# 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_exp_243
_database_code_depnum_ccdc_archive 'CCDC 1505407'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_audit_creation_date             2016-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H7 N O6'
_chemical_formula_sum            'C11 H7 N O6'
_chemical_formula_weight         249.18
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   20.178(2)
_cell_length_b                   4.0966(4)
_cell_length_c                   25.538(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.660(9)
_cell_angle_gamma                90
_cell_volume                     2081.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1243
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8440
_cell_measurement_theta_min      2.8040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3384
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.062
_diffrn_reflns_theta_min         2.048
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  66.00   1.00   87.50    --   25.37  57.00 -30.00   76
  2  ω    -49.00  63.00   1.00   87.50    --   25.37 -57.00 150.00  112
  3  ω     -7.00  61.00   1.00   87.50    --   25.37 -57.00  30.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0187459000
_diffrn_orient_matrix_UB_12      -0.0215063000
_diffrn_orient_matrix_UB_13      -0.0208881000
_diffrn_orient_matrix_UB_21      0.0247742000
_diffrn_orient_matrix_UB_22      -0.0878158000
_diffrn_orient_matrix_UB_23      0.0174323000
_diffrn_orient_matrix_UB_31      -0.0174479000
_diffrn_orient_matrix_UB_32      -0.1478105000
_diffrn_orient_matrix_UB_33      -0.0073413000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1472
_reflns_number_total             2014
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.206
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2014
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.153
_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)+(0.0431P)²+5.3130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1602
_refine_ls_wR_factor_ref         0.1721
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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
O3 O 0.44982(10) -0.0125(6) 0.27534(8) 0.0446(6) Uani 1 1 d . . . . .
C5 C 0.37673(15) -0.3076(8) 0.32278(11) 0.0386(7) Uani 1 1 d . . . . .
O6 O 0.34039(12) -0.3727(6) 0.13333(8) 0.0543(7) Uani 1 1 d . . . . .
C8 C 0.35603(15) -0.3154(8) 0.22643(11) 0.0372(7) Uani 1 1 d . . . . .
C4 C 0.43387(15) -0.1187(8) 0.32232(11) 0.0377(7) Uani 1 1 d . . . . .
C1 C 0.40342(17) -0.3140(9) 0.41720(12) 0.0446(8) Uani 1 1 d . . . . .
O4 O 0.43107(12) 0.0284(6) 0.18830(9) 0.0552(7) Uani 1 1 d . . . . .
C7 C 0.33850(15) -0.4042(8) 0.27314(11) 0.0394(7) Uani 1 1 d . . . . .
H7 H 0.3004 -0.5322 0.2729 0.047 Uiso 1 1 calc R . . . .
C6 C 0.36097(16) -0.4050(8) 0.37195(12) 0.0439(8) Uani 1 1 d . . . . .
H6 H 0.3227 -0.5281 0.3737 0.053 Uiso 1 1 calc R . . . .
O2 O 0.42534(15) -0.3410(9) 0.50905(10) 0.0821(10) Uani 1 1 d . . . . .
C2 C 0.46110(17) -0.1299(9) 0.41642(12) 0.0492(9) Uani 1 1 d . . . . .
H2 H 0.4889 -0.0742 0.4480 0.059 Uiso 1 1 calc R . . . .
N1 N 0.38775(17) -0.4195(9) 0.46877(11) 0.0588(9) Uani 1 1 d . . . . .
C3 C 0.47672(17) -0.0308(9) 0.36847(13) 0.0478(8) Uani 1 1 d . . . . .
H3 H 0.5151 0.0923 0.3670 0.057 Uiso 1 1 calc R . . . .
C9 C 0.41305(15) -0.0951(8) 0.22589(12) 0.0393(7) Uani 1 1 d . . . . .
O5 O 0.26908(12) -0.6288(7) 0.17707(9) 0.0622(8) Uani 1 1 d . . . . .
C10 C 0.31703(16) -0.4537(8) 0.17686(12) 0.0416(8) Uani 1 1 d . . . . .
C11 C 0.3083(2) -0.5263(11) 0.08437(13) 0.0740(13) Uani 1 1 d . . . . .
H11A H 0.3260 -0.4351 0.0550 0.111 Uiso 1 1 calc GR . . . .
H11B H 0.2607 -0.4884 0.0795 0.111 Uiso 1 1 calc GR . . . .
H11C H 0.3168 -0.7569 0.0862 0.111 Uiso 1 1 calc GR . . . .
O1 O 0.33770(18) -0.5821(10) 0.46933(10) 0.0983(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C4 1.365(3) . ?
O3 C9 1.395(4) . ?
C5 C4 1.390(4) . ?
C5 C7 1.425(4) . ?
C5 C6 1.404(4) . ?
O6 C10 1.321(3) . ?
O6 C11 1.452(4) . ?
C8 C7 1.350(4) . ?
C8 C9 1.464(4) . ?
C8 C10 1.486(4) . ?
C4 C3 1.387(4) . ?
C1 C6 1.370(4) . ?
C1 C2 1.390(5) . ?
C1 N1 1.470(4) . ?
