# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_am0118pbis
_database_code_depnum_ccdc_archive 'CCDC 1495135'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;
_audit_creation_date             2015-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 O5'
_chemical_formula_sum            'C25 H20 O5'
_chemical_formula_weight         400.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c25 h20 o5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.14371(17)
_cell_length_b                   7.60048(7)
_cell_length_c                   16.42538(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.4396(10)
_cell_angle_gamma                90
_cell_volume                     1988.10(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18885
_cell_measurement_temperature    293
_cell_measurement_theta_max      74.1280
_cell_measurement_theta_min      5.4440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28457
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.283
_diffrn_reflns_theta_min         5.460
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -95.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 121

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245   38.0000  150.0000 77

#__ type_ start__ end____ width___ exp.time_
  5 omega -146.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -99.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
  6 omega -146.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -99.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
  7 omega  -96.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  125.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  8 omega   20.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   57.0000 -150.0000 121

#__ type_ start__ end____ width___ exp.time_
  9 omega   20.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   57.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 10 omega  -35.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245  -77.0000  -30.0000 131

#__ type_ start__ end____ width___ exp.time_
 11 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000    0.0000 86

#__ type_ start__ end____ width___ exp.time_
 12 omega   28.00  116.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489 -111.0000  -60.0000 88

#__ type_ start__ end____ width___ exp.time_
 13 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
 14 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000  150.0000 62

#__ type_ start__ end____ width___ exp.time_
 15 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000  120.0000 86

#__ type_ start__ end____ width___ exp.time_
 16 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 17 omega   70.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   30.0000   30.0000 108

#__ type_ start__ end____ width___ exp.time_
 18 omega  100.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  111.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
 19 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
 20 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
 21 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
 22 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000  -30.0000 86

#__ type_ start__ end____ width___ exp.time_
 23 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 24 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000   90.0000 86

#__ type_ start__ end____ width___ exp.time_
 25 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
 26 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000  -30.0000 62

#__ type_ start__ end____ width___ exp.time_
 27 omega   57.00  150.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  178.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
 28 omega  -84.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   60.0000 121

#__ type_ start__ end____ width___ exp.time_
 29 omega    1.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 30 omega    1.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
 31 omega -149.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -77.0000 -180.0000 131

#__ type_ start__ end____ width___ exp.time_
 32 omega -149.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -77.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 33 omega   94.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245  125.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
 34 omega   18.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   77.0000  -30.0000 131

#__ type_ start__ end____ width___ exp.time_
 35 omega   18.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   77.0000  120.0000 131

#__ type_ start__ end____ width___ exp.time_
 36 omega   18.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   77.0000  -90.0000 131

#__ type_ start__ end____ width___ exp.time_
 37 omega   94.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245  125.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
 38 omega   18.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   77.0000   60.0000 131

#__ type_ start__ end____ width___ exp.time_
 39 omega   20.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   57.0000   60.0000 121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0414733000
_diffrn_orient_matrix_UB_12      -0.1804945000
_diffrn_orient_matrix_UB_13      0.0075834000
_diffrn_orient_matrix_UB_21      -0.0873063000
_diffrn_orient_matrix_UB_22      0.0871542000
_diffrn_orient_matrix_UB_23      -0.0165004000
_diffrn_orient_matrix_UB_31      -0.0041210000
_diffrn_orient_matrix_UB_32      -0.0300706000
_diffrn_orient_matrix_UB_33      -0.0933332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3748
_reflns_number_total             4032
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.4520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1028
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1 O 0.71287(5) -0.09888(10) 0.34143(5) 0.03681(19) Uani 1 1 d . . . . .
O2 O 0.77991(5) -0.09608(10) 0.41341(5) 0.03719(19) Uani 1 1 d . . . . .
O3 O 0.68867(6) -0.23005(11) 0.49098(6) 0.0463(2) Uani 1 1 d . . . . .
H3 H 0.7159 -0.3208 0.5010 0.069 Uiso 1 1 calc GR . . . .
O4 O 0.83700(8) -0.24080(13) 0.59075(7) 0.0672(3) Uani 1 1 d . . . . .
O5 O 0.72614(6) 0.38922(11) 0.50136(6) 0.0502(2) Uani 1 1 d . . . . .
C1 C 0.67678(7) 0.07555(14) 0.33099(7) 0.0340(2) Uani 1 1 d . . . . .
C2 C 0.63624(7) 0.11209(15) 0.40774(7) 0.0354(2) Uani 1 1 d . . . . .
H2A H 0.5878 0.0359 0.4061 0.042 Uiso 1 1 calc R . . . .
H2B H 0.6163 0.2327 0.4053 0.042 Uiso 1 1 calc R . . . .
C3 C 0.69511(7) 0.08409(14) 0.49062(7) 0.0350(2) Uani 1 1 d . . . . .
C4 C 0.74222(7) -0.09143(14) 0.48703(7) 0.0362(2) Uani 1 1 d . . . . .
C5 C 0.82256(8) -0.10544(16) 0.55250(8) 0.0428(3) Uani 1 1 d . . . . .
C6 C 0.87855(7) 0.04794(17) 0.56124(7) 0.0406(3) Uani 1 1 d . . . . .
C7 C 0.96376(8) 0.0283(2) 0.59349(8) 0.0513(3) Uani 1 1 d . . . . .
H7 H 0.9852 -0.0820 0.6100 0.062 Uiso 1 1 calc R . . . .
C8 C 1.01567(9) 0.1730(2) 0.60072(10) 0.0603(4) Uani 1 1 d . . . . .
H8 H 1.0725 0.1598 0.6213 0.072 Uiso 1 1 calc R . . . .
C9 C 0.98416(10) 0.3378(2) 0.57767(10) 0.0627(4) Uani 1 1 d . . . . .
H9 H 1.0198 0.4347 0.5830 0.075 Uiso 1 1 calc R . . . .
C10 C 0.89965(9) 0.3594(2) 0.54665(9) 0.0535(3) Uani 1 1 d . . . . .
H10 H 0.8785 0.4708 0.5319 0.064 Uiso 1 1 calc R . . . .
C11 C 0.84655(7) 0.21431(16) 0.53771(7) 0.0397(3) Uani 1 1 d . . . . .
C12 C 0.75513(7) 0.24181(15) 0.50797(7) 0.0372(2) Uani 1 1 d . . . . .
C13 C 0.64387(9) 0.08239(19) 0.56195(9) 0.0501(3) Uani 1 1 d . . . . .
H13A H 0.6029 -0.0101 0.5531 0.075 Uiso 1 1 calc GR . . . .
H13B H 0.6160 0.1935 0.5640 0.075 Uiso 1 1 calc GR . . . .
H13C H 0.6808 0.0627 0.6132 0.075 Uiso 1 1 calc GR . . . .
C14 C 0.61077(7) 0.05565(15) 0.25294(7) 0.0352(2) Uani 1 1 d . . . . .
C15 C 0.62660(8) -0.05101(17) 0.18861(7) 0.0414(3) Uani 1 1 d . . . . .
H15 H 0.6769 -0.1127 0.1934 0.050 Uiso 1 1 calc R . . . .
C16 C 0.56786(8) -0.06599(17) 0.11728(7) 0.0448(3) Uani 1 1 d . . . . .
H16 H 0.5784 -0.1397 0.0750 0.054 Uiso 1 1 calc R . . . .
C17 C 0.49366(8) 0.02804(17) 0.10864(7) 0.0419(3) Uani 1 1 d . . . . .
H17 H 0.4545 0.0181 0.0606 0.050 Uiso 1 1 calc R . . . .
C18 C 0.47814(8) 0.13626(17) 0.17135(8) 0.0447(3) Uani 1 1 d . . . . .
H18 H 0.4287 0.2011 0.1654 0.054 Uiso 1 1 calc R . . . .
C19 C 0.53602(8) 0.14915(17) 0.24357(8) 0.0438(3) Uani 1 1 d . . . . .
H19 H 0.5246 0.2212 0.2861 0.053 Uiso 1 1 calc R . . . .
C20 C 0.74216(7) 0.20914(15) 0.31258(7) 0.0359(2) Uani 1 1 d . . . . .
C21 C 0.81516(8) 0.15383(19) 0.28575(9) 0.0479(3) Uani 1 1 d . . . . .
H21 H 0.8260 0.0342 0.2821 0.058 Uiso 1 1 calc R . . . .
C22 C 0.87196(9) 0.2755(2) 0.26443(10) 0.0583(4) Uani 1 1 d . . . . .
H22 H 0.9209 0.2370 0.2471 0.070 Uiso 1 1 calc R . . . .
C23 C 0.85633(10) 0.4531(2) 0.26874(9) 0.0581(4) Uani 1 1 d . . . . .
H23 H 0.8948 0.5345 0.2549 0.070 Uiso 1 1 calc R . . . .
C24 C 0.78355(11) 0.50917(19) 0.29362(10) 0.0593(4) Uani 1 1 d . . . . .
H24 H 0.7724 0.6289 0.2961 0.071 Uiso 1 1 calc R . . . .
C25 C 0.72667(9) 0.38796(17) 0.31501(9) 0.0476(3) Uani 1 1 d . . . . .
H25 H 0.6773 0.4274 0.3312 0.057 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O2 1.4662(10) . ?
O1 C1 1.4470(12) . ?
O2 C4 1.4405(14) . ?
O3 H3 0.8200 . ?
O3 C4 1.3711(14) . ?
O4 C5 1.2081(16) . ?
O5 C12 1.2122(14) . ?
C1 C2 1.5379(16) . ?
C1 C14 1.5343(14) . ?
C1 C20 1.5301(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.5419(15) . ?
C3 C4 1.5414(15) . ?
C3 C12 1.5383(16) . ?
C3 C13 1.5410(17) . ?
C4 C5 1.5468(16) . ?
C5 C6 1.4677(18) . ?
C6 C7 1.3986(17) . ?
C6 C11 1.3963(17) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.3896(18) . ?
C11 C12 1.4914(16) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.3884(16) . ?
C14 C19 1.3870(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.3859(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.3821(18) . ?
C17 H17 0.9300 . ?
C17 C18 1.3729(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.3879(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.3893(17) . ?
C20 C25 1.3837(17) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.377(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.374(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.386(2) . ?
C25 H25 0.9300 . ?

