# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1523708'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_date             2017-05-17T10:47:59-00:00
_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

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

_chemical_formula_moiety         'C15 H16 O5'
_chemical_formula_sum            'C15 H16 O5'
_chemical_formula_weight         276.28

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6550(10)
_cell_length_b                   11.401(3)
_cell_length_c                   20.9880(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.186(2)
_cell_angle_gamma                90
_cell_volume                     2703.8(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29834
_cell_measurement_theta_min      1.807
_cell_measurement_theta_max      28.218
_cell_measurement_wavelength     0.7

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

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168

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

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.992

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7
_diffrn_radiation_type           synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'Area detector'
_diffrn_measurement_device_type  'Dectris Pilatus 2M'
_diffrn_measurement_method       'Rotating Crystal'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_number            44172
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.807
_diffrn_reflns_theta_max         28.218
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_reflns_Friedel_coverage         0
_reflns_number_total             6718
_reflns_number_gt                6477
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'ELETTRA XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabasch, 2010)'
_computing_data_reduction        XDS
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+1.2020P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.096(3)
_refine_ls_number_reflns         6718
_refine_ls_number_parameters     368
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1015
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.003 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'
O O 0.0105 0.0059 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C -0.52689(9) 0.10312(10) 0.93350(5) 0.0205(2) Uani 1 1 d . . . . .
H1A H -0.5769 0.0393 0.9108 0.031 Uiso 1 1 calc R U . . .
H1B H -0.5669 0.1426 0.9635 0.031 Uiso 1 1 calc R U . . .
H1C H -0.4512 0.0711 0.9586 0.031 Uiso 1 1 calc R U . . .
C2A C -0.50479(9) 0.18999(10) 0.88369(5) 0.0198(2) Uani 1 1 d . . . . .
H2A H -0.5804 0.2233 0.8579 0.024 Uiso 1 1 calc R U . . .
H2B H -0.4539 0.2549 0.9058 0.024 Uiso 1 1 calc R U . . .
C3A C -0.41497(8) 0.18554(9) 0.79350(5) 0.01376(18) Uani 1 1 d . . . . .
C4A C -0.34766(8) 0.10639(8) 0.75536(4) 0.01205(17) Uani 1 1 d . . . . .
C5A C -0.37213(8) 0.14989(9) 0.68330(4) 0.01410(18) Uani 1 1 d . . . . .
H5A H -0.3473 0.2337 0.682 0.017 Uiso 1 1 calc R U . . .
C6A C -0.31292(8) 0.07588(10) 0.64189(5) 0.0172(2) Uani 1 1 d . . . . .
H6A H -0.2298 0.0668 0.6484 0.021 Uiso 1 1 calc R U . . .
C7A C -0.39448(9) 0.02466(10) 0.59453(5) 0.0187(2) Uani 1 1 d . . . . .
H7A H -0.3796 -0.0269 0.5619 0.022 Uiso 1 1 calc R U . . .
C8A C -0.51162(8) 0.06182(9) 0.60145(5) 0.01672(19) Uani 1 1 d . . . . .
C9A C -0.21489(8) 0.11864(8) 0.78605(4) 0.01225(17) Uani 1 1 d . . . . .
C10A C -0.16168(8) 0.22880(9) 0.79743(5) 0.01563(19) Uani 1 1 d . . . . .
H10A H -0.209 0.2976 0.7889 0.019 Uiso 1 1 calc R U . . .
C11A C -0.03970(8) 0.23841(9) 0.82125(5) 0.01694(19) Uani 1 1 d . . . . .
H11A H -0.0047 0.314 0.829 0.02 Uiso 1 1 calc R U . . .
C12A C 0.03224(8) 0.13911(9) 0.83394(5) 0.01557(19) Uani 1 1 d . . . . .
C13A C -0.02182(8) 0.02940(9) 0.82307(5) 0.01589(19) Uani 1 1 d . . . . .
H13A H 0.0255 -0.0394 0.8318 0.019 Uiso 1 1 calc R U . . .
C14A C -0.14401(8) 0.01885(9) 0.79961(5) 0.01435(18) Uani 1 1 d . . . . .
H14A H -0.1792 -0.0567 0.7928 0.017 Uiso 1 1 calc R U . . .
C15A C 0.16489(9) 0.15145(10) 0.85665(5) 0.0205(2) Uani 1 1 d . . . . .
H15A H 0.1921 0.2105 0.8298 0.031 Uiso 1 1 calc R U . . .
H15B H 0.2023 0.076 0.8521 0.031 Uiso 1 1 calc R U . . .
H15C H 0.1864 0.1759 0.9028 0.031 Uiso 1 1 calc R U . . .
O1A O -0.44582(6) 0.12500(7) 0.84097(3) 0.01630(15) Uani 1 1 d . . . . .
O2A O -0.43281(7) 0.28853(7) 0.78279(4) 0.02100(17) Uani 1 1 d . . . . .
O3A O -0.37988(6) -0.01165(6) 0.75666(3) 0.01424(15) Uani 1 1 d . . . . .
H1O3 H -0.4535 -0.0167 0.7514 0.021 Uiso 1 1 calc R U . . .
O4A O -0.49696(6) 0.13771(7) 0.65272(3) 0.01561(15) Uani 1 1 d . . . . .
O5A O -0.60894(7) 0.03520(8) 0.56888(4) 0.02430(18) Uani 1 1 d . . . . .
C1B C 0.32774(10) 0.34568(12) 0.46089(5) 0.0258(2) Uani 1 1 d . . . . .
H1D H 0.3612 0.2673 0.4589 0.039 Uiso 1 1 calc R U . . .
H1E H 0.3822 0.4048 0.4513 0.039 Uiso 1 1 calc R U . . .
H1F H 0.2515 0.3514 0.4285 0.039 Uiso 1 1 calc R U . . .
C2B C 0.30986(10) 0.36641(10) 0.52849(5) 0.0220(2) Uani 1 1 d . . . . .
H2C H 0.3868 0.3656 0.5615 0.026 Uiso 1 1 calc R U . . .
H2D H 0.2715 0.4433 0.5305 0.026 Uiso 1 1 calc R U . . .
C3B C 0.20891(8) 0.27468(9) 0.59960(5) 0.01477(18) Uani 1 1 d . . . . .
C4B C 0.13153(8) 0.16904(9) 0.60795(4) 0.01308(18) Uani 1 1 d . . . . .
C5B C 0.15876(8) 0.13641(9) 0.68179(5) 0.01500(19) Uani 1 1 d . . . . .
H5B H 0.1413 0.2042 0.7082 0.018 Uiso 1 1 calc R U . . .
C6B C 0.09305(8) 0.02967(10) 0.69427(5) 0.0174(2) Uani 1 1 d . . . . .
H6B H 0.0094 0.0234 0.6859 0.021 Uiso 1 1 calc R U . . .
C7B C 0.16926(8) -0.05522(10) 0.71891(5) 0.0172(2) Uani 1 1 d . . . . .
H7B H 0.1496 -0.1313 0.7314 0.021 Uiso 1 1 calc R U . . .
C8B C 0.28917(8) -0.01046(9) 0.72344(4) 0.01541(19) Uani 1 1 d . . . . .
C9B C 0.00189(8) 0.20685(9) 0.58608(4) 0.01341(18) Uani 1 1 d . . . . .
C10B C -0.03914(8) 0.30184(9) 0.61629(5) 0.01647(19) Uani 1 1 d . . . . .
H10B H 0.014 0.3438 0.6502 0.02 Uiso 1 1 calc R U . . .
C11B C -0.15745(9) 0.33540(9) 0.59699(5) 0.0177(2) Uani 1 1 d . . . . .
H11B H -0.1842 0.4004 0.6178 0.021 Uiso 1 1 calc R U . . .
C12B C -0.23732(8) 0.27479(9) 0.54748(5) 0.01634(19) Uani 1 1 d . . . . .
C13B C -0.19537(8) 0.18014(9) 0.51774(5) 0.01688(19) Uani 1 1 d . . . . .
H13B H -0.2486 0.138 0.484 0.02 Uiso 1 1 calc R U . . .
C14B C -0.07706(8) 0.14597(9) 0.53649(5) 0.01553(19) Uani 1 1 d . . . . .
H14B H -0.0503 0.0813 0.5155 0.019 Uiso 1 1 calc R U . . .
C15B C -0.36592(9) 0.30971(11) 0.52738(5) 0.0222(2) Uani 1 1 d . . . . .
H15D H -0.3754 0.3767 0.4973 0.033 Uiso 1 1 calc R U . . .
H15E H -0.3928 0.3316 0.5665 0.033 Uiso 1 1 calc R U . . .
H15F H -0.4131 0.2436 0.5053 0.033 Uiso 1 1 calc R U . . .
O1B O 0.23467(6) 0.27208(7) 0.54109(3) 0.01813(16) Uani 1 1 d . . . . .
O2B O 0.23910(7) 0.35067(7) 0.63993(4) 0.02119(17) Uani 1 1 d . . . . .
O3B O 0.15109(6) 0.07198(6) 0.57083(3) 0.01572(15) Uani 1 1 d . . . . .
H2O3 H 0.2237 0.0664 0.5726 0.024 Uiso 1 1 calc R U . . .
O4B O 0.28216(6) 0.10323(7) 0.70352(3) 0.01579(15) Uani 1 1 d . . . . .
O5B O 0.38361(6) -0.06040(7) 0.74116(4) 0.02007(16) Uani 1 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
C1A C2A 1.5074(15) . ?
C1A H1A 0.98 . ?
C1A H1B 0.98 . ?
C1A H1C 0.98 . ?
C2A O1A 1.4585(12) . ?
C2A H2A 0.99 . ?
C2A H2B 0.99 . ?
C3A O2A 1.2040(13) . ?
C3A O1A 1.3320(11) . ?
C3A C4A 1.5420(13) . ?
C4A O3A 1.3993(12) . ?
C4A C9A 1.5299(12) . ?
C4A C5A 1.5502(13) . ?
C5A O4A 1.4457(11) . ?
C5A C6A 1.4959(14) . ?
C5A H5A 1 . ?
C6A C7A 1.3303(14) . ?
C6A H6A 0.95 . ?
C7A C8A 1.4703(13) . ?
C7A H7A 0.95 . ?
C8A O5A 1.2107(12) . ?
C8A O4A 1.3586(12) . ?
C9A C14A 1.3938(13) . ?
C9A C10A 1.3951(14) . ?
C10A C11A 1.3909(13) . ?
C10A H10A 0.95 . ?
C11A C12A 1.3951(14) . ?
C11A H11A 0.95 . ?
C12A C13A 1.3939(15) . ?
C12A C15A 1.5086(13) . ?
C13A C14A 1.3933(13) . ?
C13A H13A 0.95 . ?
C14A H14A 0.95 . ?
C15A H15A 0.98 . ?
C15A H15B 0.98 . ?
C15A H15C 0.98 . ?
O3A H1O3 0.84 . ?
C1B C2B 1.5024(15) . ?
C1B H1D 0.98 . ?
C1B H1E 0.98 . ?
C1B H1F 0.98 . ?
C2B O1B 1.4519(13) . ?
C2B H2C 0.99 . ?
C2B H2D 0.99 . ?
C3B O2B 1.2020(12) . ?
C3B O1B 1.3342(11) . ?
C3B C4B 1.5402(14) . ?
C4B O3B 1.4038(11) . ?
C4B C9B 1.5295(12) . ?
C4B C5B 1.5492(13) . ?
C5B O4B 1.4484(11) . ?
C5B C6B 1.4948(14) . ?
C5B H5B 1 . ?
C6B C7B 1.3297(15) . ?
C6B H6B 0.95 . ?
C7B C8B 1.4689(13) . ?
C7B H7B 0.95 . ?
C8B O5B 1.2137(12) . ?
C8B O4B 1.3583(13) . ?
C9B C14B 1.3938(13) . ?
C9B C10B 1.3972(14) . ?
C10B C11B 1.3921(13) . ?
C10B H10B 0.95 . ?
C11B C12B 1.3964(14) . ?
C11B H11B 0.95 . ?
C12B C13B 1.3938(14) . ?
C12B C15B 1.5076(13) . ?
C13B C14B 1.3935(13) . ?
C13B H13B 0.95 . ?
C14B H14B 0.95 . ?
C15B H15D 0.98 . ?
C15B H15E 0.98 . ?
C15B H15F 0.98 . ?
O3B H2O3 0.84 . ?

