# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_m49m
_database_code_depnum_ccdc_archive 'CCDC 1424361'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


_diffrn_measurement_device_type  'SMART APEX I'
#Added by publCIF


_publcif_datablock.id            {b2e21d0b-5463-464c-9ad4-7134912af6d4}

_audit_creation_date             2010-03-26T11:51:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H41 N3 O5 S'
_chemical_formula_sum            'C31 H41 N3 O5 S'
_chemical_formula_weight         567.73
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8633(16)
_cell_length_b                   11.9397(18)
_cell_length_c                   12.4101(19)
_cell_angle_alpha                88.791(2)
_cell_angle_beta                 73.634(2)
_cell_angle_gamma                78.963(2)
_cell_volume                     1514.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       hexagonal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    0.15
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_number            12268
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_full        26.52
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_reflns_number_total             6184
_reflns_number_gt                5028
_reflns_threshold_expression     >2sigma(I)

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

_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1130P)²+0.5669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6184
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1921
_refine_ls_wR_factor_gt          0.1804
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.059

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.03660(5) 0.44950(5) 0.25808(5) 0.04072(19) Uani 1 1 d . . .
O1 O 0.04424(17) 0.52060(15) 0.34590(15) 0.0560(5) Uani 1 1 d . . .
O2 O -0.02688(17) 0.49669(15) 0.17727(16) 0.0554(5) Uani 1 1 d . . .
O3 O 0.2402(2) 0.12963(17) 0.31119(19) 0.0767(6) Uani 1 1 d . . .
O4 O 0.4451(3) 0.0632(2) 0.2454(2) 0.1076(10) Uani 1 1 d . . .
O5 O 0.3254(2) 0.21132(19) 0.63242(16) 0.0720(6) Uani 1 1 d . . .
N1 N 0.3484(3) 0.13697(18) 0.25622(19) 0.0567(6) Uani 1 1 d . . .
N2 N 0.40485(18) 0.31992(16) 0.42506(15) 0.0417(4) Uani 1 1 d . . .
N3 N 0.18935(17) 0.39623(15) 0.18900(14) 0.0358(4) Uani 1 1 d . . .
C1 C 0.3695(2) 0.24577(18) 0.19199(18) 0.0393(5) Uani 1 1 d . . .
H1 H 0.4613 0.2531 0.1747 0.047 Uiso 1 1 calc R . .
C2 C 0.3307(2) 0.24097(18) 0.08578(18) 0.0391(5) Uani 1 1 d . . .
C3 C 0.3860(3) 0.1674(2) -0.0073(2) 0.0536(6) Uani 1 1 d . . .
H3 H 0.4577 0.1097 -0.0096 0.064 Uiso 1 1 calc R . .
C4 C 0.3333(3) 0.1809(2) -0.0964(2) 0.0601(7) Uani 1 1 d . . .
H4 H 0.3688 0.1317 -0.1592 0.072 Uiso 1 1 calc R . .
C5 C 0.2281(3) 0.2671(3) -0.0926(2) 0.0573(7) Uani 1 1 d . . .
H5 H 0.1934 0.2748 -0.1535 0.069 Uiso 1 1 calc R . .
C6 C 0.1721(2) 0.3424(2) -0.00175(19) 0.0474(6) Uani 1 1 d . . .
H6 H 0.1018 0.4011 -0.0008 0.057 Uiso 1 1 calc R . .
C7 C 0.2250(2) 0.32727(18) 0.08854(17) 0.0368(5) Uani 1 1 d . . .
C8 C 0.28060(19) 0.35192(17) 0.25771(17) 0.0342(4) Uani 1 1 d . . .
H8 H 0.2305 0.33 0.3311 0.041 Uiso 1 1 calc R . .
C9 C 0.3566(2) 0.44346(19) 0.27430(19) 0.0396(5) Uani 1 1 d . . .
H9 H 0.2934 0.507 0.3192 0.047 Uiso 1 1 calc R . .
C10 C 0.4254(3) 0.4904(2) 0.1622(2) 0.0526(6) Uani 1 1 d . . .
H10A H 0.4744 0.4274 0.1101 0.063 Uiso 1 1 calc R . .
H10B H 0.3606 0.5347 0.1302 0.063 Uiso 1 1 calc R . .
C11 C 0.5178(3) 0.5651(3) 0.1788(3) 0.0651(8) Uani 1 1 d . . .
H11A H 0.5563 0.598 0.1081 0.078 Uiso 1 1 calc R . .
H11B H 0.4696 0.627 0.2325 0.078 Uiso 1 1 calc R . .
C12 C 0.6241(3) 0.4946(3) 0.2211(3) 0.0681(8) Uani 1 1 d . . .
H12A H 0.6871 0.4485 0.1591 0.082 Uiso 1 1 calc R . .
H12B H 0.6692 0.5452 0.2488 0.082 Uiso 1 1 calc R . .
C13 C 0.5721(3) 0.4177(2) 0.3133(2) 0.0571(7) Uani 1 1 d . . .
H13 H 0.6278 0.3832 0.3544 0.069 Uiso 1 1 calc R . .
C14 C 0.4525(2) 0.3959(2) 0.34001(19) 0.0421(5) Uani 1 1 d . . .
C15 C 0.4997(3) 0.2522(3) 0.4746(2) 0.0598(7) Uani 1 1 d . . .
H15A H 0.528 0.301 0.5205 0.072 Uiso 1 1 calc R . .
H15B H 0.5757 0.2157 0.4157 0.072 Uiso 1 1 calc R . .
C16 C 0.4371(3) 0.1620(3) 0.5465(3) 0.0664(8) Uani 1 1 d . . .
H16A H 0.4129 0.1114 0.4993 0.08 Uiso 1 1 calc R . .
H16B H 0.5002 0.1166 0.5797 0.08 Uiso 1 1 calc R . .
C17 C 0.2324(3) 0.2794(3) 0.5851(2) 0.0618(7) Uani 1 1 d . . .
H17A H 0.1563 0.3139 0.6449 0.074 Uiso 1 1 calc R . .
H17B H 0.2042 0.2312 0.5384 0.074 Uiso 1 1 calc R . .
C18 C 0.2894(3) 0.3718(2) 0.51539(19) 0.0496(6) Uani 1 1 d . . .
H18A H 0.2247 0.4164 0.4834 0.059 Uiso 1 1 calc R . .
H18B H 0.3139 0.4224 0.5624 0.059 Uiso 1 1 calc R . .
C19 C -0.0340(2) 0.3353(2) 0.32064(19) 0.0431(5) Uani 1 1 d . . .
C20 C -0.0694(3) 0.2615(2) 0.2554(2) 0.0569(6) Uani 1 1 d . . .
H20 H -0.0603 0.2747 0.1796 0.068 Uiso 1 1 calc R . .