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
C1 O1 O2 108.17(7) . . ?
C4 O2 O1 108.65(7) . . ?
C4 O3 H3 109.5 . . ?
O1 C1 C2 106.59(9) . . ?
O1 C1 C14 102.69(8) . . ?
O1 C1 C20 110.73(9) . . ?
C14 C1 C2 111.85(9) . . ?
C20 C1 C2 116.25(9) . . ?
C20 C1 C14 107.90(9) . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C1 C2 C3 114.54(9) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C4 C3 C2 108.79(9) . . ?
C12 C3 C2 109.52(9) . . ?
C12 C3 C4 112.45(9) . . ?
C12 C3 C13 105.43(10) . . ?
C13 C3 C2 110.02(10) . . ?
C13 C3 C4 110.58(10) . . ?
O2 C4 C3 109.41(9) . . ?
O2 C4 C5 99.23(9) . . ?
O3 C4 O2 112.16(9) . . ?
O3 C4 C3 110.14(9) . . ?
O3 C4 C5 112.18(10) . . ?
C3 C4 C5 113.31(9) . . ?
O4 C5 C4 119.24(12) . . ?
O4 C5 C6 124.21(12) . . ?
C6 C5 C4 116.49(10) . . ?
C7 C6 C5 120.26(12) . . ?
C11 C6 C5 119.89(10) . . ?
C11 C6 C7 119.85(12) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.64(14) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.62(13) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.31(14) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.86(14) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 C12 121.26(11) . . ?
C10 C11 C6 119.71(12) . . ?
C10 C11 C12 118.92(11) . . ?
O5 C12 C3 118.79(10) . . ?
O5 C12 C11 120.37(11) . . ?
C11 C12 C3 120.72(10) . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C1 120.27(10) . . ?
C19 C14 C1 120.97(10) . . ?
C19 C14 C15 118.70(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.36(11) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.37(11) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.64(11) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.23(11) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.67(11) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C1 120.69(11) . . ?
C25 C20 C1 120.82(11) . . ?
C25 C20 C21 118.23(12) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.57(13) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.42(14) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.48(14) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.25(14) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 121.02(13) . . ?
C20 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_am0155pf1
_database_code_depnum_ccdc_archive 'CCDC 1495137'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;
_audit_creation_date             2016-03-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O7'
_chemical_formula_sum            'C20 H17 N O7'
_chemical_formula_weight         383.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c20 h17 n1 o7'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6077(4)
_cell_length_b                   17.9285(7)
_cell_length_c                   13.5108(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.529(4)
_cell_angle_gamma                90
_cell_volume                     1826.91(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4928
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.8160
_cell_measurement_theta_min      3.9770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12982
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.165
_diffrn_reflns_theta_min         3.461
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   21.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166  -99.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   28.00   89.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166   38.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00   66.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166  -19.0000 -180.0000 135