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
C2A C1A H1A 109.5 . . ?
C2A C1A H1B 109.5 . . ?
H1A C1A H1B 109.5 . . ?
C2A C1A H1C 109.5 . . ?
H1A C1A H1C 109.5 . . ?
H1B C1A H1C 109.5 . . ?
O1A C2A C1A 106.19(8) . . ?
O1A C2A H2A 110.5 . . ?
C1A C2A H2A 110.5 . . ?
O1A C2A H2B 110.5 . . ?
C1A C2A H2B 110.5 . . ?
H2A C2A H2B 108.7 . . ?
O2A C3A O1A 125.38(9) . . ?
O2A C3A C4A 124.08(9) . . ?
O1A C3A C4A 110.48(8) . . ?
O3A C4A C9A 109.16(7) . . ?
O3A C4A C3A 112.31(7) . . ?
C9A C4A C3A 108.59(7) . . ?
O3A C4A C5A 109.91(8) . . ?
C9A C4A C5A 107.87(7) . . ?
C3A C4A C5A 108.89(7) . . ?
O4A C5A C6A 104.20(7) . . ?
O4A C5A C4A 109.08(7) . . ?
C6A C5A C4A 112.68(8) . . ?
O4A C5A H5A 110.2 . . ?
C6A C5A H5A 110.2 . . ?
C4A C5A H5A 110.2 . . ?
C7A C6A C5A 109.56(8) . . ?
C7A C6A H6A 125.2 . . ?
C5A C6A H6A 125.2 . . ?
C6A C7A C8A 108.09(9) . . ?
C6A C7A H7A 126 . . ?
C8A C7A H7A 126 . . ?
O5A C8A O4A 121.69(9) . . ?
O5A C8A C7A 129.51(10) . . ?
O4A C8A C7A 108.80(8) . . ?
C14A C9A C10A 118.92(8) . . ?
C14A C9A C4A 119.95(8) . . ?
C10A C9A C4A 121.04(8) . . ?
C11A C10A C9A 120.32(9) . . ?
C11A C10A H10A 119.8 . . ?
C9A C10A H10A 119.8 . . ?
C10A C11A C12A 121.21(9) . . ?
C10A C11A H11A 119.4 . . ?
C12A C11A H11A 119.4 . . ?
C13A C12A C11A 118.07(9) . . ?
C13A C12A C15A 121.50(9) . . ?
C11A C12A C15A 120.40(9) . . ?
C14A C13A C12A 121.15(9) . . ?
C14A C13A H13A 119.4 . . ?
C12A C13A H13A 119.4 . . ?
C13A C14A C9A 120.33(9) . . ?
C13A C14A H14A 119.8 . . ?
C9A C14A H14A 119.8 . . ?
C12A C15A H15A 109.5 . . ?
C12A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C12A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C3A O1A C2A 116.80(8) . . ?
C4A O3A H1O3 109.5 . . ?
C8A O4A C5A 109.29(7) . . ?
C2B C1B H1D 109.5 . . ?
C2B C1B H1E 109.5 . . ?
H1D C1B H1E 109.5 . . ?
C2B C1B H1F 109.5 . . ?
H1D C1B H1F 109.5 . . ?
H1E C1B H1F 109.5 . . ?
O1B C2B C1B 106.56(9) . . ?
O1B C2B H2C 110.4 . . ?
C1B C2B H2C 110.4 . . ?
O1B C2B H2D 110.4 . . ?
C1B C2B H2D 110.4 . . ?
H2C C2B H2D 108.6 . . ?
O2B C3B O1B 124.83(9) . . ?
O2B C3B C4B 124.20(9) . . ?
O1B C3B C4B 110.94(8) . . ?
O3B C4B C9B 109.79(7) . . ?
O3B C4B C3B 111.97(8) . . ?
C9B C4B C3B 107.97(8) . . ?
O3B C4B C5B 110.15(8) . . ?
C9B C4B C5B 108.24(7) . . ?
C3B C4B C5B 108.62(7) . . ?
O4B C5B C6B 104.13(8) . . ?
O4B C5B C4B 108.78(7) . . ?
C6B C5B C4B 112.49(8) . . ?
O4B C5B H5B 110.4 . . ?
C6B C5B H5B 110.4 . . ?
C4B C5B H5B 110.4 . . ?
C7B C6B C5B 109.79(8) . . ?
C7B C6B H6B 125.1 . . ?
C5B C6B H6B 125.1 . . ?
C6B C7B C8B 107.86(9) . . ?
C6B C7B H7B 126.1 . . ?
C8B C7B H7B 126.1 . . ?
O5B C8B O4B 121.58(9) . . ?
O5B C8B C7B 129.34(10) . . ?
O4B C8B C7B 109.09(8) . . ?
C14B C9B C10B 119.22(9) . . ?
C14B C9B C4B 120.44(9) . . ?
C10B C9B C4B 120.34(8) . . ?
C11B C10B C9B 120.39(9) . . ?
C11B C10B H10B 119.8 . . ?
C9B C10B H10B 119.8 . . ?
C10B C11B C12B 120.84(9) . . ?
C10B C11B H11B 119.6 . . ?
C12B C11B H11B 119.6 . . ?
C13B C12B C11B 118.25(9) . . ?
C13B C12B C15B 120.86(9) . . ?
C11B C12B C15B 120.88(10) . . ?
C14B C13B C12B 121.43(9) . . ?
C14B C13B H13B 119.3 . . ?
C12B C13B H13B 119.3 . . ?
C13B C14B C9B 119.88(9) . . ?
C13B C14B H14B 120.1 . . ?
C9B C14B H14B 120.1 . . ?
C12B C15B H15D 109.5 . . ?
C12B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C12B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C3B O1B C2B 115.67(8) . . ?
C4B O3B H2O3 109.5 . . ?
C8B O4B C5B 109.05(7) . . ?