C21 C -0.1181(3) 0.1687(3) 0.3034(3) 0.0698(8) Uani 1 1 d . . .
H21 H -0.1411 0.1188 0.2593 0.084 Uiso 1 1 calc R . .
C23 C -0.1335(3) 0.1479(3) 0.4158(3) 0.0718(9) Uani 1 1 d . . .
C24 C -0.1005(3) 0.2234(3) 0.4791(3) 0.0745(9) Uani 1 1 d . . .
H24 H -0.1122 0.2111 0.5553 0.089 Uiso 1 1 calc R . .
C25 C -0.0506(3) 0.3173(3) 0.4337(2) 0.0596(7) Uani 1 1 d . . .
H25 H -0.0285 0.3674 0.4782 0.071 Uiso 1 1 calc R . .
C26 C -0.1842(4) 0.0432(4) 0.4662(4) 0.1149(17) Uani 1 1 d . . .
H26A H -0.1117 -0.0181 0.4636 0.172 Uiso 1 1 calc R . .
H26B H -0.2379 0.0208 0.4241 0.172 Uiso 1 1 calc R . .
H26C H -0.235 0.0605 0.5429 0.172 Uiso 1 1 calc R . .
C1S C 0.1885(8) -0.0501(5) 0.1069(5) 0.176(3) Uani 1 1 d . . .
H1S1 H 0.1522 0.0309 0.1089 0.211 Uiso 1 1 calc R . .
H1S2 H 0.2683 -0.0591 0.1295 0.211 Uiso 1 1 calc R . .
C2S C 0.2197(8) -0.0963(5) -0.0080(5) 0.168(3) Uani 1 1 d . . .
H2S1 H 0.1474 -0.0656 -0.0382 0.202 Uiso 1 1 calc R . .
H2S2 H 0.2959 -0.069 -0.0533 0.202 Uiso 1 1 calc R . .
C3S C 0.2441(8) -0.2140(6) -0.0202(5) 0.169(3) Uani 1 1 d . . .
H3S1 H 0.3321 -0.2426 -0.0153 0.203 Uiso 1 1 calc R . .
H3S2 H 0.2427 -0.2333 -0.0953 0.203 Uiso 1 1 calc R . .
C4S C 0.1573(7) -0.2743(5) 0.0582(5) 0.137(2) Uani 1 1 d . . .
H4S1 H 0.1962 -0.3549 0.053 0.164 Uiso 1 1 calc R . .
H4S2 H 0.0757 -0.2661 0.0386 0.164 Uiso 1 1 calc R . .
C5S C 0.1297(8) -0.2301(5) 0.1767(5) 0.166(3) Uani 1 1 d . . .
H5S1 H 0.06 -0.2636 0.2249 0.2 Uiso 1 1 calc R . .
H5S2 H 0.2071 -0.2544 0.2019 0.2 Uiso 1 1 calc R . .
C6S C 0.0928(10) -0.1087(6) 0.1883(5) 0.219(5) Uani 1 1 d . . .
H6S1 H 0.0863 -0.085 0.2643 0.263 Uiso 1 1 calc R . .
H6S2 H 0.0072 -0.0852 0.1764 0.263 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4198(18) . ?
S1 O1 1.4256(18) . ?
S1 N3 1.6463(18) . ?
S1 C19 1.752(2) . ?
O3 N1 1.200(3) . ?
O4 N1 1.212(3) . ?
O5 C16 1.407(3) . ?
O5 C17 1.424(3) . ?
N1 C1 1.531(3) . ?
N2 C14 1.427(3) . ?
N2 C15 1.453(3) . ?
N2 C18 1.467(3) . ?
N3 C7 1.425(3) . ?
N3 C8 1.499(2) . ?
C1 C2 1.498(3) . ?
C1 C8 1.528(3) . ?
C1 H1 0.98 . ?
C2 C7 1.381(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.375(4) . ?
C3 H3 0.93 . ?
C4 C5 1.375(4) . ?
C4 H4 0.93 . ?
C5 C6 1.377(4) . ?
C5 H5 0.93 . ?
C6 C7 1.390(3) . ?
C6 H6 0.93 . ?
C8 C9 1.539(3) . ?
C8 H8 0.98 . ?
C9 C14 1.518(3) . ?
C9 C10 1.532(3) . ?
C9 H9 0.98 . ?
C10 C11 1.521(3) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C12 1.505(4) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.504(4) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.323(3) . ?
C13 H13 0.93 . ?
C15 C16 1.522(4) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 C18 1.506(4) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C19 C25 1.381(4) . ?
C19 C20 1.385(4) . ?
C20 C21 1.371(4) . ?
C20 H20 0.93 . ?
C21 C23 1.381(5) . ?
C21 H21 0.93 . ?
C23 C24 1.368(5) . ?
C23 C26 1.514(4) . ?
C24 C25 1.379(4) . ?
C24 H24 0.93 . ?
C25 H25 0.93 . ?
C26 H26A 0.96 . ?
C26 H26B 0.96 . ?
C26 H26C 0.96 . ?
C1S C2S 1.463(7) . ?
C1S C6S 1.500(9) . ?
C1S H1S1 0.97 . ?
C1S H1S2 0.97 . ?
C2S C3S 1.383(8) . ?
C2S H2S1 0.97 . ?
C2S H2S2 0.97 . ?
C3S C4S 1.437(7) . ?
C3S H3S1 0.97 . ?
C3S H3S2 0.97 . ?
C4S C5S 1.501(8) . ?
C4S H4S1 0.97 . ?
C4S H4S2 0.97 . ?
C5S C6S 1.427(8) . ?
C5S H5S1 0.97 . ?
C5S H5S2 0.97 . ?
C6S H6S1 0.97 . ?
C6S H6S2 0.97 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.10(11) . . ?
O2 S1 N3 106.89(10) . . ?
O1 S1 N3 105.25(10) . . ?
O2 S1 C19 109.16(11) . . ?
O1 S1 C19 107.62(11) . . ?
N3 S1 C19 107.12(10) . . ?
C16 O5 C17 110.0(2) . . ?
O3 N1 O4 125.0(3) . . ?
O3 N1 C1 119.2(2) . . ?
O4 N1 C1 115.8(3) . . ?
C14 N2 C15 116.88(19) . . ?
C14 N2 C18 114.95(18) . . ?
C15 N2 C18 108.92(19) . . ?
C7 N3 C8 108.98(16) . . ?
C7 N3 S1 123.11(14) . . ?
C8 N3 S1 116.97(13) . . ?
C2 C1 C8 105.37(17) . . ?
C2 C1 N1 109.01(18) . . ?
C8 C1 N1 111.61(18) . . ?
C2 C1 H1 110.2 . . ?
C8 C1 H1 110.2 . . ?
N1 C1 H1 110.2 . . ?
C7 C2 C3 120.5(2) . . ?
C7 C2 C1 109.85(19) . . ?
C3 C2 C1 129.7(2) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
C4 C5 C6 122.3(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C7 117.3(2) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C2 C7 C6 120.9(2) . . ?
C2 C7 N3 110.82(18) . . ?
C6 C7 N3 128.1(2) . . ?
N3 C8 C1 104.79(16) . . ?
N3 C8 C9 110.62(16) . . ?
C1 C8 C9 112.83(17) . . ?
N3 C8 H8 109.5 . . ?
C1 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C14 C9 C10 111.49(19) . . ?
C14 C9 C8 110.07(17) . . ?
C10 C9 C8 111.86(18) . . ?
C14 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
C11 C10 C9 110.8(2) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 109.7(2) . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 112.6(2) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 124.4(2) . . ?
C14 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C13 C14 N2 124.3(2) . . ?
