# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_s3726ma
_database_code_depnum_ccdc_archive 'CCDC 1056923'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N O5 S Si'
_chemical_formula_weight         351.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.8463(2)
_cell_length_b                   9.1987(2)
_cell_length_c                   18.7908(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.4730(10)
_cell_angle_gamma                90.00
_cell_volume                     1700.36(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4329
_cell_measurement_theta_min      4.71
_cell_measurement_theta_max      72.19

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    2.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.476706
_exptl_absorpt_correction_T_max  0.6977
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8472
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.49
_diffrn_reflns_theta_max         72.28
_reflns_number_total             3227
_reflns_number_gt                2883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0582P)²+0.4918P] 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       0.0005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3227
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.26980(15) 0.17942(17) 0.08781(8) 0.0237(3) Uani 1 1 d . . .
C2 C 0.28223(15) 0.28296(17) 0.14153(8) 0.0237(3) Uani 1 1 d . . .
C3 C 0.32098(18) 0.42179(18) 0.11927(10) 0.0323(4) Uani 1 1 d . . .
H3 H 0.3300 0.4977 0.1534 0.039 Uiso 1 1 calc R . .
C4 C 0.3465(2) 0.4513(2) 0.04866(11) 0.0401(4) Uani 1 1 d . . .
H4 H 0.3740 0.5460 0.0353 0.048 Uiso 1 1 calc R . .
C5 C 0.3322(2) 0.3440(2) -0.00203(10) 0.0386(4) Uani 1 1 d . . .
H5 H 0.3500 0.3649 -0.0503 0.046 Uiso 1 1 calc R . .
C6 C 0.29185(18) 0.2052(2) 0.01707(9) 0.0313(4) Uani 1 1 d . . .
H6 H 0.2798 0.1305 -0.0175 0.038 Uiso 1 1 calc R . .
C7 C 0.2590(2) 0.4160(2) 0.28825(11) 0.0414(5) Uani 1 1 d . . .
H7A H 0.1981 0.4873 0.2649 0.062 Uiso 1 1 calc R . .
H7B H 0.3525 0.4527 0.2892 0.062 Uiso 1 1 calc R . .
H7C H 0.2315 0.3997 0.3371 0.062 Uiso 1 1 calc R . .
C8 C 0.0788(2) 0.1573(3) 0.24559(10) 0.0452(5) Uani 1 1 d . . .
H8A H 0.0656 0.1307 0.2953 0.068 Uiso 1 1 calc R . .
H8B H 0.0726 0.0700 0.2157 0.068 Uiso 1 1 calc R . .
H8C H 0.0084 0.2267 0.2296 0.068 Uiso 1 1 calc R . .
C9 C 0.3856(2) 0.1167(2) 0.27369(10) 0.0424(5) Uani 1 1 d . . .
H9A H 0.4747 0.1622 0.2687 0.064 Uiso 1 1 calc R . .
H9B H 0.3817 0.0252 0.2469 0.064 Uiso 1 1 calc R . .
H9C H 0.3719 0.0969 0.3241 0.064 Uiso 1 1 calc R . .
C10 C 0.24883(16) -0.17152(17) 0.01406(8) 0.0247(3) Uani 1 1 d . . .
C11 C 0.12406(17) -0.24104(18) 0.00231(9) 0.0277(3) Uani 1 1 d . . .
C12 C 0.0916(2) -0.3121(2) -0.06059(10) 0.0380(4) Uani 1 1 d . . .
H12 H 0.0066 -0.3599 -0.0675 0.046 Uiso 1 1 calc R . .
C13 C 0.1851(2) -0.3127(2) -0.11371(10) 0.0414(4) Uani 1 1 d . . .
H13 H 0.1642 -0.3618 -0.1573 0.050 Uiso 1 1 calc R . .
C14 C 0.3084(2) -0.2426(2) -0.10371(10) 0.0390(5) Uani 1 1 d . . .
H14 H 0.3712 -0.2419 -0.1407 0.047 Uiso 1 1 calc R . .
C15 C 0.34071(18) -0.17308(18) -0.03979(10) 0.0316(4) Uani 1 1 d . . .
H15 H 0.4263 -0.1263 -0.0328 0.038 Uiso 1 1 calc R . .
N1 N 0.02040(16) -0.24096(19) 0.05623(9) 0.0384(4) Uani 1 1 d . . .
O1 O 0.22136(11) 0.04084(12) 0.10924(6) 0.0284(3) Uani 1 1 d . . .
O2 O 0.44530(12) -0.06868(14) 0.09497(8) 0.0377(3) Uani 1 1 d . . .
O3 O 0.25879(15) -0.20042(14) 0.15121(7) 0.0389(3) Uani 1 1 d . . .
O4 O -0.01560(14) -0.12353(19) 0.07903(9) 0.0521(4) Uani 1 1 d . . .
O5 O -0.02662(16) -0.35843(19) 0.07271(9) 0.0538(4) Uani 1 1 d . . .
S1 S 0.30462(4) -0.10326(4) 0.09838(2) 0.02696(14) Uani 1 1 d . . .
Si1 Si 0.24949(4) 0.24186(5) 0.23813(2) 0.02661(14) 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 C6 1.377(2) . ?
C1 C2 1.389(2) . ?
C1 O1 1.4253(18) . ?
C2 C3 1.402(2) . ?
C2 Si1 1.8952(16) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 Si1 1.858(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 Si1 1.8623(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 Si1 1.869(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.386(2) . ?
C10 C11 1.394(2) . ?
C10 S1 1.7697(16) . ?
C11 C12 1.376(2) . ?
C11 N1 1.469(2) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N1 O4 1.220(2) . ?
N1 O5 1.221(2) . ?
O1 S1 1.5765(12) . ?
O2 S1 1.4253(13) . ?
O3 S1 1.4236(13) . ?

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
C6 C1 C2 124.80(15) . . ?
C6 C1 O1 119.71(14) . . ?
C2 C1 O1 115.33(13) . . ?
C1 C2 C3 115.10(15) . . ?
C1 C2 Si1 123.08(12) . . ?
C3 C2 Si1 121.82(13) . . ?
C4 C3 C2 121.74(17) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 120.34(17) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.17(16) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 117.83(17) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.56(15) . . ?
C15 C10 S1 118.04(13) . . ?
C11 C10 S1 122.81(12) . . ?
C12 C11 C10 121.61(16) . . ?
C12 C11 N1 116.76(16) . . ?
C10 C11 N1 121.63(15) . . ?
C11 C12 C13 118.93(18) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.47(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.08(17) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.34(17) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
O4 N1 O5 125.13(16) . . ?
O4 N1 C11 117.62(15) . . ?
O5 N1 C11 117.19(16) . . ?
C1 O1 S1 122.23(9) . . ?
O3 S1 O2 120.62(9) . . ?
O3 S1 O1 104.80(7) . . ?
O2 S1 O1 109.27(7) . . ?
O3 S1 C10 107.83(8) . . ?
O2 S1 C10 107.67(8) . . ?
O1 S1 C10 105.73(7) . . ?
C7 Si1 C8 110.35(9) . . ?
C7 Si1 C9 109.28(10) . . ?
C8 Si1 C9 110.56(11) . . ?
C7 Si1 C2 107.85(9) . . ?
C8 Si1 C2 110.29(8) . . ?
C9 Si1 C2 108.45(8) . . ?

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
C6 C1 C2 C3 -0.4(2) . . . . ?
O1 C1 C2 C3 -175.83(13) . . . . ?
C6 C1 C2 Si1 179.58(13) . . . . ?
O1 C1 C2 Si1 4.10(19) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
Si1 C2 C3 C4 179.20(14) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
O1 C1 C6 C5 176.69(15) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
S1 C10 C11 C12 -170.13(14) . . . . ?
C15 C10 C11 N1 -178.53(16) . . . . ?
S1 C10 C11 N1 10.4(2) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
N1 C11 C12 C13 178.75(17) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C10 -1.0(3) . . . . ?
C11 C10 C15 C14 0.0(2) . . . . ?
S1 C10 C15 C14 171.45(13) . . . . ?
C12 C11 N1 O4 -124.93(19) . . . . ?
C10 C11 N1 O4 54.6(3) . . . . ?
C12 C11 N1 O5 52.4(3) . . . . ?
C10 C11 N1 O5 -128.12(19) . . . . ?
C6 C1 O1 S1 61.65(19) . . . . ?
C2 C1 O1 S1 -122.63(13) . . . . ?
C1 O1 S1 O3 155.19(12) . . . . ?
C1 O1 S1 O2 24.61(14) . . . . ?
C1 O1 S1 C10 -91.02(13) . . . . ?
C15 C10 S1 O3 -135.10(14) . . . . ?
C11 C10 S1 O3 36.01(16) . . . . ?
C15 C10 S1 O2 -3.49(15) . . . . ?
C11 C10 S1 O2 167.62(13) . . . . ?
C15 C10 S1 O1 113.23(13) . . . . ?
C11 C10 S1 O1 -75.66(15) . . . . ?
C1 C2 Si1 C7 -173.63(14) . . . . ?
C3 C2 Si1 C7 6.30(16) . . . . ?
C1 C2 Si1 C8 -53.06(16) . . . . ?
C3 C2 Si1 C8 126.87(15) . . . . ?
C1 C2 Si1 C9 68.14(16) . . . . ?
C3 C2 Si1 C9 -111.93(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        72.28
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_s3727na
_database_code_depnum_ccdc_archive 'CCDC 1056924'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O7 S Si'
_chemical_formula_weight         396.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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)/c

