# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_SA
_database_code_depnum_ccdc_archive 'CCDC 1060811'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;
#===================================================================== 
_chemical_name_systematic        ?
_chemical_name_common            'Sinapic Acid'
_chemical_formula_moiety         'C11 H12 O5'
_chemical_formula_sum            'C11 H12 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         224.21

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   4.7531(7)
_cell_length_b                   15.683(2)
_cell_length_c                   14.170(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.383(3)
_cell_angle_gamma                90
_cell_volume                     1056.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3806
_cell_measurement_theta_min      2.5974
_cell_measurement_theta_max      25.3608
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEXII DUO'
_diffrn_measurement_method       'φ & ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14863
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_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.
;

_reflns_number_total             2159
_reflns_number_gt                1546
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1148
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_restrained_S_all      1.301
_refine_ls_number_reflns         2159
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0518P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.159
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2011.12.3.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al., 2008)'
_computing_publication_material  ?

_iucr_refine_instruction_details 
;
TITL mo_SEL_AS_EOC_SA_2_0ma in P2(1)/n
CELL 0.71073   4.7531  15.6833  14.1701  90.000  90.383  90.000
ZERR    4.00   0.0007   0.0023   0.0021   0.000   0.003   0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C  H  O
UNIT 44  48  20
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 20
SIZE 0.130 0.180 0.450
HTAB O10 O11_$1
HTAB O14 O11_$2
HTAB O14 O15
EQIV $1_[ -x+1, -y, -z+2 ]
EQIV $2_[ -x-1/2, y+1/2, -z+3/2 ]
CONF
TEMP 23.000
WGHT    0.051800
FVAR       0.11957
MOLE 1
C1    1    0.112839    0.315554    0.842585    11.00000    0.04186    0.03537 =
         0.04284    0.00481   -0.00421    0.00146
C2    1   -0.092224    0.300516    0.773294    11.00000    0.04634    0.03190 =
         0.04686    0.00281   -0.00675   -0.00027
AFIX  43
H2    2   -0.138547    0.244887    0.756600    11.00000   -1.20000
AFIX   0
C3    1   -0.225335    0.367848    0.729852    11.00000    0.03963    0.03997 =
         0.04692    0.00363   -0.00671    0.00143
C4    1   -0.163870    0.451784    0.755046    11.00000    0.04439    0.03542 =
         0.05167    0.00694   -0.00741    0.00569
C5    1    0.039503    0.467441    0.824327    11.00000    0.04830    0.03264 =
         0.05700    0.00046   -0.00758    0.00135
C6    1    0.176852    0.399488    0.866764    11.00000    0.04709    0.03867 =
         0.04914    0.00194   -0.01171    0.00044
AFIX  43
H6    2    0.314396    0.410082    0.912255    11.00000   -1.20000
AFIX   0
C7    1    0.258945    0.244946    0.889673    11.00000    0.04486    0.03608 =
         0.04276    0.00281   -0.00808    0.00028
AFIX  43
H7    2    0.408136    0.258917    0.929556    11.00000   -1.20000
AFIX   0
C8    1    0.197434    0.163136    0.880474    11.00000    0.05465    0.03804 =
         0.05281    0.00500   -0.01989   -0.00127
AFIX  43
H8    2    0.055188    0.148651    0.838037    11.00000   -1.20000
AFIX   0
C9    1    0.334766    0.093843    0.931534    11.00000    0.04672    0.03486 =
         0.04606    0.00283   -0.01060   -0.00048
O10   3    0.542924    0.113295    0.987067    11.00000    0.06005    0.03760 =
         0.06319    0.00625   -0.02831   -0.00252
H10   2    0.623643    0.064386    1.018572    11.00000    0.10466
O11   3    0.246057    0.019188    0.921759    11.00000    0.05958    0.03310 =
         0.06642    0.00802   -0.02262   -0.00479
O12   3    0.083612    0.552260    0.845729    11.00000    0.06886    0.03194 =
         0.09032   -0.00076   -0.03517    0.00368
C13   1    0.299491    0.571600    0.911208    11.00000    0.07517    0.03978 =
         0.08875   -0.00725   -0.03107    0.00046
AFIX 137
H13A  2    0.258897    0.545004    0.970597    11.00000   -1.50000
H13B  2    0.310611    0.632251    0.919585    11.00000   -1.50000
H13C  2    0.475763    0.550696    0.887967    11.00000   -1.50000
AFIX   0
O14   3   -0.298036    0.518722    0.713918    11.00000    0.06009    0.03573 =
         0.07628    0.00618   -0.02711    0.00630
H14   2   -0.425546    0.498202    0.674737    11.00000    0.09054
O15   3   -0.426453    0.361035    0.660514    11.00000    0.05733    0.04106 =
         0.06097    0.00291   -0.02361    0.00232
C16   1   -0.494707    0.278037    0.628624    11.00000    0.06322    0.04743 =
         0.05159   -0.00297   -0.01677    0.00089
AFIX 137
H16A  2   -0.329966    0.251531    0.602999    11.00000   -1.50000
H16B  2   -0.637902    0.281540    0.580681    11.00000   -1.50000
H16C  2   -0.562563    0.244727    0.680554    11.00000   -1.50000
HKLF 4
 
REM  mo_SEL_AS_EOC_SA_2_0ma in P2(1)/n
REM R1 =  0.0392 for   1546 Fo > 4sig(Fo)  and  0.0613 for all   2159 data
REM    155 parameters refined using      0 restraints
 
END  
     
WGHT      0.0548      0.2341 
REM Highest difference peak  0.156,  deepest hole -0.159,  1-sigma level  0.035
Q1    1   0.4001  0.6335  0.8745  11.00000  0.05    0.16
Q2    1   0.1643  0.6230  0.9596  11.00000  0.05    0.15
Q3    1  -0.0409  0.4607  0.7777  11.00000  0.05    0.14
Q4    1  -0.2026  0.3408  0.7672  11.00000  0.05    0.13
Q5    1  -0.0911  0.2373  0.7191  11.00000  0.05    0.13
Q6    1  -0.1285  0.4075  0.7235  11.00000  0.05    0.13
Q7    1   0.0902  0.4934  0.8255  11.00000  0.05    0.12
Q8    1   0.1768  0.3568  0.8411  11.00000  0.05    0.12
Q9    1   0.1750  0.2830  0.8783  11.00000  0.05    0.12
Q10   1   0.2865  0.0218  0.8960  11.00000  0.05    0.12
Q11   1   0.3339 -0.0204  0.9426  11.00000  0.05    0.11
Q12   1  -0.0507  0.1433  0.8682  11.00000  0.05    0.11
Q13   1  -0.2539  0.4056  0.7590  11.00000  0.05    0.11
Q14   1  -0.0572  0.6430  0.7987  11.00000  0.05    0.11
Q15   1  -0.2060  0.5704  0.7174  11.00000  0.05    0.11
Q16   1  -0.1623  0.2588  0.7785  11.00000  0.05    0.10
Q17   1   0.1099  0.3492  0.8571  11.00000  0.05    0.10
Q18   1   0.3471  0.2660  0.9583  11.00000  0.05    0.10
Q19   1   0.2018  0.2002  0.9007  11.00000  0.05    0.10
Q20   1   0.2119  0.1592  0.8554  11.00000  0.05    0.10
;

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1128(3) 0.31555(9) 0.84258(10) 0.0400(4) Uani d . 1 . .
C C2 -0.0922(3) 0.30052(9) 0.77329(10) 0.0417(4) Uani d . 1 . .
H H2 -0.1385 0.2449 0.7566 0.05 Uiso calc R 1 . .
C C3 -0.2253(3) 0.36785(9) 0.72985(11) 0.0422(4) Uani d . 1 . .
C C4 -0.1639(3) 0.45178(9) 0.75505(11) 0.0439(4) Uani d . 1 . .
C C5 0.0395(4) 0.46744(9) 0.82433(12) 0.0460(4) Uani d . 1 . .
C C6 0.1769(3) 0.39949(10) 0.86676(11) 0.0450(4) Uani d . 1 . .
H H6 0.3144 0.4101 0.9123 0.054 Uiso calc R 1 . .
C C7 0.2589(3) 0.24495(9) 0.88967(10) 0.0413(4) Uani d . 1 . .
H H7 0.4081 0.2589 0.9296 0.05 Uiso calc R 1 . .
C C8 0.1974(4) 0.16314(10) 0.88047(12) 0.0486(4) Uani d . 1 . .
H H8 0.0552 0.1487 0.838 0.058 Uiso calc R 1 . .
C C9 0.3348(3) 0.09384(9) 0.93153(11) 0.0426(4) Uani d . 1 . .
O O10 0.5429(3) 0.11329(7) 0.98707(8) 0.0537(4) Uani d . 1 . .
H H10 0.624(5) 0.0644(15) 1.0186(18) 0.105(8) Uiso d . 1 . .
O O11 0.2461(3) 0.01919(7) 0.92176(8) 0.0531(3) Uani d . 1 . .
O O12 0.0836(3) 0.55226(7) 0.84573(10) 0.0639(4) Uani d . 1 . .
C C13 0.2995(4) 0.57160(11) 0.91121(15) 0.0680(6) Uani d . 1 . .
H H13A 0.2589 0.545 0.9706 0.102 Uiso calc R 1 . .
H H13B 0.3106 0.6323 0.9196 0.102 Uiso calc R 1 . .
H H13C 0.4758 0.5507 0.888 0.102 Uiso calc R 1 . .
O O14 -0.2980(3) 0.51872(7) 0.71392(10) 0.0575(4) Uani d . 1 . .
H H14 -0.426(6) 0.4982(14) 0.6747(17) 0.091(8) Uiso d . 1 . .
O O15 -0.4265(3) 0.36103(7) 0.66051(8) 0.0532(3) Uani d . 1 . .
C C16 -0.4947(4) 0.27804(10) 0.62862(12) 0.0542(5) Uani d . 1 . .
H H16A -0.33 0.2515 0.603 0.081 Uiso calc R 1 . .
H H16B -0.6379 0.2815 0.5807 0.081 Uiso calc R 1 . .
H H16C -0.5626 0.2447 0.6806 0.081 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.393(2) ?
C1 C2 . 1.399(2) ?
C1 C7 . 1.465(2) ?
C2 C3 . 1.374(2) ?
C2 H2 . 0.93 ?
C3 O15 . 1.3704(19) ?
C3 C4 . 1.394(2) ?
C4 O14 . 1.3577(17) ?
C4 C5 . 1.395(2) ?
C5 O12 . 1.3801(18) ?
C5 C6 . 1.385(2) ?
C6 H6 . 0.93 ?
C7 C8 . 1.322(2) ?
C7 H7 . 0.93 ?
C8 C9 . 1.457(2) ?
C8 H8 . 0.93 ?
C9 O11 . 1.2518(18) ?
C9 O10 . 1.2965(17) ?
O10 H10 . 0.97(2) ?
O12 C13 . 1.412(2) ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
O14 H14 . 0.88(3) ?
O15 C16 . 1.4149(19) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 118.81(13) ?
C6 C1 C7 . . 119.99(13) ?
C2 C1 C7 . . 121.20(14) ?
C3 C2 C1 . . 120.09(14) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
O15 C3 C2 . . 125.31(13) ?
O15 C3 C4 . . 113.65(13) ?
C2 C3 C4 . . 121.04(14) ?
O14 C4 C5 . . 119.16(14) ?
O14 C4 C3 . . 121.54(15) ?
C5 C4 C3 . . 119.30(13) ?
O12 C5 C6 . . 125.16(14) ?
O12 C5 C4 . . 115.33(12) ?
C6 C5 C4 . . 119.51(14) ?
C5 C6 C1 . . 121.24(14) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
C8 C7 C1 . . 125.77(14) ?
C8 C7 H7 . . 117.1 ?
C1 C7 H7 . . 117.1 ?
C7 C8 C9 . . 125.21(15) ?
C7 C8 H8 . . 117.4 ?
C9 C8 H8 . . 117.4 ?
O11 C9 O10 . . 122.84(13) ?
O11 C9 C8 . . 119.54(14) ?
O10 C9 C8 . . 117.60(13) ?
C9 O10 H10 . . 113.1(15) ?
C5 O12 C13 . . 117.40(12) ?
O12 C13 H13A . . 109.5 ?
O12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C4 O14 H14 . . 107.9(15) ?
C3 O15 C16 . . 117.26(11) ?
O15 C16 H16A . . 109.5 ?
O15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.5(2) ?
C7 C1 C2 C3 . . . . -179.70(15) ?
C1 C2 C3 O15 . . . . 179.21(15) ?
C1 C2 C3 C4 . . . . -1.4(2) ?
O15 C3 C4 O14 . . . . 0.8(2) ?
C2 C3 C4 O14 . . . . -178.68(15) ?
O15 C3 C4 C5 . . . . -179.41(15) ?
C2 C3 C4 C5 . . . . 1.1(2) ?
O14 C4 C5 O12 . . . . 0.7(2) ?
C3 C4 C5 O12 . . . . -179.08(15) ?
O14 C4 C5 C6 . . . . 179.86(15) ?
C3 C4 C5 C6 . . . . 0.1(3) ?
O12 C5 C6 C1 . . . . 178.08(16) ?
C4 C5 C6 C1 . . . . -1.0(3) ?
C2 C1 C6 C5 . . . . 0.7(2) ?
C7 C1 C6 C5 . . . . -179.14(15) ?
C6 C1 C7 C8 . . . . 172.44(17) ?
C2 C1 C7 C8 . . . . -7.4(3) ?
C1 C7 C8 C9 . . . . -176.56(15) ?
C7 C8 C9 O11 . . . . 175.21(17) ?
C7 C8 C9 O10 . . . . -3.5(3) ?
C6 C5 O12 C13 . . . . 4.7(3) ?
C4 C5 O12 C13 . . . . -176.19(18) ?
C2 C3 O15 C16 . . . . -2.5(3) ?
C4 C3 O15 C16 . . . . 178.00(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O10 H10 O11 3_657 0.97(2) 1.68(2) 2.6410(15) 177.(2) ?
O14 H14 O11 2_456 0.88(3) 2.07(3) 2.8594(17) 149.(2) ?
O14 H14 O15 . 0.88(3) 2.16(2) 2.6561(17) 115.1(19) ?
####################################################################### 
# 
# 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_full_data
_database_code_depnum_ccdc_archive 'CCDC 1060812'
_audit_update_record             
;
2015-05-26 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            'Sinapic Acid + Nicotinamide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 O5, C6 H6 N2 O'
_chemical_formula_sum            'C17 H18 N2 O6'
_chemical_formula_weight         346.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9109(11)
_cell_length_b                   9.1732(18)
_cell_length_c                   18.814(4)
_cell_angle_alpha                99.563(7)
_cell_angle_beta                 94.601(7)
_cell_angle_gamma                90.531(7)
_cell_volume                     832.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    1281
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      21.91

