# Electronic Supplementary Material (ESI) for RSC Advances.
# 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
#  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_vb-iii-462_1553_nc

_audit_creation_date             2013-10-21T10:56:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            
;
        name
;
_chemical_formula_moiety         'C16 H21 N O5'
_chemical_formula_structural     'C16 H21 N O5'
_chemical_formula_sum            'C16 H21 N O5'
_chemical_formula_weight         307.34
_chemical_melting_point          'not measured'
_chemical_compound_source        synthetic
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.3218(2)
_cell_length_b                   13.3020(5)
_cell_length_c                   21.7280(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1538.15(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4705
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      28.445

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             656
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro
 (Agilent Technologies,2013).
;
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Agilent Technologies)'
_diffrn_source_current           50
_diffrn_source_voltage           40
_diffrn_source_power             1.6
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Sapphire3 (Agilent Technologies)'
_diffrn_detector_area_resol_mean 16.328
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_orient_matrix_ub_11      -0.0610234
_diffrn_orient_matrix_ub_12      0.0411687
_diffrn_orient_matrix_ub_13      -0.0143813
_diffrn_orient_matrix_ub_21      0.0460728
_diffrn_orient_matrix_ub_22      -0.0161111
_diffrn_orient_matrix_ub_23      -0.0289952
_diffrn_orient_matrix_ub_31      -0.1092739
_diffrn_orient_matrix_ub_32      -0.0297773
_diffrn_orient_matrix_ub_33      -0.0041882
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_number            12379
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.203
_diffrn_reflns_theta_max         26.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             3133
_reflns_number_gt                2958
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_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)+(0.0398P)²+0.1523P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3133
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1144 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.9(3)
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.026

