.062 Uiso 1 calc . . GR
H4C H -0.0276 0.4492 0.3795 0.062 Uiso 1 calc . . GR
N3 N 0.4865(4) 0.43781(16) 0.1340(3) 0.0336(7) Uani 1 d . . .
O1 O 0.2530(3) 0.49993(15) 0.2688(3) 0.0412(6) Uani 1 d . . .
O2 O 0.5305(3) 0.44318(17) 0.3978(3) 0.0478(7) Uani 1 d . . .
O3 O 0.5456(4) 0.55848(16) 0.2606(3) 0.0485(7) Uani 1 d . . .
O4 O 0.3842(3) 0.33521(14) 0.0044(3) 0.0407(6) Uani 1 d . . .
S1 S 0.47177(10) 0.48502(5) 0.27209(9) 0.0335(2) Uani 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
C0AA C19 1.550(4) . ?
C0AA C23 1.556(5) . ?
C0AA C24 1.527(5) . ?
C0AA O5 1.455(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(5) . ?
C5 N1 1.325(5) . ?
C6 C7 1.384(5) . ?
C6 C11 1.509(5) . ?
C7 C8 1.483(5) . ?
C7 N2 1.351(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.544(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.560(4) . ?
C9 C16 1.526(5) . ?
C10 C11 1.557(5) . ?
C10 C12 1.530(5) . ?
C10 C13 1.558(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9800 . ?
C13 C14 1.546(4) . ?
C13 C17 1.533(4) . ?
C14 H14 0.9800 . ?
C14 C15 1.533(4) . ?
C14 C20 1.532(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.512(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.533(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.537(5) . ?
C19 C20 1.536(4) . ?
C19 C21 1.544(5) . ?
C20 H20 0.9800 . ?
C20 C22 1.543(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.536(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1 0.8600 . ?
N1 N2 1.356(4) . ?
N2 H2 0.8600 . ?
O5 H5A 0.8200 . ?
C1 C2 1.450(5) . ?
C1 N3 1.359(4) . ?
C1 O4 1.250(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.333(5) . ?
C3 C4 1.480(5) . ?
C3 O1 1.379(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N3 S1 1.579(3) . ?
O1 S1 1.631(2) . ?
O2 S1 1.423(3) . ?
O3 S1 1.427(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
C19 C0AA C23 101.9(3) . . ?
C24 C0AA C19 115.6(3) . . ?
C24 C0AA C23 110.4(3) . . ?
O5 C0AA C19 109.4(2) . . ?
O5 C0AA C23 112.5(3) . . ?
O5 C0AA C24 107.1(3) . . ?
C6 C5 H5 125.7 . . ?
N1 C5 H5 125.7 . . ?
N1 C5 C6 108.7(3) . . ?
C5 C6 C11 131.8(3) . . ?
C7 C6 C5 105.9(3) . . ?
C7 C6 C11 122.1(3) . . ?
C6 C7 C8 126.0(3) . . ?
N2 C7 C6 107.8(3) . . ?
N2 C7 C8 126.1(3) . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C7 C8 C9 109.9(3) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C8 C9 H9 107.5 . . ?
C8 C9 C10 113.0(2) . . ?
C10 C9 H9 107.5 . . ?
C16 C9 C8 109.1(3) . . ?
C16 C9 H9 107.5 . . ?
C16 C9 C10 111.9(3) . . ?
C11 C10 C9 107.8(3) . . ?
C11 C10 C13 108.5(3) . . ?
C12 C10 C9 111.4(3) . . ?
C12 C10 C11 108.9(3) . . ?
C12 C10 C13 111.6(3) . . ?
C13 C10 C9 108.5(2) . . ?
C6 C11 C10 110.2(3) . . ?
C6 C11 H11A 109.6 . . ?
C6 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13 106.2 . . ?
C14 C13 C10 111.6(2) . . ?
C14 C13 H13 106.2 . . ?
C17 C13 C10 114.0(2) . . ?
C17 C13 H13 106.2 . . ?
C17 C13 C14 112.0(3) . . ?
C13 C14 H14 108.9 . . ?
C15 C14 C13 109.5(3) . . ?
C15 C14 H14 108.9 . . ?
C20 C14 C13 109.2(2) . . ?
C20 C14 H14 108.9 . . ?
