# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_COMPOUND1
_database_code_depnum_ccdc_archive 'CCDC 1032721'
_audit_update_record             
;
2015-03-29 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O4'
_chemical_formula_weight         283.27

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)/n

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

_cell_length_a                   6.970(4)
_cell_length_b                   16.371(8)
_cell_length_c                   11.719(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.000(8)
_cell_angle_gamma                90.00
_cell_volume                     1316.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3554
_cell_measurement_theta_min      3.051
_cell_measurement_theta_max      28.677

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9480
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7944
_diffrn_reflns_av_R_equivalents  0.1166
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2994
_reflns_number_gt                2320
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0650P)²+0.0737P] 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         2994
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O2 O 0.84400(15) 0.01570(7) 0.17089(9) 0.0493(3) Uani 1 1 d . . .
O4 O 0.64699(14) 0.07029(7) -0.01605(9) 0.0480(3) Uani 1 1 d . . .
C3 C 0.98868(18) 0.09908(8) 0.04683(11) 0.0334(3) Uani 1 1 d . . .
O3 O 1.15152(16) 0.05156(7) 0.22662(9) 0.0540(3) Uani 1 1 d . . .
C5 C 1.15169(18) 0.18416(9) -0.07554(11) 0.0349(3) Uani 1 1 d . . .
C7 C 0.97315(18) 0.19522(9) -0.15195(11) 0.0354(3) Uani 1 1 d . . .
C8 C 0.81131(18) 0.10805(9) -0.03277(11) 0.0352(3) Uani 1 1 d . . .
C9 C 0.9968(2) 0.05172(9) 0.15618(11) 0.0376(3) Uani 1 1 d . . .
C10 C 1.15260(19) 0.13559(9) 0.02267(11) 0.0350(3) Uani 1 1 d . . .
C11 C 0.80609(19) 0.15585(9) -0.12862(11) 0.0376(3) Uani 1 1 d . . .
C13 C 1.3190(2) 0.22382(10) -0.09978(13) 0.0448(4) Uani 1 1 d . . .
C15 C 1.1329(2) 0.28521(12) -0.26757(14) 0.0533(4) Uani 1 1 d . . .
C16 C 0.9697(2) 0.24697(10) -0.24824(13) 0.0470(4) Uani 1 1 d . . .
C19 C 1.3104(2) 0.27334(12) -0.19278(15) 0.0544(4) Uani 1 1 d . . .
O1 O 0.77231(15) 0.05299(8) 0.61419(10) 0.0532(3) Uani 1 1 d . . .
N1 N 0.28095(18) 0.05955(9) 0.65974(11) 0.0455(3) Uani 1 1 d . . .
C14 C 0.58602(19) 0.07113(9) 0.60325(11) 0.0389(3) Uani 1 1 d . . .
C17 C 0.5007(2) 0.12239(10) 0.51521(13) 0.0469(4) Uani 1 1 d . . .
C18 C 0.4678(2) 0.04084(10) 0.67655(13) 0.0437(4) Uani 1 1 d . . .
C20 C 0.1962(2) 0.10752(12) 0.57513(15) 0.0541(4) Uani 1 1 d . . .
C21 C 0.3083(2) 0.13986(12) 0.50127(16) 0.0571(5) Uani 1 1 d . . .
H11 H 0.681(2) 0.1635(9) -0.1793(13) 0.036(4) Uiso 1 1 d . . .
H10 H 1.2784(19) 0.1267(9) 0.0747(13) 0.040(4) Uiso 1 1 d . . .
H13 H 1.446(2) 0.2120(11) -0.0463(15) 0.049(4) Uiso 1 1 d . . .
H18 H 0.517(2) 0.0087(11) 0.7342(16) 0.049(4) Uiso 1 1 d . . .
H16 H 0.845(2) 0.2538(11) -0.2986(16) 0.055(5) Uiso 1 1 d . . .
H20 H 0.057(2) 0.1151(12) 0.5677(16) 0.061(5) Uiso 1 1 d . . .
H15 H 1.132(2) 0.3220(12) -0.3317(17) 0.062(5) Uiso 1 1 d . . .
H19 H 1.427(3) 0.2995(13) -0.2060(17) 0.067(5) Uiso 1 1 d . . .
H17 H 0.583(2) 0.1445(12) 0.4661(16) 0.056(5) Uiso 1 1 d . . .
H21 H 0.249(2) 0.1738(13) 0.4447(18) 0.065(5) Uiso 1 1 d . . .
H4 H 0.688(3) 0.0371(14) 0.053(2) 0.076(6) Uiso 1 1 d . . .
H1A H 0.203(3) 0.0298(13) 0.708(2) 0.078(6) Uiso 1 1 d . . .
H1 H 0.814(3) 0.0133(16) 0.677(2) 0.099(8) 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
O2 C9 1.2550(18) . ?
O4 C8 1.3454(17) . ?
C3 C10 1.3620(19) . ?
C3 C8 1.4211(18) . ?
C3 C9 1.490(2) . ?
O3 C9 1.2392(18) . ?
C5 C10 1.398(2) . ?
C5 C13 1.406(2) . ?
C5 C7 1.4129(19) . ?
C7 C11 1.3987(19) . ?
C7 C16 1.408(2) . ?
C8 C11 1.364(2) . ?
C13 C19 1.351(2) . ?
C15 C16 1.351(2) . ?
C15 C19 1.400(2) . ?
O1 C14 1.3163(18) . ?
N1 C18 1.319(2) . ?
N1 C20 1.321(2) . ?
C14 C18 1.381(2) . ?
C14 C17 1.382(2) . ?
C17 C21 1.353(2) . ?
C20 C21 1.369(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
C10 C3 C8 118.93(12) . . ?
C10 C3 C9 119.95(11) . . ?
C8 C3 C9 121.12(12) . . ?
C10 C5 C13 122.93(13) . . ?
C10 C5 C7 118.18(12) . . ?
C13 C5 C7 118.87(13) . . ?
C11 C7 C16 122.35(12) . . ?
C11 C7 C5 119.24(12) . . ?
C16 C7 C5 118.39(13) . . ?
O4 C8 C11 118.80(11) . . ?
O4 C8 C3 121.50(12) . . ?
C11 C8 C3 119.70(12) . . ?
O3 C9 O2 124.65(13) . . ?
O3 C9 C3 118.20(13) . . ?
O2 C9 C3 117.14(12) . . ?
C3 C10 C5 122.46(12) . . ?
C8 C11 C7 121.41(12) . . ?
C19 C13 C5 121.18(14) . . ?
C16 C15 C19 120.57(16) . . ?
C15 C16 C7 121.03(14) . . ?
C13 C19 C15 119.94(15) . . ?
C18 N1 C20 123.47(14) . . ?
O1 C14 C18 122.90(14) . . ?
O1 C14 C17 119.95(13) . . ?
C18 C14 C17 117.15(14) . . ?
C21 C17 C14 120.51(14) . . ?
N1 C18 C14 120.26(14) . . ?
N1 C20 C21 118.31(16) . . ?
C17 C21 C20 120.28(16) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1032722'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N3 O5'
_chemical_formula_sum            'C17 H17 N3 O5'
_chemical_formula_weight         343.34

