# Electronic Supplementary Material (ESI) for Soft Matter.
# This journal is © The Royal Society of Chemistry 2015

#\#CIF_1.1
 
#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2013-07-08 at 01:40:19
#  Using CIFtbx version 3.0.4  1 Sep 2006
 
#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.4.3
#  Request file    : c:\wingx\files\archive.reqdat
#  CIF files read  : dai_1_2 project
 
 
data_shelx
 
_audit_creation_date                    2013-07-08T01:40:19-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
_audit_conform_dict_name                cif_core.dic
_audit_conform_dict_version             2.4.3
_audit_conform_dict_location            ftp://ftp.iucr.org/pub/cif_core.dic
_publ_requested_category                FO
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C17 H24 N2 O5'
_chemical_formula_sum                   'C17 H24 N2 O5'
_chemical_formula_weight                336.38
_chemical_compound_source               'synthesis as described'
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'C 2/c'
_symmetry_space_group_name_Hall         '-C 2yc'
_symmetry_Int_Tables_number             15
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                          14.2575(5)
_cell_length_b                          13.1713(4)
_cell_length_c                          20.8636(8)
_cell_angle_alpha                       90
_cell_angle_beta                        108.856(4)
_cell_angle_gamma                       90
_cell_volume                            3707.7(2)
_cell_formula_units_Z                   8
_cell_measurement_temperature           100.05(10)
_cell_measurement_reflns_used           18013
_cell_measurement_theta_min             3.0134
_cell_measurement_theta_max             29.3623
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              prism
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.74
_exptl_crystal_size_mid                 0.61
_exptl_crystal_size_min                 0.44
_exptl_crystal_density_diffrn           1.205
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1440
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           0.089
_exptl_absorpt_correction_type          gaussian
_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)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
;
_exptl_absorpt_correction_T_min         0.948
_exptl_absorpt_correction_T_max         0.972
_shelx_estimated_absorpt_T_min          0.937
_shelx_estimated_absorpt_T_max          0.962
 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_source                          'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature             100.05(10)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_probe                 x-ray
_diffrn_detector_area_resol_mean        10.4875
_diffrn_measurement_device_type         'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method              'ω scans'
_diffrn_reflns_av_R_equivalents         0.024
_diffrn_reflns_number                   32143
_diffrn_reflns_limit_h_min              -19
_diffrn_reflns_limit_h_max              19
_diffrn_reflns_limit_k_min              -18
_diffrn_reflns_limit_k_max              18
_diffrn_reflns_limit_l_min              -27
_diffrn_reflns_limit_l_max              28
_diffrn_reflns_theta_min                3.02
_diffrn_reflns_theta_max                29.427
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_full
                                        0.999
_diffrn_measured_fraction_theta_max
                                        0.942
_diffrn_reflns_Laue_measured_fraction_full
                                        0.999
_diffrn_reflns_Laue_measured_fraction_max
                                        0.942
_diffrn_reflns_point_group_measured_fraction_full
                                        0.999
_diffrn_reflns_point_group_measured_fraction_max
                                        0.942
_reflns_number_total                    4847
_reflns_number_gt                       4367
_reflns_threshold_expression            'I > 2σ(I)'
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_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_refinement         'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
 
