# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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
#
#  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_1formI
_database_code_depnum_ccdc_archive 'CCDC 999254'

_audit_creation_date             2013-05-04
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H23 N3 O5'
_chemical_formula_sum            'C20 H23 N3 O5'
_chemical_formula_weight         385.41
_chemical_melting_point          ?
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8644(2)
_cell_length_b                   23.7196(5)
_cell_length_c                   10.4242(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.213(3)
_cell_angle_gamma                90.00
_cell_volume                     1933.11(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3753
_cell_measurement_temperature    176(2)
_cell_measurement_theta_max      29.9020
_cell_measurement_theta_min      2.1300
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.1655
_exptl_crystal_size_mid          0.1221
_exptl_crystal_size_min          0.1114
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11637
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         30.69
_diffrn_reflns_theta_min         2.14
_diffrn_ambient_temperature      176.15
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.8876
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -95.00  -38.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9006 -178.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
  2 omega  -90.00    6.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9006  -77.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega   37.00   64.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       21.6819  178.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   36.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       21.6819  -77.0000    0.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0079842000
_diffrn_orient_matrix_UB_12      0.0241206000
_diffrn_orient_matrix_UB_13      0.0390924000
_diffrn_orient_matrix_UB_21      0.0549248000
_diffrn_orient_matrix_UB_22      -0.0126327000
_diffrn_orient_matrix_UB_23      0.0503889000
_diffrn_orient_matrix_UB_31      0.0717775000
_diffrn_orient_matrix_UB_32      0.0123545000
_diffrn_orient_matrix_UB_33      -0.0248524000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3631
_reflns_number_total             5318
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.9013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1328
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H2A,H2B} of C2, H19 of C19, H17 of C17, H10 of C10, {H11A,H11B} of C11,
  {H12A,H12B} of C12, {H13A,H13B} of C13
 At 1.5 times of:
  {H28A,H28B,H28C} of C28, {H1A,H1B,H1C} of C1, {H22A,H22B,H22C} of C22,
  {H21A,H21B,H21C} of C21
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C17(H17), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.5985(3) 0.82907(11) 0.9493(2) 0.0644(6) Uani 1 1 d . . .
H1A H 0.5355 0.7944 0.9639 0.097 Uiso 1 1 calc R . .
H1B H 0.5830 0.8562 1.0180 0.097 Uiso 1 1 calc R . .
H1C H 0.7204 0.8204 0.9498 0.097 Uiso 1 1 calc R . .
C2 C 0.5325(3) 0.85364(9) 0.8222(2) 0.0545(6) Uani 1 1 d . . .
H2A H 0.4078 0.8603 0.8184 0.065 Uiso 1 1 calc R . .
H2B H 0.5898 0.8900 0.8087 0.065 Uiso 1 1 calc R . .
C4 C 0.5006(2) 0.82350(7) 0.6051(2) 0.0426(4) Uani 1 1 d . . .
C6 C 0.5427(2) 0.77910(7) 0.51295(18) 0.0364(4) Uani 1 1 d . . .
C9 C 0.5459(2) 0.72628(7) 0.34173(17) 0.0366(4) Uani 1 1 d . . .
C10 C 0.4712(2) 0.77257(7) 0.38422(18) 0.0413(4) Uani 1 1 d . . .
H10 H 0.3880 0.7959 0.3374 0.050 Uiso 1 1 calc R . .
C11 C 0.5311(2) 0.69390(8) 0.21959(17) 0.0395(4) Uani 1 1 d . . .
H11A H 0.6367 0.6990 0.1771 0.047 Uiso 1 1 calc R . .
H11B H 0.4341 0.7089 0.1610 0.047 Uiso 1 1 calc R . .
C12 C 0.5030(2) 0.63118(7) 0.24132(17) 0.0398(4) Uani 1 1 d . . .
H12A H 0.5989 0.6164 0.3013 0.048 Uiso 1 1 calc R . .
H12B H 0.3964 0.6261 0.2825 0.048 Uiso 1 1 calc R . .
C13 C 0.4908(2) 0.59765(8) 0.11840(19) 0.0448(5) Uani 1 1 d . . .
H13A H 0.5913 0.6054 0.0715 0.054 Uiso 1 1 calc R . .
H13B H 0.4888 0.5568 0.1381 0.054 Uiso 1 1 calc R . .
C15 C 0.3199(2) 0.58725(7) -0.07944(17) 0.0359(4) Uani 1 1 d . . .
C16 C 0.2547(2) 0.53264(7) -0.09144(17) 0.0365(4) Uani 1 1 d . . .
C17 C 0.2336(2) 0.50871(7) -0.21468(16) 0.0358(4) Uani 1 1 d . . .
H17 H 0.1850 0.4721 -0.2260 0.043 Uiso 1 1 calc R . .
C18 C 0.2823(2) 0.53733(7) -0.32044(16) 0.0362(4) Uani 1 1 d . . .
C19 C 0.3510(2) 0.59142(8) -0.30451(18) 0.0403(4) Uani 1 1 d . . .
H19 H 0.3862 0.6108 -0.3769 0.048 Uiso 1 1 calc R . .
C20 C 0.3686(2) 0.61730(7) -0.18490(18) 0.0394(4) Uani 1 1 d . . .
C21 C 0.4410(3) 0.67609(8) -0.1672(2) 0.0545(5) Uani 1 1 d . . .
H21A H 0.3586 0.7003 -0.1295 0.082 Uiso 1 1 calc R . .
H21B H 0.4634 0.6913 -0.2511 0.082 Uiso 1 1 calc R . .
H21C H 0.5480 0.6748 -0.1096 0.082 Uiso 1 1 calc R . .
C22 C 0.2153(3) 0.49979(8) 0.02513(18) 0.0453(5) Uani 1 1 d . . .
H22A H 0.1376 0.4687 -0.0020 0.068 Uiso 1 1 calc R . .
H22B H 0.1609 0.5247 0.0837 0.068 Uiso 1 1 calc R . .
H22C H 0.3216 0.4846 0.0697 0.068 Uiso 1 1 calc R . .
C23 C 0.2653(2) 0.51098(7) -0.44901(17) 0.0375(4) Uani 1 1 d . . .
C26 C 0.2170(3) 0.45189(8) -0.59663(18) 0.0423(4) Uani 1 1 d . . .
C28 C 0.1730(3) 0.40321(9) -0.68382(19) 0.0494(5) Uani 1 1 d . . .
H28A H 0.1930 0.3680 -0.6354 0.074 Uiso 1 1 calc R . .
H28B H 0.2447 0.4040 -0.7551 0.074 Uiso 1 1 calc R . .
H28C H 0.0523 0.4056 -0.7184 0.074 Uiso 1 1 calc R . .
N7 N 0.6544(2) 0.73962(6) 0.54870(15) 0.0432(4) Uani 1 1 d . . .
N24 N 0.3102(3) 0.53777(7) -0.54920(15) 0.0526(4) Uani 1 1 d . . .
N27 N 0.2065(2) 0.45705(6) -0.47441(14) 0.0406(4) Uani 1 1 d . . .
O3 O 0.56914(17) 0.81310(5) 0.72413(13) 0.0452(3) Uani 1 1 d . . .
O5 O 0.4108(2) 0.86316(6) 0.57185(16) 0.0604(4) Uani 1 1 d . . .
O8 O 0.65771(17) 0.70565(5) 0.43902(12) 0.0430(3) Uani 1 1 d . . .
O14 O 0.33606(16) 0.61355(5) 0.04001(12) 0.0398(3) Uani 1 1 d . . .
O25 O 0.2777(2) 0.49789(6) -0.65038(13) 0.0562(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.488(3) . ?
C2 O3 1.455(2) . ?
C4 C6 1.487(3) . ?
C4 O3 1.322(2) . ?
C4 O5 1.205(2) . ?
C6 C10 1.406(3) . ?
C6 N7 1.310(2) . ?
C9 C10 1.343(3) . ?
C9 C11 1.481(2) . ?
C9 O8 1.359(2) . ?
C11 C12 1.525(2) . ?
C12 C13 1.502(2) . ?
C13 O14 1.441(2) . ?
C15 C16 1.394(2) . ?
C15 C20 1.398(3) . ?
C15 O14 1.386(2) . ?
C16 C17 1.398(2) . ?
C16 C22 1.504(2) . ?
C17 C18 1.384(2) . ?
C18 C19 1.395(3) . ?
C18 C23 1.472(2) . ?
C19 C20 1.383(3) . ?
C20 C21 1.510(3) . ?
C23 N24 1.303(2) . ?
C23 N27 1.376(2) . ?
C26 C28 1.487(3) . ?
C26 N27 1.291(2) . ?
C26 O25 1.338(2) . ?
N7 O8 1.4013(18) . ?
N24 O25 1.419(2) . ?