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
O2A C3A C4A O3A -154.92(9) . . . . ?
O1A C3A C4A O3A 27.49(10) . . . . ?
O2A C3A C4A C9A 84.26(11) . . . . ?
O1A C3A C4A C9A -93.32(9) . . . . ?
O2A C3A C4A C5A -32.95(12) . . . . ?
O1A C3A C4A C5A 149.47(8) . . . . ?
O3A C4A C5A O4A 60.27(10) . . . . ?
C9A C4A C5A O4A 179.18(7) . . . . ?
C3A C4A C5A O4A -63.15(10) . . . . ?
O3A C4A C5A C6A -54.94(10) . . . . ?
C9A C4A C5A C6A 63.97(10) . . . . ?
C3A C4A C5A C6A -178.36(8) . . . . ?
O4A C5A C6A C7A -1.72(11) . . . . ?
C4A C5A C6A C7A 116.39(9) . . . . ?
C5A C6A C7A C8A 0.28(12) . . . . ?
C6A C7A C8A O5A -179.52(11) . . . . ?
C6A C7A C8A O4A 1.39(12) . . . . ?
O3A C4A C9A C14A 10.63(11) . . . . ?
C3A C4A C9A C14A 133.37(9) . . . . ?
C5A C4A C9A C14A -108.76(10) . . . . ?
O3A C4A C9A C10A -173.06(8) . . . . ?
C3A C4A C9A C10A -50.32(11) . . . . ?
C5A C4A C9A C10A 67.55(11) . . . . ?
C14A C9A C10A C11A 0.68(14) . . . . ?
C4A C9A C10A C11A -175.67(8) . . . . ?
C9A C10A C11A C12A 0.38(15) . . . . ?
C10A C11A C12A C13A -1.02(14) . . . . ?
C10A C11A C12A C15A 177.04(9) . . . . ?
C11A C12A C13A C14A 0.61(14) . . . . ?
C15A C12A C13A C14A -177.43(9) . . . . ?
C12A C13A C14A C9A 0.44(14) . . . . ?
C10A C9A C14A C13A -1.08(14) . . . . ?
C4A C9A C14A C13A 175.31(8) . . . . ?
O2A C3A O1A C2A -0.76(14) . . . . ?
C4A C3A O1A C2A 176.79(8) . . . . ?
C1A C2A O1A C3A -178.54(8) . . . . ?
O5A C8A O4A C5A 178.31(10) . . . . ?
C7A C8A O4A C5A -2.51(11) . . . . ?
C6A C5A O4A C8A 2.58(10) . . . . ?
C4A C5A O4A C8A -117.98(9) . . . . ?
O2B C3B C4B O3B -153.99(9) . . . . ?
O1B C3B C4B O3B 27.84(11) . . . . ?
O2B C3B C4B C9B 85.04(11) . . . . ?
O1B C3B C4B C9B -93.13(9) . . . . ?
O2B C3B C4B C5B -32.12(13) . . . . ?
O1B C3B C4B C5B 149.71(8) . . . . ?
O3B C4B C5B O4B 61.37(10) . . . . ?
C9B C4B C5B O4B -178.59(8) . . . . ?
C3B C4B C5B O4B -61.60(10) . . . . ?
O3B C4B C5B C6B -53.46(10) . . . . ?
C9B C4B C5B C6B 66.59(10) . . . . ?
C3B C4B C5B C6B -176.43(8) . . . . ?
O4B C5B C6B C7B -1.12(11) . . . . ?
C4B C5B C6B C7B 116.50(9) . . . . ?
C5B C6B C7B C8B -0.66(11) . . . . ?
C6B C7B C8B O5B -177.34(10) . . . . ?
C6B C7B C8B O4B 2.36(11) . . . . ?
O3B C4B C9B C14B 0.64(12) . . . . ?
C3B C4B C9B C14B 122.95(10) . . . . ?
C5B C4B C9B C14B -119.63(10) . . . . ?
O3B C4B C9B C10B 179.70(9) . . . . ?
C3B C4B C9B C10B -57.98(11) . . . . ?
C5B C4B C9B C10B 59.43(12) . . . . ?
C14B C9B C10B C11B -0.12(15) . . . . ?
C4B C9B C10B C11B -179.19(9) . . . . ?
C9B C10B C11B C12B 0.29(15) . . . . ?
C10B C11B C12B C13B -0.24(15) . . . . ?
C10B C11B C12B C15B 178.90(10) . . . . ?
C11B C12B C13B C14B 0.03(15) . . . . ?
C15B C12B C13B C14B -179.12(9) . . . . ?
C12B C13B C14B C9B 0.14(15) . . . . ?
C10B C9B C14B C13B -0.10(15) . . . . ?
C4B C9B C14B C13B 178.98(9) . . . . ?
O2B C3B O1B C2B 3.25(14) . . . . ?
C4B C3B O1B C2B -178.60(8) . . . . ?
C1B C2B O1B C3B 179.62(9) . . . . ?
O5B C8B O4B C5B 176.65(9) . . . . ?
C7B C8B O4B C5B -3.08(10) . . . . ?
C6B C5B O4B C8B 2.59(10) . . . . ?
C4B C5B O4B C8B -117.56(8) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1523707'
_audit_update_record             
;
2017-06-26 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_date             2016-12-20T14:37:12-00:00
_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

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

_chemical_formula_moiety         'C15 H13 N O5'
_chemical_formula_sum            'C15 H13 N O5'
_chemical_formula_weight         287.26
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pn21a
_symmetry_space_group_name_Hall  'P -2ac -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, y, -z+1/2'

_cell_length_a                   10.2780(3)
_cell_length_b                   10.4130(16)
_cell_length_c                   12.4050(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1327.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2854
_cell_measurement_theta_min      2.515
_cell_measurement_theta_max      29.983
_cell_measurement_wavelength     0.7

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600

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

_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7
_diffrn_radiation_type           synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'Area Detector'
_diffrn_measurement_device_type  'Dectris Pilatus 2M'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_number            24594
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.515
_diffrn_reflns_theta_max         29.983
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.966
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.97
_reflns_Friedel_coverage         0.911
_reflns_number_total             3912
_reflns_number_gt                3904
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'ELETTRA XRD1 Data Collectuion SW'
_computing_cell_refinement       XDS
_computing_data_reduction        'XDS - CCP4'
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.2492P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.197(12)
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     193
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1858 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.003 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.57978(16) 1.02645(17) 0.80412(13) 0.0261(3) Uani 1 1 d . . . . .
H1A H 0.6467 0.9682 0.7762 0.039 Uiso 1 1 calc R U . . .
H1B H 0.5793 1.0228 0.8831 0.039 Uiso 1 1 calc R U . . .
H1C H 0.5987 1.1144 0.7807 0.039 Uiso 1 1 calc R U . . .
C2 C 0.44909(15) 0.98652(16) 0.76199(11) 0.0222(3) Uani 1 1 d . . . . .
H2A H 0.4223 0.9051 0.7966 0.027 Uiso 1 1 calc R U . . .
H2B H 0.3837 1.0529 0.78 0.027 Uiso 1 1 calc R U . . .
C3 C 0.42436(12) 1.07042(13) 0.58323(10) 0.0146(2) Uani 1 1 d . . . . .
C4 C 0.44780(11) 1.04125(12) 0.46233(10) 0.0117(2) Uani 1 1 d . . . . .
C5 C 0.39970(12) 0.90457(12) 0.43657(10) 0.0118(2) Uani 1 1 d . . . . .
H5 H 0.4554 0.8399 0.4743 0.014 Uiso 1 1 calc R U . . .
C6 C 0.39310(13) 0.87430(13) 0.31876(11) 0.0154(2) Uani 1 1 d . . . . .
H6 H 0.4645 0.8772 0.2702 0.019 Uiso 1 1 calc R U . . .
C7 C 0.27135(14) 0.84261(14) 0.29264(10) 0.0173(2) Uani 1 1 d . . . . .
H7 H 0.242 0.8183 0.2229 0.021 Uiso 1 1 calc R U . . .
C8 C 0.19008(13) 0.85163(12) 0.39006(10) 0.0152(2) Uani 1 1 d . . . . .
C9 C 0.59410(12) 1.05271(12) 0.44120(9) 0.0118(2) Uani 1 1 d . . . . .
C10 C 0.63875(13) 1.15219(13) 0.37552(10) 0.0145(2) Uani 1 1 d . . . . .
H10 H 0.5781 1.2071 0.3407 0.017 Uiso 1 1 calc R U . . .
C11 C 0.77103(13) 1.17128(13) 0.36086(11) 0.0165(2) Uani 1 1 d . . . . .
H11 H 0.801 1.2393 0.3162 0.02 Uiso 1 1 calc R U . . .
C12 C 0.85968(13) 1.09068(12) 0.41160(10) 0.0148(2) Uani 1 1 d . . . . .
C13 C 0.81653(13) 0.98635(13) 0.47325(10) 0.0157(2) Uani 1 1 d . . . . .
H13 H 0.8774 0.9287 0.5045 0.019 Uiso 1 1 calc R U . . .
C14 C 0.68381(13) 0.96795(13) 0.48826(10) 0.0147(2) Uani 1 1 d . . . . .
H14 H 0.6538 0.8978 0.5305 0.018 Uiso 1 1 calc R U . . .
C15 C 0.99666(14) 1.11914(15) 0.40306(11) 0.0178(3) Uani 1 1 d . . . . .
N1 N 1.10454(13) 1.14609(14) 0.39788(11) 0.0229(3) Uani 1 1 d . . . . .
O1 O 0.45442(11) 0.96924(11) 0.64513(8) 0.0187(2) Uani 1 1 d . . . . .
O2 O 0.38674(12) 1.17216(11) 0.61574(9) 0.0238(2) Uani 1 1 d . . . . .
O3 O 0.38404(9) 1.13351(10) 0.39907(8) 0.0157(2) Uani 1 1 d . . . . .
H1O3 H 0.3036 1.1296 0.4104 0.024 Uiso 1 1 calc R U . . .
O4 O 0.26668(9) 0.89354(9) 0.47321(8) 0.01343(19) Uani 1 1 d . . . . .
O5 O 0.07640(11) 0.82809(11) 0.40339(9) 0.0215(2) Uani 1 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
C1 C2 1.500(2) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 O1 1.4618(15) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 O2 1.1977(17) . ?
C3 O1 1.3399(17) . ?
C3 C4 1.5490(17) . ?
C4 O3 1.4029(15) . ?
C4 C9 1.5310(16) . ?
C4 C5 1.5402(17) . ?
C5 O4 1.4453(15) . ?
C5 C6 1.4966(17) . ?
C5 H5 1 . ?
C6 C7 1.3340(19) . ?
C6 H6 0.95 . ?
C7 C8 1.4721(18) . ?
C7 H7 0.95 . ?
C8 O5 1.2053(18) . ?
C8 O4 1.3690(15) . ?
C9 C10 1.3955(17) . ?
C9 C14 1.4036(17) . ?
C10 C11 1.3860(18) . ?
C10 H10 0.95 . ?
C11 C12 1.3895(18) . ?
C11 H11 0.95 . ?
C12 C13 1.4007(18) . ?
C12 C15 1.4427(18) . ?
C13 C14 1.3901(18) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 N1 1.146(2) . ?
O3 H1O3 0.84 . ?