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                   7.8075(6)
_cell_length_b                   9.3259(5)
_cell_length_c                   12.6323(10)
_cell_angle_alpha                97.038(6)
_cell_angle_beta                 107.168(7)
_cell_angle_gamma                109.563(6)
_cell_volume                     802.65(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6373
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         29.51
_reflns_number_total             3723
_reflns_number_gt                2207
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0625P)²+0.0000P] 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         3723
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_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 0.3521(2) 0.76022(13) 0.02143(10) 0.0616(4) Uani 1 1 d . . .
H1 H 0.3142 0.6679 0.0240 0.092 Uiso 1 1 calc R . .
O2 O 0.2338(2) 0.52416(12) 0.10178(11) 0.0654(4) Uani 1 1 d . . .
C5 C 0.3076(2) 0.78098(16) 0.20316(14) 0.0398(4) Uani 1 1 d . . .
C6 C 0.4495(2) 1.10751(16) 0.23285(14) 0.0428(4) Uani 1 1 d . . .
C11 C 0.3210(2) 0.87531(17) 0.29883(14) 0.0419(4) Uani 1 1 d . . .
H11 H 0.2821 0.8294 0.3536 0.050 Uiso 1 1 calc R . .
C13 C 0.3642(3) 0.84986(17) 0.11753(14) 0.0431(4) Uani 1 1 d . . .
O3 O 0.1757(2) 0.55243(12) 0.26275(11) 0.0670(4) Uani 1 1 d . . .
C17 C 0.3921(2) 1.04108(17) 0.31823(14) 0.0400(4) Uani 1 1 d . . .
C18 C 0.4116(3) 1.14014(19) 0.41827(16) 0.0522(4) Uani 1 1 d . . .
H18 H 0.3738 1.0964 0.4742 0.063 Uiso 1 1 calc R . .
C19 C 0.2335(3) 0.60641(18) 0.18749(15) 0.0466(4) Uani 1 1 d . . .
C21 C 0.4318(3) 1.01050(18) 0.13379(15) 0.0483(4) Uani 1 1 d . . .
H21 H 0.4662 1.0552 0.0774 0.058 Uiso 1 1 calc R . .
C22 C 0.5395(3) 1.3651(2) 0.34963(19) 0.0657(6) Uani 1 1 d . . .
H22 H 0.5873 1.4736 0.3604 0.079 Uiso 1 1 calc R . .
C23 C 0.4849(3) 1.2988(2) 0.43444(18) 0.0622(5) Uani 1 1 d . . .
H23 H 0.4987 1.3631 0.5014 0.075 Uiso 1 1 calc R . .
C25 C 0.5238(3) 1.27423(18) 0.25282(17) 0.0558(5) Uani 1 1 d . . .
H25 H 0.5620 1.3211 0.1982 0.067 Uiso 1 1 calc R . .
N2 N 0.0293(2) 0.25238(14) 0.24648(11) 0.0414(3) Uani 1 1 d . . .
N3 N -0.07593(19) -0.01078(13) 0.14357(11) 0.0414(3) Uani 1 1 d . . .
O4 O 0.01816(18) 0.32430(12) 0.41769(10) 0.0515(3) Uani 1 1 d . . .
C8 C -0.1270(2) -0.05322(17) 0.22939(14) 0.0424(4) Uani 1 1 d . . .
C9 C -0.0217(2) 0.20495(17) 0.33326(14) 0.0410(4) Uani 1 1 d . . .
O5 O -0.20835(19) -0.20577(12) 0.22503(11) 0.0567(4) Uani 1 1 d . . .
N1 N 0.0638(2) 0.19895(17) 0.07464(13) 0.0481(4) Uani 1 1 d . . .
C14 C -0.1028(2) 0.04810(18) 0.32752(15) 0.0448(4) Uani 1 1 d . . .
H14 H -0.1394 0.0117 0.3860 0.054 Uiso 1 1 calc R . .
C16 C 0.0051(2) 0.14639(16) 0.15503(14) 0.0387(4) Uani 1 1 d . . .
C20 C -0.2390(3) -0.31938(18) 0.12571(18) 0.0633(5) Uani 1 1 d . . .
H20A H -0.3118 -0.2982 0.0581 0.095 Uiso 1 1 calc R . .
H20B H -0.3103 -0.4229 0.1306 0.095 Uiso 1 1 calc R . .
H20C H -0.1154 -0.3126 0.1223 0.095 Uiso 1 1 calc R . .
C24 C -0.0331(3) 0.2892(2) 0.51433(15) 0.0616(5) Uani 1 1 d . . .
H24A H -0.1696 0.2248 0.4890 0.092 Uiso 1 1 calc R . .
H24B H -0.0051 0.3851 0.5665 0.092 Uiso 1 1 calc R . .
H24C H 0.0409 0.2342 0.5522 0.092 Uiso 1 1 calc R . .
H1A H 0.117(3) 0.297(2) 0.0819(15) 0.056(5) Uiso 1 1 d . . .
H1B H 0.059(3) 0.133(2) 0.0096(18) 0.064(6) Uiso 1 1 d . . .
H3 H 0.094(3) 0.377(3) 0.2540(19) 0.097(7) 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 C13 1.3462(18) . ?
O2 C19 1.2491(18) . ?
C5 C11 1.360(2) . ?
C5 C13 1.429(2) . ?
C5 C19 1.499(2) . ?
C6 C21 1.393(2) . ?
C6 C17 1.418(2) . ?
C6 C25 1.425(2) . ?
C11 C17 1.418(2) . ?
C13 C21 1.377(2) . ?
O3 C19 1.2566(18) . ?
C17 C18 1.407(2) . ?
C18 C23 1.360(2) . ?
C22 C25 1.348(3) . ?
C22 C23 1.403(3) . ?
N2 C16 1.3466(19) . ?
N2 C9 1.3471(19) . ?
N3 C8 1.3212(19) . ?
N3 C16 1.3573(18) . ?
O4 C9 1.3245(18) . ?
O4 C24 1.4341(18) . ?
C8 O5 1.3362(17) . ?
C8 C14 1.386(2) . ?
C9 C14 1.368(2) . ?
O5 C20 1.443(2) . ?
N1 C16 1.3146(19) . ?

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
C11 C5 C13 119.33(13) . . ?
C11 C5 C19 120.34(13) . . ?
C13 C5 C19 120.33(14) . . ?
C21 C6 C17 120.03(13) . . ?
C21 C6 C25 122.42(15) . . ?
C17 C6 C25 117.55(15) . . ?
C5 C11 C17 122.50(14) . . ?
O1 C13 C21 119.68(13) . . ?
O1 C13 C5 121.04(13) . . ?
C21 C13 C5 119.28(15) . . ?
C18 C17 C11 123.00(14) . . ?
C18 C17 C6 119.59(14) . . ?
C11 C17 C6 117.39(15) . . ?
C23 C18 C17 120.98(16) . . ?
O2 C19 O3 124.20(13) . . ?
O2 C19 C5 118.56(13) . . ?
O3 C19 C5 117.25(15) . . ?
C13 C21 C6 121.45(14) . . ?
C25 C22 C23 121.12(15) . . ?
C18 C23 C22 119.68(18) . . ?
C22 C25 C6 121.07(16) . . ?
C16 N2 C9 120.40(12) . . ?
C8 N3 C16 115.38(14) . . ?
C9 O4 C24 117.82(12) . . ?
N3 C8 O5 119.36(15) . . ?
N3 C8 C14 125.59(13) . . ?
O5 C8 C14 115.04(13) . . ?
O4 C9 N2 112.41(12) . . ?
O4 C9 C14 127.66(14) . . ?
N2 C9 C14 119.92(15) . . ?
C8 O5 C20 118.64(12) . . ?
C9 C14 C8 116.06(14) . . ?
N1 C16 N2 117.99(13) . . ?
N1 C16 N3 119.40(15) . . ?
N2 C16 N3 122.61(13) . . ?

_diffrn_measured_fraction_theta_max 0.833
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1032723'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N3 O3'
_chemical_formula_weight         311.34

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                   7.6965(5)
_cell_length_b                   9.3446(6)
_cell_length_c                   11.9676(9)
_cell_angle_alpha                76.523(6)
_cell_angle_beta                 86.187(6)
_cell_angle_gamma                67.033(7)
_cell_volume                     770.38(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5687
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         29.47
_reflns_number_total             3568
_reflns_number_gt                2381
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0720P)²+0.1257P] 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         3568
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.8034(2) 0.29130(18) 0.77882(15) 0.0404(4) Uani 1 1 d . . .
N2 N 0.8859(2) 0.27011(16) 0.24822(12) 0.0442(4) Uani 1 1 d . . .
H2 H 0.9305 0.1682 0.2564 0.053 Uiso 1 1 calc R . .
O3 O 0.9755(2) 0.05190(14) 0.71631(12) 0.0612(4) Uani 1 1 d . . .
O2 O 0.8328(2) 0.03500(15) 0.88296(13) 0.0718(5) Uani 1 1 d . . .
C5 C 0.6746(2) 0.62326(19) 0.75570(15) 0.0422(4) Uani 1 1 d . . .
C6 C 0.7666(2) 0.55381(18) 0.66311(15) 0.0404(4) Uani 1 1 d . . .
N7 N 0.8574(2) 0.52214(16) 0.13518(13) 0.0479(4) Uani 1 1 d . . .
C8 C 0.7084(2) 0.4973(2) 0.31548(17) 0.0511(5) Uani 1 1 d . . .
H8 H 0.6333 0.5465 0.3707 0.061 Uiso 1 1 calc R . .
O1 O 0.6715(2) 0.27520(15) 0.96816(12) 0.0653(4) Uani 1 1 d . . .
H1 H 0.7126 0.1813 0.9643 0.098 Uiso 1 1 calc R . .
C10 C 0.6461(3) 0.5258(2) 0.85718(16) 0.0490(4) Uani 1 1 d . . .
H10 H 0.5853 0.5715 0.9175 0.059 Uiso 1 1 calc R . .
C11 C 0.8302(2) 0.38664(18) 0.67929(15) 0.0411(4) Uani 1 1 d . . .
H11 H 0.8928 0.3395 0.6200 0.049 Uiso 1 1 calc R . .
C12 C 0.7936(2) 0.6530(2) 0.56061(16) 0.0479(4) Uani 1 1 d . . .
H12 H 0.8505 0.6082 0.4992 0.057 Uiso 1 1 calc R . .
C13 C 0.7506(2) 0.5882(2) 0.21587(17) 0.0488(4) Uani 1 1 d . . .
C14 C 0.7062(2) 0.3638(2) 0.86939(15) 0.0454(4) Uani 1 1 d . . .
N15 N 1.0333(2) 0.29176(16) 0.07542(13) 0.0535(4) Uani 1 1 d . . .
H15A H 1.0606 0.3481 0.0145 0.064 Uiso 1 1 calc R . .
H15B H 1.0769 0.1896 0.0859 0.064 Uiso 1 1 calc R . .
C16 C 0.7784(2) 0.3350(2) 0.33124(16) 0.0458(4) Uani 1 1 d . . .
C17 C 0.6173(3) 0.7913(2) 0.74077(18) 0.0539(5) Uani 1 1 d . . .
H17 H 0.5564 0.8396 0.7999 0.065 Uiso 1 1 calc R . .
C18 C 0.7380(3) 0.8129(2) 0.54994(18) 0.0555(5) Uani 1 1 d . . .
H18 H 0.7583 0.8763 0.4821 0.067 Uiso 1 1 calc R . .
C19 C 0.9255(2) 0.36152(19) 0.15213(15) 0.0444(4) Uani 1 1 d . . .
C20 C 0.8772(2) 0.11303(19) 0.79257(16) 0.0474(4) Uani 1 1 d . . .
C21 C 0.7459(3) 0.2231(2) 0.43317(17) 0.0566(5) Uani 1 1 d . . .
H21A H 0.7028 0.1519 0.4082 0.085 Uiso 1 1 calc R . .
H21B H 0.6523 0.2825 0.4800 0.085 Uiso 1 1 calc R . .
H21C H 0.8618 0.1626 0.4771 0.085 Uiso 1 1 calc R . .
C22 C 0.6784(3) 0.7660(2) 0.1954(2) 0.0662(6) Uani 1 1 d . . .
H22A H 0.7325 0.7949 0.2523 0.099 Uiso 1 1 calc R . .
H22B H 0.5434 0.8085 0.2005 0.099 Uiso 1 1 calc R . .
H22C H 0.7129 0.8087 0.1203 0.099 Uiso 1 1 calc R . .
C23 C 0.6499(3) 0.8820(2) 0.64189(19) 0.0585(5) Uani 1 1 d . . .
H23 H 0.6135 0.9911 0.6348 0.070 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.368(2) . ?
C1 C14 1.426(2) . ?
C1 C20 1.507(2) . ?
N2 C16 1.349(2) . ?
N2 C19 1.358(2) . ?
O3 C20 1.243(2) . ?
O2 C20 1.264(2) . ?
C5 C10 1.399(2) . ?
C5 C6 1.422(2) . ?
C5 C17 1.425(2) . ?
C6 C11 1.411(2) . ?
C6 C12 1.412(2) . ?
N7 C13 1.329(2) . ?
N7 C19 1.352(2) . ?
C8 C16 1.367(2) . ?
C8 C13 1.393(3) . ?
O1 C14 1.352(2) . ?
C10 C14 1.373(2) . ?
C12 C18 1.361(2) . ?
C13 C22 1.495(2) . ?
N15 C19 1.308(2) . ?
C16 C21 1.488(3) . ?
C17 C23 1.357(3) . ?
C18 C23 1.406(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C14 118.69(14) . . ?
C11 C1 C20 120.48(15) . . ?
C14 C1 C20 120.82(16) . . ?
C16 N2 C19 121.67(14) . . ?
C10 C5 C6 119.55(14) . . ?
C10 C5 C17 122.74(16) . . ?
C6 C5 C17 117.70(17) . . ?
C11 C6 C12 122.90(15) . . ?
C11 C6 C5 117.84(16) . . ?
C12 C6 C5 119.25(15) . . ?
C13 N7 C19 117.90(16) . . ?
C16 C8 C13 119.31(17) . . ?
C14 C10 C5 121.20(16) . . ?
C1 C11 C6 122.57(15) . . ?
C18 C12 C6 121.28(17) . . ?
N7 C13 C8 122.04(15) . . ?
N7 C13 C22 116.81(18) . . ?
C8 C13 C22 121.15(17) . . ?
O1 C14 C10 118.97(15) . . ?
O1 C14 C1 120.92(15) . . ?
C10 C14 C1 120.11(17) . . ?
N2 C16 C8 117.81(17) . . ?
N2 C16 C21 116.94(15) . . ?
C8 C16 C21 125.24(17) . . ?
C23 C17 C5 121.24(17) . . ?
C12 C18 C23 119.74(18) . . ?
N15 C19 N7 119.73(17) . . ?
N15 C19 N2 118.98(15) . . ?
N7 C19 N2 121.28(16) . . ?
O3 C20 O2 124.17(15) . . ?
O3 C20 C1 119.38(16) . . ?
O2 C20 C1 116.45(15) . . ?
C17 C23 C18 120.75(17) . . ?