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

_cell_length_a                   13.5825(3)
_cell_length_b                   10.5322(2)
_cell_length_c                   12.8580(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.968(2)
_cell_angle_gamma                90.00
_cell_volume                     1799.40(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3477
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      67.63

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    2.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.477511
_exptl_absorpt_correction_T_max  0.7798
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9327
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         67.80
_reflns_number_total             3225
_reflns_number_gt                2774
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0498P)²+0.5335P] 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         3225
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_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 0.26980(14) 0.63612(18) 0.95705(14) 0.0197(4) Uani 1 1 d . . .
C2 C 0.34209(13) 0.59998(18) 0.90092(14) 0.0197(4) Uani 1 1 d . . .
C3 C 0.34966(15) 0.46823(19) 0.88626(16) 0.0250(4) Uani 1 1 d . . .
H3 H 0.3973 0.4372 0.8478 0.030 Uiso 1 1 calc R . .
C4 C 0.28929(15) 0.3820(2) 0.92646(17) 0.0277(4) Uani 1 1 d . . .
H4 H 0.2951 0.2937 0.9139 0.033 Uiso 1 1 calc R . .
C5 C 0.22057(15) 0.4249(2) 0.98480(16) 0.0270(4) Uani 1 1 d . . .
H5 H 0.1806 0.3659 1.0136 0.032 Uiso 1 1 calc R . .
C6 C 0.21033(14) 0.5542(2) 1.00094(15) 0.0252(4) Uani 1 1 d . . .
H6 H 0.1639 0.5852 1.0409 0.030 Uiso 1 1 calc R . .
C7 C 0.52677(16) 0.6290(2) 0.80320(19) 0.0345(5) Uani 1 1 d . . .
H7A H 0.5753 0.6887 0.7837 0.052 Uiso 1 1 calc R . .
H7B H 0.4955 0.5791 0.7407 0.052 Uiso 1 1 calc R . .
H7C H 0.5616 0.5719 0.8591 0.052 Uiso 1 1 calc R . .
C8 C 0.35127(18) 0.8144(2) 0.74274(17) 0.0331(5) Uani 1 1 d . . .
H8A H 0.3961 0.8571 0.7031 0.050 Uiso 1 1 calc R . .
H8B H 0.3123 0.8780 0.7725 0.050 Uiso 1 1 calc R . .
H8C H 0.3053 0.7582 0.6948 0.050 Uiso 1 1 calc R . .
C9 C 0.48767(16) 0.8224(2) 0.96641(18) 0.0328(5) Uani 1 1 d . . .
H9A H 0.5113 0.7699 1.0296 0.049 Uiso 1 1 calc R . .
H9B H 0.4383 0.8840 0.9811 0.049 Uiso 1 1 calc R . .
H9C H 0.5448 0.8675 0.9481 0.049 Uiso 1 1 calc R . .
C10 C 0.11190(13) 0.87424(18) 1.04216(14) 0.0190(4) Uani 1 1 d . . .
C11 C 0.14525(13) 0.96516(18) 1.12046(14) 0.0190(4) Uani 1 1 d . . .
C12 C 0.09485(14) 0.98780(18) 1.20128(15) 0.0214(4) Uani 1 1 d . . .
H12 H 0.1173 1.0508 1.2537 0.026 Uiso 1 1 calc R . .
C13 C 0.01073(14) 0.91561(18) 1.20300(14) 0.0211(4) Uani 1 1 d . . .
C14 C -0.02595(14) 0.82579(19) 1.12706(16) 0.0238(4) Uani 1 1 d . . .
H14 H -0.0845 0.7780 1.1308 0.029 Uiso 1 1 calc R . .
C15 C 0.02456(14) 0.80651(19) 1.04472(16) 0.0240(4) Uani 1 1 d . . .
H15 H -0.0006 0.7470 0.9902 0.029 Uiso 1 1 calc R . .
N1 N 0.23707(12) 1.04033(16) 1.12213(13) 0.0244(4) Uani 1 1 d . . .
N2 N -0.04208(12) 0.93459(17) 1.29121(13) 0.0268(4) Uani 1 1 d . . .
O1 O 0.26480(10) 0.76982(13) 0.97750(10) 0.0224(3) Uani 1 1 d . . .
O2 O 0.10094(11) 0.77963(15) 0.85381(11) 0.0299(3) Uani 1 1 d . . .
O3 O 0.20447(11) 0.97160(14) 0.90463(11) 0.0290(3) Uani 1 1 d . . .
O4 O 0.31498(10) 0.98289(14) 1.12378(12) 0.0301(3) Uani 1 1 d . . .
O5 O 0.22881(13) 1.15525(14) 1.12535(16) 0.0440(4) Uani 1 1 d . . .
O6 O -0.10776(12) 0.85893(17) 1.29994(13) 0.0384(4) Uani 1 1 d . . .
O7 O -0.01575(12) 1.02433(16) 1.35104(12) 0.0370(4) Uani 1 1 d . . .
S1 S 0.16915(3) 0.85133(4) 0.93099(3) 0.02122(15) Uani 1 1 d . . .
Si1 Si 0.42785(4) 0.71894(5) 0.85293(4) 0.02233(15) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.380(3) . ?
C1 C2 1.387(3) . ?
C1 O1 1.437(2) . ?
C2 C3 1.407(3) . ?
C2 Si1 1.8989(19) . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 Si1 1.862(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 Si1 1.868(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 Si1 1.867(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.390(3) . ?
C10 C11 1.395(3) . ?
C10 S1 1.7796(18) . ?
C11 C12 1.379(3) . ?
C11 N1 1.474(2) . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(3) . ?
C13 N2 1.476(2) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N1 O5 1.217(2) . ?
N1 O4 1.215(2) . ?
N2 O6 1.219(2) . ?
N2 O7 1.224(2) . ?
O1 S1 1.5685(13) . ?
O2 S1 1.4256(15) . ?
O3 S1 1.4203(16) . ?

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
C6 C1 C2 125.35(18) . . ?
C6 C1 O1 118.97(17) . . ?
C2 C1 O1 115.45(16) . . ?
C1 C2 C3 114.81(17) . . ?
C1 C2 Si1 122.43(14) . . ?
C3 C2 Si1 122.71(14) . . ?
C4 C3 C2 121.89(18) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 120.10(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.96(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 117.82(18) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 119.07(17) . . ?
C15 C10 S1 117.81(14) . . ?
C11 C10 S1 122.83(14) . . ?
C12 C11 C10 121.67(17) . . ?
C12 C11 N1 116.56(17) . . ?
C10 C11 N1 121.76(16) . . ?
C13 C12 C11 117.40(18) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C14 C13 C12 123.22(17) . . ?
C14 C13 N2 118.43(17) . . ?
C12 C13 N2 118.35(17) . . ?
C13 C14 C15 118.50(18) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C10 C15 C14 120.07(18) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
O5 N1 O4 125.50(18) . . ?
O5 N1 C11 116.81(16) . . ?
O4 N1 C11 117.65(16) . . ?
O6 N2 O7 124.82(17) . . ?
O6 N2 C13 117.64(17) . . ?
O7 N2 C13 117.53(17) . . ?
C1 O1 S1 122.24(12) . . ?
O3 S1 O2 120.62(9) . . ?
O3 S1 O1 106.57(8) . . ?
O2 S1 O1 110.05(8) . . ?
O3 S1 C10 107.23(9) . . ?
O2 S1 C10 107.57(9) . . ?
O1 S1 C10 103.49(8) . . ?
C7 Si1 C9 109.71(10) . . ?
C7 Si1 C8 109.96(11) . . ?
C9 Si1 C8 111.24(11) . . ?
C7 Si1 C2 108.12(10) . . ?
C9 Si1 C2 109.15(9) . . ?
C8 Si1 C2 108.60(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
C6 C1 C2 C3 2.6(3) . . . . ?
O1 C1 C2 C3 176.86(16) . . . . ?
C6 C1 C2 Si1 -174.91(15) . . . . ?
O1 C1 C2 Si1 -0.6(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
Si1 C2 C3 C4 176.88(15) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C2 C1 C6 C5 -2.5(3) . . . . ?
O1 C1 C6 C5 -176.55(16) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C15 C10 C11 C12 1.2(3) . . . . ?
S1 C10 C11 C12 174.86(14) . . . . ?
C15 C10 C11 N1 -179.87(17) . . . . ?
S1 C10 C11 N1 -6.2(3) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
N1 C11 C12 C13 -177.95(16) . . . . ?
C11 C12 C13 C14 -1.8(3) . . . . ?
C11 C12 C13 N2 177.58(16) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
N2 C13 C14 C15 -179.09(17) . . . . ?
C11 C10 C15 C14 -2.8(3) . . . . ?
S1 C10 C15 C14 -176.73(15) . . . . ?
C13 C14 C15 C10 2.1(3) . . . . ?
C12 C11 N1 O5 -54.5(2) . . . . ?
C10 C11 N1 O5 126.5(2) . . . . ?
C12 C11 N1 O4 123.05(19) . . . . ?
C10 C11 N1 O4 -55.9(2) . . . . ?
C14 C13 N2 O6 9.1(3) . . . . ?
C12 C13 N2 O6 -170.27(18) . . . . ?
C14 C13 N2 O7 -171.78(18) . . . . ?
C12 C13 N2 O7 8.8(3) . . . . ?
C6 C1 O1 S1 -68.7(2) . . . . ?
C2 C1 O1 S1 116.63(16) . . . . ?
C1 O1 S1 O3 -142.98(14) . . . . ?
C1 O1 S1 O2 -10.59(16) . . . . ?
C1 O1 S1 C10 104.12(14) . . . . ?
C15 C10 S1 O3 141.06(15) . . . . ?
C11 C10 S1 O3 -32.66(18) . . . . ?
C15 C10 S1 O2 9.95(17) . . . . ?
C11 C10 S1 O2 -163.76(15) . . . . ?
C15 C10 S1 O1 -106.52(15) . . . . ?
C11 C10 S1 O1 79.76(16) . . . . ?
C1 C2 Si1 C7 170.23(16) . . . . ?
C3 C2 Si1 C7 -7.06(19) . . . . ?
C1 C2 Si1 C9 50.94(18) . . . . ?
C3 C2 Si1 C9 -126.35(17) . . . . ?
C1 C2 Si1 C8 -70.49(17) . . . . ?
C3 C2 Si1 C8 112.22(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_s3767na
_database_code_depnum_ccdc_archive 'CCDC 1056926'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#

