# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_new



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C22 H19 N O4'

_chemical_formula_sum            
'C22 H19 N O4'

_chemical_formula_weight         361.38



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'



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1

_symmetry_space_group_name_Hall  ' -P 1'

loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   8.2827(3)

_cell_length_b                   8.3250(3)

_cell_length_c                   15.0662(7)

_cell_angle_alpha                98.787(2)

_cell_angle_beta                 93.426(2)

_cell_angle_gamma                114.758(2)

_cell_volume                     923.40(6)

_cell_formula_units_Z            2

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    7368

_cell_measurement_theta_min      2.73

_cell_measurement_theta_max      28.49



_exptl_crystal_description       Block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.45

_exptl_crystal_size_mid          0.35

_exptl_crystal_size_min          0.20

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.300

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             380

_exptl_absorpt_coefficient_mu    0.090

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9607

_exptl_absorpt_correction_T_max  0.9823

_exptl_absorpt_process_details   'SADABS (Bruker,2004)'



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            12745

_diffrn_reflns_av_R_equivalents  0.0203

_diffrn_reflns_av_sigmaI/netI    0.0219

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       7

_diffrn_reflns_limit_l_min       -20

_diffrn_reflns_limit_l_max       19

_diffrn_reflns_theta_min         1.38

_diffrn_reflns_theta_max         28.59

_reflns_number_total             4594

_reflns_number_gt                3712

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       APEXII,Bruker,2004
_computing_cell_refinement       APEXII,Bruker,2004
_computing_data_reduction        SAINT,Bruker,2004
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'





_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)+(0.0440P)²+0.2825P] 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_extinction_coef       ?

_refine_ls_number_reflns         4594

_refine_ls_number_parameters     245

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0546

_refine_ls_R_factor_gt           0.0439

_refine_ls_wR_factor_ref         0.1119

_refine_ls_wR_factor_gt          0.1041

_refine_ls_goodness_of_fit_ref   0.983

_refine_ls_restrained_S_all      0.983

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group














































O1 O 0.58124(13) 0.69248(12) 0.28694(6) 0.0424(2) Uani 1 1 d . . .
O4 O 0.73007(13) 0.91781(13) 0.53900(6) 0.0490(2) Uani 1 1 d . . .
O2 O 0.86032(14) 0.44697(14) 0.16104(6) 0.0505(2) Uani 1 1 d . . .
O3 O 0.46475(14) 0.68162(14) 0.48821(7) 0.0570(3) Uani 1 1 d . . .
C20 C 0.62244(17) 0.75929(17) 0.48578(8) 0.0388(3) Uani 1 1 d . . .
C7 C 0.62104(16) 0.57522(16) 0.33572(8) 0.0361(2) Uani 1 1 d . . .
H7 H 0.5093 0.4782 0.3459 0.043 Uiso 1 1 calc R . .
C6 C 0.72783(16) 0.49670(16) 0.28270(8) 0.0360(2) Uani 1 1 d . . .
C5 C 0.82433(16) 0.39473(16) 0.30466(8) 0.0375(3) Uani 1 1 d . . .
C8 C 0.51820(18) 0.61936(17) 0.19277(8) 0.0414(3) Uani 1 1 d . . .
H8 H 0.4204 0.4980 0.1859 0.050 Uiso 1 1 calc R . .
C19 C 0.72779(17) 0.69125(18) 0.42566(8) 0.0403(3) Uani 1 1 d . . .
H19A H 0.7720 0.6216 0.4574 0.048 Uiso 1 1 calc R . .
H19B H 0.8311 0.7937 0.4142 0.048 Uiso 1 1 calc R . .
C15 C 0.31843(19) 0.95957(18) 0.08626(9) 0.0435(3) Uani 1 1 d . . .
C12 C 0.44707(18) 0.73894(17) 0.15565(8) 0.0407(3) Uani 1 1 d . . .
C18 C 0.2551(2) 1.0791(2) 0.05287(10) 0.0509(3) Uani 1 1 d . . .
C10 C 0.75242(18) 0.52107(17) 0.19775(9) 0.0415(3) Uani 1 1 d . . .
C4 C 0.84884(18) 0.31885(18) 0.37790(9) 0.0450(3) Uani 1 1 d . . .
H4 H 0.7978 0.3323 0.4302 0.054 Uiso 1 1 calc R . .
C9 C 0.6705(2) 0.6078(2) 0.14343(9) 0.0504(3) Uani 1 1 d . . .
H9A H 0.6240 0.5365 0.0826 0.060 Uiso 1 1 calc R . .
H9B H 0.7584 0.7274 0.1394 0.060 Uiso 1 1 calc R . .
C11 C 0.90333(18) 0.36972(18) 0.22791(9) 0.0440(3) Uani 1 1 d . . .
C21 C 0.6495(2) 0.9937(2) 0.60615(10) 0.0541(4) Uani 1 1 d . . .
H21A H 0.6127 0.9194 0.6516 0.065 Uiso 1 1 calc R . .
H21B H 0.5448 0.9999 0.5775 0.065 Uiso 1 1 calc R . .
C17 C 0.2924(2) 0.66562(19) 0.09435(10) 0.0529(4) Uani 1 1 d . . .
H17 H 0.2310 0.5410 0.0762 0.064 Uiso 1 1 calc R . .
C16 C 0.2271(2) 0.7742(2) 0.05945(11) 0.0573(4) Uani 1 1 d . . .
H16 H 0.1225 0.7230 0.0182 0.069 Uiso 1 1 calc R . .
C3 C 0.9510(2) 0.2231(2) 0.37049(11) 0.0548(4) Uani 1 1 d . . .
H3 H 0.9680 0.1711 0.4185 0.066 Uiso 1 1 calc R . .
C13 C 0.5374(2) 0.9241(2) 0.18192(12) 0.0593(4) Uani 1 1 d . . .
H13 H 0.6418 0.9752 0.2234 0.071 Uiso 1 1 calc R . .
N1 N 0.2093(2) 1.1792(2) 0.02992(10) 0.0708(4) Uani 1 1 d . . .
C1 C 1.0064(2) 0.2753(2) 0.21971(11) 0.0581(4) Uani 1 1 d . . .
H1 H 1.0577 0.2615 0.1676 0.070 Uiso 1 1 calc R . .
C14 C 0.4741(2) 1.0336(2) 0.14714(12) 0.0604(4) Uani 1 1 d . . .
H14 H 0.5366 1.1583 0.1648 0.072 Uiso 1 1 calc R . .
C2 C 1.0288(2) 0.2028(2) 0.29316(12) 0.0618(4) Uani 1 1 d . . .
H2 H 1.0977 0.1386 0.2908 0.074 Uiso 1 1 calc R . .
C22 C 0.7879(2) 1.1780(2) 0.64881(13) 0.0721(5) Uani 1 1 d . . .
H22A H 0.8865 1.1694 0.6811 0.108 Uiso 1 1 calc R . .
H22B H 0.7362 1.2363 0.6903 0.108 Uiso 1 1 calc R . .
H22C H 0.8301 1.2472 0.6026 0.108 Uiso 1 1 calc 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

















































