# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_new
_audit_block_doi                 10.5517/cc1jg549
_database_code_depnum_ccdc_archive 'CCDC 1413790'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        '111 GASM 14D sovate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 O5, C4 H5 N O2, 0.5(C4 H8 O2)'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C13 H15 N O8'
_chemical_formula_iupac          ?
_chemical_formula_weight         313.26
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   4.9477(2)
_cell_length_b                   10.5762(5)
_cell_length_c                   13.8911(7)
_cell_angle_alpha                109.507(5)
_cell_angle_beta                 95.486(4)
_cell_angle_gamma                101.807(4)
_cell_volume                     660.00(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    6148
_cell_measurement_theta_min      3.0565
_cell_measurement_theta_max      30.2944
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.133
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.83662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            8239
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.063
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2581
# number of observed reflections (> n sig(I))
_reflns_number_gt                2282
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0404P)²+0.2442P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2581
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.3338(3) 0.54722(13) 0.10067(10) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.5870(3) 0.59351(13) 0.18213(9) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.7989(3) 0.70397(13) 0.18494(10) 0.0151(3) Uani 1 1 d . . . . .
H3 H 0.7809 0.7453 0.1343 0.018 Uiso 1 1 calc R U . . .
C4 C 1.0367(3) 0.75413(13) 0.26136(10) 0.0144(3) Uani 1 1 d . . . . .
C5 C 1.0612(3) 0.69205(14) 0.33472(10) 0.0150(3) Uani 1 1 d . . . . .
C6 C 0.8489(3) 0.58094(14) 0.33150(10) 0.0158(3) Uani 1 1 d . . . . .
C7 C 0.6104(3) 0.53058(13) 0.25533(10) 0.0155(3) Uani 1 1 d . . . . .
H7 H 0.4655 0.4546 0.2530 0.019 Uiso 1 1 calc R U . . .
C8 C 0.7211(3) 0.76292(14) 0.60643(10) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.9089(3) 0.78438(15) 0.70524(10) 0.0202(3) Uani 1 1 d . . . . .
H9A H 0.9789 0.7013 0.6993 0.024 Uiso 1 1 calc R U . . .
H9B H 0.8079 0.8046 0.7646 0.024 Uiso 1 1 calc R U . . .
C10 C 1.1502(3) 0.90850(15) 0.71883(11) 0.0206(3) Uani 1 1 d . . . . .
H10A H 1.1483 0.9891 0.7807 0.025 Uiso 1 1 calc R U . . .
H10B H 1.3331 0.8854 0.7267 0.025 Uiso 1 1 calc R U . . .
C11 C 1.0998(3) 0.93918(14) 0.62156(10) 0.0169(3) Uani 1 1 d . . . . .
C12 C 1.3101(3) 0.90583(15) 1.02616(12) 0.0253(3) Uani 1 1 d . . . . .
H12A H 1.1483 0.8757 0.9689 0.030 Uiso 1 1 calc R U . . .
H12B H 1.2638 0.8538 1.0724 0.030 Uiso 1 1 calc R U . . .
C13 C 1.5654(3) 0.87354(16) 0.98226(12) 0.0256(3) Uani 1 1 d . . . . .
H13A H 1.7237 0.8976 1.0398 0.031 Uiso 1 1 calc R U . . .
H13B H 1.5259 0.7729 0.9419 0.031 Uiso 1 1 calc R U . . .
N1 N 0.8452(2) 0.85331(12) 0.56284(9) 0.0180(3) Uani 1 1 d . . . . .
O1 O 0.30501(19) 0.60716(10) 0.03971(7) 0.0173(2) Uani 1 1 d . . . . .
O2 O 0.14326(19) 0.43885(10) 0.09937(7) 0.0190(2) Uani 1 1 d . . . . .
O3 O 1.2393(2) 0.86531(10) 0.26519(7) 0.0188(2) Uani 1 1 d . . . . .
O4 O 1.29617(19) 0.74577(10) 0.40928(7) 0.0187(2) Uani 1 1 d . . . . .
O5 O 0.8986(2) 0.53043(11) 0.40849(8) 0.0223(2) Uani 1 1 d . . . . .
O6 O 1.2501(2) 1.02522(10) 0.59684(7) 0.0216(2) Uani 1 1 d . . . . .
O7 O 0.4912(2) 0.67983(11) 0.56966(8) 0.0246(2) Uani 1 1 d . . . . .
O8 O 1.6424(2) 0.94915(10) 0.91683(7) 0.0224(2) Uani 1 1 d . . . . .
H1N H 0.762(4) 0.861(2) 0.5048(15) 0.044(5) Uiso 1 1 d . . . . .
H2O H -0.010(5) 0.424(2) 0.0485(16) 0.052(6) Uiso 1 1 d . . . . .
H3O H 1.384(5) 0.882(2) 0.3127(16) 0.051(6) Uiso 1 1 d . . . . .
H4O H 1.287(4) 0.694(2) 0.4463(16) 0.051(6) Uiso 1 1 d . . . . .
H5O H 0.760(4) 0.467(2) 0.4078(15) 0.046(6) Uiso 1 1 d . . . . .


#===============================================================================

# 10. 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 O1 1.2294(16) . ?
C1 O2 1.3205(16) . ?
C1 C2 1.4824(17) . ?
C2 C3 1.3876(18) . ?
C2 C7 1.3969(18) . ?
C3 C4 1.3866(18) . ?
C3 H3 0.9500 . ?
C4 O3 1.3625(16) . ?
C4 C5 1.3928(18) . ?
C5 O4 1.3615(15) . ?
C5 C6 1.3918(19) . ?
C6 O5 1.3690(16) . ?
C6 C7 1.3869(18) . ?
C7 H7 0.9500 . ?
C8 O7 1.2276(17) . ?
C8 N1 1.3694(17) . ?
C8 C9 1.5035(18) . ?
C9 C10 1.5277(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5015(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O6 1.2162(17) . ?
C11 N1 1.3848(17) . ?
C12 O8 1.4285(17) 2_877 ?
C12 C13 1.506(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O8 1.4276(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N1 H1N 0.90(2) . ?
O2 H2O 0.93(2) . ?
O3 H3O 0.87(2) . ?
O4 H4O 0.86(2) . ?
O5 H5O 0.85(2) . ?
O8 C12 1.4284(17) 2_877 ?

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
O1 C1 O2 123.02(12) . . ?
O1 C1 C2 121.75(12) . . ?
O2 C1 C2 115.23(11) . . ?
C3 C2 C7 120.78(12) . . ?
C3 C2 C1 117.78(12) . . ?
C7 C2 C1 121.42(12) . . ?
C4 C3 C2 120.19(12) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
O3 C4 C3 119.63(11) . . ?
O3 C4 C5 121.00(11) . . ?
C3 C4 C5 119.34(12) . . ?
O4 C5 C6 122.20(12) . . ?
O4 C5 C4 117.44(12) . . ?
C6 C5 C4 120.36(12) . . ?
O5 C6 C7 125.12(12) . . ?
O5 C6 C5 114.37(11) . . ?
C7 C6 C5 120.51(12) . . ?
C6 C7 C2 118.82(12) . . ?
C6 C7 H7 120.6 . . ?
C2 C7 H7 120.6 . . ?
O7 C8 N1 124.28(12) . . ?
O7 C8 C9 126.64(12) . . ?
N1 C8 C9 109.07(11) . . ?
C8 C9 C10 104.42(11) . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C11 C10 C9 104.95(11) . . ?
C11 C10 H10A 110.8 . . ?
C9 C10 H10A 110.8 . . ?
C11 C10 H10B 110.8 . . ?
C9 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?
O6 C11 N1 124.33(12) . . ?
O6 C11 C10 127.30(12) . . ?
N1 C11 C10 108.36(11) . . ?
O8 C12 C13 110.95(12) 2_877 . ?
O8 C12 H12A 109.4 2_877 . ?
C13 C12 H12A 109.4 . . ?
O8 C12 H12B 109.4 2_877 . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O8 C13 C12 111.09(11) . . ?
O8 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
O8 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C8 N1 C11 112.83(11) . . ?
C8 N1 H1N 123.3(13) . . ?
C11 N1 H1N 123.7(13) . . ?
C1 O2 H2O 107.4(13) . . ?
C4 O3 H3O 111.0(14) . . ?
C5 O4 H4O 106.9(15) . . ?
C6 O5 H5O 112.3(14) . . ?
C13 O8 C12 109.59(11) . 2_877 ?


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_t
_audit_block_doi                 10.5517/cc1jg55b
_database_code_depnum_ccdc_archive 'CCDC 1413791'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        '111 GASM hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 O5, C4 H5 N O2, H2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C11 H13 N O8'
_chemical_formula_iupac          ?
_chemical_formula_weight         287.22
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   4.7352(2)
_cell_length_b                   16.3413(5)
_cell_length_c                   15.6208(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.454(4)
_cell_angle_gamma                90
_cell_volume                     1208.34(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    1403
_cell_measurement_theta_min      2.6034
_cell_measurement_theta_max      29.1143
_cell_special_details            
;
;

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.137
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.67022
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            4986
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.609
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2366
# number of observed reflections (> n sig(I))
_reflns_number_gt                1692
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0324P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2366
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.060

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.5943(4) 0.16899(13) 0.46886(14) 0.0173(5) Uani 1 1 d . . . . .
C2 C 0.4024(4) 0.19461(13) 0.52976(14) 0.0183(5) Uani 1 1 d . . . . .
H2 H 0.3800 0.1646 0.5812 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2453(4) 0.26479(13) 0.51353(14) 0.0172(5) Uani 1 1 d . . . . .
C4 C 0.2778(4) 0.30882(13) 0.43795(14) 0.0165(5) Uani 1 1 d . . . . .
C5 C 0.4703(4) 0.28303(12) 0.37817(14) 0.0173(5) Uani 1 1 d . . . . .
C6 C 0.6284(4) 0.21314(12) 0.39367(14) 0.0167(5) Uani 1 1 d . . . . .
H6 H 0.7606 0.1953 0.3529 0.020 Uiso 1 1 calc R U . . .
C7 C 0.7670(4) 0.09416(13) 0.48216(15) 0.0202(5) Uani 1 1 d . . . . .
C8 C -0.2041(4) 0.50590(13) 0.30494(15) 0.0193(5) Uani 1 1 d . . . . .
C9 C -0.3629(4) 0.56244(13) 0.24447(15) 0.0223(5) Uani 1 1 d . . . . .
H9A H -0.4767 0.5310 0.2018 0.027 Uiso 1 1 calc R U . . .
H9B H -0.2313 0.5986 0.2140 0.027 Uiso 1 1 calc R U . . .
C10 C -0.5529(4) 0.61206(13) 0.30272(14) 0.0208(5) Uani 1 1 d . . . . .
H10A H -0.4804 0.6685 0.3102 0.025 Uiso 1 1 calc R U . . .
H10B H -0.7484 0.6146 0.2788 0.025 Uiso 1 1 calc R U . . .
C11 C -0.5430(4) 0.56645(12) 0.38630(15) 0.0175(5) Uani 1 1 d . . . . .
O1 O 0.4874(3) 0.32984(9) 0.30539(10) 0.0207(4) Uani 1 1 d . . . . .
O2 O 0.1181(3) 0.37784(9) 0.42864(11) 0.0216(4) Uani 1 1 d . . . . .
O1W O 0.9501(3) 0.21557(10) 0.72712(12) 0.0272(4) Uani 1 1 d . . . . .
O3 O 0.0588(3) 0.29210(9) 0.57332(10) 0.0217(4) Uani 1 1 d . . . . .
O4 O 0.9137(3) 0.06633(9) 0.42422(10) 0.0258(4) Uani 1 1 d . . . . .
O5 O 0.7529(3) 0.06093(10) 0.55820(11) 0.0282(4) Uani 1 1 d . . . . .
O6 O -0.6908(3) 0.57810(9) 0.44850(10) 0.0219(4) Uani 1 1 d . . . . .
O7 O 0.0037(3) 0.46502(9) 0.28889(10) 0.0233(4) Uani 1 1 d . . . . .
N1 N -0.3313(4) 0.50941(11) 0.38342(13) 0.0185(4) Uani 1 1 d . . . . .
H1N H -0.285(5) 0.4794(16) 0.4273(17) 0.043(8) Uiso 1 1 d . . . . .
H1O H 0.652(5) 0.3167(16) 0.2748(17) 0.053(9) Uiso 1 1 d . . . . .
H1WA H 1.102(6) 0.186(2) 0.742(2) 0.086(12) Uiso 1 1 d . . . . .
H1WB H 0.966(5) 0.2335(17) 0.6718(19) 0.060(10) Uiso 1 1 d . . . . .
H2O H 0.112(5) 0.4010(17) 0.3731(18) 0.057(9) Uiso 1 1 d . . . . .
H3O H -0.053(5) 0.3347(18) 0.5540(18) 0.059(9) Uiso 1 1 d . . . . .
H5O H 0.888(6) 0.014(2) 0.561(2) 0.100(12) Uiso 1 1 d . . . . .