_audit_creation_date             
;
'Mon Jan 14 14:14:05 2013'
;
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_chemical_formula_sum            'C8 H6 F3 N O5 S'
_chemical_formula_weight         285.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


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                   5.3555(6)
_cell_length_b                   12.8070(14)
_cell_length_c                   16.0563(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.773(8)
_cell_angle_gamma                90.00
_cell_volume                     1093.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    3.248
_diffrn_ambient_temperature      100(2)
_reflns_number_total             2078
_reflns_number_gt                1419
_reflns_threshold_expression     >2sigma(I)
_cell_measurement_reflns_used    2113
_cell_measurement_theta_min      2.7728
_cell_measurement_theta_max      73.9454
_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_absorpt_correction_T_min  0.63119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_reflns_number            4685
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_sigmaI/netI    0.0806
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.7728
_diffrn_reflns_theta_max         73.9454
_diffrn_orient_matrix_UB_11      0.2745557000
_diffrn_orient_matrix_UB_12      -0.0155192000
_diffrn_orient_matrix_UB_13      0.0390988000
_diffrn_orient_matrix_UB_21      -0.0892340000
_diffrn_orient_matrix_UB_22      -0.0137525000
_diffrn_orient_matrix_UB_23      0.0873093000
_diffrn_orient_matrix_UB_31      -0.0252181000
_diffrn_orient_matrix_UB_32      -0.1181735000
_diffrn_orient_matrix_UB_33      -0.0151242000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  117.71  267.71   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   73.8681   69.2087 100

#__ type_ start__ end____ width___ exp.time_
  2 phi    115.70  294.13   1.4994    8.0000
omega____ theta____ kappa____ phi______ frames
 154.8688   35.0000   73.8681     -     119

#__ type_ start__ end____ width___ exp.time_
  3 omega   93.57  234.57   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8681  304.2081 94

#__ type_ start__ end____ width___ exp.time_
  4 phi     20.47  132.92   1.4994    8.0000
omega____ theta____ kappa____ phi______ frames
  30.9187  -65.0000   73.8681     -     75

#__ type_ start__ end____ width___ exp.time_
  5 omega  107.54  190.04   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   73.8681   24.2088 55

#__ type_ start__ end____ width___ exp.time_
  6 omega  -91.79   17.71   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000   73.8681  129.2081 73

#__ type_ start__ end____ width___ exp.time_
  7 omega   91.81  165.31   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       95.0000   73.8681  329.2081 49

#__ type_ start__ end____ width___ exp.time_
  8 omega  166.71  267.21   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8681  314.2088 67

;
_diffrn_measurement_method       'ω and π scans'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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)+(0.1201P)²+0.0000P] 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         2078
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2202
_refine_ls_wR_factor_gt          0.1827
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.1562(7) 0.9565(3) 0.2932(2) 0.0394(9) Uani 1 1 d . . .
C2 C 0.0460(8) 1.0486(3) 0.3187(2) 0.0403(9) Uani 1 1 d . . .
C3 C -0.1218(8) 1.0349(3) 0.3793(3) 0.0444(9) Uani 1 1 d . . .
C4 C -0.1693(9) 0.9385(3) 0.4114(2) 0.0477(10) Uani 1 1 d . . .
H4 H -0.2823 0.9334 0.4526 0.057 Uiso 1 1 calc R . .
C5 C -0.0587(9) 0.8493(3) 0.3857(3) 0.0527(11) Uani 1 1 d . . .
C6 C 0.1067(9) 0.8601(3) 0.3254(3) 0.0491(10) Uani 1 1 d . . .
H6 H 0.1865 0.8000 0.3062 0.059 Uiso 1 1 calc R . .
C7 C 0.1699(10) 0.9698(4) 0.1159(3) 0.0560(12) Uani 1 1 d . . .
C8 C -0.1135(12) 0.7429(4) 0.4203(3) 0.0749(17) Uani 1 1 d . . .
H8A H 0.0339 0.7183 0.4570 0.112 Uiso 1 1 calc R . .
H8B H -0.1521 0.6937 0.3739 0.112 Uiso 1 1 calc R . .
H8C H -0.2577 0.7479 0.4524 0.112 Uiso 1 1 calc R . .
F1 F 0.0232(8) 0.8901(4) 0.1057(2) 0.1181(17) Uani 1 1 d . . .
F2 F 0.3169(7) 0.9704(3) 0.05698(18) 0.0780(10) Uani 1 1 d . . .
F3 F 0.0403(7) 1.0560(3) 0.1111(2) 0.0947(12) Uani 1 1 d . . .
N1 N -0.2600(8) 1.1241(3) 0.4065(2) 0.0556(10) Uani 1 1 d . . .
O1 O 0.4926(7) 0.8618(2) 0.2171(2) 0.0591(9) Uani 1 1 d . . .
O2 O 0.5177(5) 1.0544(2) 0.22448(18) 0.0481(7) Uani 1 1 d . . .
O3 O 0.0952(6) 1.1392(2) 0.28398(18) 0.0491(8) Uani 1 1 d . . .
H3 H 0.0075 1.1864 0.3024 0.074 Uiso 1 1 calc R . .
O4 O -0.4253(7) 1.1092(3) 0.4510(2) 0.0715(11) Uani 1 1 d . . .
O5 O -0.2062(8) 1.2116(3) 0.3830(3) 0.0772(13) Uani 1 1 d . . .
S1 S 0.37094(19) 0.96102(7) 0.21788(6) 0.0421(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 C6 1.376(6) . ?
C1 C2 1.401(5) . ?
C1 S1 1.766(4) . ?
C2 O3 1.327(4) . ?
C2 C3 1.411(5) . ?
C3 C4 1.373(6) . ?
C3 N1 1.456(5) . ?
C4 C5 1.372(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(5) . ?
C5 C8 1.513(6) . ?
C6 H6 0.9500 . ?
C7 F1 1.287(6) . ?
C7 F2 1.301(5) . ?
C7 F3 1.301(6) . ?
C7 S1 1.853(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 O4 1.217(4) . ?
N1 O5 1.227(5) . ?
O1 S1 1.429(3) . ?
O2 S1 1.428(3) . ?
O3 H3 0.8400 . ?

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
C6 C1 C2 122.6(3) . . ?
C6 C1 S1 117.2(3) . . ?
C2 C1 S1 120.2(3) . . ?
O3 C2 C1 120.1(3) . . ?
O3 C2 C3 125.0(3) . . ?
C1 C2 C3 114.9(3) . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 N1 118.0(4) . . ?
C2 C3 N1 119.8(4) . . ?
C5 C4 C3 122.0(4) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 117.3(4) . . ?
C4 C5 C8 122.0(4) . . ?
C6 C5 C8 120.7(4) . . ?
C1 C6 C5 121.1(4) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
F1 C7 F2 109.0(4) . . ?
F1 C7 F3 110.6(5) . . ?
F2 C7 F3 108.4(4) . . ?
F1 C7 S1 110.3(4) . . ?
F2 C7 S1 107.7(4) . . ?
F3 C7 S1 110.8(3) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 N1 O5 122.4(4) . . ?
O4 N1 C3 119.0(4) . . ?
O5 N1 C3 118.6(3) . . ?
C2 O3 H3 109.5 . . ?
O2 S1 O1 119.9(2) . . ?
O2 S1 C1 111.94(17) . . ?
O1 S1 C1 108.18(18) . . ?
O2 S1 C7 105.8(2) . . ?
O1 S1 C7 105.3(2) . . ?
C1 S1 C7 104.4(2) . . ?