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X2S'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            8751
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.306
_diffrn_reflns_theta_max         26.281
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3230
_reflns_number_gt                1746
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.12.3.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al., 2008)'
_computing_publication_material  ?
_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     
'w=1/[σ²(Fo²)+(0.0573P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3230
_refine_ls_number_parameters     240
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.995
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7025(5) 0.9066(3) 0.69313(14) 0.0353(7) Uani 1 1 d . . . . .
C2 C 0.6904(5) 0.9339(3) 0.76774(14) 0.0379(7) Uani 1 1 d . . . . .
H2 H 0.5666 0.8803 0.7887 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8602(5) 1.0400(3) 0.81133(13) 0.0333(6) Uani 1 1 d . . . . .
C4 C 1.0459(5) 1.1218(3) 0.77994(13) 0.0324(6) Uani 1 1 d . . . . .
C5 C 1.0566(5) 1.0960(3) 0.70504(13) 0.0329(6) Uani 1 1 d . . . . .
C6 C 0.8886(5) 0.9888(3) 0.66189(14) 0.0366(7) Uani 1 1 d . . . . .
H6 H 0.8993 0.9711 0.6121 0.044 Uiso 1 1 calc R U . . .
C7 C 0.5177(5) 0.7939(3) 0.65044(14) 0.0389(7) Uani 1 1 d . . . . .
H7 H 0.4036 0.7461 0.6768 0.047 Uiso 1 1 calc R U . . .
C8 C 0.4889(5) 0.7497(3) 0.57929(14) 0.0417(7) Uani 1 1 d . . . . .
H8 H 0.6030 0.7905 0.5503 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2823(6) 0.6387(3) 0.54560(14) 0.0381(7) Uani 1 1 d . . . . .
O10 O 0.2597(4) 0.6134(2) 0.47548(11) 0.0584(6) Uani 1 1 d D . . . .
H10 H 0.135(5) 0.554(3) 0.4591(16) 0.088 Uiso 1 1 d D U . . .
O11 O 0.1356(4) 0.5744(2) 0.58260(10) 0.0588(6) Uani 1 1 d . . . . .
O12 O 1.2413(4) 1.1851(2) 0.68032(9) 0.0451(5) Uani 1 1 d . . . . .
C13 C 1.2511(6) 1.1718(3) 0.60436(14) 0.0559(9) Uani 1 1 d . . . . .
H13A H 1.3021 1.0733 0.5849 0.084 Uiso 1 1 calc R U . . .
H13B H 1.3834 1.2415 0.5941 0.084 Uiso 1 1 calc R U . . .
H13C H 1.0745 1.1916 0.5827 0.084 Uiso 1 1 calc R U . . .
O14 O 1.2044(4) 1.2236(2) 0.82553(9) 0.0429(5) Uani 1 1 d D . . . .
H14 H 1.303(5) 1.265(3) 0.8013(13) 0.064 Uiso 1 1 d D U . . .
O15 O 0.8627(4) 1.0744(2) 0.88473(9) 0.0507(6) Uani 1 1 d . . . . .
C16 C 0.6633(6) 1.0039(3) 0.91932(15) 0.0520(8) Uani 1 1 d . . . . .
H16A H 0.4838 1.0257 0.9003 0.078 Uiso 1 1 calc R U . . .
H16B H 0.6840 1.0397 0.9704 0.078 Uiso 1 1 calc R U . . .
H16C H 0.6878 0.8989 0.9105 0.078 Uiso 1 1 calc R U . . .
N17 N 0.3961(4) 0.5931(2) 0.19817(12) 0.0406(6) Uani 1 1 d . . . . .
C18 C 0.2984(5) 0.5248(3) 0.13257(14) 0.0351(6) Uani 1 1 d . . . . .
H18 H 0.3767 0.5485 0.0924 0.042 Uiso 1 1 calc R U . . .
C19 C 0.0855(5) 0.4202(3) 0.12126(13) 0.0310(6) Uani 1 1 d . . . . .
C20 C -0.0312(6) 0.3889(3) 0.18154(15) 0.0461(8) Uani 1 1 d . . . . .
H20 H -0.1774 0.3218 0.1763 0.055 Uiso 1 1 calc R U . . .
C21 C 0.0699(6) 0.4575(3) 0.24964(15) 0.0525(8) Uani 1 1 d . . . . .
H21 H -0.0039 0.4361 0.2908 0.063 Uiso 1 1 calc R U . . .
C22 C 0.2824(6) 0.5584(3) 0.25488(15) 0.0475(8) Uani 1 1 d . . . . .
H22 H 0.3501 0.6049 0.3007 0.057 Uiso 1 1 calc R U . . .
C23 C -0.0274(5) 0.3481(3) 0.04765(14) 0.0349(6) Uani 1 1 d . . . . .
O24 O -0.2743(4) 0.3145(2) 0.03628(11) 0.0586(6) Uani 1 1 d . U . . .
N25 N 0.1470(5) 0.3203(3) -0.00303(12) 0.0408(6) Uani 1 1 d D . . . .
H25A H 0.098(5) 0.276(3) -0.0458(8) 0.061 Uiso 1 1 d D U . . .
H25B H 0.319(2) 0.330(3) 0.0072(14) 0.061 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.390(3) . ?
C1 C6 1.403(3) . ?
C1 C7 1.459(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 O15 1.364(3) . ?
C3 C4 1.402(3) . ?
C4 O14 1.352(3) . ?
C4 C5 1.395(3) . ?
C5 O12 1.374(3) . ?
C5 C6 1.386(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.328(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.460(3) . ?
C8 H8 0.9300 . ?
C9 O11 1.249(3) . ?
C9 O10 1.296(3) . ?
O10 H10 0.823(5) . ?
O12 C13 1.419(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O14 H14 0.823(5) . ?
O15 C16 1.425(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N17 C22 1.325(3) . ?
N17 C18 1.337(3) . ?
C18 C19 1.392(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(3) . ?
C19 C23 1.493(3) . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O24 1.241(3) . ?
C23 N25 1.327(3) . ?
N25 H25A 0.855(10) . ?
N25 H25B 0.853(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.1(2) . . ?
C2 C1 C7 118.2(2) . . ?
C6 C1 C7 122.7(2) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
O15 C3 C2 125.1(2) . . ?
O15 C3 C4 115.1(2) . . ?
C2 C3 C4 119.8(2) . . ?
O14 C4 C5 123.9(2) . . ?
O14 C4 C3 116.7(2) . . ?
C5 C4 C3 119.5(2) . . ?
O12 C5 C6 125.2(2) . . ?
O12 C5 C4 114.3(2) . . ?
C6 C5 C4 120.5(2) . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C1 129.3(3) . . ?
C8 C7 H7 115.4 . . ?
C1 C7 H7 115.4 . . ?
C7 C8 C9 121.5(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
O11 C9 O10 122.8(2) . . ?
O11 C9 C8 121.5(2) . . ?
O10 C9 C8 115.7(2) . . ?
C9 O10 H10 112(2) . . ?
C5 O12 C13 117.5(2) . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 O14 H14 108(2) . . ?
C3 O15 C16 117.8(2) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 N17 C18 117.7(2) . . ?
N17 C18 C19 123.4(2) . . ?
N17 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
C20 C19 C18 117.3(2) . . ?
C20 C19 C23 119.7(2) . . ?
C18 C19 C23 122.9(2) . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 118.2(3) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
N17 C22 C21 123.6(3) . . ?
N17 C22 H22 118.2 . . ?
C21 C22 H22 118.2 . . ?
O24 C23 N25 122.8(2) . . ?
O24 C23 C19 119.9(2) . . ?
N25 C23 C19 117.2(2) . . ?
C23 N25 H25A 122.4(18) . . ?
C23 N25 H25B 121.6(18) . . ?
H25A N25 H25B 115(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 C3 -0.4(4) . . . . ?
C7 C1 C2 C3 -179.8(2) . . . . ?
C1 C2 C3 O15 179.9(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
O15 C3 C4 O14 0.2(4) . . . . ?
C2 C3 C4 O14 179.8(2) . . . . ?
O15 C3 C4 C5 -179.2(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
O14 C4 C5 O12 -0.9(4) . . . . ?
C3 C4 C5 O12 178.5(2) . . . . ?
O14 C4 C5 C6 179.5(2) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
O12 C5 C6 C1 -178.5(2) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C7 C1 C6 C5 179.0(2) . . . . ?
C2 C1 C7 C8 179.2(3) . . . . ?
C6 C1 C7 C8 -0.2(4) . . . . ?
C1 C7 C8 C9 -177.2(3) . . . . ?
C7 C8 C9 O11 -4.4(4) . . . . ?
C7 C8 C9 O10 174.7(3) . . . . ?
C6 C5 O12 C13 3.6(4) . . . . ?
C4 C5 O12 C13 -176.0(2) . . . . ?
C2 C3 O15 C16 -4.6(4) . . . . ?
C4 C3 O15 C16 174.9(2) . . . . ?
C22 N17 C18 C19 0.0(4) . . . . ?
N17 C18 C19 C20 1.2(4) . . . . ?
N17 C18 C19 C23 178.1(2) . . . . ?
C18 C19 C20 C21 -1.8(4) . . . . ?
C23 C19 C20 C21 -178.9(3) . . . . ?
C19 C20 C21 C22 1.4(4) . . . . ?
C18 N17 C22 C21 -0.5(4) . . . . ?
C20 C21 C22 N17 -0.2(5) . . . . ?
C20 C19 C23 O24 30.7(4) . . . . ?
C18 C19 C23 O24 -146.1(3) . . . . ?
C20 C19 C23 N25 -148.1(3) . . . . ?
C18 C19 C23 N25 35.1(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
O10 H10 O11 0.823(5) 1.805(6) 2.627(3) 176(3) 2_566
O14 H14 N17 0.823(5) 1.957(17) 2.684(3) 147(3) 2_776
O14 H14 O12 0.823(5) 2.27(3) 2.717(3) 115(2) .
N25 H25A O15 0.855(10) 2.319(18) 3.063(3) 146(3) 1_444
N25 H25A O14 0.855(10) 2.486(17) 3.236(3) 147(2) 1_444
N25 H25B O24 0.853(10) 2.040(11) 2.882(3) 169(3) 1_655