#===============================================================================

# 10. 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 C6 1.391(3) . ?
C1 C2 1.396(3) . ?
C1 C7 1.483(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 O3 1.376(2) . ?
C3 C4 1.394(3) . ?
C4 O2 1.364(2) . ?
C4 C5 1.387(3) . ?
C5 O1 1.374(2) . ?
C5 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C7 O4 1.241(3) . ?
C7 O5 1.309(3) . ?
C8 O7 1.220(2) . ?
C8 N1 1.381(3) . ?
C8 C9 1.508(3) . ?
C9 C10 1.529(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.503(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O6 1.227(2) . ?
C11 N1 1.370(3) . ?
O1 H1O 0.95(3) . ?
O2 H2O 0.95(3) . ?
O1W H1WA 0.89(3) . ?
O1W H1WB 0.92(3) . ?
O3 H3O 0.92(3) . ?
O5 H5O 1.00(3) . ?
N1 H1N 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.74(19) . . ?
C6 C1 C7 118.1(2) . . ?
C2 C1 C7 121.2(2) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
O3 C3 C2 119.7(2) . . ?
O3 C3 C4 119.59(18) . . ?
C2 C3 C4 120.7(2) . . ?
O2 C4 C5 123.5(2) . . ?
O2 C4 C3 116.37(19) . . ?
C5 C4 C3 120.12(19) . . ?
O1 C5 C6 124.1(2) . . ?
O1 C5 C4 116.18(18) . . ?
C6 C5 C4 119.7(2) . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O4 C7 O5 123.5(2) . . ?
O4 C7 C1 121.1(2) . . ?
O5 C7 C1 115.4(2) . . ?
O7 C8 N1 125.3(2) . . ?
O7 C8 C9 126.7(2) . . ?
N1 C8 C9 107.98(18) . . ?
C8 C9 C10 104.12(18) . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
C11 C10 C9 104.36(17) . . ?
C11 C10 H10A 110.9 . . ?
C9 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
O6 C11 N1 124.3(2) . . ?
O6 C11 C10 127.23(19) . . ?
N1 C11 C10 108.39(19) . . ?
C5 O1 H1O 110.9(16) . . ?
C4 O2 H2O 115.6(16) . . ?
H1WA O1W H1WB 109(2) . . ?
C3 O3 H3O 113.4(17) . . ?
C7 O5 H5O 107.9(18) . . ?
C11 N1 C8 113.2(2) . . ?
C11 N1 H1N 121.9(17) . . ?
C8 N1 H1N 124.9(17) . . ?

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
C6 C1 C2 C3 0.4(3) . . . . ?
C7 C1 C2 C3 -179.57(18) . . . . ?
C1 C2 C3 O3 -178.78(18) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
O3 C3 C4 O2 0.1(3) . . . . ?
C2 C3 C4 O2 -178.73(17) . . . . ?
O3 C3 C4 C5 178.38(18) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
O2 C4 C5 O1 -2.2(3) . . . . ?
C3 C4 C5 O1 179.68(18) . . . . ?
O2 C4 C5 C6 178.55(18) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
O1 C5 C6 C1 -179.17(18) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 179.51(18) . . . . ?
C6 C1 C7 O4 -8.1(3) . . . . ?
C2 C1 C7 O4 171.87(19) . . . . ?
C6 C1 C7 O5 171.72(18) . . . . ?
C2 C1 C7 O5 -8.4(3) . . . . ?
O7 C8 C9 C10 -166.8(2) . . . . ?
N1 C8 C9 C10 11.9(2) . . . . ?
C8 C9 C10 C11 -13.8(2) . . . . ?
C9 C10 C11 O6 -170.2(2) . . . . ?
C9 C10 C11 N1 11.5(2) . . . . ?
O6 C11 N1 C8 177.4(2) . . . . ?
C10 C11 N1 C8 -4.3(2) . . . . ?
O7 C8 N1 C11 173.62(19) . . . . ?
C9 C8 N1 C11 -5.1(2) . . . . ?

#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_ra117
_audit_block_doi                 10.5517/cc1jg56c
_database_code_depnum_ccdc_archive 'CCDC 1413792'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        '221 GASM hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H6 O5), 2(C4 H5 N O2), H2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C22 H24 N2 O15'
_chemical_formula_iupac          ?
_chemical_formula_weight         556.43
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.0698(4)
_cell_length_b                   10.3449(6)
_cell_length_c                   15.3908(10)
_cell_angle_alpha                102.993(5)
_cell_angle_beta                 91.110(5)
_cell_angle_gamma                109.434(5)
_cell_volume                     1174.40(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    5075
_cell_measurement_theta_min      2.6853
_cell_measurement_theta_max      32.7188
_cell_special_details            
;
;

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.135
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.65866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      120(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            20774
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.691
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             4609
# number of observed reflections (> n sig(I))
_reflns_number_gt                3488
_reflns_threshold_expression     ?

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0832P)²+0.1567P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4609
_refine_ls_number_parameters     400
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.075

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 1.7813(3) 0.8132(2) 0.96543(14) 0.0221(5) Uani 1 1 d . . . . .
C2 C 1.9218(3) 0.8395(2) 1.02985(14) 0.0227(5) Uani 1 1 d . . . . .
H2 H 1.9422 0.9113 1.0837 0.027 Uiso 1 1 calc R U . . .
C3 C 2.0302(3) 0.7592(2) 1.01366(14) 0.0221(5) Uani 1 1 d . . . . .
C4 C 1.9976(3) 0.6524(2) 0.93619(15) 0.0231(5) Uani 1 1 d . . . . .
C5 C 1.8586(3) 0.6273(2) 0.87195(14) 0.0223(5) Uani 1 1 d . . . . .
C6 C 1.7502(3) 0.7081(2) 0.88618(14) 0.0236(5) Uani 1 1 d . . . . .
H6 H 1.6561 0.6921 0.8425 0.028 Uiso 1 1 calc R U . . .
C7 C 1.6637(3) 0.8977(2) 0.98313(14) 0.0228(5) Uani 1 1 d . . . . .
C8 C 1.7060(3) 0.1721(2) 0.50898(14) 0.0207(5) Uani 1 1 d . . . . .
C9 C 1.5680(3) 0.1260(2) 0.43997(14) 0.0212(5) Uani 1 1 d . . . . .
H9 H 1.5588 0.0492 0.3905 0.025 Uiso 1 1 calc R U . . .
C10 C 1.4451(3) 0.1941(2) 0.44484(14) 0.0220(5) Uani 1 1 d . . . . .
C11 C 1.4606(3) 0.3071(2) 0.51795(14) 0.0213(5) Uani 1 1 d . . . . .
C12 C 1.5983(3) 0.3512(2) 0.58550(14) 0.0225(5) Uani 1 1 d . . . . .
C13 C 1.7222(3) 0.2852(2) 0.58132(15) 0.0230(5) Uani 1 1 d . . . . .
H13 H 1.8171 0.3167 0.6272 0.028 Uiso 1 1 calc R U . . .
C14 C 1.8348(3) 0.0983(2) 0.50383(14) 0.0218(5) Uani 1 1 d . . . . .
C15 C 0.7172(3) 0.3571(2) 0.30049(15) 0.0237(5) Uani 1 1 d . . . . .
C16 C 0.7556(3) 0.2322(2) 0.24489(15) 0.0260(5) Uani 1 1 d . . . . .
H16A H 0.7868 0.2471 0.1851 0.031 Uiso 1 1 calc R U . . .
H16B H 0.6521 0.1444 0.2370 0.031 Uiso 1 1 calc R U . . .
C17 C 0.9127(3) 0.2242(2) 0.29862(14) 0.0257(5) Uani 1 1 d . . . . .
H17A H 0.8808 0.1329 0.3157 0.031 Uiso 1 1 calc R U . . .
H17B H 1.0154 0.2344 0.2632 0.031 Uiso 1 1 calc R U . . .
C18 C 0.9539(3) 0.3447(2) 0.38003(15) 0.0237(5) Uani 1 1 d . . . . .
C19 C 2.7618(3) 0.6646(2) 1.19441(15) 0.0244(5) Uani 1 1 d . . . . .
C20 C 2.7084(3) 0.7801(2) 1.25112(15) 0.0293(5) Uani 1 1 d . . . . .
H20A H 2.8026 0.8734 1.2587 0.035 Uiso 1 1 calc R U . . .
H20B H 2.6835 0.7628 1.3110 0.035 Uiso 1 1 calc R U . . .
C21 C 2.5415(3) 0.7743(2) 1.19923(15) 0.0290(5) Uani 1 1 d . . . . .
H21A H 2.4391 0.7514 1.2346 0.035 Uiso 1 1 calc R U . . .
H21B H 2.5577 0.8659 1.1847 0.035 Uiso 1 1 calc R U . . .
C22 C 2.5139(3) 0.6591(2) 1.11492(15) 0.0242(5) Uani 1 1 d . . . . .
O1 O 2.1731(2) 0.78658(17) 1.07454(11) 0.0278(4) Uani 1 1 d . . . . .
O2 O 2.1077(2) 0.57605(17) 0.92403(11) 0.0281(4) Uani 1 1 d . . . . .
O1W O 1.2129(2) -0.0858(2) 0.25999(12) 0.0374(4) Uani 1 1 d D . . . .
O3 O 1.8429(2) 0.52076(18) 0.79815(11) 0.0337(4) Uani 1 1 d . . . . .
O4 O 1.66966(19) 0.97887(16) 1.05625(10) 0.0269(4) Uani 1 1 d . . . . .
O5 O 1.5501(2) 0.87731(18) 0.91440(11) 0.0327(4) Uani 1 1 d . . . . .
O6 O 1.6116(2) 0.46175(17) 0.65725(11) 0.0314(4) Uani 1 1 d . . . . .
O7 O 1.3421(2) 0.37480(17) 0.52729(11) 0.0293(4) Uani 1 1 d . . . . .
O8 O 1.3030(2) 0.15951(18) 0.38348(11) 0.0294(4) Uani 1 1 d . . . . .
O9 O 1.83133(19) 0.00222(16) 0.43873(10) 0.0255(4) Uani 1 1 d . . . . .
O10 O 1.9540(2) 0.14264(16) 0.57396(10) 0.0268(4) Uani 1 1 d . . . . .
O11 O 1.06611(19) 0.37666(17) 0.44284(11) 0.0296(4) Uani 1 1 d . . . . .
O12 O 0.5996(2) 0.39951(17) 0.28370(11) 0.0325(4) Uani 1 1 d . . . . .
O13 O 2.4021(2) 0.62435(16) 1.05151(10) 0.0282(4) Uani 1 1 d . . . . .
O14 O 2.8939(2) 0.63726(17) 1.21042(11) 0.0310(4) Uani 1 1 d . . . . .
N1 N 0.8393(2) 0.4167(2) 0.37500(13) 0.0232(4) Uani 1 1 d . . . . .
N2 N 2.6410(2) 0.5976(2) 1.11995(12) 0.0234(4) Uani 1 1 d . . . . .
H1N H 0.846(3) 0.493(3) 0.4210(19) 0.043(8) Uiso 1 1 d . . . . .
H1O H 2.221(3) 0.723(3) 1.0565(17) 0.038(7) Uiso 1 1 d . . . . .
H1WA H 1.211(4) -0.108(3) 0.2012(12) 0.051(9) Uiso 1 1 d D . . . .
H1WB H 1.137(5) -0.161(4) 0.274(3) 0.107(15) Uiso 1 1 d . . . . .
H2N H 2.639(3) 0.520(3) 1.0672(19) 0.046(8) Uiso 1 1 d . . . . .
H2O H 2.073(4) 0.510(3) 0.874(2) 0.056(10) Uiso 1 1 d . . . . .
H3O H 1.764(4) 0.506(3) 0.756(2) 0.071(12) Uiso 1 1 d . . . . .
H5O H 1.474(4) 0.930(3) 0.928(2) 0.068(10) Uiso 1 1 d . . . . .
H6O H 1.527(3) 0.490(2) 0.6623(16) 0.027(6) Uiso 1 1 d . . . . .
H7O H 1.264(5) 0.333(4) 0.475(2) 0.081(11) Uiso 1 1 d . . . . .
H8O H 1.294(4) 0.088(3) 0.339(2) 0.061(10) Uiso 1 1 d . . . . .
H10O H 2.023(5) 0.091(4) 0.569(2) 0.075(11) Uiso 1 1 d . . . . .