O1 C8 1.4275(15) . ?
O1 C7 1.4358(14) . ?
O4 C20 1.3361(16) . ?
O4 C21 1.4515(15) . ?
O2 C11 1.3793(16) . ?
O2 C10 1.3791(15) . ?
O3 C20 1.1962(16) . ?
C20 C19 1.5015(16) . ?
C7 C6 1.5023(16) . ?
C7 C19 1.5140(17) . ?
C7 H7 0.9800 . ?
C6 C10 1.3403(17) . ?
C6 C5 1.4462(16) . ?
C5 C11 1.3927(18) . ?
C5 C4 1.3969(18) . ?
C8 C12 1.5076(17) . ?
C8 C9 1.5315(19) . ?
C8 H8 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C15 C14 1.380(2) . ?
C15 C16 1.383(2) . ?
C15 C18 1.4411(18) . ?
C12 C17 1.3777(19) . ?
C12 C13 1.3798(19) . ?
C18 N1 1.1381(18) . ?
C10 C9 1.4753(18) . ?
C4 C3 1.3833(19) . ?
C4 H4 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C1 1.3808(19) . ?
C21 C22 1.489(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C17 C16 1.381(2) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C3 C2 1.386(2) . ?
C3 H3 0.9300 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9300 . ?
C1 C2 1.377(2) . ?
C1 H1 0.9300 . ?
C14 H14 0.9300 . ?
C2 H2 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?



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





















































































C8 O1 C7 114.27(9) . . ?
C20 O4 C21 116.99(10) . . ?
C11 O2 C10 104.90(9) . . ?
O3 C20 O4 123.95(11) . . ?
O3 C20 C19 125.35(12) . . ?
O4 C20 C19 110.67(11) . . ?
O1 C7 C6 109.66(9) . . ?
O1 C7 C19 106.04(9) . . ?
C6 C7 C19 111.23(10) . . ?
O1 C7 H7 109.9 . . ?
C6 C7 H7 109.9 . . ?
C19 C7 H7 109.9 . . ?
C10 C6 C5 106.41(11) . . ?
C10 C6 C7 120.59(11) . . ?
C5 C6 C7 132.97(11) . . ?
C11 C5 C4 118.44(11) . . ?
C11 C5 C6 105.03(11) . . ?
C4 C5 C6 136.50(12) . . ?
O1 C8 C12 107.83(10) . . ?
O1 C8 C9 110.03(11) . . ?
C12 C8 C9 111.65(11) . . ?
O1 C8 H8 109.1 . . ?
C12 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C20 C19 C7 113.82(10) . . ?
C20 C19 H19A 108.8 . . ?
C7 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C7 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C14 C15 C16 119.57(13) . . ?
C14 C15 C18 118.55(13) . . ?
C16 C15 C18 121.88(13) . . ?
C17 C12 C13 118.98(12) . . ?
C17 C12 C8 120.69(12) . . ?
C13 C12 C8 120.33(12) . . ?
N1 C18 C15 176.93(17) . . ?
C6 C10 O2 112.69(11) . . ?
C6 C10 C9 126.52(11) . . ?
O2 C10 C9 120.72(11) . . ?
C3 C4 C5 118.20(13) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C10 C9 C8 106.02(10) . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C1 C11 O2 125.00(13) . . ?
C1 C11 C5 124.02(13) . . ?
O2 C11 C5 110.96(11) . . ?
O4 C21 C22 107.17(12) . . ?
O4 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 . . ?
O4 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 . . ?
H21A C21 H21B 108.5 . . ?
C16 C17 C12 121.06(13) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C17 C16 C15 119.56(13) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C4 C3 C2 121.55(14) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C14 C13 C12 120.44(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C2 C1 C11 116.20(14) . . ?
C2 C1 H1 121.9 . . ?
C11 C1 H1 121.9 . . ?
C13 C14 C15 120.39(13) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C1 C2 C3 121.59(14) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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


























































C21 O4 C20 O3 2.96(19) . . . . ?
C21 O4 C20 C19 -175.19(11) . . . . ?
C8 O1 C7 C6 45.83(13) . . . . ?
C8 O1 C7 C19 166.02(10) . . . . ?
O1 C7 C6 C10 -8.44(16) . . . . ?
C19 C7 C6 C10 -125.42(13) . . . . ?
O1 C7 C6 C5 169.37(12) . . . . ?
C19 C7 C6 C5 52.40(17) . . . . ?
C10 C6 C5 C11 1.07(14) . . . . ?
C7 C6 C5 C11 -176.97(13) . . . . ?
C10 C6 C5 C4 -176.81(15) . . . . ?
C7 C6 C5 C4 5.2(2) . . . . ?
C7 O1 C8 C12 168.56(10) . . . . ?
C7 O1 C8 C9 -69.45(13) . . . . ?
O3 C20 C19 C7 31.46(18) . . . . ?
O4 C20 C19 C7 -150.42(11) . . . . ?
O1 C7 C19 C20 66.41(13) . . . . ?
C6 C7 C19 C20 -174.43(10) . . . . ?
O1 C8 C12 C17 -139.69(13) . . . . ?
C9 C8 C12 C17 99.32(16) . . . . ?
O1 C8 C12 C13 41.04(17) . . . . ?
C9 C8 C12 C13 -79.95(17) . . . . ?
C14 C15 C18 N1 -24(3) . . . . ?
C16 C15 C18 N1 156(3) . . . . ?
C5 C6 C10 O2 -1.14(15) . . . . ?
C7 C6 C10 O2 177.19(11) . . . . ?
C5 C6 C10 C9 175.89(13) . . . . ?
C7 C6 C10 C9 -5.8(2) . . . . ?
C11 O2 C10 C6 0.73(15) . . . . ?
C11 O2 C10 C9 -176.49(12) . . . . ?
C11 C5 C4 C3 0.21(19) . . . . ?
C6 C5 C4 C3 177.88(14) . . . . ?
C6 C10 C9 C8 -14.22(19) . . . . ?
O2 C10 C9 C8 162.60(12) . . . . ?
O1 C8 C9 C10 48.61(14) . . . . ?
C12 C8 C9 C10 168.31(11) . . . . ?
C10 O2 C11 C1 178.22(14) . . . . ?
C10 O2 C11 C5 0.01(15) . . . . ?
C4 C5 C11 C1 -0.6(2) . . . . ?
C6 C5 C11 C1 -178.90(13) . . . . ?
C4 C5 C11 O2 177.67(11) . . . . ?
C6 C5 C11 O2 -0.66(14) . . . . ?
C20 O4 C21 C22 -173.21(13) . . . . ?
C13 C12 C17 C16 -0.2(2) . . . . ?
C8 C12 C17 C16 -179.46(14) . . . . ?
C12 C17 C16 C15 0.1(2) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C18 C15 C16 C17 -179.20(15) . . . . ?
C5 C4 C3 C2 0.4(2) . . . . ?
C17 C12 C13 C14 -0.2(3) . . . . ?
C8 C12 C13 C14 179.08(15) . . . . ?
O2 C11 C1 C2 -177.71(14) . . . . ?
C5 C11 C1 C2 0.3(2) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C16 C15 C14 C13 -0.7(3) . . . . ?
C18 C15 C14 C13 178.83(16) . . . . ?
C11 C1 C2 C3 0.4(2) . . . . ?
C4 C3 C2 C1 -0.7(3) . . . . ?