O4 C9 1.195(3) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
O2 N1 1.215(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
N1 O1 1.212(4) . ?
C3 H3 0.9300 . ?
O5 C10 1.205(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C4 O3 C9 123.4(2) . . ?
C4 C5 C7 118.2(3) . . ?
C4 C5 C6 118.6(3) . . ?
C6 C5 C7 123.1(3) . . ?
C10 O6 C11 116.4(3) . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 C10 118.1(3) . . ?
C9 C8 C10 122.1(3) . . ?
O3 C4 C5 120.2(3) . . ?
O3 C4 C3 117.3(3) . . ?
C3 C4 C5 122.5(3) . . ?
C6 C1 C2 122.8(3) . . ?
C6 C1 N1 118.6(3) . . ?
C2 C1 N1 118.6(3) . . ?
C5 C7 H7 119.1 . . ?
C8 C7 C5 121.9(3) . . ?
C8 C7 H7 119.1 . . ?
C5 C6 H6 120.9 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 H6 120.9 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
O2 N1 C1 118.9(3) . . ?
O1 N1 C1 118.5(3) . . ?
O1 N1 O2 122.6(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 C4 118.4(3) . . ?
C2 C3 H3 120.8 . . ?
O3 C9 C8 116.1(2) . . ?
O4 C9 O3 116.0(3) . . ?
O4 C9 C8 127.9(3) . . ?
O6 C10 C8 114.1(3) . . ?
O5 C10 O6 123.6(3) . . ?
O5 C10 C8 122.3(3) . . ?
O6 C11 H11A 109.5 . . ?
O6 C11 H11B 109.5 . . ?
O6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C4 C3 C2 178.8(3) . . . . ?
C5 C4 C3 C2 -1.2(5) . . . . ?
C4 O3 C9 C8 -1.8(4) . . . . ?
C4 O3 C9 O4 176.6(3) . . . . ?
C4 C5 C7 C8 -0.6(5) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C7 C5 C4 O3 4.3(4) . . . . ?
C7 C5 C4 C3 -175.7(3) . . . . ?
C7 C5 C6 C1 176.1(3) . . . . ?
C7 C8 C9 O3 5.5(4) . . . . ?
C7 C8 C9 O4 -172.8(3) . . . . ?
C7 C8 C10 O6 -175.5(3) . . . . ?
C7 C8 C10 O5 3.3(5) . . . . ?
C6 C5 C4 O3 -178.3(3) . . . . ?
C6 C5 C4 C3 1.8(5) . . . . ?
C6 C5 C7 C8 -177.9(3) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C6 C1 N1 O2 179.7(3) . . . . ?
C6 C1 N1 O1 -0.3(5) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C1 N1 O2 0.5(5) . . . . ?
C2 C1 N1 O1 -179.5(4) . . . . ?
N1 C1 C6 C5 -179.1(3) . . . . ?
N1 C1 C2 C3 179.6(3) . . . . ?
C9 O3 C4 C5 -3.0(4) . . . . ?
C9 O3 C4 C3 176.9(3) . . . . ?
C9 C8 C7 C5 -4.3(5) . . . . ?
C9 C8 C10 O6 3.1(4) . . . . ?
C9 C8 C10 O5 -178.2(3) . . . . ?
C10 C8 C7 C5 174.2(3) . . . . ?
C10 C8 C9 O3 -173.0(3) . . . . ?
C10 C8 C9 O4 8.7(5) . . . . ?
C11 O6 C10 C8 174.2(3) . . . . ?
C11 O6 C10 O5 -4.5(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-31
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.718
_oxdiff_exptl_absorpt_empirical_full_min 0.721
####################################################################### 
# 
# 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_app
_database_code_depnum_ccdc_archive 'CCDC 1505411'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N2 O7'
_chemical_formula_weight         334.28

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8470(3)
_cell_length_b                   14.2490(8)
_cell_length_c                   15.0925(8)
_cell_angle_alpha                118.000(6)
_cell_angle_beta                 90.705(4)
_cell_angle_gamma                92.192(4)
_cell_volume                     1488.03(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1713
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      19.47

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.116
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10699
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5228
_reflns_number_gt                4349
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.6334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5228
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40672(17) 0.55538(10) 0.17533(10) 0.0296(3) Uani 1 1 d . . .
O2 O 0.30194(16) 1.24166(10) -0.14336(10) 0.0291(3) Uani 1 1 d . . .
O3 O 0.12148(16) 1.10602(10) -0.21001(9) 0.0271(3) Uani 1 1 d . . .
O4 O 0.40647(14) 1.06599(9) 0.15906(9) 0.0212(3) Uani 1 1 d . . .
O5 O 0.41589(15) 0.96089(10) 0.22827(9) 0.0239(3) Uani 1 1 d . . .
O6 O 0.05784(15) 0.74281(10) 0.01183(9) 0.0236(3) Uani 1 1 d . . .
O7 O 0.40014(15) 0.73121(10) 0.27294(9) 0.0258(3) Uani 1 1 d . . .
O8 O 0.92828(16) 1.25317(10) 0.60324(10) 0.0285(3) Uani 1 1 d . . .