#===============================================================================

# 10. 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 C6 1.394(3) . ?
C1 C2 1.405(3) . ?
C1 C7 1.481(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 O1 1.382(2) . ?
C3 C4 1.384(3) . ?
C4 O2 1.362(2) . ?
C4 C5 1.397(3) . ?
C5 O3 1.364(3) . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C7 O4 1.233(3) . ?
C7 O5 1.318(3) . ?
C8 C13 1.390(3) . ?
C8 C9 1.403(3) . ?
C8 C14 1.475(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 O8 1.367(2) . ?
C10 C11 1.397(3) . ?
C11 O7 1.354(2) . ?
C11 C12 1.388(3) . ?
C12 O6 1.373(3) . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C14 O9 1.235(3) . ?
C14 O10 1.321(2) . ?
C15 O12 1.216(2) . ?
C15 N1 1.378(3) . ?
C15 C16 1.509(3) . ?
C16 C17 1.536(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.497(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O11 1.219(3) . ?
C18 N1 1.377(3) . ?
C19 O14 1.224(3) . ?
C19 N2 1.376(3) . ?
C19 C20 1.505(3) . ?
C20 C21 1.529(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.507(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O13 1.220(3) . ?
C22 N2 1.384(3) . ?
O1 H1O 0.87(3) . ?
O2 H2O 0.87(3) . ?
O1W H1WA 0.880(18) . ?
O1W H1WB 0.88(4) . ?
O3 H3O 0.85(3) . ?
O5 H5O 0.95(3) . ?
O6 H6O 0.83(2) . ?
O7 H7O 0.93(4) . ?
O8 H8O 0.87(3) . ?
O10 H10O 0.88(3) . ?
N1 H1N 0.92(3) . ?
N2 H2N 1.00(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.98(18) . . ?
C6 C1 C7 119.93(19) . . ?
C2 C1 C7 119.09(19) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
O1 C3 C4 119.60(18) . . ?
O1 C3 C2 120.02(19) . . ?
C4 C3 C2 120.38(19) . . ?
O2 C4 C3 117.89(18) . . ?
O2 C4 C5 121.65(19) . . ?
C3 C4 C5 120.43(18) . . ?
O3 C5 C6 125.39(19) . . ?
O3 C5 C4 114.52(18) . . ?
C6 C5 C4 120.1(2) . . ?
C5 C6 C1 119.09(19) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
O4 C7 O5 122.70(19) . . ?
O4 C7 C1 122.98(19) . . ?
O5 C7 C1 114.31(18) . . ?
C13 C8 C9 121.07(18) . . ?
C13 C8 C14 120.09(18) . . ?
C9 C8 C14 118.84(19) . . ?
C10 C9 C8 119.16(19) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O8 C10 C9 125.56(19) . . ?
O8 C10 C11 114.71(18) . . ?
C9 C10 C11 119.73(19) . . ?
O7 C11 C12 117.54(18) . . ?
O7 C11 C10 122.21(18) . . ?
C12 C11 C10 120.23(18) . . ?
O6 C12 C13 119.58(19) . . ?
O6 C12 C11 119.69(17) . . ?
C13 C12 C11 120.73(19) . . ?
C12 C13 C8 119.08(19) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
O9 C14 O10 122.59(18) . . ?
O9 C14 C8 122.42(19) . . ?
O10 C14 C8 114.99(18) . . ?
O12 C15 N1 125.0(2) . . ?
O12 C15 C16 126.7(2) . . ?
N1 C15 C16 108.25(17) . . ?
C15 C16 C17 104.67(17) . . ?
C15 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C18 C17 C16 104.92(17) . . ?
C18 C17 H17A 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.8 . . ?
O11 C18 N1 123.5(2) . . ?
O11 C18 C17 127.83(19) . . ?
N1 C18 C17 108.67(18) . . ?
O14 C19 N2 125.4(2) . . ?
O14 C19 C20 125.7(2) . . ?
N2 C19 C20 108.87(17) . . ?
C19 C20 C21 104.62(18) . . ?
C19 C20 H20A 110.8 . . ?
C21 C20 H20A 110.8 . . ?
C19 C20 H20B 110.8 . . ?
C21 C20 H20B 110.8 . . ?
H20A C20 H20B 108.9 . . ?
C22 C21 C20 105.12(17) . . ?
C22 C21 H21A 110.7 . . ?
C20 C21 H21A 110.7 . . ?
C22 C21 H21B 110.7 . . ?
C20 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
O13 C22 N2 124.4(2) . . ?
O13 C22 C21 127.45(19) . . ?
N2 C22 C21 108.16(18) . . ?
C3 O1 H1O 108.1(17) . . ?
C4 O2 H2O 109.9(19) . . ?
H1WA O1W H1WB 106(3) . . ?
C5 O3 H3O 118(2) . . ?
C7 O5 H5O 112.8(19) . . ?
C12 O6 H6O 117.4(17) . . ?
C11 O7 H7O 105(2) . . ?
C10 O8 H8O 113(2) . . ?
C14 O10 H10O 111(2) . . ?
C18 N1 C15 113.44(18) . . ?
C18 N1 H1N 119.3(17) . . ?
C15 N1 H1N 127.1(17) . . ?
C19 N2 C22 113.01(18) . . ?
C19 N2 H2N 130.2(15) . . ?
C22 N2 H2N 116.5(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(3) . . . . ?
C7 C1 C2 C3 179.21(19) . . . . ?
C1 C2 C3 O1 177.66(19) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
O1 C3 C4 O2 1.2(3) . . . . ?
C2 C3 C4 O2 -179.52(19) . . . . ?
O1 C3 C4 C5 -177.10(19) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
O2 C4 C5 O3 0.7(3) . . . . ?
C3 C4 C5 O3 178.9(2) . . . . ?
O2 C4 C5 C6 -179.3(2) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
O3 C5 C6 C1 179.5(2) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C7 C1 C6 C5 -178.15(19) . . . . ?
C6 C1 C7 O4 170.3(2) . . . . ?
C2 C1 C7 O4 -8.9(3) . . . . ?
C6 C1 C7 O5 -8.7(3) . . . . ?
C2 C1 C7 O5 172.04(19) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
C14 C8 C9 C10 179.34(18) . . . . ?
C8 C9 C10 O8 -179.00(19) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
O8 C10 C11 O7 0.9(3) . . . . ?
C9 C10 C11 O7 -178.22(19) . . . . ?
O8 C10 C11 C12 179.18(18) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
O7 C11 C12 O6 -1.3(3) . . . . ?
C10 C11 C12 O6 -179.6(2) . . . . ?
O7 C11 C12 C13 178.75(19) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
O6 C12 C13 C8 179.1(2) . . . . ?
C11 C12 C13 C8 -0.9(3) . . . . ?
C9 C8 C13 C12 1.0(3) . . . . ?
C14 C8 C13 C12 -178.91(19) . . . . ?
C13 C8 C14 O9 -176.1(2) . . . . ?
C9 C8 C14 O9 3.9(3) . . . . ?
C13 C8 C14 O10 3.9(3) . . . . ?
C9 C8 C14 O10 -176.07(18) . . . . ?
O12 C15 C16 C17 -178.1(2) . . . . ?
N1 C15 C16 C17 1.8(2) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C17 C18 O11 177.7(2) . . . . ?
C16 C17 C18 N1 -0.9(2) . . . . ?
O14 C19 C20 C21 177.0(2) . . . . ?
N2 C19 C20 C21 -1.1(3) . . . . ?
C19 C20 C21 C22 -1.8(3) . . . . ?
C20 C21 C22 O13 -175.1(2) . . . . ?
C20 C21 C22 N2 4.1(3) . . . . ?
O11 C18 N1 C15 -176.5(2) . . . . ?
C17 C18 N1 C15 2.2(3) . . . . ?
O12 C15 N1 C18 177.4(2) . . . . ?
C16 C15 N1 C18 -2.5(3) . . . . ?
O14 C19 N2 C22 -174.2(2) . . . . ?
C20 C19 N2 C22 3.9(3) . . . . ?
O13 C22 N2 C19 174.1(2) . . . . ?
C21 C22 N2 C19 -5.1(3) . . . . ?


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_ra66_lt_r
_audit_block_doi                 10.5517/cc1jg57d
_database_code_depnum_ccdc_archive 'CCDC 1413793'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        '421 GASM hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H6 O5), 4(C4 H5 N O2), H2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C30 H34 N4 O19'
_chemical_formula_iupac          ?
_chemical_formula_weight         754.61
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   11.4899(7)
_cell_length_b                   13.1674(7)
_cell_length_c                   13.3084(10)
_cell_angle_alpha                67.527(6)
_cell_angle_beta                 67.492(7)
_cell_angle_gamma                64.740(6)
_cell_volume                     1623.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    10911
_cell_measurement_theta_min      2.7662
_cell_measurement_theta_max      32.7710
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             788
_exptl_absorpt_coefficient_mu    0.131
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.51716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            28566
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.772
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             6385
# number of observed reflections (> n sig(I))
_reflns_number_gt                5069
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0574P)²+0.1416P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6385
_refine_ls_number_parameters     534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.060

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.37740(18) 0.55555(15) 0.16665(14) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.33334(18) 0.45919(15) 0.21987(14) 0.0158(4) Uani 1 1 d . . . . .
H2 H 0.3923 0.3843 0.2111 0.019 Uiso 1 1 calc R U . . .
C3 C 0.20305(18) 0.47361(14) 0.28565(14) 0.0152(4) Uani 1 1 d . . . . .
C4 C 0.11681(17) 0.58336(15) 0.29776(14) 0.0144(4) Uani 1 1 d . . . . .
C5 C 0.16136(18) 0.67983(14) 0.24305(15) 0.0158(4) Uani 1 1 d . . . . .
C6 C 0.29128(18) 0.66622(15) 0.17838(14) 0.0158(4) Uani 1 1 d . . . . .
H6 H 0.3218 0.7314 0.1423 0.019 Uiso 1 1 calc R U . . .
C7 C 0.51746(18) 0.54037(15) 0.09950(14) 0.0161(4) Uani 1 1 d . . . . .
C8 C -0.03054(18) 0.55222(15) 0.12663(14) 0.0155(4) Uani 1 1 d . . . . .
C9 C -0.09220(18) 0.46806(15) 0.18659(14) 0.0164(4) Uani 1 1 d . . . . .
H9 H -0.0430 0.3884 0.1889 0.020 Uiso 1 1 calc R U . . .
C10 C -0.22646(19) 0.50148(15) 0.24315(14) 0.0168(4) Uani 1 1 d . . . . .
C11 C -0.29858(18) 0.61852(15) 0.24007(14) 0.0162(4) Uani 1 1 d . . . . .
C12 C -0.23462(18) 0.70144(14) 0.18201(15) 0.0166(4) Uani 1 1 d . . . . .
C13 C -0.10144(18) 0.66901(15) 0.12462(14) 0.0174(4) Uani 1 1 d . . . . .
H13 H -0.0583 0.7259 0.0840 0.021 Uiso 1 1 calc R U . . .
C14 C 0.11191(18) 0.52321(15) 0.06334(14) 0.0161(4) Uani 1 1 d . . . . .
C15 C 0.4389(2) 0.15255(15) 0.19801(16) 0.0219(4) Uani 1 1 d . . . . .
C16 C 0.4887(2) 0.09383(18) 0.10544(18) 0.0289(5) Uani 1 1 d . . . . .
H16A H 0.5534 0.0150 0.1250 0.035 Uiso 1 1 calc R U . . .
H16B H 0.5326 0.1398 0.0338 0.035 Uiso 1 1 calc R U . . .
C17 C 0.3647(2) 0.08696(17) 0.09500(17) 0.0251(4) Uani 1 1 d . . . . .
H17A H 0.3519 0.1293 0.0185 0.030 Uiso 1 1 calc R U . . .
H17B H 0.3720 0.0050 0.1105 0.030 Uiso 1 1 calc R U . . .
C18 C 0.2513(2) 0.14321(15) 0.18167(15) 0.0197(4) Uani 1 1 d . . . . .
C19 C 0.73993(19) 0.18261(15) 0.61825(15) 0.0190(4) Uani 1 1 d . . . . .
C20 C 0.87813(19) 0.10312(15) 0.57794(15) 0.0193(4) Uani 1 1 d . . . . .
H20A H 0.8760 0.0519 0.5407 0.023 Uiso 1 1 calc R U . . .
H20B H 0.9187 0.0541 0.6417 0.023 Uiso 1 1 calc R U . . .
C21 C 0.95652(19) 0.18447(15) 0.49414(15) 0.0210(4) Uani 1 1 d . . . . .
H21A H 1.0393 0.1660 0.5141 0.025 Uiso 1 1 calc R U . . .
H21B H 0.9803 0.1779 0.4165 0.025 Uiso 1 1 calc R U . . .
C22 C 0.86345(19) 0.30426(15) 0.50387(14) 0.0170(4) Uani 1 1 d . . . . .
C23 C 0.57731(18) 0.62040(15) 0.54420(14) 0.0161(4) Uani 1 1 d . . . . .
C24 C 0.47880(19) 0.73491(15) 0.56586(16) 0.0198(4) Uani 1 1 d . . . . .
H24A H 0.4533 0.7320 0.6466 0.024 Uiso 1 1 calc R U . . .
H24B H 0.3974 0.7556 0.5429 0.024 Uiso 1 1 calc R U . . .
C25 C 0.55302(19) 0.82231(16) 0.49348(16) 0.0228(4) Uani 1 1 d . . . . .
H25A H 0.5147 0.8753 0.4293 0.027 Uiso 1 1 calc R U . . .
H25B H 0.5484 0.8693 0.5387 0.027 Uiso 1 1 calc R U . . .
C26 C 0.69380(19) 0.74903(15) 0.45281(15) 0.0173(4) Uani 1 1 d . . . . .
C27 C 0.81816(18) 1.03207(15) 0.14501(15) 0.0172(4) Uani 1 1 d . . . . .
C28 C 0.82268(19) 1.15389(15) 0.09408(15) 0.0195(4) Uani 1 1 d . . . . .
H28A H 0.7431 1.2065 0.0658 0.023 Uiso 1 1 calc R U . . .
H28B H 0.9038 1.1565 0.0310 0.023 Uiso 1 1 calc R U . . .
C29 C 0.82481(19) 1.18832(15) 0.19132(15) 0.0198(4) Uani 1 1 d . . . . .
H29A H 0.9092 1.2024 0.1747 0.024 Uiso 1 1 calc R U . . .
H29B H 0.7491 1.2595 0.2048 0.024 Uiso 1 1 calc R U . . .
C30 C 0.81318(19) 1.08611(15) 0.29129(16) 0.0203(4) Uani 1 1 d . . . . .
N1 N 0.30139(17) 0.18216(13) 0.23312(14) 0.0209(4) Uani 1 1 d . . . . .
N2 N 0.73969(16) 0.29605(13) 0.57096(13) 0.0183(3) Uani 1 1 d . . . . .
N3 N 0.69916(16) 0.63557(13) 0.48167(12) 0.0164(3) Uani 1 1 d . . . . .
N4 N 0.80863(16) 1.00120(13) 0.25656(13) 0.0179(3) Uani 1 1 d . . . . .
O1 O 0.15968(14) 0.37873(10) 0.34019(11) 0.0184(3) Uani 1 1 d . . . . .
O2 O -0.00894(13) 0.59284(11) 0.36357(10) 0.0185(3) Uani 1 1 d . . . . .
O1W O 0.12603(15) 0.97680(12) 0.13490(12) 0.0266(3) Uani 1 1 d . . . . .
O3 O 0.06826(13) 0.78330(11) 0.26192(11) 0.0202(3) Uani 1 1 d . . . . .
O4 O 0.56240(13) 0.62214(10) 0.05023(11) 0.0207(3) Uani 1 1 d . . . . .
O5 O 0.58956(14) 0.43252(10) 0.09618(11) 0.0209(3) Uani 1 1 d . . . . .
O6 O -0.28851(14) 0.41958(11) 0.30286(11) 0.0217(3) Uani 1 1 d . . . . .
O7 O -0.42959(13) 0.64586(11) 0.29840(11) 0.0208(3) Uani 1 1 d . . . . .
O8 O -0.31257(14) 0.81351(11) 0.18711(11) 0.0233(3) Uani 1 1 d . . . . .
O9 O 0.16332(13) 0.60022(10) 0.00905(10) 0.0198(3) Uani 1 1 d . . . . .
O10 O 0.17881(14) 0.41248(10) 0.06806(11) 0.0192(3) Uani 1 1 d . . . . .
O11 O 0.50472(14) 0.17143(11) 0.23748(12) 0.0300(3) Uani 1 1 d . . . . .
O12 O 0.13413(14) 0.15177(11) 0.20553(11) 0.0244(3) Uani 1 1 d . . . . .
O13 O 0.64274(14) 0.15396(11) 0.68188(11) 0.0257(3) Uani 1 1 d . . . . .
O14 O 0.88814(13) 0.39511(11) 0.46139(11) 0.0217(3) Uani 1 1 d . . . . .
O15 O 0.55655(13) 0.52842(10) 0.57672(10) 0.0211(3) Uani 1 1 d . . . . .
O16 O 0.79039(13) 0.78287(11) 0.40084(11) 0.0226(3) Uani 1 1 d . . . . .
O17 O 0.82023(14) 0.96870(11) 0.09562(10) 0.0234(3) Uani 1 1 d . . . . .
O18 O 0.80841(15) 1.07423(11) 0.38774(11) 0.0303(3) Uani 1 1 d . . . . .
H1N H 0.256(2) 0.2248(18) 0.2770(18) 0.026(6) Uiso 1 1 d . . . . .
H1O H 0.073(3) 0.400(2) 0.374(2) 0.046(8) Uiso 1 1 d . . . . .
H1WA H 0.130(2) 1.035(2) 0.151(2) 0.043(7) Uiso 1 1 d . . . . .
H1WB H 0.147(3) 0.990(2) 0.063(2) 0.054(8) Uiso 1 1 d . . . . .
H2N H 0.668(2) 0.3617(18) 0.5824(17) 0.026(6) Uiso 1 1 d . . . . .
H2O H -0.056(3) 0.667(2) 0.367(2) 0.051(8) Uiso 1 1 d . . . . .
H3N H 0.770(2) 0.576(2) 0.4660(18) 0.032(6) Uiso 1 1 d . . . . .
H3O H 0.099(2) 0.846(2) 0.2154(19) 0.040(6) Uiso 1 1 d . . . . .
H4 H 0.801(2) 0.9388(19) 0.3015(19) 0.029(6) Uiso 1 1 d . . . . .
H5O H 0.680(3) 0.424(2) 0.057(2) 0.067(9) Uiso 1 1 d . . . . .
H6O H -0.376(3) 0.453(2) 0.339(2) 0.053(8) Uiso 1 1 d . . . . .
H7O H -0.476(3) 0.725(2) 0.285(2) 0.059(8) Uiso 1 1 d . . . . .
H8O H -0.260(3) 0.858(2) 0.161(2) 0.046(7) Uiso 1 1 d . . . . .
H10O H 0.270(3) 0.402(2) 0.026(2) 0.063(8) Uiso 1 1 d . . . . .