_diffrn_measured_fraction_theta_max 0.974

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.246

_refine_diff_density_min         -0.211

_refine_diff_density_rms         0.035

_database_code_depnum_ccdc_archive 'CCDC 971411'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_new



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C21 H26 O4'

_chemical_formula_sum            
'C21 H26 O4'

_chemical_formula_weight         342.42



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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/n

_symmetry_space_group_name_Hall  ' 	-P 2yn '

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                   13.6870(5)

_cell_length_b                   8.3874(3)

_cell_length_c                   17.8893(6)

_cell_angle_alpha                90.00

_cell_angle_beta                 112.109(2)

_cell_angle_gamma                90.00

_cell_volume                     1902.65(12)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    5088

_cell_measurement_theta_min      2.46

_cell_measurement_theta_max      28.21



_exptl_crystal_description       Square

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.195

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             736

_exptl_absorpt_coefficient_mu    0.082

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9799

_exptl_absorpt_correction_T_max  0.9879

_exptl_absorpt_process_details   'SADABS (Bruker,2004)'



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            13264

_diffrn_reflns_av_R_equivalents  0.0229

_diffrn_reflns_av_sigmaI/netI    0.0270

_diffrn_reflns_limit_h_min       -15

_diffrn_reflns_limit_h_max       16

_diffrn_reflns_limit_k_min       -8

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -23

_diffrn_reflns_limit_l_max       23

_diffrn_reflns_theta_min         1.61

_diffrn_reflns_theta_max         28.31

_reflns_number_total             4213

_reflns_number_gt                2891

_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       APEXII,Bruker,2004
_computing_cell_refinement       APEXII,Bruker,2004
_computing_data_reduction        SAINT,Bruker,2004
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'




_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)+(0.0959P)²+0.4753P] 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     SHELXL

_refine_ls_extinction_coef       0.019(2)

_refine_ls_extinction_expression 
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         4213

_refine_ls_number_parameters     228

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0895

_refine_ls_R_factor_gt           0.0580

_refine_ls_wR_factor_ref         0.1798

_refine_ls_wR_factor_gt          0.1486

_refine_ls_goodness_of_fit_ref   1.063

_refine_ls_restrained_S_all      1.063

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group



















































C1 C 0.77062(18) 0.9365(3) -0.07362(13) 0.0512(5) Uani 1 1 d . . .
H1 H 0.7509 0.8820 -0.1224 0.061 Uiso 1 1 calc R . .
C2 C 0.85463(19) 1.0395(3) -0.04883(14) 0.0567(6) Uani 1 1 d . . .
H2 H 0.8934 1.0548 -0.0812 0.068 Uiso 1 1 calc R . .
C3 C 0.88285(17) 1.1214(3) 0.02361(14) 0.0557(6) Uani 1 1 d . . .
H3 H 0.9405 1.1899 0.0389 0.067 Uiso 1 1 calc R . .
C4 C 0.82740(16) 1.1036(2) 0.07365(12) 0.0472(5) Uani 1 1 d . . .
H4 H 0.8465 1.1603 0.1217 0.057 Uiso 1 1 calc R . .
C5 C 0.74230(14) 0.9988(2) 0.05039(10) 0.0372(4) Uani 1 1 d . . .
C6 C 0.66835(14) 0.9401(2) 0.08416(10) 0.0358(4) Uani 1 1 d . . .
C7 C 0.65572(14) 0.9675(2) 0.16287(10) 0.0371(4) Uani 1 1 d . . .
H7 H 0.6119 1.0621 0.1584 0.045 Uiso 1 1 calc R . .
C8 C 0.50621(13) 0.7930(2) 0.11647(9) 0.0351(4) Uani 1 1 d . . .
H8 H 0.4636 0.8903 0.1015 0.042 Uiso 1 1 calc R . .
C9 C 0.52438(15) 0.7320(2) 0.04183(10) 0.0407(4) Uani 1 1 d . . .
H9A H 0.5468 0.6215 0.0492 0.049 Uiso 1 1 calc R . .
H9B H 0.4597 0.7394 -0.0056 0.049 Uiso 1 1 calc R . .
C10 C 0.60722(14) 0.8330(2) 0.03182(9) 0.0367(4) Uani 1 1 d . . .
C11 C 0.71683(15) 0.9176(2) -0.02271(11) 0.0406(4) Uani 1 1 d . . .
C12 C 0.75897(16) 0.9867(3) 0.23400(11) 0.0465(5) Uani 1 1 d . . .
H12A H 0.8064 0.9016 0.2329 0.056 Uiso 1 1 calc R . .
H12B H 0.7911 1.0870 0.2288 0.056 Uiso 1 1 calc R . .
C13 C 0.74604(16) 0.9835(3) 0.31410(11) 0.0475(5) Uani 1 1 d . . .
C14 C 0.6473(2) 1.0814(3) 0.38806(15) 0.0702(7) Uani 1 1 d . . .
H14A H 0.7048 1.1332 0.4308 0.084 Uiso 1 1 calc R . .
H14B H 0.6405 0.9734 0.4050 0.084 Uiso 1 1 calc R . .
C15 C 0.5480(3) 1.1700(5) 0.3715(2) 0.1130(12) Uani 1 1 d . . .
H15A H 0.5542 1.2748 0.3521 0.170 Uiso 1 1 calc R . .
H15B H 0.5344 1.1786 0.4202 0.170 Uiso 1 1 calc R . .
H15C H 0.4909 1.1143 0.3314 0.170 Uiso 1 1 calc R . .
C16 C 0.45102(14) 0.6755(2) 0.15240(10) 0.0399(4) Uani 1 1 d . . .
H16 H 0.4982 0.5842 0.1731 0.048 Uiso 1 1 calc R . .
C17 C 0.43291(17) 0.7523(3) 0.22377(11) 0.0517(5) Uani 1 1 d . . .
H17A H 0.5002 0.7841 0.2641 0.062 Uiso 1 1 calc R . .
H17B H 0.3902 0.8474 0.2054 0.062 Uiso 1 1 calc R . .
C18 C 0.3780(2) 0.6388(4) 0.26185(13) 0.0704(7) Uani 1 1 d . . .
H18A H 0.4240 0.5491 0.2856 0.085 Uiso 1 1 calc R . .
H18B H 0.3641 0.6936 0.3046 0.085 Uiso 1 1 calc R . .
C19 C 0.2757(2) 0.5786(4) 0.20022(16) 0.0767(8) Uani 1 1 d . . .
H19A H 0.2268 0.6668 0.1807 0.092 Uiso 1 1 calc R . .
H19B H 0.2446 0.5018 0.2252 0.092 Uiso 1 1 calc R . .
C20 C 0.2936(2) 0.5010(3) 0.12996(16) 0.0714(7) Uani 1 1 d . . .
H20A H 0.2263 0.4690 0.0897 0.086 Uiso 1 1 calc R . .
H20B H 0.3361 0.4058 0.1487 0.086 Uiso 1 1 calc R . .
C21 C 0.34895(17) 0.6134(3) 0.09136(12) 0.0534(5) Uani 1 1 d . . .
H21A H 0.3631 0.5573 0.0491 0.064 Uiso 1 1 calc R . .
H21B H 0.3028 0.7025 0.0668 0.064 Uiso 1 1 calc R . .
O1 O 0.63295(10) 0.81651(16) -0.03555(7) 0.0430(4) Uani 1 1 d . . .
O2 O 0.60469(9) 0.83125(15) 0.17971(6) 0.0379(3) Uani 1 1 d . . .
O3 O 0.79834(14) 0.9055(2) 0.37011(9) 0.0774(6) Uani 1 1 d . . .
O4 O 0.66827(12) 1.07883(19) 0.31413(8) 0.0575(4) Uani 1 1 d . . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag






















