_diffrn_measured_fraction_theta_max 0.834
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1032724'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_audit_creation_date             2014-02-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H15 N2, C11 H7 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.40
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.2836(6)
_cell_length_b                   8.1666(10)
_cell_length_c                   34.870(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1789.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            5111
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.336
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.593
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                2211
_reflns_number_total             2979
_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       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 657 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -2.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2979
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.049
_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)+(0.0450P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1138
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C6(H6A,H6B), C9(H9A,H9B), C11(H11A,H11B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6167(4) 0.9219(3) 0.14221(7) 0.0438(7) Uani 1 1 d . . . . .
O3 O 1.2100(4) 1.6461(3) 0.21103(7) 0.0589(7) Uani 1 1 d . . . . .
H3 H 1.1078 1.6361 0.2255 0.088 Uiso 1 1 calc GR . . . .
C3 C 0.9919(4) 1.4561(4) 0.17519(9) 0.0415(8) Uani 1 1 d . . . . .
N2 N 0.4844(4) 1.0504(4) 0.21540(8) 0.0508(7) Uani 1 1 d . . . . .
H2A H 0.4043 1.0423 0.2391 0.061 Uiso 1 1 calc R . . . .
H2B H 0.5608 1.1536 0.2155 0.061 Uiso 1 1 calc R . . . .
C5 C 1.1784(5) 1.5536(4) 0.17904(9) 0.0424(8) Uani 1 1 d . . . . .
C6 C 0.4538(5) 1.0491(5) 0.14472(10) 0.0518(9) Uani 1 1 d . . . . .
H6A H 0.3526 1.0346 0.1240 0.062 Uiso 1 1 calc R . . . .
H6B H 0.5203 1.1554 0.1416 0.062 Uiso 1 1 calc R . . . .
O2 O 0.6851(4) 1.3453(4) 0.20500(8) 0.0770(9) Uani 1 1 d . . . . .
C8 C 0.9642(5) 1.3694(4) 0.14196(10) 0.0509(9) Uani 1 1 d . . . . .
H8 H 0.8422 1.3060 0.1393 0.061 Uiso 1 1 calc R . . . .
C9 C 0.6367(5) 0.9130(4) 0.21269(10) 0.0508(9) Uani 1 1 d . . . . .
H9A H 0.5604 0.8100 0.2142 0.061 Uiso 1 1 calc R . . . .
H9B H 0.7355 0.9179 0.2340 0.061 Uiso 1 1 calc R . . . .
C10 C 1.3258(5) 1.5572(4) 0.15055(10) 0.0479(9) Uani 1 1 d . . . . .
H10 H 1.4477 1.6204 0.1537 0.057 Uiso 1 1 calc R . . . .
C11 C 0.7581(4) 0.9213(5) 0.17547(9) 0.0487(9) Uani 1 1 d . . . . .
H11A H 0.8443 1.0199 0.1752 0.058 Uiso 1 1 calc R . . . .
H11B H 0.8532 0.8280 0.1738 0.058 Uiso 1 1 calc R . . . .
C12 C 1.1125(6) 1.3723(4) 0.11172(10) 0.0492(9) Uani 1 1 d . . . . .
C13 C 1.2991(5) 1.4680(4) 0.11643(10) 0.0451(8) Uani 1 1 d . . . . .
C14 C 0.3374(5) 1.0449(5) 0.18235(10) 0.0551(9) Uani 1 1 d . . . . .
H14A H 0.2410 1.1375 0.1837 0.066 Uiso 1 1 calc R . . . .
H14B H 0.2529 0.9457 0.1837 0.066 Uiso 1 1 calc R . . . .
C15 C 0.7122(5) 0.8999(4) 0.10585(10) 0.0469(9) Uani 1 1 d . . . . .
C16 C 1.4498(6) 1.4699(5) 0.08613(11) 0.0633(11) Uani 1 1 d . . . . .
H16 H 1.5732 1.5319 0.0887 0.076 Uiso 1 1 calc R . . . .
O1 O 0.8486(4) 1.5527(4) 0.23347(8) 0.0690(8) Uani 1 1 d . . . . .
C18 C 0.8295(5) 1.4487(5) 0.20669(11) 0.0523(9) Uani 1 1 d . . . . .
C19 C 0.6123(6) 0.9526(6) 0.07260(11) 0.0664(11) Uani 1 1 d . . . . .
H19 H 0.4829 1.0074 0.0743 0.080 Uiso 1 1 calc R . . . .
C20 C 0.9042(6) 0.8176(5) 0.10157(11) 0.0678(12) Uani 1 1 d . . . . .
H20 H 0.9762 0.7804 0.1232 0.081 Uiso 1 1 calc R . . . .
C21 C 1.0853(7) 1.2827(5) 0.07712(11) 0.0672(11) Uani 1 1 d . . . . .
H21 H 0.9639 1.2193 0.0736 0.081 Uiso 1 1 calc R . . . .
C22 C 1.4173(8) 1.3833(6) 0.05364(12) 0.0755(12) Uani 1 1 d . . . . .
H22 H 1.5179 1.3868 0.0341 0.091 Uiso 1 1 calc R . . . .
C23 C 0.8901(9) 0.8433(6) 0.03326(13) 0.0900(15) Uani 1 1 d . . . . .
H23 H 0.9493 0.8241 0.0092 0.108 Uiso 1 1 calc R . . . .
C24 C 0.7018(8) 0.9252(6) 0.03682(12) 0.0824(14) Uani 1 1 d . . . . .
H24 H 0.6326 0.9630 0.0150 0.099 Uiso 1 1 calc R . . . .
C25 C 1.2348(8) 1.2889(6) 0.04915(11) 0.0806(14) Uani 1 1 d . . . . .
H25 H 1.2152 1.2293 0.0267 0.097 Uiso 1 1 calc R . . . .
C26 C 0.9893(7) 0.7905(6) 0.06568(12) 0.0857(15) Uani 1 1 d . . . . .
H26 H 1.1177 0.7347 0.0636 0.103 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.461(4) . ?
N1 C11 1.461(4) . ?
N1 C15 1.414(4) . ?
O3 C5 1.362(4) . ?
C3 C5 1.423(4) . ?
C3 C8 1.369(4) . ?
C3 C18 1.500(4) . ?
N2 C9 1.478(4) . ?
N2 C14 1.478(4) . ?
C5 C10 1.359(4) . ?
C6 C14 1.503(4) . ?
O2 C18 1.241(4) . ?
C8 C12 1.408(5) . ?
C9 C11 1.507(4) . ?
C10 C13 1.405(4) . ?
C12 C13 1.419(5) . ?
C12 C21 1.421(5) . ?
C13 C16 1.419(5) . ?
C15 C19 1.387(5) . ?
C15 C20 1.388(5) . ?
C16 C22 1.351(5) . ?
O1 C18 1.268(4) . ?
C19 C24 1.387(5) . ?
C20 C26 1.379(5) . ?
C21 C25 1.355(5) . ?
C22 C25 1.390(6) . ?
C23 C24 1.365(6) . ?
C23 C26 1.361(6) . ?