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
O3 C2 C1 106.89(17) . . ?
O3 C4 C6 112.20(15) . . ?
O5 C4 C6 122.14(19) . . ?
O5 C4 O3 125.64(19) . . ?
C10 C6 C4 126.91(16) . . ?
N7 C6 C4 120.78(17) . . ?
N7 C6 C10 112.30(16) . . ?
C10 C9 C11 135.31(17) . . ?
C10 C9 O8 108.61(15) . . ?
O8 C9 C11 116.06(15) . . ?
C9 C10 C6 105.10(16) . . ?
C9 C11 C12 112.19(15) . . ?
C13 C12 C11 112.76(16) . . ?
O14 C13 C12 108.50(15) . . ?
C16 C15 C20 122.19(16) . . ?
O14 C15 C16 119.74(16) . . ?
O14 C15 C20 118.07(15) . . ?
C15 C16 C17 117.77(16) . . ?
C15 C16 C22 121.00(16) . . ?
C17 C16 C22 121.18(16) . . ?
C18 C17 C16 121.16(16) . . ?
C17 C18 C19 119.57(16) . . ?
C17 C18 C23 120.77(16) . . ?
C19 C18 C23 119.66(16) . . ?
C20 C19 C18 121.01(17) . . ?
C15 C20 C21 120.44(17) . . ?
C19 C20 C15 118.24(16) . . ?
C19 C20 C21 121.31(18) . . ?
N24 C23 C18 121.12(17) . . ?
N24 C23 N27 114.42(16) . . ?
N27 C23 C18 124.44(16) . . ?
N27 C26 C28 129.88(18) . . ?
N27 C26 O25 113.55(17) . . ?
O25 C26 C28 116.58(16) . . ?
C6 N7 O8 104.47(14) . . ?
C23 N24 O25 103.18(15) . . ?
C26 N27 C23 102.83(15) . . ?
C4 O3 C2 116.42(15) . . ?
C9 O8 N7 109.52(13) . . ?
C15 O14 C13 112.42(13) . . ?
C26 O25 N24 106.03(14) . . ?

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
C1 C2 O3 C4 171.35(17) . . . . ?
C4 C6 C10 C9 -178.65(17) . . . . ?
C4 C6 N7 O8 178.97(15) . . . . ?
C6 C4 O3 C2 -178.80(15) . . . . ?
C6 N7 O8 C9 -0.38(19) . . . . ?
C9 C11 C12 C13 -178.99(15) . . . . ?
C10 C6 N7 O8 0.2(2) . . . . ?
C10 C9 C11 C12 -128.4(2) . . . . ?
C10 C9 O8 N7 0.4(2) . . . . ?
C11 C9 C10 C6 178.2(2) . . . . ?
C11 C9 O8 N7 -178.39(15) . . . . ?
C11 C12 C13 O14 -67.4(2) . . . . ?
C12 C13 O14 C15 176.04(15) . . . . ?
C15 C16 C17 C18 2.6(3) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
C16 C15 C20 C21 -179.12(17) . . . . ?
C16 C15 O14 C13 82.7(2) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C16 C17 C18 C23 177.78(16) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C17 C18 C23 N24 179.69(18) . . . . ?
C17 C18 C23 N27 -1.9(3) . . . . ?
C18 C19 C20 C15 1.6(3) . . . . ?
C18 C19 C20 C21 -179.29(18) . . . . ?
C18 C23 N24 O25 178.71(16) . . . . ?
C18 C23 N27 C26 -178.68(17) . . . . ?
C19 C18 C23 N24 -1.4(3) . . . . ?
C19 C18 C23 N27 176.98(17) . . . . ?
C20 C15 C16 C17 -2.0(3) . . . . ?
C20 C15 C16 C22 175.54(17) . . . . ?
C20 C15 O14 C13 -97.98(19) . . . . ?
C22 C16 C17 C18 -174.97(17) . . . . ?
C23 C18 C19 C20 -179.98(17) . . . . ?
C23 N24 O25 C26 -0.1(2) . . . . ?
C28 C26 N27 C23 179.9(2) . . . . ?
C28 C26 O25 N24 -179.82(17) . . . . ?
N7 C6 C10 C9 0.0(2) . . . . ?
N24 C23 N27 C26 -0.2(2) . . . . ?
N27 C23 N24 O25 0.1(2) . . . . ?
N27 C26 O25 N24 0.0(2) . . . . ?
O3 C4 C6 C10 169.93(18) . . . . ?
O3 C4 C6 N7 -8.6(2) . . . . ?
O5 C4 C6 C10 -8.5(3) . . . . ?
O5 C4 C6 N7 172.98(19) . . . . ?
O5 C4 O3 C2 -0.4(3) . . . . ?
O8 C9 C10 C6 -0.2(2) . . . . ?
O8 C9 C11 C12 49.9(2) . . . . ?
O14 C15 C16 C17 177.23(15) . . . . ?
O14 C15 C16 C22 -5.2(3) . . . . ?
O14 C15 C20 C19 -179.33(15) . . . . ?
O14 C15 C20 C21 1.6(3) . . . . ?
O25 C26 N27 C23 0.1(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 -25 10 0.0557 -1.9996 -24.9834 9.9994 -0.1957 0.7096 -0.7007
2 25 -10 0.0557 1.9996 24.9834 -9.9994 0.1957 -0.7096 0.7007
-11 4 0 0.0754 -11.0041 4.0000 -0.0005 0.1843 -0.6550 -0.7404
11 -1 -1 0.0705 11.0040 -1.0019 -0.9994 -0.1511 0.5667 0.8023
0 19 12 0.0476 -0.0021 19.0028 12.0023 0.9276 0.3646 -0.0637
-1 -23 -11 0.0624 -0.9980 -23.0005 -11.0025 -0.9769 -0.3187 -0.0824

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1formII
_database_code_depnum_ccdc_archive 'CCDC 999255'