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_mo_SEL_AS_EOC_SA_3B_0ma-Test
_database_code_depnum_ccdc_archive 'CCDC 1060813'
_audit_update_record             
;
2015-05-26 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
;
'Sinapic Acid + 4-Pyridinecarbonitrile'
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 O5, C6 H4 N2'
_chemical_formula_sum            'C17 H16 N2 O5'
_chemical_formula_weight         328.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.893(3)
_cell_length_b                   31.878(6)
_cell_length_c                   6.5992(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.192(4)
_cell_angle_gamma                90
_cell_volume                     3120.2(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.3576
_cell_measurement_theta_max      25.6309

_exptl_crystal_description       needles
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII DUO'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            69717
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.514
_diffrn_reflns_theta_max         26.794
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6650
_reflns_number_gt                4854
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.12.3.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al., 2008)'
_computing_publication_material  ?
_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     
'w=1/[σ²(Fo²)+(0.0468P)²+5.5639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6650
_refine_ls_number_parameters     449
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1548
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.30556(19) 0.56647(9) 0.2585(4) 0.0188(6) Uani 1 1 d . . . . .
C2 C 0.31618(19) 0.52282(9) 0.2542(4) 0.0200(6) Uani 1 1 d . . . . .
H2 H 0.3747 0.5109 0.2548 0.024 Uiso 1 1 calc R U . . .
C3 C 0.24176(18) 0.49727(8) 0.2492(4) 0.0182(6) Uani 1 1 d . . . . .
C4 C 0.15452(18) 0.51404(8) 0.2496(4) 0.0172(6) Uani 1 1 d . . . . .
C5 C 0.14466(18) 0.55745(9) 0.2566(4) 0.0187(6) Uani 1 1 d . . . . .
C6 C 0.21957(19) 0.58352(9) 0.2618(4) 0.0199(6) Uani 1 1 d . . . . .
H6 H 0.2121 0.6131 0.2676 0.024 Uiso 1 1 calc R U . . .
C7 C 0.38202(19) 0.59483(9) 0.2585(4) 0.0214(6) Uani 1 1 d . . . . .
H7 H 0.3691 0.6240 0.2649 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4687(2) 0.58430(9) 0.2505(5) 0.0237(6) Uani 1 1 d . . . . .
H8 H 0.4841 0.5554 0.2472 0.028 Uiso 1 1 calc R U . . .
C9 C 0.54031(19) 0.61532(9) 0.2466(4) 0.0220(6) Uani 1 1 d . . . . .
O10 O 0.51542(13) 0.65487(6) 0.2581(3) 0.0251(5) Uani 1 1 d D . . . .
H10 H 0.5576(17) 0.6721(9) 0.247(6) 0.038 Uiso 1 1 d D U . . .
O11 O 0.61895(14) 0.60498(6) 0.2334(4) 0.0315(5) Uani 1 1 d . . . . .
O12 O 0.05749(13) 0.57072(6) 0.2592(3) 0.0223(5) Uani 1 1 d . . . . .
C13 C 0.0436(2) 0.61490(9) 0.2739(5) 0.0260(7) Uani 1 1 d . . . . .
H13B H 0.0755 0.6254 0.4001 0.039 Uiso 1 1 calc R U . . .
H13C H -0.0210 0.6207 0.2745 0.039 Uiso 1 1 calc R U . . .
H13A H 0.0668 0.6289 0.1573 0.039 Uiso 1 1 calc R U . . .
O14 O 0.08556(13) 0.48723(6) 0.2438(3) 0.0221(4) Uani 1 1 d D . . . .
H14 H 0.0351(11) 0.4990(10) 0.244(5) 0.033 Uiso 1 1 d D U . . .
O15 O 0.24437(13) 0.45426(6) 0.2436(3) 0.0246(5) Uani 1 1 d . . . . .
C16 C 0.3308(2) 0.43561(10) 0.2454(6) 0.0337(8) Uani 1 1 d . . . . .
H16A H 0.3601 0.4451 0.1265 0.051 Uiso 1 1 calc R U . . .
H16C H 0.3245 0.4050 0.2410 0.051 Uiso 1 1 calc R U . . .
H16B H 0.3675 0.4438 0.3699 0.051 Uiso 1 1 calc R U . . .
C17 C 0.96005(18) 0.75027(9) 0.2622(4) 0.0180(6) Uani 1 1 d . . . . .
C18 C 1.04844(18) 0.73593(9) 0.2750(4) 0.0175(6) Uani 1 1 d . . . . .
H18 H 1.0602 0.7066 0.2778 0.021 Uiso 1 1 calc R U . . .
C19 C 1.11924(18) 0.76393(9) 0.2836(4) 0.0174(6) Uani 1 1 d . . . . .
C20 C 1.10380(18) 0.80706(8) 0.2814(4) 0.0173(6) Uani 1 1 d . . . . .
C21 C 1.01436(18) 0.82149(8) 0.2689(4) 0.0174(6) Uani 1 1 d . . . . .
C22 C 0.94334(18) 0.79363(9) 0.2590(4) 0.0178(6) Uani 1 1 d . . . . .
H22 H 0.8831 0.8038 0.2500 0.021 Uiso 1 1 calc R U . . .
C23 C 0.88755(18) 0.71956(9) 0.2532(4) 0.0192(6) Uani 1 1 d . . . . .
H23 H 0.9044 0.6908 0.2569 0.023 Uiso 1 1 calc R U . . .
C24 C 0.79968(19) 0.72807(9) 0.2403(5) 0.0227(6) Uani 1 1 d . . . . .
H24 H 0.7814 0.7566 0.2342 0.027 Uiso 1 1 calc R U . . .
C25 C 0.73002(19) 0.69588(9) 0.2349(4) 0.0206(6) Uani 1 1 d . . . . .
O26 O 0.75803(13) 0.65667(6) 0.2400(4) 0.0266(5) Uani 1 1 d D . . . .
H26 H 0.7123(15) 0.6411(9) 0.238(6) 0.040 Uiso 1 1 d D U . . .
O27 O 0.64948(13) 0.70554(6) 0.2275(3) 0.0256(5) Uani 1 1 d . . . . .
O28 O 1.20877(13) 0.75274(6) 0.2946(3) 0.0222(4) Uani 1 1 d . . . . .
C29 C 1.2278(2) 0.70878(9) 0.2963(5) 0.0248(6) Uani 1 1 d . . . . .
H29B H 1.2043 0.6959 0.4155 0.037 Uiso 1 1 calc R U . . .
H29C H 1.2931 0.7045 0.3024 0.037 Uiso 1 1 calc R U . . .
H29A H 1.1990 0.6959 0.1722 0.037 Uiso 1 1 calc R U . . .
O30 O 1.17157(13) 0.83585(6) 0.2907(3) 0.0224(4) Uani 1 1 d D . . . .
H30 H 1.2224(11) 0.8243(10) 0.299(5) 0.034 Uiso 1 1 d D U . . .
O31 O 1.00480(13) 0.86425(6) 0.2672(3) 0.0218(4) Uani 1 1 d . . . . .
C32 C 0.91410(19) 0.88015(10) 0.2585(5) 0.0295(7) Uani 1 1 d . . . . .
H32A H 0.8800 0.8702 0.1338 0.044 Uiso 1 1 calc R U . . .
H32C H 0.9154 0.9109 0.2589 0.044 Uiso 1 1 calc R U . . .
H32B H 0.8851 0.8702 0.3770 0.044 Uiso 1 1 calc R U . . .
N33 N 0.35551(17) 0.67939(8) 0.8258(4) 0.0275(6) Uani 1 1 d . . . . .
C34 C 0.3957(2) 0.64463(10) 0.7679(5) 0.0279(7) Uani 1 1 d . . . . .
H34 H 0.3601 0.6201 0.7451 0.033 Uiso 1 1 calc R U . . .
C35 C 0.4861(2) 0.64233(10) 0.7391(5) 0.0268(7) Uani 1 1 d . . . . .
H35 H 0.5122 0.6168 0.6983 0.032 Uiso 1 1 calc R U . . .
C36 C 0.53774(19) 0.67823(9) 0.7713(5) 0.0226(6) Uani 1 1 d . . . . .
C37 C 0.4980(2) 0.71465(10) 0.8353(5) 0.0285(7) Uani 1 1 d . . . . .
H37 H 0.5321 0.7396 0.8612 0.034 Uiso 1 1 calc R U . . .
C38 C 0.4071(2) 0.71342(10) 0.8602(5) 0.0303(7) Uani 1 1 d . . . . .
H38 H 0.3795 0.7382 0.9044 0.036 Uiso 1 1 calc R U . . .
C39 C 0.6324(2) 0.67732(9) 0.7413(5) 0.0261(7) Uani 1 1 d . . . . .
N40 N 0.70728(18) 0.67525(8) 0.7164(5) 0.0330(7) Uani 1 1 d . . . . .
N41 N 0.91069(16) 0.49799(8) 0.2558(4) 0.0225(5) Uani 1 1 d . . . . .
C42 C 0.8505(2) 0.52886(9) 0.2636(5) 0.0238(6) Uani 1 1 d . . . . .
H42 H 0.8722 0.5569 0.2720 0.029 Uiso 1 1 calc R U . . .
C43 C 0.75911(19) 0.52252(10) 0.2602(5) 0.0244(6) Uani 1 1 d . . . . .
H43 H 0.7187 0.5455 0.2662 0.029 Uiso 1 1 calc R U . . .
C44 C 0.72755(19) 0.48136(9) 0.2475(4) 0.0214(6) Uani 1 1 d . . . . .
C45 C 0.78893(19) 0.44863(9) 0.2402(4) 0.0215(6) Uani 1 1 d . . . . .
H45 H 0.7692 0.4203 0.2332 0.026 Uiso 1 1 calc R U . . .
C46 C 0.87895(19) 0.45847(9) 0.2435(4) 0.0217(6) Uani 1 1 d . . . . .
H46 H 0.9209 0.4362 0.2368 0.026 Uiso 1 1 calc R U . . .
C47 C 0.6322(2) 0.47317(10) 0.2436(5) 0.0259(7) Uani 1 1 d . . . . .
N48 N 0.55618(18) 0.46694(9) 0.2391(4) 0.0353(7) 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 1.393(4) . ?
C1 C2 1.401(4) . ?
C1 C7 1.454(4) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9500 . ?
C3 O15 1.372(3) . ?
C3 C4 1.405(4) . ?
C4 O14 1.334(3) . ?
C4 C5 1.393(4) . ?
C5 O12 1.367(3) . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.339(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.457(4) . ?
C8 H8 0.9500 . ?
C9 O11 1.227(4) . ?
C9 O10 1.318(3) . ?
O10 H10 0.842(5) . ?
O12 C13 1.428(3) . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13A 0.9800 . ?
O14 H14 0.840(5) . ?
O15 C16 1.416(4) . ?
C16 H16A 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.389(4) . ?
C17 C22 1.404(4) . ?
C17 C23 1.455(4) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9500 . ?
C19 O28 1.376(3) . ?
C19 C20 1.394(4) . ?
C20 O30 1.361(3) . ?
C20 C21 1.405(4) . ?
C21 O31 1.370(3) . ?
C21 C22 1.378(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.332(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.458(4) . ?
C24 H24 0.9500 . ?
C25 O27 1.235(3) . ?
C25 O26 1.317(3) . ?
O26 H26 0.841(5) . ?
O28 C29 1.429(3) . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C29 H29A 0.9800 . ?
O30 H30 0.840(5) . ?
O31 C32 1.439(3) . ?
C32 H32A 0.9800 . ?
C32 H32C 0.9800 . ?
C32 H32B 0.9800 . ?
N33 C34 1.332(4) . ?
N33 C38 1.337(4) . ?
C34 C35 1.378(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.387(4) . ?
C36 C39 1.441(4) . ?
C37 C38 1.378(4) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 N40 1.144(4) . ?
N41 C42 1.335(4) . ?
N41 C46 1.346(4) . ?
C42 C43 1.374(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.394(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.391(4) . ?
C44 C47 1.443(4) . ?
C45 C46 1.375(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 N48 1.147(4) . ?