C1 C2 1.372(3) . ?
C1 C11 1.379(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9300 . ?
C5 C11 1.397(2) . ?
C5 C6 1.446(2) . ?
C6 C10 1.339(2) . ?
C6 C7 1.500(2) . ?
C7 O2 1.429(2) . ?
C7 C12 1.513(3) . ?
C7 H7 0.9800 . ?
C8 O2 1.432(2) . ?
C8 C16 1.523(2) . ?
C8 C9 1.535(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.479(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O1 1.3838(19) . ?
C11 O1 1.375(2) . ?
C12 C13 1.509(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.185(2) . ?
C13 O4 1.331(3) . ?
C14 O4 1.455(2) . ?
C14 C15 1.478(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.506(3) . ?
C16 C17 1.531(2) . ?
C16 H16 0.9800 . ?
C17 C18 1.523(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.506(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.515(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.528(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?



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






































































































C2 C1 C11 116.73(19) . . ?
C2 C1 H1 121.6 . . ?
C11 C1 H1 121.6 . . ?
C1 C2 C3 121.24(19) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.43(19) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C11 118.25(17) . . ?
C4 C5 C6 136.77(17) . . ?
C11 C5 C6 104.93(16) . . ?
C10 C6 C5 106.71(15) . . ?
C10 C6 C7 119.79(15) . . ?
C5 C6 C7 133.32(16) . . ?
O2 C7 C6 108.27(14) . . ?
O2 C7 C12 106.49(14) . . ?
C6 C7 C12 113.88(15) . . ?
O2 C7 H7 109.4 . . ?
C6 C7 H7 109.4 . . ?
C12 C7 H7 109.4 . . ?
O2 C8 C16 106.28(13) . . ?
O2 C8 C9 110.44(13) . . ?
C16 C8 C9 114.83(15) . . ?
O2 C8 H8 108.4 . . ?
C16 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
C10 C9 C8 107.28(14) . . ?
C10 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C6 C10 O1 112.28(15) . . ?
C6 C10 C9 127.22(15) . . ?
O1 C10 C9 120.41(14) . . ?
O1 C11 C1 125.46(18) . . ?
O1 C11 C5 110.81(15) . . ?
C1 C11 C5 123.72(19) . . ?
C13 C12 C7 113.00(16) . . ?
C13 C12 H12A 109.0 . . ?
C7 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C7 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O3 C13 O4 124.0(2) . . ?
O3 C13 C12 124.3(2) . . ?
O4 C13 C12 111.68(17) . . ?
O4 C14 C15 107.8(2) . . ?
O4 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O4 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C8 112.93(15) . . ?
C21 C16 C17 110.68(15) . . ?
C8 C16 C17 109.96(16) . . ?
C21 C16 H16 107.7 . . ?
C8 C16 H16 107.7 . . ?
C17 C16 H16 107.7 . . ?
C18 C17 C16 111.83(19) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 111.17(19) . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 C20 110.8(2) . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 C21 111.8(2) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C16 C21 C20 111.59(17) . . ?
C16 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C16 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C11 O1 C10 105.25(13) . . ?
C7 O2 C8 113.70(12) . . ?
C13 O4 C14 116.14(17) . . ?



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






















































C11 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C11 -0.4(3) . . . . ?
C3 C4 C5 C6 176.6(2) . . . . ?
C4 C5 C6 C10 -177.0(2) . . . . ?
C11 C5 C6 C10 0.21(19) . . . . ?
C4 C5 C6 C7 -2.1(4) . . . . ?
C11 C5 C6 C7 175.17(18) . . . . ?
C10 C6 C7 O2 20.7(2) . . . . ?
C5 C6 C7 O2 -153.73(18) . . . . ?
C10 C6 C7 C12 138.94(18) . . . . ?
C5 C6 C7 C12 -35.5(3) . . . . ?
O2 C8 C9 C10 -41.24(19) . . . . ?
C16 C8 C9 C10 -161.38(15) . . . . ?
C5 C6 C10 O1 -1.0(2) . . . . ?
C7 C6 C10 O1 -176.77(14) . . . . ?
C5 C6 C10 C9 175.59(17) . . . . ?
C7 C6 C10 C9 -0.2(3) . . . . ?
C8 C9 C10 C6 10.2(3) . . . . ?
C8 C9 C10 O1 -173.44(15) . . . . ?
C2 C1 C11 O1 -177.86(18) . . . . ?
C2 C1 C11 C5 1.1(3) . . . . ?
C4 C5 C11 O1 178.49(16) . . . . ?
C6 C5 C11 O1 0.64(19) . . . . ?
C4 C5 C11 C1 -0.6(3) . . . . ?
C6 C5 C11 C1 -178.50(18) . . . . ?
O2 C7 C12 C13 -50.1(2) . . . . ?
C6 C7 C12 C13 -169.34(16) . . . . ?
C7 C12 C13 O3 131.9(2) . . . . ?
C7 C12 C13 O4 -47.9(2) . . . . ?
O2 C8 C16 C21 -175.68(15) . . . . ?
C9 C8 C16 C21 -53.3(2) . . . . ?
O2 C8 C16 C17 60.16(19) . . . . ?
C9 C8 C16 C17 -177.42(15) . . . . ?
C21 C16 C17 C18 54.7(2) . . . . ?
C8 C16 C17 C18 -179.88(18) . . . . ?
C16 C17 C18 C19 -55.7(3) . . . . ?
C17 C18 C19 C20 55.7(3) . . . . ?
C18 C19 C20 C21 -55.6(3) . . . . ?
C8 C16 C21 C20 -177.83(18) . . . . ?
C17 C16 C21 C20 -54.1(3) . . . . ?
C19 C20 C21 C16 55.3(3) . . . . ?
C1 C11 O1 C10 177.91(18) . . . . ?
C5 C11 O1 C10 -1.20(19) . . . . ?
C6 C10 O1 C11 1.37(19) . . . . ?
C9 C10 O1 C11 -175.48(16) . . . . ?
C6 C7 O2 C8 -55.28(18) . . . . ?
C12 C7 O2 C8 -178.13(14) . . . . ?
C16 C8 O2 C7 -165.98(14) . . . . ?
C9 C8 O2 C7 68.86(18) . . . . ?
O3 C13 O4 C14 -1.4(3) . . . . ?
C12 C13 O4 C14 178.42(17) . . . . ?
C15 C14 O4 C13 -170.2(2) . . . . ?



_diffrn_measured_fraction_theta_max 0.890

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.934

_refine_diff_density_max         0.438

_refine_diff_density_min         -0.337

_refine_diff_density_rms         0.133

_vrf_PLAT029_new                 
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.934      
RESPONSE: Even though crystal data was collected up to 0.73 \%A 
resolution, the crystal (the largest available) still 
diffracted quite weakly at high angle. On repeated recrystallisation
we could get only small sized crystals.