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
C6 C1 C2 O3 -178.2(4) . . . . ?
S1 C1 C2 O3 2.5(6) . . . . ?
C6 C1 C2 C3 -0.6(6) . . . . ?
S1 C1 C2 C3 -179.9(3) . . . . ?
O3 C2 C3 C4 178.4(4) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
O3 C2 C3 N1 1.5(7) . . . . ?
C1 C2 C3 N1 -176.0(4) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
N1 C3 C4 C5 176.2(4) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C3 C4 C5 C8 -179.3(5) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
S1 C1 C6 C5 179.4(4) . . . . ?
C4 C5 C6 C1 0.0(7) . . . . ?
C8 C5 C6 C1 179.6(5) . . . . ?
C4 C3 N1 O4 -5.7(7) . . . . ?
C2 C3 N1 O4 171.4(4) . . . . ?
C4 C3 N1 O5 174.8(5) . . . . ?
C2 C3 N1 O5 -8.2(7) . . . . ?
C6 C1 S1 O2 -145.7(3) . . . . ?
C2 C1 S1 O2 33.6(4) . . . . ?
C6 C1 S1 O1 -11.5(4) . . . . ?
C2 C1 S1 O1 167.8(3) . . . . ?
C6 C1 S1 C7 100.3(4) . . . . ?
C2 C1 S1 C7 -80.4(4) . . . . ?
F1 C7 S1 O2 -177.7(4) . . . . ?
F2 C7 S1 O2 63.5(4) . . . . ?
F3 C7 S1 O2 -54.9(4) . . . . ?
F1 C7 S1 O1 54.4(4) . . . . ?
F2 C7 S1 O1 -64.3(4) . . . . ?
F3 C7 S1 O1 177.2(3) . . . . ?
F1 C7 S1 C1 -59.4(4) . . . . ?
F2 C7 S1 C1 -178.2(3) . . . . ?
F3 C7 S1 C1 63.4(4) . . . . ?

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
O3 H3 O5 0.84 1.85 2.569(4) 142.0 .
O3 H3 O1 0.84 2.27 2.889(4) 130.9 2
O3 H3 N1 0.84 2.46 2.900(4) 113.6 .

_diffrn_measured_fraction_theta_max 0.933
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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_s3776na
_database_code_depnum_ccdc_archive 'CCDC 1056927'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N O3'
_chemical_formula_weight         215.20

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   20.5236(9)
_cell_length_b                   7.6948(3)
_cell_length_c                   18.8253(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.529(2)
_cell_angle_gamma                90.00
_cell_volume                     2953.7(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3816
_cell_measurement_theta_min      4.34
_cell_measurement_theta_max      69.95

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.659741
_exptl_absorpt_correction_T_max  0.9409
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6146
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.34
_diffrn_reflns_theta_max         70.00
_reflns_number_total             3891
_reflns_number_gt                3658
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0805P)²+0.3519P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(19)
_refine_ls_number_reflns         3891
_refine_ls_number_parameters     437
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.69018(13) 0.3541(3) 0.21767(16) 0.0173(6) Uani 1 1 d . . .
C2 C 0.68257(12) 0.4116(3) 0.28752(15) 0.0145(5) Uani 1 1 d . . .
C3 C 0.67561(13) 0.5900(3) 0.29829(16) 0.0183(6) Uani 1 1 d . . .
H3 H 0.6706 0.6311 0.3449 0.022 Uiso 1 1 calc R . .
C4 C 0.67584(14) 0.7091(4) 0.24278(16) 0.0206(6) Uani 1 1 d . . .
H4 H 0.6715 0.8299 0.2515 0.025 Uiso 1 1 calc R . .
C5 C 0.68242(14) 0.6491(4) 0.17490(16) 0.0219(6) Uani 1 1 d . . .
H5 H 0.6819 0.7293 0.1365 0.026 Uiso 1 1 calc R . .
C6 C 0.68973(13) 0.4728(4) 0.16215(15) 0.0194(6) Uani 1 1 d . . .
H6 H 0.6944 0.4333 0.1152 0.023 Uiso 1 1 calc R . .
C7 C 0.68373(12) 0.2882(4) 0.34792(15) 0.0147(5) Uani 1 1 d . . .
C8 C 0.64986(12) 0.1302(3) 0.34035(14) 0.0154(5) Uani 1 1 d . . .
H8 H 0.6244 0.1040 0.2963 0.018 Uiso 1 1 calc R . .
C9 C 0.65268(12) 0.0115(3) 0.39585(15) 0.0165(6) Uani 1 1 d . . .
H9 H 0.6302 -0.0964 0.3901 0.020 Uiso 1 1 calc R . .
C10 C 0.68912(12) 0.0540(3) 0.46005(15) 0.0149(5) Uani 1 1 d . . .
C11 C 0.72126(12) 0.2119(3) 0.47102(15) 0.0150(5) Uani 1 1 d . . .
H11 H 0.7445 0.2398 0.5161 0.018 Uiso 1 1 calc R . .
C12 C 0.71860(13) 0.3279(3) 0.41449(15) 0.0160(5) Uani 1 1 d . . .
H12 H 0.7407 0.4362 0.4209 0.019 Uiso 1 1 calc R . .
C13 C 0.52308(12) 0.1455(3) 0.61742(16) 0.0174(6) Uani 1 1 d . . .
C14 C 0.52915(12) 0.0889(3) 0.54771(16) 0.0169(6) Uani 1 1 d . . .
C15 C 0.53476(13) -0.0908(3) 0.53651(15) 0.0176(6) Uani 1 1 d . . .
H15 H 0.5384 -0.1325 0.4896 0.021 Uiso 1 1 calc R . .
C16 C 0.53510(13) -0.2089(4) 0.59224(16) 0.0204(6) Uani 1 1 d . . .
H16 H 0.5393 -0.3297 0.5835 0.024 Uiso 1 1 calc R . .
C17 C 0.52933(14) -0.1496(4) 0.66096(16) 0.0213(6) Uani 1 1 d . . .
H17 H 0.5297 -0.2297 0.6994 0.026 Uiso 1 1 calc R . .
C18 C 0.52309(14) 0.0275(4) 0.67333(17) 0.0210(6) Uani 1 1 d . . .
H18 H 0.5188 0.0681 0.7202 0.025 Uiso 1 1 calc R . .
C19 C 0.52759(12) 0.2117(3) 0.48706(16) 0.0158(6) Uani 1 1 d . . .
C20 C 0.49022(13) 0.1743(3) 0.42171(15) 0.0166(6) Uani 1 1 d . . .
H20 H 0.4676 0.0666 0.4157 0.020 Uiso 1 1 calc R . .
C21 C 0.48588(12) 0.2922(3) 0.36582(15) 0.0174(6) Uani 1 1 d . . .
H21 H 0.4602 0.2673 0.3218 0.021 Uiso 1 1 calc R . .
C22 C 0.51992(13) 0.4479(4) 0.37564(15) 0.0154(5) Uani 1 1 d . . .
C23 C 0.55895(13) 0.4870(3) 0.43862(15) 0.0170(6) Uani 1 1 d . . .
H23 H 0.5824 0.5935 0.4437 0.020 Uiso 1 1 calc R . .
C24 C 0.56289(12) 0.3683(3) 0.49359(15) 0.0169(5) Uani 1 1 d . . .
H24 H 0.5900 0.3926 0.5368 0.020 Uiso 1 1 calc R . .
C25 C 0.83021(13) 0.8650(4) 0.41254(16) 0.0193(6) Uani 1 1 d . . .
C26 C 0.85913(12) 0.8907(4) 0.48306(15) 0.0176(6) Uani 1 1 d . . .
C27 C 0.89316(13) 1.0459(3) 0.49767(16) 0.0186(6) Uani 1 1 d . . .
H27 H 0.9145 1.0652 0.5445 0.022 Uiso 1 1 calc R . .
C28 C 0.89688(14) 1.1722(3) 0.44639(17) 0.0223(6) Uani 1 1 d . . .
H28 H 0.9210 1.2757 0.4580 0.027 Uiso 1 1 calc R . .
C29 C 0.86551(14) 1.1484(4) 0.37773(17) 0.0220(6) Uani 1 1 d . . .
H29 H 0.8665 1.2370 0.3427 0.026 Uiso 1 1 calc R . .
C30 C 0.83263(14) 0.9937(4) 0.36092(16) 0.0233(6) Uani 1 1 d . . .
H30 H 0.8116 0.9754 0.3139 0.028 Uiso 1 1 calc R . .
C31 C 0.85543(12) 0.7610(3) 0.54130(15) 0.0168(5) Uani 1 1 d . . .
C32 C 0.85779(13) 0.5818(3) 0.52916(15) 0.0179(5) Uani 1 1 d . . .
H32 H 0.8601 0.5407 0.4819 0.021 Uiso 1 1 calc R . .
C33 C 0.85680(13) 0.4634(4) 0.58400(16) 0.0198(6) Uani 1 1 d . . .
H33 H 0.8588 0.3421 0.5750 0.024 Uiso 1 1 calc R . .
C34 C 0.85275(14) 0.5254(3) 0.65296(15) 0.0215(6) Uani 1 1 d . . .
C35 C 0.85088(15) 0.7014(3) 0.66746(19) 0.0211(5) Uani 1 1 d . . .
H35 H 0.8487 0.7415 0.7149 0.025 Uiso 1 1 calc R . .
C36 C 0.85220(13) 0.8191(3) 0.61136(15) 0.0197(6) Uani 1 1 d . . .
H36 H 0.8509 0.9403 0.6207 0.024 Uiso 1 1 calc R . .
N1 N 0.69386(10) -0.0729(3) 0.51785(12) 0.0172(5) Uani 1 1 d . . .
N2 N 0.51244(11) 0.5777(3) 0.31904(13) 0.0192(5) Uani 1 1 d . . .
N3 N 0.85120(13) 0.4008(3) 0.71068(14) 0.0262(5) Uani 1 1 d . . .
O1 O 0.70029(10) 0.1813(2) 0.20866(11) 0.0215(4) Uani 1 1 d . . .
H1 H 0.7023 0.1605 0.1652 0.032 Uiso 1 1 calc R . .
O2 O 0.71303(10) -0.0212(3) 0.57855(11) 0.0232(4) Uani 1 1 d . . .
O3 O 0.67824(10) -0.2252(2) 0.50364(12) 0.0236(5) Uani 1 1 d . . .
O4 O 0.51497(10) 0.3195(2) 0.62781(11) 0.0202(4) Uani 1 1 d . . .
H4A H 0.5108 0.3382 0.6710 0.024(8) Uiso 1 1 calc R . .
O5 O 0.48891(11) 0.5314(3) 0.25862(11) 0.0269(5) Uani 1 1 d . . .
O6 O 0.52974(11) 0.7271(2) 0.33330(12) 0.0245(5) Uani 1 1 d . . .
O7 O 0.85219(14) 0.2455(3) 0.69681(14) 0.0380(6) Uani 1 1 d . . .
O8 O 0.84807(13) 0.4567(3) 0.77126(12) 0.0364(6) Uani 1 1 d . . .
O9 O 0.79913(11) 0.7129(3) 0.39582(12) 0.0308(5) Uani 1 1 d . . .
H9A H 0.7994 0.6928 0.3520 0.046 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
C1 O1 1.359(3) . ?
C1 C6 1.387(4) . ?
C1 C2 1.413(4) . ?
C2 C3 1.398(4) . ?
C2 C7 1.479(4) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.399(4) . ?
C7 C12 1.404(4) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(4) . ?
C10 N1 1.457(3) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O4 1.366(3) . ?
C13 C18 1.390(4) . ?
C13 C14 1.402(4) . ?
C14 C15 1.406(4) . ?
C14 C19 1.480(4) . ?
C15 C16 1.387(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.404(4) . ?
C19 C24 1.404(4) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(4) . ?
C22 N2 1.456(3) . ?
C23 C24 1.376(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 O9 1.352(3) . ?
C25 C30 1.392(4) . ?
C25 C26 1.405(4) . ?
C26 C27 1.395(4) . ?
C26 C31 1.491(4) . ?
C27 C28 1.378(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.400(4) . ?
C31 C36 1.401(4) . ?
C32 C33 1.379(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.395(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(4) . ?
C34 N3 1.452(4) . ?
C35 C36 1.394(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N1 O2 1.231(3) . ?
N1 O3 1.236(3) . ?
N2 O6 1.224(3) . ?
N2 O5 1.237(3) . ?
N3 O7 1.224(3) . ?
N3 O8 1.227(4) . ?
O1 H1 0.8400 . ?
O4 H4A 0.8400 . ?
O9 H9A 0.8400 . ?