N4 N 0.88187(18) 0.66298(11) 0.64235(11) 0.0183(3) Uani 1 1 d . . .
O10 O 1.21631(15) 0.62642(10) 0.61964(9) 0.0263(3) Uani 1 1 d . . .
O11 O 0.72122(19) 1.23895(11) 0.50054(10) 0.0360(3) Uani 1 1 d . . .
O12 O 0.68817(14) 0.77940(9) 0.44892(9) 0.0203(3) Uani 1 1 d . . .
O13 O 0.70883(15) 0.64124(9) 0.47517(9) 0.0224(3) Uani 1 1 d . . .
O14 O 0.99059(16) 0.82890(9) 0.74718(9) 0.0264(3) Uani 1 1 d . . .
O15 O 1.24239(16) 0.65845(10) 0.77969(10) 0.0284(3) Uani 1 1 d . . .
N1 N 0.26037(18) 0.75936(11) 0.12783(11) 0.0206(3) Uani 1 1 d . . .
H1 H 0.3305 0.8037 0.1741 0.025 Uiso 1 1 calc R . .
N2 N 0.22902(18) 1.16281(12) -0.14539(11) 0.0221(3) Uani 1 1 d . . .
N3 N 0.81038(19) 1.20268(12) 0.54333(11) 0.0240(3) Uani 1 1 d . . .
C1 C 0.5224(3) 0.55236(16) 0.24957(15) 0.0348(5) Uani 1 1 d . . .
H1A H 0.6239 0.5955 0.2568 0.052 Uiso 1 1 calc R . .
H1B H 0.5521 0.4803 0.2282 0.052 Uiso 1 1 calc R . .
H1C H 0.4679 0.5792 0.3129 0.052 Uiso 1 1 calc R . .
C2 C 0.3585(2) 0.65198(14) 0.19654(13) 0.0210(4) Uani 1 1 d . . .
C3 C 0.2411(2) 0.65105(14) 0.11501(13) 0.0215(4) Uani 1 1 d . . .
C4 C 0.1748(2) 0.79360(14) 0.07157(12) 0.0192(4) Uani 1 1 d . . .
C5 C 0.2370(2) 0.89952(14) 0.08033(13) 0.0189(4) Uani 1 1 d . . .
C6 C 0.1891(2) 0.92125(14) 0.00598(13) 0.0196(4) Uani 1 1 d . . .
H6 H 0.1153 0.8733 -0.0453 0.023 Uiso 1 1 calc R . .
C7 C 0.2493(2) 1.01628(13) 0.00429(12) 0.0193(4) Uani 1 1 d . . .
C8 C 0.2070(2) 1.04131(14) -0.07273(13) 0.0193(4) Uani 1 1 d . . .
H8 H 0.1357 0.9956 -0.1268 0.023 Uiso 1 1 calc R . .
C9 C 0.2737(2) 1.13518(14) -0.06612(13) 0.0199(4) Uani 1 1 d . . .
C10 C 0.3830(2) 1.20476(14) 0.01226(13) 0.0216(4) Uani 1 1 d . . .
H10 H 0.4261 1.2673 0.0140 0.026 Uiso 1 1 calc R . .
C11 C 0.4272(2) 1.18051(14) 0.08729(13) 0.0225(4) Uani 1 1 d . . .
H11 H 0.5018 1.2256 0.1398 0.027 Uiso 1 1 calc R . .
C12 C 0.3586(2) 1.08761(14) 0.08307(13) 0.0196(4) Uani 1 1 d . . .
C13 C 0.3559(2) 0.97314(14) 0.16034(13) 0.0193(4) Uani 1 1 d . . .
C14 C 0.2942(2) 0.57115(15) 0.00995(13) 0.0269(4) Uani 1 1 d . . .
H14A H 0.2262 0.5785 -0.0395 0.040 Uiso 1 1 calc R . .
H14B H 0.2773 0.5002 0.0012 0.040 Uiso 1 1 calc R . .
H14C H 0.4125 0.5846 0.0022 0.040 Uiso 1 1 calc R . .
C15 C 0.0591(2) 0.62497(15) 0.13621(14) 0.0270(4) Uani 1 1 d . . .
H15A H 0.0290 0.6776 0.2019 0.041 Uiso 1 1 calc R . .
H15B H 0.0540 0.5561 0.1331 0.041 Uiso 1 1 calc R . .
H15C H -0.0193 0.6250 0.0869 0.041 Uiso 1 1 calc R . .
C16 C 0.7764(2) 1.09175(13) 0.52020(13) 0.0192(4) Uani 1 1 d . . .
C17 C 0.8386(2) 1.05930(13) 0.58660(13) 0.0187(4) Uani 1 1 d . . .
H17 H 0.8992 1.1068 0.6450 0.022 Uiso 1 1 calc R . .
C18 C 0.8082(2) 0.95295(13) 0.56367(12) 0.0178(4) Uani 1 1 d . . .
C19 C 0.8673(2) 0.90952(13) 0.62646(13) 0.0186(4) Uani 1 1 d . . .