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
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 . . ?
O1 C2 C1 110.25(12) . . ?
O1 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
O1 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O2 C3 O1 125.24(13) . . ?
O2 C3 C4 123.35(13) . . ?
O1 C3 C4 111.40(11) . . ?
O3 C4 C9 108.04(10) . . ?
O3 C4 C5 111.52(10) . . ?
C9 C4 C5 110.59(10) . . ?
O3 C4 C3 109.55(10) . . ?
C9 C4 C3 107.65(9) . . ?
C5 C4 C3 109.40(10) . . ?
O4 C5 C6 104.33(10) . . ?
O4 C5 C4 108.17(10) . . ?
C6 C5 C4 114.32(10) . . ?
O4 C5 H5 109.9 . . ?
C6 C5 H5 109.9 . . ?
C4 C5 H5 109.9 . . ?
C7 C6 C5 109.38(11) . . ?
C7 C6 H6 125.3 . . ?
C5 C6 H6 125.3 . . ?
C6 C7 C8 108.49(11) . . ?
C6 C7 H7 125.8 . . ?
C8 C7 H7 125.8 . . ?
O5 C8 O4 121.27(12) . . ?
O5 C8 C7 130.52(12) . . ?
O4 C8 C7 108.21(11) . . ?
C10 C9 C14 119.58(12) . . ?
C10 C9 C4 118.74(11) . . ?
C14 C9 C4 121.67(11) . . ?
C11 C10 C9 120.38(12) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.81(12) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.55(12) . . ?
C11 C12 C15 118.86(12) . . ?
C13 C12 C15 120.56(12) . . ?
C14 C13 C12 119.39(12) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 120.15(11) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N1 C15 C12 177.48(16) . . ?
C3 O1 C2 117.58(11) . . ?
C4 O3 H1O3 109.5 . . ?
C8 O4 C5 109.42(10) . . ?

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
O2 C3 C4 O3 -17.18(18) . . . . ?
O1 C3 C4 O3 164.31(11) . . . . ?
O2 C3 C4 C9 100.06(15) . . . . ?
O1 C3 C4 C9 -78.44(13) . . . . ?
O2 C3 C4 C5 -139.71(13) . . . . ?
O1 C3 C4 C5 41.78(14) . . . . ?
O3 C4 C5 O4 -68.36(12) . . . . ?
C9 C4 C5 O4 171.39(9) . . . . ?
C3 C4 C5 O4 52.98(12) . . . . ?
O3 C4 C5 C6 47.36(14) . . . . ?
C9 C4 C5 C6 -72.88(13) . . . . ?
C3 C4 C5 C6 168.71(10) . . . . ?
O4 C5 C6 C7 -3.11(15) . . . . ?
C4 C5 C6 C7 -121.05(13) . . . . ?
C5 C6 C7 C8 0.82(16) . . . . ?
C6 C7 C8 O5 -177.60(15) . . . . ?
C6 C7 C8 O4 1.96(16) . . . . ?
O3 C4 C9 C10 5.33(15) . . . . ?
C5 C4 C9 C10 127.64(12) . . . . ?
C3 C4 C9 C10 -112.89(12) . . . . ?
O3 C4 C9 C14 -176.28(11) . . . . ?
C5 C4 C9 C14 -53.97(14) . . . . ?
C3 C4 C9 C14 65.49(15) . . . . ?
C14 C9 C10 C11 -3.11(19) . . . . ?
C4 C9 C10 C11 175.31(11) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C13 3.2(2) . . . . ?
C10 C11 C12 C15 -174.53(12) . . . . ?
C11 C12 C13 C14 -3.50(19) . . . . ?
C15 C12 C13 C14 174.14(12) . . . . ?
C12 C13 C14 C9 0.53(19) . . . . ?
C10 C9 C14 C13 2.74(18) . . . . ?
C4 C9 C14 C13 -175.63(11) . . . . ?
O2 C3 O1 C2 -4.2(2) . . . . ?
C4 C3 O1 C2 174.28(11) . . . . ?
C1 C2 O1 C3 -91.93(16) . . . . ?
O5 C8 O4 C5 175.62(12) . . . . ?
C7 C8 O4 C5 -3.98(14) . . . . ?
C6 C5 O4 C8 4.33(13) . . . . ?
C4 C5 O4 C8 126.41(10) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1523710'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_date             2017-05-17T12:50:59-00:00
_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

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

_chemical_formula_moiety         'C12 H12 S O5'
_chemical_formula_sum            'C12 H12 O5 S'
_chemical_formula_weight         268.28

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4260(8)
_cell_length_b                   8.0080(7)
_cell_length_c                   13.8850(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.063(6)
_cell_angle_gamma                90
_cell_volume                     1237.59(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7072
_cell_measurement_theta_min      1.83
_cell_measurement_theta_max      28.689
_cell_measurement_wavelength     0.7

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.44
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560

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

_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.975

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7
_diffrn_radiation_type           synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'Area detector'
_diffrn_measurement_device_type  'Dectris Pilatus 2M'
_diffrn_measurement_method       'Rotating Crystal'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_number            19220
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.802
_diffrn_reflns_theta_max         28.217
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             3168
_reflns_number_gt                3151
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'ELETTRA XRD1 data Collection SW'
_computing_cell_refinement       'XDS (Kabasch, 2010)'
_computing_data_reduction        XDS
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²+0.6237P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       1.55(4)
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.12
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.11

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.003 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'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1218 0.1208 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24246(15) 0.6027(2) 0.54513(13) 0.0292(3) Uani 1 1 d . . . . .
H1A H 0.2029 0.6329 0.4772 0.044 Uiso 1 1 calc R U . . .
H1B H 0.2607 0.7043 0.5851 0.044 Uiso 1 1 calc R U . . .
H1C H 0.1891 0.531 0.5731 0.044 Uiso 1 1 calc R U . . .
C2 C 0.35662(13) 0.51112(17) 0.54515(10) 0.0203(3) Uani 1 1 d . . . . .
H2A H 0.4101 0.583 0.5161 0.024 Uiso 1 1 calc R U . . .
H2B H 0.3984 0.4849 0.614 0.024 Uiso 1 1 calc R U . . .
C3 C 0.31884(10) 0.36998(15) 0.39094(9) 0.0136(3) Uani 1 1 d . . . . .
C4 C 0.27848(11) 0.20586(15) 0.33651(9) 0.0134(3) Uani 1 1 d . . . . .
C5 C 0.35434(11) 0.06013(15) 0.38943(9) 0.0140(3) Uani 1 1 d . . . . .
H5 H 0.3346 0.0399 0.455 0.017 Uiso 1 1 calc R U . . .
C6 C 0.34041(12) -0.09821(16) 0.33095(10) 0.0184(3) Uani 1 1 d . . . . .
H6 H 0.2673 -0.1577 0.3092 0.022 Uiso 1 1 calc R U . . .
C7 C 0.44599(13) -0.14304(15) 0.31399(10) 0.0186(3) Uani 1 1 d . . . . .
H7 H 0.4608 -0.2393 0.2786 0.022 Uiso 1 1 calc R U . . .
C8 C 0.53574(12) -0.01812(15) 0.35938(8) 0.0149(3) Uani 1 1 d . . . . .
C9 C 0.14802(11) 0.17408(16) 0.33743(10) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.09427(13) 0.16178(19) 0.41801(11) 0.0231(3) Uani 1 1 d . . . . .
H10 H 0.136 0.1767 0.4848 0.028 Uiso 1 1 calc R U . . .
C11 C -0.02902(15) 0.1247(2) 0.38844(17) 0.0356(4) Uani 1 1 d . . . . .
H11 H -0.0799 0.1123 0.4334 0.043 Uiso 1 1 calc R U . . .
C12 C -0.06751(14) 0.1086(2) 0.28950(17) 0.0366(4) Uani 1 1 d . . . . .
H12 H -0.1482 0.0839 0.2572 0.044 Uiso 1 1 calc R U . . .
O1 O 0.33193(9) 0.35581(11) 0.48813(7) 0.0176(2) Uani 1 1 d . . . . .
O2 O 0.33441(9) 0.49558(11) 0.34754(7) 0.0184(2) Uani 1 1 d . . . . .
O3 O 0.29494(9) 0.21423(11) 0.23937(6) 0.0173(2) Uani 1 1 d . . . . .
H1O3 H 0.3126 0.3125 0.2269 0.026 Uiso 1 1 calc R U . . .
O4 O 0.48003(8) 0.10164(11) 0.40320(6) 0.0140(2) Uani 1 1 d . . . . .
O5 O 0.64230(9) -0.01013(12) 0.36307(7) 0.0190(2) Uani 1 1 d . . . . .
S1 S 0.04561(3) 0.13781(5) 0.22915(3) 0.02869(18) Uani 1 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
C1 C2 1.497(2) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 O1 1.4671(15) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 O2 1.2062(15) . ?
C3 O1 1.3285(15) . ?
C3 C4 1.5342(16) . ?
C4 O3 1.4049(14) . ?
C4 C9 1.5151(17) . ?
C4 C5 1.5379(17) . ?
C5 O4 1.4441(14) . ?
C5 C6 1.4947(17) . ?
C5 H5 1 . ?
C6 C7 1.3296(19) . ?
C6 H6 0.95 . ?
C7 C8 1.4688(17) . ?
C7 H7 0.95 . ?
C8 O5 1.2087(16) . ?
C8 O4 1.3675(14) . ?
C9 C10 1.3961(19) . ?
C9 S1 1.7084(14) . ?
C10 C11 1.407(2) . ?
C10 H10 0.95 . ?
C11 C12 1.351(3) . ?
C11 H11 0.95 . ?
C12 S1 1.708(2) . ?
C12 H12 0.95 . ?
O3 H1O3 0.84 . ?