#__ type_ start__ end____ width___ exp.time_
  4 omega  -71.00   31.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166  -77.0000    0.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0352268000
_diffrn_orient_matrix_UB_12      0.0256883000
_diffrn_orient_matrix_UB_13      0.0373544000
_diffrn_orient_matrix_UB_21      0.0759734000
_diffrn_orient_matrix_UB_22      0.0048160000
_diffrn_orient_matrix_UB_23      -0.0246498000
_diffrn_orient_matrix_UB_31      -0.0427898000
_diffrn_orient_matrix_UB_32      0.0297028000
_diffrn_orient_matrix_UB_33      -0.0283125000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2968
_reflns_number_total             3863
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.7266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.83640(19) 0.58717(8) 0.27035(14) 0.0751(5) Uani 1 1 d . . . . .
O2 O 0.27025(19) 0.43788(8) 0.35542(12) 0.0657(4) Uani 1 1 d . . . . .
O3 O 0.53658(19) 0.35845(7) 0.30275(11) 0.0573(4) Uani 1 1 d . . . . .
H3 H 0.4392 0.3453 0.3163 0.086 Uiso 1 1 calc GR . . . .
O4 O 0.47108(14) 0.44251(7) 0.17095(9) 0.0412(3) Uani 1 1 d . . . . .
O5 O 0.58364(15) 0.39627(7) 0.11486(8) 0.0409(3) Uani 1 1 d . . . . .
O6 O 1.0882(2) 0.22512(10) -0.19712(13) 0.0773(5) Uani 1 1 d . . . . .
O7 O 1.3209(2) 0.24525(11) -0.09387(14) 0.0881(6) Uani 1 1 d . . . . .
N1 N 1.1622(3) 0.25094(9) -0.11926(14) 0.0579(4) Uani 1 1 d . . . . .
C1 C 0.7581(2) 0.43044(9) 0.12138(12) 0.0340(4) Uani 1 1 d . . . . .
C2 C 0.8369(2) 0.43298(10) 0.23120(12) 0.0377(4) Uani 1 1 d . . . . .
H2A H 0.9463 0.4614 0.2372 0.045 Uiso 1 1 calc R . . . .
H2B H 0.8665 0.3826 0.2536 0.045 Uiso 1 1 calc R . . . .
C3 C 0.7144(2) 0.46743(10) 0.30020(12) 0.0387(4) Uani 1 1 d . . . . .
C4 C 0.7074(2) 0.55262(10) 0.28951(14) 0.0453(4) Uani 1 1 d . . . . .
C5 C 0.5461(2) 0.59327(9) 0.30964(13) 0.0406(4) Uani 1 1 d . . . . .
C6 C 0.5500(3) 0.67077(11) 0.31548(16) 0.0565(5) Uani 1 1 d . . . . .
H6 H 0.6521 0.6964 0.3049 0.068 Uiso 1 1 calc R . . . .
C7 C 0.4038(3) 0.70961(11) 0.33675(17) 0.0638(6) Uani 1 1 d . . . . .
H7 H 0.4081 0.7614 0.3411 0.077 Uiso 1 1 calc R . . . .
C8 C 0.2509(3) 0.67244(11) 0.35169(16) 0.0578(5) Uani 1 1 d . . . . .
H8 H 0.1523 0.6992 0.3655 0.069 Uiso 1 1 calc R . . . .
C9 C 0.2438(2) 0.59609(11) 0.34618(14) 0.0470(4) Uani 1 1 d . . . . .
H9 H 0.1404 0.5712 0.3562 0.056 Uiso 1 1 calc R . . . .
C10 C 0.3913(2) 0.55590(9) 0.32562(12) 0.0376(4) Uani 1 1 d . . . . .
C11 C 0.3839(2) 0.47398(10) 0.32270(13) 0.0412(4) Uani 1 1 d . . . . .
C12 C 0.5301(2) 0.43234(9) 0.27591(12) 0.0374(4) Uani 1 1 d . . . . .
C13 C 0.8614(2) 0.37720(9) 0.06240(12) 0.0361(4) Uani 1 1 d . . . . .
C14 C 0.7793(3) 0.34149(12) -0.02305(14) 0.0542(5) Uani 1 1 d . . . . .
H14 H 0.6576 0.3466 -0.0410 0.065 Uiso 1 1 calc R . . . .
C15 C 0.8764(3) 0.29855(13) -0.08144(15) 0.0591(6) Uani 1 1 d . . . . .
H15 H 0.8212 0.2744 -0.1381 0.071 Uiso 1 1 calc R . . . .
C16 C 1.0559(3) 0.29229(10) -0.05409(14) 0.0450(4) Uani 1 1 d . . . . .
C17 C 1.1407(2) 0.32514(10) 0.03033(14) 0.0448(4) Uani 1 1 d . . . . .
H17 H 1.2623 0.3195 0.0479 0.054 Uiso 1 1 calc R . . . .
C18 C 1.0420(2) 0.36695(10) 0.08894(13) 0.0412(4) Uani 1 1 d . . . . .
H18 H 1.0978 0.3886 0.1473 0.049 Uiso 1 1 calc R . . . .
C19 C 0.7915(3) 0.45301(14) 0.40968(14) 0.0628(6) Uani 1 1 d . . . . .
H19A H 0.7880 0.4005 0.4234 0.094 Uiso 1 1 calc GR . . . .
H19B H 0.7225 0.4794 0.4530 0.094 Uiso 1 1 calc GR . . . .
H19C H 0.9120 0.4702 0.4209 0.094 Uiso 1 1 calc GR . . . .
C20 C 0.7446(3) 0.50539(11) 0.06766(16) 0.0518(5) Uani 1 1 d . . . . .
H20A H 0.7031 0.4978 -0.0018 0.078 Uiso 1 1 calc GR . . . .
H20B H 0.8592 0.5286 0.0745 0.078 Uiso 1 1 calc GR . . . .
H20C H 0.6629 0.5370 0.0965 0.078 Uiso 1 1 calc GR . . . .


