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

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

data_ODPI-1
_database_code_depnum_ccdc_archive 'CCDC 1490507'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O7'
_chemical_formula_sum            'C22 H20 N2 O7'
_chemical_formula_weight         424.40
_chemical_absolute_configuration rm

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           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '
_symmetry_space_group_name_HALL  '-C 2yc '

loop_
_symmetry_equiv_pos_as_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                   16.6850(5)
_cell_length_b                   5.0270(2)
_cell_length_c                   22.8630(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.020(2)
_cell_angle_gamma                90.00
_cell_volume                     1907.07(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3092
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.68

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      1.479
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7046
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1666
_reflns_number_gt                1401
_reflns_threshold_expression     >2σ(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 > 2σ(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)+(0.0379P)²+1.6053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1666
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_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
C1 C 0.44248(9) 0.2177(3) 0.21494(7) 0.0398(4) Uani 1 1 d . . .
C2 C 0.46475(10) 0.4305(4) 0.18194(7) 0.0424(4) Uani 1 1 d . . .
H2 H 0.5185 0.4829 0.1845 0.051 Uiso 1 1 calc R . .
C3 C 0.40764(10) 0.5660(3) 0.14512(7) 0.0404(4) Uani 1 1 d . . .
H3 H 0.4218 0.7095 0.1227 0.048 Uiso 1 1 calc R . .
C4 C 0.32878(9) 0.4803(3) 0.14291(6) 0.0360(4) Uani 1 1 d . . .
C5 C 0.30724(9) 0.2669(3) 0.17603(6) 0.0357(4) Uani 1 1 d . . .
C6 C 0.36331(10) 0.1294(3) 0.21296(7) 0.0406(4) Uani 1 1 d . . .
H6 H 0.3490 -0.0143 0.2353 0.049 Uiso 1 1 calc R . .
C7 C 0.21816(10) 0.2311(3) 0.16454(7) 0.0394(4) Uani 1 1 d . . .
C8 C 0.25512(10) 0.5832(3) 0.10879(7) 0.0396(4) Uani 1 1 d . . .
C9 C 0.10760(9) 0.4607(4) 0.09976(8) 0.0467(4) Uani 1 1 d . . .
H9A H 0.1014 0.6351 0.0817 0.056 Uiso 1 1 calc R . .
H9B H 0.0739 0.4547 0.1318 0.056 Uiso 1 1 calc R . .
C10 C 0.07865(10) 0.2522(4) 0.05468(7) 0.0449(4) Uani 1 1 d . . .
H10A H 0.0822 0.0789 0.0735 0.054 Uiso 1 1 calc R . .
H10B H 0.0223 0.2854 0.0416 0.054 Uiso 1 1 calc R . .
C11 C 0.12500(11) 0.2443(4) 0.00183(8) 0.0525(5) Uani 1 1 d . . .
H11A H 0.1819 0.2210 0.0144 0.063 Uiso 1 1 calc R . .
H11B H 0.1071 0.0941 -0.0228 0.063 Uiso 1 1 calc R . .
N1 N 0.19183(8) 0.4251(3) 0.12366(6) 0.0395(3) Uani 1 1 d . . .
O1 O 0.5000 0.0730(3) 0.2500 0.0520(5) Uani 1 2 d S . .
O2 O 0.17539(7) 0.0735(3) 0.18599(6) 0.0556(4) Uani 1 1 d . . .
O3 O 0.24777(7) 0.7674(3) 0.07437(6) 0.0558(4) Uani 1 1 d . . .
O4 O 0.11342(8) 0.4828(3) -0.03103(7) 0.0728(5) Uani 1 1 d . . .
H4 H 0.1574 0.5458 -0.0365 0.109 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(2) . ?
C1 C6 1.390(2) . ?
C1 O1 1.3899(18) . ?
C2 C3 1.383(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 C8 1.478(2) . ?
C5 C6 1.378(2) . ?
C5 C7 1.493(2) . ?
C6 H6 0.9300 . ?
C7 O2 1.2047(19) . ?
C7 N1 1.390(2) . ?
C8 O3 1.213(2) . ?
C8 N1 1.392(2) . ?
C9 N1 1.464(2) . ?
C9 C10 1.513(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.502(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O4 1.417(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O1 C1 1.3899(18) 2_655 ?
O4 H4 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.57(15) . . ?
C2 C1 O1 120.74(14) . . ?
C6 C1 O1 116.61(15) . . ?
C1 C2 C3 120.40(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 117.50(15) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.58(15) . . ?
C3 C4 C8 130.28(15) . . ?
C5 C4 C8 108.13(13) . . ?
C6 C5 C4 121.74(15) . . ?
C6 C5 C7 130.28(15) . . ?
C4 C5 C7 107.96(13) . . ?
C5 C6 C1 116.20(15) . . ?
C5 C6 H6 121.9 . . ?
C1 C6 H6 121.9 . . ?
O2 C7 N1 125.20(15) . . ?
O2 C7 C5 128.98(15) . . ?
N1 C7 C5 105.80(13) . . ?
O3 C8 N1 124.51(15) . . ?
O3 C8 C4 129.15(15) . . ?
N1 C8 C4 106.34(13) . . ?
N1 C9 C10 113.26(14) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 114.31(14) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
O4 C11 C10 110.56(15) . . ?
O4 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C7 N1 C8 111.74(13) . . ?
C7 N1 C9 124.05(13) . . ?
C8 N1 C9 124.21(14) . . ?
C1 O1 C1 116.85(18) 2_655 . ?
C11 O4 H4 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
C6 C1 C2 C3 0.2(2) . . . . ?
O1 C1 C2 C3 177.05(14) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C8 179.50(15) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C8 C4 C5 C6 -179.59(14) . . . . ?
C3 C4 C5 C7 178.71(14) . . . . ?
C8 C4 C5 C7 -0.98(17) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C7 C5 C6 C1 -178.22(15) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
O1 C1 C6 C5 -177.19(13) . . . . ?
C6 C5 C7 O2 1.0(3) . . . . ?
C4 C5 C7 O2 -177.45(17) . . . . ?
C6 C5 C7 N1 179.65(16) . . . . ?
C4 C5 C7 N1 1.20(17) . . . . ?
C3 C4 C8 O3 0.6(3) . . . . ?
C5 C4 C8 O3 -179.75(16) . . . . ?
C3 C4 C8 N1 -179.25(16) . . . . ?
C5 C4 C8 N1 0.41(17) . . . . ?
N1 C9 C10 C11 -59.85(19) . . . . ?
C9 C10 C11 O4 -65.52(19) . . . . ?
O2 C7 N1 C8 177.75(16) . . . . ?
C5 C7 N1 C8 -0.96(17) . . . . ?
O2 C7 N1 C9 -1.5(3) . . . . ?
C5 C7 N1 C9 179.74(14) . . . . ?
O3 C8 N1 C7 -179.46(16) . . . . ?
C4 C8 N1 C7 0.38(18) . . . . ?
O3 C8 N1 C9 -0.2(3) . . . . ?
C4 C8 N1 C9 179.68(14) . . . . ?
C10 C9 N1 C7 -75.3(2) . . . . ?
C10 C9 N1 C8 105.52(18) . . . . ?
C2 C1 O1 C1 46.26(12) . . . 2_655 ?
C6 C1 O1 C1 -136.66(16) . . . 2_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 0.93 2.65 3.579(2) 172.8 3
C10 H10B O4 0.97 2.54 3.460(2) 159.2 5_565
O4 H4 O3 0.82 2.10 2.8987(18) 163.4 7_565