C20 C14 C15 111.4(2) . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 112.8(3) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C9 C16 H16A 109.0 . . ?
C9 C16 H16B 109.0 . . ?
C15 C16 C9 113.0(3) . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C13 C17 H17A 108.9 . . ?
C13 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C13 113.3(3) . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
C17 C18 C19 110.2(3) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C18 C19 C0AA 117.5(3) . . ?
C18 C19 C21 109.5(3) . . ?
C20 C19 C0AA 99.9(2) . . ?
C20 C19 C18 108.4(3) . . ?
C20 C19 C21 112.3(3) . . ?
C21 C19 C0AA 109.0(3) . . ?
C14 C20 C19 114.8(2) . . ?
C14 C20 H20 106.4 . . ?
C14 C20 C22 118.7(3) . . ?
C19 C20 H20 106.4 . . ?
C19 C20 C22 103.2(3) . . ?
C22 C20 H20 106.4 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 110.9 . . ?
C20 C22 H22B 110.9 . . ?
H22A C22 H22B 108.9 . . ?
C23 C22 C20 104.5(3) . . ?
C23 C22 H22A 110.9 . . ?
C23 C22 H22B 110.9 . . ?
C0AA C23 H23A 110.5 . . ?
C0AA C23 H23B 110.5 . . ?
C22 C23 C0AA 106.4(3) . . ?
C22 C23 H23A 110.5 . . ?
C22 C23 H23B 110.5 . . ?
H23A C23 H23B 108.6 . . ?
C0AA C24 H24A 109.5 . . ?
C0AA C24 H24B 109.5 . . ?
C0AA C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C5 N1 H1 125.6 . . ?
C5 N1 N2 108.8(3) . . ?
N2 N1 H1 125.6 . . ?
C7 N2 N1 108.7(3) . . ?
C7 N2 H2 125.6 . . ?
N1 N2 H2 125.6 . . ?
C0AA O5 H5A 109.5 . . ?
N3 C1 C2 119.6(3) . . ?
O4 C1 C2 119.4(3) . . ?
O4 C1 N3 120.9(3) . . ?
C1 C2 H2A 118.1 . . ?
C3 C2 C1 123.8(3) . . ?
C3 C2 H2A 118.1 . . ?
C2 C3 C4 127.7(3) . . ?
C2 C3 O1 120.4(3) . . ?
O1 C3 C4 111.8(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 N3 S1 118.5(2) . . ?
C3 O1 S1 117.2(2) . . ?
N3 S1 O1 105.20(14) . . ?
O2 S1 N3 111.94(16) . . ?
O2 S1 O1 106.05(15) . . ?
O2 S1 O3 118.22(17) . . ?
O3 S1 N3 110.44(17) . . ?
O3 S1 O1 103.72(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 O4 0.86 1.78 2.608(4) 159.6 2_755
N2 H2 O5 0.86 1.93 2.729(4) 154.1 2_756
O5 H5A N3 0.82 2.02 2.834(3) 174.0 1_556

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
C0AA C19 C20 C14 178.2(3) . . . . ?
C0AA C19 C20 C22 47.5(3) . . . . ?
C5 C6 C7 C8 -175.8(4) . . . . ?
C5 C6 C7 N2 0.5(4) . . . . ?
C5 C6 C11 C10 152.3(4) . . . . ?
C5 N1 N2 C7 -0.3(4) . . . . ?
C6 C5 N1 N2 0.5(4) . . . . ?
C6 C7 C8 C9 -9.2(5) . . . . ?
C6 C7 N2 N1 -0.1(4) . . . . ?
C7 C6 C11 C10 -22.0(5) . . . . ?
C7 C8 C9 C10 41.5(4) . . . . ?
C7 C8 C9 C16 166.7(3) . . . . ?
C8 C7 N2 N1 176.1(4) . . . . ?
C8 C9 C10 C11 -64.3(4) . . . . ?
C8 C9 C10 C12 55.1(4) . . . . ?
C8 C9 C10 C13 178.3(3) . . . . ?
C8 C9 C16 C15 -178.9(3) . . . . ?
C9 C10 C11 C6 51.4(4) . . . . ?
C9 C10 C13 C14 -58.1(3) . . . . ?
C9 C10 C13 C17 173.8(3) . . . . ?
C10 C9 C16 C15 -53.1(4) . . . . ?