_audit_creation_date             2013-05-04
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H23 N3 O5'
_chemical_formula_sum            'C20 H23 N3 O5'
_chemical_formula_weight         385.41
_chemical_melting_point          ?
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   18.6194(5)
_cell_length_b                   8.3392(2)
_cell_length_c                   12.7669(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.331(3)
_cell_angle_gamma                90.00
_cell_volume                     1950.19(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3941
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.2090
_cell_measurement_theta_min      2.9280
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10497
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         30.60
_diffrn_reflns_theta_min         2.22
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 0.9660
_diffrn_measured_fraction_theta_max 0.8606
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -7.00   50.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       21.6819   77.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
  2 omega    9.00   35.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       21.6819   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00   82.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       21.6819   77.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   81.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       21.6819   77.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   90.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       21.6819   77.0000  150.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0109322000
_diffrn_orient_matrix_UB_12      0.0483513000
_diffrn_orient_matrix_UB_13      0.0400890000
_diffrn_orient_matrix_UB_21      -0.0364056000
_diffrn_orient_matrix_UB_22      -0.0001873000
_diffrn_orient_matrix_UB_23      -0.0284400000
_diffrn_orient_matrix_UB_31      -0.0074331000
_diffrn_orient_matrix_UB_32      -0.0700175000
_diffrn_orient_matrix_UB_33      0.0277261000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3643
_reflns_number_total             5164
_reflns_odcompleteness_completeness 96.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.4609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1674
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H2A,H2B} of C2, H10 of C10, {H11A,H11B} of C11, {H12A,H12B} of C12, {H13A,
  H13B} of C13, H17 of C17, H19 of C19
 At 1.5 times of:
  {H1A,H1B,H1C} of C1, {H28A,H28B,H28C} of C28, {H22A,H22B,H22C} of C22,
  {H21A,H21B,H21C} of C21
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C17(H17), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.73104(14) 0.0855(3) 0.86491(19) 0.0581(6) Uani 1 1 d . . .
H1A H 0.7290 0.2009 0.8787 0.087 Uiso 1 1 calc R . .
H1B H 0.7802 0.0454 0.8928 0.087 Uiso 1 1 calc R . .
H1C H 0.6956 0.0297 0.9001 0.087 Uiso 1 1 calc R . .
C2 C 0.71331(11) 0.0561(2) 0.74848(18) 0.0461(5) Uani 1 1 d . . .
H2A H 0.7484 0.1130 0.7119 0.055 Uiso 1 1 calc R . .
H2B H 0.7159 -0.0600 0.7334 0.055 Uiso 1 1 calc R . .
C4 C 0.61785(12) 0.1274(2) 0.60797(18) 0.0446(5) Uani 1 1 d . . .
C6 C 0.54399(10) 0.2008(2) 0.57829(17) 0.0390(4) Uani 1 1 d . . .
C9 C 0.44446(10) 0.3067(2) 0.48990(16) 0.0378(4) Uani 1 1 d . . .
C10 C 0.50724(11) 0.2382(2) 0.47521(17) 0.0423(5) Uani 1 1 d . . .
H10 H 0.5232 0.2193 0.4097 0.051 Uiso 1 1 calc R . .
C11 C 0.38031(10) 0.3778(2) 0.41867(16) 0.0388(4) Uani 1 1 d . . .
H11A H 0.3742 0.4902 0.4403 0.047 Uiso 1 1 calc R . .
H11B H 0.3358 0.3179 0.4273 0.047 Uiso 1 1 calc R . .
C12 C 0.38795(10) 0.3743(2) 0.30255(16) 0.0396(5) Uani 1 1 d . . .
H12A H 0.4354 0.4225 0.2951 0.048 Uiso 1 1 calc R . .
H12B H 0.3880 0.2615 0.2785 0.048 Uiso 1 1 calc R . .
C13 C 0.32760(10) 0.4634(2) 0.23256(16) 0.0402(5) Uani 1 1 d . . .
H13A H 0.3261 0.5757 0.2572 0.048 Uiso 1 1 calc R . .
H13B H 0.3364 0.4646 0.1584 0.048 Uiso 1 1 calc R . .
C15 C 0.19977(9) 0.47005(18) 0.18167(14) 0.0282(4) Uani 1 1 d . . .
C16 C 0.18066(9) 0.45225(19) 0.07144(14) 0.0290(4) Uani 1 1 d . . .
C17 C 0.12199(9) 0.54014(18) 0.01852(14) 0.0288(4) Uani 1 1 d . . .
H17 H 0.1089 0.5318 -0.0567 0.035 Uiso 1 1 calc R . .
C18 C 0.08185(9) 0.64072(18) 0.07388(13) 0.0260(3) Uani 1 1 d . . .
C19 C 0.10051(9) 0.65176(18) 0.18450(14) 0.0286(4) Uani 1 1 d . . .
H19 H 0.0723 0.7178 0.2224 0.034 Uiso 1 1 calc R . .
C20 C 0.15970(9) 0.56756(19) 0.24002(13) 0.0283(4) Uani 1 1 d . . .
C21 C 0.17983(11) 0.5793(2) 0.35941(14) 0.0380(4) Uani 1 1 d . . .
H21A H 0.1485 0.6588 0.3856 0.057 Uiso 1 1 calc R . .
H21B H 0.2310 0.6121 0.3792 0.057 Uiso 1 1 calc R . .
H21C H 0.1731 0.4746 0.3911 0.057 Uiso 1 1 calc R . .
C22 C 0.22127(10) 0.3401(2) 0.01047(16) 0.0374(4) Uani 1 1 d . . .
H22A H 0.1879 0.2990 -0.0519 0.056 Uiso 1 1 calc R . .
H22B H 0.2409 0.2503 0.0564 0.056 Uiso 1 1 calc R . .
H22C H 0.2615 0.3978 -0.0128 0.056 Uiso 1 1 calc R . .
C23 C 0.02046(9) 0.73106(18) 0.01312(13) 0.0268(4) Uani 1 1 d . . .
C26 C -0.05003(10) 0.82599(19) -0.11813(14) 0.0310(4) Uani 1 1 d . . .
C28 C -0.09022(12) 0.8779(2) -0.22304(15) 0.0428(5) Uani 1 1 d . . .
H28A H -0.0792 0.9908 -0.2347 0.064 Uiso 1 1 calc R . .
H28B H -0.1428 0.8654 -0.2250 0.064 Uiso 1 1 calc R . .
H28C H -0.0753 0.8121 -0.2790 0.064 Uiso 1 1 calc R . .
N7 N 0.50761(10) 0.2448(3) 0.65208(15) 0.0561(5) Uani 1 1 d . . .
N24 N -0.02555(8) 0.81424(17) 0.05798(12) 0.0323(3) Uani 1 1 d . . .
N27 N 0.00698(8) 0.73497(16) -0.09680(11) 0.0300(3) Uani 1 1 d . . .
O3 O 0.63961(8) 0.11555(17) 0.71140(12) 0.0473(4) Uani 1 1 d . . .
O5 O 0.65307(11) 0.0905(3) 0.54259(16) 0.0961(8) Uani 1 1 d . . .
O8 O 0.44304(8) 0.3125(2) 0.59513(12) 0.0594(5) Uani 1 1 d . . .
O14 O 0.25892(6) 0.38512(13) 0.23683(10) 0.0330(3) Uani 1 1 d . . .
O25 O -0.07366(7) 0.87949(14) -0.03107(10) 0.0337(3) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.484(3) . ?
C2 O3 1.456(2) . ?
C4 C6 1.491(3) . ?
C4 O3 1.314(2) . ?
C4 O5 1.191(3) . ?
C6 C10 1.405(3) . ?
C6 N7 1.308(3) . ?
C9 C10 1.344(3) . ?
C9 C11 1.488(3) . ?
C9 O8 1.349(2) . ?
C11 C12 1.515(3) . ?
C12 C13 1.501(3) . ?
C13 O14 1.445(2) . ?
C15 C16 1.396(2) . ?
C15 C20 1.404(2) . ?
C15 O14 1.390(2) . ?
C16 C17 1.387(2) . ?
C16 C22 1.505(2) . ?
C17 C18 1.397(2) . ?
C18 C19 1.396(2) . ?
C18 C23 1.469(2) . ?
C19 C20 1.389(2) . ?
C20 C21 1.506(2) . ?
C23 N24 1.311(2) . ?
C23 N27 1.381(2) . ?
C26 C28 1.477(3) . ?
C26 N27 1.294(2) . ?
C26 O25 1.343(2) . ?
N7 O8 1.407(2) . ?
N24 O25 1.4232(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
O3 C2 C1 107.26(18) . . ?
O3 C4 C6 112.99(18) . . ?
O5 C4 C6 121.8(2) . . ?
O5 C4 O3 125.2(2) . . ?
C10 C6 C4 126.96(19) . . ?
N7 C6 C4 120.37(19) . . ?
N7 C6 C10 112.60(18) . . ?
C10 C9 C11 134.97(19) . . ?
C10 C9 O8 109.06(18) . . ?
O8 C9 C11 115.95(16) . . ?
C9 C10 C6 104.67(18) . . ?
C9 C11 C12 112.61(16) . . ?
C13 C12 C11 112.43(16) . . ?
O14 C13 C12 109.08(15) . . ?
C16 C15 C20 122.18(16) . . ?
O14 C15 C16 119.48(15) . . ?
O14 C15 C20 118.31(16) . . ?
C15 C16 C22 121.78(16) . . ?
C17 C16 C15 118.11(15) . . ?
C17 C16 C22 120.11(16) . . ?
C16 C17 C18 121.14(16) . . ?
C17 C18 C23 118.49(16) . . ?
C19 C18 C17 119.54(16) . . ?
C19 C18 C23 121.98(14) . . ?
C20 C19 C18 120.91(15) . . ?
C15 C20 C21 121.00(16) . . ?
C19 C20 C15 118.06(16) . . ?
C19 C20 C21 120.94(15) . . ?
N24 C23 C18 123.24(16) . . ?
N24 C23 N27 114.68(15) . . ?
N27 C23 C18 122.09(14) . . ?
N27 C26 C28 128.76(16) . . ?
N27 C26 O25 113.52(16) . . ?
O25 C26 C28 117.72(15) . . ?
C6 N7 O8 104.19(17) . . ?
C23 N24 O25 102.73(13) . . ?
C26 N27 C23 102.74(14) . . ?
C4 O3 C2 117.08(17) . . ?
C9 O8 N7 109.46(15) . . ?
C15 O14 C13 112.13(12) . . ?
C26 O25 N24 106.34(12) . . ?