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.031
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform, n-Hexane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_ODPI-2
_database_code_depnum_ccdc_archive 'CCDC 1490508'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 N2 O5'
_chemical_formula_sum            'C24 H24 N2 O5'
_chemical_formula_weight         420.45
_chemical_absolute_configuration rm

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   16.4774(10)
_cell_length_b                   5.1561(4)
_cell_length_c                   24.8530(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.793(4)
_cell_angle_gamma                90
_cell_volume                     2109.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3288
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      28.06

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.323
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            8056
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.475
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2160
_reflns_number_gt                1647
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0913P)²+2.7809P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2160
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1902
_refine_ls_wR_factor_gt          0.1761
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_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_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 0.3877(3) 0.2068(8) 0.52561(15) 0.0887(11) Uani 1 1 d . . . . .
H1A H 0.3570 0.2476 0.5563 0.133 Uiso 1 1 calc R U . . .
H1B H 0.3751 0.0336 0.5138 0.133 Uiso 1 1 calc R U . . .
H1C H 0.4447 0.2192 0.5353 0.133 Uiso 1 1 calc R U . . .
C2 C 0.3659(2) 0.3986(8) 0.47997(14) 0.0792(10) Uani 1 1 d . . . . .
H2A H 0.3080 0.3878 0.4712 0.095 Uiso 1 1 calc R U . . .
H2B H 0.3775 0.5732 0.4927 0.095 Uiso 1 1 calc R U . . .
C3 C 0.40996(18) 0.3527(7) 0.43066(13) 0.0661(8) Uani 1 1 d . . . . .
H3A H 0.3988 0.1774 0.4182 0.079 Uiso 1 1 calc R U . . .
H3B H 0.4678 0.3652 0.4394 0.079 Uiso 1 1 calc R U . . .
C4 C 0.38778(15) 0.5417(6) 0.38489(12) 0.0582(7) Uani 1 1 d . . . . .
H4A H 0.3957 0.7178 0.3978 0.070 Uiso 1 1 calc R U . . .
H4B H 0.4241 0.5142 0.3559 0.070 Uiso 1 1 calc R U . . .
C5 C 0.23931(15) 0.6730(5) 0.37704(10) 0.0474(6) Uani 1 1 d . . . . .
C6 C 0.16708(14) 0.5691(5) 0.34645(9) 0.0426(6) Uani 1 1 d . . . . .
C7 C 0.08726(15) 0.6534(5) 0.34461(10) 0.0500(6) Uani 1 1 d . . . . .
H7 H 0.0716 0.7948 0.3649 0.060 Uiso 1 1 calc R U . . .
C8 C 0.03179(15) 0.5206(6) 0.31170(11) 0.0523(7) Uani 1 1 d . . . . .
H8 H -0.0223 0.5729 0.3095 0.063 Uiso 1 1 calc R U . . .
C9 C 0.05614(14) 0.3085(5) 0.28172(10) 0.0477(6) Uani 1 1 d . . . . .
C10 C 0.13568(15) 0.2214(5) 0.28405(10) 0.0457(6) Uani 1 1 d . . . . .
H10 H 0.1514 0.0783 0.2643 0.055 Uiso 1 1 calc R U . . .
C11 C 0.19030(14) 0.3561(5) 0.31691(9) 0.0412(6) Uani 1 1 d . . . . .
C12 C 0.27940(14) 0.3199(5) 0.32774(9) 0.0453(6) Uani 1 1 d . . . . .
N1 N 0.30380(12) 0.5116(4) 0.36393(8) 0.0476(5) Uani 1 1 d . . . . .
O1 O 0.0000 0.1687(5) 0.2500 0.0637(8) Uani 1 2 d S T P . .
O2 O 0.24522(13) 0.8562(4) 0.40705(8) 0.0670(6) Uani 1 1 d . . . . .
O3 O 0.32366(11) 0.1606(4) 0.30838(8) 0.0637(6) 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 C2 1.534(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.474(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.529(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.463(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O2 1.204(3) . ?
C5 N1 1.401(3) . ?
C5 C6 1.481(4) . ?
C6 C7 1.384(3) . ?
C6 C11 1.385(3) . ?
C7 C8 1.379(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(3) . ?
C9 O1 1.388(3) . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.491(3) . ?
C12 O3 1.214(3) . ?
C12 N1 1.383(3) . ?
O1 C9 1.388(3) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 113.8(3) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 114.0(3) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.6 . . ?
N1 C4 C3 112.7(2) . . ?
N1 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
O2 C5 N1 124.8(2) . . ?
O2 C5 C6 129.8(2) . . ?
N1 C5 C6 105.4(2) . . ?
C7 C6 C11 121.2(2) . . ?
C7 C6 C5 130.0(2) . . ?
C11 C6 C5 108.8(2) . . ?
C8 C7 C6 117.7(2) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 O1 117.3(2) . . ?
C10 C9 C8 122.0(2) . . ?
O1 C9 C8 120.7(2) . . ?
C11 C10 C9 116.9(2) . . ?
C11 C10 H10 121.6 . . ?
C9 C10 H10 121.6 . . ?
C10 C11 C6 121.7(2) . . ?
C10 C11 C12 130.9(2) . . ?
C6 C11 C12 107.4(2) . . ?
O3 C12 N1 125.5(2) . . ?
O3 C12 C11 128.2(2) . . ?
N1 C12 C11 106.3(2) . . ?
C12 N1 C5 112.1(2) . . ?
C12 N1 C4 123.2(2) . . ?
C5 N1 C4 124.7(2) . . ?
C9 O1 C9 117.4(3) . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O3 0.93 2.58 3.502(3) 172.7 3_455

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform, n-Hexane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_ODP3
_database_code_depnum_ccdc_archive 'CCDC 1490509'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O5'
_chemical_formula_sum            'C26 H24 N2 O5'
_chemical_formula_weight         444.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   43.491(5)
_cell_length_b                   5.2413(5)
_cell_length_c                   19.472(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.452(4)
_cell_angle_gamma                90
_cell_volume                     4298.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4299
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      22.02