H19 H 0.9274 0.9538 0.6861 0.022 Uiso 1 1 calc R . .
C20 C 0.8377(2) 0.80588(13) 0.60098(12) 0.0185(4) Uani 1 1 d . . .
C21 C 0.9095(2) 0.76680(13) 0.67016(13) 0.0192(4) Uani 1 1 d . . .
C22 C 0.9620(2) 0.61207(13) 0.69608(13) 0.0187(4) Uani 1 1 d . . .
C23 C 1.1552(2) 0.63747(13) 0.70601(13) 0.0209(4) Uani 1 1 d . . .
C24 C 1.3985(2) 0.64212(18) 0.61818(17) 0.0361(5) Uani 1 1 d . . .
H24A H 1.4322 0.7147 0.6642 0.054 Uiso 1 1 calc R . .
H24B H 1.4304 0.6266 0.5516 0.054 Uiso 1 1 calc R . .
H24C H 1.4543 0.5956 0.6377 0.054 Uiso 1 1 calc R . .
C25 C 0.7198(2) 0.88445(13) 0.47468(13) 0.0185(4) Uani 1 1 d . . .
C26 C 0.7440(2) 0.73521(13) 0.50714(13) 0.0184(4) Uani 1 1 d . . .
C27 C 0.9322(2) 0.49167(14) 0.63198(13) 0.0242(4) Uani 1 1 d . . .
H27A H 0.8119 0.4736 0.6240 0.036 Uiso 1 1 calc R . .
H27B H 0.9864 0.4562 0.6645 0.036 Uiso 1 1 calc R . .
H27C H 0.9797 0.4697 0.5673 0.036 Uiso 1 1 calc R . .
C28 C 0.8873(2) 0.64803(14) 0.79853(13) 0.0228(4) Uani 1 1 d . . .
H28A H 0.9012 0.7241 0.8369 0.034 Uiso 1 1 calc R . .
H28B H 0.9454 0.6159 0.8330 0.034 Uiso 1 1 calc R . .
H28C H 0.7681 0.6269 0.7906 0.034 Uiso 1 1 calc R . .
C29 C 0.6589(2) 0.91811(14) 0.40788(13) 0.0208(4) Uani 1 1 d . . .
H29 H 0.6009 0.8706 0.3485 0.025 Uiso 1 1 calc R . .
C30 C 0.6868(2) 1.02356(14) 0.43184(13) 0.0216(4) Uani 1 1 d . . .
H30 H 0.6459 1.0487 0.3892 0.026 Uiso 1 1 calc R . .
H4 H 0.830(3) 0.6233(17) 0.5840(16) 0.032(6) Uiso 1 1 d . . .


_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 C2 1.330(2) . ?
O1 C1 1.451(2) . ?
O2 N2 1.2282(19) . ?
O3 N2 1.2266(18) . ?
O4 C12 1.372(2) . ?
O4 C13 1.376(2) . ?
O5 C13 1.210(2) . ?
O6 C4 1.223(2) . ?
O7 C2 1.205(2) . ?
O8 N3 1.2283(19) . ?
N4 C21 1.342(2) . ?
N4 C22 1.468(2) . ?
N4 H4 0.88(2) . ?
O10 C23 1.335(2) . ?
O10 C24 1.440(2) . ?
O11 N3 1.226(2) . ?
O12 C25 1.370(2) . ?
O12 C26 1.376(2) . ?
O13 C26 1.210(2) . ?
O14 C21 1.230(2) . ?
O15 C23 1.203(2) . ?
N1 C4 1.345(2) . ?
N1 C3 1.464(2) . ?
N1 H1 0.8600 . ?
N2 C9 1.467(2) . ?
N3 C16 1.462(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.523(3) . ?
C3 C14 1.530(2) . ?
C3 C15 1.537(2) . ?
C4 C5 1.513(2) . ?
C5 C6 1.349(2) . ?
C5 C13 1.462(2) . ?
C6 C7 1.429(2) . ?
C6 H6 0.9300 . ?
C7 C12 1.398(2) . ?
C7 C8 1.406(2) . ?
C8 C9 1.376(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(2) . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.377(2) . ?
C16 C30 1.388(2) . ?
C17 C18 1.397(2) . ?
C17 H17 0.9300 . ?
C18 C25 1.390(2) . ?
C18 C19 1.435(2) . ?
C19 C20 1.349(2) . ?
C19 H19 0.9300 . ?
C20 C26 1.462(2) . ?
C20 C21 1.508(2) . ?
C22 C28 1.516(2) . ?
C22 C27 1.529(2) . ?
C22 C23 1.534(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C29 1.391(2) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.378(2) . ?
C29 H29 0.9300 . ?
C30 H30 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
C2 O1 C1 114.75(14) . . ?
C12 O4 C13 122.58(13) . . ?
C21 N4 C22 122.26(15) . . ?
C21 N4 H4 117.3(14) . . ?
C22 N4 H4 119.4(14) . . ?
C23 O10 C24 115.97(15) . . ?
C25 O12 C26 122.73(13) . . ?
C4 N1 C3 123.88(14) . . ?
C4 N1 H1 118.1 . . ?