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
C1 C2 O3 C4 168.20(18) . . . . ?
C4 C6 C10 C9 -177.82(19) . . . . ?
C4 C6 N7 O8 178.03(18) . . . . ?
C6 C4 O3 C2 -175.65(16) . . . . ?
C6 N7 O8 C9 -0.6(2) . . . . ?
C9 C11 C12 C13 -173.13(16) . . . . ?
C10 C6 N7 O8 0.9(2) . . . . ?
C10 C9 C11 C12 -1.1(3) . . . . ?
C10 C9 O8 N7 0.0(2) . . . . ?
C11 C9 C10 C6 178.7(2) . . . . ?
C11 C9 O8 N7 -178.58(17) . . . . ?
C11 C12 C13 O14 -63.3(2) . . . . ?
C12 C13 O14 C15 174.34(16) . . . . ?
C15 C16 C17 C18 -1.6(2) . . . . ?
C16 C15 C20 C19 -1.9(2) . . . . ?
C16 C15 C20 C21 177.53(15) . . . . ?
C16 C15 O14 C13 82.30(18) . . . . ?
C16 C17 C18 C19 -0.7(2) . . . . ?
C16 C17 C18 C23 179.78(14) . . . . ?
C17 C18 C19 C20 1.8(2) . . . . ?
C17 C18 C23 N24 172.06(15) . . . . ?
C17 C18 C23 N27 -8.1(2) . . . . ?
C18 C19 C20 C15 -0.5(2) . . . . ?
C18 C19 C20 C21 -179.94(15) . . . . ?
C18 C23 N24 O25 179.58(13) . . . . ?
C18 C23 N27 C26 -179.60(14) . . . . ?
C19 C18 C23 N24 -7.4(2) . . . . ?
C19 C18 C23 N27 172.39(14) . . . . ?
C20 C15 C16 C17 2.9(2) . . . . ?
C20 C15 C16 C22 -176.36(15) . . . . ?
C20 C15 O14 C13 -99.72(18) . . . . ?
C22 C16 C17 C18 177.71(15) . . . . ?
C23 C18 C19 C20 -178.72(14) . . . . ?
C23 N24 O25 C26 0.16(16) . . . . ?
C28 C26 N27 C23 179.04(18) . . . . ?
C28 C26 O25 N24 -179.28(15) . . . . ?
N7 C6 C10 C9 -1.0(2) . . . . ?
N24 C23 N27 C26 0.23(19) . . . . ?
N27 C23 N24 O25 -0.24(18) . . . . ?
N27 C26 O25 N24 -0.03(19) . . . . ?
O3 C4 C6 C10 176.15(19) . . . . ?
O3 C4 C6 N7 -0.5(3) . . . . ?
O5 C4 C6 C10 -1.2(4) . . . . ?
O5 C4 C6 N7 -177.8(3) . . . . ?
O5 C4 O3 C2 1.6(3) . . . . ?
O8 C9 C10 C6 0.5(2) . . . . ?
O8 C9 C11 C12 177.02(17) . . . . ?
O14 C15 C16 C17 -179.18(14) . . . . ?
O14 C15 C16 C22 1.5(2) . . . . ?
O14 C15 C20 C19 -179.80(14) . . . . ?
O14 C15 C20 C21 -0.4(2) . . . . ?
O25 C26 N27 C23 -0.10(18) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
23 0 5 0.0820 23.0000 -0.0000 5.0000 -0.0510 -0.9795 -0.0323
-25 0 -1 0.0563 -25.0000 0.0000 -1.0000 0.2332 0.9386 0.1581
-9 -10 9 0.0952 -9.0000 -10.0000 9.0000 -0.0243 0.0736 1.0166
-10 10 7 0.1158 -10.0000 10.0000 7.0000 0.8735 0.1631 -0.4318
11 -9 -8 0.0508 11.0000 -9.0000 -8.0000 -0.8761 -0.1713 0.3266
-16 -1 16 0.0492 -16.0000 -1.0000 16.0000 0.7680 0.1276 0.6326
14 5 -15 0.0683 14.0000 5.0000 -15.0000 -0.5126 -0.0840 -0.8700
26 -2 -1 0.0739 26.0000 -2.0000 -1.0000 -0.4210 -0.9177 -0.0810
25 0 1 0.0695 25.0000 -0.0000 1.0000 -0.2332 -0.9386 -0.1581

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2EtOH
_database_code_depnum_ccdc_archive 'CCDC 999256'

_audit_creation_date             2013-07-04
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C18 H19 N3 O5), 2(C2 H6 O)'
_chemical_formula_sum            'C40 H50 N6 O12'
_chemical_formula_weight         806.86
_chemical_melting_point          ?
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.3029(3)
_cell_length_b                   45.5165(17)
_cell_length_c                   11.0152(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.692(4)
_cell_angle_gamma                90.00
_cell_volume                     4044.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4693
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      28.2060
_cell_measurement_theta_min      2.1100
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1222
_exptl_crystal_size_min          0.0469
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18378
_diffrn_reflns_theta_full        28.78
_diffrn_reflns_theta_max         28.78
_diffrn_reflns_theta_min         1.79
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.8754
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -100.00  -61.00   0.7500   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4977 -178.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega  -76.00   49.25   0.7500   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4977    0.0000  -90.0000 167