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.373
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            31730
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.902
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4228
_reflns_number_gt                2422
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²+2.5897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4228
_refine_ls_number_parameters     324
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1484
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.019
_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_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 0.93018(6) 0.5862(5) 0.75556(14) 0.0476(7) Uani 1 1 d . . . . .
C2 C 0.90343(6) 0.7020(5) 0.76682(13) 0.0471(6) Uani 1 1 d . . . . .
H2 H 0.9047 0.8438 0.7961 0.057 Uiso 1 1 calc R U . . .
C3 C 0.87479(6) 0.5964(5) 0.73236(13) 0.0438(6) Uani 1 1 d . . . . .
C4 C 0.87277(6) 0.3840(5) 0.68968(13) 0.0448(6) Uani 1 1 d . . . . .
C5 C 0.89966(7) 0.2664(5) 0.67980(14) 0.0503(7) Uani 1 1 d . . . . .
H5 H 0.8983 0.1222 0.6514 0.060 Uiso 1 1 calc R U . . .
C6 C 0.92865(6) 0.3707(5) 0.71367(14) 0.0512(7) Uani 1 1 d . . . . .
H6 H 0.9473 0.2956 0.7083 0.061 Uiso 1 1 calc R U . . .
C7 C 0.84185(6) 0.6788(5) 0.73270(14) 0.0512(7) Uani 1 1 d . . . . .
C8 C 0.83842(6) 0.3270(5) 0.65989(14) 0.0517(7) Uani 1 1 d . . . . .
C9 C 0.78707(6) 0.5351(5) 0.67091(16) 0.0598(8) Uani 1 1 d . . . . .
H9 H 0.7824 0.6880 0.6954 0.072 Uiso 1 1 calc R U . . .
C10 C 0.77090(7) 0.5683(7) 0.59285(18) 0.0803(10) Uani 1 1 d . . . . .
H10A H 0.7703 0.7467 0.5793 0.096 Uiso 1 1 calc R U . . .
H10B H 0.7818 0.4722 0.5635 0.096 Uiso 1 1 calc R U . . .
C11 C 0.73854(9) 0.4679(12) 0.5860(2) 0.138(2) Uani 1 1 d . . . . .
H11A H 0.7239 0.6083 0.5851 0.165 Uiso 1 1 calc R U . . .
H11B H 0.7317 0.3738 0.5420 0.165 Uiso 1 1 calc R U . . .
C12 C 0.73832(9) 0.3005(8) 0.6458(2) 0.1057(14) Uani 1 1 d . . . . .
H12A H 0.7336 0.1269 0.6292 0.127 Uiso 1 1 calc R U . . .
H12B H 0.7222 0.3555 0.6690 0.127 Uiso 1 1 calc R U . . .
C13 C 0.77052(7) 0.3121(6) 0.69683(18) 0.0685(9) Uani 1 1 d . . . . .
H13A H 0.7821 0.1546 0.6959 0.082 Uiso 1 1 calc R U . . .
H13B H 0.7687 0.3418 0.7448 0.082 Uiso 1 1 calc R U . . .
C14 C 0.98128(6) 0.5828(4) 0.83857(13) 0.0425(6) Uani 1 1 d . . . . .
C15 C 0.97400(6) 0.3676(5) 0.87275(13) 0.0444(6) Uani 1 1 d . . . . .
H15 H 0.9540 0.2940 0.8584 0.053 Uiso 1 1 calc R U . . .
C16 C 0.99675(6) 0.2624(4) 0.92846(14) 0.0438(6) Uani 1 1 d . . . . .
H16 H 0.9921 0.1188 0.9521 0.053 Uiso 1 1 calc R U . . .
C17 C 1.02625(5) 0.3743(4) 0.94805(13) 0.0391(6) Uani 1 1 d . . . . .
C18 C 1.03311(5) 0.5873(4) 0.91268(13) 0.0387(6) Uani 1 1 d . . . . .
C19 C 1.01102(6) 0.6962(4) 0.85750(13) 0.0435(6) Uani 1 1 d . . . . .
H19 H 1.0158 0.8395 0.8339 0.052 Uiso 1 1 calc R U . . .
C20 C 1.05464(5) 0.3115(5) 1.00526(13) 0.0409(6) Uani 1 1 d . . . . .
C21 C 1.06651(6) 0.6633(5) 0.94523(13) 0.0443(6) Uani 1 1 d . . . . .
C22 C 1.11036(6) 0.4824(5) 1.04528(14) 0.0466(6) Uani 1 1 d . . . . .
H22 H 1.1115 0.3405 1.0786 0.056 Uiso 1 1 calc R U . . .
C23 C 1.12116(6) 0.7232(5) 1.08913(15) 0.0538(7) Uani 1 1 d . . . . .
H23A H 1.1116 0.8744 1.0639 0.065 Uiso 1 1 calc R U . . .
H23B H 1.1156 0.7149 1.1343 0.065 Uiso 1 1 calc R U . . .
C24 C 1.15679(8) 0.7245(8) 1.0995(3) 0.0866(12) Uani 1 1 d D . . . .
C25 C 1.1620(3) 0.631(3) 1.0320(7) 0.075(3) Uani 0.60(3) 1 d . . P A 1
H25A H 1.1828 0.5518 1.0395 0.089 Uiso 0.60(3) 1 calc R U P A 1
H25B H 1.1606 0.7697 0.9985 0.089 Uiso 0.60(3) 1 calc DR U P A 1
C25' C 1.1647(3) 0.510(5) 1.0569(12) 0.075(5) Uani 0.40(3) 1 d . . P A 2
H25C H 1.1808 0.5625 1.0333 0.090 Uiso 0.40(3) 1 calc R U P A 2
H25D H 1.1728 0.3664 1.0876 0.090 Uiso 0.40(3) 1 calc R U P A 2
C26 C 1.13588(7) 0.4360(7) 1.0047(2) 0.0701(9) Uani 1 1 d D . . . .
N1 N 0.82161(5) 0.5113(4) 0.68710(12) 0.0527(6) Uani 1 1 d . . . . .
N2 N 1.07795(4) 0.4912(4) 1.00047(11) 0.0435(5) Uani 1 1 d . . . . .
O1 O 0.95939(4) 0.7040(3) 0.78461(10) 0.0563(5) Uani 1 1 d . . . . .
O2 O 0.82709(5) 0.1568(4) 0.61956(11) 0.0684(6) Uani 1 1 d . . . . .
O3 O 0.83383(5) 0.8521(4) 0.76462(11) 0.0712(6) Uani 1 1 d . . . . .
O4 O 1.05803(4) 0.1454(3) 1.04952(10) 0.0524(5) Uani 1 1 d . . . . .
O5 O 1.08131(4) 0.8366(4) 0.92790(10) 0.0609(5) Uani 1 1 d . . . . .
H26B H 1.1388(9) 0.260(3) 0.994(2) 0.118(14) Uiso 1 1 d D . . . .
H24A H 1.1665(9) 0.892(4) 1.110(2) 0.150(17) Uiso 1 1 d D . . . .
H26A H 1.1291(7) 0.503(5) 0.9570(10) 0.129(16) Uiso 1 1 d D . . . .