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 119.6(3) . . ?
C6 C1 C7 118.6(3) . . ?
C2 C1 C7 121.8(3) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
O15 C3 C2 124.6(2) . . ?
O15 C3 C4 114.1(2) . . ?
C2 C3 C4 121.2(3) . . ?
O14 C4 C5 123.7(2) . . ?
O14 C4 C3 117.8(2) . . ?
C5 C4 C3 118.6(2) . . ?
O12 C5 C6 125.2(2) . . ?
O12 C5 C4 114.3(2) . . ?
C6 C5 C4 120.6(3) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C1 127.0(3) . . ?
C8 C7 H7 116.5 . . ?
C1 C7 H7 116.5 . . ?
C7 C8 C9 122.7(3) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
O11 C9 O10 122.4(3) . . ?
O11 C9 C8 121.6(3) . . ?
O10 C9 C8 116.0(3) . . ?
C9 O10 H10 114(3) . . ?
C5 O12 C13 116.7(2) . . ?
O12 C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O12 C13 H13A 109.5 . . ?
H13B C13 H13A 109.5 . . ?
H13C C13 H13A 109.5 . . ?
C4 O14 H14 114(2) . . ?
C3 O15 C16 116.5(2) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
C18 C17 C22 119.4(2) . . ?
C18 C17 C23 118.5(2) . . ?
C22 C17 C23 122.1(3) . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
O28 C19 C18 124.6(2) . . ?
O28 C19 C20 114.5(2) . . ?
C18 C19 C20 120.9(2) . . ?
O30 C20 C19 122.9(2) . . ?
O30 C20 C21 118.5(2) . . ?
C19 C20 C21 118.6(2) . . ?
O31 C21 C22 124.2(2) . . ?
O31 C21 C20 115.1(2) . . ?
C22 C21 C20 120.8(2) . . ?
C21 C22 C17 120.0(2) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C24 C23 C17 125.9(3) . . ?
C24 C23 H23 117.0 . . ?
C17 C23 H23 117.0 . . ?
C23 C24 C25 123.5(3) . . ?
C23 C24 H24 118.3 . . ?
C25 C24 H24 118.3 . . ?
O27 C25 O26 122.8(3) . . ?
O27 C25 C24 120.8(3) . . ?
O26 C25 C24 116.4(2) . . ?
C25 O26 H26 108(3) . . ?
C19 O28 C29 116.4(2) . . ?
O28 C29 H29B 109.5 . . ?
O28 C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O28 C29 H29A 109.5 . . ?
H29B C29 H29A 109.5 . . ?
H29C C29 H29A 109.5 . . ?
C20 O30 H30 112(2) . . ?
C21 O31 C32 116.6(2) . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
O31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32C C32 H32B 109.5 . . ?
C34 N33 C38 117.2(3) . . ?
N33 C34 C35 123.6(3) . . ?
N33 C34 H34 118.2 . . ?
C35 C34 H34 118.2 . . ?
C34 C35 C36 118.1(3) . . ?
C34 C35 H35 120.9 . . ?
C36 C35 H35 120.9 . . ?
C35 C36 C37 119.5(3) . . ?
C35 C36 C39 119.9(3) . . ?
C37 C36 C39 120.6(3) . . ?
C38 C37 C36 117.6(3) . . ?
C38 C37 H37 121.2 . . ?
C36 C37 H37 121.2 . . ?
N33 C38 C37 124.0(3) . . ?
N33 C38 H38 118.0 . . ?
C37 C38 H38 118.0 . . ?
N40 C39 C36 177.8(3) . . ?
C42 N41 C46 117.3(2) . . ?
N41 C42 C43 123.9(3) . . ?
N41 C42 H42 118.0 . . ?
C43 C42 H42 118.0 . . ?
C42 C43 C44 117.9(3) . . ?
C42 C43 H43 121.1 . . ?
C44 C43 H43 121.1 . . ?
C45 C44 C43 119.3(3) . . ?
C45 C44 C47 120.9(3) . . ?
C43 C44 C47 119.8(3) . . ?
C46 C45 C44 118.1(3) . . ?
C46 C45 H45 120.9 . . ?
C44 C45 H45 120.9 . . ?
N41 C46 C45 123.4(3) . . ?
N41 C46 H46 118.3 . . ?
C45 C46 H46 118.3 . . ?
N48 C47 C44 179.4(4) . . ?

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 1.3(4) . . . . ?
C7 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 O15 179.6(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
O15 C3 C4 O14 -0.2(4) . . . . ?
C2 C3 C4 O14 179.8(3) . . . . ?
O15 C3 C4 C5 179.5(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
O14 C4 C5 O12 0.6(4) . . . . ?
C3 C4 C5 O12 -179.2(2) . . . . ?
O14 C4 C5 C6 -179.8(3) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
O12 C5 C6 C1 180.0(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C7 C1 C6 C5 178.3(3) . . . . ?
C6 C1 C7 C8 -178.2(3) . . . . ?
C2 C1 C7 C8 1.5(5) . . . . ?
C1 C7 C8 C9 178.5(3) . . . . ?
C7 C8 C9 O11 -177.9(3) . . . . ?
C7 C8 C9 O10 2.1(4) . . . . ?
C6 C5 O12 C13 -1.8(4) . . . . ?
C4 C5 O12 C13 177.8(2) . . . . ?
C2 C3 O15 C16 0.7(4) . . . . ?
C4 C3 O15 C16 -179.3(3) . . . . ?
C22 C17 C18 C19 -0.3(4) . . . . ?
C23 C17 C18 C19 179.9(3) . . . . ?
C17 C18 C19 O28 -179.4(3) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
O28 C19 C20 O30 -0.4(4) . . . . ?
C18 C19 C20 O30 179.6(3) . . . . ?
O28 C19 C20 C21 179.6(2) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
O30 C20 C21 O31 0.0(4) . . . . ?
C19 C20 C21 O31 -179.9(2) . . . . ?
O30 C20 C21 C22 180.0(2) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
O31 C21 C22 C17 -179.8(3) . . . . ?
C20 C21 C22 C17 0.3(4) . . . . ?
C18 C17 C22 C21 -0.1(4) . . . . ?
C23 C17 C22 C21 179.7(3) . . . . ?
C18 C17 C23 C24 -179.9(3) . . . . ?
C22 C17 C23 C24 0.4(5) . . . . ?
C17 C23 C24 C25 -179.0(3) . . . . ?
C23 C24 C25 O27 178.4(3) . . . . ?
C23 C24 C25 O26 -1.2(4) . . . . ?
C18 C19 O28 C29 0.2(4) . . . . ?
C20 C19 O28 C29 -179.7(2) . . . . ?
C22 C21 O31 C32 1.3(4) . . . . ?
C20 C21 O31 C32 -178.8(3) . . . . ?
C38 N33 C34 C35 -1.1(5) . . . . ?
N33 C34 C35 C36 -0.3(5) . . . . ?
C34 C35 C36 C37 1.5(5) . . . . ?
C34 C35 C36 C39 -179.5(3) . . . . ?
C35 C36 C37 C38 -1.3(5) . . . . ?
C39 C36 C37 C38 179.7(3) . . . . ?
C34 N33 C38 C37 1.3(5) . . . . ?
C36 C37 C38 N33 -0.2(5) . . . . ?
C46 N41 C42 C43 0.1(4) . . . . ?
N41 C42 C43 C44 -0.1(5) . . . . ?
C42 C43 C44 C45 0.4(4) . . . . ?
C42 C43 C44 C47 180.0(3) . . . . ?
C43 C44 C45 C46 -0.8(4) . . . . ?
C47 C44 C45 C46 179.7(3) . . . . ?
C42 N41 C46 C45 -0.5(4) . . . . ?
C44 C45 C46 N41 0.8(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
O10 H10 O27 0.842(5) 1.749(6) 2.590(3) 177(4) .
O14 H14 N41 0.840(5) 1.863(17) 2.635(3) 152(3) 1_455
O26 H26 O11 0.841(5) 1.804(6) 2.644(3) 176(4) .
O30 H30 N33 0.840(5) 1.977(15) 2.771(3) 157(3) 4_675

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_SA.PTU.2MeCN_Low_Temp
_database_code_depnum_ccdc_archive 'CCDC 1060814'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;
#===================================================================== 
_chemical_name_systematic        ?
_chemical_name_common            
;
'Sinapic Acid + 6-Propyl-2-thiouracil . 2 Acetonitrile'
;
_chemical_formula_moiety         'C11 H12 O5, C7 H10 N2 O S, 2(C2 H3 N)'
_chemical_formula_sum            'C22 H28 N4 O6 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         476.54

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2922(8)
_cell_length_b                   10.5857(10)
_cell_length_c                   14.7818(15)
_cell_angle_alpha                98.274(2)
_cell_angle_beta                 94.315(2)
_cell_angle_gamma                105.620(2)
_cell_volume                     1227.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6347
_cell_measurement_theta_min      2.6554
_cell_measurement_theta_max      26.3268
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Clear colourless'
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504

_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEXII DUO'
_diffrn_measurement_method       'φ & ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16145
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_full        26.34
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_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.
;

_reflns_number_total             4920
_reflns_number_gt                4229
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1089
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.103
_refine_ls_number_reflns         4920
_refine_ls_number_parameters     319
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0539P)²+0.6056P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.374
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2011.12.3.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al., 2008)'
_computing_publication_material  ?