C3 N1 H1 118.1 . . ?
O3 N2 O2 123.64(15) . . ?
O3 N2 C9 118.37(14) . . ?
O2 N2 C9 117.99(14) . . ?
O11 N3 O8 124.11(15) . . ?
O11 N3 C16 117.98(15) . . ?
O8 N3 C16 117.90(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O7 C2 O1 123.67(17) . . ?
O7 C2 C3 123.68(16) . . ?
O1 C2 C3 112.64(15) . . ?
N1 C3 C2 104.38(13) . . ?
N1 C3 C14 109.96(14) . . ?
C2 C3 C14 111.72(14) . . ?
N1 C3 C15 111.83(14) . . ?
C2 C3 C15 106.96(14) . . ?
C14 C3 C15 111.74(15) . . ?
O6 C4 N1 124.34(16) . . ?
O6 C4 C5 119.19(16) . . ?
N1 C4 C5 116.37(15) . . ?
C6 C5 C13 119.82(16) . . ?
C6 C5 C4 117.26(15) . . ?
C13 C5 C4 122.71(15) . . ?
C5 C6 C7 121.52(16) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C12 C7 C8 118.25(16) . . ?
C12 C7 C6 117.99(16) . . ?
C8 C7 C6 123.75(16) . . ?
C9 C8 C7 118.33(16) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 122.69(17) . . ?
C8 C9 N2 118.89(15) . . ?
C10 C9 N2 118.42(15) . . ?
C11 C10 C9 119.53(17) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 118.61(16) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
O4 C12 C11 116.85(15) . . ?
O4 C12 C7 120.56(16) . . ?
C11 C12 C7 122.57(17) . . ?
O5 C13 O4 115.94(15) . . ?
O5 C13 C5 126.67(17) . . ?
O4 C13 C5 117.39(15) . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C30 122.99(16) . . ?
C17 C16 N3 118.10(15) . . ?
C30 C16 N3 118.89(16) . . ?
C16 C17 C18 118.03(16) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C25 C18 C17 118.93(16) . . ?
C25 C18 C19 117.80(15) . . ?
C17 C18 C19 123.25(16) . . ?
C20 C19 C18 121.54(16) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C26 119.80(16) . . ?
C19 C20 C21 117.71(15) . . ?
C26 C20 C21 122.46(15) . . ?
O14 C21 N4 123.19(16) . . ?
O14 C21 C20 120.03(15) . . ?
N4 C21 C20 116.77(15) . . ?
N4 C22 C28 111.37(14) . . ?
N4 C22 C27 107.68(14) . . ?
C28 C22 C27 110.09(14) . . ?
N4 C22 C23 109.25(13) . . ?
C28 C22 C23 110.62(14) . . ?
C27 C22 C23 107.71(14) . . ?
O15 C23 O10 124.06(16) . . ?
O15 C23 C22 124.81(16) . . ?
O10 C23 C22 110.99(15) . . ?
O10 C24 H24A 109.5 . . ?
O10 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O10 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O12 C25 C18 120.87(16) . . ?
O12 C25 C29 116.72(15) . . ?
C18 C25 C29 122.41(16) . . ?
O13 C26 O12 115.98(15) . . ?
O13 C26 C20 126.77(16) . . ?
O12 C26 C20 117.25(14) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C25 118.35(16) . . ?
C30 C29 H29 120.8 . . ?
C25 C29 H29 120.8 . . ?
C29 C30 C16 119.26(17) . . ?
C29 C30 H30 120.4 . . ?
C16 C30 H30 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_ncaca
_database_code_depnum_ccdc_archive 'CCDC 1505412'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_audit_creation_date             2016-05-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 N3 O10'
_chemical_formula_sum            'C25 H19 N3 O10'
_chemical_formula_weight         521.43
_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                   7.8580(8)
_cell_length_b                   11.5608(12)
_cell_length_c                   13.8689(11)
_cell_angle_alpha                108.556(8)
_cell_angle_beta                 94.723(7)
_cell_angle_gamma                91.871(8)
_cell_volume                     1188.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5550
_cell_measurement_theta_min      2.4620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.3258
_exptl_crystal_size_mid          0.2569
_exptl_crystal_size_min          0.2148
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7190
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.911
_diffrn_reflns_theta_max         24.811
_diffrn_reflns_theta_min         1.862
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2437
_reflns_number_total             4050
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      1.041
_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)+(0.0731P)²+0.5675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1887
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7), C12(H12), C13(H13), C16(H16), C17(H17),
 N2(H2), N3(H3A)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_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
C1 C -0.1660(5) 0.2780(4) 0.8434(3) 0.0510(10) Uani 1 1 d . . . . .
H1 H -0.1461 0.1987 0.8043 0.061 Uiso 1 1 calc R . . . .
C2 C -0.2565(5) 0.2984(4) 0.9262(3) 0.0546(11) Uani 1 1 d . . . . .
C3 C -0.2884(6) 0.4142(4) 0.9870(3) 0.0620(12) Uani 1 1 d . . . . .
H3 H -0.3512 0.4248 1.0429 0.074 Uiso 1 1 calc R . . . .