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 N1 C11 112.4(3) . . ?
C15 N1 C6 116.2(3) . . ?
C15 N1 C11 116.9(2) . . ?
C5 C3 C18 120.9(3) . . ?
C8 C3 C5 118.3(3) . . ?
C8 C3 C18 120.8(3) . . ?
C14 N2 C9 109.4(3) . . ?
O3 C5 C3 120.5(3) . . ?
C10 C5 O3 119.2(3) . . ?
C10 C5 C3 120.3(3) . . ?
N1 C6 C14 112.2(3) . . ?
C3 C8 C12 122.8(3) . . ?
N2 C9 C11 110.4(3) . . ?
C5 C10 C13 121.8(3) . . ?
N1 C11 C9 112.1(2) . . ?
C8 C12 C13 118.0(3) . . ?
C8 C12 C21 123.2(3) . . ?
C13 C12 C21 118.8(3) . . ?
C10 C13 C12 118.8(3) . . ?
C10 C13 C16 123.0(3) . . ?
C12 C13 C16 118.1(3) . . ?
N2 C14 C6 112.1(2) . . ?
C19 C15 N1 121.2(3) . . ?
C19 C15 C20 117.0(3) . . ?
C20 C15 N1 121.8(3) . . ?
C22 C16 C13 121.2(4) . . ?
O2 C18 C3 119.4(4) . . ?
O2 C18 O1 124.1(3) . . ?
O1 C18 C3 116.6(3) . . ?
C24 C19 C15 121.2(4) . . ?
C26 C20 C15 120.8(4) . . ?
C25 C21 C12 120.6(4) . . ?
C16 C22 C25 120.6(4) . . ?
C26 C23 C24 118.5(4) . . ?
C23 C24 C19 120.8(4) . . ?
C21 C25 C22 120.8(4) . . ?
C23 C26 C20 121.7(4) . . ?

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1032725'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35

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   p21/n

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

_cell_length_a                   7.0998(11)
_cell_length_b                   16.265(3)
_cell_length_c                   14.012(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.333(18)
_cell_angle_gamma                90.00
_cell_volume                     1604.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6499
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2832
_reflns_number_gt                1488
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0886P)²+0.0898P] 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         2832
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1966
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.5272(3) 0.12832(14) 0.12320(19) 0.0585(6) Uani 1 1 d . . .
O2 O 0.6348(3) 0.08513(12) -0.02249(17) 0.0870(6) Uani 1 1 d . . .
O3 O 0.3065(2) 0.13940(13) -0.02207(14) 0.0832(6) Uani 1 1 d . . .
H3 H 0.3992 0.1194 -0.0428 0.125 Uiso 1 1 calc R . .
C4 C 0.5631(3) 0.13978(15) 0.2210(2) 0.0693(7) Uani 1 1 d . . .
H4 H 0.6835 0.1278 0.2521 0.083 Uiso 1 1 calc R . .
C5 C 0.3444(3) 0.14868(14) 0.0754(2) 0.0593(6) Uani 1 1 d . . .
C6 C 0.2072(3) 0.17693(14) 0.1266(2) 0.0665(7) Uani 1 1 d . . .
H6 H 0.0881 0.1899 0.0945 0.080 Uiso 1 1 calc R . .
C7 C 0.2415(4) 0.18692(14) 0.2266(2) 0.0664(7) Uani 1 1 d . . .
C8 C 0.6774(4) 0.09363(15) 0.0681(2) 0.0702(8) Uani 1 1 d . . .
C9 C 0.4238(4) 0.16904(14) 0.2758(2) 0.0680(7) Uani 1 1 d . . .
O1 O 0.8352(3) 0.07579(12) 0.11243(16) 0.0941(7) Uani 1 1 d . . .
N1 N 0.9584(3) 0.06710(13) -0.11402(14) 0.0686(6) Uani 1 1 d . . .
H1A H 1.0034 0.0160 -0.1128 0.082 Uiso 1 1 calc R . .
H1B H 0.8562 0.0689 -0.0833 0.082 Uiso 1 1 calc R . .
H1C H 1.0470 0.1007 -0.0852 0.082 Uiso 1 1 calc R . .
C12 C 0.4549(5) 0.18037(19) 0.3773(2) 0.0940(10) Uani 1 1 d . . .
H12 H 0.5750 0.1705 0.4102 0.113 Uiso 1 1 calc R . .
C13 C 0.9058(4) 0.09343(15) -0.21555(19) 0.0692(7) Uani 1 1 d . . .
H13 H 0.8640 0.1508 -0.2153 0.083 Uiso 1 1 calc R . .
C14 C 0.0967(4) 0.21320(17) 0.2827(3) 0.0860(9) Uani 1 1 d . . .
H14 H -0.0242 0.2251 0.2520 0.103 Uiso 1 1 calc R . .
C15 C 0.1330(6) 0.2209(2) 0.3791(3) 0.1048(12) Uani 1 1 d . . .
H15 H 0.0359 0.2368 0.4138 0.126 Uiso 1 1 calc R . .
C16 C 0.7430(5) 0.0428(2) -0.2609(2) 0.1051(11) Uani 1 1 d . . .
H16A H 0.6352 0.0502 -0.2257 0.126 Uiso 1 1 calc R . .
H16B H 0.7781 -0.0149 -0.2575 0.126 Uiso 1 1 calc R . .
C17 C 1.0753(5) 0.0890(2) -0.2697(3) 0.1132(12) Uani 1 1 d . . .
H17A H 1.1279 0.0340 -0.2646 0.136 Uiso 1 1 calc R . .
H17B H 1.1721 0.1269 -0.2412 0.136 Uiso 1 1 calc R . .
C18 C 0.3121(7) 0.2055(2) 0.4275(3) 0.1108(12) Uani 1 1 d . . .
H18 H 0.3351 0.2122 0.4938 0.133 Uiso 1 1 calc R . .
C19 C 1.0208(8) 0.1108(3) -0.3760(4) 0.164(2) Uani 1 1 d . . .
H19A H 0.9871 0.1686 -0.3818 0.196 Uiso 1 1 calc R . .
H19B H 1.1286 0.1015 -0.4107 0.196 Uiso 1 1 calc R . .
C20 C 0.6872(8) 0.0671(3) -0.3656(3) 0.1489(17) Uani 1 1 d . . .
H20A H 0.5843 0.0323 -0.3942 0.179 Uiso 1 1 calc R . .
H20B H 0.6431 0.1236 -0.3689 0.179 Uiso 1 1 calc R . .
C22 C 0.8531(11) 0.0585(3) -0.4199(3) 0.182(3) Uani 1 1 d . . .
H22A H 0.8165 0.0750 -0.4861 0.218 Uiso 1 1 calc R . .
H22B H 0.8914 0.0012 -0.4198 0.218 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.374(3) . ?
C1 C5 1.421(3) . ?
C1 C8 1.504(3) . ?
O2 C8 1.274(3) . ?
O3 C5 1.367(3) . ?
C4 C9 1.410(4) . ?
C5 C6 1.361(3) . ?
C6 C7 1.400(3) . ?
C7 C9 1.416(4) . ?
C7 C14 1.437(4) . ?
C8 O1 1.244(3) . ?
C9 C12 1.423(4) . ?
N1 C13 1.487(3) . ?
C12 C18 1.368(4) . ?
C13 C16 1.494(4) . ?
C13 C17 1.504(4) . ?
C14 C15 1.348(4) . ?
C15 C18 1.385(5) . ?
C16 C20 1.522(5) . ?
C17 C19 1.531(5) . ?
C19 C22 1.528(7) . ?
C20 C22 1.488(7) . ?