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
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 . . ?
O1 C2 C1 110.75(12) . . ?
O1 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
O2 C3 O1 125.68(11) . . ?
O2 C3 C4 122.01(11) . . ?
O1 C3 C4 112.30(10) . . ?
O3 C4 C9 111.20(10) . . ?
O3 C4 C3 109.97(9) . . ?
C9 C4 C3 109.06(10) . . ?
O3 C4 C5 108.16(10) . . ?
C9 C4 C5 108.53(10) . . ?
C3 C4 C5 109.91(10) . . ?
O4 C5 C6 104.35(10) . . ?
O4 C5 C4 108.96(9) . . ?
C6 C5 C4 113.88(10) . . ?
O4 C5 H5 109.8 . . ?
C6 C5 H5 109.8 . . ?
C4 C5 H5 109.8 . . ?
C7 C6 C5 109.62(11) . . ?
C7 C6 H6 125.2 . . ?
C5 C6 H6 125.2 . . ?
C6 C7 C8 108.27(11) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
O5 C8 O4 120.65(11) . . ?
O5 C8 C7 130.78(12) . . ?
O4 C8 C7 108.57(11) . . ?
C10 C9 C4 129.08(12) . . ?
C10 C9 S1 110.82(10) . . ?
C4 C9 S1 120.04(10) . . ?
C9 C10 C11 111.95(15) . . ?
C9 C10 H10 124 . . ?
C11 C10 H10 124 . . ?
C12 C11 C10 113.03(16) . . ?
C12 C11 H11 123.5 . . ?
C10 C11 H11 123.5 . . ?
C11 C12 S1 112.18(12) . . ?
C11 C12 H12 123.9 . . ?
S1 C12 H12 123.9 . . ?
C3 O1 C2 116.08(10) . . ?
C4 O3 H1O3 109.5 . . ?
C8 O4 C5 109.18(9) . . ?
C12 S1 C9 92.02(8) . . ?

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
O2 C3 C4 O3 15.67(16) . . . . ?
O1 C3 C4 O3 -165.24(10) . . . . ?
O2 C3 C4 C9 -106.50(13) . . . . ?
O1 C3 C4 C9 72.59(13) . . . . ?
O2 C3 C4 C5 134.63(12) . . . . ?
O1 C3 C4 C5 -46.28(13) . . . . ?
O3 C4 C5 O4 68.46(11) . . . . ?
C9 C4 C5 O4 -170.79(9) . . . . ?
C3 C4 C5 O4 -51.61(12) . . . . ?
O3 C4 C5 C6 -47.56(13) . . . . ?
C9 C4 C5 C6 73.19(13) . . . . ?
C3 C4 C5 C6 -167.63(10) . . . . ?
O4 C5 C6 C7 0.52(14) . . . . ?
C4 C5 C6 C7 119.20(12) . . . . ?
C5 C6 C7 C8 -0.22(15) . . . . ?
C6 C7 C8 O5 179.08(13) . . . . ?
C6 C7 C8 O4 -0.19(14) . . . . ?
O3 C4 C9 C10 -178.16(13) . . . . ?
C3 C4 C9 C10 -56.74(17) . . . . ?
C5 C4 C9 C10 62.99(17) . . . . ?
O3 C4 C9 S1 4.97(14) . . . . ?
C3 C4 C9 S1 126.40(10) . . . . ?
C5 C4 C9 S1 -113.88(11) . . . . ?
C4 C9 C10 C11 -177.67(13) . . . . ?
S1 C9 C10 C11 -0.57(16) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 S1 0.11(19) . . . . ?
O2 C3 O1 C2 5.94(18) . . . . ?
C4 C3 O1 C2 -173.11(10) . . . . ?
C1 C2 O1 C3 83.45(15) . . . . ?
O5 C8 O4 C5 -178.83(11) . . . . ?
C7 C8 O4 C5 0.53(13) . . . . ?
C6 C5 O4 C8 -0.63(12) . . . . ?
C4 C5 O4 C8 -122.62(10) . . . . ?
C11 C12 S1 C9 -0.38(14) . . . . ?
C10 C9 S1 C12 0.54(12) . . . . ?
C4 C9 S1 C12 177.93(11) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1523709'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_date             2017-05-17T13:30:08-00:00
_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

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

_chemical_formula_moiety         'C14 H14 O5'
_chemical_formula_sum            'C14 H14 O5'
_chemical_formula_weight         262.25

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8770(12)
_cell_length_b                   7.9880(13)
_cell_length_c                   13.7400(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.046(3)
_cell_angle_gamma                90
_cell_volume                     1274.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15782
_cell_measurement_theta_min      2.967
_cell_measurement_theta_max      29.103
_cell_measurement_wavelength     0.7

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

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

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.995

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7
_diffrn_radiation_type           synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'Area Detector'
_diffrn_measurement_device_type  'Dectris Pilatus 2M'
_diffrn_measurement_method       'Rotating Crystal'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_number            20966
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.922
_diffrn_reflns_theta_max         28.622
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_coverage         0
_reflns_number_total             3399
_reflns_number_gt                3278
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'ELETTRA XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabasch, 2010)'
_computing_data_reduction        XDS
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+0.3954P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.485(16)
_refine_ls_number_reflns         3399
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.108
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.086

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.0031 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'
O O 0.0109 0.0061 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.74146(9) 0.61698(13) 0.44943(8) 0.0231(2) Uani 1 1 d . . . . .
H1A H 0.7829 0.649 0.5162 0.035 Uiso 1 1 calc R U . . .
H1B H 0.7201 0.7179 0.4093 0.035 Uiso 1 1 calc R U . . .
H1C H 0.7911 0.5464 0.4179 0.035 Uiso 1 1 calc R U . . .
C2 C 0.63452(8) 0.52144(12) 0.45701(7) 0.0185(2) Uani 1 1 d . . . . .
H2A H 0.585 0.5922 0.4899 0.022 Uiso 1 1 calc R U . . .
H2B H 0.5908 0.494 0.3894 0.022 Uiso 1 1 calc R U . . .
C3 C 0.68159(7) 0.37999(11) 0.61246(7) 0.01329(19) Uani 1 1 d . . . . .
C4 C 0.71887(7) 0.21364(11) 0.66611(6) 0.01244(18) Uani 1 1 d . . . . .
C5 C 0.64991(7) 0.06768(11) 0.60953(6) 0.01310(18) Uani 1 1 d . . . . .
H5 H 0.6719 0.0515 0.5438 0.016 Uiso 1 1 calc R U . . .
C6 C 0.66314(8) -0.09327(11) 0.66641(7) 0.0164(2) Uani 1 1 d . . . . .
H6 H 0.7334 -0.1522 0.6877 0.02 Uiso 1 1 calc R U . . .
C7 C 0.56145(8) -0.14114(11) 0.68268(7) 0.0166(2) Uani 1 1 d . . . . .
H7 H 0.547 -0.2394 0.7171 0.02 Uiso 1 1 calc R U . . .
C8 C 0.47537(8) -0.01586(11) 0.63826(6) 0.01392(19) Uani 1 1 d . . . . .
C9 C 0.84750(8) 0.18481(11) 0.67042(7) 0.01478(19) Uani 1 1 d . . . . .
C10 C 0.89216(8) 0.18324(13) 0.58404(7) 0.0202(2) Uani 1 1 d . . . . .
H10 H 0.8427 0.2019 0.5211 0.024 Uiso 1 1 calc R U . . .
C11 C 1.00916(9) 0.15431(14) 0.59000(9) 0.0248(2) Uani 1 1 d . . . . .
H11 H 1.0394 0.156 0.5312 0.03 Uiso 1 1 calc R U . . .
C12 C 1.08176(9) 0.12314(14) 0.68119(9) 0.0260(2) Uani 1 1 d . . . . .
H12 H 1.1612 0.1018 0.6849 0.031 Uiso 1 1 calc R U . . .
C13 C 1.03734(9) 0.12339(14) 0.76667(9) 0.0264(2) Uani 1 1 d . . . . .
H13 H 1.0867 0.1014 0.8292 0.032 Uiso 1 1 calc R U . . .
C14 C 0.92113(8) 0.15551(13) 0.76186(7) 0.0206(2) Uani 1 1 d . . . . .
H14 H 0.8919 0.1575 0.8212 0.025 Uiso 1 1 calc R U . . .
O1 O 0.66331(6) 0.36644(8) 0.51396(5) 0.01675(17) Uani 1 1 d . . . . .
O2 O 0.67211(6) 0.50672(9) 0.65769(5) 0.01892(18) Uani 1 1 d . . . . .
O3 O 0.69353(6) 0.21860(8) 0.76155(5) 0.01542(17) Uani 1 1 d . . . . .
H1O3 H 0.6846 0.3185 0.7775 0.023 Uiso 1 1 calc R U . . .
O4 O 0.52856(5) 0.10577(8) 0.59485(5) 0.01374(17) Uani 1 1 d . . . . .
O5 O 0.37289(6) -0.00964(9) 0.63525(5) 0.01795(18) Uani 1 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
C1 C2 1.5039(14) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 O1 1.4664(11) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 O2 1.2054(11) . ?
C3 O1 1.3297(11) . ?
C3 C4 1.5391(12) . ?
C4 O3 1.4060(10) . ?
C4 C9 1.5339(12) . ?
C4 C5 1.5390(12) . ?
C5 O4 1.4455(10) . ?
C5 C6 1.4957(12) . ?
C5 H5 1 . ?
C6 C7 1.3295(13) . ?
C6 H6 0.95 . ?
C7 C8 1.4693(12) . ?
C7 H7 0.95 . ?
C8 O5 1.2102(11) . ?
C8 O4 1.3623(10) . ?
C9 C14 1.3926(13) . ?
C9 C10 1.3975(13) . ?
C10 C11 1.3941(13) . ?
C10 H10 0.95 . ?
C11 C12 1.3872(16) . ?
C11 H11 0.95 . ?
C12 C13 1.3843(17) . ?
C12 H12 0.95 . ?
C13 C14 1.3918(14) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
O3 H1O3 0.84 . ?