;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 971412'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_new



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C29 H26 N2 O5 S'

_chemical_formula_sum            
'C29 H26 N2 O5 S'

_chemical_formula_weight         514.58



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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1

_symmetry_space_group_name_Hall  ' -P 1'

loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   8.1294(4)

_cell_length_b                   8.2212(4)

_cell_length_c                   19.5982(10)

_cell_angle_alpha                87.310(2)

_cell_angle_beta                 87.214(2)

_cell_angle_gamma                82.233(2)

_cell_volume                     1295.19(11)

_cell_formula_units_Z            2

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    6617

_cell_measurement_theta_min      0.00

_cell_measurement_theta_max      0.00



_exptl_crystal_description       Block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.45

_exptl_crystal_size_mid          0.35

_exptl_crystal_size_min          0.12

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.319

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             540

_exptl_absorpt_coefficient_mu    0.167

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9285

_exptl_absorpt_correction_T_max  0.9802

_exptl_absorpt_process_details   ' SADABS (Bruker,2004)'



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            16654

_diffrn_reflns_av_R_equivalents  0.0220

_diffrn_reflns_av_sigmaI/netI    0.0293

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -10

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -26

_diffrn_reflns_limit_l_max       26

_diffrn_reflns_theta_min         2.08

_diffrn_reflns_theta_max         28.24

_reflns_number_total             6020

_reflns_number_gt                4405

_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       APEXII,Bruker,2004
_computing_cell_refinement       APEXII,Bruker,2004
_computing_data_reduction        SAINT,Bruker,2004
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'




_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)+(0.0539P)²+0.3357P] 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_extinction_coef       ?

_refine_ls_number_reflns         6020

_refine_ls_number_parameters     336

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0641

_refine_ls_R_factor_gt           0.0423

_refine_ls_wR_factor_ref         0.1182

_refine_ls_wR_factor_gt          0.1057

_refine_ls_goodness_of_fit_ref   1.034

_refine_ls_restrained_S_all      1.034

_refine_ls_shift/su_max          0.003

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group































































C1 C 0.4528(2) 0.91404(19) 0.27603(8) 0.0369(4) Uani 1 1 d . . .
H1 H 0.3854 0.8393 0.3014 0.044 Uiso 1 1 calc R . .
C2 C 0.6325(2) 0.8297(2) 0.26942(9) 0.0408(4) Uani 1 1 d . . .
H2A H 0.7051 0.9069 0.2509 0.049 Uiso 1 1 calc R . .
H2B H 0.6708 0.7879 0.3138 0.049 Uiso 1 1 calc R . .
C3 C 0.63319(19) 0.69198(18) 0.22235(8) 0.0328(3) Uani 1 1 d . . .
C4 C 0.69536(19) 0.44944(18) 0.16845(8) 0.0333(3) Uani 1 1 d . . .
C5 C 0.7659(2) 0.2982(2) 0.14512(9) 0.0421(4) Uani 1 1 d . . .
H5 H 0.8693 0.2489 0.1590 0.051 Uiso 1 1 calc R . .
C6 C 0.6765(2) 0.2235(2) 0.10040(9) 0.0447(4) Uani 1 1 d . . .
H6 H 0.7208 0.1219 0.0839 0.054 Uiso 1 1 calc R . .
C7 C 0.5225(2) 0.2961(2) 0.07956(9) 0.0440(4) Uani 1 1 d . . .
H7 H 0.4655 0.2428 0.0493 0.053 Uiso 1 1 calc R . .
C8 C 0.4524(2) 0.4461(2) 0.10295(8) 0.0389(4) Uani 1 1 d . . .
H8 H 0.3484 0.4938 0.0891 0.047 Uiso 1 1 calc R . .
C9 C 0.54011(19) 0.52534(18) 0.14790(7) 0.0309(3) Uani 1 1 d . . .
C10 C 0.50621(19) 0.67816(17) 0.18198(8) 0.0316(3) Uani 1 1 d . . .
C11 C 0.3620(2) 0.81092(18) 0.17431(8) 0.0339(3) Uani 1 1 d . . .
H11 H 0.2591 0.7704 0.1913 0.041 Uiso 1 1 calc R . .
C12 C 0.4371(2) 1.07324(19) 0.31270(8) 0.0360(4) Uani 1 1 d . . .
C13 C 0.4372(2) 1.2215(2) 0.27632(9) 0.0461(4) Uani 1 1 d . . .
H13 H 0.4491 1.2230 0.2289 0.055 Uiso 1 1 calc R . .
C14 C 0.4197(3) 1.3669(2) 0.30965(9) 0.0499(5) Uani 1 1 d . . .
H14 H 0.4184 1.4661 0.2847 0.060 Uiso 1 1 calc R . .
C15 C 0.4041(3) 1.3655(2) 0.38005(9) 0.0479(4) Uani 1 1 d . . .
C16 C 0.4048(3) 1.2185(2) 0.41698(9) 0.0590(6) Uani 1 1 d . . .
H16 H 0.3952 1.2171 0.4645 0.071 Uiso 1 1 calc R . .
C17 C 0.4198(3) 1.0735(2) 0.38316(9) 0.0516(5) Uani 1 1 d . . .
H17 H 0.4181 0.9746 0.4081 0.062 Uiso 1 1 calc R . .
C18 C 0.3916(4) 1.5198(3) 0.41337(11) 0.0699(7) Uani 1 1 d . . .
C19 C 0.9341(2) 0.3432(2) 0.30200(8) 0.0389(4) Uani 1 1 d . . .
C20 C 0.8509(3) 0.3606(3) 0.36466(10) 0.0560(5) Uani 1 1 d . . .
H20 H 0.8032 0.4637 0.3785 0.067 Uiso 1 1 calc R . .
C21 C 0.8394(3) 0.2221(3) 0.40664(10) 0.0673(6) Uani 1 1 d . . .
H21 H 0.7841 0.2334 0.4492 0.081 Uiso 1 1 calc R . .
C22 C 0.9080(3) 0.0676(3) 0.38695(11) 0.0584(5) Uani 1 1 d . . .
C23 C 0.9938(3) 0.0540(2) 0.32476(10) 0.0534(5) Uani 1 1 d . . .
H23 H 1.0427 -0.0490 0.3112 0.064 Uiso 1 1 calc R . .
C24 C 1.0088(2) 0.1901(2) 0.28199(9) 0.0451(4) Uani 1 1 d . . .
H24 H 1.0683 0.1792 0.2403 0.054 Uiso 1 1 calc R . .
C25 C 0.8882(4) -0.0828(3) 0.43185(13) 0.0940(9) Uani 1 1 d . . .
H25A H 0.8569 -0.0507 0.4776 0.141 Uiso 1 1 calc R . .
H25B H 0.9916 -0.1548 0.4319 0.141 Uiso 1 1 calc R . .
H25C H 0.8036 -0.1388 0.4147 0.141 Uiso 1 1 calc R . .
C26 C 0.3472(2) 0.8701(2) 0.10029(8) 0.0404(4) Uani 1 1 d . . .
H26A H 0.4469 0.9168 0.0852 0.049 Uiso 1 1 calc R . .
H26B H 0.3404 0.7767 0.0726 0.049 Uiso 1 1 calc R . .
C27 C 0.1985(2) 0.99636(19) 0.08841(8) 0.0380(4) Uani 1 1 d . . .
C28 C 0.0865(3) 1.2141(2) 0.01515(11) 0.0585(5) Uani 1 1 d . . .
H28A H 0.0684 1.2913 0.0515 0.070 Uiso 1 1 calc R . .
H28B H -0.0155 1.1674 0.0102 0.070 Uiso 1 1 calc R . .
C29 C 0.1343(3) 1.2981(3) -0.04944(13) 0.0880(8) Uani 1 1 d . . .
H29A H 0.2306 1.3507 -0.0430 0.132 Uiso 1 1 calc R . .
H29B H 0.0442 1.3791 -0.0631 0.132 Uiso 1 1 calc R . .
H29C H 0.1593 1.2191 -0.0843 0.132 Uiso 1 1 calc R . .
N1 N 0.75458(16) 0.55221(16) 0.21468(7) 0.0374(3) Uani 1 1 d . . .
N2 N 0.3857(4) 1.6437(2) 0.43749(11) 0.1076(10) Uani 1 1 d . . .
O1 O 0.38705(14) 0.95156(13) 0.21037(6) 0.0397(3) Uani 1 1 d . . .
O2 O 0.95947(17) 0.65555(16) 0.28472(8) 0.0592(4) Uani 1 1 d . . .
O3 O 1.05805(15) 0.47135(16) 0.19120(7) 0.0536(3) Uani 1 1 d . . .
O4 O 0.07425(17) 1.01279(17) 0.12438(7) 0.0596(4) Uani 1 1 d . . .
O5 O 0.22076(15) 1.08515(14) 0.03119(6) 0.0462(3) Uani 1 1 d . . .
S1 S 0.94405(5) 0.51586(5) 0.24662(2) 0.04120(13) Uani 1 1 d . . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag



































