C4 C -0.2261(5) 0.5133(4) 0.9638(3) 0.0606(12) Uani 1 1 d . . . . .
H4 H -0.2460 0.5923 1.0035 0.073 Uiso 1 1 calc R . . . .
C5 C -0.1342(5) 0.4936(4) 0.8810(3) 0.0488(10) Uani 1 1 d . . . . .
C6 C -0.1037(5) 0.3779(3) 0.8180(3) 0.0457(9) Uani 1 1 d . . . . .
C7 C -0.0133(5) 0.3677(4) 0.7306(3) 0.0478(10) Uani 1 1 d . . . . .
H7 H 0.0048 0.2905 0.6867 0.057 Uiso 1 1 calc R . . . .
C8 C 0.0464(5) 0.4673(3) 0.7105(3) 0.0434(9) Uani 1 1 d . . . . .
C9 C 0.0258(6) 0.5874(4) 0.7817(3) 0.0569(11) Uani 1 1 d . . . . .
C10 C 0.1361(5) 0.4462(4) 0.6150(3) 0.0445(9) Uani 1 1 d . . . . .
C11 C 0.2593(4) 0.5467(3) 0.5014(3) 0.0413(9) Uani 1 1 d . . . . .
C12 C 0.2845(5) 0.4397(3) 0.4218(3) 0.0476(10) Uani 1 1 d . . . . .
H12 H 0.2446 0.3640 0.4241 0.057 Uiso 1 1 calc R . . . .
C13 C 0.3688(5) 0.4470(3) 0.3400(3) 0.0458(9) Uani 1 1 d . . . . .
H13 H 0.3851 0.3765 0.2867 0.055 Uiso 1 1 calc R . . . .
C14 C 0.4277(4) 0.5585(3) 0.3380(2) 0.0395(9) Uani 1 1 d . . . . .
C15 C 0.4036(4) 0.6661(3) 0.4151(2) 0.0386(8) Uani 1 1 d . . . . .
C16 C 0.3176(5) 0.6568(3) 0.4968(3) 0.0435(9) Uani 1 1 d . . . . .
H16 H 0.2998 0.7275 0.5493 0.052 Uiso 1 1 calc R . . . .
C17 C 0.4699(4) 0.7780(3) 0.4067(3) 0.0415(9) Uani 1 1 d . . . . .
H17 H 0.4568 0.8507 0.4584 0.050 Uiso 1 1 calc R . . . .
C18 C 0.5509(4) 0.7816(3) 0.3260(3) 0.0403(9) Uani 1 1 d . . . . .
C19 C 0.5740(5) 0.6677(3) 0.2453(3) 0.0415(9) Uani 1 1 d . . . . .
C20 C 0.6217(5) 0.9014(3) 0.3228(3) 0.0462(9) Uani 1 1 d . . . . .
C21 C 0.7533(5) 1.0164(3) 0.2243(3) 0.0496(10) Uani 1 1 d . . . . .
C22 C 0.6161(6) 1.1070(4) 0.2266(3) 0.0678(13) Uani 1 1 d . . . . .
H22A H 0.5282 1.0712 0.1718 0.102 Uiso 1 1 calc GR . . . .
H22B H 0.6664 1.1800 0.2189 0.102 Uiso 1 1 calc GR . . . .
H22C H 0.5673 1.1271 0.2907 0.102 Uiso 1 1 calc GR . . . .
C23 C 0.8310(6) 0.9816(4) 0.1217(3) 0.0736(14) Uani 1 1 d . . . . .
H23A H 0.9144 0.9223 0.1204 0.110 Uiso 1 1 calc GR . . . .
H23B H 0.8850 1.0531 0.1136 0.110 Uiso 1 1 calc GR . . . .
H23C H 0.7423 0.9474 0.0671 0.110 Uiso 1 1 calc GR . . . .
C24 C 0.8980(6) 1.0718(4) 0.3080(3) 0.0556(11) Uani 1 1 d . . . . .
C25 C 1.1483(7) 1.0353(5) 0.3992(4) 0.110(2) Uani 1 1 d . . . . .
H25A H 1.2342 1.0715 0.3705 0.165 Uiso 1 1 calc GR . . . .
H25B H 1.1944 0.9693 0.4189 0.165 Uiso 1 1 calc GR . . . .
H25C H 1.1130 1.0958 0.4582 0.165 Uiso 1 1 calc GR . . . .
N1 N -0.3250(6) 0.1940(5) 0.9518(3) 0.0804(12) Uani 1 1 d . . . . .
N2 N 0.1746(4) 0.5450(3) 0.5870(2) 0.0459(8) Uani 1 1 d . . . . .
H2 H 0.1444 0.6141 0.6253 0.055 Uiso 1 1 calc R . . . .
N3 N 0.6809(4) 0.9052(3) 0.2364(2) 0.0505(8) Uani 1 1 d . . . . .
H3A H 0.6760 0.8387 0.1855 0.061 Uiso 1 1 calc R . . . .
O1 O -0.4306(5) 0.2110(4) 1.0132(3) 0.1134(14) Uani 1 1 d . . . . .