#===============================================================================

# 10. 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 C6 1.397(2) . ?
C1 C2 1.398(2) . ?
C1 C7 1.480(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 O1 1.377(2) . ?
C3 C4 1.389(2) . ?
C4 O2 1.353(2) . ?
C4 C5 1.403(2) . ?
C5 O3 1.370(2) . ?
C5 C6 1.381(3) . ?
C6 H6 0.9500 . ?
C7 O4 1.237(2) . ?
C7 O5 1.312(2) . ?
C8 C9 1.389(2) . ?
C8 C13 1.395(2) . ?
C8 C14 1.480(3) . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 O6 1.367(2) . ?
C10 C11 1.397(2) . ?
C11 O7 1.362(2) . ?
C11 C12 1.391(2) . ?
C12 O8 1.373(2) . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C14 O9 1.234(2) . ?
C14 O10 1.316(2) . ?
C15 O11 1.214(2) . ?
C15 N1 1.384(3) . ?
C15 C16 1.501(3) . ?
C16 C17 1.527(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.502(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O12 1.223(2) . ?
C18 N1 1.373(2) . ?
C19 O13 1.224(2) . ?
C19 N2 1.381(2) . ?
C19 C20 1.504(3) . ?
C20 C21 1.531(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.503(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O14 1.217(2) . ?
C22 N2 1.384(2) . ?
C23 O15 1.216(2) . ?
C23 N3 1.383(2) . ?
C23 C24 1.505(3) . ?
C24 C25 1.530(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.496(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 O16 1.228(2) . ?
C26 N3 1.373(2) . ?
C27 O17 1.233(2) . ?
C27 N4 1.354(2) . ?
C27 C28 1.499(2) . ?
C28 C29 1.537(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.499(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 O18 1.214(2) . ?
C30 N4 1.389(2) . ?
N1 H1N 0.83(2) . ?
N2 H2N 0.92(2) . ?
N3 H3N 0.87(2) . ?
N4 H4 0.83(2) . ?
O1 H1O 0.88(3) . ?
O2 H2O 0.90(3) . ?
O1W H1WA 0.89(2) . ?
O1W H1WB 0.86(3) . ?
O3 H3O 0.93(2) . ?
O5 H5O 0.94(3) . ?
O6 H6O 0.92(3) . ?
O7 H7O 0.93(3) . ?
O8 H8O 0.90(3) . ?
O10 H10O 0.96(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.67(17) . . ?
C6 C1 C7 119.34(15) . . ?
C2 C1 C7 119.97(16) . . ?
C3 C2 C1 119.59(16) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
O1 C3 C2 119.93(15) . . ?
O1 C3 C4 119.97(16) . . ?
C2 C3 C4 120.09(15) . . ?
O2 C4 C3 117.89(15) . . ?
O2 C4 C5 122.14(16) . . ?
C3 C4 C5 119.96(17) . . ?
O3 C5 C6 124.70(15) . . ?
O3 C5 C4 114.87(16) . . ?
C6 C5 C4 120.40(16) . . ?
C5 C6 C1 119.27(16) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O4 C7 O5 122.97(17) . . ?
O4 C7 C1 123.06(16) . . ?
O5 C7 C1 113.96(15) . . ?
C9 C8 C13 120.72(17) . . ?
C9 C8 C14 122.30(16) . . ?
C13 C8 C14 116.98(15) . . ?
C10 C9 C8 119.29(16) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O6 C10 C9 119.98(16) . . ?
O6 C10 C11 119.72(17) . . ?
C9 C10 C11 120.30(16) . . ?
O7 C11 C12 122.58(16) . . ?
O7 C11 C10 117.63(15) . . ?
C12 C11 C10 119.74(17) . . ?
O8 C12 C13 124.23(16) . . ?
O8 C12 C11 115.51(16) . . ?
C13 C12 C11 120.27(16) . . ?
C12 C13 C8 119.66(16) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
O9 C14 O10 122.65(17) . . ?
O9 C14 C8 120.81(16) . . ?
O10 C14 C8 116.54(15) . . ?
O11 C15 N1 124.60(18) . . ?
O11 C15 C16 127.49(19) . . ?
N1 C15 C16 107.91(15) . . ?
C15 C16 C17 105.15(17) . . ?
C15 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C18 C17 C16 104.92(15) . . ?
C18 C17 H17A 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.8 . . ?
O12 C18 N1 124.77(18) . . ?
O12 C18 C17 126.87(16) . . ?
N1 C18 C17 108.34(17) . . ?
O13 C19 N2 124.72(18) . . ?
O13 C19 C20 126.95(16) . . ?
N2 C19 C20 108.33(16) . . ?
C19 C20 C21 104.96(14) . . ?
C19 C20 H20A 110.8 . . ?
C21 C20 H20A 110.8 . . ?
C19 C20 H20B 110.8 . . ?
C21 C20 H20B 110.8 . . ?
H20A C20 H20B 108.8 . . ?
C22 C21 C20 104.63(15) . . ?
C22 C21 H21A 110.8 . . ?
C20 C21 H21A 110.8 . . ?
C22 C21 H21B 110.8 . . ?
C20 C21 H21B 110.8 . . ?
H21A C21 H21B 108.9 . . ?
O14 C22 N2 123.92(17) . . ?
O14 C22 C21 127.73(17) . . ?
N2 C22 C21 108.35(15) . . ?
O15 C23 N3 124.56(17) . . ?
O15 C23 C24 126.88(17) . . ?
N3 C23 C24 108.54(14) . . ?
C23 C24 C25 104.29(15) . . ?
C23 C24 H24A 110.9 . . ?
C25 C24 H24A 110.9 . . ?
C23 C24 H24B 110.9 . . ?
C25 C24 H24B 110.9 . . ?
H24A C24 H24B 108.9 . . ?
C26 C25 C24 104.62(14) . . ?
C26 C25 H25A 110.8 . . ?
C24 C25 H25A 110.8 . . ?
C26 C25 H25B 110.8 . . ?
C24 C25 H25B 110.8 . . ?
H25A C25 H25B 108.9 . . ?
O16 C26 N3 124.38(18) . . ?
O16 C26 C25 126.60(16) . . ?
N3 C26 C25 109.02(16) . . ?
O17 C27 N4 124.06(16) . . ?
O17 C27 C28 126.52(16) . . ?
N4 C27 C28 109.41(15) . . ?
C27 C28 C29 104.41(14) . . ?
C27 C28 H28A 110.9 . . ?
C29 C28 H28A 110.9 . . ?
C27 C28 H28B 110.9 . . ?
C29 C28 H28B 110.9 . . ?
H28A C28 H28B 108.9 . . ?
C30 C29 C28 104.56(13) . . ?
C30 C29 H29A 110.8 . . ?
C28 C29 H29A 110.8 . . ?
C30 C29 H29B 110.8 . . ?
C28 C29 H29B 110.8 . . ?
H29A C29 H29B 108.9 . . ?
O18 C30 N4 123.16(17) . . ?
O18 C30 C29 128.46(16) . . ?
N4 C30 C29 108.38(15) . . ?
C18 N1 C15 113.49(17) . . ?
C18 N1 H1N 125.3(15) . . ?
C15 N1 H1N 121.0(15) . . ?
C19 N2 C22 113.05(16) . . ?
C19 N2 H2N 126.2(13) . . ?
C22 N2 H2N 120.8(13) . . ?
C26 N3 C23 112.56(16) . . ?
C26 N3 H3N 126.8(15) . . ?
C23 N3 H3N 120.6(15) . . ?
C27 N4 C30 113.09(15) . . ?
C27 N4 H4 125.7(15) . . ?
C30 N4 H4 121.3(14) . . ?
C3 O1 H1O 110.9(16) . . ?
C4 O2 H2O 110.8(17) . . ?
H1WA O1W H1WB 109(2) . . ?
C5 O3 H3O 111.0(15) . . ?
C7 O5 H5O 112.3(17) . . ?
C10 O6 H6O 110.6(16) . . ?
C11 O7 H7O 114.2(17) . . ?
C12 O8 H8O 109.3(17) . . ?
C14 O10 H10O 110.7(16) . . ?