C13 C14 C9 121.7(2) . . ?
N2 C14 C9 113.81(18) . . ?
N2 C15 C16 109.1(2) . . ?
N2 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
N2 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
O5 C16 C15 111.7(2) . . ?
O5 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
O5 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
O5 C17 C18 111.2(2) . . ?
O5 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
O5 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108 . . ?
N2 C18 C17 109.6(2) . . ?
N2 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
N2 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C25 C19 C20 120.3(2) . . ?
C25 C19 S1 120.1(2) . . ?
C20 C19 S1 119.59(19) . . ?
C21 C20 C19 119.4(3) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C23 121.3(3) . . ?
C20 C21 H21 119.3 . . ?
C23 C21 H21 119.3 . . ?
C24 C23 C21 118.2(3) . . ?
C24 C23 C26 121.5(4) . . ?
C21 C23 C26 120.3(4) . . ?
C23 C24 C25 122.1(3) . . ?
C23 C24 H24 118.9 . . ?
C25 C24 H24 118.9 . . ?
C24 C25 C19 118.6(3) . . ?
C24 C25 H25 120.7 . . ?
C19 C25 H25 120.7 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2S C1S C6S 111.9(5) . . ?
C2S C1S H1S1 109.2 . . ?
C6S C1S H1S1 109.2 . . ?
C2S C1S H1S2 109.2 . . ?
C6S C1S H1S2 109.2 . . ?
H1S1 C1S H1S2 107.9 . . ?
C3S C2S C1S 115.9(6) . . ?
C3S C2S H2S1 108.3 . . ?
C1S C2S H2S1 108.3 . . ?
C3S C2S H2S2 108.3 . . ?
C1S C2S H2S2 108.3 . . ?
H2S1 C2S H2S2 107.4 . . ?
C2S C3S C4S 117.5(6) . . ?
C2S C3S H3S1 107.9 . . ?
C4S C3S H3S1 107.9 . . ?
C2S C3S H3S2 107.9 . . ?
C4S C3S H3S2 107.9 . . ?
H3S1 C3S H3S2 107.2 . . ?
C3S C4S C5S 111.6(5) . . ?
C3S C4S H4S1 109.3 . . ?
C5S C4S H4S1 109.3 . . ?
C3S C4S H4S2 109.3 . . ?
C5S C4S H4S2 109.3 . . ?
H4S1 C4S H4S2 108 . . ?
C6S C5S C4S 113.1(5) . . ?
C6S C5S H5S1 109 . . ?
C4S C5S H5S1 109 . . ?
C6S C5S H5S2 109 . . ?
C4S C5S H5S2 109 . . ?
H5S1 C5S H5S2 107.8 . . ?
C5S C6S C1S 112.4(6) . . ?
C5S C6S H6S1 109.1 . . ?
C1S C6S H6S1 109.1 . . ?
C5S C6S H6S2 109.1 . . ?
C1S C6S H6S2 109.1 . . ?
H6S1 C6S H6S2 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N3 C7 -46.03(19) . . . . ?
O1 S1 N3 C7 -174.79(16) . . . . ?
C19 S1 N3 C7 70.87(18) . . . . ?
O2 S1 N3 C8 173.83(14) . . . . ?
O1 S1 N3 C8 45.07(17) . . . . ?
C19 S1 N3 C8 -69.27(16) . . . . ?
O3 N1 C1 C2 -79.8(3) . . . . ?
O4 N1 C1 C2 99.2(3) . . . . ?
O3 N1 C1 C8 36.2(3) . . . . ?
O4 N1 C1 C8 -144.8(2) . . . . ?
C8 C1 C2 C7 -4.1(2) . . . . ?
N1 C1 C2 C7 115.8(2) . . . . ?
C8 C1 C2 C3 174.6(2) . . . . ?
N1 C1 C2 C3 -65.5(3) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C1 C2 C7 C6 178.66(19) . . . . ?
C3 C2 C7 N3 -176.6(2) . . . . ?
C1 C2 C7 N3 2.3(2) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C5 C6 C7 N3 176.7(2) . . . . ?
C8 N3 C7 C2 0.6(2) . . . . ?
S1 N3 C7 C2 -142.22(16) . . . . ?
C8 N3 C7 C6 -175.5(2) . . . . ?
S1 N3 C7 C6 41.7(3) . . . . ?
C7 N3 C8 C1 -3.1(2) . . . . ?
S1 N3 C8 C1 142.31(15) . . . . ?
C7 N3 C8 C9 118.77(18) . . . . ?
S1 N3 C8 C9 -95.82(18) . . . . ?
C2 C1 C8 N3 4.2(2) . . . . ?
N1 C1 C8 N3 -113.93(19) . . . . ?
C2 C1 C8 C9 -116.17(19) . . . . ?
N1 C1 C8 C9 125.6(2) . . . . ?
N3 C8 C9 C14 -177.75(17) . . . . ?
C1 C8 C9 C14 -60.7(2) . . . . ?
N3 C8 C9 C10 -53.2(2) . . . . ?
C1 C8 C9 C10 63.8(2) . . . . ?
C14 C9 C10 C11 -46.7(3) . . . . ?
C8 C9 C10 C11 -170.4(2) . . . . ?
C9 C10 C11 C12 63.0(3) . . . . ?
C10 C11 C12 C13 -44.8(4) . . . . ?
C11 C12 C13 C14 12.8(4) . . . . ?
C12 C13 C14 N2 177.8(2) . . . . ?
C12 C13 C14 C9 3.1(4) . . . . ?
C15 N2 C14 C13 -8.1(4) . . . . ?
C18 N2 C14 C13 121.4(3) . . . . ?
C15 N2 C14 C9 167.0(2) . . . . ?
C18 N2 C14 C9 -63.5(3) . . . . ?
C10 C9 C14 C13 14.2(3) . . . . ?
C8 C9 C14 C13 138.9(2) . . . . ?
C10 C9 C14 N2 -161.0(2) . . . . ?
C8 C9 C14 N2 -36.3(3) . . . . ?
C14 N2 C15 C16 -169.7(2) . . . . ?
C18 N2 C15 C16 58.0(3) . . . . ?
C17 O5 C16 C15 58.2(3) . . . . ?
N2 C15 C16 O5 -58.9(3) . . . . ?
C16 O5 C17 C18 -58.3(3) . . . . ?
C14 N2 C18 C17 168.0(2) . . . . ?
C15 N2 C18 C17 -58.6(3) . . . . ?
O5 C17 C18 N2 58.8(3) . . . . ?
O2 S1 C19 C25 -142.6(2) . . . . ?
O1 S1 C19 C25 -10.8(2) . . . . ?
N3 S1 C19 C25 102.0(2) . . . . ?
O2 S1 C19 C20 39.3(2) . . . . ?
O1 S1 C19 C20 171.19(19) . . . . ?
N3 S1 C19 C20 -76.1(2) . . . . ?
C25 C19 C20 C21 -1.6(4) . . . . ?
S1 C19 C20 C21 176.5(2) . . . . ?
C19 C20 C21 C23 0.6(4) . . . . ?
C20 C21 C23 C24 0.8(5) . . . . ?
C20 C21 C23 C26 -178.4(3) . . . . ?
C21 C23 C24 C25 -1.3(5) . . . . ?
C26 C23 C24 C25 178.0(3) . . . . ?
C23 C24 C25 C19 0.3(5) . . . . ?
C20 C19 C25 C24 1.2(4) . . . . ?
S1 C19 C25 C24 -176.9(2) . . . . ?
C6S C1S C2S C3S -44.7(12) . . . . ?
C1S C2S C3S C4S 44.4(11) . . . . ?
C2S C3S C4S C5S -45.0(10) . . . . ?
C3S C4S C5S C6S 49.1(10) . . . . ?
C4S C5S C6S C1S -52.2(11) . . . . ?
C2S C1S C6S C5S 49.2(12) . . . . ?