_iucr_refine_instruction_details 
;
TITL mo_SEL_AS_EOC_SA_3D_1_0m in P-1
CELL 0.71073   8.2922  10.5857  14.7818  98.274  94.315 105.620
ZERR    2.00   0.0008   0.0010   0.0015   0.002   0.002   0.002
LATT 1
SFAC C  H  N  O  S
UNIT 44  56  8  12  2
L.S. 6
ACTA
BOND $H
FMAP 2
PLAN 20
SIZE 0.104 0.391 0.551
EQIV $1_[ x+1, y, z+1 ]
EQIV $2_[ -x+2, -y+2, -z+2 ]
EQIV $3_[ x-1, y, z-1 ]
EQIV $4_[ x+1, y, z ]
HTAB N18 O11_$1
HTAB N22 S23_$2
HTAB O10 O24_$3
HTAB O14 N33_$4
DFIX 0.84 0.005 O10 H10 O14 H14
DFIX 0.88 0.005 N22 H22 N18 H18
ISOR 0.005 C28
CONF
TEMP -173.140
WGHT    0.053900    0.605600
FVAR       0.21435
MOLE 2
C1    1    0.575505    0.270938    0.190457    11.00000    0.01355    0.01495 =
         0.01992    0.00385    0.00277    0.00395
C2    1    0.638796    0.336705    0.280726    11.00000    0.01662    0.01387 =
         0.02106    0.00161    0.00343    0.00507
AFIX  43
H2    2    0.627978    0.423004    0.301139    11.00000   -1.20000
AFIX   0
C3    1    0.717255    0.274923    0.339966    11.00000    0.01738    0.01646 =
         0.01710    0.00135    0.00201    0.00323
C4    1    0.735176    0.147567    0.310763    11.00000    0.01528    0.01644 =
         0.01896    0.00526    0.00206    0.00433
C5    1    0.674861    0.083767    0.220203    11.00000    0.01631    0.01236 =
         0.02226    0.00190    0.00296    0.00375
C6    1    0.594633    0.144484    0.160863    11.00000    0.01532    0.01512 =
         0.01921    0.00097   -0.00004    0.00293
AFIX  43
H6    2    0.552388    0.099937    0.099727    11.00000   -1.20000
AFIX   0
C7    1    0.484427    0.327742    0.126460    11.00000    0.01543    0.01728 =
         0.01906    0.00311    0.00247    0.00336
AFIX  43
H7    2    0.445479    0.275788    0.066969    11.00000   -1.20000
AFIX   0
C8    1    0.449497    0.444614    0.141978    11.00000    0.01699    0.01754 =
         0.01995    0.00231    0.00031    0.00423
AFIX  43
H8    2    0.492779    0.501282    0.199479    11.00000   -1.20000
AFIX   0
C9    1    0.348129    0.489835    0.075073    11.00000    0.01434    0.01574 =
         0.02208    0.00422    0.00463    0.00405
O10   4    0.289913    0.404192   -0.003296    11.00000    0.02422    0.01703 =
         0.02087    0.00185   -0.00238    0.00989
H10   2    0.230301    0.434118   -0.038553    11.00000    0.03772
O11   4    0.316835    0.597368    0.090797    11.00000    0.02596    0.01566 =
         0.02474    0.00272   -0.00070    0.00958
O12   4    0.702305   -0.038395    0.197501    11.00000    0.03055    0.01420 =
         0.02276   -0.00103   -0.00430    0.01045
C13   1    0.634538   -0.111876    0.107297    11.00000    0.02948    0.01559 =
         0.02370   -0.00305   -0.00414    0.00834
AFIX 137
H13A  2    0.512033   -0.127042    0.099150    11.00000   -1.50000
H13B  2    0.660072   -0.197686    0.100038    11.00000   -1.50000
H13C  2    0.685148   -0.061168    0.060992    11.00000   -1.50000
AFIX   0
O14   4    0.809464    0.083155    0.367084    11.00000    0.02651    0.01925 =
         0.01875    0.00413   -0.00180    0.00888
H14   2    0.844183    0.125382    0.420655    11.00000    0.04462
O15   4    0.782370    0.326926    0.429616    11.00000    0.03396    0.01954 =
         0.01703   -0.00271   -0.00320    0.01175
C16   1    0.767167    0.455542    0.465849    11.00000    0.04069    0.02192 =
         0.02338   -0.00449   -0.00180    0.01308
AFIX 137
H16A  2    0.827689    0.521213    0.430700    11.00000   -1.50000
H16B  2    0.815617    0.480433    0.530635    11.00000   -1.50000
H16C  2    0.647787    0.453032    0.461018    11.00000   -1.50000
AFIX   0
MOLE 1
C17   1    1.078775    0.798947    0.981891    11.00000    0.01529    0.01375 =
         0.02012    0.00340    0.00431    0.00475
N18   3    1.110544    0.678760    0.966006    11.00000    0.01762    0.01457 =
         0.01776    0.00333    0.00130    0.00681
H18   2    1.169390    0.660033    1.011733    11.00000    0.02492
C19   1    1.063518    0.588686    0.883631    11.00000    0.01460    0.01335 =
         0.02123    0.00226    0.00374    0.00346
C20   1    0.975717    0.629841    0.811250    11.00000    0.01572    0.01511 =
         0.01896    0.00017    0.00247    0.00360
AFIX  43
H20   2    0.938338    0.572294    0.753601    11.00000   -1.20000
AFIX   0
C21   1    0.945726    0.750359    0.824583    11.00000    0.01272    0.01484 =
         0.01696    0.00212    0.00275    0.00171
N22   3    0.996240    0.831009    0.910091    11.00000    0.01886    0.01299 =
         0.01689    0.00141    0.00092    0.00676
H22   2    0.968499    0.905902    0.918731    11.00000    0.02468
S23   5    1.141818    0.901528    1.083732    11.00000    0.02988    0.01685 =
         0.01744   -0.00065   -0.00249    0.01182
O24   4    1.099266    0.481591    0.877871    11.00000    0.02407    0.01378 =
         0.02323    0.00099   -0.00014    0.00845
C25   1    0.862650    0.810817    0.755186    11.00000    0.01819    0.01453 =
         0.01882    0.00291    0.00182    0.00566
AFIX  23
H25A  2    0.944008    0.894661    0.746794    11.00000   -1.20000
H25B  2    0.765640    0.834297    0.780921    11.00000   -1.20000
AFIX   0
C26   1    0.799973    0.724133    0.660881    11.00000    0.02157    0.01863 =
         0.01945    0.00146    0.00012    0.00390
AFIX  23
H26A  2    0.714407    0.641450    0.667543    11.00000   -1.20000
H26B  2    0.895217    0.699016    0.634173    11.00000   -1.20000
AFIX   0
C27   1    0.722774    0.798186    0.596365    11.00000    0.02528    0.02868 =
         0.02250    0.00547   -0.00050    0.00597
AFIX 137
H27A  2    0.629642    0.824253    0.623295    11.00000   -1.50000
H27B  2    0.680165    0.739953    0.536772    11.00000   -1.50000
H27C  2    0.808923    0.877923    0.587585    11.00000   -1.50000
AFIX   0
MOLE 2
C28   1    0.403195    0.837372    0.329140    11.00000    0.06259    0.06276 =
         0.14395    0.05360    0.05161    0.03121
AFIX 137
H28A  2    0.503311    0.914176    0.336097    11.00000   -1.50000
H28B  2    0.325429    0.856758    0.372297    11.00000   -1.50000
H28C  2    0.347022    0.819198    0.265973    11.00000   -1.50000
AFIX   0
C29   1    0.453297    0.721806    0.348475    11.00000    0.04399    0.03296 =
         0.04539    0.00881    0.01497    0.00726
N30   3    0.491414    0.630873    0.361002    11.00000    0.07444    0.03320 =
         0.03385   -0.00285    0.00003    0.01726
C31   1    0.112043    0.232026    0.717170    11.00000    0.04141    0.02948 =
         0.02687    0.00300   -0.00208    0.01489
AFIX 137
H31A  2    0.192860    0.320847    0.727518    11.00000   -1.50000
H31B  2    0.171898    0.165838    0.726394    11.00000   -1.50000
H31C  2    0.028255    0.229808    0.760712    11.00000   -1.50000
AFIX   0
C32   1    0.027619    0.201725    0.623499    11.00000    0.02817    0.02163 =
         0.02642    0.00737    0.00594    0.01076
N33   3   -0.040232    0.177546    0.550637    11.00000    0.03824    0.03770 =
         0.02561    0.00605    0.00063    0.01395
HKLF 4 1 1 0 0 0 1 0 0 0 1
 
REM  mo_SEL_AS_EOC_SA_3D_1_0m in P-1
REM R1 =  0.0393 for   4229 Fo > 4sig(Fo)  and  0.0474 for all   4920 data
REM    319 parameters refined using     10 restraints
 
END  
     
WGHT      0.0535      0.6081 
REM Highest difference peak  0.589,  deepest hole -0.374,  1-sigma level  0.049
Q1    1   0.4489  0.8699  0.3980  11.00000  0.05    0.59
Q2    1   0.8977  0.7761  0.7896  11.00000  0.05    0.30
Q3    1   1.0359  0.6151  0.8419  11.00000  0.05    0.29
Q4    1   0.3790  0.8244  0.3060  11.00000  0.05    0.29
Q5    1   0.5346  0.3001  0.1615  11.00000  0.05    0.29
Q6    1   0.5930  0.2921  0.2407  11.00000  0.05    0.29
Q7    1   0.6702  0.3034  0.3090  11.00000  0.05    0.28
Q8    1   1.2139  0.8588  1.1156  11.00000  0.05    0.27
Q9    1   1.1411  0.8715  1.0219  11.00000  0.05    0.26
Q10   1   0.3884  0.4593  0.1123  11.00000  0.05    0.24
Q11   1   0.9579  0.7770  0.8631  11.00000  0.05    0.24
Q12   1   0.8215  0.7674  0.7088  11.00000  0.05    0.24
Q13   1   0.7155  0.1190  0.2617  11.00000  0.05    0.24
Q14   1   0.6089  0.0970  0.1979  11.00000  0.05    0.23
Q15   1   0.7339  0.2117  0.3216  11.00000  0.05    0.23
Q16   1   0.7782  0.1234  0.3377  11.00000  0.05    0.23
Q17   1   0.9434  0.6784  0.8202  11.00000  0.05    0.23
Q18   1   1.0847  0.9566  1.0614  11.00000  0.05    0.22
Q19   1   0.6647  0.1261  0.1881  11.00000  0.05    0.21
Q20   1   0.7656  0.7593  0.6256  11.00000  0.05    0.21
;