_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
O1 C4 1.217(2) . ?
O2 C11 1.209(2) . ?
O3 H3 0.8200 . ?
O3 C12 1.373(2) . ?
O4 O5 1.4714(15) . ?
O4 C12 1.442(2) . ?
O5 C1 1.4541(19) . ?
O6 N1 1.218(2) . ?
O7 N1 1.216(2) . ?
N1 C16 1.471(2) . ?
C1 C2 1.526(2) . ?
C1 C13 1.526(2) . ?
C1 C20 1.524(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.532(2) . ?
C3 C4 1.534(2) . ?
C3 C12 1.533(2) . ?
C3 C19 1.540(2) . ?
C4 C5 1.483(2) . ?
C5 C6 1.392(3) . ?
C5 C10 1.396(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(2) . ?
C10 C11 1.470(2) . ?
C11 C12 1.542(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.386(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(3) . ?
C16 C17 1.368(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(2) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C12 O3 H3 109.5 . . ?
C12 O4 O5 107.95(11) . . ?
C1 O5 O4 108.65(10) . . ?
O6 N1 C16 118.72(19) . . ?
O7 N1 O6 122.79(18) . . ?
O7 N1 C16 118.47(18) . . ?
O5 C1 C2 108.10(12) . . ?
O5 C1 C13 103.50(12) . . ?
O5 C1 C20 109.78(13) . . ?
C13 C1 C2 111.28(13) . . ?
C20 C1 C2 115.46(15) . . ?
C20 C1 C13 108.06(14) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C1 C2 C3 114.25(13) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C2 C3 C4 111.11(14) . . ?
C2 C3 C12 108.47(13) . . ?
C2 C3 C19 109.35(14) . . ?
C4 C3 C19 105.17(15) . . ?
C12 C3 C4 111.66(14) . . ?
C12 C3 C19 111.06(16) . . ?
O1 C4 C3 120.54(16) . . ?
O1 C4 C5 119.91(17) . . ?
C5 C4 C3 119.42(15) . . ?
C6 C5 C4 119.29(16) . . ?
C6 C5 C10 118.84(17) . . ?
C10 C5 C4 121.85(15) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.41(19) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.49(18) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.17(18) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.03(18) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C11 120.37(15) . . ?
C9 C10 C5 120.07(16) . . ?
C9 C10 C11 119.56(15) . . ?
O2 C11 C10 123.48(16) . . ?
O2 C11 C12 118.65(15) . . ?
C10 C11 C12 117.87(14) . . ?
O3 C12 O4 112.19(14) . . ?
O3 C12 C3 109.82(14) . . ?
O3 C12 C11 111.23(13) . . ?
O4 C12 C3 108.46(13) . . ?
O4 C12 C11 101.18(13) . . ?
C3 C12 C11 113.71(13) . . ?
C14 C13 C1 120.93(15) . . ?
C18 C13 C1 120.58(15) . . ?
C18 C13 C14 118.36(16) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.83(18) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.65(18) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 N1 119.05(18) . . ?
C17 C16 N1 118.68(18) . . ?
C17 C16 C15 122.23(17) . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.63(17) . . ?
C18 C17 H17 120.7 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.24(16) . . ?
C17 C18 H18 119.4 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C20 H20A 109.5 . . ?
C1 C20 H20B 109.5 . . ?
C1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_am0155pf2
_database_code_depnum_ccdc_archive 'CCDC 1495138'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;
_audit_creation_date             2016-03-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O7, C H4 O0.25'
_chemical_formula_sum            'C21 H21 N O7.25'
_chemical_formula_weight         403.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c20 h17 n1 o7'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.134(6)
_cell_length_b                   7.3925(3)
_cell_length_c                   23.922(4)
_cell_angle_alpha                90
_cell_angle_beta                 135.55(3)
_cell_angle_gamma                90
_cell_volume                     4103.4(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4959
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.0320
_cell_measurement_theta_min      3.8830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15680
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.146
_diffrn_reflns_theta_min         3.351
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   56.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166  -99.0000  120.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00   27.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166   78.0000  -80.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166  178.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166   38.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   -9.00   82.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166   19.0000  120.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0220187000
_diffrn_orient_matrix_UB_12      0.0645528000
_diffrn_orient_matrix_UB_13      0.0267762000
_diffrn_orient_matrix_UB_21      -0.0086221000
_diffrn_orient_matrix_UB_22      0.0486007000
_diffrn_orient_matrix_UB_23      -0.0326799000
_diffrn_orient_matrix_UB_31      -0.0193674000
_diffrn_orient_matrix_UB_32      0.0517677000
_diffrn_orient_matrix_UB_33      -0.0027034000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3080
_reflns_number_total             4391
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1135P)²+3.6574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2016
_refine_ls_wR_factor_ref         0.2234
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: O8(0.25) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5) H21D(0.5)
 H21E(0.5) H21F(0.5) C22(0.25) H22A(0.25) H22B(0.25) C23(0.25) H23A(0.25)
 H23B(0.25)
3.a Riding coordinates:
 C21(H21A,H21B,H21C), C21(H21D,H21E,H21F), C22(H22A,H22B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.61677(9) 0.5934(2) 0.57474(13) 0.0635(6) Uani 1 1 d . . . . .
O2 O 0.71621(10) -0.0477(3) 0.68081(13) 0.0764(7) Uani 1 1 d . . . . .
O3 O 0.60222(9) -0.0380(2) 0.58698(13) 0.0604(6) Uani 1 1 d . . . . .
H3 H 0.6159 -0.1350 0.5905 0.091 Uiso 1 1 calc GR . . . .
O4 O 0.61372(7) 0.0798(2) 0.50833(10) 0.0443(4) Uani 1 1 d . . . . .
O5 O 0.55091(7) 0.0668(2) 0.43858(10) 0.0479(5) Uani 1 1 d . . . . .
O6 O 0.61105(14) 0.6662(5) 0.28718(19) 0.1092(10) Uani 1 1 d . . . . .
O7 O 0.57922(17) 0.8923(4) 0.3036(2) 0.1160(11) Uani 1 1 d . . . . .
N1 N 0.58969(13) 0.7309(5) 0.30825(17) 0.0784(9) Uani 1 1 d . . . . .
C1 C 0.52644(10) 0.2434(3) 0.42303(15) 0.0426(6) Uani 1 1 d . . . . .
C2 C 0.53864(11) 0.2972(3) 0.49557(16) 0.0452(6) Uani 1 1 d . . . . .
H2A H 0.5156 0.2213 0.4972 0.054 Uiso 1 1 calc R . . . .
H2B H 0.5261 0.4212 0.4886 0.054 Uiso 1 1 calc R . . . .
C3 C 0.60204(11) 0.2821(3) 0.57612(15) 0.0420(6) Uani 1 1 d . . . . .
C4 C 0.63644(11) 0.4431(3) 0.58763(15) 0.0446(6) Uani 1 1 d . . . . .
C5 C 0.69445(11) 0.4172(3) 0.62021(15) 0.0468(6) Uani 1 1 d . . . . .
C6 C 0.72261(14) 0.5653(4) 0.6245(2) 0.0648(8) Uani 1 1 d . . . . .
H6 H 0.7039 0.6763 0.6035 0.078 Uiso 1 1 calc R . . . .
C7 C 0.77773(16) 0.5477(6) 0.6594(2) 0.0799(11) Uani 1 1 d . . . . .
H7 H 0.7961 0.6459 0.6611 0.096 Uiso 1 1 calc R . . . .
C8 C 0.80581(15) 0.3859(7) 0.6918(2) 0.0838(11) Uani 1 1 d . . . . .
H8 H 0.8437 0.3765 0.7169 0.101 Uiso 1 1 calc R . . . .
C9 C 0.77926(13) 0.2370(5) 0.68811(18) 0.0738(9) Uani 1 1 d . . . . .
H9 H 0.7989 0.1276 0.7101 0.089 Uiso 1 1 calc R . . . .
C10 C 0.72242(11) 0.2507(4) 0.65098(15) 0.0516(7) Uani 1 1 d . . . . .
C11 C 0.69215(12) 0.0912(4) 0.64296(16) 0.0513(7) Uani 1 1 d . . . . .
C12 C 0.62579(12) 0.0997(3) 0.57895(16) 0.0443(6) Uani 1 1 d . . . . .
C13 C 0.54669(10) 0.3749(3) 0.39789(14) 0.0408(5) Uani 1 1 d . . . . .
C14 C 0.56893(12) 0.3089(4) 0.37003(17) 0.0519(7) Uani 1 1 d . . . . .
H14 H 0.5742 0.1851 0.3707 0.062 Uiso 1 1 calc R . . . .
C15 C 0.58339(13) 0.4264(4) 0.34106(18) 0.0605(8) Uani 1 1 d . . . . .
H15 H 0.5985 0.3818 0.3227 0.073 Uiso 1 1 calc R . . . .
C16 C 0.57515(12) 0.6075(4) 0.33991(15) 0.0550(7) Uani 1 1 d . . . . .
C17 C 0.55327(13) 0.6783(4) 0.36713(17) 0.0585(7) Uani 1 1 d . . . . .
H17 H 0.5484 0.8024 0.3665 0.070 Uiso 1 1 calc R . . . .
C18 C 0.53882(12) 0.5605(4) 0.39526(17) 0.0521(7) Uani 1 1 d . . . . .
H18 H 0.5234 0.6065 0.4129 0.062 Uiso 1 1 calc R . . . .
C19 C 0.60735(15) 0.2957(4) 0.64573(19) 0.0616(8) Uani 1 1 d . . . . .
H19A H 0.5940 0.4122 0.6446 0.092 Uiso 1 1 calc GR . . . .
H19B H 0.6469 0.2806 0.6955 0.092 Uiso 1 1 calc GR . . . .
H19C H 0.5844 0.2029 0.6402 0.092 Uiso 1 1 calc GR . . . .
C20 C 0.46219(12) 0.2067(4) 0.35107(18) 0.0597(7) Uani 1 1 d . . . . .
H20A H 0.4561 0.1555 0.3086 0.090 Uiso 1 1 calc GR . . . .
H20B H 0.4411 0.3180 0.3334 0.090 Uiso 1 1 calc GR . . . .
H20C H 0.4490 0.1233 0.3660 0.090 Uiso 1 1 calc GR . . . .
O8 O 0.7500 0.2500 0.5000 0.093(2) Uani 0.5 2 d S T P . .
C21 C 0.7163(4) -0.0455(10) 0.5052(5) 0.082(2) Uani 0.5 1 d . . . . .
H21A H 0.6846 -0.0534 0.4482 0.123 Uiso 0.5 1 d R . . A 1
H21B H 0.7322 -0.1638 0.5268 0.123 Uiso 0.5 1 d R . . A 1
H21C H 0.7029 0.0027 0.5268 0.123 Uiso 0.5 1 d R . . A 1
H21D H 0.6897 -0.1197 0.4584 0.123 Uiso 0.5 1 d R . . B 2
H21E H 0.7549 -0.0856 0.5364 0.123 Uiso 0.5 1 d R . . B 2
H21F H 0.7081 -0.0547 0.5364 0.123 Uiso 0.5 1 d R . . B 2
C22 C 0.7565(4) 0.0639(16) 0.5235(6) 0.048(3) Uani 0.25 1 d . . . C 1
H22A H 0.7706 0.0016 0.5045 0.058 Uiso 0.25 1 d R . . C 1
H22B H 0.7866 0.0669 0.5814 0.058 Uiso 0.25 1 d R . . C 1
C23 C 0.7103(5) 0.1326(19) 0.4826(6) 0.055(3) Uani 0.25 1 d . . . C 2
H23A H 0.6792 0.1307 0.4248 0.066 Uiso 0.25 1 calc R . . C 2
H23B H 0.6950 0.1944 0.5000 0.066 Uiso 0.25 1 calc R . . C 2