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
C6 C1 C2 C3 -0.5(2) . . . . ?
C7 C1 C2 C3 177.92(14) . . . . ?
C1 C2 C3 O1 -178.69(14) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
O1 C3 C4 O2 -0.3(2) . . . . ?
C2 C3 C4 O2 -179.43(14) . . . . ?
O1 C3 C4 C5 179.40(14) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
O2 C4 C5 O3 0.3(2) . . . . ?
C3 C4 C5 O3 -179.39(14) . . . . ?
O2 C4 C5 C6 178.70(14) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
O3 C5 C6 C1 179.20(15) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C7 C1 C6 C5 -178.63(14) . . . . ?
C6 C1 C7 O4 -1.7(2) . . . . ?
C2 C1 C7 O4 179.84(15) . . . . ?
C6 C1 C7 O5 178.74(14) . . . . ?
C2 C1 C7 O5 0.3(2) . . . . ?
C13 C8 C9 C10 1.2(2) . . . . ?
C14 C8 C9 C10 -179.37(14) . . . . ?
C8 C9 C10 O6 -179.80(14) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
O6 C10 C11 O7 0.4(2) . . . . ?
C9 C10 C11 O7 -179.17(14) . . . . ?
O6 C10 C11 C12 178.18(15) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
O7 C11 C12 O8 -0.1(2) . . . . ?
C10 C11 C12 O8 -177.77(14) . . . . ?
O7 C11 C12 C13 179.70(15) . . . . ?
C10 C11 C12 C13 2.0(2) . . . . ?
O8 C12 C13 C8 178.73(15) . . . . ?
C11 C12 C13 C8 -1.1(2) . . . . ?
C9 C8 C13 C12 -0.6(2) . . . . ?
C14 C8 C13 C12 179.98(14) . . . . ?
C9 C8 C14 O9 178.61(15) . . . . ?
C13 C8 C14 O9 -2.0(2) . . . . ?
C9 C8 C14 O10 -1.1(2) . . . . ?
C13 C8 C14 O10 178.35(14) . . . . ?
O11 C15 C16 C17 176.69(18) . . . . ?
N1 C15 C16 C17 -2.9(2) . . . . ?
C15 C16 C17 C18 0.5(2) . . . . ?
C16 C17 C18 O12 -176.48(17) . . . . ?
C16 C17 C18 N1 2.1(2) . . . . ?
O13 C19 C20 C21 175.91(17) . . . . ?
N2 C19 C20 C21 -4.04(18) . . . . ?
C19 C20 C21 C22 7.31(17) . . . . ?
C20 C21 C22 O14 171.88(16) . . . . ?
C20 C21 C22 N2 -8.30(18) . . . . ?
O15 C23 C24 C25 -173.00(16) . . . . ?
N3 C23 C24 C25 8.13(18) . . . . ?
C23 C24 C25 C26 -9.63(18) . . . . ?
C24 C25 C26 O16 -172.47(17) . . . . ?
C24 C25 C26 N3 8.25(19) . . . . ?
O17 C27 C28 C29 -177.14(18) . . . . ?
N4 C27 C28 C29 4.1(2) . . . . ?
C27 C28 C29 C30 -3.23(19) . . . . ?
C28 C29 C30 O18 -178.68(19) . . . . ?
C28 C29 C30 N4 1.5(2) . . . . ?
O12 C18 N1 C15 174.37(16) . . . . ?
C17 C18 N1 C15 -4.3(2) . . . . ?
O11 C15 N1 C18 -175.03(17) . . . . ?
C16 C15 N1 C18 4.6(2) . . . . ?
O13 C19 N2 C22 178.78(16) . . . . ?
C20 C19 N2 C22 -1.27(19) . . . . ?
O14 C22 N2 C19 -173.96(15) . . . . ?
C21 C22 N2 C19 6.22(19) . . . . ?
O16 C26 N3 C23 177.35(16) . . . . ?
C25 C26 N3 C23 -3.35(19) . . . . ?
O15 C23 N3 C26 177.87(15) . . . . ?
C24 C23 N3 C26 -3.23(19) . . . . ?
O17 C27 N4 C30 177.79(17) . . . . ?
C28 C27 N4 C30 -3.4(2) . . . . ?
O18 C30 N4 C27 -178.72(18) . . . . ?
C29 C30 N4 C27 1.1(2) . . . . ?
#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_red
_audit_block_doi                 10.5517/cc1jg58f
_database_code_depnum_ccdc_archive 'CCDC 1413794'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        '221 GASM Act solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H6 O5), 2(C4 H5 N O2), C3 H6 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C25 H28 N2 O15'
_chemical_formula_iupac          ?
_chemical_formula_weight         596.49
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.2761(4)
_cell_length_b                   11.6893(6)
_cell_length_c                   14.7645(7)
_cell_angle_alpha                108.269(4)
_cell_angle_beta                 97.664(4)
_cell_angle_gamma                101.744(4)
_cell_volume                     1297.75(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    110.00(10)
_cell_measurement_reflns_used    5455
_cell_measurement_theta_min      2.7820
_cell_measurement_theta_max      27.3690
_cell_special_details            
;
;

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.128
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.78348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            16178
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             5101
# number of observed reflections (> n sig(I))
_reflns_number_gt                4253
_reflns_threshold_expression     ?

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0520P)²+0.4312P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5101
_refine_ls_number_parameters     421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.051

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.91933(19) 0.37360(14) 0.31059(11) 0.0178(3) Uani 1 1 d . . . . .
C2 C 1.02760(18) 0.48261(14) 0.31209(11) 0.0178(3) Uani 1 1 d . . . . .
H2 H 1.1206 0.5274 0.3654 0.021 Uiso 1 1 calc R U . . .
C3 C 0.99912(18) 0.52568(13) 0.23529(11) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.86037(18) 0.46092(14) 0.15831(11) 0.0170(3) Uani 1 1 d . . . . .
C5 C 0.75250(18) 0.35179(14) 0.15739(11) 0.0179(3) Uani 1 1 d . . . . .
C6 C 0.78109(19) 0.30743(14) 0.23327(11) 0.0181(3) Uani 1 1 d . . . . .
H6 H 0.7077 0.2331 0.2326 0.022 Uiso 1 1 calc R U . . .
C7 C 0.95003(19) 0.32316(14) 0.39015(11) 0.0194(3) Uani 1 1 d . . . . .
C8 C -0.06674(19) -0.13778(14) 0.32854(11) 0.0179(3) Uani 1 1 d . . . . .
C9 C 0.03806(19) -0.02626(14) 0.33168(11) 0.0180(3) Uani 1 1 d . . . . .
H9 H 0.1282 0.0206 0.3862 0.022 Uiso 1 1 calc R U . . .
C10 C 0.00907(18) 0.01565(13) 0.25391(11) 0.0175(3) Uani 1 1 d . . . . .
C11 C -0.12354(19) -0.05446(14) 0.17429(11) 0.0171(3) Uani 1 1 d . . . . .
C12 C -0.22651(18) -0.16596(14) 0.17191(11) 0.0175(3) Uani 1 1 d . . . . .
C13 C -0.19988(19) -0.20796(14) 0.24876(11) 0.0181(3) Uani 1 1 d . . . . .
H13 H -0.2710 -0.2835 0.2475 0.022 Uiso 1 1 calc R U . . .
C14 C -0.03696(19) -0.18629(14) 0.40894(11) 0.0190(3) Uani 1 1 d . . . . .
C15 C -0.35056(18) -0.00375(13) -0.09897(11) 0.0167(3) Uani 1 1 d . . . . .
C16 C -0.44578(19) 0.00498(14) -0.18915(11) 0.0205(3) Uani 1 1 d . . . . .
H16A H -0.5621 0.0094 -0.1828 0.025 Uiso 1 1 calc R U . . .
H16B H -0.4515 -0.0682 -0.2471 0.025 Uiso 1 1 calc R U . . .
C17 C -0.34569(19) 0.12487(14) -0.19762(11) 0.0196(3) Uani 1 1 d . . . . .
H17A H -0.3051 0.1069 -0.2594 0.024 Uiso 1 1 calc R U . . .
H17B H -0.4161 0.1844 -0.1953 0.024 Uiso 1 1 calc R U . . .
C18 C -0.19963(19) 0.17681(14) -0.11123(11) 0.0178(3) Uani 1 1 d . . . . .
C19 C 0.35377(18) 0.49343(13) 0.12102(11) 0.0171(3) Uani 1 1 d . . . . .
C20 C 0.43325(19) 0.49072(14) 0.21791(11) 0.0189(3) Uani 1 1 d . . . . .
H20A H 0.4194 0.5608 0.2723 0.023 Uiso 1 1 calc R U . . .
H20B H 0.5552 0.4961 0.2225 0.023 Uiso 1 1 calc R U . . .
C21 C 0.33857(19) 0.36542(14) 0.22058(11) 0.0192(3) Uani 1 1 d . . . . .
H21A H 0.4134 0.3087 0.2172 0.023 Uiso 1 1 calc R U . . .
H21B H 0.2942 0.3770 0.2810 0.023 Uiso 1 1 calc R U . . .
C22 C 0.19644(18) 0.31422(14) 0.13189(11) 0.0164(3) Uani 1 1 d . . . . .
C23 C 0.5087(3) 0.32920(19) 0.48125(15) 0.0416(5) Uani 1 1 d . . . . .
H23A H 0.6284 0.3705 0.4904 0.062 Uiso 1 1 calc R U . . .
H23B H 0.4619 0.3771 0.5338 0.062 Uiso 1 1 calc R U . . .
H23C H 0.4472 0.3246 0.4182 0.062 Uiso 1 1 calc R U . . .
C24 C 0.4915(2) 0.20000(18) 0.48343(13) 0.0307(4) Uani 1 1 d . . . . .
C25 C 0.5221(2) 0.18603(17) 0.58067(13) 0.0333(4) Uani 1 1 d . . . . .
H25A H 0.4368 0.2130 0.6163 0.050 Uiso 1 1 calc R U . . .
H25B H 0.6347 0.2376 0.6179 0.050 Uiso 1 1 calc R U . . .
H25C H 0.5151 0.0984 0.5718 0.050 Uiso 1 1 calc R U . . .
N1 N -0.21146(16) 0.09627(11) -0.05939(10) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.21537(16) 0.39279(11) 0.07910(9) 0.0172(3) Uani 1 1 d . . . . .
O1 O 0.84912(14) 0.23246(11) 0.39389(8) 0.0263(3) Uani 1 1 d . . . . .
O2 O 1.09245(14) 0.38230(11) 0.45471(8) 0.0246(3) Uani 1 1 d . . . . .
O3 O 1.10999(14) 0.62984(10) 0.23604(8) 0.0205(2) Uani 1 1 d . . . . .
O4 O 0.83581(15) 0.50722(10) 0.08513(8) 0.0219(3) Uani 1 1 d . . . . .
O5 O 0.62091(14) 0.29732(11) 0.07810(8) 0.0226(3) Uani 1 1 d . . . . .
O6 O -0.13897(14) -0.27699(10) 0.41340(8) 0.0249(3) Uani 1 1 d . . . . .
O7 O 0.10397(14) -0.12632(11) 0.47397(8) 0.0252(3) Uani 1 1 d . . . . .
O8 O 0.11204(14) 0.12357(10) 0.25584(8) 0.0223(3) Uani 1 1 d . . . . .
O9 O -0.14593(15) -0.01008(11) 0.09950(8) 0.0228(3) Uani 1 1 d . . . . .
O10 O -0.34948(14) -0.22701(11) 0.08849(8) 0.0221(3) Uani 1 1 d . . . . .
O11 O -0.38756(13) -0.08586(10) -0.06424(8) 0.0213(3) Uani 1 1 d . . . . .
O12 O -0.08696(13) 0.27247(10) -0.08775(8) 0.0216(3) Uani 1 1 d . . . . .
O13 O 0.08297(13) 0.21887(10) 0.10748(8) 0.0219(3) Uani 1 1 d . . . . .
O14 O 0.40024(14) 0.57158(10) 0.08428(8) 0.0222(3) Uani 1 1 d . . . . .
O38 O 0.45271(17) 0.11013(13) 0.40819(9) 0.0439(4) Uani 1 1 d . . . . .
H1N H -0.136(2) 0.1117(17) -0.0038(15) 0.031(5) Uiso 1 1 d . . . . .
H2N H 0.148(2) 0.3787(18) 0.0242(15) 0.032(5) Uiso 1 1 d . . . . .
H2O H 1.103(3) 0.340(2) 0.5033(19) 0.071(8) Uiso 1 1 d . . . . .
H3O H 1.081(3) 0.650(2) 0.1877(18) 0.057(7) Uiso 1 1 d . . . . .
H4O H 0.758(3) 0.462(2) 0.0417(18) 0.056(7) Uiso 1 1 d . . . . .
H7O H 0.111(3) -0.166(2) 0.522(2) 0.073(8) Uiso 1 1 d . . . . .
H8O H 0.083(3) 0.140(2) 0.2038(18) 0.057(7) Uiso 1 1 d . . . . .
H9O H -0.228(3) -0.058(2) 0.0566(17) 0.048(7) Uiso 1 1 d . . . . .
H10O H -0.410(3) -0.2902(19) 0.0934(14) 0.035(6) Uiso 1 1 d . . . . .
H12 H 0.563(3) 0.228(2) 0.0799(16) 0.049(7) Uiso 1 1 d . . . . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