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5755(2) 0.27094(16) 0.19046(11) 0.0160(3) Uani d . 1 . .
C C2 0.6388(2) 0.33671(16) 0.28073(11) 0.0171(3) Uani d . 1 . .
H H2 0.628 0.423 0.3011 0.021 Uiso calc R 1 . .
C C3 0.7173(2) 0.27492(16) 0.33997(11) 0.0175(3) Uani d . 1 . .
C C4 0.7352(2) 0.14757(16) 0.31076(11) 0.0167(3) Uani d . 1 . .
C C5 0.6749(2) 0.08377(15) 0.22020(11) 0.0171(3) Uani d . 1 . .
C C6 0.5946(2) 0.14448(15) 0.16086(11) 0.0171(3) Uani d . 1 . .
H H6 0.5524 0.0999 0.0997 0.021 Uiso calc R 1 . .
C C7 0.4844(2) 0.32774(16) 0.12646(11) 0.0175(3) Uani d . 1 . .
H H7 0.4455 0.2758 0.067 0.021 Uiso calc R 1 . .
C C8 0.4495(2) 0.44461(16) 0.14198(11) 0.0185(3) Uani d . 1 . .
H H8 0.4928 0.5013 0.1995 0.022 Uiso calc R 1 . .
C C9 0.3481(2) 0.48983(16) 0.07507(11) 0.0172(3) Uani d . 1 . .
O O10 0.28991(15) 0.40419(11) -0.00330(8) 0.0203(3) Uani d D 1 . .
H H10 0.230(2) 0.434(2) -0.0386(13) 0.038(6) Uiso d D 1 . .
O O11 0.31683(15) 0.59737(11) 0.09080(8) 0.0217(3) Uani d . 1 . .
O O12 0.70231(16) -0.03840(11) 0.19750(8) 0.0225(3) Uani d . 1 . .
C C13 0.6345(2) -0.11188(16) 0.10730(12) 0.0236(4) Uani d . 1 . .
H H13A 0.512 -0.127 0.0992 0.035 Uiso calc R 1 . .
H H13B 0.6601 -0.1977 0.1 0.035 Uiso calc R 1 . .
H H13C 0.6851 -0.0612 0.061 0.035 Uiso calc R 1 . .
O O14 0.80946(15) 0.08316(12) 0.36708(8) 0.0212(3) Uani d D 1 . .
H H14 0.844(3) 0.125(2) 0.4207(7) 0.045(7) Uiso d D 1 . .
O O15 0.78237(16) 0.32693(12) 0.42962(8) 0.0236(3) Uani d . 1 . .
C C16 0.7672(3) 0.45554(18) 0.46585(13) 0.0290(4) Uani d . 1 . .
H H16A 0.8277 0.5212 0.4307 0.043 Uiso calc R 1 . .
H H16B 0.8156 0.4804 0.5306 0.043 Uiso calc R 1 . .
H H16C 0.6478 0.453 0.461 0.043 Uiso calc R 1 . .
C C17 1.0788(2) 0.79895(15) 0.98189(11) 0.0161(3) Uani d . 1 . .
N N18 1.11054(17) 0.67876(13) 0.96601(9) 0.0162(3) Uani d D 1 . .
H H18 1.169(2) 0.660(2) 1.0117(10) 0.025(5) Uiso d D 1 . .
C C19 1.0635(2) 0.58869(15) 0.88363(11) 0.0165(3) Uani d . 1 . .
C C20 0.9757(2) 0.62984(16) 0.81125(11) 0.0170(3) Uani d . 1 . .
H H20 0.9383 0.5723 0.7536 0.02 Uiso calc R 1 . .
C C21 0.94573(19) 0.75036(15) 0.82458(11) 0.0153(3) Uani d . 1 . .
N N22 0.99624(17) 0.83101(13) 0.91009(9) 0.0160(3) Uani d D 1 . .
H H22 0.968(2) 0.9059(11) 0.9187(14) 0.025(5) Uiso d D 1 . .
S S23 1.14182(6) 0.90153(4) 1.08373(3) 0.02102(12) Uani d . 1 . .
O O24 1.09927(15) 0.48159(11) 0.87787(8) 0.0201(3) Uani d . 1 . .
C C25 0.8626(2) 0.81082(16) 0.75519(11) 0.0170(3) Uani d . 1 . .
H H25A 0.944 0.8947 0.7468 0.02 Uiso calc R 1 . .
H H25B 0.7656 0.8343 0.7809 0.02 Uiso calc R 1 . .
C C26 0.8000(2) 0.72413(16) 0.66088(11) 0.0205(4) Uani d . 1 . .
H H26A 0.7144 0.6414 0.6675 0.025 Uiso calc R 1 . .
H H26B 0.8952 0.699 0.6342 0.025 Uiso calc R 1 . .
C C27 0.7228(2) 0.79819(19) 0.59637(12) 0.0259(4) Uani d . 1 . .
H H27A 0.6296 0.8243 0.6233 0.039 Uiso calc R 1 . .
H H27B 0.6802 0.74 0.5368 0.039 Uiso calc R 1 . .
H H27C 0.8089 0.8779 0.5876 0.039 Uiso calc R 1 . .
C C28 0.4032(4) 0.8374(3) 0.3291(3) 0.0813(11) Uani d U 1 . .
H H28A 0.5033 0.9142 0.3361 0.122 Uiso calc R 1 . .
H H28B 0.3254 0.8568 0.3723 0.122 Uiso calc R 1 . .
H H28C 0.347 0.8192 0.266 0.122 Uiso calc R 1 . .
C C29 0.4533(3) 0.7218(2) 0.34848(16) 0.0408(5) Uani d . 1 . .
N N30 0.4914(3) 0.63087(19) 0.36100(13) 0.0480(5) Uani d . 1 . .
C C31 0.1120(3) 0.2320(2) 0.71717(13) 0.0321(4) Uani d . 1 . .
H H31A 0.1929 0.3208 0.7275 0.048 Uiso calc R 1 . .
H H31B 0.1719 0.1658 0.7264 0.048 Uiso calc R 1 . .
H H31C 0.0283 0.2298 0.7607 0.048 Uiso calc R 1 . .
C C32 0.0276(2) 0.20172(17) 0.62350(13) 0.0242(4) Uani d . 1 . .
N N33 -0.0402(2) 0.17755(17) 0.55064(11) 0.0333(4) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.402(2) ?
C1 C2 . 1.404(2) ?
C1 C7 . 1.459(2) ?
C2 C3 . 1.388(2) ?
C2 H2 . 0.95 ?
C3 O15 . 1.369(2) ?
C3 C4 . 1.406(2) ?
C4 O14 . 1.3601(19) ?
C4 C5 . 1.398(2) ?
C5 O12 . 1.3718(19) ?
C5 C6 . 1.389(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.337(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.463(2) ?
C8 H8 . 0.95 ?
C9 O11 . 1.2285(19) ?
C9 O10 . 1.332(2) ?
O10 H10 . 0.842(5) ?
O12 C13 . 1.433(2) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
O14 H14 . 0.839(5) ?
O15 C16 . 1.431(2) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 N22 . 1.353(2) ?
C17 N18 . 1.359(2) ?
C17 S23 . 1.6805(16) ?
N18 C19 . 1.392(2) ?
N18 H18 . 0.881(5) ?
C19 O24 . 1.2399(19) ?
C19 C20 . 1.433(2) ?
C20 C21 . 1.354(2) ?
C20 H20 . 0.95 ?
C21 N22 . 1.385(2) ?
C21 C25 . 1.502(2) ?
N22 H22 . 0.878(5) ?
C25 C26 . 1.524(2) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 C27 . 1.526(2) ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 C29 . 1.452(4) ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 N30 . 1.126(3) ?
C31 C32 . 1.454(3) ?
C31 H31A . 0.98 ?
C31 H31B . 0.98 ?
C31 H31C . 0.98 ?
C32 N33 . 1.138(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.56(15) ?
C6 C1 C7 . . 118.22(15) ?
C2 C1 C7 . . 122.19(14) ?
C3 C2 C1 . . 119.62(14) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
O15 C3 C2 . . 125.59(14) ?
O15 C3 C4 . . 113.46(14) ?
C2 C3 C4 . . 120.95(15) ?
O14 C4 C5 . . 118.21(14) ?
O14 C4 C3 . . 122.67(15) ?
C5 C4 C3 . . 119.12(14) ?
O12 C5 C6 . . 125.01(14) ?
O12 C5 C4 . . 114.80(14) ?
C6 C5 C4 . . 120.19(14) ?
C5 C6 C1 . . 120.54(15) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
C8 C7 C1 . . 127.41(16) ?
C8 C7 H7 . . 116.3 ?
C1 C7 H7 . . 116.3 ?
C7 C8 C9 . . 123.47(15) ?
C7 C8 H8 . . 118.3 ?
C9 C8 H8 . . 118.3 ?
O11 C9 O10 . . 122.75(15) ?
O11 C9 C8 . . 122.49(15) ?
O10 C9 C8 . . 114.75(14) ?
C9 O10 H10 . . 110.8(16) ?
C5 O12 C13 . . 117.27(13) ?
O12 C13 H13A . . 109.5 ?
O12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C4 O14 H14 . . 114.9(17) ?
C3 O15 C16 . . 117.37(13) ?
O15 C16 H16A . . 109.5 ?
O15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N22 C17 N18 . . 115.64(14) ?
N22 C17 S23 . . 122.55(12) ?
N18 C17 S23 . . 121.80(12) ?
C17 N18 C19 . . 125.27(14) ?
C17 N18 H18 . . 115.5(14) ?
C19 N18 H18 . . 119.2(14) ?
O24 C19 N18 . . 119.14(15) ?
O24 C19 C20 . . 125.27(15) ?
N18 C19 C20 . . 115.59(14) ?
C21 C20 C19 . . 120.34(15) ?
C21 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C20 C21 N22 . . 118.96(14) ?
C20 C21 C25 . . 127.07(14) ?
N22 C21 C25 . . 113.96(13) ?
C17 N22 C21 . . 124.16(14) ?
C17 N22 H22 . . 118.2(13) ?
C21 N22 H22 . . 117.6(13) ?
C21 C25 C26 . . 115.93(13) ?
C21 C25 H25A . . 108.3 ?
C26 C25 H25A . . 108.3 ?
C21 C25 H25B . . 108.3 ?
C26 C25 H25B . . 108.3 ?
H25A C25 H25B . . 107.4 ?
C25 C26 C27 . . 110.69(14) ?
C25 C26 H26A . . 109.5 ?
C27 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
C27 C26 H26B . . 109.5 ?
H26A C26 H26B . . 108.1 ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C29 C28 H28A . . 109.5 ?
C29 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C29 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
N30 C29 C28 . . 178.1(3) ?
C32 C31 H31A . . 109.5 ?
C32 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C32 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
N33 C32 C31 . . 179.2(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.0(2) ?
C7 C1 C2 C3 . . . . 176.87(15) ?
C1 C2 C3 O15 . . . . -179.14(15) ?
C1 C2 C3 C4 . . . . 0.4(2) ?
O15 C3 C4 O14 . . . . 0.4(2) ?
C2 C3 C4 O14 . . . . -179.20(15) ?
O15 C3 C4 C5 . . . . -179.53(14) ?
C2 C3 C4 C5 . . . . 0.9(2) ?
O14 C4 C5 O12 . . . . -1.6(2) ?
C3 C4 C5 O12 . . . . 178.28(14) ?
O14 C4 C5 C6 . . . . 178.52(15) ?
C3 C4 C5 C6 . . . . -1.6(2) ?
O12 C5 C6 C1 . . . . -178.86(15) ?
C4 C5 C6 C1 . . . . 1.0(2) ?
C2 C1 C6 C5 . . . . 0.3(2) ?
C7 C1 C6 C5 . . . . -177.62(15) ?
C6 C1 C7 C8 . . . . 178.34(16) ?
C2 C1 C7 C8 . . . . 0.5(3) ?
C1 C7 C8 C9 . . . . -176.16(15) ?
C7 C8 C9 O11 . . . . 179.68(16) ?
C7 C8 C9 O10 . . . . 0.9(2) ?
C6 C5 O12 C13 . . . . -3.7(2) ?
C4 C5 O12 C13 . . . . 176.44(14) ?
C2 C3 O15 C16 . . . . 0.6(2) ?
C4 C3 O15 C16 . . . . -178.95(15) ?
N22 C17 N18 C19 . . . . -0.8(2) ?
S23 C17 N18 C19 . . . . -179.62(12) ?
C17 N18 C19 O24 . . . . -179.64(15) ?
C17 N18 C19 C20 . . . . 0.4(2) ?
O24 C19 C20 C21 . . . . -178.86(16) ?
N18 C19 C20 C21 . . . . 1.1(2) ?
C19 C20 C21 N22 . . . . -2.1(2) ?
C19 C20 C21 C25 . . . . 177.18(15) ?
N18 C17 N22 C21 . . . . -0.4(2) ?
S23 C17 N22 C21 . . . . 178.50(12) ?
C20 C21 N22 C17 . . . . 1.8(2) ?
C25 C21 N22 C17 . . . . -177.59(14) ?
C20 C21 C25 C26 . . . . 2.5(2) ?
N22 C21 C25 C26 . . . . -178.19(14) ?
C21 C25 C26 C27 . . . . -178.50(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N18 H18 O11 1_656 0.881(5) 1.935(7) 2.8013(18) 167.(2) ?
N22 H22 S23 2_777 0.878(5) 2.452(6) 3.3199(14) 169.6(18) ?
O10 H10 O24 1_454 0.842(5) 1.797(6) 2.6363(16) 174.(2) ?
O14 H14 N33 1_655 0.839(5) 2.012(10) 2.820(2) 161.(2) ?
####################################################################### 
# 
# 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_SA.PTU.2MeCN_Room_Temp
_database_code_depnum_ccdc_archive 'CCDC 1060815'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;
#===================================================================== 
_chemical_name_systematic        ?
_chemical_name_common            
;
'Sinapic Acid + 6-Propyl-2-thiouracil . 2 Acetonitrile'
;
_chemical_formula_moiety         'C11 H12 O5, C7 H10 N2 O S, 2(C2 H3 N)'
_chemical_formula_sum            'C22 H28 N4 O6 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         476.54

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4520(6)
_cell_length_b                   10.6050(10)
_cell_length_c                   14.9134(13)
_cell_angle_alpha                98.535(3)
_cell_angle_beta                 94.470(3)
_cell_angle_gamma                104.130(3)
_cell_volume                     1272.82(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4329
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      24.98
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Clear colourless'
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504

_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEXII DUO'
_diffrn_measurement_method       'φ & ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            15832
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_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.
;

_reflns_number_total             4437
_reflns_number_gt                2886
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1694
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         4437
_refine_ls_number_parameters     308
_refine_ls_number_restraints     8
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0989P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.397
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.019(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2011.12.3.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al., 2008)'
_computing_publication_material  ?