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 C6 122.6(3) . . ?
O1 C1 C2 117.2(2) . . ?
C6 C1 C2 120.2(2) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 C7 120.8(3) . . ?
C1 C2 C7 121.4(2) . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C12 118.5(2) . . ?
C8 C7 C2 121.0(2) . . ?
C12 C7 C2 120.5(2) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C11 122.5(3) . . ?
C9 C10 N1 118.4(2) . . ?
C11 C10 N1 119.1(2) . . ?
C12 C11 C10 118.3(2) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C7 121.1(2) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O4 C13 C18 121.4(3) . . ?
O4 C13 C14 117.6(2) . . ?
C18 C13 C14 120.9(2) . . ?
C13 C14 C15 117.6(3) . . ?
C13 C14 C19 121.8(2) . . ?
C15 C14 C19 120.5(3) . . ?
C16 C15 C14 121.6(3) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 120.3(3) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C24 118.6(3) . . ?
C20 C19 C14 120.5(2) . . ?
C24 C19 C14 121.0(2) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 118.5(3) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C23 C22 C21 122.3(3) . . ?
C23 C22 N2 118.6(2) . . ?
C21 C22 N2 119.0(2) . . ?
C24 C23 C22 118.5(2) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C19 121.2(3) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
O9 C25 C30 120.4(3) . . ?
O9 C25 C26 118.6(2) . . ?
C30 C25 C26 120.9(3) . . ?
C27 C26 C25 117.1(3) . . ?
C27 C26 C31 119.6(2) . . ?
C25 C26 C31 123.3(2) . . ?
C28 C27 C26 122.1(3) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C28 C29 120.2(3) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 119.2(3) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C29 C30 C25 120.4(3) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C32 C31 C36 118.3(2) . . ?
C32 C31 C26 122.3(2) . . ?
C36 C31 C26 119.4(2) . . ?
C33 C32 C31 121.7(2) . . ?
C33 C32 H32 119.2 . . ?
C31 C32 H32 119.2 . . ?
C32 C33 C34 118.6(2) . . ?
C32 C33 H33 120.7 . . ?
C34 C33 H33 120.7 . . ?
C35 C34 C33 121.7(3) . . ?
C35 C34 N3 119.7(3) . . ?
C33 C34 N3 118.6(2) . . ?
C34 C35 C36 118.9(3) . . ?
C34 C35 H35 120.5 . . ?
C36 C35 H35 120.5 . . ?
C35 C36 C31 120.9(2) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
O2 N1 O3 123.7(2) . . ?
O2 N1 C10 117.6(2) . . ?
O3 N1 C10 118.7(2) . . ?
O6 N2 O5 123.1(2) . . ?
O6 N2 C22 118.7(2) . . ?
O5 N2 C22 118.2(2) . . ?
O7 N3 O8 123.0(3) . . ?
O7 N3 C34 118.9(2) . . ?
O8 N3 C34 118.1(2) . . ?
C1 O1 H1 109.5 . . ?
C13 O4 H4A 109.5 . . ?
C25 O9 H9A 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
O1 C1 C2 C3 176.7(2) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
O1 C1 C2 C7 -1.6(4) . . . . ?
C6 C1 C2 C7 -179.2(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C7 C2 C3 C4 178.5(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
O1 C1 C6 C5 -176.8(3) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C3 C2 C7 C8 137.9(3) . . . . ?
C1 C2 C7 C8 -43.8(3) . . . . ?
C3 C2 C7 C12 -41.6(3) . . . . ?
C1 C2 C7 C12 136.7(3) . . . . ?
C12 C7 C8 C9 -2.8(4) . . . . ?
C2 C7 C8 C9 177.6(2) . . . . ?
C7 C8 C9 C10 1.2(4) . . . . ?
C8 C9 C10 C11 1.6(4) . . . . ?
C8 C9 C10 N1 -178.1(2) . . . . ?
C9 C10 C11 C12 -2.5(4) . . . . ?
N1 C10 C11 C12 177.2(2) . . . . ?
C10 C11 C12 C7 0.7(4) . . . . ?
C8 C7 C12 C11 1.9(4) . . . . ?
C2 C7 C12 C11 -178.6(2) . . . . ?
O4 C13 C14 C15 -177.4(2) . . . . ?
C18 C13 C14 C15 0.4(4) . . . . ?
O4 C13 C14 C19 0.6(4) . . . . ?
C18 C13 C14 C19 178.4(2) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C19 C14 C15 C16 -178.8(2) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
O4 C13 C18 C17 177.9(2) . . . . ?
C14 C13 C18 C17 0.2(4) . . . . ?
C16 C17 C18 C13 -0.5(4) . . . . ?
C13 C14 C19 C20 -135.2(3) . . . . ?
C15 C14 C19 C20 42.8(4) . . . . ?
C13 C14 C19 C24 44.4(4) . . . . ?
C15 C14 C19 C24 -137.6(3) . . . . ?
C24 C19 C20 C21 -2.8(4) . . . . ?
C14 C19 C20 C21 176.8(2) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 C23 1.4(4) . . . . ?
C20 C21 C22 N2 -176.1(2) . . . . ?
C21 C22 C23 C24 -1.2(4) . . . . ?
N2 C22 C23 C24 176.3(2) . . . . ?
C22 C23 C24 C19 -1.0(4) . . . . ?
C20 C19 C24 C23 3.0(4) . . . . ?
C14 C19 C24 C23 -176.6(2) . . . . ?
O9 C25 C26 C27 177.3(2) . . . . ?
C30 C25 C26 C27 -3.5(4) . . . . ?
O9 C25 C26 C31 -2.1(4) . . . . ?
C30 C25 C26 C31 177.1(2) . . . . ?
C25 C26 C27 C28 2.1(4) . . . . ?
C31 C26 C27 C28 -178.4(2) . . . . ?
C26 C27 C28 C29 0.8(4) . . . . ?
C27 C28 C29 C30 -2.4(4) . . . . ?
C28 C29 C30 C25 1.0(4) . . . . ?
O9 C25 C30 C29 -178.9(3) . . . . ?
C26 C25 C30 C29 2.0(4) . . . . ?
C27 C26 C31 C32 -142.9(3) . . . . ?
C25 C26 C31 C32 36.6(4) . . . . ?
C27 C26 C31 C36 34.4(3) . . . . ?
C25 C26 C31 C36 -146.1(3) . . . . ?
C36 C31 C32 C33 0.2(4) . . . . ?
C26 C31 C32 C33 177.5(2) . . . . ?
C31 C32 C33 C34 0.6(4) . . . . ?
C32 C33 C34 C35 -1.1(4) . . . . ?
C32 C33 C34 N3 179.5(3) . . . . ?
C33 C34 C35 C36 0.9(4) . . . . ?
N3 C34 C35 C36 -179.8(3) . . . . ?
C34 C35 C36 C31 -0.1(4) . . . . ?
C32 C31 C36 C35 -0.5(4) . . . . ?
C26 C31 C36 C35 -177.9(3) . . . . ?
C9 C10 N1 O2 -163.8(2) . . . . ?
C11 C10 N1 O2 16.5(3) . . . . ?
C9 C10 N1 O3 15.8(3) . . . . ?
C11 C10 N1 O3 -163.9(2) . . . . ?
C23 C22 N2 O6 -14.0(3) . . . . ?
C21 C22 N2 O6 163.5(2) . . . . ?
C23 C22 N2 O5 165.8(2) . . . . ?
C21 C22 N2 O5 -16.6(4) . . . . ?
C35 C34 N3 O7 179.2(3) . . . . ?
C33 C34 N3 O7 -1.4(4) . . . . ?
C35 C34 N3 O8 0.2(4) . . . . ?
C33 C34 N3 O8 179.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.98 2.780(3) 157.9 2_554
O4 H4A O5 0.84 2.02 2.822(3) 158.5 2_565
O9 H9A O8 0.84 2.23 2.958(3) 144.8 2_564

