# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_130802lt_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H27 N3 O5 S'
_chemical_formula_weight         565.63

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1408(17)
_cell_length_b                   10.8111(18)
_cell_length_c                   13.136(2)
_cell_angle_alpha                103.814(4)
_cell_angle_beta                 92.891(4)
_cell_angle_gamma                95.161(4)
_cell_volume                     1389.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4261
_cell_measurement_theta_min      2.4842
_cell_measurement_theta_max      25.9242

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7194
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19602
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         26.53
_reflns_number_total             5725
_reflns_number_gt                4308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_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    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0932P)²+0.4584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5725
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.63246(5) 0.81073(5) 0.86174(4) 0.01989(17) Uani 1 1 d . . .
O1 O 0.78101(16) 0.98531(15) 0.46830(13) 0.0276(4) Uani 1 1 d . . .
O2 O 0.60473(19) 0.61994(17) 0.31274(15) 0.0383(5) Uani 1 1 d . . .
O3 O 0.7165(2) 0.55579(17) 0.43856(15) 0.0413(5) Uani 1 1 d . . .
O4 O 0.65684(16) 0.92383(15) 0.94440(13) 0.0247(4) Uani 1 1 d . . .
O5 O 0.51276(15) 0.78625(15) 0.79453(13) 0.0238(4) Uani 1 1 d . . .
N1 N 0.75386(18) 0.81412(18) 0.78015(15) 0.0214(4) Uani 1 1 d . . .
N2 N 0.71463(19) 0.87689(18) 0.42735(15) 0.0223(4) Uani 1 1 d . . .
N3 N 0.9854(2) 0.7565(2) 0.48274(16) 0.0289(5) Uani 1 1 d . . .
C1 C 0.6991(3) 0.3605(3) 1.0485(2) 0.0367(6) Uani 1 1 d . . .
H1A H 0.7937 0.3570 1.0654 0.055 Uiso 1 1 calc R . .
H1B H 0.6626 0.2807 0.9985 0.055 Uiso 1 1 calc R . .
H1C H 0.6521 0.3714 1.1128 0.055 Uiso 1 1 calc R . .
C2 C 0.6823(2) 0.4718(2) 1.0003(2) 0.0271(5) Uani 1 1 d . . .
C3 C 0.6344(2) 0.4534(2) 0.8958(2) 0.0290(6) Uani 1 1 d . . .
H3A H 0.6112 0.3688 0.8540 0.035 Uiso 1 1 calc R . .
C4 C 0.6200(2) 0.5567(2) 0.85185(19) 0.0243(5) Uani 1 1 d . . .
H4 H 0.5866 0.5437 0.7808 0.029 Uiso 1 1 calc R . .
C5 C 0.6554(2) 0.6788(2) 0.91382(17) 0.0207(5) Uani 1 1 d . . .
C6 C 0.7338(2) 0.7935(2) 0.67213(17) 0.0211(5) Uani 1 1 d . . .
H6 H 0.6496 0.7784 0.6338 0.025 Uiso 1 1 calc R . .
C7 C 0.8534(2) 0.7981(2) 0.62882(18) 0.0212(5) Uani 1 1 d . . .
C8 C 0.8713(2) 0.7763(2) 0.51751(18) 0.0228(5) Uani 1 1 d . . .
C9 C 0.7497(2) 0.7694(2) 0.44521(18) 0.0222(5) Uani 1 1 d . . .
C10 C 0.5982(2) 0.8826(2) 0.35878(18) 0.0219(5) Uani 1 1 d . . .
C11 C 0.4732(2) 0.8715(2) 0.3949(2) 0.0282(5) Uani 1 1 d . . .
H11 H 0.4619 0.8590 0.4632 0.034 Uiso 1 1 calc R . .
C12 C 0.3644(2) 0.8790(2) 0.3290(2) 0.0302(6) Uani 1 1 d . . .
H12 H 0.2773 0.8705 0.3517 0.036 Uiso 1 1 calc R . .
C13 C 0.3825(2) 0.8988(2) 0.2303(2) 0.0272(5) Uani 1 1 d . . .
H13 H 0.3078 0.9036 0.1853 0.033 Uiso 1 1 calc R . .
C14 C 0.7028(2) 0.7002(2) 1.01809(19) 0.0257(5) Uani 1 1 d . . .
H14 H 0.7263 0.7850 1.0596 0.031 Uiso 1 1 calc R . .