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_manu49
_database_code_depnum_ccdc_archive 'CCDC 1424362'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


_diffrn_measurement_device_type  'SMART APEX I'
#Added by publCIF


_publcif_datablock.id            {3554bbf2-062f-4e03-8261-e5085bfa2952}

_audit_creation_date             2011-09-28T10:14:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 N2 O4 S1'
_chemical_formula_sum            'C24 H26 N2 O4 S'
_chemical_formula_weight         438.53
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.3949(14)
_cell_length_b                   9.5101(9)
_cell_length_c                   16.3426(15)
_cell_angle_alpha                90
_cell_angle_beta                 110.860(2)
_cell_angle_gamma                90
_cell_volume                     2235.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_number            12678
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             4574
_reflns_number_gt                3715
_reflns_threshold_expression     >2sigma(I)

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

_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0659P)²+1.2107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4574
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1323
_refine_ls_goodness_of_fit_ref   0.95
_refine_ls_restrained_S_all      0.95
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.042

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.12348(4) 0.69334(6) 0.19815(4) 0.05451(19) Uani 1 1 d . . .
O1 O 0.21546(13) 0.7195(2) 0.20178(12) 0.0737(5) Uani 1 1 d . . .
O2 O 0.07270(15) 0.57558(19) 0.15114(11) 0.0740(5) Uani 1 1 d . . .
O3 O -0.07655(10) 0.45210(18) 0.38308(10) 0.0576(4) Uani 1 1 d . . .
O4 O -0.11883(12) 0.4488(2) 0.23496(11) 0.0711(5) Uani 1 1 d . . .
N1 N -0.03404(13) 0.7909(2) 0.37874(15) 0.0625(6) Uani 1 1 d . . .
N2 N 0.12984(12) 0.67112(19) 0.30053(11) 0.0474(4) Uani 1 1 d . . .
C1 C 0.17940(14) 0.7656(2) 0.36863(13) 0.0442(5) Uani 1 1 d . . .
C2 C 0.26293(16) 0.8340(3) 0.38173(16) 0.0576(6) Uani 1 1 d . . .
H2 H 0.2931 0.8252 0.3418 0.069 Uiso 1 1 calc R . .
C3 C 0.29997(16) 0.9160(3) 0.45616(17) 0.0625(7) Uani 1 1 d . . .
H3 H 0.3558 0.963 0.466 0.075 Uiso 1 1 calc R . .
C4 C 0.25619(17) 0.9296(3) 0.51601(16) 0.0612(6) Uani 1 1 d . . .
H4 H 0.2828 0.9844 0.5658 0.073 Uiso 1 1 calc R . .
C5 C 0.17288(16) 0.8620(2) 0.50215(15) 0.0542(5) Uani 1 1 d . . .
H5 H 0.1429 0.8711 0.5422 0.065 Uiso 1 1 calc R . .
C6 C 0.13478(14) 0.7809(2) 0.42805(13) 0.0427(5) Uani 1 1 d . . .
C7 C 0.04534(14) 0.6992(2) 0.39832(14) 0.0448(5) Uani 1 1 d . . .
H7 H 0.0455 0.6316 0.4437 0.054 Uiso 1 1 calc R . .
C8 C 0.04428(14) 0.6195(2) 0.31510(13) 0.0438(5) Uani 1 1 d . . .
H8 H -0.0107 0.6486 0.2655 0.053 Uiso 1 1 calc R . .
C9 C 0.04506(15) 0.4596(2) 0.32199(14) 0.0463(5) Uani 1 1 d . . .
H9 H 0.0579 0.4247 0.271 0.056 Uiso 1 1 calc R . .
C10 C -0.04973(16) 0.3996(3) 0.31370(14) 0.0526(5) Uani 1 1 d . . .
C11 C -0.0480(2) 0.2405(3) 0.3142(2) 0.0734(8) Uani 1 1 d . . .
H11A H -0.0404 0.2072 0.261 0.088 Uiso 1 1 calc R . .
H11B H -0.1069 0.2054 0.3147 0.088 Uiso 1 1 calc R . .
C12 C 0.0301(2) 0.1826(3) 0.3928(2) 0.0855(9) Uani 1 1 d . . .
H12A H 0.0177 0.2047 0.4456 0.103 Uiso 1 1 calc R . .
H12B H 0.0316 0.0811 0.388 0.103 Uiso 1 1 calc R . .
C13 C 0.1237(2) 0.2418(3) 0.4008(2) 0.0789(8) Uani 1 1 d . . .
H13A H 0.1402 0.2096 0.3519 0.095 Uiso 1 1 calc R . .
H13B H 0.1705 0.2078 0.4543 0.095 Uiso 1 1 calc R . .
C14 C 0.12205(17) 0.4014(2) 0.40172(17) 0.0601(6) Uani 1 1 d . . .
H14A H 0.1815 0.4371 0.4028 0.072 Uiso 1 1 calc R . .
H14B H 0.1129 0.4334 0.4544 0.072 Uiso 1 1 calc R . .