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 C1 C5 118.7(2) . . ?
C4 C1 C8 120.6(2) . . ?
C5 C1 C8 120.7(3) . . ?
C1 C4 C9 122.4(2) . . ?
C6 C5 O3 120.1(2) . . ?
C6 C5 C1 120.1(3) . . ?
O3 C5 C1 119.8(2) . . ?
C5 C6 C7 121.4(2) . . ?
C6 C7 C9 119.6(2) . . ?
C6 C7 C14 122.4(3) . . ?
C9 C7 C14 117.9(3) . . ?
O1 C8 O2 123.8(3) . . ?
O1 C8 C1 118.9(3) . . ?
O2 C8 C1 117.3(2) . . ?
C4 C9 C7 117.7(3) . . ?
C4 C9 C12 123.9(3) . . ?
C7 C9 C12 118.4(3) . . ?
C18 C12 C9 121.4(3) . . ?
N1 C13 C16 109.5(2) . . ?
N1 C13 C17 110.5(2) . . ?
C16 C13 C17 112.6(3) . . ?
C15 C14 C7 121.1(3) . . ?
C14 C15 C18 121.3(3) . . ?
C13 C16 C20 111.0(3) . . ?
C13 C17 C19 111.1(3) . . ?
C12 C18 C15 119.8(3) . . ?
C22 C19 C17 110.5(4) . . ?
C22 C20 C16 110.0(4) . . ?
C20 C22 C19 111.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1032726'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H62 N2 O6'
_chemical_formula_weight         738.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1744(4)
_cell_length_b                   14.8970(4)
_cell_length_c                   21.1083(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.01
_cell_angle_gamma                90
_cell_volume                     4142.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6715
_cell_measurement_theta_min      3.0900
_cell_measurement_theta_max      25.5920