C15 C 0.7153(2) 0.5962(3) 1.0608(2) 0.0287(6) Uani 1 1 d . . .
H15 H 0.7468 0.6100 1.1324 0.034 Uiso 1 1 calc R . .
C16 C 0.8916(2) 0.8323(2) 0.80789(18) 0.0199(5) Uani 1 1 d . . .
C17 C 0.9559(2) 0.8233(2) 0.71489(18) 0.0208(5) Uani 1 1 d . . .
C18 C 1.0949(2) 0.8396(2) 0.71966(19) 0.0244(5) Uani 1 1 d . . .
H18 H 1.1406 0.8349 0.6577 0.029 Uiso 1 1 calc R . .
C19 C 1.1638(2) 0.8628(2) 0.8172(2) 0.0264(5) Uani 1 1 d . . .
H19 H 1.2581 0.8735 0.8219 0.032 Uiso 1 1 calc R . .
C20 C 1.0974(2) 0.8710(2) 0.90868(19) 0.0251(5) Uani 1 1 d . . .
H20 H 1.1478 0.8868 0.9743 0.030 Uiso 1 1 calc R . .
C21 C 0.9596(2) 0.8566(2) 0.90624(18) 0.0218(5) Uani 1 1 d . . .
H21 H 0.9143 0.8629 0.9686 0.026 Uiso 1 1 calc R . .
C22 C 0.6191(2) 0.9039(2) 0.26184(19) 0.0249(5) Uani 1 1 d . . .
H22 H 0.7065 0.9130 0.2398 0.030 Uiso 1 1 calc R . .
C23 C 0.5096(2) 0.9118(2) 0.1965(2) 0.0270(5) Uani 1 1 d . . .
H23 H 0.5216 0.9261 0.1288 0.032 Uiso 1 1 calc R . .
C24 C 0.6613(4) 0.4246(3) 0.3895(3) 0.0583(10) Uani 1 1 d . . .
H24A H 0.5651 0.4220 0.3709 0.070 Uiso 1 1 calc R . .
H24B H 0.7052 0.3918 0.3243 0.070 Uiso 1 1 calc R . .
C25 C 0.6827(4) 0.3458(3) 0.4627(3) 0.0519(8) Uani 1 1 d . . .
H25A H 0.7778 0.3517 0.4831 0.078 Uiso 1 1 calc R . .
H25B H 0.6499 0.2565 0.4292 0.078 Uiso 1 1 calc R . .
H25C H 0.6348 0.3758 0.5254 0.078 Uiso 1 1 calc R . .
C26 C 0.9997(2) 0.7361(3) 0.3730(2) 0.0316(6) Uani 1 1 d . . .
C27 C 0.9942(2) 0.8354(3) 0.3229(2) 0.0320(6) Uani 1 1 d . . .
H27 H 0.9766 0.9178 0.3612 0.038 Uiso 1 1 calc R . .
C28 C 1.0145(2) 0.8137(3) 0.2164(2) 0.0375(7) Uani 1 1 d . . .
H28 H 1.0101 0.8814 0.1821 0.045 Uiso 1 1 calc R . .
C29 C 1.0408(3) 0.6954(3) 0.1605(2) 0.0429(7) Uani 1 1 d . . .
H29 H 1.0546 0.6811 0.0878 0.051 Uiso 1 1 calc R . .
C30 C 1.0472(3) 0.5968(3) 0.2108(2) 0.0456(8) Uani 1 1 d . . .
H30 H 1.0650 0.5147 0.1720 0.055 Uiso 1 1 calc R . .
C31 C 1.0279(3) 0.6165(3) 0.3172(2) 0.0396(7) Uani 1 1 d . . .
H31 H 1.0339 0.5489 0.3514 0.048 Uiso 1 1 calc R . .
C32 C 0.6808(2) 0.6433(2) 0.38943(18) 0.0255(5) 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
S1 O4 1.4213(17) . ?
S1 O5 1.4301(16) . ?
S1 N1 1.676(2) . ?
S1 C5 1.751(2) . ?
O1 N2 1.279(2) . ?
O2 C32 1.200(3) . ?
O3 C32 1.331(3) . ?
O3 C24 1.457(3) . ?
N1 C6 1.384(3) . ?
N1 C16 1.410(3) . ?
N2 C9 1.315(3) . ?
N2 C10 1.463(3) . ?
N3 C8 1.282(3) . ?
N3 C26 1.422(3) . ?
C1 C2 1.506(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C15 1.391(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.390(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C14 1.387(3) . ?
C6 C7 1.367(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.448(3) . ?
C7 C17 1.455(3) . ?
C8 C9 1.504(3) . ?
C9 C32 1.478(3) . ?
C10 C22 1.370(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C23 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.389(3) . ?
C16 C17 1.400(3) . ?
C17 C18 1.401(3) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.395(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.450(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C31 1.388(4) . ?
C26 C27 1.391(4) . ?
C27 C28 1.391(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.371(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?