H24B H 1.1677(12) 0.648(11) 1.1450(18) 0.22(3) Uiso 1 1 d 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 C2 1.377(3) . ?
C1 C6 1.385(4) . ?
C1 O1 1.399(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 C7 1.498(4) . ?
C4 C5 1.377(3) . ?
C4 C8 1.491(4) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O3 1.200(3) . ?
C7 N1 1.394(3) . ?
C8 O2 1.209(3) . ?
C8 N1 1.393(3) . ?
C9 N1 1.461(3) . ?
C9 C10 1.517(4) . ?
C9 C13 1.523(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.477(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.459(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.503(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O1 1.384(3) . ?
C14 C15 1.386(3) . ?
C14 C19 1.387(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(3) . ?
C17 C20 1.479(3) . ?
C18 C19 1.374(3) . ?
C18 C21 1.487(3) . ?
C19 H19 0.9300 . ?
C20 O4 1.208(3) . ?
C20 N2 1.404(3) . ?
C21 O5 1.209(3) . ?
C21 N2 1.397(3) . ?
C22 N2 1.462(3) . ?
C22 C23 1.530(3) . ?
C22 C26 1.534(4) . ?
C22 H22 0.9800 . ?
C23 C24 1.512(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.473(10) . ?
C24 C25' 1.487(15) . ?
C24 H24A 0.975(15) . ?
C24 H24B 0.980(15) . ?
C25 C26 1.521(10) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25' C26 1.454(14) . ?
C25' H25C 0.9700 . ?
C25' H25D 0.9700 . ?
C26 H26B 0.961(15) . ?
C26 H26A 0.967(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.3(2) . . ?
C2 C1 O1 117.3(2) . . ?
C6 C1 O1 120.2(2) . . ?
C3 C2 C1 116.3(2) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C2 C3 C4 122.2(2) . . ?
C2 C3 C7 129.3(2) . . ?
C4 C3 C7 108.6(2) . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 C8 131.2(2) . . ?
C3 C4 C8 107.6(2) . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O3 C7 N1 126.0(3) . . ?
O3 C7 C3 128.5(3) . . ?
N1 C7 C3 105.6(2) . . ?
O2 C8 N1 126.2(3) . . ?
O2 C8 C4 127.3(3) . . ?
N1 C8 C4 106.4(2) . . ?
N1 C9 C10 114.9(2) . . ?
N1 C9 C13 114.1(2) . . ?
C10 C9 C13 106.3(3) . . ?
N1 C9 H9 107.0 . . ?
C10 C9 H9 107.0 . . ?
C13 C9 H9 107.0 . . ?
C11 C10 C9 104.0(3) . . ?
C11 C10 H10A 111.0 . . ?
C9 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C12 C11 C10 109.8(3) . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 C13 108.2(3) . . ?
C11 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
C11 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 C9 104.5(3) . . ?
C12 C13 H13A 110.8 . . ?
C9 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
C9 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
O1 C14 C15 122.8(2) . . ?
O1 C14 C19 115.1(2) . . ?
C15 C14 C19 122.1(2) . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 118.8(2) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 C20 131.3(2) . . ?
C18 C17 C20 108.2(2) . . ?
C19 C18 C17 122.0(2) . . ?
C19 C18 C21 129.8(2) . . ?
C17 C18 C21 108.3(2) . . ?
C18 C19 C14 116.9(2) . . ?
C18 C19 H19 121.5 . . ?
C14 C19 H19 121.5 . . ?
O4 C20 N2 124.7(2) . . ?
O4 C20 C17 128.9(2) . . ?
N2 C20 C17 106.4(2) . . ?
O5 C21 N2 126.0(2) . . ?
O5 C21 C18 127.9(2) . . ?
N2 C21 C18 106.12(19) . . ?
N2 C22 C23 115.0(2) . . ?
N2 C22 C26 114.3(2) . . ?
C23 C22 C26 104.9(2) . . ?
N2 C22 H22 107.4 . . ?
C23 C22 H22 107.4 . . ?
C26 C22 H22 107.4 . . ?
C24 C23 C22 103.9(2) . . ?
C24 C23 H23A 111.0 . . ?
C22 C23 H23A 111.0 . . ?
C24 C23 H23B 111.0 . . ?
C22 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
C25 C24 C23 105.1(5) . . ?
C25' C24 C23 107.0(6) . . ?
C25 C24 H24A 110(3) . . ?
C25' C24 H24A 131(3) . . ?
C23 C24 H24A 114(3) . . ?
C25 C24 H24B 121(4) . . ?
C25' C24 H24B 94(4) . . ?
C23 C24 H24B 112(4) . . ?
H24A C24 H24B 95(4) . . ?
C24 C25 C26 105.6(6) . . ?
C24 C25 H25A 110.6 . . ?
C26 C25 H25A 110.6 . . ?
C24 C25 H25B 110.6 . . ?
C26 C25 H25B 110.6 . . ?
H25A C25 H25B 108.8 . . ?
C26 C25' C24 108.3(9) . . ?
C26 C25' H25C 110.0 . . ?
C24 C25' H25C 110.0 . . ?
C26 C25' H25D 110.0 . . ?
C24 C25' H25D 110.0 . . ?
H25C C25' H25D 108.4 . . ?
C25' C26 C22 101.8(8) . . ?
C25 C26 C22 106.7(4) . . ?
C25' C26 H26B 106(2) . . ?
C25 C26 H26B 126(2) . . ?
C22 C26 H26B 115(2) . . ?
C25' C26 H26A 125.3(19) . . ?
C25 C26 H26A 96.5(14) . . ?
C22 C26 H26A 111(2) . . ?
H26B C26 H26A 99(3) . . ?
C8 N1 C7 111.8(2) . . ?
C8 N1 C9 125.9(2) . . ?
C7 N1 C9 122.4(2) . . ?
C21 N2 C20 111.1(2) . . ?
C21 N2 C22 125.83(19) . . ?
C20 N2 C22 122.9(2) . . ?
C14 O1 C1 119.20(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10B O2 0.97 2.59 3.203(4) 121.0 .
C23 H23A O5 0.97 2.65 3.240(3) 119.2 .

