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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  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.
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data_fv007

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H22 N2 O3 S), H2 O'
_chemical_formula_sum            'C30 H46 N4 O7 S2'
_chemical_formula_weight         638.85

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           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   20.584(4)
_cell_length_b                   16.0252(13)
_cell_length_c                   13.038(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.09(3)
_cell_angle_gamma                90.00
_cell_volume                     3384.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6040
_cell_measurement_theta_min      3.1176
_cell_measurement_theta_max      25.7822

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, δφ 1.5°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12880
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2897
_reflns_number_gt                2586
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  Platon

_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)+(0.0000P)²+25.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2897
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1549
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1227(2) 0.2455(2) 0.7844(3) 0.0290(8) Uani 1 1 d . . .
C2 C 0.1347(2) 0.2621(2) 0.9007(3) 0.0311(8) Uani 1 1 d . . .
C3 C 0.1280(2) 0.1949(2) 0.9613(4) 0.0342(8) Uani 1 1 d . . .
H3 H 0.1342 0.2047 1.0388 0.041 Uiso 1 1 calc R . .
C4 C 0.1128(2) 0.1148(2) 0.9134(4) 0.0366(9) Uani 1 1 d . . .
C5 C 0.1024(2) 0.1017(2) 0.7988(4) 0.0372(9) Uani 1 1 d . . .
H5 H 0.0931 0.0466 0.7657 0.045 Uiso 1 1 calc R . .
C6 C 0.1053(2) 0.1665(2) 0.7309(4) 0.0325(8) Uani 1 1 d . . .
C7 C 0.1563(2) 0.3486(2) 0.9591(4) 0.0369(9) Uani 1 1 d . . .
H7A H 0.2072 0.3673 0.9755 0.055 Uiso 1 1 calc R . .
H7B H 0.1643 0.3474 1.0414 0.055 Uiso 1 1 calc R . .
H7C H 0.1113 0.3871 0.8984 0.055 Uiso 1 1 calc R . .
C8 C 0.1083(3) 0.0439(3) 0.9834(5) 0.0491(11) Uani 1 1 d . . .
H8A H 0.1639 0.0223 1.0504 0.074 Uiso 1 1 calc R . .
H8B H 0.0737 -0.0006 0.9212 0.074 Uiso 1 1 calc R . .
H8C H 0.0842 0.0635 1.0246 0.074 Uiso 1 1 calc R . .
C9 C 0.0883(3) 0.1511(3) 0.6023(4) 0.0442(10) Uani 1 1 d . . .
H9A H 0.0464 0.1906 0.5373 0.066 Uiso 1 1 calc R . .
H9B H 0.0681 0.0940 0.5734 0.066 Uiso 1 1 calc R . .
H9C H 0.1392 0.1588 0.6125 0.066 Uiso 1 1 calc R . .
C10 C 0.1873(2) 0.3310(2) 0.7142(3) 0.0299(8) Uani 1 1 d . . .
H10 H 0.2363 0.2985 0.7592 0.036 Uiso 1 1 calc R . .
C11 C 0.0940(2) 0.4344(2) 0.5895(4) 0.0362(9) Uani 1 1 d . . .
H11A H 0.0593 0.4405 0.4936 0.043 Uiso 1 1 calc R . .
H11B H 0.1012 0.4897 0.6289 0.043 Uiso 1 1 calc R . .
C12 C 0.0565(2) 0.3719(2) 0.6277(4) 0.0354(9) Uani 1 1 d . . .
H12A H 0.0371 0.3999 0.6720 0.042 Uiso 1 1 calc R . .
H12B H 0.0097 0.3415 0.5505 0.042 Uiso 1 1 calc R . .
C13 C 0.2345(2) 0.4351(2) 0.6323(4) 0.0351(9) Uani 1 1 d . . .
H13A H 0.2877 0.4049 0.6885 0.042 Uiso 1 1 calc R . .
H13B H 0.2442 0.4934 0.6639 0.042 Uiso 1 1 calc R . .
C14 C 0.2052(2) 0.4350(2) 0.4931(4) 0.0340(8) Uani 1 1 d . . .
H14A H 0.1507 0.4629 0.4363 0.041 Uiso 1 1 calc R . .
H14B H 0.2444 0.4675 0.4890 0.041 Uiso 1 1 calc R . .
C15 C 0.1978(3) 0.3488(3) 0.4429(4) 0.0442(10) Uani 1 1 d . . .
H15A H 0.1590 0.3166 0.4485 0.053 Uiso 1 1 calc R . .
H15B H 0.2524 0.3213 0.5006 0.053 Uiso 1 1 calc R . .
N1 N 0.12622(18) 0.31472(19) 0.7178(3) 0.0314(7) Uani 1 1 d . . .
N2 N 0.17488(18) 0.39595(19) 0.6433(3) 0.0309(7) Uani 1 1 d . . .
O1 O 0.1696(2) 0.2576(2) 0.2581(3) 0.0571(9) Uani 1 1 d . . .
O2 O 0.2180(2) 0.3975(2) 0.2760(3) 0.0609(9) Uani 1 1 d . . .
O3 O 0.07993(17) 0.37423(18) 0.1990(3) 0.0446(7) Uani 1 1 d . . .
O4 O 0.0000 0.4846(2) 0.2500 0.0386(9) Uani 1 2 d SD . .
H4 H 0.030(3) 0.452(2) 0.245(5) 0.058 Uiso 1 1 d D . .
S1 S 0.16355(6) 0.34383(7) 0.28119(10) 0.0400(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0255(17) 0.0330(19) 0.0316(19) 0.0027(15) 0.0191(16) 0.0034(15)
C2 0.0272(18) 0.036(2) 0.0301(19) -0.0019(15) 0.0177(16) 0.0008(15)
C3 0.0270(19) 0.042(2) 0.034(2) 0.0031(17) 0.0190(17) 0.0019(16)
C4 0.0267(19) 0.038(2) 0.041(2) 0.0051(17) 0.0185(17) 0.0022(16)
C5 0.034(2) 0.0287(19) 0.045(2) -0.0040(17) 0.0228(19) -0.0007(16)
C6 0.0274(18) 0.036(2) 0.035(2) -0.0047(16) 0.0197(17) 0.0023(15)
C7 0.040(2) 0.035(2) 0.038(2) -0.0044(17) 0.0252(19) -0.0001(17)
C8 0.048(3) 0.043(2) 0.057(3) 0.013(2) 0.032(2) 0.004(2)
C9 0.050(2) 0.047(2) 0.041(2) -0.0101(19) 0.031(2) -0.001(2)
C10 0.0249(18) 0.034(2) 0.0283(18) -0.0045(15) 0.0154(15) 0.0028(15)
C11 0.036(2) 0.037(2) 0.040(2) 0.0051(17) 0.0258(19) 0.0088(16)
C12 0.031(2) 0.039(2) 0.039(2) 0.0054(17) 0.0231(18) 0.0099(16)
C13 0.034(2) 0.039(2) 0.034(2) 0.0001(16) 0.0215(18) -0.0027(16)
C14 0.036(2) 0.037(2) 0.036(2) 0.0077(16) 0.0261(18) 0.0042(16)
C15 0.060(3) 0.038(2) 0.042(2) 0.0093(18) 0.035(2) 0.013(2)
N1 0.0289(16) 0.0327(16) 0.0356(17) 0.0037(13) 0.0214(14) 0.0045(13)
N2 0.0315(16) 0.0333(16) 0.0316(16) 0.0007(13) 0.0214(14) 0.0031(13)
O1 0.079(2) 0.0533(19) 0.0412(17) 0.0045(14) 0.0379(17) 0.0258(17)
O2 0.056(2) 0.092(3) 0.0493(19) 0.0045(18) 0.0396(17) -0.0041(18)
O3 0.0400(16) 0.0505(17) 0.0421(16) -0.0010(13) 0.0248(14) 0.0121(13)
O4 0.032(2) 0.036(2) 0.052(2) 0.000 0.028(2) 0.000
S1 0.0456(6) 0.0459(6) 0.0348(5) 0.0076(4) 0.0280(5) 0.0171(5)