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.92192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.710
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27764
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.214
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             7316
_reflns_number_gt                5005
_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 FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
_computing_molecular_graphics
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0444P)²+0.6347P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7316
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
N1 N -0.06946(10) -0.11742(9) 0.03819(6) 0.0473(4) Uani 1 1 d . . . . .
H1A H -0.0024 -0.0905 0.0386 0.057 Uiso 1 1 d R U . . .
H1B H -0.1061 -0.0915 0.0028 0.057 Uiso 1 1 d R U . . .
C36 C -0.12283(12) -0.08939(11) 0.09794(8) 0.0484(4) Uani 1 1 d . . . . .
H36 H -0.0830 -0.1103 0.1343 0.058 Uiso 1 1 calc R U . . .
C37 C -0.22804(13) -0.12902(13) 0.10243(9) 0.0563(5) Uani 1 1 d . . . . .
H37A H -0.2239 -0.1940 0.1011 0.068 Uiso 1 1 calc R U . . .
H37B H -0.2685 -0.1092 0.0667 0.068 Uiso 1 1 calc R U . . .
C38 C -0.27830(15) -0.09977(14) 0.16376(10) 0.0656(5) Uani 1 1 d . . . . .
H38A H -0.3466 -0.1240 0.1655 0.079 Uiso 1 1 calc R U . . .
H38B H -0.2406 -0.1239 0.1993 0.079 Uiso 1 1 calc R U . . .
C39 C -0.28286(15) 0.00131(15) 0.16928(10) 0.0700(6) Uani 1 1 d . . . . .
H39A H -0.3087 0.0173 0.2108 0.084 Uiso 1 1 calc R U . . .
H39B H -0.3297 0.0246 0.1378 0.084 Uiso 1 1 calc R U . . .
C40 C -0.17988(16) 0.04452(13) 0.15991(10) 0.0674(5) Uani 1 1 d . . . . .
H40A H -0.1372 0.0310 0.1961 0.081 Uiso 1 1 calc R U . . .
H40B H -0.1881 0.1092 0.1578 0.081 Uiso 1 1 calc R U . . .
C41 C -0.12740(14) 0.01220(12) 0.09990(9) 0.0572(5) Uani 1 1 d . . . . .
H41A H -0.1641 0.0341 0.0632 0.069 Uiso 1 1 calc R U . . .
H41B H -0.0591 0.0364 0.0983 0.069 Uiso 1 1 calc R U . . .
C42 C -0.05660(13) -0.21613(11) 0.02507(8) 0.0501(4) Uani 1 1 d . . . . .
H42 H -0.1233 -0.2415 0.0149 0.060 Uiso 1 1 calc R U . . .
C43 C 0.01090(15) -0.22577(13) -0.03251(9) 0.0624(5) Uani 1 1 d . . . . .
H43A H 0.0750 -0.1957 -0.0246 0.075 Uiso 1 1 calc R U . . .
H43B H -0.0212 -0.1967 -0.0684 0.075 Uiso 1 1 calc R U . . .
C44 C 0.03101(19) -0.32384(15) -0.04859(11) 0.0812(6) Uani 1 1 d . . . . .
H44A H -0.0318 -0.3520 -0.0620 0.097 Uiso 1 1 calc R U . . .
H44B H 0.0789 -0.3272 -0.0834 0.097 Uiso 1 1 calc R U . . .
C45 C 0.07340(17) -0.37384(15) 0.00796(11) 0.0786(6) Uani 1 1 d . . . . .
H45A H 0.0812 -0.4369 -0.0025 0.094 Uiso 1 1 calc R U . . .
H45B H 0.1398 -0.3501 0.0185 0.094 Uiso 1 1 calc R U . . .
C46 C -0.01384(15) -0.26627(12) 0.08127(9) 0.0612(5) Uani 1 1 d . . . . .
H46A H -0.0607 -0.2622 0.1166 0.073 Uiso 1 1 calc R U . . .
H46B H 0.0499 -0.2392 0.0941 0.073 Uiso 1 1 calc R U . . .
C47 C 0.00348(17) -0.36435(13) 0.06436(11) 0.0764(6) Uani 1 1 d . . . . .
H47A H 0.0328 -0.3952 0.1004 0.092 Uiso 1 1 calc R U . . .
H47B H -0.0612 -0.3924 0.0548 0.092 Uiso 1 1 calc R U . . .
N2 N -0.48275(10) -0.37743(8) 0.04334(6) 0.0439(3) Uani 1 1 d . . . . .
H2A H -0.4654 -0.3950 0.0004 0.053 Uiso 1 1 d R U . . .
H2B H -0.5323 -0.4203 0.0588 0.053 Uiso 1 1 d R U . . .
C24 C -0.59890(16) -0.12630(13) -0.02720(11) 0.0712(6) Uani 1 1 d . . . . .
H24A H -0.5711 -0.1338 -0.0694 0.085 Uiso 1 1 calc R U . . .
H24B H -0.6350 -0.0696 -0.0261 0.085 Uiso 1 1 calc R U . . .
C25 C -0.51351(16) -0.12395(12) 0.02017(11) 0.0656(5) Uani 1 1 d . . . . .
H25A H -0.5405 -0.1090 0.0616 0.079 Uiso 1 1 calc R U . . .
H25B H -0.4656 -0.0775 0.0082 0.079 Uiso 1 1 calc R U . . .
C26 C -0.45873(13) -0.21353(11) 0.02382(9) 0.0544(5) Uani 1 1 d . . . . .
H26A H -0.4269 -0.2266 -0.0166 0.065 Uiso 1 1 calc R U . . .
H26B H -0.4060 -0.2107 0.0558 0.065 Uiso 1 1 calc R U . . .
C27 C -0.53337(12) -0.28701(10) 0.04025(8) 0.0454(4) Uani 1 1 d . . . . .
H27 H -0.5631 -0.2737 0.0818 0.054 Uiso 1 1 calc R U . . .
C28 C -0.61805(13) -0.29146(12) -0.00826(9) 0.0559(5) Uani 1 1 d . . . . .
H28A H -0.6663 -0.3375 0.0040 0.067 Uiso 1 1 calc R U . . .
H28B H -0.5901 -0.3077 -0.0492 0.067 Uiso 1 1 calc R U . . .
C29 C -0.67231(15) -0.20197(13) -0.01359(11) 0.0686(6) Uani 1 1 d . . . . .
H29A H -0.7222 -0.2052 -0.0473 0.082 Uiso 1 1 calc R U . . .
H29B H -0.7079 -0.1897 0.0257 0.082 Uiso 1 1 calc R U . . .
C30 C -0.38922(13) -0.38672(11) 0.08320(8) 0.0484(4) Uani 1 1 d . . . . .
H30 H -0.3369 -0.3471 0.0656 0.058 Uiso 1 1 calc R U . . .
C31 C -0.40622(16) -0.36063(14) 0.15160(9) 0.0647(5) Uani 1 1 d . . . . .
H31A H -0.4582 -0.3987 0.1700 0.078 Uiso 1 1 calc R U . . .
H31B H -0.4294 -0.2989 0.1538 0.078 Uiso 1 1 calc R U . . .
C32 C -0.30822(18) -0.37074(15) 0.18863(11) 0.0823(7) Uani 1 1 d . . . . .
H32A H -0.2591 -0.3275 0.1731 0.099 Uiso 1 1 calc R U . . .
H32B H -0.3210 -0.3575 0.2329 0.099 Uiso 1 1 calc R U . . .
C33 C -0.26407(17) -0.46416(16) 0.18312(11) 0.0814(7) Uani 1 1 d . . . . .
H33A H -0.3078 -0.5062 0.2051 0.098 Uiso 1 1 calc R U . . .
H33B H -0.1981 -0.4655 0.2034 0.098 Uiso 1 1 calc R U . . .
C34 C -0.25296(16) -0.49327(16) 0.11471(11) 0.0790(6) Uani 1 1 d . . . . .
H34A H -0.2322 -0.5557 0.1133 0.095 Uiso 1 1 calc R U . . .
H34B H -0.2003 -0.4578 0.0946 0.095 Uiso 1 1 calc R U . . .
C35 C -0.35164(14) -0.48223(12) 0.07822(9) 0.0596(5) Uani 1 1 d . . . . .
H35A H -0.3408 -0.4974 0.0341 0.071 Uiso 1 1 calc R U . . .
H35B H -0.4024 -0.5228 0.0952 0.071 Uiso 1 1 calc R U . . .
O4 O -0.39720(10) -0.10813(9) 0.42515(6) 0.0643(4) Uani 1 1 d . . . . .
O11 O -0.19692(11) 0.06914(8) 0.34124(7) 0.0726(4) Uani 1 1 d . . . . .
H11 H -0.2479 0.0782 0.3625 0.087 Uiso 1 1 d R U . . .
O13 O -0.35825(10) 0.03213(9) 0.40057(7) 0.0726(4) Uani 1 1 d . . . . .
C13 C -0.04752(18) -0.32643(18) 0.27970(11) 0.0828(7) Uani 1 1 d . . . . .
H13 H -0.0378 -0.3875 0.2731 0.099 Uiso 1 1 calc R U . . .
C14 C 0.02403(18) -0.2652(2) 0.25770(11) 0.0902(8) Uani 1 1 d . . . . .
H14 H 0.0814 -0.2861 0.2367 0.108 Uiso 1 1 calc R U . . .
C15 C 0.01141(15) -0.17530(18) 0.26645(10) 0.0772(7) Uani 1 1 d . . . . .
H15 H 0.0600 -0.1354 0.2513 0.093 Uiso 1 1 calc R U . . .
C16 C -0.07583(13) -0.14208(14) 0.29864(8) 0.0542(5) Uani 1 1 d . . . . .
C17 C -0.09374(14) -0.05033(14) 0.30812(8) 0.0582(5) Uani 1 1 d . . . . .
H17 H -0.0458 -0.0089 0.2943 0.070 Uiso 1 1 calc R U . . .
C18 C -0.18002(13) -0.02031(12) 0.33712(8) 0.0503(4) Uani 1 1 d . . . . .
C19 C -0.25133(12) -0.08281(11) 0.36224(7) 0.0430(4) Uani 1 1 d . . . . .
C20 C -0.23379(12) -0.17241(11) 0.35372(7) 0.0456(4) Uani 1 1 d . . . . .
H20 H -0.2800 -0.2135 0.3701 0.055 Uiso 1 1 calc R U . . .
C21 C -0.14788(13) -0.20491(12) 0.32083(8) 0.0486(4) Uani 1 1 d . . . . .
C22 C -0.13114(16) -0.29738(13) 0.31067(9) 0.0645(5) Uani 1 1 d . . . . .
H22 H -0.1782 -0.3389 0.3255 0.077 Uiso 1 1 calc R U . . .
C23 C -0.34299(14) -0.05185(13) 0.39875(8) 0.0503(4) Uani 1 1 d . . . . .
O7 O -0.63537(10) 0.09856(8) 0.11797(6) 0.0665(4) Uani 1 1 d . . . . .
H7 H -0.6824 0.1069 0.0932 0.080 Uiso 1 1 d R U . . .
O17 O -0.87895(10) -0.06352(10) 0.07080(7) 0.0789(4) Uani 1 1 d . . . . .
O27 O -0.79752(10) 0.06474(10) 0.05701(6) 0.0684(4) Uani 1 1 d . . . . .
C2 C -0.59654(18) -0.26469(16) 0.27390(11) 0.0813(7) Uani 1 1 d . . . . .
H2 H -0.6020 -0.3205 0.2933 0.098 Uiso 1 1 calc R U . . .
C3 C -0.51654(17) -0.20790(17) 0.28973(10) 0.0764(6) Uani 1 1 d . . . . .
H3 H -0.4695 -0.2257 0.3201 0.092 Uiso 1 1 calc R U . . .
C4 C -0.50680(14) -0.12723(15) 0.26127(9) 0.0632(5) Uani 1 1 d . . . . .
H4 H -0.4523 -0.0905 0.2719 0.076 Uiso 1 1 calc R U . . .
C5 C -0.57792(12) -0.09723(12) 0.21543(8) 0.0478(4) Uani 1 1 d . . . . .
C6 C -0.66045(13) -0.15434(12) 0.20035(8) 0.0490(4) Uani 1 1 d . . . . .
C7 C -0.66663(16) -0.23913(14) 0.23033(10) 0.0685(6) Uani 1 1 d . . . . .
H7A H -0.7195 -0.2779 0.2200 0.082 Uiso 1 1 calc R U . . .
C8 C -0.73330(13) -0.12283(12) 0.15696(8) 0.0496(4) Uani 1 1 d . . . . .
H8 H -0.7877 -0.1600 0.1468 0.059 Uiso 1 1 calc R U . . .
C9 C -0.72789(12) -0.04032(11) 0.12901(7) 0.0435(4) Uani 1 1 d . . . . .