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_s3883ma
_database_code_depnum_ccdc_archive 'CCDC 1056928'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N2 O5 S Si'
_chemical_formula_weight         352.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.2148(2)
_cell_length_b                   10.9938(2)
_cell_length_c                   12.0527(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.8790(10)
_cell_angle_gamma                90.00
_cell_volume                     1624.90(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9042
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      72.16

_exptl_crystal_description       cuboid
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    2.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.553297
_exptl_absorpt_correction_T_max  0.6695
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15650
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_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         3.60
_diffrn_reflns_theta_max         72.15
_reflns_number_total             3176
_reflns_number_gt                2930
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0470P)²+0.5935P] 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         3176
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0807
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_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 1.06569(14) 0.27306(16) 1.31857(14) 0.0333(3) Uani 1 1 d . . .
H1A H 1.1347 0.2281 1.3452 0.050 Uiso 1 1 calc R . .
H1B H 1.0132 0.2298 1.3440 0.050 Uiso 1 1 calc R . .
H1C H 1.0782 0.3547 1.3538 0.050 Uiso 1 1 calc R . .
C2 C 0.99433(12) 0.13015(13) 1.08706(14) 0.0269(3) Uani 1 1 d . . .
H2A H 0.9520 0.1343 1.0009 0.040 Uiso 1 1 calc R . .
H2B H 0.9562 0.0785 1.1252 0.040 Uiso 1 1 calc R . .
H2C H 1.0664 0.0957 1.1009 0.040 Uiso 1 1 calc R . .
C3 C 1.10184(12) 0.38372(14) 1.10455(14) 0.0276(3) Uani 1 1 d . . .
H3A H 1.1720 0.3426 1.1228 0.041 Uiso 1 1 calc R . .
H3B H 1.1135 0.4613 1.1476 0.041 Uiso 1 1 calc R . .
H3C H 1.0682 0.3988 1.0183 0.041 Uiso 1 1 calc R . .
C4 C 0.87076(11) 0.35718(12) 1.10459(12) 0.0196(3) Uani 1 1 d . . .
C5 C 0.80076(11) 0.35047(11) 0.97868(12) 0.0181(3) Uani 1 1 d . . .
C6 C 0.65888(12) 0.45423(14) 1.03208(14) 0.0278(3) Uani 1 1 d . . .
H6 H 0.5879 0.4887 1.0067 0.033 Uiso 1 1 calc R . .
C7 C 0.72719(13) 0.46662(14) 1.14578(14) 0.0305(3) Uani 1 1 d . . .
H7 H 0.7056 0.5104 1.2012 0.037 Uiso 1 1 calc R . .
C8 C 0.83276(12) 0.41317(13) 1.18248(13) 0.0251(3) Uani 1 1 d . . .
H8 H 0.8787 0.4166 1.2646 0.030 Uiso 1 1 calc R . .
C9 C 0.62654(10) 0.43994(12) 0.70992(12) 0.0204(3) Uani 1 1 d . . .
C10 C 0.59350(12) 0.56075(13) 0.69596(13) 0.0261(3) Uani 1 1 d . . .
H10 H 0.5586 0.5951 0.7447 0.031 Uiso 1 1 calc R . .
C11 C 0.61238(13) 0.63021(14) 0.60987(14) 0.0276(3) Uani 1 1 d . . .
H11 H 0.5914 0.7133 0.5987 0.033 Uiso 1 1 calc R . .
C12 C 0.66240(11) 0.57562(13) 0.54068(12) 0.0232(3) Uani 1 1 d . . .
C13 C 0.69559(12) 0.45538(14) 0.55366(13) 0.0269(3) Uani 1 1 d . . .
H13 H 0.7298 0.4211 0.5042 0.032 Uiso 1 1 calc R . .
C14 C 0.67763(12) 0.38636(13) 0.64050(13) 0.0260(3) Uani 1 1 d . . .
H14 H 0.6999 0.3037 0.6524 0.031 Uiso 1 1 calc R . .
N1 N 0.69129(9) 0.39111(10) 0.95080(10) 0.0208(2) Uani 1 1 d . . .
N2 N 0.68155(11) 0.65015(12) 0.44819(11) 0.0294(3) Uani 1 1 d . . .
O1 O 0.82686(8) 0.31140(9) 0.89842(8) 0.0228(2) Uani 1 1 d . . .
O2 O 0.60870(9) 0.22655(9) 0.79679(10) 0.0299(2) Uani 1 1 d . . .
O3 O 0.49524(8) 0.39589(11) 0.81973(10) 0.0327(3) Uani 1 1 d . . .
O4 O 0.73680(10) 0.60634(12) 0.39643(10) 0.0380(3) Uani 1 1 d . . .
O5 O 0.64149(12) 0.75162(12) 0.42897(12) 0.0450(3) Uani 1 1 d . . .
S1 S 0.59573(3) 0.35218(3) 0.81561(3) 0.02270(11) Uani 1 1 d . . .
Si1 Si 1.01031(3) 0.28570(3) 1.15196(3) 0.01942(11) 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 Si1 1.8686(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 Si1 1.8595(15) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 Si1 1.8617(15) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C8 1.3652(19) . ?
C4 C5 1.4553(19) . ?
C4 Si1 1.8867(14) . ?
C5 O1 1.2198(16) . ?
C5 N1 1.4293(17) . ?
C6 C7 1.338(2) . ?
C6 N1 1.3919(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.424(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.387(2) . ?
C9 C10 1.389(2) . ?
C9 S1 1.7624(14) . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(2) . ?
C12 N2 1.4793(19) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
N1 S1 1.7027(12) . ?
N2 O5 1.2194(19) . ?
N2 O4 1.2221(18) . ?
O2 S1 1.4203(11) . ?
O3 S1 1.4304(11) . ?