_atom_sites_solution_hydrogens          mixed
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0516P)²+2.6713P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           mixed
_refine_ls_extinction_method            SHELXL
_refine_ls_extinction_expression
                                    Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef              0.0007(2)
_refine_ls_number_reflns                4847
_refine_ls_number_parameters            226
_refine_ls_number_restraints            0
_refine_ls_number_constraints           0
_refine_ls_R_factor_all                 0.043
_refine_ls_R_factor_gt                  0.0388
_refine_ls_wR_factor_ref                0.106
_refine_ls_wR_factor_gt                 0.1026
_refine_ls_goodness_of_fit_ref          1.039
_refine_ls_restrained_S_all             1.039
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.434
_refine_diff_density_min                -0.244
_refine_diff_density_rms                0.041
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
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_calc_flag
    _atom_site_disorder_assembly
    _atom_site_disorder_group
H2N H 0.0710(10) -0.0720(11) 0.3481(7) 0.025(3) Uiso 1 d . .
H1N H 0.1760(11) -0.3315(11) 0.1765(7) 0.029(3) Uiso 1 d . .
O3 O 0.21772(5) 0.09717(5) 0.35832(4) 0.01973(15) Uani 1 d . .
O2 O -0.01465(5) -0.21865(6) 0.16016(4) 0.02338(17) Uani 1 d . .
N1 N 0.14248(6) -0.28350(6) 0.18779(4) 0.01778(17) Uani 1 d . .
O1 O 0.01673(5) -0.37530(6) 0.12684(4) 0.02796(19) Uani 1 d . .
O4 O 0.17682(6) 0.03011(7) 0.49167(4) 0.03035(19) Uani 1 d . .
O5 O 0.10732(6) 0.18454(6) 0.47307(4) 0.03094(19) Uani 1 d . .
N2 N 0.09173(6) -0.00972(6) 0.35297(4) 0.01697(17) Uani 1 d . .
C12 C 0.17612(7) 0.01449(7) 0.34089(4) 0.01524(17) Uani 1 d . .
C13 C 0.04395(7) 0.05987(7) 0.38738(5) 0.01677(18) Uani 1 d . .
C8 C 0.21708(7) -0.06238(7) 0.30413(5) 0.01595(18) Uani 1 d . .
C6 C 0.19733(7) -0.20439(7) 0.22787(5) 0.01599(18) Uani 1 d . .
C7 C 0.15721(7) -0.13634(7) 0.26312(4) 0.01539(17) Uani 1 d . .
H7 H 0.0905 -0.1404 0.2592 0.018 Uiso 1 calc . .
C5 C 0.04232(7) -0.28628(7) 0.15830(5) 0.01796(19) Uani 1 d . .
C9 C 0.31726(7) -0.05636(8) 0.31077(6) 0.0235(2) Uani 1 d . .
H9 H 0.3574 -0.0074 0.3385 0.028 Uiso 1 calc . .
C14 C 0.11932(7) 0.08875(8) 0.45587(5) 0.01987(19) Uani 1 d . .
C11 C 0.29744(7) -0.19729(8) 0.23386(6) 0.0238(2) Uani 1 d . .
H11 H 0.3245 -0.2416 0.2099 0.029 Uiso 1 calc . .
C15 C -0.03797(7) 0.00089(9) 0.40397(5) 0.0235(2) Uani 1 d . .
H15A H -0.0096 -0.0563 0.432 0.035 Uiso 1 calc . .
H15B H -0.0859 -0.0224 0.3627 0.035 Uiso 1 calc . .
H15C H -0.0698 0.0445 0.4276 0.035 Uiso 1 calc . .
C10 C 0.35643(8) -0.12427(9) 0.27548(6) 0.0286(2) Uani 1 d . .
H10 H 0.4234 -0.1207 0.2798 0.034 Uiso 1 calc . .
C16 C -0.00071(8) 0.15063(9) 0.34270(6) 0.0269(2) Uani 1 d . .
H16A H 0.0508 0.1874 0.3324 0.04 Uiso 1 calc . .
H16B H -0.0326 0.1944 0.3661 0.04 Uiso 1 calc . .
H16C H -0.0485 0.1273 0.3014 0.04 Uiso 1 calc . .
C4 C -0.08797(8) -0.40039(9) 0.08914(7) 0.0327(3) Uani 1 d . .
C1 C -0.07996(10) -0.50995(12) 0.06892(10) 0.0593(5) Uani 1 d . .
H1A H -0.0394 -0.5134 0.0402 0.089 Uiso 1 calc . .
H1B H -0.1449 -0.5357 0.045 0.089 Uiso 1 calc . .
H1C H -0.0506 -0.5501 0.1088 0.089 Uiso 1 calc . .
C3 C -0.15155(11) -0.39373(13) 0.13450(9) 0.0502(4) Uani 1 d . .
H3A H -0.1255 -0.4382 0.1726 0.075 Uiso 1 calc . .
H3B H -0.2181 -0.4136 0.1095 0.075 Uiso 1 calc . .
H3C H -0.1515 -0.3252 0.1502 0.075 Uiso 1 calc . .
C17 C 0.16783(12) 0.21418(12) 0.54046(7) 0.0466(4) Uani 1 d . .
H17A H 0.1546 0.2838 0.5482 0.07 Uiso 1 calc . .
H17B H 0.2366 0.2067 0.5448 0.07 Uiso 1 calc . .
H17C H 0.1525 0.1718 0.5732 0.07 Uiso 1 calc . .
C2 C -0.12399(11) -0.33282(13) 0.02788(7) 0.0512(4) Uani 1 d . .
H2A H -0.0813 -0.3401 0.0008 0.077 Uiso 1 calc . .
H2B H -0.1234 -0.2635 0.0421 0.077 Uiso 1 calc . .
H2C H -0.1903 -0.3518 0.0016 0.077 Uiso 1 calc . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_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
O3 C12 1.2372(11) . ?
O2 C5 1.2145(11) . ?
N1 C5 1.3606(12) . ?
N1 C6 1.4049(12) . ?
N1 H1N 0.870(15) . ?
O1 C5 1.3357(12) . ?
O1 C4 1.4822(12) . ?
O4 C14 1.1962(14) . ?
O5 C14 1.3379(13) . ?
O5 C17 1.4455(15) . ?
N2 C12 1.3449(11) . ?
N2 C13 1.4614(12) . ?
N2 H2N 0.867(15) . ?
C12 C8 1.4979(13) . ?
C13 C16 1.5231(14) . ?
C13 C14 1.5326(13) . ?
C13 C15 1.5326(13) . ?
C8 C9 1.3920(13) . ?
C8 C7 1.3919(13) . ?
C6 C7 1.3941(12) . ?
C6 C11 1.3951(13) . ?
C7 H7 0.93 . ?
C9 C10 1.3856(15) . ?
C9 H9 0.93 . ?
C11 C10 1.3836(15) . ?
C11 H11 0.93 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C10 H10 0.93 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
C4 C2 1.505(2) . ?
C4 C3 1.510(2) . ?
C4 C1 1.5181(17) . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C3 H3C 0.96 . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C2 H2A 0.96 . ?
C2 H2B 0.96 . ?
C2 H2C 0.96 . ?
 