C15 C 0.05658(15) 0.8453(2) 0.15765(13) 0.0487(5) Uani 1 1 d . . .
C16 C 0.09772(18) 0.9758(3) 0.17208(16) 0.0619(6) Uani 1 1 d . . .
H16 H 0.1609 0.9852 0.2038 0.074 Uiso 1 1 calc R . .
C17 C 0.0434(2) 1.0930(3) 0.13857(19) 0.0734(7) Uani 1 1 d . . .
H17 H 0.0708 1.1815 0.1488 0.088 Uiso 1 1 calc R . .
C18 C -0.0499(2) 1.0823(3) 0.09062(16) 0.0715(8) Uani 1 1 d . . .
C19 C -0.0889(2) 0.9507(4) 0.07799(18) 0.0794(8) Uani 1 1 d . . .
H19 H -0.1522 0.9414 0.0464 0.095 Uiso 1 1 calc R . .
C20 C -0.03711(18) 0.8324(3) 0.11079(17) 0.0680(7) Uani 1 1 d . . .
H20 H -0.0651 0.7442 0.1014 0.082 Uiso 1 1 calc R . .
C21 C -0.1066(3) 1.2131(4) 0.0545(2) 0.1095(13) Uani 1 1 d . . .
H21A H -0.1452 1.2337 0.088 0.164 Uiso 1 1 calc R . .
H21B H -0.1451 1.1977 -0.0056 0.164 Uiso 1 1 calc R . .
H21C H -0.0657 1.2909 0.0581 0.164 Uiso 1 1 calc R . .
C22 C -0.0967(2) 0.8607(4) 0.3650(3) 0.1036(12) Uani 1 1 d . . .
C23 C -0.1913(2) 0.5156(4) 0.2547(2) 0.0966(11) Uani 1 1 d . . .
H23A H -0.2517 0.483 0.216 0.116 Uiso 1 1 calc R . .
H23B H -0.1882 0.6169 0.2494 0.116 Uiso 1 1 calc R . .
C24 C -0.17439(17) 0.4740(4) 0.34727(19) 0.0778(8) Uani 1 1 d . . .
H24A H -0.1931 0.5481 0.3783 0.093 Uiso 1 1 calc R . .
H24B H -0.2078 0.3885 0.3497 0.093 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4181(18) . ?
S1 O2 1.4239(19) . ?
S1 N2 1.6545(18) . ?
S1 C15 1.761(2) . ?
O3 C24 1.424(3) . ?
O3 C10 1.428(3) . ?
O4 C23 1.418(4) . ?
O4 C10 1.425(3) . ?
N1 C22 1.126(3) . ?
N1 C7 1.441(3) . ?
N2 C1 1.422(3) . ?
N2 C8 1.502(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.388(3) . ?
C2 C3 1.385(4) . ?
C2 H2 0.93 . ?
C3 C4 1.377(4) . ?
C3 H3 0.93 . ?
C4 C5 1.379(3) . ?
C4 H4 0.93 . ?
C5 C6 1.378(3) . ?
C5 H5 0.93 . ?
C6 C7 1.503(3) . ?
C7 C8 1.552(3) . ?
C7 H7 0.98 . ?
C8 C9 1.525(3) . ?
C8 H8 0.98 . ?
C9 C14 1.519(3) . ?
C9 C10 1.527(3) . ?
C9 H9 0.98 . ?
C10 C11 1.513(4) . ?
C11 C12 1.516(4) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.509(4) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.519(4) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 C16 1.375(3) . ?
C15 C20 1.377(3) . ?
C16 C17 1.384(4) . ?
C16 H16 0.93 . ?
C17 C18 1.372(4) . ?
C17 H17 0.93 . ?
C18 C19 1.372(4) . ?
C18 C21 1.514(4) . ?
C19 C20 1.373(4) . ?
C19 H19 0.93 . ?
C20 H20 0.93 . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C23 C24 1.494(4) . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
C24 H24A 0.97 . ?
C24 H24B 0.97 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.58(12) . . ?
O1 S1 N2 106.35(10) . . ?
O2 S1 N2 105.58(10) . . ?
O1 S1 C15 108.27(11) . . ?
O2 S1 C15 107.90(12) . . ?
N2 S1 C15 107.51(9) . . ?
C24 O3 C10 106.71(18) . . ?
C23 O4 C10 109.7(2) . . ?
C22 N1 C7 178.2(3) . . ?
C1 N2 C8 109.80(16) . . ?
C1 N2 S1 122.20(14) . . ?
C8 N2 S1 117.56(14) . . ?
C6 C1 C2 120.5(2) . . ?
C6 C1 N2 110.72(18) . . ?
C2 C1 N2 128.8(2) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2 121 . . ?
C1 C2 H2 121 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 120.9(2) . . ?
C5 C6 C7 128.87(19) . . ?
C1 C6 C7 110.23(18) . . ?
N1 C7 C6 111.47(17) . . ?
N1 C7 C8 110.93(17) . . ?
C6 C7 C8 104.96(16) . . ?
N1 C7 H7 109.8 . . ?
C6 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
N2 C8 C9 110.68(16) . . ?
N2 C8 C7 104.08(16) . . ?
C9 C8 C7 115.14(17) . . ?
N2 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
C14 C9 C8 114.18(18) . . ?
C14 C9 C10 111.65(18) . . ?
C8 C9 C10 112.58(18) . . ?
C14 C9 H9 105.9 . . ?
C8 C9 H9 105.9 . . ?
C10 C9 H9 105.9 . . ?
O4 C10 O3 105.55(19) . . ?
O4 C10 C11 109.8(2) . . ?
O3 C10 C11 110.81(19) . . ?
O4 C10 C9 109.86(18) . . ?