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 1.393(2) . ?
C1 C6 1.396(2) . ?
C1 C7 1.486(2) . ?
C2 C3 1.389(2) . ?
C3 O3 1.3634(18) . ?
C3 C4 1.394(2) . ?
C4 O4 1.3618(18) . ?
C4 C5 1.395(2) . ?
C5 O5 1.3682(18) . ?
C5 C6 1.387(2) . ?
C7 O1 1.2301(18) . ?
C7 O2 1.3158(18) . ?
C8 C9 1.395(2) . ?
C8 C13 1.398(2) . ?
C8 C14 1.481(2) . ?
C9 C10 1.394(2) . ?
C10 O8 1.3608(18) . ?
C10 C11 1.394(2) . ?
C11 O9 1.3663(18) . ?
C11 C12 1.392(2) . ?
C12 O10 1.3714(18) . ?
C12 C13 1.380(2) . ?
C14 O6 1.2391(18) . ?
C14 O7 1.3116(19) . ?
C15 O11 1.2283(18) . ?
C15 N1 1.3704(19) . ?
C15 C16 1.498(2) . ?
C16 C17 1.527(2) . ?
C17 C18 1.504(2) . ?
C18 O12 1.2192(18) . ?
C18 N1 1.384(2) . ?
C19 O14 1.2248(18) . ?
C19 N2 1.3729(19) . ?
C19 C20 1.505(2) . ?
C20 C21 1.529(2) . ?
C21 C22 1.506(2) . ?
C22 O13 1.2190(18) . ?
C22 N2 1.3777(19) . ?
C23 C24 1.499(3) . ?
C24 O38 1.215(2) . ?
C24 C25 1.490(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.86(14) . . ?
C2 C1 C7 120.89(14) . . ?
C6 C1 C7 118.24(14) . . ?
C3 C2 C1 119.75(14) . . ?
O3 C3 C2 119.02(13) . . ?
O3 C3 C4 121.22(13) . . ?
C2 C3 C4 119.75(13) . . ?
O4 C4 C3 117.87(13) . . ?
O4 C4 C5 122.02(13) . . ?
C3 C4 C5 120.11(13) . . ?
O5 C5 C6 125.07(14) . . ?
O5 C5 C4 114.44(13) . . ?
C6 C5 C4 120.49(14) . . ?
C5 C6 C1 119.02(14) . . ?
O1 C7 O2 123.37(14) . . ?
O1 C7 C1 121.76(14) . . ?
O2 C7 C1 114.87(13) . . ?
C9 C8 C13 121.07(14) . . ?
C9 C8 C14 120.61(14) . . ?
C13 C8 C14 118.31(14) . . ?
C10 C9 C8 119.28(14) . . ?
O8 C10 C9 119.66(13) . . ?
O8 C10 C11 120.70(13) . . ?
C9 C10 C11 119.63(14) . . ?
O9 C11 C12 122.09(13) . . ?
O9 C11 C10 117.45(13) . . ?
C12 C11 C10 120.45(14) . . ?
O10 C12 C13 125.04(14) . . ?
O10 C12 C11 114.49(13) . . ?
C13 C12 C11 120.46(14) . . ?
C12 C13 C8 119.10(14) . . ?
O6 C14 O7 123.21(14) . . ?
O6 C14 C8 121.72(14) . . ?
O7 C14 C8 115.07(13) . . ?
O11 C15 N1 124.13(14) . . ?
O11 C15 C16 126.90(13) . . ?
N1 C15 C16 108.97(13) . . ?
C15 C16 C17 104.88(12) . . ?
C18 C17 C16 104.85(12) . . ?
O12 C18 N1 123.62(14) . . ?
O12 C18 C17 128.07(14) . . ?
N1 C18 C17 108.31(12) . . ?
O14 C19 N2 124.33(14) . . ?
O14 C19 C20 127.12(13) . . ?
N2 C19 C20 108.54(13) . . ?
C19 C20 C21 104.64(12) . . ?
C22 C21 C20 104.49(12) . . ?
O13 C22 N2 123.94(14) . . ?
O13 C22 C21 127.46(14) . . ?
N2 C22 C21 108.59(12) . . ?
O38 C24 C25 121.51(18) . . ?
O38 C24 C23 120.79(18) . . ?
C25 C24 C23 117.69(17) . . ?
C15 N1 C18 112.97(13) . . ?
C19 N2 C22 113.07(13) . . ?
#===END
# start Validation Reply Form
_vrf_PLAT112_red                 
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem.      b/2         92 %Fit  
RESPONSE: We have attempted to solve the structure by forcefully invoking
 pseudo-symmetry element b/2. The ellipsoids of all the atoms became very 
bad and solvent had been completely disordered. Therefore, structure was
 solved without any disorder upon not considering b/2.
;
# end Validation Reply Form_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_smv
_audit_block_doi                 10.5517/cc1jg59g
_database_code_depnum_ccdc_archive 'CCDC 1413795'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        '331 GASM EtOAc solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C7 H6 O5), C4 H6 O2, 3(C4 H5 N O2)'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C37 H39 N3 O23'
_chemical_formula_iupac          ?
_chemical_formula_weight         893.71
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   9.1318(4)
_cell_length_b                   14.0453(6)
_cell_length_c                   15.5062(7)
_cell_angle_alpha                79.362(4)
_cell_angle_beta                 85.337(3)
_cell_angle_gamma                79.211(3)
_cell_volume                     1917.82(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4563
_cell_measurement_theta_min      2.6640
_cell_measurement_theta_max      27.3640
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             932
_exptl_absorpt_coefficient_mu    0.131
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.84129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            27372
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.493
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             8795
# number of observed reflections (> n sig(I))
_reflns_number_gt                5136

_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0840P)²+0.5506P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8795
_refine_ls_number_parameters     629
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1873
_refine_ls_wR_factor_gt          0.1542
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.065

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.4345(2) 0.18347(16) 0.50207(14) 0.0179(5) Uani 1 1 d . . . . .
C2 C 0.5791(2) 0.17987(16) 0.46492(14) 0.0178(5) Uani 1 1 d . . . . .
H2 H 0.6551 0.1253 0.4835 0.021 Uiso 1 1 calc R U . . .
C3 C 0.6109(2) 0.25702(16) 0.40043(14) 0.0162(5) Uani 1 1 d . . . . .
C4 C 0.4982(2) 0.33619(15) 0.37230(14) 0.0158(5) Uani 1 1 d . . . . .
C5 C 0.3545(2) 0.33866(15) 0.41061(14) 0.0164(5) Uani 1 1 d . . . . .
C6 C 0.3214(2) 0.26289(16) 0.47515(14) 0.0174(5) Uani 1 1 d . . . . .
H6 H 0.2232 0.2647 0.5009 0.021 Uiso 1 1 calc R U . . .
C7 C 0.3944(2) 0.10358(16) 0.57175(14) 0.0182(5) Uani 1 1 d . . . . .
C8 C 0.7579(2) 0.17531(16) 0.17275(14) 0.0169(5) Uani 1 1 d . . . . .
C9 C 0.9039(2) 0.17030(15) 0.13724(14) 0.0172(5) Uani 1 1 d . . . . .
H9 H 0.9785 0.1154 0.1570 0.021 Uiso 1 1 calc R U . . .
C10 C 0.9394(2) 0.24627(15) 0.07274(14) 0.0156(4) Uani 1 1 d . . . . .
C11 C 0.8285(2) 0.32664(15) 0.04361(14) 0.0163(5) Uani 1 1 d . . . . .
C12 C 0.6837(2) 0.33025(16) 0.07998(15) 0.0180(5) Uani 1 1 d . . . . .
C13 C 0.6467(2) 0.25553(16) 0.14391(14) 0.0183(5) Uani 1 1 d . . . . .
H13 H 0.5473 0.2583 0.1681 0.022 Uiso 1 1 calc R U . . .
C14 C 0.7167(2) 0.09665(16) 0.24349(14) 0.0187(5) Uani 1 1 d . . . . .
C15 C 0.9015(2) -0.17774(16) 0.16298(14) 0.0167(5) Uani 1 1 d . . . . .
C16 C 0.7559(2) -0.17333(16) 0.19956(14) 0.0176(5) Uani 1 1 d . . . . .
H16 H 0.6812 -0.1178 0.1817 0.021 Uiso 1 1 calc R U . . .
C17 C 0.7219(2) -0.25146(16) 0.26262(14) 0.0165(5) Uani 1 1 d . . . . .
C18 C 0.8326(2) -0.33230(15) 0.28915(14) 0.0167(5) Uani 1 1 d . . . . .
C19 C 0.9774(2) -0.33524(15) 0.25194(14) 0.0171(5) Uani 1 1 d . . . . .
C20 C 1.0124(2) -0.25820(16) 0.18934(14) 0.0172(5) Uani 1 1 d . . . . .
H20 H 1.1112 -0.2601 0.1645 0.021 Uiso 1 1 calc R U . . .
C21 C 0.9430(2) -0.09812(16) 0.09378(14) 0.0183(5) Uani 1 1 d . . . . .
C22 C 0.6895(2) 0.63247(16) 0.10060(14) 0.0173(5) Uani 1 1 d . . . . .
C23 C 0.5837(2) 0.72264(16) 0.05998(15) 0.0195(5) Uani 1 1 d . . . . .
H23B H 0.5712 0.7214 -0.0026 0.023 Uiso 1 1 calc R U . . .
H23A H 0.6207 0.7834 0.0642 0.023 Uiso 1 1 calc R U . . .
C24 C 0.4363(2) 0.71701(16) 0.11388(14) 0.0200(5) Uani 1 1 d . . . . .
H24A H 0.4113 0.7712 0.1482 0.024 Uiso 1 1 calc R U . . .
H24B H 0.3536 0.7209 0.0752 0.024 Uiso 1 1 calc R U . . .
C25 C 0.4635(2) 0.61887(16) 0.17369(14) 0.0168(5) Uani 1 1 d . . . . .
C26 C 1.1983(2) 0.39204(16) 0.14927(14) 0.0169(5) Uani 1 1 d . . . . .
C27 C 1.2239(2) 0.29795(16) 0.21384(14) 0.0189(5) Uani 1 1 d . . . . .
H04A H 1.3029 0.2982 0.2538 0.023 Uiso 1 1 calc R U . . .
H04B H 1.2534 0.2409 0.1832 0.023 Uiso 1 1 calc R U . . .
C28 C 1.0736(2) 0.29391(16) 0.26478(14) 0.0176(5) Uani 1 1 d . . . . .
H05A H 1.0379 0.2324 0.2614 0.021 Uiso 1 1 calc R U . . .
H05B H 1.0819 0.2976 0.3273 0.021 Uiso 1 1 calc R U . . .
C29 C 0.9696(2) 0.38256(16) 0.22022(14) 0.0180(5) Uani 1 1 d . . . . .
C30 C 0.8662(2) 0.38870(16) 0.48619(14) 0.0163(5) Uani 1 1 d . . . . .
C31 C 0.8950(2) 0.29498(16) 0.55174(14) 0.0190(5) Uani 1 1 d . . . . .
H31A H 0.9761 0.2961 0.5900 0.023 Uiso 1 1 calc R U . . .
H31B H 0.9229 0.2374 0.5217 0.023 Uiso 1 1 calc R U . . .
C35 C 1.3388(3) 0.0214(2) 0.1423(2) 0.0465(8) Uani 1 1 d . . . . .
H35C H 1.3790 -0.0260 0.1035 0.070 Uiso 1 1 calc R U . . .
H35B H 1.4199 0.0504 0.1585 0.070 Uiso 1 1 calc R U . . .
H35A H 1.2642 0.0734 0.1117 0.070 Uiso 1 1 calc R U . . .
C33 C 0.7475(2) 0.29131(16) 0.60506(14) 0.0189(5) Uani 1 1 d . . . . .
H33B H 0.7115 0.2295 0.6033 0.023 Uiso 1 1 calc R U . . .
H33A H 0.7591 0.2957 0.6671 0.023 Uiso 1 1 calc R U . . .
C34 C 0.6413(2) 0.37877(15) 0.56196(14) 0.0158(5) Uani 1 1 d . . . . .
C36 C 1.2665(3) -0.0308(2) 0.22438(19) 0.0395(7) Uani 1 1 d . . . . .
C37 C 1.1511(3) 0.00596(18) 0.35936(19) 0.0336(6) Uani 1 1 d . . . . .
C38 C 1.1053(3) 0.0823(2) 0.41573(18) 0.0414(7) Uani 1 1 d . . . . .
H38C H 1.1799 0.1253 0.4087 0.062 Uiso 1 1 calc R U . . .
H38A H 1.0974 0.0504 0.4773 0.062 Uiso 1 1 calc R U . . .
H38B H 1.0083 0.1214 0.3984 0.062 Uiso 1 1 calc R U . . .
N1 N 1.0501(2) 0.43382(14) 0.15465(13) 0.0177(4) Uani 1 1 d . . . . .
N2 N 0.7187(2) 0.42994(14) 0.49427(12) 0.0172(4) Uani 1 1 d . . . . .
N3 N 0.6110(2) 0.57753(14) 0.16453(13) 0.0183(4) Uani 1 1 d . . . . .
O1 O 0.26526(17) 0.10272(12) 0.60030(10) 0.0242(4) Uani 1 1 d . . . . .
O2 O 0.50792(18) 0.03412(12) 0.59976(11) 0.0243(4) Uani 1 1 d . . . . .
O3 O 0.75339(17) 0.25522(12) 0.36486(11) 0.0206(4) Uani 1 1 d . . . . .
O4 O 0.53428(18) 0.40926(12) 0.30817(11) 0.0224(4) Uani 1 1 d . . . . .
O5 O 0.25407(18) 0.42052(11) 0.37849(11) 0.0216(4) Uani 1 1 d . . . . .
O6 O 1.08297(17) 0.24216(12) 0.03918(11) 0.0212(4) Uani 1 1 d . . . . .
O7 O 0.86820(18) 0.39995(12) -0.01904(11) 0.0232(4) Uani 1 1 d . . . . .
O8 O 0.58660(18) 0.41329(12) 0.04623(11) 0.0243(4) Uani 1 1 d . . . . .
O9 O 0.58657(17) 0.09566(12) 0.27028(10) 0.0238(4) Uani 1 1 d . . . . .
O10 O 0.83003(18) 0.02940(12) 0.27411(11) 0.0245(4) Uani 1 1 d . . . . .
O11 O 1.07321(17) -0.09716(12) 0.06637(10) 0.0233(4) Uani 1 1 d . . . . .
O12 O 0.82997(18) -0.02987(12) 0.06372(11) 0.0231(4) Uani 1 1 d D . . . .
O13 O 0.57918(17) -0.24828(12) 0.29698(11) 0.0212(4) Uani 1 1 d . . . . .
O14 O 0.79392(18) -0.40608(12) 0.35109(11) 0.0229(4) Uani 1 1 d . . . . .
O15 O 1.07576(18) -0.41873(11) 0.28267(11) 0.0225(4) Uani 1 1 d . . . . .
O16 O 0.37207(17) 0.58083(11) 0.22389(10) 0.0224(4) Uani 1 1 d . . . . .
O17 O 0.82174(17) 0.60873(12) 0.08127(10) 0.0234(4) Uani 1 1 d . . . . .
O18 O 0.83734(17) 0.40725(12) 0.23781(10) 0.0226(4) Uani 1 1 d . . . . .
O19 O 1.29089(16) 0.42819(11) 0.09850(10) 0.0225(4) Uani 1 1 d . . . . .
O20 O 0.95665(16) 0.42448(11) 0.43327(10) 0.0210(4) Uani 1 1 d . . . . .
O21 O 0.50963(17) 0.40267(11) 0.58134(10) 0.0222(4) Uani 1 1 d . . . . .
O25 O 1.21300(19) 0.04148(12) 0.28045(12) 0.0343(5) Uani 1 1 d . . . . .
O26 O 1.1325(2) -0.07706(15) 0.38051(14) 0.0396(5) Uiso 0.9 1 d . . P . .
O26A O 1.299(2) -0.1034(16) 0.2370(14) 0.046(5) Uiso 0.1 1 d . . P . .
H1N H 1.008(3) 0.485(2) 0.1252(18) 0.032(8) Uiso 1 1 d . . . . .
H2N H 0.673(4) 0.480(2) 0.461(2) 0.054(10) Uiso 1 1 d . . . . .
H2O H 0.471(4) -0.013(3) 0.640(2) 0.078(13) Uiso 1 1 d . . . . .
H3N H 0.655(3) 0.523(2) 0.196(2) 0.050(9) Uiso 1 1 d . . . . .
H3O H 0.760(4) 0.303(3) 0.326(2) 0.072(12) Uiso 1 1 d . . . . .
H4O H 0.455(4) 0.452(3) 0.300(2) 0.060(11) Uiso 1 1 d . . . . .
H5O H 0.169(3) 0.418(2) 0.4022(19) 0.042(9) Uiso 1 1 d . . . . .
H6O H 1.090(3) 0.290(2) 0.003(2) 0.048(10) Uiso 1 1 d . . . . .
H7O H 0.791(4) 0.442(3) -0.026(2) 0.064(11) Uiso 1 1 d . . . . .
H8O H 0.500(3) 0.4125(19) 0.0698(17) 0.030(8) Uiso 1 1 d . . . . .
H10O H 0.796(5) -0.009(3) 0.314(3) 0.094(15) Uiso 1 1 d . . . . .
H12O H 0.864(4) 0.010(2) 0.0211(18) 0.076(13) Uiso 1 1 d D . . . .
H13O H 0.570(4) -0.295(3) 0.331(2) 0.073(13) Uiso 1 1 d . . . . .
H14O H 0.870(4) -0.452(3) 0.356(2) 0.068(12) Uiso 1 1 d . . . . .
H15O H 1.164(3) -0.416(2) 0.2597(19) 0.039(8) Uiso 1 1 d . . . . .