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
O4 S1 O5 120.74(10) . . ?
O4 S1 N1 107.13(10) . . ?
O5 S1 N1 104.38(10) . . ?
O4 S1 C5 108.48(11) . . ?
O5 S1 C5 110.20(10) . . ?
N1 S1 C5 104.65(10) . . ?
C32 O3 C24 115.2(2) . . ?
C6 N1 C16 108.62(18) . . ?
C6 N1 S1 124.69(16) . . ?
C16 N1 S1 126.64(15) . . ?
O1 N2 C9 122.3(2) . . ?
O1 N2 C10 114.60(18) . . ?
C9 N2 C10 123.13(19) . . ?
C8 N3 C26 119.2(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C15 C2 C3 118.9(2) . . ?
C15 C2 C1 119.6(2) . . ?
C3 C2 C1 121.5(2) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C14 121.8(2) . . ?
C4 C5 S1 119.32(17) . . ?
C14 C5 S1 118.83(19) . . ?
C7 C6 N1 109.9(2) . . ?
C7 C6 H6 125.1 . . ?
N1 C6 H6 125.1 . . ?
C6 C7 C8 125.4(2) . . ?
C6 C7 C17 107.0(2) . . ?
C8 C7 C17 127.6(2) . . ?
N3 C8 C7 120.7(2) . . ?
N3 C8 C9 122.0(2) . . ?
C7 C8 C9 117.2(2) . . ?
N2 C9 C32 122.0(2) . . ?
N2 C9 C8 118.0(2) . . ?
C32 C9 C8 119.7(2) . . ?
C22 C10 C11 122.7(2) . . ?
C22 C10 N2 117.8(2) . . ?
C11 C10 N2 119.5(2) . . ?
C10 C11 C12 118.4(2) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C23 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C23 C13 H13 119.8 . . ?
C15 C14 C5 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C5 C14 H14 120.5 . . ?
C14 C15 C2 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C2 C15 H15 119.6 . . ?
C21 C16 C17 122.9(2) . . ?
C21 C16 N1 129.8(2) . . ?
C17 C16 N1 107.29(19) . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 C7 107.25(19) . . ?
C18 C17 C7 133.3(2) . . ?
C19 C18 C17 118.2(2) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 121.7(2) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C16 C21 C20 116.5(2) . . ?
C16 C21 H21 121.8 . . ?
C20 C21 H21 121.8 . . ?
C10 C22 C23 118.5(2) . . ?
C10 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C13 C23 C22 119.9(2) . . ?
C13 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 O3 108.8(3) . . ?
C25 C24 H24A 109.9 . . ?
O3 C24 H24A 109.9 . . ?
C25 C24 H24B 109.9 . . ?
O3 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C31 C26 C27 119.9(2) . . ?
C31 C26 N3 118.8(2) . . ?
C27 C26 N3 121.2(2) . . ?
C26 C27 C28 119.8(3) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 120.5(3) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 119.6(3) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C29 C30 C31 120.8(3) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C26 C31 C30 119.3(3) . . ?
C26 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
O2 C32 O3 124.0(2) . . ?
O2 C32 C9 127.3(2) . . ?
O3 C32 C9 108.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.53
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.078
_database_code_depnum_ccdc_archive 'CCDC 1020243'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
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data_mo_140816_0m_a

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O6'
_chemical_formula_weight         384.38