O3 C10 C9 109.64(17) . . ?
C11 C10 C9 111.0(2) . . ?
C10 C11 C12 112.0(2) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 112.4(2) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 110.8(2) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C9 111.5(2) . . ?
C13 C14 H14A 109.3 . . ?
C9 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C9 C14 H14B 109.3 . . ?
H14A C14 H14B 108 . . ?
C16 C15 C20 120.2(2) . . ?
C16 C15 S1 120.28(18) . . ?
C20 C15 S1 119.50(19) . . ?
C15 C16 C17 118.8(2) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 121.9(3) . . ?
C18 C17 H17 119 . . ?
C16 C17 H17 119 . . ?
C19 C18 C17 117.8(3) . . ?
C19 C18 C21 122.0(3) . . ?
C17 C18 C21 120.2(3) . . ?
C18 C19 C20 121.7(3) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C15 119.5(3) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C23 C24 104.1(2) . . ?
O4 C23 H23A 110.9 . . ?
C24 C23 H23A 110.9 . . ?
O4 C23 H23B 110.9 . . ?
C24 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?
O3 C24 C23 103.4(2) . . ?
O3 C24 H24A 111.1 . . ?
C23 C24 H24A 111.1 . . ?
O3 C24 H24B 111.1 . . ?
C23 C24 H24B 111.1 . . ?
H24A C24 H24B 109 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N2 C1 48.03(19) . . . . ?
O2 S1 N2 C1 177.24(16) . . . . ?
C15 S1 N2 C1 -67.76(18) . . . . ?
O1 S1 N2 C8 -170.71(15) . . . . ?
O2 S1 N2 C8 -41.50(18) . . . . ?
C15 S1 N2 C8 73.50(17) . . . . ?
C8 N2 C1 C6 0.5(2) . . . . ?
S1 N2 C1 C6 144.36(16) . . . . ?
C8 N2 C1 C2 178.1(2) . . . . ?
S1 N2 C1 C2 -38.0(3) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
N2 C1 C2 C3 -176.7(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 -179.3(2) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
N2 C1 C6 C5 176.65(19) . . . . ?
C2 C1 C6 C7 178.80(19) . . . . ?
N2 C1 C6 C7 -3.4(2) . . . . ?
C22 N1 C7 C6 -121(10) . . . . ?
C22 N1 C7 C8 122(10) . . . . ?
C5 C6 C7 N1 64.5(3) . . . . ?
C1 C6 C7 N1 -115.5(2) . . . . ?
C5 C6 C7 C8 -175.3(2) . . . . ?
C1 C6 C7 C8 4.7(2) . . . . ?
C1 N2 C8 C9 -121.85(18) . . . . ?
S1 N2 C8 C9 92.39(18) . . . . ?
C1 N2 C8 C7 2.4(2) . . . . ?
S1 N2 C8 C7 -143.34(14) . . . . ?
N1 C7 C8 N2 116.37(19) . . . . ?
C6 C7 C8 N2 -4.1(2) . . . . ?
N1 C7 C8 C9 -122.3(2) . . . . ?
C6 C7 C8 C9 117.19(19) . . . . ?
N2 C8 C9 C14 65.8(2) . . . . ?
C7 C8 C9 C14 -51.9(2) . . . . ?
N2 C8 C9 C10 -165.56(16) . . . . ?
C7 C8 C9 C10 76.8(2) . . . . ?
C23 O4 C10 O3 -6.5(3) . . . . ?
C23 O4 C10 C11 113.0(3) . . . . ?
C23 O4 C10 C9 -124.6(2) . . . . ?
C24 O3 C10 O4 25.0(2) . . . . ?
C24 O3 C10 C11 -93.9(2) . . . . ?
C24 O3 C10 C9 143.3(2) . . . . ?
C14 C9 C10 O4 -175.86(19) . . . . ?
C8 C9 C10 O4 54.2(2) . . . . ?
C14 C9 C10 O3 68.6(2) . . . . ?
C8 C9 C10 O3 -61.4(2) . . . . ?
C14 C9 C10 C11 -54.2(3) . . . . ?
C8 C9 C10 C11 175.85(19) . . . . ?
O4 C10 C11 C12 175.0(2) . . . . ?
O3 C10 C11 C12 -68.8(3) . . . . ?
C9 C10 C11 C12 53.3(3) . . . . ?
C10 C11 C12 C13 -54.3(3) . . . . ?
C11 C12 C13 C14 54.6(4) . . . . ?
C12 C13 C14 C9 -55.2(3) . . . . ?
C8 C9 C14 C13 -175.4(2) . . . . ?
C10 C9 C14 C13 55.4(3) . . . . ?
O1 S1 C15 C16 -29.2(2) . . . . ?
O2 S1 C15 C16 -161.27(19) . . . . ?
N2 S1 C15 C16 85.3(2) . . . . ?
O1 S1 C15 C20 150.23(19) . . . . ?
O2 S1 C15 C20 18.2(2) . . . . ?
N2 S1 C15 C20 -95.3(2) . . . . ?
C20 C15 C16 C17 -0.1(4) . . . . ?
S1 C15 C16 C17 179.3(2) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C16 C17 C18 C21 -179.5(3) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C21 C18 C19 C20 179.9(3) . . . . ?
C18 C19 C20 C15 0.0(4) . . . . ?
C16 C15 C20 C19 0.5(4) . . . . ?
S1 C15 C20 C19 -178.9(2) . . . . ?
C10 O4 C23 C24 -13.4(3) . . . . ?
C10 O3 C24 C23 -32.8(3) . . . . ?
O4 C23 C24 O3 28.1(3) . . . . ?