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   62.00   0.7500   90.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2790  -99.0000  -60.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0430378000
_diffrn_orient_matrix_UB_12      -0.0106144000
_diffrn_orient_matrix_UB_13      -0.0273836000
_diffrn_orient_matrix_UB_21      -0.0192539000
_diffrn_orient_matrix_UB_22      -0.0109151000
_diffrn_orient_matrix_UB_23      0.0403276000
_diffrn_orient_matrix_UB_31      -0.0742078000
_diffrn_orient_matrix_UB_32      -0.0033217000
_diffrn_orient_matrix_UB_33      -0.0449042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6305
_reflns_number_total             9215
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         9215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0375P)²+2.7632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1401
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H19B of C19B, {H11A,H11B} of C11B, {H13A,H13B} of C13B, {HA,HB} of C201,
  {HG,HH} of C101, {H12A,H12B} of C12B, H17B of C17B, H10B of C10B, {HZ,H0AA}
  of C13A, HV of C10A, HU of C17A, {HP,HQ} of C12A, HO of C19A, {HM,HN} of C11A
 At 1.5 times of:
  HF of O102, {HC,HD,HE} of C200, HL of O3A, {HI,HJ,HK} of C100, {H21A,H21B,
  H21C} of C21B, {H28A,H28B,H28C} of C28B, {H22A,H22B,H22C} of C22B, H3B of O3B,
   H of O202, {HW,HX,HY} of C21A, {HR,HS,HT} of C22A, {H1AA,H2AA,H3AA} of C28A
2.a Secondary CH2 refined with riding coordinates:
 C11B(H11A,H11B), C13B(H13A,H13B), C12B(H12A,H12B), C201(HA,HB), C101(HG,HH),
 C11A(HM,HN), C12A(HP,HQ), C13A(HZ,H0AA)
2.b Aromatic/amide H refined with riding coordinates:
 C17B(H17B), C10B(H10B), C19B(H19B), C19A(HO), C17A(HU), C10A(HV)
2.c Idealised Me refined as rotating group:
 C21B(H21A,H21B,H21C), C22B(H22A,H22B,H22C), C28B(H28A,H28B,H28C), C200(HC,HD,
 HE), C100(HI,HJ,HK), C22A(HR,HS,HT), C21A(HW,HX,HY), C28A(H1AA,H2AA,H3AA)
2.d Idealised tetrahedral OH refined as rotating group:
 O3B(H3B), O202(H), O102(HF), O3A(HL)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O14B O 0.13775(18) 0.02068(4) 0.96345(14) 0.0308(4) Uani 1 1 d . . .
N27B N 0.6042(3) 0.07949(4) 1.45902(18) 0.0355(5) Uani 1 1 d . . .
O8B O 0.0258(2) -0.07430(4) 0.67641(15) 0.0388(4) Uani 1 1 d . . .
O3B O -0.2829(2) -0.09898(4) 0.35214(16) 0.0458(5) Uani 1 1 d . . .
H3B H -0.3585 -0.1017 0.2874 0.069 Uiso 1 1 calc R . .
O5B O -0.3912(2) -0.05371(4) 0.34448(16) 0.0421(4) Uani 1 1 d . . .
N7B N -0.0786(3) -0.08760(4) 0.57201(18) 0.0373(5) Uani 1 1 d . . .
O202 O -0.5114(3) -0.11275(4) 0.15809(16) 0.0545(6) Uani 1 1 d . . .
H H -0.5573 -0.1292 0.1569 0.082 Uiso 1 1 calc R . .
C18B C 0.4706(3) 0.04324(5) 1.2947(2) 0.0278(5) Uani 1 1 d . . .
O25B O 0.7802(2) 0.04938(4) 1.57916(16) 0.0459(5) Uani 1 1 d . . .
C17B C 0.3793(3) 0.06497(5) 1.2205(2) 0.0299(5) Uani 1 1 d . . .
H17B H 0.3939 0.0849 1.2461 0.036 Uiso 1 1 calc R . .
C10B C -0.1271(3) -0.03877(5) 0.5714(2) 0.0284(5) Uani 1 1 d . . .
H10B H -0.1747 -0.0201 0.5457 0.034 Uiso 1 1 calc R . .
C20B C 0.3369(3) 0.00634(5) 1.1472(2) 0.0285(5) Uani 1 1 d . . .
C4B C -0.2938(3) -0.07221(5) 0.3937(2) 0.0304(5) Uani 1 1 d . . .
N24B N 0.6902(3) 0.03232(5) 1.4783(2) 0.0436(6) Uani 1 1 d . . .
C23B C 0.5894(3) 0.05120(5) 1.4118(2) 0.0303(5) Uani 1 1 d . . .
C19B C 0.4468(3) 0.01402(5) 1.2589(2) 0.0293(5) Uani 1 1 d . . .
H19B H 0.5062 -0.0009 1.3112 0.035 Uiso 1 1 calc R . .
C15B C 0.2507(3) 0.02861(5) 1.0729(2) 0.0274(5) Uani 1 1 d . . .
C6B C -0.1675(3) -0.06597(5) 0.5119(2) 0.0282(5) Uani 1 1 d . . .
C11B C 0.0973(3) -0.02755(5) 0.7770(2) 0.0315(5) Uani 1 1 d . . .
H11A H 0.2136 -0.0344 0.7923 0.038 Uiso 1 1 calc R . .
H11B H 0.0583 -0.0312 0.8539 0.038 Uiso 1 1 calc R . .
C16B C 0.2668(3) 0.05799(5) 1.1091(2) 0.0306(5) Uani 1 1 d . . .
C21B C 0.3097(3) -0.02534(5) 1.1080(2) 0.0377(6) Uani 1 1 d . . .
H21A H 0.3548 -0.0289 1.0347 0.056 Uiso 1 1 calc R . .
H21B H 0.1907 -0.0297 1.0870 0.056 Uiso 1 1 calc R . .
H21C H 0.3660 -0.0381 1.1767 0.056 Uiso 1 1 calc R . .
C13B C 0.2038(3) 0.02248(6) 0.8544(2) 0.0391(6) Uani 1 1 d . . .
H13A H 0.3173 0.0142 0.8726 0.047 Uiso 1 1 calc R . .
H13B H 0.2091 0.0433 0.8290 0.047 Uiso 1 1 calc R . .
C26B C 0.7206(3) 0.07683(6) 1.5596(2) 0.0369(6) Uani 1 1 d . . .
C9B C -0.0060(3) -0.04495(5) 0.6729(2) 0.0285(5) Uani 1 1 d . . .
C12B C 0.0916(3) 0.00521(6) 0.7504(2) 0.0385(6) Uani 1 1 d . . .
H12A H 0.1254 0.0088 0.6714 0.046 Uiso 1 1 calc R . .
H12B H -0.0238 0.0123 0.7394 0.046 Uiso 1 1 calc R . .
C22B C 0.1603(3) 0.08154(6) 1.0322(3) 0.0462(7) Uani 1 1 d . . .
H22A H 0.1676 0.0996 1.0815 0.069 Uiso 1 1 calc R . .
H22B H 0.0448 0.0749 1.0090 0.069 Uiso 1 1 calc R . .
H22C H 0.1994 0.0853 0.9565 0.069 Uiso 1 1 calc R . .
C28B C 0.7973(4) 0.09942(7) 1.6522(3) 0.0540(8) Uani 1 1 d . . .
H28A H 0.9066 0.1047 1.6396 0.081 Uiso 1 1 calc R . .
H28B H 0.8095 0.0916 1.7368 0.081 Uiso 1 1 calc R . .
H28C H 0.7265 0.1169 1.6416 0.081 Uiso 1 1 calc R . .
C201 C -0.5421(4) -0.10148(6) 0.0369(3) 0.0479(7) Uani 1 1 d . . .
HA H -0.4772 -0.1130 -0.0113 0.058 Uiso 1 1 calc R . .
HB H -0.5016 -0.0810 0.0411 0.058 Uiso 1 1 calc R . .
C200 C -0.7160(4) -0.10186(8) -0.0307(3) 0.0731(11) Uani 1 1 d . . .
HC H -0.7268 -0.0934 -0.1141 0.110 Uiso 1 1 calc R . .
HD H -0.7815 -0.0902 0.0151 0.110 Uiso 1 1 calc R . .
HE H -0.7565 -0.1222 -0.0386 0.110 Uiso 1 1 calc R . .
O102 O -0.1912(2) -0.14771(4) -0.44015(15) 0.0362(4) Uani 1 1 d . . .
HF H -0.1527 -0.1308 -0.4450 0.054 Uiso 1 1 calc R . .
C101 C -0.2362(3) -0.15084(6) -0.3231(2) 0.0388(6) Uani 1 1 d . . .
HG H -0.3120 -0.1678 -0.3278 0.047 Uiso 1 1 calc R . .
HH H -0.2964 -0.1330 -0.3071 0.047 Uiso 1 1 calc R . .
C100 C -0.0881(4) -0.15534(7) -0.2166(2) 0.0527(8) Uani 1 1 d . . .
HI H -0.1248 -0.1586 -0.1394 0.079 Uiso 1 1 calc R . .
HJ H -0.0172 -0.1379 -0.2071 0.079 Uiso 1 1 calc R . .
HK H -0.0254 -0.1725 -0.2336 0.079 Uiso 1 1 calc R . .
O8A O -0.78813(19) -0.18206(4) -0.93447(14) 0.0317(4) Uani 1 1 d . . .
O14A O -1.04246(19) -0.27604(4) -1.16941(14) 0.0306(4) Uani 1 1 d . . .
O3A O -0.4351(2) -0.15755(4) -0.63396(15) 0.0417(5) Uani 1 1 d . . .
HL H -0.3593 -0.1557 -0.5687 0.063 Uiso 1 1 calc R . .
C18A C -1.4016(3) -0.30033(5) -1.4837(2) 0.0257(5) Uani 1 1 d . . .
O25A O -1.7179(2) -0.30606(4) -1.76475(15) 0.0398(4) Uani 1 1 d . . .
C23A C -1.5219(3) -0.30815(5) -1.6002(2) 0.0271(5) Uani 1 1 d . . .
N27A N -1.5251(2) -0.33522(5) -1.65742(18) 0.0349(5) Uani 1 1 d . . .
N24A N -1.6337(2) -0.28976(5) -1.65913(18) 0.0364(5) Uani 1 1 d . . .
N7A N -0.6698(2) -0.16903(4) -0.83761(17) 0.0300(4) Uani 1 1 d . . .
C9A C -0.8134(3) -0.21024(5) -0.9021(2) 0.0270(5) Uani 1 1 d . . .
C20A C -1.2838(3) -0.26373(5) -1.3288(2) 0.0270(5) Uani 1 1 d . . .
C16A C -1.1745(3) -0.31383(5) -1.3102(2) 0.0271(5) Uani 1 1 d . . .
C6A C -0.6303(3) -0.18952(5) -0.7526(2) 0.0269(5) Uani 1 1 d . . .
C11A C -0.9366(3) -0.22752(5) -0.9954(2) 0.0280(5) Uani 1 1 d . . .
HM H -0.9103 -0.2258 -1.0782 0.034 Uiso 1 1 calc R . .
HN H -1.0484 -0.2191 -1.0023 0.034 Uiso 1 1 calc R . .
C19A C -1.3980(3) -0.27190(5) -1.4369(2) 0.0279(5) Uani 1 1 d . . .
HO H -1.4753 -0.2578 -1.4798 0.034 Uiso 1 1 calc R . .
C12A C -0.9384(3) -0.25981(5) -0.9604(2) 0.0309(5) Uani 1 1 d . . .
HP H -0.8303 -0.2687 -0.9626 0.037 Uiso 1 1 calc R . .
HQ H -0.9523 -0.2614 -0.8738 0.037 Uiso 1 1 calc R . .
C15A C -1.1703(3) -0.28487(5) -1.26778(19) 0.0264(5) Uani 1 1 d . . .
C22A C -1.0552(3) -0.33673(5) -1.2422(2) 0.0344(6) Uani 1 1 d . . .
HR H -1.1031 -0.3464 -1.1794 0.052 Uiso 1 1 calc R . .
HS H -0.9505 -0.3273 -1.2009 0.052 Uiso 1 1 calc R . .
HT H -1.0347 -0.3514 -1.3020 0.052 Uiso 1 1 calc R . .
C4A C -0.5061(3) -0.18322(5) -0.6333(2) 0.0308(5) Uani 1 1 d . . .
C17A C -1.2911(3) -0.32103(5) -1.4194(2) 0.0273(5) Uani 1 1 d . . .
HU H -1.2951 -0.3405 -1.4504 0.033 Uiso 1 1 calc R . .
O5A O -0.4794(2) -0.20020(4) -0.54776(17) 0.0533(5) Uani 1 1 d . . .
C10A C -0.7159(3) -0.21598(5) -0.7880(2) 0.0276(5) Uani 1 1 d . . .
HV H -0.7071 -0.2338 -0.7422 0.033 Uiso 1 1 calc R . .
C21A C -1.2795(3) -0.23271(5) -1.2805(2) 0.0371(6) Uani 1 1 d . . .
HW H -1.3080 -0.2327 -1.1992 0.056 Uiso 1 1 calc R . .
HX H -1.3596 -0.2207 -1.3396 0.056 Uiso 1 1 calc R . .
HY H -1.1680 -0.2246 -1.2715 0.056 Uiso 1 1 calc R . .
C13A C -1.0754(3) -0.27681(5) -1.0468(2) 0.0305(5) Uani 1 1 d . . .
HZ H -1.0771 -0.2974 -1.0178 0.037 Uiso 1 1 calc R . .
H0AA H -1.1843 -0.2677 -1.0486 0.037 Uiso 1 1 calc R . .
C26A C -1.6448(3) -0.33246(6) -1.7555(2) 0.0356(6) Uani 1 1 d . . .
C28A C -1.7090(4) -0.35360(7) -1.8581(3) 0.0563(8) Uani 1 1 d . . .
H1AA H -1.6478 -0.3512 -1.9234 0.085 Uiso 1 1 calc R . .
H2AA H -1.8270 -0.3498 -1.8934 0.085 Uiso 1 1 calc R . .
H3AA H -1.6945 -0.3737 -1.8253 0.085 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O14B C15B 1.389(3) . ?
O14B C13B 1.436(3) . ?
N27B C23B 1.383(3) . ?
N27B C26B 1.292(3) . ?
O8B N7B 1.403(2) . ?
O8B C9B 1.361(3) . ?
O3B C4B 1.312(3) . ?
O5B C4B 1.203(3) . ?
N7B C6B 1.312(3) . ?
O202 C201 1.397(3) . ?
C18B C17B 1.389(3) . ?
C18B C23B 1.472(3) . ?
C18B C19B 1.388(3) . ?
O25B N24B 1.415(3) . ?
O25B C26B 1.342(3) . ?
C17B C16B 1.392(3) . ?
C10B C6B 1.404(3) . ?
C10B C9B 1.344(3) . ?
C20B C19B 1.392(3) . ?
C20B C15B 1.390(3) . ?
C20B C21B 1.507(3) . ?
C4B C6B 1.494(3) . ?
N24B C23B 1.298(3) . ?
C15B C16B 1.393(3) . ?
C11B C9B 1.487(3) . ?
C11B C12B 1.518(3) . ?
C16B C22B 1.514(3) . ?
C13B C12B 1.514(3) . ?
C26B C28B 1.483(3) . ?
C201 C200 1.460(4) . ?
O102 C101 1.432(3) . ?
C101 C100 1.499(4) . ?
O8A N7A 1.400(2) . ?
O8A C9A 1.361(3) . ?
O14A C15A 1.385(3) . ?
O14A C13A 1.440(3) . ?
O3A C4A 1.309(3) . ?
C18A C23A 1.472(3) . ?
C18A C19A 1.391(3) . ?
C18A C17A 1.387(3) . ?
O25A N24A 1.417(2) . ?
O25A C26A 1.339(3) . ?
C23A N27A 1.381(3) . ?
C23A N24A 1.304(3) . ?
N27A C26A 1.289(3) . ?
N7A C6A 1.308(3) . ?
C9A C11A 1.491(3) . ?
C9A C10A 1.350(3) . ?
C20A C19A 1.385(3) . ?
C20A C15A 1.402(3) . ?
C20A C21A 1.506(3) . ?
C16A C15A 1.396(3) . ?
C16A C22A 1.509(3) . ?
C16A C17A 1.392(3) . ?
C6A C4A 1.493(3) . ?
C6A C10A 1.406(3) . ?
C11A C12A 1.520(3) . ?
C12A C13A 1.512(3) . ?
C4A O5A 1.198(3) . ?
C26A C28A 1.484(3) . ?