C10 C -0.64409(12) 0.01594(11) 0.14403(8) 0.0455(4) Uani 1 1 d . . . . .
C11 C -0.57160(12) -0.01276(12) 0.18602(8) 0.0501(4) Uani 1 1 d . . . . .
H11A H -0.5170 0.0245 0.1952 0.060 Uiso 1 1 calc R U . . .
C12 C -0.80808(13) -0.01156(14) 0.08253(8) 0.0528(5) 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
N1 C36 1.503(2) . ?
N1 C42 1.506(2) . ?
N1 H1A 0.9699 . ?
N1 H1B 0.9699 . ?
C36 C37 1.510(2) . ?
C36 C41 1.515(2) . ?
C36 H36 0.9800 . ?
C37 C38 1.518(3) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.512(3) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.515(3) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.521(3) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C46 1.511(2) . ?
C42 C43 1.513(2) . ?
C42 H42 0.9800 . ?
C43 C44 1.523(3) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.514(3) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C47 1.512(3) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.521(3) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
N2 C30 1.498(2) . ?
N2 C27 1.504(2) . ?
N2 H2A 0.9701 . ?
N2 H2B 0.9700 . ?
C24 C25 1.505(3) . ?
C24 C29 1.513(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.519(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.512(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.516(2) . ?
C27 H27 0.9800 . ?
C28 C29 1.517(2) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C35 1.510(2) . ?
C30 C31 1.512(2) . ?
C30 H30 0.9800 . ?
C31 C32 1.517(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.513(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.515(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.520(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
O4 C23 1.234(2) . ?
O11 C18 1.354(2) . ?
O11 H11 0.8200 . ?
O13 C23 1.268(2) . ?
C13 C22 1.352(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.424(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.401(3) . ?
C16 C21 1.413(2) . ?
C17 C18 1.366(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.425(2) . ?
C19 C20 1.367(2) . ?
C19 C23 1.505(2) . ?
C20 C21 1.413(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.411(2) . ?
C22 H22 0.9300 . ?
O7 C10 1.353(2) . ?
O7 H7 0.8201 . ?
O17 C12 1.238(2) . ?
O27 C12 1.265(2) . ?
C2 C7 1.358(3) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.419(2) . ?
C4 H4 0.9300 . ?
C5 C11 1.406(2) . ?
C5 C6 1.417(2) . ?
C6 C8 1.407(2) . ?
C6 C7 1.415(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.365(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.422(2) . ?
C9 C12 1.504(2) . ?
C10 C11 1.371(2) . ?
C11 H11A 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
C36 N1 C42 118.57(12) . . ?
C36 N1 H1A 107.7 . . ?
C42 N1 H1A 107.7 . . ?
C36 N1 H1B 107.7 . . ?
C42 N1 H1B 107.7 . . ?
H1A N1 H1B 107.1 . . ?
N1 C36 C37 111.94(14) . . ?
N1 C36 C41 108.60(13) . . ?
C37 C36 C41 110.64(15) . . ?
N1 C36 H36 108.5 . . ?
C37 C36 H36 108.5 . . ?
C41 C36 H36 108.5 . . ?
C36 C37 C38 109.99(15) . . ?
C36 C37 H37A 109.7 . . ?
C38 C37 H37A 109.7 . . ?
C36 C37 H37B 109.7 . . ?
C38 C37 H37B 109.7 . . ?
H37A C37 H37B 108.2 . . ?
C39 C38 C37 111.65(16) . . ?
C39 C38 H38A 109.3 . . ?
C37 C38 H38A 109.3 . . ?
C39 C38 H38B 109.3 . . ?
C37 C38 H38B 109.3 . . ?
H38A C38 H38B 108.0 . . ?
C38 C39 C40 112.19(17) . . ?
C38 C39 H39A 109.2 . . ?
C40 C39 H39A 109.2 . . ?
C38 C39 H39B 109.2 . . ?
C40 C39 H39B 109.2 . . ?
H39A C39 H39B 107.9 . . ?
C39 C40 C41 112.42(16) . . ?
C39 C40 H40A 109.1 . . ?
C41 C40 H40A 109.1 . . ?
C39 C40 H40B 109.1 . . ?
C41 C40 H40B 109.1 . . ?
H40A C40 H40B 107.9 . . ?
C36 C41 C40 110.91(15) . . ?
C36 C41 H41A 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C36 C41 H41B 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 108.0 . . ?
N1 C42 C46 112.36(14) . . ?
N1 C42 C43 107.86(14) . . ?
C46 C42 C43 111.39(15) . . ?
N1 C42 H42 108.4 . . ?
C46 C42 H42 108.4 . . ?
C43 C42 H42 108.4 . . ?
C42 C43 C44 111.86(16) . . ?
C42 C43 H43A 109.2 . . ?
C44 C43 H43A 109.2 . . ?
C42 C43 H43B 109.2 . . ?
C44 C43 H43B 109.2 . . ?
H43A C43 H43B 107.9 . . ?
C45 C44 C43 111.12(18) . . ?
C45 C44 H44A 109.4 . . ?
C43 C44 H44A 109.4 . . ?
C45 C44 H44B 109.4 . . ?
C43 C44 H44B 109.4 . . ?
H44A C44 H44B 108.0 . . ?
C47 C45 C44 110.49(18) . . ?
C47 C45 H45A 109.6 . . ?
C44 C45 H45A 109.6 . . ?
C47 C45 H45B 109.6 . . ?
C44 C45 H45B 109.6 . . ?
H45A C45 H45B 108.1 . . ?
C42 C46 C47 110.27(17) . . ?
C42 C46 H46A 109.6 . . ?
C47 C46 H46A 109.6 . . ?
C42 C46 H46B 109.6 . . ?
C47 C46 H46B 109.6 . . ?
H46A C46 H46B 108.1 . . ?
C45 C47 C46 111.47(17) . . ?
C45 C47 H47A 109.3 . . ?
C46 C47 H47A 109.3 . . ?
C45 C47 H47B 109.3 . . ?
C46 C47 H47B 109.3 . . ?
H47A C47 H47B 108.0 . . ?
C30 N2 C27 118.13(12) . . ?
C30 N2 H2A 107.8 . . ?
C27 N2 H2A 107.8 . . ?
C30 N2 H2B 107.7 . . ?
C27 N2 H2B 107.8 . . ?
H2A N2 H2B 107.1 . . ?
C25 C24 C29 111.65(17) . . ?
C25 C24 H24A 109.3 . . ?
C29 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C29 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 111.61(16) . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C27 C26 C25 109.79(15) . . ?
C27 C26 H26A 109.7 . . ?
C25 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
C25 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
N2 C27 C26 111.71(13) . . ?
N2 C27 C28 108.44(13) . . ?
C26 C27 C28 110.82(14) . . ?
N2 C27 H27 108.6 . . ?
C26 C27 H27 108.6 . . ?
C28 C27 H27 108.6 . . ?
C27 C28 C29 111.01(15) . . ?
C27 C28 H28A 109.4 . . ?
C29 C28 H28A 109.4 . . ?
C27 C28 H28B 109.4 . . ?
C29 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C24 C29 C28 111.57(16) . . ?
C24 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
C24 C29 H29B 109.3 . . ?
C28 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
N2 C30 C35 108.52(13) . . ?
N2 C30 C31 112.99(14) . . ?
C35 C30 C31 110.93(15) . . ?
N2 C30 H30 108.1 . . ?
C35 C30 H30 108.1 . . ?
C31 C30 H30 108.1 . . ?
C30 C31 C32 109.91(17) . . ?
C30 C31 H31A 109.7 . . ?
C32 C31 H31A 109.7 . . ?
C30 C31 H31B 109.7 . . ?
C32 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
C33 C32 C31 112.27(18) . . ?
C33 C32 H32A 109.2 . . ?
C31 C32 H32A 109.2 . . ?
C33 C32 H32B 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C32 C33 C34 111.95(18) . . ?
C32 C33 H33A 109.2 . . ?
C34 C33 H33A 109.2 . . ?
C32 C33 H33B 109.2 . . ?
C34 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C33 C34 C35 111.68(17) . . ?
C33 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 107.9 . . ?
C30 C35 C34 110.31(16) . . ?
C30 C35 H35A 109.6 . . ?
C34 C35 H35A 109.6 . . ?
C30 C35 H35B 109.6 . . ?
C34 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
C18 O11 H11 109.4 . . ?
C22 C13 C14 120.2(2) . . ?
C22 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C21 119.06(16) . . ?
C17 C16 C15 122.89(19) . . ?
C21 C16 C15 118.05(19) . . ?
C18 C17 C16 121.55(17) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
O11 C18 C17 119.19(17) . . ?
O11 C18 C19 120.72(15) . . ?
C17 C18 C19 120.09(17) . . ?
C20 C19 C18 118.54(15) . . ?
C20 C19 C23 120.16(15) . . ?
C18 C19 C23 121.28(15) . . ?
C19 C20 C21 122.32(16) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C22 C21 C16 119.42(16) . . ?
C22 C21 C20 122.28(17) . . ?
C16 C21 C20 118.29(16) . . ?
C13 C22 C21 120.9(2) . . ?
C13 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
O4 C23 O13 124.40(16) . . ?
O4 C23 C19 119.16(16) . . ?
O13 C23 C19 116.44(17) . . ?
C10 O7 H7 109.4 . . ?
C7 C2 C3 120.5(2) . . ?
C7 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C11 C5 C6 118.94(16) . . ?
C11 C5 C4 122.95(17) . . ?
C6 C5 C4 118.08(17) . . ?
C8 C6 C7 123.33(17) . . ?
C8 C6 C5 117.99(16) . . ?
C7 C6 C5 118.67(17) . . ?
C2 C7 C6 120.9(2) . . ?
C2 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C9 C8 C6 123.08(16) . . ?
C9 C8 H8 118.5 . . ?
C6 C8 H8 118.5 . . ?
C8 C9 C10 118.35(15) . . ?
C8 C9 C12 120.11(16) . . ?
C10 C9 C12 121.52(16) . . ?
O7 C10 C11 119.16(15) . . ?
O7 C10 C9 120.76(15) . . ?
C11 C10 C9 120.07(16) . . ?
C10 C11 C5 121.56(16) . . ?
C10 C11 H11A 119.2 . . ?
C5 C11 H11A 119.2 . . ?
O17 C12 O27 124.01(18) . . ?
O17 C12 C9 118.83(18) . . ?
O27 C12 C9 117.15(17) . . ?