_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
O1 C4 1.212(3) . ?
O2 C11 1.216(3) . ?
O3 H3 0.8200 . ?
O3 C12 1.377(3) . ?
O4 O5 1.472(3) . ?
O4 C12 1.439(3) . ?
O5 C1 1.439(3) . ?
O6 N1 1.222(4) . ?
O7 N1 1.226(4) . ?
N1 C16 1.469(4) . ?
C1 C2 1.527(3) . ?
C1 C13 1.527(3) . ?
C1 C20 1.529(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.536(4) . ?
C3 C4 1.530(3) . ?
C3 C12 1.539(3) . ?
C3 C19 1.548(3) . ?
C4 C5 1.483(4) . ?
C5 C6 1.394(4) . ?
C5 C10 1.393(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.399(4) . ?
C10 C11 1.469(4) . ?
C11 C12 1.542(4) . ?
C13 C14 1.388(3) . ?
C13 C18 1.390(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.363(4) . ?
C16 C17 1.377(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O8 C22 1.443(12) . ?
O8 C22 1.443(12) 7_656 ?
O8 C23 1.370(14) 7_656 ?
O8 C23 1.370(14) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9595 . ?
C21 H21D 0.9601 . ?
C21 H21E 0.9599 . ?
C21 H21F 0.9598 . ?
C21 C22 1.338(13) . ?
C21 C23 1.382(15) . ?
C22 H22A 0.9696 . ?
C22 H22B 0.9701 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

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
C12 O3 H3 109.5 . . ?
C12 O4 O5 108.71(17) . . ?
C1 O5 O4 108.28(15) . . ?
O6 N1 O7 123.6(3) . . ?
O6 N1 C16 118.0(3) . . ?
O7 N1 C16 118.4(3) . . ?
O5 C1 C2 107.42(19) . . ?
O5 C1 C13 110.76(19) . . ?
O5 C1 C20 101.8(2) . . ?
C2 C1 C13 116.6(2) . . ?
C2 C1 C20 110.6(2) . . ?
C13 C1 C20 108.7(2) . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C1 C2 C3 114.97(19) . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C2 C3 C12 108.5(2) . . ?
C2 C3 C19 110.4(2) . . ?
C4 C3 C2 110.20(19) . . ?
C4 C3 C12 112.5(2) . . ?
C4 C3 C19 104.9(2) . . ?
C12 C3 C19 110.3(2) . . ?
O1 C4 C3 118.1(2) . . ?
O1 C4 C5 120.8(2) . . ?
C5 C4 C3 120.9(2) . . ?
C6 C5 C4 119.1(2) . . ?
C10 C5 C4 121.0(2) . . ?
C10 C5 C6 119.8(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.3(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C5 C10 C9 119.1(3) . . ?
C5 C10 C11 120.4(2) . . ?
C9 C10 C11 120.6(3) . . ?
O2 C11 C10 123.8(3) . . ?
O2 C11 C12 119.1(3) . . ?
C10 C11 C12 117.0(2) . . ?
O3 C12 O4 112.2(2) . . ?
O3 C12 C3 109.32(19) . . ?
O3 C12 C11 112.4(2) . . ?
O4 C12 C3 109.44(19) . . ?
O4 C12 C11 99.55(19) . . ?
C3 C12 C11 113.7(2) . . ?
C14 C13 C1 119.9(2) . . ?
C14 C13 C18 118.2(2) . . ?
C18 C13 C1 121.7(2) . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 N1 119.0(3) . . ?
C15 C16 C17 121.9(3) . . ?
C17 C16 N1 119.0(3) . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.3(3) . . ?
C18 C17 H17 120.8 . . ?
C13 C18 H18 119.1 . . ?
C17 C18 C13 121.8(3) . . ?
C17 C18 H18 119.1 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C20 H20A 109.5 . . ?
C1 C20 H20B 109.5 . . ?
C1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 O8 C22 180.0 7_656 . ?
C23 O8 C23 180.0 . 7_656 ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 109.8 . . ?
C22 C21 H21C 109.6 . . ?
C23 C21 H21D 109.4 . . ?
C23 C21 H21E 109.7 . . ?
C23 C21 H21F 109.3 . . ?
O8 C22 H22A 105.0 . . ?
O8 C22 H22B 104.5 . . ?
C21 C22 O8 127.7(8) . . ?
C21 C22 H22A 105.1 . . ?
C21 C22 H22B 104.4 . . ?
H22A C22 H22B 109.5 . . ?
O8 C23 C21 130.3(9) . . ?
O8 C23 H23A 104.7 . . ?
O8 C23 H23B 104.7 . . ?
C21 C23 H23A 104.7 . . ?
C21 C23 H23B 104.7 . . ?
H23A C23 H23B 105.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_am0163pf1
_database_code_depnum_ccdc_archive 'CCDC 1495140'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 N O6'
_chemical_formula_sum            'C19 H13 N O6'
_chemical_formula_weight         351.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9834(3)
_cell_length_b                   17.6071(6)
_cell_length_c                   12.0243(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.179(4)
_cell_angle_gamma                90
_cell_volume                     1652.17(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5483
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.2580
_cell_measurement_theta_min      4.1480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12211
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.145
_diffrn_reflns_theta_min         3.425
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   36.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0572 -178.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   30.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0572  -99.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00  -63.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0572  178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   66.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385   19.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
  5 omega   11.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385   38.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega  -66.00   -1.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385  -57.0000  150.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0373290000
_diffrn_orient_matrix_UB_12      -0.0334647000
_diffrn_orient_matrix_UB_13      0.0274089000
_diffrn_orient_matrix_UB_21      -0.0728667000
_diffrn_orient_matrix_UB_22      -0.0053374000
_diffrn_orient_matrix_UB_23      0.0241747000
_diffrn_orient_matrix_UB_31      -0.0394350000
_diffrn_orient_matrix_UB_32      -0.0217805000
_diffrn_orient_matrix_UB_33      -0.0480352000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2779
_reflns_number_total             3434
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.8979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1267
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O -0.1181(2) 0.30839(13) 0.3504(2) 0.0959(7) Uani 1 1 d . . . . .
O2 O -0.0263(3) 0.25297(13) 0.2168(2) 0.1130(9) Uani 1 1 d . . . . .
O3 O -0.04412(18) 0.43663(8) 0.21570(13) 0.0574(4) Uani 1 1 d . . . . .
O4 O -0.2335(2) 0.51037(11) 0.38791(14) 0.0689(5) Uani 1 1 d . . . . .
O5 O -0.53278(19) 0.57005(12) 0.27005(15) 0.0765(6) Uani 1 1 d . . . . .
O6 O 0.04754(17) 0.59577(10) 0.11585(13) 0.0593(4) Uani 1 1 d . . . . .
N1 N -0.0069(3) 0.29308(11) 0.3001(2) 0.0658(6) Uani 1 1 d . . . . .
C1 C 0.2000(2) 0.39986(10) 0.35099(15) 0.0366(4) Uani 1 1 d . . . . .
C2 C 0.3656(2) 0.42213(11) 0.40145(17) 0.0433(4) Uani 1 1 d . . . . .
H2 H 0.3925 0.4736 0.4070 0.052 Uiso 1 1 calc R . . . .
C3 C 0.4908(3) 0.36934(13) 0.44342(19) 0.0550(5) Uani 1 1 d . . . . .
H3 H 0.6009 0.3855 0.4767 0.066 Uiso 1 1 calc R . . . .
C4 C 0.4537(3) 0.29347(13) 0.4362(2) 0.0624(6) Uani 1 1 d . . . . .
H4 H 0.5386 0.2582 0.4648 0.075 Uiso 1 1 calc R . . . .
C5 C 0.2905(3) 0.26892(12) 0.3867(2) 0.0609(6) Uani 1 1 d . . . . .
H5 H 0.2647 0.2174 0.3810 0.073 Uiso 1 1 calc R . . . .
C6 C 0.1676(2) 0.32219(11) 0.34626(18) 0.0457(5) Uani 1 1 d . . . . .
C7 C 0.0688(2) 0.45606(10) 0.29451(15) 0.0374(4) Uani 1 1 d . . . . .
C8 C 0.0839(2) 0.53683(10) 0.33538(16) 0.0380(4) Uani 1 1 d . . . . .
H8A H 0.1865 0.5593 0.3182 0.046 Uiso 1 1 calc R . . . .
H8B H 0.0952 0.5377 0.4173 0.046 Uiso 1 1 calc R . . . .
C9 C -0.0721(2) 0.58387(10) 0.27942(15) 0.0358(4) Uani 1 1 d . . . . .
C10 C -0.2341(2) 0.55047(11) 0.30685(16) 0.0418(4) Uani 1 1 d . . . . .
C11 C -0.4055(2) 0.57125(11) 0.23005(18) 0.0442(5) Uani 1 1 d . . . . .
C12 C -0.4062(2) 0.59038(10) 0.11136(16) 0.0361(4) Uani 1 1 d . . . . .
C13 C -0.5639(2) 0.59854(11) 0.03494(19) 0.0471(5) Uani 1 1 d . . . . .
H13 H -0.6657 0.5910 0.0592 0.056 Uiso 1 1 calc R . . . .
C14 C -0.5670(3) 0.61791(13) -0.07696(19) 0.0555(6) Uani 1 1 d . . . . .
H14 H -0.6712 0.6241 -0.1279 0.067 Uiso 1 1 calc R . . . .
C15 C -0.4157(3) 0.62798(14) -0.11303(19) 0.0577(6) Uani 1 1 d . . . . .
H15 H -0.4189 0.6418 -0.1881 0.069 Uiso 1 1 calc R . . . .
C16 C -0.2601(3) 0.61794(12) -0.03969(17) 0.0485(5) Uani 1 1 d . . . . .
H16 H -0.1592 0.6235 -0.0659 0.058 Uiso 1 1 calc R . . . .
C17 C -0.2534(2) 0.59958(10) 0.07286(15) 0.0349(4) Uani 1 1 d . . . . .
C18 C -0.0824(2) 0.59136(10) 0.15174(16) 0.0373(4) Uani 1 1 d . . . . .
C19 C -0.0549(3) 0.66554(12) 0.3289(2) 0.0555(6) Uani 1 1 d . . . . .
H19A H -0.0492 0.6635 0.4094 0.083 Uiso 1 1 calc GR . . . .
H19B H -0.1524 0.6951 0.2932 0.083 Uiso 1 1 calc GR . . . .
H19C H 0.0477 0.6885 0.3149 0.083 Uiso 1 1 calc GR . . . .