#----------------------------------------------------------------------------#
#                   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
O4 O 0.2591(3) 0.20156(11) 0.36158(6) 0.0475(4) Uani 1 d . .
O3 O 0.4663(3) 0.19928(11) 0.15038(6) 0.0432(4) Uani 1 d . .
O2 O 0.8979(3) 0.44841(11) 0.26722(8) 0.0504(4) Uani 1 d . .
O1 O 0.7245(3) 0.33345(10) 0.17612(6) 0.0378(3) Uani 1 d . .
N5 N 0.5497(3) 0.21924(11) 0.28849(7) 0.0379(4) Uani 1 d . .
O5 O 0.4140(4) 0.06381(11) 0.31401(7) 0.0577(5) Uani 1 d . .
C7A C 0.8621(4) 0.27908(15) 0.22169(9) 0.0369(4) Uani 1 d . .
H7A H 1.0361 0.2665 0.2091 0.044 Uiso 1 calc . .
C6 C 0.5822(4) 0.32636(14) 0.30203(9) 0.0398(5) Uani 1 d . .
H8A H 0.5701 0.3394 0.3459 0.048 Uiso 1 calc . .
H8B H 0.4588 0.3669 0.2805 0.048 Uiso 1 calc . .
C2 C 0.6164(4) 0.27903(16) 0.12669(8) 0.0398(5) Uani 1 d . .
C1' C 0.2058(4) 0.10268(16) 0.45621(9) 0.0385(4) Uani 1 d . .
C3 C 0.4386(5) 0.35115(19) 0.09645(11) 0.0587(6) Uani 1 d . .
H3A H 0.5291 0.4097 0.0832 0.088 Uiso 1 calc . .
H3B H 0.3107 0.3705 0.1253 0.088 Uiso 1 calc . .
H3C H 0.362 0.3194 0.0615 0.088 Uiso 1 calc . .
C7 C 0.8468(4) 0.34650(15) 0.27817(9) 0.0394(5) Uani 1 d . .
H7 H 0.9671 0.3217 0.3088 0.047 Uiso 1 calc . .
C13 C 0.4102(4) 0.15416(15) 0.32048(8) 0.0387(5) Uani 1 d . .
C4A C 0.7280(4) 0.18297(14) 0.24140(9) 0.0389(5) Uani 1 d . .
H14 H 0.8493 0.1373 0.2606 0.047 Uiso 1 calc . .
C4 C 0.6033(5) 0.13055(15) 0.18789(9) 0.0471(6) Uani 1 d . .
H4A H 0.7305 0.0975 0.1631 0.056 Uiso 1 calc . .
H4B H 0.49 0.0794 0.2034 0.056 Uiso 1 calc . .
C2' C 0.0906(5) 0.02541(17) 0.48722(11) 0.0549(6) Uani 1 d . .
H2' H -0.0502 -0.0054 0.4702 0.066 Uiso 1 calc . .
C1 C 0.8153(5) 0.2405(2) 0.08255(11) 0.0604(7) Uani 1 d . .
H1A H 0.7384 0.1972 0.0526 0.091 Uiso 1 calc . .
H1B H 0.9401 0.2036 0.1051 0.091 Uiso 1 calc . .
H1C H 0.8932 0.2963 0.062 0.091 Uiso 1 calc . .
C6' C 0.4147(5) 0.14682(19) 0.48178(11) 0.0522(6) Uani 1 d . .
H6' H 0.4953 0.1991 0.4613 0.063 Uiso 1 calc . .
C5 C 0.0937(4) 0.13796(19) 0.39634(10) 0.0534(6) Uani 1 d . .
H5A H 0.0503 0.0798 0.3716 0.064 Uiso 1 calc . .
H5B H -0.0602 0.1744 0.4049 0.064 Uiso 1 calc . .
C4' C 0.3873(7) 0.0371(2) 0.56821(12) 0.0700(9) Uani 1 d . .
H4' H 0.448 0.0152 0.606 0.084 Uiso 1 calc . .
C5' C 0.5053(5) 0.1135(2) 0.53804(12) 0.0649(7) Uani 1 d . .
H5' H 0.6469 0.1434 0.5552 0.078 Uiso 1 calc . .
C3' C 0.1812(7) -0.0070(2) 0.54318(13) 0.0717(9) Uani 1 d . .
H3' H 0.1012 -0.0591 0.5638 0.086 Uiso 1 calc . .
H1 H 0.804(6) 0.469(2) 0.2359(13) 0.068(9) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   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
O4 C13 1.357(2) . ?
O4 C5 1.436(3) . ?
O3 C2 1.424(2) . ?
O3 C4 1.425(3) . ?
O2 C7 1.403(2) . ?
O2 H1 0.89(3) . ?
O1 C2 1.417(2) . ?
O1 C7A 1.428(2) . ?
N5 C13 1.336(3) . ?
N5 C6 1.465(2) . ?
N5 C4A 1.476(3) . ?
O5 C13 1.210(2) . ?
C7A C7 1.522(3) . ?
C7A C4A 1.526(3) . ?
C7A H7A 0.98 . ?
C6 C7 1.524(3) . ?
C6 H8A 0.97 . ?
C6 H8B 0.97 . ?
C2 C3 1.499(3) . ?
C2 C1 1.517(3) . ?
C1' C2' 1.373(3) . ?
C1' C6' 1.375(3) . ?
C1' C5 1.506(3) . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C3 H3C 0.96 . ?
C7 H7 0.98 . ?
C4A C4 1.510(3) . ?
C4A H14 0.98 . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C2' C3' 1.377(4) . ?
C2' H2' 0.93 . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?
C6' C5' 1.387(3) . ?
C6' H6' 0.93 . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C4' C3' 1.357(5) . ?
C4' C5' 1.363(4) . ?
C4' H4' 0.93 . ?
C5' H5' 0.93 . ?
C3' H3' 0.93 . ?