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
C15B O14B C13B 113.48(17) . . ?
C26B N27B C23B 102.5(2) . . ?
C9B O8B N7B 108.78(16) . . ?
C6B N7B O8B 104.75(19) . . ?
C17B C18B C23B 120.0(2) . . ?
C19B C18B C17B 119.6(2) . . ?
C19B C18B C23B 120.4(2) . . ?
C26B O25B N24B 106.17(18) . . ?
C18B C17B C16B 121.0(2) . . ?
C9B C10B C6B 104.6(2) . . ?
C19B C20B C21B 121.1(2) . . ?
C15B C20B C19B 118.4(2) . . ?
C15B C20B C21B 120.5(2) . . ?
O3B C4B C6B 112.8(2) . . ?
O5B C4B O3B 126.0(2) . . ?
O5B C4B C6B 121.2(2) . . ?
C23B N24B O25B 103.3(2) . . ?
N27B C23B C18B 122.7(2) . . ?
N24B C23B N27B 114.6(2) . . ?
N24B C23B C18B 122.7(2) . . ?
C18B C19B C20B 120.8(2) . . ?
O14B C15B C20B 118.0(2) . . ?
O14B C15B C16B 119.8(2) . . ?
C20B C15B C16B 122.1(2) . . ?
N7B C6B C10B 112.5(2) . . ?
N7B C6B C4B 119.5(2) . . ?
C10B C6B C4B 128.0(2) . . ?
C9B C11B C12B 112.85(19) . . ?
C17B C16B C15B 118.0(2) . . ?
C17B C16B C22B 120.8(2) . . ?
C15B C16B C22B 121.1(2) . . ?
O14B C13B C12B 108.3(2) . . ?
N27B C26B O25B 113.4(2) . . ?
N27B C26B C28B 129.6(3) . . ?
O25B C26B C28B 116.9(2) . . ?
O8B C9B C11B 115.36(19) . . ?
C10B C9B O8B 109.33(19) . . ?
C10B C9B C11B 135.3(2) . . ?
C13B C12B C11B 112.2(2) . . ?
O202 C201 C200 114.7(3) . . ?
O102 C101 C100 112.2(2) . . ?
C9A O8A N7A 108.89(16) . . ?
C15A O14A C13A 116.48(17) . . ?
C19A C18A C23A 119.9(2) . . ?
C17A C18A C23A 120.8(2) . . ?
C17A C18A C19A 119.3(2) . . ?
C26A O25A N24A 106.32(17) . . ?
N27A C23A C18A 123.3(2) . . ?
N24A C23A C18A 122.4(2) . . ?
N24A C23A N27A 114.3(2) . . ?
C26A N27A C23A 102.9(2) . . ?
C23A N24A O25A 103.13(19) . . ?
C6A N7A O8A 104.82(18) . . ?
O8A C9A C11A 116.11(18) . . ?
C10A C9A O8A 109.31(19) . . ?
C10A C9A C11A 134.6(2) . . ?
C19A C20A C15A 118.2(2) . . ?
C19A C20A C21A 120.6(2) . . ?
C15A C20A C21A 121.1(2) . . ?
C15A C16A C22A 121.6(2) . . ?
C17A C16A C15A 117.9(2) . . ?
C17A C16A C22A 120.4(2) . . ?
N7A C6A C4A 119.8(2) . . ?
N7A C6A C10A 112.79(19) . . ?
C10A C6A C4A 127.4(2) . . ?
C9A C11A C12A 112.42(18) . . ?
C20A C19A C18A 121.2(2) . . ?
C13A C12A C11A 112.72(18) . . ?
O14A C15A C20A 118.7(2) . . ?
O14A C15A C16A 119.3(2) . . ?
C16A C15A C20A 121.8(2) . . ?
O3A C4A C6A 112.6(2) . . ?
O5A C4A O3A 125.5(2) . . ?
O5A C4A C6A 121.9(2) . . ?
C18A C17A C16A 121.5(2) . . ?
C9A C10A C6A 104.2(2) . . ?
O14A C13A C12A 107.22(18) . . ?
O25A C26A C28A 116.7(2) . . ?
N27A C26A O25A 113.4(2) . . ?
N27A C26A C28A 129.9(2) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
12 2 -2 0.0361 11.9995 2.0053 -1.9984 0.5499 -0.3335 -0.8074
0 -15 -15 0.0522 0.0005 -14.9794 -14.9988 0.5697 -0.4414 0.7232
-10 3 10 0.0586 -10.0002 2.9837 9.9980 -0.7358 0.5632 0.2832
-1 -64 1 0.0235 -1.0061 -64.0083 1.0000 0.6087 0.7584 0.2424
1 64 -1 0.0235 1.0061 64.0083 -1.0000 -0.6087 -0.7584 -0.2424