_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
O1 N1 1.205(3) . ?
O2 N1 1.209(3) . ?
O3 C7 1.211(2) . ?
O4 C10 1.203(2) . ?
O5 C11 1.213(2) . ?
O6 C18 1.207(2) . ?
N1 C6 1.478(3) . ?
C1 C2 1.390(2) . ?
C1 C6 1.391(3) . ?
C1 C7 1.496(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(3) . ?
C7 C8 1.501(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.529(2) . ?
C9 C10 1.519(2) . ?
C9 C18 1.526(3) . ?
C9 C19 1.551(3) . ?
C10 C11 1.525(3) . ?
C11 C12 1.465(3) . ?
C12 C13 1.400(2) . ?
C12 C17 1.402(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 C18 1.496(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 N1 O2 124.6(2) . . ?
O1 N1 C6 118.0(2) . . ?
O2 N1 C6 117.4(2) . . ?
C2 C1 C6 116.57(17) . . ?
C2 C1 C7 121.47(16) . . ?
C6 C1 C7 121.69(16) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.23(19) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 N1 120.60(17) . . ?
C5 C6 N1 116.32(18) . . ?
C5 C6 C1 123.04(19) . . ?
O3 C7 C1 120.18(17) . . ?
O3 C7 C8 121.26(16) . . ?
C1 C7 C8 118.54(14) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C9 111.55(14) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 C19 109.58(14) . . ?
C10 C9 C8 110.28(15) . . ?
C10 C9 C18 112.60(14) . . ?
C10 C9 C19 106.63(16) . . ?
C18 C9 C8 110.84(15) . . ?
C18 C9 C19 106.73(15) . . ?
O4 C10 C9 123.07(17) . . ?
O4 C10 C11 118.74(17) . . ?
C9 C10 C11 118.15(16) . . ?
O5 C11 C10 118.40(18) . . ?
O5 C11 C12 123.97(18) . . ?
C12 C11 C10 117.63(15) . . ?
C13 C12 C11 118.77(17) . . ?
C13 C12 C17 119.69(18) . . ?
C17 C12 C11 121.53(15) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.54(19) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.05(18) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.11(19) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C18 121.36(16) . . ?
C16 C17 C12 119.59(16) . . ?
C16 C17 C18 119.04(16) . . ?
O6 C18 C9 119.81(16) . . ?
O6 C18 C17 120.35(17) . . ?
C17 C18 C9 119.66(15) . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_am0163pf2
_database_code_depnum_ccdc_archive 'CCDC 1495141'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H15 N O7)'
_chemical_formula_sum            'C38 H30 N2 O14'
_chemical_formula_weight         738.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.7759(4)
_cell_length_b                   12.0137(4)
_cell_length_c                   13.2565(5)
_cell_angle_alpha                105.781(3)
_cell_angle_beta                 107.535(3)
_cell_angle_gamma                92.139(3)
_cell_volume                     1706.28(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6481
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.9260
_cell_measurement_theta_min      3.8680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21392
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.035
_diffrn_reflns_theta_min         3.452
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   32.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0572  -99.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385   38.0000    0.0000 110

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385   38.0000 -120.0000 109

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385   38.0000   90.0000 86

#__ type_ start__ end____ width___ exp.time_
  5 omega  -13.00   56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385  -99.0000 -180.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega  -56.00   48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385  -65.0000  -71.2376 104