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

_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                   11.8424(8)
_cell_length_b                   10.9091(8)
_cell_length_c                   16.0091(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.318(2)
_cell_angle_gamma                90
_cell_volume                     1994.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.4586
_cell_measurement_theta_max      26.3804

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8871
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            15944
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.783
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4076
_reflns_number_gt                2546
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+0.2652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4076
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.30150(16) 0.27874(18) 0.50426(12) 0.0446(5) Uani 1 1 d . . . . .
C2 C 0.39452(18) 0.18583(19) 0.53675(12) 0.0471(5) Uani 1 1 d . . . . .
C3 C 0.59943(19) 0.1491(2) 0.58387(18) 0.0735(7) Uani 1 1 d . . . . .
H3A H 0.5983 0.1304 0.6429 0.088 Uiso 1 1 calc R U . . .
H3B H 0.5943 0.0728 0.5520 0.088 Uiso 1 1 calc R U . . .
C4 C 0.7053(2) 0.2127(4) 0.5833(3) 0.1413(16) Uani 1 1 d . . . . .
H4A H 0.7092 0.2235 0.5247 0.212 Uiso 1 1 calc R U . . .
H4B H 0.7716 0.1656 0.6147 0.212 Uiso 1 1 calc R U . . .
H4C H 0.7061 0.2913 0.6104 0.212 Uiso 1 1 calc R U . . .
C5 C 0.19151(16) 0.24086(18) 0.44666(12) 0.0447(5) Uani 1 1 d . . . . .
C6 C 0.08127(18) 0.2783(2) 0.46738(14) 0.0526(5) Uani 1 1 d . . . . .
C7 C -0.1169(2) 0.3356(3) 0.4099(2) 0.0958(10) Uani 1 1 d . . . . .
H7A H -0.1342 0.2843 0.4544 0.115 Uiso 1 1 calc R U . . .
H7B H -0.1162 0.4204 0.4282 0.115 Uiso 1 1 calc R U . . .
C8 C -0.2045(3) 0.3187(4) 0.3297(3) 0.1502(19) Uani 1 1 d . . . . .
H8A H -0.1823 0.3627 0.2845 0.225 Uiso 1 1 calc R U . . .
H8B H -0.2782 0.3491 0.3353 0.225 Uiso 1 1 calc R U . . .
H8C H -0.2115 0.2331 0.3156 0.225 Uiso 1 1 calc R U . . .
C9 C 0.40191(17) 0.43754(18) 0.60374(12) 0.0455(5) Uani 1 1 d . . . . .
C10 C 0.4181(2) 0.3793(2) 0.68183(14) 0.0585(6) Uani 1 1 d . . . . .
H10 H 0.3726 0.3120 0.6876 0.070 Uiso 1 1 calc R U . . .
C11 C 0.5035(2) 0.4229(3) 0.75165(15) 0.0723(7) Uani 1 1 d . . . . .
H11 H 0.5158 0.3850 0.8053 0.087 Uiso 1 1 calc R U . . .
C12 C 0.5707(2) 0.5224(3) 0.74216(17) 0.0735(7) Uani 1 1 d . . . . .
H12 H 0.6298 0.5497 0.7891 0.088 Uiso 1 1 calc R U . . .
C13 C 0.5510(2) 0.5813(2) 0.66395(16) 0.0666(6) Uani 1 1 d . . . . .
H13 H 0.5958 0.6493 0.6583 0.080 Uiso 1 1 calc R U . . .
C14 C 0.46500(18) 0.54013(19) 0.59373(14) 0.0530(5) Uani 1 1 d . . . . .
H14 H 0.4499 0.5806 0.5408 0.064 Uiso 1 1 calc R U . . .
C15 C 0.09163(16) 0.10426(18) 0.33081(13) 0.0457(5) Uani 1 1 d . . . . .
C16 C 0.05702(19) 0.1209(2) 0.24275(13) 0.0557(5) Uani 1 1 d . . . . .
H16 H 0.0995 0.1716 0.2155 0.067 Uiso 1 1 calc R U . . .
C17 C -0.0416(2) 0.0612(2) 0.19542(16) 0.0704(7) Uani 1 1 d . . . . .
H17 H -0.0674 0.0729 0.1359 0.084 Uiso 1 1 calc R U . . .
C18 C -0.1014(2) -0.0149(3) 0.2356(2) 0.0791(8) Uani 1 1 d . . . . .
H18 H -0.1682 -0.0546 0.2033 0.095 Uiso 1 1 calc R U . . .
C19 C -0.0648(2) -0.0337(2) 0.32299(19) 0.0786(8) Uani 1 1 d . . . . .
H19 H -0.1060 -0.0869 0.3495 0.094 Uiso 1 1 calc R U . . .
C20 C 0.0335(2) 0.0262(2) 0.37218(15) 0.0595(6) Uani 1 1 d . . . . .
H20 H 0.0594 0.0138 0.4317 0.071 Uiso 1 1 calc R U . . .
N1 N 0.31174(14) 0.39457(15) 0.52937(10) 0.0471(4) Uani 1 1 d . . . . .
N2 N 0.19433(13) 0.16937(15) 0.38061(10) 0.0449(4) Uani 1 1 d . . . . .
O1 O 0.28928(12) 0.14894(15) 0.35920(9) 0.0611(4) Uani 1 1 d . . . . .
O2 O 0.07539(15) 0.28612(19) 0.54060(11) 0.0827(6) Uani 1 1 d . . . . .
O3 O -0.00342(12) 0.30301(14) 0.39749(9) 0.0594(4) Uani 1 1 d . . . . .
O4 O 0.23716(13) 0.47519(14) 0.49157(10) 0.0666(5) Uani 1 1 d . . . . .
O5 O 0.37129(13) 0.08317(14) 0.55322(10) 0.0637(4) Uani 1 1 d . . . . .
O6 O 0.50079(12) 0.22907(13) 0.54302(9) 0.0550(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.322(2) . ?
C1 C5 1.443(3) . ?
C1 C2 1.486(3) . ?
C2 O5 1.199(2) . ?
C2 O6 1.323(2) . ?
C3 C4 1.435(4) . ?
C3 O6 1.466(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N2 1.322(2) . ?
C5 C6 1.487(3) . ?
C6 O2 1.196(2) . ?
C6 O3 1.318(3) . ?
C7 C8 1.433(4) . ?
C7 O3 1.453(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.370(3) . ?
C9 C14 1.378(3) . ?
C9 N1 1.451(2) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.371(3) . ?
C15 C16 1.372(3) . ?
C15 N2 1.452(2) . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 O4 1.280(2) . ?
N2 O1 1.2787(19) . ?