C10 C13 C14 C15 58.1(3) . . . . ?
C10 C13 C14 C20 -179.6(2) . . . . ?
C10 C13 C17 C18 -178.5(3) . . . . ?
C11 C6 C7 C8 -0.3(6) . . . . ?
C11 C6 C7 N2 176.0(3) . . . . ?
C11 C10 C13 C14 -175.0(3) . . . . ?
C11 C10 C13 C17 56.9(4) . . . . ?
C12 C10 C11 C6 -69.6(4) . . . . ?
C12 C10 C13 C14 65.0(3) . . . . ?
C12 C10 C13 C17 -63.1(4) . . . . ?
C13 C10 C11 C6 168.8(3) . . . . ?
C13 C14 C15 C16 -54.6(4) . . . . ?
C13 C14 C20 C19 55.0(4) . . . . ?
C13 C14 C20 C22 177.7(3) . . . . ?
C13 C17 C18 C19 -56.6(4) . . . . ?
C14 C13 C17 C18 53.6(4) . . . . ?
C14 C15 C16 C9 53.0(4) . . . . ?
C14 C20 C22 C23 -159.1(3) . . . . ?
C15 C14 C20 C19 176.1(3) . . . . ?
C15 C14 C20 C22 -61.2(4) . . . . ?
C16 C9 C10 C11 172.1(3) . . . . ?
C16 C9 C10 C12 -68.5(3) . . . . ?
C16 C9 C10 C13 54.7(4) . . . . ?
C17 C13 C14 C15 -172.8(3) . . . . ?
C17 C13 C14 C20 -50.5(3) . . . . ?
C17 C18 C19 C0AA 168.6(3) . . . . ?
C17 C18 C19 C20 56.5(4) . . . . ?
C17 C18 C19 C21 -66.3(4) . . . . ?
C18 C19 C20 C14 -58.4(4) . . . . ?
C18 C19 C20 C22 170.9(3) . . . . ?
C19 C0AA C23 C22 27.1(4) . . . . ?
C19 C20 C22 C23 -30.8(4) . . . . ?
C20 C14 C15 C16 -175.6(3) . . . . ?
C20 C22 C23 C0AA 2.0(4) . . . . ?
C21 C19 C20 C14 62.8(4) . . . . ?
C21 C19 C20 C22 -67.9(3) . . . . ?
C23 C0AA C19 C18 -162.2(3) . . . . ?
C23 C0AA C19 C20 -45.4(3) . . . . ?
C23 C0AA C19 C21 72.5(3) . . . . ?
C24 C0AA C19 C18 -42.5(4) . . . . ?
C24 C0AA C19 C20 74.4(3) . . . . ?
C24 C0AA C19 C21 -167.8(3) . . . . ?
C24 C0AA C23 C22 -96.3(3) . . . . ?
N1 C5 C6 C7 -0.6(4) . . . . ?
N1 C5 C6 C11 -175.6(4) . . . . ?
N2 C7 C8 C9 175.2(3) . . . . ?
O5 C0AA C19 C18 78.6(3) . . . . ?
O5 C0AA C19 C20 -164.6(3) . . . . ?
O5 C0AA C19 C21 -46.7(3) . . . . ?
O5 C0AA C23 C22 144.1(3) . . . . ?
C1 C2 C3 C4 173.1(4) . . . . ?
C1 C2 C3 O1 -3.7(6) . . . . ?
C1 N3 S1 O1 -39.6(3) . . . . ?
C1 N3 S1 O2 75.2(3) . . . . ?
C1 N3 S1 O3 -150.9(3) . . . . ?
C2 C1 N3 S1 18.9(4) . . . . ?
C2 C3 O1 S1 -23.1(4) . . . . ?
C3 O1 S1 N3 42.0(3) . . . . ?
C3 O1 S1 O2 -76.8(3) . . . . ?
C3 O1 S1 O3 158.0(3) . . . . ?
C4 C3 O1 S1 159.6(2) . . . . ?
N3 C1 C2 C3 6.5(5) . . . . ?
O4 C1 C2 C3 -168.8(3) . . . . ?
O4 C1 N3 S1 -165.8(3) . . . . ?

_olex2_date_sample_data_collection 2015-05-28
_olex2_submission_special_instructions 'No special instructions were received'