#__ type_ start__ end____ width___ exp.time_
  7 omega  -24.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385  -95.0000   55.9279 79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0266080000
_diffrn_orient_matrix_UB_12      0.0479291000
_diffrn_orient_matrix_UB_13      0.0237417000
_diffrn_orient_matrix_UB_21      -0.0080194000
_diffrn_orient_matrix_UB_22      -0.0280879000
_diffrn_orient_matrix_UB_23      0.0384700000
_diffrn_orient_matrix_UB_31      0.0573283000
_diffrn_orient_matrix_UB_32      0.0272540000
_diffrn_orient_matrix_UB_33      0.0375528000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4339
_reflns_number_total             7092
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0675
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+1.1620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1754
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7A), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C22(H22), C23(H23), C24(H24), C25(H25), C31(H31), C32(H32), C33(H33), C34(H34)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7), O14(H14A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.1000(3) -0.2259(3) 0.2101(3) 0.1503(15) Uani 1 1 d . . . . .
O2 O 0.1888(4) -0.0876(3) 0.1839(3) 0.1318(13) Uani 1 1 d . . . . .
O3 O 0.30347(17) 0.20698(16) 0.44460(19) 0.0698(6) Uani 1 1 d . . . . .
O4 O 0.25163(17) 0.30096(16) 0.40153(18) 0.0672(6) Uani 1 1 d . . . . .
O5 O 0.1835(3) 0.53490(19) 0.4597(2) 0.1130(11) Uani 1 1 d . . . . .
O6 O -0.0301(2) 0.11284(18) 0.20290(18) 0.0751(6) Uani 1 1 d . . . . .
O7 O 0.1868(2) 0.3632(2) 0.55575(18) 0.0934(8) Uani 1 1 d . . . . .
H7 H 0.2126 0.4328 0.5823 0.140 Uiso 1 1 calc GR . . . .
N1 N 0.1739(3) -0.1423(3) 0.2431(3) 0.0851(9) Uani 1 1 d . . . . .
C1 C 0.2761(3) 0.0061(3) 0.4252(3) 0.0612(8) Uani 1 1 d . . . . .
C2 C 0.3504(4) 0.0273(3) 0.5337(3) 0.0889(11) Uani 1 1 d . . . . .
H2 H 0.3678 0.1031 0.5814 0.107 Uiso 1 1 calc R . . . .
C3 C 0.3992(4) -0.0623(4) 0.5725(3) 0.1019(13) Uani 1 1 d . . . . .
H3 H 0.4494 -0.0459 0.6454 0.122 Uiso 1 1 calc R . . . .
C4 C 0.3739(4) -0.1749(4) 0.5042(4) 0.0956(12) Uani 1 1 d . . . . .
H4 H 0.4071 -0.2346 0.5307 0.115 Uiso 1 1 calc R . . . .
C5 C 0.3000(3) -0.1994(3) 0.3976(3) 0.0802(10) Uani 1 1 d . . . . .
H5 H 0.2812 -0.2758 0.3512 0.096 Uiso 1 1 calc R . . . .
C6 C 0.2533(3) -0.1091(3) 0.3593(3) 0.0643(8) Uani 1 1 d . . . . .
C7 C 0.2168(3) 0.1038(2) 0.3869(2) 0.0559(7) Uani 1 1 d . . . . .
H7A H 0.1989 0.0870 0.3067 0.067 Uiso 1 1 calc R . . . .
C8 C 0.1039(3) 0.1228(3) 0.4167(3) 0.0612(8) Uani 1 1 d . . . . .
H8A H 0.1212 0.1315 0.4949 0.073 Uiso 1 1 calc R . . . .
H8B H 0.0443 0.0549 0.3753 0.073 Uiso 1 1 calc R . . . .
C9 C 0.0521(2) 0.2313(3) 0.3915(2) 0.0595(7) Uani 1 1 d . . . . .
C10 C 0.1532(3) 0.3331(2) 0.4414(2) 0.0623(8) Uani 1 1 d . . . . .
C11 C 0.1273(3) 0.4408(3) 0.4002(3) 0.0745(10) Uani 1 1 d . . . . .
C12 C 0.0396(3) 0.4251(2) 0.2909(2) 0.0652(8) Uani 1 1 d . . . . .
C13 C 0.0192(3) 0.5198(3) 0.2497(3) 0.0869(12) Uani 1 1 d . . . . .
H13 H 0.0619 0.5928 0.2915 0.104 Uiso 1 1 calc R . . . .
C14 C -0.0634(4) 0.5062(3) 0.1480(3) 0.0975(13) Uani 1 1 d . . . . .
H14 H -0.0767 0.5701 0.1212 0.117 Uiso 1 1 calc R . . . .
C15 C -0.1271(3) 0.3986(3) 0.0850(3) 0.0930(12) Uani 1 1 d . . . . .
H15 H -0.1834 0.3901 0.0160 0.112 Uiso 1 1 calc R . . . .
C16 C -0.1073(3) 0.3035(3) 0.1241(3) 0.0788(10) Uani 1 1 d . . . . .
H16 H -0.1502 0.2308 0.0811 0.095 Uiso 1 1 calc R . . . .
C17 C -0.0240(3) 0.3153(3) 0.2273(2) 0.0624(8) Uani 1 1 d . . . . .
C18 C -0.0013(2) 0.2112(3) 0.2668(2) 0.0562(7) Uani 1 1 d . . . . .
C19 C -0.0523(3) 0.2568(4) 0.4390(3) 0.1037(14) Uani 1 1 d . . . . .
H19A H -0.1108 0.1885 0.4109 0.156 Uiso 1 1 calc GR . . . .
H19B H -0.0892 0.3202 0.4172 0.156 Uiso 1 1 calc GR . . . .
H19C H -0.0218 0.2774 0.5184 0.156 Uiso 1 1 calc GR . . . .
O8 O 0.4009(3) 0.8584(2) 0.0050(2) 0.1104(10) Uani 1 1 d . . . . .
O9 O 0.3668(2) 0.7599(2) 0.1086(2) 0.0890(7) Uani 1 1 d . . . . .
O10 O 0.61428(17) 0.52040(16) 0.12742(16) 0.0597(5) Uani 1 1 d . . . . .
O11 O 0.55021(17) 0.40742(15) 0.11382(14) 0.0561(5) Uani 1 1 d . . . . .
O12 O 0.5644(3) 0.2141(2) 0.2342(2) 0.1084(10) Uani 1 1 d . . . . .
O13 O 0.27242(19) 0.5281(2) 0.1530(2) 0.0806(7) Uani 1 1 d . . . . .
O14 O 0.6606(2) 0.43030(19) 0.29831(18) 0.0826(7) Uani 1 1 d . . . . .
H14A H 0.6885 0.3693 0.3014 0.124 Uiso 1 1 calc GR . . . .
N2 N 0.4349(3) 0.8102(2) 0.0766(2) 0.0741(8) Uani 1 1 d . . . . .
C20 C 0.6113(3) 0.7213(2) 0.1629(2) 0.0547(7) Uani 1 1 d . . . . .
C21 C 0.5636(3) 0.8139(3) 0.1286(2) 0.0633(8) Uani 1 1 d . . . . .
C22 C 0.6342(5) 0.9159(3) 0.1425(3) 0.0995(14) Uani 1 1 d . . . . .
H22 H 0.6002 0.9761 0.1176 0.119 Uiso 1 1 calc R . . . .
C23 C 0.7575(6) 0.9252(5) 0.1950(4) 0.127(2) Uani 1 1 d . . . . .
H23 H 0.8068 0.9926 0.2061 0.152 Uiso 1 1 calc R . . . .
C24 C 0.8055(4) 0.8365(5) 0.2300(4) 0.1180(18) Uani 1 1 d . . . . .
H24 H 0.8879 0.8438 0.2648 0.142 Uiso 1 1 calc R . . . .
C25 C 0.7350(3) 0.7359(3) 0.2151(3) 0.0806(10) Uani 1 1 d . . . . .
H25 H 0.7705 0.6764 0.2404 0.097 Uiso 1 1 calc R . . . .
C26 C 0.5385(2) 0.6094(2) 0.1505(2) 0.0457(6) Uani 1 1 d . . . . .
H26 H 0.4631 0.5948 0.0887 0.055 Uiso 1 1 calc R . . . .
C27 C 0.5135(2) 0.6130(2) 0.2575(2) 0.0479(6) Uani 1 1 d . . . . .
H27A H 0.5872 0.6418 0.3196 0.057 Uiso 1 1 calc R . . . .
H27B H 0.4556 0.6666 0.2681 0.057 Uiso 1 1 calc R . . . .
C28 C 0.4650(2) 0.4928(2) 0.2554(2) 0.0488(6) Uani 1 1 d . . . . .
C29 C 0.3371(3) 0.4560(2) 0.1734(2) 0.0545(7) Uani 1 1 d . . . . .
C30 C 0.2910(3) 0.3284(3) 0.1259(2) 0.0584(7) Uani 1 1 d . . . . .
C31 C 0.1696(3) 0.2949(3) 0.0686(3) 0.0777(10) Uani 1 1 d . . . . .
H31 H 0.1191 0.3507 0.0557 0.093 Uiso 1 1 calc R . . . .
C32 C 0.1236(4) 0.1770(4) 0.0304(3) 0.0947(13) Uani 1 1 d . . . . .
H32 H 0.0424 0.1542 -0.0095 0.114 Uiso 1 1 calc R . . . .
C33 C 0.1972(5) 0.0948(4) 0.0511(3) 0.1028(15) Uani 1 1 d . . . . .
H33 H 0.1652 0.0166 0.0269 0.123 Uiso 1 1 calc R . . . .
C34 C 0.3172(4) 0.1263(3) 0.1071(3) 0.0923(12) Uani 1 1 d . . . . .
H34 H 0.3664 0.0697 0.1210 0.111 Uiso 1 1 calc R . . . .
C35 C 0.3663(3) 0.2439(3) 0.1436(2) 0.0660(9) Uani 1 1 d . . . . .
C36 C 0.4946(3) 0.2781(3) 0.2005(2) 0.0699(9) Uani 1 1 d . . . . .
C37 C 0.5461(3) 0.4052(2) 0.2207(2) 0.0565(7) Uani 1 1 d . . . . .
C38 C 0.4579(3) 0.4952(3) 0.3701(2) 0.0735(9) Uani 1 1 d . . . . .
H38A H 0.5362 0.5208 0.4245 0.110 Uiso 1 1 calc GR . . . .
H38B H 0.4300 0.4184 0.3682 0.110 Uiso 1 1 calc GR . . . .
H38C H 0.4032 0.5480 0.3890 0.110 Uiso 1 1 calc GR . . . .