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
N1 C1 C5 117.57(17) . . ?
N1 C1 C2 123.07(17) . . ?
C5 C1 C2 119.25(17) . . ?
O5 C2 O6 125.83(19) . . ?
O5 C2 C1 121.48(19) . . ?
O6 C2 C1 112.69(17) . . ?
C4 C3 O6 107.7(2) . . ?
C4 C3 H3A 110.2 . . ?
O6 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
O6 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C1 118.09(16) . . ?
N2 C5 C6 123.38(17) . . ?
C1 C5 C6 118.44(17) . . ?
O2 C6 O3 126.1(2) . . ?
O2 C6 C5 121.4(2) . . ?
O3 C6 C5 112.52(17) . . ?
C8 C7 O3 108.8(2) . . ?
C8 C7 H7A 109.9 . . ?
O3 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
O3 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 122.2(2) . . ?
C10 C9 N1 119.62(18) . . ?
C14 C9 N1 118.09(18) . . ?
C9 C10 C11 118.4(2) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 118.5(2) . . ?
C13 C14 H14 120.8 . . ?
C9 C14 H14 120.8 . . ?
C20 C15 C16 121.8(2) . . ?
C20 C15 N2 119.57(18) . . ?
C16 C15 N2 118.63(18) . . ?
C15 C16 C17 118.9(2) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 118.2(2) . . ?
C15 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
O4 N1 C1 121.12(16) . . ?
O4 N1 C9 115.62(15) . . ?
C1 N1 C9 123.14(16) . . ?
O1 N2 C5 121.83(16) . . ?
O1 N2 C15 115.85(15) . . ?
C5 N2 C15 122.25(16) . . ?
C6 O3 C7 117.25(19) . . ?
C2 O6 C3 116.84(17) . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.035

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 1022207'