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_sda43
_database_code_depnum_ccdc_archive 'CCDC 1428310'
_audit_update_record             
;
2015-09-29 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


_diffrn_measurement_device_type  'SMART APEX I'
#Added by publCIF


_publcif_datablock.id            {80c145f9-d76a-476f-9181-44b41c27695f}

_audit_creation_date             2011-09-20T16:29:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O6'
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.42
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4217(9)
_cell_length_b                   10.6970(9)
_cell_length_c                   11.3310(10)
_cell_angle_alpha                68.2230(10)
_cell_angle_beta                 65.3910(10)
_cell_angle_gamma                66.0660(10)
_cell_volume                     1018.20(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_number            8203
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_full        26.4
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_reflns_number_total             4113
_reflns_number_gt                3411
_reflns_threshold_expression     >2sigma(I)

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

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0571P)²+0.2474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4113
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038

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

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

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8790(2) 0.20817(15) 0.31208(17) 0.0922(6) Uani 1 1 d . . .
O2 O 0.81870(14) 0.35698(14) 0.13988(12) 0.0576(3) Uani 1 1 d . . .
O3 O 0.53050(17) 0.79112(15) 0.86229(15) 0.0706(4) Uani 1 1 d . . .
O4 O 0.98057(12) 0.56190(13) 0.10442(12) 0.0523(3) Uani 1 1 d . . .
H4A H 1.0311 0.5954 0.0303 0.079 Uiso 1 1 calc R . .
O5 O 0.40080(13) 0.89304(13) 0.22582(13) 0.0546(3) Uani 1 1 d . . .
O6 O 0.41646(19) 0.9115(2) 0.40918(17) 0.0900(5) Uani 1 1 d . . .
N1 N 0.67339(17) 0.58758(16) 0.70848(15) 0.0543(4) Uani 1 1 d . . .
N2 N 0.82840(16) 0.32960(16) 0.25351(15) 0.0517(4) Uani 1 1 d . . .
C22 C 0.3448(2) 0.9375(2) 0.3398(2) 0.0582(5) Uani 1 1 d . . .
C1 C 0.9822(2) 0.2988(2) 0.62820(19) 0.0599(5) Uani 1 1 d . . .
H1 H 1.0251 0.35 0.5441 0.072 Uiso 1 1 calc R . .
C2 C 1.0671(2) 0.1706(2) 0.6851(2) 0.0737(6) Uani 1 1 d . . .
H2 H 1.1666 0.1362 0.6392 0.088 Uiso 1 1 calc R . .
C3 C 1.0051(3) 0.0947(2) 0.8085(2) 0.0699(6) Uani 1 1 d . . .
H3 H 1.0622 0.0084 0.8465 0.084 Uiso 1 1 calc R . .
C4 C 0.8592(3) 0.1454(2) 0.8760(2) 0.0655(5) Uani 1 1 d . . .
H4 H 0.8175 0.0935 0.9602 0.079 Uiso 1 1 calc R . .
C5 C 0.7731(2) 0.2730(2) 0.82043(17) 0.0535(4) Uani 1 1 d . . .
H5 H 0.6737 0.3065 0.8672 0.064 Uiso 1 1 calc R . .
C6 C 0.83431(18) 0.35151(17) 0.69509(15) 0.0434(4) Uani 1 1 d . . .
C7 C 0.74253(18) 0.48975(18) 0.63526(16) 0.0445(4) Uani 1 1 d . . .
C8 C 0.7388(2) 0.5955(2) 0.7966(2) 0.0589(5) Uani 1 1 d . . .
H8A H 0.8048 0.6534 0.7457 0.071 Uiso 1 1 calc R . .
H8B H 0.7964 0.5017 0.8321 0.071 Uiso 1 1 calc R . .
C9 C 0.6218(3) 0.6566(2) 0.9090(2) 0.0687(6) Uani 1 1 d . . .
H9A H 0.5616 0.5938 0.9646 0.082 Uiso 1 1 calc R . .
H9B H 0.6678 0.6645 0.9638 0.082 Uiso 1 1 calc R . .
C10 C 0.4612(2) 0.7805(2) 0.7840(2) 0.0721(6) Uani 1 1 d . . .
H10A H 0.3984 0.8732 0.7531 0.087 Uiso 1 1 calc R . .
H10B H 0.3986 0.7199 0.8395 0.087 Uiso 1 1 calc R . .
C11 C 0.5689(2) 0.7231(2) 0.6658(2) 0.0679(6) Uani 1 1 d . . .
H11A H 0.516 0.7101 0.6203 0.081 Uiso 1 1 calc R . .
H11B H 0.6226 0.7896 0.6035 0.081 Uiso 1 1 calc R . .
C12 C 0.72838(19) 0.51626(18) 0.51217(16) 0.0471(4) Uani 1 1 d . . .
H12 H 0.6831 0.6086 0.4733 0.056 Uiso 1 1 calc R . .
C13 C 0.77745(18) 0.41377(17) 0.44125(16) 0.0437(4) Uani 1 1 d . . .
H13 H 0.8129 0.3199 0.4838 0.052 Uiso 1 1 calc R . .
C14 C 0.77640(17) 0.44297(17) 0.31456(15) 0.0419(4) Uani 1 1 d . . .
C15 C 0.73160(17) 0.58738(16) 0.23152(14) 0.0391(3) Uani 1 1 d . . .
C16 C 0.83841(17) 0.64582(17) 0.12754(15) 0.0403(4) Uani 1 1 d . . .
C17 C 0.79783(19) 0.78400(18) 0.05516(17) 0.0485(4) Uani 1 1 d . . .
H17 H 0.8689 0.8214 -0.0163 0.058 Uiso 1 1 calc R . .
C18 C 0.6523(2) 0.86644(18) 0.08864(18) 0.0495(4) Uani 1 1 d . . .
H18 H 0.6251 0.9595 0.0405 0.059 Uiso 1 1 calc R . .
C19 C 0.54855(18) 0.80984(18) 0.19338(17) 0.0446(4) Uani 1 1 d . . .
C20 C 0.58597(18) 0.67098(17) 0.26373(16) 0.0433(4) Uani 1 1 d . . .
H20 H 0.5134 0.6336 0.3328 0.052 Uiso 1 1 calc R . .
C21 C 0.1863(2) 1.0197(2) 0.3617(3) 0.0788(7) Uani 1 1 d . . .
H21A H 0.1478 1.0509 0.4424 0.118 Uiso 1 1 calc R . .
H21B H 0.1321 0.9612 0.3695 0.118 Uiso 1 1 calc R . .
H21C H 0.1766 1.1 0.2874 0.118 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.2256(19) . ?
O2 N2 1.2482(18) . ?
O3 C10 1.412(2) . ?
O3 C9 1.414(2) . ?
O4 C16 1.3571(18) . ?
O4 H4A 0.82 . ?
O5 C22 1.356(2) . ?
O5 C19 1.3991(19) . ?
O6 C22 1.187(2) . ?
N1 C7 1.355(2) . ?
N1 C8 1.465(2) . ?
N1 C11 1.469(2) . ?
N2 C14 1.421(2) . ?
C22 C21 1.485(3) . ?
C1 C6 1.381(2) . ?
C1 C2 1.383(3) . ?
C1 H1 0.93 . ?
C2 C3 1.365(3) . ?
C2 H2 0.93 . ?
C3 C4 1.364(3) . ?
C3 H3 0.93 . ?
C4 C5 1.380(3) . ?
C4 H4 0.93 . ?
C5 C6 1.387(2) . ?
C5 H5 0.93 . ?
C6 C7 1.487(2) . ?
C7 C12 1.375(2) . ?
C8 C9 1.488(3) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 C11 1.494(3) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.402(2) . ?
C12 H12 0.93 . ?
C13 C14 1.355(2) . ?
C13 H13 0.93 . ?
C14 C15 1.480(2) . ?
C15 C20 1.384(2) . ?
C15 C16 1.394(2) . ?
C16 C17 1.385(2) . ?
C17 C18 1.380(2) . ?
C17 H17 0.93 . ?
C18 C19 1.369(2) . ?
C18 H18 0.93 . ?
C19 C20 1.380(2) . ?
C20 H20 0.93 . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?