O2 O -0.2745(6) 0.0942(4) 0.9090(3) 0.1071(14) Uani 1 1 d . . . . .
O3 O -0.0706(4) 0.5942(2) 0.86165(19) 0.0599(8) Uani 1 1 d . . . . .
O4 O 0.0854(5) 0.6812(3) 0.7784(3) 0.0961(12) Uani 1 1 d . . . . .
O5 O 0.1685(4) 0.3431(2) 0.5683(2) 0.0607(8) Uani 1 1 d . . . . .
O6 O 0.5134(3) 0.5618(2) 0.25594(17) 0.0445(6) Uani 1 1 d . . . . .
O7 O 0.6449(3) 0.6583(2) 0.16868(19) 0.0558(7) Uani 1 1 d . . . . .
O8 O 0.6234(4) 0.9932(2) 0.39809(19) 0.0617(8) Uani 1 1 d . . . . .
O9 O 0.9237(4) 1.1790(3) 0.3548(2) 0.0741(9) Uani 1 1 d . . . . .
O10 O 1.0012(4) 0.9886(3) 0.3234(2) 0.0713(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.362(5) . ?
C1 C6 1.396(5) . ?
C2 C3 1.380(6) . ?
C2 N1 1.461(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(5) . ?
C5 C6 1.387(5) . ?
C5 O3 1.363(4) . ?
C6 C7 1.430(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.347(5) . ?
C8 C9 1.448(5) . ?
C8 C10 1.506(5) . ?
C9 O3 1.378(4) . ?
C9 O4 1.183(5) . ?
C10 N2 1.351(4) . ?
C10 O5 1.209(4) . ?
C11 C12 1.404(5) . ?
C11 C16 1.360(5) . ?
C11 N2 1.414(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(5) . ?
C14 C15 1.389(4) . ?
C14 O6 1.380(4) . ?
C15 C16 1.396(5) . ?
C15 C17 1.422(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.344(4) . ?
C18 C19 1.459(5) . ?
C18 C20 1.490(5) . ?
C19 O6 1.356(4) . ?
C19 O7 1.216(4) . ?
C20 N3 1.333(4) . ?
C20 O8 1.228(4) . ?
C21 C22 1.522(5) . ?
C21 C23 1.534(5) . ?
C21 C24 1.521(6) . ?
C21 N3 1.452(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O9 1.204(4) . ?
C24 O10 1.334(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 O10 1.460(6) . ?
N1 O1 1.213(5) . ?
N1 O2 1.213(5) . ?
N2 H2 0.8600 . ?
N3 H3A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.5 . . ?
C2 C1 C6 118.9(4) . . ?
C6 C1 H1 120.5 . . ?
C1 C2 C3 122.8(4) . . ?
C1 C2 N1 119.1(4) . . ?
C3 C2 N1 118.1(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 123.1(4) . . ?
O3 C5 C4 117.1(4) . . ?
O3 C5 C6 119.8(3) . . ?
C1 C6 C7 124.0(4) . . ?
C5 C6 C1 117.5(3) . . ?
C5 C6 C7 118.5(4) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 C10 117.2(3) . . ?
C9 C8 C10 123.6(4) . . ?
O3 C9 C8 117.6(4) . . ?
O4 C9 C8 126.2(4) . . ?
O4 C9 O3 116.3(4) . . ?
N2 C10 C8 117.2(3) . . ?
O5 C10 C8 118.5(4) . . ?
O5 C10 N2 124.2(3) . . ?
C12 C11 N2 122.4(3) . . ?
C16 C11 C12 119.5(3) . . ?
C16 C11 N2 118.1(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 122.1(3) . . ?
C13 C14 O6 117.7(3) . . ?
O6 C14 C15 120.2(3) . . ?
C14 C15 C16 117.6(3) . . ?
C14 C15 C17 118.1(3) . . ?
C16 C15 C17 124.3(3) . . ?
C11 C16 C15 121.6(3) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C15 C17 H17 119.1 . . ?
C18 C17 C15 121.7(3) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 C20 119.3(3) . . ?
C19 C18 C20 121.3(3) . . ?
O6 C19 C18 117.9(3) . . ?
O7 C19 C18 125.9(3) . . ?
O7 C19 O6 116.1(3) . . ?
N3 C20 C18 118.1(3) . . ?
O8 C20 C18 120.1(3) . . ?
O8 C20 N3 121.8(4) . . ?
C22 C21 C23 110.3(3) . . ?
C24 C21 C22 111.0(3) . . ?
C24 C21 C23 107.4(3) . . ?
N3 C21 C22 110.7(3) . . ?
N3 C21 C23 107.9(3) . . ?
N3 C21 C24 109.5(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O9 C24 C21 125.2(4) . . ?
O9 C24 O10 121.9(4) . . ?
O10 C24 C21 112.9(3) . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O10 C25 H25A 109.5 . . ?
O10 C25 H25B 109.5 . . ?
O10 C25 H25C 109.5 . . ?
O1 N1 C2 118.6(5) . . ?
O1 N1 O2 123.6(5) . . ?