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_ODPI-4
_database_code_depnum_ccdc_archive 'CCDC 1490510'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 N2 O5'
_chemical_formula_sum            'C30 H30 N2 O5'
_chemical_formula_weight         498.56
_chemical_absolute_configuration rm

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   32.3856(16)
_cell_length_b                   5.3119(2)
_cell_length_c                   15.6793(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.527(3)
_cell_angle_gamma                90
_cell_volume                     2526.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3885
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.76

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.310
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            9708
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.774
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             9708
_reflns_number_gt                6820
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1195P)²+3.8015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9708
_refine_ls_number_parameters     170
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2360
_refine_ls_wR_factor_gt          0.2056
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_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_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 0.01955(12) 0.8888(6) 0.3302(2) 0.0685(10) Uani 1 1 d . . . . .
C2 C 0.05661(12) 0.7784(6) 0.3926(3) 0.0743(11) Uani 1 1 d . . . . .
H2 H 0.0692 0.6340 0.3787 0.089 Uiso 1 1 calc R U . . .
C3 C 0.07385(12) 0.8948(7) 0.4766(2) 0.0687(10) Uani 1 1 d . . . . .
C4 C 0.05482(12) 1.1091(7) 0.4964(2) 0.0703(10) Uani 1 1 d . . . . .
C5 C 0.01814(13) 1.2172(6) 0.4325(3) 0.0731(10) Uani 1 1 d . . . . .
H5 H 0.0059 1.3640 0.4458 0.088 Uiso 1 1 calc R U . . .
C6 C 0.00025(12) 1.1043(6) 0.3498(2) 0.0724(10) Uani 1 1 d . . . . .
H6 H -0.0249 1.1713 0.3063 0.087 Uiso 1 1 calc R U . . .
C7 C 0.11233(15) 0.8240(9) 0.5581(3) 0.0855(12) Uani 1 1 d . . . . .
C8 C 0.07845(14) 1.1816(9) 0.5912(3) 0.0824(12) Uani 1 1 d . . . . .
C9 C 0.14476(15) 0.9985(11) 0.7183(3) 0.130(2) Uani 1 1 d . U . . .
C10 C 0.18467(15) 1.1264(10) 0.7275(4) 0.1203(17) Uani 1 1 d . U . . .
H10A H 0.1765 1.2968 0.7060 0.144 Uiso 1 1 calc R U . . .
H10B H 0.1962 1.0481 0.6846 0.144 Uiso 1 1 calc R U . . .
C11 C 0.22158(17) 1.1481(12) 0.8134(4) 0.138(2) Uani 1 1 d . U . . .
H11A H 0.2480 1.1352 0.7978 0.166 Uiso 1 1 calc R U . . .
H11B H 0.2208 1.3198 0.8338 0.166 Uiso 1 1 calc R U . . .
C12 C 0.2292(2) 1.0013(16) 0.8886(5) 0.182(3) Uani 1 1 d . U . . .
H12A H 0.2542 1.0723 0.9367 0.219 Uiso 1 1 calc R U . . .
H12B H 0.2381 0.8367 0.8746 0.219 Uiso 1 1 calc R U . . .
C13 C 0.1930(3) 0.9609(16) 0.9274(4) 0.173(3) Uani 1 1 d . U . . .
H13A H 0.2059 0.8750 0.9853 0.208 Uiso 1 1 calc R U . . .
H13B H 0.1835 1.1253 0.9403 0.208 Uiso 1 1 calc R U . . .
C14 C 0.15501(17) 0.8259(10) 0.8758(3) 0.1161(16) Uani 1 1 d . U . . .
H14A H 0.1333 0.8567 0.9042 0.139 Uiso 1 1 calc R U . . .
H14B H 0.1627 0.6490 0.8853 0.139 Uiso 1 1 calc R U . . .
C15 C 0.13247(16) 0.8562(11) 0.7798(3) 0.1251(18) Uani 1 1 d . U . . .
H15A H 0.1285 0.6866 0.7552 0.150 Uiso 1 1 calc R U . . .
H15B H 0.1032 0.9157 0.7736 0.150 Uiso 1 1 calc R U . . .
N1 N 0.11306(11) 1.0024(8) 0.6251(2) 0.0886(11) Uani 1 1 d . . . . .
O1 O 0.0000 0.7562(6) 0.2500 0.0817(11) Uani 1 2 d S T P . .
O2 O 0.07167(9) 1.3508(6) 0.63491(19) 0.1018(10) Uani 1 1 d . . . . .
O3 O 0.13812(11) 0.6552(6) 0.5675(2) 0.1079(11) 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 C2 1.385(5) . ?
C1 O1 1.386(4) . ?
C1 C6 1.389(5) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(5) . ?
C3 C7 1.487(5) . ?
C4 C5 1.382(5) . ?
C4 C8 1.466(5) . ?
C5 C6 1.361(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O3 1.199(5) . ?
C7 N1 1.409(6) . ?
C8 O2 1.196(5) . ?
C8 N1 1.424(6) . ?
C9 C15 1.389(6) . ?
C9 C10 1.422(6) . ?
C9 N1 1.461(5) . ?
C10 C11 1.459(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.362(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.513(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.408(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.434(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O1 C1 1.386(4) 2 ?

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 O1 115.6(3) . . ?
C2 C1 C6 122.6(3) . . ?
O1 C1 C6 121.4(3) . . ?
C3 C2 C1 116.3(4) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 C7 108.7(4) . . ?
C2 C3 C7 130.0(4) . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 C8 109.2(4) . . ?
C5 C4 C8 129.5(4) . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O3 C7 N1 125.7(4) . . ?
O3 C7 C3 129.2(5) . . ?
N1 C7 C3 105.1(4) . . ?
O2 C8 N1 124.6(4) . . ?
O2 C8 C4 130.0(5) . . ?
N1 C8 C4 105.4(4) . . ?
C15 C9 C10 131.4(4) . . ?
C15 C9 N1 115.4(3) . . ?
C10 C9 N1 112.9(4) . . ?
C9 C10 C11 123.6(4) . . ?
C9 C10 H10A 106.4 . . ?
C11 C10 H10A 106.4 . . ?
C9 C10 H10B 106.4 . . ?
C11 C10 H10B 106.4 . . ?
H10A C10 H10B 106.5 . . ?
C12 C11 C10 126.5(5) . . ?
C12 C11 H11A 105.7 . . ?
C10 C11 H11A 105.7 . . ?
C12 C11 H11B 105.7 . . ?
C10 C11 H11B 105.7 . . ?
H11A C11 H11B 106.1 . . ?
C11 C12 C13 120.0(6) . . ?
C11 C12 H12A 107.3 . . ?
C13 C12 H12A 107.3 . . ?
C11 C12 H12B 107.3 . . ?
C13 C12 H12B 107.3 . . ?
H12A C12 H12B 106.9 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 H13A 107.6 . . ?
C12 C13 H13A 107.6 . . ?
C14 C13 H13B 107.6 . . ?
C12 C13 H13B 107.6 . . ?
H13A C13 H13B 107.0 . . ?
C13 C14 C15 124.5(5) . . ?
C13 C14 H14A 106.2 . . ?
C15 C14 H14A 106.2 . . ?
C13 C14 H14B 106.2 . . ?
C15 C14 H14B 106.2 . . ?
H14A C14 H14B 106.4 . . ?
C9 C15 C14 128.7(4) . . ?
C9 C15 H15A 105.1 . . ?
C14 C15 H15A 105.1 . . ?
C9 C15 H15B 105.1 . . ?
C14 C15 H15B 105.1 . . ?
H15A C15 H15B 105.9 . . ?
C7 N1 C8 111.5(4) . . ?
C7 N1 C9 123.9(4) . . ?
C8 N1 C9 124.6(4) . . ?
C1 O1 C1 118.9(4) . 2 ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform, n-Hexane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_ODPI-5
_database_code_depnum_ccdc_archive 'CCDC 1490511'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H40 N2 O5'
_chemical_formula_sum            'C40 H40 N2 O5'
_chemical_formula_weight         628.74
_chemical_absolute_configuration rm