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
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 . . ?
O1 C2 C1 111.05(8) . . ?
O1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108 . . ?
O2 C3 O1 125.46(8) . . ?
O2 C3 C4 121.79(8) . . ?
O1 C3 C4 112.75(7) . . ?
O3 C4 C9 111.94(7) . . ?
O3 C4 C5 107.31(7) . . ?
C9 C4 C5 109.06(7) . . ?
O3 C4 C3 109.04(7) . . ?
C9 C4 C3 109.44(7) . . ?
C5 C4 C3 110.04(7) . . ?
O4 C5 C6 104.29(7) . . ?
O4 C5 C4 108.73(7) . . ?
C6 C5 C4 113.61(7) . . ?
O4 C5 H5 110 . . ?
C6 C5 H5 110 . . ?
C4 C5 H5 110 . . ?
C7 C6 C5 109.57(8) . . ?
C7 C6 H6 125.2 . . ?
C5 C6 H6 125.2 . . ?
C6 C7 C8 108.19(8) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
O5 C8 O4 120.71(8) . . ?
O5 C8 C7 130.53(8) . . ?
O4 C8 C7 108.76(8) . . ?
C14 C9 C10 119.12(9) . . ?
C14 C9 C4 119.53(8) . . ?
C10 C9 C4 121.33(8) . . ?
C11 C10 C9 120.12(9) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.46(10) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.40(10) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.64(10) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.24(10) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C3 O1 C2 116.41(7) . . ?
C4 O3 H1O3 109.5 . . ?
C8 O4 C5 109.20(7) . . ?

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
O2 C3 C4 O3 23.38(11) . . . . ?
O1 C3 C4 O3 -157.32(7) . . . . ?
O2 C3 C4 C9 -99.36(10) . . . . ?
O1 C3 C4 C9 79.94(9) . . . . ?
O2 C3 C4 C5 140.82(9) . . . . ?
O1 C3 C4 C5 -39.88(10) . . . . ?
O3 C4 C5 O4 65.66(8) . . . . ?
C9 C4 C5 O4 -172.90(6) . . . . ?
C3 C4 C5 O4 -52.85(9) . . . . ?
O3 C4 C5 C6 -49.97(9) . . . . ?
C9 C4 C5 C6 71.47(9) . . . . ?
C3 C4 C5 C6 -168.48(7) . . . . ?
O4 C5 C6 C7 -0.23(10) . . . . ?
C4 C5 C6 C7 117.99(9) . . . . ?
C5 C6 C7 C8 -0.16(10) . . . . ?
C6 C7 C8 O5 179.79(9) . . . . ?
C6 C7 C8 O4 0.52(10) . . . . ?
O3 C4 C9 C14 4.53(12) . . . . ?
C5 C4 C9 C14 -114.05(9) . . . . ?
C3 C4 C9 C14 125.53(9) . . . . ?
O3 C4 C9 C10 -177.05(8) . . . . ?
C5 C4 C9 C10 64.37(11) . . . . ?
C3 C4 C9 C10 -56.05(11) . . . . ?
C14 C9 C10 C11 -0.64(15) . . . . ?
C4 C9 C10 C11 -179.06(9) . . . . ?
C9 C10 C11 C12 1.46(16) . . . . ?
C10 C11 C12 C13 -0.94(17) . . . . ?
C11 C12 C13 C14 -0.39(17) . . . . ?
C12 C13 C14 C9 1.20(16) . . . . ?
C10 C9 C14 C13 -0.68(15) . . . . ?
C4 C9 C14 C13 177.78(9) . . . . ?
O2 C3 O1 C2 3.00(13) . . . . ?
C4 C3 O1 C2 -176.27(7) . . . . ?
C1 C2 O1 C3 83.72(10) . . . . ?
O5 C8 O4 C5 179.98(8) . . . . ?
C7 C8 O4 C5 -0.67(9) . . . . ?
C6 C5 O4 C8 0.56(9) . . . . ?
C4 C5 O4 C8 -120.96(7) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1523706'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_date             2016-12-23T13:15:01-00:00
_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

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

_chemical_formula_moiety         'C14 H13 Cl O5'
_chemical_formula_sum            'C14 H13 Cl O5'
_chemical_formula_weight         296.69

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6510(5)
_cell_length_b                   11.4870(19)
_cell_length_c                   20.733(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.181(4)
_cell_angle_gamma                90
_cell_volume                     2690.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    31547
_cell_measurement_theta_min      1.811
_cell_measurement_theta_max      29.998
_cell_measurement_wavelength     0.7

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

_exptl_crystal_description       rod
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232

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

_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.978

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'Area detector'
_diffrn_measurement_device_type  'Dectris Pilatus 2M'
_diffrn_measurement_method       'Rotating Crystal'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_number            50687
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.811
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             8125
_reflns_number_gt                7690
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'ELETTRA XRD1 Data Collection SW'
_computing_cell_refinement       'XDS, Kabasch 2010'
_computing_data_reduction        'XDS - CCP4'
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.9381P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0347(15)
_refine_ls_number_reflns         8125
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.091
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.086