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2DMSO
_database_code_depnum_ccdc_archive 'CCDC 999257'

_audit_creation_date             2013-07-04
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H19 N3 O5, C2 H6 O S'
_chemical_formula_sum            'C20 H25 N3 O6 S'
_chemical_formula_weight         435.49
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.7775(3)
_cell_length_b                   7.21311(13)
_cell_length_c                   21.4071(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.4904(16)
_cell_angle_gamma                90.00
_cell_volume                     2127.32(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4582
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.4080
_cell_measurement_theta_min      2.9470
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.2228
_exptl_crystal_size_mid          0.1221
_exptl_crystal_size_min          0.082
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11563
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         1.90
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.8881
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -94.00   32.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.5108    0.0000  120.0000 126

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00  -64.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.5108 -178.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -60.00   -7.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.5108  -37.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega   63.00   96.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       22.2921 -178.0000   90.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0421053000
_diffrn_orient_matrix_UB_12      -0.0251013000
_diffrn_orient_matrix_UB_13      0.0168542000
_diffrn_orient_matrix_UB_21      -0.0219901000
_diffrn_orient_matrix_UB_22      -0.0324738000
_diffrn_orient_matrix_UB_23      -0.0280056000
_diffrn_orient_matrix_UB_31      0.0198145000
_diffrn_orient_matrix_UB_32      -0.0893902000
_diffrn_orient_matrix_UB_33      0.0054401000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4502
_reflns_number_total             5806
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+0.9072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1245
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H13A,H13B} of C13, {H12A,H12B} of C12, {H11A,H11B} of C11, H19 of C19, H17
  of C17, H10 of C10
 At 1.5 times of:
  {H22A,H22B,H22C} of C22, {H10D,H10E,H10F} of C103, {H21A,H21B,H21C} of C21,
  {H10A,H10B,H10C} of C102, H3 of O3, {H28A,H28B,H28C} of C28
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C10(H10)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C102(H10A,H10B,H10C), C22(H22A,H22B,H22C), C103(H10D,
 H10E,H10F), C28(H28A,H28B,H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S100 S 0.41273(3) 0.72600(6) 0.227581(19) 0.03117(11) Uani 1 1 d . . .
O14 O -0.04758(8) 0.63301(15) 0.65753(5) 0.0287(2) Uani 1 1 d . . .
O101 O 0.48495(9) 0.78977(19) 0.27711(5) 0.0368(3) Uani 1 1 d . . .
C18 C -0.16729(12) 0.7034(2) 0.83354(7) 0.0261(3) Uani 1 1 d . . .
N27 N -0.30751(10) 0.7004(2) 0.90715(7) 0.0349(3) Uani 1 1 d . . .
O25 O -0.22783(9) 0.7701(2) 0.99353(6) 0.0402(3) Uani 1 1 d . . .
C23 C -0.20991(12) 0.7226(2) 0.89586(7) 0.0283(3) Uani 1 1 d . . .
C19 C -0.06698(11) 0.7163(2) 0.82512(7) 0.0264(3) Uani 1 1 d . . .
H19 H -0.0261 0.7414 0.8600 0.032 Uiso 1 1 calc R . .
O3 O 0.42408(9) 0.7334(2) 0.38884(6) 0.0409(3) Uani 1 1 d . . .
H3 H 0.4428 0.7552 0.3523 0.061 Uiso 1 1 calc R . .
C17 C -0.22743(11) 0.6698(2) 0.78210(7) 0.0271(3) Uani 1 1 d . . .
H17 H -0.2955 0.6596 0.7879 0.032 Uiso 1 1 calc R . .
C20 C -0.02612(11) 0.6930(2) 0.76648(7) 0.0252(3) Uani 1 1 d . . .
C16 C -0.18929(11) 0.6509(2) 0.72233(7) 0.0262(3) Uani 1 1 d . . .
C15 C -0.08897(11) 0.6621(2) 0.71559(7) 0.0246(3) Uani 1 1 d . . .
N24 N -0.15791(11) 0.7639(2) 0.94525(7) 0.0392(4) Uani 1 1 d . . .
O8 O 0.28544(9) 0.6854(2) 0.55531(6) 0.0448(3) Uani 1 1 d . . .
C4 C 0.33622(13) 0.7989(2) 0.39600(8) 0.0329(4) Uani 1 1 d . . .
N7 N 0.34867(11) 0.6996(3) 0.50449(7) 0.0440(4) Uani 1 1 d . . .
O5 O 0.29015(10) 0.8836(2) 0.35715(6) 0.0499(4) Uani 1 1 d . . .
C6 C 0.29434(12) 0.7611(2) 0.45876(7) 0.0300(3) Uani 1 1 d . . .
C10 C 0.19690(13) 0.7882(3) 0.47687(8) 0.0342(4) Uani 1 1 d . . .
H10 H 0.1443 0.8312 0.4518 0.041 Uiso 1 1 calc R . .
C11 C 0.12170(12) 0.7371(2) 0.58778(8) 0.0314(3) Uani 1 1 d . . .
H11A H 0.1366 0.8379 0.6178 0.038 Uiso 1 1 calc R . .
H11B H 0.1266 0.6181 0.6106 0.038 Uiso 1 1 calc R . .
C21 C 0.08215(11) 0.6952(2) 0.75801(8) 0.0305(3) Uani 1 1 d . . .
H21A H 0.1141 0.7160 0.7985 0.046 Uiso 1 1 calc R . .
H21B H 0.0997 0.7950 0.7292 0.046 Uiso 1 1 calc R . .
H21C H 0.1032 0.5759 0.7409 0.046 Uiso 1 1 calc R . .
C102 C 0.48131(15) 0.7072(3) 0.15783(8) 0.0428(4) Uani 1 1 d . . .
H10A H 0.5073 0.8291 0.1467 0.064 Uiso 1 1 calc R . .
H10B H 0.4394 0.6619 0.1239 0.064 Uiso 1 1 calc R . .
H10C H 0.5350 0.6201 0.1645 0.064 Uiso 1 1 calc R . .
C9 C 0.19545(12) 0.7394(2) 0.53748(7) 0.0296(3) Uani 1 1 d . . .
C12 C 0.01850(13) 0.7608(3) 0.56408(8) 0.0378(4) Uani 1 1 d . . .
H12A H 0.0157 0.8679 0.5352 0.045 Uiso 1 1 calc R . .
H12B H -0.0010 0.6488 0.5404 0.045 Uiso 1 1 calc R . .
C22 C -0.25536(13) 0.6171(3) 0.66728(8) 0.0356(4) Uani 1 1 d . . .
H22A H -0.3145 0.5546 0.6813 0.053 Uiso 1 1 calc R . .
H22B H -0.2222 0.5388 0.6367 0.053 Uiso 1 1 calc R . .
H22C H -0.2725 0.7358 0.6479 0.053 Uiso 1 1 calc R . .
C13 C -0.05203(13) 0.7916(2) 0.61675(8) 0.0344(4) Uani 1 1 d . . .
H13A H -0.0345 0.9054 0.6401 0.041 Uiso 1 1 calc R . .
H13B H -0.1187 0.8065 0.5998 0.041 Uiso 1 1 calc R . .
C103 C 0.34418(13) 0.9261(3) 0.20746(8) 0.0387(4) Uani 1 1 d . . .
H10D H 0.3040 0.9627 0.2430 0.058 Uiso 1 1 calc R . .
H10E H 0.3023 0.8984 0.1714 0.058 Uiso 1 1 calc R . .
H10F H 0.3884 1.0277 0.1969 0.058 Uiso 1 1 calc R . .
C28 C -0.40029(14) 0.7306(3) 1.00690(9) 0.0457(5) Uani 1 1 d . . .
H28A H -0.4071 0.8519 1.0270 0.069 Uiso 1 1 calc R . .
H28B H -0.3930 0.6346 1.0390 0.069 Uiso 1 1 calc R . .
H28C H -0.4582 0.7047 0.9814 0.069 Uiso 1 1 calc R . .
C26 C -0.31349(13) 0.7313(3) 0.96653(8) 0.0344(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
S100 O101 1.5190(13) . ?
S100 C102 1.7789(18) . ?
S100 C103 1.7761(18) . ?
O14 C15 1.3879(18) . ?
O14 C13 1.4399(19) . ?
C18 C23 1.469(2) . ?
C18 C19 1.398(2) . ?
C18 C17 1.394(2) . ?
N27 C23 1.377(2) . ?
N27 C26 1.294(2) . ?
O25 N24 1.4197(19) . ?
O25 C26 1.339(2) . ?
C23 N24 1.306(2) . ?
C19 C20 1.390(2) . ?
O3 C4 1.310(2) . ?
C17 C16 1.394(2) . ?
C20 C15 1.404(2) . ?
C20 C21 1.504(2) . ?
C16 C15 1.393(2) . ?
C16 C22 1.503(2) . ?
O8 N7 1.4032(18) . ?
O8 C9 1.352(2) . ?
C4 O5 1.208(2) . ?
C4 C6 1.492(2) . ?
N7 C6 1.305(2) . ?
C6 C10 1.414(2) . ?
C10 C9 1.345(2) . ?
C11 C9 1.487(2) . ?
C11 C12 1.515(2) . ?
C12 C13 1.511(2) . ?
C28 C26 1.481(2) . ?