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
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C8 C4 C5 119.09(13) . . ?
C8 C4 Si1 123.24(11) . . ?
C5 C4 Si1 117.66(10) . . ?
O1 C5 N1 118.96(12) . . ?
O1 C5 C4 125.95(12) . . ?
N1 C5 C4 115.07(11) . . ?
C7 C6 N1 120.31(13) . . ?
C7 C6 H6 119.8 . . ?
N1 C6 H6 119.8 . . ?
C6 C7 C8 119.02(13) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C4 C8 C7 122.78(14) . . ?
C4 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C14 C9 C10 122.33(13) . . ?
C14 C9 S1 119.93(11) . . ?
C10 C9 S1 117.67(11) . . ?
C11 C10 C9 118.83(13) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C10 118.30(13) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 123.40(14) . . ?
C11 C12 N2 118.02(13) . . ?
C13 C12 N2 118.58(13) . . ?
C14 C13 C12 118.25(13) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C9 118.88(13) . . ?
C13 C14 H14 120.6 . . ?
C9 C14 H14 120.6 . . ?
C6 N1 C5 122.70(12) . . ?
C6 N1 S1 119.07(10) . . ?
C5 N1 S1 118.11(9) . . ?
O5 N2 O4 124.28(14) . . ?
O5 N2 C12 117.76(13) . . ?
O4 N2 C12 117.96(13) . . ?
O2 S1 O3 120.07(7) . . ?
O2 S1 N1 107.86(6) . . ?
O3 S1 N1 104.44(6) . . ?
O2 S1 C9 110.05(7) . . ?
O3 S1 C9 107.98(7) . . ?
N1 S1 C9 105.39(6) . . ?
C2 Si1 C3 112.84(7) . . ?
C2 Si1 C1 108.74(7) . . ?
C3 Si1 C1 109.50(8) . . ?
C2 Si1 C4 108.11(6) . . ?
C3 Si1 C4 109.85(6) . . ?
C1 Si1 C4 107.66(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
C8 C4 C5 O1 174.27(13) . . . . ?
Si1 C4 C5 O1 -6.33(18) . . . . ?
C8 C4 C5 N1 -7.57(18) . . . . ?
Si1 C4 C5 N1 171.84(9) . . . . ?
N1 C6 C7 C8 -0.7(2) . . . . ?
C5 C4 C8 C7 -0.5(2) . . . . ?
Si1 C4 C8 C7 -179.87(12) . . . . ?
C6 C7 C8 C4 5.0(2) . . . . ?
C14 C9 C10 C11 -0.1(2) . . . . ?
S1 C9 C10 C11 -177.17(11) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C10 C11 C12 N2 179.54(13) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
N2 C12 C13 C14 179.86(13) . . . . ?
C12 C13 C14 C9 0.5(2) . . . . ?
C10 C9 C14 C13 -0.5(2) . . . . ?
S1 C9 C14 C13 176.50(11) . . . . ?
C7 C6 N1 C5 -8.2(2) . . . . ?
C7 C6 N1 S1 167.76(12) . . . . ?
O1 C5 N1 C6 -169.62(13) . . . . ?
C4 C5 N1 C6 12.07(18) . . . . ?
O1 C5 N1 S1 14.43(16) . . . . ?
C4 C5 N1 S1 -163.88(9) . . . . ?
C11 C12 N2 O5 -8.0(2) . . . . ?
C13 C12 N2 O5 172.20(14) . . . . ?
C11 C12 N2 O4 171.73(14) . . . . ?
C13 C12 N2 O4 -8.1(2) . . . . ?
C6 N1 S1 O2 -130.05(11) . . . . ?
C5 N1 S1 O2 46.05(11) . . . . ?
C6 N1 S1 O3 -1.25(12) . . . . ?
C5 N1 S1 O3 174.85(10) . . . . ?
C6 N1 S1 C9 112.42(11) . . . . ?
C5 N1 S1 C9 -71.48(11) . . . . ?
C14 C9 S1 O2 -12.37(13) . . . . ?
C10 C9 S1 O2 164.77(11) . . . . ?
C14 C9 S1 O3 -145.15(12) . . . . ?
C10 C9 S1 O3 31.99(13) . . . . ?
C14 C9 S1 N1 103.67(12) . . . . ?
C10 C9 S1 N1 -79.19(12) . . . . ?
C8 C4 Si1 C2 130.89(12) . . . . ?
C5 C4 Si1 C2 -48.48(12) . . . . ?
C8 C4 Si1 C3 -105.59(13) . . . . ?
C5 C4 Si1 C3 75.03(11) . . . . ?
C8 C4 Si1 C1 13.58(14) . . . . ?
C5 C4 Si1 C1 -165.80(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_s3898ma
_database_code_depnum_ccdc_archive 'CCDC 1056929'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O5'
_chemical_formula_weight         274.23

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   15.6137(4)
_cell_length_b                   7.7484(2)
_cell_length_c                   21.2252(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.1920(10)
_cell_angle_gamma                90.00
_cell_volume                     2410.03(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8091
_cell_measurement_theta_min      4.42
_cell_measurement_theta_max      72.31

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    1.010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.658587
_exptl_absorpt_correction_T_max  0.8633
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12895
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         6.04
_diffrn_reflns_theta_max         72.30
_reflns_number_total             4561
_reflns_number_gt                4263
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0411P)²+2.7535P] 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         4561
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
C12 C 0.59808(12) 1.0577(2) 0.09708(10) 0.0193(4) Uani 1 1 d . . .
C1 C 0.87580(12) 1.0754(2) 0.28709(9) 0.0148(3) Uani 1 1 d . . .
C2 C 0.91676(12) 1.0929(2) 0.35703(9) 0.0157(4) Uani 1 1 d . . .
C3 C 0.87453(12) 1.0361(2) 0.40158(9) 0.0164(4) Uani 1 1 d . . .
H3 H 0.9048 1.0484 0.4486 0.020 Uiso 1 1 calc R . .
C4 C 0.78886(12) 0.9622(2) 0.37733(9) 0.0168(4) Uani 1 1 d . . .
C5 C 0.74735(12) 0.9462(2) 0.30761(9) 0.0154(3) Uani 1 1 d . . .
H5 H 0.6880 0.8971 0.2904 0.018 Uiso 1 1 calc R . .
C6 C 0.78875(12) 0.9985(2) 0.26255(9) 0.0146(3) Uani 1 1 d . . .
C7 C 0.74048(13) 0.9003(3) 0.42356(10) 0.0215(4) Uani 1 1 d . . .
H7A H 0.7845 0.8900 0.4693 0.032 Uiso 1 1 calc R . .
H7B H 0.7127 0.7874 0.4083 0.032 Uiso 1 1 calc R . .
H7C H 0.6928 0.9832 0.4231 0.032 Uiso 1 1 calc R . .
C8 C 0.73787(12) 0.9843(2) 0.18910(9) 0.0141(3) Uani 1 1 d . . .
C9 C 0.76857(11) 0.9094(2) 0.14048(9) 0.0137(3) Uani 1 1 d . . .
C10 C 0.71653(12) 0.9060(2) 0.07273(9) 0.0163(4) Uani 1 1 d . . .
H10 H 0.7395 0.8521 0.0416 0.020 Uiso 1 1 calc R . .
C11 C 0.63083(12) 0.9817(2) 0.05067(9) 0.0186(4) Uani 1 1 d . . .
H11 H 0.5949 0.9815 0.0043 0.022 Uiso 1 1 calc R . .
H12 H 0.5395 1.1103 0.0824 0.022 Uiso 1 1 d R . .
C13 C 0.65039(12) 1.0573(2) 0.16483(9) 0.0172(4) Uani 1 1 d . . .
H13 H 0.6261 1.1082 0.1958 0.021 Uiso 1 1 calc R . .
C14 C 0.15558(12) 0.9176(2) 0.27953(9) 0.0143(3) Uani 1 1 d . . .
C15 C 0.18140(12) 0.8991(2) 0.34939(9) 0.0164(4) Uani 1 1 d . . .
C16 C 0.26641(12) 0.9545(2) 0.39303(9) 0.0174(4) Uani 1 1 d . . .
H16 H 0.2812 0.9426 0.4402 0.021 Uiso 1 1 calc R . .
C17 C 0.32873(12) 1.0260(2) 0.36803(9) 0.0177(4) Uani 1 1 d . . .
C18 C 0.30377(12) 1.0432(2) 0.29822(9) 0.0160(4) Uani 1 1 d . . .
H18 H 0.3467 1.0909 0.2804 0.019 Uiso 1 1 calc R . .
C19 C 0.21902(12) 0.9934(2) 0.25411(9) 0.0146(3) Uani 1 1 d . . .
C20 C 0.42146(13) 1.0866(3) 0.41342(10) 0.0230(4) Uani 1 1 d . . .
H20A H 0.4231 1.0882 0.4600 0.034 Uiso 1 1 calc R . .
H20B H 0.4329 1.2031 0.4002 0.034 Uiso 1 1 calc R . .
H20C H 0.4685 1.0078 0.4095 0.034 Uiso 1 1 calc R . .
C21 C 0.19810(12) 1.0083(2) 0.18033(9) 0.0147(3) Uani 1 1 d . . .
C22 C 0.11891(12) 1.0817(2) 0.13427(9) 0.0156(4) Uani 1 1 d . . .
C23 C 0.10097(13) 1.0801(2) 0.06552(9) 0.0191(4) Uani 1 1 d . . .
H23 H 0.0462 1.1295 0.0358 0.023 Uiso 1 1 calc R . .
C24 C 0.16347(13) 1.0061(3) 0.04054(10) 0.0214(4) Uani 1 1 d . . .
H24 H 0.1514 1.0028 -0.0065 0.026 Uiso 1 1 calc R . .
C25 C 0.24385(13) 0.9369(2) 0.08473(10) 0.0206(4) Uani 1 1 d . . .
H25 H 0.2877 0.8888 0.0680 0.025 Uiso 1 1 calc R . .
C26 C 0.26025(12) 0.9376(2) 0.15322(9) 0.0176(4) Uani 1 1 d . . .
H26 H 0.3153 0.8887 0.1826 0.021 Uiso 1 1 calc R . .
N1 N 1.00602(10) 1.1728(2) 0.38556(8) 0.0182(3) Uani 1 1 d . . .
N2 N 0.85757(10) 0.82166(19) 0.15886(7) 0.0152(3) Uani 1 1 d . . .
N3 N 0.11929(11) 0.8229(2) 0.37863(8) 0.0188(3) Uani 1 1 d . . .
N4 N 0.05083(10) 1.1705(2) 0.15646(8) 0.0170(3) Uani 1 1 d . . .
O1 O 0.91173(8) 1.12926(17) 0.24140(6) 0.0169(3) Uani 1 1 d . . .
H1 H 0.9643 1.1686 0.2611 0.025 Uiso 1 1 calc R . .
O2 O 1.04624(9) 1.2205(2) 0.34719(7) 0.0272(3) Uani 1 1 d . . .
O3 O 1.03987(9) 1.19057(19) 0.44657(7) 0.0270(3) Uani 1 1 d . . .
O4 O 0.89216(8) 0.76516(16) 0.21612(6) 0.0169(3) Uani 1 1 d . . .
O5 O 0.89210(9) 0.8054(2) 0.11542(7) 0.0252(3) Uani 1 1 d . . .
O6 O 0.07566(8) 0.86681(16) 0.23442(6) 0.0165(3) Uani 1 1 d . . .
H6 H 0.0420 0.8279 0.2546 0.025 Uiso 1 1 calc R . .
O7 O 0.14144(10) 0.8148(2) 0.43988(7) 0.0285(3) Uani 1 1 d . . .
O8 O 0.04440(9) 0.7680(2) 0.34080(7) 0.0283(3) Uani 1 1 d . . .
O9 O 0.07594(9) 1.23378(16) 0.21309(6) 0.0186(3) Uani 1 1 d . . .
O10 O -0.02747(9) 1.1812(2) 0.11664(7) 0.0279(3) 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
C12 C13 1.387(3) . ?
C12 C11 1.388(3) . ?
C12 H12 0.9498 . ?
C1 O1 1.343(2) . ?
C1 C2 1.406(3) . ?
C1 C6 1.409(2) . ?
C2 C3 1.397(3) . ?
C2 N1 1.453(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(3) . ?
C4 C7 1.509(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C8 1.489(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.402(2) . ?
C8 C9 1.405(2) . ?
C9 C10 1.386(3) . ?
C9 N2 1.474(2) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C14 O6 1.343(2) . ?
C14 C15 1.403(2) . ?
C14 C19 1.409(2) . ?
C15 C16 1.398(3) . ?
C15 N3 1.445(2) . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.402(3) . ?
C17 C20 1.511(3) . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 C21 1.490(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.399(2) . ?
C21 C22 1.405(2) . ?
C22 C23 1.388(3) . ?
C22 N4 1.473(2) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N1 O3 1.226(2) . ?
N1 O2 1.244(2) . ?
N2 O5 1.225(2) . ?
N2 O4 1.2276(19) . ?
N3 O7 1.226(2) . ?
N3 O8 1.243(2) . ?
N4 O10 1.226(2) . ?
N4 O9 1.230(2) . ?
O1 H1 0.8400 . ?
O6 H6 0.8400 . ?