_iucr_refine_instruction_details 
;
TITL scan_0m_a.res in P-1
CELL  0.71073   8.4520  10.6050  14.9134   98.535   94.470  104.130
ZERR    2.000   0.0006   0.0010   0.0013    0.003    0.003    0.003
LATT 1
SFAC C  H  N  O  S
UNIT 44  56  8  12  2
L.S. 5
ACTA
BOND $H
HTAB O10 O24_$2
HTAB O14 O15
HTAB O14 N33_$4
HTAB N18 O11_$5
HTAB N22 S23_$6
HTAB C28 O12_$7
HTAB C31 O12_$8
EQIV $2_[ x+1, y, z ]
EQIV $4_[ x-1, y, z-1 ]
EQIV $5_[ x-1, y, z ]
EQIV $6_[ -x, -y, -z+1 ]
EQIV $7_[ -x+1, -y+2, -z+1 ]
EQIV $8_[ -x+1, -y+2, -z+1 ]
FMAP 2
PLAN 5
CONF
OMIT     0   0   1
OMIT     0  -1   1
OMIT     0   1   0
ISOR 0.002 c28
SIZE 0.14 0.22 0.27
dfix 0.89 0.005 N18 H18 N22 H22
TEMP 27.000
WGHT    0.098900
EXTI    0.019335
FVAR       0.50323
C1    1    0.428097    0.730383    0.309922    11.00000    0.03733    0.04047 =
         0.04393    0.00884    0.00339    0.01565
C2    1    0.364321    0.662747    0.222357    11.00000    0.05151    0.03797 =
         0.04718    0.00316    0.00534    0.02009
AFIX  43
H2    2    0.374545    0.577707    0.203841    11.00000   -1.20000
AFIX   0
C3    1    0.285354    0.722861    0.162776    11.00000    0.05322    0.04777 =
         0.03720    0.00070    0.00357    0.02003
C4    1    0.267084    0.848942    0.190406    11.00000    0.04336    0.04381 =
         0.04123    0.00950    0.00061    0.01621
C5    1    0.328245    0.916203    0.279107    11.00000    0.04664    0.03471 =
         0.05169    0.00608    0.00228    0.01653
C6    1    0.408315    0.855703    0.337712    11.00000    0.04753    0.04103 =
         0.04041   -0.00014   -0.00464    0.01671
AFIX  43
H6    2    0.449487    0.899918    0.396695    11.00000   -1.20000
AFIX   0
C7    1    0.519118    0.674705    0.373996    11.00000    0.04416    0.04506 =
         0.04298    0.00716   -0.00082    0.01592
AFIX  43
H7    2    0.557344    0.726948    0.431039    11.00000   -1.20000
AFIX   0
C8    1    0.553739    0.558748    0.360602    11.00000    0.05122    0.04215 =
         0.04565    0.00475   -0.00188    0.01839
AFIX  43
H8    2    0.511332    0.502403    0.305485    11.00000   -1.20000
AFIX   0
C9    1    0.653896    0.513513    0.426489    11.00000    0.04529    0.04162 =
         0.04767    0.00932    0.00572    0.01541
O10   4    0.712724    0.598998    0.503127    11.00000    0.06971    0.04811 =
         0.05263    0.00428   -0.01033    0.03107
AFIX 147
H10   2    0.767738    0.566991    0.536640    11.00000   -1.50000
AFIX   0
O11   4    0.684188    0.406158    0.412236    11.00000    0.07709    0.04380 =
         0.06276    0.00300   -0.01085    0.03111
O12   4    0.300232    1.036941    0.300260    11.00000    0.08661    0.04530 =
         0.05888   -0.00546   -0.01836    0.03441
C13   1    0.364915    1.113067    0.387917    11.00000    0.09819    0.04422 =
         0.06932   -0.01529   -0.01992    0.02977
AFIX 137
H13A  2    0.322307    1.064759    0.434175    11.00000   -1.50000
H13B  2    0.333551    1.194760    0.394050    11.00000   -1.50000
H13C  2    0.482583    1.131109    0.394744    11.00000   -1.50000
AFIX   0
O14   4    0.190767    0.911436    0.133749    11.00000    0.07319    0.05367 =
         0.04707    0.00988   -0.01167    0.02718
AFIX 147
H14   2    0.152807    0.860898    0.085562    11.00000   -1.50000
AFIX   0
O15   4    0.219898    0.668273    0.075239    11.00000    0.10172    0.06500 =
         0.04349   -0.00928   -0.01464    0.04331
C16   1    0.235247    0.542529    0.038708    11.00000    0.12474    0.06617 =
         0.05546   -0.02142   -0.01860    0.03928
AFIX 137
H16A  2    0.349258    0.542784    0.043746    11.00000   -1.50000
H16B  2    0.190118    0.520275   -0.024418    11.00000   -1.50000
H16C  2    0.176859    0.478561    0.071822    11.00000   -1.50000
AFIX   0
C17   1   -0.081502    0.200828    0.519617    11.00000    0.04822    0.03707 =
         0.04160    0.00689    0.00537    0.01923
N18   3   -0.113422    0.320662    0.535374    11.00000    0.05131    0.03708 =
         0.04123    0.00549    0.00047    0.02281
AFIX   3
H18   2   -0.174815    0.343652    0.492449    11.00000    0.06688
AFIX   0
C19   1   -0.066853    0.410297    0.616176    11.00000    0.04457    0.03530 =
         0.04686    0.00548    0.00560    0.01576
C20   1    0.020142    0.369348    0.687139    11.00000    0.05047    0.03581 =
         0.04113   -0.00045    0.00019    0.01536
AFIX  43
H20   2    0.055393    0.425607    0.742961    11.00000   -1.20000
AFIX   0
C21   1    0.052137    0.249989    0.674486    11.00000    0.03795    0.03656 =
         0.03865    0.00547    0.00381    0.01179
N22   3    0.001782    0.169408    0.590718    11.00000    0.05024    0.03804 =
         0.03839    0.00385    0.00093    0.02235
AFIX   3
H22   2    0.032679    0.094713    0.584615    11.00000    0.04851
AFIX   0
S23   5   -0.144142    0.098041    0.419799    11.00000    0.09155    0.05218 =
         0.04249   -0.00484   -0.01403    0.04159
O24   4   -0.103068    0.517003    0.621659    11.00000    0.07116    0.03808 =
         0.05804    0.00103   -0.00561    0.02834
C25   1    0.135282    0.190558    0.742903    11.00000    0.04908    0.03993 =
         0.04326    0.00750    0.00323    0.01988
AFIX  23
H25A  2    0.227583    0.165723    0.717279    11.00000   -1.20000
H25B  2    0.058814    0.110178    0.751906    11.00000   -1.20000
AFIX   0
C26   1    0.197849    0.276936    0.835780    11.00000    0.05789    0.05300 =
         0.04413    0.00431   -0.00161    0.01933
AFIX  23
H26A  2    0.278562    0.356091    0.828490    11.00000   -1.20000
H26B  2    0.107312    0.303442    0.862356    11.00000   -1.20000
AFIX   0
C27   1    0.274996    0.203715    0.899238    11.00000    0.07578    0.07923 =
         0.05178    0.01368   -0.00790    0.02609
AFIX 137
H27A  2    0.193672    0.127746    0.908880    11.00000   -1.50000
H27B  2    0.316998    0.261003    0.956671    11.00000   -1.50000
H27C  2    0.363226    0.175974    0.872396    11.00000   -1.50000
AFIX   0
C28   1    0.419738    0.847873    0.845690    11.00000    0.20807    0.20899 =
         0.24826    0.05643    0.06266    0.06077
AFIX 137
H28A  2    0.511690    0.905578    0.825987    11.00000   -1.50000
H28B  2    0.397853    0.888162    0.903805    11.00000   -1.50000
H28C  2    0.324848    0.832216    0.801712    11.00000   -1.50000
AFIX   0
C29   1    0.456514    0.725889    0.853934    11.00000    0.16288    0.09698 =
         0.15056    0.03783    0.06179    0.05719
N30   3    0.489465    0.636661    0.859558    11.00000    0.25258    0.11097 =
         0.09896   -0.01052   -0.00526    0.07411
C31   1    0.898755    0.773601    0.785873    11.00000    0.14258    0.09997 =
         0.06496    0.00395   -0.02055    0.05339
AFIX 137
H31A  2    0.843466    0.841105    0.778505    11.00000   -1.50000
H31B  2    0.819956    0.689094    0.774937    11.00000   -1.50000
H31C  2    0.978018    0.773892    0.743115    11.00000   -1.50000
AFIX   0
C32   1    0.981523    0.798833    0.878059    11.00000    0.09275    0.06795 =
         0.05699    0.01487   -0.00099    0.03455
N33   3    1.044807    0.819355    0.948301    11.00000    0.11722    0.12754 =
         0.06499    0.02232   -0.01465    0.04340
HKLF 4
 
REM  scan_0m_a.res in P-1
REM R1 =  0.0522 for    2886 Fo > 4sig(Fo)  and  0.0995 for all    4437 data
REM    308 parameters refined using      8 restraints
 
END  
     
WGHT      0.1005      0.0000 

REM Highest difference peak  0.612,  deepest hole -0.397,  1-sigma level  0.072
Q1    1   0.3778  0.8209  0.7951  11.00000  0.05    0.61
Q2    1   0.4763  0.8806  0.9155  11.00000  0.05    0.58
Q3    1  -0.2007  0.0598  0.4657  11.00000  0.05    0.30
Q4    1   0.3161  0.6195  0.8457  11.00000  0.05    0.27
Q5    1   0.4768  1.1601  0.3551  11.00000  0.05    0.24
;