C1 O1 1.4218(18) . ?
C1 C12 1.510(2) . ?
C1 C2 1.532(2) . ?
C1 H1 0.9800 . ?
C2 C3 1.493(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C10 1.351(2) . ?
C3 N1 1.4185(19) . ?
C4 C5 1.386(2) . ?
C4 C9 1.399(2) . ?
C4 N1 1.4109(19) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.438(2) . ?
C10 C11 1.498(2) . ?
C11 O1 1.4254(17) . ?
C11 C26 1.514(2) . ?
C11 H11 0.9800 . ?
C12 C17 1.381(2) . ?
C12 C13 1.383(2) . ?
C13 C14 1.376(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 C18 1.443(2) . ?
C16 C17 1.379(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N2 1.137(3) . ?
C19 C20 1.377(3) . ?
C19 C24 1.387(2) . ?
C19 S1 1.7542(18) . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(3) . ?
C22 C25 1.505(3) . ?
C23 C24 1.382(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.503(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 O4 1.199(2) . ?
C27 O5 1.328(2) . ?
C28 O5 1.450(2) . ?
C28 C29 1.474(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N1 S1 1.6749(13) . ?
O2 S1 1.4215(13) . ?
O3 S1 1.4214(14) . ?



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 C1 C12 107.12(12) . . ?
O1 C1 C2 110.56(13) . . ?
C12 C1 C2 112.79(13) . . ?
O1 C1 H1 108.8 . . ?
C12 C1 H1 108.8 . . ?
C2 C1 H1 108.8 . . ?
C3 C2 C1 106.77(13) . . ?
C3 C2 H2A 110.4 . . ?
C1 C2 H2A 110.4 . . ?
C3 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C10 C3 N1 108.59(13) . . ?
C10 C3 C2 123.19(14) . . ?
N1 C3 C2 128.11(13) . . ?
C5 C4 C9 122.04(14) . . ?
C5 C4 N1 130.16(15) . . ?
C9 C4 N1 107.79(12) . . ?
C6 C5 C4 117.32(16) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C7 121.60(15) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 121.00(15) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 118.81(16) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C8 C9 C4 119.23(14) . . ?
C8 C9 C10 133.85(15) . . ?
C4 C9 C10 106.92(12) . . ?
C3 C10 C9 108.96(13) . . ?
C3 C10 C11 122.38(13) . . ?
C9 C10 C11 128.59(13) . . ?
O1 C11 C10 110.59(12) . . ?
O1 C11 C26 105.42(13) . . ?
C10 C11 C26 110.71(13) . . ?
O1 C11 H11 110.0 . . ?
C10 C11 H11 110.0 . . ?
C26 C11 H11 110.0 . . ?
C17 C12 C13 118.84(15) . . ?
C17 C12 C1 120.52(15) . . ?
C13 C12 C1 120.64(14) . . ?
C14 C13 C12 120.65(16) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.02(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.94(15) . . ?
C16 C15 C18 121.55(17) . . ?
C14 C15 C18 118.48(17) . . ?
C15 C16 C17 119.71(16) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 120.83(16) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
N2 C18 C15 177.2(3) . . ?
C20 C19 C24 120.60(17) . . ?
C20 C19 S1 119.72(14) . . ?
C24 C19 S1 119.68(14) . . ?
C19 C20 C21 118.87(19) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 121.6(2) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C23 C22 C21 118.32(19) . . ?
C23 C22 C25 120.6(2) . . ?
C21 C22 C25 121.1(2) . . ?
C22 C23 C24 121.40(19) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 119.12(18) . . ?
C23 C24 H24 120.4 . . ?
C19 C24 H24 120.4 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C11 113.39(14) . . ?
C27 C26 H26A 108.9 . . ?
C11 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C11 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
O4 C27 O5 124.12(15) . . ?
O4 C27 C26 125.10(16) . . ?
O5 C27 C26 110.75(15) . . ?
O5 C28 C29 107.63(18) . . ?
O5 C28 H28A 110.2 . . ?
C29 C28 H28A 110.2 . . ?
O5 C28 H28B 110.2 . . ?
C29 C28 H28B 110.2 . . ?
H28A C28 H28B 108.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C4 N1 C3 107.72(12) . . ?
C4 N1 S1 123.58(11) . . ?
C3 N1 S1 128.45(10) . . ?
C1 O1 C11 114.09(11) . . ?
C27 O5 C28 115.77(14) . . ?
O3 S1 O2 120.38(9) . . ?
O3 S1 N1 106.97(7) . . ?
O2 S1 N1 105.45(7) . . ?
O3 S1 C19 108.74(8) . . ?
O2 S1 C19 110.02(8) . . ?
N1 S1 C19 103.96(7) . . ?