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
C13 C12 C11 120.36(17) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O1 C1 C2 125.54(16) . . ?
O1 C1 C6 117.02(16) . . ?
C2 C1 C6 117.41(16) . . ?
C3 C2 C1 122.37(16) . . ?
C3 C2 N1 117.46(16) . . ?
C1 C2 N1 120.17(16) . . ?
C4 C3 C2 120.06(17) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 117.77(16) . . ?
C3 C4 C7 121.84(17) . . ?
C5 C4 C7 120.38(17) . . ?
C6 C5 C4 123.13(16) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 C1 119.24(17) . . ?
C5 C6 C8 119.54(16) . . ?
C1 C6 C8 121.07(16) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 115.66(16) . . ?
C13 C8 C6 117.07(15) . . ?
C9 C8 C6 127.25(16) . . ?
C10 C9 C8 122.92(16) . . ?
C10 C9 N2 115.30(15) . . ?
C8 C9 N2 121.74(15) . . ?
C11 C10 C9 119.62(17) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 119.27(17) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C12 C13 C8 122.16(17) . . ?
C12 C13 H13 118.9 . . ?
C8 C13 H13 118.9 . . ?
O6 C14 C15 125.50(16) . . ?
O6 C14 C19 116.87(15) . . ?
C15 C14 C19 117.62(16) . . ?
C16 C15 C14 121.97(16) . . ?
C16 C15 N3 117.71(16) . . ?
C14 C15 N3 120.32(16) . . ?
C17 C16 C15 120.28(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 118.05(17) . . ?
C16 C17 C20 121.95(17) . . ?
C18 C17 C20 120.00(17) . . ?
C19 C18 C17 122.66(16) . . ?
C19 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
C18 C19 C14 119.39(16) . . ?
C18 C19 C21 120.02(15) . . ?
C14 C19 C21 120.44(15) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 116.17(16) . . ?
C26 C21 C19 118.06(16) . . ?
C22 C21 C19 125.72(16) . . ?
C23 C22 C21 122.54(17) . . ?
C23 C22 N4 115.73(15) . . ?
C21 C22 N4 121.70(16) . . ?
C24 C23 C22 119.53(17) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 119.54(17) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.20(17) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 121.98(17) . . ?
C25 C26 H26 119.0 . . ?
C21 C26 H26 119.0 . . ?
O3 N1 O2 121.82(15) . . ?
O3 N1 C2 119.33(15) . . ?
O2 N1 C2 118.85(15) . . ?
O5 N2 O4 123.44(15) . . ?
O5 N2 C9 117.91(15) . . ?
O4 N2 C9 118.63(14) . . ?
O7 N3 O8 121.69(16) . . ?
O7 N3 C15 119.40(16) . . ?
O8 N3 C15 118.91(15) . . ?
O10 N4 O9 123.52(16) . . ?
O10 N4 C22 117.99(15) . . ?
O9 N4 C22 118.47(14) . . ?
C1 O1 H1 109.5 . . ?
C14 O6 H6 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
O1 C1 C2 C3 178.92(16) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
O1 C1 C2 N1 -0.9(3) . . . . ?
C6 C1 C2 N1 -179.32(15) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
N1 C2 C3 C4 178.73(15) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C3 C4 C7 -179.56(16) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C7 C4 C5 C6 -179.14(16) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C8 -177.10(16) . . . . ?
O1 C1 C6 C5 -177.79(15) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
O1 C1 C6 C8 -2.3(2) . . . . ?
C2 C1 C6 C8 176.28(15) . . . . ?
C5 C6 C8 C13 51.7(2) . . . . ?
C1 C6 C8 C13 -123.74(18) . . . . ?
C5 C6 C8 C9 -130.06(19) . . . . ?
C1 C6 C8 C9 54.5(2) . . . . ?
C13 C8 C9 C10 -0.3(2) . . . . ?
C6 C8 C9 C10 -178.50(16) . . . . ?
C13 C8 C9 N2 -177.51(15) . . . . ?
C6 C8 C9 N2 4.3(3) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
N2 C9 C10 C11 178.54(15) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C13 C12 C11 C10 -0.3(3) . . . . ?
C11 C12 C13 C8 1.2(3) . . . . ?
C9 C8 C13 C12 -0.9(3) . . . . ?
C6 C8 C13 C12 177.53(16) . . . . ?
O6 C14 C15 C16 179.54(16) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
O6 C14 C15 N3 -1.2(3) . . . . ?
C19 C14 C15 N3 179.76(15) . . . . ?
C14 C15 C16 C17 -1.5(3) . . . . ?
N3 C15 C16 C17 179.21(16) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C15 C16 C17 C20 -179.68(17) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C20 C17 C18 C19 -178.61(17) . . . . ?
C17 C18 C19 C14 -1.9(3) . . . . ?
C17 C18 C19 C21 -177.45(16) . . . . ?
O6 C14 C19 C18 -177.96(15) . . . . ?
C15 C14 C19 C18 1.1(2) . . . . ?
O6 C14 C19 C21 -2.4(2) . . . . ?
C15 C14 C19 C21 176.68(15) . . . . ?
C18 C19 C21 C26 50.6(2) . . . . ?
C14 C19 C21 C26 -124.87(18) . . . . ?
C18 C19 C21 C22 -132.04(19) . . . . ?
C14 C19 C21 C22 52.5(2) . . . . ?
C26 C21 C22 C23 2.1(3) . . . . ?
C19 C21 C22 C23 -175.28(17) . . . . ?
C26 C21 C22 N4 -175.95(15) . . . . ?
C19 C21 C22 N4 6.7(3) . . . . ?
C21 C22 C23 C24 -1.0(3) . . . . ?
N4 C22 C23 C24 177.15(16) . . . . ?
C22 C23 C24 C25 -1.0(3) . . . . ?
C23 C24 C25 C26 1.7(3) . . . . ?
C24 C25 C26 C21 -0.6(3) . . . . ?
C22 C21 C26 C25 -1.3(3) . . . . ?
C19 C21 C26 C25 176.29(16) . . . . ?
C3 C2 N1 O3 -1.4(2) . . . . ?
C1 C2 N1 O3 178.36(16) . . . . ?
C3 C2 N1 O2 178.17(16) . . . . ?
C1 C2 N1 O2 -2.0(2) . . . . ?
C10 C9 N2 O5 23.9(2) . . . . ?
C8 C9 N2 O5 -158.62(16) . . . . ?
C10 C9 N2 O4 -154.34(15) . . . . ?
C8 C9 N2 O4 23.1(2) . . . . ?
C16 C15 N3 O7 2.5(2) . . . . ?
C14 C15 N3 O7 -176.81(16) . . . . ?
C16 C15 N3 O8 -177.87(16) . . . . ?
C14 C15 N3 O8 2.9(2) . . . . ?
C23 C22 N4 O10 25.3(2) . . . . ?
C21 C22 N4 O10 -156.58(17) . . . . ?
C23 C22 N4 O9 -152.82(16) . . . . ?
C21 C22 N4 O9 25.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.88 2.5880(18) 141.6 .
O1 H1 O9 0.84 2.36 2.9419(17) 127.2 1_655
O1 H1 N1 0.84 2.49 2.921(2) 112.7 .
O6 H6 O8 0.84 1.88 2.5853(18) 141.3 .
O6 H6 O4 0.84 2.25 2.8655(17) 130.4 1_455
O6 H6 N3 0.84 2.49 2.917(2) 112.6 .

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.077