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
C13 O4 C5 115.83(17) . . ?
C2 O3 C4 113.40(17) . . ?
C7 O2 H1 108.3(18) . . ?
C2 O1 C7A 118.35(15) . . ?
C13 N5 C6 126.26(17) . . ?
C13 N5 C4A 120.41(16) . . ?
C6 N5 C4A 112.40(16) . . ?
O1 C7A C7 103.48(15) . . ?
O1 C7A C4A 112.27(16) . . ?
C7 C7A C4A 104.02(16) . . ?
O1 C7A H7A 112.2 . . ?
C7 C7A H7A 112.2 . . ?
C4A C7A H7A 112.2 . . ?
N5 C6 C7 102.22(17) . . ?
N5 C6 H8A 111.3 . . ?
C7 C6 H8A 111.3 . . ?
N5 C6 H8B 111.3 . . ?
C7 C6 H8B 111.3 . . ?
H8A C6 H8B 109.2 . . ?
O1 C2 O3 109.53(14) . . ?
O1 C2 C3 105.16(17) . . ?
O3 C2 C3 106.30(17) . . ?
O1 C2 C1 111.62(18) . . ?
O3 C2 C1 111.60(18) . . ?
C3 C2 C1 112.31(19) . . ?
C2' C1' C6' 118.8(2) . . ?
C2' C1' C5 118.7(2) . . ?
C6' C1' C5 122.4(2) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C7 C7A 114.97(17) . . ?
O2 C7 C6 114.01(18) . . ?
C7A C7 C6 102.73(16) . . ?
O2 C7 H7 108.3 . . ?
C7A C7 H7 108.3 . . ?
C6 C7 H7 108.3 . . ?
O5 C13 N5 125.0(2) . . ?
O5 C13 O4 123.23(19) . . ?
N5 C13 O4 111.76(16) . . ?
N5 C4A C4 113.72(19) . . ?
N5 C4A C7A 102.80(14) . . ?
C4 C4A C7A 112.11(16) . . ?
N5 C4A H14 109.3 . . ?
C4 C4A H14 109.3 . . ?
C7A C4A H14 109.3 . . ?
O3 C4 C4A 111.66(16) . . ?
O3 C4 H4A 109.3 . . ?
C4A C4 H4A 109.3 . . ?
O3 C4 H4B 109.3 . . ?
C4A C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C1' C2' C3' 120.7(3) . . ?
C1' C2' H2' 119.6 . . ?
C3' C2' H2' 119.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1' C6' C5' 120.1(2) . . ?
C1' C6' H6' 120 . . ?
C5' C6' H6' 120 . . ?
O4 C5 C1' 113.27(18) . . ?
O4 C5 H5A 108.9 . . ?
C1' C5 H5A 108.9 . . ?
O4 C5 H5B 108.9 . . ?
C1' C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C3' C4' C5' 120.1(2) . . ?
C3' C4' H4' 119.9 . . ?
C5' C4' H4' 119.9 . . ?
C4' C5' C6' 120.1(3) . . ?
C4' C5' H5' 119.9 . . ?
C6' C5' H5' 119.9 . . ?
C4' C3' C2' 120.1(3) . . ?
C4' C3' H3' 119.9 . . ?
C2' C3' H3' 119.9 . . ?

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
C2 O1 C7A C7 -155.62(16) . . . . ?
C2 O1 C7A C4A -44.1(2) . . . . ?
C13 N5 C6 C7 149.6(2) . . . . ?
C4A N5 C6 C7 -19.3(2) . . . . ?
C7A O1 C2 O3 53.0(2) . . . . ?
C7A O1 C2 C3 166.91(17) . . . . ?
C7A O1 C2 C1 -71.1(2) . . . . ?
C4 O3 C2 O1 -58.9(2) . . . . ?
C4 O3 C2 C3 -172.07(17) . . . . ?
C4 O3 C2 C1 65.2(2) . . . . ?
O1 C7A C7 O2 -46.6(2) . . . . ?
C4A C7A C7 O2 -164.10(18) . . . . ?
O1 C7A C7 C6 77.81(17) . . . . ?
C4A C7A C7 C6 -39.67(19) . . . . ?
N5 C6 C7 O2 160.65(17) . . . . ?
N5 C6 C7 C7A 35.60(18) . . . . ?
C6 N5 C13 O5 -168.7(2) . . . . ?
C4A N5 C13 O5 -0.7(3) . . . . ?
C6 N5 C13 O4 11.7(3) . . . . ?
C4A N5 C13 O4 179.77(16) . . . . ?
C5 O4 C13 O5 -2.2(3) . . . . ?
C5 O4 C13 N5 177.40(17) . . . . ?
C13 N5 C4A C4 64.0(2) . . . . ?
C6 N5 C4A C4 -126.42(18) . . . . ?
C13 N5 C4A C7A -174.61(17) . . . . ?
C6 N5 C4A C7A -5.0(2) . . . . ?
O1 C7A C4A N5 -83.73(19) . . . . ?
C7 C7A C4A N5 27.48(19) . . . . ?
O1 C7A C4A C4 38.8(2) . . . . ?
C7 C7A C4A C4 150.00(17) . . . . ?
C2 O3 C4 C4A 57.5(2) . . . . ?
N5 C4A C4 O3 70.0(2) . . . . ?
C7A C4A C4 O3 -46.1(2) . . . . ?
C6' C1' C2' C3' 0.5(4) . . . . ?
C5 C1' C2' C3' -177.7(2) . . . . ?
C2' C1' C6' C5' -0.2(3) . . . . ?
C5 C1' C6' C5' 177.9(2) . . . . ?
C13 O4 C5 C1' 91.2(2) . . . . ?
C2' C1' C5 O4 -166.4(2) . . . . ?
C6' C1' C5 O4 15.6(3) . . . . ?
C3' C4' C5' C6' 0.3(4) . . . . ?
C1' C6' C5' C4' -0.1(4) . . . . ?
C5' C4' C3' C2' -0.1(4) . . . . ?
C1' C2' C3' C4' -0.3(4) . . . . ?
#----------------------------------------------------------------------------#
#                        END OF CIF                                          #
#----------------------------------------------------------------------------#
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1009272'