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 C1 C2 C3 -50.50(17) . . . . ?
C12 C1 C2 C3 -170.40(13) . . . . ?
C1 C2 C3 C10 14.9(2) . . . . ?
C1 C2 C3 N1 -160.80(16) . . . . ?
C9 C4 C5 C6 -0.2(3) . . . . ?
N1 C4 C5 C6 178.67(16) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C4 -0.8(2) . . . . ?
C7 C8 C9 C10 -179.65(17) . . . . ?
C5 C4 C9 C8 0.6(2) . . . . ?
N1 C4 C9 C8 -178.50(14) . . . . ?
C5 C4 C9 C10 179.73(15) . . . . ?
N1 C4 C9 C10 0.66(17) . . . . ?
N1 C3 C10 C9 1.45(18) . . . . ?
C2 C3 C10 C9 -174.99(15) . . . . ?
N1 C3 C10 C11 -175.77(14) . . . . ?
C2 C3 C10 C11 7.8(2) . . . . ?
C8 C9 C10 C3 177.66(17) . . . . ?
C4 C9 C10 C3 -1.32(18) . . . . ?
C8 C9 C10 C11 -5.3(3) . . . . ?
C4 C9 C10 C11 175.67(15) . . . . ?
C3 C10 C11 O1 4.5(2) . . . . ?
C9 C10 C11 O1 -172.12(14) . . . . ?
C3 C10 C11 C26 120.97(17) . . . . ?
C9 C10 C11 C26 -55.7(2) . . . . ?
O1 C1 C12 C17 151.47(17) . . . . ?
C2 C1 C12 C17 -86.7(2) . . . . ?
O1 C1 C12 C13 -27.5(2) . . . . ?
C2 C1 C12 C13 94.37(19) . . . . ?
C17 C12 C13 C14 -0.2(3) . . . . ?
C1 C12 C13 C14 178.77(17) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C13 C14 C15 C18 178.0(2) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C18 C15 C16 C17 -178.9(2) . . . . ?
C15 C16 C17 C12 1.2(3) . . . . ?
C13 C12 C17 C16 -0.8(3) . . . . ?
C1 C12 C17 C16 -179.79(19) . . . . ?
C16 C15 C18 N2 147(6) . . . . ?
C14 C15 C18 N2 -31(6) . . . . ?
C24 C19 C20 C21 -1.6(3) . . . . ?
S1 C19 C20 C21 177.74(15) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C23 2.0(3) . . . . ?
C20 C21 C22 C25 -177.4(2) . . . . ?
C21 C22 C23 C24 -1.4(3) . . . . ?
C25 C22 C23 C24 178.02(19) . . . . ?
C22 C23 C24 C19 -0.7(3) . . . . ?
C20 C19 C24 C23 2.2(3) . . . . ?
S1 C19 C24 C23 -177.12(13) . . . . ?
O1 C11 C26 C27 -63.93(17) . . . . ?
C10 C11 C26 C27 176.46(13) . . . . ?
C11 C26 C27 O4 -24.1(2) . . . . ?
C11 C26 C27 O5 157.74(14) . . . . ?
C5 C4 N1 C3 -178.77(17) . . . . ?
C9 C4 N1 C3 0.19(17) . . . . ?
C5 C4 N1 S1 6.6(3) . . . . ?
C9 C4 N1 S1 -174.47(11) . . . . ?
C10 C3 N1 C4 -1.03(18) . . . . ?
C2 C3 N1 C4 175.18(16) . . . . ?
C10 C3 N1 S1 173.29(12) . . . . ?
C2 C3 N1 S1 -10.5(3) . . . . ?
C12 C1 O1 C11 -168.14(13) . . . . ?
C2 C1 O1 C11 68.60(17) . . . . ?
C10 C11 O1 C1 -42.43(18) . . . . ?
C26 C11 O1 C1 -162.12(13) . . . . ?
O4 C27 O5 C28 3.2(2) . . . . ?
C26 C27 O5 C28 -178.60(14) . . . . ?
C29 C28 O5 C27 179.87(18) . . . . ?
C4 N1 S1 O3 44.90(15) . . . . ?
C3 N1 S1 O3 -128.60(15) . . . . ?
C4 N1 S1 O2 174.17(13) . . . . ?
C3 N1 S1 O2 0.67(17) . . . . ?
C4 N1 S1 C19 -70.07(15) . . . . ?
C3 N1 S1 C19 116.44(15) . . . . ?
C20 C19 S1 O3 170.50(14) . . . . ?
C24 C19 S1 O3 -10.12(16) . . . . ?
C20 C19 S1 O2 36.71(17) . . . . ?
C24 C19 S1 O2 -143.92(14) . . . . ?
C20 C19 S1 N1 -75.80(15) . . . . ?
C24 C19 S1 N1 103.58(14) . . . . ?



_diffrn_measured_fraction_theta_max 0.940

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.983

_refine_diff_density_max         0.297

_refine_diff_density_min         -0.252

_refine_diff_density_rms         0.040

_database_code_depnum_ccdc_archive 'CCDC 971413'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_SJG-VPS-84-B

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H23 N O7 S'
_chemical_formula_moiety         'C22 H23 N O7 S'
_chemical_formula_weight         445.49
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_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_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.440(5)
_cell_length_b                   10.513(7)
_cell_length_c                   13.472(9)
_cell_angle_alpha                83.084(17)
_cell_angle_beta                 86.07(2)
_cell_angle_gamma                86.796(18)
_cell_volume                     1042.4(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1626
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      31.30
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468.00
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.961