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
C10 O3 C9 109.76(15) . . ?
C16 O4 H4A 109.5 . . ?
C22 O5 C19 117.04(13) . . ?
C7 N1 C8 121.59(15) . . ?
C7 N1 C11 121.53(15) . . ?
C8 N1 C11 112.06(15) . . ?
O1 N2 O2 121.12(15) . . ?
O1 N2 C14 120.70(15) . . ?
O2 N2 C14 118.16(14) . . ?
O6 C22 O5 122.83(18) . . ?
O6 C22 C21 127.1(2) . . ?
O5 C22 C21 110.08(18) . . ?
C6 C1 C2 120.64(18) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.95(19) . . ?
C4 C3 H3 120 . . ?
C2 C3 H3 120 . . ?
C3 C4 C5 120.59(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.21(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.49(16) . . ?
C1 C6 C7 121.02(15) . . ?
C5 C6 C7 120.49(16) . . ?
N1 C7 C12 121.94(15) . . ?
N1 C7 C6 116.56(14) . . ?
C12 C7 C6 121.50(15) . . ?
N1 C8 C9 110.73(16) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O3 C9 C8 111.71(17) . . ?
O3 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
O3 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
O3 C10 C11 112.98(18) . . ?
O3 C10 H10A 109 . . ?
C11 C10 H10A 109 . . ?
O3 C10 H10B 109 . . ?
C11 C10 H10B 109 . . ?
H10A C10 H10B 107.8 . . ?
N1 C11 C10 110.31(17) . . ?
N1 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C7 C12 C13 124.56(16) . . ?
C7 C12 H12 117.7 . . ?
C13 C12 H12 117.7 . . ?
C14 C13 C12 124.06(15) . . ?
C14 C13 H13 118 . . ?
C12 C13 H13 118 . . ?
C13 C14 N2 118.78(15) . . ?
C13 C14 C15 124.08(14) . . ?
N2 C14 C15 117.06(13) . . ?
C20 C15 C16 118.94(14) . . ?
C20 C15 C14 120.72(14) . . ?
C16 C15 C14 120.04(14) . . ?
O4 C16 C17 123.10(15) . . ?
O4 C16 C15 116.71(14) . . ?
C17 C16 C15 120.18(15) . . ?
C18 C17 C16 120.27(15) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.30(16) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.26(16) . . ?
C18 C19 O5 119.16(15) . . ?
C20 C19 O5 119.53(15) . . ?
C19 C20 C15 119.97(15) . . ?
C19 C20 H20 120 . . ?
C15 C20 H20 120 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C19 O5 C22 O6 1.8(3) . . . . ?
C19 O5 C22 C21 -177.97(16) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 179.43(19) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -179.37(17) . . . . ?
C8 N1 C7 C12 -147.91(18) . . . . ?
C11 N1 C7 C12 5.5(3) . . . . ?
C8 N1 C7 C6 32.4(2) . . . . ?
C11 N1 C7 C6 -174.21(17) . . . . ?
C1 C6 C7 N1 -123.27(19) . . . . ?
C5 C6 C7 N1 56.2(2) . . . . ?
C1 C6 C7 C12 57.0(2) . . . . ?
C5 C6 C7 C12 -123.56(19) . . . . ?
C7 N1 C8 C9 -152.80(18) . . . . ?
C11 N1 C8 C9 51.5(2) . . . . ?
C10 O3 C9 C8 59.9(2) . . . . ?
N1 C8 C9 O3 -56.6(2) . . . . ?
C9 O3 C10 C11 -59.1(3) . . . . ?
C7 N1 C11 C10 154.40(19) . . . . ?
C8 N1 C11 C10 -49.9(3) . . . . ?
O3 C10 C11 N1 54.2(3) . . . . ?
N1 C7 C12 C13 -169.59(17) . . . . ?
C6 C7 C12 C13 10.1(3) . . . . ?
C7 C12 C13 C14 -173.12(17) . . . . ?
C12 C13 C14 N2 -179.66(15) . . . . ?
C12 C13 C14 C15 3.7(3) . . . . ?
O1 N2 C14 C13 -3.0(3) . . . . ?
O2 N2 C14 C13 175.80(15) . . . . ?
O1 N2 C14 C15 173.81(18) . . . . ?
O2 N2 C14 C15 -7.4(2) . . . . ?
C13 C14 C15 C20 -68.5(2) . . . . ?
N2 C14 C15 C20 114.86(17) . . . . ?
C13 C14 C15 C16 105.12(19) . . . . ?
N2 C14 C15 C16 -71.5(2) . . . . ?
C20 C15 C16 O4 176.63(14) . . . . ?
C14 C15 C16 O4 2.9(2) . . . . ?
C20 C15 C16 C17 -2.2(2) . . . . ?
C14 C15 C16 C17 -175.88(15) . . . . ?
O4 C16 C17 C18 -176.26(15) . . . . ?
C15 C16 C17 C18 2.4(2) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C20 -1.8(3) . . . . ?
C17 C18 C19 O5 -179.07(15) . . . . ?
C22 O5 C19 C18 -108.11(19) . . . . ?
C22 O5 C19 C20 74.5(2) . . . . ?
C18 C19 C20 C15 2.0(2) . . . . ?
O5 C19 C20 C15 179.35(14) . . . . ?
C16 C15 C20 C19 -0.1(2) . . . . ?
C14 C15 C20 C19 173.62(14) . . . . ?

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
O4 H4A O2 0.82 1.96 2.7676(17) 169.2 2_765

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