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
C5 N1 C6 126.16(8) . . ?
C5 N1 H1N 116.5(10) . . ?
C6 N1 H1N 116.8(10) . . ?
C5 O1 C4 121.65(8) . . ?
C14 O5 C17 115.33(11) . . ?
C12 N2 C13 122.05(8) . . ?
C12 N2 H2N 119.7(9) . . ?
C13 N2 H2N 117.1(9) . . ?
O3 C12 N2 121.77(8) . . ?
O3 C12 C8 121.08(8) . . ?
N2 C12 C8 117.14(8) . . ?
N2 C13 C16 111.15(8) . . ?
N2 C13 C14 108.42(8) . . ?
C16 C13 C14 113.85(8) . . ?
N2 C13 C15 107.65(8) . . ?
C16 C13 C15 109.73(8) . . ?
C14 C13 C15 105.73(7) . . ?
C9 C8 C7 120.44(9) . . ?
C9 C8 C12 117.89(8) . . ?
C7 C8 C12 121.64(8) . . ?
C7 C6 C11 119.47(9) . . ?
C7 C6 N1 123.13(8) . . ?
C11 C6 N1 117.36(8) . . ?
C8 C7 C6 119.97(8) . . ?
C8 C7 H7 120 . . ?
C6 C7 H7 120 . . ?
O2 C5 O1 125.47(9) . . ?
O2 C5 N1 125.51(9) . . ?
O1 C5 N1 109.02(8) . . ?
C10 C9 C8 119.16(9) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O4 C14 O5 124.24(10) . . ?
O4 C14 C13 123.68(9) . . ?
O5 C14 C13 111.86(9) . . ?
C10 C11 C6 119.98(9) . . ?
C10 C11 H11 120 . . ?
C6 C11 H11 120 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C10 C9 120.97(9) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C4 C2 109.13(11) . . ?
O1 C4 C3 111.11(10) . . ?
C2 C4 C3 112.87(12) . . ?
O1 C4 C1 101.89(9) . . ?
C2 C4 C1 111.21(13) . . ?
C3 C4 C1 110.10(14) . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
 
# END of CIF