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8560(7)
_cell_length_b                   20.5314(11)
_cell_length_c                   13.6341(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.970(2)
_cell_angle_gamma                90.00
_cell_volume                     3456.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5518
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      21.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      1.207
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26924
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6085
_reflns_number_gt                3725
_reflns_threshold_expression     >2σ(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 > 2σ(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)+(0.1030P)²+0.5452P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6085
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1906
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_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
C1 C 0.2341(2) 0.37490(13) 0.7255(2) 0.0578(8) Uani 1 1 d . . .
C2 C 0.1939(3) 0.35968(16) 0.7988(3) 0.0796(10) Uani 1 1 d . . .
H2 H 0.1492 0.3891 0.8104 0.096 Uiso 1 1 calc R . .
C3 C 0.2194(3) 0.30149(16) 0.8546(3) 0.0824(11) Uani 1 1 d . . .
H3 H 0.1917 0.2908 0.9032 0.099 Uiso 1 1 calc R . .
C4 C 0.2869(2) 0.25961(14) 0.8363(2) 0.0566(7) Uani 1 1 d . . .
C5 C 0.3279(2) 0.27574(12) 0.7640(2) 0.0486(6) Uani 1 1 d . . .
C6 C 0.3022(2) 0.33350(13) 0.7064(2) 0.0562(7) Uani 1 1 d . . .
H6 H 0.3294 0.3440 0.6573 0.067 Uiso 1 1 calc R . .
C7 C 0.3288(3) 0.19441(14) 0.8825(2) 0.0600(8) Uani 1 1 d . . .
C8 C 0.3978(2) 0.22174(13) 0.7627(2) 0.0539(7) Uani 1 1 d . . .
C9 C 0.4544(2) 0.11425(12) 0.8599(2) 0.0469(6) Uani 1 1 d . . .
C10 C 0.5582(2) 0.11254(13) 0.9482(2) 0.0513(7) Uani 1 1 d . . .
C11 C 0.6104(2) 0.05265(14) 0.9718(2) 0.0599(8) Uani 1 1 d . . .
H11 H 0.6785 0.0491 1.0318 0.072 Uiso 1 1 calc R . .
C12 C 0.5642(3) -0.00111(14) 0.9091(3) 0.0639(8) Uani 1 1 d . . .
H12 H 0.6013 -0.0406 0.9265 0.077 Uiso 1 1 calc R . .
C13 C 0.4630(3) 0.00272(14) 0.8201(3) 0.0617(8) Uani 1 1 d . . .
H13 H 0.4331 -0.0341 0.7772 0.074 Uiso 1 1 calc R . .
C14 C 0.4050(2) 0.06071(13) 0.7935(2) 0.0509(7) Uani 1 1 d . . .
C15 C 0.6115(3) 0.17149(15) 1.0176(2) 0.0676(8) Uani 1 1 d . . .
H15 H 0.5774 0.2102 0.9732 0.081 Uiso 1 1 calc R . .
C16 C 0.5940(4) 0.1742(2) 1.1186(3) 0.1189(16) Uani 1 1 d . . .
H16A H 0.6289 0.2122 1.1609 0.178 Uiso 1 1 calc R . .
H16B H 0.6241 0.1360 1.1624 0.178 Uiso 1 1 calc R . .
H16C H 0.5178 0.1762 1.0971 0.178 Uiso 1 1 calc R . .
C17 C 0.7326(3) 0.1761(2) 1.0538(4) 0.1178(15) Uani 1 1 d . . .
H17A H 0.7455 0.1743 0.9904 0.177 Uiso 1 1 calc R . .
H17B H 0.7688 0.1403 1.1019 0.177 Uiso 1 1 calc R . .
H17C H 0.7598 0.2164 1.0921 0.177 Uiso 1 1 calc R . .
C18 C 0.2941(2) 0.06371(15) 0.6969(2) 0.0645(8) Uani 1 1 d . . .
H18 H 0.2674 0.1083 0.6927 0.077 Uiso 1 1 calc R . .
C19 C 0.2987(4) 0.0501(3) 0.5911(3) 0.137(2) Uani 1 1 d . . .
H19A H 0.2270 0.0524 0.5310 0.205 Uiso 1 1 calc R . .
H19B H 0.3280 0.0074 0.5939 0.205 Uiso 1 1 calc R . .
H19C H 0.3440 0.0819 0.5806 0.205 Uiso 1 1 calc R . .
C20 C 0.2152(3) 0.0190(3) 0.7115(5) 0.135(2) Uani 1 1 d . . .
H20A H 0.2140 0.0288 0.7798 0.202 Uiso 1 1 calc R . .
H20B H 0.2372 -0.0254 0.7123 0.202 Uiso 1 1 calc R . .
H20C H 0.1441 0.0252 0.6518 0.202 Uiso 1 1 calc R . .
C21 C 0.1492(2) 0.44083(12) 0.5643(2) 0.0479(6) Uani 1 1 d . . .
C22 C 0.1444(2) 0.50278(12) 0.5226(2) 0.0498(7) Uani 1 1 d . . .
H22 H 0.1835 0.5365 0.5694 0.060 Uiso 1 1 calc R . .
C23 C 0.0818(2) 0.51493(12) 0.4117(2) 0.0498(7) Uani 1 1 d . . .
H23 H 0.0783 0.5565 0.3830 0.060 Uiso 1 1 calc R . .
C24 C 0.02500(19) 0.46407(11) 0.3447(2) 0.0414(6) Uani 1 1 d . . .
C25 C 0.0312(2) 0.40262(12) 0.3878(2) 0.0465(6) Uani 1 1 d . . .
C26 C 0.0928(2) 0.38956(12) 0.4972(2) 0.0532(7) Uani 1 1 d . . .
H26 H 0.0965 0.3478 0.5253 0.064 Uiso 1 1 calc R . .
C27 C -0.0499(2) 0.46212(12) 0.2266(2) 0.0461(6) Uani 1 1 d . . .
C28 C -0.0403(2) 0.35890(14) 0.2976(2) 0.0572(7) Uani 1 1 d . . .
C29 C -0.1714(2) 0.37615(12) 0.0993(2) 0.0487(6) Uani 1 1 d . . .
C30 C -0.1436(2) 0.34975(13) 0.0215(2) 0.0567(7) Uani 1 1 d . . .
C31 C -0.2270(3) 0.32846(17) -0.0762(3) 0.0743(9) Uani 1 1 d . . .
H31 H -0.2116 0.3105 -0.1302 0.089 Uiso 1 1 calc R . .
C32 C -0.3331(3) 0.33378(18) -0.0942(3) 0.0817(10) Uani 1 1 d . . .
H32 H -0.3884 0.3186 -0.1600 0.098 Uiso 1 1 calc R . .
C33 C -0.3585(3) 0.36091(18) -0.0173(3) 0.0762(9) Uani 1 1 d . . .
H33 H -0.4307 0.3644 -0.0317 0.091 Uiso 1 1 calc R . .
C34 C -0.2779(2) 0.38319(15) 0.0818(2) 0.0593(7) Uani 1 1 d . . .
C35 C -0.0279(3) 0.34365(18) 0.0424(3) 0.0808(10) Uani 1 1 d . . .
H35 H 0.0161 0.3716 0.1052 0.097 Uiso 1 1 calc R . .
C36 C 0.0113(4) 0.2743(2) 0.0732(4) 0.1299(17) Uani 1 1 d . . .
H36A H 0.0853 0.2712 0.0863 0.195 Uiso 1 1 calc R . .