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.003 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'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1456 0.155 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.18511(2) 0.34312(2) 0.63999(2) 0.02436(7) Uani 1 1 d . . . . .
Cl2 Cl 0.37792(2) 0.18464(2) 0.97554(2) 0.02566(7) Uani 1 1 d . . . . .
O3A O 0.37532(6) 0.50905(6) 0.74377(3) 0.01549(12) Uani 1 1 d . . . . .
H1O3 H 0.4493 0.5146 0.751 0.023 Uiso 1 1 calc R U . . .
O1A O 0.44104(6) 0.37395(6) 0.65906(3) 0.01735(13) Uani 1 1 d . . . . .
O4A O 0.49477(6) 0.36184(6) 0.84880(3) 0.01747(13) Uani 1 1 d . . . . .
O4B O -0.28548(6) 0.39930(6) 0.79672(3) 0.01749(13) Uani 1 1 d . . . . .
O3B O -0.15380(6) 0.42577(6) 0.93220(3) 0.01694(13) Uani 1 1 d . . . . .
H2O3 H -0.2265 0.4318 0.9302 0.025 Uiso 1 1 calc R U . . .
O5B O -0.39030(6) 0.55914(7) 0.75749(4) 0.02168(14) Uani 1 1 d . . . . .
O1B O -0.23965(6) 0.22503(6) 0.95800(3) 0.01908(13) Uani 1 1 d . . . . .
O2A O 0.42796(7) 0.21081(6) 0.71721(4) 0.02310(15) Uani 1 1 d . . . . .
O2B O -0.24357(7) 0.15359(7) 0.85648(4) 0.02425(15) Uani 1 1 d . . . . .
O5A O 0.60901(7) 0.46449(8) 0.93256(4) 0.02650(16) Uani 1 1 d . . . . .
C5A C 0.36965(8) 0.34978(8) 0.81903(4) 0.01578(15) Uani 1 1 d . . . . .
H5A H 0.3447 0.2668 0.821 0.019 Uiso 1 1 calc R U . . .
C4B C -0.13498(8) 0.33193(8) 0.89278(4) 0.01436(15) Uani 1 1 d . . . . .
C3A C 0.41033(8) 0.31327(8) 0.70680(4) 0.01528(15) Uani 1 1 d . . . . .
C9B C -0.00553(8) 0.29376(8) 0.91428(4) 0.01459(15) Uani 1 1 d . . . . .
C4A C 0.34364(7) 0.39159(7) 0.74586(4) 0.01349(14) Uani 1 1 d . . . . .
C5B C -0.16175(8) 0.36851(8) 0.81873(4) 0.01655(16) Uani 1 1 d . . . . .
H5B H -0.1426 0.3035 0.791 0.02 Uiso 1 1 calc R U . . .
C14B C 0.07344(8) 0.35175(8) 0.96571(4) 0.01646(16) Uani 1 1 d . . . . .
H14B H 0.0464 0.4148 0.9877 0.02 Uiso 1 1 calc R U . . .
C6A C 0.31191(8) 0.42472(9) 0.86093(4) 0.01937(17) Uani 1 1 d . . . . .
H6A H 0.2289 0.4342 0.8548 0.023 Uiso 1 1 calc R U . . .
C12B C 0.22985(8) 0.22548(8) 0.95244(5) 0.01776(16) Uani 1 1 d . . . . .
C12A C -0.03257(8) 0.35746(8) 0.66752(4) 0.01745(16) Uani 1 1 d . . . . .
C10B C 0.03511(8) 0.20104(8) 0.88219(4) 0.01807(16) Uani 1 1 d . . . . .
H10B H -0.0183 0.1614 0.8471 0.022 Uiso 1 1 calc R U . . .
C13B C 0.19181(8) 0.31776(8) 0.98503(5) 0.01782(16) Uani 1 1 d . . . . .
H13B H 0.2456 0.3573 1.02 0.021 Uiso 1 1 calc R U . . .
C3B C -0.21315(8) 0.22631(8) 0.89897(4) 0.01634(16) Uani 1 1 d . . . . .
C9A C 0.21072(7) 0.37898(7) 0.71554(4) 0.01375(15) Uani 1 1 d . . . . .
C7A C 0.39457(9) 0.47625(9) 0.90817(5) 0.02115(18) Uani 1 1 d . . . . .
H7A H 0.3808 0.5285 0.941 0.025 Uiso 1 1 calc R U . . .
C8B C -0.29471(8) 0.51227(8) 0.77664(4) 0.01730(16) Uani 1 1 d . . . . .
C14A C 0.13941(8) 0.47774(8) 0.70232(4) 0.01592(15) Uani 1 1 d . . . . .
H14A H 0.1745 0.5528 0.7096 0.019 Uiso 1 1 calc R U . . .
C11B C 0.15303(9) 0.16619(8) 0.90122(5) 0.01940(17) Uani 1 1 d . . . . .
H11B H 0.1804 0.1029 0.8795 0.023 Uiso 1 1 calc R U . . .
C7B C -0.17563(8) 0.56011(9) 0.78306(5) 0.01904(17) Uani 1 1 d . . . . .
H7B H -0.1573 0.6367 0.7715 0.023 Uiso 1 1 calc R U . . .
C8A C 0.51105(8) 0.43785(9) 0.90052(4) 0.01916(17) Uani 1 1 d . . . . .
C13A C 0.01724(8) 0.46771(8) 0.67852(4) 0.01788(16) Uani 1 1 d . . . . .
H13A H -0.0312 0.5352 0.6699 0.021 Uiso 1 1 calc R U . . .
C1A C 0.52331(9) 0.39949(9) 0.56630(5) 0.02189(18) Uani 1 1 d . . . . .
H1A H 0.4484 0.4337 0.5416 0.033 Uiso 1 1 calc R U . . .
H1C H 0.5625 0.3615 0.5351 0.033 Uiso 1 1 calc R U . . .
H1B H 0.5747 0.4609 0.5905 0.033 Uiso 1 1 calc R U . . .
C10A C 0.15854(8) 0.26907(8) 0.70372(5) 0.01789(16) Uani 1 1 d . . . . .
H10A H 0.2067 0.2013 0.7124 0.021 Uiso 1 1 calc R U . . .
C11A C 0.03664(8) 0.25793(8) 0.67936(5) 0.01942(17) Uani 1 1 d . . . . .
H11A H 0.0014 0.1831 0.671 0.023 Uiso 1 1 calc R U . . .
C2A C 0.49928(9) 0.31079(9) 0.61500(5) 0.02098(18) Uani 1 1 d . . . . .
H2A H 0.4474 0.2481 0.5913 0.025 Uiso 1 1 calc R U . . .
H2B H 0.5742 0.2757 0.6406 0.025 Uiso 1 1 calc R U . . .
C6B C -0.09783(8) 0.47695(9) 0.80801(4) 0.01916(17) Uani 1 1 d . . . . .
H6B H -0.0142 0.4852 0.8176 0.023 Uiso 1 1 calc R U . . .
C2B C -0.31739(9) 0.13109(9) 0.96799(5) 0.02233(18) Uani 1 1 d . . . . .
H2C H -0.2823 0.0546 0.9618 0.027 Uiso 1 1 calc R U . . .
H2D H -0.3954 0.1376 0.9357 0.027 Uiso 1 1 calc R U . . .
C1B C -0.33103(10) 0.14281(11) 1.03800(5) 0.0263(2) Uani 1 1 d . . . . .
H1D H -0.2541 0.1307 1.0694 0.039 Uiso 1 1 calc R U . . .
H1E H -0.3875 0.0845 1.0459 0.039 Uiso 1 1 calc R U . . .
H1F H -0.3604 0.2209 1.0443 0.039 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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
Cl1 C12A 1.7362(9) . ?
Cl2 C12B 1.7380(9) . ?
O3A C4A 1.4023(10) . ?
O3A H1O3 0.84 . ?
O1A C3A 1.3293(10) . ?
O1A C2A 1.4577(11) . ?
O4A C8A 1.3596(12) . ?
O4A C5A 1.4437(10) . ?
O4B C8B 1.3590(12) . ?
O4B C5B 1.4455(11) . ?
O3B C4B 1.4021(10) . ?
O3B H2O3 0.84 . ?
O5B C8B 1.2129(12) . ?
O1B C3B 1.3338(11) . ?
O1B C2B 1.4558(12) . ?
O2A C3A 1.2051(11) . ?
O2B C3B 1.2027(11) . ?
O5A C8A 1.2108(12) . ?
C5A C6A 1.4948(13) . ?
C5A C4A 1.5487(12) . ?
C5A H5A 1 . ?
C4B C9B 1.5285(12) . ?
C4B C3B 1.5412(13) . ?
C4B C5B 1.5480(12) . ?
C3A C4A 1.5420(12) . ?
C9B C14B 1.3952(12) . ?
C9B C10B 1.3983(12) . ?
C4A C9A 1.5288(12) . ?
C5B C6B 1.4955(13) . ?
C5B H5B 1 . ?
C14B C13B 1.3944(12) . ?
C14B H14B 0.95 . ?
C6A C7A 1.3323(14) . ?
C6A H6A 0.95 . ?
C12B C13B 1.3868(13) . ?
C12B C11B 1.3882(13) . ?
C12A C11A 1.3859(13) . ?
C12A C13A 1.3884(13) . ?
C10B C11B 1.3921(13) . ?
C10B H10B 0.95 . ?
C13B H13B 0.95 . ?
C9A C14A 1.3931(12) . ?
C9A C10A 1.3967(12) . ?
C7A C8A 1.4721(13) . ?
C7A H7A 0.95 . ?
C8B C7B 1.4677(12) . ?
C14A C13A 1.3924(12) . ?
C14A H14A 0.95 . ?
C11B H11B 0.95 . ?
C7B C6B 1.3311(14) . ?
C7B H7B 0.95 . ?
C13A H13A 0.95 . ?
C1A C2A 1.5082(14) . ?
C1A H1A 0.98 . ?
C1A H1C 0.98 . ?
C1A H1B 0.98 . ?
C10A C11A 1.3918(13) . ?
C10A H10A 0.95 . ?
C11A H11A 0.95 . ?
C2A H2A 0.99 . ?
C2A H2B 0.99 . ?
C6B H6B 0.95 . ?
C2B C1B 1.5046(14) . ?
C2B H2C 0.99 . ?
C2B H2D 0.99 . ?
C1B H1D 0.98 . ?
C1B H1E 0.98 . ?
C1B H1F 0.98 . ?