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4281(3) 0.7304(2) 0.30992(16) 0.0395(6) Uani d . . . 1 . .
C C2 0.3643(3) 0.6627(2) 0.22236(17) 0.0445(6) Uani d . . . 1 . .
H H2 0.3745 0.5777 0.2038 0.053 Uiso calc U . R 1 . .
C C3 0.2854(3) 0.7229(3) 0.16278(16) 0.0456(6) Uani d . . . 1 . .
C C4 0.2671(3) 0.8489(2) 0.19041(16) 0.0419(6) Uani d . . . 1 . .
C C5 0.3282(3) 0.9162(2) 0.27911(17) 0.0436(6) Uani d . . . 1 . .
C C6 0.4083(3) 0.8557(2) 0.33771(17) 0.0434(6) Uani d . . . 1 . .
H H6 0.4495 0.8999 0.3967 0.052 Uiso calc U . R 1 . .
C C7 0.5191(3) 0.6747(3) 0.37400(17) 0.0437(6) Uani d . . . 1 . .
H H7 0.5573 0.7269 0.431 0.052 Uiso calc U . R 1 . .
C C8 0.5537(3) 0.5587(2) 0.36060(17) 0.0460(6) Uani d . . . 1 . .
H H8 0.5113 0.5024 0.3055 0.055 Uiso calc U . R 1 . .
C C9 0.6539(3) 0.5135(2) 0.42649(17) 0.0439(6) Uani d . . . 1 . .
O O10 0.7127(2) 0.59900(18) 0.50313(12) 0.0555(5) Uani d . . . 1 . .
H H10 0.7677 0.567 0.5366 0.083 Uiso calc U . R 1 . .
O O11 0.6842(2) 0.40616(18) 0.41224(13) 0.0602(5) Uani d . . . 1 . .
O O12 0.3002(2) 1.03694(18) 0.30026(13) 0.0635(6) Uani d . . . 1 . .
C C13 0.3649(4) 1.1131(3) 0.3879(2) 0.0729(9) Uani d . . . 1 . .
H H13A 0.3223 1.0648 0.4342 0.109 Uiso calc U . R 1 . .
H H13B 0.3336 1.1948 0.394 0.109 Uiso calc U . R 1 . .
H H13C 0.4826 1.1311 0.3947 0.109 Uiso calc U . R 1 . .
O O14 0.1908(2) 0.91144(19) 0.13375(12) 0.0570(5) Uani d . . . 1 . .
H H14 0.1528 0.8609 0.0856 0.085 Uiso calc U . R 1 . .
O O15 0.2199(3) 0.6683(2) 0.07524(13) 0.0695(6) Uani d . . . 1 . .
C C16 0.2352(5) 0.5425(3) 0.0387(2) 0.0845(10) Uani d . . . 1 . .
H H16A 0.3493 0.5428 0.0437 0.127 Uiso calc U . R 1 . .
H H16B 0.1901 0.5203 -0.0244 0.127 Uiso calc U . R 1 . .
H H16C 0.1769 0.4786 0.0718 0.127 Uiso calc U . R 1 . .
C C17 -0.0815(3) 0.2008(2) 0.51962(16) 0.0408(6) Uani d . . . 1 . .
N N18 -0.1134(2) 0.32066(19) 0.53537(13) 0.0416(5) Uani d . . D 1 . .
H H18 -0.1748 0.3437 0.4924 0.067(8) Uiso d . . DR 1 . .
C C19 -0.0669(3) 0.4103(2) 0.61618(16) 0.0415(6) Uani d . . . 1 . .
C C20 0.0201(3) 0.3693(2) 0.68714(16) 0.0428(6) Uani d . . . 1 . .
H H20 0.0554 0.4256 0.743 0.051 Uiso calc U . R 1 . .
C C21 0.0521(3) 0.2500(2) 0.67449(15) 0.0375(5) Uani d . . . 1 . .
N N22 0.0018(2) 0.1694(2) 0.59072(13) 0.0408(5) Uani d . . D 1 . .
H H22 0.0327 0.0947 0.5846 0.049(7) Uiso d . . DR 1 . .
S S23 -0.14414(10) 0.09804(7) 0.41980(5) 0.0606(3) Uani d . . . 1 . .
O O24 -0.1031(2) 0.51700(17) 0.62166(12) 0.0548(5) Uani d . . . 1 . .
C C25 0.1353(3) 0.1906(2) 0.74290(16) 0.0427(6) Uani d . . . 1 . .
H H25A 0.2276 0.1657 0.7173 0.051 Uiso calc U . R 1 . .
H H25B 0.0588 0.1102 0.7519 0.051 Uiso calc U . R 1 . .
C C26 0.1978(3) 0.2769(3) 0.83578(17) 0.0517(7) Uani d . . . 1 . .
H H26A 0.2786 0.3561 0.8285 0.062 Uiso calc U . R 1 . .
H H26B 0.1073 0.3034 0.8624 0.062 Uiso calc U . R 1 . .
C C27 0.2750(4) 0.2037(3) 0.8992(2) 0.0685(8) Uani d . . . 1 . .
H H27A 0.1937 0.1277 0.9089 0.103 Uiso calc U . R 1 . .
H H27B 0.317 0.261 0.9567 0.103 Uiso calc U . R 1 . .
H H27C 0.3632 0.176 0.8724 0.103 Uiso calc U . R 1 . .
C C28 0.4197(10) 0.8479(9) 0.8457(6) 0.217(3) Uani d U . . 1 . .
H H28A 0.5117 0.9056 0.826 0.325 Uiso calc U . R 1 . .
H H28B 0.3979 0.8882 0.9038 0.325 Uiso calc U . R 1 . .
H H28C 0.3248 0.8322 0.8017 0.325 Uiso calc U . R 1 . .
C C29 0.4565(7) 0.7259(6) 0.8539(4) 0.1285(19) Uani d . . . 1 . .
N N30 0.4895(8) 0.6367(5) 0.8596(3) 0.1539(19) Uani d . . . 1 . .
C C31 0.8988(5) 0.7736(4) 0.7859(3) 0.1015(13) Uani d . . . 1 . .
H H31A 0.8435 0.8411 0.7785 0.152 Uiso calc U . R 1 . .
H H31B 0.82 0.6891 0.7749 0.152 Uiso calc U . R 1 . .
H H31C 0.978 0.7739 0.7431 0.152 Uiso calc U . R 1 . .
C C32 0.9815(4) 0.7988(3) 0.8781(2) 0.0703(9) Uani d . . . 1 . .
N N33 1.0448(4) 0.8194(4) 0.9483(2) 0.1020(11) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.386(3) ?
C1 C2 . 1.391(3) ?
C1 C7 . 1.459(3) ?
C2 C3 . 1.387(3) ?
C2 H2 . 0.93 ?
C3 O15 . 1.361(3) ?
C3 C4 . 1.389(4) ?
C4 O14 . 1.364(3) ?
C4 C5 . 1.400(3) ?
C5 O12 . 1.355(3) ?
C5 C6 . 1.386(3) ?
C6 H6 . 0.93 ?
C7 C8 . 1.323(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.456(3) ?
C8 H8 . 0.93 ?
C9 O11 . 1.219(3) ?
C9 O10 . 1.326(3) ?
O10 H10 . 0.82 ?
O12 C13 . 1.421(3) ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
O14 H14 . 0.82 ?
O15 C16 . 1.404(4) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 N18 . 1.353(3) ?
C17 N22 . 1.354(3) ?
C17 S23 . 1.673(3) ?
N18 C19 . 1.383(3) ?
N18 H18 . 0.8915 ?
C19 O24 . 1.236(3) ?
C19 C20 . 1.421(3) ?
C20 C21 . 1.347(3) ?
C20 H20 . 0.93 ?
C21 N22 . 1.376(3) ?
C21 C25 . 1.492(3) ?
N22 H22 . 0.8873 ?
C25 C26 . 1.520(3) ?
C25 H25A . 0.97 ?
C25 H25B . 0.97 ?
C26 C27 . 1.514(3) ?
C26 H26A . 0.97 ?
C26 H26B . 0.97 ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?
C28 C29 . 1.422(9) ?
C28 H28A . 0.96 ?
C28 H28B . 0.96 ?
C28 H28C . 0.96 ?
C29 N30 . 1.062(6) ?
C31 C32 . 1.449(5) ?
C31 H31A . 0.96 ?
C31 H31B . 0.96 ?
C31 H31C . 0.96 ?
C32 N33 . 1.104(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.8(2) ?
C6 C1 C7 . . 118.2(2) ?
C2 C1 C7 . . 122.0(2) ?
C3 C2 C1 . . 119.6(2) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
O15 C3 C2 . . 125.4(2) ?
O15 C3 C4 . . 114.1(2) ?
C2 C3 C4 . . 120.5(2) ?
O14 C4 C3 . . 122.3(2) ?
O14 C4 C5 . . 117.8(2) ?
C3 C4 C5 . . 119.9(2) ?
O12 C5 C6 . . 125.6(2) ?
O12 C5 C4 . . 115.5(2) ?
C6 C5 C4 . . 119.0(2) ?
C5 C6 C1 . . 121.1(2) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
C8 C7 C1 . . 127.7(3) ?
C8 C7 H7 . . 116.1 ?
C1 C7 H7 . . 116.1 ?
C7 C8 C9 . . 124.3(3) ?
C7 C8 H8 . . 117.8 ?
C9 C8 H8 . . 117.8 ?
O11 C9 O10 . . 122.1(2) ?
O11 C9 C8 . . 122.9(2) ?
O10 C9 C8 . . 115.0(2) ?
C9 O10 H10 . . 109.5 ?
C5 O12 C13 . . 118.4(2) ?
O12 C13 H13A . . 109.5 ?
O12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C4 O14 H14 . . 109.5 ?
C3 O15 C16 . . 119.3(2) ?
O15 C16 H16A . . 109.5 ?
O15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N18 C17 N22 . . 115.3(2) ?
N18 C17 S23 . . 122.09(17) ?
N22 C17 S23 . . 122.60(19) ?
C17 N18 C19 . . 125.35(19) ?
C17 N18 H18 . . 119.0 ?
C19 N18 H18 . . 115.5 ?
O24 C19 N18 . . 119.0(2) ?
O24 C19 C20 . . 125.4(2) ?
N18 C19 C20 . . 115.6(2) ?
C21 C20 C19 . . 120.8(2) ?
C21 C20 H20 . . 119.6 ?
C19 C20 H20 . . 119.6 ?
C20 C21 N22 . . 118.6(2) ?
C20 C21 C25 . . 127.2(2) ?
N22 C21 C25 . . 114.1(2) ?
C17 N22 C21 . . 124.3(2) ?
C17 N22 H22 . . 120.6 ?
C21 N22 H22 . . 115.0 ?
C21 C25 C26 . . 116.3(2) ?
C21 C25 H25A . . 108.2 ?
C26 C25 H25A . . 108.2 ?
C21 C25 H25B . . 108.2 ?
C26 C25 H25B . . 108.2 ?
H25A C25 H25B . . 107.4 ?
C27 C26 C25 . . 110.9(2) ?
C27 C26 H26A . . 109.5 ?
C25 C26 H26A . . 109.5 ?
C27 C26 H26B . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 108.1 ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C29 C28 H28A . . 109.5 ?
C29 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C29 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
N30 C29 C28 . . 177.4(8) ?
C32 C31 H31A . . 109.5 ?
C32 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C32 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
N33 C32 C31 . . 179.3(4) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.8(4) ?
C7 C1 C2 C3 . . . . -177.0(2) ?
C1 C2 C3 O15 . . . . 179.0(2) ?
C1 C2 C3 C4 . . . . -1.1(4) ?
O15 C3 C4 O14 . . . . -0.4(3) ?
C2 C3 C4 O14 . . . . 179.8(2) ?
O15 C3 C4 C5 . . . . 179.7(2) ?
C2 C3 C4 C5 . . . . -0.2(4) ?
O14 C4 C5 O12 . . . . 1.9(3) ?
C3 C4 C5 O12 . . . . -178.2(2) ?
O14 C4 C5 C6 . . . . -179.1(2) ?
C3 C4 C5 C6 . . . . 0.8(4) ?
O12 C5 C6 C1 . . . . 178.7(2) ?
C4 C5 C6 C1 . . . . -0.2(4) ?
C2 C1 C6 C5 . . . . -1.1(4) ?
C7 C1 C6 C5 . . . . 177.7(2) ?
C6 C1 C7 C8 . . . . -178.9(2) ?
C2 C1 C7 C8 . . . . -0.1(4) ?
C1 C7 C8 C9 . . . . 176.2(2) ?
C7 C8 C9 O11 . . . . -179.8(2) ?
C7 C8 C9 O10 . . . . -0.9(4) ?
C6 C5 O12 C13 . . . . 3.7(4) ?
C4 C5 O12 C13 . . . . -177.4(2) ?
C2 C3 O15 C16 . . . . -2.1(4) ?
C4 C3 O15 C16 . . . . 178.1(3) ?
N22 C17 N18 C19 . . . . 0.6(3) ?
S23 C17 N18 C19 . . . . 179.46(17) ?
C17 N18 C19 O24 . . . . 179.7(2) ?
C17 N18 C19 C20 . . . . -0.6(3) ?
O24 C19 C20 C21 . . . . 179.3(2) ?
N18 C19 C20 C21 . . . . -0.4(3) ?
C19 C20 C21 N22 . . . . 1.3(3) ?
C19 C20 C21 C25 . . . . -177.2(2) ?
N18 C17 N22 C21 . . . . 0.4(3) ?
S23 C17 N22 C21 . . . . -178.49(17) ?
C20 C21 N22 C17 . . . . -1.3(3) ?
C25 C21 N22 C17 . . . . 177.43(19) ?
C20 C21 C25 C26 . . . . -3.1(4) ?
N22 C21 C25 C26 . . . . 178.3(2) ?
C21 C25 C26 C27 . . . . 178.4(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O10 H10 O24 1_655 0.82 1.83 2.644(2) 172.3 ?
O14 H14 O15 . 0.82 2.24 2.673(3) 113.6 ?
O14 H14 N33 1_454 0.82 2.11 2.864(4) 152.3 ?
N18 H18 O11 1_455 0.89 1.92 2.808(2) 172.8 ?
N22 H22 S23 2_556 0.89 2.45 3.329(2) 173.6 ?
C28 H28A O12 2_676 0.96 2.60 3.466(8) 149.6 ?
C31 H31A O12 2_676 0.96 2.35 3.255(4) 156.9 ?

#====END