H36B H -0.0326 0.2456 0.0142 0.195 Uiso 1 1 calc R . .
H36C H 0.0062 0.2622 0.1387 0.195 Uiso 1 1 calc R . .
C37 C -0.0097(4) 0.3655(3) -0.0548(4) 0.1286(17) Uani 1 1 d . . .
H37A H 0.0654 0.3605 -0.0367 0.193 Uiso 1 1 calc R . .
H37B H -0.0301 0.4104 -0.0709 0.193 Uiso 1 1 calc R . .
H37C H -0.0529 0.3393 -0.1179 0.193 Uiso 1 1 calc R . .
C38 C -0.3061(3) 0.41248(17) 0.1682(3) 0.0732(9) Uani 1 1 d . . .
H38 H -0.2400 0.4334 0.2228 0.088 Uiso 1 1 calc R . .
C39 C -0.3899(4) 0.4643(3) 0.1239(4) 0.1306(17) Uani 1 1 d . . .
H39A H -0.3685 0.4963 0.0861 0.196 Uiso 1 1 calc R . .
H39B H -0.3974 0.4847 0.1834 0.196 Uiso 1 1 calc R . .
H39C H -0.4578 0.4454 0.0736 0.196 Uiso 1 1 calc R . .
C40 C -0.3343(5) 0.3609(2) 0.2278(4) 0.142(2) Uani 1 1 d . . .
H40A H -0.2782 0.3285 0.2548 0.213 Uiso 1 1 calc R . .
H40B H -0.4016 0.3409 0.1785 0.213 Uiso 1 1 calc R . .
H40C H -0.3412 0.3800 0.2886 0.213 Uiso 1 1 calc R . .
N1 N 0.39594(17) 0.17516(10) 0.83621(17) 0.0488(6) Uani 1 1 d . . .
N2 N -0.08657(17) 0.39769(10) 0.20300(16) 0.0476(5) Uani 1 1 d . . .
O1 O 0.20928(18) 0.43609(9) 0.67668(15) 0.0709(6) Uani 1 1 d . . .
O2 O 0.4462(2) 0.21680(11) 0.7096(2) 0.0904(8) Uani 1 1 d . . .
O3 O 0.3096(2) 0.16238(12) 0.9453(2) 0.0915(8) Uani 1 1 d . . .
O4 O -0.0583(2) 0.30206(10) 0.30091(17) 0.0936(8) Uani 1 1 d . . .
O5 O -0.07748(17) 0.50516(9) 0.15942(16) 0.0634(5) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.379(4) . ?
C1 C2 1.383(4) . ?
C1 O1 1.390(3) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 C7 1.481(4) . ?
C5 C6 1.377(4) . ?
C5 C8 1.478(4) . ?
C6 H6 0.9300 . ?
C7 O3 1.202(3) . ?
C7 N1 1.397(3) . ?
C8 O2 1.194(3) . ?
C8 N1 1.394(3) . ?
C9 C14 1.391(4) . ?
C9 C10 1.396(4) . ?
C9 N1 1.445(3) . ?
C10 C11 1.388(4) . ?
C10 C15 1.507(4) . ?
C11 C12 1.365(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9300 . ?
C14 C18 1.505(4) . ?
C15 C16 1.504(5) . ?
C15 C17 1.522(5) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.498(5) . ?
C18 C20 1.509(5) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O1 1.376(3) . ?
C21 C22 1.383(3) . ?
C21 C26 1.381(4) . ?
C22 C23 1.383(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(3) . ?
C24 C27 1.468(4) . ?
C25 C26 1.368(3) . ?
C25 C28 1.481(4) . ?
C26 H26 0.9300 . ?
C27 O5 1.203(3) . ?
C27 N2 1.401(3) . ?
C28 O4 1.199(3) . ?
C28 N2 1.400(3) . ?
C29 C34 1.391(4) . ?
C29 C30 1.392(4) . ?
C29 N2 1.438(3) . ?
C30 C31 1.381(4) . ?
C30 C35 1.501(4) . ?
C31 C32 1.381(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.368(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.383(4) . ?
C33 H33 0.9300 . ?
C34 C38 1.522(4) . ?
C35 C36 1.514(6) . ?
C35 C37 1.525(5) . ?
C35 H35 0.9800 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.486(5) . ?
C38 C40 1.492(5) . ?
C38 H38 0.9800 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 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
C6 C1 C2 122.1(3) . . ?
C6 C1 O1 120.6(3) . . ?
C2 C1 O1 117.2(2) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 118.0(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 C7 131.1(3) . . ?
C5 C4 C7 108.1(2) . . ?
C6 C5 C4 121.9(2) . . ?
C6 C5 C8 129.9(2) . . ?
C4 C5 C8 108.2(2) . . ?
C5 C6 C1 116.5(3) . . ?
C5 C6 H6 121.8 . . ?
C1 C6 H6 121.8 . . ?
O3 C7 N1 125.1(3) . . ?
O3 C7 C4 128.8(3) . . ?
N1 C7 C4 106.1(2) . . ?
O2 C8 N1 125.2(2) . . ?
O2 C8 C5 128.5(2) . . ?
N1 C8 C5 106.3(2) . . ?
C14 C9 C10 123.5(2) . . ?
C14 C9 N1 118.6(2) . . ?
C10 C9 N1 118.0(2) . . ?
C11 C10 C9 116.6(3) . . ?
C11 C10 C15 120.7(3) . . ?
C9 C10 C15 122.7(2) . . ?
C12 C11 C10 121.6(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C9 116.9(3) . . ?
C13 C14 C18 120.2(3) . . ?
C9 C14 C18 122.9(2) . . ?
C16 C15 C10 111.6(3) . . ?
C16 C15 C17 108.2(3) . . ?
C10 C15 C17 114.0(3) . . ?
C16 C15 H15 107.6 . . ?
C10 C15 H15 107.6 . . ?
C17 C15 H15 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C14 111.3(3) . . ?
C19 C18 C20 111.3(4) . . ?
C14 C18 C20 111.9(3) . . ?
C19 C18 H18 107.4 . . ?
C14 C18 H18 107.4 . . ?
C20 C18 H18 107.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 C22 114.5(2) . . ?
O1 C21 C26 124.0(2) . . ?
C22 C21 C26 121.4(2) . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 118.4(2) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C23 C24 C25 120.3(2) . . ?
C23 C24 C27 131.0(2) . . ?
C25 C24 C27 108.6(2) . . ?
C26 C25 C24 122.2(2) . . ?
C26 C25 C28 129.6(2) . . ?
C24 C25 C28 108.2(2) . . ?
C25 C26 C21 117.3(2) . . ?
C25 C26 H26 121.3 . . ?
C21 C26 H26 121.3 . . ?
O5 C27 N2 124.2(2) . . ?
O5 C27 C24 129.6(2) . . ?
N2 C27 C24 106.2(2) . . ?
O4 C28 N2 124.9(3) . . ?
O4 C28 C25 129.2(3) . . ?
N2 C28 C25 105.9(2) . . ?
C34 C29 C30 123.2(2) . . ?
C34 C29 N2 117.9(2) . . ?
C30 C29 N2 118.9(2) . . ?
C31 C30 C29 117.3(3) . . ?
C31 C30 C35 120.7(3) . . ?
C29 C30 C35 121.9(3) . . ?