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_COMPOUND7
_database_code_depnum_ccdc_archive 'CCDC 1032727'
_audit_update_record             
;
2015-03-29 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_audit_creation_date             2015-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H9 N2, C11 H8 O3, C11 H7 O3'
_chemical_formula_sum            'C34 H24 N2 O6'
_chemical_formula_weight         556.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   16.4090(10)
_cell_length_b                   11.6515(4)
_cell_length_c                   15.1195(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.910(7)
_cell_angle_gamma                90
_cell_volume                     2621.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14293
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         29.432
_diffrn_reflns_theta_min         2.328
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4274
_reflns_number_total             6182
_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       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0385P)²+0.5326P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Restrained distances
 O4-H4
 0.85 with sigma of 0.01
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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
N1 N 0.10784(10) 0.79182(12) 0.01230(11) 0.0345(3) Uani 1 1 d . . . . .
O4 O 0.00474(8) 0.96113(10) -0.38680(10) 0.0439(3) Uani 1 1 d D . . . .
O5 O 0.02302(8) 1.15055(10) -0.38663(9) 0.0476(3) Uani 1 1 d . . . . .
C5 C 0.15976(11) 0.93546(14) -0.21821(12) 0.0314(4) Uani 1 1 d . . . . .
C6 C 0.13396(11) 1.04111(13) -0.26178(12) 0.0308(4) Uani 1 1 d . . . . .
N2 N -0.00737(9) 0.92242(12) -0.13781(11) 0.0379(3) Uani 1 1 d . . . . .
O6 O 0.16615(10) 1.24525(10) -0.25480(11) 0.0557(4) Uani 1 1 d . . . . .
C9 C 0.23915(11) 0.91983(13) -0.13250(12) 0.0329(4) Uani 1 1 d . . . . .
C10 C 0.06131(11) 0.97583(13) -0.06507(12) 0.0326(4) Uani 1 1 d . . . . .
C12 C 0.12176(11) 0.90681(13) 0.01314(12) 0.0318(4) Uani 1 1 d . . . . .
C14 C 0.04850(11) 1.05441(14) -0.35126(12) 0.0334(4) Uani 1 1 d . . . . .
C16 C 0.18859(12) 1.13827(13) -0.21738(13) 0.0368(4) Uani 1 1 d . . . . .
C17 C 0.26644(12) 1.12512(16) -0.13438(14) 0.0428(4) Uani 1 1 d . . . . .
C18 C 0.26533(13) 0.81163(16) -0.08665(14) 0.0410(4) Uani 1 1 d . . . . .
C21 C 0.07700(12) 1.09512(14) -0.06153(14) 0.0381(4) Uani 1 1 d . . . . .
C22 C 0.29392(11) 1.01701(15) -0.09034(13) 0.0379(4) Uani 1 1 d . . . . .
C24 C -0.06178(13) 0.98807(16) -0.20992(15) 0.0442(4) Uani 1 1 d . . . . .
C25 C 0.19484(12) 0.95502(15) 0.09158(13) 0.0393(4) Uani 1 1 d . . . . .
C26 C 0.01688(14) 1.16014(16) -0.14026(16) 0.0457(5) Uani 1 1 d . . . . .
C27 C 0.23316(13) 0.76632(18) 0.16131(15) 0.0474(5) Uani 1 1 d . . . . .
C28 C 0.16011(12) 0.72219(16) 0.08283(14) 0.0401(4) Uani 1 1 d . . . . .
C29 C 0.15092(15) 1.14268(17) 0.01945(16) 0.0500(5) Uani 1 1 d . . . . .
C31 C 0.37367(13) 1.00099(19) -0.00367(16) 0.0536(5) Uani 1 1 d . . . . .
C34 C 0.25066(13) 0.88159(18) 0.16543(15) 0.0490(5) Uani 1 1 d . . . . .
C35 C -0.05177(14) 1.10686(16) -0.21413(16) 0.0468(5) Uani 1 1 d . . . . .
C36 C 0.20720(15) 1.07681(17) 0.09195(16) 0.0516(5) Uani 1 1 d . . . . .
C39 C 0.34198(14) 0.80001(18) -0.00352(15) 0.0505(5) Uani 1 1 d . . . . .
C41 C 0.39649(15) 0.8958(2) 0.03806(17) 0.0586(6) Uani 1 1 d . . . . .
O1 O 0.15181(8) 1.45169(10) 0.01620(10) 0.0473(3) Uani 1 1 d . . . . .
C11 C 0.30350(11) 1.41437(13) 0.04563(13) 0.0360(4) Uani 1 1 d . . . . .
C13 C 0.39654(11) 1.28375(14) 0.17472(13) 0.0390(4) Uani 1 1 d . . . . .
O2 O 0.20800(9) 1.54241(11) -0.07527(11) 0.0610(4) Uani 1 1 d . . . . .
C19 C 0.31849(11) 1.35075(14) 0.12758(13) 0.0369(4) Uani 1 1 d . . . . .
C20 C 0.46095(11) 1.28250(15) 0.13456(14) 0.0432(4) Uani 1 1 d . . . . .
C23 C 0.21552(12) 1.47452(14) -0.00844(14) 0.0409(4) Uani 1 1 d . . . . .
O3 O 0.35987(11) 1.48190(15) -0.06899(12) 0.0718(5) Uani 1 1 d . . . . .
C32 C 0.54399(15) 1.1369(2) 0.25197(19) 0.0660(7) Uani 1 1 d . . . . .
C33 C 0.37111(12) 1.41705(16) 0.00991(14) 0.0450(5) Uani 1 1 d . . . . .
C37 C 0.41015(14) 1.21263(17) 0.25580(15) 0.0493(5) Uani 1 1 d . . . . .
C38 C 0.44704(13) 1.35230(18) 0.05343(16) 0.0516(5) Uani 1 1 d . . . . .
C40 C 0.48150(15) 1.14006(19) 0.29282(18) 0.0602(6) Uani 1 1 d . . . . .
C42 C 0.53518(14) 1.2067(2) 0.17676(18) 0.0590(6) Uani 1 1 d . . . . .
H5 H 0.1209(11) 0.8707(13) -0.2473(12) 0.031(4) Uiso 1 1 d . . . . .
H17 H 0.3001(12) 1.1909(15) -0.1044(14) 0.046(5) Uiso 1 1 d . . . . .
H19 H 0.2728(12) 1.3505(14) 0.1520(13) 0.039(5) Uiso 1 1 d . . . . .
H24 H -0.1128(13) 0.9489(15) -0.2626(14) 0.049(5) Uiso 1 1 d . . . . .
H26 H 0.0262(12) 1.2397(16) -0.1413(13) 0.048(5) Uiso 1 1 d . . . . .
H28 H 0.1427(12) 0.6409(16) 0.0739(13) 0.045(5) Uiso 1 1 d . . . . .
H39 H 0.3593(13) 0.7253(16) 0.0262(14) 0.052(5) Uiso 1 1 d . . . . .
H27 H 0.2701(13) 0.7149(16) 0.2102(15) 0.056(6) Uiso 1 1 d . . . . .
H34 H 0.3033(14) 0.9130(17) 0.2205(16) 0.063(6) Uiso 1 1 d . . . . .
H35 H -0.0948(13) 1.1484(16) -0.2708(15) 0.057(6) Uiso 1 1 d . . . . .
H29 H 0.1583(13) 1.2246(17) 0.0210(14) 0.058(6) Uiso 1 1 d . . . . .
H18 H 0.2293(12) 0.7474(16) -0.1145(13) 0.045(5) Uiso 1 1 d . . . . .
H37 H 0.3663(13) 1.2151(16) 0.2819(14) 0.054(6) Uiso 1 1 d . . . . .
H31 H 0.4090(13) 1.0666(17) 0.0222(15) 0.058(6) Uiso 1 1 d . . . . .
H1 H 0.0595(13) 0.7619(16) -0.0392(14) 0.048(5) Uiso 1 1 d . . . . .
H38 H 0.4902(14) 1.3509(16) 0.0295(15) 0.060(6) Uiso 1 1 d . . . . .
H41 H 0.4504(15) 0.8865(18) 0.0966(17) 0.070(7) Uiso 1 1 d . . . . .
H32 H 0.5945(16) 1.0860(19) 0.2784(17) 0.079(7) Uiso 1 1 d . . . . .
H42 H 0.5738(14) 1.2041(16) 0.1455(15) 0.057(6) Uiso 1 1 d . . . . .
H36 H 0.2596(15) 1.1074(17) 0.1472(16) 0.066(6) Uiso 1 1 d . . . . .
H40 H 0.4854(15) 1.0894(19) 0.3439(18) 0.075(7) Uiso 1 1 d . . . . .
H6 H 0.1085(17) 1.238(2) -0.3078(19) 0.089(8) Uiso 1 1 d . . . . .
H3 H 0.303(2) 1.519(2) -0.087(2) 0.111(10) Uiso 1 1 d . . . . .
H4 H -0.0511(9) 0.968(2) -0.4313(16) 0.116(11) 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
N1 C12 1.358(2) . ?
N1 C28 1.327(2) . ?
O4 C14 1.2886(19) . ?
O5 C14 1.2358(19) . ?
C5 C6 1.376(2) . ?
C5 C9 1.410(2) . ?
C6 C14 1.491(2) . ?
C6 C16 1.424(2) . ?
N2 C10 1.350(2) . ?
N2 C24 1.323(2) . ?
O6 C16 1.354(2) . ?
C9 C18 1.416(2) . ?
C9 C22 1.419(2) . ?
C10 C12 1.429(2) . ?
C10 C21 1.410(2) . ?
C12 C25 1.401(2) . ?
C16 C17 1.371(2) . ?
C17 C22 1.407(2) . ?
C18 C39 1.360(3) . ?
C21 C26 1.405(3) . ?
C21 C29 1.424(3) . ?
C22 C31 1.421(3) . ?
C24 C35 1.398(3) . ?
C25 C34 1.399(3) . ?
C25 C36 1.433(3) . ?
C26 C35 1.357(3) . ?
C27 C28 1.382(3) . ?
C27 C34 1.369(3) . ?
C29 C36 1.338(3) . ?
C31 C41 1.357(3) . ?
C39 C41 1.402(3) . ?
O1 C23 1.277(2) . ?
C11 C19 1.374(2) . ?
C11 C23 1.500(2) . ?
C11 C33 1.424(2) . ?
C13 C19 1.410(2) . ?
C13 C20 1.424(3) . ?
C13 C37 1.417(3) . ?
O2 C23 1.248(2) . ?
C20 C38 1.408(3) . ?
C20 C42 1.420(3) . ?
O3 C33 1.357(2) . ?
C32 C40 1.403(3) . ?
C32 C42 1.356(3) . ?
C33 C38 1.365(3) . ?
C37 C40 1.359(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28 N1 C12 123.12(16) . . ?
C6 C5 C9 122.31(15) . . ?
C5 C6 C14 120.64(14) . . ?
C5 C6 C16 118.67(15) . . ?
C16 C6 C14 120.65(14) . . ?
C24 N2 C10 116.54(15) . . ?
C5 C9 C18 122.52(16) . . ?
C5 C9 C22 118.36(15) . . ?
C18 C9 C22 119.11(16) . . ?
N2 C10 C12 117.72(14) . . ?
N2 C10 C21 124.16(16) . . ?
C21 C10 C12 118.12(15) . . ?
N1 C12 C10 119.49(15) . . ?
N1 C12 C25 118.95(16) . . ?
C25 C12 C10 121.56(15) . . ?
O4 C14 C6 115.89(14) . . ?
O5 C14 O4 123.82(16) . . ?
O5 C14 C6 120.29(15) . . ?
O6 C16 C6 121.89(16) . . ?
O6 C16 C17 118.03(15) . . ?
C17 C16 C6 120.09(15) . . ?
C16 C17 C22 121.50(16) . . ?
C39 C18 C9 120.88(19) . . ?
C10 C21 C29 119.47(17) . . ?
C26 C21 C10 116.57(17) . . ?
C26 C21 C29 123.96(17) . . ?
C9 C22 C31 118.19(16) . . ?
C17 C22 C9 119.05(16) . . ?
C17 C22 C31 122.75(17) . . ?
N2 C24 C35 123.93(19) . . ?
C12 C25 C36 118.01(17) . . ?
C34 C25 C12 118.03(16) . . ?
C34 C25 C36 123.96(18) . . ?
C35 C26 C21 119.58(17) . . ?
C34 C27 C28 119.55(19) . . ?
N1 C28 C27 119.72(18) . . ?
C36 C29 C21 121.69(18) . . ?
C41 C31 C22 120.9(2) . . ?
C27 C34 C25 120.62(19) . . ?
C26 C35 C24 119.21(19) . . ?
C29 C36 C25 121.13(19) . . ?
C18 C39 C41 120.15(19) . . ?
C31 C41 C39 120.7(2) . . ?
C19 C11 C23 120.61(16) . . ?
C19 C11 C33 118.79(16) . . ?
C33 C11 C23 120.51(16) . . ?
C19 C13 C20 118.00(17) . . ?
C19 C13 C37 122.65(18) . . ?
C37 C13 C20 119.22(17) . . ?
C11 C19 C13 122.27(17) . . ?
C38 C20 C13 119.26(17) . . ?
C38 C20 C42 123.0(2) . . ?
C42 C20 C13 117.73(19) . . ?
O1 C23 C11 117.52(16) . . ?
O2 C23 O1 123.68(17) . . ?
O2 C23 C11 118.80(17) . . ?
C42 C32 C40 120.9(2) . . ?
O3 C33 C11 120.42(17) . . ?
O3 C33 C38 119.32(18) . . ?
C38 C33 C11 120.24(18) . . ?
C40 C37 C13 121.0(2) . . ?
C33 C38 C20 121.28(19) . . ?
C37 C40 C32 119.8(2) . . ?
C32 C42 C20 121.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