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            7918
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3594
_reflns_number_gt                2680
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0769
_refine_ls_wR_factor_ref         0.1773
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3588
_refine_ls_number_parameters     280
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0491P)²+0.6790P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.86154(13) 0.24681(10) 0.45514(8) 0.0146(3) Uani 1.0 2 d . . .
O2 O 0.7552(4) 0.5889(3) 0.9066(3) 0.0213(8) Uani 1.0 2 d . . .
O3 O 0.8776(4) 0.3827(3) 0.4424(3) 0.0187(8) Uani 1.0 2 d . . .
O4 O 0.7114(4) 0.3773(3) 0.9169(3) 0.0226(8) Uani 1.0 2 d . . .
O5 O 1.0036(4) 0.1651(3) 0.4987(3) 0.0181(8) Uani 1.0 2 d . . .
O6 O 0.4937(4) 0.3432(3) 0.4347(3) 0.0181(8) Uani 1.0 2 d . . .
O9 O 0.9665(4) 0.2912(3) 0.7477(3) 0.0246(8) Uani 1.0 2 d . . .
O12 O 0.5057(4) 0.3517(3) 0.7359(3) 0.0158(7) Uani 1.0 2 d . . .
N32 N 0.6783(5) 0.2125(3) 0.5352(3) 0.0128(8) Uani 1.0 2 d . . .
C8 C 0.3705(6) 0.3749(4) 0.6635(4) 0.0168(11) Uani 1.0 2 d . . .
C10 C 0.8306(5) 0.0660(4) 0.3303(4) 0.0159(10) Uani 1.0 2 d . . .
C11 C 0.7323(6) 0.2438(4) 0.1713(4) 0.0191(11) Uani 1.0 2 d . . .
C13 C 0.6821(5) 0.3928(4) 0.7031(4) 0.0157(10) Uani 1.0 2 d . . .
C14 C 0.7970(5) 0.0258(4) 0.2401(4) 0.0162(10) Uani 1.0 2 d . . .
C15 C 0.7291(6) 0.5058(4) 0.7548(4) 0.0188(11) Uani 1.0 2 d . . .
C16 C 0.8158(6) 0.2784(4) 0.7218(4) 0.0167(10) Uani 1.0 2 d . . .
C17 C 0.5108(6) 0.2772(4) 0.5153(4) 0.0146(10) Uani 1.0 2 d . . .
C18 C 0.6995(6) 0.1149(4) 0.6203(4) 0.0154(10) Uani 1.0 2 d . . .
C19 C 0.6627(6) -0.0099(4) 0.6093(4) 0.0184(11) Uani 1.0 2 d . . .
C20 C 0.7583(5) 0.1470(4) 0.7097(4) 0.0148(10) Uani 1.0 2 d . . .
C21 C 0.7655(6) 0.2850(4) 0.2610(4) 0.0206(11) Uani 1.0 2 d . . .
C22 C 0.7463(6) 0.1134(4) 0.1588(4) 0.0174(11) Uani 1.0 2 d . . .
C23 C 0.7298(6) 0.4798(4) 0.8671(4) 0.0160(10) Uani 1.0 2 d . . .
C24 C 0.3643(6) 0.2682(4) 0.5969(4) 0.0160(10) Uani 1.0 2 d . . .
C25 C 0.7325(6) -0.0740(5) 0.7802(4) 0.0230(12) Uani 1.0 2 d . . .
C26 C 0.7572(6) 0.5788(4) 1.0149(4) 0.0214(11) Uani 1.0 2 d . . .
C27 C 0.6784(6) -0.1045(4) 0.6904(4) 0.0195(11) Uani 1.0 2 d . . .
C28 C 0.7752(6) 0.0501(4) 0.7894(4) 0.0178(11) Uani 1.0 2 d . . .
C29 C 0.8146(6) 0.1960(4) 0.3414(4) 0.0142(10) Uani 1.0 2 d . . .
C30 C 0.7903(8) 0.7099(5) 1.0410(4) 0.0344(13) Uani 1.0 2 d . . .
C31 C 0.7083(7) 0.0681(5) 0.0616(4) 0.0284(12) Uani 1.0 2 d . . .
H8A H 0.3940 0.4563 0.6207 0.0201 Uiso 1.0 2 calc R . .
H8B H 0.2509 0.3854 0.6994 0.0201 Uiso 1.0 2 calc R . .
H10 H 0.8646 0.0052 0.3846 0.0190 Uiso 1.0 2 calc R . .
H11 H 0.6994 0.3048 0.1169 0.0229 Uiso 1.0 2 calc R . .
H13 H 0.6844 0.4203 0.6293 0.0188 Uiso 1.0 2 calc R . .
H14 H 0.8083 -0.0631 0.2328 0.0194 Uiso 1.0 2 calc R . .
H15A H 0.8499 0.5332 0.7281 0.0225 Uiso 1.0 2 calc R . .
H15B H 0.6414 0.5781 0.7375 0.0225 Uiso 1.0 2 calc R . .
H19 H 0.6271 -0.0309 0.5472 0.0221 Uiso 1.0 2 calc R . .
H21 H 0.7551 0.3739 0.2683 0.0247 Uiso 1.0 2 calc R . .
H24A H 0.3769 0.1841 0.6382 0.0192 Uiso 1.0 2 calc R . .
H24B H 0.2459 0.2736 0.5670 0.0192 Uiso 1.0 2 calc R . .
H25 H 0.7404 -0.1384 0.8358 0.0276 Uiso 1.0 2 calc R . .
H26A H 0.8541 0.5165 1.0389 0.0257 Uiso 1.0 2 calc R . .
H26B H 0.6403 0.5495 1.0465 0.0257 Uiso 1.0 2 calc R . .
H27 H 0.6518 -0.1903 0.6839 0.0234 Uiso 1.0 2 calc R . .
H28 H 0.8165 0.0697 0.8507 0.0213 Uiso 1.0 2 calc R . .
H30A H 0.7991 0.7063 1.1136 0.0413 Uiso 1.0 2 calc R . .
H30B H 0.6901 0.7695 1.0201 0.0413 Uiso 1.0 2 calc R . .
H30C H 0.9031 0.7396 1.0064 0.0413 Uiso 1.0 2 calc R . .
H31A H 0.8075 0.0097 0.0410 0.0341 Uiso 1.0 2 calc R . .
H31B H 0.6969 0.1419 0.0102 0.0341 Uiso 1.0 2 calc R . .
H31C H 0.5956 0.0229 0.0699 0.0341 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b23 (Rigaku, 2012)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b23'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b23'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 O3 1.429(3) yes . .
S1 O5 1.436(3) yes . .
S1 N32 1.706(4) yes . .
S1 C29 1.745(5) yes . .
O2 C23 1.349(6) yes . .
O2 C26 1.451(6) yes . .
O4 C23 1.209(5) yes . .
O6 C17 1.226(6) yes . .
O9 C16 1.216(6) yes . .
O12 C8 1.439(6) yes . .
O12 C13 1.429(5) yes . .
N32 C17 1.412(5) yes . .
N32 C18 1.455(6) yes . .
C8 C24 1.522(7) yes . .
C10 C14 1.376(7) yes . .
C10 C29 1.391(6) yes . .
C11 C21 1.374(7) yes . .
C11 C22 1.398(6) yes . .
C13 C15 1.515(7) yes . .
C13 C16 1.526(6) yes . .
C14 C22 1.402(6) yes . .
C15 C23 1.505(7) yes . .
C16 C20 1.500(6) yes . .
C17 C24 1.493(6) yes . .
C18 C19 1.382(6) yes . .
C18 C20 1.394(7) yes . .
C19 C27 1.392(6) yes . .
C20 C28 1.395(6) yes . .
C21 C29 1.398(6) yes . .
C22 C31 1.496(8) yes . .
C25 C27 1.379(8) yes . .
C25 C28 1.382(7) yes . .
C26 C30 1.501(7) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O3 S1 O5 119.56(18) yes . . .
O3 S1 N32 108.07(17) yes . . .
O3 S1 C29 109.56(19) yes . . .
O5 S1 N32 103.40(17) yes . . .
O5 S1 C29 109.31(19) yes . . .
N32 S1 C29 105.98(19) yes . . .
C23 O2 C26 116.5(4) yes . . .
C8 O12 C13 116.3(4) yes . . .
S1 N32 C17 119.1(3) yes . . .
S1 N32 C18 118.6(3) yes . . .
C17 N32 C18 122.3(4) yes . . .
O12 C8 C24 113.7(4) yes . . .
C14 C10 C29 119.6(4) yes . . .
C21 C11 C22 121.1(4) yes . . .
O12 C13 C15 111.3(4) yes . . .
O12 C13 C16 108.2(3) yes . . .
C15 C13 C16 112.2(4) yes . . .
C10 C14 C22 121.4(4) yes . . .
C13 C15 C23 114.8(4) yes . . .
O9 C16 C13 121.5(4) yes . . .
O9 C16 C20 119.4(4) yes . . .
C13 C16 C20 119.0(4) yes . . .
O6 C17 N32 119.4(4) yes . . .
O6 C17 C24 122.6(4) yes . . .
N32 C17 C24 117.8(4) yes . . .
N32 C18 C19 118.3(4) yes . . .
N32 C18 C20 120.5(4) yes . . .
C19 C18 C20 121.2(4) yes . . .
C18 C19 C27 119.3(5) yes . . .
C16 C20 C18 123.0(4) yes . . .
C16 C20 C28 118.6(4) yes . . .
C18 C20 C28 118.2(4) yes . . .
C11 C21 C29 120.0(4) yes . . .
C11 C22 C14 118.1(5) yes . . .
C11 C22 C31 121.2(4) yes . . .
C14 C22 C31 120.7(4) yes . . .
O2 C23 O4 123.4(5) yes . . .
O2 C23 C15 110.3(4) yes . . .
O4 C23 C15 126.4(5) yes . . .
C8 C24 C17 111.6(4) yes . . .
C27 C25 C28 120.1(4) yes . . .
O2 C26 C30 106.9(4) yes . . .
C19 C27 C25 120.2(5) yes . . .
C20 C28 C25 120.8(5) yes . . .
S1 C29 C10 119.5(4) yes . . .
S1 C29 C21 120.6(4) yes . . .
C10 C29 C21 119.9(5) yes . . .



#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 971414'