#===============================================================================

# 10. 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 1.393(3) . ?
C1 C6 1.397(3) . ?
C1 C7 1.484(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 O3 1.369(2) . ?
C3 C4 1.397(3) . ?
C4 O4 1.359(2) . ?
C4 C5 1.393(3) . ?
C5 O5 1.371(2) . ?
C5 C6 1.379(3) . ?
C6 H6 0.9500 . ?
C7 O1 1.227(3) . ?
C7 O2 1.324(3) . ?
C8 C9 1.395(3) . ?
C8 C13 1.400(3) . ?
C8 C14 1.485(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 O6 1.366(2) . ?
C10 C11 1.400(3) . ?
C11 O7 1.359(3) . ?
C11 C12 1.391(3) . ?
C12 O8 1.372(2) . ?
C12 C13 1.376(3) . ?
C13 H13 0.9500 . ?
C14 O9 1.228(3) . ?
C14 O10 1.318(3) . ?
C15 C20 1.392(3) . ?
C15 C16 1.398(3) . ?
C15 C21 1.482(3) . ?
C16 C17 1.393(3) . ?
C16 H16 0.9500 . ?
C17 O13 1.363(2) . ?
C17 C18 1.395(3) . ?
C18 O14 1.355(3) . ?
C18 C19 1.395(3) . ?
C19 O15 1.370(2) . ?
C19 C20 1.381(3) . ?
C20 H20 0.9500 . ?
C21 O11 1.231(3) . ?
C21 O12 1.321(3) . ?
C22 O17 1.219(2) . ?
C22 N3 1.379(3) . ?
C22 C23 1.510(3) . ?
C23 C24 1.533(3) . ?
C23 H23B 0.9900 . ?
C23 H23A 0.9900 . ?
C24 C25 1.503(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O16 1.223(3) . ?
C25 N3 1.370(3) . ?
C26 O19 1.223(3) . ?
C26 N1 1.373(3) . ?
C26 C27 1.496(3) . ?
C27 C28 1.532(3) . ?
C27 H04A 0.9900 . ?
C27 H04B 0.9900 . ?
C28 C29 1.509(3) . ?
C28 H05A 0.9900 . ?
C28 H05B 0.9900 . ?
C29 O18 1.216(3) . ?
C29 N1 1.378(3) . ?
C30 O20 1.225(3) . ?
C30 N2 1.368(3) . ?
C30 C31 1.502(3) . ?
C31 C33 1.526(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C35 C36 1.514(4) . ?
C35 H35C 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35A 0.9800 . ?
C33 C34 1.501(3) . ?
C33 H33B 0.9900 . ?
C33 H33A 0.9900 . ?
C34 O21 1.215(2) . ?
C34 N2 1.382(3) . ?
C36 O26A 0.99(2) . ?
C36 O25 1.448(3) . ?
C37 O26 1.192(3) . ?
C37 O25 1.354(3) . ?
C37 C38 1.485(4) . ?
C38 H38C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
N1 H1N 0.82(3) . ?
N2 H2N 0.85(3) . ?
N3 H3N 0.87(3) . ?
O2 H2O 0.92(4) . ?
O3 H3O 0.82(4) . ?
O4 H4O 0.85(3) . ?
O5 H5O 0.84(3) . ?
O6 H6O 0.80(3) . ?
O7 H7O 0.83(4) . ?
O8 H8O 0.85(3) . ?
O10 H10O 0.83(4) . ?
O12 H12O 0.863(18) . ?
O13 H13O 0.78(4) . ?
O14 H14O 0.85(4) . ?
O15 H15O 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.1(2) . . ?
C2 C1 C7 121.5(2) . . ?
C6 C1 C7 117.4(2) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
O3 C3 C2 119.64(19) . . ?
O3 C3 C4 120.22(19) . . ?
C2 C3 C4 120.14(19) . . ?
O4 C4 C5 122.22(19) . . ?
O4 C4 C3 117.98(19) . . ?
C5 C4 C3 119.8(2) . . ?
O5 C5 C6 124.84(19) . . ?
O5 C5 C4 114.46(19) . . ?
C6 C5 C4 120.70(19) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
O1 C7 O2 123.2(2) . . ?
O1 C7 C1 121.9(2) . . ?
O2 C7 C1 114.90(19) . . ?
C9 C8 C13 120.9(2) . . ?
C9 C8 C14 120.93(19) . . ?
C13 C8 C14 118.12(19) . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
O6 C10 C9 119.35(19) . . ?
O6 C10 C11 120.76(19) . . ?
C9 C10 C11 119.88(19) . . ?
O7 C11 C12 122.18(19) . . ?
O7 C11 C10 118.02(19) . . ?
C12 C11 C10 119.8(2) . . ?
O8 C12 C13 125.1(2) . . ?
O8 C12 C11 113.85(19) . . ?
C13 C12 C11 121.1(2) . . ?
C12 C13 C8 118.9(2) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
O9 C14 O10 123.6(2) . . ?
O9 C14 C8 121.7(2) . . ?
O10 C14 C8 114.66(19) . . ?
C20 C15 C16 121.0(2) . . ?
C20 C15 C21 117.6(2) . . ?
C16 C15 C21 121.4(2) . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
O13 C17 C16 119.18(19) . . ?
O13 C17 C18 120.75(19) . . ?
C16 C17 C18 120.07(19) . . ?
O14 C18 C19 122.28(19) . . ?
O14 C18 C17 117.75(19) . . ?
C19 C18 C17 119.97(19) . . ?
O15 C19 C20 125.02(19) . . ?
O15 C19 C18 114.54(19) . . ?
C20 C19 C18 120.44(19) . . ?
C19 C20 C15 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
O11 C21 O12 123.2(2) . . ?
O11 C21 C15 121.9(2) . . ?
O12 C21 C15 114.86(19) . . ?
O17 C22 N3 123.9(2) . . ?
O17 C22 C23 127.6(2) . . ?
N3 C22 C23 108.44(18) . . ?
C22 C23 C24 104.45(17) . . ?
C22 C23 H23B 110.9 . . ?
C24 C23 H23B 110.9 . . ?
C22 C23 H23A 110.9 . . ?
C24 C23 H23A 110.9 . . ?
H23B C23 H23A 108.9 . . ?
C25 C24 C23 104.63(17) . . ?
C25 C24 H24A 110.8 . . ?
C23 C24 H24A 110.8 . . ?
C25 C24 H24B 110.8 . . ?
C23 C24 H24B 110.8 . . ?
H24A C24 H24B 108.9 . . ?
O16 C25 N3 124.3(2) . . ?
O16 C25 C24 126.91(19) . . ?
N3 C25 C24 108.82(18) . . ?
O19 C26 N1 123.7(2) . . ?
O19 C26 C27 127.33(19) . . ?
N1 C26 C27 108.96(18) . . ?
C26 C27 C28 104.75(17) . . ?
C26 C27 H04A 110.8 . . ?
C28 C27 H04A 110.8 . . ?
C26 C27 H04B 110.8 . . ?
C28 C27 H04B 110.8 . . ?
H04A C27 H04B 108.9 . . ?
C29 C28 C27 104.59(17) . . ?
C29 C28 H05A 110.8 . . ?
C27 C28 H05A 110.8 . . ?
C29 C28 H05B 110.8 . . ?
C27 C28 H05B 110.8 . . ?
H05A C28 H05B 108.9 . . ?
O18 C29 N1 124.3(2) . . ?
O18 C29 C28 127.4(2) . . ?
N1 C29 C28 108.37(18) . . ?
O20 C30 N2 124.1(2) . . ?
O20 C30 C31 127.21(19) . . ?
N2 C30 C31 108.72(18) . . ?
C30 C31 C33 104.65(17) . . ?
C30 C31 H31A 110.8 . . ?
C33 C31 H31A 110.8 . . ?
C30 C31 H31B 110.8 . . ?
C33 C31 H31B 110.8 . . ?
H31A C31 H31B 108.9 . . ?
C36 C35 H35C 109.5 . . ?
C36 C35 H35B 109.5 . . ?
H35C C35 H35B 109.5 . . ?
C36 C35 H35A 109.5 . . ?
H35C C35 H35A 109.5 . . ?
H35B C35 H35A 109.5 . . ?
C34 C33 C31 104.98(17) . . ?
C34 C33 H33B 110.8 . . ?
C31 C33 H33B 110.8 . . ?
C34 C33 H33A 110.8 . . ?
C31 C33 H33A 110.8 . . ?
H33B C33 H33A 108.8 . . ?
O21 C34 N2 124.35(19) . . ?
O21 C34 C33 127.46(19) . . ?
N2 C34 C33 108.19(18) . . ?
O26A C36 O25 132.6(13) . . ?
O26A C36 C35 115.0(13) . . ?
O25 C36 C35 107.3(2) . . ?
O26 C37 O25 123.6(3) . . ?
O26 C37 C38 123.7(3) . . ?
O25 C37 C38 112.7(2) . . ?
C37 C38 H38C 109.5 . . ?
C37 C38 H38A 109.5 . . ?
H38C C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38C C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C26 N1 C29 113.07(19) . . ?
C26 N1 H1N 127.5(19) . . ?
C29 N1 H1N 119.4(19) . . ?
C30 N2 C34 113.23(19) . . ?
C30 N2 H2N 127(2) . . ?
C34 N2 H2N 120(2) . . ?
C25 N3 C22 113.20(19) . . ?
C25 N3 H3N 125(2) . . ?
C22 N3 H3N 121(2) . . ?
C7 O2 H2O 108(2) . . ?
C3 O3 H3O 112(3) . . ?
C4 O4 H4O 106(2) . . ?
C5 O5 H5O 111(2) . . ?
C10 O6 H6O 110(2) . . ?
C11 O7 H7O 104(2) . . ?
C12 O8 H8O 110.9(18) . . ?
C14 O10 H10O 107(3) . . ?
C21 O12 H12O 108(2) . . ?
C17 O13 H13O 112(3) . . ?
C18 O14 H14O 106(2) . . ?
C19 O15 H15O 111.2(19) . . ?
C37 O25 C36 115.1(2) . . ?