_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 1.382(5) . ?
C1 C2 1.403(5) . ?
C1 N1 1.438(5) . ?
C2 C3 1.391(5) . ?
C2 C7 1.510(5) . ?
C3 C4 1.377(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(6) . ?
C4 C8 1.497(5) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C6 C9 1.507(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N2 1.308(5) . ?
C10 N1 1.312(5) . ?
C10 H10 0.9500 . ?
C11 N2 1.484(5) . ?
C11 C12 1.524(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N1 1.483(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N2 1.463(5) . ?
C13 C14 1.517(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.496(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 S1 1.765(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O1 S1 1.436(3) . ?
O2 S1 1.448(3) . ?
O3 S1 1.440(3) . ?
O4 H4 0.84(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.4(3) . . ?
C6 C1 N1 119.7(3) . . ?
C2 C1 N1 117.8(3) . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 C7 121.7(3) . . ?
C1 C2 C7 121.3(3) . . ?
C4 C3 C2 122.5(4) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 118.1(4) . . ?
C3 C4 C8 120.9(4) . . ?
C5 C4 C8 121.0(4) . . ?
C4 C5 C6 122.3(4) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 117.6(3) . . ?
C1 C6 C9 121.4(4) . . ?
C5 C6 C9 121.0(3) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 N1 114.2(3) . . ?
N2 C10 H10 122.9 . . ?
N1 C10 H10 122.9 . . ?
N2 C11 C12 102.7(3) . . ?
N2 C11 H11A 111.2 . . ?
C12 C11 H11A 111.2 . . ?
N2 C11 H11B 111.2 . . ?
C12 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
N1 C12 C11 103.1(3) . . ?
N1 C12 H12A 111.1 . . ?
C11 C12 H12A 111.1 . . ?
N1 C12 H12B 111.1 . . ?
C11 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
N2 C13 C14 112.2(3) . . ?
N2 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 112.5(3) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 S1 115.0(3) . . ?
C14 C15 H15A 108.5 . . ?
S1 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
S1 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C10 N1 C1 125.6(3) . . ?
C10 N1 C12 109.2(3) . . ?
C1 N1 C12 124.7(3) . . ?
C10 N2 C13 127.0(3) . . ?
C10 N2 C11 109.7(3) . . ?
C13 N2 C11 122.7(3) . . ?
O1 S1 O3 112.8(2) . . ?
O1 S1 O2 113.1(2) . . ?
O3 S1 O2 111.7(2) . . ?
O1 S1 C15 105.75(19) . . ?
O3 S1 C15 106.70(19) . . ?
O2 S1 C15 106.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         1.152
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.073

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 1.000 0.160 0.250 77 12 ' '
2 0.500 0.660 0.250 77 12 ' '
3 0.500 0.340 0.750 77 12 ' '
4 1.000 0.840 0.750 77 12 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 1002517'