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
O101 S100 C102 105.04(9) . . ?
O101 S100 C103 105.48(8) . . ?
C103 S100 C102 98.26(9) . . ?
C15 O14 C13 114.03(12) . . ?
C19 C18 C23 120.94(15) . . ?
C17 C18 C23 119.63(14) . . ?
C17 C18 C19 119.43(14) . . ?
C26 N27 C23 102.88(15) . . ?
C26 O25 N24 106.27(13) . . ?
N27 C23 C18 123.16(15) . . ?
N24 C23 C18 122.39(15) . . ?
N24 C23 N27 114.45(15) . . ?
C20 C19 C18 121.10(15) . . ?
C18 C17 C16 121.07(14) . . ?
C19 C20 C15 117.92(14) . . ?
C19 C20 C21 121.14(14) . . ?
C15 C20 C21 120.92(14) . . ?
C17 C16 C22 120.34(14) . . ?
C15 C16 C17 118.12(14) . . ?
C15 C16 C22 121.53(14) . . ?
O14 C15 C20 117.63(13) . . ?
O14 C15 C16 119.96(14) . . ?
C16 C15 C20 122.33(14) . . ?
C23 N24 O25 103.03(13) . . ?
C9 O8 N7 109.51(13) . . ?
O3 C4 C6 113.86(15) . . ?
O5 C4 O3 125.64(16) . . ?
O5 C4 C6 120.50(16) . . ?
C6 N7 O8 104.51(14) . . ?
N7 C6 C4 120.93(15) . . ?
N7 C6 C10 112.41(15) . . ?
C10 C6 C4 126.65(15) . . ?
C9 C10 C6 104.49(15) . . ?
C9 C11 C12 113.65(14) . . ?
O8 C9 C11 115.03(14) . . ?
C10 C9 O8 109.08(15) . . ?
C10 C9 C11 135.85(17) . . ?
C13 C12 C11 111.97(14) . . ?
O14 C13 C12 108.15(14) . . ?
N27 C26 O25 113.37(16) . . ?
N27 C26 C28 129.12(17) . . ?
O25 C26 C28 117.51(15) . . ?

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
C18 C23 N24 O25 179.23(14) . . . . ?
C18 C19 C20 C15 2.1(2) . . . . ?
C18 C19 C20 C21 -176.22(14) . . . . ?
C18 C17 C16 C15 1.5(2) . . . . ?
C18 C17 C16 C22 -179.19(15) . . . . ?
N27 C23 N24 O25 -0.2(2) . . . . ?
C23 C18 C19 C20 178.12(14) . . . . ?
C23 C18 C17 C16 -179.96(14) . . . . ?
C23 N27 C26 O25 -0.3(2) . . . . ?
C23 N27 C26 C28 179.20(19) . . . . ?
C19 C18 C23 N27 -176.14(15) . . . . ?
C19 C18 C23 N24 4.5(2) . . . . ?
C19 C18 C17 C16 -0.7(2) . . . . ?
C19 C20 C15 O14 -177.98(13) . . . . ?
C19 C20 C15 C16 -1.3(2) . . . . ?
O3 C4 C6 N7 12.0(2) . . . . ?
O3 C4 C6 C10 -169.38(17) . . . . ?
C17 C18 C23 N27 3.1(2) . . . . ?
C17 C18 C23 N24 -176.28(16) . . . . ?
C17 C18 C19 C20 -1.1(2) . . . . ?
C17 C16 C15 O14 176.16(13) . . . . ?
C17 C16 C15 C20 -0.5(2) . . . . ?
C15 O14 C13 C12 164.25(14) . . . . ?
N24 O25 C26 N27 0.2(2) . . . . ?
N24 O25 C26 C28 -179.36(16) . . . . ?
O8 N7 C6 C4 178.68(15) . . . . ?
O8 N7 C6 C10 -0.2(2) . . . . ?
C4 C6 C10 C9 -178.49(16) . . . . ?
N7 O8 C9 C10 0.2(2) . . . . ?
N7 O8 C9 C11 -177.99(15) . . . . ?
N7 C6 C10 C9 0.3(2) . . . . ?
O5 C4 C6 N7 -167.76(19) . . . . ?
O5 C4 C6 C10 10.9(3) . . . . ?
C6 C10 C9 O8 -0.3(2) . . . . ?
C6 C10 C9 C11 177.36(19) . . . . ?
C11 C12 C13 O14 -59.7(2) . . . . ?
C21 C20 C15 O14 0.3(2) . . . . ?
C21 C20 C15 C16 177.02(14) . . . . ?
C9 O8 N7 C6 0.0(2) . . . . ?
C9 C11 C12 C13 -169.94(15) . . . . ?
C12 C11 C9 O8 -168.48(16) . . . . ?
C12 C11 C9 C10 14.0(3) . . . . ?
C22 C16 C15 O14 -3.1(2) . . . . ?
C22 C16 C15 C20 -179.80(15) . . . . ?
C13 O14 C15 C20 -102.76(16) . . . . ?
C13 O14 C15 C16 80.44(18) . . . . ?
C26 N27 C23 C18 -179.10(15) . . . . ?
C26 N27 C23 N24 0.3(2) . . . . ?
C26 O25 N24 C23 -0.01(18) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-18 -1 9 0.0505 -17.9971 -1.0034 8.9958 0.9346 0.1764 -0.2180
19 0 3 0.0426 19.0169 0.0020 3.0001 -0.7502 -0.5023 0.3930
2 -10 -4 0.1085 2.0244 -9.9977 -4.0037 0.0982 0.3923 0.9120
1 10 -4 0.0939 0.9668 9.9992 -3.9937 -0.3590 -0.2341 -0.8964
-19 -1 -3 0.0627 -19.0141 -1.0018 -3.0006 0.7752 0.5347 -0.3035
5 0 29 0.0410 5.0428 -0.0036 28.9915 0.2764 -0.9227 0.2580
-5 0 -29 0.0410 -5.0428 0.0036 -28.9915 -0.2764 0.9227 -0.2580
-4 -10 3 0.1027 -3.9702 -9.9994 2.9939 0.4686 0.3282 0.8315


#===END