# start Validation Reply Form
_vrf_PLAT222_smv                 
;
PROBLEM:Isotropic non-H Atoms in Main Residue(s) .......          1 Report
RESPONSE: There is a positional disorder present in the ethylacetate solvent molecule with respect to carbonyl oxygen and disorder has been treated by occupancy of 90% and 10 % in both carbonyl oxygens and both oxygens have kept isotropic.
;

# end Validation Reply Form

#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_ra68_ag_2
_audit_block_doi                 10.5517/cc1jg5bh
_database_code_depnum_ccdc_archive 'CCDC 1413796'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        '221 GASM THF solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H6 O5), 2(C4 H5 N O2), C4 H8 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C26 H30 N2 O15'
_chemical_formula_iupac          ?
_chemical_formula_weight         610.52
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_symmetry_Int_Tables_number      1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z

_cell_length_a                   5.927(5)
_cell_length_b                   8.342(5)
_cell_length_c                   13.899(5)
_cell_angle_alpha                79.829(5)
_cell_angle_beta                 84.029(5)
_cell_angle_gamma                77.411(5)
_cell_volume                     658.6(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    110.00(10)
_cell_measurement_reflns_used    6797
_cell_measurement_theta_min      2.5285
_cell_measurement_theta_max      32.6011
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.128
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.81592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      110.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            16835
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.534
_diffrn_reflns_theta_max         32.674
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             8553
# number of observed reflections (> n sig(I))
_reflns_number_gt                7113
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0575P)²+0.0863P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.3(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8553
_refine_ls_number_parameters     421
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.601
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.056

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 -0.8427(6) -0.2343(4) -0.3206(2) 0.0174(6) Uani 1 1 d . . . . .
C2 C -1.0216(5) -0.2681(4) -0.2399(2) 0.0160(6) Uani 1 1 d . . . . .
C3 C -0.9654(6) -0.3977(4) -0.1642(2) 0.0168(6) Uani 1 1 d . . . . .
H3 H -0.8156 -0.4675 -0.1649 0.020 Uiso 1 1 calc R U . . .
C4 C -1.1283(5) -0.4263(4) -0.0867(2) 0.0155(6) Uani 1 1 d . . . . .
C5 C -1.3511(5) -0.3232(4) -0.0878(2) 0.0153(6) Uani 1 1 d . . . . .
C6 C -1.4051(5) -0.1933(4) -0.1645(2) 0.0150(6) Uani 1 1 d . . . . .
C7 C -1.2430(6) -0.1674(4) -0.2430(2) 0.0164(6) Uani 1 1 d . . . . .
H7 H -1.2827 -0.0828 -0.2975 0.020 Uiso 1 1 calc DR U . . .
C8 C -1.3835(6) -0.1298(4) -0.5257(2) 0.0154(6) Uani 1 1 d . . . . .
C9 C -1.2078(5) -0.0932(4) -0.6050(2) 0.0146(6) Uani 1 1 d . . . . .
C10 C -1.2683(6) 0.0389(4) -0.6832(2) 0.0151(6) Uani 1 1 d . . . . .
H10 H -1.4192 0.1072 -0.6841 0.018 Uiso 1 1 calc R U . . .
C11 C -1.1013(5) 0.0652(4) -0.7578(2) 0.0148(6) Uani 1 1 d . . . . .
C12 C -0.8810(5) -0.0351(4) -0.7581(2) 0.0142(6) Uani 1 1 d . . . . .
C13 C -0.8233(5) -0.1668(4) -0.6807(2) 0.0132(6) Uani 1 1 d . . . . .
C14 C -0.9880(5) -0.1959(4) -0.6051(2) 0.0144(6) Uani 1 1 d . . . . .
H14 H -0.9513 -0.2859 -0.5532 0.017 Uiso 1 1 calc R U . . .
C15 C -0.7316(5) -0.5214(4) -0.8129(2) 0.0150(6) Uani 1 1 d . . . . .
C16 C -0.8456(6) -0.6013(4) -0.7194(2) 0.0166(6) Uani 1 1 d . . . . .
H16A H -0.7667 -0.5932 -0.6616 0.020 Uiso 1 1 calc R U . . .
H16B H -0.8413 -0.7201 -0.7213 0.020 Uiso 1 1 calc R U . . .
C17 C -1.0946(6) -0.5034(4) -0.7156(2) 0.0166(6) Uani 1 1 d . . . . .
H17A H -1.2045 -0.5753 -0.7201 0.020 Uiso 1 1 calc R U . . .
H17B H -1.1336 -0.4559 -0.6541 0.020 Uiso 1 1 calc R U . . .
C18 C -1.1019(5) -0.3673(4) -0.8033(2) 0.0165(6) Uani 1 1 d . . . . .
C19 C -1.1356(5) 0.1460(4) -0.1307(2) 0.0175(7) Uani 1 1 d . . . . .
H19A H -1.0950 0.0988 -0.1923 0.021 Uiso 1 1 calc R U . . .
H19B H -1.0271 0.2188 -0.1259 0.021 Uiso 1 1 calc R U . . .
C20 C -1.3874(6) 0.2433(5) -0.1274(3) 0.0191(7) Uani 1 1 d . . . . .
H20A H -1.3935 0.3627 -0.1268 0.023 Uiso 1 1 calc R U . . .
H20B H -1.4663 0.2325 -0.1845 0.023 Uiso 1 1 calc R U . . .
C21 C -1.4973(5) 0.1656(4) -0.0340(2) 0.0154(6) Uani 1 1 d . . . . .
C22 C -1.1266(5) 0.0090(4) -0.0429(2) 0.0152(6) Uani 1 1 d . . . . .
C23 C -0.5038(6) -0.6256(5) -0.4972(3) 0.0248(8) Uani 1 1 d . . . . .
H23A H -0.4075 -0.5402 -0.5149 0.030 Uiso 1 1 calc R U . . .
H23B H -0.4578 -0.7074 -0.5430 0.030 Uiso 1 1 calc R U . . .
C24 C -0.4708(6) -0.7121(4) -0.3919(2) 0.0296(6) Uani 1 1 d . . . . .
H24A H -0.4077 -0.6438 -0.3541 0.036 Uiso 1 1 calc R U . . .
H24B H -0.3654 -0.8223 -0.3899 0.036 Uiso 1 1 calc R U . . .
C25 C -0.7205(7) -0.7300(5) -0.3515(3) 0.0286(9) Uani 1 1 d . . . . .
H25A H -0.7272 -0.8480 -0.3276 0.034 Uiso 1 1 calc R U . . .
H25B H -0.7743 -0.6653 -0.2972 0.034 Uiso 1 1 calc R U . . .
C26 C -0.8654(6) -0.6606(4) -0.4390(2) 0.0299(6) Uani 1 1 d . . . . .
H26A H -0.8854 -0.7514 -0.4725 0.036 Uiso 1 1 calc R U . . .
H26B H -1.0202 -0.5993 -0.4182 0.036 Uiso 1 1 calc R U . . .
N1 N -1.3422(5) 0.0304(4) 0.0077(2) 0.0150(5) Uani 1 1 d . . . . .
N2 N -0.8867(5) -0.3866(4) -0.8543(2) 0.0172(6) Uani 1 1 d . . . . .
O1 O -0.6505(4) -0.3316(3) -0.32287(18) 0.0229(6) Uani 1 1 d . . . . .
O2 O -0.8993(4) -0.0990(3) -0.38275(18) 0.0247(6) Uani 1 1 d D . . . .
O3 O -1.6171(4) -0.0876(3) -0.16536(18) 0.0203(5) Uani 1 1 d . . . . .
O4 O -1.5170(4) -0.3454(3) -0.01473(17) 0.0215(6) Uani 1 1 d . . . . .
O5 O -1.0966(4) -0.5477(3) -0.00731(18) 0.0193(5) Uani 1 1 d . . . . .
O6 O -1.5786(4) -0.0279(3) -0.52067(19) 0.0239(6) Uani 1 1 d . . . . .
O7 O -1.3323(4) -0.2616(3) -0.46276(19) 0.0239(6) Uani 1 1 d D . . . .
O8 O -0.6111(4) -0.2691(3) -0.68150(17) 0.0180(5) Uani 1 1 d . . . . .
H8O H -0.5271 -0.2334 -0.7294 0.027 Uiso 1 1 calc R U . . .
O9 O -0.7148(4) -0.0110(3) -0.83172(17) 0.0200(5) Uani 1 1 d . . . . .
O10 O -1.1368(4) 0.1889(3) -0.83858(18) 0.0206(5) Uani 1 1 d . . . . .
O11 O -1.6957(4) 0.2114(3) 0.00087(18) 0.0201(5) Uani 1 1 d . . . . .
O12 O -0.9622(4) -0.1005(3) -0.01877(17) 0.0197(5) Uani 1 1 d . . . . .
O13 O -1.2651(4) -0.2559(3) -0.82936(18) 0.0218(5) Uani 1 1 d . . . . .
O14 O -0.5341(4) -0.5667(3) -0.84744(18) 0.0195(5) Uani 1 1 d . . . . .
O15 O -0.7400(4) -0.5511(3) -0.50255(16) 0.0304(4) Uani 1 1 d . . . . .
H1N H -1.366(9) -0.041(7) 0.060(4) 0.057 Uiso 1 1 d . U . . .
H2N H -0.857(9) -0.324(7) -0.919(4) 0.058 Uiso 1 1 d . U . . .
H2O H -0.769(6) -0.105(6) -0.418(3) 0.057 Uiso 1 1 d D U . . .
H3O H -1.688(11) -0.108(9) -0.118(5) 0.12(3) Uiso 1 1 d . . . . .
H4O H -1.461(7) -0.430(5) 0.033(3) 0.027(10) Uiso 1 1 d . . . . .
H5O H -0.956(10) -0.597(7) 0.001(4) 0.074(19) Uiso 1 1 d . . . . .
H7O H -1.426(7) -0.296(5) -0.409(2) 0.054 Uiso 1 1 d D U . . .
H9O H -0.764(13) 0.051(10) -0.881(6) 0.11(3) Uiso 1 1 d . . . . .
H10O H -1.279(6) 0.257(4) -0.830(2) 0.013(8) Uiso 1 1 d . . . . .


#===============================================================================

# 10. 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 O1 1.247(4) . ?
C1 O2 1.298(4) . ?
C1 C2 1.494(5) . ?
C2 C3 1.379(5) . ?
C2 C7 1.395(5) . ?
C3 C4 1.394(4) . ?
C4 O5 1.358(4) . ?
C4 C5 1.410(4) . ?
C5 O4 1.356(4) . ?
C5 C6 1.386(4) . ?
C6 O3 1.368(4) . ?
C6 C7 1.397(4) . ?
C8 O7 1.279(4) . ?
C8 O6 1.281(4) . ?
C8 C9 1.474(4) . ?
C9 C14 1.394(4) . ?
C9 C10 1.417(4) . ?
C10 C11 1.381(4) . ?
C11 O10 1.384(4) . ?
C11 C12 1.389(4) . ?
C12 O9 1.364(4) . ?
C12 C13 1.406(4) . ?
C13 O8 1.357(4) . ?
C13 C14 1.385(4) . ?
C15 O14 1.224(4) . ?
C15 N2 1.368(4) . ?
C15 C16 1.516(4) . ?
C16 C17 1.523(5) . ?
C17 C18 1.509(4) . ?
C18 O13 1.222(4) . ?
C18 N2 1.385(4) . ?
C19 C22 1.514(5) . ?
C19 C20 1.536(5) . ?
C20 C21 1.496(5) . ?
C21 O11 1.231(4) . ?
C21 N1 1.371(4) . ?
C22 O12 1.212(4) . ?
C22 N1 1.385(4) . ?
C23 O15 1.406(4) . ?
C23 C24 1.525(4) . ?
C24 C25 1.556(5) . ?
C25 C26 1.519(5) . ?
C26 O15 1.428(4) . ?

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
O1 C1 O2 124.4(3) . . ?
O1 C1 C2 119.6(3) . . ?
O2 C1 C2 115.9(3) . . ?
C3 C2 C7 121.4(3) . . ?
C3 C2 C1 119.6(3) . . ?
C7 C2 C1 119.1(3) . . ?
C2 C3 C4 120.0(3) . . ?
O5 C4 C3 126.4(3) . . ?
O5 C4 C5 114.4(3) . . ?
C3 C4 C5 119.2(3) . . ?
O4 C5 C6 118.0(3) . . ?
O4 C5 C4 121.9(3) . . ?
C6 C5 C4 120.1(3) . . ?
O3 C6 C5 121.2(3) . . ?
O3 C6 C7 118.3(3) . . ?
C5 C6 C7 120.5(3) . . ?
C6 C7 C2 118.7(3) . . ?
O7 C8 O6 122.3(3) . . ?
O7 C8 C9 118.2(3) . . ?
O6 C8 C9 119.4(3) . . ?
C14 C9 C10 120.8(3) . . ?
C14 C9 C8 119.3(3) . . ?
C10 C9 C8 119.8(3) . . ?
C11 C10 C9 118.0(3) . . ?
O10 C11 C10 124.1(3) . . ?
O10 C11 C12 114.2(3) . . ?
C10 C11 C12 121.7(3) . . ?
O9 C12 C11 122.2(3) . . ?
O9 C12 C13 117.8(3) . . ?
C11 C12 C13 120.0(3) . . ?
O8 C13 C14 119.9(3) . . ?
O8 C13 C12 120.6(3) . . ?
C14 C13 C12 119.4(3) . . ?
C13 C14 C9 120.1(3) . . ?
O14 C15 N2 124.3(3) . . ?
O14 C15 C16 127.0(3) . . ?
N2 C15 C16 108.7(3) . . ?
C15 C16 C17 104.9(3) . . ?
C18 C17 C16 104.5(2) . . ?
O13 C18 N2 122.8(3) . . ?
O13 C18 C17 128.3(3) . . ?
N2 C18 C17 108.9(3) . . ?
C22 C19 C20 104.8(2) . . ?
C21 C20 C19 104.6(3) . . ?
O11 C21 N1 124.1(3) . . ?
O11 C21 C20 126.7(3) . . ?
N1 C21 C20 109.2(3) . . ?
O12 C22 N1 124.8(3) . . ?
O12 C22 C19 127.3(3) . . ?
N1 C22 C19 107.9(3) . . ?
O15 C23 C24 107.1(3) . . ?
C23 C24 C25 103.2(3) . . ?
C26 C25 C24 103.9(3) . . ?
O15 C26 C25 105.7(3) . . ?
C21 N1 C22 113.3(3) . . ?
C15 N2 C18 112.8(3) . . ?
C23 O15 C26 106.5(2) . . ?


# start Validation Reply Form
_vrf_PLAT222_ra68_ag_2           
;
PROBLEM: ADDSYM Detects (Pseudo) Centre of Symmetry .....         97 %Fit  
RESPONSE:We have attempted to solve the structure in the space group P-1,
 but the solvent had been disordered over special position making it 
difficult to resolve. Although analysis of crystal packing shows a
 pseudo-centre of symmetry between the acid-imide pairs, the presence 
of asymmetric solvent molecule (THF) breaks the centre of symmetry. 
The structure could be solved without structural disorder in P1.
;
_vrf_PLAT250_ra68_ag_2           
;
PROBLEM:  ADDSYM Suggests Possible Pseudo/New Space group.        P-1 Check  
RESPONSE: We have attempted to solve the structure in the space group P-1,
 but the solvent had been disordered over special position making it 
difficult to resolve. Although analysis of crystal packing shows a
 pseudo-centre of symmetry between the acid-imide pairs, the presence 
of asymmetric solvent molecule (THF) breaks the centre of symmetry. 
The structure could be solved without structural disorder in P1.
;

# end Validation Reply Form


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