O2 N1 C2 117.8(4) . . ?
C10 N2 C11 126.8(3) . . ?
C10 N2 H2 116.6 . . ?
C11 N2 H2 116.6 . . ?
C20 N3 C21 123.1(3) . . ?
C20 N3 H3A 118.5 . . ?
C21 N3 H3A 118.5 . . ?
C5 O3 C9 123.0(3) . . ?
C19 O6 C14 122.6(3) . . ?
C24 O10 C25 116.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.4(6) . . . . ?
C1 C2 N1 O1 -166.6(4) . . . . ?
C1 C2 N1 O2 12.3(6) . . . . ?
C1 C6 C7 C8 -179.0(4) . . . . ?
C2 C1 C6 C5 1.6(5) . . . . ?
C2 C1 C6 C7 -177.4(4) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C2 N1 O1 12.6(6) . . . . ?
C3 C2 N1 O2 -168.4(4) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C3 C4 C5 O3 -178.4(4) . . . . ?
C4 C5 C6 C1 -2.1(6) . . . . ?
C4 C5 C6 C7 177.0(4) . . . . ?
C4 C5 O3 C9 179.2(4) . . . . ?
C5 C6 C7 C8 2.0(6) . . . . ?
C6 C1 C2 C3 -0.5(6) . . . . ?
C6 C1 C2 N1 178.7(4) . . . . ?
C6 C5 O3 C9 -0.6(6) . . . . ?
C6 C7 C8 C9 3.1(6) . . . . ?
C6 C7 C8 C10 -178.5(3) . . . . ?
C7 C8 C9 O3 -6.8(6) . . . . ?
C7 C8 C9 O4 172.6(5) . . . . ?
C7 C8 C10 N2 171.0(3) . . . . ?
C7 C8 C10 O5 -8.8(5) . . . . ?
C8 C9 O3 C5 5.6(6) . . . . ?
C8 C10 N2 C11 179.4(3) . . . . ?
C9 C8 C10 N2 -10.7(5) . . . . ?
C9 C8 C10 O5 169.5(4) . . . . ?
C10 C8 C9 O3 175.0(3) . . . . ?
C10 C8 C9 O4 -5.7(7) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C11 C16 C15 -0.6(5) . . . . ?
C12 C11 N2 C10 13.3(5) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C12 C13 C14 O6 179.0(3) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
C13 C14 C15 C17 179.9(3) . . . . ?
C13 C14 O6 C19 178.6(3) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
C14 C15 C17 C18 1.3(5) . . . . ?
C15 C14 O6 C19 -1.4(5) . . . . ?
C15 C17 C18 C19 -0.9(5) . . . . ?
C15 C17 C18 C20 -178.4(3) . . . . ?
C16 C11 C12 C13 0.3(5) . . . . ?
C16 C11 N2 C10 -166.9(3) . . . . ?
C16 C15 C17 C18 -179.6(3) . . . . ?
C17 C15 C16 C11 -179.0(3) . . . . ?
C17 C18 C19 O6 -0.7(5) . . . . ?
C17 C18 C19 O7 -179.9(4) . . . . ?
C17 C18 C20 N3 -171.2(3) . . . . ?
C17 C18 C20 O8 8.4(5) . . . . ?
C18 C19 O6 C14 1.8(5) . . . . ?
C18 C20 N3 C21 -179.8(3) . . . . ?
C19 C18 C20 N3 11.4(5) . . . . ?
C19 C18 C20 O8 -169.1(4) . . . . ?
C20 C18 C19 O6 176.8(3) . . . . ?
C20 C18 C19 O7 -2.5(6) . . . . ?
C21 C24 O10 C25 177.1(4) . . . . ?
C22 C21 C24 O9 -15.9(6) . . . . ?
C22 C21 C24 O10 166.3(3) . . . . ?
C22 C21 N3 C20 -67.5(5) . . . . ?
C23 C21 C24 O9 104.8(5) . . . . ?
C23 C21 C24 O10 -73.1(4) . . . . ?
C23 C21 N3 C20 171.7(3) . . . . ?
C24 C21 N3 C20 55.1(5) . . . . ?
N1 C2 C3 C4 -179.6(4) . . . . ?
N2 C11 C12 C13 -179.9(3) . . . . ?
N2 C11 C16 C15 179.5(3) . . . . ?
N3 C21 C24 O9 -138.3(4) . . . . ?
N3 C21 C24 O10 43.8(4) . . . . ?
O3 C5 C6 C1 177.6(3) . . . . ?
O3 C5 C6 C7 -3.3(5) . . . . ?
O4 C9 O3 C5 -173.8(4) . . . . ?
O5 C10 N2 C11 -0.9(6) . . . . ?
O6 C14 C15 C16 -179.3(3) . . . . ?
O6 C14 C15 C17 -0.1(5) . . . . ?
O7 C19 O6 C14 -178.9(3) . . . . ?
O8 C20 N3 C21 0.7(6) . . . . ?
O9 C24 O10 C25 -0.8(6) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.222 0.173 0.164 30.1 0.9 ?
2 -0.222 0.827 0.836 30.1 0.9 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