C30 C31 C32 120.3(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C33 C32 C31 121.3(3) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C32 C33 C34 120.6(3) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C29 117.2(3) . . ?
C33 C34 C38 120.6(3) . . ?
C29 C34 C38 122.2(3) . . ?
C30 C35 C36 110.5(3) . . ?
C30 C35 C37 113.2(3) . . ?
C36 C35 C37 109.7(3) . . ?
C30 C35 H35 107.8 . . ?
C36 C35 H35 107.8 . . ?
C37 C35 H35 107.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 C40 112.3(4) . . ?
C39 C38 C34 113.3(3) . . ?
C40 C38 C34 111.3(3) . . ?
C39 C38 H38 106.4 . . ?
C40 C38 H38 106.4 . . ?
C34 C38 H38 106.4 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C8 N1 C7 111.3(2) . . ?
C8 N1 C9 124.3(2) . . ?
C7 N1 C9 124.4(2) . . ?
C28 N2 C27 111.0(2) . . ?
C28 N2 C29 124.0(2) . . ?
C27 N2 C29 124.4(2) . . ?
C21 O1 C1 119.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(5) . . . . ?
O1 C1 C2 C3 -176.7(3) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C2 C3 C4 C7 -179.9(3) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C7 C4 C5 C6 179.1(3) . . . . ?
C3 C4 C5 C8 179.5(3) . . . . ?
C7 C4 C5 C8 -0.5(3) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C8 C5 C6 C1 -179.8(3) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
O1 C1 C6 C5 175.8(2) . . . . ?
C3 C4 C7 O3 2.5(6) . . . . ?
C5 C4 C7 O3 -177.4(3) . . . . ?
C3 C4 C7 N1 -178.8(3) . . . . ?
C5 C4 C7 N1 1.2(3) . . . . ?
C6 C5 C8 O2 -1.0(5) . . . . ?
C4 C5 C8 O2 178.6(3) . . . . ?
C6 C5 C8 N1 180.0(3) . . . . ?
C4 C5 C8 N1 -0.4(3) . . . . ?
C14 C9 C10 C11 -3.2(4) . . . . ?
N1 C9 C10 C11 177.3(2) . . . . ?
C14 C9 C10 C15 178.5(3) . . . . ?
N1 C9 C10 C15 -1.0(4) . . . . ?
C9 C10 C11 C12 2.6(4) . . . . ?
C15 C10 C11 C12 -179.1(3) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 -1.3(4) . . . . ?
C12 C13 C14 C9 0.7(4) . . . . ?
C12 C13 C14 C18 -179.3(3) . . . . ?
C10 C9 C14 C13 1.6(4) . . . . ?
N1 C9 C14 C13 -178.9(2) . . . . ?
C10 C9 C14 C18 -178.4(3) . . . . ?
N1 C9 C14 C18 1.1(4) . . . . ?
C11 C10 C15 C16 -84.0(4) . . . . ?
C9 C10 C15 C16 94.3(4) . . . . ?
C11 C10 C15 C17 39.0(4) . . . . ?
C9 C10 C15 C17 -142.8(3) . . . . ?
C13 C14 C18 C19 -63.1(4) . . . . ?
C9 C14 C18 C19 116.8(4) . . . . ?
C13 C14 C18 C20 62.1(4) . . . . ?
C9 C14 C18 C20 -117.9(4) . . . . ?
O1 C21 C22 C23 -176.5(2) . . . . ?
C26 C21 C22 C23 0.4(4) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C22 C23 C24 C27 177.6(2) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
C27 C24 C25 C26 -178.1(2) . . . . ?
C23 C24 C25 C28 178.4(2) . . . . ?
C27 C24 C25 C28 0.1(3) . . . . ?
C24 C25 C26 C21 0.2(4) . . . . ?
C28 C25 C26 C21 -177.6(3) . . . . ?
O1 C21 C26 C25 176.1(2) . . . . ?
C22 C21 C26 C25 -0.5(4) . . . . ?
C23 C24 C27 O5 2.0(5) . . . . ?
C25 C24 C27 O5 -179.9(3) . . . . ?
C23 C24 C27 N2 -178.2(2) . . . . ?
C25 C24 C27 N2 -0.1(3) . . . . ?
C26 C25 C28 O4 -1.4(5) . . . . ?
C24 C25 C28 O4 -179.4(3) . . . . ?
C26 C25 C28 N2 178.0(3) . . . . ?
C24 C25 C28 N2 0.0(3) . . . . ?
C34 C29 C30 C31 -1.5(4) . . . . ?
N2 C29 C30 C31 178.8(3) . . . . ?
C34 C29 C30 C35 179.2(3) . . . . ?
N2 C29 C30 C35 -0.5(4) . . . . ?
C29 C30 C31 C32 0.1(5) . . . . ?
C35 C30 C31 C32 179.4(3) . . . . ?
C30 C31 C32 C33 1.0(5) . . . . ?
C31 C32 C33 C34 -0.8(5) . . . . ?
C32 C33 C34 C29 -0.6(5) . . . . ?
C32 C33 C34 C38 -179.1(3) . . . . ?
C30 C29 C34 C33 1.8(4) . . . . ?
N2 C29 C34 C33 -178.6(3) . . . . ?
C30 C29 C34 C38 -179.8(3) . . . . ?
N2 C29 C34 C38 -0.1(4) . . . . ?
C31 C30 C35 C36 -77.8(4) . . . . ?
C29 C30 C35 C36 101.5(4) . . . . ?
C31 C30 C35 C37 45.7(4) . . . . ?
C29 C30 C35 C37 -135.0(3) . . . . ?
C33 C34 C38 C39 -51.0(5) . . . . ?
C29 C34 C38 C39 130.6(4) . . . . ?
C33 C34 C38 C40 76.8(4) . . . . ?
C29 C34 C38 C40 -101.6(4) . . . . ?
O2 C8 N1 C7 -177.8(3) . . . . ?
C5 C8 N1 C7 1.2(3) . . . . ?
O2 C8 N1 C9 1.1(5) . . . . ?
C5 C8 N1 C9 -179.8(2) . . . . ?
O3 C7 N1 C8 177.2(3) . . . . ?
C4 C7 N1 C8 -1.5(3) . . . . ?
O3 C7 N1 C9 -1.7(5) . . . . ?
C4 C7 N1 C9 179.5(2) . . . . ?
C14 C9 N1 C8 -87.6(3) . . . . ?
C10 C9 N1 C8 91.9(3) . . . . ?
C14 C9 N1 C7 91.2(3) . . . . ?
C10 C9 N1 C7 -89.2(3) . . . . ?
O4 C28 N2 C27 179.4(3) . . . . ?
C25 C28 N2 C27 0.0(3) . . . . ?
O4 C28 N2 C29 7.3(5) . . . . ?
C25 C28 N2 C29 -172.1(2) . . . . ?
O5 C27 N2 C28 179.9(3) . . . . ?
C24 C27 N2 C28 0.1(3) . . . . ?
O5 C27 N2 C29 -8.1(4) . . . . ?
C24 C27 N2 C29 172.1(2) . . . . ?
C34 C29 N2 C28 87.1(3) . . . . ?
C30 C29 N2 C28 -93.2(3) . . . . ?
C34 C29 N2 C27 -83.9(3) . . . . ?
C30 C29 N2 C27 95.8(3) . . . . ?
C22 C21 O1 C1 -169.7(3) . . . . ?
C26 C21 O1 C1 13.4(4) . . . . ?
C6 C1 O1 C21 66.8(4) . . . . ?
C2 C1 O1 C21 -117.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O5 0.93 2.50 3.386(4) 159.9 3_566

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.060

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform, n-Hexane'
_exptl_crystal_preparation       ', Luminescent'