_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
O1 N1 1.193(4) . ?
O2 N1 1.197(4) . ?
O3 O4 1.471(3) . ?
O3 C7 1.443(3) . ?
O4 C10 1.436(4) . ?
O5 C11 1.218(3) . ?
O6 C18 1.217(3) . ?
O7 H7 0.8200 . ?
O7 C10 1.384(4) . ?
N1 C6 1.475(4) . ?
C1 C2 1.388(5) . ?
C1 C6 1.387(4) . ?
C1 C7 1.515(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C7 H7A 0.9800 . ?
C7 C8 1.506(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.534(4) . ?
C9 C10 1.526(4) . ?
C9 C18 1.527(4) . ?
C9 C19 1.546(4) . ?
C10 C11 1.542(4) . ?
C11 C12 1.461(4) . ?
C12 C13 1.390(4) . ?
C12 C17 1.398(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.367(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(4) . ?
C17 C18 1.485(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O8 N2 1.218(3) . ?
O9 N2 1.222(3) . ?
O10 O11 1.467(3) . ?
O10 C26 1.446(3) . ?
O11 C37 1.440(3) . ?
O12 C36 1.216(4) . ?
O13 C29 1.207(3) . ?
O14 H14A 0.8200 . ?
O14 C37 1.390(3) . ?
N2 C21 1.458(4) . ?
C20 C21 1.389(4) . ?
C20 C25 1.392(4) . ?
C20 C26 1.510(4) . ?
C21 C22 1.391(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.393(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.351(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.374(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9800 . ?
C26 C27 1.524(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.523(3) . ?
C28 C29 1.532(4) . ?
C28 C37 1.519(4) . ?
C28 C38 1.539(4) . ?
C29 C30 1.499(4) . ?
C30 C31 1.385(4) . ?
C30 C35 1.395(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.393(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.368(6) . ?
C33 H33 0.9300 . ?
C33 C34 1.367(6) . ?
C34 H34 0.9300 . ?
C34 C35 1.400(4) . ?
C35 C36 1.456(5) . ?
C36 C37 1.543(4) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

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
C7 O3 O4 106.39(18) . . ?
C10 O4 O3 109.2(2) . . ?
C10 O7 H7 109.5 . . ?
O1 N1 O2 122.2(4) . . ?
O1 N1 C6 118.6(4) . . ?
O2 N1 C6 119.1(3) . . ?
C2 C1 C7 120.3(3) . . ?
C6 C1 C2 116.2(3) . . ?
C6 C1 C7 123.4(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.1(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 N1 120.9(3) . . ?
C5 C6 N1 116.0(3) . . ?
C5 C6 C1 123.1(3) . . ?
O3 C7 C1 105.6(2) . . ?
O3 C7 H7A 110.1 . . ?
O3 C7 C8 109.2(2) . . ?
C1 C7 H7A 110.1 . . ?
C8 C7 C1 111.8(2) . . ?
C8 C7 H7A 110.1 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C7 C8 C9 112.0(2) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 C19 109.8(3) . . ?
C10 C9 C8 108.3(2) . . ?
C10 C9 C18 109.7(2) . . ?
C10 C9 C19 111.8(3) . . ?
C18 C9 C8 111.1(2) . . ?
C18 C9 C19 106.2(2) . . ?
O4 C10 C9 109.4(2) . . ?
O4 C10 C11 99.2(3) . . ?
O7 C10 O4 112.1(2) . . ?
O7 C10 C9 109.0(3) . . ?
O7 C10 C11 111.2(2) . . ?
C9 C10 C11 115.7(2) . . ?
O5 C11 C10 118.0(3) . . ?
O5 C11 C12 123.1(3) . . ?
C12 C11 C10 118.9(2) . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 C17 119.6(3) . . ?
C17 C12 C11 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C18 121.1(2) . . ?
C16 C17 C12 119.1(3) . . ?
C16 C17 C18 119.8(3) . . ?
O6 C18 C9 120.8(3) . . ?
O6 C18 C17 121.3(3) . . ?
C17 C18 C9 117.7(2) . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 O10 O11 108.18(17) . . ?
C37 O11 O10 108.08(17) . . ?
C37 O14 H14A 109.5 . . ?
O8 N2 O9 123.6(3) . . ?
O8 N2 C21 118.5(3) . . ?
O9 N2 C21 117.9(3) . . ?
C21 C20 C25 116.6(3) . . ?
C21 C20 C26 124.7(3) . . ?
C25 C20 C26 118.6(3) . . ?
C20 C21 N2 121.4(2) . . ?
C20 C21 C22 122.7(4) . . ?
C22 C21 N2 115.8(3) . . ?
C21 C22 H22 121.0 . . ?
C21 C22 C23 118.0(4) . . ?
C23 C22 H22 121.0 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(4) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.3(5) . . ?
C25 C24 H24 119.3 . . ?
C20 C25 H25 119.4 . . ?
C24 C25 C20 121.1(4) . . ?
C24 C25 H25 119.4 . . ?
O10 C26 C20 104.3(2) . . ?
O10 C26 H26 110.6 . . ?
O10 C26 C27 109.8(2) . . ?
C20 C26 H26 110.6 . . ?
C20 C26 C27 110.9(2) . . ?
C27 C26 H26 110.6 . . ?
C26 C27 H27A 109.3 . . ?
C26 C27 H27B 109.3 . . ?
H27A C27 H27B 108.0 . . ?
C28 C27 C26 111.5(2) . . ?
C28 C27 H27A 109.3 . . ?
C28 C27 H27B 109.3 . . ?
C27 C28 C29 110.3(2) . . ?
C27 C28 C38 110.4(2) . . ?
C29 C28 C38 106.9(2) . . ?
C37 C28 C27 109.1(2) . . ?
C37 C28 C29 109.5(2) . . ?
C37 C28 C38 110.6(2) . . ?
O13 C29 C28 120.7(3) . . ?
O13 C29 C30 120.6(3) . . ?
C30 C29 C28 118.5(2) . . ?
C31 C30 C29 118.9(3) . . ?
C31 C30 C35 119.7(3) . . ?
C35 C30 C29 121.3(3) . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C32 119.7(4) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.3(4) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.7(4) . . ?
C34 C33 H33 119.6 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.1(4) . . ?
C35 C34 H34 120.0 . . ?
C30 C35 C34 119.4(3) . . ?
C30 C35 C36 120.1(3) . . ?
C34 C35 C36 120.5(3) . . ?
O12 C36 C35 124.8(3) . . ?
O12 C36 C37 117.4(3) . . ?
C35 C36 C37 117.8(2) . . ?
O11 C37 C28 108.2(2) . . ?
O11 C37 C36 103.7(2) . . ?
O14 C37 O11 111.0(3) . . ?
O14 C37 C28 111.2(2) . . ?
O14 C37 C36 109.7(2) . . ?
C28 C37 C36 112.8(3) . . ?
C28 C38 H38A 109.5 . . ?
C28 C38 H38B 109.5 . . ?
C28 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