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
C4A O3A H1O3 109.5 . . ?
C3A O1A C2A 117.20(7) . . ?
C8A O4A C5A 109.27(7) . . ?
C8B O4B C5B 109.17(7) . . ?
C4B O3B H2O3 109.5 . . ?
C3B O1B C2B 115.51(7) . . ?
O4A C5A C6A 104.32(7) . . ?
O4A C5A C4A 108.89(7) . . ?
C6A C5A C4A 112.50(7) . . ?
O4A C5A H5A 110.3 . . ?
C6A C5A H5A 110.3 . . ?
C4A C5A H5A 110.3 . . ?
O3B C4B C9B 109.55(7) . . ?
O3B C4B C3B 112.13(7) . . ?
C9B C4B C3B 108.11(7) . . ?
O3B C4B C5B 110.32(7) . . ?
C9B C4B C5B 108.16(7) . . ?
C3B C4B C5B 108.46(7) . . ?
O2A C3A O1A 125.48(8) . . ?
O2A C3A C4A 124.15(8) . . ?
O1A C3A C4A 110.33(7) . . ?
C14B C9B C10B 119.37(8) . . ?
C14B C9B C4B 120.31(8) . . ?
C10B C9B C4B 120.31(8) . . ?
O3A C4A C9A 109.04(7) . . ?
O3A C4A C3A 112.01(7) . . ?
C9A C4A C3A 108.59(7) . . ?
O3A C4A C5A 109.81(7) . . ?
C9A C4A C5A 107.99(7) . . ?
C3A C4A C5A 109.31(7) . . ?
O4B C5B C6B 104.10(7) . . ?
O4B C5B C4B 108.82(7) . . ?
C6B C5B C4B 112.75(7) . . ?
O4B C5B H5B 110.3 . . ?
C6B C5B H5B 110.3 . . ?
C4B C5B H5B 110.3 . . ?
C13B C14B C9B 120.43(8) . . ?
C13B C14B H14B 119.8 . . ?
C9B C14B H14B 119.8 . . ?
C7A C6A C5A 109.63(8) . . ?
C7A C6A H6A 125.2 . . ?
C5A C6A H6A 125.2 . . ?
C13B C12B C11B 121.64(8) . . ?
C13B C12B Cl2 119.09(7) . . ?
C11B C12B Cl2 119.26(7) . . ?
C11A C12A C13A 121.45(8) . . ?
C11A C12A Cl1 118.96(7) . . ?
C13A C12A Cl1 119.57(7) . . ?
C11B C10B C9B 120.66(8) . . ?
C11B C10B H10B 119.7 . . ?
C9B C10B H10B 119.7 . . ?
C12B C13B C14B 119.06(8) . . ?
C12B C13B H13B 120.5 . . ?
C14B C13B H13B 120.5 . . ?
O2B C3B O1B 124.86(9) . . ?
O2B C3B C4B 124.05(8) . . ?
O1B C3B C4B 111.07(7) . . ?
C14A C9A C10A 119.24(8) . . ?
C14A C9A C4A 119.94(8) . . ?
C10A C9A C4A 120.75(8) . . ?
C6A C7A C8A 107.88(9) . . ?
C6A C7A H7A 126.1 . . ?
C8A C7A H7A 126.1 . . ?
O5B C8B O4B 121.43(8) . . ?
O5B C8B C7B 129.44(9) . . ?
O4B C8B C7B 109.13(8) . . ?
C13A C14A C9A 120.73(8) . . ?
C13A C14A H14A 119.6 . . ?
C9A C14A H14A 119.6 . . ?
C12B C11B C10B 118.83(8) . . ?
C12B C11B H11B 120.6 . . ?
C10B C11B H11B 120.6 . . ?
C6B C7B C8B 107.76(8) . . ?
C6B C7B H7B 126.1 . . ?
C8B C7B H7B 126.1 . . ?
O5A C8A O4A 121.71(9) . . ?
O5A C8A C7A 129.42(9) . . ?
O4A C8A C7A 108.86(8) . . ?
C12A C13A C14A 118.91(8) . . ?
C12A C13A H13A 120.5 . . ?
C14A C13A H13A 120.5 . . ?
C2A C1A H1A 109.5 . . ?
C2A C1A H1C 109.5 . . ?
H1A C1A H1C 109.5 . . ?
C2A C1A H1B 109.5 . . ?
H1A C1A H1B 109.5 . . ?
H1C C1A H1B 109.5 . . ?
C11A C10A C9A 120.56(8) . . ?
C11A C10A H10A 119.7 . . ?
C9A C10A H10A 119.7 . . ?
C12A C11A C10A 119.09(9) . . ?
C12A C11A H11A 120.5 . . ?
C10A C11A H11A 120.5 . . ?
O1A C2A C1A 105.94(8) . . ?
O1A C2A H2A 110.5 . . ?
C1A C2A H2A 110.5 . . ?
O1A C2A H2B 110.5 . . ?
C1A C2A H2B 110.5 . . ?
H2A C2A H2B 108.7 . . ?
C7B C6B C5B 109.82(8) . . ?
C7B C6B H6B 125.1 . . ?
C5B C6B H6B 125.1 . . ?
O1B C2B C1B 106.70(8) . . ?
O1B C2B H2C 110.4 . . ?
C1B C2B H2C 110.4 . . ?
O1B C2B H2D 110.4 . . ?
C1B C2B H2D 110.4 . . ?
H2C C2B H2D 108.6 . . ?
C2B C1B H1D 109.5 . . ?
C2B C1B H1E 109.5 . . ?
H1D C1B H1E 109.5 . . ?
C2B C1B H1F 109.5 . . ?
H1D C1B H1F 109.5 . . ?
H1E C1B H1F 109.5 . . ?

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
C8A O4A C5A C6A -2.08(9) . . . . ?
C8A O4A C5A C4A 118.24(8) . . . . ?
C2A O1A C3A O2A 1.00(14) . . . . ?
C2A O1A C3A C4A -176.68(7) . . . . ?
O3B C4B C9B C14B -0.61(11) . . . . ?
C3B C4B C9B C14B -123.08(9) . . . . ?
C5B C4B C9B C14B 119.67(9) . . . . ?
O3B C4B C9B C10B 179.95(8) . . . . ?
C3B C4B C9B C10B 57.48(10) . . . . ?
C5B C4B C9B C10B -59.77(10) . . . . ?
O2A C3A C4A O3A 155.88(9) . . . . ?
O1A C3A C4A O3A -26.40(10) . . . . ?
O2A C3A C4A C9A -83.65(11) . . . . ?
O1A C3A C4A C9A 94.07(8) . . . . ?
O2A C3A C4A C5A 33.94(12) . . . . ?
O1A C3A C4A C5A -148.35(7) . . . . ?
O4A C5A C4A O3A -60.77(9) . . . . ?
C6A C5A C4A O3A 54.36(9) . . . . ?
O4A C5A C4A C9A -179.55(7) . . . . ?
C6A C5A C4A C9A -64.42(9) . . . . ?
O4A C5A C4A C3A 62.48(9) . . . . ?
C6A C5A C4A C3A 177.61(7) . . . . ?
C8B O4B C5B C6B -1.08(9) . . . . ?
C8B O4B C5B C4B 119.38(8) . . . . ?
O3B C4B C5B O4B -63.04(9) . . . . ?
C9B C4B C5B O4B 177.15(7) . . . . ?
C3B C4B C5B O4B 60.13(9) . . . . ?
O3B C4B C5B C6B 51.92(10) . . . . ?
C9B C4B C5B C6B -67.88(9) . . . . ?
C3B C4B C5B C6B 175.09(7) . . . . ?
C10B C9B C14B C13B 0.02(13) . . . . ?
C4B C9B C14B C13B -179.43(8) . . . . ?
O4A C5A C6A C7A 1.50(10) . . . . ?
C4A C5A C6A C7A -116.37(9) . . . . ?
C14B C9B C10B C11B 0.17(14) . . . . ?
C4B C9B C10B C11B 179.62(8) . . . . ?
C11B C12B C13B C14B -0.07(14) . . . . ?
Cl2 C12B C13B C14B 178.93(7) . . . . ?
C9B C14B C13B C12B -0.07(14) . . . . ?
C2B O1B C3B O2B -3.97(14) . . . . ?
C2B O1B C3B C4B 177.61(8) . . . . ?
O3B C4B C3B O2B 154.01(9) . . . . ?
C9B C4B C3B O2B -85.12(11) . . . . ?
C5B C4B C3B O2B 31.94(12) . . . . ?
O3B C4B C3B O1B -27.55(10) . . . . ?
C9B C4B C3B O1B 93.32(8) . . . . ?
C5B C4B C3B O1B -149.63(8) . . . . ?
O3A C4A C9A C14A -11.23(11) . . . . ?
C3A C4A C9A C14A -133.53(8) . . . . ?
C5A C4A C9A C14A 108.04(9) . . . . ?
O3A C4A C9A C10A 171.81(8) . . . . ?
C3A C4A C9A C10A 49.51(10) . . . . ?
C5A C4A C9A C10A -68.92(10) . . . . ?
C5A C6A C7A C8A -0.40(11) . . . . ?
C5B O4B C8B O5B -178.13(8) . . . . ?
C5B O4B C8B C7B 1.53(9) . . . . ?
C10A C9A C14A C13A 0.95(13) . . . . ?
C4A C9A C14A C13A -176.06(8) . . . . ?
C13B C12B C11B C10B 0.26(14) . . . . ?
Cl2 C12B C11B C10B -178.74(7) . . . . ?
C9B C10B C11B C12B -0.31(14) . . . . ?
O5B C8B C7B C6B 178.22(10) . . . . ?
O4B C8B C7B C6B -1.40(11) . . . . ?
C5A O4A C8A O5A -178.26(9) . . . . ?
C5A O4A C8A C7A 1.92(10) . . . . ?
C6A C7A C8A O5A 179.25(11) . . . . ?
C6A C7A C8A O4A -0.95(11) . . . . ?
C11A C12A C13A C14A -0.37(14) . . . . ?
Cl1 C12A C13A C14A 178.27(7) . . . . ?
C9A C14A C13A C12A -0.59(13) . . . . ?
C14A C9A C10A C11A -0.36(13) . . . . ?
C4A C9A C10A C11A 176.62(8) . . . . ?
C13A C12A C11A C10A 0.95(14) . . . . ?
Cl1 C12A C11A C10A -177.70(7) . . . . ?
C9A C10A C11A C12A -0.58(14) . . . . ?
C3A O1A C2A C1A 179.80(8) . . . . ?
C8B C7B C6B C5B 0.69(11) . . . . ?
O4B C5B C6B C7B 0.20(10) . . . . ?
C4B C5B C6B C7B -117.58(9) . . . . ?
C3B O1B C2B C1B 177.48(8) . . . . ?

